---
title: "Lenny's Podcast — 2023 Q1 合集"
date: "2023-01-01"
source: "Lenny's Podcast"
url: "https://www.lennysnewsletter.com/"
---

<div v-pre>


# Lenny's Podcast - 2023 Q1 (22 episodes)

This file contains 22 articles/episodes.

---

## [1/22] Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack)

**Jules Walter** (00:00:00):
If you give me feedback, I'll be like, "Hey, thank you so much. This is super helpful," because people are like, "Oh, he actually likes the feedback." Now, inside my heart might be melting. I'm like, "Oh, I thought I got better at this." You know what I mean? 

**Lenny** (00:00:14):
Yeah. 

**Jules Walter** (00:00:14):
But externally, I'm like, "Hey, thank you," and I mean it. I think that's the key that most people don't focus on. And if you get more feedback, then you'll just get better at the things.

**Lenny** (00:00:26):
Welcome to Lenny's Podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. Today, my guest is Jules Walter. Jules is a product leader at YouTube. Before that, he spent four and a half years at Slack, where he was their first growth PM and then went on to lead their monetization teams and also their mobile team. He's also the co-founder and a board member of the Black Product Managers Network and CodePath, both of which are nonprofits that aim to increase diversity within tech. Jules and I have collaborated on a number of projects over the years, including a killer guest post on building product sense that continues to be one of the most shared and beloved posts in my newsletter. 

**Jules Walter** (00:03:52):
Hey, Lenny. Thanks for having me. I'm really excited.

**Lenny** (00:03:54):
I am even more excited. This chat has been a long time coming. I've been hoping to get you on this podcast ever since this podcast even launched. And then in the meantime, while we've been waiting to schedule it, a number of guests have mentioned how useful you've been to them in their career, and so I'm just really excited to finally have you on.

**Jules Walter** (00:04:11):
Yeah, same here.

**Lenny** (00:04:12):
Let's just start with a quick overview of your background. Could you share some of the wonderful places you've worked, some of the wonderful projects you've worked on, and then just a bit about what you're working on today?

**Jules Walter** (00:04:25):
Yeah, happy to. Some quick background, grew up in Haiti, studied computer science in college, went to business school. My first career was actually not in tech; it was in medical devices. I was a GM for a company based out of France and also overseeing West Africa business for them. After doing that, I moved back to the US, launched my own startup, which didn't work out, and then I moved to the Bay Area roughly eight years ago. In the Bay Area I wanted to become a PM, which was really hard to get into. At first, I joined a startup, series a company, became head of product for them, and then join Slack as the first PM on their growth team. Then from their, help scale the growth team at Slack. When I joined revenue was around 50 million; when I left roughly four years ago was 10x that. And then after Slack I recently joined YouTube Google about two years ago. At Google I'm a product lead at YouTube, where I'm driving a product called Primetime Channels, which actually recently launched in November in the US. And in that product, we're bringing streaming services to YouTube so that users can watch their favorite movies, shows, and sports content.

**Lenny** (00:05:35):
Amazing. The reason that I think we pushed this schedule of this podcast recording out is because you've been working on that product for many months and I'm glad to hear that it's finally launched. How did the launch go?

**Jules Walter** (00:05:45):
So far so good. It's really exciting to take a product from nothing to something. 

**Lenny** (00:05:49):
Especially at a company like Google.

**Jules Walter** (00:05:51):
Yeah. And then over time we are adding more exciting content onto the product. We just recently you announced that we're adding NFL Sunday Ticket in 2023 to primetime channels and also to YouTube TV. It's been a really exciting project.

**Lenny** (00:06:05):
That's awesome. I bet there's a lot of stories there, but I know you can't talk too much about what's happening at Google, so we'll move on. I like the point that you made about joining a startup, like you were trying to get into product management and you joined a startup as their first PM. I think you mentioned that's how you got into the PM path or I guess... Correct me if I'm wrong, but that's an interesting example of one of the paths into product management: joining a startup, getting into product there.

**Jules Walter** (00:06:27):
Not as their first PM, but I joined as one of their first PMs. Yeah. 

**Lenny** (00:06:31):
As one of their first PMs? 

**Jules Walter** (00:06:32):
Yeah. 

**Lenny** (00:06:33):
That's something I hear often is just one of the paths to product management is join a startup, start doing product, and then you're a PM. And then you have a PM title on your resume and you can now join other companies. Is that something you found or anything you can take away from that experience?

**Jules Walter** (00:06:46):
Yeah. It's really, really hard to get into product and there isn't a really set path to do that. What I've seen is the path that we just talked about, join a startup and then from there go into different companies. And then the other path that is typical is being at a company and then switching product management, especially if you develop domain expertise and there's a need for a PM. So, that's even more frequent. Of course there's also acquisitions that sort of thing, but making that initial transition is really hard.

**Lenny** (00:07:19):
I didn't realize you were the first growth PM at Slack. That is a big role. How did that work out? How did you become the first growth PM at Slack? Was that the first time you're doing growth? What's the story there?

**Jules Walter** (00:07:30):
I joined Slack early 2016 and the role that was available at the time was growth. I did not know anything about growth, but I was like, "Hey, this is my way in at such a great company." So, that's what I joined to do. And then what I did there was really take a learning mindset and lean on mentors, and we can talk about that to really learn the practice of growth and applied for Slack.

**Lenny** (00:08:00):
Cool. We're definitely going to talk about some of those things. Just thinking about that experience and that ride at Slack, what's like maybe the most tangible memory or most, I don't know, interesting story of just riding that rocket ship of Slack growth as one of their early PMs?

**Jules Walter** (00:08:14):
There's many, many stories. My experience was I got in, didn't know much about growth, and then through mentorship, in particular, one mentor, Bangaly Kaba, sort of learned how to apply growth frameworks to my work. And then when I did that within six months, I was able to ship changes in the new user experience, especially on mobile. That moved the needle by a lot, like double-digit percentages within your [inaudible 00:08:38]. And we're talking about top line metrics like activation. It was just interesting being able to have such impact very quickly at a company, and then the company itself went through all these milestones. I mentioned I joined 50 million, the next thing it's a hundred, and it keep doubling, going through a public offering. So, there's just so many stories that are unique to hyper growth.

**Lenny** (00:09:01):
You also didn't mention in your background all these kind of extracurricular activities that you have. I've always been impressed with how much time you put into things that are kind of just volunteer projects on the side. Can you talk about some of the stuff that you do outside of your actual day job?

**Jules Walter** (00:09:15):
Outside of my work at YouTube now and also my family and young kids, I'm also involved with two nonprofits that I co-founded. Both of them are actually about improving diversity in tech, which is something I'm really passionate about. The first one is called CodePath and it's improving diversity for software engineers, and the second one is Black PMs focused on product management. With CodePath specifically, what we do is we train over 5,000 students every year at universities, typically the university with strong underrepresented populations, and we help them find internships and jobs at top tech companies. And then with Black PMs, we have a community of over a thousand PMs and aspiring PMs and then we help them find community and also grow their skills. Both of them are nonprofits that I wasn't actually setting out to build them. It's more like I had the need myself or I wish I had those sort of support when I was earlier in my career. And then I started helping folks and then one thing led to the other, especially my co-founders, and then these became big.

**Lenny** (00:10:22):
Sounds like a classic startup story, solve your own problem and turns into a larger and larger thing. I think I try to work with Black PMs as much as I can, and I know that you recently had a conference, which is so cool. I don't know, it was a really big conference that you organized. I don't know how you all had time for all that, but anything you can share about this conference and is there another one coming?

**Jules Walter** (00:10:42):
Now we have a really good team at Black PMs. The CEO, Brittany Bankston and the team, Benin Saffo and others, have helped put together that amazing conference that I was able to attend. It's amazing that it's hard for underrepresented community to see themselves in podcasts, at conferences, at speakers, that sort of thing. So, it gave that opportunity and it also enables us to realize that you're not alone. Because part of why I created Black PMs with my co-founders is... Actually, I'll tell you the story. 

**Jules Walter** (00:11:17):
I think it was around 2016, I was at a barbecue. I met another Black PM, Maryanna Quigless. I didn't know her and I was like, "Oh, you're a Black PM at Facebook. How many of you are there at the company?" And we're joking and we're like, "Hey, I bet we can list all the Black PMs we know." And we had basically roughly 15 between the two of us and we're like, "Hey, let's bring them all together in a room and to have a community." From there, started helping each other and that grew from 15 to now over a thousand.

**Lenny** (00:11:45):
Wow. Amazing. It's really inspiring, the work that you do. I don't know how you find time for all this. I love that you found ways to kind of delegate this and have other people run the program now.

**Jules Walter** (00:11:55):
Yeah. Now, I'm mostly on the board of these organizations. We have really solid teams for both Black PMs and CodePath, and the teams are just really amazing.

**Lenny** (00:12:03):
This touches on the stuff that I want to spend most of our time on our chat, which is around mentorship and just generally becoming a stronger product manager through all the ways you can become a stronger product manager. You mentioned you had a lot of great mentors. I've heard from other people, you've been a great mentor to them and you've also just been really successful at a number of really world-class companies. What I want to chat about is just, what have you found to be the most important skills to develop as a PM as you advance in your career, and then how to actually build those skills partly with mentorship, partly other ways? Maybe just to start, what have you found to be the most important skills in your career that have most helped you advance in your career and other PMs around you?

**Jules Walter** (00:12:50):
In terms of skills, I think of it in terms of two buckets. One are IQ skills, intellectual skills, like what sometimes people call hard skills. And then the other things are the EQ skills, oftentimes called soft skills. What I've seen in my career is that early on, I leaned more into the hard skills, the IQ stuff. That was what was most helpful to me. And then later on, I spent more time getting better at the EQ skills. The reality with PMs is that within each of these buckets, there's so many skills and then you can feel overwhelmed, so my advice is really just start skill by skill. What I did specifically is I joined Slack, I was in ICPM. When you join a new company, especially if you're earlier in the mid-career, you really want to get good at things like execution, IQ skills, execution, product sense, strategy. So, those were critical for me, especially my first year at Slack. 

The other skill that I'll also call out, which nobody talks about for some reason, is interview skills, because so much of what gives you a chance to become better as a PM is working at a great company. How you get that job beyond networking is actually becoming good at interviewing. If you think about my career, getting into Slack changed my trajectory and I was able to do that because I got slightly somewhat good enough at interviewing. I barely got the job and then I was really good at execution and got better at these other things, product sense, strategy, et cetera. In that phase, the things that I was working on, as I mentioned earlier, were things like improving user activation. So, it relies on those skills: identifying the opportunities, running experiments, executing quickly, and so on. That's the first set of skills.

**Lenny** (00:14:49):
Before we move on, and the second set is EQ, right? Is that where you're going? 

**Jules Walter** (00:14:51):
Yeah. 

**Lenny** (00:14:52):
Cool. Maybe just one quick thread I want to pull on is this interviewing skill. That's really interesting. Your point here is you're not... And I think you're going to get to this of just how to get better at these skills. You mentioned one of the best ways is to be surrounded by amazing people who can help you get better at these skills, but you won't get there if you can't actually get into a company like Slack. Is there something you've found to be useful in building these interview skills? When you say interview, it's being interviewed, not interviewing other people, like passing these interview tests. 

**Jules Walter** (00:15:22):
Yeah. 

**Lenny** (00:15:22):
Yeah. I guess what have you found has been most helpful in helping you become a better interviewee?

**Jules Walter** (00:15:28):
When people tell me, "Hey, I'm going to a interview at this company." First question I ask is, "How many mock interviews have you done?" And the answer typically is zero. It's, "Oh, I read a bunch of stuff. I practiced in my head." But I'm like, "How many actual mock interviews have you done?" And I would recommend people to do dozens of those mock interviews. Now, the other thing about practice is it's always better if you deliberate practice. If you mock interview with somebody who's actually good at interviewing, then you'll get better faster. But even if you don't do that, just going from zero mocks to practicing in your head to actually doing mocks with peers and others is going to get you to another level. And then the other thing I'll say is interviewing can be quite traumatic and difficult for a lot of people, even me. I mean before I got this job, I interviewed at Google, I don't know how many times, over the last decade or two.

**Lenny** (00:16:22):
Wait. You're saying you're interviewed at Google many times and you didn't get in then you kept looking for new opportunities?

**Jules Walter** (00:16:27):
Yeah. I graduated from MIT and I think even since internship times in '07, I'd interviewed for roles at Google and I didn't get those roles or Meta or various other companies. It's because I wasn't good at interviewing and I didn't know people at those companies. By the way, most things you do, people give you some feedback so you can get better at it, but interviewing you never get any feedback. That's the thing people don't talk about, but it's actually an important skill or a barrier to underrepresented folks.

**Lenny** (00:17:01):
To actually get feedback?

**Jules Walter** (00:17:02):
Yeah. You won't get feedback after an interview at any company.

**Lenny** (00:17:05):
That's a really good insight of just people see you join a YouTube and are like, "Oh, yeah, of course he's going to get into YouTube." But you're saying that you actually tried to interview and get into Google many times and it took a number of attempts and advancing your career a little bit before you actually... So, don't feel so discouraged if it doesn't work out. 

**Jules Walter** (00:17:23):
Yeah. 

**Lenny** (00:17:24):
In terms of this mock, that's a really important point of just actually doing the interviews, like practicing, practicing, practicing. Not just reading questions but actually testing and practicing interview. If you were interviewed at a big company, there's a lot of videos out there of like, "Here's the questions they ask. Here's what they look for." And you're saying find people that work at the company and do these sorts of interviews with them. For companies that are smaller that maybe don't... It's not as obvious what they're going to ask you. Do you have any advice on how to find someone to do a mock interview with or how or what to actually be talking through?

**Jules Walter** (00:17:56):
Yeah, it's hard at smaller companies. However, I think interviewing even at bigger companies will help you [inaudible 00:18:04]. A lot of the times the bigger companies have more rigorous processes. So if you can do well there, then it is a bit easier elsewhere. But the key is really that practice part, which people overlook.

**Lenny** (00:18:18):
Cool. Well, maybe one last question there and we'll move on. Do you have any favorite resources or just advice of where to go find the questions to mock interview with and then who do you look forward to do these interviews with, like just find someone at the company or one of these larger companies that you respect to mock interview with?

**Jules Walter** (00:18:34):
I mentor a bunch of people who talk about various communities that exist out there. I can follow up on those, but there are large communities of people prepping for these companies. The key is really just being a part of a community and doing the mocks. And then the last thing I'll say on this is interviewing is hard and especially, I think, hard for underrepresented folks because it's high pressure. It's high stress, high ambiguity-

**Lenny** (00:19:02):
So much stress.

**Jules Walter** (00:19:03):
... coming into a company. I've gone into companies like an interview and then the whole panel, nobody looks like me. I walk into the cafeteria, nobody looks like me. And then you are interviewing and you have all this self-talk about, "Hey, do I even want to work there? Will I belong," while you're trying to solve complex problems. So, that's also the other part companies don't think about. What I do, like folks at Black PMs that I coach, is really help them find groups of people, like small groups. Let's say three of us, et cetera, three to five, and then you practice with that group who are going through the process. And because you like the people, then it makes it a bit more fun and it also can help you prep for your own nerves in those interviews.

**Lenny** (00:19:48):
What I'm hearing is, and I know we hear this all the time, if you're, say, a Black product manager, it's so much harder to not just get in because there's potentially bias at the company, but you're just psychologically not feeling as comfortable because nobody looks like you. You're worried that they're going to have bias against you. Is that what you find?

**Jules Walter** (00:20:07):
Yeah, that has been my experience and it's also what I hear from a lot of people I mentor.

**Lenny** (00:20:13):
Your advice there, and this is helpful to anyone also, is just practice even more because that's probably the best way to get over that as much as you can.

**Jules Walter** (00:20:21):
Yeah. You want to basically practice so much that even at your worst, you're good enough. I've always felt like most interviews, I literally did my worst. It's just that it was good enough to pass. You're so stressed out, you don't relate to the person, et cetera.

**Lenny** (00:20:38):
Got it. Okay. Let's go back to the question I asked that I pushed us away from. We were talking about what skills as a PM you want to be focusing on that mostly will help you in your career, and we started with IQ. I wrote a couple notes, so there's the concrete skills, execution, products and strategy, interviewing, and then there's a second bucket of EQ.

**Jules Walter** (00:20:57):
So, the IQ I already talked about. Those are the skills that help me at, especially in my first year at Slack, drive big good experiments, design good product experiences, and then drive results. But then what happened is as I get promoted, managed people and then start having larger scope, then there's a lot of ambiguity and stress that comes in with that increase in scope. And that's where the EQ stuff shows up a lot, specifically things like communications, because it's no longer my team. It's like cross-functional partners, other teams, executives, so you have to communicate all the time to different people. And then the other thing is things like leadership. Now, I'm driving initiatives that involve multiple teams, basic company level OKRs, and then the other thing too is beyond leadership, which is managing your team as well. How do you be a good manager? How do you deal with the ambiguity, stress? How do you influence various people? 

**Jules Walter** (00:21:58):
These are the EQ skills. What I've seen is, number one, it's much harder to learn these skills than the IQ stuff. The IQ is very intellectual. Sometimes, you just need a mental model, practice a bit. The EQ, I'm still learning these things. It's just like every... I'm trying to get better. Then the other thing beyond it being hard to learn is that the EQ stuff... What you need to focus on is specific to you, so you learn it. You probably work on something different than what I would work on versus if we're both trying to be better at strategy or execution, there's a lot more overlap. So, there's a lot of self-awareness that you need to have to know even what to work on and then you need to continuously practice it.

**Lenny** (00:22:44):
What did you find was the most important EQ skill for your career that helped you in this journey?

**Jules Walter** (00:22:50):
I don't know if there is one that single-handedly was the most important. I had to develop on many of these things. I can tell you, for example, communication is something that is helpful, especially as I become more senior. What happened for me is, early in my career, it was more about clarity and then conciseness. Then later it became more about how do you tell a story, and then also how do you communicate in an empathetic way. Specifically, you're telling the same story or presentation but to different audiences, and each time you have to adjust it because the CEO will care about this part, the CFO will care about this other part, and so on. I think that's one area where I spend a lot of time. And then the other thing also that has been helpful is the self-awareness part that I mentioned, where through mentorship, especially mentors who were very honest and help me see my blind spots, I was able to see my own patterns.

**Jules Walter** (00:23:54):
When I'm under stress, for example, I tend to withdraw and not see anything. So, then you might think I'm disengaged. By the way, in an interview context you might be like, "Oh, does this person even want to work here?" Then once you know these patterns you know, "Okay, I'm stressed right now, but I need to say something so that people see that I'm actually interested in this problem; I'm just thinking through it. Well, let me verbalize my thought process." So, that's me as an example. For you, it might be the opposite. The self-awareness piece has been really helpful and it's something I continue to work on.

**Lenny** (00:24:26):
That's an interesting point that it's important to understand how you react and to figure out what's unique about you that you want to be working on, especially within EQ. For this example you gave about how stress impacts you, how did you actually discover that? Was that this mentor just pointing out, "Hey, Jules, I've noticed this happens," or is there anything else there that maybe folks would find useful?

**Jules Walter** (00:24:47):
Generally, you need someone to put a mirror in front of you irritably. Sometimes, it's like you hire a coach, I talk to, and they see patterns. I've done group coaching too. In this case specifically, he was a mentor. His name is Lawrence Ripsher. He was head of product at Pinterest and became a mentor and now a close friend. One day I was preparing for... I think I need to do a representation and he was like, "Hey, I've noticed that when you are thinking, you're just quiet. Let me tell you what's going on in my own head when I see that." And then he was like, "Hey, I'm telling myself that he's not interested in what we're doing." And I'm like, "Really? That's the least thing." And then I realized that's a pattern I have. Over time, through him and others, I've also observed other patterns.

**Lenny** (00:25:38):
I missed this, but was he a manager or just a mentor you had within the company?

**Jules Walter** (00:25:42):
We didn't work at the same company. When I was at Slack, he was head of product at Pinterest. We met at a dinner and then from there, over time, he became a mentor and then we started meeting. When I would hit difficult situations, sometimes I would call him and ask for advice, and then through those interactions he's helped me identify some of my blind spots.

**Lenny** (00:26:08):
Okay, awesome. We're definitely going to talk about mentorship and how to work with a mentor, but let's kind of wrap up this EQ piece. You mentioned within EQ, skills to think about working on communication, leadership, and management. Is there anything else and then is there an example of one of these skills and how, I don't know, it helped you in your career or held you back until you figure out how to work on this?

**Jules Walter** (00:26:30):
High level, I think those buckets are pretty broad: comms, leadership, management. Within each of them, there are various skills like setting vision, strategy, listening to learn, those sort of things. It's actually the type of things that Matt Mochary talked about when he came to speak at your podcast. I mentioned communications was one thing, right? What happened was, when I was at Slack, I was pretty good at writing, which by the way I was terrible at long time ago. It took me years, maybe decade, to get better at. But then when it was time to present... I was fine at presenting, but then if you ask me questions, things would crumble. That even happened to me once at an interview, where I did well presenting and then they asked me a question and then I just gave an answer that wasn't good. 

**Jules Walter** (00:27:22):
Then the self-awareness part helped me figure out what was going on. For me specifically, I realized whenever people ask me questions, if I didn't know the answer, I would have all this negative self-talk and I basically... You'd ask me a question and of course it could be something like, "Why are we doing it this way?" And it might come from a place of curiosity, you're just like, "Hey, I don't know. Can you tell me why you have more context," right? But in my head I would hear, "I don't agree with this." And that would be my self-talk. "Oh, this person doesn't agree with this," instead of being present and trying to understand where are they coming from and maybe asking follow-ups like, "Hey, thanks for asking the question. Is your concern more about, I don't know, scalability of this approach or is it more that you don't think it's effective even if it's not scalable?" 

**Jules Walter** (00:28:10):
You know what I mean? For someone else, it might be the easiest thing, but for me it took me months and months to, first of all, figure out that I had this pattern. And then once I figured out the pattern, it took also a while to now actually act on it so that now I'm comfortable. If you ask me a question, sometimes I don't know and I'll say, "Hey, let me get back to you." Sometimes I don't know and I'll say, "Hey, I don't know, but here's what I'm thinking." This little thing that may seem so obvious to you took me a while and different people have different versions of these blockers.

**Lenny** (00:28:45):
**Jules Walter** (00:30:24):
I will share my approach. It might not work for everyone and later when we talk about strengths and weaknesses. You might see why that works for me. What I do specifically is when I'm trying to learn something new, I try to think about what is an outcome that I could drive. And if I drive this outcome, it will be proof that I'm better at this thing. If we go back to this story of when I joined Slack, I didn't know anything, literally anything about growth. And I was telling myself, "I hope they don't fire me." But then the outcome I wanted is, within six months, I wanted to ship enough experiments that were successful, that drove activation by, let's say, X percent. So, that's very concrete. 

**Jules Walter** (00:31:06):
Then once I have this outcome, I work backwards to figure out how am I going to do that. One of the things we can talk about later when we talk about strength is that, for me, I'm really good at asking questions. What I do then is I start asking questions like, "Okay, I'm trying to drive activation for Slack. What are some frameworks that I should use to drive activation? What are best practices? What are examples?" I have a sense of the kind of question that, if I were to answer them, I'd be able to drive the outcome. And then what I do is I read a little bit, not a lot about the topic, just to make sure I'm asking the right question. Then I refine my questions and then I find the best people in the field and I just go talk to them. That's where we'll talk later about the mentorship part. 

**Jules Walter** (00:31:54):
In the case of activation, I was like, "Okay, what's the company that defined growth?" At the time, Facebook. "Who are the people that I can reach out to that do growth at Facebook?" And one of them was Bangaly Kaba and also Adriel Frederick who spoke at your podcast. I had met both of them at a random event. Then I'm like, "I need to find a way to have a chat with these folks and to help answer those questions with them." So, that's what I did with Bangaly in particular and also Adriel to a certain extent. I then learned, "Okay, here are frameworks to use for growth." For example, understand, identify, execute. Spend a lot more of your time understanding why people aren't staying on Slack versus anything else, so then I had pointers. 

**Jules Walter** (00:32:40):
Once I have the pointers, then I try to go through the thing. I'm like, "Okay, now let me..." I call the user researcher, "Hey, can we do a research on people who are signing up on Slack?" Data analysts, let's look at the data. What correlates with activation?" Those sort of things. Then after I go through a look, where I actually see results, whether they're good or bad, I go back to the mentor and I'm like, "Hey, I did this. It was actually successful. Thanks a lot." Now, I'm thinking about this other problem." I keep going and that's how I rinse and repeat, and over time I drive the outcome and I also know I'm getting better at this thing by working with the experts.

**Lenny** (00:33:18):
There's a few interesting takeaways there. One, is that you kind of create a forcing function for yourself to learn a thing. It's like, "Hey, I'm going to learn this thing. Let's create a goal that my ass is on the line to hit and then that's going to force me to go figure this out." And then two, it's interesting how often you come back to mentors and other people around you helping you out, which is a really good reminder. You don't have to figure things out for yourself; there's people out there that know these things and they're happy to help. A question I want to ask and I'll save this, because I we're going to talk about mentorship specifically a little bit later, just like how to find these people. Not everyone has access to Bangaly and Adriel, and I'm curious just how you found these folks, how you recommend other people find folks like that. But that's an awesome example. One tactic you're talking about here is just work backwards from a forcing function you've created for yourself to learn a thing. And in this case, what was it you were trying to learn? You were trying to learn growth, is that right?

**Jules Walter** (00:34:11):
Yeah, I was trying to learn growth and I wanted to do it in a context of activation, like new onboarding. And then later I also wanted to learn growth but in a different context, which was monetization. How do you drive revenue growth, not just get more users? And then later it was things like, "How do I learn how to create a growth org? How do I structure my team? How do I set work streams that add up to a coherent strategy?" And you just keep going

**Lenny** (00:34:42):
In those examples, did you do the same thing, you found people to talk to? 

**Jules Walter** (00:34:46):
Yeah. Yeah. It's the same approach. Sometimes what happens is I have a few mentors that I just keep going to over the years and it's just a top exchange and sometimes I sort of get new mentors who are experts at these new topics. It's a combination of those two things for me. And the thing is you obviously can learn without this approach, but this approach makes you, at least for me, makes me learn so much faster.

**Lenny** (00:35:14):
That's probably one of the most interesting things I've learned about mentors, and you're touching on this, that people want to help. They're happy to help if people come ask, unless they're just dumb questions or they're just overwhelmed. People are generally very happy to help. People are always worried like, "Why would they spend any time trying to help me with this random thing?" It's really the opposite; they're happy to help.

**Jules Walter** (00:35:34):
Yeah, exactly.

**Lenny** (00:35:35):
Coming back to the EQ and IQ buckets, are there other examples of ways you've learned to improve, say, strategy, execution, product sense, things like that?

**Jules Walter** (00:35:46):
Whether you have a mentor or not, there's other things you kind of have to do. For me, for example, one thing I do is I try to identify what's the best practice for something. For example, let's say strategy. There was a phase where I got feedback, "Hey you need to be better at strategy." Then I'm like, "Okay. Well, can you help me understand what are people at this company that was awhile back, where you think have done a great job at strategy or what are examples of artifacts?" Then I get these artifacts and I reverse engineering them. I try to think, "Okay, what are the top questions, the answer? Maybe I'm not answering all these questions. How do they do it?" And you start seeing the patterns like, "This person did it in a memo, this person did it in a deck." So, it's not about the format, but what is it about? Then this person had a lot of data, this person is quantitative, qualitative. So, that's a big part of what I do as well. It's true for all these things. 

For execution, it would be things like me attending another PMs meeting. "Oh, I heard this person is amazing at executing. Let me just see how they're on a meeting." And then you're like, "Whoa, things we didn't notice." Or somebody is great at communicating and I'm like, "Okay. Well, did you send this email? It's great. Let me save it." I'd have docs where I saved templates of things, and a lot of the reason, I think, people don't learn through osmosis that way is because one is you're not at a company where you can see great artifacts sometimes. That's why I mentioned if you can get a better company, do that. The other thing, too, is even if you see the greatness around you, some people don't try to break it down, to understand: "Why is this one great and not that one?" So, I actually do spend a lot of time every week reflecting like, "Oh, I saw these docs that were great or I saw this presentation this person gave." I sometimes crash presentation audits PMs give to executives, just to see how they handle questions or these sort of things. A lot of it is just spending time observing as well.

**Lenny** (00:37:54):
I love this advice, it's so powerful. Just like, "Who is amazing at this skill? And let me just go watch them and learn from them."

**Jules Walter** (00:38:01):
Yeah. 

**Lenny** (00:38:02):
Something that you touched on here is, and I talk about this a bunch, that one of the benefits of working at a large company like Google, like Slack, is that you have access to a ton of real examples of strategy documents and vision documents and roadmaps and things like that, that once you're out of a company, like me, nobody shares these things publicly because they're sensitive. One of the best benefits of working at a large company is they have access to real life strategy documents, vision documents, things like that, so you should really savor that and collect them and, to your point, just study them. And I love your advice of just working backwards from like, "Okay, here's a strategy that work. What is it about the strategy that I can use when I'm building my strategy? What questions are they answering? How are they structuring it?" Things like that. That's awesome.

**Jules Walter** (00:38:48):
Similar to the mentor point, people are actually happy to talk to you. They're even flattered because no one else asked them. "Well, hey, I read your doc. Can we talk about it?"

**Lenny** (00:38:54):
Right. Whoever gets the... What PM ever gets someone coming to them? "I love your strategy doc. Tell me all about it. I'd love to talk about that."

**Jules Walter** (00:39:06):
Yeah. And then the other thing I'll say, too, is a lot of learning happens through the iterations and not by seeing the final product. We all see these products, like the iPhone and name your favorite product, but you don't know what versions they tried and sort of eliminated. And that's the benefit you also get at a company that has great product management. I actually sometimes tell the PM like, "Hey, don't just show me the one you just did. When are you going to do your next strategy? Can I join you then? I just want to sit and watch you write down the outline and just understand your thought process," or "I want to see when you're going to write your next exec update and understand how are you..." And you see them go through these iteration and you see them do things like get feedback that you didn't know they were getting all this feedback from. So, seeing the backstage is also really helpful.

**Lenny** (00:39:58):
It's interesting. Just as you're talking, I'm reflecting on how many benefits there are to working at a world class company. You are surrounded by really smart people who you can talk to and ask for advice and watch how they operate. You have access to really incredible documents and artifacts that you can learn from. Also, just the logo on your resume is really powerful for future job opportunities, which then comes back to the interview skills that you talked about and how important it is to be good at that to get into a company like that.

**Jules Walter** (00:40:24):
Yeah, totally.

**Lenny** (00:40:25):
Interesting. Okay. What about on EQ? Any examples of how you learned some of those skills that you talked about communication or leadership or management or anything along those lines?

**Jules Walter** (00:40:36):
Yeah. On the communications side, I read some stuff like Minto's Pyramid Principles. Extremely helpful and I know you had an article on that. 

**Lenny** (00:40:44):
Mm-hmm.

**Jules Walter** (00:40:45):
I mentioned also that whenever I see a great email exec update or whatever, I literally save it in a special folder.

**Lenny** (00:40:54):
I love that.

**Jules Walter** (00:40:55):
Also, by the way, I always ask for feedback more than I think many people and I try to see patterns in feedback. For me, one thing I've observed is I tend to write long sentences, coming from a Haitian-French background, but then I see that because I've seen enough feedback that are about it so I see the patterns. Or as I mentioned earlier, I used to not be clear like, "Are you saying this solution or that solution?" It's better sometimes to be wrong but clear than the other way around. That's on the comms side. And then the other things, it's mostly, for me, through mentorship, people like Lawrence helping me be real with myself. I've had a coach for a while and I also do group coaching, which I really love. Right now I'm doing group coaching with a company called Pathways to Leadership.

These sort of things have helped me infer what my strengths and weaknesses are and then work on them. And then one thing I'll say also about the EQ: it was the most frustrating learning for me. For the IQ stuff, within six months, sometimes three months, I can see clear progress when you see enough documents. You see five, six of them, you start seeing 80% of the patterns. But then with the EQ stuff, it's things I've been working on for years. I am better at them, but I still feel like I'm continuing to work on those things. And a lot of it is like lifting weights or building muscles; you have to do it every day or every week. And then if you stop doing it, over time you atrophy again. That's something that people need to acknowledge, too. Give yourself time and then also learn these skills one at a time ideally.

**Lenny** (00:42:45):
Oh, interesting. Can you talk a bit more about that learning skills one at a time? Is your approach just like, "Here's the thing, I'm working on this the next six months. I'm going to focus on that."

**Jules Walter** (00:42:53):
Yeah. My approach is typically I'll say, "I'm giving myself, I don't know, three months, six months." It depends on what [inaudible 00:43:00] I want to see in my behavior for these things and then I just go all in on that skill. Let's say I wanted to learn strategy, I'll be like, "Okay, I'm giving myself, let's say, six months." Every week, I'm going to do something related to learning strategy. It's going to be maybe I read the strategy for another feature product at my company and you just divide, right? Let's just say there's 10 features or 20, it doesn't matter. You just do one a week, so 20 weeks. You see what I'm saying? And then the other thing is, every week I'm also going to practice it towards my outcome. I'm going to spend, I don't know, three hours a week, maybe one hour a day, just thinking through my own product strategy. And I do that for six months. You do it enough that you get over the hump and then actually develop the skill. Now, the other approach you could take is... What most people do is they read an article on your newsletter or some other place and then like, "Oh, great. I learned an insight." And then you go back to usual.

**Lenny** (00:44:00):
And it's not like at the end of these six months, you're done. I'm strategy expert, I am good on strategy. To your point, it's building this muscle that will never be fully built. It just will get stronger. And every time you invest time learning something, it gets stronger.

**Jules Walter** (00:44:15):
Yeah, exactly. It's not that within six months you are clearly better. Now, you can invest another six months to get to the next level. Or you could say, "Now I'm going to switch focus to another skill and get that one to a similar level."

**Lenny** (00:44:28):
Is there a skill you're working on right now?

**Jules Walter** (00:44:30):
Always working on something. One I can call out is listening. One thing about the EQ stuff, too, by the way is you hear these words, and depending on how familiar you are, you understand or don't understand what it actually means. When I say listening, I'm good at seeking information to solve a problem. If you come to me and you're like, "Hey, Jules, I have this problem," I will know what to listen for and what to ask you. "Hey, Lenny, can you tell me A, B?" And then I'll help you solve the problem. However, there's also different listening patterns, one of which is you just create space for someone. It's not like you're seeking a particular information, just give them space to tell you what they want to tell you. And then the other side of it, too, is you help that person feel heard, "Hey, I feel like you actually understand me and you've heard what I'm saying." So, that's the part I am working on.

**Lenny** (00:45:25):
You mentioned the Matt Mochary episode. I imagine you've been listening to that, because that has a lot of great advice.

**Jules Walter** (00:45:29):
Yeah. Yeah, exactly. It's those kinds of things, right? And then he talked about saying back to people what you heard, asking for more information, et cetera.

**Lenny** (00:45:38):
Awesome. You mentioned that you asked for feedback from your peers, and I wrote that down. I wanted to double-click on that a little bit. How do you actually approach asking for feedback? Do you sound like a survey? Do you just ask people in meeting? How do you do that?

**Jules Walter** (00:45:51):
The feedback piece, it's something that I had to get better at. Over time, I'm asking for it, because what I realize is if people don't feel comfortable with you, they won't give you feedback. It's depending on the risk, right? Especially if it's constructive feedback. By the way, that's also something that's hard about being underrepresented. People sometimes don't have the same natural level of connection with you. I basically learned to go out of my way to make people comfortable giving me feedback. There's different techniques and Matt Mochary also talks about some of them. Sometime it's basically ask in a very specific way, "Hey, I did this presentation. I'm working on, I don't know, having more executive presence. Did you feel that? To which extent did you feel that I showed executive presence?" So, it's a very specific thing versus, "Hey, how did it go?" That's one thing you can do. 

**Jules Walter** (00:46:45):
Other thing you can do sometimes is you give yourself critical feedback in front of them and then you give them a chance to agree or disagree. "Hey, I feel like this presentation didn't go well for this reason. What do you think? But actually I thought it would've been fine; however, this other thing could have been better." And then the other thing I'll say that is very, very important if you're asking people for feedback is if you manage to get them to take the risk to give you the feedback, your answer has to be enthusiastically grateful. That's the key. What people knew at Slack, Google, et cetera, is if you give me feedback, I'll be like, "Hey, thank you so much. This is super helpful," because people are like, "Oh, he actually likes the feedback." Now, inside, my heart might be melting. I'm like, "Oh, I thought I got better at this." You know what I mean?

**Lenny** (00:46:45):
Yeah. 

**Jules Walter** (00:47:42):
But externally, I'm like, "Hey, thank you," and I mean it. I think that's the key that most people don't sort of focus on. And if you get more feedback, then you'll just get better at the things.

**Lenny** (00:47:51):
That is such a good advice, all these very tactical ways of getting actual real feedback from people.

**Jules Walter** (00:47:55):
Yeah. And then one thing I'll say, too, by the way, it's harder to get feedback on the EQ stuff, and that's also why it's harder to develop and why a lot of people reach terminal levels in product, because people are like, "Oh, they lack emotional intelligence." They say that in calibration rooms but not in your face, so that's also what you want when you hear feedback. You don't want just to like, "Hey, here's my piece of feedback that I can prove." You also want the part that is like, "Here's how you make me feel or how you come across that... If this is taken out of context, it won't be good for... I don't want this to be shared publicly or taken out of context, but I want you to know." And it could be things like, "Hey, when I talk to you, sometimes I feel like, I don't know, you're angry." And then I'm like, "Oh, really? In what scenario?" And then it's like, "Oh, I was so focused and listening to you intently that I could see now why I come across that way." 

**Jules Walter** (00:48:55):
But you could literally go your whole career and then nobody ever says these things, right? And that's the kind of feedback that I personally find most helpful is the subjective feedback, because nobody will tell me those things. Once somebody I trust tell me and I'm like... Oh, here's an example. I mentioned earlier I'm good at asking questions. I had somebody ask like, "Tell me. Hey, sometimes when you ask questions, you sound more junior." And I was like, "Huh." And then I can see that because I asked the question plainly like, "Hey, why did you do this or how did you that," instead of also saying where I'm coming from, "Hey, I noticed this blah, blah, why, blah?" You know what I'm saying? Instead of showing I have an understanding of the thing and then asking a follow-up question, I just ask the question bluntly without context and people feel like, "Hey, I'm asking a very basic question." So, that's the kind of feedback that I particularly value.

**Lenny** (00:49:48):
The feedback you're getting is pretty incredible, like the stuff you shared about someone saying you come across as angry in a meeting if you ask questions or you sound a junior. I don't know if I've ever gotten anyone to give me that brutally honest feedback. When those specific cases, what was it about these people that helped them give you this feedback? Is that what you talked about, you built trust with them over the years or is there something you did to get that kind of feedback?

**Jules Walter** (00:50:10):
I mean, it's definitely they trusted me and they cared about me. They trust that if they tell me the feedback without translating, that I would see the intent behind it. And they were able to do that, because after months and years of working together, they know how to respond to feedback. Because what happens is most people, when you have to get feedback, you kind of have to really do a lot of translation work so that it lands, "I don't want to hurt your feeling. I don't want you to take this." I just told people, "You don't have to that with me." That's one. And then the other thing, too, is people reciprocate also how you talk. I'm not saying I talk to people like this, but I try to be vulnerable with people so they know we can be vulnerable and things are safe like, "I really want to hear things the way you experience it."

**Lenny** (00:50:59):
Got it. So, there's a lot of foundation setting that you do to create this environment where people are like, "Jules, here's something that's going wrong. You can work on this." 

**Jules Walter** (00:51:05):
Yeah. 

**Lenny** (00:51:06):
That's an awesome takeaway. One other thread I wanted to pull on is you mentioned focusing on strengths and how that ends up being really important. Something I'm a big believer in is focusing on strengths versus trying to make your weaknesses much, much stronger. Is there any advice you can share to better understand what your strengths are, why that's an approach to take in developing your skills?

**Jules Walter** (00:51:28):
For the strengths, breakthroughs. For me, a lot of it was talking to my mentor, Lawrence Ripsher. And I organized this event for Black PMs at Pinterest, where Lawrence was speaking, and then we were talking about, "Hey, watch should we talk about, et cetera." I don't know how, but in the conversation he talked about doubling down your strengths more than on fixing your weaknesses, and then he used me as an example. Then the fun part is he had this approach of how you actually find your strength. It's a very simple question, where basically he's like, "Hey, what is something that a lot of people say you're good at, but you think it's not a big deal or it's not that important?" And that's the key. I always that's what resonated with me. I was like, "Oh, a lot of people keep saying I'm really good at networking."

I'm like semi-introvert, so I'm like, "Hold on, I don't know." [inaudible 00:52:32] not everyone or people will tell me, "Hey, you have asked great questions." And I'm like, "I asked basic questions." And then he helped me understand, "Actually, that's how you know it's a strength." Now, what you need to figure out is how do you get more out of that strength. An analogy, by the way, is imagine that you saw a fish and you were like, "Hey, you're really good at swimming." And then the fish would be like, "Oh. Duh, doesn't everybody swim?" And so, that's the key and I invite people to think about that question like, "What's something people keep telling you you're good at, but you yourself don't think is a big deal?" And that's how I was able to find a bunch of my strengths. ]

For me, generally I'm thoughtful, ask great questions. I also simplify problems a lot. I mean, we work together on a product sense article, which is a very complex thing, made it more simple. And then once you identify the strength, then it helps to also think about why are you good at this thing? Because that's the underlying resource that you have. A big part for me is I'm actually quite curious. And fun fact, I don't think of myself as curious, but people keep telling me I am. And even my mom was telling me when I was a kid, I used to always try to unscrew toys to see how they work in the inside. That's one thing: being curious help me ask the questions and so on. And then the other thing, too, is once you have the strength, you want to understand the shadow side of it, and that's the connection between your strength and weaknesses.

**Jules Walter** (00:54:02):
That was a key breakthrough for me, especially Lawrence helped me understand that. Strengthen and weakness, it's not a binary thing. It's like the same thing, but it's a dial. In some context it's good, in other contexts it's serving you. An example in my cases is... I talked about I ask great questions, but sometimes I ask a question without context, I might come across as less knowledgeable. Or another thing for me is I'm able to take very complex problems and then create a mental model that's much simpler, whether it's growth or other things. But until I come up with that mental model, if I'm in a meeting with you, I won't talk much about that topic. Basically, I'm more quiet than other people when people want to hear my point of view because I'm just listening and trying to create a mental model of the situation. You're seeing how the same strength is perceived as a weakness depending on context. And once you have that... For me, I feel more empowered. I'm like, "Oh, I just have to dial down a little bit here or dial a little bit here," and I also know this thing is serving me, which is why I keep doing the bad side of it.

**Lenny** (00:55:10):
Awesome. This all often comes back to mentors in your life. I want to get to talking about mentorship and how you find your mentors, how you work with them, all that kind of stuff; something we've been touching on a bunch and I'm excited to begin to. Maybe to start, can you just talk about some of the mentors you've had in your life, some of the most impactful mentors that you've had?

**Jules Walter** (00:55:35):
I've definitely had a large number of mentors over the years. Fun fact, when I came to the area eight years ago, I didn't know anyone.

**Lenny** (00:55:42):
Wow.

**Jules Walter** (00:55:43):
It took a while to build those relationships. I talked earlier about Bangaly Kaba who sort of helped me figure out how to grow Slack even though he wasn't working outside, but helped me have the frameworks. I talked about Lawrence Ripsher. He helped me discover my strengths and also how to lean into them. Aaron Teague is another friend and mentor who brought me to Google, actually. And there's also Bradley Horowitz, former VP of Google Photos, also helped me in terms of how do you think about leadership and so on. Many other folks, Nikhyl Singhal, VP at Meta helped me with PM career. So, lots of mentors for sure.

**Lenny** (00:56:23):
Okay, that's the killer list. Two questions. One, what do you look for in a mentor when you're trying to find someone to work with? And then two, how do you actually find these people? Most people listening are like, "Wow, I would love an amazing mentor to help me in my career. I don't know how to find one." What advice do you have for folks to finding a mentor?

**Jules Walter** (00:56:41):
I look for two things. One is, are you good at one specific thing I'm trying to get better at? And then two is, are you good at explaining it? Those two, at least for me, they're important. I know people are really good at their roles, at their job and at the subject, but they don't actually know how they do it or they don't really want to explain or cannot explain easily. So, that's what I look for. And then in terms of where I find these people, it's really everywhere. If you look at the list I mentioned earlier, Bangaly I met at an event. Facebook had a recruiting event, I showed up, I see this guy, I'm like, "Oh. Hi." Chat a little bit. I talked about Lawrence, who's now a close friend. I met Lawrence at a dinner. He organized a dinner for underrepresented PMs, we chatted, one thing led to the other, and then he became a mentor and friend. Bradley was at a fundraiser. And Nikhyl was an intro via email. Somebody was like, "Oh, you should meet Nikhyl." 

**Jules Walter** (00:57:41):
I know this sounds counterintuitive. I don't think the hard part is where to find them; it's more about finding the right person and then how do you get a foot in? Now, what I've seen... A lot of people, sometimes they get mentors who are too senior or who don't actually think about the topic they're interested in. Maybe they did five years ago, but once you find the right person, the key is like, "How do you have that initial conversation? How do you get the foot in the door?" And what I've found is you should make the smallest ask possible, which is the opposite of what 95% of people do. 95% of people is like, "Hey, I've never met you, but I heard your talk or I saw you on LinkedIn or whatever. Can we set up a call?"

**Jules Walter** (00:58:29):
That's like a big ask. What I do... For example, there's this person who came to Slack, he was head of product of a major company and then he gave a talk about different methods to improve products. He had this concept of finding the heat for products. He spoke at the company, I got his email, and I reached out in the evening and I was like, "Hey, thanks so much for speaking today. We talked about finding the heat for products. Is there an example of product that you think was created with this approach?" Something he could answer in literally two minutes via email? That was my question. It wasn't like, "Hey, you talked. Now, I feel entitled to meet with you." But then the key is once you get that foot in the door, it could be a quick email, a tweet, a quick chat at an event, that sort of thing, and you get some advice that's useful, the key is to circle back with them at a later point and show that you've actually made good use of the advice. 

**Jules Walter** (00:59:30):
I think that's the thing nobody does. What I would do... For example, there's currently the CEO of a top tech company I met an event. She spoke there and then she gave some advice that was useful. I emailed her a follow-up type thing and then she gave me advice about how to rethink the mission statement for my nonprofit, all via email. Then at some point I was like, "Hey, I've applied your problem trend competency framework to crafting the mission for my nonprofit. Here's where we landed. That was super helpful. Thank you so much." Replies back. And then what I would do then later is maybe a month later or two months, X months later, I can reach out again for another problem and maybe I could say, "Hey, this time it's a little bit more nuanced. Can we grab 15 minutes?" And the person was like, "Yeah, sure." That person was very, very busy. I was like, "Hey, let's do it." And then over time we become Facebook friends, that sort of thing, but that's the approach I take.

**Lenny** (01:00:29):
That's such a good advice. It reminds me of Tim Ferris's advice also, which is just like, "Don't go up to someone and be like, 'Will you be my mentor?'" Everyone's going to be like, "I don't have time for that." Instead, to your point, it's the exact opposite. Just start asking simple questions and then over time build up relationship, and then over time, maybe you start meeting regularly. But don't start big; start small.

**Jules Walter** (01:00:50):
You. As small as possible.

**Lenny** (01:00:53):
It's not like you just have one mentor. You've listed a whole bunch of people that have helped you over your career. It's not like, "Here's the person, they have to be perfect." It sounds like you kind of identify, "Here's a skill or an area I want to focus and this person is going to be really good at that." 

**Jules Walter** (01:01:06):
Yeah.

**Lenny** (01:01:07):
Then I also just love the point about it feels really hard to find an amazing mentor. From what I'm hearing, the main thing you do is just go to things, attend events, basically go events, meet people, right? That's kind of the foundation in which you're sharing is just meet as many people as you can, and amongst that group, you'll find people that are probably going to be helpful.

**Jules Walter** (01:01:26):
Yeah. And I understand it can be harder for some folks. I mean, now I have two young kids, so I don't do as many events. I've also met quite a few people through introductions, sometimes being cold outreach. I had a chat with Shishir through cold outreach [inaudible 01:01:44] a very clear question, and then he offered to come to Black PMs and share some insights. Those kinds of things happen, too, but you have to show the person that you're going to make really good use of their time. You have to give really specific contexts like, "Hey, let's grab coffee." It's like, "Hey, here's a very specific question. Can you share some thoughts or point via email?" And then they might offer, "Hey, why don't we just talk?" That sort of thing, too. Yeah.

**Lenny** (01:02:09):
That works really well. Anytime I get an email request of, "Hey, could we do a 15-minute Zoom or a copy chat," I quickly do not have time for that. But an actual question that I can be really helpful with really quickly, that's so much easier, so that makes a lot of sense. The next thing I wanted to ask you is: how do you build and continue this relationship? And then once you actually start engaging regularly, what do you suggest folks talk about in these meetings if they're ongoing.

**Jules Walter** (01:02:37):
I make sure to bring something very specific that I'm dealing with where they can provide input. And this is the opposite of what many people do where they're like, "Hey, can you tell me about how you... Whatever, your path to PM," which may or may not be relevant to them, versus, "Hey, I've interviewed for three companies. I'm trying to decide among those three. Can I walk you through my thought process and get your feedback?" So, it's very different. I definitely make sure I bring a very specific context, and sometime it could be... I mentioned the example of Bangali like, "Hey, I'm now a growth PM at Slack. I'm trying to improve activation. Can I talk to you about how you approach growth in general?" Or it could be, "Hey, I'm having internal..." Let's say I have internal mentors at Google and I have a few, then it's like, "Hey, I'm about to have this negotiation with this team. Can I walk you through my thought process and hear your advice?" So, it's very specific things. 

And then the other thing I'll say, too, is when I talk to mentors, I always take notes. I mean, I'm seeing you even here in this interview. You're taking notes. These are basic things people don't actually think about it sometimes. And then when I follow up, whether it's via email or in person, I bring up older conversations. It's like, "Hey, remember last time we told about X? I did it," or "Hey, how's your daughter? I know she was going to college this semester. How did that go?" So, it always feels like a continuation of a conversation and it feels like an actual relationship instead of transactional interactions. And then the other thing, too, is I try really hard to identify ways that I can be helpful. Sometimes, at the end of chat I'll be like, "Hey, is there anything I can help you with? Anything top of mind for you?" And sometimes the person could be senior or wealthy, doesn't matter, and they're like, "Actually, yes. I'd love to better understand how the team is really doing. Nobody will tell me the truth," or "Hey, I am trying to hire for this role. You have [inaudible 01:04:43] Black PMs. Do you mind sharing?" There's always ways you can help, but most people are so focused on themselves that they miss out on these opportunities.

**Lenny** (01:04:52):
The point about coming back to the person and sharing what impact their advice had and how it went is so good, because to your point, it just feels like you're sharing all this advice and just isn't going anywhere. And then note-taking, such great stuff. This is really good advice. I could see how it would work on me if someone's asking me for advice.

**Jules Walter** (01:05:10):
By the way, I mean we didn't know each other two years ago, right?

**Lenny** (01:05:10):
Yeah, that's right.

**Jules Walter** (01:05:14):
Yeah. It's like a similar process, where we got to know each other mostly via email and led to the other, and we try to help each other.

**Lenny** (01:05:22):
And look at us now. Any final thoughts before we wrap up and head to our very exciting lightning round?

**Jules Walter** (01:05:31):
I have found the process of learning how to be a PM very difficult and I also find it quite rewarding. And I want to set expectation, especially for people who are early in their career, people may be frustrated by the process, because you have all these skills. We listed, I don't know, half a dozen, a dozen that you want to get better at. So, be patient. Then also it takes a while to see massive differences, but once you see those differences, you set yourself apart from your peers. That's one thing. And then the other thing, too, is it's really building muscles more so for the EQ stuff, but even for the IQ stuff. You have to practice. It's not just read Lenny's top 10 articles for two hours and then you're good. Read them, do what they say, get feedback after you do what they say and say like, "Huh, it worked for me. It didn't work for me." Reread them again, find mentors, et cetera. It's a long process and I don't think people have that mental model around how to learn in general, but also specifically how to learn the PM skills.

**Lenny** (01:06:41):
And I imagine there's also this one step forward, two step back experience that often happens, too, where you're just like, "Oh, I thought I figured out how to think about strategy, and this one failed." And you're like, "Oh, that was useless." No, this is how you learn. You fail sometimes. Oftentimes, it works out slowly but surely you move forward.

**Jules Walter** (01:06:57):
Yeah, totally.

**Lenny** (01:06:58):
Amazing. Well, with that, we have reached our very exciting lightning round. Since we've gone a little long, I'm going to keep it just four questions. I'm just going to go through them pretty fast, whatever comes to mind. Fire off. You ready? 

**Jules Walter** (01:07:10):
Yeah. 

**Lenny** (01:07:10):
What are two or three books that you've recommended most to other people?

**Jules Walter** (01:07:15):
One of them is Never Split the Difference by Chris Voss. It's about negotiations. There's actually also a masterclass on it.

**Lenny** (01:07:21):
I was just going to say that. I watched that. That was really good. 

**Jules Walter** (01:07:24):
Yeah. Yeah. And then another one is Connect by Carole Robin. It's inspired by Stanford's Touchy-Feely class, if you've ever heard of it.

**Lenny** (01:07:33):
Yeah. She did a guest post for the newsletter, actually.

**Jules Walter** (01:07:35):
Oh, really? Awesome. Yeah. It's really a helpful especially as you are thinking about the EQ skills and how to improve your relationships with people.

**Lenny** (01:07:44):
Awesome. I highly recommend that book. I haven't read it, but I read a lot of things about the class and my friends have been in that class and she wrote this guest post. That sounds like a really good pick for EQ, so I'm actually going to re-pick it up. Next question: favorite other podcast that isn't this podcast.

**Jules Walter** (01:08:02):
Lex Fridman is one I'll call out. Brings really interesting speakers and also on diverse topics, so I find it really helpful.

**Lenny** (01:08:11):
Awesome. I also love that podcast. Favorite recent movie or TV show?

**Jules Walter** (01:08:15):
I watch fewer now. Top Gun: Maverick is a movie I really like. I'm sure many people have seen it. For me, it's like just going back in the 80s. And then TV show is Never Have I Ever. It's coming of age in America, Indian teenager. Pretty funny and also deep.

**Lenny** (01:08:34):
Awesome. I haven't heard of that one. We'll check it out. Final question: favorite interview question that you like to ask folks when you're interviewing them?

**Jules Walter** (01:08:41):
One I used to ask a lot is: what's something work related that you're trying to get better at? Sometimes I change the wording of it, but a big part of it is trying to understand how self-aware people are, to which extent they have a growth mindset, and then also how honest and vulnerable they can be. What I will say, though, about interview question, by the way, is I don't anchor a lot on the first question. What I find the most value from are the follow-ups. Once you ask that question, you can take in various directions like, "Why did you focus on this versus other things? How did this come to your attention? Was it feedback you sought or feedback people gave you, et cetera?" Yeah.

**Lenny** (01:09:24):
Awesome advice. Jules, this interview was a longtime coming. It was everything I hoped it would be and more. Thank you again so much for being here. Two final questions: where can folks find you online if they want to reach out and learn more, and how can listeners be useful to you? 

**Jules Walter** (01:09:39):
In terms of finding me, Twitter is one place to start. My handle is @julesdwalt. And then in terms of how people can be useful, it's really about paying it forward and then sharing this with others, especially parts that people find useful.

**Lenny** (01:09:55):
Amazing. Jules, thank you so much. We'll chat again soon.

**Jules Walter** (01:10:00):
Yeah, thanks for having me.

**Lenny** (01:10:03):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [2/22] Yuhki Yamashata

**Lenny** (00:00:00):
There's something controversial about this idea that everyone can see what you're doing or that multiple designers can be in the file at the same time. We like to say that one of the first responses we saw Lenny [inaudible 01:08:35] Figma was, if this is the future of design, I'm quitting, right? I'm changing careers.

**Lenny** (00:00:17):
And there's that tension of that narrative tension, but that is signal that you're part of this revolution and you're trying to change something. And when it equips your customers or user base with that, then I think that's something that they can really get behind and champion.

**Lenny** (00:00:35):
So it's not just that they're championing for a tool, they're also championing for a new way of working. Obviously, that's a tall order or don't want to come up with that, but hopefully, if you're a founder and you're working on something, your vision is so big that you have those kind of ideas and it's like, how do you actually equip your customers to want to talk about that?

**Lenny** (00:00:58):
Welcome to Lenny's podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products, interview world class product leaders and growth experts to learn from their hard won experiences, building and scaling today's most successful companies.

**Lenny** (00:01:12):
Today my guest is Yuhki Yamashita. Yuhki is Chief Product Officer at Figma, where he's been for almost four years. Prior to Figma, he was at Uber, both as a Product Leader and also, interestingly, as Head of Design for one of their bigger product teams. Before Uber, Yuhki spent time at Google and Microsoft, even taught an introductory computer science course at Harvard.

**Lenny** (00:01:33):
In our conversation, we explore Figma's product development philosophy, how they build such consistently great products, how they hire, what habit Yuhki has found to be the most instrumental in his success in his career, and also what Yuhki and his product team have learned by building a product led growth business.

**Yuhki Yamashita** (00:04:30):
Thank you for having me, Lenny.

**Lenny** (00:04:32):
I'm quite honored to have you on this podcast. For folks who don't know, we actually collaborated already on a newsletter post that has quickly become my fourth most popular post of all time, which you can find if you search for how Figma builds product. And so I am really excited to dig into a lot of the stuff that we, maybe, didn't cover in that newsletter. Also, just like how product works at Figma in more depth, how the PM team works, how you think about product, and things like that. So again, thank you for joining me.

**Yuhki Yamashita** (00:05:00):
Hi, team, as a huge fan of this podcast, so really honored to be here.

**Lenny** (00:05:04):
Wow, that means a lot. I really appreciate that. So you are currently Chief Product Officer at Figma, which is such an epic role. It's such an epic company. Could you take just, maybe, a minute or two to high level share your career arc, how you got to where you're today as CPO at Figma?

**Yuhki Yamashita** (00:05:22):
My first job out of college is actually at Microsoft, and I was the Product Manager on Hotmail. If anyone, any listener remembers Hotmail, and I didn't really know what product management was at the time, and I mute it as a interdisciplinary function that will give me exposure to all my other functions so that I can actually decide which function's interesting to me.

**Yuhki Yamashita** (00:05:48):
And so, spent a couple years at Microsoft. Through that, also, moved on to Hotmail to Windows. And at the time, they were working on Windows 8 and Windows 8 was really interesting because it's a very touch forward version of Windows. And so there's just a lot of conversations about UI and UX, and that was really fun for me.

**Yuhki Yamashita** (00:06:07):
And as I was thinking about what's next, I really felt the draw of Silicon Valley and I ended up at YouTube, and I believe Shishir has been on this podcast before?

**Lenny** (00:06:19):
[inaudible 00:06:19] you.

**Yuhki Yamashita** (00:06:19):
Yeah, so Shishir was leading YouTube at the time, and he continues to be a great mentor of mine, but had the opportunity to lead the YouTube app on iOS over there. And it was really funny because I had never touched the iPhone before my first day, so my manager, on my first day, just sent me to the Apple Store to buy an iPhone. But that was my next job and that was a really interesting change for me, too, of, and we can talk about this later, as well as different companies and different styles of product management and really figuring out, I think it was a place that taught me a lot about some of my product last weeks to date.

**Yuhki Yamashita** (00:06:58):
And this is also around a time where there are a lot of interesting companies that were working in the physical and digital space. And so Airbnb was one of them, Uber was another. So I felt this draw just because it seemed just a really interesting space to be in. So eventually, ended up at Uber. Uber was another company where I feel like a lot of my philosophy that, hopefully we can get into today, around how to build products, how to build products in the kind of environment that's really fast moving. And so that I learned a lot from there.

**Yuhki Yamashita** (00:07:33):
And to date, all those companies has really been focusing on the core experiences on consumer products, and that's really been most of my career. And as part of that, worked with a lot of amazing designers. But at Uber, I realized that I wanted to dip my toes into design directly. For the tail end, I actually switched from PM to design and managed a few design teams working on our bikes and scooter efforts just to understand what that's like. And it was around this time, around my Uber career, where we encountered this tool called Figma.

**Yuhki Yamashita** (00:08:08):
I'd happened to be working on a project that experimentally brought Figma into the company. It was a time in the company where we were trying to transform our culture to be much more transparent and inclusive, and Figma was the perfect fit for that. So, I got to watch how Figma changed the way it worked, how it's spread within the company. We got to know the Figma team a little bit, as well. And yeah, I was really drawn to that mission and as a product manager who's been straddling that boundary between design and products for all my career, I really loved how Figma proactively blurred that boundary and opened up that process of participating in design. So I really got behind that mission and that's how I ended up here, at Figma.

**Lenny** (00:08:49):
It's so fascinating that you moved into design from product, and then back into product. At Uber, were, what was the role? You were Head of Design for the mobility team?

**Yuhki Yamashita** (00:08:59):
Yeah, it's called New Mobility, focused on just our micro mobility efforts, basically. Yeah.

**Lenny** (00:09:05):
Do you recommend this path for PMs to switch into design? I know it's not something anyone can do, but do you feel like that is an important skill role to experience as a PM, you encourage people to try that?

**Yuhki Yamashita** (00:09:16):
Well, I decided it's not for everyone, but I think that it's, first of all, a really great empathy building exercise of understanding that point of view, and also pushing yourself to push on the product from a different angle. Because I think as a PM, you're in the center facilitating all these different trade offs, and when you go into design, you have to ignore some of those other aspects to really be insistent on pushing on the best experience possible. Just suspend everyone's disbelief in business feasibility or engineering feasibility to push on a vision. And that's just an interesting exercise to do.

**Yuhki Yamashita** (00:10:00):
And then, I think the last thing is, I actually think it's an opportunity for in design and PM to learn from each other. When I became manager of design teams, one of the things that I coach designers on, are how to win over PMs, and how to speak in PM's language, and likewise, it's important for PMs to understand that, as well. So those are some of the things that I thought were helpful, but again, it has to come from a place of passion that you know you really want to do this.

**Lenny** (00:10:29):
Which job would you say is harder; design or product management?

**Yuhki Yamashita** (00:10:32):
They're hard for different reasons. I would say managing designers is harder than managing product managers.

**Lenny** (00:10:38):
Interesting.

**Yuhki Yamashita** (00:10:39):
And I think part of it is that designers are, it's really important to focus on growing their craft and helping them develop as designers. So it might not be that the company's biggest problem is one where you can actually learn this new thing you're trying to learn as a designer, and this probably happened for engineers, too, right? You could be working on the onboarding funnel, and that might not be the best place to be learning micro interactions, or maybe it is, but those aren't always aligned.

**Yuhki Yamashita** (00:11:10):
Whereas, with Pms, it's a little bit more like PMs are just hungry for impact, and so you can point them to the biggest problems a company has. And while PMs also do want to understand different kinds of problems or have the experience working on different kinds of problems, at the end of the day, I feel they want to be working on the thing that matters most in the company. So from that perspective, it's easy.

**Yuhki Yamashita** (00:11:31):
But as you know, and the reason this podcast exists is because PM isn't easy. And so the discipline, I think, is harder in a sense that it's sometimes hard on a day-to-day pace to know if you're doing the best thing you could possibly be doing. And so I think that makes it a little bit harder as a PM, as well.

**Lenny** (00:11:52):
I had a designer friend who moved into a PM role, I had a product role at a startup and she's like, "Holy shit, I had no idea how hard being a product manager was, and a product leader. I have so much more empathy for the PM role." And so, it's interesting, it works in both ways. Similarly, I was actually a manager of engineers, at one point, and I felt the same way where managing PMs was a lot easier than managing engineers. So, translates to a lot of different roles.

**Yuhki Yamashita** (00:12:19):
Yeah, I can see that.

**Lenny** (00:12:20):
Folks listening to your career arc and just all the places you've been, all the wonderful things you've done. Imagine many people are like, wow, how do I have a career like that? Microsoft, Google, Figma, Uber. If you had to think back and identify maybe one habit, or one skill, or behavior that you think has most contributed to your success as a leader, as a product leader, what do you think that would be?

**Yuhki Yamashita** (00:12:45):
People who work with me know that I often talk about storytelling and, in fact, if you've ever reported to me, storytelling has showed up in some kind of performance review, I feel, and that's how much I care about it. And I actually think that a lot of being a great product manager is being a great storyteller. And I know a lot of us have already talked about it out there. I think the importance of storytelling is understood, but maybe I would share two things that are specific about it that I think are interesting.

**Yuhki Yamashita** (00:13:13):
One is to understanding the power of synthesis and it's this idea that maybe even as a early career PM, you're inside some of these reviews and a lot of people say, "Hey, at least you could take some notes for the meeting so that you're adding value." And so that's common advice, here, but I think the most powerful part of that is that in some ways, you can synthesize what happened. And a lot of things are said in a review and there's still this bring it all together into a distillation of a message. And even that's like, that's a lot of power, I think. And what do you take away from all these different opinions that all these leaders had, and how do you push that, push the project forward from there? So that's one example.

**Yuhki Yamashita** (00:14:02):
Or another example is, I really love thinking through frameworks and offering ways of talking about a problem or ways of thinking about a problem. And that's synthesis, too, of figuring out all these different disparate parts and coming up with a way to a lens to look at something. And I feel like it's something that was, I learned, mostly through literature classes almost, where you're doing literary commentary and you're reading a William Yates poem and you're trying to, you observe all these interesting things, but then you have to take those different observations and distill it into a thesis, into something cohesive. And I think that's what a good PM can do. All these different ideas, and opinions, and problems, and how do you distill it down? And so I think that's one aspect of storytelling that's really important.

**Yuhki Yamashita** (00:14:54):
And the other aspect of storytelling, of course, is a story is only as good as the action that it's capable of driving. And a lot of times that I often coach my product managers are on, we're living in a world where everyone is constantly distracted, and you get these 30 seconds of attention at a time. And so, just the ability to really tell something powerful that sticks is really important, the memorability of it.

**Yuhki Yamashita** (00:15:21):
And I often talk about memification, which is this idea that I found this out most at Uber, I feel, where there's certain insights, data insights, research insights that were memmified to the point where someone like Travis or Dara would just cite this insight in the middle of a meeting, and you know that you've really done your job as, maybe, a researcher or a data scientist or product manager if people are able to do that and draw from that in that way. And that's what, ultimately, sticks.

**Yuhki Yamashita** (00:15:52):
And so when you start thinking about it from that perspective, it's really powerful because it's the way in which knowledge is transferred within the company and you compel action for it. Or when I'm being, maybe, asked questions by other leaders or stakeholders, the thing that's going through my head is, okay, there's this story that, that leader is trying to develop, or a meme about what this project is about or what the biggest problem is. And so, what story are they trying to create in their head so that they can remember or talk about what's happened?

**Yuhki Yamashita** (00:16:28):
And if you take that mindset, you just realize that it's a really useful way to think about everything.

**Lenny** (00:16:35):
I'm really excited to chat about this idea because it comes up a lot. The power of storytelling, it's similar to being good at vision. It's like PMs are always told, "Hey, you got to improve in vision." Here's a skill the great PMs are really strong at. And I feel like storytelling is similar. It's this vague cloud of a skill that you build over time. And you mentioned a few things that you recommend to people that you work with. Think of it as a meme, maybe.

**Lenny** (00:17:01):
Is there anything else? When you're doing a performance review with a PM and one of their skill gaps is storytelling, is there anything else you recommend they specifically do to get better at the skill, or is it just do it again and again and watch me do it, watch other people do it and you'll learn?

**Yuhki Yamashita** (00:17:16):
Yeah, I think of it as resetting the internal computer of my brain a little bit so that I start from scratch again. And when I'm starting from no context at all, can I build up the story from bare and explain what's happening? And oftentimes, you're just caught in the middle of everything and you have all this context that might not be obvious if you step away from it for just a second.

**Yuhki Yamashita** (00:17:39):
I guess the way to think about it is, put yourself in another user's shoes, and that user is someone who has no idea what's happening and still wants to understand, in a nuanced enough way, what you're grappling with. And so, that reset moment, and to pull yourself out helps you tell a better story, in many cases. So that's one thing that comes to mind, yeah.

**Lenny** (00:18:03):
Got it. So it's escape the curse of knowledge a little bit and just assume people don't know anything about the context, the background, why this is important, come back to the beginning.

**Yuhki Yamashita** (00:18:12):
Yeah, I think another thing that where I learned storytelling is through teaching. So when I was a course assistant for a computer science class and I had to explain pointers, you're like, okay, I really have to borrow on real world metaphors or something that is much more grounding because if you assume a lot of knowledge, then it can be inaccessible to a lot of people. And so if you can tell a story that any student can understand, then you've really done your job. And once you've learn that skill of being able to tell anyone who has no context, then it becomes much easier to turn to these other audiences that are closer and closer.

**Lenny** (00:18:51):
When I asked you in our newsletter interview what one of the core philosophies of product managers is, in the way you think about product and the role of PM at Figma, an interesting thing that you highlighted is that to you, it's really important that PMs own the why of a product and an idea. And I think it connects to what you're talking about, now. I'm curious just why you think that's so important for product managers and why that's so core to the way you think about product, and at Figma.

**Yuhki Yamashita** (00:19:17):
I really can't remember why I heard this, but it really stuck with me because oftentimes, there's this debate about well, is a PM the person who comes up with the idea. And the answer is usually no, it doesn't have to be at all. And in many cases, in our case, your customers come up with a ton of different ideas and certainly, the what and how are things that are shared within the company and not something that PM uniquely drives. But I do think the why is something that I really always hold the PM uniquely responsible for.

**Yuhki Yamashita** (00:19:48):
And I think the place where I learned this, the importance of this the most, was actually first, at YouTube. I had been working at Microsoft for a long time and I was early in my career, so I was just really focused on my, what we called, our feature crew, our engineer designer, our tester, and just writing specs that really specified exactly how everything works. And so that was the Microsoft culture back then, and your specs had to be perfect, right?

**Yuhki Yamashita** (00:20:19):
Then moved over to YouTube, and all of a sudden, you're responsible for an entire app, and you have a pretty big team, and you cannot specify everything that happens. And so, naturally, designers and engineers are just making their own choices. Made is an error handling situation, and in Microsoft culture, you would've had a table that specifies exactly what happens during that error. But in Google culture, it's like, okay, well the engineers and designers, they can figure it out.

**Yuhki Yamashita** (00:20:47):
So then it's like, how do they make a really great decision? How do they make all these local decisions that you're not a part of, how do you make it so that a great decision's made? And if everyone has an understanding of why we're doing this, what problem we're solving, then people can make really great decisions. It's the only way you can really scale. So that's where it came from.

**Yuhki Yamashita** (00:21:06):
And then since then, I've started to realize, also, that there are other functions that do this well. So for example, our engineering team at Figma, whenever we do a retro or postmortem, we do this thing called five why's. And it's the idea behind it, it's like, well, why did this happen, outage happen, okay, and why did that thing happen? And go deep enough where you can find the root cause and go fix all those things.

**Yuhki Yamashita** (00:21:28):
And I think a PM can do this, too, which is a customer is asking for a feature, but then you would say, okay, why are they asking for it, and back up the problem. But I think there's one more step you can take, which is, why do they have that problem in the first place? And maybe there's something there, and that could be an opportunity to make a bigger product impact by fixing that underlying condition that created the problem in the first place.

**Lenny** (00:21:55):
That's so cool that you actually do the five whys. I hear people talking about the five whys all the time, and I don't know, I haven't heard people actually using it. So you actually do this at your post-mortems, you said?

**Yuhki Yamashita** (00:22:03):
Yes. Engineering team that's accepting them, yeah.

**Lenny** (00:22:07):
That's so interesting. Can you talk a bit more about these postmortems? Is this just when something goes wrong or is this just every project you retrospective postmortem thing?

**Yuhki Yamashita** (00:22:14):
As it relates to five whys, it's more when something went wrong. But I do think we have a retro culture, [inaudible 00:22:24], where there's always opportunity to make things better. And if you don't create the environments to talk about it, then some of those will go unaddressed forever, so.

**Lenny** (00:22:33):
Cool. Okay.

**Yuhki Yamashita** (00:22:33):
Yeah.

**Lenny** (00:22:34):
Another attribute of the product team and how you build product at Figma that you shared that was really interesting is you mentioned that you just have an obsession with a proximity to customers, that you make sure your PMs and product team are really close to customers. When you hear that, you're just, imagine everyone listening is like, oh yeah, we're really close to customers, we talk to customers all the time. Of course you got to talk to customers. I'm curious what it is that, maybe, you think sets you apart, in terms of how you think about being close to customers, and if there's a story, maybe, of just, wow, this is how close we are to customers and maybe something that emerged out of that, that'd be really cool to hear.

**Yuhki Yamashita** (00:23:07):
Well, I think a lot of it starts with our origin story in many ways, which is that way back when, when Dylan, the small group of people were building Figma, this is the time when no one believed it was possible to have a design editor in the browser. And so it just seemed like science fiction, almost. And yet, what Dylan did consistently throughout, was just put the product in front of designers, ask them for feedback, come back to them the next time with that feedback implemented, and it becomes better and better and better.

**Yuhki Yamashita** (00:23:40):
And at no moment was there a tentative expectation that the designer suddenly turns around and implements that tool in their organization. It was really just about listening really carefully to what the community had to say, and through that process, making them evangelists. And that's where a lot of how Figma came to be and why we have such a strong connection with our community where we've actually, they've really helped shape the product to date, and there's a deep belief in that, and they're the ones in that are now advocating for Figma and helping us spread within the community and within their company.

**Yuhki Yamashita** (00:24:20):
So that's the backdrop for why we have such a strong connection with our customers, and there's a lot of things that you see. So for example, maybe someone on my team Sho, and oftentimes, Sho will tweet out to the community, here's what we're thinking, or we're actually thinking about focusing a lot more in prototyping. What are the top problems you're seeing? And people come back with all these different answers because everyone's passionate. And we go in there and just look at all the feedback and understand what people are saying and just have a stronger pulse on how people are feeling. And that's not to say that everything is then implemented verbatim, but we really find it useful to feel like we have a sense of what people are thinking.

**Yuhki Yamashita** (00:25:05):
And I think the most crazy version of it, maybe, is Dylan's always reading customer feedback. In fact, has reads the most customer feedback of all of us and has been doing that for a decade. And oftentimes, there used to be this thing where he would drop in tweets that he sees into different Slack channels to be like, hey, this seems concerning, or we're getting this feedback. And it got to a point where we got big enough where people would feel like they had to drop everything and deal with that tweet.

**Yuhki Yamashita** (00:25:31):
So Chris, our CTO, and I intervened. We created this new channel, private channel called Concerning Tweets, and it just, we're this small group of us that Dylan can drop us in. And these are tweets that aren't going viral, by any means. They're just things that you see is with one like, sometimes zero likes, but he feels there's an essence of truth to them and we make sure that we look at what's going on there and see if there isn't something much bigger that we should be focusing on. But that's the extent to which someone like Dylan, from top down, implements this idea that we need to be staying close to what our users are saying.

**Lenny** (00:26:13):
That's an awesome idea for a channel, a way to contain that potential madness that it creates. Is there anything else you've learned around hearing feedback like that in a tweet, let's say, or just a few loud voices and deciding what to actually work on? Do you have an approach there? Just deciding what's worth paying attention to?

**Yuhki Yamashita** (00:26:31):
As we built out our research and data functions, it's really important to balance out the vocal minority with what's actually happening. So I really view some of those tweets more as canaries in the coal mine, in a way, and inputs into, many inputs we have around everything our customers could possibly be experiencing. And it's important to realize that we have certain forums, like our support tickets, where customers are, tend to be much more dissatisfied. And we have other kinds of inputs that are sales conversations with prospects, where it's really more about perceptions around Figma, in some cases.

**Yuhki Yamashita** (00:27:11):
And I think it's just important, especially as a product manager, to feel like you have this balanced portfolio of different kinds of feedback to know that you don't have any blind spots. So I think that's one of the things that I focused a lot on when I came in, which is the Figma team is very good at Twitter and staying on top of the sentiments. And luckily for us, a lot of designers are on Twitter, but the reality is that most of our audience, at this point, probably aren't. And so building our capabilities to extract feedback or more insight from those other sources, as well.

**Lenny** (00:27:46):
That reminds me, I think Twitter was really instrumental to the beginnings of Figma. I believe Dylan made this social graph of the most influential designers on Twitter, and that was his go-to market strategy, get those designers on Figma, and then I think he open sourced his code to do that. Is that right?

**Yuhki Yamashita** (00:28:02):
Yeah, that sounds right to me. And he is very intentional about which designers we need to win over. I think it was very novel at time.

**Lenny** (00:28:11):
What is it like to work with Dylan Field? As an outsider, he's a legend, feels like he's an incredibly smart, talented, hardworking, CO. There's always tension a little bit between a Chief Product Officer and a CO, and so I'm just curious, what do you like to work with as a product leader? And then, is there, I don't know, a memory that comes to mind of just a way that encapsulates what it's like to work with Dylan?

**Yuhki Yamashita** (00:28:32):
We're very different, actually. And Dylan is very, he's very based on intuition and instinct. And that intuition is actually built off of thousands and hundreds of thousands of customer interactions where he might look at something and be like, "You know what? This isn't going to land well," or, "Here's the biggest problem right now." And you're like, well, how does it conclude that? And part of my job is to build out that logic streak for him of how did you arrive at that conclusion so that people can understand that at scale, in a way. But he's very much about that.

Or I think there's a way which, sometimes, it's a product manager, you want to lay out a problem and say, okay, we're going to first focus on this problem, and then [inaudible 00:29:21] these three approaches. We're going to take this approach and have a review at every step along the way. But for Dylan, I think, it's very hard for him to really fully get bought into it until he sees the end implementation to viscerally feel if this is a good solution or not. And so I think that's the kind of thinker he is where he really needs to see it to feel it. But it's not totally random. It's based on all these interactions with customers and somehow encoded in him to build up some of those intuitions.

**Yuhki Yamashita** (00:29:55):
And I think one of the things that's really interesting about him is that he actually really cares very deeply about any given user and how they're feeling about Figma. I remember when, during the height of the pandemic, we were doing a one-on-one walking around Delores Park, because this is the era where you would take meetings, if you take meetings, they're all outside, and then he needed to use the bathroom. So he came out to my house in the Castro, he used the bathroom, and then he met my partner, and my partner was on Figma, had Figma pulled up because he is just doing work. And then Dylan just went straight in there and wanted to ask what the biggest problems were or what's not working, and they started geeking out on some issue around Google fonts, and this is the first major interaction between the two of them.

**Yuhki Yamashita** (00:30:45):
But it's one of those things where that's how much Dylan cares. And on one level it's just easy to say, "Hey, this is a single user who just happens to be using your product," and be dismissive with it or not care that deeply because you think you already know all the biggest problems, but that's not his attitude. And so that's the level of, I guess, customer obsession, if you will, that he exhibits and then, in turn, informs his intuitions.

**Lenny** (00:31:16):
That's amazing. Figma is 10 years old at this point. He's been at this for a long time, like a decade. And the fact that he's still so obsessed with just a random person just using Figma and he's taken the opportunity to experience it in real time every chance he gets, sounds like.

**Yuhki Yamashita** (00:31:31):
Yeah.

**Lenny** (00:31:33):
Hey, Ashley, Head of Marketing at Flatfile, how many B2B SaaS companies would you estimate need to import CSP files from their customers?

**Ashley** (00:31:41):
At least 40%.

**Lenny** (00:31:42):
And how many of them screw that up, and what happens when they do?

**Ashley** (00:31:45):
Well, based on our data, about a third of people will consider switching to another company after just one bad experience during onboarding. So if your CSP importer doesn't work right, which is super common, considering a customer files are chalk full of unexpected data and formatting, they'll leave.

**Lenny** (00:32:05):
I am 0% surprised to hear that. I've consistently seen that improving onboarding is one of the highest leverage opportunities for both signup conversion and increasing long-term retention. Getting people to your a-ha moment more quickly and reliably is so incredibly important.

**Ashley** (00:32:19):
Totally. It's incredible to see how our customers like Square, Spotify and Zora are able to grow their businesses on top of Flatfile. It's because Wallace data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:32:36):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny.

**Lenny** (00:32:44):
As an outsider, it feels like Figma is just always firing in all cylinders, shipping the best product. People love it. I use it, I should've mentioned this, but I use it probably every day for my newsletter for illustrations and banners and all this stuff. Yeah, I don't know what I do without it. And it always feels like Figma is just killing it. I know that's never the reality. I'm curious, is there a story of something that just, maybe, didn't work out the way you hoped? Whether it's a feature, a launch, or something like that that just shows people that it's, not everything always works out.

**Yuhki Yamashita** (00:33:14):
We run experiments all the time that don't come back with winning results, and we certainly have built a lot of more complex features that took a while to take off.

**Yuhki Yamashita** (00:33:24):
So a good example of this is in the design system space, we have something called branching and merging. And branching and merging is this workflow of maybe you're building a really complex design system, and then you don't want anyone ever randomly touching your components that are used by thousands of other projects, so you create this workflow of, someone, maybe, effectively suggesting a change, you're reviewing it and then pushing it in.

**Yuhki Yamashita** (00:33:48):
And so, in theory, makes a lot of sense and things that our customers asked us for, but once we built it, in the initial stages, just didn't really see that much adoption and didn't feel great because it's a really big investment for us. It's a lot of work that we put into it and there's just many different reasons. Some of it was performance, some of it was, this is a foreign workflow and it just takes time, and us helping customers implement some of those workflows, we realized some gaps because we don't really use it that much ourselves.

**Yuhki Yamashita** (00:34:20):
And so, I think as we're getting bigger, one of the things that I'm realizing is that we're starting to build a lot of features that are not, necessarily, for organizations like ours. And when we do that, we really need to be creative about how we understand how effective those are because we've had such a strong culture of internal testing and dogs looting, and those are the things that really helped make sure the quality of our product was good enough. But now we're working with really new types of customers and needing to push ourselves and build that muscle, as well.

**Lenny** (00:34:54):
Speaking of high quality software, again, I'll repeat, I think Figma is one of the most beloved software products. It's become central to a lot of the ways people work. It's also, I think, one of the fastest growing SaaS products, in general. And I don't know, this is maybe the ultimate softball question, but I'm just curious, what is it that you do at Figma to build such high quality software? Because it's rare for B2B software, especially. What do you do as a product leader, as a product team to just set this high bar, make sure that the stuff that you put out is great consistently, and the more tactical the better?

**Yuhki Yamashita** (00:35:27):
It's so important that you're using your own products. And I think we're in a very lucky position where all of us can get creative around using Figma in some way. And obviously, designers are the, internally within Figma, are the most vocal and the ones who are in the product six hours a day, essentially. But even for PMs, one of the first things I did when I arrived was we were a little bit more of a memo culture, and I was like, you know what? We should be a deck culture because we can build those decks in Figma, and just that act alone allows you to encounter a lot of issues and for you to get familiar with it.

**Yuhki Yamashita** (00:36:06):
And so I think there are ways in which, sometimes, you have to get creative to enable your company, your entire company to use a product more. Or as an example, recently, we just did calibrations for performance reviews in FigJam, and our Head of Design, Noah, came up with this amazing template and we distributed it through HR and that was another reason for everyone to use FigJam. And so that's the biggest thing. The more hours people are spending inside your product, internally, I think, just naturally becomes better. Because a lot of times, it's not just about people raising their hands and saying this is the problem, it's more about you just want to make your own workflows, your own day-to-day better, and derive satisfaction from improving that.

**Lenny** (00:36:50):
So the takeaway there is get your product teams to use the product as often as possible. That is a really clever way of doing that at Figma. I know you mentioned in our newsletter interview that you switch from memos to decks. Usually, it goes the other way around, and now I get the second order effects of that where people are building their decks in Figma. That is very clever, and not everyone's building collaboration software, but that is a really clever idea. And I think there's probably a bit of trickle down from Dylan's obsession with the product in making it, just continuing to just be obsessed with making a great experience combined with that, people using the product and this trickle down of we really need to make this as awesome as possible.

**Ashley** (00:37:27):
There are other companies, for example, when I was at Uber, especially working on the driver's side, of course we went out and driving, and that speaks to some aspects of it. But one of the things that I've realized is when you are logging a bug and you add some engineers to it, to have them look into it, the degree of motivation is so different if that engineer has, somehow, experienced a problem in some way.

**Ashley** (00:37:51):
So for example, everyone at Uber would take Ubers into work, and if an engineer working a driver app saw a driver struggling with something, they would find it embarrassing and feel personally accountable to go and fix that. And when you can create that sense of personal accountability, then all these crazy things happen and all this progress happens. So I think for us, as getting creative at Uber about, okay, well how do we increase those interaction points at the point where, if someone building feels like they have some kind of personal relationship with the end user, and this is what happens, at Figma, too, where a lot of our designers feel personally accountable, in a way, because all their customers are people they already know in the community on Twitter and all those kinds of things, so they feel like they have to put something out there that's defensible or that they're really proud of. So I think that personal accountability can really make a difference.

**Lenny** (00:38:48):
That begs a question of, I imagine this engineer at Uber coming back to their desk and like, I've got to fix this bug. And then their PM's like, no, we got goals to hit, here's our priorities, we got this roadmap, we don't have time to fix this right now. It's just one random bug. And so there's a two part question, just like you have a approach to that, do you encourage engineers, designers just fix stuff that seems broken/you mentioned that you have a fun experience with OKRs and how you've approached OKRs at Figma, and you've gone back and forth a little bit. And so maybe, as a second part, just talking about your experience with OKRs at Figma.

**Yuhki Yamashita** (00:39:21):
The first part, I would say that I think one of the most powerful things, especially for startups, is that bottoms up energy, and maybe a developer noticing something is wrong and just going off and fixing it. And for the most part, I try not to get in the way of that because if people are doing that constantly, and everyone the company is trying to make the product better, that is sometimes a way more effective way to improve the quality of experience than this top down of, oh, let's define this quality experience metric and try to change all the things, because you might miss these things. So that's one aspect.

**Yuhki Yamashita** (00:40:01):
And the second thing is, I think a lot of PMs have grown to realize this, which is, if you ask an engineer about how much time it'll cost to go and build something, and it's something that they came up with or they're advocating for, it's almost always half the time as something that you are asking for, as a PM. And that motivation is so different.

**Yuhki Yamashita** (00:40:24):
And that's why getting the buy-in of developers is really important, because you want to feel like they're personally vested in this problem, and then, all of a sudden, their willingness or their creativity, or all these things spike. And so when you think about all those things, when there's a situation where an engineer or a designer's trying to fix a real custom problem, I'm like, by all means.So that's on that.

**Yuhki Yamashita** (00:40:50):
OKR is totally bigger topic, and maybe I'll set the conflicts of why I have such this love-hate relationship with it, which is that a lot of my career, I've actually just worked on core experiences, and OKRs were the bane of my existence, in a way. Because when you're working on a core experience, sometimes you're just, I'm just trying to make the experience better. And sure, I can come up with this BS way to measure what that looks like, but that's not what I'm thinking about every day, anyway. So it just seems very performative, and there's just a lot of work that goes into it.

**Yuhki Yamashita** (00:41:26):
And you encounter one of two situations. One is, you come up with some secondary metric that nobody actually cares about that, technically, you can measure and, technically, you can move, but you haven't actually proven that it really matters. So maybe it is some satisfaction metric that you have on some survey, but you haven't actually done the work to show that, that actually has correlations with retention or anything that actually "matters for real" in the business, or it's some weird usage metric or something like that.

And then the other extreme is to say, no, we're going to be ambitious and we're going to send it for business goals. So for example, even if I was the PM for the rider experience at Uber, I'd be like, you know what? We're going to contribute incremental trips because the experience is going to be so good that we can get more people to come back. And I think the reality for a lot of that is, it's a metric that you don't have full control over or there are many hops until it can affect it, and okay, well maybe we can make the experience better and maybe that improves your attention and maybe this. And by the time you get there, you actually can't even prove that you moved the top level metrics. So either you anchor something that matters, but you can't move, or you anchor something that you can't move but doesn't actually matter. So that's the relationship I've had with [inaudible 00:42:45], so even it's really frustrating.

**Yuhki Yamashita** (00:42:47):
So when I write that thinking about, one of the things I realized is that we had OKRs, but people were treating it almost as a to-do list or a task list of, okay, here's how, by the end of quarter, I need to complete these tasks and then I'll feel like I did my job, kind of thing. And we would have these dreadful meetings where we go through these spreadsheets and have people stand up in front of everyone and talk about those commitments, or those key results, rather. But they were dreadful for a reason, which is that you just couldn't really understand what the team actually really cared about. And it got to this point where we had all these, and this is similar to the secondary metric problem, but either you couldn't approve that you actually moved it, or you're trying to work on something that I don't actually understand why it's useful.

**Yuhki Yamashita** (00:43:39):
And so that was when I deprecated it and said, "I just want to understand your headline. What are you trying to do, philosophically?" And just don't stress about whether you can measure it or not. I just don't understand what you're optimizing for, and let's first have that to date. And then once we get there, then let's talk about, okay, well what are some ways that you can measure it? And some of it's qualitative, so it's quantitative, and that's fine. And I almost feel like sometimes, it's better to take the report card approach of saying, Hey, just give yourself a score, tell me how you derive that score, let's all understand that the metrics and those inputs that go into it can change over time, and we're going to get more sophisticated about how we measure it. But at least everyone understands what on earth you're trying to go for.

**Yuhki Yamashita** (00:44:29):
So that's where I moved in my first year, I would say, and then we hired a Head of Data who is a friend of mine from Uber, too. And one of the things she felt was, okay, but it's still very loosey goosey, and super subjective, so let's just try to bring OKRs back and see if we can just do them better next time. And so we've done that, and they were definitely better than when I first arrived just because we had a data science team and we had more rigor around metrics and things like that. But again, this time it was less about not understanding what people were doing, but more not understanding if teams are actually committed to moving those OKRs. And one of the problems that you find is we have these OKRs, but they feel like these post-rationalizations of the projects that you're working on, anyway.

And at the end the quarter, you come back and see if those OKRs move, fingers crossed. But if you stop an engineer in the middle of the hallway or the virtual hallway, so to speak, and ask them, okay, what are your team's biggest goals or OKRs? [inaudible 00:45:31], they wouldn't be able to say it. They're just like, well, I'm working on this project that's really important. And so it's, well, what's the point of publishing this OKR if you're actually not thinking about moving it on a daily basis almost, right?

**Yuhki Yamashita** (00:45:46):
And so that's when we've tried to experiment with this terminology, well, maybe if we should call it commitments instead, people would take it a little bit more seriously. And it's my belief that oftentimes, commitments are this care between the why and the what, and sometimes the face of the commitment is the what.

**Yuhki Yamashita** (00:46:05):
It's a project and there are many why's behind it, or it's the why and there are many projects behind it. So that what's trying to formalize that idea, but it definitely felt a little bit complicated, a little bit. Sometimes people are like, well, OKRs exist for a reason and this is, basically, an OKR with just a different name. So my honest sense is we still haven't figured it out and we're still iterating on a bunch of different things, but I think I've developed some philosophies around it, which is, no matter what you call it, because it doesn't matter as much.

**Yuhki Yamashita** (00:46:38):
I think that, for me, there are three things that really matter about the good OKR, and one is legibility. People look at it and understand what it is, and it's not some weird obfuscated metric that doesn't mean anything to anyone. I think actionability, I want OKR to inspire action. You look at that and you're like, it's stirs action, makes me want to do something differently. And the third one is authenticity, which is, does this actually, honestly depict what you're doing, what you're trying to do on a day-to-day basis? Because if it doesn't, then it's hard for me to trust that, that it matters. Or if that's something that just happens to describe what you're doing but isn't really connected in a meaningful way, then I question the value of it all.

**Yuhki Yamashita** (00:47:28):
So that's why I am in the process. But I definitely am all ears to advice around this kind of stuff, because I feel like we haven't quite cracked the code.

**Lenny** (00:47:38):
I love hearing that. That ,hole journey. I feel like you always hear from product teams, here's what we do now. You never hear, here's the experiments we've been through, here's what we've tried, here's what worked for a while, here's what doesn't work now, and here's what we're doing now. So it's really cool just to hear all the experimentation you've done. Clearly, Figma is a company where you encourage experimentation and trying new things that aren't working, and it's cool they have the flexibility to just like, let's just do headlines for now, and no more specific goal metrics. We're just going to build things that we think are important.

**Lenny** (00:48:09):
And in the newsletter post, for folks that are listening, you actually show the templates that you're using these days for planning your projects and laying out your OKRs, so folks can check those out if they're interested in seeing how you're doing that, now. You also mentioned you've hired this awesome data scientist, and maybe just expanding that further, I imagine a lot of the success of Figma and the product that you built is the people that you hire. At Figma, I believe you have 22 product managers, which sounds very small for a company like Figma, and I imagine they're all amazing. I'm curious what you look for in product leaders and product managers that you hire that, maybe, other folks aren't as focused on, and just what does the interview process look like at Figma?

**Yuhki Yamashita** (00:48:51):
Yeah, I shared some of these things. I really feel passionately about storytelling, and not to give it away or anything, but one of my favorite interview questions is asking, "describe to me a time when you're part of controversial product decision, and what did you do," and all those things. And I think it's really revealing because if they can set up this conflict and understand why this problem was really important and represent both sides in such that you can understand why that conflict existed in the first place, then they can do it in this even-keeled way, where you realize that they can take on these different perspectives. You start to learn a lot about that person, I think.

**Yuhki Yamashita** (00:49:35):
Or sometimes, I just ask them for basic things, okay, talk about a big problem that you worked on. And the thought experiment, for me, is always coming out of that, do I feel compelled to work on that problem? And no matter how boring it sounds on the surface, I think a really great product manager can cash something, it's like, well, this is why it's so existential for us, and this why it's so interesting, and really rally the troops up. So that's one big thing of storytelling communication because at the end of the day, so much of our job, it's around that.

**Yuhki Yamashita** (00:50:07):
I think other than that, some of the things that I value or things I think about as, hi Dan with UX conversations, it's like we talk about problem, and I think about when you're exploring solutions, it's this tree of, okay, there's just these branches of explorations and you finally arrive at these solutions. And a ton of people who can go up and down branches really quickly, have a really high command of all these different altitudes, as well, so that we can talk through a lot of things at the end of the day, feel like we walk away with some progress.

**Yuhki Yamashita** (00:50:43):
And I think that at Uber, our first two Product Officer, Jeff Holden, was someone who often talked about fast forwarding to the future and this idea that, okay, let's just pretend we ran that experiment. What do you think it'll come back with? Or let's pretend we ran that, you just use a study. And the PMs who have the ability to imagine those outcomes, I think, it helps us be much more efficient, too, because we're like, well, if we all think that it's going to go there and that's not going to compel us to take any action, why do it at all?

**Yuhki Yamashita** (00:51:17):
And so I think a lot of PM is about those shortcuts that you have to take. And it's not just about what we build, it's about building the right things. And sometimes, it's just as important to decide not to build something, but it's all only possible if you can have that kind of imagination or that ability to see around corners.

**Lenny** (00:51:37):
I love that. I was going to ask you for your favorite interview questions in our lightning round and you jumped ahead, which is great. And those are really good examples. Hopefully, they don't give too much away. I want to chat a bit about growth and how Figma grows. If you ask people about product led growth, and just whenever people talk about product led growth, they're always companies like Figma, Slack... Figma is always seen as a model of product led growth and a product that grew through product.

**Lenny** (00:52:04):
I imagine now, there's a very robust sales team, and I imagine, even earlier than people, probably, imagined there was a sales team. I'm curious, as a product leader, what you've learned about how to effectively work with sales and what you teach your product managers about how to work with sales to collaborate effectively.

**Yuhki Yamashita** (00:52:24):
We're really lucky to have a sales team that understands their product really well and can hold their own with customers who are often also design leaders, product leaders and things like that. And I think that kind of credibility goes a really long way. One of the things that we all are collectively realizing is, we talk about product like growth, but in some ways, I like to think about it more as community led growth or there are certain people inside a company that feel so strongly about Figma and that they're helping push for it in these advocates and evangelizing for Figma.

**Yuhki Yamashita** (00:53:03):
And so oftentimes, what the sales team does is really empower those individuals to make a stronger case or connect them to the rest of the company so that we can get a wider deployment or more leadership buying and things like that. And so oftentimes, a sales team is playing that role of creating those human connections and helping equip designers that feel passionately inside a company with the data, with the stories and all those things to help make a case. And I think that's the most powerful way in which we can spread where the space of Figma is not the sales team, but in fact, it's the internal designer.

**Yuhki Yamashita** (00:53:47):
And so that's the mental model that I think we've been using it. We're fortunate enough to have people inside companies who are so passionate to want to play that role. And so when you take that lens on, then you start to understand, okay, how can we help set this person up for success? And the sales team has different ways to do it. The product team can help, in terms of giving them visibility into how we're thinking about evolving the product or what other customers might be doing. And so, I really see it as this partnership to enable that much as possible. And I think that's what, to me, product growth looks like at Figma, is that.

**Lenny** (00:54:29):
That is really interesting. Basically, making your champion inside the company a superhero, helping them be more effective at what they're already doing, which is evangelizing this product that they really love. Interesting.

**Lenny** (00:54:42):
Is there anything that you think Figma did early on that you think was really important for it to start to grow, either in this way or in a different way? Imagine there's just a lot of product led growth founders that are trying to create a product led growth product, and they fail. And so I'm curious, just what do you think people often miss and what do you think Figma did right that got it going?

**Yuhki Yamashita** (00:55:02):
I think a lot of it was about the level of intention around building community. And the more there are organic conversations happening about Figma, the better. And one of the nice things about Figma is you can share out a file that you've been working on, and effectively open source something, but it's your way of showing, here's how we do it at so X, Y, Z company, and sharing that with the rest of the community. And when people see that and when people feel like they have this insider view in how other companies work, that's where there's a lot of interest.

**Yuhki Yamashita** (00:55:38):
And more recently, over the last few years, we've really been focused on a program called Friends of Figma where we have people who are passing about Figma, and all our different geographies come together in a Discord channel. They meet regularly and are helping us evangelize. And again, that's that human connection between users, and then between us and the users is something that really helps build that kind of loyalty, which is the thing that, then, fuels all the champions to really push for it, internally, and give people the enthusiasm and courage to do that inside their organization.

**Lenny** (00:56:16):
It's interesting how many corollaries there are to Notion and how they got started. I recently chatted with Camille, I don't know if you heard that episode, but there's a lot of similarities with how Notion use their community to help jumpstart growth and continue to grow.

**Yuhki Yamashita** (00:56:29):
Totally.

**Lenny** (00:56:30):
It's interesting that you can call that community growth, product growth. There's a lot of overlap there, potentially.

**Yuhki Yamashita** (00:56:36):
For sure.

**Lenny** (00:56:37):
What advice would you have for folks that are, I don't know, maybe you already shared this, but just if you're a product led growth founder listening to this, do you have any other piece of advice to that founder about how to get started with their product, their community, their growth strategy? Anything else you'd want to share there?

**Yuhki Yamashita** (00:56:52):
Maybe a different way to talk about what we just talked about, is just, there has to be this, almost irrational, this emotional response to your product and this like love for it. First, it has to be cultivated internally, too. People, internally, have to authentically love something to really stand behind it. But then, externally, too, if people are loving something to the point where they can sing at the top of their lungs and just really talk about how Figma's, great, if we can get there, that's a wonderful place to be.

And I think that's both a combination of you've really solved their problems well, but you also equip people with a philosophy around a different way of working. And I think that's what worked well for Figma, too, which is, there's something controversial about this idea that everyone can see what you're doing, or that multiple designers can be in the file at the same time. We like to say that one of the first responses we saw [inaudible 00:57:51] Figma was, if this is a future of design, I'm quitting. I'm changing careers. And there's that tension of that narrative tension, but that is signal that you're part of this revolution and you're trying to change something. And when it can equips your customers or user base with that, and I think that's something that they can really get behind and champion, so it's not just that they're championing for a tool, they're also championing for a new way of working.

Obviously, that's a tall order or [inaudible 00:58:23] come up with that. But hopefully, if your a founder, you're working on something, your mission is so big that you have those kind of ideas, and it's how do you actually equip your customers to want to talk about that?

**Lenny** (00:58:35):
That's awesome. Reminds me of a quote and a tagline that the Airbnb's first growth team had for a long time. Love drives growth, not the other way around. They made posters of this, put it all over the product teams.

**Yuhki Yamashita** (00:58:48):
I love that.

**Lenny** (00:58:49):
Part of the office and seemed to have worked for Airbnb, clearly working for Figma.

**Lenny** (00:58:54):
One last question feels like a question we have to touch on. I don't know how much you can say about all this stuff, but with the potential acquisition with Adobe, which I know isn't done, yet, but I'm just curious, what do you think will change, may change, you're hoping will change, you're hoping won't change in how you build product at Figma within Adobe?

**Yuhki Yamashita** (00:59:12):
Totally. Yeah. As you said, it hasn't closed, yet, and so we're still independent companies, but when we think about that theoretical future, I think about people often ask me, so what's going to happen, in terms of the products that you work on, and how is that going to influence Figma? And the answer is, we don't know, yet, but I get excited about two avenues. One is just really continuing our current mission of making product design better. And the reality is we look at product design, a lot of people are still using both Adobe and Figma alongside each other. And maybe you're creating that micro interaction in After Effects, or maybe you're doing that intricate illustration in Illustrator, or editing Raster in Photoshop, and then you're bringing some of those things into Figma. But when you think about the end product development process, there's so many ways in which, if we can make all those things seamless so that you're not juggling a bunch of apps, or maybe you can have one single source of truth, that's really exciting to me to think about. So concretely what that means, I don't know, yet, but as thinking through those journeys, that gets exciting for me.

**Yuhki Yamashita** (01:00:22):
And then the other thing is really collaborating with the rest of Adobe and thinking about, we've figured out something really interesting in the form of realtime multiplayer collaboration, and that, as a platform. Adobe has a much broader set of use cases that they've been pursuing, and what do those two things together, what could that enable? And that gets exciting for me to think about all the creative tools that I've used in the past, be it video editing or 3D objects or things like that where it's, okay, if we can bring in the power of the browser, of multiplayer, of this feeling of openness, would that make it way easier for people? Would it make it much easier for people to share work or get involved?

**Yuhki Yamashita** (01:01:04):
So those are the things that go through my heads, in terms of what's possible. In terms of what I don't want change. I really think that we've figured out something really amazing, in terms of our relationship with the community. We talked about proximity to community and our users. Those are things that we intend to keep and keep doubling down on. And I think it's such an important part of the magic of how Figma works. So it's something that, I think, I will continue to do and that's what I draw a lot of motivation from in the first place.

**Lenny** (01:01:34):
Awesome. You also get to work with Scott Delski, which is going to be pretty sweet and hoping to get Scott on this podcast at some point, too.

**Yuhki Yamashita** (01:01:41):
That'll be awesome.

**Lenny** (01:01:42):
Any closing thoughts before we get to our very exciting lightning round?

**Yuhki Yamashita** (01:01:46):
It's really easy to listen to some of these podcasts and feel like, oh, these people have kind of figured everything out.

**Yuhki Yamashita** (01:01:53):
But the reality is, we haven't, and we're still experimenting with a lot of things. OKRs is a really good example of that, but a lot of other things. And so, just the other day I wrote about this idea of us living in a work in progress world, and I was talking about more from the context of we live in a world where all of our products, our product players, our strategies are work in progress, and how do you work in a world like that, when what you're reviewing can change the next day.

**Yuhki Yamashita** (01:02:23):
But in a similar way, I think the way we work, the way we run product processes as product managers is, itself, very much a work in progress. So I would love to encourage this kind of conversation, Lenny, that you're facilitating just because you have so much to learn from each other. And I'd love to continue to learn more from all of you on interesting ways that you grapple with these age old problems around things like how to set goals, or how to review work, or how to plan.

**Yuhki Yamashita** (01:02:54):
So anyway, just wanted to signal that we are very far from perfect, and I really eager to learn from everyone else, as well.

**Lenny** (01:03:04):
I love that. That also reminds me of something the Airbnb founders always came back to. Joe and Brian were both designers, and as you learn to be a designer, you are taught that everything around you is designed by someone. Someone just decided this webcam's going to look this way and work in this way, this chair, somebody decided very specifically, it's going to be like this. And we assume the things that we are working within are just, they're figured out. Someone much smarter than me figure this out. But it's usually just someone just like you that had to figure something out quickly, and then that's what you're doing now. And so they always encouraged everyone to just remember someone designed this, doesn't mean it's the perfect solution, and you should always rethink things like that and not assume.

**Yuhki Yamashita** (01:03:44):
Yep.

**Lenny** (01:03:44):
Well, with that, we've reached our very exciting lightning round. I've got six short quick questions for you. I'll just go through them pretty quick, whatever comes to mind, share, and we'll see how it all goes. Sound good? All right.

**Yuhki Yamashita** (01:03:56):
Sounds great.

**Lenny** (01:03:56):
Awesome. What are two or three books that you've most recommended to other folks?

**Yuhki Yamashita** (01:04:02):
First one that comes to mind is Switch, and it's really about how to affect organizational change, something that's Shishir recommended to me and we have the difficulty of affecting change in a large organization, basically, and how to overcome that.

**Yuhki Yamashita** (01:04:16):
The second one I would say is my favorite book of all time is one called The Story of the Stone, and it's a Chinese novel, one of the most famous Chinese novels of all time. And it's thousands of pages. It all takes place in a garden, but it's one of the most beautiful piece of work I've read, so I like to recommend that, even though it's nothing to do with PM.

**Lenny** (01:04:38):
Did you say thousands of pages?

**Yuhki Yamashita** (01:04:39):
Yeah.

**Lenny** (01:04:41):
About a stone. Wow. I will check this out. I love it. I've not heard this one before. Favorite other podcast, other than the one you're currently on?

**Yuhki Yamashita** (01:04:49):
Well, I'll have to admit, I'm actually much more of a visual learner, not a listener, and so I rarely listen to podcasts, but the two that I have listened to, in earnest, was first one was Cereal a long time ago, and then yours.

**Yuhki Yamashita** (01:05:04):
So I think some of the best, actually, but otherwise, more into reading.

**Lenny** (01:05:09):
Awesome. This show's also on YouTube, for folks that don't listening and like watching things. Plug, plug. Favorite recent movie or TV show?

**Yuhki Yamashita** (01:05:18):
The last movie I watched was called The Good Nurse, and it was about a serial killer working in a hospital, but it was a very different take on it. It was very human. It wasn't grotesque at all, and was talking about how broken our system was. So, highly recommend it. Quite sad, but yeah.

**Lenny** (01:05:37):
Okay, good tip. What are some SaaS products that you love that you, maybe, use at Figma or that you just discovered that you find very useful?

**Yuhki Yamashita** (01:05:45):
Kind of cheating, but as I mentioned earlier, we're starting to use FigJam for everything from calibrations, to interview debriefs, to product reviews, to everything. So that's thoroughly started to dominate our usage. It's been cool to see. And then we have our usual suspects like Slack and Asana, and then we're all over the place on the rest. Some of us use Notions, some of these use Dropbox Paper, some of these uses Koda, and so we're still figuring that one, out, I'd say.

**Lenny** (01:06:16):
Dropbox Paper. Very cool.

**Yuhki Yamashita** (01:06:17):
Yeah.

**Lenny** (01:06:18):
I love that product, but I feel like no one uses it anymore, but it's cool that you guys do. Final question, favorite FigJam or Figma plugin or template?

**Yuhki Yamashita** (01:06:27):
We have this one called the Alignment Scale, which is a widget that you can insert into FigJam or Figma Design, actually. And we use it all the time. So basically, it's just a simple scale and whenever people click it, their face appears on one end of the spectrum or the other. And so it's our quick way of being like, we're doing a product review, we on a pulse check, we drop it in and we're like, how are people feeling aligned, not aligned?

**Yuhki Yamashita** (01:06:52):
And if people are aligned, we just move on. If not, then you know that it's worth a discussion. So it's just a fast way to figure out where all the hotspots are.

**Lenny** (01:07:01):
Awesome. And if folks want to find that, they can actually go to the newsletter interview that we did. I think if you just Google how Figma builds product, it comes up number one, and then there's a link to actual template, so you can plug that right in.

**Lenny** (01:07:13):
Yuhki, thank you so much for being here. I am going to go play with Figma and FigJam right after this. Two final questions. Where can folks find you online, if they want to reach out, learn more? Are you guys hiring, anything there? And then, two, how can listeners be useful to you?

**Yuhki Yamashita** (01:07:30):
Yes, you can find me online on Twitter or LinkedIn. Feel free to reach out there.

**Yuhki Yamashita** (01:07:36):
In terms of how you can be useful to us? We're really starting to build a lot of products for this audience, for product managers. FigJam is one example of this, so definitely try it out, give us the feedback, tell me all about all the cool things that you're doing or you wish you could do on FigJam or Figma. And you can tweet at me, you can find me anywhere. And, of course, we're also hiring, so if you know great people or are interested, yeah, there's a lot of roles, so please get in touch.

**Lenny** (01:08:06):
Awesome. Yuhki, thank you so much for being here.

**Yuhki Yamashita** (01:08:08):
Thank you so much for having me, Lenny.

**Lenny** (01:08:11):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [3/22] How to price your product | Naomi Ionita (Menlo Ventures)

**Naomi Ionita** (00:00:00):
Do not set it and forget it. I see companies do this, where they labor over designs and features. And they build this perfect product that's delightful to use. And then pricing's sort of plucked out of thin air, and then they don't revisit it. This was Evernote. It was many, many years before we went back and overhauled the pricing. So, think about your pricing just like you do your roadmap. Every 6 to 12 months, there's probably something meaningful that you're launching for users. So, treat that as an opportunity to revisit your monetization strategy and making sure you're compensated appropriately.

**Lenny** (00:00:32):
Welcome to Lenny's Podcast. I'm Lenny. And my goal here is to help you get better at the craft of building and growing product. Today, my guest is Naomi Ionita. Naomi was one of the first early leaders in product life growth and monetization, having built early teams and infrastructure over a decade ago at Evernote. She was also an early contributor to Reforge when it was just getting started and helped create some of their early programs. She's also VP of growth at Invoice2go. And currently, she's a full-time VC at Menlo Ventures.

**Lenny** (00:00:59):
In her work as a full-time investor, she gets to see what works and doesn't work across many companies. And one area that she spends a lot of time on is monetization, when it's best to start charging for your product, how to decide what to charge, and how to evolve your pricing. And that's what we spend the bulk of our conversation around. We also touch on a really interesting framework Naomi has been developing that she calls the Modern Growth Stack, which is essentially all the areas that new starter products can help take the load off your plate and help your product grow. Naomi is awesome, and I'm excited to share this episode with you. With that, I bring you Naomi Ionita right after a word from our wonderful sponsors.

**Lenny** (00:01:36):
Today's episode is brought to you by Miro. Creating a product, especially one that your users can't live without, is damn hard. But it's made easier by working closely with your colleagues to capture ideas, get feedback, and being able to iterate quickly. That's where Miro comes in. Miro is an online visual whiteboard that's designed specifically for teams like yours. I actually used Miro to come up with a plan for this very ad. With Miro, you can build out your product strategy by brainstorming with sticky notes, comments, live reactions, voting tools, even a timer to keep your team on track.

**Lenny** (00:02:10):
You can also bring your whole distributed team together around wire frames where anyone can draw their own ideas with the pen tool or put their own images or mock-ups right into the Miro board. And with one of Miro's ready-made templates, you can go from discovery and research to product roadmaps to customer journey flows to final mocks. Want to see how I use Miro? Head on over to my Miro board at miro.com/lenny to see my most popular podcast episodes, my favorite Miro templates. You can also leave feedback on this podcast episode and more. That's miro.com/lenny.

**Lenny** (00:02:47):
This episode is brought to you by Notion. If you haven't heard of Notion, where have you been? I use Notion to coordinate this very podcast, including my content calendar, my sponsors, and prepping guests for launch of each episode. Notion is an all-in-one team collaboration tool that combines note-taking, document sharing, wikis, project management, and much more into one space that's simple, powerful, and beautifully designed. Not only does it allow you to be more efficient in your work life, but you can easily transition to using it in your personal life, which is another feature that truly sets Notion apart. The other day, I started a home project and immediately opened up Notion to help me organize it all. Learn more and get started for free at notion.com/lennyspod. Take the first step towards an organized, happy team today, again, at notion.com/lennyspod. Naomi, welcome to the podcast.

**Naomi Ionita** (00:03:45):
Thank you.

**Lenny** (00:03:46):
Did you know that you're one of the very few VCs that I've ever had on this podcast, and so you're basically representing VC kind here? How do you feel about that?

**Naomi Ionita** (00:03:54):
Wow. Well, thank you. I think early growth folks like us have a unique bond and a lens on startups and investing. So, my operating background is something I lean on every day and has actually informed a lot of the thesis areas where I spend time now as an investor. So, hopefully, we'll bring it all together in that capacity.

**Lenny** (00:04:15):
Awesome. That's exactly what I was just going to say, so I'm glad that you covered that. And so that's a good segue just to... Let's get into your background briefly. Can you talk about some of the wonderful things that you've done in your career both at Reforge, which you'll touch on, and growth stuff, and then your VC life now?

**Naomi Ionita** (00:04:29):
Perfect. So, I'm a partner at Menlo Ventures. I focus on early-stage SaaS from seed to series B. I started my career in engineering and consulting before getting into tech back in '06. Fell in love with product. Did some new product development at a big media company before business school. And while at business school, I spent time at the Design Institute at Stanford. So, this was an opportunity to kind of bridge my analytical background with this refreshing view on human-centered design and learning from the founder of IDEO.

**Naomi Ionita** (00:04:56):
So, brought that with me then to Evernote back in 2011, early days over there. I was there from about 10 to 100 million users. And over that arc, I shifted from more of a core product role to starting our growth product function. This was super organic. I started just collaborating with colleagues from across the business, come up with hypotheses, do user research, run experiments, drive metrics. This was a new way of building product back then. This was a decade ago, so the acronym PLG had not been coined yet. And I really just thought of myself as a user and data-driven product person.

**Naomi Ionita** (00:05:33):
After Evernote, I joined a bootstrapped mobile SMB company called Invoice2go. It was the top-grossing business app at the time. There, I built teams across product, data, growth engineering, design and research, and again, focused on product-led growth and monetization. Over those two jobs, I found myself doing a lot more advising and speaking on the side on these topics. And my board members used to farm me out to their companies to help their founders think through things around product growth and pricing and various topics like that. And Reforge came together at the same time, so I would come in and speak on topics through that community. So, that really accelerated my transition into venture. I realized how much I love having that portfolio view of the world and helping founders look around corners. So, I think it's an incredible privilege to get to do the work that I do.

**Lenny** (00:06:22):
One thing you mentioned is Evernote. I don't know how much you can talk about this, but they just got sold, right? Someone bought Evernote. And if I think back to Evernote, it feels like they could have been Notion, which is killing it right now. Any thoughts on what maybe they missed and didn't turn into Notion along the way?

**Naomi Ionita** (00:06:39):
Yeah. We're going to clear some cobwebs here. It's been a while. But one challenge that Evernote really struggled with was this evolution from single-player to multiplayer to team to enterprise. It's a chasm that a lot of bottom-up SaaS businesses struggle to cross. Evernote was philosophically antisocial. It was meant to be your second brain, kind of your personal tool. And I think that capped the company's growth potential. I always used to say you can't retrofit collaboration. You have to be collaboration-first. And a lot of companies now really take that for granted. But back in mid-2000s, this was kind of a new way of building product. And so we missed that bridge.

**Naomi Ionita** (00:07:20):
If companies do that well, it benefits every metric. That bridge from single-player to multiplayer. Acquisition goes up. You grow organically through referrals and shared workflows. Retention goes up because now you have these shared workflows that are incredibly sticky. Employees are accountable to each other to say, "This is how work gets done." Design in Figma, roadmap planning and ticketing in Jira are linear. It just becomes the default platform. And modernization goes up. Revenue scales with usage. And so the more people using it, the more they use it. You start tripping the wire on paying more and more over time. And so Evernote really struggled in crossing that chasm from the prosumer tool of choice that employees wall-to-wall were using, but never became this larger high-ACV contract from a sales perspective.

**Lenny** (00:08:06):
Yeah. It's always easy in hindsight to see what could have been better, what could have worked out, what didn't work out. So, what are you going to do? You mentioned monetization. And I know that you spent a lot of time with founders working on pricing, monetization, especially using monetization as a lever for growth. And so I want to spend some time there to pick your brain about what founders and growth teams can do and how they should think about monetization in terms of growth.

**Naomi Ionita** (00:08:06):
Perfect.

**Lenny** (00:08:31):
And then you also have this cool concept that you've been developing that you call the Modern Growth Stack, which is kind of this play on modern data stack. And so I want to spend some time there.

**Naomi Ionita** (00:08:40):
Perfect.

**Lenny** (00:08:40):
Cool. So, to dive into that first topic of monetization, if you think about when you're starting a company, what are some of the biggest challenges you face? Start building a product, especially a B2B product, I always think about pricing and trying to figure out how much to charge, how to charge, your pricing model, how to evolve your pricing, when to charge, all these things. And so I know that you work with founders helping them figure these sorts of things out. And so maybe a first question here is just what do you find startups most often miss or get wrong when they're starting to think about monetization?

**Naomi Ionita** (00:09:12):
There's a lot to cover here. I'll cover a few missteps that I think are most common. One is waiting too long to monetize. Another one is underpricing. And this isn't just setting the base price too low, but it's also leaving money on the table by not offering different plans to cater to different segments. And the third one is all too often with pricing, people set it and forget it. So, this idea that when your product development work is never done, neither is your pricing, and you need to combat that along the way. So, those are three areas I think we can cover here.

**Naomi Ionita** (00:09:47):
Maybe starting with one, I can jump right in, I think waiting too long to monetize. The beginning of a startup's journey is all about creating something of value. Right? That's the whole point. Hopefully, founders have some unique market insight or some authenticity around a pain point and some novel solution that's going to change the world. So, that business value is really critical. But the other side of the same coin is being properly compensated for that value as a business. I understand the vulnerability of being a new startup. You just want people to use your product. And I view that early free beta user feedback loop as an R&D cost to make sure you're building the best possible product and that they're driving a lot of value.

**Naomi Ionita** (00:10:28):
But I see companies way too long to make that shift from building a product to building a business. And I think that's the true signal of product-market fit, is ultimately having people open up their wallets and pay you, so looking for people to get to that end goal. And so again, these things aren't mutually exclusive. You're going to create business value, but you're going to be compensated for it and prioritize your roadmap over time so that you're building based on what people actually want and are willing to pay you for.

**Naomi Ionita** (00:10:55):
So, when you don't monetize, I think you're doing yourself a disservice. The things that I see as the pain of leaving money on the table, you're inadvertently cheapening your product. People attribute a lower dollar value or a $0 value to what you've built. You're missing out on critical feedback loops to understand what people are willing to pay. And you're shooting your future self in the foot because this is the other problem, is at some point you're going to start charging, and you're going to experience some backlash. So, it's nice to get ahead of that. A few things to think about, kind of food for thought around delaying and kicking the can down the road from a monetization-

**Lenny** (00:11:29):
So, just to reinforce that, your general piece of advice is if you're building a B2B product, start charging immediately. Don't give it away for free. At least have some... You could probably give it away for free but make it clear, "We're going to charge you this much soon." How do you think about that?

**Naomi Ionita** (00:11:45):
Yeah, I don't think those are mutually exclusive. So, this isn't to say that I don't like freemium models. Evernote was the darling of freemium over a decade ago. So, I'm still a big believer in that. It's more a question of where you put the paywall. How much do you give up for free? And then how do you price and package a paid version of your product? So, freemium is all about getting that top-of-funnel excitement, getting people to build habit formation. You're collapsing time to value. You're building habit formation. You're building all these champions to use your product. But the idea is to shepherd them along into a paid version of your product and to, again, not delay the idea of, "What should our premium features even be? What should that paid plan even look like?" Again, going back to the misstep at Evernote, I think there was always a premium plan, but it didn't really bridge into enterprise. So, we can talk more about that.

**Lenny** (00:12:35):
This is kind of a tangent, I know, because you have these two other pieces of underpricing and setting it and forgetting it. Been talked about, but do you have any advice for deciding what goes into freemium and what-

**Naomi Ionita** (00:12:44):
If it gets you to the aha moment, that path to habit formation, that has to be free. That's the core utility of your product. And so the idea is that in that first session or first day, someone's getting to see the delight and saying, "Oh, my God. I'm never going back to the old way. This is how X gets done." If you're looking for some virality or network effect, that's the other thing. Your free users, you might not be getting revenue from, but the idea is that they help you manage CAC. So, these are folks that are driving organic growth for you and helping reduce the incremental cost of your next set of users. So, that's another part of the math equation to think about in giving up revenue.

**Lenny** (00:13:23):
You also have this model that you didn't mention that you mentioned in a previous chat we were having offline of this idea of day one versus day 100, stuff people need on day one versus what they need down the road. Do you still believe in that? And what should people know about that?

**Naomi Ionita** (00:13:36):
I do believe in that. That was tied to... We had done this experiment at my last company, Invoice2go, where... Typically on the demand curve, the higher you raise the price, the average revenue per user or ARPU, the lower the conversion rate. So, these things are inversely correlated. And we were able to do this rebalancing of our pricing and packaging so that we actually doubled our upgrade rate from our starter plan to our pro plan.

**Naomi Ionita** (00:14:00):
... We doubled our upgrade rate from our starter plan to our pro plan while also increasing the price of the pro plan. So, to actually get twice as many people to upgrade while paying something like 30% more for that new plan is pretty rare to get the compounding benefits of that. And what we did was thought a lot about what is a day one premium feature? What is a premium feature that you can get value from the very first time you engage with the product? That's different than your day 100 features. Those are the ones that represent more advanced functionality. Maybe they're ones where the value is derived from having a certain scale of data in the platform.

**Naomi Ionita** (00:14:37):
And so, those you shouldn't waste cognitive load for your users to have to even understand or try to appreciate when they're first getting going. Push those into a more advanced pro version of your product, and monetize them down the road through an upsell. So, big believer in how do you really keep pricing simple? And we've all seen those SaaS pricing pages where there's a laundry list or just a gnarly matrix of features and functionality. So, do what you can to think about that journey for a user and how they're going to continue to increase value with your product over time, and how you can map your pricing and packaging against that journey.

**Lenny** (00:15:13):
I really like that framework, because it's so straightforward and simple. As you use it, you'll need more enterprise features innately, because you're sharing it more widely. Your head of security's going to be like, "What are you doing with this thing?" Your finance team's going to be like, "Oh, how do we pay for this thing?" And so, that's a really nice simple way of thinking about what to put in freemium in your free plan versus not. So, glad we touched on that. Okay, so we were going through the three things that companies and founders do wrong when they're starting to price. And so, the first you said was they go too late and I tangentized us, so I'll give it back to you to keep going through this.

**Naomi Ionita** (00:15:53):
[inaudible 00:15:53] This is by far the most common issue. And so, one framework I like to use here is matching price to value. When you do that, you create alignment with your user. So, this entails picking the right value metric. So, this is the unit of value that they derive from using your product, and it creates this natural escalator, because as people use it more, you get paid more over time. SaaS was historically built on a seat based model. That's been historical SaaS pricing. And now with the rise of PLG, we've seen more of these usage based approaches gaining speed, so that's pretty exciting to see. Whether it's number of API calls or messages sent or terabytes of storage used or words written, this usage-based approach really matches price to value over the lifetime of a customer. The other thing that happens when you match price to value is it helps you understand who you're building for, and it lets you target different customer segments.

**Naomi Ionita** (00:16:46):
In doing that, you're able to better serve each segment, but you're also able to maximize revenue for the business. Evernote always had a business model. From its beginning, it had $45 a year for an annual subscription. And this set the foundation for the company and tens of millions in revenue, early revenue growth, but the approach was suboptimal. So, as a growth team, we started doing surveys. I was really curious to understand why people converted from our free version to our premium subscription. And one of the most popular answers without fail was, "Well, I just feel guilty. I use it so much. I get so much value from it that I just feel obligated to pay." And take that in for a second, because if guilt is one of the main reasons why people are paying you, then your free version is too good, and you are leaving money on the table.

**Naomi Ionita** (00:17:36):
So, a single premium tier is often a mistake, and you're going to be leaving money on the table for specific segments, and it's important to drill down and understand who those are. Our additional research helped us understand that brand-new users with low perceived value of Evernote looked at it like their Apple Notepad app that was pre-installed on their device. And so, they couldn't understand the idea of paying $45 for Evernote. But then we talked to avid users, and these were people that were cross client using it on desktop and mobile, every device they had. They were using it for work and personal, they were leveraging OCR capabilities and the web clipper, and it was truly their second brain. They could not imagine life without it. And these people were floored that they were only paying $45 a year. They told us that they were getting hundreds of value from Evernote.

**Naomi Ionita** (00:18:28):
Here, the perceived value for avid users was far outpacing what we were asking from them. And this intuition and research really led to a bifurcated strategy of having different plans for different personas based on the value they got from the product and their willingness to pay.

**Lenny** (00:18:45):
That makes sense. When I heard you say that it costs $45 for a year, that sounds way too low. So I could see how that sets the pattern for Evernote just not making enough money over the long term. Cool. And then the third was that you don't evolve your pricing, right? That's like the third biggest mistake.

**Naomi Ionita** (00:19:03):
Yes. So, do not set it and forget it. I see companies do this where they labor over designs and features, and they build this perfect product that's delightful to use, and then pricing plucked out of thin air, and then they don't revisit it. This was Evernote. It was many, many years before we went back and overhauled the pricing. So, think about your pricing just like you do your roadmap. Every six to 12 months, there's probably something meaningful that you're launching for users. Treat that as an opportunity to revisit your monetization strategy and making sure you're compensated appropriately.

**Lenny** (00:19:33):
What advice do you have for founders around just how to decide in your initial price? Clearly Evernote didn't get that correct, and I'm sure you've learned a lot from that and then other companies you've worked with. How do you actually decide what to start charging?

**Naomi Ionita** (00:19:45):
Yeah, there's a full pricing process here, so I'm happy to walk through it. The idea here is understanding who your customers are, why they pay you, what is it that they want or value, and how much are they willing to pay you. I'd encourage you to put together a pricing committee. This is not a single-threaded exercise that lives in one department or another. This very much is a cross-functional exercise. If you are a PLG company like companies I worked at, this was the product growth org that I ran. So the combination of PMs and data scientists, folks like that to iterate on pricing. If you are an enterprise SaaS business, of course, sales and finance and rev ops play a role. Think about who that committee should be at your company, and commit to being that cross-functional team that really owns and iterates on pricing over time.

**Naomi Ionita** (00:20:31):
Then, they are responsible for talking to customers. This is by far and away the most basic thing you can do to just increase those feedback loops and understand how much you can push the envelope on pricing. You do that with surveys, with interviews, there's some questions that we like to use around understanding the relative prioritization of features. Going back to that laundry list of features and matrices on a pricing page, it's very rare that people convert equally across all of those features. There's typically one or two that are the main points for conversion. So it's good for you to understand the relative rank there and how to reconcile some of your pricing and packaging accordingly. So, we would make a list of our features that we had and maybe new things we wanted to build and have people rank them as a must-have, nice to have, or not necessary that help us understand the relative prioritization.

**Naomi Ionita** (00:21:23):
You can also get at it with a hundred point question where you give users a hundred points and say, "Spend them across these different features." And the more points you give a feature, the more value you're assigning to it. This is to get to the demand or the features and functionality that you've created. It's step one. It's understanding what people will actually want and making sure that they're not just saying everything but the kitchen sink, but they're actually getting a good sense for what's most important to them. And then the other side is understanding their willingness to pay. I'd say the easiest on-ramps here for companies to start digging into that is to use Van Westendorp's method here. I don't know if you're familiar with that. You're nodding a little bit.

**Lenny** (00:22:05):
Yeah. Yeah. Comes up a bunch on this podcast.

**Naomi Ionita** (00:22:08):
Oh, great. So I might be repeating myself here, but...

**Lenny** (00:22:10):
No, this is great. This is how we learn. We hear it again.

**Naomi Ionita** (00:22:13):
If you take the packages that users designated as nice to have and must have, you make that collection of features in the survey, then ask them, "What's such a cheap price that you start to question the quality of the product?" Ask them, "What's a good deal or sounds like the right price for this package?" Ask them, "What's expensive, but they would still pay?" So you're starting to get to that level of discomfort. And then ultimately, "What's prohibitively expensive? What would people just say, 'Okay, that's it.' You've crossed the line of how much I'm willing to pay here." And by plotting those four curves, you start to get a sense of how to inform your pricing. That's a great way to marry the questions around demand and then the questions around willingness to pay.

**Lenny** (00:22:52):
Awesome. I wish that survey name was simpler to say, because I can never remember exactly to pronounce it, but you got it. So Van Westendorp.

**Naomi Ionita** (00:22:52):
You got it.

**Lenny** (00:23:01):
So, say that you got a price, you launched with something. How do you think about and how do you suggest folks experiment with pricing changes? And then, what impact have you seen from making a pricing change, either in terms of revenue or growth? Because I know you work with a lot of startups on these sorts of things, so I'm curious. How big of an impact can you see from pricing changes?

**Naomi Ionita** (00:23:22):
Oh, it can be huge. Our friends at OpenView do a really good job of pumping out content and doing these great SaaS benchmarking surveys. They did something recently that showed that roughly half of companies that instituted a pricing change saw at least a 25% increase in ARR. So that's a pretty massive step function improvement in your revenue from something that doesn't require massive technological overhaul. I find that most companies regret not doing it sooner. ProfitWell is another group that I have friends at and have a lot of respect for them and the content that they've put out. They did a survey once on I think it was over 500 SaaS companies, and they looked at for a 1% improvement on acquisition, retention, and monetization, how did it impact a company's bottom line? And they found that the impact with an improvement on monetization was 4X that of acquisition.

**Naomi Ionita** (00:24:13):
So, this idea of how can you efficiently improve your business monetization is really underappreciated as a growth lever. Definitely something people should be thinking about. That's part of my goal of doing this podcast, is making sure founders are compensated in a way that they deserve. So, let's hope everyone makes a little more money after today. And I've seen a lift upwards of 10X on revenue, but it's sometimes hard to parsh just the pricing change, because usually it can be coupled with big product changes, a rebrand, a lot of PR, the launch of a new plan, like a team or an enterprise plan. So, it's hard to sometimes understand just the pricing change in isolation, but it really can be pivotal.

**Lenny** (00:24:54):
Cool. And when you think through the pricing changes that you've seen, is the impact often from raising the price just broadly? Is it segmenting more intelligently? Is it changing freemium versus paid? Is there a bucket you think of, like "Here's generally where the biggest impact ends up being?"

**Naomi Ionita** (00:25:13):
Yeah, it comes from doing it holistically. I think it's very rarely as impactful if you just pick a new price or just launch a new plan. I really think of it as rebalancing pricing and packaging overall. So it's doing this whole exercise of understanding what people actually want, what their willingness to pay is, and mapping it to that user journey like we talked about from single-player mode to multi-player, that first other person you connect with and have a workflow with, spreading it to your whole teams and ultimately spreading it wall to wall across an organization. So it's a longitudinal view of the user lifecycle and thinking about your whole business model holistically.

**Lenny** (00:25:53):
I don't know if you can talk about any of these, but is there a company or an example that comes to mind where you did a pricing change and just talking about what they changed just to make this even more concrete?

**Naomi Ionita** (00:26:02):
I have a specific story there with one of our companies, Envoy. This is a fun one. He was just getting started. This is Envoy, the visitor registration tool that I'm sure a lot of people have used, especially before COVID.

**Lenny** (00:26:16):
Probably mostly in SF, so I imagine folks in other countries don't know about it. Maybe describe it.

**Naomi Ionita** (00:26:20):
Yeah. So, if you visit an office instead of just signing in to that piece of paper in the lobby with your name and your email address and what time you checked in, it is a digital iPad based way of checking in and sharing information with the person you're visiting. And so, in talking to Larry and getting a feel for his evolution around pricing, he tells a story that I love. He was meeting with a big hospitality company, and the conversation was going really well. This prospect was really leaning in and excited about using Envoy, and the conversation shifted to pricing. So in that moment, because Larry was feeling some good vibes, he decided to 10X the price that he was typically charging people. So, just in the moment he decided to just go for it. Go out on a limb, and ask for 10X the typical price.

**Naomi Ionita** (00:27:13):
And in that moment, the exec said, "Okay, sure. Sounds good." Not a minute of hesitation, not a second of hesitation. And what he learned in that moment was that, one, he was wildly underpriced. It was very clear that he hadn't even thought about what the ceiling was. But the truth was he probably could have pushed it even further, considering there was no hesitation. So, what I encourage users to do, especially in these enterprise conversations, is to continue to ask for more, to understand where the upper bound might be, and to understand that it's okay sometimes to lose some deals due to price. Something on the order of 20 to 30% is reasonable so that you can get a sense for where the limit might be. The vast majority of companies are definitely undercharging like we discussed. So, go out on a limb like Larry at Envoy, and you can see that sometimes you can...

**Naomi Ionita** (00:28:00):
... like Larry at Envoy and you can see that sometimes you can 2X, 4X, even 10X your price.

**Lenny** (00:28:07):
That's an awesome story and it touches on exactly what you said where people often underprice. I imagine it's strategically smarter not to go straight to 10X and maybe go two or three X until people start pushing back because you lose a lot of data there. But that's one way to just zoom to an answer.

**Naomi Ionita** (00:28:22):
Yeah, they're all feedback loops, so I think there's some incrementality to it. But you got to understand who these different segments are, and if you don't have enough data points, it's hard to really understand how to continue to optimize.

**Lenny** (00:28:33):
Any other tips that you want to leave listeners with around pricing or monetization, or even testing pricing? Anything there before we shift to our second topic?

**Naomi Ionita** (00:28:43):
Yes. So we talked a bit about research methods and different surveys you can do to help inform your pricing. And with Enterprise, it's all about continuously asking for more. But if you're a PLG company and you have a public facing pricing page, I'd encourage you to experiment. This is something people shy away from, and frankly, there haven't historically been great tools for companies and infrastructure to be able to do this work.

**Naomi Ionita** (00:29:08):
So at Invoice2go, we invested very heavily in some internal pooling. We had a whole metering and human management and experimentation system in-house. It was a big growth engineering undertaking. And with that we tested different value metrics. We tested different quota limits, price points, promotions, you name it. We tracked the consumption of our pay as you go model and looped that back into the product so we can nudge users along the lifecycle to get them to convert, or upgrade or renew, once quota limits were reached.

**Naomi Ionita** (00:29:38):
So there's a lot there. I'm excited about this new wave of modern tools to actually help you do this and not sync a bunch of engineering time into building something in-house. So that's something we can talk about in a bit. But that investment was very worthwhile. We had huge revenue gains by being able to iterate in a way that was more streamlined.

**Naomi Ionita** (00:29:57):
There's some things to watch out for though. It's hard to test pricing. There's a lot of different variables to isolate. So you've got to make sure you're bringing a consistent test experience to the in product experience, your pricing page, maybe mobile app stores or lifecycle emails that you're sending.

**Naomi Ionita** (00:30:14):
One trick you can do is we would segment these tests by geo. So we would do some tests in Canada or Australia before rolling out in the US. That was a nice way to just put some constraints around our experimentation.

**Naomi Ionita** (00:30:28):
And the other thing you really have to think about is the long-term nature of pricing experimentation. So knowing if you succeeded and failed often requires understanding the implications on churn. Let's say part of your test is year one discount. You need to understand how users perform in year two and have a sense of the trade-offs around user growth, retention, ARPU. So all of these things are different levers that you want to optimize over time.

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**Lenny** (00:32:13):
There's a question I wanted to ask you, and maybe it's too big of a question to answer simply, but it's this question you just raised of trading off revenue versus growth. That's one of the most common trade-offs founders have to make. Do you have any just general thoughts, advice there? Is there one you should generally index on? What have you seen works best? Which kind of direction should you lean, growth or revenue, for your, let's say, B2B company? Like early stage?

**Naomi Ionita** (00:32:40):
Yeah, if you know that you have a bridge to move up market, then giving up the long tail of individual users can be very worthwhile.

**Naomi Ionita** (00:32:50):
So I think Figma is a great example of that. This was a company that took a while to monetize. And even having free usage at the individual level, that was the way to just drive insane community and love for this product. Designers around the world just fell for this product overnight. But this idea that once they were using it in a more corporate setting, once they were collaborating with more people across the business, they were tripping a wire to pay. And so what happened there was you had this massive top of funnel of individual users, but knowing that design is inherently collaborative, you're interfacing with engineers, you're interfacing with PMs, with marketers, with researchers, with execs, more than half of Figma users weren't even designers once it was embedded in the enterprise. And so this idea of these compounded growth loops that you got by interfacing with so many different parts of the company and making design truly collaborative and in the browser, they were able to just have this exponential curve on monetization once they shifted into more of a team or enterprise based package.

**Naomi Ionita** (00:33:54):
So that's a good example of saying, they were willing to trade off on monetizing the individual because they knew that it would be so sticky and would go so wall to wall within a company.

**Lenny** (00:34:05):
Got it. So your feeling is if it's a multiplayer PLG-ish product, you probably want to optimize for growth. Let it just take over and not go charge as much as you can immediately, versus say like a sales led B2B enterprise-y product, maybe they're focused on revenue immediately versus making it feel cheap. Is that right?

**Naomi Ionita** (00:34:27):
And I think if you do have a few free users, crafting it as more of a sweetheart discount, like more of a year one discount, but getting paid over time. I mean, again, I am a big believer in having some early users being your design partners and really giving you that tight feedback loop to make sure you're building the right product. So it's not that you should really optimize for revenue on day one. I mean, it is a journey, but I just oftentimes see companies just take too long. Or in Evernote's case, I mean the free version was just too good. So that's just something to consider, where to put the paywall and be really, really strategic about that.

**Lenny** (00:35:02):
Just don't optimize for guilt in your paid driver.

**Lenny** (00:35:07):
So you're talking about pricing testing and I was going to ask what tools you found that are useful for testing pricing. And that's probably a good segue to talking about the modern growth stack. Would that fit into this concept of modern growth stack, testing your pricing?

**Naomi Ionita** (00:35:21):
Yeah, let's do it.

**Lenny** (00:35:22):
Okay, let's do it. So just to set it up, there's this term modern data stack that I think it'd be useful for you to explain because not everyone is aware of that, and you've kind of been thinking more about this adjacent idea of a modern growth stack. So can you just talk about these two things, and then we'll lead to some questions there?

**Naomi Ionita** (00:35:37):
So the modern data stack is basically a collection of cloud native tools to more easily move and manage data. It consists of a fully managed ELT, data pipeline, a destination for that data. So a cloud-based data warehouse, like a Snowflake or Redshift, data transformation tool like DBT, and then finally a platform for visualization on top, so people can access the data. The play on modern data stack was very intentional. I think of the modern growth stack, or my core thesis area right now at Menlo, as the evolution of what you do with the data. So these are the workflows that the data enables to drive the business forward for product growth and revenue teams like I used to run. It's the modern replacement for infrastructure that teams like mine built or bought. When you're responsible for driving things like activation or monetization or retention, there tends to be a lot of these internal tools that are built because you're really powering cross-functional teams to do this work. It's not mapped easily into legacy departments.

**Lenny** (00:36:39):
Awesome. And the general idea here is, there's so many more tools now to help you grow with the data stack. There's just all these tools now that make it so much easier to collect data, use data, make decisions off data, and you're finding the same things happening with growth. What are some of the tools that you found to be super helpful? I know you're an investor in some, you're not a investor in others. It'd be good to just talk about, here's just like a bunch of cool tools and how do they fit together as much as possible to help you grow your startup.

**Naomi Ionita** (00:37:05):
And I want to reinforce some different themes before I get into some layers of the stack because I think it's important to frame the benefits of the modern growth stack. So one is data, two is workflow, and three is impact.

**Naomi Ionita** (00:37:18):
So starting with data, the modern growth stack companies really are powered by these smart integrations and the automation that you get as a result. So with this proliferation of SaaS, it's created this need for more data access and interoperability. We've all felt that pain of siloed data. Modern growth stack companies leverage reverse ETL companies, like Hightouch or Census, to break down these silos and help companies, or employees across the company, access data and be more productive. So that's a big data theme with modern growth stack companies.

**Naomi Ionita** (00:37:49):
The other theme that they unlock is around workflow. Here, it's really the enablement of people and process. So rather than employees sitting in their departmental silos, modern growth stack companies build bridges between them. So by unlocking data access, the business side can often self-serve and be more self-sufficient without relying on an engineer or a data scientist to run queries or stitch together data sets for them.

**Naomi Ionita** (00:38:16):
The other thing here is lots of growth work is inherently cross functional. So the efforts to drive growth requires new tools and collaborative workflows like we're discussing. Without purpose-built software, many teams like mine felt no choice but to build in-house. So we spent sacred hours building and maintaining tooling for experimentation, personalization, billing, monetization. These were resources that could have been reallocated to building proprietary features for the business had we been able to buy something purpose-built.

**Naomi Ionita** (00:38:50):
And finally, these products really drive impact. So the idea here is driving hard ROI in the form of cost reduction. So automation means time savings, and oftentimes, that can be mapped directly to cost reduction for a company. But they also help product and growth and go to market teams better engage and monetize customers. So they're driving hard ROI in the form of revenue impact too. I'm really compelled by companies that can drive hard ROI both across cost saving and revenue generation. And I think that ROI story is even more compelling now in a softer macroeconomic climate. You just have to be able to continue to retain sales and pricing power, and I think that's derived from a strong ROI story like I described.

**Naomi Ionita** (00:39:35):
So those are general themes and consistencies across the companies that I get particularly excited about. So happy to talk about a few layers in the stack, and I think you might be familiar with a few of these as well, especially based on your growth background at Airbnb and tools that you probably build yourself.

**Lenny** (00:39:54):
Yeah, exactly. That's what I was going to say, that so many of these things are just coming out of startups that have built these in-house. And then they're just like, "Hey, I could start a company doing this and provide it to all these other companies." And so I just love that there's all these tools coming out that just make it easier to build startups and grow startups, and do less work, and have less people. Just reminds me of the number one app in the App Store at this point. I don't know if it still is Gas, which is just like four people, and it's higher than TikTok and YouTube, and all the things, and Facebook, and it's four people. And so it just shows you the power of what tools can do for you to build new startups and disrupt people, and companies that have been around for a long time.

**Naomi Ionita** (00:40:33):
And you have to help companies do more with less now. There's a lot of frozen budgets and that's a good way to break through. So I love that these companies can do that for the buyer.

**Naomi Ionita** (00:40:44):
So one that's come up a bit and gotten a lot of airtime recently is product-led sales. This idea of companies that serve PLG businesses and harness the power of all that product usage data to inform the customer facing team around which accounts are most upgradable. It's really free money when you shine a light on an account that nobody was paying attention to and some inside sales team can drive a large account expansion. So I don't know what better ROI you should get than that.

**Naomi Ionita** (00:41:14):
And there's a bunch of companies that are doing this. Endgame happens to be one that I work with. They have customers like Figma, Loom, Calendly. There's other players too. I think Pocus has done a phenomenal job of building content and community to help inform the market around the power of product led sales. So there's just a lot of goodness about all the players in this space really waking everyone up to this opportunity of layering on sales to a product led motion and how to maximize revenue along the way.

**Lenny** (00:41:45):
I'm an investor in both of those actually, and I'm going to, just in the show notes, note the one I'm an investor in because I'm investor in a lot of these companies, it turns out. And we've invested in a few, so I'm just going to keep it simple and I'll write in the show notes. Here's ones I'm an investor, just to avoid.

**Naomi Ionita** (00:41:59):
I love that. Double- dipping means you're a believer in the category as well.

**Lenny** (00:42:03):
I am.

**Naomi Ionita** (00:42:00):
... tipping means you're a believer in the category as well.

**Lenny** (00:42:03):
I am. I love it. There's so much school stuff happening there and I'm really excited. Yeah.

**Naomi Ionita** (00:42:08):
Yep. Cool. I think another layer in the stack is experimentation. So this is really critical infrastructure, in my opinion, for these cross-functional product data growth teams to A/B test hypotheses and understand their impact on the business. How do you know if you make a change in the product or your pricing, whether you succeeded or failed without having infrastructure like this along the way? Category creators like Optimizely really paved the way. I was an early buyer of Optimizely and they targeted marketing personas, and it was just game changing to be able to start to A/B test things and bring hypotheses to life.

**Naomi Ionita** (00:42:44):
I'm also biased as an investor, but some of the modern tools here, like Eppo, which offers experimentation for the modern data stack. So unlike Optimizely, which focused on more kind of click through metrics, Eppo ties directly to the metrics in your data warehouse. So tying an experiment result to things like subscriptions or revenue or margins, really like board level metrics that you're trying to move. They make that full trip really convenient and understand the impact on those business KPIs directly. So it's a lot of automation around the experimentation, results. And analysis they used to live off to the side in Excel or Jupyter Notebooks now is automated away with Eppo. I think you're familiar with that one.

**Lenny** (00:43:29):
Yeah, we definitely didn't plan this, but Eppo's both a happy sponsor of this podcast. I'm also an investor in Eppo. Go Eppo, but this was not planned.

**Naomi Ionita** (00:43:38):
Well, this is Airbnb roots. [inaudible 00:43:41].

**Lenny** (00:43:40):
Love it. It is. Yeah. It's my colleague.

**Naomi Ionita** (00:43:42):
[inaudible 00:43:42] was an early data scientist at Airbnb.

**Lenny** (00:43:45):
Exactly, I worked with him at Airbnb and he was amazing and I had to invest in anything that he built. He built an awesome thing.

**Naomi Ionita** (00:43:49):
Yeah, but exactly like you describe, I love these founders that have steep authenticity around the problem because they built it internally and now they're commercializing it for the masses. And so the story of chain Eppo is a good one on that dimension. And there's other players too. I'm also a big fan of Amplitude and a buyer of that tool as well, and I love a lot of the team there. So if you do not have a data team or a data warehouse and you still want to leverage being able to do behavioral kind of ad hoc analysis or experimentation, that's a great tool for you as well. So a lot of different ways to solve this problem in the market.

**Lenny** (00:44:22):
Also, a happy sponsor, go Amplitude.

**Naomi Ionita** (00:44:25):
Cool.

**Lenny** (00:44:26):
I love it. This is great. Hitting on all my favorites. Okay, let's keep going. What else have we got?

**Naomi Ionita** (00:44:32):
Well, I talked a lot about billing and monetization, so I'd have to talk about that one. I think platforms for managing, billing and iterating on your pricing and packaging, this is just such a big need. I think these will transform business models. For SaaS in particular, most companies have been seat-based like we described, so the historical incumbents like a [inaudible 00:44:54] really serve that model. But in this shift to more usage based, there's new entrants that are servicing companies in that dimension. And there's also lots of sort of clunky workflows when you think of bridging from engineering to product and growth to finance or RevOps.

**Naomi Ionita** (00:45:11):
So there's a lot of just streamlined workflow that these new tools can offer. Some early breakout players in the world of usage-based billing are Metronome and Orb. There's also more room to handle the full monetization infra-layer. So for example, I like how Orb marries the billing component with the data infrastructure to actually inform what your pricing and packaging iteration should be and help you forecast and optimize revenue. So there's other players that are doing different components from this journey of the metering piece all the way through to the experimentation piece, and it's been really, really fun to get to know players in that space. And I wish I could have been a buyer of them many moons ago.

**Lenny** (00:45:57):
Not an investor in these yet. And so that's cool. Quick tangent, do you have a strong opinion on pricing models, usage based versus seed based versus something else? What's your guidance to founders? Is this the way to go, usually one of them, or is it super dependent? What do you recommend?

**Naomi Ionita** (00:46:12):
Yes, this is a similar answer I had before. I don't think that they're mutually exclusive. And so if you look at all the companies that in different pricing models in SaaS, a small sliver less than 10%, around roughly 5% have just pure natural escalator kind of usage-based model. The vast majority have a hybrid approach. And so what I mean by that is they're typically some good, better, best subscription model where there's some consumption component across each tier, like some quota limit for your given value metric. So in Slack there might have been number of messages sent or Dropbox number of terabytes of storage. Invoice2go might be number of invoices. There's some dimension that's been sort of packaged in with a given pricing plan, and once you reach that limit, it is a trigger to get you to upgrade to the next plan over, or sometimes there's overages that you can pay for.

**Naomi Ionita** (00:47:02):
So I don't believe that you should just be seat-based or just be usage-based. I think one challenge with purely usage-based models is that's not always how CFOs want to buy. I think buyers sometimes want predictability. They want to be able to budget for your tool, and I've lived that. I remember using tools like Mixpanel and Segment and even Jira to an extent where I was paying a cheap amount to get going, and all of a sudden I realized we had grown quickly and I looked at all of our SaaS spend and I was blown away by how much more we were paying. So it's the other side of this... I'm advocating for people getting paid and compensated for the value that they're delivering, but there can be a breaking point. And so how do you think about packaging a fixed and variable component so that people can more predictably buy your software?

**Lenny** (00:47:48):
Any other layers of the stack that you want to touch on slash which would you be most excited about in the future? Do you think people should be paying more attention to that maybe they're not paying attention to?

**Naomi Ionita** (00:47:57):
I mean, I wouldn't be doing my job as a VC if I didn't mention Generative AI right now. It's really having a moment. So there's a bunch of breakout applications there that sit within this theme of the modern growth stack. When you think of using AI to create images or text or code or audio or video, these capabilities change the way teams work. So writing a blog or writing copy for an ad, SDR is doing their work and can outbound sales efforts. There's just a lot of these touchpoints where it's humans kind of tinkering and iterating and laboring over every word. And if the machine, if AI can tell you what's going to be a more performant version of something, that's a very, very hard ROI exercise there. You save time and hopefully you've improved your performance across the various marketing or sales campaign.

**Lenny** (00:48:48):
Where do you think AI will be the most help on growth in terms of growth? Do you have an idea there?

**Naomi Ionita** (00:48:54):
I think what I described around marketing and sales, just because they really touch the dollars. It can be this ROI story around saving time, but also driving revenue. There'll be plenty of really effective examples within things like customer support. I mean the cost savings potential. There's going to be massive. We'll see what happens in engineering, which generating code. I think there's a lot of areas where it is going to touch the enterprise, but from a modern growth stack standpoint, I think something that's really revenue generating and can point to attributable ROI on that dimension is going to be pretty relevant to where I'm spending time right now.

**Lenny** (00:49:32):
I'm excited. Any last thoughts before we get to a very exciting lightning round?

**Naomi Ionita** (00:49:37):
I'm happy to hand it over to the lightning round here.

**Lenny** (00:49:40):
Well, we've reached the very exciting lightning round. I'm only going to have four questions for you. I'm going to ask them pretty quick. We'll go through them fast, whatever comes to mind. No pressure. Question one, what are a couple books that you've recommended most to other people?

**Naomi Ionita** (00:49:56):
My buddy Madhavan from Simon Kucher's wrote a book called Monetizing Innovation. This is a great read. He and others there have done pricing engagements with hundreds of tech companies, so there's a lot of stories and practical tips there. I often gift that one to founders, so I can't do this whole talk without giving a nod to my friend, Madhavan, and his bible.

**Lenny** (00:50:19):
Awesome. I just recorded an episode with Madhavan, and so that's a great pick. Question number two, favorite recent movie or TV show that you really enjoyed?

**Naomi Ionita** (00:50:28):
I have little kids, so I don't know if this is going to be as interesting for folks, but we like Story Bots on Netflix. They're these little cartoon characters that answer kids questions. So people sort of call in and ask questions and they do a whole episode on why is the sky blue? How do airplanes fly? How do I see? And I inevitably learned something from watching those. So those are very kind of playful and educational shows. I critically need a new-

**Lenny** (00:51:00):
No, those are... I don't know the answer to any of those questions. I need to watch this. Okay, so question three. I'm looking at my notes and I've never asked this question before, so I don't know where this came from, but I love it. Who's been the biggest inspiration to you in your life?

**Naomi Ionita** (00:51:14):
I mean, this one's pretty easy. For me, it's my parents. They're from South America originally and lived on three different continents before immigrating to the US for graduate school. It's a pretty cliché American dream, but they came here with nothing. Just this idea of building a family and taking advantage of the educational and professional opportunities in America. They progressed through school and building their career in three different languages with no financial support, no entrenched kind of resources or networks to lean on, and I just can't imagine doing that. Just the stress or cognitive load of kind of restarting your life in whole new geographies and cultures and languages and just betting on yourself and figuring it all out along the way. So my drive has always been rooted in their story and I'm forever indebted to them.

**Lenny** (00:52:03):
I need to ask this question more often. That was an amazing answer on the spot. Naomi, we have reached the end of our chat. Two final questions. Where can folks find you online if they want to learn more, maybe pitch you startup ideas, contact you if they want to ask you questions, and then finally, how can folks be useful to you?

**Naomi Ionita** (00:52:23):
I'm a partner at Menlo Ventures, so you can find more about me in the firm at menlovc.com or else on LinkedIn or Twitter. My DMs are open.

**Lenny** (00:52:33):
Amazing. Naomi, thank you so much for being here.

**Naomi Ionita** (00:52:35):
My pleasure. I look forward to talking to more folks who are building things across workflow automation, data AI, and the modern growth stack. So thank you. It's always a pleasure.

**Lenny** (00:52:48):
All right, DMs are coming in as we speak.

**Naomi Ionita** (00:52:50):
Thanks, Lenny.

**Lenny** (00:52:53):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [4/22] What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess)

**John Cutler** (00:00:00):
Let's say you're a founder and you're trying to decide, should I invest more on processes, or should I invest more in people. The first thing is introspection. What do you believe in, really? What do you believe in, and what do the people around you believe in, and how can you be a coherent leader? And you know what? You can nudge yourself a little bit away from your happy plate, but you're not going to go super far. You're not going to go from like a process-driven meritocratic, X, Y, Z person all the way to like I'm going to start a collectivist company where everything is sort of a consensus decision to do that. You're not going to do that. But I think it starts with self-awareness and then that's how people form their authentic leadership vibe, and then they flex a little bit and then they embrace other perspectives.

**Lenny** (00:00:49):
Welcome to Lenny's Podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products. I interview world-class product leaders and growth experts to learn from their hard-won experiences building and scaling today's most successful companies. Today my guest is John Cutler. John is one of the most prolific, beloved, and longtime writers and sharers of product wisdom online, and as you'll hear at the start of this episode, thanks to his really unique role at Amplitude, he's worked with a large percentage of product teams and product managers around the world. I've learned a lot from John's writings over the years and share his stuff often, and so it was a real honor to chat in depth with John. I anticipated this would happen and it happened, this ended up being the longest episode I've done yet, and honestly, we could have kept going for a lot longer.

**John Cutler** (00:04:21):
Yeah, thanks for having me, Lenny.

**Lenny** (00:04:23):
I kind of know you as John Cutler. I feel weird to call you just John. Do you find that to be true, and also do people call you John Cuttlefish because of your Twitter handle?

**John Cutler** (00:04:32):
Yeah, John Cuttlefish. There is this, I learned yesterday, there's a DJ, a famous DJ called Jon Cutler without the H, so I don't know if are people into house music knew that. Yeah, I think usually it just, like most Johns, it forms into Cutler or JC or something like that, but just John is good, yeah, for now, or Cuttlefish, you could just call me Cuttlefish. That'd be fine.

**Lenny** (00:04:51):
You said that actually, we were talking before this, you said you do some music, so is that DJ actually you?

**John Cutler** (00:04:57):
No, but that would be really funny. In fact, the person yesterday who reached out over Twitter said, "Dude, I don't know what you're doing now in your career, but I really like your earlier work." But that would've been pretty cool to be Jon Cutler, the DJ. I wrote songs and played rock music and stuff, not like a house DJ.

**Lenny** (00:05:15):
Okay, this could be the next phase of your career which we'll talk a bit about. But let me just say that I'm so incredibly excited for this conversation. I've been hoping to do this for a long time, and now that you're between gigs, we finally found an opportunity to do this, and I just have a feeling this is going to be one of the longest episodes we've done because there's so much I want to ask you, and there's so much interesting stuff that you've had access to and that I think that you can share. So, I hope you're ready for potentially a marathon of an episode.

**John Cutler** (00:05:40):
Sure, yeah, I'm ready. This is exciting. I'm on vacation now between jobs, so this is the highlight of my day. We can go all day if you want.

**Lenny** (00:05:47):
All right. Eight hours. Let's do it.

**John Cutler** (00:05:49):
Terrific.

**Lenny** (00:05:50):
So, I was thinking that we start with a little bit about this unique role that you had at Amplitude which you just left after about four years, and what's most interesting about it is it give you access to an incredible number of product teams and product managers, unlike anything else I've seen or any other role I've seen before. So, could you just talk a little bit about this role that you had at Amplitude, and what it was like to work with so many product teams and so many product managers?

**John Cutler** (00:06:16):
Yeah, absolutely. So, first off, I remember almost specifically the day that Sandhya from Amplitude reached out and was sort of floated this idea of this role to me, and I'm so grateful for Sandhya, and Justin, Matt Althauser, Spencer, the whole team, because it was really, it was really kind of a weird role from the beginning. They were starting to get more and more customers who were not traditional startups or kind of growth stage startups showing up, and they needed to figure out how to convey expertise and convey things to the broader product public in a way that would land with those companies, right? I guess, kudos to them thinking this weird idea could work. So, I'm really, really grateful for that.

**John Cutler** (00:07:06):
But yeah, my official title was product evangelist. I don't think that I super fit that role, but that was the title that we had, and basically my job was to wake up every morning and do things that would overlap Amplitude the product, but then help uplevel our customers, sort of uplevel the broader product community. I call them current customers and future customers. That's how I woke up every day, I'm either talking to a current customer, I'm talking to a future customer. This product transformation's happening all around the world, just means it's a matter of time, eventually they'll become Amplitude customers, so I should just try to make them awesome and try to help them with different expertise.

**John Cutler** (00:07:46):
But my day-to-day was spent a lot advocating for different ways of working, doing coaching, doing workshops. I wrote the North Star Playbook in partnership with Jason who was a co-writer with that. We did a lot of one-to-one coaching sessions. I had these things called product therapy sessions when I would just wake up in the morning and just kind of soak in whatever problem people were having for the day. I did meet with hundreds and hundreds of people and did workshops for thousands and thousands of people and talks for more than that, tens of thousands, really, in terms of the talks. So, it was just a, yeah, crazy experience doing that. So, the technical details is I predominantly reported into marketing and product marketing, and then I did a stint actually where I was on our product team as we were sort of getting our education efforts going, ultimately we moved that over to customer success, and I went back to marketing. So, that's the technical side of it, I reported into marketing.

**John Cutler** (00:08:45):
But I do remember the day I arrived and probably a couple weeks later, we had our all hands annual kickoff, and there was a big presentation about our goal being the trusted expert, and that still resonates with me the whole time I was there that an evangelist is there to help uplevel the world with trusted expertise, and in a product like analytics product, there's the product analytics, but then there's whole other ways of working that overlap that. So, yeah, generally that was my role. It kind of is a crazy role, for sure.

**Lenny** (00:09:16):
That is wild. You're basically like a free product coach for product team. You just come in, help them uplevel the way they build product, and then Amplitude becomes... You need to figure out how to work with data, Amplitude can help you be more data informed. I imagine that's kind of the general idea.

**John Cutler** (00:09:30):
Yeah, it's funny, I joke with our professional services team. I mean, so if you're a SaaS company, I think sometimes you have a professional services team. At Amplitude, especially the way that we saw that is companies put money in and that sort of creates skin in the game. They're really paying you less for the professional services and more for the accountability and the access to the expertise. So, I would joke with Jenna from that team that maybe we should have monetized all these workshops. I know Gibb and other people, they're charging a good chunk for North Star workshops and here we were just kind of doing them for free.

**John Cutler** (00:10:04):
So, ultimately, maybe there was another strategy there, but that we did those generally for free, and sometimes I kind of stuck my foot in it. In the middle of the pandemic at one point we were like, "What are we going to do? We can't travel for workshops." And I would put in my newsletter, "Hey, anyone want a workshop?" And then suddenly, our sales team, we had to grapple with what are we going to do with these 120 leads, how are we going to work with them. It was funny having to deal with it.

**John Cutler** (00:10:32):
But yeah, in general, this is a unique role. I would definitely consider a SaaS company's think about a role like this, but it's really nuanced. We can share some links later as I reflected on what we did right and wrong, but ultimately, I think you shouldn't rely on individual people. You should think of evangelists as almost like concentric circles of your community and some people who just happen to have more expertise. Look, our internal team's amazing, Ibrahim, Justin, and Abbie, and when Sandhya was at the company, and just, everyone's an advocate. Everyone's a potential evangelist. It's just that there's only so many hours in the day. So, you could think of your community as just these concentric circles of evangelists and advocates. It's just like how you design it right that does it. So, yeah, recommended. It's a little tricky, but yeah, it was a cool move to do.

**Lenny** (00:11:19):
That sounds like a future post, how to do this in a different way where they don't have a John Cutler in place. You said you worked with hundreds of teams. Maybe just give us some numbers roughly of how many companies have you worked with, how many product managers do you think you've spoken to in this career.

**John Cutler** (00:11:32):
Oh geez.

**Lenny** (00:11:33):
This phase of your career.

**John Cutler** (00:11:34):
So, I think I did it... There might have been over the four years, maybe 800 one-on-ones, individual leader one-on-ones. I'm thinking it was at the peak, it was in one year's 150 workshops and then overlapped in the next year, then between 200, but mostly the average maybe let's say three or 400 workshops, a hundred a year. It's heavy. And then there was these just general conference talks and other things that we're doing. I tried to total, I exported all my Google Calendar invites, I tried to categorize all them at some point, but really also you have to think about it is that what we did with the North Star Playbook, it was truly a team effort at Amplitude.

**John Cutler** (00:12:19):
We started to have our, I think it was Sandhya who needed to like, we had three days to go in to close a customer and they were looking for us for trusted expertise, and she pulled together this workshop and she came up with these three games of product which is a really tricky and cool way to describe how your North Star inputs and North Star should be, and it started this ball rolling, and then they wrote a blog post about it.

**John Cutler** (00:12:42):
So, if you search North Star, you get to Sandhya's post. It's an amazing post, and then our CSM started to learn how to do it, and then we were like, "We should write a playbook for it." And then it got to the point where if you go on LinkedIn, people are like, "We used," and I made a whole point of saying we did not invent this thing, but people will say, "We use Amplitude's North Star framework," and I have to always chime in, like, "No, we did not invent that thing. You should go to Sean or you should go to any of these people who've done it in the past." But yeah, the whole point is that a lot of this stuff was evolved over time. It wasn't just some snap marketing campaign to do it.

**John Cutler** (00:13:17):
Same thing are our retention playbooks and engagement playbooks. When I arrived at Amplitude, people would send pictures of those playbooks sitting on their desks and people thought, "Oh, it's just this piece of marketing content. How did they pull it together?" I did some research and our CS team developed 110-page bulk of research from working directly with customers around retention engagement, then we had a PM and a great content writer, Archana, zero in and kind of make it palatable, then we did ARC for it. So, it didn't just magically appear. People think that these artifacts that Amplitude has just magically appeared, but they were just... It's a company filled with passionate experts of these things, and it was like tested, iterated, tested, iterated, expanded, tested, put into motion, put into practice, and that's how you create these kind of franchise cornerstone pieces of content for your company. You don't just snap your fingers one day. So, anyway, I wanted to point that out. Huge group effort for all these things.

**Lenny** (00:14:22):
How does it feel to have left Amplitude at this point? I imagine you're going through some rollercoaster emotions.

**John Cutler** (00:14:26):
Oh geez. Well, the immense amount of gratitude, definitely, mention that, wonderful people, wonderful customers. Just imagine like if you're a product nerd, one day you're with Amazon, one day you're with Ikea, one day you're with LEGO, one day you're with Intercom, then you're with a two-person startup, and then you're with Figma. So, really, once in a lifetime experience to be able to do that. In fact, if I had been a paid consultant, I never would've been able to do that. Another thing too is that there's this sort of selection bias. If you're a consultant, people come to you to work with you, but often I just had to talk to whatever team wanted access to expertise at Amplitude, not necessarily me. So, I didn't get to dictate A lot of times the conversation. It's like, shit, I'm not doing a very good job here. This person thinks in a very different way to do that.

So, yeah, a lot of gratitude. I would say it got really heavy a lot in the sense that my son was born, three months later, I start the job, and then the pandemic kicks in, and every day you're absorbing just attention from teams. You're meeting leaders who are about to leave. Five days later, you're meeting people who are trying to save their team from the pandemic, imploding everything they're doing. Yeah, I'm joke about the product therapy thing, but I would finish the day at 2:00 or 3:00 and then have to do another one. Wake up at 5:00 to do an EMEA workshop, 5:00 to 7:00, be two in workshop, then take a break, then do another two-hour workshop, and then talk to a leader about how everything was going to explode, and then another leader. And then I was still on a team in Amplitude, so I might go to my own meeting where we're working through our own challenges, and then it's 4:00 or 5:00 in the afternoon. I'm done. Oh, to be able to do that.

**John Cutler** (00:16:16):
And then I think it also left me with a couple key lessons we could probably go into later when we're doing it. One, you are talking to a bunch of different companies, achieving the almost similar results in very, very different ways. They behave in different ways, the context in the pandemic or the economy. You would see the pandemic kick in and then you would talk to 50 companies that were dealing with the ramifications of it. So, it's kind of funny, I joked with someone at Amplitude, they're like, "We were going through our own shit," and I'm like, "Yeah, and I've seen how 50 other companies are going through their own shit," where this is you're doing it. So, the power of context.

**John Cutler** (00:16:52):
The regional differences were so fascinating. I was on with a teen that was based in India and just the passion and curiosity. There was not one jaded person in the room. There was not one person like, "Been there, done that. When's the performance review cycle ending?" or anything like that. It was just all-out passion and hunger for information. So, those days were amazing. So, yeah, you talk a lot about it, but it definitely, it feels like a relief in some ways because the amount of tension to do it. And so, for my next plan actually what I'm doing is I'm going to work at Toast in a couple weeks, and I've been in touch with a leader there, Craig Daniel, for a long time, kind of really liked what he did at Drift.

**John Cutler** (00:17:40):
But I think that what I realized over the course of these four years is that I wanted to pivot back to help put most of my energy into helping my own company. They're growing super fast, so the numbers are in the hundreds of everything or in the thousands of everything, and they're not just the POS business. They've got these different businesses, like guest services and back office stuff and things. Amplitude is a super horizontal, if you think about it, it's almost like a diagonal, and so it made your head spin, and I kind of wanted to go back to a vertical SaaS. There's a company here in Santa Barbara called AppFolio that I like working at, and I really had a soft spot for vertical SaaS, but I'm thinking put my energy into an internal team for a little bit to pivot back into that. And so, I'll be helping enable product teams and sort of doing what I was doing, but within a company as well. So, it's going to be an interesting shift.

**Lenny** (00:18:29):
You touched on so many topics that I want to dig further into, and you also talked about where you're heading next, which I was going to ask, so that's great. Thank you for covering all that. By the way, I was just going to also say, lucky Toast, wow, to get John Cutler. Go them.

**John Cutler** (00:18:42):
Oh, lucky me. I mean, Jesus, Toast is this gem. I just was joking with Craig the other day. I was like, "I did not know all that stuff was going on at Toast."

**Lenny** (00:18:52):
Awesome. Okay. So, before we dig into some of the stuff that you brought up like cultural differences between companies, what the best teams are doing differently, things like that, I actually, and you noticed, I asked on Twitter what I should ask you. You have a lot of fans on Twitter and there's a ton of questions, and one actually got pretty spicy and I want to touch on it briefly. This guy, Jason Cohen pointed out that a lot of the stuff you share online in your newsletter and tweets and things like that, it often doesn't have a clear recommendation of here's what you should do or concrete piece of advice you could take away. It's kind of messy which is appropriate because your newsletter is called A Beautiful Mess. And so, my question to you is why have you found that you like to embrace the mess in your writing and your thinking and your advice?

**John Cutler** (00:19:38):
I was reflecting that the newsletter, it's almost like an emo band, The Beautiful Mess, it's so angsty. It couldn't have been more... If I had a band, I did not have an emo band when I was 16, but if I did, I would've called it The Beautiful Mess. So, it's probably pretty consistent with personality to do those things. I mean, I actually really appreciated Jason pointing that out, and in fact, at the end of this year, I put this post out to people saying, "Hey, here are things I'm grappling with, like the actionability of the content that I put out there, diversity of product advice, it's important to me," and then what it's like to just be a weirdo. We all have our weird freak things to do these things. And so, what does it mean to embrace those things? So, it was really timely I thought that Jason put that out there, and so maybe I'll give a little background about the newsletter and what I was looking for that.

**John Cutler** (00:20:29):
And so, I think that the first thing that I did was four years ago, I kind of scanned the product advice landscape and I noticed three things. First, there's sort of three perspectives that pervaded, and again, I just want to make a huge caveat, this is not a judgment on any of these particular perspectives. It's more like I noticed a lot of it. And the first was that to be successful, number one, maybe success is tools, skills, mindset. So, that's kind of one group of particular things. The second that in terms of worldviews, we mentioned international worldviews too, but there was a high percentage of product advice that was kind of grounded where you think it would be grounded. So, it was grounded in this idea of meritocracy. Success is primarily about merit, very highly individualistic, and we don't realize that in the US until you do meetings with other teams, just how individualistic we can be when it comes to how we think about teams should be set up and stuff.

**John Cutler** (00:21:28):
And then I think the third thing I realized was that it was very often very context free, and I mean that actually in the nicest way. It was optimized to make sure that it could be actionable, that someone could take that away. That's what I really like about the content that you put out there, and I like about a lot of the guests on the podcast. They kind of lay it out in those particular things. And so, to kind of go through, yeah, those tools, skills, mindset, that makes sense, right? Who does not want tools to be better? In fact, a lot of the podcasts I like, we can get into that later, are like, "We're going to give you the tools and tactics that the best people do." So, I really like that kind of stuff as well.

**John Cutler** (00:22:04):
The second part of that is this idea of success be mostly about individual skills in jobs. So, this idea of great leaders, high performing teams, 10 x people, kind of go on and on. And then the product mindset stuff which is a little bit like you have it or you don't, or you develop or you don't. It's very mysterious. So, again, I'm going to go through these things and then think about how they inspire me. Part of me was like, "Okay, there's a lot of that stuff, but maybe not as much stuff kind of unraveling the dynamics that happen behind those things."

**John Cutler** (00:22:36):
So, the meritocracy stuff and the individualism stuff, it's basically the people rise to the top, they try the hardest, they work the hardest, the best in companies employ them. There's top tier companies, there's second tier companies. So, there's this very hierarchical view, and as I started to also dig in more into the stuff in Amplitude, I was like, "Wait, there's something right and wrong about this at the same time, there's something true but not true at the same time." So, that's something that I wanted to be able to explore in doing it. And then the context free advice was obviously I noticed more and more that people trying to put tools in play out of context sometimes had worse effects than them just not doing it at all to do that.

**John Cutler** (00:23:18):
So, anyway, I kind of thought about it as a product, like, "Okay, what's my opportunity here? There's a lot of this great advice. It's very actionable. I don't know. In the US were pretty individualistic, so the advice probably lands with people really, really well, and then also it's really actionable," and said, "Okay, well, what would be my particular angle?" So, I thought about the angle, about wanted to explore three things. I think the first one is this idea we do work in these complex adaptive systems, and so I really went deep in that particular area.

**John Cutler** (00:23:47):
So, we work in environments. There's lots of things that are interdependent on each other. We don't work in closed systems. I mean, if you're in the Bay Area, you're in this broader system called the Bay Area that's in this broader system called California that's in this broader system called the United States. Your team is in a team of many, many teams in your company. The systems are non-linear. The bird flapping its wings in Brazil creates the tornado type of stuff. And so, I wanted to make sure that we got dug into that particular stuff in The Beautiful Mess stuff.

**John Cutler** (00:24:21):
The next thing is that I'm a sucker for weird counterintuitive dynamics in companies. I don't know what it is. I absolutely love that. And so, maybe I'll give two examples. One, I'm obsessed with this idea of high work in progress, from a human level and a team level. How even though we know that if you try to do less at once, you'll be more effective, teams routinely just load themself up with work? And so, in the newsletter, I wanted to explore stuff like that, like why, when a bunch of people know irrationally that you should not load yourself up with work, why do really, really smart, capable, intelligent, passionate people in their personal lives and on their teams just load themself up with work? What are they optimizing about? So, that'd be like one example of counterintuitive stuff.

**John Cutler** (00:25:09):
The other stuff is strategy stuff. Every company has these three pillars, and it seems really smart for the CEO to have this really clear three pillars, but then everyone walks away from the meeting and be like, "I don't know what we're with doing." That's another example of a counterintuitive thing. So, that was the second thing, the counterintuitive stuff. I love the complex stuff. And then frankly, I think the other thing is I just wanted to help people who are weird like me do those things. So, I would say I'm really, really triggered. People will say, "But it's probably triggered by Jason." He said, "Why? Bring solutions not just problems." That's my krypton, right? I like the systems thinking stuff. I like all that. So, anyway, long story short, wanted to help people like me. I like the complexity stuff. I like all these weird counterintuitive dynamics. And then I thought that there's a lot of representation for the very deterministic advice that people have.

**Lenny** (00:26:02):
That's a really good explanation. There-

**John Cutler** (00:26:00):
... advice that people have.

**Lenny** (00:26:02):
That's a really good explanation. There's a piece of what does the market want and let me deliver it, and then there's a piece of how is my brain working?

**John Cutler** (00:26:10):
I love the fact that people scan the market and say, "People want to know about prioritization and so I'm going to tell the world about prioritization." I really like that. In fact, I admire, I'm jealous of people who can produce that kind of content realistically. Interestingly enough, probably in my doodling in post I've probably given frameworks to do that. I just don't think too much about it. I just kind of go in these things. There's always this balance and one way that I think about is to get anything done, we need to reduce the world a little bit. That's the difference.

**John Cutler** (00:26:41):
Back to this thing of complex problems, I think it's the difference between oversimplification and focusing. You can have a really complex problem and you can oversimplify it and that's not great, but you can have a complex problem and be like, "You know what? I need to hold some things constant." Not going to make any progress unless we hold some things constant to do that. That's, to me, the balance I'm playing all the time between how many variables to hold constant to make sure that people can get some value out of it. I don't know about you, but that's the tension I have. But you write really actionable stuff and so I really admire that too. I'm jealous.

**Lenny** (00:27:15):
I try, but then I'm jealous of always having to nail it down to something very concrete and simple. This last post actually was a little bit of an balancing act where I wrote about how virality is mostly a myth, and I added the word mostly to it at the end. Then I was like, "Should I just go for it and be like virality is fully a myth?" But no, it's not actually, so I can't really go that far.

**John Cutler** (00:27:35):
See, it's kind of messy.

**Lenny** (00:27:36):
It's kind of messy.

**John Cutler** (00:27:38):
I love that. In the spectrum of advice, every post of mine will say mostly, maybe, it depends, so we all have some opportunity to flex into the other direction.

**Lenny** (00:27:49):
Shifting a little bit, coming back to just the bigger picture of John Cutler, you've had more exposure I think to product teams and product managers, you're definitely in the top 1% of people that have talked to and met with and seen what happens within product teams. There's a lot of stuff I want to dig into there and the first is around what you've found differentiates the highest performing teams. Let me just ask you this very succinct question and see where it goes. If you had to just boil it down, what have you seen most differentiates the highest performing product teams?

**John Cutler** (00:28:26):
First of all, they're top 1%, they're super, super productive, they can levitate, they can do ... they have no emotion. No, I'm just kidding. No. Okay, this is my tack for answering the question. First of all, I have this friend Josh Arnold and he had this great principle that held true in my experience talking with teams and he calls it the reverse Anna Karenina principle. In Anna Karenina, Tolstoy is basically the like, "The dysfunctional families are all different and the happy families are the same," and what he said is it's the reverse of that with product teams, that actually the dysfunctional companies are all the same and then the happy companies or the higher performing companies can be very, very different.

**John Cutler** (00:29:07):
That's something that stuck with me because either you have easy to identify anti patterns, and I'm going to admit earlier in my career, maybe five or six years ago, my content was about identifying things that people would be like, "How did you know that was working in my company?" and I would just be like, "Well, I just know." Even Spencer and I had this thing. I put something on Twitter and Spencer writes me, he's like, "John, is this about amplitude?" and I'm like, "No man. It's like that Carly Simon song, Spencer. You probably think this song is about you, but it's not." It just is. It's just like those things. Either you have the very easy to identify anti patterns or you have the high level principles, like you must trust each other or you must do something like that.

But the way that companies achieve those particular high performing things can be vastly, vastly, vastly different. Let's just start with that as a basic thing, which is one reason why it makes me hard to answer the question. A great example here is great product leadership. We need great product leaders. But you meet [inaudible 00:30:11] product leaders and you see that some people are these humble, curious servant product leaders. They're not really talking a lot and they're just growing the system that way. You know what? There's other companies with really successful people that are just badass, strong, dominant, they like to spar. I need people who can spar with me. That's just one potential example there of okay, you meet enough teams and you see that there's many ways to achieve great leadership [inaudible 00:30:41] example.

**John Cutler** (00:30:42):
Another example would be, and then I'm going to start listing these things off and then hopefully this makes more sense.

**Lenny** (00:30:46):
Yeah, it feels great.

**John Cutler** (00:30:48):
You meet lots of great teams and the better teams make high, better decisions faster. Now, that's like that high level thing that I say that to you and you're probably like, "Well, no shit. That's what I would assume to do that." But if you think about good decisions and stuff, like what do you need for good decisions? You need information, pays to have diverse perspectives, you need to be able to analyze the data. You probably need chops, some kind of chops in the domain to be able to do it. You usually need a goal in mind, like what are you optimizing for? It's very hard to make a decision just to make a decision to be able to do that.

Those are the basics, but still none of that's all that interesting, right? You're like, "Oh, you're saying you need information to make decisions and it's kind of not very satisfying to do that." But then if you think about three companies. We could even play the game together. I'll give you two, you could give me the third one. But let's say company A buys into the whole idea of an extremely rigorous decision-making process. It's very process driven. It's like you do this, you do that, we red team our decisions, we bring in people to push back, we've got this particular thing. Maybe that's how they achieve it. Company B, maybe they're just all about this kind of mushy, diverse perspectives thing. They're not very process driven, but they achieve really good decisions by making sure that there's these serendipitous connections between people at the right time with the right set of [inaudible 00:32:08].

**John Cutler** (00:32:08):
There are highly successful companies that achieve both of those particular things. I don't know, what am I missing? Lenny, you think about it. There's the rigorous process driven approach, then there's the company that's all about the ad hoc work together collaborative approach. What's another way that some companies make really good decisions all the time?

**Lenny** (00:32:28):
What comes to mind is a very top down CEO driven, here's what we're doing, here's the roadmap.

**John Cutler** (00:32:32):
Absolutely. So this is the thing, I'm sitting there and the very idealistic product managers are like, "You got to have empowered teams and you got to push decision-making down to the bottom," and I'm like, "Huh, well that company's doing pretty well and the CEO just tells everyone what to do and in fact, they attracted people who just don't mind that and like their vision and they do it." You find people who really like the process driven approach and you find people who do those things. That's one principle done a different way. But then I'll just take a couple principles. I just wanted to get that out of the way, that every one of these I mentioned could be achieved in a couple different ways.

**John Cutler** (00:33:10):
The first thing you notice is the companies that are very high performing have coherence between the structure of their company and their current strategy. This is a structural thing, I think when there's startups, things are very fluid and the strategy's in flux, and so they have a fluid structure, but then as companies grow, there's sort of a physics to the problem that starts to catch up to the particular things. Their funding approach, their incentives, the org structure, the architecture, even their technical architecture supports their strategy back and forth. The reason why I mentioned this one is you can have brilliant teams. You meet these brilliant teams where they've just hired in the best of the best and they're just struggling with a strategy structure mismatch and no amount of let's empower people or no amount of doing whatever is going to knock them out of that.

**John Cutler** (00:34:01):
So what do you need? You need a strategy, then you need to line the structure around it. This is different than saying ... you're asking me what do I observe when they're doing really well? Now, the tactics to achieve this might be different depending on the company, but you could get that. I think the second thing, if I admit it, is the strong opinions loosely held, which is there is this balance of believing in certain things, believing maybe in the power of products or the power of connecting with customers or maybe key strategic things that they need to do, or even believing that this is a done deal and you just need to move faster than everyone else in the space, or even the belief that you need to just go straight to commodity pricing like Amazon with whatever you're doing.

**John Cutler** (00:34:41):
There is just a stubborn, strongly held belief that is then balanced with their ability to have the loosely held thing. I would just observed this in meeting after meeting with these teams that seem to be having a bout of being more high performing. They would be stubborn about some things that they were doing even when it didn't make sense in the short term and then they would do that. I think that that's another thing. I think related to that when it comes to the product world is just a core belief in the power of products. The Jeff Bezos thing, that the success of today was set in motion three years ago, that product is a layer cake and that you are layering on decisions, the success you're having now is a layer cake of decisions from the last bunch of years that you're doing it.

**John Cutler** (00:35:26):
You could rationalize that all you want, but at the end of the day, it's often because either the founders or other people involved have seen how that can work because there is a leap of faith and there's a leap of faith that no amount of data or no amount of AB testing or no amount of rationalizing or no amount of spreadsheet math to figure out the ROI of what you're doing will ever help you. It's just not. I just noticed that pattern over and over that there was just a slightly irrational belief in the power of what it would take to have a nine craft level product versus a seven craft level product or six craft level product. I think that that's another component. I have a couple more in depth like that.

**John Cutler** (00:36:10):
Definitely the leadership is coherent, so that's walking the walk, talking the talk and I think this is one of the most fascinating ones because it's very much about being who you are and not being embarrassed about that thing. There are companies probably all know that outspoken, domineering believe that the company just should be run a certain way and they set this vibe, this coherent ... that their actions and words match together. When you think about it that way, it makes more sense. The company that's like, "Oh, well we want to empower our teams and do whatever and we believe in our customers," and their actions don't match those particular things, that's not very, very coherent to do these particular things. I think that that's one, the coherent things.

**John Cutler** (00:37:06):
Okay, so you've got those high level ones. I think you can definitely add skills and experience. I mean, those definitely matter. I think one thing that happens a lot is how the company views its skills. Here's a challenge we had in Amplitude, just sharing this, is you could view Amplitude as just another B2B SaaS company or maybe just an analytics company. But one of the challenges we had when it was how to build our team is to think about where do you draw the line between someone who's just done B2B SaaS for the last 10 years, is a pro at what they're doing and then how someone could embrace this kind of weird problem, sort of bottom-up motion, top-down motion. It's in product, it's a messy space. You need to be more strategic to do that so the skills need to be mediated obviously between the environment to do those things.

**John Cutler** (00:37:51):
Then like all the other, they know how to build software, things don't break, they can experiment without risks. I don't know. They have positive habits. I could go on and on. Hopefully this is helpful just hearing my thought process to go through these things. But I think that the TLDR of this whole thing is those top ones I mentioned seem like common sense and it's like how do you put it in motion in your company? I was just reading that working backwards book about Amazon and they're in this chapter about basically their bar raisers thing and I share it with my partner who's the head of HR at a company. She's like, "Yeah, this is sort of common sense hiring. They're just talking about de-biasing the hiring and having standards and having those linked into the jobs and just not rushing it."

**John Cutler** (00:38:41):
It's like these things that seem so common sense are actually hard with what they're doing. I don't know if you've noticed that, but it's like a lot of the advice is common sense. That doesn't mean it's easy to put in motion.

**Lenny** (00:38:53):
Yeah, and there's also a lot of power to just making it a very important value to the company. Just calling it bar raisers-

**John Cutler** (00:39:02):
[inaudible 00:39:02]. I'll use the example of a company. I mentioned this company AppFolio here in Santa Barbara, but Klaus and Jon who founded that company, it's just a gem of a company, it's an amazing vertical B2B SaaS company. But I think in the story that they tell us when they started AppFolio, they're like, "We want to find a place where the money flows and we want to be really close to customers and we just want to ..." Well, they were engineers who had seen the light around customer development, just getting close to customers, just being in service to the customers, not just gold plating every technical decision you did. They bought in early to the ideas of test-driven development, pair programming because they believe that the quality ... you should never be worried about the quality. They just believe that quality wasn't something you sacrifice as the norm. It's just got to work.

**John Cutler** (00:39:51):
They believed that was possible and when you think about it, those things are always debated. Like, "Oh, should we get technical debt or not? Or how much customer contact is it not?" These two founders basically are like, "That's it. We don't sacrifice on those things." They've done really well with that.

**Lenny** (00:40:08):
That's a thread I want to actually follow up on, is just the power of culture and values and things like that. But before we do that, let me just summarize maybe the top five attributes and kind of traits you just shared and then I have a two part question around this. I wrote these down. Basically the things you've found are true for the companies that seem to be best at building product and software and running product teams. One is coherence between what they're doing and what their strategy is. Two is strong opinions loosely held. Three is belief in the power of product. Four is the leadership is coherent, that their advice matches their words and their actions. Then five is just the necessary skills and experience in building stuff they're building.

**John Cutler** (00:40:51):
Contextual skills too. Yeah, exactly.

**Lenny** (00:40:54):
Kind of a two part question. One is if there's a pie chart of what contributes to this working out, what percentage would you say is just the people that they hire that contributes to them succeeding here? Then related question is just like can you change a team to be high performing? Does that happen or is it often just like this is just the way they are and their culture and their founders are this way and it's really hard?

**John Cutler** (00:41:18):
The pie chart, that's the problem. I mean, that is the trillion dollar question so I don't really have an answer. I have a couple thoughts on it. What do we know? We know that you can have a bunch of geniuses in the room and if there's not coherent leadership and there's not coherent structure in what you're doing, they'll fail. Okay, so we know there's a limit on one side of this particular problem and we know on the other side of the problem is if no one's done this before, who knows? Because how many startups were started by people who hadn't done it before, who had passion for doing something? Now, they made a lot of mistakes. Now, granted people would say, "All right, now after three failures, I'm going to tell you what we need to do to succeed," so maybe they have to fail a couple times to do that.

**John Cutler** (00:42:03):
With the right things in motion, you can do that. Also, another data point. At a lot of companies that are known to be higher performing, they're one of two categories. Either everyone in the company is this extremely vetted genius at what they're doing, or they have a culture where people stay for three, four, five, six years, they build their career or seven, eight, nine years. There is a concentration of people who are very skilled, but they have a knack for bringing people up. They have a knack for taking someone who has some of the raw materials to be able to do it and making them really good at their job to be able to do it. I'm not going to throw out a percentage point into it. I'm just going to note that I think that the biggest challenge is that we all need to challenge our biases.

**John Cutler** (00:42:46):
I do too. Four or five years ago, I would've said, well, personal skill's nothing. It's all the environment. There's people on Twitter who do this all the time. They're like, "Bad management kills everything. Skills aren't important. You should just be able to do anything with anyone." I used to be one of those particular people and I also have this sort of humanist bent to what I'm doing, and so I very much want to believe ... I'm always the person that's like, "Oh, we should give them the seventh chance." I know myself right to do that and I would suggest that there's people on the other end of the spectrum who could benefit from shifting a little bit to embrace some other ideas too. They're the people who are like, "Well, it's 100% their skill. We will hire complete A plus players all a particular time. Everything will work out as expected." Or they trace everything back to leadership anyway. So when anything's wrong, they're like, "Well, this happened under this person's watch, therefore they are a failure."

But how many companies in general will hire a string of highly qualified people into a particular department and then fail each particular time? I don't know. I don't have the answer for you on that one, but I think that everyone can benefit from challenging maybe their happy place, me included [inaudible 00:43:57].

**Lenny** (00:43:57):
I like that. It's like it's an optimistic perspective basically and anyone can change, anyone can improve. Don't assume that it's just not possible.

**John Cutler** (00:44:05):
And give it a shot and then can you create a coherent environment where maybe that could happen. Frankly, we're maybe getting into this later, there's a lot of companies that were flying high and are not flying high anymore. High performance is not this state you achieve. It's actually a continuum that you're always ... we have this in our personal lives too. We're flying high and we think we do everything and then we get to that point and then we go back down into feeling we don't know anything again and we feel those lows. That's kind of how I think about that particular thing.

**Lenny** (00:44:37):
**John Cutler** (00:46:12):
It's the latter and I think that's why I called the damn thing the beautiful mess. Because I think we all have confirmation bias. We'll point to that company and say ... I mean, let me just use an example. Satya Nadella and Microsoft. You could argue you obviously have someone who's this very humble, very capable leader in that particular thing. But I imagine that at some point in the future there'll be books written about that and they'll say like, "Hey, it was kind of that. But you know what he did? He got rid of some bad people and created the air cover and set in motion the couple of strategic imperatives that we're going to let the things going." Now imagine Microsoft didn't have all the wealth of talent that it had, or all the wealth of structures or the good parts of the tradition, or let's say the bad parts served them well for a long time, but maybe they started to become a little bit outdated and then they were putting them in a competitively bad situation.

**John Cutler** (00:47:07):
Even that situation, you can idolize that particular leader for doing it, but there's many things that could happen to be able to do that. There's this idea of great man theory, and this is something I talk about a lot where in great man theory success is the result of these highly influential, highly effective men, in a lot of cases, and that you can explain history through these heroic men. That's sort of a thing. A lot of people base history on doing that. I think that this, again, just the other perspective here is that things are a lot messier and you can't just trace everything to these sort of single heroes men in many cases that make it happen. I'm just presenting both sides of it as we kind of dig into it. I think, though, let's say you're a founder and you're trying to decide, "Should I invest more on processes or should I invest more in people?"

**John Cutler** (00:47:57):
The first thing is introspection. What do you believe in really? Not just what do I believe in that you think the whole rest of the world ... I think the rules of the world are that blank happens. It's like what do you believe in and what do the people around you believe in and how can you be a coherent leader? You know what? You can nudge yourself a little bit away from your happy place, but you're not going to go super far. You're not going to go from a process-driven, meritocratic, X, Y, Z person all the way to I'm going to start a collectivist company where everything is sort of the consensus decision to do that. You're not going to do that. But I think it starts with self-awareness and then that's how people form their authentic leadership vibe and then they flex a little bit and then they embrace other perspectives. That's just my perspective on it.

**Lenny** (00:48:49):
That really resonates. It makes me think about companies, especially in the past couple years, that did really well because the market was pulling them and everything was just killing it. They're just growing crazy and you would assume it's the founder, the CEO, that's the result of that. But then when the market tanks, things stop working, and that's a really good, I think, example of just, it's not necessarily the person. Could just be other factors that make it feel like everything's going great.

**John Cutler** (00:49:16):
And people are great. There are people that have an outsized effect in particular companies. A great example there is people forget that, for example, leaders or CEOs also have a lot of formal structural power at their disposal to be able to change things. So well, there's that great man leaders, genius. They do have more knobs to move, and even then they're not the boss. You know what? There's a board, there's investors. If you talk to any CEO, they'll be like, "You think [inaudible 00:49:47]. I've got people bossing me around too." It's always a mix. That's the way I see it.

**Lenny** (00:49:54):
Which is why if things don't go well, their ass is on the line.

**John Cutler** (00:49:58):
Yeah, exactly.

**Lenny** (00:49:59):
Coming back to a thought I had as you were talking earlier about values and culture, it's interesting that wasn't on your list of just the power and importance of, I don't know, strong value, strong culture. Have you found that that's just not essential? What are your thoughts on-

**John Cutler** (00:50:13):
No, I think it's kind of the fabric that creates those other things. It's the fabric that creates coherence. Coherent around what? If culture is what we're doing, is what we're acting and the way we act is sort of a function of some of the belief systems and the culture and the value systems that we have, maybe I just almost take it for granted that that's sitting underneath those particular things. But here's an example where sometimes nuances matter. I'll just use Amplitude. We had some values and we had HOG, humility, and it's this idea of ownership and a growth mindset to do these things.

**John Cutler** (00:50:52):
Ownership defined in an individualistic culture is going to look very, very different than ownership defined in a collectivist culture. What I find with companies is that ... and certainly we struggled to communicate this too, and I think we were pretty good at communicating where we sat on this particular thing, but a lot of times people write up these cultural documents and they're just like, "Well, this is our culture. We're into ownership." It's not saying much, saying that you believe in ownership without the addition of ... what we would do successfully and Spencer and other people do successfully is talk about the behaviors that represented that level of ownership, then that tells you something about what the culture is. Maybe when I was answering that, I kind of took that for granted. But there's a set of beliefs and values that sit underneath all those things, I bet.

**Lenny** (00:51:38):
When you think of the companies you work with over the years, and you don't have to answer this if you don't want, but when you think of the companies with the best culture or the best way, or some of the best companies in terms of how they build product, who comes to mind?

**John Cutler** (00:51:52):
I will mention some companies, but I'm not going to mention what people think in doing this. I'm just going to mention moments where I was like, "This thing is really clicking," and not because it wasn't easy-

**John Cutler** (00:52:00):
I was like, this thing is really clicking.

**Lenny** (00:52:01):
Yeah.

**John Cutler** (00:52:02):
And not because it wasn't easy, or there is a leader at Lego and her name is Angela. And when I'm talking to her, I'm just like, this person just has it dialed in. This is really hard. This business is transforming. They've got one of the biggest, most iconic brands in the whole world at their hands. And I'm sitting and I'm just going to single out her. Yeah, there's this situation here. It's not easy, it's not great. It's not high performing by any, you take a tiny Silicon Valley company. Yeah, it's hard to be Lego with thousands of people trying to build this and trying to take an iconic brand and turn it into something having to do with digital stuff. But I just want to give a shout out to her.

**John Cutler** (00:52:47):
That's what I got to say to this question. I think of it more of these moments where I'm like, "Wow, this shits hard. It's not ideal." And that people are coming to work every day and there's a group of people in this room who are extremely well-meaning. And you know what? The impact of their work might not even be seen in their tenure at that company.

**John Cutler** (00:53:06):
Some of these larger companies might take a decade to really work themselves through. And so I don't know, when you asked that question, I thought more about individual moments where I spent time with teams or like that team I mentioned to you in India where it's like everyone's super humble and whatever. So...

**Lenny** (00:53:21):
Awesome.

**John Cutler** (00:53:22):
Yeah, I'm not going to give a lot of names.

**Lenny** (00:53:22):
No, it's great.

**John Cutler** (00:53:23):
But just shout out Angela. She's doing an awesome job.

**Lenny** (00:53:25):
Go Angela. That reminds me of something I wanted to ask around the cultural differences between product teams in different countries. You talked about India, you talked about Lego. What have you found to be the main differences in how product teams operate and companies operate across different countries like say California versus Paris versus Australia?

**John Cutler** (00:53:46):
Yeah. And again, I'm not an expert in this and I think Erin Meyer wrote that or Meyer, I'm not sure how to pronounce her name, wrote that book, The Culture Map. And so you should just find what those people wrote because they're much smarter than I am about this. But here's the individual things that I noticed is definitely the individualist and what I would call almost like communitarian vibe.

**John Cutler** (00:54:05):
The idea of individualism versus the idea of the team being sort of a community of people together. So that's one, and you pick up about that a lot when you go to different places. I mean, in the United States you'll find this situation where you've got this one engineering manager and they are brokering the projects with every single engineer on their team and everyone wants the promotion.

**John Cutler** (00:54:27):
And there's this whole, instead of the PM working with the team, it's like the PM brokering stuff with an engineering manager to give everyone their premier project. No one's really working together. There's no pair programming. There's nothing like that. That's a whole other debate, but. And so that's highly individualistic and it might work in that particular environment.

**John Cutler** (00:54:47):
In fact, it might be optimized for environments where you're burning through people every 18 months or 24 months or... Because you just want to put another cog into the particular machine so that you can grow and so you can do stuff. And that's an extreme example, but then you compare that to other parts of the world, it's much more consensus driven. The team perceives itself as a team having a team goal.

**John Cutler** (00:55:08):
They have a team objective. And certainly even in the Bay Area, there's companies that are more the collectivist vibe and the more. So to say that it's just about the world is not really just right. So I think that yeah, the collectivist individualistic thing is important. I do think that certain cultures are much more sort of hierarchically oriented.

**John Cutler** (00:55:26):
There's much more deference to the hierarchy in the particular where people are sitting and the information flows in a certain way. And some companies tend to that being more bureaucratic. And then some countries tend to that being like, it's still a tall company, but it's very much like you manager, you own this, you do this. So it's not like rules are flowing from the top down. It's more just a pretty big org chart. So those are some of the things that come to mind, yeah, as we're going through it. So yeah.

**Lenny** (00:55:55):
This relates a lot to something else. You often talk about that much of the advice on the internet and books, newsletters like ours is geared towards Silicon Valley type tech startups.

**John Cutler** (00:56:06):
Yeah.

**Lenny** (00:56:06):
And in reality, most PMs don't work at companies like that. A lot of them are going through transformations.

**John Cutler** (00:56:11):
Yeah.

**Lenny** (00:56:11):
They're trying to transform the way their culture works. And I imagine a lot of companies you work with are trying to get to that point and that just a lot of advice doesn't actually work for them. What have you found along those lines of just companies going through this and things you've learned there?

**John Cutler** (00:56:24):
So putting myself in the shoes of those particular companies, like I said, I think some of my most rewarding interactions have been with these non Silicon Valley companies. I certainly learn a lot when I talk to companies in the Bay Area and in the United States to do those particular things.

**John Cutler** (00:56:41):
I think that the first thing to keep in mind is that those, let's just take these bigger companies for a second, big enterprise companies. Part of the thing is just realizing how much inertia they're up against when you're chatting them. So I do believe that there's some structural things that probably they could avoid, but then there's also just structural things that are just part of the game to do that.

**John Cutler** (00:57:11):
So they'll be in situations where maybe none of the executives have shipped product before. They also assume that there's only one way to do things. Certainly in a lot of high performing companies, I have friends who will go and work at those companies. They're like, "Oh no, no one changes the rules here. We just do it this way at Amazon or we just do it," whatever.

**John Cutler** (00:57:29):
So this similar thing happens in these particular companies, like there's only one way to do things. They've got these crazy annual budgeting cycles and planning cycles, or maybe there's a big IT industrial complex that they're sort of trying to transform into doing these things. So anyway, my point is, is that they, so many of these companies just have structural things that make it very difficult to just immediately convert that particular advice as they're doing that.

**John Cutler** (00:57:59):
So I think the first thing that comes to mind with that is how to adapt that advice maybe for some of those larger kind of transforming companies. And I think that the couple things that I sort of remark on is that one, reps matter in those particular situations. So in many of those companies, they should focus on creating these sort of areas or pods where a company can, a team can get in the reps that they're trying to be able to do.

**John Cutler** (00:58:29):
So it's sort of a little miniature version of that. And there's a whole problem with innovation labs. There's a whole problem with that kind of idea. But the idea that you can create these little bastions where a team can get in the reps is important.

**Lenny** (00:58:41):
And reps meaning shipping, shipping product.

**John Cutler** (00:58:43):
Shipping and learning, going through the full loop. Can they go through the full loop of what they're doing? And I think that the other thing that comes up with that is that most of those companies need to think of frameworks appropriately.

**John Cutler** (00:58:57):
They'll read about these particular frameworks or what particular companies do or don't do. And I think that for a lot of those companies, they see adopting the frameworks as the end goal. They kind of look there. And sometimes maybe even you write a post, it's like, "Well, how does Figma work?" And they're like, "We use these frameworks."

**Lenny** (00:58:57):
Yeah.

**John Cutler** (00:59:15):
And so this company's like, "Well, we've got to use these framework." And I think that the way that I tend to think about frameworks is that they're more like a job aid. They're more like a learning tool that the team kind of uses to keep themself on track. But part of the thing is that those companies will reinvent the things they're using when things aren't working out.

**John Cutler** (00:59:34):
So I think that that's another thing maybe some of those companies could benefit from doing, where we're getting kind of more into the kind of digital transformation or the big company space. But I think back to that particular question, I think you need to view a lot of advice coming from Silicon Valley just contextually. It's startup. There's a tradition of how these companies work. Many of them are just optimized very much for that first big arc of growth.

**John Cutler** (00:59:58):
They've never really been disrupted. The only disruption has come from scale, not from being a legacy, a huge global brand or huge global business, and then being disrupted by new things. The only problems, not the only because it's really hard, but the problems have been primarily scaling. So they're kind of optimized for wrapping their head around that.

**John Cutler** (01:00:20):
And then many of them are just pure digital product companies. And so I think this is a thing that a lot of the big rideshare and food delivery conglomerates are figuring out. They're like, " Oh, this is a lot harder than we thought." When you're dealing with moving people around and logistics and things, it's an order of magnitude more complex to do that.

**John Cutler** (01:00:42):
So I don't know if that helps kind of explain my perspective on that, but I think that it's like you have to adapt the advice and you also need to acknowledge that for some of these companies there are these sort of just structural areas of inertia that they're trying to work through and that a lot of them maybe need to adapt this advice on the small instead of thinking they're just going to install all the frameworks or install everything they're doing.

**Lenny** (01:01:02):
Yeah, this is really, really good advice. I imagine folks are listening that may be working at a company like that. It feels like there's two sides to it. One is there should just be an awareness of this may not work at us, we're not going to be Figma.

**John Cutler** (01:01:02):
Yeah.

**Lenny** (01:01:15):
And let's just get used to that. And then two, this good reflection for me that I'm probably causing some damage with people reading a post on here's how Figma builds product. And then not adding a little bit of, maybe this won't work at your company.

**John Cutler** (01:01:29):
But maybe it can. And I talk about this a lot, this sort of I do believe there's sort of this fundamental attribution bias at play where people in these high performings don't acknowledge the amount that luck and inertia has been a part of what they're doing. And that the people in the big companies, or these not, these companies that believe that it's not the way that they can do that actually overestimate the kind of systemic drag in their organization and underestimate what can be possible.

**John Cutler** (01:01:57):
And you think about that, we do that a lot in just our lives in general. We see someone being really successful and we'll say, "Well, but my situation is this." And when things are working for us, we're like, "I'm a genius. I'm a genius doing this particular thing." When things work, we're competent. When things don't, it's like the system and everyone else's incompetence to be able to do it.

**John Cutler** (01:02:18):
So I do think that there's opportunities. I think there's another thing too, that there's a vast spectrum of companies. We paint some of these large enterprises on one end of the spectrum and then these other company, these modern product companies. But I brought up that plumbing company in Australia. You meet these companies, you know what? Their revenue is literally 50 startups. They are not doing bad. They are not doing bad.

**John Cutler** (01:02:44):
And you know what? They're actually doing interesting things. One of Amplitude's customers, Anheuser-Busch has this thing called BEES. And BEES is basically a liquor distribution app. And it's literally one of the biggest B2B companies in the world. And you know what? Anheuser-Busch, it's like what? We're going to distribute beer because the pandemic. And so we're going to have, and I think actually they started to become more even used for logistics.

**John Cutler** (01:03:06):
You're a bodega in one of those countries, you can order beer for doing it. So I think that we tend to kind of paint this world of, there's the big smoke companies and then there's the fast nimble companies, but there's everything in between. Another example is a lot of tech companies started 2000 to 2008, kind of are on their third or fourth act at the moment, second or third or fourth act, bought a lot of companies, they're trying to absorb them.

**John Cutler** (01:03:33):
They might be trying a product-led growth motion by spanning all the different acquisitions they had. You know what? They are on top of their game. This is not a slouch company, but it's really hard for them to do that. Or we at Amplitude, we'd have a lot of, not old FinTech, but not newest companies. They're printing money and they're just embracing this particular thing. And then compare that to, I did a big Northstar session or more of a coaching session at NewBank in Brazil when there was just 15 people in a room and now they're massive.

**John Cutler** (01:04:06):
So I think that we tend to paint things as a form of modern product adoption. There's the high performing companies and the low performing companies when in fact there's just a whole plethora and diversity of different companies riding different waves, adopting different things at different times. And many of them doing really wholesome, humble, good work, just dealing with their circumstances at the particular time.

**John Cutler** (01:04:33):
So I think everyone should absolutely know how Figma works, for example. And then we need to try to boost the stories of Angela and her team or some of these companies that you'd never even expect. There's a company here in Santa Barbara that's like, they do refrigeration, use AI to refrigerate industrial facilities. And Carrie, who's the leader there, that company is one of the best leaders I know.

**John Cutler** (01:04:57):
And Jesse, who's one of the founders is Harvard PhD student who understands AI doing these things. And I actually would encourage a lot of PMs to think about, look, especially in this economy, what are these unsexy businesses that are kicking butt and small here, it's in sunny Santa Barbara? So I don't know. I think that there's a lot more diversity than just the high performing, low performing spectrum. There's just a whole universe of fun companies out there.

**Lenny** (01:05:26):
Well, as you were talking, I was thinking about there's a small group of people like you and Marty Kagan and a few other folks that have worked with tons of different and diverse product teams and not just say, Silicon Valley teams. And I'm curious if there's any other names of folks you think listeners should follow if they work at maybe a non-Silicon Valley type team. Marty Kagan is who comes to mind first, but I don't know if you have anyone else. And if not, that's all good.

**John Cutler** (01:05:52):
Well, yeah, there's a couple people, but I feel like I should go back and just generate this full list for people. Maybe it would be interesting. Maybe I'll take that as an action item to...

**Lenny** (01:06:00):
Yeah.

**John Cutler** (01:06:01):
List a couple of these.

**Lenny** (01:06:01):
We'll put it in the show notes.

**John Cutler** (01:06:02):
And I'll give you an example of one guy, and his name is John Smart, and he wrote this book called Better, Sooner, Safer, Happier. And he, I think he was at Barclays Bank. I think that's how you say it in England. And what, he led this transformation. And then I think he's gone on to, he has a consultancy now for doing things. And the guy is just awesome to talk to.

**John Cutler** (01:06:27):
He's really, really humble about what the thing book, the book is really interesting. And the thing that I noticed when talking to John is the order of magnitude of complexity of problems that has unraveled and what he had to put in motion to take an old school bank and at least try to get some part of some kind of transformation working in that particular company, I think there's a whole realm of people like that. And I'm going to list a, maybe I'll follow up with a couple more lists of people.

**Lenny** (01:06:57):
Yeah.

**John Cutler** (01:06:58):
Who can do that. And then I do think there's the people like Teresa Torres and others that have come up with a technique that is universal. You can teach an element of product thinking with her techniques or this opportunity solution tree or this continuous discovery thing that everyone can find accessible no matter where your company is at. And I have a lot of respect for those types of techniques because they're more universal versus some very arcane niche activity.

**Lenny** (01:07:36):
Awesome. Cool. And then we'll do our best to include whatever full list you come up with in the show notes.

**John Cutler** (01:07:41):
Yeah.

**Lenny** (01:07:42):
So I've been asking a lot of very specific questions. I want to give us a chance to kind of zoom out a little bit.

**John Cutler** (01:07:46):
Yeah.

**Lenny** (01:07:47):
And see what other advice you may have for product managers and the product community broadly. It feels like you're in this kind of reflective phase after working with all these companies and you take time, you have more time to think. So I'm curious what comes to mind when you think of just, here's advice I have to share.

**John Cutler** (01:08:04):
Yeah. I think kind of going back to the reps thing, I think that there's this fire hose of amazing information that's out there and I contributed to it and you contribute to it. And there's just, I mean, think what a time to be alive. You can literally just.

**Lenny** (01:08:04):
Yeah.

**John Cutler** (01:08:19):
Get these podcasts going. You can listen to anything you want.

**Lenny** (01:08:22):
Yeah.

**John Cutler** (01:08:23):
That's pretty amazing. And I was thinking to myself the joke as I saw you put this thing about Andrew Huberman about who gives these sort of life hacks thing. It's like there is absolutely a place for this type of content. I just want someone to summarize what the hell I should do when I wake up in the morning.

**Lenny** (01:08:38):
Right. Cold plunge.

**John Cutler** (01:08:39):
Can I be healthier.

**Lenny** (01:08:40):
Sunlight. Yeah.

**John Cutler** (01:08:41):
Yeah. I got my sunlight. I went from my sunlight before screens to prepare for our talk today.

**Lenny** (01:08:47):
Wait, actually?

**John Cutler** (01:08:47):
Yeah.

**Lenny** (01:08:48):
That's great.

**John Cutler** (01:08:49):
I have it in my habit tracker, sunlight before screens every day. Yeah, I got my watch that I got a couple, I'm on vacation. I'm between jobs now. So it's about all health.

**Lenny** (01:08:59):
Yeah. Optimizing.

**John Cutler** (01:09:02):
But I think that you need to keep in mind that this is a skill and skill is knowledge times practice mediated by your environment, the habits you form and the motivation that you have and the particular things. And so I think that I learned about that a lot working with learning experience designers in Amplitude that we tend to think that this is just a function of the knowledge that we pick up and the number of podcasts that we listen to. But really it's about going through this loop. So in Amplitude, we have this data informed product loop that we would teach, and it's basically, you need a strategy, you need to develop qualitative models, you need to add measurement to those models. So Northstar framework would be an example of a qualitative model. You need to add measurement to those models, figure out how you're doing it.

**John Cutler** (01:09:48):
You need to prioritize where to focus. You need to design bets, you need to measure the impact of those bets. And then you need to circulate what you learned back into the strategy, back into your models, back into how you prioritize, et cetera. And it helps you figure out where you're kind of weak at the moment.

**John Cutler** (01:10:02):
So for example, you need a strategy. Without that, nothing is possible. But you could have an amazing strategy and you don't deploy it with the right models, no one can prioritize them. We could do all that right, but you don't design any bets and can't ship anything. Oh, that's kind of a problem. But you could do all that right and you don't know the impact of anything you ship.

**John Cutler** (01:10:18):
But you could even do all that right and not circulate the learning back in your company and then you're still not going to succeed in these things. So that's an example of when I mean by the loop. And so one thing you could think about for your career that I think people should focus on, and also in terms of sharing the content that they share.

**John Cutler** (01:10:33):
So we're sharing a lot of content around knowledge and job aids, knowledge and job aids, and maybe a little bit of motivation, like how did that person succeed and do that and... But if you think about your career, just think about how many times can you get around that loop and what are you putting, because I worry that people are loaded up with knowledge and feel almost... I meet some of these leaders and they feel beaten up by the advice industry.

**John Cutler** (01:11:03):
They feel beaten up that they can never be good enough. They cannot be like whatever company, or they feel like their company's never good enough, like they can't empower their team, they just can't follow anyone's advice. And so I think people are beating themselves up when I think that you shift for some people to focus to taking that knowledge and just getting that loop going for your teams or getting that loop going for your career or getting that loop going for your company is probably a pretty safe bet. So I would think that that's one thing that comes to mind.

**Lenny** (01:11:31):
Partly being responsible for some of that is what I...

**John Cutler** (01:11:34):
Yeah, me too.

**Lenny** (01:11:35):
My advice to people is don't feel like you need to read everything coming across your plate.

**John Cutler** (01:11:40):
Yeah.

**Lenny** (01:11:40):
It's instead wait for the moment when you need that thing. I'm working on SEO right now. Cool.

**John Cutler** (01:11:40):
Perfect.

**Lenny** (01:11:45):
I saved that thing about SEO, I'm going to go do it. Just like a just in time learning because you learn it so much better and like, "Oh, shit. I have to load all the stuff in my head in case it becomes useful."

**John Cutler** (01:11:53):
Absolutely. And I think one thing you think of is think about the podcast you listen to and think about that content is almost like you don't know what you don't know often. So I think that the challenge is, is that if you've been doing PM for a while, product management for a while, you don't really, I don't fit everything in my head.

**John Cutler** (01:12:13):
I just, for example, pricing. I know pricing is a thing. I know that there's some people are amazing at pricing. I know that if someone told me like, "Well, you should just price it like this," my spidey sense would say, "You don't know what you're talking about because I know that there's more to it than just what you just said." You develop your spidey sense for things and you know that there's people. You have to dip your toes in understanding. That's the beauty of podcasts, your mind can get blown and then it puts in the back of your brain. You're like, there are some people who know a lot about that versus the founder who believes that they're going to figure everything out for themselves and is just like, no, it's actually a thing.

Pricing is a thing or you know what? Meeting design is a thing. There's people who obsess about it or service design is a thing or interaction design or strategy [inaudible 01:12:56]. So that's building on what you said, I think that there is a, especially if you're starting out, there is a definite value of almost seeing the 501 level courses or hearing that genius lecturer.

**John Cutler** (01:13:07):
When you're in college as a freshman, I remember, I dropped out, but you would see the genius professor and you wouldn't understand any of it, but you'd know it's a thing and then it helped you guide the way you're doing. So I think that you should kind of balance out those things. But to your point, at the end of the day, you got to just put this stuff in motion somehow.

**Lenny** (01:13:25):
Yeah.

**John Cutler** (01:13:26):
How to do it.

**Lenny** (01:13:26):
And then just know that it's there when you need it. Find some way to store it.

**John Cutler** (01:13:30):
Yeah.

**Lenny** (01:13:30):
Save it. Maybe even just assume Google will find it for you.

**John Cutler** (01:13:33):
Yeah.

**Lenny** (01:13:33):
One more question along that same thread is you talked about the importance of going through these loops. At some companies, you just can't really, the company moves slowly, it's super waterfall, they plan really long. Do you have any advice for someone that's like, "Oh, I want to go through loops more often? This is really good advice."

**John Cutler** (01:13:47):
Point number one is you often underestimate what loops are available to you in that company. They throw up their hands. I've tried to mentor people like this and I think we've done a decent job, but the first thing I'm like, "Just don't throw up your hands and say it's all going to shit." Just at least document what was the.

**John Cutler** (01:14:03):
So even if someone from on high says, "Build X," you can at least say, "You know what? Selected option is X. What would the one-pager look like if X was one of five options?" Write the one-pager. Go and talk to that executive and say, "Look, I know you've told me to do this, but what would we observe if this was working versus not working? I'm here to help you with that."

Great. You've got some metrics along [inaudible 01:14:29] is what you're doing. Just nudge it. Just one little thing. Hey, nothing's stopping you from writing down all the potential assumptions and risks that you have. Even if someone's like, "Forget all that, you're just going to build the thing." You've gone through the motions for doing it.

**John Cutler** (01:14:44):
And I think people underestimate that because the environments are kind of feel like stellifying, I guess is one word, or stilted. And so they just sort of throw up their hands. But I would say that work with what you've got, because the last thing you want is to have a job opportunity two or three years from then and all you can do is shrug your shoulders and say, "I worked at a fucked up. I worked at a messed up company."

**Lenny** (01:15:09):
You can curse. It's all good.

**John Cutler** (01:15:10):
Yeah. Well, yeah. So you, "I worked at a messed up company. It was all shit." You're not really honoring yourself for doing that. So I'd say that that's my point about the fundamental attribution bias. Is it hard? Yes. Is it easier in those Silicon Valley companies? Well, maybe not. Maybe those are a shit show too. I've talked to plenty of them that are shit shows.

**John Cutler** (01:15:28):
But do you have an opportunity to kind of nudge things forward in your space? Probably. And bring to the systems thing, is it true that some people don't have the privilege of leaving their company for whatever reason? That is true also. So many things can be true, but that doesn't mean that you can't try, I think to kind of almost write your portfolio as you go. Because if you wait two years, you're going to think it was just all a blur and messed up. Whereas the opportunities might be there in your day-to-day as you're working through.

**Lenny** (01:15:55):
I love how much your advice is optimistic and empowering and not just, "That's the way it is." And...

**John Cutler** (01:16:00):
Yeah.

**Lenny** (01:16:02):
And your point about how top tier companies can also be messed up and everything could be going to shit is very true. Especially a hyper-growth company where you're just...

**John Cutler** (01:16:11):
Yeah.

**Lenny** (01:16:11):
Constantly changing. It's also very chaotic and things are just breaking all the time.

**John Cutler** (01:16:16):
And there's people too who just assume it just has to be that way. I would say that one model that I use is the sort of the chronic and acute challenges of the companies. And especially in the last year, you meet a bunch of companies dealing with the same economic conditions. And I will tell you, no, not all companies are equally dysfunctional.

**John Cutler** (01:16:34):
And no, not all high performing companies are equally beautiful in all roses. Legitimately some companies work down the chronic issues, which allows them to face the acute stressors, and other companies are just mired in acute issues to do those things. So it's kind of, again, both things can be true. It's like, yeah, there's nothing perfect in product. However, it is true that some companies are healthier than others.

**John Cutler** (01:16:58):
An example of that is the companies that leaned in to responding to the pandemic instead of counting the days until it was over. Massive difference. I've seen this over and over, probably with 15 to 20 companies. The companies that were intentional in designing their response to the pandemic versus being like, "Just let managers deal with it, whatever, we're just going to sort it out," have had an order of magnitude better.

**John Cutler** (01:17:22):
Now maybe the share price hasn't necessarily reflected it, but the happiness of the people there, they're going to come out of this stronger than the companies that were just like, "It's going to go back to normal and we're going to delay all these org design decisions until some future date." So I don't know if that tells you about high performing, but it's like the high performing companies saw the threat of what existed and then took deliberate steps, coherent steps to frame what their response would be. So that's just an example of that.

**Lenny** (01:17:54):
Awesome. I took us off track a little bit. I think you were going to go onto a second piece of advice.

**John Cutler** (01:18:00):
Yeah, I think that there's, well, okay, so one, definitely slightly annoy.

**John Cutler** (01:18:00):
Yeah, I think that there's, well, okay, so one definitely slightly annoying to me recently... I'll just get into the stuff that annoys me is that-

**Lenny** (01:18:06):
Let's do it.

**John Cutler** (01:18:07):
I personally don't think, I used to use words a lot, like product sense and product mindset and product things like that. I'm personally trying to do a better job this year about trying to unpack those things as legitimate skills and competencies. So if you think about product sense, what is it? Might be the ability to model problems, systems thinking, decision-making under conditions of uncertainty, facilitation tools that you have the ability to look at a competitive ecosystem and maybe see a thing and yeah, maybe there's a little bit of sense to it. It's like, "I want to help customers," or whatever. But I think that I'm trying to make a concerted effort to unpack those things into things that could be taught.

**John Cutler** (01:18:50):
And that's going to certainly be part of my role at toast. The last thing I want to do is be like you have a product mindset or you don't. A great example, I was even talking with Craig just the other day and we were talking about how in some environments there's this should/can divide, which I really like, which is some people are just locked into the can. They're uber pragmatic people, so it's like, "Can we do this? Is it possible, given the debt, whatever constraints that you have?" And then there's people who for some reason go in and say, "Should we do it? What should we do here? If those things were not an issue, what should we do?" So it's very easy to... I joked with Craig, it's like it's so easy to go down the path of being like, "Well there's can people and should people, there's high agency people and low agency people, there's this person and that person."

**John Cutler** (01:19:44):
It's much more interesting to go and be like, "Yeah, there might be a little bit of a personality component to it, but what skills is the should person bringing to bear on that particular situation?" Maybe it's a level of systems thinking, maybe it's a level of looking at the environment and being able to decouple the current tactics from maybe the optimal tactics for doing it. So that's one thing that I'm excited about, to do that. And yeah, there's a bunch of other things. The diverse perspectives, diverse mental models, maybe working with someone like you to try to raise up some of this more diverse... I really want someone to be like who's working at some company X, to be able to go and say, " Now that leader I can relate to, they're dealing with certain challenges that we are having to deal with at our company," and I'd love them to be able to have role models like that.

**Lenny** (01:20:41):
Like highlight people that aren't on Twitter that are doing the work.

**John Cutler** (01:20:46):
And not like meeting here. Not any of these particular people where they can say, "Well that leader..." I was speaking to someone recently, I wrote about this in my newsletter and she was just sort of forlorn. She was like, "I follow these people in this space and I know what my beliefs are and I know that that person has beliefs that I'm not sure vibing with completely. But the message to me is, the only way to get ahead in tech is to have those beliefs. And John, is that right? Do you need to believe this?" In this case, it was this very individualistic, very meritocratic kind of get ahead, push ahead type of vibe, which I respect that thought leader for putting out there, but this person didn't buy into it, which would've all been okay except she said, "Is there a place for me in this environment. Will I need to sacrifice my beliefs to get ahead?"

**John Cutler** (01:21:42):
And I told her about some companies that I know. I told her about Carrie, who I just mentioned, who's been working on building the diversity, even in a small company. I told her about different leaders in different companies that, "Hey, there's some companies where it is a real team vibe and there's some companies that that", and she was like, "That's really good to know. So I think that that's one thing I want to work on in the next year, to make sure that people have role models and not the people talking like me, but actual... Maybe I could be a role model to people in my new role, but ideally there's role model leaders who they can relate to. That would be great.

**Lenny** (01:22:16):
Awesome. I love that. I feel like you just talking about that makes an impact there. Something I'm definitely trying to do with this podcast is not just have all the same people that we see on Twitter all day and have a lot of people people have never heard of, but if you have suggestions, let's definitely talk offline. I'd love to do more and more of this.

**John Cutler** (01:22:31):
Yeah.

**Lenny** (01:22:33):
So those are clearly some of the things on your mind as you're kind of in this period of reflection. I'm curious if you are going to keep writing and keep your newsletter up, maybe publish more books and then just broadly, how do you make time, while you have a day job, to write? Because a lot of people always wonder that. I'm curious if you have any pieces of advice.

**John Cutler** (01:22:54):
I'm obsessed with the writing, obviously, and I think a bit of background about me is I was pretty involved in music and song writing and it was similar kind of thing, I just liked writing lots of songs. I like that there's a certain buzz you get when you're creating. And in the case of music, it'd be like you record the demo and you get it out there. I think what people have correctly picked up on is because I have a full-time job, sometimes it'll be Thursday night and my kid's finally asleep and it's one in the morning and I'm just like, "I've got to write this post." And so sometimes it comes off as being a little bit rough or even accentuating the fact that I don't give them an answer because it's like two o'clock in the morning now and I don't want to give them an answer. I want to go to sleep to do these things.

So I think one of the things I'm going to hope to do is maybe be more deliberate about trying to provide at least maybe some mental models for dealing with the mess. I mean there's things like that out there. There's this thing [inaudible 01:23:57], which is a way to understand the systems and decision-making problems have, are you dealing with a clear system, a complicated system, a complex system, or a chaotic system? And I like things like that because that helps do two things I like. One, I want to give people something actionable to be able to address what they're doing, but it doesn't remove the complexity in the particular situation. So I have role models in that. This guy, Simon Wardly does this kind of mapping, which I think is great. There's these other techniques that I want to try to lean into and maybe develop some of my own that sort of help people have something actionable and embrace the mess, if that makes sense.

**John Cutler** (01:24:41):
So for example, I recently wrote about something called the leadership, the Pyramid of Leadership, self awareness. And it's a simple model, but it goes deep how I want it to go deep. So the idea is that at first we know nothing about ourself and then the next level is that we start to become self-aware, but believe the whole world is wired just like we're wired. And then you go up to the next level and you believe that the world thinks different things, but you still think your way is the best way to be able to do that. So an example is, I remember talking to an executive and they're like, "People only stay because of their managers and because of their money. That's it." And I said, "Everyone?" They said, "Yes." "Do you believe that?" "Yes, because everyone believes it. It's a physical law of light." And here I am like, "Oh my God, I joined a company because the mission of the company or whatever."

**John Cutler** (01:25:23):
So they're kind of stuck down on that second level where they believe that, "Yeah, the world thinks different things, but I'm absolutely right." And then as you get up to the top, you become a little bit more aware that there's other valid views and then at the top you're sort of like, "No, you don't dishonor yourself and throw away who you are, but you realize that this is a huge asset in the world, that there's diverse views that you can bring together to do really, really amazing things." So that's an example of some writing I've even done recently where I'm kind of like, it's a complex topic, but I try to make it more actionable to do that. So that's one whole thing. The other thing too is leveraging all the crap that I have. I think it's like 700, 800 posts, maybe 900.

**Lenny** (01:25:23):
Wow.

**John Cutler** (01:26:07):
I had this whole blog beforehand that I did it. And then I have these hundreds of images with these frameworks and then it's like 50, 70 talks that I've done floating on YouTube and then there's all the mural boards I made at Amplitude. It's a different model. So I kind of feel like I could pull some of that together to make it more actionable for people, give people almost like a meta guide to Cutler content so that they're not just dropped into me writing something at 1:00 AM and being like, "Oh, just another one of those." Like, "Damn it, you didn't give me an alternative to NPS. This newsletter sucks." I mean, frankly, I would say the same thing too if I just stumbled into the newsletter to do it. So those are a couple things that I'm thinking about for the content, definitely not going to stop doing those, sharing those things and doing that. So yeah, excited about this next year.

**John Cutler** (01:26:52):
Also, the question about writing, I mean, one thing with a full-time job where most of my work is internal, obviously I need to respect my team. Again, I go back to that funny thing with Spencer, he is like, "You're writing about Amplitude." I'm like, "No, dude, I'm not writing about Amplitude. It's like every company has that problem." But if I'm working alongside people, I obviously can't be like, "No," I can't say, "Oh, your manager sucks." It's like Craig's going to read that to do that particular thing, but I can, what I'm really excited about is that part of my job will be involving doing a lot of writing and a lot of teaching, is hopefully work it out with the company so that I can share things that are not too specific about the company, but much more. They've got five different businesses at Toast, they've got all these people, so it's going to be a education every day. So I'm hoping to maybe get that inspiring my work in different ways.

**Lenny** (01:27:40):
Amazing. I imagine you might rename your newsletter The Beautiful Mess, slightly less messy.

**John Cutler** (01:27:46):
Yeah. Jam and Toast. The Jam and Toast decision. The addition.

**Lenny** (01:27:50):
Delicious.

**John Cutler** (01:27:51):
Yeah, there we go. 2023.

**Lenny** (01:27:52):
Also, as you were talking, I imagined a chat GBT three type chat bot powered by John Cutler content could be something to try.

**John Cutler** (01:28:01):
Oh, it could be a funny, yeah, I mean I'm sort of obsessed. I like the ChatGPT thing because I like having things, having a developer inspired by Hemmingway debate, a developer inspired by Tolstoy discussing how to resolve a GIT issue. So that's what I've been obsessed by lately is when you know how ChatGPT works, you can actually make it do really funny things. And back to the worldview things, it's actually really effective. This is a very actionable tip, if you feel you're heavily grounded in let's say the, I don't know, maybe you're like a hardcore objectivist or you believe in individualism, you can just type into ChatGPT and say, "Take this situation and interpret it by five different worldviews." And it'll be like, you'll get the humanist view and you'll get the communitarian view and you'll get the collectivist view. You'll do that. So anyway, it's a fun tool for that. It's really cool.

**Lenny** (01:28:52):
It is awesome. We checked the checkbox talking about AI, very, very hot these days.

**John Cutler** (01:28:57):
Yep. Score.

**Lenny** (01:28:57):
Score. One final question before we get to our exciting lightning round, I'm going to come back to the questions that folks asked you on Twitter. And there's a question that I saved up and the question, it was by Jeff Fedor and his question to you, he was, "What have you always wanted to say but couldn't now that you're between gigs?"

**John Cutler** (01:29:18):
Oh, that's good. So one thing is I didn't really need to filter myself very much when I was at Amplitude, which is kind of the beauty of the gig. I wrote this blog post, probably six years ago called How to Know You're Working in a Feature Factory. And I've always, this has all been my jam. The outcome, outcome and impact focus thing. So it's not like I've really had to hide anything. And so one thing I could say is the power of qualitative data, but even Spencer says that too. He's talking about early on in Amplitude you can rely a lot on qualitative data. So that wouldn't be all that controversial. That's a funny thing. There's not that much, I pretty much say what I say partially under the guise that I'm talking to so many teams. So therefore it's never about Amplitude. Absolutely not.

**John Cutler** (01:30:07):
I think the one thing that I would change, I don't think that many people in the company would disagree with me, but one anti pattern I see a lot on the part of implementing analytics is that people go in and undertake this huge implementation. They want to implement all their events, they want to get, they want to treat it like this big project. And again, I don't think it's too controversial internally, but I think I might have been much more adamant to people that's just like use our free plan and get 20 events going and you might wipe them out later, but you don't even know what you don't know yet. You would see these companies that are really qualified companies and it would be a couple months of back and forth of them trying to document every question they have and every metric they need and everything that you had.

**John Cutler** (01:31:02):
And I would watch them and I understood why they were doing that, but I really just wanted to shake them, which again, I wouldn't have done this because then I would've been talking about the companies I was talking about every day. I just wanted to shake them and just, "Sit me down with the developers at your company for three hours and let's like Hello world, a couple events here, this is, you could be getting value this whole time." And again, I don't think that people at Amplitude would disagree, but I think that that's, I wasn't going to talk about that all day because that would be sort of belittling customers who do want this big implementation thing. So pretty kind of inside baseball for analytics, but that's one thing that I was thinking about for Jeff.

**Lenny** (01:31:41):
Awesome. Great answer. Also actionable advice. How about that?

**John Cutler** (01:31:44):
Yeah, can do. You just need to find it. You just send me a message and say, "Do you have the actionable advice for it?" I probably do somewhere. I just maybe didn't have the time to organize it.

**Lenny** (01:31:53):
Good tip. You're going to get a lot of DMs. With that, we've reached our very exciting lightning round. I've got five questions for you. I'm just going to go through and whatever comes to mind fire away. Are you ready?

**John Cutler** (01:32:06):
Yeah, yeah, absolutely.

**Lenny** (01:32:07):
What are two or three books that you've recommended most to other people?

**John Cutler** (01:32:11):
Yeah, this one's pretty easy because they are fairly similar lately. So I really like the book How to Measure Anything, finding Intangibles or Finding the Value of Intangibles in Business. So that's by Douglas Hubbard. And the reason why I like that is again, at Amplitude the number of people who would come in like, "What are all our competitors measuring? We want to know exactly which metric to measure." And again, I'm laughing with you because I know you have these posts. Here's exactly the metrics that you should track. I really respect those posts and that's the power that you have. That's all really good. But what Hubbard reminds you is why the hell are you measuring things to begin with? It's to reduce uncertainty for critical decisions or to achieve certain objectives that you have. The reason why it's important to read that book is A, you figure out someone who's again, actionable, has thought this through. So he gives you kind of a framework to thinking about it.

**John Cutler** (01:33:02):
But B, he really challenges this idea of when making decisions in conditions of uncertainty, you only need to reduce the uncertainty to an acceptable amount to be able to make the next decision that you need to make. And we never have, people are like, "Product is science." It's really an art, like a game that's being played out. You never have complete information to do it. So I think that's a good book to remind people about what... To be more creative and thinking about measurement instead of thinking about measurement and metrics is just about adopting the exact metrics that everyone has and doing that.

**John Cutler** (01:33:36):
The second one I think would probably be Accelerate. So Nicole Forsgren, Gene Kim, Jez Humble, that's just one of the best books in the world about the factors contributing to performance. And it's built on many... It's six, I don't know, it's been out for a while now, 10 years? They did the Dora report, which was their yearly report where they did big surveys, like 10, 20, 30, 40,000 people responding to it. And Nicole Forsgren is an amazing scientist. So they structure their thing correctly. They would have a hypothesis about what is equal to performance and how all these individual practices contribute to it.

**John Cutler** (01:34:19):
And then they've updated it over time. And I think that Google bought Dora, I don't know exactly how all the parts came into place, but that book is amazing, just sort of teaching you how to think about the idea of performance because they'll include things like the Western topology, which is your company operating a bureaucracy or... These certain culture elements to it, but then also the practices and things that you're doing. So that's a great book when you're trying to think about, "How do I model performance?" And then it's also an amazing book because you can just literally put the stuff into motion about improving your development practices and things you're doing.

**John Cutler** (01:34:58):
And then I think probably the last one, man, I just love this book, this Jeff Patton book about user story mapping. I love what Jeff Patton did. He took this extremely simple idea, which is that you can lay out a customer journey and then organize, take a slice across that journey and develop it. And he gives this pretty basic straightforward method to do it. But I tell you, I'll go into companies like a year after they had Jeff in and learned this and they're still like buzzing about, "Hey, user story map." And it's just, he's a super humble guy and he would never outstate the value of this. He'd be like, "Yeah, it's just a journey map with a couple sticky notes on it." But I always, when someone's new at product management, I'm like, "Hey, this is a deceptively simple book. You'll learn this very basic idea, but it'll teach you a lot about product when I do that." So those are three that come to mind.

**Lenny** (01:35:50):
Killer suggestions, I love answers of books I've never heard of that seem really amazing. So you check the checkbox there. Thank you. Next question. Favorite other podcast other than the one you're currently on?

**John Cutler** (01:36:02):
I'm in a... I got a four-year-old. I don't really spend a lot of time... I'm the sort of, I'm such a lightweight, it's like I'll do knowledge project because Shane sent me, you know what I mean? I'll just listen to some, I'll binge things, but I do really like, I've actually been going through old episodes of Maggie Crowley's podcast that she did when she was at Drift. Lots of good guests and I really like Maggie's perspective and I like the guests that she had on there. So sometimes I'll go back to an old podcast. He does these really great memes and stuff, but Jason Knight actually has a fun podcast that I listen to and some of those things. So I think that, but realistically I'm not a huge podcast listener. I'd like to go back to a podcast that hasn't been out for a while, like Maggie's and just sort of catch up on all the guests because I thought that was really good.

**Lenny** (01:36:52):
Awesome. Jason, we love hearing that. Next question. Favorite recent movie or TV show that you really enjoyed?

**John Cutler** (01:36:57):
Oh man, again, I have a kid. It's nothing. There's this thing called, there's a show called Sunny Bunnies. It's these fluffy bunnies. That's really good. And then there's this animated series called Booba and he's this funny guy. I like Booba [inaudible 01:37:13].

**Lenny** (01:37:13):
Great. I'm sure these will be useful to families.

**John Cutler** (01:37:17):
Hardcore product, movies. Really, those are going to up your game a lot.

**Lenny** (01:37:22):
Yeah, I'm sure there's something to learn. Two more questions. Favorite interview question that you like to ask folks?

**John Cutler** (01:37:30):
Oh, so one that I like to do is, I do the behavioral questions like, "Tell me about stuff," but then I'll ask them like, "Imagine I'm interviewing a person you worked with. Now answer in there, tell me about of the same situation." So you'll be like, "Oh, Lenny, tell me about a time that you were faced with adversity and you did this and then you worked with the team to do it. And you would go through it and then you'd answer it.

**John Cutler** (01:37:55):
And then maybe in the process of doing that, you mentioned someone you work with and I'll be like, "Now imagine that you're Mary, who you just spoke about, and things, and how would she answer the tell me about thing as it relates to you?" And so I think it can show some really interesting self awareness. Often people answer that question like they are the hero of the story and the other people are the accomplices in it, but then if you challenge them, "What was that story from the perspective of one of the people you worked with?" I think it's really interesting.

**Lenny** (01:38:21):
Awesome. [inaudible 01:38:23].

**John Cutler** (01:38:23):
So it is a behavioral question. I do think that's the right way and if you dig enough you can really get the depth of the story, but I do think it's fun to challenge people to see how flexible their thinking could be about that situation. I don't know if that's right from an HR perspective, but I like it.

**Lenny** (01:38:39):
I like it too. Final question, you mentioned you have kids. What's the best lesson someone taught you about raising kids?

**John Cutler** (01:38:45):
It's a challenge every day. I just think they operate better when they are fed. The kid as a product is like if you feed the product, then they were just, everything's better. And when you don't, like everything falls apart. So just have snacks with you. That's basically the advice that I have for people.

**Lenny** (01:39:04):
Very practical. Look at you, actionable advice left and right.

**John Cutler** (01:39:07):
Yeah. You got it.

**Lenny** (01:39:09):
John, and I feel comfortable calling you John now, I feel like I just got to know you. You're just like, "I'm John now." We hit our goal of, I think it's going to be the longest episode I've done. This was amazing. John, we've reached the end. Two final questions. Where can folks find you online if they want to learn more, reach out, ask questions if you want them to? And then two, how can listeners be useful to you?

**John Cutler** (01:39:32):
I still am using Twitter a fair amount I think, but LinkedIn could be good. John Cuttlefish on Twitter and then just John Cutler at LinkedIn. Yeah, I think what I would love to hear from people is just send recommendations of people we should hear more from. I think that would be really helpful. Even in the role that I have, I want to start like a guest speaker series to bring people in to talk to our team. And so I think that that would be something that I can work on.

**Lenny** (01:40:02):
Amazing. John, thank you so much for doing this. I'm really excited for this new adventure that you're on, and I'm excited to maybe follow up maybe in a couple years of just what you've learned from this next phase of life.

**John Cutler** (01:40:14):
I really enjoyed the show and thank you for having me.

**Lenny** (01:40:17):
Awesome. Thanks, John.

**Lenny** (01:40:20):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lenny'spodcast.com. See you in the next episode.

---

## [5/22] An inside look at Mixpanel’s product journey | Vijay Iyengar (Head of Product)

**Vijay Iyengar** (00:00:00):
The issue for us at the time was that we took people away from the investment in our core product to go do those other things. We moved people, right? And so the trap there is that you leave yourself right for disruption in your core because someone else can out invests you in that core. And so if you are the leader in some core product, our takeaway here is you should continue to out invests everyone else in that core and then invest the profits that come out of that core into the next venture. Invest profits and not people, or venture capital, which is maybe net present value of profits or something to that effect. But don't take people away from the core to go to these other things because then you end up distracted.
**Lenny** (00:00:40):
Welcome to Lenny's Podcast where I interview world class product leaders and growth experts to help you get better at the craft of building and growing products. Today my guest is Vijay Iyengar. Vijay is currently head of product at Mixpanel. He actually has a very similar career trajectory to myself where he started as an eng intern at Amazon. Then he was an engineer for a while at Uber, then he became an eng manager at Mixpanel. But then he shifted from an ENG manager to director of product, and now head of product at Mixpanel. You don't often see people moving from an leadership role straight to director of product, so it was really interesting to hear what he took from his eng experience and brought into his approach to product leadership. But we spent the bulk of our time talking about what he's learned from the journey that Mixpanel has been on, where they started with a simple product, then scaled to a number of different products, solving many problems for customers, and then made the hard decision to scale back to just a single core focused analytics product.
**Lenny** (00:01:33):
We talk about why they made that choice, what they learned about when it makes sense to expand a new product and when you probably shouldn't, and how they approach that organizationally. We also talk about how Mixpanel builds product, how they think about products philosophy, how they prioritize, and also what you're probably doing wrong in how you set up your analytics for your own product. With that, I bring you Vijay Iyengar after a short word from our wonderful sponsors.
**Lenny** (00:01:56):
This episode is brought to you by Pando, the always on employee performance platform. How much do you love the performance review process? Yeah, it's time consuming subjective bias, and there's rarely any transparency. With the rapid shift to distributed work, it's a struggle to create the structure and transparency that you want to help your employees have the highest impact and growth in their careers. Pando is disrupting the old paradigm of performance management, including a continuous employee-centric approach so employees stay engaged, see their progression in real time, and know exactly when and how they can level up. With Pando, managers can leverage competency-based frameworks to effectively coach and develop their teams and align on consistent growth standards, resulting in higher quality feedback and higher performing teams. Visit pando.com/lenny for more info and get a special discount when you sign up and reference this podcast. That's pando.com/lenny.
**Lenny** (00:02:54):
This episode is brought to you by Notion. If you haven't heard of Notion, where have you been? I use Notion to coordinate this very podcast, including my content calendar, my sponsors, and prepping guests for launch of each episode. Notion is an all-in-one team collaboration tool that combines note-taking, document sharing, wikis, project management, and much more into one space that's simple, powerful and beautifully designed. And not only does it allow you to be more efficient in your work life, but you can easily transition to using it in your personal life, which is another feature that truly sets Notion apart. The other day, I started a home project and immediately opened up notion to help me organize it all. Learn more and get started for free at notion.com/lennyspod. Take the first step towards an organized happy team today, again at notion.com/lennyspod. Vijay, welcome to the podcast.
**Vijay Iyengar** (00:03:52):
Thank you, Lenny. Great to be here. Huge fan of the pod, and so glad I can contribute.
**Lenny** (00:03:57):
I definitely want to talk about Mixpanel's journey both as a product team and a product. But before we get there, as an engineer, you were in a longtime engineer and then you became a product leader, is there anything you had to unlearn as an engineer in the way you thought about leadership and product and business?
**Vijay Iyengar** (00:04:13):
One of the things after you've been in engineering for a while is that develop this tendency to immediately respond with no to new ideas. And I think from the engineering perspective, this is because you spend a lot of your time building and maintaining ideas that maybe are half thought out or didn't really go anywhere, and you just feel like the full brunt of the maintenance cost of that. And so you build up the scar tissue and this immune response to say no to new ideas, and it's a hard no, like no, we're definitely not going to do it. And I think I had to unlearn that moving into product because you get a lot of ideas coming from a lot more places in the organization, and ideas are fragile in their agency and it's a hard no can really kill a whole direction that you could potentially go.
**Vijay Iyengar** (00:04:55):
They could be very high reach and high impact. So, one thing that I've found is the best way to get to a no, if you ultimately need to get there, is to try to make it work. Start trying to make yes work and document how you've tried to make yes work. And do that earnestly, not as an exercise of just an alternative that you're considering. Try to do it sincerely and get to know after trying to make yes work. And so that's one thing I've been trying to just apply my engineer problem solving brain to do that instead of thinking about how it might not work and saying no.
**Lenny** (00:05:25):
Is that something that you recommend engineers work on looking back? I know as a PM, it's like, oh, I love when engineers say yes. This is awesome. I'm going to actually help everyone learn to say yes. But as an engineer, obviously that's a challenge often. What do you recommend to folks that are engineers currently that maybe want to improve on this or shift in how they think about saying yes, saying no when they're asked about something new?
**Vijay Iyengar** (00:05:48):
I think some of the best engineers that I've worked with actually already do this, but [inaudible 00:05:53] they're able to balance both in their head. So, ultimately this balancing act, you just want on-call, you were woken up three times at 3:00 AM due to various bad ideas, and the next morning you wake up and then stand up, it's like, "Hey, can we do this new thing?" You kind of have to have that empathy and do that. So yeah, I think the exercise is just take 10 minutes to consider the idea and just sincerely consider how might we make it work. And if at the end of those 10 minutes, it's like futile and there's no path, it's fine to say no. And it's a good instinct to say no, actually in a lot of cases. But yeah, I would recommend that to engineers. I think it would've been better in my career, for sure, if I had learned that sooner.
**Lenny** (00:06:26):
I want to spend some time on the Mixpanel product journey. It's been an interesting rollercoaster. I think the company's been around for how many years? Since 2010? 2009?
**Vijay Iyengar** (00:06:34):
20009, yeah.
**Lenny** (00:06:35):
So, I know it started as kind of a very simple product analytics product back in the day. And then as you do with ambitious companies, you look for more problems to solve. You look for more problems to solve from your customers. So as I understand it, you guys added a lot more products to the suite of Mixpanel products. And then I know that there are some challenges with scaling that, and maybe the products didn't stick as much as you're hoping. And what I understand is recently, you moved back to just the single core analytics product. And so I'd love to just hear that journey of what that process was like, what you learned as a product leader and as a company about scaling, expanding, trying to solve a lot of problems, and then coming back to one core straightforward problem.
**Vijay Iyengar** (00:07:15):
Mixpanel started in 2009 as provide product analytics to EPD teams. And I think early on, it saw a lot of success because it built this in-house database called Arb, which stands for arbitrary segmentation. And that was necessary because events data, which is the fuel for product analytics, is few orders of magnitude larger than most other types of data that people collect, and so you need a specialized approach to deal with it. And so that I think spurred the first wave of explosive growth, because product analytics was a really burning problem at the time. People were shipping mobile apps like crazy and they needed a solution that could scale, and that was kind of a durable mode for Mixpanel for a while. And I think because we had this SDK that was installed in so many apps and we had this really scalable event collection and analytic interface, it was just natural to expand into a few adjacencies that would leverage those same technologies.
**Vijay Iyengar** (00:08:04):
So, the first one was messaging, being able to send targeted messages to users, which is something that's fairly natural, you might want to do, especially if you have an SDK already installed. Yeah. The other aspect that we've added into was data infrastructure and trying to be the single source of truth of data in companies. And what ended up happening was that by 2018, we had this big churn problem. We had something like 40% churn, revenue churn, our core product. And when we dug into, it wasn't that people were churning because they didn't need product analytics anymore. They had the need. They were just churning to competition because we were just not up to the market in terms of the features we had in our core. And when we dug into why that was, it was just that we had a 50% engineering team that was building products across three domains, product analytics, messaging, and data engineering stuff.
**Vijay Iyengar** (00:08:52):
Our engineering team was just spread too thin to address all of those core gaps in functionality. And so we made a really hard call at the time. We said the hard no to those two other categories and decided to focus our entire engineering team on closing the gap on product analytics and innovating there. And from a process standpoint, how we operationalize this was we threw away all our planning and all the execution and that we work that we'd planned to do so far, and we did something very simple. We took all the churn reasons that our customer success and sales teams had been painstakingly collecting for years, grouped them by category, which was roughly product features we needed to build, sorted descending by ARR, took the top 10 things and made that our roadmap, just give every engineer direct access to customers and give them a bucket to go work on, which I think goes against about a million product best practices out there of just doing that.
**Vijay Iyengar** (00:09:41):
But I think given the context at the time, we needed to optimize for speed, and speed comes when you have extreme clarity on what you want to do and focus. And so we really just optimize for speed in that time. And so in that first year we moved really quickly and we shipped something like a hundred features in that year and closed a lot of gaps. Again, these are all vanity metrics. Measuring number of features doesn't mean anything.
**Lenny** (00:10:04):
And what year was this by the way?
**Vijay Iyengar** (00:10:06):
This is 2018 to 2019.
**Lenny** (00:10:09):
Got it.
**Vijay Iyengar** (00:10:09):
Yeah. So, we moved really fast shipping all these features and instantly saw the improvements to win rate and to retention. But one of the cracks that started to emerge was we neglected the holistic design of our product at the time, right? And if you're shipping features that quick leads, you don't have time to stop and think, where does this go, and how does this fit into our overall system architecture? And what started to happen was that we were hitting diminishing returns with some of these features. And not considering the holistic design and consistency meant the reach of every feature was low. You had to rebuild it for every part of the product that we were in. And so at the time we made... We spun up the second stream that was very design led. And I think this was also coincided around the time we adopted Figma, and it's a really broad design at seat at the table of the company, and we just set up this goal to make design one of our key differentiators.
**Vijay Iyengar** (00:10:53):
So, this design driven initiative was really about how can we think about the system architecture of our product? What are the key building blocks of Mixpanel? Where do they need to fit? How few of them can we have, which is a really important step? And then how will users discover them and how do they relate to each other? But I think this realization was born out of the fact that so many great products win or lose based on their architecture. I think Notion, for example, that pages in blocks architecture is so strong, and you can hang so many features off of those core building blocks in a way that has such high impact on region and discovery of those features.
**Vijay Iyengar** (00:11:26):
So anyway, we did that in parallel with the.... And continued that grind on core jabs. And so the end result of that phase, which is from 2018 to maybe late 2021, 2022, was our retention went from about 60% to 90%, and our NPS went from 16 to 50. So I think, yeah, there's a lot in there to unpack, but refocusing on the core really helped us achieve those results.
**Lenny** (00:11:52):
Got it. Yeah. I have a lot of questions about this. So interesting. So, that phase that you went through where you sorted things by potential ARR, was that the phase of expanding to multiple products or that was post we're going to focus on analytics and go all in there?
**Vijay Iyengar** (00:12:06):
Oh, that was post focusing on analytics.
**Lenny** (00:12:08):
Okay.
**Vijay Iyengar** (00:12:08):
Yeah. Yeah.
**Lenny** (00:12:09):
And you're saying that you had a stream of just builds all the features that were lacking that are causing customers to churn, and in parallel, there was a track of let's build this product, such that it all connects and works together well and it's really well thought through long term?
**Vijay Iyengar** (00:12:24):
The first thing, I might have made it seem like it was just the buckets were features. We did take the step of turning them into problems and being clear, exposing engineers directly to the customers that had those problems and then invent a solution to solve them. So I mean, loosely there were features involved, but a lot of them were kind of core problems we needed to solve.
**Lenny** (00:12:40):
That first approach is so interesting. It's kind of like, yes, we will make more money if we focus on these features. To your point, it ends up being just a bunch of features and products that kind of maybe don't synergize. Looking back, was that a good idea to approach it that way, at least for a while?
**Vijay Iyengar** (00:12:54):
It highly depends on your context. In a very competitive context where there are just table stakes features that customers need and that it's been validated by the market, you need to optimize for speed more so than anything else. But it is an approach that outlives it's usefulness pretty fast, and we've put that approach behind us relatively quickly after that phase. And I would actually say that design driven phase was the next phase, where it was, okay, we're not bleeding on the table stakes anymore, but we want to make a holistic product that has high reach, high impact on the features and is actually usable. And so that was I think a follow-on phase that's necessary. Obviously, depending on your particular circumstances and competitive dynamics, you can sequence them differently, but I think it was the right call to just... Sort of the on-call thing again where when you're in trouble, you got to get out of trouble. You can't mow your lawn while your house is on fire. You kind of put out the fire and then deal with everything else.
**Lenny** (00:13:47):
Yeah.
**Vijay Iyengar** (00:13:47):
So, that's kind of the approach we took.
**Lenny** (00:13:49):
What's an example of a feature or product that you launched within that first track? And then what's an example of something that came out of the designer led approach, if anything comes to mind?
**Vijay Iyengar** (00:14:00):
I think out of the first track, oh man, there's so many that were just core. We didn't have a good cohorts product at the time, just being able to create behavioral cohorts users and create them from any report that we built, right? And I think that, I mean it's just table stakes and analytics to be able to do that. So, that was one of the first things we built, and it was fairly obvious. There's a lot of other things in more advanced types of funnel analytics and a flows and visualization that was really interactive. I think on the design-led phase, the biggest thing I think was visualization consistency and making our charts interactive in a consistent way across our entire product. And so there's two things that enabled. One was that every time we added a new visualization or a new enhancement to a visualization or how something is sorted in one report, it just instantly applied everywhere.
**Vijay Iyengar** (00:14:46):
So, just the reach was multiplied for everything we added. And the other thing is it just made the product more accessible, let us add dark mode. So, it made our visualizations really stunning and really easy to see what the takeaways were. And then every new visualization we added inherited all those benefits.
**Lenny** (00:14:59):
I'm trying to think about being at a company that goes through this phase of, "Hey, we're just going to build a bunch of stuff that we know we need." And it feels like hearing it, it's like, "Oh yeah, and then we're just going to make it all look great and connect and work well." I imagine that wasn't planned, and I imagine that wasn't easy to get people to maybe slow down on just building more products and features or push it in a direction where it's all going to make sense. Can you talk at all about what that process was, how hard it was to shift from we're just going to knock through all this checklist of things to let's just bigger, let's slow down, let's spend a lot of time designing?
**Vijay Iyengar** (00:15:35):
It was definitely more messy internally than I described it. One of the key junctures was when we had this really talented design team and we were putting them on these very tactical projects that was, frankly, that was very engineering led, right? And design would often come in at the end and be asked like, "Hey, can you just make this look nice and put some pixels on it?" And it's just such a waste of your design team to have them do that. But at the same time, the pace was so high that they didn't have time to come up for air and do anything else. And so there's actually this moment where I was an engineering manager at part of this.
**Vijay Iyengar** (00:16:05):
And had a meeting with our BM and our head of design at the time, and we said, "Hey, we can actually do the next three months of projects about any design," which was a kind of controversial thing to say, "but we're doing this so that you can take three months with a set of designers and go think about the system architecture of the product, and we'll wait for that to be done before we do any architectural things that might impact the architecture." And I think that gave designers a bit of breathing room to go do that, just separating them for a bit from the tactical fire. Because what was happening instead was we would get towards the end of the project, bring design in, and they would use each project as an opportunity to squeeze in like, oh, and we can simplify here. And that's just a classic way to blow up scope at the end of the project because there wasn't a dedicated space for design led projects.
**Vijay Iyengar** (00:16:48):
And I think that that was kind of a key friction point that we ultimately had to decouple for a bit, and then regroup and say, "Okay, now we'll look what's our strategy," and just take on projects purely for the sake of improving consistency, reach depth of our UX.
**Lenny** (00:17:02):
Also, looking back, the process you went through adding a bunch of products to solve more customer problems, something every founder and product team thinks about, when should we add new product lines? When should we expand beyond the core? I'm curious what you take away as a lesson and what you'd advise other founders and companies when it comes to when is the time to expand and think about a new product and a third product and a fourth product?
**Vijay Iyengar** (00:17:28):
I don't know if there's a hard and fast rule here. I can just maybe say what made sense and didn't make sense in our context. The issue for us at the time was that we took people away from the investment in our core product to go do those other things. We moved people, right? And so the trap there is that you leave yourself ripe for disruption in your core because someone else can out invest you in that core. And so if you, you're the leader in some core product, our takeaway here is you should continue to out invest everyone else in that core, and then invest the profits that come out of that core into the next venture. Invest profits and not people, or venture capital, which is maybe net present value of profits or something to that effect. But don't take people away from the core to go to these other things because then you end up distracted.
**Vijay Iyengar** (00:18:10):
And the other aspect of that is that those secondary products we took on were in categories of their own. And it's really tempting and you'll often get dragged into accidentally entering another category, and then you'll end up building these bolt-on products that are the best in their category, right? And the adjacent categories for analytics are CDPs or message targeting or feature flagging or something, but there's not that many people that need the sixth best CDP or the eighth best feature flagging or the 10th best message targeting tool. And it ends up being, in aggregate will contribute five to 10% to your revenue, won't seriously accelerate your growth rate, and then takes engineers away from the core product. And so those were the circumstances that we were.
**Vijay Iyengar** (00:18:50):
And I think if you're seeing churn to your competitor on your core product and you're not best in class on any of the other ones, then maybe it's time to reevaluate. And then the last thing I'll say there is that it's also 10x more painful than you think to cut mild successes than anything else, and just organizationally painful. And there's teams that have whole roadmaps, and it's a really painful experience, so you have to think really hard before you kick those off.
**Lenny** (00:19:18):
That is really, really insightful advice, makes me think about if you bundle good enough solutions, there needs to be kind of this anchored tenant that I will not give this thing up and I'll use the third best version of something else, if you have it. But if you're not that valuable and important, you're not going to convince people to use something because they're competing against the best in every category.
**Vijay Iyengar** (00:19:39):
Exactly. Yeah.
**Lenny** (00:19:40):
That is really interesting. I've been doing this kind of series on how different companies approach building product and I have a few questions I'd love to ask around the product development process and Mixpanel.
**Vijay Iyengar** (00:19:50):
Sure.
**Lenny** (00:19:51):
The first is just like, how do you plan? How do you plan? I know it evolves, but just how do you plan currently? How long are your planning cycles? How far ahead do you plan in detail? Do you use OKRs? Maybe let's start there, those three kind of sub-questions.
**Vijay Iyengar** (00:20:04):
We have these unsolved problems and analytics that we're going after. For us that’s like, people always want more power, more simplicity, better data trust, faster onboarding, better collaboration, better price performance. And so we largely organize our teams around those problems and those missions. One quick aside there is that some of those problems have attention with each other. Power and simplicity, there's a trade off there, right? And we want one team to own both, so that they're kind of forced to confront that tension and beat that trade off. And so that's kind of how we think about generally our product team, is these cross-functional EPD teams, each of which that's focused on solving these long-lived paired problems for customers [inaudible 00:20:41] our core analysis team focused on that power, simplicity, trade off problem. In terms of planning, the way it works is that we plan on a six month time horizon. And I can talk about our most recent planning cycle actually, because we're just completing it.
**Lenny** (00:20:53):
Yeah, let's do it.
**Vijay Iyengar** (00:20:54):
Yeah, basically it started out with this strategy memo that our leadership team wrote that basically just conveys this is where we want to go as a company in the next year, and here's how the product team can contribute most of that and just established these key pillars. We shared that with the teams, and they took that and also combined that with all the quantitative and qualitative context they're constantly consuming about the problem they're working on and our customers, and ideated and developed the series of bets for the next six months, which I think are some extent similar to OKRs, where ABET... The anatomy of ABET is that it's problem we want to solve, our hypothesis on the solution, and then some plan to win, some plan to actually get there and a way to measure that you got there.
**Vijay Iyengar** (00:21:32):
And I think one of the unique things that we did relative to other companies that do planning is... I think it usually is sort of this W process of there's the strategy memo, and then teams generate bets and there's a review, and then they go back and I iterate and then they finalize. And we kind of collapsed the middle part of the W where myself and our head of design actually spend time with each of the teams actually ideating on the bets and participating in the solution discovery process, going into the jam sessions and adding fig must keys ourselves with ideas and thoughts on things, which we did because we aren't a huge product team, and we are not going to do 50 things and a half. We're going to do maybe 10 to 12 things.
**Vijay Iyengar** (00:22:12):
And so that's enough that we don't... We can do something that doesn't scale if that enables high bandwidth communication between us and the teams. And it ends up being more messy and unstructured ABET in that phase because we're in there contributing ideas as well. But by the end of it, I think the team leaves feeling both more competent in their bets because there's more thought that's gone into it, and then more aligned top to bottom line why we made certain decisions. And so I think that that's one thing that's different. And then we conclude that process with the roadshow where we presented the rest of the company, and then get their feedback as well.
**Lenny** (00:22:41):
How long is this process generally?
**Vijay Iyengar** (00:22:43):
The teams did pre-work for a couple of weeks, like two weeks in December, and then we did a two week sort of sprint on solutioning and ideation in January, the first two weeks of January.
**Lenny** (00:22:53):
Awesome. And what's the end result of planning for each team? Did they deliver a document with, here's our strategy, here's the big bets, here's a roadmap? Is there a template you pass around? How do you get to a thing that people share and present and comment on?
**Vijay Iyengar** (00:23:10):
Yeah, I think there's basically three artifacts that are kind of linked to each other. So, the first is we use Notion, and so we have a database in notion called bets, which is where each page in the database is [inaudible 00:23:22]. And that has a template, yeah. So, it's kind of roughly what I described with a few more sections of what problem we're solving? What's the evidence of demand? What's the region impact of this problem? How do we know we're successful? And then what's the key driving hypothesis behind the solution? And then a rough line. And then that's tied with a presentation that's kind of like a tight summary of that that has one slide per bet, and then is also tied with more of an execution focused, how do we sequence and staff this thing and eliminate dependencies, which the engineering team contributes to. So, I think those are the three artifacts that are linked together.
**Lenny** (00:23:54):
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**Lenny** (00:25:08):
I know you have some insights on prioritization and some strong opinions on how to prioritize. Can you talk a bit about that and how you advise your product teams to prioritize?
**Vijay Iyengar** (00:25:17):
One really common framework in prioritization is RICE, reach, impact, confidence, effort. And I think it's simple and fairly robust, which is generally good qualities of a framework. But one of the traps with RICE that we observed is that the C and E, the confidence and effort tends to cause you to prematurely deprioritize potentially high reach, high impact bets, really innovative things. And we encountered this on one of our teams early last year were we just RICE'd everything, all the ideas, and a lot of the high reach, high impact things ended up at the bottom because confidence and effort were just so murky for them, as they should be typically for high reach, high impact ideas.
**Vijay Iyengar** (00:25:55):
And so one exercise that we push our teams on is just ignore the C and E for a little longer than it's comfortable, and just sit with those high reach, high impact ideas with engineers and designers in the room committed to actually trying to solve them. Give it a fair shot. And you'll often find if you spend a week on that set of ideas, you can get pretty far in understanding the confidence and the effort. You can probably find a higher confident lower effort way to do them. Then add the C and E back in, and then RICE as usual. And the goal is to end up with a reasonable mix of innovative bets, incremental bets, and then ones that are technical debt or product debt that you need to address.
**Lenny** (00:26:31):
I usually just cut out the C myself. I find that it's not that powerful. Do you do this in a Google Sheet? Do you use this in Notion? How do you actually recommend teams do this prioritization, or just eyeball it?
**Vijay Iyengar** (00:26:43):
I'm not super opinionated on the exact tools that teams use. I think this is a team local exercise typically, but most teams use Notion and just simple tables or databases in Notion-
**Lenny** (00:26:51):
Sweet.
**Vijay Iyengar** (00:26:52):
... work fine for this. I think the other thing on prioritization that's always tricky is estimation. And every engineer will value you estimates are all lies, and if you say it'll take eight weeks, it'll take eight months. But I think the core problem with estimation is you're asked to estimate things before what the thing is, and it's just a strange output to be expected to produce. And one approach that I found really interesting is from this book called Shape Up by Basecamp, which this idea of appetite overestimates, where instead of making the estimate an output of planning, you make the time box or an appetite the input, and you say, "We want to solve X problem and we're willing to invest six weeks solving that problem."
**Vijay Iyengar** (00:27:31):
The obvious question there is how do you pick that time window? It just seems arbitrary. And so the base camp people suggest just pick six weeks for everything, and they're really austere about if you can't scope hammer something down to six weeks, you're doing it wrong, which I think is... It can work and has a lot of benefits if you creates a rhythm in your company, but one approach I found that works better is pick a reasonable sounding appetite and just explore the two to three options around it. Pick six weeks, and then say, "What would we do differently if we only had four weeks or eight weeks?" And you'll kind of naturally find the efficient frontier of cost and impact, and then align on that. And the important thing is that you check in after that time period and say, "Is there any new information that's just we should continue? Did we uncover the biggest risks, and are we just on the long tail of things?" And actually be honest with yourself about that. I think that's important regardless of what framework you use.
**Lenny** (00:28:23):
I really like that. So, is that how you actually operate, you create a time box, we have four weeks for this project, whatever we get done, we ship whatever we don't, we push out?
**Vijay Iyengar** (00:28:30):
We operated that way in engineering, particularly on the infrastructure side, because we have this series of projects that would just take forever, and the longer it takes, the longer it's going to take. And so we've done that exercise quite a bit. I'd say more on the more engineering heavy projects than others, but we're starting to adopt it more in the product side as well. The main exercise we've taken on the product side is more the consider, what would you do differently with different time boxes approach?
**Lenny** (00:28:56):
Just a thought exercise.
**Vijay Iyengar** (00:28:58):
Yeah, it's a good thought exercise. Then it just forces everyone to truly score the requirements. Critical, nice to have, is nice, but really if in two weeks, you're going to get pulled off to do something completely different, what would be a complete solution that addresses the core problem. And it forces you to peel the meat of the problem in first, as opposed to just doing the things that are surrounding it.
**Lenny** (00:29:17):
That's cool. I really like that. I've done that myself. I'm curious if anyone ever does the shape up process for real or it's just like we will ship anything that is ready within six weeks and not actually have specific deadlines or kind of concrete goals of products they need to ship in specific ways.
**Vijay Iyengar** (00:29:32):
Yeah. Well, I think the shape up process, if you run it all the way. They do... Their idea is that you can actually predict on a six week time horizon. So, you can just hammer down scope to something that is complete. It needs to be complete. It can't be milestone one that's like a half baked thing in six weeks, which I think that rigor... The rigor they applied to that across the board, you need to do it all the way. You can't adopt the process halfway. I think the is the challenge. Otherwise you end up with people shipping milestone one and then moving on, which is not the complete product.
**Lenny** (00:30:01):
Makes sense. A couple more questions around how you build product. You mentioned that you have a unique approach to keeping product teams close to customers. And I'm curious what you've learned there, what you found to be helpful and just kind of keeping product teams close to your customers.
**Vijay Iyengar** (00:30:15):
I think this is one thing that is something we invested in pretty early on at Mixpanel. Actually around that time, in 2018, when we refocused on our core product, one of our sales engineers, Aaron, built this automation where he piped all these customer gaps that we got that were reported by our customer success and sales teams, piped that into Slack and just a feed. And what this created was this culture where all engineers and designers could consume that raw feed of direct points of customer with no gatekeeper, no process to access it, no pre-aggregation, right? And I think this scale's pretty far. At a product team of our scale and with our reach of customers, we don't get so much feedback that someone couldn't read it in 20 minutes every day. And for four or five years in engineering, every day I would read all the gaps that we got, and many engineers would do that.
**Vijay Iyengar** (00:31:04):
And one of the rituals that it's enabled is we'll find that engineers will go into that channel and react with a message with an email emoji, which means I'm going to email this customer and find out more, right? And they'll just email the customer and say, "Hey, I'm the engineer that built this feature. I saw you said this specific thing. Can you tell me more? I'd love to understand." They ask the five why's, and then they improve the product on their own. And I think that culture is just so important, and it just empowers all engineers and designers to think a PM a little bit, which I think takes a little bit of a load off on the PM to be the gatekeeper of all that information.
**Vijay Iyengar** (00:31:39):
And then over time, we've evolved it quite a bit as our data stack stack's involved. So, we now not just take customer requests, but we take things that are posted on Twitter and NPS survey feedback and win loss notes from our competitive deals and pipe them both into Slack and into Notion so that we can both get the realtime feed, and then we can sort and aggregate and tag things accordingly. But the key artifact of this is that it's all open. There's no gatekeeper behind that process.
**Lenny** (00:32:04):
That sounds both amazing and wild. Do you still allow engineers just to email customers and ask them questions about this stuff, or is that harder to do it as you've grown?
**Vijay Iyengar** (00:32:12):
Oh no, we still allow that. Yeah.
**Lenny** (00:32:14):
Wow, that's awesome.
**Vijay Iyengar** (00:32:15):
One nice thing about the stack actually, the data stack, is that... So, basically all these feeds information land in our data warehouse, which is BigQuery. And from there, they're pushed out via a reverse CTL tool we use called Census to Slack and Notion that make the note code. But one of the benefits of that is that we can enrich all of these feeds with who's the account? What's their ARR? Who's the CSM? And all that other contact information. So, it's usually not an engineer's blindly reaching out to a customer without letting a CSM know if it's a million dollar account or something. The idea is just trust them with that context, and they can tag the right people and make the right call on that.
**Lenny** (00:32:50):
I'm so curious how that gets prioritized and how PMs are looped into all that, but we don't have to get too deep in that. That's a really cool process. I haven't seen that before. Our engineers were just emailing customers, digging into questions and problems.
**Vijay Iyengar** (00:33:01):
The trap of course is what you just called out is you can't be reacting to everything all the time. And certainly if you ship a redesign, the first two weeks of that, there's going to be a bunch of feedback that's like, I hate this. Go back. And I think that's sort of an organizational muscle you have to build, balance the reaction, and that's just a thing we've had to practice doing, but I think the trade offs are worth it.
**Lenny** (00:33:20):
Awesome. One last question along these lines, can you just talk about the tools you use, the SaaS products you use to run your product team for collaboration, communication, notes, docs. You mentioned Notion as an example.
**Vijay Iyengar** (00:33:31):
I think our stack is actually fairly standard these days. So, we have Slack, Zoom for communication, Notion for docs and any long form writing, and it's a [inaudible 00:33:42] database, and Figma and FigJam for design and whiteboarding. I think what's actually more interesting is our data stack and the productivity we get out of that. I briefly touched on this, where basically all of our data gets EPL'd out of all the systems we have, lands in BigQuery, gets joined and modeled, and then pushed out via census to all the other tools in our stack. And I think that's been a huge productivity unlock because you can build internal tools with very little code. If you can write SQL, you can build an internal tool basically, and that pushes information to the teams that need it. And so that, I think, just has unlocked a lot of these types of things like automating qualitative signals with no code in a reliable way.
**Vijay Iyengar** (00:34:22):
And then if someone like, "Oh, can I get ARR on this?" Yeah, sure it takes two seconds to do that. So, I think that data stack has been a huge productivity unlock for us.
**Lenny** (00:34:29):
Awesome. Have you guys shared that anywhere online, just to show kind of the stack you guys have built?
**Vijay Iyengar** (00:34:33):
We have a couple blog posts that talks about our stack for... We use this both for our PLG infrastructure and our product, let sales, defining a PQL and alerting a new user who fits that criteria, but then we also use it for internal tools. We have a few blog posts on that topic.
**Lenny** (00:34:48):
Sweet. We'll follow up and include some of that in the show notes.
**Vijay Iyengar** (00:34:51):
Yeah, definitely.
**Lenny** (00:34:53):
Final line of questioning, you're one of the smartest people in the world on product analytics heading product for Mixpanel. I'm curious what you think most people get wrong when they're setting up product analytics for their site, their product, their company.
**Vijay Iyengar** (00:35:08):
It's maybe a bit of a hot take because I think so many people-
**Lenny** (00:35:11):
There we go.
**Vijay Iyengar** (00:35:12):
Yeah, so many people still do this, but I think the biggest mistake is setting up analytics using client side SDKs, client side tracking. So, web and mobile SDKs, putting a mixpanel.track or segment.track in your web app or your mobile apps. And reason it's a hot take is that for many people that's product analytics and SDK tracking are synonymous. They're like, "All right, Mixpanel means SDK, I have to put an SDK in my web and mobile app. But that's a mistake because it... We've just seen time and time again, it leads to poor data quality and difficulty to maintain that data. So, the problem on web is, just due to app blockers and other unreliable things, in the JavaScript world, you end up dropping 20 to 30% of your events, and so it just doesn't match your internal databases.
**Vijay Iyengar** (00:35:55):
And then on mobile there's two problems. The first is that you have to reinvent tracking for both iOS and Android because it's two different languages and two different platforms, generally speaking. And so you end up with many duplicate events that semantically mean the same thing, but are just different because of the two platforms, and you might have two teams owning that. And the second issue, which is I think even worse, is that you are kind of beholden to clients updating their mobile app to get to the latest version that has your latest tracking. So if you want to add new tracking, it'll only apply to people at the latest version and beyond. Whereas yet all of your old tracking, whether it's broken or you made a mistake, is still out there in the wild, and so you're constantly getting events that are old and broken.
**Vijay Iyengar** (00:36:32):
And so what we recommend instead, and that we've seen a lot more customers adopt recently is just track events from your servers instead of your clients. And that has three benefits. One, it's instantly cross platform. Web and mobile and TV and whatever other platform, they're all going to go through your servers, so you instantly get a hundred percent reach. The second is it's in an environment you control. So if you want to update tracking, you can update it and updates for a hundred percent of users. And then the third thing is that... And this is I think maybe unintuitive, but it's true, is that engineers have been tracking events from servers forever. It's called logs, right? And events are just logs where they user ID in them. And so they don't need to deal with learning a new SDK and dealing with all of that. They just have to track logs that have some structure and a user ID in them. They're tracking events.
**Vijay Iyengar** (00:37:18):
And so if it's easier for the developer, it'll get done in a higher quality way. So, I think the really simple advice there is just start tracking events from your servers instead of from your clients. And if you need to supplement it later on with context that's only on the client, you can add that on later, but server side should be the default.
**Lenny** (00:37:34):
Maybe a last question is just what's changed most and how companies work with analytics in the past few years? And then just where do you think things are going in the space of analytics?
**Vijay Iyengar** (00:37:43):
Yeah, so I think one huge trend is the rise of the data warehouse. So these are Snowflake, BigQuery, Redshift, and they're really scalable and they speak this SQL standard, which has led to this explosion of tools that have emerged around them and make it really easy and cheap to load data into the data warehouse, and then also easy to push data out of the data warehouse by tools that can just do that. And this has a few implications. So, the first is that the data warehouse becomes the center of gravity for all data in your company. Whether it's product marketing and sales data, they all land there. And I think that's really valuable today in this product led growth world, and a lot of incus filled my bad. But from a data standpoint, that means all these teams need to be operating off of the same version of the truth, and that version of the truth is sitting in the warehouse, and it just needs to be joined correctly.
**Vijay Iyengar** (00:38:33):
The second thing in terms of where things are going is the events, a time series of users at this action at this time, are the universal data model for analytics. And the reason for that is every action, every interaction a customer has, whether it's with your sales team, like a gong call, or with your marketing team, they clicked on that or viewed marketing article or their product, which is more well known, those are all events. They can all be modeled as events. And it's super granular, super intuitive as a way to understand what people are doing. And it's really powerful, because oftentimes you want to ask questions about sequences of events, right? Which user has spent this much time on my pricing page and then looked at three developer docs? That's probably a user I want to reach out to. So many things can be modeled off of that.
**Vijay Iyengar** (00:39:17):
And so I think data warehouse is becoming the loading dock for all this data, which can be very easily modeled this events, but it's not a very great analytical tool for events because SQL is optimized for rows and tables and joints, and not events and sequences of events and segmentations of events. And so one of the things that we're spending a lot of time thinking about is how do we get that really rich, trusted, comprehensive dataset from the data warehouse into a tool that's optimized from the UI down to the data model for events, because that unlocks really fast intuitive exploration of data on dataset that people already have in trust? So, that's, I think, one of the big trends we're excited about and what we see as the future.
**Lenny** (00:39:56):
Interesting. And you think Mixpanel is in a good place to help people do that? Is that how see this, there's something that companies like yours will help people solve, or is this something everyone's going to have to figure out for themselves, or there's like a whole new class of startups launching to help them make the mess out of data warehouses?
**Vijay Iyengar** (00:40:11):
No, there's always a new class of startups joining in the analytics space. It's never dull moment. Yeah, I think this is something that we are looking to solve, because I mean, analytics only as good as the data. And if people are already collecting great data in the warehouse, I mean we integrate with the warehouse really well, then we get access to that good data. Increasingly, what we've been seeing is that companies like in the reverse ETL phase, like Census and Hightouch are effectively reinventing the CDP reinventing, data movement tool like segment on top of the data warehouse. And so really our strategy there is just tightening our integration with those tools. And we've seen just huge growth and people using their data warehouse as the source for events, not adding SDK tracking anywhere, and just saying, "I already have events sitting here. I trust all of them. They're from all parts of my business. Why can't I do analytics on my support tickets and my gong calls just as easily as I can do it about my user behavior." And so I think that's something we're seeing and we're investing in.
**Lenny** (00:41:04):
Awesome. Anything else you'd like to share before we get to our very exciting lightning round?
**Vijay Iyengar** (00:41:09):
Yeah, we opened talking about the transition from engineering to product, and I think one of the things that's just been really fruitful in my career, both on the engineering side and product side, is just adopting that product mindset and getting closer to customers, consuming the raw feed of customer context, taking every opportunity to talk to them. And I'm really excited to see things like this podcast and your newsletter and other forums for engineers to also develop that product mindset then and get closer to customers, because I think long term, that just means better products and services at lower and lower prices, which is just innovation. So, I'm really excited to see more of that in the world.
**Lenny** (00:41:45):
Here, here. With that, we've reached our very, very exciting lightning round. I've got six quick questions for you. I'm just going to go through them pretty fast. Whatever comes to mind, just share, and we'll see how it all goes. Sound good?
**Vijay Iyengar** (00:41:57):
Sure. Let's do it.
**Lenny** (00:41:58):
Okay. What are couple books that you recommend most to other people?
**Vijay Iyengar** (00:42:02):
On the business book standpoint, there's this book called The Goal by Eliyahu Goldratt. And it's kind of an old book, but I like it because it's sort of written in this fast-paced thriller model. It's like a fiction book, but it's about this idea of the theory of constraints, finding constraints in a system and how you can remove them to improve productivity. So, I found it's just a fun read, and also really insightful non-technical books that I recommend to folks, particularly those that live in SF, which is Cool Gray City of Love by Gary Kamiya, who is a longtime SF president. And it just goes into the history and the communities, and even the geography of San Francisco, and I've just discovered so many little pockets in the city from reading that book, so it's something I recommend to people who live in San Francisco.
**Lenny** (00:42:46):
What's a favorite other podcast that you enjoy other than this podcast?
**Vijay Iyengar** (00:42:50):
I'll do non-tech one for this. So, I'm a huge fan of the show The West Wing, and so there's this podcast called The West Wing Weekly that goes into each episode of the West Wing and brings in actors from the show, as well as folks from government to talk about each episode, and it's just a delight to listen to if you love The West Wing.
**Lenny** (00:43:06):
Wait, so they go back to the old show, The West Wing and talk about old episodes with politicians?
**Vijay Iyengar** (00:43:11):
Yeah.
**Lenny** (00:43:12):
That's cool.
**Vijay Iyengar** (00:43:12):
Yeah.
**Lenny** (00:43:13):
Wow.
**Vijay Iyengar** (00:43:14):
Exactly. So, the show's over. The podcast is over.
**Lenny** (00:43:18):
Oh, okay.
**Vijay Iyengar** (00:43:18):
You have all seven seasons, but I think it started in 2016 or 2015 or something.
**Lenny** (00:43:22):
Got it. So cool. Favorite recent movie or TV show that you've really enjoyed?
**Vijay Iyengar** (00:43:27):
Pretty mainstream TV tastes. So, I really enjoyed We Crushed and Severance. Those are two good shows I really enjoyed last year.
**Lenny** (00:43:35):
Awesome. Favorite interview question that you like to ask people that you're interviewing?
**Vijay Iyengar** (00:43:39):
I'm a big fan of open-ended questions, and so one of the questions I ask in the behavioral interview at the start is, walk me through the story of you from college to now, or high school to now, if they're a more junior candidate. And couple interesting things here, interesting to see where people spend most of their time talking and where they don't, and also how they describe the other people on that journey. And do they use a standard framework to describe everyone, or do they go into each person uniquely? So, just tons of follow up questions from that.
**Lenny** (00:44:09):
Final question is, who else in the industry do you most respect as a thought leader?
**Vijay Iyengar** (00:44:14):
Got a lot of inspiration from Gibson Biddle and his product strategy medium thing. And in particular, there's a piece on proxy metrics and the shape of metrics you should use, which I found is a really... The way he frames it is a really elegant way to measure, reach and impact at the same time of your metrics. And then also a big fan of Shishir from Coda, specifically his essays liaison on [inaudible 00:44:37] questions, framing problems, and the one on marginal churn contribution. It's really interesting.
**Lenny** (00:44:42):
Amazing. Both guests of this podcast and people I love. Great choices. Vijay, this was awesome. Thank you so much for joining me. Two final questions. Where can folks find you online if they want to reach out, learn more about what you're up to? And then how can listeners be useful to you?
**Vijay Iyengar** (00:44:57):
I'm on Twitter and LinkedIn. I think my handles will be in the show notes. Not super active there, but I definitely check DMs and would love to connect on either of those. And then how can listeners be useful to me? Yeah, I mean, ultimately at Mixpanel, we're building a product for product teams. So, two things. If you haven't used Mixpanel in the last four years, we've changed a lot, as I've described on the pod, so check it out, and happy to take any feedback to help us improve the product.
**Lenny** (00:45:23):
Awesome, Vijay, thank you so much.
**Vijay Iyengar** (00:45:26):
Thanks, Lenny. It's been great.
**Lenny** (00:45:29):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [6/22] Lessons from Airtable’s unconventional growth strategy | Zoelle Egner

**Zoelle Egner** (00:00:00):
There is sometimes a recommendation or an instinct just like, "Ship things super, super quickly and get them out there." And I'm not saying don't move fast. Obviously you need to move fast in the early days, but make sure someone rereads your email so that it sounds good. Invest in having a decent photo or a decent illustration. If you have sample content, this is actually a big one, sample content for your productivity app as an example. Take the time to not have it be like Jane Doe 12 times in the name list. Have it be references to your industry so that people are like, "Oh, hey. That's a joke about Steve Jobs. I'm a designer. This person is thinking about me."
**Zoelle Egner** (00:00:35):
It's small stuff, but it tells that person, like, "The people who worked on this were thinking about me as a customer, they built it with me in mind, and that means that it is more likely that this is going to fit my needs than something generic." And that builds up both the brand trust that we've talked about, but also the personality of the company, and makes people want to root for you. And frankly, when you are small, you need everyone rooting for you that you can possibly get.
**Lenny** (00:01:02):
Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard won experiences building and scaling today's most successful companies. Today my guest is Zoelle Egner. Zoelle was one of the earliest employees at Airtable, where she led their early marketing and customer success teams, and generally just helped Airtable grow into the legendary business that it is today. She also spent time in Box. She's advised dozens of startups on marketing and growth, and is now head of marketing and growth at a startup called Block Party. 
**Zoelle Egner** (00:04:12):
Hi, thanks for having me.
**Lenny** (00:04:14):
It's very much my pleasure. Something that is pretty cool is that we actually met in my newsletter Slack community. I actually looked this up of how we actually started chatting, and it was me cold DMing you to get a discount on Airtable for the newsletter subscribers. And you very happily got me that, hooked us up, and then you became a go-to Airtable person for advice on what Airtable did right and wrong over the years. And so thank you for being that person and also I'm really excited to have you on this podcast and to learn from you.
**Zoelle Egner** (00:04:43):
I am super excited to chat.
**Lenny** (00:04:45):
Awesome. You're probably best known for your time at Airtable, which, correct me if I'm wrong, you're employee number 11.
**Zoelle Egner** (00:04:53):
That's right.
**Lenny** (00:04:55):
Okay, and at Airtable you led marketing, you led the customer success teams, so we're going to chat about all that stuff. But before we get into that, I want to chat briefly about this other project that you worked on, that from the outside felt like a really fascinating thing, and a really impactful project, and a really cool team. And it's called Vaccinate California, I think, is that how you pronounce it?
**Zoelle Egner** (00:05:13):
Mm-hmm.
**Lenny** (00:05:13):
See, I just-
**Zoelle Egner** (00:05:13):
VaccinateCA.
**Lenny** (00:05:15):
VaccinateCA. Okay. Could you just talk a little bit about what this was? What were you trying to do? What was the impact you had? How did it all go?
**Zoelle Egner** (00:05:21):
Yeah, absolutely. So VaccinateCA existed to help people in California find and get a COVID vaccine as quickly as possible, and that sounds really trivial right now, but you have to wind back to January of 2020, when vaccines were first coming out, and it was really hard. So just as a reminder, because most of us have blocked that from our memory. 
**Lenny** (00:05:40):
Yeah.
**Zoelle Egner** (00:05:41):
The federal and state systems didn't really exist yet, and so everything was this horrible hodgepodge, where eligibility depended on not only what state you were in, it was down to the county, and even sometimes the individual facility. You would be at a Walgreens, and talk to them, and they'd be like, "Oh, you have to be over 65, and also in one of these 12 categories of employment in order to get the vaccine." And then you'd go a mile away and they would tell you something totally different. So people would stand in line for hours. There were phones going off the hook, utterly madness, and really, really scary for a lot of people who were trying to figure out how to keep themselves safe. 
**Lenny** (00:06:17):
Yeah, I remember those days well.
**Zoelle Egner** (00:06:19):
Yeah. So this organization was founded essentially by a tweet by Patrick McKenzie, for those of you who are on Hacker News Patio11. And he had basically this really simple premise, which is, "If you call a pharmacist, and you ask them who they can give a vaccine to, and what vaccine they have, and then you put that answer on a map, someone else doesn't have to make the same phone call. And that takes lots of pressure also as a healthcare system and also helps people to match supply and demand." 
**Zoelle Egner** (00:06:47):
So surprisingly, somehow, that tweet, which is essentially like, "Call people, put in spreadsheet, put online," turned into an entire, full nonprofit that was mostly on Discord, Zoom, Airtable, and not only had this entire hundreds of volunteers who were making phone calls in the state of California and eventually, actually, nationally, we became Vaccinate The States eventually, we were also doing this thing called web banking. So we would go and scrape all the official sources as they started coming out, and then validate them because they were not always correct. And eventually we had the most comprehensive database and map of locations in the entire country, including more comprehensive than the federal government and most of the states because they had really complicated limitations on what they could and couldn't publish based on some relationships they had. We didn't have those limitations.
**Zoelle Egner** (00:07:37):
So it meant that we became this clearing house, essentially, for this information and we built an API. We were working directly with Google. And if you ever looked up vaccine locations on Google Maps, that was us feeding that to them, which was really cool. And we also made maps you could see on county websites, so it would help you understand what was available in your area. One of the coolest things that I've ever worked on.
**Lenny** (00:08:01):
Okay, exactly. That's exactly I imagined how epic this was. Just to make sure people understand what you're describing, basically you had hundreds of people sitting there on phones calling vaccine locations, getting the specifics of who is able to get a vaccine there, and then just giving people a pointer of where they can get a vaccine.
**Zoelle Egner** (00:08:18):
Exactly. So I came in initially, a colleague of mine at Airtable had been helping out with the building out of the backend. And they started getting media attention. And they thought, "Oh, well this will help more people understand that this resource is available." So I got brought in to do some PR help, basically help them figure out how to get the word out, and then ended up actually quitting my job at Airtable to work on it full-time.
**Lenny** (00:08:40):
Oh wow.
**Zoelle Egner** (00:08:41):
Yeah, I was on the board and also managing all outreach and other stuff. So we did lots of really cool education, helping people understand their eligibility at all. Built a bunch of fun tools for that as well, but it was a pretty incredible six months, where we filled a really critical gap in the infrastructure of the country. 
**Lenny** (00:08:58):
It's wild that was the best solution, is just call people and create your own. 
**Zoelle Egner** (00:09:03):
You know?
**Lenny** (00:09:03):
I imagine there was, at Airtable, were you using to store the data?
**Zoelle Egner** (00:09:07):
Oh yes. 
**Lenny** (00:09:07):
Okay.
**Zoelle Egner** (00:09:07):
We built an entire insane database, and then eventually custom software on top of that, to make the people who are making the phone calls more easily get the information in. It was a whole thing. Very cool to see, though, not just tech people get involved. We had, in our volunteer base, people from absolutely every walk of life, not just in California, globally. I remember there was a volunteer who said that he decided to join, he was based in Israel, and he had had no trouble getting the vaccine whatsoever, but seen something on Twitter about it, and just decided he wanted to make sure that people were able to get the vaccine as easily as he did. And he spent dozens of hours calling folks, even though he was in a totally different time zone. But really lovely to see all these different people, retired teachers. I think we had a bunch of 12 year olds who were helping out on the code, of all things, all who just really wanted to make sure that they could keep their community safe.
**Lenny** (00:10:02):
What happened with this organization? It's a nonprofit that now continues to run or what's happening?
**Zoelle Egner** (00:10:06):
No, we did something which is not common. We actually decided to shut it down after six months. Partially, that's because the existing system finally caught up. And frankly we didn't want to be in a place where we were pulling away resources that could be put towards other things that are going to be more impactful. We always saw ourselves as a stop gap, and once we got to the place where we felt like we weren't really being additive, we wanted to get people's time back, so they could work on other things. So it doesn't exist anymore. I think you can still go check out the archive. We found some researchers who are doing interesting research on it, because there's very fascinating data in there about the equitability of some of the distribution of the vaccine based on where it was available, but the organization is gone. We had that beautiful moment in time and have all moved on. Hoping we don't have to get the band back together, because hopefully it's not necessary anymore.
**Lenny** (00:10:58):
Oh, man. I'm watching The Last of Us right now about this-
**Zoelle Egner** (00:11:02):
Mushroom people.
**Lenny** (00:11:03):
... mushroom based disease, and that scares me now. 
**Zoelle Egner** (00:11:06):
Yep.
**Lenny** (00:11:06):
Anyway, on this podcast I try to get to things people learn from these experiences, and so I have to ask what you learn about forming something like this, just ad hoc, pulling a bunch of people together, and having them focus, and get things done, or just scaling it, or even shutting down. I guess what have you taken away from that experience that you maybe will bring to either future one-off things like this or even just your work in general?
**Zoelle Egner** (00:11:31):
Yeah, I'd say probably three things. One, the incredible power of a simple idea to bring people together. One of the reasons why VaccinateCA was so powerful and got so many people to help is everybody immediately understood why it would be useful and how they specifically could be making a difference. And combining those two things was an incredible way to bring a lot of people on board very quickly, because from a messaging perspective, messaging, something very important to me as a marketer, it was so concise. Like, "Pick up phone, help save lives." Really straightforward. People really, really got that. It allowed them to feel like they had agency in a time when everything felt really, really out of control. I think there's a lot of opportunities we have to activate our communities and give people that sense of control that are both going to be helpful more broadly for society, but also just for those individuals as well to make them feel a little bit more safe, a little bit more like they can actually have a difference in things. 
**Zoelle Egner** (00:12:34):
I think in tech we often don't jump into these problems. This was not sophisticated technology. It was phones, Discord, and Airtable mostly being used like a spreadsheet. It wasn't anything wild. Even that very simple infrastructure was enough to make a huge difference. And we have some evidence that we saved a lot of lives as a result of it, which is pretty special. I think part of it is also just saying, "We don't have to be hesitant to jump into these problems. It's important to engage with experts in the field, is not to say that tech solutionism is always the answer." And again, this is not super sophisticated technology, but because we were able to go in and talk to the people who are actually affected, get into the system that already existed, and make something really simple, really fast, it actually did have a huge difference and that's really exciting.
**Lenny** (00:13:24):
Just to double-click on that one, actually reminds me, some founders of companies I've invested in, I often hear how much easier it is for companies that have a mission that people are excited about for them to hire versus companies that don't. And so it's a really good reminder of just the power of having a mission and a vision that is really compelling to people versus some B2B software that people aren't [inaudible 00:13:47] excited about, even though there's a great reason to have great B2B software. Love B2Bs.
**Zoelle Egner** (00:13:50):
There are. I love great B2B software. I've spent most of my career on it. But I agree with you. I think if you have an authentic mission and people aren't just like, "Oh, sure, okay. You're connecting the world." But really it's some telephony startup. Like, "Okay."
**Lenny** (00:13:50):
Yeah. 
**Zoelle Egner** (00:14:05):
If people feel like it's genuinely authentic to what you're building, it can be incredibly meaningful.
**Lenny** (00:14:11):
Yeah. I just remember a founder who, he is a second company, because the first company did not have an amazing mission. The second one did. And like, "Wow. So much easier to hire for this new startup."
**Zoelle Egner** (00:14:20):
Yes. 
**Lenny** (00:14:20):
So totally get that. 
**Zoelle Egner** (00:14:20):
Absolutely. 
**Lenny** (00:14:22):
Okay, number two and three.
**Zoelle Egner** (00:14:23):
Number two and three, I'll try and be more brief. 
**Lenny** (00:14:25):
It's all good.
**Zoelle Egner** (00:14:26):
Number two, I would say just the importance of relentlessly repeating the exact same stuff over and over again, even if you feel like everyone definitely knows. This is something that I've seen play out in every single leadership role that I've had, but it was never more acute than here, particularly because we had this broad coalition of hundreds of people with very different backgrounds. Some people coming to the meeting, some people not, whatever else. I think I repeated the same three talking points about why what we were doing mattered 5,000 times. Cannot overemphasize how many times I said the same stuff, and so did every other member of the board. It really is important and people will fill in the blanks with totally wild things if you don't continuously have that discipline of repeating yourself. You just have to get used to saying the same stuff. And if you do it correctly, it's super motivating. Even if you're sitting there being like, oh my gosh, "I have to say it again." it's worth it.
**Lenny** (00:15:22):
This reminds me, I don't know where I saw this, it's just in my head right now, that the CEO and founder's job, their actual title is repeater in chief.
**Zoelle Egner** (00:15:22):
It absolutely should be.
**Lenny** (00:15:31):
It resonates. Yeah.
**Zoelle Egner** (00:15:31):
I've worked with some leaders who never wanted to. They're like, "No, this is going to be boring for people." And you just have to be like, "Honestly, most people are never listening as much as you think that they are."
**Lenny** (00:15:39):
Yeah.
**Zoelle Egner** (00:15:39):
"We wish that they would. But you have to say it 12 different ways in writing, and out loud, and all this other stuff. You're never as important as you think you are, unfortunately, when it comes to that." 
**Lenny** (00:15:48):
Oh, these are great lessons. Okay. What else do you tell? 
**Zoelle Egner** (00:15:51):
I think my last learning was really about the power of having a laughably small MVP for something. By the end of this, we were covering the entire United States. We had an API, we had custom software on the front end, this whole behemoth of stuff that we got to in four months or something. In the beginning it was truly, basically, a spreadsheet, and phones, and that was it. Even that, for the first few weeks while we were getting the rest of the infrastructure really going, not only had tremendous impact at one of the most important parts in the pandemic, but also gave us so much information about we actually needed to build that was going to be helpful. And I remember having all of these assumptions about what was going to be necessary to manage this coalition of people to make sure that we had really good data quality.
**Zoelle Egner** (00:16:41):
Because one of the most important things you can do if you're trying to be a trusted source of truth is actually have the correct information. Sounds trivial, it's not at all at that scale. And I was totally wrong about all my assumptions. I thought we were going to have to have totally different types of oversight. I thought we were going to have totally different tooling. And it turned out we could do something way lighter weight that would allow us to move much faster as the regulatory landscape kept changing, as all the rule making at individual places kept changing. And that agility, that willingness to do just the smallest possible thing is obviously a little bit of a trope in the industry. 
**Zoelle Egner** (00:17:15):
People talk about it a lot, but it's never been driven home to me so much, because we're talking about something that had incredibly high stakes as people's health, and we're still able to do it in that context. So if we could do it there, you can imagine that the applications of that in other industries are just tremendous. So yeah, if you're listening to this, and you were thinking maybe you needed to add more stuff, I bet you could prune.
**Lenny** (00:17:39):
And it's nice to have the forcing function where the world is changing so quickly and the team's probably small, where you are forced to build small. Which I think is why this reminder is so important. Oftentimes you have more resources, and you end up building more just because you can. And yeah, what you're saying is oftentimes, "It'll shoot you in the foot."
**Zoelle Egner** (00:17:55):
Yes.
**Lenny** (00:17:56):
Amazing. I didn't expect to get into this much detail with VaccinateCA and so I'm glad we did. Let's zoom out a little bit, and just fill in some gaps on your background, briefly. Can you just highlight some of the other wonderful things you've done in career? Airtable, we talked about, VaccinateCA, just broadly, what else have you been up to? 
**Zoelle Egner** (00:18:13):
Yeah, absolutely. Okay, so I'll try and be brief. I worked in tech for more than a decade, mostly marketing and customer success, a little bit of ops. Before I got into tech, I was a little bit of a dilettante, so some non-profit, healthcare, dying big box retail, because I graduated right into the recession and I was certain no one would hire me. Turns out that was actually wrong. But on the plus side, now I know what dysfunction looks like at great scale, which is actually quite an education and very useful. But I always knew I wanted to get into tech, partially because I'm from the Bay area, and partially because I had been obsessively power mapping the industry, and looking at its flocking patterns, and who had what types of influence, because I'm a nerd. And I really wanted to see if I could get in, in the first place. Because- 
**Lenny** (00:18:59):
Wait, can you talk about this, which, what is it you did? What did you call, a flocking pattern?
**Zoelle Egner** (00:19:05):
Sure. You can imagine in any community, there are nodes of influence, people who know a lot of folks, they have money, whatever it might be. And they're able to direct how that community or that ecosystem evolves. In the tech industry, typically VCs will often play a role in this, but so will certain types of executives. And you can follow how they move between different companies, and who they worked with, and then see that influences who gets investment in the future. It influences the different partnerships that evolve. It influences the assumed wisdom in various different careers. And because I'm a big old nerd, I was literally drawing diagrams based on-
**Lenny** (00:19:48):
Whoa.
**Zoelle Egner** (00:19:48):
... reading people's blog posts of who was influential in what way? Because I was non-technical. I tried programming, and I hated it, frankly. And so I was like, "Okay, it's 2010, it's 2011. There's not clear ways to get into the industry as a non-technical person. I need to figure out how to do this with people. Because otherwise I'm not sure why someone would take a chance on me with what I have done historically. And that sounds a little insane, but it's very effective. And I ended up getting my start in tech basically by identifying a company where I thought I had a unique set of connections or understanding of the space that they were working in, where I thought I could maybe email the CEO and be helpful.
**Lenny** (00:20:29):
And did this connect to that diagram you drew? Did this help you point in that direction?
**Zoelle Egner** (00:20:34):
Yeah, absolutely. So I was closely tracking YCombinator and that whole ecosystem. So I knew I wanted to find a smaller company, where they maybe were having more difficulty hiring, because they were less well known or a little bit less, I don't know, sexy. But while they were still connected into that broader group, because it has with a pedigree that people would take you seriously if you had worked at a YC backed startup.
**Lenny** (00:20:55):
Right.
**Zoelle Egner** (00:20:55):
Anyway, I got really pointy hat strategic about this, but it was effective. 
**Lenny** (00:21:00):
Do you still-
**Zoelle Egner** (00:21:00):
And-
**Lenny** (00:21:00):
... have this diagram, by the way? It'd be so funny to look at it right now.
**Zoelle Egner** (00:21:03):
No, I don't think I have it anymore. I might be able to dig it up, but alas, I think it may have been lost in one of my many moves since then. 
**Lenny** (00:21:03):
All right.
**Zoelle Egner** (00:21:03):
It's been-
**Lenny** (00:21:03):
No problem.
**Zoelle Egner** (00:21:03):
... more than a decade. 
**Lenny** (00:21:18):
Okay. I imagine that was true. Okay, so I think I cut you off. You were talking about some of the things you've done in your career.
**Zoelle Egner** (00:21:20):
Yeah, ended up using my studies of the space to get into a role as employee one at a developer focus YC backed startup. And the funny story on that is that I got that role by cold emailing the CEO while I was still in college. And then he actually followed up with me almost immediately, because I'd offered to introduce him to some professors, which was useful for the type of business. And then I ignored him for two years because I got busy with my thesis, and got other jobs, and whatever, came back to it and wrote this ridiculous apology email, being like, "I promise I respond to emails faster. I see that you're hiring. Would you give me a second chance? Please, can I come work for you? I have no experience that's useful, but I work really hard." And I figured he would either laugh me off of the internet or give me a job, and very fortunately for me, he gave me a job. So thanks, Ryan. Appreciate that. That was how I got into tech.
**Lenny** (00:22:11):
Thanks, Ryan. 
**Zoelle Egner** (00:22:12):
Yes, we appreciate it. So that startup got acquired by Box. And when I went over to Box, they had never had paying developers before. So we were bringing over seven figure contracts. So I started developer success programs there. And then in a totally wild shift, I ended up moving over to run their social media editorial and internal comms, which doesn't sound related to developer success, but I had always been a writer, and I wrote this blog post about what it was like to be an early stage non-technical employee. There was a little spicy, talking about some of the challenges, and I didn't tell anyone I was going to do it. And I got this email from PR being like, "We need to have a meeting." And I was like, "Oh, they're going to fire me. I went too far." I thought I was being circumspect, that I went too far. And in the meeting they were like, "Hey, we really think you should apply for this job. We would love to have you run social media." Which is not the outcome I expected.
**Lenny** (00:23:05):
That's a cool learning, there. Just like, "Do stuff." You know? "Don't be afraid."
**Zoelle Egner** (00:23:08):
Yeah, it was definitely not the expected outcome, but one that was very exciting. So got to go run those programs for a couple years through the IPO, which is a whole education in and of itself, to see how comms changes when you become a public company. And then I was on Hacker News obsessively at the time, and I saw the beta for Airtable come out. Immediately signed up, and became obsessed with the product, and evangelizing it to everybody that I knew and ultimately ended up figuring out a way to finagle my way into that role as employee 11 there. 
**Zoelle Egner** (00:23:43):
And it sounds like we're going to talk about Airtable more, so I won't belabor that, but marketing and customer success stuff, ended up leaving for VaccinateCA, and then the last little bit here is just when that ended, I really thought I wanted to start my own company. So I gave myself a certain window in which to try out different ideas, and at the same time was advising and consulting. Ultimately didn't end up finding anything that I felt so much conviction that it was worth blowing up absolutely everything else about my life in order to go heads down on a company. So eventually decided to go in-house with one of the companies I've been advising, Block Party, and now I run marketing and growth there.
**Lenny** (00:24:19):
Can you just explain Block Party briefly? [inaudible 00:24:21]-
**Zoelle Egner** (00:24:21):
Absolutely. We're an online safety company. We help users have more control over their digital experience. And our first product is anti-harassment and anti-spam tools for Twitter.
**Lenny** (00:24:30):
So you've worked at Box, Airtable, now Block Party. You've advised a lot of companies around marketing product growth. I'm curious if there's a thread that has maintained through all of those experiences in terms of what works well for marketing, and growth, and things you've learned that just consistently- [inaudible 00:24:52]
**Zoelle Egner** (00:24:52):
A few pieces that go into how I choose companies that create that thread. And part of this is about me wanting to match what I think I'm really good at with what will have the greatest leverage for a company that I work at. I've mentioned I'm a writer, really care about telling stories, and helping people to understand new or novel things. I also really care about product quality. I'm a little bit of a product snob. And one of my strengths is enthusiasm. So if I can't genuinely go to a customer and tell them, "This product is going to solve a real problem for you and it's going to be amazing." I can't do my job. So all of the companies that I've chosen to go to have had this foundation of an incredible product experience that maybe people didn't fully understand, and where I could come in and help connect the dots between that amazing product that's going to be really, really helpful and the opportunities for a much wider range of people to benefit from that.
**Zoelle Egner** (00:25:46):
So in practice, what that means is I often end up working at companies that are in a position to really punch above their weight from a brand perspective. They're typically much lower headcount than you would ever expect. They're typically way earlier stage than you would expect, but I've been able to put together a brand or an experience that allows people to invest themselves into the company with a high level of trust, I guess. 
**Zoelle Egner** (00:26:13):
I'll be more specific because that's really ambiguous. Airtable, it manages mission critical workflows, highly sensitive data. It's super important. You only use tools you can trust for that type of thing. The same thing is true at Block Party, online safety. You have to trust the company that you're entrusting your safety to. And in my experience, people, and especially founders really underestimate how much every single touchpoint a customer has from word of mouth or the ad that brings them in the door, landing pages, signup flows, customer service experiences. Every single one of those moments is building a brand that is adding or removing trust.
**Zoelle Egner** (00:26:48):
So for me in the early days, that means thinking about like, "What are the signals that I can provide to future customers that say, 'We understand you specifically, and our solution is designed for a person like you.' And two, that will say, 'Hey, we're actually operating on a much higher level than you might expect for a company of our size or our stage. We take this really seriously. We have all the things in place to take care of you. So you shouldn't be afraid to spend six figures or put your safety in our hands because we've got your back. We're doing this the right way.'" Has tremendous dividends when you're in a business that is often driven by word of mouth. Because if you take care of people and you follow up that brand experience with a product experience that is really powerful and actually does the things that says it's going to do, then your word of mouth can become a huge driver of growth for the company.
**Zoelle Egner** (00:27:40):
Of course, the outcome of this in practice is really funny. So I remember really distinctly having to invite customers to go out to lunch with us when they would come to San Francisco back in the Airtable days, because we had 15 people in a teeny tiny office. It's not that I wanted to mislead anyone, but I didn't need to reinforce the fact that they were spending six figures with us when we had 15 people. If they had gone to look on LinkedIn, they could have figured that out, but we didn't need to remind them that we were so small, and they were running some of their most important processes with our product. I think I was on the phone with Slack at one point. And they were like, "Oh, well you guys are probably about the same size company as we are, right?" And I was like, "Not quite. A little smaller, just an entire order of magnitude, no big deal, it's totally fine. We're all smooth. We'll take care of you. It's going to great." But it-
**Lenny** (00:27:40):
Amazing.
**Zoelle Egner** (00:28:27):
... really makes a difference, all of those little things.
**Lenny** (00:28:31):
That reminds me, I heard stories of very early Airbnb days where they had to take meetings in a bathroom, or in the hallway, and they did interviews, I think in the hallway because there was no space.
**Zoelle Egner** (00:28:41):
We did a lot of calling from the hallway at Airtable, also from this weird internal patio you could only get to through climbing through a window. The window kept breaking. And so I, at one point, remember someone getting stuck outside trying to interview someone with the windows closed. Utter, utter ridiculous nonsense. But you know, that's all the fun things that happened in the early days before you become bigger.
**Lenny** (00:29:06):
Yeah, I love those early day stories. 
**Zoelle Egner** (00:29:08):
Yeah.
**Lenny** (00:29:09):
I really love the concept of punching above your weight as a startup. What else did you do at Air Table or other places that help you do that? One is just don't let them see how small you are, necessarily. Are there any other technical things you recall that like, "Oh, here's things that really worked really well for punching above our weight as a small company at that point."
**Zoelle Egner** (00:29:29):
A couple of these things are very unsexy, but very useful. One, make sure that your landing pages, and your emails, and other things have a level of polish that makes them feel a little bit more done. I think there is sometimes a recommendation or an instinct just like, "Ship things super, super quickly and get them out there." And I'm not saying don't move fast. Obviously you need to move fast in the early days, but make sure someone rereads your email so that it sounds good. Invest in having a decent photo or a decent illustration. If you have sample content, this is actually a big one, sample content for your productivity app as an example. Take the time to not have it be like Jane Doe 12 times in the name list. Have it be references to your industry so that people are like, "Oh, hey. That's a joke about Steve Jobs. I'm a designer. This person is thinking about me."
**Zoelle Egner** (00:30:20):
It's small stuff, but it tells that person, like, "The people who worked on this were thinking about me as a customer, they built it with me in mind, and that means that it is more likely that this is going to fit my needs than something generic." And that builds up both the brand trust that we've talked about, but also the personality of the company, and makes people want to root for you. And frankly, when you are small, you need everyone rooting for you that you can possibly get.
**Zoelle Egner** (00:30:45):
So those little bits of polish that don't take a ton of time are absolutely worth it. The last thing I would say is making sure that in your public communications launches, if you ever talk to press, which some companies can and some companies can't, having more of a point of view than just about your product, you can try and say, like, "We are part of something bigger. Here's the broader circle or movement that we are a part of." It makes it feel more inevitable and more like you're not just self servingly talking about your tiny corner of the world, but that it's actually part of this much bigger trend. It will be more compelling and it feels like you're operating at a different level of sophistication that can be really helpful.
**Lenny** (00:31:28):
I love that. On the first point, basically, it's attention to detail and obsession with quality is what I'm hearing. 
**Zoelle Egner** (00:31:34):
Yes. 
**Lenny** (00:31:34):
Just to make it clear, this isn't just a tiny team just pushing the stuff out. I imagine most founders would be like, "Yes, I would love, we are going to focus on quality. We'll make sure everything looks great." In reality it always is this trade off against other things they could be doing. 
**Zoelle Egner** (00:31:50):
Yep. 
**Lenny** (00:31:50):
What do you think folks can do to help keep that level of quality high? Is it just one person being obsessed and just reviewing everything like a founder? Is having someone like you that's just very detail oriented, just review everything? How do you actually execute that when you have 1,000 things to do?
**Zoelle Egner** (00:32:05):
100%. I'd say there's one of two approaches and you articulated them here. One is you can have the founder that is the avatar of quality, who is just relentlessly being like, "Hey, we're going to do the 15 minute check. Yes, we're going through it. Yes, I'm going to send you a copy of this email, and someone else going to click every link in it, and make sure they're not broken." Or, you can have someone else be the avatar of that who is in the company. I would say in many of the companies I have worked at, that has been me, because I've been the marketing human who cares. But it doesn't have to be a marketing person, it can be someone on product. It can be, honestly, even someone on customer success if you're willing to let them provide their feedback on the way that you're showing up in the world, which you should because they have fantastic insight. There just needs to be someone. 
**Zoelle Egner** (00:32:50):
And I think building that into how you interview can be very helpful, as well. So finding people who understand those trade-offs and that balance, and who are willing to put in the extra 15 minutes, but aren't going to spend an extra week trying to obsessively QA everything. You don't want to go that far. Just who has that bent towards detail can be very helpful. Also, just make yourself a checklist. It doesn't have to be complicated. "Every time we put out a blog post, these are the three things we're going to do. Every time we send out an email, it needs to be seen by at least one other person." None of this is rocket science. You just need to make a little process for yourself, and then it can be very fast and lightweight, but the dividends are worth it, I think.
**Lenny** (00:33:31):
I like how simple this is, just to look like a bigger company, is just pay attention and focus on the little things. It's not a big, whole thing. [inaudible 00:33:39]
**Zoelle Egner** (00:33:39):
There are some bigger things you can do if you really need to. My favorite silly example of this is Airtable, back in the day, got roasted on Twitter for having billboards that were not super specific about a specific problem or whatever. They were just billboards that we had out. And everyone was like, "This makes no sense. Why are you doing this? We don't understand." They were actually super effective for us because we had a different goal than everyone thought that we did. 
**Zoelle Egner** (00:34:03):
For us, it was all about signaling to some very large companies that we were a legitimate and large enough company that they could trust, and we had geographical concentration in specific areas, because we were in the fashion industry, the media industry in New York, we knew exactly where all of their offices were and we knew if they saw our billboards, walking to work, and then got the request to IT for the budget in order to pay six figures for Airtable, they were more likely to be like, "Oh, it's not just some weird startup we never heard of." Like, "Oh, I've seen that billboard, they must be legitimate." And that sounds really silly, but it wasn't actually that expensive.
**Zoelle Egner** (00:34:40):
We got mostly remnant inventory, which is at the end of a particular buying cycle. Sometimes they haven't fully sold everything, and you can get the slightly less good ones that are still maybe where you want them for really cheap. And everyone thinks that you only buy billboards if you're huge. So that small signaling thing was a way for us to make sure that we remove some of the risk of not being able to close deals because we were so small. So you can get creative about it. Most of the time you're not going to do that. Most of the time it's like, "Reread your emails." But you could also push it even further if you need to.
**Lenny** (00:35:12):
What is that full rough cost of billboards like? Because I think people think about billboards and it's hard to even know what they cost. What's a number?
**Zoelle Egner** (00:35:20):
It really, really depends, so I'm hesitant to give you a number because which metro you're in, it ranges vastly. I would say you can expect that some of that inventory is in the low thousands of dollars, which is way lower than you might expect.
**Lenny** (00:35:34):
For one billboard.
**Zoelle Egner** (00:35:36):
Yeah. So you don't need to get a million. And I'm not suggesting you go get one on 101. Good luck to you on that. That's expensive. But you can get one in a reasonable neighborhood in New York for way less money than you might expect, if you're willing to do remnant.
**Lenny** (00:35:52):
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**Lenny** (00:36:41):
Following this thread a bit, my next question is, and this may be the answer, is when you think about Airtable's growth strategy, growth tactics over time, what would you say are one, or two, or three of the most impactful marketing or growth tactics that work best over time? And maybe billboards are one of them.
**Zoelle Egner** (00:37:02):
I wouldn't say they were the highest ROI, but they're certainly one of the more interesting things that we did. They were useful, don't get me wrong. But I think maybe some other ones are more interesting. The boring answer that I will caveat this with is that one of the pieces of our acquisition playbook, it was very standard, that did work quite well, was some unconventionally targeted Facebook ads. That era is over. So don't expect that that is going to work for your B2B business now because that that's totally changed.
**Lenny** (00:37:29):
And when you say unconventional, what do you mean?
**Zoelle Egner** (00:37:31):
We spent a lot of time thinking about a psychographic profile for our users. So the challenge of Airtable is that you can use it for anything. It can be used in every department within an organization. It can be used for personal stuff, you name it, it has a use, because you're functionally building your own software and you can build software for anything. Unfortunately, if you go out to the market with a message of, like, "Build your own software." The vast majority of people are like, "I want to do that. That sounds hard. That sounds stupid. No." 
**Zoelle Egner** (00:38:01):
And so we couldn't really use super generic messaging, but to go really specific into verticals, which we did end up ultimately doing, didn't give us the broad coverage to go find new opportunities. You go really deep into one particular vertical or two particular verticals at a time with a small team, but then we weren't surfacing new opportunities that might be even more important. So we tried to balance that vertical specific work that we did with also trying to find this type of person who we had discovered was going to be the best champion for us. 
**Zoelle Egner** (00:38:33):
And this is a tinkerer persona, someone who likes new technology, they like putting together the Lego building blocks of things, and you couldn't really find Tinkerer's Magazine. There's not like a place those people hang out. They don't just have one title. It's a psychographic profile as a type of person that could have many, many different roles. And so instead-
**Lenny** (00:38:56):
And Facebook doesn't let you do that anymore, right?
**Zoelle Egner** (00:38:59):
No. You can't target based on-
**Lenny** (00:39:01):
[inaudible 00:39:01] go.
**Zoelle Egner** (00:39:02):
... like, "They have a tinkerer mentality," unfortunately. 
**Lenny** (00:39:04):
Okay, got it.
**Zoelle Egner** (00:39:05):
It's so sad. 
**Lenny** (00:39:05):
Okay. I see-
**Zoelle Egner** (00:39:05):
But-
**Lenny** (00:39:05):
... that it's not possible. 
**Zoelle Egner** (00:39:07):
Yeah. But what you can do is you can say, "That type of person often likes these types of media. We've heard that they often are really into these podcasts, so they're really into reading about this type of personal development." And often that is associated with people who have these broad set of roles but have this typical mentality. So we would find clusters of interests that people might have, that often were shared by those people, and do targeting around that. And then when that worked, they'll look alike based on it.
**Lenny** (00:39:38):
Did not expect Facebook ads as one of these answers. So that's interesting. 
**Zoelle Egner** (00:39:42):
No, and it's not a good idea anymore. Don't do it now. 
**Lenny** (00:39:44):
Disclaimer.
**Zoelle Egner** (00:39:44):
Back in the day, it was great. Now I would not recommend. But I have some unconventional ones that I can suggest that are- 
**Lenny** (00:39:44):
Get into it.
**Zoelle Egner** (00:39:52):
... not Facebook. There's a few different things, but I want to give some context first for people who are not as familiar with Airtable's business, because I do think these are really helpful pieces of context. The first is because of the types of industries that we are often very successful in, had a very similar network effect that we would see, where basically it was within specific professions, we would see people who, in order to distinguish themselves in that job market, would build a brand around the tools that they used, essentially. We found different ways to accelerate their process of identifying those roles, where it was really, really helpful to build a brand for yourself so that you could hop around to different jobs more quickly, accelerate your process, et cetera, and thus bring along a tool with you and evangelize for it a lot. So that's one set of things we were trying to achieve.
**Zoelle Egner** (00:40:46):
The second set of things we were trying to achieve that's also useful context here, is although industry virality was really important for us, even more important was inside of company virality, that was the real superpower of Airtable. We'd go from 10 people to 1,000 people a year. And so we were always looking for ways to make that happen within companies in more and more efficient ways.
**Zoelle Egner** (00:41:08):
And then the third piece here is no one had a good generic explanation of Airtable that worked for everybody. This is perhaps partially my fault as marketing, but it's also the fault of the fact that the market was not ready for the good, generic explanation to mean anything, like I mentioned before, people just did not care about the generic explanation. And the magic of Airtable was always seen in its specificity. 
**Zoelle Egner** (00:41:32):
So we knew if we can get to the right people and we can connect the dots to them to the correct use case, so they want to go and evangelize to improve their careers, they will do that both externally and within their companies, and more importantly within the companies, they'll be able to go to their friends and say, "Hey, I'm using Airtable as a content calendar, but you have a UX research problem. And I understand Airtable enough that I can help you build a system. And now I'm a superhero internally because I helped you build this whole new thing. Look at me, I'm amazing." And they suddenly have fully done a sales pitch for Airtable without us having to do any work or understand their use case, which is great and very necessary when you are as horizontal as we are. So we had to figure out essentially, "How do we catalyze that word of mouth and build champions at scale?"
**Zoelle Egner** (00:42:21):
All of that is to say the two interesting things that we did were all around that. In the very early days, what that meant in practice was we literally had a Slack integration that we pulled in a whole bunch of information about anyone who signed up for Airtable, including their title, the company that they worked at, et cetera. And literally would sit there and had a little button in each of the records that came in that would allow us to email them immediately if we had decided that they might be someone we want to talk to. And we set up this whole automated system so that it would take two seconds to reach out to a ton of different people, being like, "Hey, we'd really love to get your feedback and help make sure you're as successful as possible on Airtable." 
**Zoelle Egner** (00:43:02):
This is not scalable in the long term because there's a whole bunch of sending emails and doing meetings. But what it meant is that we were able to start building our mental model for what these champions looked like in practice by finding the patterns across them. And building the foundation is what ultimately became our customer success motion very early. And then we were able to say, "Okay, we found five people who have a content calendar use case with this type of title. And now we'll be able to go run an ad campaign based on that. We can build a bunch of templates based on that. Here's all these different hooks we can use, because we know this is what a champion can look like," in a way that was not going to be obvious if we hadn't talked to a ton of people. So it seems really unobvious as an investment, per se, but tremendous number of human hours going into just having an efficient way to talk to as many people as possible to build those mental models. That's number one.
**Lenny** (00:43:57):
That is fascinating. Essentially, you weren't even sure who would be excited about Airtable. Part of this is like, "Figure out the personas and groups of people that we believe are the right target to encourage and help support." And then part of that is, "Get it spreading within a company once you figure out these folks within a company." It's such a cool idea to just have a feed of ... I imagine the squad had certain attributes of the person, like, "Here's the company they work. Here's how big it is." And then they talk about, there's a mention of what they're using it for. Is that part of this?
**Zoelle Egner** (00:44:31):
Ideally. Though we were always very privacy minded, so we couldn't actually get much information about what they were doing in Airtable. We could never see their data, because that would be a tremendous failure of trust, to go back to what we were talking about before. So a lot of this, we would have guesses, and maybe we could see that they'd use certain templates but we didn't otherwise really know. And that was part of the reason why we wanted to talk to them in the first place. 
**Zoelle Egner** (00:44:54):
The second reason is that if we could talk to them early, we could help them build their first space, and from there, if they were successful, they would have the tools to go and help other people within their organization. So if we catch them at the beginning, make sure one person was successful by over investing in them, then they essentially became support for everybody else. I should also clarify, these were not necessarily people who were going to be the buyers. The buyers and the champions here look very, very different for Airtable, which is a really an interesting dynamic that many companies do not have. But for us, the person who is going to sit down with a glass of wine on a Friday and build an Airtable base was not the person who had the budget who was going to pay for this thing. 
**Zoelle Egner** (00:45:36):
And so we weren't initially looking for buyers, we were looking for champions, in part so that we could then go to IT six months down the line and be like, "Look, you have 500 people using this product, it's been very useful for them. It is time for you to pay now." Not sure IT loved those conversations, but they were really effective for us and meant that it was very, very easy to sell.
**Lenny** (00:45:57):
Fascinating. It makes me think a lot about the product led sales movement and how this is essentially that, but even earlier, because it's people just signed up and they're just helping them be successful, versus like, "This company's got 14 people using it. You should go try to sell them on an enterprise contract." Essentially this was a tool to help you figure out how to, basically scaling customer success and helping you prioritize who to go after, and being very hands-on with the strongest potential future big buyers.
**Zoelle Egner** (00:46:24):
Exactly. And I think what's interesting here is it helped us bootstrap two things. One was, to your point, building out the personas, and champions, and so on. And ultimately there's more scalable ways to reach those people in the long run. But secondarily, it also helped us deal with a real product education problem that we had in the early days. Because it was really complicated. Airtable, unfortunately, has two education issues that it needs to solve. It's not just, "How do I put the Lego blocks together?" It is also, "How do I design a piece of software and a workflow?"
**Zoelle Egner** (00:47:01):
And unfortunately if you're selling to content marketing manager or a UX researcher, there's no guarantee that they know how to make a workflow. Most software is opinionated, and it does that work for you, and you're like, "It either works for you or it doesn't." And maybe you're frustrated about what it forces you to do in order to work, but you can't really control it, which means when suddenly, you have the ability to create whatever workflow that you want, there's actually some education that needs to go into it in order to be able to make that successful. 
**Zoelle Egner** (00:47:28):
It's not enough to just make an Airtable base that's pretty or that functions. You can't get your team to use it effectively if it doesn't fit into the broader context of the organization. It's still going to fail. And so a lot of this was us figuring out, like, "Okay, how do we help these people not only use our product but build something that is going to be durable, so that we do see that growth, so they don't see it as a failure, so it doesn't fail at that second order moment when it starts to get spread out to more people?"
**Lenny** (00:47:53):
It's a really good tactic for any SaaS product that just is hard to understand and needs, Airtable had both problems. Like, "I don't know what this is for and I don't know exactly how it's going to fit into my workflow." Imagine most-
**Zoelle Egner** (00:48:05):
But-
**Lenny** (00:48:05):
... companies still have to deal with both those problems. 
**Zoelle Egner** (00:48:07):
No, hopefully not. Hopefully not. 
**Lenny** (00:48:07):
Yeah.
**Zoelle Egner** (00:48:08):
But once you actually get in with folks, it's very difficult to remove it. So suddenly your retention rates are incredible, your word of mouth is incredible, if you're willing to do that initial work. A lot of people think that Airtable was a pure product led growth company, and missed that huge customer success component that was always very, very important in the early days. And that helped us ultimately move more towards that PLG motion for a while, but was essential to getting it set up in the first place.
**Lenny** (00:48:35):
Fascinating.
**Zoelle Egner** (00:48:36):
The other one that we did related to this champions at scale was we spent a hilarious amount of money on really fancy swag. I know this sounds silly, but branded AirPods level of fancy swag. Admittedly more people were in the office back then. Now they are more remote and this would not work as well. But back in the day, if you gave people something really good, not a pen or a sticker, really good, they would show it off to absolutely everyone that they talked to, because they were so excited they got branded AirPods. People would ask about it, walking by their desks. It sounds so like trivial. But for that couple hundred bucks that we spent knowing like, "Hey, this person's already a champion and if someone asks them, they're going to give a really good pitch." Totally worth it. Sometimes better to not skimp on swag. Hard to measure, very effective.
**Lenny** (00:49:27):
That's a great tip. And it connects to the general idea of find your champions and just do a lot to make sure they're successful, excited, want to evangelize, and an AirPod here and there feel like a really good ROI investment.
**Zoelle Egner** (00:49:40):
Was for us.
**Lenny** (00:49:41):
Anything else along those lines?
**Zoelle Egner** (00:49:42):
I think those are the big ones that I would highlight. The only other small note I would make from a process perspective is if you are going to overinvest in customer success, which I recommend, make sure that you have also set up a process to take the insights that your customer success people are coming up with and turn them into as much content as you can. Because that's where you're going to find scale in the long run. So for us, what that meant was we would talk to a bunch of customers and then customer success would have helped them build bases, and then we would create templates. So were not exact copies, because we're not trying to steal their intellectual property. We would say, "What is the fundamental workflow here, that other companies might have? How do we make a template that is useful from this?" And some blog posts that explain it, whatever else, that we can then put out into the market. 
**Zoelle Egner** (00:50:25):
And the next time a smaller company that's not a Fortune 500 wants this sort of thing, someone can just email them that template and we don't have to go through this whole build process, they have something to start with. If you can find those insights and put them genuinely into use as a little conveyor belt, it will be much easier to scale. It will be much easier to come up with genuinely compelling content because it's coming from your customers, so they already care about it. You have strong signal that's going to be valuable if you already built it for them. Use that to your advantage, make that into a little machine. And it makes all of the go-to market that you need to do later easier.
**Lenny** (00:50:57):
I know that you have the strong opinion that customer success and marketing are basically the same thing and should be maybe one team. Can you speak to that?
**Zoelle Egner** (00:51:05):
Yeah. This is my spicy opinion, but both of them have to do the same things. They have to identify customer needs. They have to help the customers see your product as a solution to those needs. They need to remove friction from the process of getting value. They are hopefully both encouraging those customers to share with other people, and both of them should be engaged in translating insights from those individuals into resources that can help everybody. 
**Zoelle Egner** (00:51:31):
They use different tactics. Marketing is going to use more scalable tactics. Customer success is going to be in the weeds, really talking to individual people, but all of the things they care about are actually the same thing. They just use different ways to do it. And if you, as a marketer, are not pretty confident in being able to say, like, "What I'm doing is getting the right people to get genuine value from this product," so much so that they want to tell other people about it because it's going to make them look good, then maybe figure out if there's ways to bring more of that to your process, because it will make what you are doing more effective.
**Zoelle Egner** (00:52:05):
And frankly, there's not a better evangelist than a person whose career you have materially helped to improve based on matching the right person to the solution so that they can have more impact at their company. So much said, one of my unofficial metrics for both marketing and customer success at Airtable, unofficial, was how many people we'd gotten promoted for using the product. I had a running tally of those people, and I knew if we were getting those at the major accounts we were trying to win, something good was happening and we were going to be successful with really large deals.
**Lenny** (00:52:36):
So curious how you tracked that. I guess you just check in with them occasionally?
**Zoelle Egner** (00:52:40):
No, I had my CSMs literally, they had really strong relationships. We were actually tracking it. It was a little embarrassing, but it worked really well.
**Lenny** (00:52:47):
I love it, with the great KPI. It's like dating apps and how many people get married, I guess.
**Zoelle Egner** (00:52:52):
Exactly. 
**Lenny** (00:52:53):
Zooming out a little bit, you advise a lot of companies on marketing, customer success, growth, and things like that. Maybe there's a two part question, and see where you want to take it. 
**Zoelle Egner** (00:53:03):
Yeah.
**Lenny** (00:53:03):
One is just what are activities that marketing, and growth, and customer success teams often do that are impactful and consistently impactful, things that you think startups should invest in that maybe they aren't, or they already aren't and they should definitely keep doing this. And on the flip side, things that don't work, things that maybe they should avoid. So maybe let's start there and there's going to be a followup. 
**Zoelle Egner** (00:53:26):
Cool. Okay. I'm going to start with things to avoid, because I try and not to make too many blanket statements on this, but I have a couple that I am willing to make. So this is all with the caveat that channel market fit is really real, and sometimes these things might work for you. Don't discount just because I say that they don't work for me. There are certain types of flashy event marketing and sponsorships that you will get relentlessly invited to do, that will seem like they're going to be really great for signaling purposes, or for leads, or whatever. 
**Zoelle Egner** (00:53:55):
And they're almost always a waste of your time, unless you are in an industry where you desperately need to get to a trade show, because that's where everyone hangs out. At that point, yeah, of course you're going to have to go do that. But if you're in more standard B2B SaaS, or that's not really a thing, there are better ways to get in front of those people than having your logo out there. That doesn't tell them anything. Maybe you get a branded session at the conference or whatever, but who's going to go to that branded session? Probably not that many people. And then you will have spent so much money and gotten nothing for it. Go to the event, do not fund your money on the sponsorship. It's stupid. And then the second one, which is definitely a very spicy opinion, but I'm going to go there. 
**Lenny** (00:54:40):
Go there. 
**Zoelle Egner** (00:54:41):
A lot of people think that the epitome of product marketing is creating your own category. And while I agree that it is useful to have strong differentiators, because it is, I think creating a category, getting a new thing in Gartner or whatever, is often a waste of your time. It is a huge lift, absolutely enormous, particularly in B2B SaaS, and I'm not always sure that it's helpful to have your super teeny tiny, little niche over here where you're like, "Oh, we have no competitors." That's not actually how buyers work. It's not really worth it. 
**Zoelle Egner** (00:55:21):
That said, there are things you can do that feel like category creation that are actually effective, and that I do think make more sense. And specifically if you can elevate a profession instead of a category, that can make way more sense. So the great example of this is that Gainsight creating customer success or many companies altogether carving out DevOps, or rebranding DevOps, to be a thing that was suddenly a sexy job to have. 
**Zoelle Egner** (00:55:47):
And I think that's valuable because a job is an identity and people will fight for an identity. A category of software is a line item on your budget. No one is excited about that. But people are very excited about their job being meaningful, and their job being important, and being taken seriously. And so if you could hold up either an existing or a brand new job and say, "This is really important for much broader business metrics, whatever else. We're going to create community for those people to come together and it's all about the job," and not about you. That can be very powerful and they'll take them with you. You become part of the identity of that career. Amazing. Do that, for sure. But like the Gartner Square, there's some opportunities for that where it makes sense. A lot of the times it doesn't. Don't do that.
**Lenny** (00:56:34):
Amazing. I love that. Is there more you wanted to add, there?
**Zoelle Egner** (00:56:34):
No. 
**Lenny** (00:56:34):
Okay.
**Zoelle Egner** (00:56:39):
I think that's enough on not to do.
**Lenny** (00:56:40):
What this reminds me of broadly is just, "Stay focused on the customer and their problems. Don't obsess with who you are, who are you selling to and how will you make their life better." Reminds me of this old idea from Kathy Sierra. Does that ring a bell? 
**Zoelle Egner** (00:56:55):
Yeah.
**Lenny** (00:56:55):
Where-
**Zoelle Egner** (00:56:55):
Oh totally. 
**Lenny** (00:56:56):
... you make your customer a superhero, you want them to feel like a superhero. And if they-
**Zoelle Egner** (00:56:56):
It works-
**Lenny** (00:56:59):
... feel like a superhero. And yeah, that sounds like that's essentially what you did with Airtable, a lot of these companies you worked with.
**Zoelle Egner** (00:57:05):
That that is always the goal. Like, "How can you make them the hero of the story and not you? Because no one cares about your company, what they care about is themselves, frankly."
**Lenny** (00:57:12):
Are there any products or companies you think of off the top of your head that are really good at this, that are just like they nailed this?
**Zoelle Egner** (00:57:18):
Yeah, that's a good question. Certainly the two that I mentioned, that helped rebrand some of the professions, so like the Gainsights of the world. I'm blanking a little bit on the ones that have done this for DevOps really effectively, but there's certainly some that have.
**Lenny** (00:57:32):
Maybe Datadog?
**Zoelle Egner** (00:57:33):
Yeah, Datadog has done a pretty good job of that. I think where I get excited is when the companies do this in a way that feels less self-serving, or less obviously self-serving. And that means that sometimes you have to be willing to invest in things that will not have super obviously immediate ROI for you, but they will for the community, and for building the community. Oh, actually one really good example, I think Notion has actually done a pretty good job of this. People are really, really invested in the templates that they create, because it feels like you're not pushing Notion, you're pushing the beautiful creation that you have to solve a problem. I think they've done a really nice job on that process, and several of their competitors, I think have done a pretty decent job as well, but they certainly come to mind.
**Lenny** (00:58:18):
Thinking of templates, I know Airtable, known for templates, and you've mentioned this being a big part of the success, and I imagine a lot of companies now are just creating templates left, because they imagine that's the core, what helped a lot of these companies, Notion being an example. What is your take on the power and importance of templates for software?
**Zoelle Egner** (00:58:38):
I think they can be tremendously helpful if you are horizontal because they help to narrow the surface area for a user, so they understand how to connect the dots between their problem and your product. And if it is not obvious to someone how they can solve a specific problem, they're going to be like, "Oh, hey, that seems really cool. When I think of something I'll definitely come back." And then you have lost them. And so if you can be like, "Here are three templates that a person you might be excited about." That can be really helpful. Where people sometimes get confused about templates, or have the wrong expectations about templates, is when they think that templates are going to be an acquisition mechanism, and they don't build in the foundation that is necessary for that to be true. So a lot of people think that templates were what drove Airtable's top of funnel. That is not the case. 
**Zoelle Egner** (00:59:27):
I was having a conversation with someone who worked a lot on SEO at Airtable in the much later days, and laughing over the fact that people thought that was a big source of traffic, because it was not. We did not optimize them for that. Good luck finding them in search most of the time. Not at all useful. Where they were helpful, narrowing that surface area, helping with matching patterns, helping people understand how the product worked, super helpful. Expansion within companies, tremendously useful. 
**Zoelle Egner** (00:59:55):
But they were not a top of funnel mechanism for us, because we didn't put the work in to do that. We did not have an SEO engine. We weren't Zapier. Zapier has done a great job with that. They get a ton of traffic because they built it as a programmatic SEO play, but you have to be clear about what your goals are and what problem they're solving, because otherwise it is very easy to be like, "I'll just build a bunch of templates, and then all of the leads will appear," And that's not going to happen unless you invest in a lot more than at least Airtable did. So it can be useful to build them, know what you're doing it for, and how you're going to measure it, or otherwise you'll waste your time.
**Lenny** (01:00:29):
Do you think Airtable could have taken advantage of that top of funnel approach if they invested from an SEO perspective or do you think it wasn't an opportunity that worked?
**Zoelle Egner** (01:00:37):
I think it could have been. We would've needed to hire more humans. Airtable was an incredibly lean team for a very, very long time. From 2015, when I joined, until 2017 or 2018, we had barely 50 people. It was small for many, many years and so we had to make really difficult choices about what to prioritize and what not to prioritize. Should we have hired more people and done more things? I would argue in retrospect, absolutely, yes, there were opportunities that were left on the table, but in early days you leave good opportunities because you have to focus on other things.
**Lenny** (01:01:13):
Got it. And so a takeaway here is templates could be really useful for customer success versus SEO top of funnel. Right? That's-
**Zoelle Egner** (01:01:13):
Yeah.
**Lenny** (01:01:20):
... where they became powerful. 
**Zoelle Egner** (01:01:21):
Still maybe helpful. Maybe for you, it makes sense to do the SEO play, just know that that is not a small play. It is an investment. It is not and not just like, "Have some people make some templates." You got to do way more than just that. It's not going to be sufficient.
**Lenny** (01:01:35):
Final potential question, depending on where this goes, and I'm curious how spicy this answer gets, and-
**Zoelle Egner** (01:01:35):
Oh boy.
**Lenny** (01:01:40):
It's around launches and PR. You work with a lot of startups, I imagine founders are always trying to plan a launch, get PR. I'm curious your take on the value of investing a bunch of resources in a big launch, the value of just getting PR as an early stage startup.
**Zoelle Egner** (01:01:56):
Yeah, just getting PR is not a good goal. I know that's been well stated in the market, but just to reiterate it, most of the time PR is not going to get you leads or users, it's just not. And you have to think about when you are creating a launch or doing a piece of PR, what are the breadcrumbs that bring someone back to something that can actually convert? If you have your big tech crunch piece and it's super exciting, it says all these great things about you, and it maybe links to you once, somewhere in the 12th paragraph or whatever, how many people are actually going to click on that link? Not that many people. How many people are going to read that and remember to go Google it? Not as many as you want. Okay? There's going to be so much coming out of the funnel, it is not a useful acquisition mechanism.
**Zoelle Egner** (01:02:43):
What it is good for is credibility. And that's where, if you have really clear goals, and you know how you are ready to leverage the asset of a piece of PR coverage, then it can be helpful to you. So the two goals I always recommend to founders when thinking about using PR, are either hiring or maybe improving the response rate for your cold outbound. Those are the two that I think make the most sense, because in both cases they have a different distribution mechanism. In hiring, you're going to include that in an email that you're sending to a candidate. And so it's going to increase the likelihood that they take you seriously, and get excited about the company, and maybe actually end up ultimately joining your team. 
**Zoelle Egner** (01:03:22):
Cold outbound, you're using it as credibility to say, "Hey, we're a real company you can trust." Great. Both of those things are all emails that you are proactively sending. You know exactly who they're going to, and you know that asset is going to have, hopefully, the impact that you're looking for, and you can measure whether it makes a difference or not. But just getting a piece of PR, to get a piece of PR is like it'll help with your internal morale, but I'm not sure it's going to do much help for you. So have really clear goals and have realistic goals, or you will be disappointed.
**Zoelle Egner** (01:03:51):
Launches however, do not need to just be about PR. In fact, in many cases PR is a distraction, and instead you can have not just one big launch but a series of launches that allow you to stay top of mind, to create momentum with your users, and to show up in lots of different places because audiences respond to novelty, it gives them a reason to care about your company. And so have your big, annual launch or whatever, but also have one two months from then, and another one, and another one. Find ways to use that novelty to your advantage and to get into communities that you think are going to be good fits for your company.
**Lenny** (01:04:26):
I love that advice. Any final thoughts before we get to our very exciting lightning round?
**Zoelle Egner** (01:04:34):
Mostly just all of this is easier if you talk to your customers more. Build a system for yourself that will allow you to have those touchpoints. That's not just making everyone answer customer support tickets, though I do think that is a great idea, because it gives so much empathy and it's really helpful. You as a founder, if you're a founder, or a product manager, or whatever else, should find a way to get that on your calendar weekly or monthly. Go talk to people, it makes it better. You will have a better mental model. The other thing is strongly consider investing in customer success if you are a B2B company, early. Airtable had it before sales, which is a very unconventional approach, but early is worth it. It has huge dividends if you actually listen to them. If you're not going to listen to them, though, don't hire them, because that's sad.
**Lenny** (01:05:22):
I have followup questions on the customer success piece, say someone wants to invest in customer success, is there a resource, or person, or anything that you could point folks to, to understand and think about how to do this well?
**Zoelle Egner** (01:05:36):
There's a lot for people within that profession. There's not as much for founders out there right now, unfortunately. This is an area that I very eagerly am looking for more resources to share with people. Minimally. I'll say, if you care about this, send me a message. I will give you some advice. All of our industry will be better if there are more people working on customer success. So I will help you. Send me a note. Otherwise, I'll try and dig out some other things and maybe you can share them, but there's not a ton. So people in customer success, please share your learnings more with founders. All of us-
**Lenny** (01:05:36):
Have-
**Zoelle Egner** (01:05:36):
... would like to see it.
**Lenny** (01:06:09):
Yeah, I've actually been looking for someone to write a guest post in the newsletter, about just how to set up a customer success team. And so if you're listening, you think you could be that person. Let me-
**Zoelle Egner** (01:06:21):
Yeah, I have some people that I will not put on the spot right now, that I will send your way that I think- [inaudible 01:06:26]
**Lenny** (01:06:26):
Amazing. [inaudible 01:06:27]. Let's make this happen.
**Zoelle Egner** (01:06:28):
Yeah.
**Lenny** (01:06:29):
And then I wanted to ask you a question on the first piece of advice, which is, "Founders talk to the customers more often." Is there one tactical piece of advice you could recommend for how to do that?
**Zoelle Egner** (01:06:37):
Yeah.
**Lenny** (01:06:37):
How to find a customer, how to set it up consistently?
**Zoelle Egner** (01:06:40):
Totally. The simplest way to do this is to write a template email for yourself that you can send out very easily, that essentially says like, "Hey, thank you so much for using the product. I would really love to hear about your experience so far and get your feedback. Do you have 10 minutes to talk on the phone?" I know it is important that it's on the phone and not a survey because you get way more instinct from unstructured conversation than you're going to get from sending them three things in a Google survey.
**Zoelle Egner** (01:07:05):
Set it up, come up with a hypothesis of the type of person that you want to talk to and then run a query against your database, find someone and send three of those emails a week. And it's not exciting, but you can automate most of it and it will be helpful. None of this stuff has to be complicated. You just got to have a system.
**Lenny** (01:07:23):
Great advice. With that, we've reached our very exciting lightning round. 
**Zoelle Egner** (01:07:27):
Yes.
**Lenny** (01:07:27):
I've got six questions for you. I'm going to go through them pretty quick. Whatever comes to mind, let's see where it goes. 
**Zoelle Egner** (01:07:34):
Okay.
**Lenny** (01:07:34):
Question number one. What are two or three books that you recommend most to other people?
**Zoelle Egner** (01:07:40):
Okay, I hate this question because I take pride in making highly targeted recommendations, but I will do it anyway. I'm pretty sure you mostly talk to product and growth people. Right now, obviously, AI is a big topic of conversation, so here are two books that will enrich your mental model for artificial intelligence and encourage you to think about it from different perspectives. The first one, a little bit academic, highly recommend it, though. It's a book called Computing Taste by Nick Seaver. 
**Zoelle Egner** (01:08:09):
He's a professor of anthropology and he did this study of people and companies who build music recognition algorithms. And it's a really interesting book for a bunch of reasons, including that it's a academic take on both tech culture, and more specifically, the unspoken and underlying assumptions that many workers who are building in this space have. It can be a little spicy and uncomfortable for a person in tech to read, but I think it is a fascinating perspective and very relevant to the stuff that's going on in AI right now. So go check it out. Computing Taste by Nick Seaver.
**Zoelle Egner** (01:08:42):
The second is a fiction book, but the Ancillary Justice series by Anne Leckie, about a spaceship AI that ends up separated from its ship and trapped in a body. I'm going to leave it at that. Worth reading for a different way of thinking about AI.
**Lenny** (01:08:56):
I think we need a Zoelle full episode on book recommendations. These are amazing. Let's keep going.
**Zoelle Egner** (01:08:56):
So fair.
**Lenny** (01:09:02):
What other podcast of yours that you love to listen to other than this podcast?
**Zoelle Egner** (01:09:07):
Probably either Happiness Lab or Gastropod. I love food and also psychology, one of those two.
**Lenny** (01:09:13):
Interesting. Okay, we'll keep going. Favorite recent movie or TV show?
**Zoelle Egner** (01:09:17):
Movie, Everything Everywhere All at Once. And TV show, there's a Korean drama called Extraordinary Attorney Woo. That, I really enjoyed.
**Lenny** (01:09:26):
Favorite interview question that you like to ask?
**Zoelle Egner** (01:09:29):
Yeah. Okay, so this one is related to customer success. It's my favorite question of all. People hate it, sorry. But I like to ask anyone who's going to be in a customer facing role, who needs to be able to keep their cool, and also learn stuff on the fly, and respond to customers, to solve an unfamiliar problem using Zapier. And they can use the internet to look things up, whatever, but I basically lay out for them a problem that I, as the customer want to solve, and have them build it for me live. This both is surprising for most people, so you get to see how they respond to an unfamiliar situation, which every client will give you at some point, and it shows how they learn things in a very concrete way, which is really interesting. So check it out. It works really well for customer success.
**Lenny** (01:10:10):
I've not heard that one before. Fascinating. Top five SaaS products that you enjoy and an Airtable cannot be one?
**Zoelle Egner** (01:10:18):
Ugh. Okay, then I'll try and avoid any company that I have worked for. I really like using Figma. It's nice when designers let me play with things. I've been really enjoying working with Webflow, also means that I can do stuff on my own. This is maybe spicy, but I actually love Google Docs. I'm not a Notion's fan stand, sorry.
**Lenny** (01:10:18):
Hey.
**Zoelle Egner** (01:10:36):
But Google Docs-
**Lenny** (01:10:37):
Can't [inaudible 01:10:37] them all.
**Zoelle Egner** (01:10:36):
... is like my best friend.
**Lenny** (01:10:37):
Google Docs is great.
**Zoelle Egner** (01:10:38):
Yeah. And then there is a personal CRM company that I invested in, so sorry, maybe this is not allowed, but called Clay, and it is the only way I've ever been able to keep track of my-
**Lenny** (01:10:47):
Wow. [inaudible 01:10:47]-
**Zoelle Egner** (01:10:47):
... relationships in a real way.
**Lenny** (01:10:48):
Clay's great product.
**Zoelle Egner** (01:10:49):
They're the best. And then I don't know if I love it, but I use Zoom so much that I feel like I must say it, because I spend so much of my time on it and it's categorically better than Google Meet.
**Lenny** (01:11:01):
Final question, favorite book, course, article, any resource on marketing that non marketers can learn from?
**Zoelle Egner** (01:11:10):
Okay, it's a newsletter. Does that work?
**Lenny** (01:11:12):
Absolutely.
**Zoelle Egner** (01:11:13):
Amazing. Okay, so there is a specialist VC firm called MKT1. It's run by Emily Kramer and Kathleen Estreich, sorry if I pronounced your last name, there, wrong, Kathleen. It's all about marketing. They are marketing experts and operators who now invest, but they make the best frameworks that you can immediately apply. And there's templates and all sorts of super, super tactical stuff, which a lot of tactical marketing content is terrible because it's actually content marketing for some bad platform. Theirs is not. It is genuinely good. Go check it out. 
**Lenny** (01:11:43):
A huge fan. Emily has been on the podcast. 
**Zoelle Egner** (01:11:45):
Oh, [inaudible 01:11:47].
**Lenny** (01:11:47):
Yeah. And I look at that newsletter as the Lenny's newsletter of marketing, and it's exactly how you described.
**Zoelle Egner** (01:11:53):
It's the best.
**Lenny** (01:11:53):
Huge fan. Great recommendation. With that, Zoelle, thank you so much for being here. This was a lot of fun. And we got through a lot of stuff, which makes me really happy. Two final questions, where can folks find you online if they want to reach out, learn more, and how can listeners be useful to you?
**Zoelle Egner** (01:12:09):
I am on Twitter @Zoelle. I'm also on LinkedIn, so I live there, come find me there. Otherwise, how can you be useful to me? Mostly like go forth and believe in customer success, and talk to your users, number one, because I am an avid user of technology, and I want it all to be better. Number two, no, that's all I got. Just go do those things and I will be so happy. Also, if you want to talk about customer success, anytime, hit me up. I'm here.
**Lenny** (01:12:35):
I'm going to add a couple more things, which you mentioned to me offline, that you're hiring at Block Party.
**Zoelle Egner** (01:12:39):
Yes.
**Lenny** (01:12:39):
You're hiring growth people, PMs, engineers, and then you're also advising on the side with marketing customer success. Anything else you want to add, there?
**Zoelle Egner** (01:12:48):
Yeah, absolutely. Love advising early stage companies. I'm especially helpful for pre seed and seed, usually, anything PLG, positioning, messaging, figuring out your channels, experimentation, all that early, fun stuff. I love it. Happy to help anytime. And we are hiring across all of the teams, but especially mine. So if you would like to come and do all sorts of fun experimentation, and also help keep people online safe, come look up, Block Party. I'd love to have you on my team. 
**Lenny** (01:13:18):
Blockparty.com, or where do folks- [inaudible 01:13:19]
**Zoelle Egner** (01:13:18):
Blockpartyapp.com. Did not-
**Lenny** (01:13:18):
App.com
**Zoelle Egner** (01:13:19):
... get blockparty.com. 
**Lenny** (01:13:19):
You didn't. Zoelle, thank you. Very good.
**Zoelle Egner** (01:13:23):
Thank you. 
**Lenny** (01:13:28):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [7/22] How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe)

**Eeke de Milliano** (00:00:00):
Process, by definition, is variance reducing. You're introducing it, because you worry that the variance in your org is too high. You want people to sort of meet a certain standard.
**Eeke de Milliano** (00:00:13):
And the cost of that is obviously, while you are reducing the standard and bringing folks up to the average, you're also bringing other folks down to the average. And oftentimes, the folks you're bringing down are your highest performers, your most creative thinkers. The folks who, I think actually don't really need process to do their best work.
**Eeke de Milliano** (00:00:34):
And so, that, I think is always the tension that you have with process. And obviously one of the reasons why companies introduce process much more and more, as companies get bigger, is because it's harder to get all these folks who don't need processing. You actually want to reduce the variance.
**Lenny** (00:00:52):
Welcome to Lenny's podcast, where I interview world-class product leaders and growth experts, to learn from their hard own experiences, building and scaling today's most successful companies.
**Lenny** (00:01:01):
Today, my guest is Eeke de Milliano. Eeke is head of product at Retool. Prior to that, she was a longtime PM at Stripe. She was actually one of their very first PMs, where she helped build some of their foundational products like Stripe Checkout, Stripe Connect, Stripe Radar, and Stripe Chargeback Protection.
**Lenny** (00:01:18):
I had a total blast chatting with Eeke. We covered Stripe's internal culture and what makes it so unique and innovative. How to foster and protect innovation at your own company. What is the right amount of process by stage of company? How to build a talent portfolio. And so much more.
**Lenny** (00:01:32):
**Eeke de Milliano** (00:03:39):
Thanks so much for having me, Lenny.
**Lenny** (00:03:41):
It's absolutely my pleasure. A bunch of people have told me that I need to have you on this podcast. And actually, a big thank you to Snir Kodesh, who I believe is a colleague of yours, who gave me a bunch of interesting questions to ask you. So, I hope you're ready.
**Eeke de Milliano** (00:03:53):
Awesome. Very ready. Snir is the best, so yeah, I'm excited.
**Lenny** (00:03:57):
So you're currently head of product at Retool, but before that you spent a lot of time at Stripe. You spent six years at Stripe. And so, before we get to Retool, I actually want to spend a little time on Stripe.
**Lenny** (00:04:08):
To set a little foundation, could you just talk about some of the things you worked on at Stripe? And maybe some of the things you're most proud of, during that time?
**Eeke de Milliano** (00:04:15):
Yeah. So when I joined Stripe, I joined Stripe in 2013. It was pretty small at the time, it was around 50 people. And Stripe didn't have any product managers at that time.
**Eeke de Milliano** (00:04:23):
And I think Stripe was kind of famous for that. And it really wasn't because we were anti-PM in any way. It was mostly just because we were building this product for developers. We had a lot of really talented engineers, who were essentially doing the PM job.
**Eeke de Milliano** (00:04:36):
So I actually joined Stripe as the first account executive, which I think is pretty funny, now that I've seen real account executives do their jobs. Because I really just had no business doing that job. But it also really wasn't your typical sales job, in that most of Stripes volume was inbound. So I was really just spending all of my day talking to customers, helping them figure out how Stripe might work for their particular business flows, and payment models.
**Eeke de Milliano** (00:05:03):
And a lot of it was, I think, what PMs do. It was just talking to customers, understanding their pain points, and really helping them figure out how the product might do that. And to this day, when people ask me, "Hey, what's your advice for going into product management?" I'm like, "Well, you should go get a sales job. I think it's pretty valuable."
**Eeke de Milliano** (00:05:21):
But, it's kind of a long story to explain that, at the time there was this one sort of business model, the two-sided marketplace business model, that was just becoming huge. And you can't even really sort of imagine that now, but back then, Airbnb, Lyft, Uber, all those marketplaces, it was quite a new way of doing business.
**Eeke de Milliano** (00:05:41):
And so, I was talking to all these customers and they had pretty complicated payment needs. So it was like, one payer putting in funds and it's getting paid out to a recipient. So an Airbnb guest and an Airbnb host. Or multiple payers putting funds in and it's getting paid out to one recipient, like a GoFundMe campaign. Or one payer putting in money and it going out to multiple recipients, like with ClassPass, where you get a subscription and then it gets paid out to a bunch of studios.
**Eeke de Milliano** (00:06:10):
And then on top of that, all these platforms and marketplaces started having all these pretty complex regulatory and compliance requirements that were pretty different, country to country.
**Eeke de Milliano** (00:06:18):
So it was just this really complicated financial infrastructure problem, and Stripe actually didn't really have the right solution for it. And no one else in the market did, either.
**Eeke de Milliano** (00:06:28):
So at the time, this Stripe engineer, Brian Krausz, started poking around at this problem. Because I was talking to so many of these customers, we started talking about this problem together and poking around. And that actually resulted in us launching this sort of evolution of this product that we had at the time, called Stripe Connect.
**Eeke de Milliano** (00:06:46):
That was easily, I think, one of my favorite products I worked on. Not only, it ended up actually being really quite significant for Stripe's business. But also, because it was the first product and I think that's always pretty special.
**Eeke de Milliano** (00:06:58):
And then, the second product that I think of very fondly during my time at Stripe, was this product, Stripe Radar. So Stripe obviously processes a lot of payments. Wherever there's money, fraudsters will kind of follow.
**Eeke de Milliano** (00:07:12):
And there were certainly some merchants who were just particularly vulnerable to payments fraud. So, someone's using stolen credit card information to essentially purchase a good.
**Eeke de Milliano** (00:07:21):
And if you're not in payments, this is going to sound kind of shocking. But if a merchant processes a payment from a customer and that customer used a stolen credit card, the merchant is ultimately on the hook for those funds. So it can be detrimental. The merchant who's trying to run a real business is just losing all of this money, because there are all of these frauds who are buying stuff from them online.
**Eeke de Milliano** (00:07:48):
So I really liked working on that product. So the product at Stripe was essentially, we built a bunch of machine learning models to try and predict when a payment was fraudulent. And then we built a product on top of that, to help customers understand why we were blocking payments, and help them write their own rules around that too.
**Eeke de Milliano** (00:08:03):
And that was really fun, both from an anthropological perspective. Because we were kind of hanging out in corners of the internet where you wouldn't usually go if you were doing only legal things. So we were trying to understand who these fraudsters were.
**Eeke de Milliano** (00:08:16):
But it was also really cool from a product perspective, because of all the kind of complicated product questions around how humans should interact with AI and models. And I imagine a lot of the folks in the latest movement in AI are thinking a lot about that too. It's like, "How do you explain a model to humans? How do you let them interact with it?"
**Eeke de Milliano** (00:08:33):
So, both those things were really, really neat.
**Lenny** (00:08:37):
I actually use Stripe for my newsletter. It's how folks subscribe. And when I log into my Stripe Dashboard, there's so many products. I don't even know what many of them do. But I've often seen Radar being pitched to me as something I should pay for.
**Eeke de Milliano** (00:08:53):
Nice.
**Lenny** (00:08:53):
And I feel like I should probably turn it on. That sounds really useful.
**Lenny** (00:08:57):
One thing, that I want to dig in on... So you said when you joined, there were no PMs at Stripe. How many PMs were there when you moved into product at Stripe?
**Eeke de Milliano** (00:09:06):
That's a great question. I want to say maybe three or four.
**Lenny** (00:09:10):
Wow. Incredible.
**Eeke de Milliano** (00:09:12):
Yeah.
**Lenny** (00:09:13):
And you said Stripe is kind of known for being really late to PM and... I don't know if I want to say anti-PM, but there's a lot of sense of, "Why do we need PMs? We have amazing engineers who can decide what to build."
**Lenny** (00:09:23):
Is there anything you can share around that general philosophy of Stripe? And was it effective? Was it good? Because a lot of companies are anti-PM. And I think they always point to Stripe, and Snap is another example of, "We don't need PMs. Look how far these companies got with without PMs."
**Lenny** (00:09:38):
Is there something unique to Stripe that allowed them not to have PMs? I think there was like 200 employees probably, by the time they had their first PM.
**Eeke de Milliano** (00:09:44):
I think we actually had our first PM at... I want to say at about 100 employees.
**Lenny** (00:09:47):
Okay.
**Eeke de Milliano** (00:09:48):
But yeah, no, it was late in the game. And actually, maybe just to pattern match. Retool also didn't really have PMs for a while.
**Eeke de Milliano** (00:09:57):
And I think actually both in the Stripe case and the Retool case, the thing that both of these companies have in common is, you're building for developers. The people who are building the product are the customers in a lot of ways. So, they get it. There's really no reason why you should have, in some ways, a middle man trying to figure out, "Hey, who's the customer, and what is it that they need?" And what are their pain points?"
**Eeke de Milliano** (00:10:19):
And I think the moment at which it became clear, "We really do need PMs at Stripe." And I think we felt the same way at Retool is, your customer base starts expanding. You start having different kinds of customers. You need to understand the whole market, all of the ICPs that you're going after.
**Eeke de Milliano** (00:10:35):
And the organization gets more complex. I think Stripe... Gosh, in particular, it's just an extremely matrixed organization in business. Because every time you launch a product, you're having to think about, "Well, how do we do this in other countries? There's different financial infrastructure. How do we think about the legal side, the compliance side, et cetera?"
**Eeke de Milliano** (00:10:51):
And I think PMs can really kind of bring that whole story together and make the whole machine move. In addition to understanding the customers, and the value prop, and what the overall strategy was.
**Lenny** (00:11:04):
That's a really good reminder of, engineers and designers can do the work of a PM, but often they don't want to. There's a lot of non-fun parts to it. They're like, "Oh, I wish we could have someone here do these things." And PMs enjoy that work. They're good at it. And so, eventually engineers and designers realize, "Okay, I see why maybe we should hire a PM."
**Eeke de Milliano** (00:11:23):
I say this often actually, to folks who are thinking about going into product management. "That's awesome. Just be really, really sure about what you're signing up for."
**Eeke de Milliano** (00:11:33):
It's kind of the same as, I think a lot of people want to become a manager. But just so you know, being a manager is like, "Hey, you're doing performance reviews a lot. And you're in one-on-ones a lot." You have to really love that kind of work. And I think in the product management case, it's also like, you're constantly working across a lot of different teams. You're trying to influence a lot of people who don't report into you directly, to do a bunch of stuff.
**Eeke de Milliano** (00:11:54):
And if you love that, that's great. But you've got to be sure you know you're signing up for it.
**Lenny** (00:12:00):
Yeah, that's a really good comparison. When I first became a manager, I was an engineer, actually. And I was managing engineers. And then, when I moved on to something as an IC engineer, again, I was like, "I will never manage again. That was no fun at all. Why would I want to do this?"
**Lenny** (00:12:12):
And I imagine people get into product thinking they're going to have all this control, power, influence. And then they're like, "Oh my God, this job is so freaking crazy. What did I sign up for?"
**Eeke de Milliano** (00:12:20):
It's so hard.
**Lenny** (00:12:23):
Yeah. That reminds me, something that I heard you did at Stripe is, you wrote their internal culture guide. It was like a quick start guide to culture at Stripe, that I think was maybe shared with early employees.
**Lenny** (00:12:33):
And if that's true, I'm curious what it is about Stripe's culture? If you could just briefly share just what makes Stripe so special. Clearly, it's one of the most successful companies in the world, in history. I know there's been a a slowdown with the market. Everyone's slowed down a bit.
**Lenny** (00:12:48):
But it feels like Stripe has been incredibly successful and continues to innovate like crazy. Hires incredible people. People that are starting amazing companies.
**Lenny** (00:12:56):
So I guess back to my question, what is it that you think makes Stripe's culture unique and special?
**Eeke de Milliano** (00:13:01):
Yeah, that quick guide to Stripe's culture. I think we wrote it, maybe when we were around 150 people or so. And we actually wrote it to share with candidates.
**Eeke de Milliano** (00:13:10):
Because the idea was like, "Look, we're kind of opinionated about how we do things here. Most companies struggle to describe what their culture is. Like, how does a fish describe water? But it's worthwhile getting a sense of the things that we feel opinionated about, and that you might like or you might not like."
**Eeke de Milliano** (00:13:29):
And actually, when we put out the guide, our metric of success was that, more of the right people would apply to Stripe and fewer of the wrong people. And there was a whole section in there, I was like, "Hey, look, we work pretty hard here and that is certainly not for everyone. And hopefully you're excited to come and work really hard with colleagues who really care, and that's the reward." So, that's maybe one example.
**Eeke de Milliano** (00:13:56):
On Stripe's culture and what's made it so successful. I've really been thinking a lot about, "Were there one or two pivotal points or decisions for Stripe, that really set it on its path to success?" And I don't think there are, actually. Every time I'm like, "Well, if this hadn't happened..."
**Eeke de Milliano** (00:14:16):
I can always reason my way into, "If these other things would've happened, Stripe would've kind of ended up in the same place."
**Eeke de Milliano** (00:14:24):
So I think what Stripe was actually particularly good at... And by the way, you should take all this with a humongous grain of salt, because I haven't worked there since 2019. But, at least my experience when I was there, what Stripe was really good at was just making, not just one or two good decisions. It was making a lot of really good decisions all the time, big or small.
**Eeke de Milliano** (00:14:44):
And that, I think, was quite cultural. There was this humongous respect and enthusiasm for thinking. It was such a part of the culture. One of the values was, think rigorously. Every meeting was very much like, "Hey, how do we think about this thing from first principle?"
**Eeke de Milliano** (00:15:03):
No one would ever say, for example, "It's a best practice to do X." People would be like, "Well, why?" You had to go a few levels deeper. So that was, I think, one piece.
**Eeke de Milliano** (00:15:14):
The other piece... And a lot has been written about this already. Stripe had a very strong writing culture. All communication was along from writing business reviews, strategy memos, product reviews. There was a lot of writing that happened.
**Eeke de Milliano** (00:15:26):
And I very strongly believe this. I don't think you can be a good writer, unless you're a clear thinker. And if you couldn't write well, I think it was actually pretty hard to be successful at Stripe, at least in the early days. So I think Stripe just cultivated a lot of really good writers, and by input into that, a lot of really good thinkers.
**Eeke de Milliano** (00:15:44):
And then, I think the last thing that Stripe was really good at, was not overthinking decisions. Because that's kind of the flip side of this really rigorous approach, is that you lock yourself into a room and can't come out for five days. You have to be good at making a lot of decisions, and the right decisions, quickly.
**Eeke de Milliano** (00:16:01):
And one of the things that we would always sort of kick around a lot was just the idea of, "Is it a trapdoor decision?" Which I think is an Amazon concept.
**Lenny** (00:16:12):
One-way door, or two-way door.
**Eeke de Milliano** (00:16:13):
It's like, "If you make this decision, is it one door, or is it two doors? Can you come back from this decision?"
**Eeke de Milliano** (00:16:16):
And I thought Stripe was actually really good at being rigorous... Back to the rigorous point. About what actually was a trapdoor decision.
**Eeke de Milliano** (00:16:22):
So I think a lot of people, for example, think pricing is a trapdoor decision. But actually, it's really easy to grandfather your existing users into some existing pricing model and change pricing for future users. And if you believe that the product's going to be successful, your early users are only going to be a fraction of that pricing model.
**Eeke de Milliano** (00:16:41):
And if the product's not successful, then Who cares if you change the pricing model? So I think that's a really good example of, people think that's a trapdoor decision, but actually you can move much more quickly on that decision than you think.
**Eeke de Milliano** (00:16:52):
And then, a decision that definitely felt to us very much like a trapdoor decision, that I think Stripe took a long time being really rigorous about, was titles. I think Stripe's kind of famous for not really having titles.
**Eeke de Milliano** (00:17:03):
And I think it was right to be rigorous around that decision, because once you've given someone a title, you can't really take it away. So you better be sure about the title you want to give someone.
**Lenny** (00:17:16):
Yeah, the titles are hilarious. I put together a career ladder doc of all company leveling names across all the big companies.
**Eeke de Milliano** (00:17:26):
Is everyone a lead, at Stripe?
**Lenny** (00:17:26):
And it's like, product manager, product manager, product manager, product manager... Yeah. And there's a lead here and there. Yeah, VPs are basically a product manager or a product leader, something like that.
**Eeke de Milliano** (00:17:36):
Yep. Yeah.
**Lenny** (00:17:37):
Hilarious. You talked about this idea of first principles. People talk about that often as, "We want to be first principle thinkers. We're going to think from first principles."
**Lenny** (00:17:47):
How did Stripe actually operationalize that, implement that? Or was that just founder, top-down, continued questioning people, and that trickles down? Or is there anything else that they did to instill that mentality?
**Eeke de Milliano** (00:17:57):
I definitely think it's founder, top-down. They were really good about hiring people who thought that way, too. So it's just all that stuff. It just really, really trickles.
**Eeke de Milliano** (00:18:05):
And actually, to this day, when I'm preparing a memo, or a board deck, or something. I imagine in my head, I'm like, "What if I had to present this to Patrick?" And my ideas just get so much better, because I can sort of think about the questions they would ask.
**Eeke de Milliano** (00:18:23):
So, I think that was one. I think the other one was just sort of this writing culture piece. Once you start writing things down, you realize, "Hey, that actually doesn't make a lot of sense."
**Eeke de Milliano** (00:18:33):
And then, I think the third thing actually was, there was just always a lot of questioning about the status quo. So if something had been done in an industry for a long time, people would always be like, "Well, why was it done that way?"
**Eeke de Milliano** (00:18:46):
And I think this is actually how Stripe got its start. I think when Stripe started, if you wanted to set up a merchant account, it could take weeks. And everyone just assumed that's what it took. And of course John and Patrick were like, "Well, it doesn't actually make that much sense why it should take that long."
**Lenny** (00:19:00):
You shared some of the values... I don't know if they're just called values, core values, at Stripe. But, is there other ones you can share? You said one is think rigorous, or don't overthink. What are the other values at Stripe?
**Eeke de Milliano** (00:19:10):
Yeah, think rigorously was one. And I think they might have actually updated these on the website recently, so my recollection is very likely out of date.
**Eeke de Milliano** (00:19:19):
And Stripe would call them operating principles, actually. Which, I think is actually better. Because values, you can't really tell people what to value. Everyone has their own value set. But you can tell people like, "Hey, here's how we operate."
**Eeke de Milliano** (00:19:32):
Another one that I loved was, move with urgency and focus. It was just really this idea that you're biggest compatriot and your biggest enemy as a startup, is time. So you have to move really, really, really fast on it.
**Eeke de Milliano** (00:19:48):
Customers first, was the other one. Or, users first, as Stripe would refer to customers as users. So those are some of my favorites.
**Lenny** (00:19:56):
When I think back to what made Airbnb special in a similar way, the values... We call them core values. I think were actually really, really important, and turned the company into what it ended up being. And I was actually there around the time they created these values.
**Eeke de Milliano** (00:20:08):
Oh, awesome.
**Lenny** (00:20:09):
I'm curious, at Stripe, do you have any recollection of how they came to these operating principles? Because, as I mentioned, founders are listening. "How do I come up with these for our company?"
**Eeke de Milliano** (00:20:19):
I'm pretty sure Patrick wrote them. Yeah. I think they came from... Patrick and John wrote them.
**Eeke de Milliano** (00:20:26):
Actually, the other value that I love... I don't think they have it anymore, but it was good, the operating principles. Micro pessimists, macro optimists.
**Lenny** (00:20:33):
Wow.
**Eeke de Milliano** (00:20:34):
Yeah. It was just this idea that, "In the long term, we expect the curve to go up. We very much believe in the upward trajectory of just about everything. But on the day-to-day decisions, on the minutiae, we're quite critical. How do we make sure this thing works?" And we'd think about all the ways in which it doesn't work.
**Lenny** (00:20:53):
So zooming out a little bit. We've been talking about Stripe. Retool also is a very first principles, innovative company.
**Lenny** (00:20:59):
Something that I think of when I think of Retool is, during the wild market days of long ago, last year. I know Retool was very conservative in how they raised money, and the valuations they raised at. Which, looking back, ended up being a really good idea. While everyone's raising at $100 billion, I think their last round is a few billion. And it's a very reasonable, conservative way to think about fundraising.
**Lenny** (00:21:23):
And so, I guess just thinking about innovation in general. Why do you think some teams are able to run innovation machines, continue to put out new products, disrupt industries, while other companies kind of plod along and stay conservative?
**Lenny** (00:21:37):
Is there anything you've seen, something you bring to teams you work on, to help foster innovation and big thinking?
**Eeke de Milliano** (00:21:43):
Yeah, I actually think about the extremes of that question. So not, "Why are some teams innovative?" But, "Why isn't every team innovative?" I feel like no one wakes up in the morning and thinks, "Yeah, today I want to work on boring, incremental stuff."
**Eeke de Milliano** (00:21:57):
But, most teams do end up working on pretty incremental stuff. I always wonder, "What is it that's stopping folks from being creative and thinking bigger?" And I think it comes down to a couple of things that companies do sort of unwillingly, or not even realizing it.
**Eeke de Milliano** (00:22:14):
And one is this fear of failure. I think leaders want the upside of innovation, but they're not really willing to deal with the cost of innovation. Which is like, "Look, if you're going to swing big, you will invariably stumble sometimes."
**Eeke de Milliano** (00:22:29):
So I think if you want to mitigate that, you have to start shining light on failure. That's really the only way. You have to start normalizing it a little bit. And obviously, if an individual, or if a team is consistently failing and not learning. That, you need to deal with.
**Eeke de Milliano** (00:22:46):
But I think sometimes it's good to fail. And when you do fail, use it as an opportunity. Don't squander that moment to not learn.
**Eeke de Milliano** (00:22:57):
But yeah, one example is, instead of calling something a postmortem, call it a retrospective, so that it's a positive thing. Like, "Hey, we're learning from this thing."
**Eeke de Milliano** (00:23:07):
And then, I think the other way to kind of mitigate the feeling of failure is, you have to figure out how to give folks more at BATS. Because obviously, anything that takes one year to ship, and you haven't gotten any customer feedback, the stakes of that are just going to feel so, so high. If you get it wrong, it's going to be devastating. So you have to figure out how to lower the stakes.
**Eeke de Milliano** (00:23:27):
And honestly, I think in some ways it's kind of easy. It's like, "Look, don't put too many resources against these bigger swings. Have them be small teams." And then also, just get customer feedback as quickly as possible. Don't wait until the thing is perfect. And that way, you can limit the risk.
**Eeke de Milliano** (00:23:44):
So yeah, I think fear of failure, that's definitely one thing that stops teams from being innovative.
**Eeke de Milliano** (00:23:49):
There's a very practical one. Sometimes teams are just getting bogged down by really urgent work. There's too much tech debt. There's too much product debt. Bugs, instability. It's a massive hierarchy of needs. There's just no way that they're going to be able to focus on the enlightened, bigger, creative stuff if they're just heads-down dealing with incidents all day. So if that's the case, yeah, diagnose it and get your team out of that.
**Eeke de Milliano** (00:24:18):
And then, I think the last reason why teams aren't always that innovative is because, I think thinking big is really hard. And to some people it comes pretty naturally. But for most of us mortal souls, it's just really, really hard. And it takes time. And when you're at a startup and you're just grinding day-in, day-out, you're treading water just trying to make it through the day.
**Eeke de Milliano** (00:24:45):
Taking the time to really think about the strategy, and where things should go, and get creative. It's pretty hard. So I call this... You have to give teams permission to think. So create these moments in your company culture, in your overall business processes, where you're asking people, you're literally saying, "Hey, this is part of your job to think bigger."
**Eeke de Milliano** (00:25:09):
So at Retool, we have these team charters and we do team planning. And at the bottom of every team charter we have a section called, Think Bigger. "With 20% more time, what would you do that isn't on this list already?"
**Eeke de Milliano** (00:25:21):
And then another really neat tradition that we had at Stripe, and we have a Retool now, too. Is this thing called, Crazy Ideas. So at the beginning of every year, David will send out a blank doc to the org and it's titled Crazy Ideas.
**Eeke de Milliano** (00:25:39):
And the Prompt is, "Crazy ideas are ideas that we shouldn't, obviously, do. There's a 90% chance that they make no sense. But in the 10% chance that they do, they will make a 10x to 100x difference for the retail business." And then, it's literally just a request for crazy ideas.
**Eeke de Milliano** (00:25:57):
And the org loves it. It's amazing. The energy around it is so cool. And it's not just product ideas, it's different ways of how we should run our organization. Or, it's really cool marketing ideas in there.
**Eeke de Milliano** (00:26:12):
So, that doc is awesome. And whenever I have a down day, I just scroll through that doc.
**Lenny** (00:26:17):
I know that you've launched three different products this year which I want to talk about, which maybe came out of this big thinking. But a couple more questions just to dig into some of the stuff you just shared.
**Lenny** (00:26:26):
One is this big doc of awesome ideas. What's come out of that? Because I think of hackathons, and people have all this energy, and it's exciting. And then they do all these cool things and they don't go anywhere.
**Lenny** (00:26:35):
Do things come out of this? Does it lead to actual ideas that people follow up on?
**Eeke de Milliano** (00:26:38):
Yeah. Yeah, yeah. So every year that we send out the doc, we look at the doc from the past year, and we're like, "Okay, did we do anything on this list?" And consistently, we do anywhere between three to eight things on the list.
**Lenny** (00:26:49):
Wow.
**Eeke de Milliano** (00:26:50):
Yeah.
**Lenny** (00:26:51):
Is there an example of a product that launched, that came from that list, that comes to mind?
**Eeke de Milliano** (00:26:54):
Actually, at least one, if not two of the three products that we launched this last year were on the crazy ideas list at one point. Like, a year ago, if you'd asked me, "What is Retool's product?" I would've told you, "Retool helps you build internal frontends really, really fast."
**Eeke de Milliano** (00:27:09):
But if you were trying to schedule a query to run at a later point in time, or have something trigger, or run an ETL task, you couldn't do that in Retool. So that was actually one of the crazy ideas. And that ended up becoming Retool Workflows, which we launched just last year, in November.
**Lenny** (00:27:28):
Okay. We're definitely going to chat a bit about that. I want to go back to the two other suggestions you had. One is embrace failure, make it okay to fail. And then two is, don't let people get sucked into urgent stuff, and have time to focus on important stuff.
**Lenny** (00:27:42):
Is there an example of just how to help people embrace failure? You talked about retrospectives. Is there anything else that you've found works, either as a tactic, as a process, as a framework, just to help people get out of that?
**Lenny** (00:27:55):
Because I hear that a lot, "Embrace failure." And then people are like, "Oh, but I failed and I suck." So yeah, is there anything else along those lines that you found effective to create that feeling?
**Eeke de Milliano** (00:28:04):
To me, it's always in the follow-ups. So have people talk about the failure in these sort of public forums, where usually you talk about the successes. So have someone actually write a note that's like, "Hey, here are all my learnings from this thing that we did." And send it to the org.
**Eeke de Milliano** (00:28:18):
At Retool we have a shipped email list. If you ship something, you'll always send to that.
**Eeke de Milliano** (00:28:24):
Have them send that email to the org. It's just an awesome way to celebrate. Or have them present it all-hands and share what they learned. And it almost always results in, I think, a really positive twist.
**Lenny** (00:28:38):
At Airbnb, I think for a period, there was an award for the biggest failure project and feature.
**Eeke de Milliano** (00:28:42):
Really? That's so cool.
**Lenny** (00:28:43):
Yeah, like a trophy or something. It was a short-lived idea, but it was funny.
**Eeke de Milliano** (00:28:47):
Yeah, yeah, yeah.
**Lenny** (00:28:48):
And then, on the second bullet point of urgency, giving people a chance to think longer term. Is there anything there, that you found to be actually effective, to create that culture, and give PMs and product teams a chance to think longer term, and not just be stuck in the fires that they're dealing with?
**Eeke de Milliano** (00:29:02):
There's a couple of top-down things, and a couple of bottom-up things.
**Eeke de Milliano** (00:29:06):
On the top-down, sometimes you just have to be willing to fund someone with something. Like, they come to you with an idea and you're like, "Look, yeah, take an engineer and go do it." And you just have to give folks that sort of organizational buy-in.
**Eeke de Milliano** (00:29:21):
Actually, I was thinking back to that engineer, Brian Krausz at Stripe, who started poking around on this marketplace model. And I was thinking, I can't remember a moment when someone formally said to him, "This is now your job." I think he just went and looked, and went and dug into it. And at some point, I think a manager was like, "All right, this is now your job."
**Eeke de Milliano** (00:29:43):
But yeah, no, I think you have to be able to fund folks' time and give that. Hackathons, I think, are pretty good for that stuff. It is kind of a moment for folks to take a step back.
**Eeke de Milliano** (00:29:55):
And then, I think more than anything, in people's planning processes, I really like asking folks the 20% more time question. Or the other question was, "Look, if you doubled the team today, what would you do?" That shows up in our planning processes as well.
**Eeke de Milliano** (00:30:08):
And I think it really helps people kind of break out of this... I think you end up planning towards the team that you have and not the team that you should have. So, that's how folks can break out of that process.
**Lenny** (00:30:20):
Awesome. I really like the think bigger bucket in your planning docs. Just like, "What would you do if you had more resources?" Maybe a quick question there. Is there a bunch of detail that you ask them to put into that, or is it just a bullet point of big ideas?
**Eeke de Milliano** (00:30:32):
Folks can just go crazy on it. It's however they want to take it. I've seen folks actually create entire demos.
**Eeke de Milliano** (00:30:40):
But I actually think the trick is less structure, in those cases. Because you don't really want to sort of pigeonhole... Or make it even that intimidating for folks. If someone just wants to write down a few bullets, that's great.
**Lenny** (00:30:53):
**Eeke de Milliano** (00:32:28):
So the three products we launched, one was Retool Workflows that I talked to you a little bit about. It's like, if you want to be able to, essentially create a workflow. Like schedule an alert, run a task, you can kind of do it in the Retool way. Where it's this visual, sort of easier builder of creating these different sort of workflows. But you can write your own code on top of it, as well.
**Eeke de Milliano** (00:32:50):
The second product is Retool Mobile. So you could pretty easily build incredible web apps with Retool. But there are plenty of folks who don't sit behind their laptop at a desk all day. And for those folks... We had a lot of companies who were like, "I want a mobile native app." And so, we launched that product.
**Eeke de Milliano** (00:33:09):
And then the third product was Retool Database. So until very recently, if you came to Retool, you could connect your data via your APIs, your database, directly into Retool.
**Eeke de Milliano** (00:33:20):
But what we found is that actually, a lot of folks either don't have access to their database, or they're just trying to build an internal tool and they don't necessarily want to store that data in their production database.
**Eeke de Milliano** (00:33:29):
So we built... Essentially, we spin up a post [inaudible 00:33:32] database for you. And you can just access it via a really nice UI and manage it directly in Retool.
**Lenny** (00:33:38):
Amazing. Okay, back to the other two questions.
**Eeke de Milliano** (00:33:42):
Yes. Okay. So I think your second question was, "Was this a good idea?"
**Lenny** (00:33:44):
Right.
**Eeke de Milliano** (00:33:46):
Yeah. You know what? I think in hindsight, if I were to do it again, I think sequencing it would've been slightly better. Just because, I think what we ended up doing is, we ended up launching the idea behind all three of these products at around the same time. And they all ended up maturing at around the same time, and that was just a lot of headspace from the org. Even though actually, the teams themselves were not that big.
**Eeke de Milliano** (00:34:18):
It was just like, we had all these products and we were just waiting for them to launch and waiting for them to launch. Whereas, maybe if we'd sequenced it, I think that would've felt more satisfying to the whole organization.
**Eeke de Milliano** (00:34:28):
But, I mean, it ended up working out. I think that's kind of the crazy thing. It's like, we were able to pull off launching these three products.
**Eeke de Milliano** (00:34:36):
And by the way, I should caveat that, the further I get along my career, the more I realize I'm just kind of building on the shoulders of giants. And a lot of these ideas, et cetera, were very much in the works and were happening before I came along.
**Eeke de Milliano** (00:34:50):
But yeah, it was really neat to see how we got that all over the finish line in a year.
**Lenny** (00:34:55):
And then, the last question there is just, what do you think you did to allow for this? Because it's pretty rare you can build so much. And I know the team's not huge. How many people work at Retool, roughly?
**Eeke de Milliano** (00:35:05):
Today, we're around 300 people.
**Lenny** (00:35:07):
Yeah. So how do you structure an org to build three and launch... I didn't realize they launched around the same time. It's like, I'm picturing Elon Musk launching three rockets at once. How do you allow for that to happen?
**Eeke de Milliano** (00:35:20):
Yeah, I'm sure our product marketing team felt that way. Yeah, a couple of things. We started really small with all of these initiatives.
**Eeke de Milliano** (00:35:30):
So I think I mentioned, we really had one or two people working on each of these products for the first six months. So it was one engineer and one designer, or one engineer and one PM. And they really didn't get funding until it was clear that there was something there.
**Eeke de Milliano** (00:35:46):
So those teams, they spent a ton of time with customers. They spent a ton of time building, a ton of time prototyping. And it was kind of the moment where it was like, "Okay, they are there." That we started bringing more people onto the team.
**Eeke de Milliano** (00:35:59):
So, that was the first piece. The second piece is that, we really treated them like startups. We're like, Retool's the VC, and Retool funds with resources and Retool's existing customer base. Which is obviously quite valuable, because you have all these customers you can market to and promote to.
**Eeke de Milliano** (00:36:15):
But then, the teams really had to prove that ROI. Either in engagement, or eventually revenue, in order to be able to move forward.
**Eeke de Milliano** (00:36:25):
And then the third thing... And this one, actually I think it can be quite controversial. Is, we were really deliberate about keeping these teams separate from the rest of the org, especially early on. Now, a lot of them, they're very much a part of the overall organizational processes.
**Eeke de Milliano** (00:36:42):
But very early on, they were running on their own. They were meeting quite independently with one, or two, or three folks from the leadership team. And they were also just quite separate from the product itself.
**Eeke de Milliano** (00:36:56):
I think Retool Mobile's actually a really good example, where we had a lot of debate about whether or not we should build Retool Mobile out of the core web app builder. Because a lot of the primitives are the same.
**Eeke de Milliano** (00:37:09):
And we eventually decided that we were going to run it as a separate team, because we wanted the team to be able to move really, really quickly. And we didn't want it to get bogged down in, what are just the realities of running a product that has product market fit, like bugs, yada, yada, et cetera.
**Eeke de Milliano** (00:37:24):
And I think that was absolutely the right call, because Retool Mobile actually has quite a different target customer. Which, we only really realized maybe like halfway through the project. And I don't think we would've been able to really understand that, or even get broader in that kind of thinking, had we sort of been stuck in the core retail product.
**Eeke de Milliano** (00:37:43):
But yeah, there was a cost to that, too. Which is like, "Okay, now we have these two products, and we have to..." I think obviously the strength will be, "How do all these products interact with each other, and how do they build on top of each other?"
**Eeke de Milliano** (00:37:52):
So, we have to go and invest in that now. But I think it's totally worth it, because your team can just move more quickly, be more independent, and think more independently, too.
**Lenny** (00:38:00):
In the time that you worked at Stripe and Retool... I know we chatted before we started recording. You think a lot about, "What is the right level of process for companies at different stages?"
**Lenny** (00:38:12):
And I'd love to just hear your thoughts, because I know that's a challenge a lot of companies face. "How much do we put in now? Do we get inspiration from big companies? Do we try to stay lean?"
**Lenny** (00:38:22):
Something here, that we actually run into. I'll just mention briefly that, there was a huge resistance to process for a long time. And so the product team was just kind of a little crazy for a bit. And then we were like, "Okay, we need product development process. We need deadlines and specs." And that helped a lot.
**Lenny** (00:38:40):
So let me ask again, just how do you think about the right level of process for a stage of company, and what have you learned there?
**Eeke de Milliano** (00:38:45):
Yeah. What I would really love from companies is just sort of like this time capsule, where you can see what their processes were when they were like 20 people, and 50 people, and 100 people, and 500 people.
**Eeke de Milliano** (00:38:55):
Because when we were at Stripe and we were trying to figure out our planning process, we actually talked to Amazon, and Atlassian, and Apple, and all these companies that we really, really respect and look up to.
**Eeke de Milliano** (00:39:07):
And I remember taking down notes from these companies and being like, "Yeah, this is awesome, but there's no way that this will work for Stripe." Stripe was so much smaller than any of these companies.
**Eeke de Milliano** (00:39:17):
So yeah, they were showing us where we had to go, but no idea how to get there. And so, yeah, Lenny, maybe you can help us figure out time capsules for companies and what processes make sense.
**Lenny** (00:39:27):
Yeah. I am working on that, roughly.
**Eeke de Milliano** (00:39:28):
Oh, nice.
**Lenny** (00:39:30):
I'm going company by company, about how they think process and about process. And then maybe I'll check in every couple of years.
**Eeke de Milliano** (00:39:36):
Cool. I love that. But yeah, to answer your question directly. Process... Yeah, it really gives people a bitter taste in their mouth, I think.
**Eeke de Milliano** (00:39:47):
Process, by definition, is variance reducing. You're introducing it, because you worry that the variance in your org is too high. You want people to sort of meet a certain standard.
**Eeke de Milliano** (00:40:00):
And the cost of that is obviously, while you are reducing the standard and bringing folks up to the average, you're also bringing other folks down to the average. And oftentimes, the folks you're bringing down are your highest performers, your most creative thinkers. The folks who, I think actually don't really need process to do their best work.
**Eeke de Milliano** (00:40:21):
And so, that, I think is always the tension that you have with process. And obviously one of the reasons why companies introduce process much more and more, as companies get bigger, is because it's harder to get all these folks who don't need processing. You actually want to reduce the variance.
**Eeke de Milliano** (00:40:38):
This is actually a little bit of an aside, but it's kind of relevant, so I'm just going to mention it. And you can feel free to let me know if it's too much of an aside.
**Lenny** (00:40:44):
Let's get into it.
**Eeke de Milliano** (00:40:47):
But, I was just listening to this awesome podcast with Russ Roberts, who's a professor. He hosts EconTalk. I don't know if you listen to it.
**Eeke de Milliano** (00:40:56):
And he was in interviewing this guy, Ian Leslie, who's this great writer and has just written this article that's... Basically, something along the lines of what it means to be human in the age of AI.
**Eeke de Milliano** (00:41:07):
And I thought he just articulated this idea well. Which is, we're all really so impressed when we see ChatGPT-3 spit out this piece of writing that feels very human-like.
**Eeke de Milliano** (00:41:20):
But what we're kind of forgetting is that, over the last 10, 20, 30 years, we're actually asking humans to be a lot more robot-like. In that, we're really asking everyone to standardize in a lot of ways. And we're making people a lot more formulaic. If you think about how we teach people to write, it's like, "Well, there's five paragraphs. And there's your opening paragraph. And you state your topic."
**Eeke de Milliano** (00:41:43):
So anyway, I think the point is, the more formulaic, the more sort of mass produced you're trying to make something. The more you kind of quench people's creativity, and the further away you get from the really, really high highs. And that, to me, is the cost of process, and rules, and templates.
**Eeke de Milliano** (00:42:05):
So if you're going to introduce it, be really, really sure that you're okay with that cost. And give folks escape hatches.
**Eeke de Milliano** (00:42:13):
So I've started referring to this as the MVP, the minimum viable process. So if I give folks a template, I'm like, "Look, use the template. But if you want to break out of it, please absolutely do." And I've started writing this at the top of templates now.
**Eeke de Milliano** (00:42:26):
It's like, "If this doesn't work for what you're trying to explain, don't use it. But just know that this is the minimum viable thing. We're setting the bar here, but go higher if you can, please."
**Eeke de Milliano** (00:42:38):
So anyway, that's my sort of long drive on process. With all that said, I do think that companies, there's just a set of documents that are really, really viable. That every sort of level of the organization should have throughout its lifecycle.
**Eeke de Milliano** (00:42:54):
And then, I think how sort of involved it is, or how long term it is really depends on how big you are.
**Eeke de Milliano** (00:43:00):
But those documents, to me, are the charter. So, "What is your mission, your vision and your strategy?" The goals, "What are you aiming to do and how are you going to measure success?" And then the roadmap, "What is the thing that you're shipping?"
**Eeke de Milliano** (00:43:15):
And I think the whole company needs these, the whole function. So in product, you need all three of these. And then, within each team you need all three of these.
**Eeke de Milliano** (00:43:26):
And I've kind of noticed two things about this framework for myself. One, I've actually noticed that teams often work their way from the bottom-up, versus top-down. They start with a roadmap. They're like, "What are all the things we're going to ship?" Especially early on. And then they kind of work their way into a charter. But I think it's really, really worth it to start from the top-down.
**Eeke de Milliano** (00:43:47):
And then, the second thing that I've noticed is that your time horizon really shifts as you get more mature. So if you're very early on, you don't have PMF, you should have a charter, but your charter should be like three months in the future. Because you can't look that much further.
**Eeke de Milliano** (00:44:01):
And if you're a company that's humming and going, your charter is probably... The horizon's maybe a decade.
**Lenny** (00:44:11):
Wow. There is so much there. I could go into so many different directions. One thing I wanted to follow up on a little bit, is this idea... Such a great point. That process brings the best people down and kind of averages them out to create consistency.
**Lenny** (00:44:28):
And I'm curious if there's anything else you've seen succeed in allowing the best and most innovative brains to just do their thing. I know part of it is probably hiring amazing people. But yeah, is there anything else that's an escape hatch of just like, "Oh yeah, this person, just go. Go figure this out."
**Eeke de Milliano** (00:44:45):
To me, the unlock for organizations is managers, for this. Because you need managers to both detect the high performers and be like, "This person doesn't need the process." And then you need managers to give that person air cover to be like, "We're honestly..." Because what you're doing is, you're giving them some special treatment and you need to be kind of okay with that.
**Eeke de Milliano** (00:45:02):
And you also need to be okay with the organizational cost for that. Claire, who used to be the COO of Stripe, would always say, "Are you willing to break the org for this person?" And I always thought that was a really nice framing. And you kind of need to decide who you want to do it for, too.
**Eeke de Milliano** (00:45:17):
But yeah, some people are just that good that like, "Yeah, of course you'll break the org for them." They're going to break the org in the best way possible.
**Lenny** (00:45:27):
Yeah. I love that term. I think Claire's coming on this podcast. She just wrote a book, right? Is that the same person?
**Eeke de Milliano** (00:45:29):
Yeah.
**Lenny** (00:45:30):
Okay, great.
**Eeke de Milliano** (00:45:30):
Yeah, she just wrote a book. Yep.
**Lenny** (00:45:33):
All right, we just booked her. Come, and maybe we'll spend some time together.
**Eeke de Milliano** (00:45:36):
That's awesome.
**Lenny** (00:45:37):
Do you have any other product building philosophies that you found especially useful in your time at Stripe, and Retool, and anywhere else?
**Eeke de Milliano** (00:45:45):
I have a couple of, I guess, specific mental models that I use. The first is, build for your best user, not your worst user.
**Eeke de Milliano** (00:45:53):
And what I mean by that is, I think it's actually really easy to get stuck, or to focus on, "What if there's abuse of this product?" Or think about all the ways in which the product won't be used well. And then you end up sort of shaping the product in these really weird funky ways to make up for that.
**Eeke de Milliano** (00:46:11):
Whereas in reality, the worst users, they should be a fraction of your users anyway. So you shouldn't really be building for them.
**Eeke de Milliano** (00:46:19):
I think a really good example of this is onboarding processes. Where, you're probably going to be building an onboarding process, where you're trying to collect a lot of data. Or trying to figure out, "Hey, how do I help this user who maybe isn't well suited for my product to be successful?"
**Eeke de Milliano** (00:46:37):
Really, you should just be building an onboarding process for the user who's going to jump into your product and get it immediately.
**Eeke de Milliano** (00:46:42):
I was thinking about this actually just the other day. Because we were in this product review, and we were talking about this other new product that we're thinking of exploring.
**Lenny** (00:46:48):
More products? It never ends.
**Eeke de Milliano** (00:46:52):
Yeah, exactly. And we're kind of going down this path of like, "Oh, well if this gets really big, there's going to be all this abuse of the product." And Anthony, our founder was like, "Wouldn't that be an amazing problem to have?" And we're like, "Yeah, that's a really good point."
**Eeke de Milliano** (00:47:03):
So we kind of put that on the back burner.
**Lenny** (00:47:07):
That's an interesting approach, because usually you're trying to optimize a flow, get more people through it, which are the least good users.You're saying you found more success just focusing...
**Lenny** (00:47:16):
Is this more initially, focus on the users that will understand this, and be excited about it, and make that work really well. And then, over time, build on that?
**Eeke de Milliano** (00:47:23):
Yeah, totally. Yeah, sure. If you're going to look at the end, and you're trying to optimize, et cetera, absolutely. But in that sort of early product development stage, it's just not worth it to be too focused on that.
**Lenny** (00:47:33):
Got it. Sweet.
**Eeke de Milliano** (00:47:34):
So, that's one. The other one, our head of design, Ryan, always kind of reminds us of is, build the scooter, not the axle.
**Eeke de Milliano** (00:47:44):
So if you're trying to build the minimum viable product for a car, don't build just the wheels and the axle, build the scooter first. And then from there, you build the bicycle, and the motorcycle, and then the car.
**Eeke de Milliano** (00:47:54):
And it's always just such a good reminder. You always want to start building the whole thing. But really try and think about the slice that gets the customer to complete value on a smaller thing first.
**Eeke de Milliano** (00:48:06):
So with Retool Mobile for example, there's just so much you could be building there. And we decided very specifically, "Hey, we're only going to build this for companies that have field workers and they would need to do inventory management."
**Eeke de Milliano** (00:48:18):
And it's a very specific slice, but it helps get through from something that was actually viable, beginning to end.
**Lenny** (00:48:25):
Got it. So it's an approach for MVPs, basically. Make something simple and functional, not just something barely... Not actually working, but getting you to some dream product eventually.
**Eeke de Milliano** (00:48:37):
Yeah. And then the last one is this idea of 70/20/10 split investments. I really think that a lot of product management can sometimes be reduced to funnels and portfolios.
**Eeke de Milliano** (00:48:51):
So the 70/20/10 investments model in my head is just like, 70% of your building time should really be going to your core product, that has product market fit. 20% of your time should be going to strategic initiatives that aren't core, but they're strategic to the company, that you know have to do them. And then, 10% of your time should be going towards bets.
**Lenny** (00:49:11):
That's actually exactly the same heuristic I've always used. One question there is, how do you think about maintenance and bugs within that?
**Eeke de Milliano** (00:49:19):
Yeah. To me, that falls squarely in the 70%. So yeah, core product, tech debt, sort of the maintenance mode type stuff. And core product, obviously you're also doing a bunch of new stuff there too.
**Eeke de Milliano** (00:49:31):
But yeah, no more than 70% of your resources should be going there.
**Lenny** (00:49:35):
What did you say the 20% was?
**Eeke de Milliano** (00:49:37):
Strategic initiatives that aren't your core, but you just know, based on your strategy, you have to do these things.
**Lenny** (00:49:45):
Got it. So the way I break it up is, 20% is where I put bugs and maintenance. And then 10% was big, ambitious bets. So it was similar ratios, but different things go into the buckets.
**Eeke de Milliano** (00:49:56):
Cool.
**Lenny** (00:49:57):
But, let me ask a similar question. How do you, at Retool, and maybe even at Stripe, think about finding time to do maintenance and bugs? Do you build it into roadmaps? Do you set off time to just fix all the bugs? I know it's probably an evolution, and it goes back and forth. But, any thoughts?
**Eeke de Milliano** (00:50:11):
Yeah. This, I think, is really one of the trickiest parts of product management, in my mind.
**Eeke de Milliano** (00:50:18):
We don't have a company-wide sort of process on this. It's pretty team specific. Some teams do Friday bug bashes. Other teams are just, as products roll out, will work on them as they go.
**Eeke de Milliano** (00:50:33):
I was actually speaking to a product manager at a different company, who mentioned that they just spent the last 18 months doing just product polish and bugs. And I think they landed in a place where they had to do it, because they just had so much debt. But luckily, we're not there yet.
**Eeke de Milliano** (00:50:54):
Right now, we let most of the teams just kind of do it themselves and figure out what makes sense for them.
**Lenny** (00:50:59):
Okay. Awesome. I wanted to go back to something that I've heard about Retool, that you all are really good at. Which is PM's being really close to customers. And I'm curious what you've done there, or what the team has done there, that it's been really effective?
**Eeke de Milliano** (00:51:13):
Well, I do think every good product team figures out how to get close to customers. But just based off of my observations from Retool, and what I've seen at other companies, there are a couple things that are more pronounced at Retool than I've seen in a lot of other places.
**Eeke de Milliano** (00:51:28):
The first is, we have a lot of PMs who used to be in customer-facing roles, at Retool. I obviously am a big fan of that. I think there's just nothing like really understanding the value of your product, at the moment where a customer actually has to put money down. And so, I really like that about PMs, who have had those conversations with customers and they really get it.
**Eeke de Milliano** (00:51:53):
Second is, because the retail product is so technical... And I do think this just depends on what product you have. Our PMs are really, very technical. Everyone has either a CS degree, or has done some sort of engineering in the past.
**Eeke de Milliano** (00:52:06):
Third is, we use Slack very heavily to talk to our customers and interact with them. So at this point, I think we have hundreds of Slack channels with customers. Every time we're testing a new product, or a new customer who's somewhat large, comes online. We will work with them in Slack, to get there off-the-cuff feedback, just back and forth. It's really nice. We just have this direct line to them, which is awesome.
**Eeke de Milliano** (00:52:34):
And then, the fourth thing we do is, we use Retool to build Retool. So our product roadmap lives in a Retool app. And the app that we use to have feature flags for particular features, is a Retool app. So PMs are just in the product all day long, every day. They're their own customers in a lot of ways, and that really helps as well.
**Lenny** (00:52:57):
Wow, I didn't know that. That is very cool. So you build a task management product using Retool?
**Eeke de Milliano** (00:53:03):
Oh, yeah. Well, we built many... Basically, all of our internal tooling happens in Retool. Like, our PMs, all their team dashboards are in Retool. All of their task tracking is in Retool. Submitting linear requests or bug requests happens in Retool, and then goes to Linear. So yeah, it's how we run the company.
**Lenny** (00:53:23):
You haven't been able to replace Linear yet? That's cool. I'm a big fan of Linear.
**Lenny** (00:53:29):
Okay, two more questions and then I'll let you go. One is around product growth. Which, I don't want to get too into. We've talked about it a bunch on this podcast.
**Lenny** (00:53:37):
But, it's interesting that Stripe was very product-led growth. It was just self-serve PMs, engineers, whoever, just started using it. It grew and became enterprisey down the road.
**Lenny** (00:53:49):
Retool, on the other hand, I think people think it's product-led growth. I imagine it's actually sales-led, mostly.
**Lenny** (00:53:54):
And so, I'm just curious what you've learned about the difference between building product and leading product teams within a sales-led org, versus a product-led org.
**Eeke de Milliano** (00:54:04):
I have a couple of insights on that. One interesting insight is that, teams that have one always want the other.
**Lenny** (00:54:10):
That's so true.
**Eeke de Milliano** (00:54:12):
Whenever I talk to candidates, I feel like you can always tell what their company has, because they'll be asking a lot of questions about the opposite. If they're probably a growth company they'll be like, "Well, how are you guys thinking about Enterprise?"
**Eeke de Milliano** (00:54:24):
And then, if they are more of a sales-led growth company, they're like, "Well, how are you guys thinking about your self-serve motion, or your product-led growth?"
**Eeke de Milliano** (00:54:31):
And my main takeaway, just in... And I don't know if I would even use the dichotomy of product-led growth, or sales-led growth, with Retool. I think we do have a lot of product-led growth. But we work with a lot of enterprise customers, and a lot of our revenue comes from enterprise customers, and we have a fantastic sales team.
**Eeke de Milliano** (00:54:49):
And I think the main thing is that, you just have to really figure out your interaction mechanisms with sales. And that just has to be so, so tight.
**Eeke de Milliano** (00:55:00):
And it goes in both directions. There's obviously, how you get feedback from them, because they are so often on the front lines talking to customers. Moreso than product managers, even.
**Eeke de Milliano** (00:55:08):
But it also goes the other way. If you are going to ship something, or if you are going to put out a roadmap, like, "How do you make sure that the sales team has everything that they need..." The sales, and in Retool's case, the success team and the support team, "Has everything they need to accurately talk to customers about that?"
**Eeke de Milliano** (00:55:26):
And I've always actually found that really hard, because it's really hard to figure out the right altitude. If you're giving a presentation on the roadmap, people are either going to feel like it's too high level. Or, it's too low level for folks who maybe are new.
**Eeke de Milliano** (00:55:40):
So this year, we're actually trying something different. We are doing a science fair. Where, each product team has a little booth. And they get to stand there, and anyone who has questions about the product can come... You know, from the go-to-market side, can come and ask questions, and get demos, and go as deep as they need to.
**Eeke de Milliano** (00:55:57):
So, I'll let you know how that goes. But I'm excited to experiment with it.
**Lenny** (00:56:04):
Okay. Are there going to be foam core boards, and will there be ribbons?
**Eeke de Milliano** (00:56:08):
There may be prizes. Who knows?
**Lenny** (00:56:10):
Oh my God. I can't wait to see a picture of this. Final topic. You have this concept that you call the product talent portfolio. What does that mean, and how have you found that useful in your product leadership life?
**Eeke de Milliano** (00:56:25):
Yeah. Yeah, it's back to like, all of product management is portfolios and funnels.
**Eeke de Milliano** (00:56:29):
I think it's really tempting as a manager, to build a team in your image, because you understand their skillsets and you value those skillsets. And you're going to be able to detect and assess those skillsets better.
**Eeke de Milliano** (00:56:43):
But the best product teams, in my mind, have really figured out how to balance the talent portfolio. So instead of having a bunch of PMs who all spike in one particular area, figure out how you can create complimentary skillsets for the whole PM team, so the whole is much stronger.
**Eeke de Milliano** (00:57:04):
And one way in which I like to do that is, I really like to balance product teams with homegrown product managers, who really get the product. They've probably been in it. They're amazing culture carriers, often. They really set the tone. But they may not have seen product management at other companies, and they may not have some of the more conventional and traditional product management skillsets.
**Eeke de Milliano** (00:57:25):
So I want to balance that with product managers who've come from other companies, and have done it, and can bring a little bit more of that product manager rigor. Even though they don't have, in the Retool case, the core Retool product management vibe.
**Eeke de Milliano** (00:57:41):
So, that's one example. I think there's others as well. Some PMs are just incredible execution machines. Other PMs are amazing visionaries. You kind of want a little bit of all of them.
**Eeke de Milliano** (00:57:51):
And you want to also balance within all of your different pillars. So we have three different sort of product pillars at Retool, and there's leads for all those pillars. And I always push the leads to hire people who don't look like them, so that we have balance everywhere.
**Lenny** (00:58:08):
I love that. Do you, actively, as you're hiring, "Hey, well you're strong in these areas. Here's the person we need, here. We want this specific, super strategy minded person." Is that actually how you think about this?
**Eeke de Milliano** (00:58:20):
Yeah. I do a little personal exercise for myself every six months, where I chart out the team that we have today, and write down all of the strengths that we have, all of the weaknesses that we have, as a team. And then I try to hire specifically for those weaknesses.
**Lenny** (00:58:35):
Amazing. Any last pieces of wisdom or thoughts, before we get to our very exciting lightning round?
**Eeke de Milliano** (00:58:42):
I think that's it on my end.
**Lenny** (00:58:43):
Okay. We got through everything I was hoping to get through.
**Lenny** (00:58:46):
So with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?
**Eeke de Milliano** (00:58:52):
I'm ready.
**Lenny** (00:58:53):
What are two or three books that you recommend most, to other people?
**Eeke de Milliano** (00:58:57):
Bird by Bird: Instructions on Writing and Life by Anne Lamott. It's incredible. So touching. Really, really great. Also, I think product managers should be great writers. So, I love that.
**Eeke de Milliano** (00:59:08):
And then the other book that I was going to say, but I'm glad you mentioned Claire, is Claire's book, Scaling People, which is coming out. I had a very small hand in ghost writing for her a little bit, in the first draft. So I use a lot of the early chapters from that book still, in management. And I still recommend the tactics in there, so I'm excited for her to get it out.
**Lenny** (00:59:29):
Wow. I've been hearing about ghost writing as a career recently, and it feels like it could be an option for you down the road.
**Lenny** (00:59:36):
I'm excited to read the book. I haven't gotten a copy yet. I think you could pre-order it now, and we'll link to it in the show notes.
**Eeke de Milliano** (00:59:41):
Nice.
**Lenny** (00:59:42):
What's a favorite other podcast that you like to listen to, other than maybe the one you're on right now?
**Eeke de Milliano** (00:59:46):
Yeah, this one's great. I can't choose between these two, though. One is Lex Fridman. And then the other is EconTalk by Russ Roberts. I really like that both of them are... Their agenda is curiosity, which I love.
**Lenny** (00:59:59):
Totally resonate there. What is a favorite recent movie or TV show that you've enjoyed?
**Eeke de Milliano** (01:00:04):
Is it too basic to say White Lotus?
**Lenny** (01:00:07):
Cool. That's the most mentioned one, which says a lot, right? That just says how good that is, because I love it too. But, that works. Season one or season two?
**Eeke de Milliano** (01:00:17):
Oh, season two, all the way.
**Lenny** (01:00:19):
Yeah, same. I'm excited for season three. No spoilers. Favorite interview question that you like to ask candidates?
**Eeke de Milliano** (01:00:27):
To what do you attribute your success? And you can't say luck.
**Lenny** (01:00:32):
Interesting. Because most people look for, do they believe it's luck, versus their innate skill? So you don't even allow them to say luck? Interesting.
**Eeke de Milliano** (01:00:41):
Yeah. Because I think humble people will always say luck in some way. And I always kind of wanted to know, "How self aware are you, and how curious are you?"
**Eeke de Milliano** (01:00:51):
And I think people who have really gone back and reflected on why are they where they are today, really says a lot about how they think about the world.
**Lenny** (01:01:03):
I love that. What are some SaaS tools that you love, or use often, at your current company, or anywhere else?
**Eeke de Milliano** (01:01:08):
Yeah. Well, first and foremost, it's Retool. And then, the other SaaS tools that we use a lot, Slack, Gong, Linear and FullStory.
**Lenny** (01:01:18):
Awesome. Favorite new product that you found, maybe in life, maybe at work?
**Eeke de Milliano** (01:01:24):
**Eeke de Milliano** (01:01:31):
Nice. Yeah. I mean, I think it's really incredible what they've done.
**Lenny** (01:01:35):
Maybe describe it briefly, just so folks know what that is.
**Eeke de Milliano** (01:01:38):
It basically records everything that you're doing on your computer and then makes it really easy for you to search it. Which, it's just incredible. I don't know if you work this way, Lenny. But I feel like nowadays, I don't really go to tabs anymore. I kind of directly search for the thing that I'm searching for. And I think Rewind just fits that user behavior so, so well.
**Lenny** (01:02:06):
Amazing. Eeke, this was so much fun. We got through everything I was hoping for, and more.
**Lenny** (01:02:09):
Two final questions. Where can folks find you online if they want to reach out, learn more, see what you're up to? And, how can listeners be useful to you?
**Eeke de Milliano** (01:02:16):
Definitely find me online on Twitter. It's @EekeDM. And, how can they help us? Try out the Retool product and give us some feedback.
**Lenny** (01:02:25):
Amazing. Retool.com, right?
**Eeke de Milliano** (01:02:25):
Yes.
**Lenny** (01:02:26):
Awesome. Thank you again, for being here.
**Eeke de Milliano** (01:02:28):
Thanks, Lenny.
**Lenny** (01:02:31):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.
**Lenny** (01:02:39):
Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all the past episodes or learn more about the show, at LennysPodcast.com. See you in the next episode.

---

## [8/22] AI and product management | Marily Nika (Meta, Google)

**Marily Nika** (00:00:00):
There is something called the shiny object trap, and I'm always telling people, "Hey, don't do AI for the sake of doing AI." Make sure there is a problem there. Make sure there is a pain point that needs to be solved in a smart way. Once you have identified what that problem is and what that very, very high-level solution is, then reach out and try to figure out how to actually implement it.

**Lenny** (00:00:28):
Welcome to Lenny's podcast where I interview world-class product leaders and growth experts to learn from their hard one experiences building and scaling today's most successful companies. Today my guest is Marily Nika. Marily teaches the most popular course on Maven on AI and product management. She's currently product lead at Meta focusing on Metaverse, avatars and identity. Prior to Meta, she was at Google for over eight years working on Google Glass, computer vision and machine learning around speech recognition. In our conversation, we touch on what PMs should be paying attention to when it comes to what's happening in AI. We talk about a bunch of resources that'll help you get started in the world of AI. How AI tools available today can already help you do your job better as a PM.

**Lenny** (00:01:12):
We also get relatively technical into what exactly is a model, how are models trained, all kinds of fun stuff like that. Enjoy this conversation with Marily Nika after a short word from our wonderful sponsors.

**Speaker 3** (00:01:26):
This episode is brought to you by Amplitude. If you're setting up your analytics stack but not using Amplitude, what are you doing? Anyone can sell you analytics while Amplitude unlocks the power of your product and guide you every step of the way. Get the right data, ask the right questions, get the right answers, and make growth happen. To get started with Amplitude for free, visit amplitude.com. Amplitude, power to your products.

**Lenny** (00:01:53):
This episode is brought to you by EPPO. EPPO is a next-generation AB testing platform built by Airbnb alums for modern growth teams. Companies like Netlify, Tenfold and Cameo rely on EPPO to power their experiments. Wherever you work, running experiments is increasingly essential, but there are no commercial tools that integrate with a modern growth in stack. This leads to waste of time building internal tools or trying to run your experiments through a clunky marketing tool. When I was at Airbnb, one of the things that I loved about our experimentation platform was being able to easily slice results by device, by country, and by user stage. EPPO does all that and more, delivering results quickly and avoiding annoying prolonged analytics cycles and helping you easily get to the root cause of any issue you discover.

**Lenny** (00:02:41):
EPO lets you go beyond basic clickthrough metrics and instead you turn north star metrics like activation, retention, subscriptions and payments. And EPPO supports test on the front end, the backend, email marketing and even machine learning clients. Check out EPPO at geteppo.com, get E-P-P-O.com and 10x your experiment velocity.

**Lenny** (00:03:06):
Marilee, welcome to the podcast.

**Marily Nika** (00:03:08):
Thank you. Hello, thank you for having me.

**Lenny** (00:03:10):
It's very much my pleasure. We've interacted a little bit on Twitter. We've never actually talked before just right now. I've seen your course just all over the place, your course on AI and PM. And so I just thought it'd be really fun to have you on and help us all understand what the hell is happening in AI and especially AI and product. So thanks again for being here.

**Marily Nika** (00:03:33):
Yes, thank you. I'm really excited.

**Lenny** (00:03:36):
I would love your help as a former full-time PM/everyone listening that is a current PM, to help us understand what is going on with AI and product tech in general and tools in general. Move really fast, if you're trying to pay attention to what's happening, it's really hard to stay up to date on where things are going and it feels especially hard in AI.

**Lenny** (00:03:57):
It feels like there's just something coming out every day. And so I have a bunch of questions along these lines. The first is just like what media do you pay attention to stay on top of what's happening and what's new and what's interesting in the world of AI and machine learning?

**Marily Nika** (00:04:11):
As you know very well, subscribing to newsletters is something that's really impactful. And of course, I subscribe to your newsletter, but I am a big, big, big fan of the download by MIT Ecology Review or Atelier. And they're not necessarily AI-centric, but what I'm advocating for and what I'm telling people is that in the future everything will be AI by default. So even if you have something that's technology focused, you'll see a lot of AI starting to get sprinkled in there.

**Lenny** (00:04:40):
I want to follow up on what you just said there, but maybe we'll save it a little bit. Maybe going in a different direction first, what do you think is overhyped in the space of AI right now? What do you think is under hyped and undervalued?

**Marily Nika** (00:04:52):
I would like to discuss strategy between, which is both under hyped and over hyped at the same time. I was reading this article this morning where there are writers complaining and they're very, very fearful and they think, "Oh, writing online is going to die. Everything we've studying for is going to be replaced. They're going to take our jobs and so on." And I'm just like, "No, no, no. Charging PT and technology is enhancing our work. It's enhancing us. It does not steal from us." So that's what comes across right now. And there are other things that are under hype, but obviously ChatGPT is amazing. I'm using it day to day, but there are other things AI can do in an amazing manner.

**Marily Nika** (00:05:34):
I was reading a research article the other day that said that AI can now detect place. So lie detection, whether I is for security reasons or at work or anything like that is now possible. So I encourage people to go to these newsletters and go to these online blogs, 10 prints and so on, and just read what's happening. It's not all about chat reading, there's more, there's more about AI, but you should read a lot.

**Lenny** (00:05:58):
You mentioned that you use ChatGPT in your work life. Talk about that. What are you actually using it for?

**Marily Nika** (00:06:04):
Even when I'm at work and I am trying to come up with a nice mission statement, when we're PMs will come up with mission statements, it's just crucial part and it's where the core begins. You want to get people excited, you want to get people inspired. There is nothing I can write that's going to be as good as what ChatGPT looks like. So what I do is I literally go to ChatGPT and I say rewrite this mission statement from me and even the first try produces something which is fantastic, so that.

Number two, it helps me create user segments in a fantastic way. It will think of user segments that your mind wouldn't even go there, it just wouldn't go there. And it will provide the motivations, it will provide the pinpoints and you just come up with ideas as you read it. And then the last thing that it does is it provides ideas for you whether AI enhanced. So I just use a day-to-day, even [inaudible 00:07:00] day-to-day workflow, but I'm not making it do my job for me, I'm asking it after I have already had a mission in my head and what it is I want to do.

**Lenny** (00:07:10):
So is the way you're approaching it is you just put in, come up with a better mission statement then and then you give it your version of the mission statement?

**Marily Nika** (00:07:18):
Exactly.

**Lenny** (00:07:19):
Interesting. And you're saying that that comes up with a better mission statement than the one you had?

**Marily Nika** (00:07:25):
It's better because the mission statement is going to be read by all disciplines. It's not just going to be read by PMs that already have a lot of context and understand. It's going to be read by leadership, by junior people, by stakeholders, by other departments, by competitors. And you needed to be on Orient ending the words that are meant to be understood by everyone. Even a kid could understand and they would get inspired by you as well.

**Lenny** (00:07:49):
And then you also said he use it for personas. How do you actually frame that prompt with ChatGPT?

**Marily Nika** (00:07:55):
Let's say you're working for a specific product area and you know want to create some fitness band, so you would say something like, who would be interested in the fitness band that doesn't have a screen? And it will provide a bulleted list all of people like, hey, young professionals are that they're interested but don't have enough time. People that do not want to charge their wearables every day. Then the list goes on. It's just fantastic.

**Lenny** (00:08:24):
You were talking about how you think the future of AI is, it's the default and is what you mean there that it's basically baked into every product we use and it helps the user do better things, it helps the product work better. Is that what you mean or is it something else?

**Marily Nika** (00:08:39):
I believe that ballpark managers will be AI product managers in the future. And this is because we see all products needing to have a personalized experience, a recommender system that is actually good. I mean you cannot watch to Netflix, you cannot even watch a movie without needing that. After you watch White Lotus or Stranger Things, you will want something similar to watch. You're not going to want a romantic thing to be suggested or recommended to you.

**Marily Nika** (00:09:06):
Also, automation is another thing. We need to keep improving on society. We need to keep making technological advancements. You're not going to be able to do that if you don't have an AI centric view in every sector that you're working on.

**Lenny** (00:09:20):
When you say that every PM will be an AI PM is your thinking that you'll be using AI tools in your job as a PM or that you'll be building AI into everything you're building with? How do you think about that?

**Marily Nika** (00:09:35):
I think it's that you will need to get comfortable with having a partner that's a research scientist and you will need to understand that these people can produce a smart model. They'll be able to do some automation, some personalization, some recommendations on. In a lot of people, truly uncomfortable, a lot of people don't know how to approach the researchers. A lot of people don't like the uncertainty that research has. A lot of PMs are very, very used to, "Okay, I'm going to do this, I'm going to launch, I'm going to do this, I'm going to launch." Whereas when you're working with research, it's more like we're going to try this and then in a year if it doesn't work out we're going to shut the written down and repeated completing [inaudible 00:10:17]. So I feel that if people get more used to uncertainty and research, things are going to be good in the end for them.

**Lenny** (00:10:28):
I thought you were comparing ChatGPT as a researcher you're working with, but you're actually saying people will have PhD researchers on their teams helping them build models into their product to make their product better. Is that what you're saying?

**Marily Nika** (00:10:43):
Correct. This is exactly what I'm-

**Lenny** (00:10:45):
Interesting.

**Marily Nika** (00:10:47):
And from a product perspective I can imagine like three bubbles in my head. So you want to find the intersection both something that's desirable by users, something that is going to be a viable business and something that is going to be feasible from a research scientist and technical perspective. And then when you have that, it's just going to be a capacity product for desktop launch that you can run with. So yeah, whenever I say researcher, research scientist that can produce an AI machine learning model.

**Lenny** (00:11:15):
Wow. Didn't think about how every cross-functional team might end up with a research scientist. Interesting, interesting. For PMs who are curious about learning how to do this stuff, what are a couple things that PMs today who have no experience with AI, what can they do to start learning how to build AI tooling into their products, understand what the hell's happening in the space of AI?

**Marily Nika** (00:11:40):
This is a good question and I guess the message I want to pass is you shouldn't be overwhelmed by these technologies if you don't have a technical background because you can learn these things and as a PM you'll never need to actually train or code. Also, even if you want to train, there are no code approaches for training models. But to answer the question, if you're working on any product, you can always sprinkle in a smarter feature. So you can make it more secure, you can personalize it, you can enhance it with fraud detection, you can make it more ethical. If it's healthcare, you can make it faster, you can make it more accurate. If it's shopping, you can create better accommodations. Basically anything where you can get data behind the behavior with users can be improved with AI.

So I guess it's all about changing the mindset of PMs. Taking a step back and just thinking about, okay, I have all this data that's just lying and sitting around what is it that I can do with it? I've been meeting PMs that said, "Oh, we're not collecting any data, we're [inaudible 00:12:46] dashboard." So even that is a huge first step towards AI. And then just start thinking about it, where you could deal, get a data science intern and just see what they are going to do. There's just so much people can do.

**Lenny** (00:13:00):
So say you want to start investing in some sort of model, some sort of AI within your team, you're saying maybe hire data scientists who can help you start to build something that you can start integrating. Is that your advice on the first step of once you start, you want to start getting serious about building some sort of AI component.

**Marily Nika** (00:13:19):
There is something called the shiny object trap and I'm always telling people, "Hey, don't do AI for the sake of doing AI". Make sure there is a problem there. Make sure there is a pain point that needs to be solved in a smart way. Once you have identified what that problem is and what that very, very high level solution is, then reach out and try to figure out how to actually implement it. And there's a definition I like giving. I usually say that the generalist PM helps their team and their company build and ship the right product. But the AI PM helps their team or company solve the right problem. So if you want to get into AI PM figure out what the problem is that you will get a data scientist to create a model for solving, but there needs to be a problem, there needs to be audience, there needs to be a user and a pin going for it.

**Lenny** (00:14:11):
What are signs that AI may not be a good approach to solving a problem? You said that, and this happened on a lot of my teams, oh we're going to build a really cool model, it's going to do something really smart in this case and it often ended up being a very low ROI investment and took six months to a year before you even knew what the hell what was happening. Do you have any thoughts on signs that maybe this isn't a place you should be putting a lot of time into AI versus this is definitely an opportunity. Yes, we should do this, invest a lot of time into this.

**Marily Nika** (00:14:42):
Don't do it for your MVP. It makes zero sense. Do not waste time of data scientists that can train models with using powerful machines that are going take weeks to train. This is because if you have an MVP and you just want to get buy-in for an idea or feature that may use AI in the future, take it, create a little figma prototype and just show it some users, just fake what the AI is going to be doing. So a lot of young early stage entrepreneurs reach out to me and they say, "Oh, should train this model to do this and that because we want to prove that there is a market." "No, do not use AI. You should use AI where you think you already have some data or data from an adjacent product that you feel you can leverage for your own product to create something that's meaningful, recommendation automation, what we talking about. But not for an MVP. Please people, this is my advice.

**Lenny** (00:15:46):
How much data do you think you need for AI ML to have a chance to contribute? You have a heuristic of if you have anything less than this, it's not going to work at all.

**Marily Nika** (00:15:59):
This is a good question and it honestly depends on what I'm what I'm trying to do. If you're trying to classify, if the photo is a category dog, obviously even if you have, I don't know like 15, 20 labeled photos, what's going to work. But if you want to create voice recognizers or complicated NLP applications, you're going to need thousands of [inaudible 00:16:19] of data. And this what's making this not be easy? AI systems are not easy to develop. There is a life cycle of a machine learning project and after scoping you need to figure out, "Oh god, how much data do we need? Where do I find this data as well, how much data?" Sometimes I've seen people synthesizing their own fake data just so that they can have something to train with and test their models. But the exact amount is hard to be defined, especially from a [inaudible 00:16:50]. I'm sure data scientists have a different opinion.

**Lenny** (00:16:53):
Yeah, my guess is most startups are going to have nowhere near enough data to build their own model and make it something really interesting. So do you have a thought on when it makes sense to try to build your own model, try to train your own GPT type thing versus use something that's already out there like say GPT or aJourney or all those guys.

**Marily Nika** (00:17:17):
If you are a big tech company and you're offering a service that is going to do speech or permission or then it's going to have their own tragedy, you want to use more data and more diverse data to train and retain and train because if you don't then your quality is going to be the same as every other companies. There are agencies that are selling data, packages of data, that are ready so you can get them and train your models. But the question is if everyone takes that exact dataset, then the quality that every single company is producing is going to be the exact same. So you do want to diversify, you do want to collect your own data. And I guess a good question from my prem perspective is when is the quality of your product good enough to lunch?

**Marily Nika** (00:18:08):
And that is a really interesting point because it's totally your responsibility as a PM to decide, "Okay, the recognition of whether this folder is a category dog is good enough for the users, it's like 70% accurate, 80% accurate, where is the bar, where do we launch?" And that's why I'm like the AI PM role is so cool because you have problems like that to solve that no one else was tackled before. So it's all on you.

**Lenny** (00:18:34):
We've thrown out these words model and we talk about training models. Do you have a good succinct explanation for what a model is for folks that aren't that technical and then just the general idea of training a model. What is a simple way to think of, here is what a model is.

**Marily Nika** (00:18:52):
So I have a three-year-old girl and I'm teaching hear about life and everything. So I was recently teaching her about the animals and you explain things to her once or twice, what the mammals is or rhino and so on. But you will end up training your kids brain by repeating the same information again. So you will say, "Hey, here's what the rhino looks like, here's what an elephant looks like, here's what the rhino looks like, here's what an elephant looks like." And once you've done this enough times, then your kid will see an animal on the street and they'll be able to recognize and say, "Oh yeah, that's like rhino what we're talking about." This is exactly what a model is. The model is like a kid's brain. It has the ability to take an input, which means it has the ability to take an image and say, "Oh I recognize what this is. That looks like a rhino. But I'm 70% sure about this." So you will output the probability as well of the certainty.

**Lenny** (00:19:51):
And you said image, but it could be text for say in ChatGPT. In the future I imagine video there's also voice like whisper. That's an awesome explanation. Basically it's like trying to recreate the human brain is a nice way of thinking about it. And then training a model, can you talk about what that means?

**Marily Nika** (00:20:08):
The problems of training the model for example is providing a lot of images that are legal and say, "Hey, here's what card looks like, here's what it all looks like," and we're talking about thousands and thousands of data sets for this. And once you do this, there's a process where the model is just processing this information and it's learning, it's finding patterns through it and the patterns are not in the form of, oh if this is gray then this means this. No, it just learns in the smart brain how to identify specific things that we don't even understand. And then it's able to output the probability of whether photo is going to contain the cutter and top.

**Lenny** (00:20:49):
Just conceptually what is the output of the training? Is it code that is auto-generated with these decision trees and weights and things like that? Is it a database of weight? Just conceptually what is the output of a training that becomes a model? What's the simplest way to think about that?

**Marily Nika** (00:21:05):
So it's what it speaks. Speech is a great example. For example, I'm talking to a device which is like a home system and I say, "Hey, what is the weather like today?" This is going to take my folies and audio and it's going to process it and the output is going to be a transcription. So it's literally going to be text that corresponds to what I sent to it.

**Lenny** (00:21:24):
Thinking about the stuff you've worked on at Google, at Meta, anywhere else you've worked on, side projects even, what are some of the cooler applications of AI machine learning that you've worked on, contributed to, or even seen that you can talk about? I imagine there's a lot of sensitive stuff too going on.

**Marily Nika** (00:21:40):
One thing I want to talk about is the team I used to work for, Google, which was then the RVR team and they were working on an air glass and actually they had a video on last year's Google IO. They were able to have the Google glass on someone that spoke one language and then this other person was sat in front of them that spoke a different language and the glass will take as an input that audio that came from that other person and it will transcribe it, it will translate it and show it on the screen for that person in their language. So we're talking about the ability for this devices to unlock the borders of communication and that is not science fiction. This is what amazing and mind-blowing, there's no science fiction anymore. These things are real, the technology is here, it's just a matter of connecting the pieces to the puzzle in order to see them coming to life. So I think that one was one of the most impactful things I've ever seen.

**Lenny** (00:22:46):
I remember that demo and it was pretty incredible. Okay, so thinking a little more broadly, do you think ChatGPT or just say GPT four or GPT five, GPT six, do you think at some point this will replace product managers? Something I see on Twitter a lot. People are like, "Oh my god, product managements done. This thing made my product requirements document for me." Or you talked about how it makes your mission statement better. Do you think there's a place where PMs aren't necessary anymore?

**Marily Nika** (00:23:13):
Oh, absolutely not. As I said, it makes everything better. If anything it's going to free out time for me to do other things that are less tedious. For example, I am running so many projects and they only their peer [inaudible 00:23:27] and the peer [inaudible 00:23:28] have all these areas that are common across all of them. If I had a system that can actually write the continuous stuff for me so that I can focus on more strategic side of things, that would be incredible. It will make us smarter. If [inaudible 00:23:42], you will unlock new areas of product management that we haven't realized that, but are there.

**Lenny** (00:23:48):
Are there areas, do you think with your kind of vision of all PMs will be AI PMs, are there areas that you think PMs should invest more skill-wise or areas they should less focus on invest because say some machine learning model is going to do that for them.

**Marily Nika** (00:24:04):
I'd like to see people being less overwhelmed, less intimidated, less afraid to start learning how to code, how to train a little model on their own. This is because even if ChatGPT or this no code applications may be able to do this for us, it gives you a different approach, a different mindset, a different if you want confidence to know how things work. And here's a silly example, I was learning how to play the piano when I was young and when my teacher came in I was like, "Oh, I want to learn how to play this cool song." There were some songs that I really liked. And she said, "No, you need to start with a classical music," and I just hated it all the time. And I said, "Why do I have to do this?" Because she said, "If you learn the fundamentals and how you know where things started and the beginning of music, it's going to help you along the way to create music on your own if you want to." And she was right. I just loved it.

**Marily Nika** (00:25:00):
So it's the same with coding. I encourage people to just take an online course, understand more, get your hands dirty, pair up with someone else that's in the same boat as you because this is going to give you the skillset to understand how that tool that's going to help you in your day-to-day was even created in the first place instead of blindfoldedly distrusted to do your job.

**Lenny** (00:25:23):
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**Lenny** (00:26:21):
For someone that actually wants to do that and learn to code, which I love that advice, do you have any resources, places that you point people to for learning to code, getting started down that path?

**Marily Nika** (00:26:31):
It depends on what type of learner you are. There are some people that learn offline, so just go to Coursera, there are so many courses. There is an amazing one actually introduction to AI by Stanford that they're going to encourage people to take a look at. But I know that a lot of people don't like, don't have the time, don't have the discipline to actually take time off or after work, after they put their kids to sleep to just do it. So if you enjoy learning with others, if you enjoying being part of a team, if you enjoy going through a journey together, then I recommend these resources. So there is something called Career Foundry, which is a fantastic on coding school, General Assembly and then Coding Dojo.

I was actually give a talk, Ages of God Coding Dojo [inaudible 00:27:17] by Python, and all it takes is just a few weeks of your time and passion and just for you to roll up your sleeves and just realize that this is not intimidating and realize the benefits you can get by learning.

**Lenny** (00:27:31):
Awesome, thanks for sharing those. We'll include links in the show notes. Going back to a PM trying to become better in AI. If you think about a PM that's early in their career and wants to become a very strong AI PM. I know you have a whole course about this, which we can talk about now or later, whatever is easier, what should that PM be doing? We talked a bit about learn to code, maybe start playing with tools. What else do you suggest PMs that want to become really strong AI PMs do now and invest in?

**Marily Nika** (00:28:02):
So I do have a course that's coming up on February 6th on [inaudible 00:28:06], which is for current and aspiring product managers that want to build AI products. But I also have offline recordings. I have the same course on an offline basis on my website. I'd be happy to talk to you here, you already chat to me about this. What I feel people should understand is what it takes to manage an AI product. Of course people are very familiar with the stages of product development in general, but AI product development is different. As I mentioned before, sometimes you're actually managing the problem and not the product and you're trying to secure out if there is a problem that makes sense to be answered by a smart solution.

**Marily Nika** (00:28:45):
So it's a very interesting and more complicated process than regular product management. So number one, figure out how it differs from general product management. Number two, if you're already at the company that is actually having AR researchers and AI research scientists, I encourage people to just maybe talk to them and shadow them and spend an hour of their week just talking to them and experiencing what they're doing. This is going to open your mind, this is going to give you so much context as to what it is and the endless potential that you can identify there.

**Lenny** (00:29:22):
Awesome. And is there anything else you want to share from your course that you think might be interesting to folks?

**Marily Nika** (00:29:30):
So we talked about why it's awesome to be an AI PM, but I do want to call out that there are a few challenges that people need to be aware of. Number one, and I kind of mentioned it before, is the uncertainty. You may have been working on all of these incredible research and ideas in hypothesis, but then when you actually train the model, the results you may be getting may not be optimal, may not be answering the questions or the hypothesis that you actually had in mind. So that's number one. You need to be able to encourage the teams throughout this process because you're like the captain of the ship, you need to be the one that's cheerleading the team, making sure everyone keeps going.

Number two, you are going to have to [inaudible 00:30:15]. You are going to have to change the action in managing this from a leadership perspective can be tricky and it can be challenging.

**Marily Nika** (00:30:22):
Number three, we talked about data, but getting good data is hard. You may need to be creative, figure out ways for data collection that you never thought you'll do. You may get on the street and ask for people to actually contribute data for what it is you're doing. You need to be able to and willing to do everything. And the last thing is from a career trajectory, usually product managers get ahead the more they launch. But if you're in a research or if you're not going to launch as often, so you need to make sure to clarify with the hiring managers early on, "Hey, what does progress mean? How am I going to get a sense in a research work which is different than what I've been doing so far." So it's challenging but I always encourage people to flex different muscles and this is the zero to one muscle. The other thing is this crucial when it comes to product management.

**Lenny** (00:31:15):
This actually is a great segue to a question I definitely wanted to ask, which is around getting buy-in for investment at a company for ML. So there's sometimes all this energy for a zero to one, let's just try something, sometimes not, so maybe there's a two part question here. Do you have any advice on just getting buy-in for we want to try something with ML. It's going to take us six months to figure out if it's worth the effort, but we think there's something here. And then sometimes there's a lot of energy initially and then you get some win, like your search ranking's smarter and it's great.

**Lenny** (00:31:48):
But then maintaining that, having all these really expensive people working and just tweaking this model and continuing to make it smarter and a little more efficient, often it's hard to continue to get buy-in for that sort of team. Do you have any advice on initial buy-in, let's try something here, and then down the road just keeping a team going, trying to make this thing smarter and smarter.

**Marily Nika** (00:32:09):
People should know that there is an excellent source of inspiration and something that could kind of de-risk things, which is adjacent products. Maybe the company has already launched the product that has been successful, those AI firsts. And whenever I try to convince leadership about something that I want to do that's a big bet, I always use examples and I'm like, "Hey, this seemed crazy at the time, here's how they work. What I'm proposing is very similar to this crazy thing. And then I propose a little contingency plan, like hey, if that doesn't work out, here's the rollback plan, here's the maximum impact it will have done in a negative way, which is not going to be too much. And you kind of take it all on [inaudible 00:32:55].

**Marily Nika** (00:32:55):
And it's interesting because the more you work on this specific company, the more trust you get. And if the culture is such, then failing is going to be welcome. So a lot companies that welcome pain because you can just go ahead and do this sort of thing.

**Lenny** (00:33:09):
Do tell me if I'm wrong, but I feel like most investments in ML are not successes and often not great uses of time. I'm curious if that changes with more tooling and more public models that people can plug into without having to build their own. I wonder if it becomes like, "Oh okay look we're put in three weeks, we'll get something really useful."

**Marily Nika** (00:33:27):
Exactly. And also the other thing, and I wanted to add on the question you asked before about hey how do you keep updated about new niche tech? We shouldn't underestimate academia and research blogs and there's a website called Archive where you can see new papers come up, because this is where... ChatGPT and [inaudible 00:33:49] used to be there for a long time, there was a lot of information on this sort thing. But it's now recent where we see that research scientists and research orgs are not as siloed as they used to be. So the more companies invest on staffing, this layer between productionizing and research, academic research, the more PMs you're going to add there, then the more you're going to see this bridge creating goods, products, [inaudible 00:34:20]. So sometimes you have amazing ideas by research scientists but you need a PM to take it and actually figure out ways to also monetize it.

**Marily Nika** (00:34:28):
That's the other thing, if you're a PM you need to come up with ways to actually be able to monetize and ChatGPT is now free for everyone. But I don't know if you saw, there was a signup forum that was coming around saying, "Hey, would you pay for this? What would be the minimum you pay? What would the maximum you pay? What would you like to see if you paid?" So having PMs breached the tap is crucial for companies to be able to take the research and actually come up with meaningful use cases for users.

**Lenny** (00:34:56):
I think they actually started charging the other day. I think it's like $40, $42 a month to start using it. I think people have been talking about on Twitter, I don't know if that's live yet. And then you talked about research papers, when I think that, I always think of Tyler Cohen, he has this awesome blog marginal revolution and he is really good at sharing insights from research papers that he's reading. So that's another place for folks to check out. He's just this really smart dude. He's really excited about AI and GPT in general and so he shares a lot of really interesting insights about it all. Segueing a little bit to your course, I have a couple questions about it. One is can you just talk about the broad framework of your course? How long is it, what do you learn, what are the workshops broadly? And then I have a couple follow up questions.

**Marily Nika** (00:35:39):
My course is three week long. It's meant for people that are either aspiring or current PMs that want to understand how to sprinkle in AI solutions or they wanted a full-time AI course. Week one is more about introduction, what the product development lifecycle is for regular products and how it differs for AIPN specifically. And then we talk about idea creation. How on earth do you come up with ideas? And I love what Steve Job said where he used to say, "Well, users don't know what they want until you show it to them." And that's exactly the mindset I want to invite two people and say, "Hey, people don't know how on earth you use AI." People will never have imagined ChatGPT can be what it is.

**Marily Nika** (00:36:26):
And then we take that and we dive deep and we talk about how on the earth do you productionize something like this? What are the different partners you're working with? What is a research scientist and how on the earth do you collaborate and how do you partner with them? How do you convince them what you have in mind for their precious research to be converted into a product? How on earth do you convince them to trust you and how do you influence them? And then at the end we're talking about how you actually will be able to pave your pathway PM all the way from interviewing for this role, from what resumes look like, and doing some mock interviews because the more you practice the better it is.

**Lenny** (00:37:03):
How many workshops are there through the course?

**Marily Nika** (00:37:05):
Nine workshops.

**Lenny** (00:37:06):
Nine workshops. Of the nine workshops, which of them are you finding is the most exciting, game-changing for someone, most interesting?

**Marily Nika** (00:37:15):
So throughout the duration of all these workshops, people have homework and they actually take home an exercise where they need to create and develop their own AI product end to end, and they can pair up with each other. By the way, there was this two students pair up and actually where I would raise funding, which is mind blowing to me, which is really great.

**Lenny** (00:37:15):
That's awesome.

**Marily Nika** (00:37:35):
But to continue, the most exciting part is when everyone at the great end are actually presenting their work and they're actually asking questions and getting feedback and they're just really excited and proud for what they created.

**Lenny** (00:37:48):
That's a good reminder of a lot of the learning that you do is just doing it, not just reading about it and following Twitter. Can you share any examples of stuff people built after the course?

**Marily Nika** (00:37:57):
Someone was able to actually, and I kid you not, create a little model that was able to take us an input x-rays that they found online and was able to tell us what was wrong if something was wrong with that patient. And it's just crazy to think that you can do that within three weeks. Obviously it was just by photos we were able to crawl online for x-rays. But the concept is there that you can build something like that, you can create it. And to take it a bit further, they wanted to create a lower recommender system and say, "Hey, we think this is what's wrong with you, here are the steps you should follow." Obviously we're not trying to play doctors or to pretend that or medical in any way, but being able to see that actually functioning is just, it's very impactful.

**Lenny** (00:38:48):
That's amazing. Do they already know how to code, do this team that built this thing?

**Marily Nika** (00:38:51):
They did not, but part of the course is to teach people the basics that you are going to need, prove it PM lens. And there are some no click tools as I mentioned that are going to allow you to drive and drop and train these models and input photos in it and be able to do it.

**Lenny** (00:39:07):
Can you mention those tools again because that is really interesting and it's just like a peek at your course, but if someone wanted to start building something like this, what are some of these tools they could check out?

**Marily Nika** (00:39:16):
One of the tools I would like to recommend to people is actually Auto ML. This is offered by World of Cloud and essentially it allows you to train high quality custom machine learning models, which minimal effort, you don't need to be able to code anything like that. You need to have a lot of photos and images that you have already corrected but it's not going to do the collection for you. And a great application I had to seen, there is actually a YouTube video about this. There was this company that actually had a lot of winter banks and what they did is in order to maintain these, they will actually have people manually have huge ladders and go take a look and see if everything was okay. So eventually they just [inaudible 00:39:59] drones and they had these drones fly on all of these machines and take photos of everything. And then they downloaded all these photos and they uploaded on Auto ML and they were able to see which ones needed maintenance and which did not.

**Marily Nika** (00:40:12):
And I think they reduced time from three weeks of work to a few hours of knowing which needed maintenance and just be able to send people there. So it's this type of thing that you can do on your own by applying this sort of tools.

**Lenny** (00:40:25):
Saying that tool is called Auto ML?

**Marily Nika** (00:40:28):
Yes, Auto ML.

**Lenny** (00:40:28):
Amazing. We'll link to that in the show notes. Coming back to your course and maybe just a couple more questions. Can you just talk about what it takes to build a course like the course you built, how much time did it take you? How much work did it take? Anything that you want to share.

**Marily Nika** (00:40:43):
It treated creating like course like a product. This is what I did is, I came up with some hypothesis as to who the audience was and as to what they were looking to get out of it. And I started reaching out to people and I started saying, "Hey, first of all, would you like to learn from me? Second of all, what would you like to learn? What are the specific questions that you would need answered?" Because these are people that are working, people [inaudible 00:41:09] that have families. In order to take a break from all that you need to provide something to them that is meaningful. And there were quite a few activations. In the beginning I was focusing the course more for software engineers that wanted to become AI product managers. But then I realized, no, there are a lot of PMs that want to become AI product managers.

**Marily Nika** (00:41:31):
So I did a little online shift there. So what it takes is make sure you find the right audience, make sure to figure out what that audience wants, make sure to have the right duration. One week I find it too short. Two weeks, it'll still be rushed. Three weeks is excellent because you give the opportunity to everyone to present and to keep to know each other on an offline discord community, which is another important part. And then the last thing, you need to have a personal relationship with everyone. So I've messaged everyone, I've seen everyone's application. I met with some people as well just to make sure to answer any questions and concerns because I wanted to make sure that people were comfortable just trusting a stranger like me and paying them to provide knowledge for their course. So it took quite a few iterations, but I was able to get there and now I'm very, very happy about it and I recorded it offline as well for people.

**Lenny** (00:42:27):
Has anything had to change in this course? Maybe it's just as the last question, things are moving so fast. Is there anything you've had to rethink, redo since you first built it?

**Marily Nika** (00:42:35):
I actually added bonus sections and one bonus section was [inaudible 00:42:38] and how it was trained. This is because I started this new cohort in December and on day one the question I got is, what is this? How did it start? What is going on? How did they train it? So I added the dedicated section for it and I point people to it.

**Lenny** (00:42:52):
Amazing. Anything else that you'd like to share before we get to our very exciting lightning round?

**Marily Nika** (00:42:58):
It was someone that recommended, I actually did a course and in the beginning I laughed and I said, "Wait, people would want to learn from me. Really?" And of course they did. And I'm teaching so many people. So what I want to tell people is don't underestimate this. Try creating your own courses as well. People may want to learn what you take for granted. For them it may be game changing, it can be life changing. So building courses is an amazing thing and we're living in the full [inaudible 00:43:30]. So the course is content, so go try this.

**Lenny** (00:43:33):
I find that teaching and at least crystallizing thoughts is one of the best ways to learn it yourself. I imagine you learned a lot about AI much more than even came into it with just putting it together into a course.

**Marily Nika** (00:43:44):
Absolutely. And I got some uncomfortable questions that I had no idea how to tackle. People on day one were like, how do I assess the tradeoffs between these two different months? And I had to figure out how to answer these things and how to incorporate them in my course. So learning from the students, learning from the course, learning from explaining is just so viable. So skills that we can get.

**Lenny** (00:44:07):
Well with that, we've reached our very, very exciting lightning round. I've got five questions for you. I'm going to go through them pretty quick. Whatever comes to mind, share. We'll see how it all goes. Sound good?

**Marily Nika** (00:44:18):
Sounds good.

**Lenny** (00:44:19):
Two or three books that you recommend most to other people.

**Marily Nika** (00:44:22):
Inspired. It's all about how to create tech products people love.

**Lenny** (00:44:28):
Marty Kagan, right?

**Marily Nika** (00:44:29):
Yes, that's the one. Great.

**Lenny** (00:44:34):
Cool. Anything else? Or that's the one that comes to mind.

**Marily Nika** (00:44:35):
You Look Like a Thing and I Love You and I have it right here. It's a great thing, super, super cool. It's about how AI works and why it's making the world a weirder place. It's actually a very fun book. And there's one more, which is a book, a workbook I originally launched with Alana Karen and it's a workbook for women in tech trying to navigate working in tech. It's called Adventures of Women in Tech Workbook. So that's another thing that they want to shamelessly plug in.

**Lenny** (00:45:02):
Ah, that's a great choice to plug. Where can folks find that? Is that on Amazon?

**Marily Nika** (00:45:06):
Yeah, Amazon.

**Lenny** (00:45:07):
Amazing. What's a favorite other podcast that you like to listen to?

**Marily Nika** (00:45:11):
I like Boz's podcast. I don't know if you're aware of it. Boz is the CEO of Facebook. He has a great podcast.

**Lenny** (00:45:19):
I have not heard it. I do know of Boz. I'll check that out. I didn't know he had a podcast. He had some great writing over the years. Maybe that's why he doesn't write it anymore. He has his podcast. What is a favorite recent movie or TV show that you've loved?

**Marily Nika** (00:45:30):
Oh my God, The White Lotus. People were talking about this thing. I ended up just trying it out and me and my husband, we just binge watched the whole thing. Is just so different, so mind blowing, get you excited about going to Hawaii again. It's just really good.

**Lenny** (00:45:45):
Have you seen the second season?

**Marily Nika** (00:45:46):
I've seen it and it's so much better than the first, which is rare.

**Lenny** (00:45:50):
I agree. Awesome. Love that show. What is a favorite interview question you like to ask, and bonus point if it's AI related.

**Marily Nika** (00:45:57):
I love to ask people, how would you explain a database to a three year old? And I know it's kind of an AI, not everyone say ai, but I love asking it because people are thinking the [inaudible 00:46:11], like what did you just ask me? But it's so important to be able to explain things in a simple ring and have the storytelling to convince a kid and really explain technical terms to non-technical people.

**Lenny** (00:46:23):
Favorite AI based tool that you think people should check out.

**Marily Nika** (00:46:27):
Talk about ChatGPT, now I have this on ChatGPT, this is what comes to mind. Well, the Lensa app was pretty cool too, right? We all plugged in our [inaudible 00:46:36] and we're able to see what they would look like as fantastic heroes. I have to say, I tried being the mail version because it was so much cooler than the KingL version, so that's when I recommend to people, try the mail version.

**Lenny** (00:46:48):
That's fun. And they actually have pets now. That's what got me the download and pay for it. You can take pictures of your pets and they look so fun. That's like a killer feature right there. Good job Lensa. And the app is Lensa, right?

**Marily Nika** (00:47:01):
Yeah. [inaudible 00:47:02]

**Lenny** (00:47:02):
Amazing. Marily, thank you so much for spending time with me, sharing your wisdom. Two final questions, where can folks find you online if they want to learn more and reach out and how can listeners be useful to you?

**Marily Nika** (00:47:12):
Thank you so much. People can find me on Instagram. I also have a product channel on YouTube that you can check out. I just started it. I'm getting used to the whole process. I'm also kicking off a newsletter, just any social reach out and you'll see all my links.

**Lenny** (00:47:28):
How do they find the YouTube channel? How do they find the newsletter?

**Marily Nika** (00:47:31):
Typing Marily Nika.

**Lenny** (00:47:32):
Marily, thank you again for being here.

**Marily Nika** (00:47:34):
Thank you so much, Lenny. It was a pleasure.

**Lenny** (00:47:38):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [9/22] Leading with empathy | Keith Yandell (DoorDash, Uber)

**Keith Yandell** (00:00:00):
Every business that you have heard of has gotten rejected by at least a handful of venture capitalists at one point or another. And so that drive to keep going if you believe in the business is critical, absolutely critical. I mean, we were weeks of runway situation and had been told no by everyone. And it was just Tony's drive, really, to keep going. And the way he explains it to me is it's just the difference between a founder and a non-founder. If you're really a founder, you just have to find a way. You have to keep going. There's no question. And I mean, that's the only advice I can give folks, is it only takes one yes. But you got to keep going.

**Lenny** (00:00:44):
Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Keith Yandell. Keith is a longtime leader at DoorDash, where he's been for about seven years. And in that time, get this, he's led the legal team, the HR team, the marketing team, the customer support team, and currently he leads the BD and corporate development teams. Before DoorDash, he led litigation at Uber. He's also managed folks like Gokul Rajaram, who was previously on this podcast and who suggested that I have Keith on. And damn, was he right. Before I had this chat with Keith, I didn't know that much about him, but now you can count me as a huge Keith fanboy. I suspect you'll feel the same way after you listen to this episode. I'm just going to jump right in and bring you Keith Yandell after a short word from our wonderful sponsors.

**Lenny** (00:01:38):
Today's episode is brought to you by OneSchema, the embeddable CSV importer for SaaS. Customers always seem to want to give you their data in the messiest possible CSV file. And building a spreadsheet importer becomes a never-ending sink for your engineering and support resources. You keep adding features to your spreadsheet importer. The customers keep running into issues. Six months later, you're fixing yet another date conversion edge case bug. Most tools aren't built for handling messy data, but OneSchema is. Companies like Scale AI and Paved are using OneSchema to make it fast and easy to launch delightful spreadsheet import experiences from embeddable CSV import to importing CSVs from an SFTP folder on a recurring basis. Spreadsheet import is such an awful experience in so many products. Customers get frustrated by useless messages like, "Error on line 53" and never end up getting started with your product. OneSchema intelligently corrects messy data so that your customers don't have to spend hours in Excel just to get started with your product. For listeners of this podcast, OneSchema's offering a $1,000 discount. Learn more at oneschema.co/lenny.

**Lenny** (00:02:45):
This episode is brought to you by Amplitude. If you're setting up your analytics stack but not using Amplitude, what are you doing? Anyone can sell you analytics, while Amplitude unlocks the power of your product and guides you every step of the way. Get the right data, ask the right questions, get the right answers, and make growth happen. To get started with Amplitude for free, visit amplitude.com. Amplitude, power to your products. Keith, welcome to the podcast.

**Keith Yandell** (00:03:15):
Thanks so much for having me, Lenny.

**Lenny** (00:03:17):
First off the bat, I just want to give a big thank you to Gokul Rajaram and Micah Moreau for suggesting you be on the podcast, helping make this happen, and also just suggesting a bunch of questions to ask you. So, I hope you're ready to be in the hot seat.

**Keith Yandell** (00:03:29):
Definitely as ready as I'm going to be. And those are two good folks to talk to.

**Lenny** (00:03:34):
Awesome. And Gokul's been on the podcast. Maybe we'll get Micah on the podcast at some point. I wanted to start off with a story. Apparently, there's a story of you interviewing what is now your VP of engineering. And I hear that in the interview, you called him an asshole. And more interestingly, he joined DoorDash because you did that. Can you just talk about that story and share that story?

**Keith Yandell** (00:03:55):
Yeah, actually, it wasn't during the interview. We were debriefing. And for me, one of the top things I always hear about DoorDash from an executive standpoint when we do the internal survey is it's a "no politics, no asshole" culture. And I'm not one to swear a lot, but after interviewing Ryan Sokol, who's now our VP of eng, he was just kind of aloof. He came off as aloof to me, really curt answers. And I just didn't have a great feeling about him. And I pride myself on being able to discern when people are really engaged or not. And I went to Tony Xu, who's our founder and CEO. I said, "Tony, I think this guy's a jerk. I don't think we want him at the company." And Tony was great. He said, "Keith, I want you to just have dinner with him, please, because I got a completely different impression. And if you have dinner with him, and you still think he's a jerk, we won't hire."

**Keith Yandell** (00:04:51):
And so I ended up meeting Ryan down the street. We actually live in the same general area. We went out to dinner, and I started right away. I said, "Ryan, during the interview you kind of seemed like an asshole. Are you an asshole?" And he was so great. It completely changed my perspective in a good two minutes. He wanted to know what he had said. He said, "I'm super embarrassed, and what could I do differently? Regardless of how this works out for me in this circumstance, that's just not how I want to be perceived." And we talked and joked about the things he had done, and he kind of told me the background for how he reacted or why he reacted the way he did. And by the end of the dinner, we ended up staying super late. We had a couple beers afterwards. Ryan and I have become really good friends.

**Keith Yandell** (00:05:37):
And six months later, he told me that one of the reasons why he joined DoorDash was that we were going to blackball him potentially from joining just because of his attitude, because his perspective is life's too short to work with people you don't really enjoy, and a lot of people pay lip service. And he knew he was going to be a tough hire for us at the time. And the fact we were willing to go all the way down the path and have someone super qualified but didn't meet the culture bar, for him was what pushed him over the edge to join the company.

**Lenny** (00:06:06):
I love that. I love the directness of that meeting, of just like, "Are you an asshole?"

**Keith Yandell** (00:06:11):
Think about it, right? And if someone really was a jerk, they probably wouldn't have taken it very well. Right? It's just like when you're interviewing someone, giving them tough feedback after the interview if there's an area of concern, but you otherwise like them, can be a really great way to see how they would interact with you personally as well as how they take feedback. And so that was my learning from the situation, is if you really enjoy an interview, except for maybe something on the culture side, to give the direct feedback and see how people engage.

**Lenny** (00:06:39):
This touches on another question I wanted to ask you, which is just about DoorDash's culture, which feels really unique, just feels very driven, very pragmatic. There's a story I heard where when you guys celebrated one of your biggest milestones, you bought the cheapest champagne and plastic flutes, and I think the founders brought that to everyone. Could you just talk about what makes DoorDash's culture so interesting and unique? And maybe if there's a story of just a microcosm of what DoorDash culture is like, that'd be awesome to hear.

**Keith Yandell** (00:07:07):
Founder-led companies tend to take on the personality of their founders. And if you spend any time with our founder, Tony Xu, you realize that he's a humble leader. He's competitive. He really wants to win, and he'll do whatever it takes to win. And the example you're referring to, I think, is when we raised our Series D funding, which was a really tough fundraise for us... We had very little runway left. We almost went out of business, and it was a huge relief when we had finally gotten the funding secured.

**Keith Yandell** (00:07:40):
And I remember I was in a meeting. I was running policy and communications, among other things, at the time, and I was in the meeting with a couple other folks, and we were talking about the press release strategy. Tony was there. And someone ran down and got some, I think it was Korbel or something champagne and some plastic flutes. And one of the women who was in the meeting with me was going to leave to go put those together. This is a very smart woman, who I think Tony recognized could add more value. And he said, "Whoa, whoa, whoa. You stay here. I'm going to go put together the champagne flutes." And he called the other two co-founders, Andy Fang and Stanley Tang. They came, stayed up all night, put together... I don't know... 500 champagne flutes, plastic ones, for this cheap champagne and let the people who are closest to the problem try to work out the comms piece. And I do think that's one great example of the culture.

**Keith Yandell** (00:08:31):
The other thing I think that really exemplifies DoorDash's culture is a level of customer obsession. And that manifests in a few different ways. We have a program called WeDash, where, four times, a year all employees are required to go do deliveries. And I love doing it. I do it more than four times a year, and I usually take my daughters with me. And one time, I was out with my daughter, who was eight at the time. We got a delivery, and it was not the best delivery. There's clearly something wrong with the system. We got a sandwich and a coffee, and we're supposed to drive 18 and a half miles to drop it off. And that didn't make sense for the customer. It didn't make sense for us as drivers.

**Keith Yandell** (00:09:13):
And she'd gotten to know Tony over the years, and she said, "I really want to call Tony and tell him this thing's broken." "Honey, I like my job. I'd like to keep my job. Can we not call Tony right now?" But she was adamant, and I was so proud of her for feeling so strongly that she wanted to fix this thing that was broken. I figured, "He's not going to answer anyway. We can just call." So call. Tony picks up on the first ring. And I'm like, "Oh, this might go badly." And she just lays into him. She said, "This is going to take us 36 minutes to drop off. The coffee's not going to be hot. How could you allow this experience if you really care about your customers?"

**Lenny** (00:09:52):
Whoa.

**Keith Yandell** (00:09:52):
And I kind of sucked in my breath and said, "Well, that's how my time at DoorDash ended." But Tony was great. He was like, "Hey, Alice, we have people who do deliveries for months. We have people who deliveries for years, and they're always providing me feedback. And this is one of the most insightful pieces of feedback I've gotten recently. And you've only been dashing for a few different times." And by the time we got home, he'd actually sent an email out to the product organization, calling out the problem, suggesting the fix. And they were already working on it. And that shows the bias to action that I think really is at the heart of DoorDash, alongside that customer obsession. And it's not unusual for Tony to do customer support. It wasn't like just because he heard this from my daughter that he actioned it. He does support every day. And again, this goes back to that level of humility and companies really taking on the ethos of their founder.

**Lenny** (00:10:47):
What an awesome story. I want to chat a bit more about the, what is it called? WeDash? Is that the program?

**Keith Yandell** (00:10:52):
Yeah. Yeah.

**Lenny** (00:10:52):
So you say that you're supposed to do it how many times a year, four times a year?

**Keith Yandell** (00:10:55):
Yeah, at least four times a year.

**Lenny** (00:10:56):
And then you said that you do it a lot more often. How often are you doing it? And then, is there any other fun stories of that experience, someone like you delivering someone's sandwich?

**Keith Yandell** (00:11:05):
I probably do it once a month.

**Lenny** (00:11:06):
Wow.

**Keith Yandell** (00:11:07):
And there, there's all kinds of great WeDash stories, but I don't know how interesting they're going to be to the broader public because, for me, it's just about getting out and experiencing the product. I almost always find something that's broken, and I send an email to... We have a Slack channel that's devoted to experiences via WeDash. It's everything from, I found a bug once where it wasn't routing you necessarily the fastest route. It was going using straight line as opposed to road. That was something that we fixed. And for me, the best parts about WeDash are the experiences, the interactions with the restaurants, the interactions with colleagues. So I'll go delivering with Ryan Sokol, the head of engineering. I'll give him a hard time about refining the product and things like that. But that's, by far, my favorite WeDash story, is the one with my daughter.

**Lenny** (00:11:57):
That's a good one. So at Airbnb, we actually had a similar program, where Brian wanted everyone to be a host on Airbnb. But as you can imagine, that's much harder. Not everyone is able to. Not everyone has a place to. So it's always kind of a challenge to make people do that. I imagine DoorDash is a lot easier because a lot of people can go around and deliver things. But yeah, such a killer idea, such a good way of dogfooding your product.

**Keith Yandell** (00:12:19):
Yeah, it's a good point, but not everyone is able, for a host of reasons, at DoorDash to do it. And so there are alternatives. So you can do customer support, for example, in lieu of actually going and doing deliveries. It's just about making people have empathy and get closer to the product. It's also, going back to the culture point you raise, it's a great way to weed out people that maybe we wouldn't want to work with, right, because not every software engineer wants to hop in their Tesla and go out and deliver McDonald's to some kids. Right? It takes a certain level of humility, a certain amount of customer obsession, to even sign up for that. So we're really vocal during the interview process that this is something that's expected. And it serves as a governor to attract the people that we think are going to be most successful at the company.

**Lenny** (00:13:02):
I love that. Imagine all your programs have the Dash in there somewhere. Something Dash.

**Keith Yandell** (00:13:07):
We try. I think when I was head of a marketing, we did a much worse job. I think we're doing much better now.

**Lenny** (00:13:13):
Nice. And Airbnb, it was always Air Something. Okay. So, I think one of the most interesting things about you and your background, and maybe unusual things, is the number of teams that you've led over your time at DoorDash. I have a list here. So over your time at DoorDash, you've led the HR team. You've led the customer support team, led the sales team, the marketing team. Now you lead the BD and corp dev team. Initially, I think, you were chief legal officer. So here's my question. As someone that, I imagine, doesn't have a ton of expertise and experience in a lot of these areas, how are you able to credibly lead these teams? And I ask partly because as a founder, you have to learn how to lead teams and people that you don't actually know what they're doing as well as they do. And so I'm just curious what you've learned about being able to lead teams in such disparate skill sets and functions.

**Keith Yandell** (00:14:03):
Yeah, the one thing I'll say is, I did not run sales. That's maybe one of the very few non-technical functions I did not lead. But the question is a good one. And I had massive imposter syndrome the first time Tony asked me to take on something that I wasn't a subject matter expert in. And I told him I didn't want to do it. And he had me read this book called Range by David Epstein. And the general thesis is that generalists are better than specialists. And it goes through all these examples of about how Nobel Prize winners are usually amazing in something other than the field that they actually win the Nobel Prize in.

**Keith Yandell** (00:14:38):
And Tony believes pretty deeply in this philosophy, and the way he explained it to me is as follows. If you want to achieve a 10x outcome, hiring someone that's an expert in the field, it's maybe unlikely you're going to achieve that 10x outcome, because they're likely to do things the way things have always been done. So you might achieve incremental benefits, but the odds of completely reinventing the system and doing something that's vastly superior to others is much lower. And he said, "I know you don't know how to do this stuff. That's why I'm putting you in the role." And I said, "Okay."

**Keith Yandell** (00:15:10):
So, first thing he helped me do was believe that I could add value here. And then, the second thing for me was to go out and find the best people that really were the subject matter experts, and add the value I could to help them be successful. And I found that they were actually really attracted to wanting to work with someone like me, who came into the interview process and said, "Good news, bad news. I don't know your field anywhere near as well as you do. Here's the ways I intend to help you. Here's what I think you can provide. And at the end of the day, I'm going to get out of your way." And that's really proven true. So, I ran marketing. Hired initially a head of brand, Kofi, who now is our CMO. Hired ahead of legal, who's now our GC, Tia Sherringham. And these people have really just excelled at their function and, with the warmup that I was able to provide, have really proven that they're much better at the jobs than I was.

**Lenny** (00:16:08):
You don't strike me as someone that is trying to build empires and take over all these teams. I imagine this kind of came at you because you've been doing a great job at other things. Is that how it worked? And, I guess, is there anything, any lessons there that you can take away?

**Keith Yandell** (00:16:21):
Yeah, hundred percent. I run a 12-person org today. So I've gone from running 1,500 people in the company to 12. And for me, people talk a lot about hiring people better than you are. People don't talk a lot about what you do when you hire those people. And if you really care about the company and your long-term brand as an individual, as a manager, you realize what you want to do when you find the person that's better than you is you want to slowly get out of the way. And it's really good for the company. It's my favorite part of my job, is seeing people that either I've hired or managed be successful on their own.

**Keith Yandell** (00:17:02):
And I think it's a big part of our success, is this desire to be successful, regardless of who's in charge. And that comes from the fact when I joined DoorDash, we were getting our tails kicked. We were in fourth place in the space. Uber had just launched food and rocket to market share leadership. And I think that was really good for us as a company because we realized unless we all worked together, and it wasn't about who was doing what or things like that, we weren't going to have a shot at being successful. And I think that ethos has really pervaded and persisted since then.

**Lenny** (00:17:40):
Yeah. I think most people don't realize DoorDash actually has the biggest market share in food delivery. Imagine that's still true. I've always seen these line charts of market share, and DoorDash is always the top. And I think people kind of think Uber Eats is winning, but it's not true.

**Keith Yandell** (00:17:52):
Yeah, I mean, the category charts I've seen are consistent with what you said by a pretty wide margin. But we try not to focus on things like that. We try to focus on the customer experience. And it's humbling in our space because we're doing millions and millions and millions of deliveries a day, and those deliveries will go wrong, no matter how hard you try. And we read those experiences. We do customer support, and we understand that there's a long ways to go. So we're just getting started, and we know that.

**Lenny** (00:18:21):
You mentioned that you ran this 1,500-person org at one point, and something that I've heard you do, that helps you do that, is you have this document that you put together that kind of explains how to work with Keith, and also, just broadly, how things work at DoorDash. Can you talk about this document, and why you thought it was necessary, and kind of the impact something like this has had? And then we're going to share a link to a redacted version of this in the show notes.

**Keith Yandell** (00:18:45):
One thing I've learned is it's super hard to scale culture, especially when you're growing as fast as DoorDash has since I joined. We were two or three X'ing the company, from a head count perspective, for the vast majority of my time every year. And so one thing I noticed is, it's hard to come into a place and be new and understand how things work and what it means to be successful there. And so the idea was to do our best to scale that. And one thing that Tony taught me is one thing that scales really well is written work [inaudible 00:19:16]. And so I put together this document. There's three basic subject matters. It's my expectations slash what I've seen as traits in successful people within the company.

**Keith Yandell** (00:19:28):
Two are how I can improve, like basically, feedback I've gotten in things I'm working on. For example, I'm a litigator by training, and so I tend to argue about things, even if I agree with people to the test levels of conviction. And I got feedback from my team that was really confusing because I'd be arguing against something, and then we would execute that exact thing. And so I try to be transparent about that and explain how I work through problems, but also in saying, "Hey, this is something I'm trying to improve on, is not being quite so argumentative for sport." And then it talks about what my commitments are to team. So, "I'm committed to finding you your next job even if that's not at DoorDash. Life's too short to be in a job you don't like," things like that.

**Lenny** (00:20:16):
I've heard from a few people how impactful this document ended up being. I guess, what impact have you seen this have on the org that you've run in the company and then, yeah, any other examples of just why this is powerful? Because I imagine some people listening are like, "Oh, I should do something like this."

**Keith Yandell** (00:20:32):
Yeah, I mean, for me, one of an executive's main jobs is to attract and retain top talent. And going back to why people have joined DoorDash, Kofi Amoo-Gottfried, who's now our CMO, joined me as head of brand when I was running marketing. And it's comical because this person is a legend in the marketing space, and I had no idea what was going on. And so convincing him to join, I was really nervous about. And the point where he decided to join, I had sent him this document. He wanted to know what it was like to work with me. I said, "Well, I've actually written that down."

**Keith Yandell** (00:21:01):
And he later told me that that was a really important factor for him, that someone was so transparent about their areas for growth, how they thought they could be helpful, and he liked the fact that I knew that I didn't know. And so he knew he was going to have a lot of autonomy on the role, and that was really important to him. But more broadly within the organization, how it's been helpful is just being able to have people engage with me in a way, and with the company in a way that is so consistent with the culture from day one. I've had people come and tell me, that I'd never met before, that they'd read the doc, even if they're on a different team, and just how helpful it's been to try to acclimate to this fast-paced environment, where you're learning while drinking from the fire hose, effectively.

**Lenny** (00:21:44):
Yeah, that makes sense. Touching a little bit on it, you talked about all these amazing people you've led and how you've been able to do that. Something else I've heard that you do that's pretty unusual is you help people that you manage find their next job, which may not necessarily be within the company, maybe at another company. You kind of help them land it and find something else to do. I've never heard of that before, really. I'd love to hear why you decided to do that, how you do that, and just the kind of impact, second-order impact, maybe, that has, maybe that leads you to be doing this.

**Keith Yandell** (00:22:15):
It wasn't a calculated decision why I started doing it. Then I gave it a lot of thought because I was afraid that I might get some blowback when people started taking jobs elsewhere. And as I thought about it, I realized it really is better for the company to have that type of open dialogue with people that work on your team. I think that's true for a few reasons. In this "How to work with Keith" document, I say, "I will help you find your next job." And what that means is, number one, people are going to be transparent with you, or more transparent, if they're looking for something else or if they're not happy. That's going to allow you to lay the foundation for a backfill so you're much less likely to get surprised when someone leaves.

**Keith Yandell** (00:22:59):
Number two, what's going to happen is if someone runs a blind reference on me at this point with someone that I've managed, which in the current environment is more and more common, people diligencing the managers, what they're going to hear is, "Keith's going to put you first." And I think that's really motivating for a lot of people. So if you're thinking on a five-, 10-year horizon of your career as a manager, whether you're an entrepreneur hiring people into your company, whether you're a product manager who's trying to build a team, building that long-term reputation, I think people take much too shortsighted perspective on that.

**Keith Yandell** (00:23:34):
And so now if I get a blind reference, people are going to hear that, "It's not all about the company. It's not all about Keith. It's about you and your career," and that's going to pay back 10x. Maybe you lose one really talented person, but they probably shouldn't be there anyway. They're probably going to leave anyway. And this way, you can participate in that and really drive value for them, as well as for the company in the future, by creating a much better reputation for the group of managers. So it's been really helpful for me. I keep in touch with a lot of people who have left, and we get a lot of boomerangs, too. There's a lot of people who leave DoorDash and come back. And that's something I love seeing because it shows that people have gone out and seen what else is out there and realized this is the right place for them.

**Lenny** (00:24:20):
Can you talk a bit about how you operationalize this? Because this is just out there. "Tell me if you're thinking about a new job, and I will talk to you through your options and help you find something." Or is there anything else there for folks that maybe want to offer this to their employees?

**Keith Yandell** (00:24:33):
So, first of all, I put it in this document. And so I say how I run one-on-ones in my "how to work with Keith" document, and the last 10 minutes of my one-on-ones are career development conversations. That's a really fertile ground for having the discussion. But for particularly more senior folks, if I get pinged for a GC job, or when I would get pinged by a recruiter for a GC job, I would forward that to Tia Sherringham, who's now our general counsel but was basically head of legal for years before she got the general counsel title. And I'd say, "Hey, Tia, I don't know when this job's going to be available here. I'm still liking what I'm doing. I think I'm still adding value. If you think it's time for you to leave, I think this is a really good opportunity."

**Lenny** (00:25:11):
Wow, that's [inaudible 00:25:12].

**Keith Yandell** (00:25:11):
And I say, in addition to that, "You're going to learn the questions they asked during the interview process. You're going to learn what type of qualifications they're looking for. And if I'm not getting you that experience, you can tell me." And thankfully for me, Tia decided to stay and has now grown into the general counsel of DoorDash, and doing a much better job at the role than I ever did. But she had the opportunity to leave, and I think she learned from some of those in-bounds and the experiences she had.

**Lenny** (00:25:40):
Wow. That's amazing, that your bosses forward you recruiter pitches to go work somewhere else.

**Keith Yandell** (00:25:48):
Think it made her want to stay. Right? If I wasn't invested in her success, she could have left any time and gotten a job, super qualified. But I think she felt a sense of loyalty based on my sense of loyalty, and I think it worked out best for all involved.

**Lenny** (00:26:04):
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**Lenny** (00:27:23):
Something else I hear about you, which I'm sensing as we chat more and more, and I could see why this is true, is that on the DoorDash kind of C-suite and board meeting and board in general, you play this really strong unifying force that helps the group come to fast decisions on really complicated topics. And I'm curious. One, would you agree with that? And two, what is it that you do that helps a lot of strongly opinionated people come to decisions on really complicated decisions?

**Keith Yandell** (00:27:51):
I hope that's true. I think that, for me, it all comes down to empathy. And what I mean by that is, you have to understand what different people's motivations are in the room. Different people are goaled on different things. People come from different life experiences and different work experiences. And I think it's really important to make each person feel heard. We had a situation, for example, where we were deciding between a trade-off between two business lines. It was a profitability question for one business line, to make one business line much more profitable to do a certain partnership, but it would come at the expense of the growth of another business line that was more nascent.

**Keith Yandell** (00:28:30):
And so it's hard when you get the GMs for all these businesses together, and they have very strong perspectives and good reasons on both sides about why path A is better profitability, path B is better for growth. And they're arguing very strenuously, in part because they want to hit their numbers, in part because they believe it. One thing I found super effective in those contexts is I try to ask the other side. So, let's take the profitability side. I ask them to make the growth case. I say, "Tell me the three best reasons why we should actually focus on growth here." That generates instant empathy for the other side. And sometimes, they'll even persuade themselves as they're talking and say, "I think you're right that we should focus on growth here. We can achieve this profitability measure later" or vice versa. And so generating empathy and having empathy for the other side, understanding how they're goaled and what they're bringing to the conversation, I think is the first step to having those really tough conversations.

**Lenny** (00:29:25):
I love that. What other steps are there? I like that as a first step. Is there anything else you have that you end up finding is really helpful there?

**Keith Yandell** (00:29:32):
Sometimes these conversations can go on forever. Right? People just want to keep going back to an argument they've already made, because they're not willing to settle, and there needs to be someone that says, "All right. We got to be clear on who the decision maker is here. If we haven't reached a consensus, who's the tiebreaker?" And a lot of time that's our CEO, Tony Xu, but a lot of times it's the GM for a certain business line or a head of product or a head of engineering, depending on the decision to be made. I think being really clear about, "Hey, we're all going to come together. We're going to have a healthy debate. We're going to make sure everyone's perspectives are heard. We're going to try to reach consensus, but the end of the day, here's the person that's going to make the decision, and we're going to make it on this time horizon. And once the decision is made, we're going to [inaudible 00:30:16]."

**Keith Yandell** (00:30:17):
And I think that having someone that's in the room that has run a lot of the functions that are trying to articulate the perspective is helpful, and someone who's been at the company as long as I have and given up as much as I have... Right? To your point earlier, everyone knows I'm not trying to build an empire. I'm trying to find a way to win. And I think it gives me some credibility to call the question, figure out who decision maker is, set a time line, and move on. The only way it works is if there's empathy on both sides.

**Lenny** (00:30:46):
This is great, so I just took a few notes. One is there's essentially the steel man component. Have them steel man the other side, argue why that's the better decision. Clarify a decision maker. Make it clear like, "There's the tiebreaker. If we can't get there, this person's going to make the decision." And then create a time horizon of like, "We need to make a decision by this time." Is there anything else, before we move on to a different question?

**Keith Yandell** (00:31:08):
I think that's the right framework. I can tell you're product guy. You're very good at distilling it down to the essence. I think that's a good summary.

**Lenny** (00:31:16):
Yeah, you got to do it. You mentioned the one-on-one meetings. And I took a note on this, actually, and I wanted to come back to it. You mentioned at the end of your one-on-one meetings you have this kind of coaching career conversation. Is there anything else you could share about just your approach to one-on-one meetings, your agenda or how you think about one-on-ones?

**Keith Yandell** (00:31:32):
This is super tactical. It's something I think is really important, is I'm very clear, in the document we talked about earlier, about how I like to work, is I demand feedback for me. And so we set aside time during one-on-ones where I want the feedback. First, constructive feedback. And I expect it, and if you don't give it to me, I'm going to press you on constructive feedback. And then I give feedback. I tell this to managers all the time. If you create a space where you require constructive feedback, it's a lot easier to give feedback. One of the top things I hear from managers, especially new managers, they don't like giving constructive feedback. They want to be positive. They want to be liked and things like that. And so it's a nice way to create space to have that dialogue.

**Keith Yandell** (00:32:15):
And that's something I actually learned from Travis, when I was at Uber. We had a system called T3 B3, where during reviews or pulse check-ins, you'd have to say three positives about your manager and three constructive pieces of feedback for your manager. And the first time I did it, I just did the T, the tough things, for my manager, who was the general counsel at the time. And Travis came over, and, "This is totally unacceptable. You have to provide constructive feedback," which made me super uncomfortable but created the right environment, where people could have these tough conversations because, "My manager can't get mad at me, because she knows the CEO's going to come give me a hard time if I don't provide some constructive feedback." And I think having that as an expectation is super important to building open lines of communication.

**Lenny** (00:33:05):
Wow. I like this T3 B3. So T is top good things and B is three bad things.

**Keith Yandell** (00:33:10):
Yeah.

**Lenny** (00:33:11):
Cool. I'm trying to imagine you in this meeting with the CMO you mentioned, and them having to give you constructive feedback. That's always hard, even though you expect it. Is there anything else you do to help people feel comfortable giving you hard feedback in meetings like that?

**Keith Yandell** (00:33:26):
You have to thank them for it. Right? I mean, there's a saying, "Feedback is a gift," but you have to say stuff, and you have to action. And that's one thing I've found that can be really demotivating for folks. A lot of these companies have these pulse surveys, or they talk about what the company can do better, and they put the results on the screen, and, "We're going to work on it," and that's the end of it.

**Keith Yandell** (00:33:50):
And that was something I learned early on at DoorDash that people didn't like, unless you were going to come back and say, "Hey, this was our lowest performing area in the pulse survey. Here are the three things we did to action it," because that's how you would treat the business. Right? If we got feedback from a customer or from another business line, you would say, "Heard it. We're going to come back and report out on what we're going to do differently, and then we're going to track the progress." And so I think that's really important when you receive feedback. You have to show people that you're actioning it and say, "I heard this from you. Checking in. Am I doing better? Here are the things that I've changed." And so making sure that there's that feedback loop, I think, is another important part of creating the right structure for a good, healthy culture.

**Lenny** (00:34:33):
Another guest on the podcast had the same exact advice for getting feedback, and the way he described it is you want to be enthusiastic about like, "Thank you so much for that." And the way he described it is even though you're melting inside because you don't want to hear, "Thank you so much. That was so helpful."

**Keith Yandell** (00:34:48):
It's really good advice.

**Lenny** (00:34:49):
I want to zoom out a little bit and talk about the DoorDash kind of journey. There's been a lot of high highs with DoorDash. There's been some low lows. I know that there was a funding round at one point, where it was very precarious and may not have worked out. Question I have for you around that is just, leading through hardships and through tough times, what have you learned, as a leader, about how to lead through challenging times? And ask partly because a lot of companies are going through that right now. It's pretty hard for a lot of folks out there, a lot of layoffs. And so yeah, I'm curious what you've learned about leading through challenging times.

**Keith Yandell** (00:35:23):
Yeah. I'm going to regurgitate some advice I got from some folks on our board at the same time, when we were having really tough times, which I really didn't like hearing at the time, but I was kind of new to the space. And that is, "Tough times make companies," for a host of reasons. I mean, this is super healthy for the start-ups out there right now. It's because, number one, you're going to find out who the mercenaries are on the team, that are people that are there for the mission, versus they're there because they think this is going to be a quick road to riches. We had a lot of people leave the company when Uber launched food, and we fell quickly behind. And that was good for us because the people that stayed were there because they wanted to work on this team, on this mission, and they really believed in it.

**Keith Yandell** (00:36:11):
The second thing is it forces discipline. It's a good thing to focus on unit economics. And we didn't have the funding that a lot of our competitors did, which forced us to be super focused on our unit economics and efficient and serve the customer in unique ways from the start. And I think a lot of our success, even to this day, emanates from those tough times. The last thing I'll say is if you're a founder, and you're looking for talent, tough times are great because there's a lot more talent out there. I saw... I think it might have been Bill Gurley. Someone tweeted, "This is the best time in recent memory, since 2008, to start a company." And that really resonated with me because there's a lot of talented folks out there who are looking for their next thing. And three years ago, it was tough to find talent. And so I think there's a lot to like about tough times.

**Keith Yandell** (00:36:59):
The last thing I'll say is, one thing that I found surprising is, from our surveys internally, people actually like crises at DoorDash. And I dug into that recently, and I was trying to figure out [inaudible 00:37:10] like these crises, and it's because there's singularity of focus. You know what the job is. You know you're going to get whatever resources the company has, when you're focused on the main thing. And these tough economic times will create that work. It's crystal clear. You got to cut, burn, and everyone's going to be doing what they need to do to achieve that outcome. And I think talented folks really like that, one, resourcing, and two, singularity of focus about what the main thing is. And crises manifests those for folks.

**Lenny** (00:37:42):
It's interesting that there's all these benefits to tough times. It's hard to recreate artificially. Reminds me a little bit of Frank Slootman, I think his name... and his book Amp It Up, where he talks a lot about the importance of urgency, always creating urgency. And obviously, a downturn like we have today is an urgent situation. Have you found that to be true, the power of creating urgency? And then, is there something you've learned about how to create that urgency at a company [inaudible 00:38:07]?

**Keith Yandell** (00:38:07):
Yeah, this is something Tony's talked about since the day I joined, and he's very good at, frustratingly good, at that, because just when you think you've achieved the goal, the goal might go up. It might get shorter if you're from the product side. And speaking specifically on the product, compound interest is a really hard concept to fully explain to people, to make them truly appreciate. But that's something Tony is fantastic at, which is, he understands that by pushing a road map up, even by a week, if you can continuously push up what you ship by a week, you're going to end up lapping competitors who are just one week behind because you're going to start the next thing a week sooner, and you're getting that 1.1, 1.01x return. And then it grows and grows and grows.

**Keith Yandell** (00:38:51):
And he's as good as I've ever seen, combined with our president, Christopher Payne, at creating that sense of urgency and just pushing people. "Do we really need to test this thing again or can we ship it? How can we move that much faster?" Even if it's by a small margin, understanding that you can compound those gains over time has been really impactful for our success.

**Lenny** (00:39:11):
I saw the same thing at Airbnb. It feels like, "Things are going well. Maybe we could take a little break," but it's constant just like, "How do we go faster? How do we go bigger? Okay, what's next? We launched this thing. Let's move on." And it feels like such a pattern across companies that do really well, is the founders continuing to keep that pressure on.

**Keith Yandell** (00:39:28):
I remember our IPO day. We had this thing. I had to wake up super early. It was a virtual bell ringing, and the second it was over, we had our weekly business review, and there were tough questions being asked. There was not champagne being passed around. I mean, people were in a good mood, but it wasn't like, "Wow, this is so great." It's just like, "Hey, how are we going to serve our customers today?" And I thought that was really emblematic of, "Hey, if we take too deep of a breath and are patting ourselves on the back..." It reminds me of the saying, "Somewhere, someone out there is practicing, and when you meet them, they will beat you." It's the same kind of thing. It's if you take too long to be self-congratulatory, you're going to fall behind the people who are still hungry. So it's important to stay hungry.

**Lenny** (00:40:12):
Wow. Reminds me, I think it's Bill Gates talking about someone's in a garage building the next Microsoft, and he's always trying to stay ahead of them.

**Keith Yandell** (00:40:18):
So true.

**Lenny** (00:40:20):
The other thing this makes me think about is just, it's wild that founders... like Airbnb founders have been at this 15 years. Tony, I'm not exactly sure. We're probably a similar amount of time. It's just like they have to keep that pressure on within the company and also keep themselves motivated and excited and continuing to push. Just such a hard path. There's benefits to being that founder, but it's such a challenging life, too.

**Keith Yandell** (00:40:42):
Yeah, I think it can be lonely to be a founder, for sure. I know that Tony's tried to develop a community, for him, of people who are similarly situated from other companies, and that's been helpful. And the real founders that I've come across, that drive, though, is something they can't turn off. They don't have to try to keep it, because there's a handful of traits I've seen that are pretty common. One is a level of obsessiveness. Two is hypercompetitiveness. And I think they're good at manufacturing straw men, even if everyone's saying nice things. It's like Michael Jordan used to take things out of context and make bulletin board material. There's definitely an element of that in the great founders that I've come across. And there's just a raw curiosity. So it's the competitiveness, but the curiosity in learning how things are working, and those all come together to create a drive that just never stops.

**Lenny** (00:41:33):
That resonates. Coming back to the DoorDash journey a little bit, I imagine the pandemic was kind of this microcosm of high highs and low lows, where, as an external observer, felt like everyone needed DoorDash immediately, and it was just probably the best thing for your business. On the other hand, I imagine you had to scale like crazy and keep the wheels on the bus through this time. Can you just talk about that part of history for DoorDash?

**Keith Yandell** (00:41:55):
I mean, it was just a wild rollercoaster. We were trying to get ready to go public, first of all, and so there was that overlay. And then, what you saw was our volume dropped right away, like the first or second day of lockdown. And I was like, "Well, this is going out of business because no one wants to order food from restaurants anymore." People didn't know how COVID was transmitted. And so just basically volume dropped out a cliff. And I was like, "Oh, went from a super high. We're getting ready to IPO. Super low. Volume's going to zero." And then, all of a sudden, volume doubled. And that was really exciting for a second, till we realized that our customer support center... I was running support at the time. All the support centers around the world shut down. So you're doubling volume. You have no one to serve it, from a customer support perspective.

**Keith Yandell** (00:42:39):
And our infrastructure, we weren't planning to grow that fast. We didn't think there was a chance of two or three exiting in a very short window. And so every Friday night, the app would crash. And if you're running customer support, there's few things you like less than the app going down. Set aside what it means for the customers and for the business. Selfishly, it's just super painful. The irony of it was, is our NPS was going up and that people were just so grateful to have the product, to be able to safely get the things they needed, for people to be able to earn money at times when they really needed it because maybe their job had been shut down, or they weren't allowed to go in. It became a really essential service for folks. And that was really motivating for me, and I think for the team, is to really be able to fulfill the big part of our mission of empowering local economies in a very unique way in a very special time.

**Keith Yandell** (00:43:30):
And the last thing I'll say on the pandemic was, one of my most vivid DoorDash memories was being on a Zoom call, where we were trying to figure out what to do to help restaurants. And again, we were trying to go public. And Tony made a decision, and I admit, I'm on the wrong set of history. I was arguing that this seemed extreme, just to cut commissions by basically 100 million bucks for restaurants, to help them stay in business. And I'm like, "Hold on. We're trying to go public. This is going to completely change the bottom line perspective. No one's asking us to do this."

**Keith Yandell** (00:44:06):
And Tony says, "Keith, you think too short-term." He's like, "This is the right thing to do." And reminded me of the Ted Lasso quote, which is, "Doing the right thing is never the wrong thing." And talk about how sometimes there's healthy debate. He didn't want to hear any debate on this one. He said, "Just shut it down." And he's like, "Founder-led decision. This is the right thing to do. We're going to cut these commissions." And I woke up the next morning and never been happier to kind of been overruled in a debate before than there. It was just such a meaningful moment for the company, and I was so proud to be a part of the organization.

**Lenny** (00:44:40):
Is there anything else you took away from that experience of just living through this up and down of pandemic times at DoorDash?

**Keith Yandell** (00:44:48):
It actually reminds me of the best advice I got when we were having our first kid. And everyone thinks they're going to give you the insight that's really going to be transformative. But one that stuck with me is, "For better and for worse, everything's temporary. So the highs, you can't get too high. The lows, you can't get too low." That really resonated with me during that period of time, as well as this general idea that you have to try to find opportunities to reach the potential for the business. And decisions sometimes have to be made in very short time horizons, and being able to seize those moments, I think, is really important.

**Lenny** (00:45:24):
I have a few questions about product that I want to get to. But one bigger question about DoorDash is, you've been involved in a lot of the bigger fundraising moments, DoorDash. I think you've worked probably with every major firm out there, raised large dollar amounts for DoorDash. Are there any memories or lessons that you can share from that experience?

**Keith Yandell** (00:45:44):
We've definitely tried to raise from everyone, been told no many, many times. I mean, raising the Series D was really difficult. Tony and I worked together very closely on that one. And there was a lull in the tech market publicly, and it translated pretty quickly to the private markets. And people didn't believe in either the TAM or the profitability of the business model. And it was difficult. I think one thing that process taught me is after we raised the D, almost every round, or I think every round ended up being led by someone who had passed in a previous round. And that was because we put up numbers we were highly confident we were going to hit.

**Keith Yandell** (00:46:25):
I'm an operating partner at a venture firm on the side, and I see that most people put up stretch plans, but they [inaudible 00:46:31]. But that was just not in our DNA. We wanted to make sure that we put forth numbers that we knew were going to hit, and that cost us some dilution upfront in the form of lower valuations, I think. And there's just a trust that builds from that, where when we tell people we're going to do something, that they have conviction that we're going to do it. And I would trade a couple of points of dilution for that level of trust with the right investor base over time.

**Lenny** (00:46:58):
For founders that are going through fundraising right now, maybe having a hard time, any just advice from that period for founders, yeah, that are having a hard time raising these days?

**Keith Yandell** (00:47:08):
It's fortunate because you only need one yes. Right? And you see all the people post the how many rejections they got. Every business that you have heard of has gotten rejected by at least a handful of venture capitalists at one point or another. And so that drive to keep going, if you believe in the business, is critical, absolutely critical. I mean, we were weeks of runway situation and had been told no by everyone, and it was just Tony's drive, really, to keep going. And the way he explains it to me is it's just the difference between a founder and a non-founder. If you're really a founder, you just have to find a way. You have to keep going. There's no question. And I mean, that's the only advice I can give folks, is it only takes one yes. But you got to keep going.

**Lenny** (00:48:00):
Awesome. Shifting a little bit to a few product questions. Most listeners to this podcast are product builders, growth people, founders, and so I have a couple questions here. Today you're currently leading the corp dev and BD team, and I imagine you work closely with the product team. And so I'm curious what you've found to be an effective relationship between BD and product and from the experience you've had at DoorDash doing that.

**Keith Yandell** (00:48:26):
Yeah, I joke that our head of product, Rajat Shroff, is actually the head of BD, because he's both interested and good at it. And to do impactful BD, the two really have to go hand-in-glove. So when I think through how to make that relationship work, the first challenge I've confronted, and maybe mistake I made, is trying to figure out what the right cadence is. When do you bring in the product team? Because if you bring them in too early on a deal that really has no chance of getting done, you waste valuable cycles. And our tech talent is our most precious resource, probably, at DoorDash. And so you have to be really mindful about when you bring them in. But if you bring them in too late, it may be a situation where you've given on terms that you really shouldn't have, and that can be really detrimental to the partnership as well.

**Keith Yandell** (00:49:17):
So I think one thing to do is just give visibility. So without actually bringing them and having a full discussion, like, "Here's the pipeline. If you see things that are super impactful, let us know. If you think things you're not so sure that are going to make a difference, please let us know." That's been really helpful.

**Keith Yandell** (00:49:32):
Another thing that Rajat's taught me is the importance of building platforms, and whenever you can. So what we used to do is, I'd go out and negotiate a deal. We had a lot of deals around DashPass, which is our subscription product, and I'd ask the product team to go build a bespoke thing for this particular partnership, Chase or whatever partnership we were negotiating at the time. And Rajat said, "Why don't you figure out what the scalable solution is for this? We will build you a product. You won't need to come ask us every time to build something. And then you'll know the parameters in which you can negotiate. You can negotiate a better velocity. We might spend more time on the first version of this, but very little effort for the next. And we'll have a high return on the product hours and the engineering hours spent." And so that was a super valuable insight that I garnered from him, is to try to figure out how to create these type of platforms.

**Lenny** (00:50:27):
Any other lessons of just building an effective BD team within a product company, especially at the scale you're at?

**Keith Yandell** (00:50:35):
A few other things. Number one... This is something else that Rajat taught me. One of our core values is, "Dream big, start small." And he really brought that to the BD product org. And there were some painful times. We invested heavily in a partnership with a hotel chain. We thought we were going to build, "Hey, we're going to make sure that this is the new dine-in experience when you're at a hotel. We can actually replace room service." And asked for a lot of product worked. And it was a total flop. And the realization I had is that we should have gone out and tested this at one hotel with just some hacky operations and seen what the uptick was. And what I would've realized is this particular hotel chain was franchised. So even though corporate thought this was an important thing they were going to prioritize, if the franchisee doesn't care about it, they're not going to give you the visibility, in room or otherwise, to make it work. So we built all this great integration [inaudible 00:51:32] that was totally wasted because the operations weren't right.

**Keith Yandell** (00:51:35):
And I have probably two or three other examples of situations where I learned I should have just gone out and stood out front with a promo code, and handed it out in certain forums, and seen if that changed customer behavior, before going and asking for the product resources. And Rajat correctly was like, "Hey, this is how we have to think about these things going forward." So yeah, definitely building platforms, "Dream big, starts small," use operations to test a thesis around a deal before you actually expend the product resources, I think has been super helpful. And then, the last thing would be to engage early, but not too early, on deal opportunities.

**Lenny** (00:52:12):
It's interesting how the advice of doing things that don't scale just continues to be useful, even at the scale of a DoorDash. Like you said, you could just stand out there and see if people want room service through DoorDash before building a whole solution.

**Keith Yandell** (00:52:24):
Yeah, early DoorDash, that was a core value. Do things that don't scale. It's as relevant today as it was then.

**Lenny** (00:52:31):
Same at Airbnb, is something the founders brought up all the time. And speaking of that, another area that you have a lot of expertise on is legal. So, you led legal for a while at DoorDash. And I was thinking, as thinking about this question, "I wonder what's more difficult, to be head of legal at Airbnb or head of legal at DoorDash," both fraught businesses and ideas. But we'll avoid that question for now. So my question is just legal and product. It's always this interesting relationship, how much legal has say over what happens versus how much product has final decision-making powers. Any lessons there about just how to set up a product and legal relationship within a software business?

**Keith Yandell** (00:53:12):
Yeah. And both for the product folks that are listening as well as the entrepreneurs who want to be founders, I've had the pleasure of working with two founders who are very product-driven, product-first folks, in Travis and Tony. And I've found that the way they engage on the legal side is with the curiosity I referenced earlier, which is they're both hyper curious, and they will ask questions until they understand the law in the particular area about as well as the lawyers. And then they will apply a first principles product mindset to their understanding of the law, and they will push the lawyers to make sure that they're not being overly conservative, which sometimes they can be.

**Keith Yandell** (00:53:51):
And so, when you're on the product team, especially if you're in a consumer-facing business, it may not be as pronounced for SaaS businesses, but if you're in a consumer-facing business, working on a consumer-facing product, you had better have at least a general understanding of what type of regulations are going to apply to your business, and what type of constraints there are, and how to push those constraints. Yeah, and so for me it's just about that level of curiosity and actually engaging in the profession. Right? There's nothing magic about the law. There's a finite number of things that you can learn. And just like all the other functions I've learned, I think you can engage them in a way, till you are proficient and actually really accretive to your business.

**Lenny** (00:54:31):
Keith, this has been incredible. I can see why people want to work for you, why they keep giving you more teams to run. I learned a ton. I'm really excited for folks to listen to this and learn from you. Two final questions. Where can folks find you online, or if they want to reach out or learn more, where do you point them? And then, two, how can listeners be useful to you?

**Keith Yandell** (00:54:50):
If you want to find me, LinkedIn is the place you can locate me. You can locate me there. I don't do any other social media. It is maybe unusual in this day and age, but that's my preferred medium. And then, as far as being helpful, always looking for referrals for great people. That would be the number one thing. And everyone has an opportunity to use our product. So if you have product feedback, I always welcome that as well.

**Lenny** (00:55:16):
For folks that maybe want to join DoorDash after hearing this, is there specific roles you're hiring for? Anything you want to share there, folks that might be interested?

**Keith Yandell** (00:55:24):
Yeah, I mean, select roles definitely on the product and engineering side is a place we're focused right now. But even if there's not a role open today, I like meeting great people. I've found that building relationships over time, even when you're not looking, is impactful.

**Lenny** (00:55:37):
Awesome. Keith, thank you so much again for doing this.

**Keith Yandell** (00:55:40):
Thanks, Lenny.

**Lenny** (00:55:43):
Thanks for listening. You can find the full episode on YouTube, or head on over to lennyspodcast.com.

---

## [10/22] Mastering onboarding | Lauryn Isford (Head of Growth at Airtable)

**Lauryn Isford** (00:00:00):
An activation rate that falls in a lower percentage range, maybe for most companies five to 15%, is better than one that falls in a higher percentage range because it means that there's likely much higher correlation with long-term retention and you're really working hard to get most of your users to reach a state that they're not reaching today.

**Lenny** (00:00:24):
Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to help you get better at the craft of building and growing products. Today my guest is Lauryn Isford. Lauryn was most recently head of growth at Airtable. Before that, she was a product growth lead at Facebook, working on user growth, internet.org, and growth of Facebook at India. Before that, interestingly, she led growth for Blue Bottle's e-commerce business. In our conversation, we dive deep into Lauryn's favorite topic, onboarding, why it's one of the biggest and most undervalued growth levers, what she's learned about optimizing onboarding flow through her work redoing Airtable's onboarding flow, what she's seen work and common pitfalls around onboarding, plus a ton of advice around figuring out your activation metric. I could talk all day with Lauryn about growth, but we had to cut this off to keep this to a reasonable length. Enjoy my conversation with Lauryn Isford after a short word from our wonderful sponsors.

**Lauryn Isford** (00:03:28):
Thank you. I'm so excited to be here.

**Lenny** (00:03:31):
We've chatted a bunch over Slacks, like all these different Slacks we're in and Twitter and emails, but we've never actually chatted real time, and so I have a million questions that I want to ask you. So, thank you again for being here.

**Lauryn Isford** (00:03:42):
We have never chatted real time, so everybody's getting the first conversation and I'm really looking forward to it.

**Lenny** (00:03:48):
I know that you have this pretty spicy contrarian take on experimentation and that I think you believe people run experiments too often and maybe not everything should be an experiment. Can you talk about that?

**Lauryn Isford** (00:04:00):
Yes. So, experimentation is a really big part, growth culture, growth hacking culture, PLG culture, growth marketing culture, any kind of growth, at least in my sphere, and sometimes teams can be really, really dependent on experimentation when trying to grow a business. A great example of this would be consumer growth at scale. Think your classic big social company. I worked at one of them. I am a former employee of Meta back when it was called Facebook. When you're at scale trying to grow a social app, experimenting can feel second nature. It can feel like a necessary step in your product development process that you want to drive more signups or you want to drive better activation with new customers. So, you change some buttons, change a design, and A/B test it, and then see if numbers go up or down, and then make your ship decision based on it.

**Lauryn Isford** (00:04:56):
I find that there's generally two reasons why a grow team wants to experiment, and one of them is to understand more precisely the metric impact of what they're building and what they're putting in front of customers, and the other is risk mitigation where you're making so many big dramatic changes that there's some risk that while this could be really great for the business, it could also be really bad and it would be good to understand that before everybody's experiencing that in production. So, with that framework in mind, sometimes you don't need to experiment. Sometimes if the business, let's say activation, right, activation rates go up 6% versus 7%, that precision actually doesn't help all that much beyond being able to say in your performance review, "Hey, I increased activation by 7%." So, it also is expensive to have folks on the ground, be it engineers, analysts, product managers, spending time understanding the results of an experiment that could otherwise be spent on road mapping, on foundational analysis, on shipping things. So, experiments can be expensive.

**Lauryn Isford** (00:06:09):
So, with all that said, generally my advice is to experiment when you need to and to primarily see it as a risk mitigation tactic when you're making dramatic changes and to let the product development process do more work. So, spend more time with customers, be more rigorous in understanding precisely what problem you're solving, get mocks in front of people and see how they react, and hopefully have more conviction than you otherwise would when you ship something that it's okay if every customer sees it tomorrow and that the experiment doesn't actually matter as much.

**Lenny** (00:06:44):
It's so interesting hearing that from a head of growth person. Working at Airbnb for a long time, and you talked about this, there's so much value put into the amount your experiment moves the metric is so important to, like you said, your performance review, your team's status, your team's ability to show they were successful. People look at like, you drove this metric 14%, which oftentimes you add up from experiments you've ran. How do you work in a culture like that, or is it just in that culture you may as well run experiments because that's the only way you get credit for the work you do, or is there a way to just be like, "Wow, that is how we measure it, but it's still maybe not worth running everything as an experiment"? How do you kind of find that balance?

**Lauryn Isford** (00:07:29):
It feels to me like that is the default culture, especially as growth teams become organizations and as those organizations grow with companies into growth stage public company territory and beyond. However, I do think you can build a different culture, and the only way to escape the trap of experimenting everything is to have a very intentional culture about doing right by customers and doing the right thing for the business. A growth team or a growth org exists in service of improving the business and delivering results for the business, and whether or not you measure those precisely in an A/B test, you still shipped them or you didn't.

**Lauryn Isford** (00:08:09):
So, the rigor around your process was either there or it wasn't. This means though that there have to be other ways to motivate, reward, retain, and develop really good talent. So, a culture around the impact you had on customers as measured by qualitative feedback or as measured by deals that were closed or deals that weren't lost, or other kinds of indicators that you did the right thing for customers is important and there shouldn't be, especially in engineering within the world of growth, a culture around having to point to numbers to demonstrate your impact because if there is, then the team will biased experiments all the time, and that's not necessarily the right thing for the business. It's a very expensive cost.

**Lenny** (00:08:50):
Wow. It's so wild hearing this from, again, a head of growth, someone that's so analytical like you. Is there an example of something you launched that maybe most people would've run an experiment and you decided not to for one of these reasons?

**Lauryn Isford** (00:09:01):
There is a feature, a product really, that Airtable offers called Airtable Forms. It's possible you've used it. I'm not sure if you have, but-

**Lenny** (00:09:10):
No, I don't think so, but I will go check it out.

**Lauryn Isford** (00:09:12):
You can check it out. There are some new features I'm about to tell you about, so maybe that will entice you.

**Lenny** (00:09:16):
There we go. Scoops.

**Lauryn Isford** (00:09:18):
So, Airtable Forms is much like other forms products. You can create a form and then send it to anybody to submit. The people who submit your form don't need to be a user of Airtable.

**Lenny** (00:09:30):
Oh yeah, I have used that. Okay. It's just like the turn an Airtable into a form. Yes, I've used it. Okay.

**Lauryn Isford** (00:09:35):
Exactly. So, something we noticed is that there was a gap in feature parity for Airtable Forms where the submitter could not request a copy of their submission. So, I might send my T-shirt size to Lenny for a form around ordering swag for the company and then I might want to remember which T-shirt size that I ordered and get a copy of that in my email. We created that feature which as a result was gated on creating an account with Airtable, and we just turned it on and wanted to see what would happen because we knew from rigor of a wonderful product team doing robust customer analysis and also doing the data work that this is something that people wanted, that it was a feature that would bring value to customers, and that even if it didn't move certain metrics like a signup percentage, even if it might affect the mix shift of activation rate from folks who signed up, it would be net good for customers who were using forms and who were submitting them.

**Lauryn Isford** (00:10:35):
So, we did roll that one out without an A/B test. It did have a big enough impact on our signup metrics that we saw at top line and didn't need the A/B test to see what was happening. And we also were able to use attribution to make some analysis possible after we rolled it out so we could learn from what was happening to the base afterward.

**Lenny** (00:10:53):
Fascinating. That's a really good example, and I imagine that helps a lot when the head of growth is encouraging the team not to run as an experiment versus a PM on a subteam, like, "Nah, we don't need to run this as an experiment," because in that case you're already acknowledging that team, "You did a great job, look at this metric. Clearly this one moved. Clearly customers want it." So, to your point, basically this kind of stuff has to come top down probably for it to work well.

**Lauryn Isford** (00:11:15):
I think it does, and it also cannot be an excuse for rigor around building well and being precise in what customers need, but overall, if you can be a results-oriented organization that just wants to do the right thing and move with urgency, then in my opinion, that's the way that you can have the most impact.

**Lenny** (00:11:33):
Cool. Okay. I didn't expect to spend that much time on that question, but there's so much there. That was really interesting. What I want to spend the bulk of our time on is onboarding. Something that I found myself, and I think you agree with a lot of this but I'll confirm, is that I've done a lot of research into the growth stories of the most successful startups, and what I find, one, is that retention ends up being the thing you got to crack. If you can't crack retention, nothing else matters. And then, two, more interestingly, onboarding ends up being one of the biggest levers to increasing retention which basically A then B equal C, onboarding ends up being one of the biggest areas of opportunity for growth teams both early on and late stage. And so, I guess the first question, would you agree with that general sentiment that onboarding is this huge opportunity and often undervalued?

**Lauryn Isford** (00:12:22):
Yes, I definitely agree. It depends of course on the shape of business. Not every business should prioritize onboarding first, but if you have some sort of self-serve element of your product, if someone can give your product a try, maybe you have a playground or a sandbox demo, if there's a premium element to your pricing scheme, if you maybe offer things totally for free and don't even have monetization yet, onboarding is that first really important choke point that from which downstream of onboarding so many important metrics and results flow for the business, from converting someone to a paid customer to closing a deal to growing, how many people in an organization are using your product. So, all of that really comes back to onboarding and if you can get that right, lots of good things will follow.

**Lenny** (00:13:13):
Okay, great. I'm glad we agreed. I already know this, but you spent a lot of time on Airtable's onboarding flow.

**Lauryn Isford** (00:13:20):
Yes.

**Lenny** (00:13:21):
And so, I'm curious just to learn about what did you do over the time that you spent optimizing Airtable's onboarding experience, what kind of impact did you see through the work that you did there, and then just any big kind of general takeaways that either you think people should know or that you'll take with you to future opportunities around optimizing an onboarding experience?

**Lauryn Isford** (00:13:43):
We could talk about onboarding all day. This is one of my favorite things to chat about recently. So, we did have a wonderful activation team rebuild Airtable's onboarding flow over the past 12 to 18 months. This included many projects, including several big ones. So, what you've probably experienced if you signed up for Airtable recently or what you might experience if you create a new account soon is we've built an immersive wizard that we called Guided Onboarding that helped guide you through setting up your first workflow on Airtable, and in doing that reduced the cognitive load of getting started, helped you make more progress faster, and created scaffolding that more than 90% of customers would benefit from to be able to get up and running on a product that's pretty complicated. That was the first piece.

**Lauryn Isford** (00:14:39):
We also then introduced some personalization to use case on top of that. So, instead of helping you build something generic, having you build something that's relevant to you. And then we also worked on ongoing education. So, once you're in a workflow, once you've built something, how do we help you level it up to go from beginner to intermediate to advanced? One funny anecdote about this is that we actually called that project The Mole, M-O-L-E, because the design pattern in product looks like a mole. It pops up from the bottom of the screen and gives you tips as you're exploring. So, those are some of the biggest changes we made. We did retire a bunch of our tooltips which were a big part of onboarding for a really long time. So, happy to chat more about that, and then also did a bunch of more incremental optimizations as well. In general, tried to take a portfolio approach to what we did.

**Lenny** (00:15:36):
Cool. Okay. A few questions real quick.

**Lauryn Isford** (00:15:38):
Yeah.

**Lenny** (00:15:38):
What were the three buckets real quick? So personalization, ongoing education, what was the first one?

**Lauryn Isford** (00:15:38):
The first one was guided onboarding.

**Lenny** (00:15:38):
Guided onboarding.

**Lauryn Isford** (00:15:38):
Exactly.

**Lenny** (00:15:46):
What was the impact of this work, just to give people a sense of the kind of impact you can have on conversion and then whatever other metrics you looked at there?

**Lauryn Isford** (00:15:53):
We were working on activation for a few years before I arrived at Airtable. There was already an awesome activation team, hard at work. Overall, the investments we made in onboarding over about a six to eight month period that included the wizard, The Mole with ongoing education, and also some personalization together drove a 20% lift in activation rate for Airtable.

**Lenny** (00:16:20):
Wow. That sounds quite impactful, especially at a company at that scale.

**Lauryn Isford** (00:16:24):
It's awesome. I would say celebrate any clear statistical significant improvement in activation rate. It's a big victory, and credit goes to the team that really spent many, many hours with customers and designing precisely to build something that could have that big of an impact. I think it speaks to the importance of really understanding what a user needs to be onboarded well, which is not the same as what your business wants the user to be onboarded to. So, delineating those and building carefully is really what made it successful.

**Lenny** (00:16:57):
Which of these three buckets would you say had the biggest impact? Because I want to kind of get a couple levels deeper to get to what exactly did you do that worked really well.

**Lauryn Isford** (00:17:05):
I would say that the guided onboarding wizard which is the immersive wizard that helps you figure out how to get started was the most impactful thing we did.

**Lenny** (00:17:14):
And it's interesting that you had tooltips and this feels like a tooltip-y thing. What is it conceptually? What's the simple way to think about the onboarding wizard versus a bunch of tooltips telling you like, "Hey, Lauryn, click here, next go here, and then check this thing out"?

**Lauryn Isford** (00:17:26):
Totally. Imagine being in a step-by-step guide where you are asked question, for example, pick which kind of project you're working on, pick what kinds of things you'd like to track for this project, and then as you select from beautiful, easy-to-click buttons that require very little work on your part, something is visualized for you on the right half of the screen. So, you can see your workflow visually come to light as you do the work on the left half of the screen, and all of this is done for you in a very guided and instructive way.

**Lenny** (00:17:59):
Are there any generalized learnings from that experience of just how to do a great onboarding experience? It sounds like probably avoid tooltips, instead just kind of ask questions and show them progress as they're going through it in kind of like an immersive experience versus here's the product, check out all the cool features.

**Lauryn Isford** (00:18:18):
I think there is something to be said for reducing reliance on tooltips, but I'm not sure I would go so far as to say the tooltip is dead, as much as I maybe would like to because there are too many of them out there. The reason for this is that I do believe Airtable's customers had a very specific need which was that the effort required to build basic scaffolding was too much and they needed more support, guardrails, bumpers to help them through that, and this kind of guided or immersive wizard was the best mechanism we could come up with to reduce that effort required and to make them feel more supported in their journey. I'm not sure that this pattern is one that works for every product. I think it's one that works well for a complicated product, where figuring out where to go next and how to get started is actually very challenging or has a high cognitive load.

**Lauryn Isford** (00:19:14):
So, I would keep that in mind, but in this case, it did work really well for us. I have seen some other products in the wild adopt similar patterns which gives me confidence that it is transferrable beyond Airtable and that there's probably something to it. That's definitely a big learning. I think one other big learning for us was that we had to meet users where they are. We have some awesome advanced features of really cool stuff you can do with Airtable, automations being a great example. However, users don't necessarily need to get that started on day one. They don't need to learn about the advanced stuff when they haven't even looked at a workflow before. So, we really worked hard to prioritize what the user actually needed and to consider what was necessary education versus what could be ongoing education and building it up.

**Lenny** (00:20:06):
Can you talk a bit more about what that was? What did you actually do to understand the type of user, and then what did you change for them? Because we actually did something like this at Airbnb, and it was a tiny bit successful for host onboarding but it wasn't anything big. And so, I'm curious what it is you specifically did. Did you ask them a few questions and then grouped them in a group and then changed the way the rest of the flow went, or, yeah, what'd you do there?

**Lauryn Isford** (00:20:31):
Good question. So, at the very, very beginning, we sort of said new users broadly need help. Who are they? What do we know about them? How can we help them? We spoke to a bunch of customers and also watched them get started and looked for patterns in behavior and also clusters. So, someone who is familiar with databases, somewhat technical and prefers to and has experience in building things might have a different need from onboarding than someone who is exploring a tool that was recommended to them for a project minute. With that in mind, there were some clear segments of personas or buckets of users that we could split out to give different experiences. Now that said, when we rolled out the guided onboarding wizard, it was actually just one generic onboarding that was one-size-fits-all, and while escape patches are great, we felt like we could solve, as I think I referenced earlier, more than 90% of use cases or users needs with one generic onboarding to start and then we could personalize from there.

**Lauryn Isford** (00:21:34):
When we started to personalize, generally we found bucketing customers by their learning style and their building style was more effective than more classic segmentation, like do you work in marketing, do you work in product management, do you work in operation. The reason for this is that there are many different types of building or workflows that are possible in Airtable. Some are sophisticated for use at work, some are simple for use at work, some are somewhere in between and are for a hobby use case or a consulting use case. Knowing how someone would go about building was more effective than what do you actually want to see on the other side.

**Lauryn Isford** (00:22:19):
This means that something like a template which can give you an example of how to build a use case for project management can be helpful for inspiration but might not actually be the best way to teach you how to use a product like Airtable, when instead, we could learn that you're someone who needs more familiarity with databases to be able to get to the next level, or who might need a more visual learning experience instead of a more data-forward learning experience. So, we tried to segment the experience that way and found that that yielded better results on activation than some of the more traditional segments.

**Lenny** (00:22:52):
And how did you decide which segment that a user was in? Was it a question you asked them right at the beginning?

**Lauryn Isford** (00:22:57):
We had a really awesome research team that would do some surveys and conversations with customers away from our production experience and away from individual projects. So, we had a really robust read going in to the project of who these different personas were, different building types, different learning types. That said, we do also ask folks when they sign up some questions and depending on who you are or what we might think we know about you or want to know about you, we might ask you different questions and that's in service of helping you get started.

**Lauryn Isford** (00:23:27):
I had some big ideas for how we might bring this to life even further that might come to life in the future, such as if somebody's there to just help out, if they're may be a teammate rather than a builder, if they're just there to work with someone else because Lenny invited Lauryn to work on her table because he needed Lauryn to do something or update a sprint, whatever. Lauryn needs really different onboarding than Lenny. So, actually getting that data in the flow is really useful because then we can route customers to a fully different experience. It's amazing how much low-hanging fruit there is to personalize and segment that onboarding experience in so many products that are out there. You just need to be really detail-oriented and precise on who you're working with.

**Lenny** (00:24:11):
You talked about this experience as activation, and so just digging a little bit further into that idea. One of the important kind of metrics, milestones you got to figure out when you're working on onboarding is what is an activated user, what's the activation milestone, what's the activation metric. I know you have some strong opinions and some really interesting insights into activation milestones based on your experience at Airtable. Can you chat a bit about that and just share what Airtable's activation metric ended up being?

**Lauryn Isford** (00:24:37):
Yes. So, overall, every growth team needs a north star metric. It's so important to have singular focus on what the business results are that you are working to drive in your team. On our activation team, which as I mentioned focused on onboarding, though in theory there could be other ways that you want to focus on driving activation, we had one north star metric which was what we called our team activation metric. So, this representative, a team of people were activated on Airtable's product and using it in a way that suggested they would be long-term retained. For us, that was week four, multi-user, meaning in the fourth week, more than one person on that team is active and contributing to a workflow on Airtable.

**Lauryn Isford** (00:25:23):
This metric is something that our wonderful analytics team determined to be highly correlated with long-term retention. It's also a metric that holds a relatively high bar, so it requires a number of things to be true, that something of substance has been built, that people persist and continue to collaborate, that they're collaborating on a weekly cadence, and also holds a relatively high bar on exactly how they're contributing, meaning that the sum total of this is somewhat hard to achieve which means that we have a hard job and also a high bar as an activation team to achieve that for as many customers as possible.

**Lauryn Isford** (00:25:58):
In general, I think an activation rate that falls in a lower percentage range, maybe for most companies five to 15%, is better than one that falls in a higher percentage range because it means that there's likely much higher correlation with long-term retention and you're really working hard to get most of your users to reach a state that they're not reaching today.

**Lenny** (00:26:22):
I really like that heuristic. So, the idea there is when you're picking an activation metric, you want it to be in the single digits potentially because you're saying that's more likely to be correlated with retention because retention's probably pretty low long term. Is that kind of the rough idea?

**Lauryn Isford** (00:26:38):
That's a rough idea. Of course, the metric should be correlated with retention no matter what, but if 40% of your customers are still active at week four maybe with a metric that would be week four active rate, then only a fraction of those are still going to be active in month 12, in month 18, and month 24, and I would much prefer to pick a more specific, more precise metric that maybe only 5% of users reach, but know that those 5% of users will be with us for the long haul, and if we could get that 5% even to 6% or 7%, it would have huge downstream effects on long-term metrics for the business. So, that's why I would opt for a more specific metric.

**Lenny** (00:27:22):
Okay. So, this activation metric, week four multi-user active is a really interesting metric. Can you talk a bit about how you actually operationalize this and put this to work on your team to help people understand what to work on and make sure they're moving the right sorts of numbers?

**Lauryn Isford** (00:27:39):
Totally. So, one of the first things that we did when me and my team started to revisit week four multi-user active right before we started to rebuild onboarding is break that metric down into all of its component. So, if you really think about what goes into that number, how many teams sign up as a team versus as an individual, how many of them make it to week four, how many of them have more than two people invited versus more than two people who've ever been active, versus more than two people who were active in the fourth week, maybe they have one person active in the fourth week, and then what does active mean, and what are the different kinds of behaviors that constitute contribution or being active. Doing that really detailed work on the metric helped us understand what levers we could pull to have a really big impact on activation overall.

**Lauryn Isford** (00:28:34):
Additionally, we actually started using more metrics. So, we didn't just use our activation rate metric week four multi-user active to make all of our decisions. We introduced a few more, and one of them with purely a retention metric for an individual. Are you week two retained? Are you week four retained? The other was what we called Build with a capital B, and this was roughly a sophistication score. So, for someone who's building something, have they reached sort of intermediate levels of use of Airtable? The reason why we added these metrics is we were building new mechanisms for onboarding that were helping users build more effectively and find more value in Airtable, but sometimes those treatments helped users become more sophisticated but didn't help them invite more teammates, or sometimes those new mechanisms made someone more interested in giving us a shot for a few more weeks, but what they built was actually not any more impressive than if they had done it on their own.

**Lauryn Isford** (00:29:38):
So, this group of metrics actually really set us free. It gave us those constraints where we could actually measure success in a few different ways and think about activation as being more complicated than just a single metric and celebrate anything we could do to help on a couple of dimensions. So, I know it's a little unconventional to have a few metrics that you work with, but we did find that that was really helpful when we were making big changes.

**Lenny** (00:30:04):
That is actually really interesting. So, it makes it feel like the core activation metric you talked about was more of an output metric and you kind of realized here's the things we could actually be moving directly. Is that roughly how you thought about it?

**Lauryn Isford** (00:30:15):
Exactly. It also helped us grapple with some of the tensions we felt which I know a lot of teams working on activation and onboarding feel, which is picking one metric doesn't paint the whole picture of what you're trying to achieve when you help a user onboard to your product and when you educate them about what's possible. So, in having sophistication and retention and an element of team use all as part of the fabric of how we talked about activation, it made us much more well-rounded as a team.

**Lenny** (00:30:46):
That connects a bit to, so we worked on this post together about how to choose an activation metric and you shared part of this story for that post, and there's a little bit of a debate amongst folks that contributed their opinion on how to decide an activation metric, where it's a debate between is it okay to have a workspace activation metric where it's like how many boards somebody creates, how many Airtables somebody has created versus a user action, like user has created 10 tables or user using it two times a week. I think you're on the side of workspace is maybe a more interesting metric for a collaboration tool, and it's interesting that you end up with both in the end which I think is kind of where folks landed. You probably look at how's the company using this tool and then per user, are they using it consistently. So, I guess the question is just what's your take on user specific activation metric versus workspace level activation metric?

**Lauryn Isford** (00:31:39):
I really like this question. I agree it is a great debate. I'm not sure there's a clear answer because it does depend on your product. In the case of Airtable, which is a product that has seat-based pricing and generally horizontal adoption, it totally makes sense to have a workspace activation measure because you want to understand in an account, in an organization how many folks are actually using a product and finding value. That can be different for tools that might look like Airtable but have different mechanisms for growth or different pricing or different vertical personas that tend to adopt it. So, I do think there is some variance. I do have a reaction to share with you that's a little spicy-

**Lenny** (00:32:19):
Please.

**Lauryn Isford** (00:32:20):
... is that it's important that growth teams are agile and this means that north stars, key metrics, focus metrics will change, and if you're working on the same metric forever, there's probably some inefficiency in actually chasing the biggest impact for the business. So, I would be open-minded about if a workspace or team or account activation metric is always the right thing to focus on. Team activation looks really healthy because your growth team did some really amazing work on it, maybe user retention is the right place to focus next year. Maybe it's more about conversion. Maybe it's more about some other signal for long-term retention, and I would be open to being dynamic and changing that metric over time. Stability in metric is great, it helps with momentum, it helps with building expertise, but sometimes we overfocus on picking the perfect north star metric and by the time you feel like you've found the perfect one, it's actually time to move on to something different and work on a different opportunity.

**Lenny** (00:33:24):
**Lauryn Isford** (00:34:43):
I've gone through it plenty of times. We actually at the organizational level on the Airtable growth award changed our north star metric a couple times which is a big deal that manifests for several teams. Roughly the arc of that change for us was shifting from being a growth org focused on revenue to a growth organization focused on user growth and customer growth. This for us was a really important moment where we decided that it was most essential in our work to grow the business to bring millions more people onto the platform, using the product and finding value in the product, because we were taking a decade's long view that they could always become monetized or converted customers later, and there wasn't really a rush. We felt that focusing on revenue led us to make some decisions that were a bit more short-term oriented than would be ideal.

**Lauryn Isford** (00:35:39):
There's also a dynamic here where in the world of enterprise SaaS, the world of B2B SaaS, there's a new theme called product-led sales that's very hot right now, and this means that often in a PLG company there's some ideal end goal of handing off certain customers to have a sales conversation or to close an enterprise contract. In that case, you might actually prefer to delay revenue for months or quarters or years to manifest it later, and when that's the case, your growth team should be fully aligned in lockstep with sales and with go-to-market team and focusing on user growth is actually the right call. So, that's an example of a big pivot that we made, and in doing that, we felt more strategic clarity and were able to move faster.

**Lenny** (00:36:25):
That is an awesome story. How long did that process take and any advice for folks that might be going through a similar journey of maybe we should rethink our north star metric not and not be revenue? Any advice there?

**Lauryn Isford** (00:36:36):
In general, I would say having stability in north star metric for at least six months feels like table stakes to me and that's for the reasons that I cited before, for building momentum, for building domain expertise, and also for compounding impact in areas where you see success, where you notice growth flywheels that you can optimize. However, if you're reaching a point where that north star metric feels like it's old news, maybe you're outgrowing it, maybe you want to work on different things, I think that's great. Be open-minded about changing it up. I would generally try to start with the mechanics of the business and what you think you might be able to drive in terms of metric impact with the resources you have on your growth team. That can look different for every growth team because some of them have marketing, some are more product and engineering, some are kind of a mix of both or even something different than that.

**Lauryn Isford** (00:37:27):
So, I would start with what impact do we think we could have? Where do we think the biggest opportunity is to chase? You can literally draw a funnel on a whiteboard and map it out and brainstorm together, do some analysis on the side, and when you see what opportunity feels like the most important thing to chase, try to build a north star metric that reflects the output of that work, rather than drives all of your decision-making from the beginning. A north star metric should really be a measure of what you plan to do, the strategy you plan to deliver is delivering results for the business on the other side, rather than the other way around.

**Lenny** (00:38:05):
So, you mentioned trials and freemium at one point and I want to spend a little time on this, and I know you also have some strong opinions about this kind of debate. Another debate people have, there's always debates in growth, between offering a trial or offering a freemium product, self-serve, and I think your perspective is you should do both, and I think maybe you call it a reverse trial because I was doing some research. So, I guess is that true?, Is that how you see the world, and then just generally, why do you believe that that is the right approach?

**Lauryn Isford** (00:38:31):
What is it about all these growth people with their strong opinion?

**Lenny** (00:38:34):
Right?

**Lauryn Isford** (00:38:35):
I guess I have so many of them. You're educating me on my own perspectives today. Freemium and free trials. So, to get on the same page with definitions for all of our wonderful listeners, a free trial is when you can use the product for free for a limited time and then your only option beyond that limited time is to pay for use of the product. Freemium would be when there are multiple options for how to use the product and one of those options is an infinitely free version of the product. So, you can use Airtable for free forever or you can pay some amount and have access to premium features.

**Lauryn Isford** (00:39:14):
So, with all that in mind, personally I'm in the camp of offering a reverse trial. Funky name, but what that means is offer a trial but also offer freemium. Do both. The reason why I like this is you get an opportunity when somebody shows up and says, "Hey, I'm going to give your product a try today," to show them everything that's possible. Onboarding is a huge component of that. Help somebody get started, have those aha moments and experience initial value, but also this is your moment to showcase everything that can be done with your really cool product, and you have some limited number of days, maybe seven days, 14 days, 30 days, to showcase all of the cool things that your company is building for your customers. That is the beauty of a free trial. It's not just that someone can try your product without paying. It's that they can try even more of the product, all of the premium, amazing advanced offerings that could be possible if they decide they want to settle on a premium plan.

**Lauryn Isford** (00:40:17):
When you are deciding if this is something you want to do, I would actually take a big step back from looking at competitive pricing pages and getting into the details and reading blogs and just think about what your philosophy is as a business on monetizing customers. The reason for this is generally the reason to offer a free plan or a free trial but really a free plan, the freemium type of pricing model is if you value letting millions, tens of millions of customers give your product a try, even if they never pay you a dollar. That shows to me prioritization and value of user grab, brand awareness, and exposure of your product more than just revenue. And if that's the case, a freemium pricing structure can be really great for your product, and it give you the space to see if your product can become that household name that everybody is familiar with and can give a try and get some early value and even experience some aha moments.

**Lauryn Isford** (00:41:24):
On top of that, you can offer a free trial to show what's possible with premium value and then that really can just be focused space for you to say, "Hey, look what's possible if you pay us $5 a month, $10 a month," and you might even get some extra conversion out of that and some more paid customers. So, in general, that's how I think about it. I like the reverse trial because user growth is important and if you're in a long game where you're trying to grow a business for a decade or more, ideally you're trying to get millions of people onto your product and you can always have that monetization conversation later, but you only get a couple moments where you can say, "Hey, pull out your credit card or let's get on the phone and talk about an enterprise contract," with a customer before you lose trust or lose patience. And so, that focus on helping them discover value and build loyalty to you is much more important.

**Lenny** (00:42:13):
I really like this concept, a super cool name too. I'm also thinking back to some of the SaaS tools I've used that have had this where I go straight into the pro plan and then I'm like, "Oh, I don't want to lose all these features," and then I actually end up buying it. So, when I'm hearing this, it sounds to me like it's a better version of the freemium approach. I imagine there's still many SaaS tools that are very enterprise-y, take handholding, maybe this goes away. I know Elena Verna who's been on the podcast is just a huge proponent of everyone will be product-led, self-serve eventually, but until that day they're still like, I don't know, I think of Retool I think is very hands-on, handhold-y, front I think is like that. There's all these tools that people don't get really quickly.

**Lenny** (00:42:57):
And so, I guess do you still think there's a need for some of these tools that need sales and customer success involvement to stick with just trial at least for now, or do you think they should all kind of find a way to get to self-serve and a reverse trial?

**Lauryn Isford** (00:43:12):
I do really agree with what Elena said. I really look forward to the day when self-serve and freemium are possible for every product, but I also recognize that that can be really expensive to build and implement and is not for everyone. So, that's cool too. There are other options. In general, I think freemium and also free trials tend to be most effective when there's something that the person who signed up can actually do on their own without being handheld. It doesn't have to be full functionality. It can be exploring a sandbox or a demo or something they can poke around in and experience value, see that aha moment. That's great. That's a moment where you can give value to that person who's chosen to spend time with your product. If that's not possible, there are different ways to be creative that don't require having premium pricing. You can think about how to use concepts related to PLG and related to top of funnel adoption in different ways.

**Lauryn Isford** (00:44:16):
So, maybe you can create custom landing pages or experiences that help showcase value without a full signup or free plan or free trial experience. Maybe you give folks the ability to sign up and while they've sort of signed up as an interested customer, they're not fully experiencing things, they might not even have the option to pay for something yet, but they can learn. There's some resources. There's some education for them to experience. Or, maybe you can think about top of funnel adoption or traffic as being most helpful for extension within customers you already. So, if you've signed contracts with a couple really large Fortune 500 companies and somebody wants to join and signs up on your website from the same email domain, then you can provide an experience for them that might feel like it helps them learn the mechanics that's actually only available to folks who are part of organizations that already have contracts with you.

**Lauryn Isford** (00:45:19):
It's a different way of thinking about PLG and not necessarily something you would offer for free, they're already an enterprise customer, but some of those concepts can still have a lot of value and help you grow the footprint of an account in an organization, and those are definitely awesome things to try if you can't offer something self-serve.

**Lenny** (00:45:36):
So, what I'm hearing is find ways to make things some component of it self-serve so that you don't need to necessarily talk to someone immediately. They can start to understand some element of it on maybe an interactive planning page or some very simple part of the product.

**Lauryn Isford** (00:45:50):
Exactly. I think the key is to figure out what it would be like for someone to experience value when there's no human sitting next to them, and that value doesn't have to be full functionality of the product.

**Lenny** (00:46:02):
Awesome. Coming back to onboarding, and this is my last onboarding question, I have another topic I wanted to touch on. Do you have any just general pieces of advice, either probably this will work if you're working on onboarding/things that probably won't work and are common traps that people fall into when they're trying to optimize onboarding activation flows in general?

**Lauryn Isford** (00:46:26):
I do see a very common trap that I would love to caution against, which is that employees of a company build onboarding for customers, but they build what they think customers want rather than what customers actually want, and that manifests in an onboarding experience that's not very helpful. So, there are two patterns that I typically see. One is naming features. So, imagine you're using Airtable for the first time and you see a tooltip and it says, "This is automations," and it explains what automations is to you. That's not that useful for a user who doesn't really know what's going on yet because they aren't sure if automations are relevant to them, if they're suited to their use case, what exactly the word automation entails. We've named a feature, but it's really sort of an announcement of something awesome that Airtable built, rather than an application that can help educate the user on how they'll receive more value from that feature. Try not to name features. It can be very tempting in practice, even though it sounds easy in theory.

**Lenny** (00:47:32):
Before you move on, what have you learned about how to actually name things in such a way people understand? Is there some you do there?

**Lauryn Isford** (00:47:39):
Ooh, naming things in a way people understand.

**Lenny** (00:47:41):
Versus the feature name, like you just said.

**Lauryn Isford** (00:47:43):
So, instead of that, I think what would be more useful, given the constraints of using a tooltip that's pushing someone to try an automation would be to explain how the automation is relevant to them, or even better, to enable a one-touch turn-on of the automation feature or set up an automation to complete your workflow where we actually do some of the work and if you click into here, we will show you what value is possible and help you get it to the finish line. So, really focusing on that contextual application or helping to drive towards an outcome, rather than just educating on a name.

**Lenny** (00:48:23):
And there's an element of smart defaulting, just like starting to do it for them versus do you want this or not.

**Lauryn Isford** (00:48:29):
Exactly. There's also an element here of segmentation or personalization where you should be sensible about if everybody needs to know what an automation is or if there are only certain folks who actually need to learn about it and others might not need to know.

**Lenny** (00:48:42):
Awesome. All right. Back to your other suggestions.

**Lauryn Isford** (00:48:46):
Oh yes, there is one other suggestion which is if you're working on a SaaS product, especially a freemium product, there's probably some pricing and packaging scheme that explains which features are available for free, which features are not, how many you get, and sort of maps out usage of the product, both for free users if you offer a free plan, and then for premium users if you offer premium plans. I find sometimes teams working on onboarding will map onboarding to that pricing or packaging. So, for example, maybe automations, to use the same example of the same feature, is something that's generally premium, that if somebody uses automations they're more likely to be a paying customer. It can be tempting then for an onboarding team to try to push automations to people when they're getting started because of course, we'd prefer if customers use premium features because then they might be more likely to become premium customers, but that is not in the best interest of educating a user on how to get started.

**Lauryn Isford** (00:49:44):
So, I do think it's very important to be careful that you are rooted in the customer need and rooted in helping that customer achieve maximum value, rather than sitting in the priors of what your packaging scheme might suggest or what might be in the best interest of the company.

**Lenny** (00:50:02):
As a growth leader, how do you operationalize that? Is it set some drag metrics? Is it just philosophically, let's make sure we're optimizing the right metric? What's worked to actually avoid that problem?

**Lauryn Isford** (00:50:15):
I think north star metrics help because a team can be singularly focused on the most important result for their roadmap and their charter. However, guardrail metrics are equally important. So, an onboarding team that builds amazing onboarding that causes a 10% drop in revenue would need some sort of guardrails to make sure that they knew that that might not be the right trade for the business, and importantly, should have the rigor and passion to go deep and understand what caused that drop in revenue and figure out what it was about that onboarding that ultimately caused a guardrail metric to suffer. So, with that in mind, I think guardrail metrics can be very useful and are important to choose wisely. I love working with strong analytics partners on a growth team because rigor and education around how to think about guardrail metrics is something that we should always be thinking about, whether you are a data analyst in functional specialty or a PM or an engineer or a designer.

**Lauryn Isford** (00:51:19):
So, that's how I kind of like to think about it. I do think guardrail metrics help and then just being well reasoned and thinking about what's best for the business and speaking about your work as being what's best for the business and the customer overall, rather than being too narrow in your own swim lanes of what you work on.

**Lenny** (00:51:35):
Great advice. I want to shift to a different topic and this will be much shorter. You have this really cool framework for thinking about the PLG funnel, product-led growth, and interestingly kind of trickles down to the team you build, metrics you choose, and things like that. So, can you just briefly talk about just this framework that you use to think about PLG growth in the PLG funnel?

**Lauryn Isford** (00:51:55):
When I think about how to grow with PLG in a business that has some element of PLG, self-server, freemium, I usually start with a funnel that roughly maps to the same scaffolding, regardless of business. Whether I've worked on the business, whether I'm supporting the business as an advisor, I love starting with this framework. The first step is join, the second is evaluate, the third is upgrade, and the fourth is expand. This funnel represents the journey of a customer in a PLG product as they advance and develop in their lifetime of using the product. It starts with becoming a part of the account that's using the product or signing up, and you might join because you found Airtable on Twitter or you might join because Lenny invited you to use Airtable. So, there are different ways that you can join that product in the first place.

**Lauryn Isford** (00:52:55):
Then importantly, you evaluate if it's right for you, and that word choice of evaluate is deliberately not onboard or activate because it's about what the user needs to see that they are going to get the value that they want in using your product and in building a habit around it. Next is upgrade. Ideally, someone has gone from beginner to intermediate or even advanced in their ongoing education and in getting to know your product over some amount of time and they see premium value and raise their hand and say, "I will convert to it." Now if you offer self-serve premium plans, that's awesome. They can do it with a credit card right in the product. Sometimes this means raising their hand to talk to sales and that's great too, but they upgrade to some sort of premium experience or to more value than what they have when they got started.

**Lauryn Isford** (00:53:43):
And finally expand, and vertical says this can be nuanced but with more horizontal tools. Ideally, a few folks, maybe one, maybe a few are using a tool in an organization and then many more adopt it over time, and that expansion drives net dollar retention, it drives brand awareness, it drives more usage in more pockets of the company, it is awesome for renewal rates if you're working with enterprise contracts, and ultimately then also brings new referrals into the product that loop all the way back to the beginning at join.

**Lenny** (00:54:19):
I love it. And what's cool is upgrade and expansion kind of bake in retention. You're not going to upgrade, you're not going to expand if you're not retained. Can you talk a little bit about how you use this framework? Do you bucket? Do you have these four teams on your growth team that focus on each of these stages? Is it more of a conceptual framework? Do you come up with KPIs for each of these steps? How do you actually operationalize this concept?

**Lauryn Isford** (00:54:40):
I think this framework is a step to abstract to represent exactly how you should structure your teams or to be represented with four metrics, for KPIs. However, it's a really good conceptual way of grounding your team or your organization in the mechanics of how machine that is the business you work on run. From there, it can become much easier to communicate with each other on where you see opportunity on specific pockets of the product that might be impactful. So, for example, you might be working on a strategy related to landing pages and be able to name that that's going to help drive joins in new organization, and that's a really awesome way to communicate why you might invest there versus investing in something related to onboarding that would help with evaluate.

**Lauryn Isford** (00:55:32):
So, I love this framework because it helps everyone communicate clearly and also you can derive from it more specifically what are the opportunities that are relevant to us with this framework in mind, and then revisit it over time to gut check if you feel like maybe what you're investing in now is a bit outdated and needs a refresh, or if there are other pockets of the business that need more attention that you might be able to work.

**Lenny** (00:55:58):
Can you talk a bit about how you structured the growth team potentially based on this framework and just generally how you thought about building the growth team at Airtable?

**Lauryn Isford** (00:56:06):
We had what I think is a pretty relevant set of teams. If you're thinking about building out a few in your own product or organization that focuses on sort of a PLG shape of business, we had one team working on acquisition and they were really responsible for the join. So, they mapped actually really well to this funnel. One team working on activation and they mapped pretty closely to evaluate. It wasn't a full representation of what's possible in evaluate. We were pretty focused on the self-serve business and that was different than, for example, helping an enterprise customer evaluate the right offering for them, but that activation team was most closely tied to that second step in the funnel.

**Lauryn Isford** (00:56:50):
And then we had a monetization team that worked on monetization and pricing and they mapped really closely to the upgrade part of the funnel. They did touch some other things as well. So, they worked on churn prevention and downgrades. They worked on some billing related projects, but in general, they were most thematically aligned with that upgrade step of the funnel. One area that is more emerging that's interesting is expand. So, when we got started on Airtable growth, we didn't have a team dedicated to that expand piece and it became increasingly interesting to us over time as we started to notice that larger companies were using the product. This meant that there was a bigger opportunity than there had been before to really help drive expansion and get more folks using the product in those accounts. That's an area that emerged later. That's a really good example of revisiting your priors and being resilient or agile in your org structure because it wasn't something we set out to work on initially, but it became a really clear opportunity later.

**Lenny** (00:57:53):
You mentioned that Airtable is thinking a little bit more about B2B growth versus just kind of B2C where I think it's been historically. Can you talk about that and just how you're thinking about that?

**Lauryn Isford** (00:58:04):
B2B growth is an emerging space for growth practitioners and hobbyists like me because the playbook hasn't been written the same way that B2C growth or consumer social growth has been. It's a new space, and there are quite a few companies that are really excited about exploring B2B growth and how to apply the DNA and the mechanics of a growth organization to more of that B2B motion or to working with more upmarket customers or enterprise customers. So, it's very top of mind for me. It's a active conversation in the growth community, especially in San Francisco. Overall, I'm really excited to see what we can do by applying this approach to growing businesses, to new types of businesses. It will require some differences in execution model. So, in B2C or in consumer social as two examples, you can experiment at large volumes or you can make changes that impact thousands or millions of people pretty easily.

**Lauryn Isford** (00:59:15):
In B2B growth, generally you're working with a much smaller set of customers and also the risk profile can be very different because smaller numbers of customers that represent larger percentages of your company's total revenue must be treated with absolute care, as opposed to a world where you might have millions of folks coming through your product every day and small changes might not have as big of an impact. In an enterprise organization, it's important to be very careful and rigorous and to prioritize that customer's needs all the time. This means that rigor, that customer conversations, that beta testing, that live prototypes and demos are significantly more important and that face time with the customer is significantly more important than it is in B2C growth. So, we'll see what happens. I'm really excited to see more folks who have given growth a try in B2C or in consumer spaces try applying it to B2B because it will become increasingly common in the industry.

**Lenny** (01:00:19):
Well, with that, we have reached our very exciting lightning round. I've got six questions for you. I'll go through it pretty fast. Are you ready?

**Lauryn Isford** (01:00:27):
I'm ready.

**Lenny** (01:00:28):
All right. First question, what are two or three books that you recommend most to other people?

**Lauryn Isford** (01:00:34):
Ride of a Lifetime by Bob Iger. I give this to new reports on my team. Great book to read when you're thinking about your leadership style, and Rocket Men, really fun story. I love a good story about ambition and achieving awesome things.

**Lenny** (01:00:50):
What's a favorite other podcast, other than the one you're currently on?

**Lauryn Isford** (01:00:54):
I like Fifth & Mission which is a local San Francisco podcast on local politics.

**Lenny** (01:01:01):
Favorite recent movie or TV show that you have watched that you've really enjoyed?

**Lauryn Isford** (01:01:05):
I really like the White Lotus Season 2. White Lotus was very fun to watch. I also, on the movie front, I'm in a habit of watching Best Picture nominees every year and last year there were a couple movies I really enjoyed, one of them was Belfast.

**Lenny** (01:01:22):
Oh man, that was an intense movie. I watched that recently. And also, if we should turn this into a drinking game, every time someone mentions White Lotus, we drink. It's an amazing show, but it's definitely comes up often. So interesting.

**Lauryn Isford** (01:01:35):
Comes up too much.

**Lenny** (01:01:37):
It deserves to come up often. I love it.

**Lauryn Isford** (01:01:39):
That's true.

**Lenny** (01:01:41):
It's great, but that'd be okay. We're going to do a drinking game from now on and I'll have a shot here. Love White Lotus. Favorite interview question that you like to ask people?

**Lauryn Isford** (01:01:50):
Tell me about a time that you delivered something that was impactful.

**Lenny** (01:01:58):
What do you look for in an answer when you ask that question? What's your kind of a good sign and what's maybe a bad sign?

**Lauryn Isford** (01:02:02):
I'm looking for someone to help me understand how they define impact and what it means to them. I think a good answer for growth practitioner is intrinsic motivation about having an impact on the business.

**Lenny** (01:02:19):
Hear, hear. What are five SaaS products that you use day to day, and you can't say Airtable?

**Lauryn Isford** (01:02:25):
Figma, Miro, Slack, Gmail, and my fifth one, I need to think about it.

**Lenny** (01:02:36):
It's because I cut out Airtable. I got you.

**Lauryn Isford** (01:02:39):
I know, I always say Airtable. Airtable's definitely number five.

**Lenny** (01:02:42):
Okay. Probably number one. Okay, final question. Speaking of Airtable, what's the coolest use of Airtable you've seen?

**Lauryn Isford** (01:02:48):
There was a great embedded view, which is the internal term for when you put Airtable on your website in an embedded way so people can check out cool stuff, related to finding COVID vaccine when they came out, which was really awesome. I also appreciated that a similar use of Airtable has become quite popular this year in support of facilitating folks who've been laid off to help them find new opportunities.

**Lenny** (01:03:15):
Lauryn, this was amazing. I learned a ton. We got through everything I was hoping to get through which I did not expect. Two final questions, where can folks find you online if they want to reach out and learn more and to reach out to you, and then two, how can listeners be useful to you?

**Lauryn Isford** (01:03:28):
You all can find me on Twitter. I'm @laurynisford. I love hearing about how folks with all different kinds of cool products are thinking about growth. In general, I find all of us are better at growing businesses when we study the awesome wins and learnings of others. So, please, my DMs are open. Send me cool things you're working on. I'd love to learn about it.

**Lenny** (01:03:51):
Amazing. Lauryn, thank you. Let's go drive some growth.

**Lauryn Isford** (01:03:54):
All right.

**Lenny** (01:03:57):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [11/22] Understanding the role of product ops | Christine Itwaru (Pendo)

**Christine Itwaru** (00:00:00):
Speaking as a former PM, I would not ever give up spending time with customers and watching their pain. That's how I fell in love with product was I saw my internal customer 12 years back now fighting with the keyboard, fighting with the mouse, and I was just like, "Oh, my gosh. What's this guy doing?"
**Lenny** (00:00:23):
Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard won experiences building and growing today's most successful products. Today, my guest is Christine Itwaru. Christine is a long-time product ops leader at Pendo, a role that she transitioned into from product management. I've been hearing more and more about the rise of product ops and I've never really understood what the role was until I have this conversation with Christine. 
**Christine Itwaru** (00:02:37):
Thank you. I'm so happy to be here, Lenny.
**Lenny** (00:02:39):
First of all, I just wanted to give a big thank you to Ben Williams who is a previous guest on this podcast who suggested you join this podcast and who connected us. We were chatting earlier and you said you have a story about Ben. So, what is that? 
**Christine Itwaru** (00:02:51):
I do. Absolute thanks to Ben for connecting us. So, when he made the intro, I was super excited, one because it's you, and two, because I love hearing from Ben. I was like, "Oh, great, he's doing all these wonderful things and whatnot." I just remember in that moment, my first conversation with Ben, which was really early in the days of starting product operations at Pendo and we were going through all these just really crazy things that he was going through and his team was a customer of Pendo at the time. He's sitting there just staring and I was like, "Oh, you're okay?" He was like, "Yeah, I'm fine. I thought that I was just throwing them off at every return." 
**Christine Itwaru** (00:03:28):
He said to me, "I bet you I'm not the only person who has these questions and I bet you I'm not the only person that's thinking about all these problems that probably seem very normal and natural." I don't know. All of us are going through this. This is why I'm building product ops here. But what he said and he was just like, "I really think there are a lot more people that you need to talk to about this stuff." It's just full circle. I think he connected us and he was one of the reasons I started to say... One of the best things that my first boss product always told me was, "You have to find a way to give back." When he said that to me, I was like, "I wonder if this is one of the ways that I can start to give back to the product community."
**Lenny** (00:04:08):
Awesome. Well, here we are, and obviously, we're going to be talking about product ops. You've been in the product ops role for seemingly feels like as long as the role has existed. I'd love to know when you think the role actually and we're going to talk about just when this spurred happened in product ops. I hate this term, but it feels like you're a thought leader in the product ops space. I've never actually worked with anyone in product ops. I've never had a product ops team, so I have a ton of questions. I imagine many people listening also have and are also just curious about this emerging role. 
**Lenny** (00:04:38):
So, what I'm hoping we do with our chat is to help people understand, "Do they need a product ops team? Would that be beneficial to their company? Whether people should be consider moving into product ops, whether they're in PM or something else right now, and then just generally helping people understand this emerging role of product ops." Does that sound good? 
**Christine Itwaru** (00:04:56):
Yes, thank you, number one. That was really kind. Two, yeah, I'm happy to dive in. Yeah. 
**Lenny** (00:05:01):
Okay, sweet. So, I think we have to start with the basics. What's just the simplest way to understand the role of product ops, especially in relation to product management? 
**Christine Itwaru** (00:05:11):
I've had many ways of describing this in the past and it generally centered around the ladder of what I'm going to tell you or the second part of this, but I'm breaking it down now into two simple things. One is it is a thing you do. Product operations for a VP or a head of product or a product manager is the creation of some system that allows you to thrive or allows your team to thrive in product management. The second is what we've seen more of over the last couple years, and it's the more common definition. 
**Christine Itwaru** (00:05:44):
The emergence of the role itself is why it's so common. It's a person or the people, the group of individuals who are strong partners to the product manager and then for more mature product ops teams end up people being more strategic advisors to the head of products. So, your CPO or your VP again. When it comes to data, qualitative, quantitative, anything that they feel can help the CPO or the head of product make more strategic decisions and well-informed decisions. 
**Lenny** (00:06:11):
Got it. It feels like there's been this big inflection and emergence of the role in the past couple years, past few years. I'm curious what you think triggered that and if that's true, if it feels like it's just emerged in the last couple years and then just like why do you think that has happened? 
**Christine Itwaru** (00:06:28):
This is interesting, because as a former product manager and product leader, I don't think that things are new. Absolutely. When I go back to the story about Ben, I'm like, "No, none of this stuff feels really interesting and it's just stuff that we had to deal with in product." So, the problems have always been there. I think maybe that is because I have a product background. So, I felt that pain very acutely, but I will say for the majority of people I always speak to who don't have that product background, they're coming from consulting or from technical success or from some other group marketing maybe, it does feel relatively new because they're starting to dive into that space a little bit. 
**Christine Itwaru** (00:07:06):
But I will say that for me in particular at Pendo, it was the summer of 2019 that this really picked up and I remember a colleague of mine, shout out to Shannon. He's no longer with us, but he is one of the original people on the Pendo product team. He said, "I think this is the summer of the birth of product ops." I just started laughing and he was like, "I'm telling you, it's everywhere." All of a sudden, everybody's just like, "We need something. We need to make product better." I thought that was awesome because we had already started talking about it. 
[NEW_PARAGRAPH]So, it took me a bit to understand what was going on across tech that was making this thing so big. I'm very grateful because we have so many great customers that reach out and say, "Help us understand how you're doing this." I'm like, "Well, help me understand what's going on." So, for me, it went beyond the problems that we would solve as a product team with the Pendo product. It went into, "How can we help you as an organization solve pain that you're feeling within your product team that trickles out to the business?" 
**Lenny** (00:08:07):
That's interesting. That was the summer of product ops. What happened there? Why was there a summer of product ops? Why was everyone starting to get excited and creating product ops teams? 
**Christine Itwaru** (00:08:17):
Yeah, I'll dive in. The customers started to come up and we started to feel it a bit more and I felt like there was this huge need for a voice of customer management and synthesis of both this qualitative and quantitative data as a theme that I saw arising across our customer base or even just folks that were reaching out about this role as they saw Pendo was putting it down. There was a lot of pain around internal alignment in general, transparency to stakeholders up across your revenue team members. Then for a lot of people during this time, growth was a massive propeller of the need for product ops. I remember just sitting here in this office and getting these random... 
**Christine Itwaru** (00:08:58):
Every industry almost was like, "Yeah, I'm thinking about doing this and I really need to do this, the pandemic, blah, blah, blah." Because it was growth during the pandemic, especially within industries such as home furnishings and making their living space a whole lot better. All of a sudden, we started to see that rise, but we were all experiencing this massive amount of growth across some of these startups and really rapidly growing companies. We're also moving more towards these product-led tactics, product-led growth. All of these things I feel like made this perfect storm for product operations to come in and start calming things down. 
**Christine Itwaru** (00:09:34):
I personally believe there's this natural evolution that happens at any mature function when it starts to grow in an industry and across an organization. So, think about marketing or sales. This just started to happen with product managers. For me, I was sitting there going, "Well, you can appoint a PM to liaise with other ops teams and the business, but at what risk?" Their product portfolio, the growth and adoption of their product, all these goals that they have to hit today in order to build a better tomorrow for their customers. So, I feel like that was the moment to say, "Okay, how do we give them the structure that they needed to thrive?" Because the CPO is in charge of so much more than product people have historically been in charge of, right? 
**Christine Itwaru** (00:10:17):
I'll probably talk about Marty Cagan several times here. I really do admire and respect him, and I think one of the things that he always talks about is future teams versus high performing teams and focusing on outcomes. CPOs went from deliver, deliver, deliver to really increased business metrics or just help drive the bottom line versus just really look at the product. You really have to figure out what that means for the product team at large. 
**Lenny** (00:10:45):
Got it. So, the way to think about this role, because I imagine most people haven't ever had a product ops person in their company is there's a slice of the PM role that companies are finding is valuable to put on a different person that has different skillsets that can take this endless load that PMs have. PMs have so many things to do and their job is so full of responsibilities that there's a sliver of stuff that a product ops person can take off. I'd be curious too and feel free to comment on that, but I'm also curious, you mentioned a few specific things that the product ops folks do. 
**Lenny** (00:11:19):
It'd be cool to just go through a bullet list of just those sorts of things, like you said, responsible for voice of the customer, pieces, alignment across stakeholders, whatever. If you could just go through some of those, that makes it really concrete I think for people to understand wow, this person that could have someone do all these for me, that'd be amazing. 
**Christine Itwaru** (00:11:37):
In some ways, I've got this question a lot from product managers who are concerned about the rise of this role or product leaders who are concerned that it was going to create some controversy or friction between product ops people and product managers. The way I've coached people to get around that is really, "What are your people responsible for? What are you holding them accountable to? Are you holding the product manager accountable to elevating these strategic insights so that they are going to elevate it to everyone else and then everyone else is going to go out there and build thing and drive the value or are you holding them accountable to truly understanding the customer in whatever way possible?" 
**Christine Itwaru** (00:12:15):
Especially going on and talking to the customer, please don't let anybody ever take that for granted. Really spending time with their engineers and the customers in order to drive a better experience. So, if they've got to spend all this time, which is our most valuable asset with those two entities, everything else still has to give. So, I think that yes, there was a point of friction, but I feel like now it's been a nice change where I'm seeing people in products saying, "No, I want to do product ops now," who was a former product manager. The second part of that, you said, let's go through the list of tactical things. Yes, voice of customer management is definitely one of the things that we're seeing more... 
**Christine Itwaru** (00:12:54):
I don't want to say mature because then I feel like I'm seeing mature of your peak, but the ones who have matured a bit, I feel like they are focusing more on the voice of customer elements. So, quantitative analysis, qualitative, bringing all of these different inputs that would traditionally be handled by product manager through looking across the aisle at their PM or looking at different data sources to the surface when they're going through their product development lifecycle planning, and really figuring out too what that balance is. I think there's an art. You can do voice of customer in two ways. 
**Christine Itwaru** (00:13:27):
You can do it one in this process way where you're feeding it to a really mature longstanding product team who has switchboard product or you have this voice of customer thing that you have to do for teams that are actually building something new. They're really trying to move fast, so how do you really get them what they need in order to experiment and iterate on the next thing that they're doing? That's one aspect. Another one is tooling. We see this more for folks who don't yet have tools under control in their product org. I'm not saying everybody has this, right? We had someone at one point handle whatever tools connected to Pendo and make sure that those systems are set up for maximum outcomes for the product manager. 
**Christine Itwaru** (00:14:10):
So, Pendo's connected to Salesforce. We're connected to Looker. We're connected to all these different. So, what does the product manager need to achieve out of all those things that ultimately drives our experience for Pendo ourselves? We get very meta here. That person was responsible for that. That's all also a part of the data component. The other things that we're seeing are more of along the lines of content strategy and being really intentional about making content and education a part of the product process and the delivery process. So, taking a look at how they maximize the outcomes from the outcome that the product manager is driving so that they can help increase retention, growth, and all of that good stuff for the product. 
**Christine Itwaru** (00:14:57):
So, those are some of the things that we're seeing. Then there's also this component that happens or this piece of it that happens in the beginning when you're standing a product ops for a product team that does not have much process in and that's the process piece. That's the bit that's a bit controversial, because folks are like, "Is this just program management? Is this just a different flavor of agile?" 
**Christine Itwaru** (00:15:20):
So, what we're seeing is this, what are these folks doing? Are they managing and facilitating the product development lifecycle? Are they doing things with the rest of the organization? So I feel like this one's a little bit up in the air. Some are actually agile facilitators as well, but I am seeing emergence of some companies that have the program management team under the product's umbrella to help with this massive amount of things that they have to manage across the board. 
**Lenny** (00:15:49):
Oh, that's a really interesting point on the last piece. I want to dig in on that a little bit just to summarize what you shared. So, some of the key roles of a product ops person, there's this voice of customer element and just to understand what you mean by that. The team is aggregating feedback from customers and feedback from the customer support and sales and things like that and sharing it with the product manager to give them clear conclusions and takeaways so that the PM doesn't have to sit there and filter their data. Is that a way to think about it? 
**Christine Itwaru** (00:16:19):
That's one part of it. We actually developed this really cool way of doing it here at Pendo, which is the transparency is a word that we love here. What we found that there was just not this need for the revenue org to be transparent and say, "Hey, this is what we're hearing. Product people, please listen," or vice versa. Here's what we're doing for your customer. There was this interesting moment where we realized that our sales team was screaming for something and our success team was screaming for something else, but [inaudible 00:16:46] looking at something else. So, they're all wonderful relevant things that our customers wanted, but we were like, "What if they're aware that they've got all these amazing things and they're talking about it separately?" 
**Christine Itwaru** (00:16:59):
Our PMs, they would get the whole readout with us, but we brought those folks in a room together. It was really cool because I think our head of professional services team at one point was like, "Whoa, this could truly impact what we do from an onboarding perspective and now we have this data. Then how do we then strengthen this area and the product?" So, it wasn't just about the components. So, I don't know if other companies are doing it like that, but I was very proud of the way we ended up doing that here. But the PM got risk data, high-priority deals, feedback from our feedback product. What are we hearing from prospects versus paying customers. What segments are saying what? 
**Christine Itwaru** (00:17:35):
All that stuff got fed over to the PM and then validated through our research team or disputed through our research team, which was really cool. This is a really good partnership with our research team. But on the other side, what was really nice too was we were able to educate our revenue team on behalf of the product team and say, "Guys, not everything requires a product change." So if you're saying there's customers that have friction around this one area of this product, maybe it's enabling. Maybe it's something that we need to help you guys understand a little bit better so that you can make their experience better or maybe we need to help update. It's just very simple things like that that just ended up coming up this voice of customer process. 
**Lenny** (00:18:15):
So essentially, it's just finding ways to make the PM more focused and allow them to focus on the things they want to focus on and reduce workload. On the user research piece, so it feels like there's user research coming in. PMs are involved, user research. There's a research team. Where does the product ops team fit in there or is it focused on internal alignment, stakeholder feedback more versus external customer feedback? 
**Christine Itwaru** (00:18:41):
Yeah. Again, I'll say these probably several times. Every company's doing it in their own little bit of flavor. I'll tell you that here and from a couple companies that I'm seeing outside of Pendo, our user research team sits with our UX team. They report into our head of UX and they are responsible for proactive research and making sure that we are aligning to our strategy and saying, "Okay, here's what our folks are saying. Here's why we're going after this market or this new thing that we're doing. Let's start going out there and validating or checking with some of these key personas and what we need to do." Then they are also a part of the ongoing development process or product development process. 
**Christine Itwaru** (00:19:21):
So, testing stuff out, making sure that they're doing user interviews, and all that good stuff. So, they sit as a partner to us. We work very closely together. Again, I'll give you that example of voice of customer, which is we have all of this input coming in from our customer success or post-sales teams and we know we're about to invest in our guides area of the product. We have all of these. What do we do with it? Well, we couple that with I'm personal responsible for NPS or I was for a very long time. I'm seeing a lot of noise around guides. 
**Christine Itwaru** (00:19:52):
So, I take all of that, we pull it all together, and we give it to our head of research and say, "All right. Let's all make sense of all this together. Is this something that is in line with the direction that the product team is going, the guides team, or is this something that we're going to need to dig a little bit more into to see if their efforts right now where they're growing are not where there should be going?" 
**Lenny** (00:20:10):
The other two bullet points, just to make sure I totally understand, you help with tooling. The product ops teams help, just optimize the tooling to build product. Is that a simple way to think about it, just make sure the product development process is efficient? 
**Christine Itwaru** (00:20:24):
Yeah, we partner with the program management team and the tools that they use for product development stuff. I would say it's more, "What are the things that the product manager needs in order to be successful?" So, we look at Pendo, right? We do use our own product like I mentioned quite a lot. Salesforce is another thing, so how does that all plug into our own product and what data are we looking to get out of there? So, our PMs have a complete picture in Pendo. Tray is another one I mentioned. Zapier was another one that we had used. So, it's more about the PM's tool stack versus the PM's planning tool stack if you want to draw that distinction. 
**Lenny** (00:20:59):
Got it. Okay. That is helpful. Then content strategy, by that, you mean internal documentation to train sales and customer support or is there also help the product team build out product marketing content and things like that? 
**Christine Itwaru** (00:21:13):
Neither or a bit. I guess what we have done is fed into both of those technical documentation. We use Zendesk as another tool, so we use Zendesk as another part of our tool stack to support our customers. So, a brand new feature comes out. Natural thing to do, let's write up this thing in Zendesk, but it's also about how we weave education into the product and we use Pendo again. Sorry, that's all right. It's actually really good tool. So, we do use Pendo guides and we just release our NPS themes. So, a pain in my team's butt has been manual labor around NPS themes and qualitative data. So, we designed this experience for customers who are in this beta. So, that they can in the product understand what it is. 
**Christine Itwaru** (00:21:59):
Then if they really need more, they can go out to the technical documentation, but it's about the education for the customer. I mentioned earlier treating content is a part of the development lifecycle process. You really want to treat it as a part of definition of done. When you think about product-led growth and the emergence of that in particular over the last couple years, it's all about creating that experience and keeps people in and helps them upgrade. So, they work alongside product marketing to develop these playbooks for what they're doing in app to create less friction and drive more engagement. 
**Lenny** (00:22:36):
Got it. Okay, that makes a lot more sense. Would it be safe to say that product ops is essentially for B2B companies where there's all these internal stakeholders, sales, customer support, marketing, things like that and that's the work that you can take off the product manager's plate? 
**Christine Itwaru** (00:22:53):
My personal experience and I think a lot of people would agree with me has led me to believe that's not accurate. It's emerged a lot more in B2B or I think we've seen it a lot more in B2B or at least people talking about it. I'm curious as to why and I wonder if it's because we're sharing because we're all trying to go through this thing together serving each other and then the other is serving the customer. So, it's not like, "Hey, you helped me figure this thing out." I understand I was so lucky and I still am so lucky to work with so many people in my network, in our customer base to help them understand the role or determine whether they even needed this thing or not. 
**Christine Itwaru** (00:23:28):
Without calling out names, there were some really big companies in retail and finance and some industries that you would not expect who are B2C, larger, well established companies who we all know and love and maybe not even love. Maybe the experience is bad for us. So, they also do have a lot more cross-functional engagement internally than we would even think of. So, I don't know if it's because we're used to this world and we haven't thought about that side of it, but it's really interesting. I think the common thread is the cross-functional transparency and then transparency out to the customer. 
**Christine Itwaru** (00:24:04):
So, I mentioned transparency is a big word for us, but readiness is another one and so readiness means a lot. You have your teams you need to get ready internally, but you really need to get customers ready for something new as well and everybody needs to feel aligned. So, it plays a massive part in what the product manager and the product team needs to consider, advocate for, deliver, and communicate about, I feel like no matter the size or industry. 
**Lenny** (00:24:28):
I imagine a lot of PMs listening to this have this two minded view right now of on the one hand, somebody could take all his work off my plate. That's awesome. On the other, it's like, "Oh, okay, there's another stakeholder that have loop into every meeting and they're going to be doing this work that's cool and important that I'm not going to get to do anymore." That's weird. What have you found is the best way to convince a PM to this is like, "Wow, this would make your life so much better"?
**Christine Itwaru** (00:24:54):
Yeah, I go back to that question that I have asked leaders when helping them stand this up, which is what are you looking at your PMs to drive and how are you measuring their success? That generally just helps everybody get on the same page really quickly. I've had customers or I've had folks come to me in the product community that say, "I've tried this and it's just not going anywhere." There's resistance to the role because they feel like it's stepping on too many toes and whatnot. Generally, I will tell you it's because they still have a bit of buying in the top to get done. 
**Christine Itwaru** (00:25:32):
I'm seeing that the most successful ones that are drawing the lines and showing that this role is valuable are the people that have their buy-in from their CEO or CPO at that level or their head of product and saying, "Hey, this is what this role means for you." So, I don't want to say it needs to be directive. I do want to say that you need to be able to articulate the value to somebody who's heading up essentially businesses and saying, "Here's what this role is going to drive for you at the end of the day." The very mature product ops end up having people that are strategic advisors too, a product leader. So, once you can show that this is what you'll also get as a result of me and this other person or me and this team doing this, it ends up being an easier conversation. 
**Lenny** (00:26:17):
What are a couple bullet points that are most effective to convince a product leader product op is going to make a big impact and benefit you and then just an ICPM who's like, "I don't want this person on my team"? What actually works there to get buy-in? 
**Christine Itwaru** (00:26:31):
Yeah. Number one, do you want your PMs to constantly be fielding questions from your revenue team when they could be spending time with customers? Yeah, you're shaking your head. That one seems to be the one. 
**Lenny** (00:26:43):
Yeah. Yeah, that's a good one. 
**Christine Itwaru** (00:26:44):
Yeah, I can count on one hand the companies who have blocked their product managers from speaking to customers and those companies are not product companies. I mean they do not believe in product management. They might say they do, but they don't. So, that's number one. Number two is how are you measuring your outcomes and where are you making this all transparent? Is this happening consistently across the board? So, one probably seeing product teams across so many different places is you might have somebody who's really passionate and really good at doing this stuff for their own vertical and then it doesn't scale. 
**Christine Itwaru** (00:27:20):
So, how are you doing this at scale so that your stakeholders are building this trust in you and making sure that they get the best out of the product team at any given turn? I say those are the two bullet points that seem to stick the most is that quality time, giving the PM what they need, which is their time to be able to drive the outcomes for the customer. 
**Lenny** (00:27:41):
What is it that you think a PM will never offload, if that makes sense? In your perspective, what's like the core of a PM's role versus maybe product ops for now and then maybe potentially other roles that take off some of the stuff on their plate? 
**Christine Itwaru** (00:27:57):
Speaking as a former PM, I would not ever give up spending time with customers and watching their pain. That sounds really bad to customers. I'm sorry. That's how I fell in love with product was I saw my internal customer 10, 12 years back now fighting with the keyboard, fighting with the mouse. I was just like, "Oh, my gosh. What's this guy doing?" 
**Christine Itwaru** (00:28:23):
I think it was an experience that some people might say, "Oh, I never want to be in that situation again because it made me feel very uncomfortable that my product is not doing for this person what it needs to," but for me, it was, "How do I make this thing do what it needs to for this gentleman? How do I make this thing better?" I cannot see product managers saying, "I don't want to be a part of that conversation." Then you know what? I'm going to say it then don't be in product. 
**Lenny** (00:28:50):
Love it. Yeah. I'm so curious what parts of the role get sliced off over time because I love that. That's the core of it is just build great products that your customers want and use and want to pay for. Then what else can people help you with along the side? Because yeah, PM role is just crazy. There's so many things going on.
**Christine Itwaru** (00:29:06):
It's crazy how this article that I wrote, I dug into the history of product management and it's like 100 years old not in its current form, but it's about 100 years old and just the evolution of what product managers have historically been responsible for. Then if you think about just really sit down and think about what the world has turned into today and how much noise we have coming at us. We talked about put yourself onto not disturb mode and I learned a long time ago, put myself onto disturb mode. So, imagine having a partner that helps you filter that noise. 
**Lenny** (00:29:44):
Yeah, quite useful. Along those lines, I was going to go in a different direction, but as you mentioned that, there's all these roles adjacent to PM. There's program managers, project managers, agile product owners, and all and then now product ops. I guess before team has product ops, let me just ask this one straightforward question. Which of those roles generally does the thing that product ops can do for you? Is it the PM or is it one of these other roles? 
**Christine Itwaru** (00:30:11):
It's a PM. It's PM. Yeah, it's a PM and then I would say, because what I'm seeing in less mature product orgs who first bring in product ops, the first thing they ask them to do is streamline the planning process. So, I would say it's a PM and maybe the agile. That's probably what it is today. I feel like program management and agile are starting to get a little bit close to each other in what they do. So, it's most of the PM stuff because we're doing elements of their job that they have off to the side versus being able to focus on. But again, in lesser mature orgs, the first thing is, "How do I actually just get the people to plan the same way and give me the thing that they're planning and doing?" 
**Lenny** (00:30:56):
That's interesting, what you said there, that maybe often a wedge to a product ops person joining their company maybe as a first product ops person is the planning, helping with the planning process. Is that what you find? 
**Christine Itwaru** (00:31:07):
It could be. The only thing that distinguishes product operations folks from program managers and agile is that product operations people know, understand the product, the customer, and the inner workings of the business. 
**Lenny** (00:31:20):
Cool. Yeah, Marty Cagan has some hot takes there about how product owners are never going to be great product managers. They don't really understand the customer needs and building product in any way. That's a whole other topic. I want to talk about the career path, but before we get there, I want to go in a spicy direction. So, Casey Winners, he is a guest on this podcast at one point. He wrote this hot take many years ago about this premise that operations in general often is a Band-Aid for inefficiency at a company. 
**Lenny** (00:31:54):
Companies often hire a bunch of ops people to just solve a problem and often they're much better ways to solve that problem. For example, tooling or a new process. His take is a person doing the thing often should be the last resort or it's a temporary gap and then over time you should strive to find a more efficient way to solve that problem than people. I don't think he's saying ops people in general or not necessary. It's an easy default. So, I'm curious what you think of that take. Generally, do you think product ops is this long term we're going to need more and more of this or is there a different path that's solving the problem that product ops? Spicy take warning.
**Christine Itwaru** (00:32:41):
Yes, I remember this. I'll address that inefficiency comment first, right? I mentioned a little bit earlier as roles in any industry or I guess any role matures like marketing or sales, this ops thing ends up being this natural progression. It's not just because the role itself is maturing. It's also because the org is maturing. So, what I found and what I'm finding with customers is that ops alignment across companies is what often ends up keeping the companies moving and keeping everybody aligned. So, to say ops teams are generally a sign of inefficiency or the need for them is a sign of inefficiency is not always accurate, it's generally a sign of growth and opportunity. 
**Christine Itwaru** (00:33:21):
People are really just trying to stay in aligned and do the best for the people that are doing the thing, the product managing, the marketing, the selling within that org. Overall though, I will say I will agree with his points about getting in and maybe giving it off and using humans for other things. I wrote something recently and I highlighted something that he mentions here in this article and what he mentioned on your podcast, which is we as product ops want to and should be standing up whatever processes or systems are needed and then get out of the way so we can focus on driving more strategic value. 
**Christine Itwaru** (00:33:58):
I keep mentioning that more mature product ops folks end up being a very good strategic advisor to leaders in product and to the product teams and that continues to be my belief. From day one, this has been my own personal goal for myself and for my team. I myself recently switched roles here at Pendo because I did what I said I was going to do, which was stand up the system, stand up the things that we knew we needed to do that were going to either be given off to another team or automated and then get the rest of the humans that are here to do the other strategic things for the product team.
**Christine Itwaru** (00:34:34):
Some of those are, "How do we increase retention? Like I mentioned, how do we focus on growth in this one area? How do we make the experience better in app? How do we do a better voice of customer management?" My energy now at Pendo is I'm able to now go towards more impactful things for not just the product team and the product community, but for our customers at large. So, I'm basically saying, "Look, I did what I needed to do and I'm ready to go." 
**Christine Itwaru** (00:34:56):
So I think that's something though that people need to be very, very comfortable with, very comfortable with. If you change course and change your tune two, three years into doing this and you built this team, you're like, "Here's what you're doing, manage this process," people are going to lose their mind. Change is constant, but telling someone, "I no longer need you to do that," it makes them a little bit nervous. So, for years when I was interviewing folks from my team, I made that one point abundantly clear to them, get into this role if you're comfortable letting go of things and moving on to something that is well worth your time. The company's going to change. 
**Christine Itwaru** (00:35:36):
Our process is going to need to be tweaked. The company is going to change. Something's going to need to be automated. We're going to need to cut something else. Maybe ChatGPT is going to make things very clear that humans are not always going to be doing the same things and we need to focus our energy elsewhere, but people do need to get comfortable with that role. 
**Lenny** (00:35:54):
I love that take. Generally, I think it aligns with what Casey's saying. What I'm hearing is you may be a product person today doing a bunch of stuff. Your job in a sense should be to automate as much of that as you can and find more strategic higher level things you could be doing instead of sitting there connecting Salesforce to Zendesk and maintaining that. It'd be great in customer feedback in theory. That could be a tool that could do that for you. That's part of the job. Is that roughly what you're saying? 
**Christine Itwaru** (00:35:54):
That's exactly what I'm saying. 
**Lenny** (00:36:24):
**Christine Itwaru** (00:37:51):
I touched on this quite a bit, but that lack of transparency in many directions across, down. Sometimes people are on very transparent about, "Hey, this came up in planning and here's what we need to do." So it's relevant for stakeholder management, getting stuck out to customers, internal teams, and making sure they're aligned, revenue teams in particular. 
**Christine Itwaru** (00:38:11):
That was the first thing we focused on at Pendo was really aligning our success org and our sales org to the product team. We monitored success just within... I think a quarter was the time-bound space that we had it in on quality of inbound to the product team. So, that was really cool. It was just more thematic questions around tell us what you guys do because our customers would benefit from this versus teach me how to do this thing. 
**Lenny** (00:38:36):
I wanted to dig into the transparency piece. Is that the same point as the transparency piece or are those two different heuristics? 
**Christine Itwaru** (00:38:42):
That's transparency. Yeah, so what happened was we realized that we share this story actually quite openly and I'll share it here again, which is one of the things that kicked off products for us was we had a really bad launch, a really, really bad launch. It was a moment in company history where we realized that there was not transparency across the aisle and there was this lack of readiness across the organization and out to customers for what was coming. It wasn't this piece that folks say, "Oh, well, they didn't know this was coming." Well, there's two things. There's the knowing something's coming and then there's the knowing what to do with it. 
**Christine Itwaru** (00:39:18):
You can use just some status keeping thing to say, "This is coming in Q4 and as we get closer, here's the date," but it's what to do with it and how to position it and how to talk about it and all the things that was missing from it. It was really bad and it was my fifth week here. It was a moment of, "Well, I promised myself I'm going to let this happen." That was one of the things where I said, "I'm going to start to focus a little bit more on product ops within this director position I had just as director of product." Then I spun off and I think we need to do this thing and make it a bit more formal. 
**Lenny** (00:39:53):
Just to dig it on a story a little bit, so I didn't know this, so you were a product manager at Pendo. There was this bad launch and you recognize there's this gap that maybe I could fill, that somebody needs to fill and that you want to take that on. Can you talk a bit more about that? It's really interesting. 
**Christine Itwaru** (00:40:12):
Yeah. They brought me in as their first director level. So, I was doing a bit of director plus a little bit of IC stuff because we were starting to build up our product team. Yes, that launch happened and the product area was under development for about eight months from what I can remember. I came in with the assumption and also knowing fully well that I'm a brand new leader in this product team and product people want ownership. They crave autonomy, they crave trust, and all of that good stuff. I know that firsthand. I did not want to jump in and say, "Have you done X, Y, and Z?", especially in the first four weeks of me being there. Yeah, it did not go very well. 
**Christine Itwaru** (00:40:54):
So, we recognized that we had more opportunity that we should have grabbed onto to test more with customers, to find feedback loops that were going to be healthy for the team and for our customers, to stand up ways for us to measure changes and impact of changes that this thing was making to our customers. This was the biggest launch in our company history since the launch of the product. So, it was a moment where we all sat down very openly and shared with each other what we all could have done better. It wasn't just the product team. 
**Christine Itwaru** (00:41:25):
So, I truly believe with a really healthy product operations person or team, you have that ability to impact change across the company. So, yes, we look at that story. I remember us sitting there and being, "One day, we're going to look back at this story and we're going to say, 'Oh, yeah, I remember that.'" We do now four years later or four and a half years later, but yes, I felt really passionate about making sure that that didn't happen. 
**Lenny** (00:41:48):
The gaps you found are there's just like this lack of internal alignment. Sales didn't know what was going on. Customer support didn't know what was going on. That felt like that's where the gap was because that's what led to this product ops opportunity, right? 
**Christine Itwaru** (00:42:00):
Yes. There was a lack of alignment across again, they knew it was coming, they just didn't know the extent of what to expect and how to prepare customers or prospects or the change the way that we should have. There was definitely training. There was stuff being done. It just could have been a whole lot better. So, there were gaps there. One more point was the piece after that was I love people. I love managing people. I love healthy team environment and dynamics. 
**Christine Itwaru** (00:42:32):
As a product person, it means a lot to have that, because if you have direct reports, you obviously want them to be happy and healthy, but as a product person, you have this system around you even if you're not having people that report into you where you feel ownership to make sure these people are healthy. I remember even in my early days of being a PM, I wanted my engineers to be super happy. I wanted them to be proud of work that they were doing and I wanted them to be comfortable letting go of things that we no longer needed. 
**Christine Itwaru** (00:42:58):
I remember that moment looking around and looking at our engineers and seeing that they were like, "Hold on. What? Where do we go now? What do we do right now?" We wanted to take that moment and make it less about firefighting and more about being responsible and really customer obsessed. So, that was our moment or one of our moments for thinking about, "Okay, we might need product operations formalized here."
**Lenny** (00:43:24):
It's interesting that your mind went to product ops, because I think most companies would be like, "Oh, the product manager of this product screwed up. They didn't communicate enough to ensure sales. They didn't set up the marketing material well." It often falls on the product team and the product manager. What made you realize, "Oh, this is a product ops role and I need to move into that role versus here we are"? 
**Christine Itwaru** (00:43:46):
Yeah, I didn't say in that moment we need a product ops role. All I said in that moment was we need to create a system so that this doesn't happen again. That goes back to my definition of what product ops is. It's a thing and it is also a person or a group of people. It could be one or the other. So, I want to make sure we decouple that. It does not have to be humans. It can be that there's a system being created that is from a strong product person who knows how to get this team to be healthy. 
**Lenny** (00:44:12):
That's a really good way of thinking about it. That clarifies it in a big way. Thank you. You were talking about transparency and just like a sign that maybe you need product ops. I think the thing that stuck with me there is just the quality of questions the product team gets from sales, right? 
**Christine Itwaru** (00:44:27):
Yeah. I get a lot of questions around, "I'm investing in this. How do I measure the effectiveness of the team, all of these things?" It's really not easy to measure this in a quantitative measure just yet. Maybe one day, right? Actually, yes. Now one day, I feel like it might be coming sooner than we think. So, what we did was we looked at that transparency problem. We sent out this survey across both product managers and the sales and success teams and we said, "Where's your time going, PMs? How much time are you giving on average to the revenue team to firefight? How much time do you with customers that's quality time."
[NEW_PARAGRAPH]Then on the flip side to the revenue team, how many times do you find yourself asking questions? We gave all of these one to five and blah, blah, blah, those sorts of things, so that we can figure out where to place our energy. We came up with this, "Okay, well, it seems like there's a lack of transparency across the two groups. Let's start with getting data out or information out to the revenue team from the product org." We created this product digest. It's like today and it's matured quite a bit, but I go back to this whole people can know when they're coming, but they need to know what it is they need to do with it. So, this thing was less about this thing's coming next quarter, go tell your customers. 
**Christine Itwaru** (00:45:43):
It's more about here's how you get ready for it, here's how you get jazzed about, and then the handoff, which is probably the question you're going to have at some point, which is, "What's your line between PMM and products?" The handoff is that we don't teach them to sell. We don't teach them to position, but we know that the product intimately enough to help them understand the new value, to help them understand how to use the thing and to make sure that they're hitting the ground. 
**Lenny** (00:46:08):
Let's ask that question. If there's anything more, what is that line between product ops and product marketing? 
**Christine Itwaru** (00:46:13):
Yeah, I always say this and it and it's worked. I haven't seen anybody dispute it yet, but product marketing positions help the revenue team sell their lead gen for all of the outbound and the campaigns that they're running. They are marketing. They're helping you at the end of the day make this thing sound amazing and do the right things with it. For us, it's about educating and it's about helping our internal folks, our internal revenue team understand, "What is the added value? How do you now do this thing? How does this impact your role?" 
**Christine Itwaru** (00:46:48):
We focus a bit on the customer success persona, for example, on Pendo. Customer success managers can go in. They can see their account health and what's going on and blah, blah, blah. How does this impact you as a customer success rep and how do you then help your customers understand the value? Not hey, can you help us upsell this thing and here's how you do it. 
**Lenny** (00:47:06):
Great answer. Makes a lot of sense to me. Final topic, the career path of a product ops person. A lot of people listening to this podcast are either PMs today or I want to be PMs or thinking about becoming product manager, because PM can mean a lot of things. It's interesting, there's this new path that people can explore, product ops. I'm curious who you think might be a fit for the product ops role versus the product manager role. Someone deciding, "Oh, man, maybe I should go down this other route." What do you think are just signs that maybe you'd be a better fit where you enjoy that route better? 
**Christine Itwaru** (00:47:41):
Yeah, I love that question because it makes me feel that this role has become embraced a bit more. What I hear questions like in the past, it was, "Do we need this role and how do we help get the buy-in?" Now it's more the acceptance from a product manager to maybe want to even become this. I'm seeing more PMs, like I said, go into the space. So, it's no longer being seen so much as a threat. It's being seen as this partner. So, just one, I'll say that I think if you're someone like me who absolutely loves and I mentioned the story about the engineers and the team health and stuff, if you love creating that healthy team environment and one where there's cross-functional collaboration and it fuels you to empower the team more, it's a wonderful fit for you. 
**Christine Itwaru** (00:48:22):
Again, I was a PM for years and I felt that pain so much and how much we had to do in order to make this small change and then figure out whether it's valuable. I knew that there had to be a better way to get better outcomes to happen, but I also know that better outcomes don't just mean for the product. It means better outcomes for the entire product team, for the customer experience at large, and ultimately for the business. So, I think that that's one thing. If you're curious and you really want to learn more about that side of the house, one of the beautiful things I saw was one of my products managers fall more in love with understanding the business as she was starting to assure in her product ops career. I thought that was really cool. 
**Christine Itwaru** (00:49:04):
She had already had product background and she was like, "I want to understand the inner workings here so that I know how to help these people." So the other thing is if you're a PM having issues with the role that you're currently in, I think you need to remember that you are there to solve problems. That's a very simple thing that we talked about. What are the things that PMs won't shed and shouldn't shed and that go and talk to customers? We get to talk to customers in order to solve the problems, figure out the right problems to solve. You do that in product ops as well. You don't have to go out to customers externally, but my customers and the people I speak to are internally. They are helping me understand the pain that the product team is tied to. 
**Christine Itwaru** (00:49:47):
So, if you don't love solving problems through building brand new features and building a product, then how can you help contribute to solving other ones? If you're a true problem solver, think about whether you want to do that. So, if you know the pain, what can you do to build a better experience overall? You can ultimately impact your business. 
**Lenny** (00:50:03):
Do you find most product ops people, at least at this point, are former product managers? What would be the pie chart of last job was product manager versus not of existing product ops people? 
**Christine Itwaru** (00:50:13):
I got to put on a new survey. I do. I really have to put on a new survey. Initially, I saw a lot more folks moving in from management consulting, from customer success, from technical success. I haven't seen anyone from sales move in yet, and I have seen a couple PMs. Now, that's the day-to-day product ops manager. I will tell you that the people who are standing up the product ops orgs and being the first product ops hire at the leadership level are former product people. 
**Christine Itwaru** (00:50:45):
I strongly advocate for product ops leaders to have done that role, to have actually had hands-on product experience building and understanding customer problems and feeling that pain, because you very quickly realize where to place your efforts and where your team's efforts should go. That helps you from an efficiency perspective and the business knows you're not just dilly-dallying. 
**Lenny** (00:51:11):
That's really interesting. That makes a lot of sense. Just the roles you named again, where product op people come from. You said customer success. What are the others again?
**Christine Itwaru** (00:51:19):
I have seen technical success. I've seen management consulting. The management consulting piece makes a ton of sense to me. I think there's that data piece that they really like to lean into and advisory, and then the leadership ones coming in from product to leader roles. That's been a happy change too, seeing a director say, "I now want to move into a position to coach the teams and to help build a stronger product team overall. I don't feel like building product." 
**Lenny** (00:51:46):
Fascinating. For someone that's like, "Wow, I want to do this job. This sounds rad," what advice would you give for people to pursue this role and get a gig in product ops? 
**Christine Itwaru** (00:51:58):
Well, one, it's a good thing that there's no shortage of these roles. I would say that there are a lot of these roles open out in the industry. Be intentional about what you want to do, because right now, it's still in a bit of, "Well, what are we doing in product operations as a product management community?" There's no consistency industry to industry, size to size, team to team. It is very different. So, really think about your strengths. Do you love data? Are you a person who thrives on being able to make beauty out of this mess that you're seeing and advise people and help them understand maybe this is a direction that we should be going in? 
**Christine Itwaru** (00:52:40):
Are you technical where you're like, "No, I actually really enjoy doing the quantitative side of things," and you truly enjoy working with data science teams and you really like to bring that data aspect to the product teams? You could probably find a mix of both. There are people who do like doing both of those things. Generally, I mentioned this and I keep saying it, standing up that system because you know that if you had it, you would've been a better PM. 
**Christine Itwaru** (00:53:05):
I think that that's a big thing there. If people realize that there's a better way to do it and they no longer have to do it all but they can do a slice of it in order to drive efficiency for the organization, then start thinking about going out there and doing it. The other thing too is look at those roles and make sure that you fine-tooth comb those job descriptions. Some of them are very vague because they're trying to figure it out on their own as well. So, the more you know what you want to do as a product person, the more you know what to lead out from these roles. 
**Lenny** (00:53:36):
Are there red flags when you're looking at a product job description of, "Hmm, this isn't really the role you want"? 
**Christine Itwaru** (00:53:43):
I think this is a red flag for any role. I mentioned that it's really hard right now to put a number to the success of the role or on the success of the role, but if there's no, "This is how you will be measured or this is what we're looking at as a successful outcome for this person in this role," I would say that's probably a red flag. That's table stakes people need to have on their job descriptions. 
**Lenny** (00:54:06):
Final question. Something I try to get to with people from new companies that I haven't talked to before is just to get a general sense of how the product org is structured at the company. Just because people are always curious, how do you structure product teams? So I guess broadly I'd love to hear just how is the Pendo team product team structured? What are the buckets? Then also, is their product ops person integrated into each cross-functional product team? 
**Christine Itwaru** (00:54:31):
Yeah, I too love to learn about this. We're broken into major areas of the business or revenue streams and we have general managers over those. The GMs actually sit in the product team, which is nice. All have PM background, all really, really experienced and incredible. We also have a head of growth, so there's that component to it as well. Then you've generally got the senior directors. There are teams of product managers who are responsible for different areas in the product. So, we've got one product that's our core product and very mature, broken down into different components there. We have a newer product where that's just one straight product team versus having many different directors. 
**Christine Itwaru** (00:55:06):
We do have a product ops person integrated into these teams. I'd say probably all of them at this point, but the key thing here is they share themselves across two or three teams. Something going through listeners' minds right now is, "Christine, is there a ratio of product ops people to the team?" I would say that at one point, I felt like there might have been and I don't think that's the case anymore. Again, based on my experience and what I'm learning, we operate pretty lean and a lot of people are having to operate very lean right now. So, every few quarters, we look at our goals. We determine who or what goals need a product ops person and for what reason. We're really intentional about it. 
**Christine Itwaru** (00:55:44):
As an example, I use this saying respect the hustle with my team a little bit for the newer product that's still finding its way. The last thing you want to do as a product, which for somebody who I had a legacy product in my last job, one that I was building from the ground up and one that I was just responsible for getting out the door, sun setting at some point, you don't want anyone stifling creativity with any process or some time bound this or anything like that. So, the last thing you want to do is introduce something in there that feels like that you want them to hit the ground running. 
**Christine Itwaru** (00:56:18):
So, we don't over-index on things like a certain planning process or you need to get this to us because the other teams have. We need to know this thing by this timeframe. We'll do what we need to do from there. That's it. We're also quicker with the data. Voice of customer stuff takes a little bit longer for a more mature product team or this is more like, "What are we learning right now and how quickly can we communicate this over to that team so they can iterate really quickly?"
**Lenny** (00:56:47):
Awesome. To come back to the structure just briefly, so you have GMs, business units. Within the business units, you have directors of product that report up to the GM within each and the directors or product have cross-functional product team that they operate that builds specific features and elements of the larger product. Then there's a product ops person supporting some of these teams and they're shared across teams. Got it. 
**Christine Itwaru** (00:57:14):
You've got everybody rolls up to a CPO. CPO's got all of this. 
**Lenny** (00:57:15):
Christine, with that, we've reached our very exciting lightning round. I've got six questions for you. I'm going to just fire them away. Does that sound good? 
**Christine Itwaru** (00:57:23):
Yes, let's do it. 
**Lenny** (00:57:24):
Let's do it. Two or three books that you recommend most to other people.
**Christine Itwaru** (00:57:28):
Classic is Inspired by Marty Cagan. It's one of the reasons I really fell in love with the product. It's inspirational. Leaders Eat Last, Simon Sinek. I really like that book too. That's more leadership style and making sure you putting in your team first, which is something I strongly believe in. This is a plug, but I also really like the book and it's very practical so it falls in that category, which is the Product-Led Organization by our CEO Todd Olsen. Really good book for right now, especially with people really going through this transformation. 
**Christine Itwaru** (00:58:00):
There's an old book that I have that's sitting on that shelf. It's Product Roadmaps Relaunched. It is really old. I mean I don't want to date myself, but it's almost 20 years old when I was in college. But it's really, really valuable and I can reference it just for a quick yeah, I forgot about that from a communication perspective for a roadmap. This is really cool. 
**Lenny** (00:58:21):
Favorite other podcast?
**Christine Itwaru** (00:58:22):
The Product Experience Podcast from Mind the Product. I really like that one. A little bit similar to this other favorite one I'm on right now, but lots of really good product people and just very practical advice too. For leadership, I like HBR IdeaCast. Again, I like to balance the business side and the people side of leaderships.
**Lenny** (00:58:44):
Favorite recent movie or TV show?
**Christine Itwaru** (00:58:46):
Because I have kids, my brain is flooded generally with kid shows. I would say this year, it was between the new Matilda movie, which is based on the Broadway production, which was based on the old Matilda movie, but it's really, really good. Really well done. Then there's this movie. I think it's called Rise. Have you seen it? It's about the Giannis... I cannot say, forgive me, his last name, but he's on the Milwaukee Bucks, basketball player. It's about overcoming adversity and just struggle and really pushing through and giving it your all. I think that one is really good. Add it to your list if you haven't. It's called RISE. TV, I have Food. I don't have a favorite TV show. I've just finished watching White Lotus if that's qualified. 
**Lenny** (00:59:33):
It's the most popular mentioned TV show on this podcast. 
**Christine Itwaru** (00:59:40):
Yeah, I would say for TV in general, you give me anything food. I love cooking. I'll cook an entire massive meal, three course, whatever, sit down, and eat it while I'm watching. Yeah. 
**Lenny** (00:59:53):
Yum. Favorite interview question that you like to ask when you're interviewing people? 
**Christine Itwaru** (00:59:58):
If you could choose any career outside of what you're doing, what would it be and why? 
**Lenny** (01:00:04):
What do you look for in an answer there that tells you that this is a strong candidate versus not? 
**Christine Itwaru** (01:00:08):
There are skills that are a part of that other role that I would lean into. So, if somebody were to ask me that question, I would tell you a chef. It's about experience and it's about constantly refining your craft and it's about constantly looking to delight. I think that speaks to my love for product. It's all about that end state for the customer. So, I always ask that question and I look to see, "What is it? Are they looking for fame? Are they looking for the temporary role?" It's really telling. You dig into the qualities of what makes a good candidate for the other thing. You can figure out a lot. 
**Lenny** (01:00:47):
Fascinating. If they're watching this and learning the secret, that's a good sign too. They're doing the research. 
**Christine Itwaru** (01:00:52):
Yeah.
**Lenny** (01:00:53):
Top five SaaS products that you love, use at work other than Pendo. 
**Christine Itwaru** (01:00:53):
I got to say Pendo.
**Lenny** (01:00:59):
We already know. We already know that's on the list. 
**Christine Itwaru** (01:01:01):
Yeah, I love Miro. I love Miro so much. During the pandemic, this became an essential tool for so many teams. I brought it into our company and I was a big advocate, part of my last one as well, just the collaboration and connection. Figma along the same lines, I think Figma is really great at that for our design team and the rest of products. So, that one's been really good. Seismic is one that I really like as well. That's the content management system for our go-to-market teams. So, it really plays well into how do we make sure we give them what they need and the tool that they need to be in. 
**Christine Itwaru** (01:01:36):
Gong is another one. I think Gong's really great. I've watched them go from the early days and I think we were an early customer or we were using it early on. I think they've pivoted at some point or they've definitely updated messaging on the coaching for their teams and us being able to dig into the qualitative insights that we get on those calls of people is really good too. So, yeah.
**Lenny** (01:02:01):
Great list. Ones that people haven't mentioned before, so that's always fun. Final question, what's something relatively minor that you've changed in Pendo's product development process that has had a tremendous impact on the way that you build product? 
**Christine Itwaru** (01:02:15):
This one's going to sound really elementary or for some people really elementary, but for some people, they're going to be like, "Uh-huh, I totally feel that." Early on, we started bringing in engineers to customer meetings more and more and you don't want to typecast or profile an engineer, but generally, they're not raising their hand and being like, "Yeah, I'm going to come and join, blah, blah, blah." They want to make sure they're doing their job and building the experience, but it's so simple and it's so effective. When we started doing it, the response from the engineering team was great and then also it helped us dig into a different side of the customer while we were on call sometimes. Some of them were flies on the walls. 
**Christine Itwaru** (01:02:52):
Some of them were actually engaging with the engineers and help them increase their confidence in speaking to customers. So, I don't know. I feel like that just ended up changing a lot of the way that we started planning and making sure that their voice had a certain amount of weight or even more weight than it did before in the product development lifecycle. We respect their time. I remember some were very nervous and be like, "Oh, I got to do all this other stuff," but they're like, "Okay, I'll try it." 
**Christine Itwaru** (01:03:21):
Then all of a sudden, they're like, "Whoa, I really want to do this more and more." But it's just really being able to see that pain for them firsthand from a customer or the delight and frustration was very impactful. So, that's my answer and I feel like if you're not doing that as a product manager or product leader, then you better get on that train real fast because it's life changing for the entire team. 
**Lenny** (01:03:42):
That is an awesome answer. This is the first time I've asked this question. I think I'm going to make it a standard question now because I feel like we're going to get all kinds of cool nuggets. So, thank you for starting it off with a bang. Christine, thank you so much for joining me. I learned more about product ops in an hour than I've learned in years and years of reading about it online. 
**Christine Itwaru** (01:04:02):
Thank you. 
**Lenny** (01:04:02):
So, thanks for making the time. Thanks for sharing all your wisdom. Two final questions. Where can folks find you online if they want to reach out, learn more, maybe ask you some questions about product ops and then how can listeners be useful to you? 
**Christine Itwaru** (01:04:13):
They can connect with me on LinkedIn. You'll put that up, I'm sure. Twitter, same. I've got my own site, so the productcraft.com. I started posting on product management products. I'm going to start doing some stuff on careers, all that good stuff. How can they be useful? So don't laugh at me, people. I needed a Twitter reset and so I had that for 13 years and then I no longer did and now I took it. So, just help me rebuild over there and just get back on that site. That's more immediate, but I would say help me understand what's going on in product and product ops. I will continue to do things like this and share more about what I'm learning, but I need to learn more from other people as well. That's an amazing, incredible part of my job that I'm about to do. 
**Christine Itwaru** (01:05:00):
There's just like a lot of pain right now all around us in the tech industry. I think about today and probably the next year or so. For people who are really questioning their next steps in their product careers, whether they stay in it, whether they move into something adjacent or relevant, they're looking to sharpen their skills, maybe make a site pivot to ops, whatever it is. I'm really interested to just gather more data on this and see how it all plays out while also trying to see if I can make some connections. So, I've been able to do that. Full circle back to Ben, Ben did this for me and you. I think that it's really important that the product community is smaller than we think. It's large and it feels expansive, but it's smaller than we think. 
**Christine Itwaru** (01:05:43):
I think we're all facing an interesting time where people may be, again, questioning that next move or struggling. It would just be amazing for us to share. So, cheesy as it may sound, product ops for me was an easy way to be able to connect the dot and be that partner, right? Talk about the transparency and alignment. If there's a way that this community can help empower me to do more of that for all of you, I think that that would be incredibly helpful. 
**Lenny** (01:06:06):
What a beautiful way to end it. Christine, thank you again for being here. 
**Christine Itwaru** (01:06:10):
Thank you. This was so fun. 
**Lenny** (01:06:12):
So much fun. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [12/22] 10 lessons on bootstrapping a $200m business | Patrick Campbell (ProfitWell)

**Patrick Campbell** (00:00:00):
The bratty thing here is that real professional ship. At the end of the day, real... I don't care if you're a marketer or a product person, engineer, ops person, people ops, real professional ship, and they ship at a pretty high frequency for whatever they're doing. In my opinion, your tempo framework is more important than your org design. And so if you've ever had a team that seems really, really smart, but they're always planning or they don't really ship a lot, or you've had trouble where everyone kind of gets it at the leadership level, but then the team below them and below them seems to be kind of going in a different direction, you probably don't have enough alignment and you don't have enough alignment on what good looks like in terms of tempo.

**Audio** (00:00:45):
Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Patrick Campbell. Patrick is the founder and CEO of ProfitWell, which he bootstrapped and sold without any funding for over $200 million. I've been a big fan of ProfitWell and of Patrick for many years. He's one of the most insightful and smartest people that I know, constantly sharing wisdom on Twitter and in his newsletter, primarily on pricing and retention and team building and all of the elements of building a successful SaaS business.

**Patrick Campbell** (00:03:33):
Thanks for having me, man. Good to finally... we've been texting, chatting for years now and I just realized we've never had an actual conversation, so this is where the relationship and the friendship ends because we realize how awkward we are together, I guess.

**Lenny** (00:03:48):
I highly doubt it. I hope that doesn't happen. I've wanted to get you on this podcast ever since I started this podcast. It's always been on my list. You're just generally one of the smartest humans and most amazing humans I know, and so thank you for joining me on this podcast.

**Patrick Campbell** (00:04:02):
We've got to introduce you to more people, but I appreciate that. I appreciate that.

**Lenny** (00:04:07):
You're a humble, humble man. So usually what I do with these podcasts is I have this one main topic that I focus on, but I feel like you're such a renaissance man of a brain that I thought would be more fun to go through 10 different topics and power through them and see your perspective. I feel like you have all these contrarian takes on things and these interesting insights. And so what I want to do is just go through 10 topics and just get a sense of what's a big mistake founders companies make in this area, what's maybe a big opportunity they miss, or just like what's a hot take on this topic. How's that sound?

**Patrick Campbell** (00:04:43):
Yeah, 100%. Let's do it. I'm going to change my Twitter bio to that, renaissance of a brain. That's [inaudible 00:04:50] for me. Yeah, I appreciate that.

**Lenny** (00:04:52):
Yeah, just renaissance [inaudible 00:04:55] that quote. That'd be hilarious. People will be like, "What the hell's he..." Anyway, let's just jump right in. First topic is building your team as a founder or just a leader of any kind. So here's the question, just what are the biggest mistakes people make building their team? What are the biggest opportunities people miss when they're building their team? Or just generally what's like your take on how to best approach building your team as a founder or just a leader of people?

**Patrick Campbell** (00:05:23):
You always have to start answers with cliches, and I think the biggest cliche with building a team is, team is everything, right? If you're listening, you've heard that, you've probably said that to somebody or gotten mentored on that. And I was told that in the early days of building, and I actually thought it was terrible advice. I thought it was going to be the product or marketing or something that was going to hold us back. But I think that although team is everything, and I truly believe that, if you look at most data or most behaviors that most companies make, this isn't actually how we think or what we do.

**Patrick Campbell** (00:05:55):
Let me give you two fundamental issues. I think the first one is we confuse team by being everything to all people to accommodating to every single person, and especially in tech the last couple of years, maybe that's going to change a little bit now, but it was always like, "Oh, everyone needs to be happy." And I think that's a really, really big misconception because you're not there to make everyone happy. You're there for some sort of mission and some sort of goal and you want to set up the culture and the team in a way that gets to that particular goal.

**Patrick Campbell** (00:06:24):
And I think the little bit more actionable way to look at this is, I don't think we actually focus on our team. The average tenure of a manager in tech right now is about 15.7 months. I actually went and looked into this mainly because we got into hyperdrive about team a couple of years ago. The average time a report has the same manager in corporate tech is only about 10.8 months, so just under 11 months. And there's no way that team is everything, or at least we actually believe that when the purveyors of your team, your management only lasts that long, it's just impossible.

**Patrick Campbell** (00:06:57):
And I think for the most part, people ops is an afterthought. And even if you get into the history of HR, which we should not do because that's an entire podcast, it's all about reacting. It came out of the labor movement in the mid 1900s, and it was all about, "Hey, how do we CYA?" rather than, "How do we push our team forward?" And I think in tech we had the opportunity to do that, but we haven't really focused on our team as much. So I don't know if I answered your question, but that's the scope of that problem I think, is we don't actually focus on our team, we don't actually focus on our team in the context of the mission. We just hire people, hope they're really happy. And obviously I'm generalizing, but if you look at the stats and you look at what's happening, that's how it shakes out.

**Lenny** (00:07:38):
Is there something you've done in building your company that has been counter to that, something you've learned about? Because I totally agree, people always talk about team, team, team and then that's often really sucky to work at a lot of companies and clearly they don't care that much about your experience.

**Patrick Campbell** (00:07:52):
So super actionable things that we've done. I think, one, it comes back to the baseline feedback or advice you've probably received, or if you're listening to this before, which is you can't be everything to all people, so who are you for? Who are you for and who are you not for? I think really defining that in your values, and values aren't values unless there's an actual trade-off. And so we had things like optimize for the long-term. There's a clear trade-off when we optimize for the long-term, you probably give up short-term revenue.

**Patrick Campbell** (00:08:22):
You also have different types of people that do better at the particular company than not. One of the more controversial things we did is we talked a lot about behaviors and the one thing that we had is this concept known as the most charitable interpretation. It's not something we made up, but there's this idea that basically when there's conflict or when there's some sort of confrontation, the way that you handle that confrontation was really, really important to us. And the way that we wanted our teams or the people that we wanted to hire for basically would take the most charitable interpretation of that confrontation.

**Patrick Campbell** (00:08:53):
So Lenny, if you were like, "Hey, Patrick, I like your shirt," and I just didn't like when people commented on my shirt, instead of getting pissed off, going to HR, or getting mad at you, what we would do is we'd say, "Hey, the right way at ProfitWell wall to handle that was be like, 'He didn't know, so I'm not going to bring it up,' or 'Hey, Lenny. You probably didn't know, but I don't really like when people comment on my shirt.'"

**Patrick Campbell** (00:09:14):
It seems super trivial, but when you have over 20 people, all of a sudden these things start to come up. And I think most of the time we infantilize our teams where we let them run to HR, we have different policies or all of these different things, when at the end of the day you're paying an exorbitant amount of money for very smart human beings to basically do stuff and you want them basically working together and not having to go in this runaround with policies and people to push things forward.

**Lenny** (00:09:41):
I love that. It reminds me of something at Airbnb where our head of product was always encouraging us to assume good intent from the other person that just like, "What is the good version of what they're trying to achieve? It's unlikely they're trying to cause harm."

**Patrick Campbell** (00:09:54):
But the important part is, and this is where you really care about your team, is if you believe that, and it's okay to have a culture that doesn't believe that, it's not a culture for me, and that's okay, that's the entire point, but if you believe that, then people who have trouble assuming positive intent or who have trouble taking the most charitable interpretation, they can't be at your company, and they have to go and you have to find... And we would have people, and we didn't always defend this and when we started defending it, everything got better. But all of a sudden we would say, "Hey, it seems like this is really tough. This is how we think about things. This is how we handle this type of behavior here. If that's hard for you, let's find you another job." And thankfully we're not digging ditches here, we're all working in tech. And so it's "easy", quote-unquote, enough to find another gig even in economies like now.

**Lenny** (00:10:41):
That reminds me of there's this guy Douglas Atkin, who I worked with for a while who helped us craft the core values at Airbnb, and he made this point that your values need to be clear, exactly like you said, who doesn't fit, who doesn't belong. Because if it's everybody, it's worthless. Integrity, trust, everyone wants that and it fits into that, but it's only valuable if it's clear who's not a fit, exactly how you're saying it.

**Patrick Campbell** (00:11:07):
Well, we get this fear of that accommodation culture, again, where it starts even in the interview process, we're like, "Oh my god, we need these hires, we need these salespeople, we need these engineers." So we don't end up being upfront with these values and these trade-offs in the interview process. And then all of a sudden you spend a lot of time and a lot of money hiring someone who just doesn't fit. And I think that's really, really bad for them, it's really bad for you. And so that was the other thing is we would pull all of this forward into the interview process and talk about it and basically say like, "Hey, if this is not how you think, that's okay. We're not better than you, you're not better than us, it's just this is how we do things here."

**Patrick Campbell** (00:11:42):
And I think a lot of times we're scared to do that because we have that founder, that exact fear of, "Hey, we have to get this thing done and the only way to do that is to do X, Y or Z Z when in reality that's actually going to make your deadline go out further than actually focusing on alignment as much as humanly possible.

**Lenny** (00:12:00):
Next topic, bootstrapping. I feel like you're probably in the bootstrap hall of fame. You built a company-

**Patrick Campbell** (00:12:06):
Here we go. That's all I've ever wanted.

**Lenny** (00:12:09):
I think you're in there. So you tell me if I'm missing anything, but basically you bootstrapped a company, sold it for 200 million. I don't know if I've heard of anything like that. So what's your hot take? What are mistakes people make around bootstrapping?

**Patrick Campbell** (00:12:22):
The basic idea is bootstrapping is for lifestyle businesses that want to cash flow. Funding is for companies trying to create a billion dollars in annual revenue. And that answer offends everybody. That answer offends the indie friends I have, they're going to be like, "Oh, what about Basecamp [inaudible 00:12:43], ProfitWell?" And I'll tell you, ProfitWell, this was a big mistake. Yes, it was a great exit, we sold for over $200 million, et cetera, but we probably, if we had taken money, we could have had a billion-dollar exit or we could have kept going.

**Patrick Campbell** (00:12:56):
And we should have taken money earlier in our life cycle. This was actually a big mistake because we got hooked on the efficiency and that was great, but we could have moved even quicker than we were. And hindsight is 20/20, and I'm obviously not crying over this, but it's one of those things that I think that you have to know who you are and you have to know what your goals are for a company. And our biggest thing was we wanted to build a big company and we were going after that, but we weren't doing the things in order to actually make that happen, which is i.e. getting funded. So yeah, that's my hot take and hopefully I offend everyone. But it's also just the end of the Twitter argument where it's like, "Yeah, it depends," but that's the thing to think about.

**Lenny** (00:13:38):
It's interesting because usually you hear from the other end, someone that raised VC money is like, "I shouldn't have raised money, I should have bootstrapped this thing longer." It's cool to hear from the other side someone that did that like, "No, we maybe should have raised the VC money along the way."

**Patrick Campbell** (00:13:50):
Well, I think there's a lot of ideas that should not raise money. There's a lot of ideas that should just be great cash flowing and they can be large businesses. There's large businesses cash flowing tens of millions of dollars without funding. And I think it's just one of those things that you need your goals, your model, and ultimately your funding situation all to match. And I think a lot of folks, they go in the opposite direction where they're just like, "Oh, everything on TechCrunch, everything on Twitter is like, "Hey, I need to raise money, raise money, raise money." And they don't take a step back and go like, well that idea, it's just not a very good business to get money. And money is so plentiful even now still that it is, quote-unquote, "relatively easy" to raise money on, just not a great idea, and so that's obviously problematic.

**Lenny** (00:14:37):
I've been thinking about writing a post on that exact topic, something like, "Your startup probably is not venture scale," because a lot of people think they could raise money and build a huge business. What's a heuristic that maybe tells a founder that they shouldn't raise money, it's never going to be a billion-dollar company?

**Patrick Campbell** (00:14:53):
I used to look at it 10 years ago you'd say, "Is this a company that can get to 100 million in annual revenue?" And now those numbers are all changed because IPOs are happening closer to 200, 250 million and the markets are all over the place depending on the day. I look at this as if you are going to be that large company, you need to get to a billion in revenue per year. It doesn't have to be overnight, it can be over 20 years, it's not something that has to happen quickly, but that's how I think about it. And if I don't feel like there's a clear path to that, it doesn't mean I don't raise money. It just means that I take a step back and really think about that particular idea because when you get on that treadmill, there's plenty of ideas that will sell for 400 million, 500 million.

**Patrick Campbell** (00:15:38):
But then if you're on the funding treadmill and you look at how much money that founder that exec team ends up getting at the end of it's like you might have been better just building a 50 million cash flowing business that you're getting more money from that and you still have the choice to sell it.

**Patrick Campbell** (00:15:52):
So that's how I think about it. It's a spectrum and it's on the margins there. It's not a fixed rule. But the other thing I also think about when I think about building my next company, we're going to be bootstrapped for, I don't know what... It's not a timeline, but I had imagined probably the first 18 to 24 months because I don't want to give up that equity for that funding on figuring out the idea. Obviously, I had an exit so I'm able to afford that and I'm in a position where I don't have to worry about my own livelihood.

**Patrick Campbell** (00:16:22):
But I think it's one of those things if you can bootstrap, even if you're going after a funded idea, if you can bootstrap for the initial ideation and maybe even through product market fit, which is not an easy thing to do, but that's the ideal time then to raise because then you're just going and you're going for the fences at that point.

**Lenny** (00:16:37):
I really like that very concrete stat you shared and that's exactly how we think about it, that if you don't think you can get to a billion dollars in revenue a year eventually that it probably is not a venture-scale business. And I think that just boils down to how large is the market. If there's not enough people that are going to pay enough money to make this a billion dollar a year in revenue business, you probably shouldn't go down the VC treadmill.

**Patrick Campbell** (00:16:59):
And I think when you think about that, it opens up this world of options for you as someone listening to this. And so think of it this way, you don't have to have the pressure to create a billion dollars in revenue If you can take a step back and be like, "Okay, I can create a $10-million business." You're listening to this and probably you're like, "I don't know." But if you were a director level somewhere at a corporate company or you're leading product somewhere, you can go create a $10-million business. It might not happen overnight, it might take 10 years, all these other things. But that's amazing. That's insane.

**Patrick Campbell** (00:17:33):
Think of 20, 30, 40, 50 years ago, you'd have to have a corner store and you'd have to work 18 hours a day to build that type of ability or that wealth to then hopefully retire when you're 65 and sell the business for 1X. Now you can build a software company that's doing a million a year, have an amazing life, reduce the number of hours if you want, or go all in, make it into a 10 or $100-million company over time. And I think that's amazing and we should celebrate that rather than if it's not a billion, you're failing. But we should just know our limits. I think that's the thing a lot of people fail out with funding.

**Lenny** (00:18:09):
Next topic, pricing. You are probably the most... okay, you're in the top 1% smartest, most experienced people on pricing. We could have done a whole podcast on pricing, maybe we will in the future, but as maybe one of 10 topics, what comes to mind as maybe the biggest mistake people make in pricing, biggest opportunity they miss, biggest hot take?

**Patrick Campbell** (00:18:31):
It's super boring, but the biggest hot take is you just have to do something once a quarter. That's it. I've been trying to teach about pricing for a decade now. I've done a lot of different approaches on this, and I think the easiest thing is, listen, you have three growth levers. You have acquiring customers, monetizing them, and retaining them. You're spending a lot of time and money on acquisition. You're spending some time and money on retention. You're probably do nothing on pricing and monetization and it's because you think it's this nebulous thing and there are some nebulous aspects to it.

**Patrick Campbell** (00:19:06):
But to make it super concrete, it is the revenue per customer. Look at that number, that one KPI, and you want that number going up and to the right, it's obviously going to go to the right over time, but you want it to going up over time every single quarter, not as high as your sales volume or your lead volume or your revenue maybe. But you want that number gradually going up and just do one thing per quarter. The least sexy thing when it comes to pricing is have a pricing committee. If it's a two-person company, it's you and your co-founder. If it's a 100,000-person company, it might be 30 people, but really it's only eight people central to that particular product.

**Patrick Campbell** (00:19:42):
And then just realize there's a lot of things that influence that revenue per customer. There's the actual price, your packaging, your add-on strategy, your discount strategy, your price localization, freemium. There's a whole host of different things there, but just find one thing you're going to do every three months, put a calendar invite, let it renew every three months. You're going to snooze it a couple of times, I get it, I've seen this many, many times before. But just do something, even if it's super small. I guarantee you it's just like any other thing you measure, as soon as you start measuring and caring about it, you're going to start to do some stuff, some of it is going to go poorly, some of it is going to go great. Then you're going to do more stuff, and then just over time, all of a sudden that number's going to go up into the right. But just do something. That's the basic idea.

**Lenny** (00:20:24):
I love the simplicity of that. If I think about the pie chart of the things you will do and may change, you mentioned a few. One is raise prices. One may be lower prices. One's probably change your pricing model. There's a couple more. I guess, in your experience, where have you found the biggest opportunities end up being maybe early in the early phase of a startup in that pie chart?

**Patrick Campbell** (00:20:47):
The number one thing to figure out when you're thinking about the different pricing pieces, pound for pound, it's the pricing metric or the value metric. That's how you charge per user, per thousand visits, per thousand what's its, whatever it is. Consumer companies, it's a little bit harder. Physical good products, it's really hard obviously because you have that physical good, the physics you can't get over. But the reason this is so powerful is because if you get everything else in your pricing wrong or not great, but you get that right, you tend to be okay when it comes to monetization.

**Patrick Campbell** (00:21:21):
And the reason is because, first, from an acquisition standpoint like acquiring customers, you end up making sure that you get Disney coming into your product, they're paying Disney prices, and then you get Johnny or Jane's startup coming in and they're paying Johnny and Jane prices. You don't want them paying the same thing because obviously the value's different, even if they're consuming almost the same amount. So this allows you to figure that line out.

**Patrick Campbell** (00:21:44):
And then what's really beautiful about it is churn tends to be about 20 to 25% lower because people will downgrade, but they're using... you don't get this like, "I'm paying for so much and end up not using a lot of it." It's like, "Oh, I'm using eight seats this month, I'm going to downgrade," or it's just automatic. And then your expansion revenue's typically double when you're using a particular value metric because instead of me having to resell you and being like, "Hey, Lenny, there's this really cool feature in this upper tier, do you want this?" And you're like, "I already use the product, I don't really want this." Instead, I just go, "Hey, Lenny, congratulations. You now have 100 videos in your account. That's awesome. You guys must be growing. I'm just going to bump you up to the 100-video plan. Let me know if you have any questions." It's just a very, very implicit way to get expansion revenue. So that's the thing pound for pound that's the best.

**Patrick Campbell** (00:22:30):
And then I would say if you have a lot of politics internally, which everyone does with pricing because it sits in the center of so many different teams, I would actually start with a price increase. You should be increasing your overall price once per year if you're building. If you're not building and your support sucks and your NPS is low, then don't worry about it. But if your NPS is over 20, which is not a very high NPS, you should raise your prices once per year. The reason I suggest that is because it gets all of the BS and all the politics on the mat. You're going to have to collect some data, you're going to have to prove it to sales, you're going to have to make sure you have the enablement, you're going to have to make sure your messaging is...

**Patrick Campbell** (00:23:06):
But it's a tight enough non-nebulous thing that you're doing versus a value metric where you can have a bunch of debates about this metric or that metric, and should you give 10 away versus 100 away. It's a good way to rip the bandaid off. And most companies don't change their actual number that they're charging once per every three years. So if you haven't done it for three years, you're overdue for it. So it's a good one to kind of rip the bandaid off.

**Lenny** (00:23:30):
So this episode already pound for pound I think is up there. This is amazing. I'm excited to get to the next topic, but first I'll plug. You wrote a guest post in my newsletter about pricing and we'll link to that in the show notes, and that goes deeper into this value metric and how to think about pricing. So check that out.

**Lenny** (00:23:46):
Next topic, retention. So when I think Patrick Campbell, I think pricing and retention. So again, this could be its own podcast episode, but let's just pick one thing to talk about. What are the biggest mistakes people make, retention opportunities, or just hot take?

**Patrick Campbell** (00:24:00):
The reason I started writing about retention and publishing data on it is because I didn't want to be the pricing guy. I was trying to basically differentiate myself and then I was trying to be the SaaS guy, but that's too broad. But anyway, so retention, the hottest of hottest takes, and this is the one to offend 90% of the list... no, it's not going to offend, but this is a product podcast, that's how I think about it. Product homies. You fail at realizing most of the time that there are two types of retention. There is strategic retention and then there's tactical retention.

**Patrick Campbell** (00:24:38):
Strategic retention is all the stuff that you as a great product leader, a great product team are doing. Your ICPs, your time to value, road mapping, the right features, figuring out your mission metric, agonizing over every little thing, all the paper cuts of being a great product leader. But because you're so focused and so biased towards that, you miss out typically on this thing we call tactical retention, and these are things like payment failures, term optimization, cancellation flows, offboarding, et cetera. And if you're past product market fit this area, this tactical retention, it's typically about 25 to 40% of your churn problem, which is a significant amount, but you don't really look at it because again, you're like, "I've got to go focus on features, I've got to do this, and I'm going to go be this great product leader."

**Patrick Campbell** (00:25:26):
And so because product is so entrenched in that thinking that that problem can be solved with two months of work, it's not that much work putting in, basically, a marketing funnel when people's credit cards fail. Not that hard, not rocket science. Doing offboarding, being really smart with offboarding. And one little tidbit. I looked at two million cancellation flows. We built some products for this, that's why I have this data, just to be clear. But looked at two million cancellation flows and we found you have about 18 to 30 seconds when someone hits that cancel button, we found you should ask two questions. One, "Why are you leaving?" Multiple choice. Don't do the free response. You get one out of 100 great responses, and the 99 are not great.

**Patrick Campbell** (00:26:08):
And then the other question we found works really, really well is, "What did you like about the product?" And the reason that works so effectively is because that person's on a freight train to basically cancel. They're like, "I'm already done. Oh yeah, this is why I'm leaving." The minute you ask them what they like, you're basically tapping into this nostalgia effect and you're stopping that freight train. And then when I have that information, it's great for a product team, it's great to figure out, "What's working, what's not? What should we do more of? Was this a good customer?"

**Patrick Campbell** (00:26:34):
But then based on their engagement data, their plan, whatever, all their firmographics about them plus their answers, then I can offer up a salvage offer or a pause plan or a maintenance plan or these types of things. But all this type of stuff, this is really, really powerful. And I always suggest finance teams should just take this on because product teams are always going to be thinking so much more on the future rather than fixing this right now. But that's the hottest take I've got for retention.

**Lenny** (00:27:00):
That's a great, awesome take. And I want to plug ProfitWell right here, actually. I know you guys offer a product that does this and I've used it. So I don't know if that's still true, I know after an acquisition, things change. So I use ProfitWell for my newsletters. I just plug it into my Stripe account and it's the most amazing free product because it just tells me everything I want to know. And then it's got this cool feature, you just turn it on and it does these things for you like it tells people, "Your credit card is about to expire." Hey, this card failed, you should try putting in a new card." So that's a cool reason to check out ProfitWell.

**Patrick Campbell** (00:27:29):
Thanks, man. I appreciate that. And it's actually cool because I think for us, because the fact that product teams don't really think about this stuff, we stumbled into this whole thesis that could be a whole episode, which is all the product features are done for you. So what I mean by that is, you noticed this, but when you log in and set this up, you're not writing emails, you're not setting up the flows. And the reason is because we have all this data from $30 billion in ARR flowing through our metrics product that we can study and understand what works and what doesn't.

**Patrick Campbell** (00:28:02):
And that kind of stumbling that is useful for folks is what we discovered is this anti-active usage type product, it retains itself at a really, really high rate because people are just getting the value and they don't have to use it. And so what we found is a little bonus thing on retention. When we look at churn rates across different types of products, those products that are workflow products you use every single day or mostly every single day, or those products you don't have to log into but you still get the value, that's where the lowest churn rates are, the highest retention. Anything in the middle, it's like death. And this is why ProfitWell metrics ended up being free because we were just like, "It's terrible to build a metrics and analytics product. It's so hard because people just don't appreciate how much work goes into it, therefore they don't retain at a high rate, they're not willing to pay that much," et cetera.

**Lenny** (00:28:49):
I think that alone is a really interesting story, and I don't know if we should get too deep, but just to highlight what you just said, so many startups build an analytics product that it's just a better way to measure and track all the stuff that's going on. And what you've found is you won't make money doing that, people don't want to pay for a SaaS analytics tool.

**Patrick Campbell** (00:29:08):
You have two options. You go up market and you pretty much become a data product with a UI or you go super niche. And even super niche, it's super hard and it's just because, I don't know, everyone's trying to kill a spreadsheet, and it's like, "You're not going to kill a spreadsheet." All real analysts will do everything in a spreadsheet. So for us it was we want to give you a clean UI and then we want to help you get this data into spreadsheets or email or whatever you're using for your databases, things like that.

**Lenny** (00:29:38):
Yeah. I don't want to make this an ad for ProfitWell, but it's like founders come to me with pitches of, "Hey, we've built this sweet analytics." So I'm like, "Just look up what ProfitWell is giving away for free, that's going to be a high bar to exceed."

**Patrick Campbell** (00:29:49):
Yeah. Yeah. We were going to try to sell it. We were trying to sell it in the beginning, but what ended up happening is we ran into all this, that's why we didn't.

**Lenny** (00:29:56):
All right, back on track. Topic number five, shipping. What have you learned about shipping? What are mistakes people make when trying to ship faster, ship more efficiently?

**Patrick Campbell** (00:30:05):
Yeah. The bratty thing here is that real professional ship. At the end of the day, real... I don't care what if you're a marketer or product person, engineer, ops person, people ops, real professional ship, and they ship it a pretty high frequency for whatever they're doing. And so the thing that we thought a lot about is, in my opinion, your tempo framework, and I'll explain a little bit more of what that means in a second, is more important than your org design. And so if you've ever had a team that seems really, really smart, but they're always planning or they don't really ship a lot, or you've had trouble where everyone gets it at the leadership level, but then the team below them and below them seems to be kind of going in a different direction, you probably don't have enough alignment and you don't have enough alignment on what good looks like in terms of tempo.

**Patrick Campbell** (00:30:56):
And so the way we looked at this was we have to establish mission metric and guiding principles at the top so, what do we do? How are we measuring it? And how we're going to get there? So for us was we automate subscription growth. Our mission metric was the amount of revenue that was on ProfitWell because that was good from acquisition, but it also meant we were doing our jobs. Then how we're going to get there. We want to be the most helpful brand in SaaS. And then we also we're going to do it for you, this whole thing that I just talked about.

**Patrick Campbell** (00:31:25):
Then what we did is we established that at the leadership level, every org leader, so marketing, sales, et cetera, they need a framework that fits into that overall. So marketing at ProfitWell was this whole inbound media, so lots of podcast, video series, et cetera. And the most important part of that was they needed to determine what good looked like in terms of shipping. So if we're like, "Hey, we're doing sales," blah, blah, blah, blah, blah, or marketing in this case, "this many episodes per month, it's this many product launches per month, this many big product launches per quarter," whatever it is.

**Patrick Campbell** (00:31:57):
And then your leadership is basically a conversation of, "Great, that's what good looks like, we agree. How do we close that gap?" And then all of those conversations are like, "Okay, you only shipped one thing per quarter, we want to do one per month. Why?"

**Patrick Campbell** (00:32:10):
"Well, I don't have enough resources."

**Patrick Campbell** (00:32:12):
We solve that problem or we figure out how to get the more resources, then they're not doing it again. "Okay, why?"

**Patrick Campbell** (00:32:17):
"Well, there's this problem."

**Patrick Campbell** (00:32:18):
And then all of a sudden you start to create this very high output team across the board, and you also have this alignment so you don't wake up nine months into someone being at your company and being like, "Well, I think Tim sucks."

**Patrick Campbell** (00:32:30):
And it's like, "Well, why did you just all of a sudden wake up and think Tim sucks."

**Patrick Campbell** (00:32:34):
"Well, he's not shipping blah, blah, blah, blah."

**Patrick Campbell** (00:32:35):
"Well, it's probably an org problem rather than a Tim problem," because again, you vetted Tim. Tim was at this other company and apparently was a really great rockstar. So what's the difference here? You screwed up the hiring? Well, maybe because that is really, really hard, but most of the time you just haven't set an expectation of what good looks like in terms of tempo, and then you haven't had that constant conversation to make sure that Tim has what he needs in order to ship.

**Lenny** (00:33:00):
What was a big learning, I guess, in doing that? Is that just something you built up over time of we need to create this tempo at ProfitWell?

**Patrick Campbell** (00:33:05):
Yeah. Complete misalignment if you don't call it out on what good looks like, just complete misalignment. Like so-and-so is going and building, they think one product launch per quarter. Or I'm sitting there and I'm like, "Well, we should have a medium one per month and then we should have a big one per quarter." Complete misalignment. And if you don't have a way to talk about that, some sort of nexus to have that conversation, you end up not having it, and then you end up creating this friction and resentment on both sides because everyone thinks, again, "Tim isn't doing well." And it's like, "That's not what's happening. It's just the expectations aren't set."

**Patrick Campbell** (00:33:40):
And then what was really cool is that you start to find out that the why they aren't hitting what good looks like is all solvable, and most of the time it's this team isn't talking to this team. "Oh, great. Well, marketing wants to do these launches, product isn't providing them stuff. All right, let's get these two people together, have this conversation because we didn't have product marketing or official product marketing." They have this conversation and then all of a sudden it's like, "All right, Neil, you need to provide one thing a month. There's so much stuff we've built, a lot of it we haven't announced, you just need to provide one thing a month. Marketing will worry about how to position it in a way that isn't too far, isn't overselling it, but also gets us something per month, and you can approve that positioning." And then all of a sudden you start getting this tempo going, which obviously is the goal.

**Lenny** (00:34:27):
Reminds me, David Sacks has this awesome post called The Cadence around how marketing and product and sales should operate and create this kind of cadence. So being aligned but also offset schedule, which will link to them in the show notes if you haven't seen it.

**Patrick Campbell** (00:34:41):
Yeah, that's great.

**Lenny** (00:34:42):
Next topic. First principles thinking. As a renaissance man of a brain, I feel like you've spent a lot of time thinking about from first principles and in our conversations you always have really interesting approaches to things. What have you learned about actually implementing first principle thinking, which people are always talking about. How do I [inaudible 00:35:00] first principle?

**Patrick Campbell** (00:35:01):
Yeah, people always talk about it. And there are no good courses that I have found on first principles thinking. There are good blog posts, but the good blog posts kind of explain what it is, and then that's it. It's like, "This is what it is, and here's an example." And most of them quote Elon Musk about rockets and breaking down the different parts. So what I kind of found is there's the five whys, which I think someone's talked before or at least I've read it in the newsletter before, which is just you keep asking why. Kind of, "Well, this is this way."

**Patrick Campbell** (00:35:36):
"Well, why is that?"

**Patrick Campbell** (00:35:36):
"Well, this is this way."

**Patrick Campbell** (00:35:37):
"Why is that?"

**Patrick Campbell** (00:35:38):
I found the model that people who aren't great at first principal thinking or aren't great at talking about it that kind of helps them unlock is this thing called problem, cause, solution. So I learned this in debate in college and high school, and it basically is you have a problem that you're trying to solve. Well, you can't actually solve a problem. So if we talk about world hunger, you can't just solve world hunger because it's kind of the symptom, it's this problem that exists.

**Patrick Campbell** (00:36:06):
Well then I want to break down what are all the causes of world hunger? And it's a little more brainstormy when you have these conversations with folks, especially again when they struggle with this. And all of a sudden I could list out all the causes, irrigation crisis, aid not getting to where it needs to be, famines, drought, et cetera. And then what I can do is I can rank those causes in terms of magnitude. So if we're trying to solve world hunger, and for some reason we discovered irrigation was the biggest problem, if we solved irrigation, everything would be great, well then I'm going to align my solutions to all of those different causes. And you get this nice alignment between, well, I can solve a cause, and if I solve the cause that's big enough and proper enough, I'm going to eventually solve the actual problem or mitigate the problem, I should say.

**Patrick Campbell** (00:36:50):
So that's the framework that I found really, really useful. And also, it's great for using for presentations, it's great for a mission, it's great for all of these different things because it's a little bit more actionable than just the five whys, which is more of a way to have a conversation.

**Lenny** (00:37:06):
So the way you operationalize this, say problem, cause, solution. You're saying on strategy templates, you write out, "Here's the problem we're trying to solve, here's the source of the issue, and then here's how we're approaching it." Can you talk a bit more about how you implement this at your company and the people you work with?

**Patrick Campbell** (00:37:22):
Yeah, totally. So I'll say big, medium and small things, and I'll try to be really quick. So big things it's like, "What are we facing?"

**Patrick Campbell** (00:37:30):
"Oh, we're going to try to charge for this metrics product. Now there's a bunch of competitors. The customers don't really care about it."

**Patrick Campbell** (00:37:37):
So we have this problem and the problem is growth. How do we grow a product like this? How do we grow our company? And what's really interesting about a big problem or a nebulous problem like that is you end up having a lot of conversations about the problem, which I think is more useful sometimes about, "Well, what are we actually trying to do? Let's get alignment as much as possible." And then it's like, "Okay. Well, what are the causes of our growth problem?"

**Patrick Campbell** (00:38:00):
"Well, people aren't willing to pay for metrics. Getting accuracy is really, really hard. Actually, the market stance," all these other things.

**Patrick Campbell** (00:38:08):
"Well, what are some of the solutions?"

**Patrick Campbell** (00:38:10):
"Well, we could do this, could do this, could do this."

**Patrick Campbell** (00:38:12):
And normally what ends up happening is the solution ends up being kind of an approach. So our approach that mitigated or solved for some of these causes and mitigate the problem was freemium, and then these paid products that were all pay-for-performance because with pay-for-performance, you could charge a significant amount more in a market that only has 100,000 logos, which is a really small market. And so that kind of an example there.

**Patrick Campbell** (00:38:37):
Medium and small, let's talk about a support ticket. This person's pissed off. They're coming in, they're pissed off. What are the causes? Well, there's a lot of different causes that were probably like, "Oh, we didn't get back to them in time, and then we gave a crappy solution, we gave this..." It just kind of allows us to look at the problem. And so it's more of a way of thinking on that level. And it's not happening. We're not going to have an hour-long conversation about a support ticket. But the support folks that I've talked to about this, they go, "Okay, cool. Why is he upset?"

**Patrick Campbell** (00:39:06):
"Well, we didn't get the answer in time."

**Patrick Campbell** (00:39:08):
Okay, my first line is going to be, "I understand we didn't get you an answer quick enough. Apologies for that." It just allows them to have a little bit of an extra second to think through things and move forward with that.

**Lenny** (00:39:21):
I love that. I love that big example and a small example.

**Audio** (00:39:26):
**Patrick Campbell** (00:40:27):
I think I have the 85-year-old curmudgeonly man perspective on customer research. So here's the thing. Everything in your business, it does not matter what type of business you have, everything is used to drive someone to a point of conversion or justify the product or the price that you're offering up. That customer is a human being you're driving to that point of conversion and it's your job to understand how they perceive you, how they perceive their problem, how they perceive the world around them, around your products.

**Patrick Campbell** (00:41:00):
We all know this on a philosophical level, but here are some fun facts. So one, only one in five companies have buyer personas or ICPs, only one in five. So we talk about this all the time, we retweet the articles, we give the advice, so many of us give the advice. But then we look at our own companies, only one in five have some sort of segmentation ICPs. And then only one out of 10 companies actually do customer research or development on a quarterly basis. This should be a continuous thing, it should be a monthly, weekly type thing. Not saying you're sending up surveys or having all these conversations on a weekly basis, but only one out of 10 are doing quarterly. So that means the number they're doing monthly is even smaller than that. And I just think that's insane.

**Patrick Campbell** (00:41:44):
And when we look at all data, and we have a lot of data on this, and this is something where I've been talking about customer development for a long time. Everything is better. Everything is better. NPS is higher for organizations that have customer development functions or even just ICPs or buyer personas, depending on what framework you're using. Willingness to pay is typically higher. The funnel is more efficient. LTV to CAC is normally much, much higher. All those growth numbers, you're typically growing in a much higher rate, like a 15, 20%, not a small delta, 15-20% higher rate. Retention's better. All these things are better.

And the thing that, I think, 20 years ago or 10 years ago you didn't have to do customer development because, and this is where Keith [inaudible 00:42:30] is just like customer research is dumb or whatever his famous quote is, but you didn't have to do it because there just wasn't a lot of stuff out there and we all were riding the wave of the internet. But now the market's harder and harder. So what are you going to do? Are you just going to keep throwing stuff up against the wall or are you going to actually do the stuff that all of us talk about doing and actually do the research? And the research is hard. It's never going to be 100% accurate because you're going to have to use your judgment, but that's your job.

**Patrick Campbell** (00:42:54):
And so that's more of a rant, I guess, than a hot take. But I also think this is one of those things that AI starts solving, especially all this generative AI because now you can just throw all that stuff into a workload and then all of a sudden you'll get back a lot of the sentiment or all that kind stuff so you don't even to do the hard part anymore. Yeah, that's my rant.

**Lenny** (00:43:14):
Love the rant. Maybe one follow-up question. Why do you think it is that companies don't do this? I love the point you made of the retweeting, "Yeah, research is great." Writing blogs that research is use useful, "We've got to do research." Why do you think companies don't do it? And then what's one thing that maybe they could do tomorrow that'll bring them closer down that path?

**Patrick Campbell** (00:43:35):
The one thing you can do, put a number on a whiteboard. You're going to have 10 customer conversations a month, just 10 non-sales conversations. You're just going to talk to 10 people. Or you're going to send one survey. And people are terrible at sending surveys. Surveys are actually great. You just have to be good at sending them. And good, it's not a high bar, it just means that you have 30 to 45 seconds of someone's time unless you're compensating them. And don't send 45-question surveys by email where the first question is, "What's your email?" Don't do that. But just put a number on the board.

**Patrick Campbell** (00:44:09):
I think the reason we don't do it is because it was, quote-unquote, "easy" to get away with not doing it. If you really think about a funded environment... and some products are so paradigm-shifting that the biggest misconception about customer research is I have to listen to them. You don't have to listen to them at all, you just have to understand where they are, and then you're filtering all of that with all this other data and then you're making a decision and you're earning your paycheck as a product person. Typically, it's the product person, but also in marketing.

**Patrick Campbell** (00:44:37):
So I think it's just one of those things where you could get away with not doing it. Now though, the way the market's going, you're just starting to see this more and more, you're starting to see more tooling. The reason you're seeing more tooling is because they're starting to connect it to actually being useful rather than you having to set up your own customer development program. I think the other reason typically people haven't had to do this is because there's a lot of brute forcing that's done in startup land and it only lasts so long.

**Patrick Campbell** (00:45:06):
So all of these companies that raise a bunch of money, get the $100 million dollar exit, everyone's clapping because it's a big number, but cap table screwed, everything's bad. It's a win because it's a win, but all of those companies are ones who were able to brute force to a certain level and they never learned how to actually understand their market or their customer. And I think that that kind of story will continue to happen as long as we have a lot of capital flowing in the market. But I would rather not be that company. I would rather be the company that gets the $100 million, 200 million exit with bootstrapping, or builds the billion-dollar annual revenue company because I know my market, I know my customer so well.

**Lenny** (00:45:47):
Talking to customers is good, you should do it. Great reminder. People are going to listen to this like, "Yes, we should do this," and then we'll just move on. And then-

**Patrick Campbell** (00:45:55):
My joke when I give talks is, "Only 20% of you are going to do this when I give a talk on it, and so I'm not even going to talk deeply on it. You 20%, come talk to me, I've got a whole framework for you," that type of a thing because I think people just nod their heads and they tweet it, and they just don't end up doing it.

**Lenny** (00:46:10):
Status quo is hard to overcome sometimes. We're onto our eighth topic, we've got three to go, and it's on competitive intelligence. And this touches on a really interesting part of your background that I don't know a lot of people know.

**Patrick Campbell** (00:46:24):
Yeah. So my background, I started my career... I worked in US Intelligence, I worked for NSA. And I was just a entry level intel analyst, basically, I was only there for just over a year. And what was interesting is you get taught first principles thinking in so many different ways because you're solving essentially puzzles every day. Now those puzzles are finding a bad guy or a gal or finding this piece of information. Those are all the puzzles, but you have to think through how to figure this out. And a lot of those puzzles involve, "You have these number of entities, how are they going to react?" And you're trying to predict how they're going to react, and you're also trying to help figure out how you're going to react or act in the context of them, so like node analysis, basically.

**Patrick Campbell** (00:47:09):
And what's interesting from a startup or a business perspective is I think that don't focus on your competitors is terrible advice. It's amazing advice for product teams. When you have a competitive intelligence program or you have competitive intel, I try never to share that with product ever because products should just focus on the customer, they should not give two craps what's going on with competitor A or competitor B. But as an overall missive, don't focus on your competitors is terrible advice. And if I'm being charitable, it's just outdated because some fun facts, and I alluded to some of them before, over the past decade, if you're building in tech, particularly in SaaS or subscriptions, you now have 16 times the number of competitors if you started a business today, than if you did 10 years ago, and this is because everyone and their mother can spin up a website, a server, they can drive traffic to that site.

**Patrick Campbell** (00:48:02):
So there's just a bunch of stuff in the market. And then because of all that stuff, all these marketing channels are getting denser and denser. CAC and B2B is up about 110% over the past 10 years. Consumer, it's up 145%. If you're selling sales and marketing software, it's up 220% because there's just so much sales and marketing software doing sales and marketing things in the market. And so the other reason for this is we haven't had a brand new marketing channel since 2015, and that was Snapchat. We have TikTok, but TBD, depending on how you think about it. But we're going from brand new marketing and advertising innovation every quarter to basically every five years.

**Patrick Campbell** (00:48:42):
My point is, if you are not in a Blue Ocean, you're not in the Peter Teal, go to a market of one, you're not in those types of things, which is most of us, and even some of us who think we're in those things, we're actually not, you do have to focus on your competitors on some level. And the levels I particularly think are a bare minimum, just knowing who they are, having a strategy. So for ProfitWell we never had comparison pages because we very quickly went from a challenger in this very competitive market to the leader in the market. So all of a sudden we were going to be above the fray, that was the idea, that was the strategy that we had, which is, "We're going to have a lot of intel on what's going on with them, why people care about this product." We had white label NPS surveys and customer development surveys going to our competitors' customers. That's the level. And it was just automated. It wasn't like it was taking a lot of time, but we just wanted that intel.

**Lenny** (00:49:34):
When you say white labeled, that means you're emailing your competitor's customers to see what they think of your competitors, right?

**Patrick Campbell** (00:49:41):
Exactly. So we're basically, and we did it as a third party basically, which was, I think one of them was analyticssoftware.com, stuff like that. So it wasn't like we were spoofing as our competitor because I think that crosses a little bit of a line. But basically we would have this intel. There's a whole program here. Basically, I'd have sources... Basically, these customers I knew were always going to stay because they liked the founder or something like that. I would get on the phone with them every quarter or two just to be like, "Hey, what are you liking? Why haven't you switched yet?" these types of things, or I'd see them at conferences.

**Patrick Campbell** (00:50:14):
So there's a whole program there. And again, it's not like it's distracting anything, it's just I want the intel so I can predict what's going on, I can predict who to care about, who not to care about. But even then, if you're a challenger, competitor marketing pages are really powerful. And the thing is, your customers, especially in a denser market, they know your competitors exist or they're looking at them. Don't infantilize your customers, help them, "Hey, this is how we compare to X, Y, Z competitor," and be honest as much as possible. Well, we should always be honest, but be as upfront as possible, I should say, with where you're bad at and where you're great at, those types of things.

**Patrick Campbell** (00:50:55):
But long story short, having something awareness and then choosing a particular strategy, and then depending on your strategy, you might ramp up how much you actually do with the actual intelligence program.

**Lenny** (00:51:06):
This is amazing. Two questions. Should every startup have a former spy on their team to help them operationalize these ideas? And then two, is there anything else that you found super valuable that you did based on your training there?

**Patrick Campbell** (00:51:20):
We didn't have a formal program, but I love hiring veterans, either veterans of intelligence, so they're citizens, so they're not veterans from a military perspective, but people who had worked in Intel or people who were actual veterans of different military branches. There's a lot of reasons for this, but I think that the intelligence folks, it's a way of thinking. Now you ought to be careful, and this is just purely my opinion, because depending on how long they were in... the reason I left is because it's the government, it's super bureaucratic. It was one of the most fulfilling jobs I will ever have, and I was only there for a short amount of time. But it's just one of those things where it's just so bureaucratic.

**Patrick Campbell** (00:52:01):
So the 15-year person there is not thriving, they're not trying to change the world necessarily. They have a job. So you've got to be careful with that. But yeah, I think there's these really smart people that just think in a different way. And a broader point is I think it's just really, really good to go to different industries. All this customer development stuff, you go to any major retailer or any major e-commerce company, they have entire teams just dedicated to this stuff. Hallmark was one of our first pricing customers back in the day before we went subscription focused. They had 119 people in customer insights and research. And this was one of the reason we were like, "Well, you guys don't need our help, you've got enough people." But those are great people to hire, even though they don't necessarily have the actual industry knowledge, they have a lot of domain expertise.

**Patrick Campbell** (00:52:50):
In terms of things I learned, I'll put it this way, not to get political, if I was in charge of budget, I would give so much more money into the intel community. I saw conflicts or heard about conflicts being stopped just because of intelligence that didn't go hot in terms of war fighting. I think it's one of those things where I would put so much more money there than the actual other side of the defense budget.

**Patrick Campbell** (00:53:12):
And also everyone asks me about Snowden. So again, not to get political, it's a lot more complicated, I think, than a lot of people think. It's one of those things that the issues that were brought up, obviously they got really sensationalized, but they're really important conversations to have, but it's not as simple as, "Oh, stop doing this, start doing that."

**Patrick Campbell** (00:53:33):
You don't have to worry about the NSA, the NSA's all outward-looking. You should worry about the FBI. The FBI are the ones who get a little testy with certain things, and you're seeing that in the court cases and stuff like that. But just know there's a lot of really hardworking, very well-intentioned people who you might disagree in terms of trade-offs, in terms of safety and things like that. They're also some of the most privacy orientated people on the planet, so that's worth a whole conversation. So hopefully I didn't throw too many grenades in this part.

**Lenny** (00:54:02):
No, we need more grenades. That's the first time Snowden was brought up on this podcast, so that's cool. There you go. And this is actually a good segue to the next topic, which is around local strategies like FBI versus NSA. I think you have a strong perspective that local strategies are much more likely to [inaudible 00:54:19] so we'll just get into that one.

**Patrick Campbell** (00:54:21):
Yeah, yeah. Just to give you a tease, I'll tell you what I think of Snowden after the podcast. So the world doesn't get to know except that I'll tell you what my opinion is afterwards.

**Lenny** (00:54:30):
What a tease.

**Patrick Campbell** (00:54:31):
Local strategies. Local strategies, very basic. People like to buy from people, but we as operators get so excited about the scale of the internet that we forget the basics of humanity. Here's some fun data points, we did a bunch of studies on this. So prospects who meet you in person, and this is not just for profit, all the data I've shared, it's all global-level data or segmented depending on how we did it. It's not just our findings, it's like we looked at probably a minimum of 2,000 companies per factoid and most of the time much more. But prospects who meet you in person have 10 to 30% higher willingness to pay than those who didn't. Churn for those folks who you meet in person is typically 20% lower than those folks who have never met you. Expansion revenue is typically 15 to 20% higher.

**Patrick Campbell** (00:55:23):
And this is not only in hand-to-hand kind of sales, coffee meetings, lunches, lunch and learns this type of thing, but it's also in scaled products, so products that cost 20, 50 bucks per month. And so my suggestion is to you, especially in a post-COVID, I don't know if that's the right term, but in a world that hopefully does not see another pandemic in our lifetimes, knock on wood, do meetups, do lunches, go to conferences, unless you're Lenny who is not a big fan of conferences. But get out of the office. Make sure you get out of the office. And the budget doesn't have to be as big as you think. Breakfast and lunches are super cheap. We would push all of our P2 and P3s to a meetup, and all of our P1s, we would have one-on-one coffee dates. It's super cheap.

**Lenny** (00:56:08):
What do the Ps mean? Is that priority?

**Patrick Campbell** (00:56:10):
Priority 1, we want these people to convert, they're very good fits, all this other stuff. P2s are like, they're probably good fits, but they're just not as big. And then P3s are with a content play, they just love our content and stuff, but they're not necessarily good fits for us. And so people make the mistake, they push everyone to dinners and it's like, I don't want to spend all of my money on P2s and P3s.

**Patrick Campbell** (00:56:34):
And so breakfast and lunches are cheaper than dinners. Meetups can be extremely inexpensive, get creative. We like to do barbecue type stuff for, not dive bars, but the unique dive bar, I guess is the best way to put it. So it's not fancy. People just want to meet people, they want to talk to you, especially if you're doing content and things like that. The Lenny Newsletter, Lenny Empire Meetups, I see the pictures of those all the time. There's just an urge to learn from one another and hang out. So yeah, that's the biggest thing, get out of the office or get out of your desk at home.

**Lenny** (00:57:07):
Yeah, that's right. You're on Zoom. And you're saying it's not just the founders, it could be anyone on the team, salespeople, that all works.

**Patrick Campbell** (00:57:14):
Anyone. I led marketing as part of my role as CEO, and so I do a lot of this and I'm also the one doing a lot of the content and stuff like that, or the face of a lot of our content, so I did a lot of it. But your head of sales... and you just have to position this a little differently. If they're going to meet with a salesperson, it's the same thing as if they get a email from a BDR, they're like, "I'm not going to figure it out. I don't want to deal with this." But if it's like, "Hey, we're hosting..." We're doing these lunch and learns right now. I was in Paris, New York, and London last week, it's probably why I'm so sick this week, and all of a sudden we did these lunch and learns. People just want to hang out.

**Patrick Campbell** (00:57:47):
So we had 10 people, we had 20 people at one, 10 people, all priority 1 leads. And then we did these meetups with 100-plus people at each. Just think of that brand equity. And you just hang out. It wasn't just me at all of these things. I ran the content, but then all of our sales folks were hanging out and doing their thing. But it doesn't have to be super complicated. It's just those touchpoints that people want. And it's so high leverage because there are a lot of people who will not answer your email but will come to an event to meet you or meet someone from your team because it's something to do, especially if you're buying them breakfast or coffee or something like that. It doesn't have to be something that's extravagant.

**Lenny** (00:58:25):
I love this advice. Basically, it's like if your sales aren't where you want it to be, find a way to meet your potential leads or someone in your team meeting your leads. That's a very actionable thing you could do like, "We're not hitting our numbers, let's just go meet some people, find opportunities to hang out in real life."

**Patrick Campbell** (00:58:41):
Well, in the early days, pre-product market fit, this is all we would do too. I would stay at the worst hotels, I would stay at hostels, but just to get to, "Okay, I want to sell to these people." The best information I'm going to get isn't in a Zoom or I'm asking them questions, it's going to be like, "Hey." I gave a talk on pricing because that was a high leverage thing I could do because no one knows anything about pricing, but they know it's important, so a lot of people want to listen. But then afterwards it's like, "Oh yeah, how do you think about this? What are you doing for this? What are you doing for..." all of those fun producty questions. It's just really, really high leverage. And I think it's one of those things that... It depends on your role, it depends on your stage, but everyone can use something there.

**Lenny** (00:59:21):
Great segue to our final topic. A lot of people spend time on top of funnel driving visitors, driving traffic, getting the word out. A lot of people spend time at the end of the funnel, closing customers, increasing within an organization. You have this perspective that the middle of the funnel is maybe the biggest opportunity these days. Can you talk about that?

**Patrick Campbell** (00:59:40):
Pound for pound biggest opportunity. So take a quick step back. Demand generation exists for more than just supporting the sales team. We forget that. So sales and marketing, the past decade, it's all been the funnel, we're top of the funnel, middle of funnel, bottom of the funnel. HubSpot's trying to make it a flywheel, but marketers are still talking about funnels. And when you look at the data, it depends a little bit on the price point and a little bit on the vertical, but 80% of sales and marketing budgets tend to go to the top of the funnel and the bottom of the funnel. So sales folks and ad-type spend, field events, whatever it is, that's where it goes.

**Patrick Campbell** (01:00:24):
And the whole point is you're trying to move someone from a lack of awareness at the top of the funnel to being aware about you and then to a sales combo or a conversion point, if you're not doing sales. The problem is bottom of the funnel efficiency and top of the funnel efficiency has plummeted the past decade, just plummeted. And it's not only because of the factoids I was saying before about CAC and all these other things and so many competitors being in the market, it's just one of those things that the days of just hiring a bunch of BDRs, not training them, not having them in account-based marketing, not doing all these other things, those days are not here anymore. Those days are gone. Maybe in some specific verticals, in specific parts of the market.

**Patrick Campbell** (01:01:11):
But here's the other problem. Sales today is so much more about timing than it once was. Because there's so much stuff out there, it's one of those things where people are waiting until it's the right time. They're aware of you, but they're waiting. So the question we have to ask ourselves to not bury the lead any further is do we need to make this river of demand generation, basically what demand generation works? But that's table space.

**Patrick Campbell** (01:01:37):
If we want to be even increasingly more successful, that middle of the funnel needs to get bigger. That pool of users who is aware of you, interacting with you on a regular basis. What if you had leads basically hanging out there in the middle of the funnel, interacting with you on a regular basis before all of a sudden their timing was right and then all of a sudden they go to the bottom of the funnel, and even better they opt into them. You don't have to keep going after them and doing sales processes that are very kind of churn and burn. So that pool of leads.

**Patrick Campbell** (01:02:07):
And so the best way to create pools of leads, freemium. I'm a huge fan of freemium. I used to write articles about how freemium is terrible, so I'm a big convert. I wrote a book on freemium as well. The thing with freemium is CAC is still up over the past decade, but it's up a lot less than overall CAC. Customers who convert from freemium and become paid customers, their retention is typically about 10 to 20% higher than those who converted from a free trial or converted from a traditional sales process. And then on top of that, NPS or CSAT, we measured it through NPS, is typically about double because they're converting on their own timeline, not on some artificial timeline of a free trial or artificial timeline of sales.

**Patrick Campbell** (01:02:47):
You should still have those things, but I want this pool of people who are aware of me and are using something of my product because at the end of the day, what better content do you have than your actual product? Even if you're a big enterprise solution, give them something to interact with. And then the other way to fill that middle of the funnel is, I think inbound marketing is just becoming SEO and eBooks. Kieran from HubSpot gets offended when I say that, but I love you, buddy. It's okay. I'm still a huge fan. And this is just because CAC and inbound marketing has gone up and it's all about a lot of SEO and we'll see what AI does to that.

**Patrick Campbell** (01:03:21):
But this whole thing of inbound media, we got on this train about five years ago, and inbound media is just podcast video series. When we sold the company, we had eight different podcasts and video series, all very niche like Pricing Page Tear Down, which was a show about we collected data and tore down pricing pages, the good and the bad. We had Boxed Out, which was a retention focused show for the subscription e-commerce industry.

**Patrick Campbell** (01:03:44):
So all of that was to build this pool so that people were aware of us. And then over time, all of a sudden they're like, "Oh, we have a pricing problem, we should go talk to these guys. Oh, we have this content or this retention thing, we should go talk to these guys." But I think the pool is kind of the future and a lot of people are still treating it as just this gateway between the top and the bottom of the funnel.

**Lenny** (01:04:02):
Middle of the funnel is the new top of funnel. We need a bumper sticker.

**Patrick Campbell** (01:04:05):
There you go. I don't know if that's going to sell well, but I will buy one, so.

**Lenny** (01:04:09):
The most nerdiest of all bumper stickers. Patrick, we've gone through 10 topics. Is there anything else you want to touch on before we get to our very exciting lightning rounds?

**Patrick Campbell** (01:04:18):
I think what I will say is this is all still hard. So I'm giving some heuristics, I'm giving some benchmarks, but your mileage is going to vary. But again, that's your job, whether you're a founder, a product person, an exec, whatever you are, your job is to take in information, your job is to analyze the problem, and then ultimately come up with the best solution. And so I think it's one of those things that there's some hard truths I think we talked about, but then there's a lot of this that you have to evaluate it for yourself. So just a general, I may come off like a know-it-all, but I understand that mileage varies I guess is the best way...

**Lenny** (01:04:54):
Well, with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

**Patrick Campbell** (01:05:01):
I'm ready.

**Lenny** (01:05:02):
Okay.

**Patrick Campbell** (01:05:03):
I feel like I need a buzzer.

**Lenny** (01:05:05):
I'm going to add a buzzer someday. Anyway, here we go. What are two or three books that you recommend most to other people?

**Patrick Campbell** (01:05:11):
I have read High Output Management probably 20 times in the past 10 years. I read it at least once a year now. I commissioned a bronze bust of Andy Grove, so that's being done. I'm a big Andy Grove fan.

**Lenny** (01:05:25):
Oh, it's in progress?

**Patrick Campbell** (01:05:26):
Yeah, yeah, yeah. It's in progress. It's not done. I'll send you a mockup after this. But yeah, High Output Management. Thinking in Bets, going to that first principles thinking. I find that a good book to share with people so that they can think about things and get on board with that.

**Patrick Campbell** (01:05:40):
And then Powerful by Patty McCord. Anything around HR to kind of break your brain a little bit about what you think about HR and people ops. That's the gateway drug. That was the one where I was like, "Oh, we can choose how to design our people ops teams."

**Lenny** (01:05:55):
Okay, next question. Favorite recent movie or TV show?

**Patrick Campbell** (01:05:58):
I don't have one that's recent, but I watch The West Wing at least once per week, so I've done that for a long time. I love Sorkin, I think the writing's just so good, so I'll just throw that out.

**Lenny** (01:06:10):
Great one. Someone was telling me there's a podcast to analyze each episode, which [inaudible 01:06:14].

**Patrick Campbell** (01:06:13):
It is a great podcast and I've listened to most of them, so yeah.

**Lenny** (01:06:18):
Okay, great. You're all over it. Favorite interview question that you like to ask because you're interviewing.

**Patrick Campbell** (01:06:22):
I have a controversial one. I'm not going to be able to go through the entire question in a lightning round. But what I do is I do a mini... I did all the final interviews at ProfitWell, and we did a very hard culture check in the final interview. There's a mini case study, it only lasts about a couple of minutes, I'm not going to go through it, but I asked them if someone in Slack responded to someone sharing something benign, like some report they found on the internet from McKinsey, they shared it in Slack, and then someone responded to that with something indirectly offensive.

**Patrick Campbell** (01:06:55):
So it's changed over the years, sometimes I say, "Oh, they called it the R word, they said it was stupid," something indirectly offensive. And I say, "What would you do, and what do you think the company should do?" And no matter what they say, I challenge them, and I always tell them, "I've never seen that at ProfitWell," which is always good just to make sure they don't have a bunch of fear in this position.

**Patrick Campbell** (01:07:19):
But it gave me a really, really good opportunity to talk through our culture, particularly the most charitable interpretation piece. And I would say there were about 10% of people who had a zero tolerance policy for whatever the situation was. And I would tell them, I would say, "Hey, listen. We have zero tolerance for the obvious things, we probably all agree on those." But for this type of situation, we would ask some questions, we'd want to figure it out, we want to see, there's probably some judgment around what happened, how long if they'd been doing this for a while, that type of thing. And then we would make a decision on what would happen. And a lot of times nothing would happen except, "Hey, don't be an idiot, you're smarter than that, use better words," or something like that. And so that was a good culture check to opt them in or out.

**Lenny** (01:08:05):
That is very cool. It circles back to the value of culture and values and being aligned within your company on culture and values. And it's interesting that that's the question you ask, and not something technical or skill-based.

**Patrick Campbell** (01:08:16):
Yeah. Well, I do all the final interviews. So they've already gone through a skill-based and they've done culture screen already and stuff like that. So this is more of the, here's why you should not work here, that type of conversation basically.

**Lenny** (01:08:30):
I love that. Next question, what are five SaaS products that you or your company uses that you love? And bonus points for ones maybe people haven't heard,

**Patrick Campbell** (01:08:39):
That's hard to answer too because at the end of the day, we'd all say Zoom, Google Workspace or whatever they're calling it these days because those are the things that are so central. I've got to give a shout-out to Notion, we use Notion for all of our documentation. I use Notion for my personal... all these things. I know Code is a sponsor, so I apologize but-

**Lenny** (01:08:59):
They're both sponsors, and so we're friends with everyone over here. Both are great-

**Patrick Campbell** (01:09:02):
Amazing. Lenny's Podcast, friends of all products. Descript. I use Descript quite a bit. I use Descript not only for... it's like a video recording and editing tool, or you can bring in video to edit. But it's got some cool features that... I use it more than Loom a lot of times because it just works in my workflow, not only for creating, but also for those quick conversations.

**Patrick Campbell** (01:09:25):
K-Tool. Here's a fun one. This is an indie product, K-Tool. There's probably other products that exist like this, but I actually really like the interface of it, it's super simple. Basically if I'm online or someone sends me a PDF or something like that, I can basically choose to send that to my Kindle. So if someone sends me something I could just choose to send and then I can batch all of those things into a weekly newsletter that I can curate. So my Sundays and my Monday morning are just spent reading. So I have this weekly newsletter of someone wants me to review this thing or someone wants me to read this article or something like that. So I batch that into a little newsletter and it's just a Chrome extension that works really well.

**Patrick Campbell** (01:10:03):
Tweet Hunter, I'm trying to be more on Twitter. I went through lulls, so now I'm trying to be consistent. So Tweet Hunter's pretty good. It's got some AI fun stuff into it to make discovery better. And then it's not a SaaS application, but the last one is this Apple Watch Ultra. So I don't carry my phone anymore. I just don't... I found myself being on a computer, walking away with my phone, going, doing stuff and then just never being off-screen. So I have this for when I'm not in front of my computer and I'm this close to also doing it when I travel to when I've been traveling, my phone will stay in my suitcase, but it connects if I need to make a phone call. It connects via Bluetooth, all that kind of stuff. But just trying to take my attention away from my phone basically, so that's, that's been the unlock.

**Lenny** (01:10:51):
Damn. What a list. That was incredible. I'm going to ask just one more question. What's favorite lesson from your NSA experience that helps you in life day to day?

**Patrick Campbell** (01:11:02):
I shouldn't say everything, but most things are more complicated than it seems. And that's not like a sinister thing, it just means when that person's coming at you and super angry about something, whether it's your fault or not, something's there, they're having a bad day, on top of it, you really messed up, you tapped into a particular emotion that you didn't realize you did. Or hey, there's even the story in the news about this politician's bad or something like that. Everything's a lot more complicated, and not in a it's too hard to understand way, it's just you should always caution yourself on believing the first reaction that you have.

**Patrick Campbell** (01:11:44):
And I developed that there because there's so many things where... And it was also my first job, so a lot of this stuff happens because it's your first job, many people may have this experience at a different place, but it was like, "Oh, this geopolitical thing that's happened. Oh, here's my first instinct, that means this is bad." They're like, "Well, actually, there's this other thing going on over here and this other thing going over there, and those are actually connected. That's why this is caused." So that's helped me, one, not get so pissed off at the news. That's also helped me, I think just as a human, along with most charitable interpretation, to just be like, "Okay, let me not overreact here. Let me seek to understand and then react or respond, versus react."

**Lenny** (01:12:23):
What a beautiful way to end it. Patrick Campbell, renaissance man of a brain. This may be the most action-packed episode we've had, and I'm not surprised. Two final questions where can folks find you online if they want to ask you questions, reach out, learn more about what you're up to? And how can listeners be useful to you?

**Patrick Campbell** (01:12:38):
Yeah, so I am on Twitter @patticus, childhood nickname, P-A-T-T-I-C-U-S. LinkedIn, Patrick Campbell. I don't check my LinkedIn messages, I'm going to get around to it, it's just there's so much spam in there. But yeah, you could find me there or just pc@patticus.com, that's my personal email. So yeah, if I can be helpful or you want to see more of the data or you have this question or that question, we've probably written or recorded something on some of the things we talked about today, so I'm happy to send it over and just obviously want to be helpful, so yeah, feel free to hit me up.

**Lenny** (01:13:08):
Amazing. Patrick, thank you again for being here.

**Patrick Campbell** (01:13:11):
Thanks for having me, man.

**Lenny** (01:13:12):
Bye, everyone.

**Audio** (01:13:14):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [13/22] An inside look at how CNN builds product | Upasna Gautam

**Upasna Gautam** (00:00:00):
It happens all the time, right? That is the nature of breaking news. I mean, you have to be ready to pivot at the drop of a hat. I had a big working session planned with my users to do research with them, or do user testing, and breaking news breaks, and it takes so much time and effort to gather a team of editors across the globe to do a user testing session. And when breaking news happens, they have to prioritize that over everything. So what do you do in that situation? You can be frustrated, absolutely it's frustrating. But we always have to have the ability to A, pivot of course, but also have backup and buffers in those types of scenarios.
**Lenny** (00:00:45):
Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Upasna Gautam. Upasna is a product manager at CNN, where she leads the team responsible for the content management system that journalists use to write and publish their stories. She's also on the frontlines of elevating the discipline of product management within newsrooms through her work at the News Product Alliance. She's also a longtime meditation and mindfulness teacher, which as we discuss ends up being pretty damn handy working at a place like CNN. We dig into how the product team operates within CNN, how they collaborate with journalists for breaking news, dress rehearsals, and also some simple tricks to build your own mindfulness in your day-to-day work as a PM.
**Lenny** (00:01:31):
Enjoy this episode with Upasna Gautam after a short word from our wonderful sponsors. This episode is brought to you by Amplitude. If you're setting up your analytics stack but not using Amplitude, what are you doing? Anyone can sell you analytics, while Amplitude unlocks the power of your product and guides you every step of the way. Get the right data, ask the right questions, get the right answers, and make growth happen. To get started with Amplitude for free, visit Amplitude.com. Amplitude, power to your products. Today's episode is brought to you by OneSchema, the embeddable CSV importer for SaaS. Customers always seem to want to give you their data in the messiest possible CSV file, and building a spreadsheet importer becomes a never-ending sink for your engineering and support resources.
**Lenny** (00:02:19):
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**Upasna Gautam** (00:03:15):
Thank you Lenny, I'm so excited to be here.
**Lenny** (00:03:18):
As you probably know, I'm on this kind of quest to understand how different companies build product, especially companies that are kind of outside the Silicon Valley, just like standard tech scene. And I've always wondered what it was like to build product at a company like CNN, which is very different from where most, I don't know, tech PMs work. And so I'm really excited to have you on and to give us a little glimpse into what it's like to build product at CNN.
**Upasna Gautam** (00:03:42):
Awesome, I'm very excited to share as well.
**Lenny** (00:03:44):
So I was doing a little research on you before this chat, and I noticed that you've been teaching and studying meditation and mindfulness for, I don't know, maybe a decade? And I imagine that comes in handy at a company like CNN, which also I imagine is quite hectic at times with breaking news all the time. And so here's my question, what have you learned or brought from that practice to your ability to lead and ability to just like keep your team calm and focused during I imagine many hectic moments?
**Upasna Gautam** (00:04:16):
Love that question, and working in product in news is a very [inaudible 00:04:22]. We hear a lot about having the skills to thrive in ambiguity in order to be a successful product manager, but to be a successful product manager in news you have to be able to thrive in chaos. And equanimity is the most important skill I've developed I think across my entire life, and it's due to all of those years of practicing mindfulness and meditation. And equanimity is one of my favorite words, it means mental calmness, composure, evenness of temper, especially in crazy, stressful situations. It's the ability to remain un-rattled in like the highest of highs and the lowest of lows. And if you think about it in the dynamic of a workplace or human interaction, it's really the ability to pause before reacting.
**Upasna Gautam** (00:05:11):
And reactivity is the root cause of so many of our workplace woes and product management frustrations, and when you're able to pause before reacting you can start to undo and break a lot of those negative patterns in your brain. And in news, and especially the world's biggest breaking news organization, you can cut through that chaos with equanimity because it also really gives you this outsized advantage in everything from stakeholder management, team morale, to the way you're able to translate user feedback, to product development philosophy. And the thing is is you're always going to hear things and feedback that you don't like, and opinions that you don't like, and you're going to get frustrated. That's product management, that's life.
**Upasna Gautam** (00:05:59):
But real power to me comes from equanimity, and that comes from managing your emotional reactions, and not trying to control others. So I think when you're able to cultivate that level of self-awareness for yourself, you're able to chart a clear path forward for your team and serve as a compass in the chaos.
**Lenny** (00:06:22):
Is there a story or an example that comes to mind where things were just like, "Oh shit," and you were able to tap into that skill that you built to stay calm and focused, or even just like help your team stay focused?
**Upasna Gautam** (00:06:33):
I mean, it happens all the time right? That is the nature of breaking news. I mean, you have to be ready to pivot at the drop of a hat. And so I think more than just like the big, chaotic moments in those daily interactions when there's chaos, I think that's when it really shows its power and helps me navigate those day-to-day interactions when I had a big working session planned with my users to do research with them, or do user testing, and breaking news breaks, and it takes so much time and effort to gather a team of editors across the globe to do a user testing session. And when breaking news happens, they have to prioritize that over everything. So what do you do in that situation? You can be frustrated, absolutely it's frustrating. But you always have to have the ability to, A, pivot of course, but also have backup and buffers in those types of scenario. So any time we're planning we build in buffers for all of that chaos that's happening on a daily basis.
**Lenny** (00:07:41):
Wow, that's cool. Is that a real thing that happened? You were like, in a big meeting with all the researchers and then something went off the rails in the world?
**Upasna Gautam** (00:07:47):
Oh yeah, absolutely. Happens all the time.
**Lenny** (00:07:49):
I don't know how much you can go into all this, but what is it that you would do in that case, like as a product team? What are they looking for you to do at that moment?
**Upasna Gautam** (00:07:56):
For us it's not really anything we have to do. It is more so, "Okay, well our goal at this session was to get user testing done, or user feedback from that user testing session with our editors. And so, what do we do? Okay, well good thing we had a backup planned, right?" We don't actually have to go into that scenario, but since our editors and our journalists are customers we're there to serve their needs, but they're not here to serve our needs. They have a whole another job that they have to do. And so we have to have the ability to adapt and accommodate to those really chaotic schedules across global time zones. And so that happens again like, it's not like once in a while, it's a very regular thing that we have to be aware of and also account for.
**Lenny** (00:08:46):
Okay, again, it's like the journalists are the ones in the meeting that like, "Oh, they have to go write about the stuff uncovered."
**Upasna Gautam** (00:08:50):
Totally.
**Lenny** (00:08:51):
I see, that makes sense. You said that you built in some buffer time to kind of account for these things. Is there like a systematic way of doing that, or is it just broadly, "Let's add buffer time"? Is there like a rule of thumb you think about there?
**Upasna Gautam** (00:09:02):
It depends on the scope of the work we're doing at that time. So one of my main responsibilities is to rebuild our content management system, which also involves onboarding our editors and journalists to it off of our legacy platform and onto our new one. So when we're thinking about onboarding especially the teams, our onboarding cycle's very long. It involves training, testing, lots of dialogue and feedback. And then only do we actually test, and then we onboard. And so it is a long cycle, and it's longer than it maybe seems like it needs to be because we have to build in those buffers. Sometimes that buffer is a day or two, and sometimes it's a week or a month. And sometimes when we think we need a buffer, we get it done in a day and we quickly move onto the next phase.
**Upasna Gautam** (00:09:53):
And so I think that quick decision-making in those times is super-important, because you have to be able to assess the situation as it stands. And so I think mindfulness is so important too in practices like this, because being able to objectively see the scenario for what it is, make a quick decision and move on to the next phase is something we have to analyze every single day.
**Lenny** (00:10:16):
Makes me think a little bit about a lot of CEOs are very busy and pulled into a lot of things, and so you have to kind of account for their schedule. And it sounds like you have many, many people that you work with that have crazy schedules.
**Upasna Gautam** (00:10:29):
Yes.
**Lenny** (00:10:30):
I wanted to dig a little bit deeper into how you, your team works with the news team. It's such a unique way of working, most product teams don't have a whole set of journalists that they have to work with as stakeholders. So I'm curious specifically, say a journalist has like, "Hey, I'd love to build a special immersive experience for this story," or, "I need some special feature to help support this work that I'm doing." How does that work? Do they come to you, and, "Okay, here's a roadmap [inaudible 00:10:57] maybe in the quarter [inaudible 00:10:59]." Imagine it's like, "I need this next week." How do you work with the journalist team, basically, on product?
**Upasna Gautam** (00:11:04):
Yep. This is pretty much the foundation of all of my work. We talk to our editorial staff every single day, and after a lot of observation and learning I implemented a system to manage that kind of intake with four different touch points or events. So we have weekly demo days, working sessions, breaking news dress rehearsals, and office hours. So with weekly demo days, I facilitate those with my product design lead and my tech lead. And we use that as an open form of communication to deep dive into features that exist on our platform, also to preview or give a sneak peek of new features to come, and kind of recreate their workflows and do a show and tell. Again, we wanted to open that up as a forum to not just our editorial partners but also anyone across the business who is interested in learning about the product and which is our platform.
**Upasna Gautam** (00:12:00):
And it was also a great way to kind of evangelize the product too. Coming off of a legacy system after several years onto a brand-new one is a big change at a place like CNN, and so we definitely tried to make sure that smart repetition in different ways is top priority. So, weekly demo days is one. Working sessions are interesting. I use the term working session because it's a combination of several things. This is a really critical part of our onboarding process where we gather breakout groups of our journalists and editors to work with us to recreate their workflows in the new platform. This allows us to address any friction or issues of course that are occurring in their workflows. But also we're able to gather a lot of awesome feedback from them in those sessions.
**Upasna Gautam** (00:12:54):
We used to call them user testing sessions, but decided to move away from that and just call them working sessions so they're more collaborative. And again, it's a really critical part of our onboarding process. We usually do three to six of them depending on the size of the group before the team is actually onboarded for two hours per session. So they're like deep dives into their specific workflows, so as you can imagine the way the politics team programs content is wildly different than the way the entertainment team does, or the way that the health team does, and very different than the way that the CNN homepage even interacts. So all of those are separate teams we have to work with when it comes to getting feedback. So in addition to that, we also do I mentioned breaking news dress rehearsals.
**Upasna Gautam** (00:13:44):
And you can imagine this is exactly what it sounds like. We create a script and do a simulation of a breaking news scenario to stress test our platform, because all breaking news scenarios are definitely not the same either. So this gives us a lot of great feedback in that short amount of time at the speed of breaking news. And then last but not least, we have office hours which I just started last year, and that's also probably what you can imagine, open blocks of time where me and my product design partner and my tech lead are just there to answer questions, help people troubleshoot any friction they might be experiencing in their workflow, get their feedback. We just wanted to open up another line of communications, so we do those right now once a week. Sometimes they go up to two times a week if we're in a really vigorous onboarding phase.
**Upasna Gautam** (00:14:33):
After those conversations and sessions and events happen, you know it's our job to translate their needs into the functions that we, A, either maybe already have that we can optimize, B, we build anew, or we tell them it's not viable. And the good thing is that because they've been along for the ride with us throughout the product discovery process we've earned their trust and respect. So that when we tell them something like it's not viable, they usually get it.
**Lenny** (00:15:07):
Man, I have so much questions about just working with journalists. I feel like pushing back on a journalist is probably extra hard versus other types of stakeholders.
**Upasna Gautam** (00:15:14):
It is.
**Lenny** (00:15:15):
Can we zoom out a little bit, and you talked about what you work on at CNN, which is the content management system and things around that. Can you just talk about whatever you can share, just like what does the product team look like at CNN, how many PMs are there, how's like the product work structured and where do you fit in there?
**Upasna Gautam** (00:15:31):
Yes. I mentioned earlier my team sits on CNN Digital, and I think when most people think of CNN of course you think of TV and linear programming. I have nothing to do with that, CNN Digital is digital, and it's made up of several teams that are structured around a lot of different product areas. It includes everything from the content management platforms that I work on, to data infrastructure, to personalization, to video experience, which includes like the products of video editor, and the video player, to podcasts, there's a lot. So each of those are product teams. And so we also split out... The way CNN is split out into CNN Digital is because there's a separate core content platform that powers broadcast and linear TV.
**Upasna Gautam** (00:16:21):
And the one that I work on powers CNN Digital. So on my team, the core platform team, our stakeholders and our customers, like I mentioned, are journalists and are editors. Which presents a really unique dynamic, and it's one that I love. We have direct access to our customers at all times of day, for better or for worse, and they're embedded into our product development process. And each of those teams under CNN Digital is kind of like a squad, very similar to how it is at other larger tech companies. We have PMs, we have engineers, designers, and delivery managers embedded in those squads. And since my team is a core platform team, our main responsibility is to A, build our newer, faster, more flexible content management platform to replace our legacy one, and B, onboard our entire editorial staff to it.
**Upasna Gautam** (00:17:19):
And so even more specifically my role is focused on rebuilding the tooling and the editorial experience of that platform, as well as doing the actual onboarding of our journalists. So we work cross-functionally because our team kind of is the umbrella over a lot of different teams, so we truly work cross-functionally to make sure that we're serving our journalists with the tools that they need to do their job in the most efficient way possible.
**Lenny** (00:17:48):
What would surprise people most about how product is built at CNN?
**Upasna Gautam** (00:17:54):
I think the most surprising thing may actually be that there's just so many different types of products that we build. Like I said, I think when most people think of CNN you see TV, and you think of Anderson Cooper, and all of the things that are very publicly visible. Most of our product work and product teams all sit behind the scenes, and so I think just that in itself, like the sheer size of that is surprising to a lot of people. So I mentioned like all of the different teams, product teams that are based off of function, content management platforms, infrastructure, personalization, video, podcasts, linear TV. And I think that in itself, like the sheer size of it, we're not the size of Google by any means. But at the same time we have the expertise and the depth and breadth of a lot of those larger tech companies.
**Lenny** (00:18:52):
I'm curious about the day-to-day operational work of how you build product at CNN. So our first question here is just, you use like OKRs, and OKRs with like key objectives, and outcomes, and 70% of a goal is success.
**Upasna Gautam** (00:19:06):
Yeah, absolutely, we do. We've used OKRs for a long time, and they've served as an anchor for my team over the last three years. I can't go into specifics on like what our OKRs are, but I did kind of cover the two main parts of it, which is rebuilding our content management platform and onboarding our users to it. So again, it's a long game at CNN when you're working on a core platform to replace a legacy one. And so we break those OKRs down of course even further into, we look two to three years out and build goals based off of that. Then we break them down by quarter and month, and then out of that for my team and what I do I need to, for my own sake and my team's sake, break those down by the week. And when we're in rapid development phases, we're planning on a daily basis.
**Lenny** (00:20:01):
How about in terms of just planning broadly? How far out does the product team at CNN plan in detail, like have an actual roadmap? And is that standardized across teams, or can each team kind of do their own approach?
**Upasna Gautam** (00:20:13):
It's a combination of both. So we have one that is an over-arching roadmap that tracks to like our company OKRs and our product organization OKRs. And then from there I mentioned we have our squads, product teams, and we have OKRs on those as well track up to the larger, broader ones. And so once we get down to that level though, there is flexibility and we have autonomy to tackle those how we want. Which is really great, because the scope of work across our different product teams is drastically different. Working on core platform, like I do, versus working on video experience, versus podcasts. I mean, it's apples and oranges. And so it's really awesome that we have the flexibility to kind of make it work for us, while also having these larger goals that we know that, "Okay, this is what we need to work towards."
**Upasna Gautam** (00:21:12):
And I mean, like the saying we always hear in product, of, "Stay firm on the goal, but flexible on the process." And we've definitely been able to use that and leverage that in the way that we track against our goals.
**Lenny** (00:21:27):
Something else that a lot of people are always curious about is product review meetings and design review meetings. You talked about a couple of these meetings that you have, but do you have standard product review meetings where folks get together and just review stuff and progress? And if so, how do they work? Like who runs them, who comes to them, how do you make decisions, things like that?
**Upasna Gautam** (00:21:46):
We have multiple variations of those. Some are standing ceremonies of course, and some are ad-hoc. Again, it's really based on the work we're doing in whatever phase we're in. But when it comes to product review, and product discovery or design review meetings, in addition to my design lead I've made it a point to bring in my tech lead and engineers along for this product discovery ride, and that's definitely been a game-changer as well. When our engineers are able to understand our journalists' needs at the same level as we are, they're able to define the how to do it with so much greater clarity and precision. And so my tech lead is embedded also in our product discovery process, he joins our user testing sessions, and our design jams, and our editorial conversation planning sessions.
**Upasna Gautam** (00:22:37):
And it's helped him and the rest of our tech and engineering team become experts on the why are we doing this and what are we working towards, to better determine technical feasibility. And he's done an amazing job of also passing that knowledge down to the rest of our engineers on our team, so it's really like this mentality of getting that important feedback from our journalists, understanding their pain points and then sharing and teaching it across the team. And I think the key takeaway on that is it's so important to think of your engineers as partners and not just resources. And when they are embedded into the process right upfront, it makes the whole process in general more efficient.
**Lenny** (00:23:21):
So it sounds like that was maybe an evolution of the way the team works, as engineering has been looped into a lot of this early stuff more recently?
**Upasna Gautam** (00:23:30):
Totally, yeah. Recently-
**Lenny** (00:23:33):
Cool.
**Upasna Gautam** (00:23:33):
... meaning, I mean... Again, long game right? Because it's been a couple of years.
**Lenny** (00:23:39):
Got it. Going in a slightly different direction, I'm curious if there's any fun or unique traditions or rituals that the CNN product team has. These are always fun to hear about.
**Upasna Gautam** (00:23:51):
I'll be very honest, we are not one of the cool teams. The politics team and the breaking news teams have all these cool rituals and fun things that they do.
**Lenny** (00:24:02):
What kind of stuff do they do?
**Upasna Gautam** (00:24:03):
It's different also because they're usually in-person in the newsroom and I work remotely, and so... And actually most of my team works remotely. And so they have their rituals, but I will say one of the things that we started to do is... So onboarding teams has been a big goal of ours, and that we've slowly checked off the list over 2022. And any time we successfully onboard a team or launch a new feature, it's not anything crazy or fun, like there's only so much you can do when you work remotely. But we definitely make it a point to celebrate, and it's been hard to figure out ways to keep team morale up when you're all-remote. And it started with... We knew we needed to start doing something when we would have a big launch, and it was so anticlimactic.
**Upasna Gautam** (00:24:51):
And we literally hit publish and onboard onto like a politics page, and we were like, "Oh, okay, so I guess that's it." So one thing we started doing is sending like these gift boxes of like random tchotchkes and stuff that mean things to us from the whole year, and it's like just cheap little gag gifts and stuff that we send to each other. I have random stuff all over my desk, I don't even know if I can share some of it. So we try to make it a point to at least share and celebrate, and then when we're in-person we do too. But again, being remote, there's definitely a challenge there.
**Lenny** (00:25:32):
Are you ever able to get like a cameo from an Anderson Cooper, or someone else on-air to thank the teams? That feels like a cool feature potentially.
**Upasna Gautam** (00:25:41):
So one of my key stakeholders, she leads the video team at CNN, and she is a... We've had some discussions about doing a sizzler reel for our content management platform, since we're onboarding people and building new features. And there have been discussions with her about getting a celebrity to come and promote the product for us, so working on it.
**Lenny** (00:26:07):
Yeah, it feels like a missed opportunity, you've got so much talent around.
**Upasna Gautam** (00:26:11):
Totally.
**Lenny** (00:26:12):
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But getting a SOC to your port can be a huge burden, especially for startups. It's time-consuming, tedious, and expensive. Enter, Vanta. Over 3,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC 2. Vanta can get you ready for security audits in weeks instead of months, less than a third of the time that it usually takes. For a limited time, Lenny's Podcast listeners get $1,000 off Vanta. Just go to Vanta.com/lenny, that's V-A-N-T-A.com/lenny to learn more and to claim your discount. Get started today. Coming back a little bit to the way y'all built product, I'm curious how you balance new product work and new features versus maintenance and bugs. Do you have kind of a... Is there like a philosophy at CNN of how much goes to bugs, maintenance versus new stuff, or is it per team and just, how do y'all think about that?
**Upasna Gautam** (00:27:45):
It's certainly team-specific, because again, the scope of work across teams really varies. But since my team's product is an entire platform, it's my job to ensure we're still clear on our goals because like I said, they may change on a week-by-week basis. One sprint might be high-priority feature development, in another sprint maybe we're focused on medium-priority optimizations and bug fixes. But we know that any time there's a critical incident in production, it also takes critical priority over everything else. So it's a balancing and juggling act that relies heavily on intuitive decision-making. But I will say we're also really fortunate to have a global, 24/7 editorial support team that we work really closely with.
**Upasna Gautam** (00:28:35):
So they are the ones who handle, troubleshoot, escalate incidents up to the relevant teams. There are a lot of layers to that protocol when a critical incident occurs. And so our editorial support team is that first layer of support, whereas my team might be the second or third depending on the level of severity and who it gets escalated to. So there's definitely a lot of processes in place, we're not always that first line of defense, which is actually... It alleviates a lot of stress, to know that we have an entire team around the clock globally dedicated just to that.
**Lenny** (00:29:12):
When you're talking about these incidents and moments it makes me wonder, is there a memory of just like a wild time of something happened in the news, or just like, "Oh man, we've got to get on top of this thing"? Is there like a memory that you think of like, "Wow, that was crazy"?
**Upasna Gautam** (00:29:26):
It's funny but also crazy and amazing, is... So our new content management platform, we've been building it for a while and stress testing it for a while. And politics and election season at CNN is Superbowl like times a hundred. And so we have to be all hands on deck, like all layers of support intact. And so we have also a lot of layers of fallback in case something happened, right? Like there's layers and layers of infrastructure fallback if CNN.com goes down, or another service goes down. And so it actually did happen a couple of years ago in the 2020 election, and one of the fallbacks at that time, because we were not...
**Upasna Gautam** (00:30:14):
We're still on our current content management platform, but we had our new one as we're building it as one of the levels of fall. And if X, Y, Z fails, then it goes to our current platform, and it did. And so that's actually happened, where our new platform saved the day even though it wasn't fully ready. But that just goes to show we think about that kind of stuff like in granular detail, when we think about everything that could possibly go wrong. Because it has happened, and it will happen, and it does go wrong. So that was kind of cool, it was validation to know that the platform we have is really stable, and strong, and secure, that it was a fallback for the election.
**Lenny** (00:31:03):
Okay, and it must have felt good, it feels like a promotion material right there that your work-in-progress system saved the day.
**Upasna Gautam** (00:31:10):
Yeah, I agree.
**Lenny** (00:31:12):
You talked about how you have like these breaking news dress rehearsals. I just noted that, and I thought it would be cool to just revisit that briefly. Like, how does that work? You just get the team together, and like, "Here's a news story that just broke. What do we do?" Like, how does that work?
**Upasna Gautam** (00:31:27):
It is scripted, right. So we can only get so close to the real thing. But one thing we do is we script everything, like the teams and the players that we need involved in it, what the incident is. And it usually starts when breaking news occurs with an email, the news-gathering team sends an email to our writers and our producers. And then from there it goes out all the places it needs to go. There's a video that needs to be created, there's an article that needs to be written. Again, the TV side I have no insight into, it's like a foreign land to me. But as far as the digital scope goes, there's a lot of work that has to be done. Even things like photo and imagery, we have a whole team dedicated just to selecting photos.
**Upasna Gautam** (00:32:11):
The photo desk is very involved with that process. And so that is all scripted out, and so we say, "Okay, here's the news, here's how it's going to break," and then we run it. And so we use interpersonal communication tools at work of course, email, and we run the whole thing from the minute the email is sent to... And of course since we're testing the platform with this breaking news dress rehearsal, to the minute you hit publish on that page. And there's a lot of stuff that goes on in there, and it all happens in the span of minutes. And so while that is happening, while that dress rehearsal is happening, we have our engineers and our editorial support team on hand as well. So they're observing what's happening while it's usually me and one of our editorial stakeholders and leads facilitating the actual rehearsal part.
**Upasna Gautam** (00:33:02):
And you know, getting user feedback on, "Okay, did something break, did everything work as it was supposed to work?" And also allows us to understand like how far we can go with stress testing different features on our system. So each one is different, but it's a crazy amount of stuff and information you can gather in such a short span of time. Because if it cannot serve the needs of breaking news, then it's useless. So it's a lot of work that goes into it for this three-minute event.
**Lenny** (00:33:35):
That is cool. It feels like just a cool tactic you could use anywhere, and that's a good segue to the next question I had, is just having built product at CNN and seeing how the product team works, what is it that you think you'll take with you to future product teams and future companies if you ever move on to anything else?
**Upasna Gautam** (00:33:53):
So I of course can't speak for the entire scene and product team, but I can speak for myself and my specific team. In order to stay competitive in our modern news landscape, building this content management platform and the technology behind it has taught us how to enable rapid development and integration of new features and workflows. And we've been able to quickly test hypotheses while reducing risk, and again, time is of the essence when it comes to breaking news. And when you layer that with a very complex content management technology, there's a lot of moving parts. And we've been able to do that successfully, and it's pretty amazing. And because of that we've developed, I think, this unique skill of high agency under high pressure.
**Upasna Gautam** (00:34:49):
And I really think that that skill or combination of skills is our superpower, and that is something you can take anywhere, that is something that is an asset to any product development team.
**Lenny** (00:35:03):
Let's circle back to our original topic about mindfulness and meditation. Other than just living through it and either becoming a meditation expert or having worked at a company like CNN that has a lot of this, is there any, I don't know, tactic you could share, something that someone could take tomorrow and be like, "Okay, I'm going to get better at dealing with crazy, unexpected events," based on the experience you've had?
**Upasna Gautam** (00:35:25):
Two parts to this. So one, I would be remiss as a meditation educator if I didn't say that there is no substitution for meditation. So just do it, it takes a long time, and it's a lifelong work-in-progress. But the good thing is that it also... Like the more you do it and consistently you do it, it compounds over time. Okay, if you think of any job description for a product manager it's mostly the same core stuff. You need to be able to lead a team without having authority, you need to have great communication skills, you need to be able to bribe in ambiguity, you need to be able to work with a lot of different people on the technical side and business side, all of the stuff that we hear all the time right?
[NEW_PARAGRAPH]But how do you actually become better at those things? Like, there's only so much you can gain from reading a book. To me it's either A, you've got to go do it, and B, meditation has helped so much because of the clarity of mind and clarity of thinking you're able to cultivate because of it, especially when it comes to communication. And this comes back to another tactic I think. So meditation is one, you can't get around it. It's a very, very powerful tool, I will die on that hill. But thinking about workplace tactics, communication is so essential. When I started at CNN it was a very new chapter for me, it's my first official product management role after working a decade in tech, in data and search infrastructure.
**Upasna Gautam** (00:36:57):
And it was really scary to make that change so far into my career. But when I asked my boss why he took such a big chance on me he said, "It's because of your communication skills and relationship-building skills, and that I've seen you in a room where engineers listen to you and what you have to say, and you listen to them." And he was like, "That in itself is really, really hard to teach." And I was like, "Okay, yeah, I can do that." So when I think about what communication means I also attach that to mindfulness. Like mindful communication is so critical for successful product management, no matter what type of product environment you're in. And it means being like deeply aware of the conversation you're having.
**Upasna Gautam** (00:37:43):
And when I'm having this conversation with you, I'm only having this conversation with you. When I'm talking to my design lead, I'm only talking to my design lead. When one of my journalists is venting because this feature is not working the way we told them it was going to, I am shutting my mouth and I'm listening to them vent, and then I'm extracting what the root cause of the problem is. And I think the takeaway and the tactic is that goes back to exactly what we talked about in the beginning is the ability to pause before reacting is the key to mindful communication and being a successful product manager. I think a lot of times we are taught to have all the answers, or we're expected to have all of the answers.
**Upasna Gautam** (00:38:27):
And people assume we have all of the answers so it's a really frustrating, sometimes, place to be in. But, if you listen and you know where to go to get the answers, that in itself is like a tremendous place to be. So I think the power of meditation, being able to pause before reacting lets you do things like conversate in the language of the listener. So when I'm talking to my journalists I'm not using technical terms or like content management technology terms. They have a whole different vocabulary that they use, they have shortcuts that they have lingo for in our content management system. They call things nicknames, and so you have to speak many different languages as a product manager. And if there's one thing that learning and teaching mindfulness has strengthened, it is that communication, yes, it's very important.
**Upasna Gautam** (00:39:24):
How do you become an effective communicator? I think a lot of times we think of speaking articulately first and foremost, or we think about writing well, which those two are really, really important things. But those can't be effective for us as product leaders if we're not listening, so I think listening and being able to converse in the language of the listener is the utmost importance. And how do you do that in your day-to-day? It's like, okay, if you're having a conversation with your customer are you actually listening to what they say, or are you going in with your own assumptions? Because maybe you're a user of the product. And it was very interesting, because I actually started writing freelance for CNN this past year.
**Upasna Gautam** (00:40:12):
And I was like, "Oh, okay, I'm a user now." And no I'm not, I'm not going to say that it helped me understand their pain points so much more and where they're coming from in a whole different light. But again, I am merely a proxy, I'm not actually the user. What they do is still drastically different. And so when having those customer interactions and stakeholder interactions, the priority should be to listen. And I think that is one of the most important things I've learned, and it's also helped build trust and respect between a previously fragmented structure where product and editorial didn't talk to each other, and now we're a unified partnership.
**Lenny** (00:41:00):
Oh, I love that. I love the reminder that a lot of communication is incredibly important for product managers, and so much of it is not actually you talking, it's you being really good at listening, and that makes you a better communicator. I imagine some people listening to this are going to be like, "Yeah, meditation, I should be doing that." What's like one thing someone could do to move forward on the path to starting to meditate? Is there a resource to recommend, a tip of just starting to do something there?
**Upasna Gautam** (00:41:27):
Totally. I think when people think of meditation, you immediately think of sitting on a mediation cushion like a monk for an hour. And that doesn't have to be true, especially if you're just starting. And there's also of course social media has commercialized what meditation is a lot as well. But at its core, all it is is being deeply aware of the present moment. So I always tell people who are for example like really busy moms who have no time in the morning for an hour-long meditation is, "Okay, take something in your day that you do every single day. You brush your teeth every morning, right? Okay, take brushing your teeth. Can you brush your teeth and just brush your teeth? And when you're brushing your teeth you are engaging all of your senses, and being fully present and aware of how it feels, how it smells, how it sounds."
**Upasna Gautam** (00:42:27):
That's two, three minutes of your day. That's meditation, and I think it's an amazing way and an easy way... Oh, sorry, not easy. Simple, not easy way, always, to think about what meditation actually is. Is like, instead of like having to uproot your whole life and the way you live to bring meditation in, think about what you already do every day and how you can just be more present, like fully present. And that's one of the core examples I give, is start with brushing your teeth and just brush your teeth. There's an old app I've been using for a long time if you're into that, I stopped using it recently but it's still amazing. It's called Insight Timer, the free version is amazing. It started as like a single-frame app probably about 10 years ago, and it's turned into this...
**Upasna Gautam** (00:43:18):
They've done amazing things with that product. So that's what I recommend, but again, you don't... I think, again, when people have a vision of meditation in their mind they're like, "Well I need these tools, and I need these resources, and I need these things, and I need knowledge." You don't need anything, you need five minutes and yourself, and that's it.
**Lenny** (00:43:37):
Amazing. I imagine many people listening to this coming into thinking, "I'm going to learn about CNN and how they build product," and then get a free meditation lesson. What a bonus, that was awesome. I'm going to be brushing my teeth very mindfully today-
**Upasna Gautam** (00:43:49):
Love it.
**Lenny** (00:43:49):
... my takeaway.
**Upasna Gautam** (00:43:50):
Love it.
**Lenny** (00:43:52):
Final question, around something that I know is important to you, that is basically there's this growing shift of product thinking in the news industry at large. And I know that's something that you're passionate about and something you're trying to create, is just to kind of move the media industry and the news industry toward more product thinking. So I'd love for you to just talk about what you're doing there, what's happening there, and then maybe if there's anything people could do to help in that effort.
**Upasna Gautam** (00:44:16):
Compared to the rest of product management as a discipline and the tech industry, product management in news is still in its, I will say infancy. And that's just because it hasn't been an integrated role for as long as it has been in big tech. But it is starting to become more and more not just prominent now, but people are realizing the value and power of it because especially in smaller newsrooms... I mean, CNN, places like The New York Times, The Washington Post, we have great, embedded, strong product teams. But that is not the case for the majority of newsrooms across the country and the world. Newsrooms are strapped for resources, they are strapped in all resources, including financial resources.
**Upasna Gautam** (00:45:07):
And so first, bringing in product and tech talent is expensive, and that in itself has forced editorial staff and journalists to take on other jobs that they never signed up for. And so they've had to learn how to do things product management, and engineering, and coding hacks, because there was nobody else to do it. And so it's interesting because a lot of times when you talk to editors and journalists, they're doing so many other things other than just their reporting of the news, right? They've had to take on other roles because of those restraints in the newsroom. And so there was a group established and a community established during the pandemic called the News Product Alliance. And there was like a realization occurring all at the same time that, "Wow, there's a lot of us doing this work.
[NEW_PARAGRAPH]"Like, what do we call it? Is this product management?" And it was, it's product management at so many different levels. And so the News Product Alliance was formed during the pandemic in 2020 I believe by several media and news executives, who had been there and have seen people in their newsrooms do that. And the goal of it is to increase the awareness and education of product thinking and product management in newsrooms, while also increasing the diversity of thought and the diversity of people in those positions as well. And making the resources more readily available, especially for those smaller newsrooms that don't have the money to hire tech talent. And that in itself has...
**Upasna Gautam** (00:46:56):
So that group, the News Product Alliance, has grown dramatically in the past three years since I've been a part of it, since the beginning. And we regularly produce the resources that are catered... Product management resources that are catered to working in a newsroom, because it is different, it is very unique. But there are of course frameworks and processes that are still relevant, right? Like editors who have been cobbling together how to make this thing that they want, but hey, maybe this PRD framework will help you, just to keep it on track. So these very simple, like rudimentary types of things have helped them so much. And so last year we kicked off a mentorship network in which we had about 400 people apply.
**Upasna Gautam** (00:47:46):
We accepted 150 mentees from across the world, and matched them with 50 mentors from different newsrooms across the world in leadership positions. And each mentee defined a goal that they wanted to work on, and all of course having to do with product management. And some of them were creating a product management role for themselves in the newsroom. Some of it was creating a product management practice, maybe they were given the title of product manager and said, "Okay, you can hire a couple of people." But it was all on them, and they had no idea what to do, right? And so some of it, it's across the board, and it's amazing to see people doing this from scratch who never in a million years thought they'd walk into it.
**Upasna Gautam** (00:48:32):
You know, they're not coming from big tech, they don't have startup backgrounds. They had journalism degrees from around the world, and they're learning how to do product, and build... Not just learning how to do it, they're building product practices, they're actually building and developing products and features, and they're creating more leaders in this space as well, and across their newsrooms to empower each other. So it's been really amazing to see, and it's the most valuable professional organization I've been a part of just because it is so niche that talking about product management is always fun. But when you talk about it at a level that specific, it becomes even more valuable.
**Lenny** (00:49:16):
That is some really impactful product work. Where can people find that if they want to maybe participate, maybe apply if you're doing another cohort in the future?
**Upasna Gautam** (00:49:24):
Go to Newsproduct.org, there is a very active Slack group with a couple thousand people in it, a very active and popular job board as well. And you just have to submit an application on the website... A form, sorry, on the website to join the Slack, and ten you'll get an invitation to join the Slack. And then you'll have all of the resources at your fingertips, it's very low barrier to entry, and we want everyone and everyone who is interested in the intersection of news and product to be a part of it. And the cool thing about it is like I mentioned, it's a global network. We have people from the biggest newsrooms across the world, to all of the regional ones, to even big tech, one of my fellow board members was doing news at Twitter.
**Upasna Gautam** (00:50:10):
One was working on the Google News Initiative. So it's a really, really awesome group of people, and everyone is so hungry and passionate about sharing and paying it forward.
**Lenny** (00:50:23):
We'll put a link to this in the show notes. One last question, and what kind of people are you looking for? Who should apply, if they're listening?
**Upasna Gautam** (00:50:29):
If you are interested in working in news and have a product background, or the inverse of that, if you work in news and you're interested in breaking into product. So either side of the coin or any combination of that, news media, product technology, even... We have a lot of audience development, and analytics, and data science folks in there too. It's just an amazing community for knowledge sharing in tech and news, so there will be a fit for you somewhere, or to learn something, or at the very least to meet other really amazing people.
**Lenny** (00:51:07):
Well, with that we've reached our very exciting lightning round. I've got five questions for you, and are you ready?
**Upasna Gautam** (00:51:14):
I'm ready.
**Lenny** (00:51:16):
All right. What are two or three books that you recommend most to other people, or that you've recommended most?
**Upasna Gautam** (00:51:21):
One, Mindfulness in Plain English. Two, How To Win Friends and Influence People. I have to attribute a lot of my communication skills to my dad forcing me to read that book when I was like 10 years old, and-
**Lenny** (00:51:36):
Wow, 10 years old. Intense.
**Upasna Gautam** (00:51:39):
He was an engineer, and they were in their very beginning phases of introducing... Well, at that time there was no product, but product-type stuff into his engineering practice. And so he had to read the book and was like, "You need to read this book." So I never forgot about it. And then the third one is actually, it's not a book, but it's an article that I think is still very powerful and relevant to this day. It's The New Product Development Game, published by Harvard Business Review in 1986. And it looks at a really different approach, one that I resonate a lot with because it's a lot along the lines of how we work at CNN, around rapid development, and time and flexibility being like key anchors of successful product development. So, I threw that in there as well.
**Lenny** (00:52:29):
Favorite recent movie or TV show? And it can't be White Lotus.
**Upasna Gautam** (00:52:32):
Okay, I haven't even seen that show.
**Lenny** (00:52:34):
Okay, great. That's come up so many times, we've got to not allow it anymore.
**Upasna Gautam** (00:52:38):
TV show is a toss up between The Mandalorian and Ted Lasso. I know it's not very new, but I don't watch tons and tons of TV, and I usually find like the few that I latch onto, and then I get obsessed with, and then I've got to take a break for a while. So, those are my last two obsessions. Movie is Everything Everywhere All At Once, the last amazing one that really, really struck a chord with me.
**Lenny** (00:53:02):
If you like Mandalorian check out Andor, it's incredible.
**Upasna Gautam** (00:53:05):
Oh yeah, it's good too.
**Lenny** (00:53:06):
It's like the best Star Wars thing. Okay, you've seen it. Okay, great, you're on it.
**Upasna Gautam** (00:53:09):
I still love Mandalorian more, I do like that one too.
**Lenny** (00:53:11):
Wow.
**Upasna Gautam** (00:53:12):
My husband is obsessed.
**Lenny** (00:53:15):
Okay, okay. Wow, contrarian. Favorite interview question that you like to ask candidates?
**Upasna Gautam** (00:53:21):
What's something that would not exist without your initiative?
**Lenny** (00:53:28):
Mm-hmm. And what do you look for in an answer that's a sign that this is someone you may want to hire?
**Upasna Gautam** (00:53:31):
The whole point of the question is like, do you have and can you exhibit high agency? And especially again, working in news it's so important. And so there's not like a specific answer, I think the ability to actually define something specific and tangible in itself is a really, really, really good sign. I think a lot of people definitely get startled by that question sometimes, because it requires you to kind of have to know what it is that you put on the table, right? So yeah, it's different every single time. But if they can define something out of that question, it's usually a positive sign.
**Lenny** (00:54:15):
Cool, thanks for sharing that additional detail. Next question, what's something relatively minor you've changed in your product development process at CNN or on your team specifically that's had a tremendous impact on your ability to execute?
**Upasna Gautam** (00:54:29):
Bridging the gap between product and editorial, that mutual trust and respect has had an outsized impact on our success as a high-performing team.
**Lenny** (00:54:38):
Sadly not something other people can use, but that's cool to know. Then we'll have to hire some journalists now, I think, to take advantage of that learning.
**Upasna Gautam** (00:54:46):
I can add onto that to make it relevant for others-
**Lenny** (00:54:50):
Sure.
**Upasna Gautam** (00:54:50):
... which is, it just goes back to, there's no substitute for having those direct conversations with your customers and your users. And it's like, when you understand that the assumptions you make are not one to one, or ever going to be one to one with their actual feedback. And developing that line of communication with your users and your customers is of utmost importance, I think that in itself is the key takeaway. It's like, how do you bridge the gap between collecting that feedback, having those conversations. Like, how far are you from your users, how frequently are you having conversations, how consistently are you having conversations? And I always think the more frequently and the more consistently, and earlier on in the process that you're having those conversations, the better.
**Lenny** (00:55:44):
Final question, maybe you already answered this. What's the most crazy or most memorable story from working at CNN?
**Upasna Gautam** (00:55:51):
Every election season is absolutely crazy in the best way possible. It's incredible to see our democracy in action, and watch history unfold. And while that's happening, using the platform you had a direct hand in building, and it's never lost on me that my work impacts the world every single day. And on the crazy, frustrating, stressful days, that is what serves as my anchor.
**Lenny** (00:56:19):
Awesome. Plus, this was amazing, I learned how to brush my teeth more mindfully, about elections, downtime, Trump, all these things. Final two questions, where can folks find you online if they want to reach out and learn more, and how can listeners be useful to you?
**Upasna Gautam** (00:56:34):
It's very easy to find me. Online I'm pretty active on Twitter and Instagram. I recently became an amateur content creator, so I share lots of stuff here and there on social. So any social platform... Well not any, only on Twitter, LinkedIn and Instagram. So any of those three is good, and I always love to hear feedback on stuff that resonated and made sense, and the stuff that there are further questions on. Always love having conversations around that. So yeah, DMs are always open.
**Lenny** (00:57:10):
I know we'll link to this in the show notes, but just, what's your handle on these networks?
**Upasna Gautam** (00:57:12):
It's my first and last name, very creative. I thought about it all by myself.
**Lenny** (00:57:16):
Awesome. And then I don't know if you answered the second question, how can listeners be useful to you?
**Upasna Gautam** (00:57:21):
It's the feedback, right? Like I love to hear what you found valuable, what helped you, what's a tactic that you took away and employed that helped you, things that made sense, things that didn't make sense, what you'd like to hear more about, any specific topic that would be valuable to do a deeper dive on. All of those things are very valuable to me.
**Lenny** (00:57:42):
Amazing. Again, thank you for being here, and adios.
**Upasna Gautam** (00:57:46):
Thank you.
**Lenny** (00:57:49):
Thank you so much for listening. If you found this valuable you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lennyspodcast.com. See you in the next episode.

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## [14/22] Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO)

**Annie Pearl** (00:00:00):
Strategy is really just an integrated set of choices that outline how you're going to win in whatever marketplace you choose. And so, a good product strategy is going to answer questions like what's your winning aspiration? But maybe more importantly, where are you going to play? What are the markets you're going to go after? What are the segments of those markets? What are the personas in the segments of those markets? And then, how are you going to win with a target audience?

**Lenny** (00:00:27):
Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard one experiences building and growing today's most successful products. Today, my guest is Annie Pearl. Annie is currently chief product officer at Calendly. Before that, she was chief product officer at Glassdoor. And before, that she was director of product management at Fox. She's also a member of Skip, a community for chief product officers, and she's on the board of two different companies. 

**Lenny** (00:00:54):
In our conversation, we cover a lot of ground, including how Calendly builds product, how Calendly has grown, including the wild story of how they got their first 1,000 users, and also how they built a sales team on top of what historically has been a very product-led growth company. Annie also shares a ton of great advice on how to get into product management. I learned a ton from Annie and I know you'll too. Annie also shares a few killer tips for using Calendly, which I loved. And so, with all that, I bring you Annie Pearl through a short word from our wonderful sponsors. 

**Annie Pearl** (00:03:53):
Thanks for having me, Lenny. Super excited to be here.

**Lenny** (00:03:55):
I've been a big fan of yours from afar. We've crossed paths a little bit on Reforge, on Twitter, probably been at events that maybe we didn't know each other at yet. So, I'm really excited to finally be chatting, real life, in real time, at least.

**Annie Pearl** (00:04:09):
Me as well.

**Lenny** (00:04:09):
I've got a Calendly question to kick things off. It feels like with Calendly one of the most awkward elements of it is I have to put the burden on someone else to book at Calendly. So, I'm sending a link and I haven't figured out a good way to send it to someone without it coming across like a power move. So, my question to you is how do I send a Calendly to someone without it feeling bad?

**Annie Pearl** (00:04:31):
All right, well I love this question to kick us off. We actually have a whole blog post about this if you're curious to learn more.

**Lenny** (00:04:31):
Oh, okay.

**Annie Pearl** (00:04:37):
But I think that at a high level, I think I recommend first really just kind of opening the door for the person you're trying to schedule time with to share their availability first. So instead of just sending the link, I usually start the email with something like looking forward to connecting, feel free to share, sometimes you're available or if easier, you can choose to find time on my calendar using the Calendly link here. So, opening the door to let them choose before you offer up your Calendly link, I think is a little bit of a subtle way to let them take the lead if they want. 

**Annie Pearl** (00:05:08):
And the second piece I would recommend too is once you opened that door, you can further reduce the effort on the recipient by adding times you're available directly in the email. So, when you go to share a Calendly link, there's an option to add times to email and you can then just paste those directly into the email you're creating, so that reduces yet another sort of point of friction to ask the user to click the link and get taken to Calendly. So, opening the door and then adding times to email are two things that I do to really make sure that it's not awkward and it doesn't put the burden on the other person.

**Lenny** (00:05:39):
That is awesome advice. That first one is what I ended up doing actually. That's really interesting where you don't send the link immediately. You first just ask, "Hey, send me your Calendly." And actually, I always say, "Send me your Calendly." I assume that's what they're using. That's kind of funny.

**Annie Pearl** (00:05:53):
Right.

**Lenny** (00:05:53):
I don't even know what else is out there.

**Annie Pearl** (00:05:54):
That's good. That's what we like to hear.

**Lenny** (00:05:56):
Yeah, absolutely. It's like its own word now. Okay, that was awesome. So, there's this already actionable advice for anyone listening. 

**Annie Pearl** (00:06:03):
Sweet. 

**Lenny** (00:06:04):
Transitioning a little bit to product, the main focus of chat, you transitioned into product from being a lawyer. You told me at one point that a lot of people ask you for advice about how to transition into product from other functions, especially non-technical functions as someone without a technical background. So, what advice do you give people when they ask you how to transition into a product role?

**Annie Pearl** (00:06:25):
I got what I'll call lucky, which is I kind of stumbled into product management after law school, joined the founding team of a startup and ended up doing product management there. But when I think about folks who are looking to get in their product management, I think there's really two paths. I think one is more formal in nature. There are associate product manager programs out there and many scaled companies, Google, Meta. All have APM programs that you can formally apply to. And actually, when we were at Box, much earlier stage company than either of those companies I just mentioned, we actually created an APM program to help grow our bench of more junior PM. So, I think you can actually find APM programs even at smaller, earlier stage companies than even kind of big tech. So that's one, it's just formal APM programs.

**Annie Pearl** (00:07:07):
I think another "more formal" way to get into PM is really by just directly applying to a junior PM role where there's no expectation of any sort of experience. I've usually seen this work best when you're already working somewhere in some product adjacency. Maybe you're in customer support, implementation, or maybe you're a sales engineer. But you can look at the internal job board and find junior PM roles that are posted and that's one way to make the move. So that's kind of on the formal side like APM programs and just applying via internal job boards.

**Annie Pearl** (00:07:38):
I think on the informal side, really two suggestions here. The first one is to seek out opportunities to shadow or partner closely with a product manager and maybe even offer to take on some work. So, some of the best PMs that I've brought over to product from other functions, they really start by expressing interest in product and then start partnering closely with the product manager and maybe even doing a little bit of product work before they make that transition.

**Annie Pearl** (00:08:02):
And one tactical suggestion is there's oftentimes companies will have subject matter expert programs where they want to pair someone from a go-to-market function with a certain product squad or a certain product area. And so that's becoming a SME. It allows you to really get more involved and embedded into the product team. So, that's one suggestion. And then maybe last one is just the path I did, which is joining an early stage startup. There's really usually an expectation that everyone's going to get their hands dirty doing a lot of different things. And so, I think that's one way where you might have an opportunity to try product management if you end up joining an early stage company.

**Lenny** (00:08:38):
So, maybe it was four, maybe it was more paths that you described. Join APM program. What was the second one again?

**Annie Pearl** (00:08:45):
Internal job board apply, when you're in the company.

**Lenny** (00:08:48):
As just like a junior PM. Two is, find someone that mentors you and helps you start doing the role. And is that internal? Is that the internal transfer app?

**Annie Pearl** (00:08:58):
Yeah, exactly. 

**Lenny** (00:08:58):
Cool. 

**Annie Pearl** (00:08:59):
And then, another flavor of that is sometimes companies will have these SME programs.

**Lenny** (00:09:03):
What is a SME program?

**Annie Pearl** (00:09:05):
Subject matter expert. So, you'll say, "Hey, I want to make sure we have subject matter expert in our CS team on this area of the product." And they'll partner really closely with the product manager and designer within that area.

**Lenny** (00:09:16):
Got it. And then the fourth bucket is, join a startup, start doing PM work and then you end up being a PM. 

**Annie Pearl** (00:09:21):
You got it. 

**Lenny** (00:09:21):
Which of those four do you find most common? And would you push people in one direction or another?

**Annie Pearl** (00:09:26):
Yeah, I've brought a lot of folks over internally for the path of someone's really interested in product, they express they're interested, they want to help, they want to learn, they're eager, they're curious. And so, they make that really well known and they're even willing to do some work on the side to help out and really show and demonstrate the skills before they have the job. So, I've seen that one to actually probably bring the most folks over in my role in terms of being on the product leadership side.

**Lenny** (00:09:53):
On the APM program route, are there any APM programs you recommend? Because I'm sure people hear this and they're like, "Yeah, but I don't know where to apply. I don't know which ones are good." I don't know if you have a list, but just what comes to mind as APM programs to go pursue? 

**Annie Pearl** (00:10:05):
The folks who started it all was Google, with the Google APM program. And Meta obviously has a pretty strong robust APM program. But as I mentioned around Box, I think those are obviously very, very competitive and most people want to get into them. It may be better to try and find a company like Box or a company that's a bit earlier stage, not as scaled to think about looking at those APM programs. And I'm sure if you want to, go to glassdoor.com where I used to work at Glassdoor, so had to throw that in there. You could search for associate product manager and I think you'll find a whole host of open roles that you might be able to apply to. 

**Lenny** (00:10:39):
That is a cool tip. I haven't heard of that. Go to Glassdoor and search for APM. So, you search for companies that have an APM title.

**Annie Pearl** (00:10:45):
Yes. You could just use associate product manager and you'll see all the open jobs out there and then go apply to them.

**Lenny** (00:10:50):
That's cool. Okay, good tip. What I find, and you mentioned this the best, if you have the option is internal transfer. If you're just like another function, you find someone that can help you move into the role.

**Annie Pearl** (00:11:01):
You have the relationships, you can show your work really well. The other thing I would say is when I think about folks who have successfully transferred over, I think they tend to have a couple of characteristics. They're usually very curious, they tend to be really passionate about the product and solving customer problems. And sometimes, they've even tinkered with a side project as a way to hone their PM skills. So, I think as you're thinking about making that transition, those types of characteristics really showing eagerness and interest in the product itself and solving customer problems are also great ways to get noticed and increase your chances.

**Lenny** (00:11:36):
Why do you think it is that not more companies have an APM program? It feels like such a win for so many people. Why is it just so rare? 

**Annie Pearl** (00:11:42):
Yeah, I think when we built this at Box, so drawing on that experience, it was a lot of work. If you're going to do it, you want to do it really well and you want to create an environment where you can help the associate product managers be successful, the goal is to ultimately graduate everyone from the APM program into being a product manager. And so, I think it takes a lot of intentionality and for us, it took a lot of work. We had to make sure we had clarity around the interview process. We had to make sure we had clarity around expectations in the role. We wanted to have a training element. 

**Annie Pearl** (00:12:16):
We wanted to make sure that, again, we're setting people up for success. So, I think companies have to be at a stage of scale where they can really invest and they have the excess capacity to build the program in a way. I think that's going to help make sure everyone who comes through it has a chance at really learning, growing and ultimately being successful.

**Lenny** (00:12:33):
That's the same thing we found at Airbnb. There's a PM that was so excited to make the APM program and it just never really happens. It just takes so much work. And to your point, you have to set up for success. You want to make sure there's clear paths and you upgrade to a regular PM and have the interview.

**Annie Pearl** (00:12:49):
And are we doing, is this really an APM program for internal folks? Is this external? Are we going to be really trying to promote this? So, I think there's a lot of ancillary activities around the actual program itself that have to be taken into consideration to make sure that it is actually very successful.

**Lenny** (00:13:06):
Yeah. Maybe a last point we should probably imagine you agree with is generally just hard to get into product management. That's like the default. There's just not that many roles at companies versus say, engineers or some other functions. 

**Annie Pearl** (00:13:17):
Right.

**Lenny** (00:13:17):
So, I think that's just like there are not that many roles. It's a difficult role to break into, but these are the ways you can do it if you actually want to. 

**Annie Pearl** (00:13:17):
That's right. Yep.

**Lenny** (00:13:27):
Okay. So, I want to transition a little bit to talking about Calendly. 

**Annie Pearl** (00:13:29):
Sure. 

**Lenny** (00:13:29):
There are two areas I want to go. One is just how do you build product at Calendly? What have you learned about product development and team building? And then two, talk about how Calendly grows and what you've learned about growing a product like Calendly. It's such an interesting product, especially from a growth perspective. So, to start on just how product is built at Calendly, just a little context. How many product managers are there and how many PMs are there? How many people total, roughly? Yeah, just to give us a little bit of [inaudible 00:13:57].

**Annie Pearl** (00:13:56):
Let's see, when I joined about two years ago, I think the company was about 150 people and I think we're about 600 now. And then the product team, there were about 15 product managers and designers when I joined again about two years ago, and I think we're around 60 this year.

**Lenny** (00:14:08):
Wow. So, 60 product managers.

**Annie Pearl** (00:14:14):
Product managers, designers, and a research team. Yeah.

**Lenny** (00:14:16):
Got it. What about just PMs?

**Annie Pearl** (00:14:20):
PMs probably, my guess is 20. 

**Lenny** (00:14:23):
Cool.

**Annie Pearl** (00:14:24):
Twenty-ish. Yeah.

**Lenny** (00:14:25):
Cool. And then, can you talk about how the product team is structured roughly? If you think about a tree, [inaudible 00:14:30] tree.

**Annie Pearl** (00:14:30):
Yeah. So, as I mentioned, we've got product managers, we have designers, we have a research team, and then product operations. And then, on my product leadership team, we have head of design, head of research, head of product operations. And then, within the product management team, I have leaders across core, across enterprise and platform.

**Lenny** (00:14:50):
Got it. So, you manage the design team and engineering team, you said?

**Annie Pearl** (00:14:54):
Not engineering. Design, product and research. Yeah.

**Lenny** (00:14:56):
Got it. Something that I find is one of the big differences between product orgs is design reporting up to a product leader versus not. What's the rationale there? And then has Calendly tried a different approach?

**Annie Pearl** (00:15:08):
Yeah. So, when I was at Glassdoor in the CPO role, I had the opportunity to lead design for the first time. So, coming into Calendly, I had led both product and design as well as research. And so, I think it made sense given I'd already done it once to keep that structure coming into Calendly. I think at the end of the day, the real benefit of the structure is really to say at the end, we want to be thinking about everything we're doing through the lens of the end-to-end user experience. And so, if we have product managers who are really prioritizing the problems we're going to go after, and we've got designers who are really trying to think about how do we bring solutions to life to solve those problems, having both of those functions roll into one person just really allows us to think more holistically around the end-to-end user experience.

**Annie Pearl** (00:15:53):
So, certainly, it can work where you have product and design reporting into different leaders that ultimately report into the CEO, but when you get to this level of scale from just a pure people management, but also just the scale of the business, you know often see this consolidation where product and design start to roll into one leader. And at least in my experience, I think it can help ensure that all the different pieces of work are integrated well together and ultimately deliver a better experience for customers.

**Lenny** (00:16:23):
So, it sounds like before you joined it wasn't like that. And if that's true, was there something that improved with that shift?

**Annie Pearl** (00:16:29):
So, the structure was there that way. At that time, we didn't have a head of design, so we had a lot of really great individual contributors and who had been, many of whom had been with the company for quite some time and really contributed to the great user experience that existed in the product. But we didn't have a design leader. So, one of the first leadership hires I made was to bring in a head of design to really build out that function. And then, that head of design is a peer partnering with the different heads of products across the product management organization as well.

**Lenny** (00:16:59):
What about in terms of the structure, whatever you can share one level below, how do you structure teams? Is it around outcomes? Is it around features of the product? Is it around type of persona? How do you think about that? 

**Annie Pearl** (00:17:13):
Yeah, yeah. So, we have a core team who's really responsible for the core end to-end user experience. In many ways, they're both doing feature development and then they're also doing growth work. So, they're thinking about how do we build new features and functionalities to help our core personas, which is typically folks who are in sales, recruiting and customer success. So, anyone in an externally facing role, we're really trying to help them do their jobs better. So, the core team's thinking about features and functionalities to really help our core end user persona. And then growth work to think about the PLG funnel, everything from acquisition, activation, conversion, and retention. So, that's one group. 

**Annie Pearl** (00:17:49):
And then, second group is our "enterprise group." And they're really thinking about two different personas. One is the IT admin, the person who needs to make sure that Calendly is secure and that they have all the reporting mechanisms to be able to manage their account and all the tools to manage users and groups at scale. And the second piece of that is also departmental leaders. So as Calendly selling into or being used by a sales organization, the head of sales is not the IT admin, but they are a Teams admin who needs to manage their organization within Calendly. So, the enterprise group really thinks both about the admin, but also sort of the departments and how do we better serve departments. 

**Annie Pearl** (00:18:31):
And then lastly, we have a platform team who's really thinking about how do we embed Calendly into the business processes of the organizations that we support and that we provide our product into. And so, that's everything from partnerships and integrations to our APIs.

**Lenny** (00:18:46):
Interesting. So, it's like problem focused/persona focused. Who are you trying to sell it to?

**Annie Pearl** (00:18:54):
That's right, that's right. Yeah, trying to sell it to, and then the persona of who's going to be using the functionality. And then, really having those teams hone and own those personas as they're developing functionality within the product.

**Lenny** (00:19:07):
What's your take on OKRs? Do you all use OKRs in some form?

**Annie Pearl** (00:19:11):
Yes, we do. We use OKRs both at the company level. So, we have three main OKRs that we're focused on for this year, for example, across the whole company. And then we have department level OKRs, many of which are in support of the company level OKRs, but then there's some additional things that we'll be doing at the department level, for example, that aren't going to show up at the company level. So yeah, we use them both at the company as well as on the product side.

**Lenny** (00:19:34):
Is there anything you've learned about making OKRs work? People love them. People hate them. 

**Annie Pearl** (00:19:39):
Yeah.

**Lenny** (00:19:39):
Is there something you do to make OKRs work? Something you've changed, something you've learned over time in how to work with OKRs?

**Annie Pearl** (00:19:44):
Yeah. When I first joined, I'd say we didn't have this muscle well built out. We didn't really have a clear product strategy at the time or clear OKRs guiding the work. And so, there was a lot of great work happening, but it really was unclear how it all fit together or how we were going to measure success in that work. So that was a first phase. I think the second phase for us was we developed a product strategy. We then had product team OKRs that corresponded to that product strategy, but they were really contained to the product team and each department across the organization had their own kind of siloed OKRs. 

**Annie Pearl** (00:20:20):
And then, phase three, where really, I'd say we headed into this year, we have a really clear set, as I mentioned, of company OKRs and then in these really tightly integrated plans across the company around how we're going to support the key results and ultimately deliver on the objectives. And this has been a really incredible transformation of dependency mapping, being able to make sure that we're pulling all the levers across the organization to drive our most important objective.

**Annie Pearl** (00:20:47):
So, I think it's just the kind of maturing of the business from almost no OKRs to product team OKRs to now company OKRs in a really tight planning process to make sure there's a lot of integration across the company to support what we need to do as a business.

**Lenny** (00:21:01):
So, what I'm hearing is one of the biggest changes in learnings was to connect OKRs across from the top to the bottom, right?

**Annie Pearl** (00:21:08):
Absolutely. Absolutely.

**Lenny** (00:21:09):
Is there anything else that has made a big impact on your ability to build and ship and execute as a company in terms of changes you've made in terms of how the company and how the teams build?

**Annie Pearl** (00:21:20):
I think one of the biggest changes that we've made, when I first joined, again, we had a product that served a lot of horizontal users. We help solo users who are freelancers, consultants. We help sales teams, we help recruiting teams, we help customer success, we help folks in education. So, we had a very broad user base. And what that means is that product managers in particular are I think had a really hard time prioritizing. At any point in time, it was really difficult to say, should I do work on feature A or for feature B without that clarity? And so, I think one of the most impactful things we did pretty early on in my tenure here was to hone in on our overall product strategy, but a poor piece of that being what's the actual market we're going after? What are the segments of that market? Who are the personas within the segments of that market?

**Annie Pearl** (00:22:09):
And so, we've made a pretty clear distinction now that while a lot of the feature work that we'll do to support our target personas of sales teams, customer success teams and recruiting teams will impact folks who are not in those personas. Those are the core ICPs that we're going after. And so, historically, that would've been always a sort of trade off decision and a question. And now I think we have a lot of rigor around who our target market and then persona we're going after. And so, teams can use that to prioritize and also just deliver better value for those users.

**Lenny** (00:22:45):
So, it sounds like the biggest unlock and one of the biggest unlocks for making the team more efficient, move faster, make decisions quicker, is narrowing in on exactly who you're going to be selling to.

**Annie Pearl** (00:22:55):
I think it's one of the harder things for companies to do. So, it sounds relatively easy, and I think most companies believe that they have clarity around this. But then when you go down into the weeds of asking someone who's product manager or a designer, I don't know that it's always as clear because there's always a bit of a hesitation to say no, right? And the idea of saying no is scary. When in reality, the ability to say no is going to allow you to make sure you're building something that's going to be amazing for the people that matter most and not something that's going to be average or okay for a lot of different people.

**Lenny** (00:23:28):
Was there anything that was really hard about actually executing that, convincing people we're going to narrow and not worry about these people and any lessons from going through that process? Because I imagine a lot of founders listening are like, "Oh, that sounds we should be doing this, but oh man, we're leaving all this money on the table, people are going to be pissed."

**Annie Pearl** (00:23:45):
Yeah, I think it's a pretty big cultural shift. So, some of this intersects with the shift from product led growth to adding in a sales motion. So, when I joined Calendly, all of our ARR came from our PLG channel. We didn't have a sales team, we just hired a CRO who was going to build out a sales team. And so, in that world, the way you think about product, the way you think about processes, even the people you have on the team are tailored to that business model. And then, as we sort of moved up market and have now explicitly started to go after teams of users and departments of users and organizations of larger scale, everything about people, process, and product all changes. 

**Annie Pearl** (00:24:29):
I think I touched on culture because I think that's pervasive across the entire organization. The way that things get done has to be highly integrated versus can be a bit more siloed when you're just sort of the self-service PLG business that in many ways runs itself through the product being well optimized. So, there's a lot of process change that needs to happen, the type of people that you need to bring into the organization, that changes as you layer in the new selling motion. And then the product itself of course has to change. 

**Annie Pearl** (00:24:56):
So, I guess let's just say the example of PLG and SLG or the direct selling motion is tied in to your question around what are the things that need to change in order to get clear on your target user? And I think it's highly cultural in nature across people, across process, and then obviously across the actual product itself.

**Lenny** (00:25:15):
I have a whole bunch of questions about how Calendly grows and maybe we just get into some of the stuff because I imagine a lot of people are interested. First, let me ask this. I imagine Calendly mostly grows through, I sign up for Calendly, they send it to everyone when I book a meeting and they're like, "Oh, what is this?" And they're like, "Oh, cool, I'm going to use this." And then they start using, it spreads, and then sales eventually finds people at a company that are using it a lot and tries to get the whole company in it. Is that roughly right?

**Annie Pearl** (00:25:39):
Yeah. Seventy percent of our signups come through that viral loop that you referred to. And then, of those signups, then they're usually solo users and then they start to invite team members in and then the team starts using Calendly and then usually the head of that team either inbounds to us or we have some sort of PQL data to know we should go after that team lead to try and have a conversation around expanding Calendly across their entire organization.

**Lenny** (00:26:05):
And PQL, product qualified lead, right?

**Annie Pearl** (00:26:08):
You got it. Yep.

**Lenny** (00:26:08):
Wow, what a loop. What a magical way to grow that everybody wishes they could have.

**Annie Pearl** (00:26:14):
It's pretty incredible, I will say.

**Lenny** (00:26:16):
Oh man. Okay, so going back to the question. When did Calendly hire their first salesperson, like any learnings about just how to start down that road once you start a product?

**Annie Pearl** (00:26:25):
Yeah. As I mentioned, when I joined two years ago, we just hired our first CRO and the PLG business really represented 99% of our ARR. And then, over the last two years, we've scaled the sales team in our SLG motion. Our sales led growth motion now represents about 20% of our ARR and it's actually the fastest growing segment of the business. I think there's probably two things I would touch on in terms of early sales hires. I think the first is, when you're making that transition from PLG to adding in the sales led motion, because you're starting from PLG, it's tends to be much more inbound in nature. You've got these sales reps who are working leads who have usually proactively reached out interested or as we mentioned PQLs. They have data to tell them that this is someone who has usage within their team, and therefore, we should reach out. 

**Annie Pearl** (00:27:17):
And so, that's a very different profile of a sales team member than you might need after you need to pursue more of a heavy outbound motion, more of a hunter profile than a grower profile. So, I think that's the first piece is just make sure you think about the motion when you're moving towards a sales led model. In those early days, it's more inbound in nature, and so the type of sales reps you might need are not necessarily going to be outbound, heavy kind of hunting sales reps.

**Lenny** (00:27:46):
Just one quick question on that actually, because that's really interesting. I don't know how involved you are in hiring these folks, but is it like, look at their background and they've worked at a company like that? Or is it personality type? Is there anything to look for specifically there?

**Annie Pearl** (00:27:58):
Yeah, I think it is mostly background and the type of selling that they've done previously more so than personality type. But I think the second piece, that's important too, and I'll answer your question on that one too, which is the target buyer. So, when you transition from PLG to sales led or adding this direct sales motion, the buyer is usually just the department head. It's the head of sales, it's the head of rev ops, it's the head of recruiting and it's not a senior person in IT or the CIO. And so, selling into this audience is different than selling into IT.

**Annie Pearl** (00:28:32):
And so, I think you have to be sure again that you have the right fit of sales folks with the target buyer in those early days. And so, to your question around what's that mean? You wouldn't necessarily want to bring on a bunch of sales folks who are at Oracle who are heavy in selling into CIOs in the early days because that's just not who you're the buyer's going to be. I mean, think we will graduate there eventually, but it's probably going to start from team lead to someone in IT to eventually a CIO led purchase, but that's certainly several years away. And so, making sure that the profile, the folks you're bringing on early match that target buyer in addition to match the motion around how you're going to be acquiring customers.

**Lenny** (00:29:15):
And to see that, is it similar? You look at the companies they worked at, it's like PLG-ish companies.

**Annie Pearl** (00:29:20):
Definitely. Yeah, exactly. Yep. Yep. 

**Lenny** (00:29:23):
Okay. So, along the same lines, as a product leader working with a strong and large sales team, anything you've learned about just how to build that relationship and build a product org that works really closely and well with a sales org?

**Annie Pearl** (00:29:37):
The first piece that really starts with is customer empathy. And at the end of the day, seeing the sales team and the go-to-market team as this really great asset that can help you as a product manager get closer to the customer. So, I've certainly seen organizations or been in organizations where the product team doesn't necessarily want to be bothered by sales, but I sort of flip that on the head and say sales and sort of the go-to-market teams in general could be your biggest asset to helping you get your job done well.

**Annie Pearl** (00:30:07):
When I was at Box, I was a product manager on the enterprise team and I spent a ton of time in the field and I don't know how I would possibly know how to have what to have built or how to build it to solve the needs of our customers if I didn't have that close relationship with the sales team and be able to lean on them because they're talking to, 10X of them were customers that I was able to ever talk to within any given week, really lean on them to be the voice of the customer to help me make the best product decisions that I could.

**Lenny** (00:30:35):
**Annie Pearl** (00:32:09):
The core challenge of being a product manager, right?

**Lenny** (00:32:12):
Just to add that I feel like the core job of PM is just tell people what's next, what's the next thing.

**Annie Pearl** (00:32:16):
That's right, and hopefully, you have a good reasoning as to why that thing, next is going to have the biggest impact, which is really where I start. I think it really starts with a clear product strategy that will dictate a few things. And I like this framework that's taken from a book called Playing to Win and it talks about how strategy is really just an integrated set of choices that outline how you're going to win in whatever marketplace you choose. And so, a good product strategy is going to answer questions like, what's your sort of winning aspiration, but maybe more importantly, where are you going to play? What are the markets you're going to go after? What are the segments of those markets? What are the personas in the segments of those markets? And then, how are you going to win with a target audience?

**Annie Pearl** (00:32:59):
And so, what I think this framework does kind of dovetails back to what I was saying before around prioritization is it forces you to create clarity around where you're going to play and where you're not going to play. And so, this really helps the product team hone in on delivering value for a very clear set of people versus trying to build something for everyone. And so, once you've established what that strategy is or what the playing field you're going to go after, then I think you can divide up your product work and service of that strategy. 

**Annie Pearl** (00:33:28):
So, I'll give you an example. At Calendly, we have the sort of vision, our winning aspiration to become the best place to schedule, prepare for and follow up on your external meetings. And then, we've articulated three horizons around how we're going to get there. Now, the year one that I was here, the percentage of resources we spent on that first horizon and the second horizon was about a 70/30 split and we put 0% of our resources on horizon three. That was too far out in the future and we didn't want to make any investments there quite yet, but we knew where we were going.

**Annie Pearl** (00:34:00):
In year two, it shifted. We went to a 50/50 split between horizon one and horizon two, but still, no explicit investments in Horizon three. And then, as we're entering to year three now, we've significantly scaled back the investment in horizon one, that's about 30% and then we've got 60% in horizon two and call it 10 in horizon three. So, I think just to close on the question of prioritization, I think it starts with a really clear product strategy which defines where you're going to play and how you're going to win. And then, the work and the percentage of allocation just should feed right into that product strategy and how you're doing against where you need to be in order to achieve ultimately your winning aspiration.

**Lenny** (00:34:38):
I don't know how much you could share here, but is there a feature that is people keep asking for it and it hasn't been built because of the strategy, the long-term vision, something that's like, "Nope, it doesn't fit. We're not going to do this."

**Annie Pearl** (00:34:50):
Yeah, I think the best example I can give is there's lots of small businesses and solopreneurs who would love us to have a Venmo integration. We have a PayPal integration. But our target market that we're really trying to go after as our primary persona are as I've mentioned, these sort of core ICPs within organizations. So, sales teams, recruiting teams, customer success teams. And so, it doesn't make sense within those personas to pursue something like a Venmo integration. Now, there's a lot of things we'll build for those personas that are going to help the small business, the solopreneur, the freelancer, but that specific feature is something that would be clearly deprioritized given the current strategy.

**Lenny** (00:35:29):
That's an awesome example. I want to get back to the growth stuff, but before I do that, we're kind of on this topic of planning and a cares and prioritization. I'd love to know just how you do planning at Calendly? How far out do you plan in detail? How far do you have roadmaps? How often do you plan? Anything you can share there?

**Annie Pearl** (00:35:45):
This starts again, I sound like a broken record, but with this really clear strategy around where we're going over the next couple of years and then we take that and we break that down into what are the most important things we need to do as a company this year in order to be able to make the right progress against that strategy. So, we have the company level OKRs and I mentioned that we have about three of those this year. And then, those KRs within the company, OKRs are measured annually, but we have milestones across a quarterly basis so we can measure progress more frequently than obviously on the annual or semi-annual basis.

**Annie Pearl** (00:36:19):
So, I think that's kind of at the high level. And then, obviously our product roadmaps are going to be in support of those key results that we needed to deliver to the business over the course of the year, but then broken down on a quarterly basis.

**Annie Pearl** (00:36:30):
I think one thing I'll just touch on real fast on is estimations and dates. Something we've done over the last year is really kind of moved to a model of talking about dates and promising and committing to dates that are within our control. And so, if you think about the product development life cycle, we can commit to a discovery effort of doing research around a certain problem space and we can have a general sense of when we know that effort's going to conclude. We don't know if we're going to actually end up going, and based on the results whether we're going to actually move forward with investing in that area, but that's a body of work we can commit to. 

**Annie Pearl** (00:37:05):
From there, we then move into, "Okay, if this is something a problem space we want to go after, we're going to go work on a couple different solutions and we're going to go do some user testing and we're going to land on a solution," and that's another sort of phase we can commit to. Then, once we actually have that completed and we actually know not just the problem but the solution, we can do estimation planning and actually have a date for delivery from an engineering perspective. And so, we've gotten a lot better at making the commitments around the work that's right in front of us versus making a commitment around a project six months out when we haven't even done enough discovery, enough design and ideation to have a real clear understanding of estimation.

**Lenny** (00:37:43):
That is really cool. Do you have terms for these phases, like these phases you have to get through these kinds of gates? Yeah, how do you describe that?

**Annie Pearl** (00:37:50):
Yeah, so the first phase we just call generally discovery. The second phase, we call solutioning. The third phase, build. And then, the fourth phase is launch, measure and iterate. 

**Lenny** (00:37:50):
Cool. 

**Annie Pearl** (00:38:01):
And then, we've designed the product development lifecycle around that framework.

**Lenny** (00:38:04):
So, discovery for example, is that a roadmap item for a quarter and that's like what you've committed to? And if that goes well, the next quarter has the next step.

**Annie Pearl** (00:38:12):
Yeah, exactly. You got it.

**Lenny** (00:38:14):
Sweet. Okay. In terms of the strategy artifacts, how does that look or do you have a Google Doc with a template that you all use? What does that look like? What's interesting about people not working at a company or working at just one company is they only have, strategy documents are really hard to see and see examples of. So, I'm always curious what these looks like. So, whatever you can share about what they look like and where you put them and how long and that kind of thing.

**Annie Pearl** (00:38:40):
We have a couple of different layers of this. I think the first is this high-level three-year strategy and this is actually called at the company level. So, if the doc, it also has slides that have been presented many times to the company when we're in the process of making sure that, that is part of new hire orientation so that everyone should understand where are we going over the next three years and then therefore how does this year's objectives fit into that. So, I think that's at that level. 

**Annie Pearl** (00:39:07):
And then, from there, we've got our product team OKRs. These generally start by docs and we write them in docs. So, they usually get translated into slides at some point for presentation purposes to the company and those are stored centrally in a location and then you get down to the feature level or the project level. And we have different kind of templates for the teams to use based on the type of work that they're going to be doing. And we're a pretty heavy Confluence culture, so we tend to use Confluence as one of the tools for housing and storing information around the work that's being done.

**Lenny** (00:39:39):
Cool. So, maybe on that topic, what else is in the stack of Calendly product team tools?

**Annie Pearl** (00:39:44):
We talked about roadmap planning, some combination of starts with docs, there's mural boards involved. Usually, it ends in slides. Then actually roadmap tracking, we use Aha and we use Airtable collaboration/communication. We use Slack, we use Loom, bug management, we use Jira. I'm trying to think of, is there any other?

**Lenny** (00:39:44):
Confluence, you mentioned.

**Annie Pearl** (00:40:05):
Confluence. Yep. Confluence is what we use quite a bit. Pando, we use quite a bit of Pando to help educate users within the product when we're launching new features. Yeah, I think that's the main stack.

**Lenny** (00:40:16):
And docs is Google Docs and slides is Google Slides.

**Annie Pearl** (00:40:19):
You got it. Yep. 

**Lenny** (00:40:20):
Sweet. 

**Annie Pearl** (00:40:21):
That's right. 

**Lenny** (00:40:21):
Okay. I'm going to bounce around and go back to growth questions and then I have a couple more product team questions. How did Calendly get their first thousand users? 

**Annie Pearl** (00:40:30):
A great question and I had to fact check it with my CEO earlier this morning, but there's actually a few really interesting things about this story and a few things that Tope did in the early days to get 2,000 users. So, for those who aren't familiar Tope, our CEO and founder started his career in sales and he spent lots of years in sales. And so, he was very used to the challenges of trying to organize external meetings with prospective customers. So, he knew the problem space really, really well. And he had evaluated all the scheduling solutions that were on the market and came to conclusion that there really weren't any great products out there and especially there weren't any great products for the recipient of the actual booking service. And so, I think he saw this as an opportunity for disruption. So, he raided his 401k, he took out all his savings. He didn't make raise any money. 

**Lenny** (00:41:23):
That's a lot of penalties, taking out money at that point. 

**Annie Pearl** (00:41:23):
Sort of. That's a very good point. I've never asked him about that. And he hired an outside development firm actually in out of the Ukraine to build the first version of Calendly. So, that's the background on Calendly. Why it's important is that the first 10 users were actually customer success agents at a company in the education space that contracted with the same firm that Tope was using to build Calendly. So, he really found his first set of users through the firm that he was using to build the product. 

**Annie Pearl** (00:41:51):
And then, those CSMs or customer success managers were actually using Calendly to schedule calls with parents in K through 12 education. And so, then those parents started using Calendly for their own parent-teacher conference scheduling. And then from there, the school started using it and then all the parents within the school started using it for lots of other use cases and it grew organically from there. So that was one piece.

**Annie Pearl** (00:42:17):
I think the other piece that's really important is that he started off by just having a free tier. The entire product was free. Some of this came from honestly not being able to actually build the billing infrastructure that would be required to actually charge. So, it came a little bit out of necessity, but it was also free. So not only was it a better product than the alternatives out there, but it was also free. So, the combination of the viral loop and coming in through getting those first 10 users as part of the firm he was using and then the free aspect or I think what led to the first 2,000, and then 10,000, and millions of users from there.

**Lenny** (00:42:52):
That is crazy. I have never heard a story like that where the team that is building your product ends up being the source of initial growth.

**Annie Pearl** (00:42:58):
I know, pretty crazy.

**Lenny** (00:43:00):
Oh my God. So many nice things happening in this history of Calendly.

**Annie Pearl** (00:43:03):
I know.

**Lenny** (00:43:03):
And wow, in Ukraine. So, I'm actually from Ukraine.

**Annie Pearl** (00:43:08):
Oh nice. That's awesome.

**Lenny** (00:43:08):
That's pretty cool.

**Annie Pearl** (00:43:09):
Yeah, they're great. [inaudible 00:43:11].

**Lenny** (00:43:11):
Yeah, and it's also interesting that it's rare that you hear a successful business starts with contractor engineers. I think OICs are like, "Do not do that." So that's a cool counter example of it can actually work out, especially if they're your first users and spread it to others. 

**Annie Pearl** (00:43:27):
And we still work with them. They're fantastic and they have incredible engineers, so they're still part of our culture, which is great.

**Lenny** (00:43:32):
So, Calendly got big in Ukraine, it sounds like initially.

**Annie Pearl** (00:43:35):
There you go. There you go.

**Lenny** (00:43:37):
What's something that would surprise people in terms of how Calendly grows today or grew through its history?

**Annie Pearl** (00:43:43):
Most people probably think about Calendly as the scheduling link and really for individual users to reduce the back and forth of email and scheduling. So, they think of that one-on-one use case and I think people would be surprised to learn that our team's business, so multiple users in an organization who want to collaboratively schedule together is growing much faster than our solo user business. And that's really where the future of where we think growth will come from is supporting these teams of users who are in externally facing roles and selling into departments and supporting multi-departmental deployments of Calendly across an entire organization. 

**Annie Pearl** (00:44:17):
So, I think it's still really well known as this solo user tool to eliminate the back and forth of email, but the growth of what we're seeing and where we think it's going to go is actually more teams of users and departments of users and then multiple departments in an organization.

**Lenny** (00:44:32):
It's interesting when you hear the story of Calendly that just has so many good things happening, basically for free, it's just grows so well. I think people don't realize you eventually will, that'll slow down, it'll taper off eventually. You'll need to drive growth very actively in these new ways that you're describing. And I think people don't often realize that they just wanted to find something that was viral and then things are going to go great, but it tapers off.

**Annie Pearl** (00:44:54):
Yeah. I mean, there's only so many people who, solo users who are going to pull out a credit card. And I think once you also get to hundreds of millions of dollars of revenue scale, just the law of large numbers, it means that growth will slow. And so, you have to figure out where's that next growth curve going to come from. I think the beauty of Calendly is that while we certainly have built features and functionality to support teams and departments, we got pulled there. It wasn't one of those things where we sort of said, "We need to find our next growth lever. Let's go build X." Our customers really pulled us there by the way that they were using the product. 

**Annie Pearl** (00:45:30):
And so again, a very fortunate position to be in, but when you can see in the data and see how customers are using it, that they want to be working on scheduling with their teams, that was our early sign, that's where the business was going to go in the future.

**Lenny** (00:45:46):
I don't think I mentioned this, I'm paying user of Calendly. It's what I use for booking these podcast episodes.

**Annie Pearl** (00:45:50):
All right.

**Lenny** (00:45:50):
You got me. I think I started when it was totally free and I was like, "How will they ever make money?" This is too much power. 

**Annie Pearl** (00:45:56):
And then, now, you learned that it was free almost by accident.

**Lenny** (00:46:02):
Yep. I was like, "Yeah, please take my money. This makes my life easier." What are some fun or unique traditions and cultural kind of components of the Calendly product team?

**Annie Pearl** (00:46:12):
A couple of fun ones I thought we could talk about. One, we have a meeting called OPA, which stands for opportunity/problem, assessment. And so, what this is, it's a meeting where basically PMs, I don't even go to it's a meeting for PMs to really debate and discuss with each other and spar around either areas and problems that they want to go investigate or after they've gotten data back or research back from evaluating an opportunity, deciding whether we actually want to move forward and go try to develop a solution. So, it's really in the product development lifecycle of letting product managers really get into a room with each other on a frequent basis and just think through things, debate, discuss. And I know that they all get a lot of value out of that.

**Lenny** (00:46:59):
It reminds me of something just like a bad version of that. I had a friend who was a PM at Zynga and he said there's a meeting where PMs present their plans to all the other PM. It was like you're in a shark tank where everyone's coming to destroy you. They just point out all the problems. That's all it ever is in this.

**Annie Pearl** (00:47:15):
I would say on this one, it's the opposite where I feel like everyone really needs the meeting. They're like, "Ugh, I really need to take this to OPA because I need to, I'm working through these problems and I really want to bounce it off of other people." So, I could imagine a world where it would be that. Actually, part of the reason I don't go to the meeting is that I really want everyone to be able to be open and transparent and provide feedback and not feel like there's any judgment from me or any needing to act a certain way because I'm in the room. So, that's sort of why I intentionally don't go. 

**Annie Pearl** (00:47:44):
Another fun one we do is something we call competitive work gaming. So, on some sort of time interval, sometimes it's been quarterly, we'll have assigned people into groups for the quarter to own a competitor. And their job is to essentially spend a lot of time immersing themselves into the product of the competitor, really trying to think through the lens of, do a SWAT analysis, really try to think through the lens of where's this competitor going and how Calendly only think about that and as it relates to our strategy. 

**Annie Pearl** (00:48:12):
And so, we spent a quarter doing that and then we have the competitive war gaming day where every team comes and presents and there's prizes and it's a lot of fun, but it's a really great way to stay on top of what's happening across the market without requiring every product manager designer to be deep in the weeds, there are a lot of different competitors. We can bring all of that knowledge together through what we call competitive work gaming. 

**Lenny** (00:48:34):
That is cool. It's really impressive how you do these exercises and they seem really positive and friendly and constructive. It sounds like there is a pretty unique culture at Calendly. I'm curious if there's anything else that's core to the values or the way that you think about the principles of building product at Calendly.

**Annie Pearl** (00:48:51):
What I touched on earlier is really core to how we build product, which is honing in on this target user and honing in on our target market. I do think it's quite rare. I think in most organizations that I've seen, I think there's a desire to do that. But I think, again, when it push comes to shove, it's really hard for executives to make decisions that say no to things. One of Calendly's actually core principles is focus wisely. It's pretty deeply embedded into our culture. And so, I think one of the reasons that I've been successful in being able to create the clarity around who the target personas are is because I think it's embedded into the culture of Calendly to focus wisely. 

**Annie Pearl** (00:49:29):
So, I don't know that it'll work in every organization. I think many organizations really struggle to say no, and they're always adding more onto the plate versus taking off. But I do think from an ethos perspective, there is something around focusing and the ability to focus to therefore deliver the highest quality of product that you can to your target customers. That is unique and I think it starts with some of the broader cultural paradigms that exist at the company and then we've now embedded that into the way we think about how we build product.

**Lenny** (00:49:59):
Is there anything else you do to instill that? It sounds like it's a core value. Do you put posters around the office? So how else do you keep people focused? 

**Annie Pearl** (00:50:06):
We're a fully remote company. So, now you've got my brain going on. Are there some sort of virtual sticky notes that you could get people to put onto their laptops to remind them?

**Lenny** (00:50:15):
Backgrounds to show us [inaudible 00:50:16]. 

**Annie Pearl** (00:50:15):
Yeah, exactly. Yeah, it's embedded into a lot of the documentation. So, it's embedded into the templates that I talked about in terms of, everything from sort of the way we structure that OPA, document that folks are going to be working on and debating too when they go to create the actual sort of PRD. When teams come in to present as part of our product reviews, we have a template that keeps reinforcing who's the target customer, who's the target user within that customer base, what are their needs and then how are we going to solve their needs better than any alternative that there is on the market. So, I think there's lots of different reinforcing mechanisms to that focus.

**Lenny** (00:50:57):
I feel like sometimes things like that come from a big problem the company had and then you index weigh the other side, focus, here's the four people we all build for. It becomes instilled in the culture.

**Annie Pearl** (00:51:08):
And I think you're right. I mean, because Calendly started as such a horizontal product, which was amazing because that's how it grew so virally and so it had the entry, the wedge into scheduling and how our first horizon and becoming the best horizontal scheduling automation platform was because we had that horizontal focus. And so, it was a blessing. But as we think about transitioning to horizon two, which is really about deepening our support for these teams and departmental users as well as verticals, that's I think the inflection point where we said, in order to shift us from horizon one to horizon two, we need to be making some real trade off decisions and we need to create this focus so that we can actually allow teams to go do that. 

**Annie Pearl** (00:51:52):
So, I think it's a really good point. We sort of had to create clarity around focus because we were trying to make a shift from broad horizontal platform serving lots of users to a deeper investment into specific users and specific teams of users within departments.

**Lenny** (00:52:07):
Before Calendly, you were at Box. Before that, you were at Glassdoor. I'm going to ask two different questions. You could pick which direction you want to go. What would you say are the biggest differences culturally between these three? If you had to bucket, here's how I'd describe Glassdoor, Box, Calendly. Or what did you take from those two places that you bring with you to Calendly and future opportunities?

**Annie Pearl** (00:52:27):
I love this question. So, they're all different, which is why I just feel so fortunate to have had experiences that were all quite different. So, starting with Box, maybe I'll take your second question. Box, when I joined, we were in the process of moving up market and trying to capture as much enterprise market share as possible, and I was on the enterprise product management team. So, I spent a lot of time, as I mentioned earlier, talking to customers. And in my first year in particular trying to ramp on the business. And I'd say my biggest learning during that time was around how to ask the right questions to really understand the why behind what a customer was asking for and then figuring out how to build a solution to their problem that would also meet the needs of a broader swath of customers.

**Annie Pearl** (00:53:07):
It became very clear early to me if I would just go build what customer A wanted and what customer B wanted and the customer C wanted, not only would that be wasted effort to do it three times, but more importantly, what they wanted me to go build was going to have a negative impact on the end user experience. And preserving that end user experience was so critical. So, learning how to ask the right questions to understand the actual problem and then build the solution that's going to be most scalable to that problem set across lots of customers was probably my biggest learning from Box.

**Annie Pearl** (00:53:37):
Moving to Glassdoor, totally different business model. Glassdoor is actually really more of a consumer business and 60 million unique users go to Glassdoor every month and it's a marketplace between job seekers and employers and it's highly, highly dependent on the consumer engagement, growing traffic, getting that traffic to come and engage and apply to jobs. And so, during my time as CPO there, I was responsible now for both sides of that marketplace, the consumer business and the B2B. And so, I learned all about how do you build PR consumer products, how do you think about optimization of a funnel? How do you think about building up a growth team and growth as a discipline? How do you use data and AB testing to make decisions? 

**Annie Pearl** (00:54:17):
So, I think that kind of consumer mentality and how you approach product, I then have brought with me to Calendly, which is really a blend of both, right? Calendly is first, as we've talked about a PLG business and it looks a lot more like a consumer business like Glassdoor. And then, it's got this direct selling business that looks a lot more like Box's enterprise business. So, I think I've been able to take kind of lessons learned from both Box and Glassdoor and apply them together to Calendly.

**Lenny** (00:54:43):
What a cool set of experiences. I'm trying to imagine you using all three in the same day. Sending a Calendly, storing your files in a Box and looking at reviews...

**Annie Pearl** (00:54:53):
And recruiting.

**Lenny** (00:54:54):
And recruiting. Yeah, yeah. Not looking for anything new. Okay. Final question. You are part of something called the Skip community, which I believe Nikhyl and a few people run. And so, I'd love to just hear a little bit about that and maybe how folks can join if they might be a fit.

**Annie Pearl** (00:55:08):
Yeah, as you mentioned about two years ago, Nikhyl, who was the former CPO of Credit Karma and is now a VP of product at Meta, got a small group of CPOs together who were all going through similar phases of companies' growth, late stage growth companies, and we all were facing the same challenges in our roles. And he formalized this community as a way to help us gather advice from one another, talk through how to manage challenges we're facing and just make us more successful in the roles. And we always joke, we're like the support group. 

**Annie Pearl** (00:55:37):
We meet on Sundays and it has been incredibly valuable as I've sort of gone through the last couple of years in my role at Calendly. Since then, we've grown the group to about 23 heads of products and CPOs and expanded the charter a bit, which I think is interesting to help product leaders not just be successful in their current role, but also how to think about setting them up for success in the role after this.

**Annie Pearl** (00:55:59):
And so, we're experimenting with a couple of different interesting ways to help product leaders grow. One of them is we're actually partnering with some companies right now to experiment with how can we help them as they're looking to make their first head of product hire or their first C O hire really hone in on what they're looking for and partnering with the talent partners we know to really help try to increase the success that they find the right candidates. That's something interesting we're doing. 

**Annie Pearl** (00:56:23):
We also recently launched a podcast covering some topics like, how do you manage the next job search, how do you avoid burnout, breaking down things like equity, and other kind of timely topics. And then also, we just have an active Discord server where we've got all sorts of channels from topics, how to manage the CEO/CPO partnership, compensation, even sharing planning, even sharing some advising opportunities or other CPO roles that kind of come across our radar. 

**Annie Pearl** (00:56:53):
So, it's been a really, really cool kind of experiment to see how the power of the community. And I know Lenny, you do a ton of stuff around community, how that has helped all of us. I think it's just more effective in our roles and feel like we have a group of people who are behind us supporting us during what is a very hard role.

**Lenny** (00:57:11):
I love this. I imagine when people look at a CPO, they imagine they just know everything already. They have a bunch of friends in the same role, but I think in reality, it's a lonely role a lot of times. And so, I could see the power of something like this just to help people understand who'd be a good fit for this, how do they go find it and yeah, it's like the [inaudible 00:57:33].

**Annie Pearl** (00:57:33):
The best thing to do is just follow the Skip community on LinkedIn. And then, we're targeting head of products, call it series B, C and beyond, up to late stage growth companies and up to CPOs. So, I'd say start by following the Skip community and if you see folks in there who are in the group, reach out to them to get a sense of what it's like and what it would be like to join.

**Lenny** (00:57:57):
And then, it sounds like if you're a company hiring a CPO, maybe reach out too.

**Annie Pearl** (00:58:00):
Yeah, that'd be great. That'd be great. Yeah.

**Lenny** (00:58:03):
Okay. And they do that by going to LinkedIn also and looking for the Skip community?

**Annie Pearl** (00:58:06):
Yeah, that'd be great.

**Lenny** (00:58:07):
Okay, cool. We'll put all the links in the show notes as well. Well, with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

**Annie Pearl** (00:58:15):
Let's do it.

**Lenny** (00:58:17):
What are two or three books that you recommend most to other people?

**Annie Pearl** (00:58:20):
Playing to Win, so, I reference that one earlier, Good to Great, and Hooked.

**Lenny** (00:58:25):
Awesome. What's a favorite other podcast that you enjoy other than maybe this podcast?

**Annie Pearl** (00:58:30):
I think I got introduced to you by Harry from the 20VC, I think. But if not, either way, I'll cross promote his podcast, which is a great one.

**Lenny** (00:58:39):
Yeah, Harry's responsible for this podcast. I was on his podcast and he's like, "Lenny, you should be [inaudible 00:58:43]".

**Annie Pearl** (00:58:43):
You got to do it.

**Lenny** (00:58:46):
He's the godfather of this podcast. 

**Annie Pearl** (00:58:48):
He is. That's great. 

**Lenny** (00:58:49):
What's a favorite recent movie or TV show? And you cannot say White Lotus.

**Annie Pearl** (00:58:53):
I have two young kids. So, whether I like it or not, Sing 2. It's a great movie, especially if you have young children.

**Lenny** (00:59:00):
Sing 2. So, it's like the second of Sing?

**Annie Pearl** (00:59:03):
It is. It is. Distinct from Sing 1. Sing 2 is better.

**Lenny** (00:59:07):
It's better. Okay, cool. I haven't seen it.

**Annie Pearl** (00:59:10):
I would hope you haven't.

**Lenny** (00:59:11):
Okay, cool. Favorite interview question that you like to ask people you interview.

**Annie Pearl** (00:59:15):
Talk me through your biggest product flop. What happened and what did you do about it?

**Lenny** (00:59:21):
What do you look for in an answer? What's a sign of something good in their answer?

**Annie Pearl** (00:59:24):
People being brutally honest around how bad it was and why it failed. The rest of the interview, they're trying to tell you all the wonderful things they did and all the accomplishments they had. And so, I think the rawer the answer in terms of how bad it was and why, the better.

**Lenny** (00:59:38):
Awesome. Next question. I think, you might have answered, what are top five SaaS products you use day-to-day, either at work or home, whatever?

**Annie Pearl** (00:59:46):
Slack, Miro, Loom, Pendo, and Confluence.

**Lenny** (00:59:51):
Awesome. And these are actually, unlike other people's answers, so that's really interesting. Kind of a unique stack you got there. 

**Annie Pearl** (00:59:57):
I love it.

**Lenny** (00:59:58):
Final question. What's your best Calendly Pro tip?

**Annie Pearl** (01:00:01):
Yeah, so we just launched a new feature that I'm loving personally called Customized Once and Share. So, this really allows you to make changes on the fly to an event type and tweak things like title or duration or override a date based on the person you're actually sending it to without having to go create a brand new event type just to make one small change based on the recipient. So, it's that one-off use case where you need to make a little bit of a change on the fly depending on who you're sending it to, but you don't want to go through the effort of creating a brand-new event type. So, I'm loving it and you should check it out. 

**Lenny** (01:00:34):
That is awesome. I need that. I find that I need to block dates out and change times and I just like go do that on my calendar, in my Calendly.

**Annie Pearl** (01:00:42):
There you go there. 

**Lenny** (01:00:43):
All right. Annie, this was amazing. We learned a ton about Calendly growth product building. Two final questions. Where can people find you online if they want to learn more and reach out, maybe ask some questions. And two, how can listeners be useful to you?

**Annie Pearl** (01:00:56):
Finding me, best place online is LinkedIn. And then, in terms of being helpful to me, one we're hiring at Calendly. So, explore open roles on the product team at Calendly if you're interested. Share any feedback for me on this episode@a.pearl@calendly.com. And then, as we talked about, would love to have you follow the Skip community on LinkedIn as well.

**Lenny** (01:01:15):
Awesome. We'll have all those links in the show notes. Annie, thank you again for being here.

**Annie Pearl** (01:01:20):
Thank you so much, Lenny.

**Lenny** (01:01:22):
Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [15/22] Gustaf Alstromer

**Gustaf Alströmer** (00:00:00):
If I drill down what makes companies fail, it's quite simple. It's just like they don't talk to users, which means they don't find product market fit. And if they don't find product market fit, nothing else really matters. What mistakes do people make is like it is all about that. It's all about talking to customers and learning that you're building something that's actually useful. YC Slack headline is make things people want, and it's still true and it's always going to be true.

**Lenny** (00:00:30):
Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard one experiences building and growing today's most successful products. Today my guest is Gustaf Alstromer. Gustaf is a group partner at Y Combinator where he's been for almost six years. Prior to that, Gustaf was at Airbnb for over four years where he started the original Airbnb growth team and where I was very lucky to get to work alongside him for a number of years. Gustaf is also at the heart of YC's increased focus on climate tech, and in my opinion is one of a handful of people who've had an incredible impact on the increasing amount of investment and people flowing into climate tech.

**Gustaf Alströmer** (00:04:17):
Thank you, Lenny. Honestly, it's so great to see you. I'm excited to be talking to you.

**Lenny** (00:04:22):
I've been looking forward to this conversation for a while ever since we booked this. We worked together at Airbnb for many years. I was really lucky to get to work with you before you moved on to bigger and better things at YC. Speaking of Airbnb, you once tweeted about how special an experience that was for you, and I think even more interestingly, how many of the people that have left Airbnb can't find another place that's as special that just like that bar has been set too high. And so my first question is just like, what do you think it was that made Airbnb so special? Why was it such an important experience for you and other people? And even more importantly, just what is it that you take from that experience that you bring to startups that you work with now?

**Gustaf Alströmer** (00:05:02):
Yeah, it's funny. I think this year in a couple of months it'll be 10 years ago since you and me started Airbnb.

**Lenny** (00:05:07):
Wow.

**Gustaf Alströmer** (00:05:08):
It was 2012. The reason I treated that was I asked everyone that I'd met after Airbnb, because I had this experience of like, this was the highlight of my career up until then, at least being in the team like that and I asked everyone, "Have you found anything better?" Besides maybe one or two people, I haven't heard anybody say that they found something better. And they all missed that dearly. I thought a lot about why that was the case, but I would say Airbnb did not feel like a normal job. It felt like more like a group of friends trying to just do something together and we were friends. At least in the beginning it did not feel like this was a job. It was sort of like an ongoing project and an assembly of amazing people. I think in the end we managed to build two things, like a really successful company, thanks to Joe and Nate and Brian just for starting this. Without them there would be nothing to build.

**Lenny** (00:06:04):
I think people don't like to use the word family, but I feel like that way because when I go and meet with Airbnb alumnis from that team. We have a very special bond that reminds me of close social connections more than anything else. It does not remind me of coworkers. I asked myself why this was the case. The best answer I have is probably we brought in a special type of people. We had very diverse backgrounds. A lot of us was former founders. Not many of us were career people from the technology industry of the early days, not many of us.

**Lenny** (00:06:37):
I think that bar that we set, the first, I believe when I joined there was probably five or seven PMs and there was 30 engineers or something and you joined a little bit before me, those people set the bar or set the standard of what we were looking for afterwards. I think it took a long time to change that narrative. I mean, eventually you have to hire people that only had big corporation careers, but I don't remember we did that for a long time. When I actually read my goodbye note recently, my words there still means a lot to me and it means sort of like you're trying to reflect on exactly these things on like, building a great company that became successful and being part of this sort of family of really close friends.

**Lenny** (00:07:21):
So it sounds like if you had to boil down what Airbnb did, it sounds like hiring was the main piece that impacted the way it turned out just like the founders being very specific about the type of people they were hiring.

**Gustaf Alströmer** (00:07:32):
Absolutely.

**Lenny** (00:07:32):
Is there anything that's like, I don't know, a take away there of just what you recommend to founders, like hiring. People know, be very careful who you hire. The first, I don't know, 10 people will impact the culture long term. But I don't know. Is there anything just abstracting away there of just what to look for in that first batch of hires?

**Gustaf Alströmer** (00:07:50):
It's a tricky one because I would like to say that all the things that we did were the cost of the outcome of this, but that's not really how the world works. Some of the things we did work, some of the things that we did did not work. It's hard for us to actually disentangle what those things are, but I think we can talk about the things that we did. First of all, we made sure we hired people that were really excited to be there, right? They wanted to build Airbnb and they were really excited to work on Airbnb. That was the most important thing. Of course people had other offers, but I think you can figure out from those offers are you excited to be here or not. So that was probably the first thing.

**Lenny** (00:08:30):
The second thing I think is trying to understand the true motivations of the people that were there, like lower, "Why are you here?" We did something we call culture interviews that I think the founders have written about or there's probably content online about this. We did a lot of culture interviews early on to try to figure out we got the people that were there that mapped our core values and were really excited to work on Airbnb. I think finally, I don't know how this happened, we did pick people from diverse backgrounds. Most startups don't have most of the PMs being former founders, but I believe that was the case for the first 10 or 12 or 15 PMs at Airbnb. A lot of us were former founders. I think that that made a big difference for how you make decisions and how you get started on things.

**Lenny** (00:09:21):
I think I actually see this a lot in the Airbnb founders. They really care about the time at YC and they tried to recreate YC inside Airbnb a couple of times with demo day and with so new products completely isolated from the rest, starting with doing things that don't scale and talking to customers. So I think that that experience had made a big impact on them, but it's hard to say just these two things go and apply these things. It's actually kind of hard to say, "Well that will work at it as Airbnb." I think that's a really tricky question to answer.

**Lenny** (00:09:51):
The last thing I would say is Airbnb had an incredible business model, an incredible business from early on and it was hard to fail. What I mean by that is it's hard to fail with a company. You can fail with individual things inside the company, but a company was still going to succeed. I think we all felt that. A lot of companies don't have the ability to take risks like Airbnb did early on because they don't have something that's so obviously great.

**Lenny** (00:10:18):
That's a really interesting point on the last piece that you may have the most amazing culture and hire incredibly well, but if the company doesn't work out, it's not going to be looked back as like, "Wow, that was an amazing experience, but we failed."

**Gustaf Alströmer** (00:10:18):
Yeah.

**Lenny** (00:10:30):
Yeah, that's interesting. So you mentioned YC and this kind of is a good segue to where I want to focus most of our time. You mentioned that you've worked with over 600 companies at this point, which is absurd. It feels like it's you get some statistical significance on takeaways at this point of what works and doesn't work. So I have just a bunch of questions about your experience working at YC and with all these companies. The first is I think about this quote that Elad Gill tweeted once and he wrote, I think, a post about it. Elad Gill is a legendary angel investor. He said that starting a company is an act of desperation. You're either desperate to change the trajectory of your career or you're desperate to make a bunch of money, you're desperate to achieve some kind of mission or build a specific product that you're just like, "I need this to exist." I'm curious if you agree with that sentiment and then I have a follow-up question around that.

**Gustaf Alströmer** (00:11:20):
Yeah, actually I haven't heard it before, but you know me, I'm an optimistic person. I think it probably reflects on my view of this question, but I would say desperation sounds like a negative place that you're starting at. I actually think that most people to start companies start from a positive place. But the motivations, I agree with what he said, can be very diverse for successful founders, right?

**Lenny** (00:11:41):
So we actually asked this in one of the early Group Office Hours sessions. We asked them, "Why are you doing this?" And we don't want to hear an answer like, "I found this niche of the market.' That's not the why. The why is like, "Why will you come in and work late after four years when you have no money left and everything's going to shit?", right? Then the niche market is not the answer. There's something deeper than that. We've learned that it varies a lot for people's motivations to start companies. Some of them just want to solve some technical problem that they feel are passionate about solving. Some of them want to prove themselves in front of others or prove themselves towards themselves. Some have grand really important motivations to change the world and they will say things like, "I want to give everyone water or I want to solve climate change or I want to democratize publishing." You can imagine any number of large ideas. Some people just want to start a big company and just want to be successful.

**Lenny** (00:12:44):
It doesn't matter, in my experience, what your motivation is. I don't think either of these motivations. It sounds like some of them will be better than others. In my experience, it's not the case. The motivation will change over time to just running this thing, right? Like once something becomes big, it's hard to think every day about exactly why you got started because the motivation is just like it can be fun and work on boring things because it's fun to build something big. Everything doesn't have to be shiny and big and grandiose because there are many ideas that are "boring," but just the idea of running the company becomes the motivation eventually.

**Lenny** (00:13:17):
That is really interesting that one of the main things you look for, it sounds like when you're interviewing, is how strong and durable is that drive to build this company. Is that what you're saying?

**Gustaf Alströmer** (00:13:26):
It's actually kind of hard for screen for motivation, I would say, in interviews because the purpose of this kind of Office Hour question is to highlight why someone is there and highlight the diversity of reasons people are there and sometimes even highlight from one founder to another co-founder why they are doing this. They might have never talked about this. Actually, surprisingly, often founders have not talked about why they're doing this. And just knowing why someone is here really helps with conflict resolution for example, really helps with understanding why someone is there on a certain day or something like that. So it's not something we screen for as much as I think we try to help founders discover this among themself and really know this about themself. I've just accepted that the motivations to start companies is widely diverse.

**Lenny** (00:14:13):
Do you ever discourage founders from starting a company when you see that maybe it won't be a durable kind of lasting motivation or whatever other reasons just knowing how hard starting a company ends up being?

**Gustaf Alströmer** (00:14:23):
It's a good question. I would say sometimes if someone doesn't have a motivation or don't know why they're doing this, they're doing this because they read that it would be a natural career step. So a good reason to not start a company is if you think of starting a company as a career step. Well, it is not. Because if it's successful, it'll be your entire career. It'll be 10 years most likely. And if it's not successful, then it's not something that people generally aspire to start. So non-successful startups. So I think people will start companies because this is sort of something they want to put on their resume. They have not understood what startups are or why you should do them.

**Lenny** (00:14:58):
Sometimes you can screen and kind of figure this out, but sometimes people don't even know why they're starting a company when they get started and it kind of gets figured out along the way. And that's okay. I don't want to discourage people who don't know exactly why they're starting this company just to start a company. They might figure out along the way and find the true motivation after doing this for a little bit or finding that it's really fun.

**Lenny** (00:15:21):
I think I discourage people to start startups if they have so many other things that are important than their life that are more important than the startup. So if there are financial constraints or family constraints or relationship constraints and they are going to trump this, then yeah, you should think a second time perhaps because startups are hard. They're much harder than a normal job. Equally hard if they're successful or failure, right? There's no middle way, we're like, "Oh, my company is doing great so I can chill." That doesn't work that way either. So I don't really discourage or encourage people, I just want them to have all the information.

**Lenny** (00:16:03):
You mentioned YC Office Hours and I had a question around this. I'm working on this piece where I'm interviewing a bunch of B2B founders of companies that are doing super well and I asked them a few questions like, "How'd you come up with the idea? How'd you find your first few customers?" it's shocking how many of them bring up a conversation in YC Office Hours as the most pivotal point that set them on the trajectory that they're on now. I'm curious what happens in these Office Hours? What are the most common pieces of advice that you give or maybe most surprising pieces of advice that you give in these Office Hours so that people can get maybe a glimpse into these conversations you have?

**Gustaf Alströmer** (00:16:43):
So at YC we have two type of Office Hours, two of the common ones. We have regular Office Hours, which is usually a one-on-one or basically the founders talking to me, or me plus another partner. They happen every week or every other week throughout the entire program. And they happen years after the program on the regular basis. Then we have Group Office Hours, which is you and six or seven other startups talking to us. They have [inaudible 00:17:07] a little bit different purpose. So the goal of the regular Office Hour, I always ask the question, "What's holding you back from moving faster? We don't want to hear updates, we don't want to hear strategy questions. We want to understand what's slowing you down or what's holding you back from moving even faster. You generally have a specific goal."

**Lenny** (00:17:27):
And I think that question of what's slowing you down or were holding you back crystallizes the priorities. There are only so many things you can do as a startup and there are only so many things that matters at that stage. And by asking that question, we can start digging into, "Okay, what's the goal? What are the things that drives towards that goal? What are the things that's slowing you down towards that goal?" Usually, the founders don't know what's slowing it down, so the conversation and us probing questions actually leads to us or them discovering what it is just slowing them down.

**Lenny** (00:17:59):
In the Group Office Hour, it's a little bit different. The Group Office Hour holds a couple of different purposes. One of them is if I think back on Paul and Jessica's motivation to start YC, this is a surprise to them, but starting a company is incredibly lonely. You can't really lean on your employees and say, "Hey, I'm feeling really shitty as a founder today. Everything is going to shit." Employees isn't going to take that well. So you lean on perhaps your investors, but they're not really available. But what you can lean on is other founders because they're all in the same situation. It's sort of like when you ask a founder the question, "How are things going?", it's so emotional for them to answer that question because it's never going well, right? It's never like, "Oh, everything is going fantastic." They might say that, but everybody knows all founders, when they look each other's eyes, then no, that's not the answer.

**Lenny** (00:18:48):
So founders have infinite number of problems that they're thinking about all the time, which is why they're allergic to the question, "How are things going?" But when YC started, we put all the founders in a group together in a room and they started learning that all founders, all companies are broken in some way, right? They're all having these massive problems and they're all feeling that anxiety when they hear the question, "How are things going?" And just hearing other founders explain their problems, perhaps solving their problems, is a really good way for yourself to both feel motivated to do it yourself and see how problems get solved when other companies are having similar problems. Nowadays because of the scale at YC, we group companies together that have the same problems or the same area that they're operating in.

**Lenny** (00:19:30):
The second thing that Group Office Hours do well is accountability, right? We ask you, "What were your goals? What were your goals for the last two weeks? Did you hit them?" And then that gives founders accountability because founders are competitive. They don't want to look bad. They don't want to come back after two weeks and say "Nothing worked," or at least like, "We didn't learn anything." They want to learn something and make progress whether it's positive or negative.

**Lenny** (00:19:54):
Group Office Hours to me is the most magical moment because it really creates this very intense three or four month period. Founders often come back to us afterwards and say, "Hey, we want to do that again. We don't have this really intense, really productive period. We don't have a program exactly. We have other programs, but we don't have anything exactly that mimics that experience." But we do encourage founders to continue with Group Office Hours after YC. Many of them do and many of them, ad hoc, continue to meet for years in this group setting where they ask the same kind of questions to each other, to hold themselves accountable, to learn from each other, and to just have someone else to lean on. I think this was unknown and somehow the world didn't know before that starting company is super lonely and you have all these anxiety. By just talking to other people who have the same problems, it's just one of the best thing you can do.

**Lenny** (00:20:45):
There's so many things that come up when you talk about this. One is I had a startup at one point and we worked in the coworking space. We joined the coworking space because we're like, "Oh, we'll meet other founders. It'll be social, we won't be alone." But it turns out everyone's just heads down, headphones on, "I don't have time for anything. I just need to work." It's like a microcosm of that experience that even if you're surrounded by founders, no one has time to do anything. They're just working.

**Gustaf Alströmer** (00:21:09):
You got to schedule it and force it and put the laptops on the floor and the phones on the floor and you just sit there with pen and paper. That's how you have to do it. We tried to mimic that as much as we could over Zoom. But honestly the best experience of this was in person, in a ring, in mountain view with no computers and everyone just paying attention to everyone. That was the best experience. Yeah, that's what I remember is one of the most meaningful parts of YC. I didn't have it myself when I did YC, but now everyone has it.

**Lenny** (00:21:36):
The other thing that's made me think about is someone tweeted once, "Don't ever ask a founder how they're doing or how it's going. It just creates all this anxiety because nothing's ever going great."

**Gustaf Alströmer** (00:21:44):
Don't do it. Everybody looks at each other's eyes and they know that they're allergic to that question.

**Lenny** (00:21:50):
That's hilarious. So just to summarize the questions you said you asked, the one is in the individual Office Hours, is what's holding you back. And then in the group setting, what was the question again that you asked?

**Gustaf Alströmer** (00:22:01):
What are your goals for next two weeks and what were your goals for the last two weeks and did you hit the goals? And if you didn't hit them, what came in the way of hitting the goals? It's very simple. That can uncover lots of problems that other founders are having exactly in the same way. Just by talking about the things that held you back or the things that allowed you to hit your goals, uncover something material for the other seven companies doing that in the ring.

**Lenny** (00:22:26):
If you kind of zoomed out a little bit and thought about the startups you've worked with, what would you say are the most common mistakes that early stage startups make broadly?

**Gustaf Alströmer** (00:22:36):
There's so many. I mean, this is how I initially learned about startups, by searching for that on Google and landing on Paul Graham's articles because he kept-

**Lenny** (00:22:45):
Wow.

**Gustaf Alströmer** (00:22:45):
I think I've written many articles about this topic because it is so common. So this topic can go on forever. But if I take the most recent experience I've had in YC, I would say startups fail, one, because they don't talk to customers. And if you don't talk to customers or users, you don't actually know what's important. If you don't know what's important, it doesn't matter what you build, it doesn't matter kind of what ideas you have in your head if you don't actually know what it is that you need to build and you don't validate with customers. That's where a lot of the failure stems from. A lot of early YC for us or early part of the program is us pushing and probing founders to be like, "Tell us about the conversations you've had with the customers. What did you learn? Can you show us the organizations?" Or like all these questions, like, "What are the software they're using? What are they paying for? What problems do they have? How are they describing the intensity of that problem?" So that's what we spent a lot of time early at YC.

**Lenny** (00:23:43):
After that, I would say one of the commons mistakes in... I'm not talking about generally startups here, I'm talking inside YC. The second most common thing I see in YC is people are just afraid to talk to customers. They're just not trying hard enough to get in front of customers. I think this comes from, technical people tend to think that software is just sort of solution to everything. But really what you should need to do is to talk to someone over Zoom or over phone or in person, even better. People are just afraid of doing that and they're afraid of being rejected. These are common, people that want to build good products are just really afraid of people saying no.

**Lenny** (00:24:25):
The problem is, which anyone who hasn't done sales before that joined YC, they realize this, is that if you take the average customer group in the world, 90% are not early adopters. It doesn't matter if you have something new and cool, they're just not interested. They are not incentivized to take risks in their job to try something new. They're just incentivized to not take risks and just continue what they're doing. Those 10 percents are the early adopters. They're The ones that you actually want to reach. But that means you have to reach 10 to find one. And then you convince that one person to get on the phone or a video call with you. And that takes work and it takes a lot of work. I think people don't really think of this. This is common knowledge, basic stuff for salespeople, but founders should never done sales before just get surprised by the percentages and the sort of what it means to do this.

**Lenny** (00:25:12):
If I think of more generally outside of YC, so these are two kind of things I experience within YC, but I think generally outside of YC, I would say the two most common problems the same one is not talking to customers, the other one is not being technical and not knowing what it takes to build successful technology company. It means having technical founders and it means being able to build the first prototype. This is something we screen for when we interview people in YC and we aren't accepting a whole lot of team that don't know how to build or get their first prototype built themselves because we know it is a super common value pattern.

**Lenny** (00:25:50):
I can go on and on and on and on for this one, but honestly if I drill down what makes companies fail, it's quite simple. It's just like they don't talk to users, which means they don't find product market fit. And if they don't find product market fit, nothing else really matters. What mistakes do people make is it is all about that. It's all about talking to customers and learning that you're building something that's actually useful. YC Slack headline is make things people want, and it's still true and it's always going to be true.

**Lenny** (00:26:23):
This is really interesting and good advice. It's interesting that... Like, "Talk to customers," people hear that all the time. They're like, "Of course we're going to talk to customers. We're going to do that of course." And your experience is they know this but they just don't do it probably because they're afraid. Maybe also because they think they already know what they need to build and it's like, "Yeah, we're good."

**Gustaf Alströmer** (00:26:41):
And you have all these validators, right? So the people are validating that even if you don't talk to customers, why has he accepted you? This investor invested in you. This investor said you were great, like blah blah blah. All these different validations that you confuse with product market fit, right? We have to remind everyone on the first day in YC, "None of you have product market fit because you probably don't," right? Almost nobody has. Because people confuse this external validation with the thing that matters the most, which is talking to customers and learning what matters. It's just like a thing that just keeps coming back. Some get really good at it. And that is the source of successful startups, is when you really get good at this.

**Lenny** (00:27:21):
It reminds me coming back to Airbnb, one of the most important moments in Airbnb history was Paul Graham telling the founders of Airbnb, "Where are your customers?" And they're like, "Oh, they're in New York" and he's like, "Why are you talking to me and not in New York right now talking to them?" And they talk about that all the time.

**Gustaf Alströmer** (00:27:35):
Yeah, it's absolutely true. I think he wrote the article Do Things That Don't Scale as a learning.... The learning there was the Airbnb founders doing the trips to New York and learning about how to build Airbnb, which is a very counterintuitive idea, which is when you have to spend the most amount of time with your customers. I think Airbnb is sort of one of the best stories inside YC of doing this well.

**Lenny** (00:27:57):
This also reminds me, I've been talking to a bunch of founders recently. I asked them, "How many customers have you talked to help figure out this idea?" So just the other day it was 150 financial CROs that they talked to before they actually started raising this round. Another company, actually two Airbnb guys that started, they actually ran ads I think on LinkedIn to find specific people to talk to and that specific role. And they talked to probably at least 100, maybe 200. So there's a strong correlation there.

**Gustaf Alströmer** (00:28:26):
Yeah, I think that's the volumes that people don't expect. They think they might have to talk to five, but I think you have to talk to 25 to 50. That means you have to reach out to a lot more to be able to get to people that are potentially early adopters. Those ones you talk to are also the ones that become your customers. So you are already doing most of the sales by just doing this work anyway.

**Lenny** (00:28:45):
Do you have maybe one tactical tip you could share of just either getting over your fear of talking to customers or just holding yourself accountable to actually doing it?

**Gustaf Alströmer** (00:28:55):
Yeah, I tell this story, I actually told this story yesterday. So remember when you sign up first service that's a cool service and you hear about in TechCrunch or something like that and then you realize you already signed up a year ago, right? And then from the founder's perspective, you sign up to something you never used it. So the founders who build those services, their inclination to think is that "Everybody hates me because they sign up and they never use me." They never use the service. The fear of that is that basically the fear of rejection. So if I put my thing out there and most people won't use it and they will tell all their friends how shitty this thing is, you should never even sign up for it, that's the fear people have, but the truth is that people sign up for it and be like, "Oh, I'm busy. I got something else to do." And they actually don't remember or care.

**Lenny** (00:29:43):
So whenever you sign for something that you signed up a year ago, think of yourself that that is the common customer experience, which is that you just sign up for a lot of stuff you don't even remember you. You never have this, "I hate this thing' reaction. You always have this like, "I'm indifferent to this thing. I don't actually care to even complete the sign up flow or try it out," right? I think that's the thing that people need to remember, is that the worst thing that can happen to startup is not that people hate what you're doing, it's that they're completely indifferent to what you're doing. It's not the worst thing, but the most common thing that happens is people just is indifferent. But it doesn't give you a second chance. Let's say, it always gives you a second chance and you really need to internalize that people have busy lives and if people don't actually use what you're building, that's fine. You can reach out to them a year from now or six months from now or two weeks from now and they probably will if you make some improvements.

**Lenny** (00:30:37):
I think people just have this fear that, "If I get a lot of rejection, that means everything is bad." But the rejection should be put in context to the early adopter idea and that most people who don't care are not early adopters, who don't want to dig into new things. And that the more narrow of a solution you have to a specific problem, the fewer people actually want to dig in. But that's where you have to start because you cannot build the whole thing right up front and make everybody loves you. That doesn't really work that way.

**Lenny** (00:31:07):
Even Airbnb was like air mattresses or staying in someone's homes when they're home. That was not the complete solution of Airbnb. But there were early adopters who dug in and be like, "Yep, I like that. I like those two things. I want to have people stay in my living room in my mattress." But that's not what Airbnb is about today, and a lot of those things were unknown at the time. But I think people are just afraid of rejection and you just need to overcome that fear and just learn that there's nothing that's really that bad that can happen when people don't use the service or sign up and don't care. It's not really that bad.

**Lenny** (00:31:42):
It reminds me of a quote that I always love for Mark Andreessen, that everyone's time is already allocated. They don't have space for your product right now. They already have plans for their day.

**Gustaf Alströmer** (00:31:42):
Totally.

**Lenny** (00:31:51):
And it takes a lot to convince someone to pay attention to anything. I guess that just comes back to why it's so important that your product is solving a real pain and not just a nice little toy that is better than what's out there, but not so much better that you're like, "I need this right now." So maybe just along those lines, do you have any thoughts on just the importance of that pain and just how critical that is?

**Gustaf Alströmer** (00:32:15):
I actually recorded... I'm happy of these videos, but I've recorded two videos on YouTube as part of YC Startup School last fall. You can go watch them on YouTube right now. One of them is how to talk to users and the other one is how you sell or how you use sales. The one about talking to users, I think there's a difference in asking someone, "Do you have a problem with X, Y, Z? Is this podcasting setup working for you?" And people say, "Yeah, it's kind of working." But if you are a podcasting setup experts and you watch people use some other thing that's really shitty, they might also think that it's pretty good. But you have to watch them do it. And the best way for you to figure out what is the intensity of the problem is not to ask them but to watch them or to watch them solve the thing that they do.

**Lenny** (00:33:06):
You know how a lot of non-technical people don't know how to automate things? So they will do the same thing in Excel like a million times by just tapping because that's the only thing that they know and they're not technical enough to write some kind of script to do it, and you just have to watch those people to just feel the pain. You can't actually ask them how difficult is it to do X, y, z because they won't even know that it's that difficult to them. So the best thing I've learned about how to discover the pain is to watch people, have them screen share, have them walk you through their daily workflow about the area where you're doing some discovery. That is the best thing.

**Lenny** (00:33:43):
I'll give you another example. So there's a bunch of waste companies that are doing EV charging for electric cars and they're like, "What are the problems in EV charging?" And I was like, "Just rent an EV and go and charge at all the non Tesla chargers and see what they say, see what you experience." And the truth is that it's just like garbage. A lot of EV charting systems are just so shitty and the apps are terrible. You just have to just use them yourself to know how bad it is.

**Lenny** (00:34:13):
It's cool how often it just comes back to, "Just go do the thing. Do things that don't scale." Classic YC advice. I want to come back to something you mentioned that I want to pull a thread on as the technical co-founder, being technical early on, just to cover that. So I know YC looks to... Having a technical founder is an important variable in you're deciding to accept a company. Say someone doesn't have a technical co-founder, do you have any advice for what they could do, like what often can work?

**Gustaf Alströmer** (00:34:41):
Yeah, I think the first thing is to understand the value of technical co-founder. So some people who are in this situation where they have an idea of something they want to build and they don't have anyone to help build them in building it, I had a friend Paul who gave this incredible quote, he said, "I have an idea for a song, I just need a musician to help me make it," right? That's kind of similar to how it is with engineering. If you view output of engineering as like, "I just have an idea for a song, I just need someone to actually make it for me" and then you're not valuing software engineering or mechanical engineering or any engineering skill set deep enough, right?

**Lenny** (00:35:17):
The truth is that the engineering part is the really hard part. The first thing I would say is you need to learn how to value the engineering piece. Let me give you an example of how you don't do that. You applied to YC and you have 90% for yourself and 10% for the engineer. You're basically saying that like, "Oh, the engineering part of this company is only worth 1/10th of me. I'm the non-technical person." So that to me is a signal that you're not really valuing engineering.

**Lenny** (00:35:44):
Okay, so how do you go out about and find someone? Well, the truth is that there are a lot of technical co-founders. The technical people, they also want to find business co-founders. They don't want to do other part. They don't want to do sales and they actually don't really care that much about fundraising. They just want to solve the problem. And that's fine. We built something called co-founder matching where those funders can meet, but if you don't participate in that, you can just start by asking the best technical people that you know. "Are you interested in starting a company with me?" Same thing with rejection. Many of them will just say, "No, I have a great job, I'm really happy." But some of them will have thought about starting a company for a while and was hoping that someone would come and ask them to do that. So you have to remove your fears and go and ask the best people.

**Lenny** (00:36:29):
The reason you want to have a technical co-founder and not a hired engineer or not a hired contracting team is because so many of the decisions you're going to make are technical and so many of the iterations you're going to make relies on engineering. And if you don't understand that, you won't actually make the right decisions anyway. It's not like service. You have an idea for a product, you build a product and you're done. There's infinite number of iterations in that process.

**Lenny** (00:36:54):
And then finally, I would say a lot of people learn how to code themselves, right? So there are a lot of places online that you can learn the skillset that takes to build a prototype. You might not be the best engineers. So there are many successful startup founders who are not the best engineers because they stop coding when they hire three or four engineers, that's fine. But you need to be sufficiently good that you understand the value of engineering and that you understand that the best way to solve most of the problem is with software. There are a lot of founders who just, for whatever reason, study something else that doesn't have to be a conscious or very precise reason that you had when you were 18 or 19 and then you're 25, you're like, "Oh, I wish I know how to code" and then just learn to code and they learn how to code. It's not that more difficult than that.

**Lenny** (00:37:42):
Have you ever seen a startup work out if they had a contracting firm, like engineering firm build a product? Does that ever work or were you just like, "No, do not ever do this"?

**Gustaf Alströmer** (00:37:53):
Basically, I can't recall any specific ones where people have a contracting firm but I've recalled founders where let's say you had two non-technical founders, but they valued engineering and they had an ability to build a team of great people that were not co-founders and they gave them equity and they become successful. There are many examples of that I would say, but I don't remember any specific examples where you had a contracting team building the whole thing. I think the reason for that is it takes more than just sort of riding a spec to build a product. You can't actually spec yourself to a great product. You have to just be part of the iterations yourself. That's why I think someone being the engineer, having the idea of what iteration looks like and just doing it is how you do things.

**Lenny** (00:38:38):
I think that the cases where I've seen non-technical founders make this work is that they have really good engineering teams who feel like they're founding team. It might not be co-founders per YC-7 definition of having 10%, but they feel like they're the bonding team.

**Lenny** (00:38:52):
This reminds me of a story of just the recent podcast interview I did with the CPO of Calendly. She talked about how when Calendly started, they actually had a Ukrainian dev team built the first product. Not only did they help them build the first product, they actually ended up driving all the growth initially because they saw Calendly and started using it within their firm.

**Gustaf Alströmer** (00:39:14):
Wow.

**Lenny** (00:39:14):
And then everyone that they knew started using it and spread within Ukraine and they actually continue to work with that firm. They're still the [inaudible 00:39:20] team for Calendly or some part of it.

**Gustaf Alströmer** (00:39:22):
Wow.

**Lenny** (00:39:24):
Yeah

**Gustaf Alströmer** (00:39:24):
Wow, that's cool.

**Lenny** (00:39:24):
There's a success story.

**Gustaf Alströmer** (00:39:26):
I mean, I would say it's certainly the case that in some countries people have other jobs while they start the startups, so like the engineers. In Ukraine for example or in Eastern Europe, it's very common that if they start their own startup, they actually have a full-time job as a contractor while they're starting the startup because that's how you pay the bill because often you can't raise money. And that's fine too.

**Lenny** (00:39:46):
Amazing. That's some hustle.

**Gustaf Alströmer** (00:41:04):
I would say the most common reason that I've seen founders succeed or companies succeed, it comes down to the founders and characteristics of those individuals. The most important characteristics of those individuals are they're really determined to win and they don't give up when things are hard and they have an internal motivation that's just really infectious to people around them, which is how they end up building really good teams around them. People are actually going to want to go and work for them. I have numerous examples of people like this where the CEO or one of the founders are just really inspirational people.

**Lenny** (00:41:42):
The second thing I would say is they are technical. So that's kind of like they're technical enough. If I would grade companies on a scale of technical to less technical, more technical founders are more likely to succeed, I would say. And then I would say they figure out how to talk to users and move fast early on so they don't wait for permission from their investors or from YC or from someone else to make progress. They're like, every day or every week there's continuous progress. They're not doing this for someone else, they're doing this for the customers. They're not doing this for the investors, that's for sure. The investors are sort of in the way more or less. And they're just naturally focusing on the customers.

**Lenny** (00:42:29):
Finally, what I would say is the skill that's really attributed to great founders is excellent communication skills. So the ability to communicate really complicated ideas clearly, to enjoy the communication part, right? Enjoying communication is often kind of correlated with enjoying doing fundraising, which is an important part of some companies' success. Not all of them, but for some of them. I would say communication or storytelling is part of the same arc, right? And those are part of the same thing that actually motivates people around you. If you can communicate why you're building, what you're building and why it's important to the world, tell a story about that, that can motivate people around you to just want to follow you. I think it's rare that I've seen founders succeed where the founder isn't in some way an inspirational person or someone that is a good communicator. Most of the time, you at least have respect or you somewhere know that they're going to succeed, right? And that is what inspires you to be around them or be on their team.

**Lenny** (00:43:33):
That is a really cool list. So just to summarize, one, they have the strong will to win, and with that they're inspirational. They kind of pull people along and get people really excited. Two is they're more likely to succeed if they're technical and can build a thing. Three, they figure out how to talk to customers, don't wait, just start doing it. And they're just obsessed with that versus what investors want them to do and they don't want to talk to the investors to make time for the customers. And then excellent communication skills, which comes back to the first. They're able to story tell and get people excited. Is that right?

**Gustaf Alströmer** (00:44:06):
Yeah, I would say those are the attributes of successful things. To be a super successful company, there's something else that have to happen. Those things are not things you can put on a list because they are the outliers, right? If you look at startups on a typical YC batch, there'd be a couple billion companies. Those are the outliers. They'll almost certainly have all the things that we've talked about. Many other companies in the batch will have that too, but then what makes someone a true outlier is something that is unknown. That's why so many investors said no to Airbnb when they were not trying to raise money because that was an outlier idea. It was an idea that was not logical and did not make sense to most people. Those kind of ideas, the ones that end up succeeding often don't make sense to people. There's some reason that no one has done this before because they're just not natural next step of the world.

**Lenny** (00:44:57):
That's a great segue to a question I've been meaning to ask, which is, how good are you at predicting in a batch which startups are going to be the monster hits? So maybe like you and then just generally YC, how good are you all at knowing what's going to work out, is going to be the next Airbnb or Dropbox?

**Gustaf Alströmer** (00:45:14):
I think the truth is that we're not very good at knowing what's going to succeed. Certainly we cannot figure out who's going to be the really successful company in the batch. That's not possible. What we're good at is knowing what failure looks like. What we sometimes like to tell founders at the beginning of the batch is like, "If you fail, please do it in some new exciting way. Not one that we've seen 100 times." Because we have seen people fail for a large number of reasons. The best way for us to sort of not predict, but the best way for us to make more companies succeed is to tell them how they might fail, right? Be very direct and honest with them and say, "You doing these three things, these things are likely going to lead that you won't succeed." And if we do our job well, most people get that feedback and they're on the track for succeeding.

**Lenny** (00:46:06):
Now, which of those companies end up becoming the best? There are so many things that are uncorrelated to being the best, and it's the things that people don't like. I'm in a hot industry, I was writing up on TechCrunch like, this investor started talking to me. You'd be surprised how many of the things I just mentioned are uncorrelated to outlier success, right? That's why it's so hard to actually do this. I think people really want these questions to be answered. People really want to believe that you can pick really great companies at the seed stage, but everything I've learned from the plus 600 companies that I've worked with is that it's just not that easy and it's maybe not even possible and certainly not possible when you talk about finding the outlier companies. I don't think it's that easy. And if it was easy, then we would accept a lot fewer companies. We just accept those ones, but it's just not that easy.

**Lenny** (00:46:59):
Do you have a sense of which ones are likely to work out better than others? Or is it just like, "We have 150 really unclear, but one of these, hopefully."

**Gustaf Alströmer** (00:47:09):
One good indicator is if each new Office Hour there is really exciting new stuff, right? We're not talking about the same thing we talked about two weeks ago or four weeks ago. They've already done that stuff, right? Like, "Oh, I was trying to sell to these three customers. Well, they already bought it. I'm not actually talking to seven others." And now we are talking about a different price and different product because they're like, they want more of what we're doing. If I'm experiencing that, and that's like a consistent trend, then when people draw this revenue graph of this 10% weekly growth rate kind of situation, those are the companies that we attribute that to. It's like if you're able to make that progress on that short amount of timescale, you are on track to do something well.

**Lenny** (00:47:51):
Now, a lot of other things have to go well for you to ultimately be able to succeed, but progress on this weekly or biweekly timescale is a really good indicator of someone who'll succeed. To me, much better indicator than I am in this market or I'm talking to this investor or something like that. But those are much worse indicators of someone succeeding than I'm making progress and it's pretty fast clip.

**Lenny** (00:48:17):
Interesting. And so what I'm hearing is at the beginning of a batch, we're just in a bet on a bunch of companies that have a lot of potential founders, technical maybe, they have the strong will to win and all these things. Through the batch, you're looking at the companies that are exceeding your expectations week to week in terms of progress that they're making.

**Gustaf Alströmer** (00:48:34):
I mean, sometimes it could be different reasons that people are not making progress. But if you are making continuous progress, and I think Paul and Jessica said this, this was true early days in YC, if you are hitting your goals and you're making progress continuously, if that continues, that's a really strong correlation to some success. But again, going back to the question, can we predict who's going to be the best ones? No. And that's why we really focus on trying to meet people not to fail. Especially good teams can't fail. If you have a really talented team who's really technical in how to build a product but they make some other basic mistakes, like not talking to customers or something like that or trying to build everything all at once, I feel like it's our responsibility to make sure they don't make the basics mistakes that we've seen many times. We need to help them at least make some spectacular mistake that we haven't seen before. Then that's a high potential team. If someone's on a good track for a decent idea but they're still early, that's a really good potential.

**Lenny** (00:49:30):
I have kind of a fun question that I wanted to try, which is kind of connected to this idea around attributes of successful founders and companies. So I had this founder friend named Flow, and he was asking me recently, "If you had to think about the most successful founders, which attributes do they have?" And he kind of gave me this list and it's kind of like two ends of a spectrum. So I thought it'd be fun to just go through this list and see, in your experience, which end of the spectrum, if any, are associated and correlated with the most successful founders. Does that sound good?

**Gustaf Alströmer** (00:50:01):
Sure. Sure. Let's do it.

**Lenny** (00:50:03):
Okay. So the first is speed versus quality. Is there end of the spectrum where you find that most successful founders are either speed-focused or quality-focused?

**Gustaf Alströmer** (00:50:10):
Sometimes founders ask us this question, "What should I focus on? Growth or retention?" And the answer is, they're asking us for permission to not do one or the other. The truth is, to succeed, you have to do both. I would argue that speed versus quality, there's different level of speed and different level of quality at different stage of the company. But the truth is that you always have to move fast and you have to understand what the meaning of quality is, right?

**Lenny** (00:50:35):
So I think I actually don't see that as a spectrum, but I would say if you move fast with talking to customers, you'll build something that have potential having quality because you know a lot about the problem. I think when people think about quality, they often think about, "What is my personal definition of quality?" I have a bar of quality, but quality to me of a good product idea, a good startup idea, has more to do with the customer think is valuable. And if you move fast by talking to customers and having customer learnings and know the problems, then you will actually come up with something that's high quality. So they're not at a spectrum to me.

**Lenny** (00:51:11):
All right. Let's try another one. Confidence versus humility as a founder?

**Gustaf Alströmer** (00:51:16):
I don't think that they're on a spectrum. I think that learning to predict confidence as a founder is critical going back to this communication piece of motivating people around you, right? I wouldn't want to join a company where the founder's completely not confident in their own idea, right? Because that is going to shine through. An investor isn't going to want to invest in someone who's completely not confident in that idea. So learning to first build your own confidence for what you're working on and then predicting that confidence to the people around you I think is critical. A lot of people will have doubt around you. And if you're not predicting that confidence, it's not clear that anybody else will if you're the founder. You're the one who's have to do it.

**Lenny** (00:51:58):
I think that you can predict that confidence while having a strong sense of humility towards the people around you. But I think when it comes to startups, learning to have that confidence is an important piece of the early days, right? And especially if you're building something that's very difficult, that takes a lot of work and a lot of money, protecting the confidence that you will succeed is critical for everybody that's doubting you. And those doubting you is a lot of people around you, right? And you just need to have an unnatural amount of confidence to prove them wrong. I think, again, this is not on the spectrum with humility. In fact, the most successful founders are often the most... You cannot inspire people around you if you don't have a strong sense of humility. People don't actually want to spend time with you, which means they don't want to work for you or invest in you. Again, you need both, but they serve different purposes when you get started.

**Lenny** (00:52:48):
Tough gig this founder life. You got to got to be everything. Let's see if there's a big difference in this next one. Execution and tactics versus focusing on strategy and kind of higher level stuff. How deep do founders go that you find that are most successful?

**Gustaf Alströmer** (00:53:02):
So this one actually I have a strong opinion about. I think that the reason that we talk about strategy a lot is because it goes back to business school. The origin of business school was to teach people to join the corporate world. And in the corporate world, strategy matters, right? So when you join a big company, you're employee number 2,010 or something, then you probably might have a business school job where thinking about corporate strategy is an important thing. When you are a small startup, strategy does not matter because there's not that much a strategy as about. Maybe later on you might be fruitful to think about strategy, but strategy kind of assumes that you can do multiple things at the same time, which small startups cannot. They can just do one thing at the same time. So execution is the thing that matters for companies.

**Lenny** (00:53:51):
Whenever someone wants to have a strategy conversation, it assumes that they don't understand their priorities. The priorities is always a list from top to bottom where there's one thing that's more important than the others. You can't really have a strategy session about the other things because there's only one thing to work on. So to me, a clear answer here is the good founders are execution-oriented and they just continually have one priority of what they're trying to go for. And then they're just hitting that priority all the time and then new priorities will come up and you don't really have time to have a discussion about company strategy. Company strategy also assumes that you have product market fit because you already have something that's working. If you don't have that, then getting to people wanting your product, that is your strategy. You don't have any other strategy.

**Lenny** (00:54:36):
Awesome. Okay. We found one that's quite different one on the spectrum or the other. How about autocratic and kind of like, I don't know, I think of Steve Jobs-like versus kind of consensus, collaborative driven, if this is a spectrum at all. And then where do you find founders might fit that are most successful?

**Gustaf Alströmer** (00:54:53):
I don't know if I have an answer to that question because I think when you work at early stage, you might look different than when you work at late stage. I don't spend a lot of time with founders that have thousands of employees and hearing how they are in the... When I talk to those founders, I talk to them one-one-one and I only hear from their perspective. So I don't actually know how they're peering in a large corporate setting. But when you're a small company, you're three people or five people or 10 people, you cannot be an autocratic decision maker. The founding team have a founding team decision making dynamic that could look different. Sometimes it's like everybody decides together on everything and sometimes you say, "I have my area of expertise and you have yours. We split it up, the decision making." Either of those things are fine. I think you just have to have a process so you don't rehash every decision after you made them a million times.

**Lenny** (00:55:42):
I would say the thing that matters the most at that point is to be willing to adhere to the process that you and your founding team have come up with. Your individual nature could be different in a different role in a different company. But for a startup to work out, you have to have a specific process on how you make decisions. Those are on a very short sprints, like weekly or biweekly. And everyone needs to feel good about decisions after the fact. At least they feel good about the process. I don't think that you can just decide... You can't also be fully collaborative, everyone gets decided about everything. So small startups agree on how they decide together. So after that, everyone just follow the process. That's usually how things work out.

**Lenny** (00:56:27):
Okay, I got one more. Cares more about the product or cares more about the distribution and growth strategy?

**Gustaf Alströmer** (00:56:33):
Well, there's a lot of assumptions built into that, I would say, because caring about the product to me is caring about the customers. Sometimes if I would say something like, "Oh, great founders care about the product," a lot of founders misinterpret that as in my personal perception of the product or my ideas of what the product is. And that's wrong. The right perception there is the expectations or the use of the product from the customers. So if you are meaning focus on the product or cares about the product in that sense that your customers care about, then absolutely, I think that's a really, really critical, important thing to have early on, like talking to users, doing things you don't scale. Once you get big, if you don't figure out a scalable distribution strategy, you won't succeed. And those are different for different companies, but they're not doing anything that don't scale.

**Lenny** (00:57:27):
Doing things that don't scale is not a scalable strategy. Eventually, something specific will be the things that work for you. If you're lucky, people will talk about your product and you'll have organic growth. But in many cases, that sales, that is some kind of consumer distribution strategy. You can't start with that. I've seen a lot, and this is when I had to reset my thinking coming from a growth team joining YC, is you can't start a startup ethic with a growth team mindset because that is just scalable things all the time. And really what you need to go back to is doing things that don't scale and unscale your way of thinking about customers. But it's really useful to have the growth mindset once something is working, right? Once you have thousands of people signing up everything every day, well how do you get to 2,000? Well, that's probably something that looks more like this thing that the growth team would do or distribution team would do.

**Lenny** (00:58:21):
I would say everyone has different experiences of this based on their prior experience, right? So if you work for a company that was infinitely successful, then you won't care so much about this. If you work for Google, you'll never even think about this because distribution is just the website. But if you work for a really small shitty product, then you think a lot about distribution because that's natural to you on how you succeed. So I think at the end of the day, talking to customers matters the most. That is what it means to care about a product to me. And then distribution is something that you will definitely invest a lot in once something is working.

**Lenny** (00:58:53):
Awesome. All right. I have probably a hundred other questions I want to ask along these lines, but I want to make sure we get to another topic which I know is near and dear to your heart, which is climate tech. So my understanding is you're instrumental in pushing YC to focus on climate tech as a focus area. I believe you led the charge on their initial request for startups I think is the term where you all put out like, "Here's who we want to fund." I think you've mentioned you funded a couple dozen climate tech companies and the last few batches, is that all generally correct?

**Gustaf Alströmer** (00:59:24):
First, request for startup was actually Sam Altman and a few other folks that was kind of that one who drove that. The second one that we wrote into our actual request for startup, I wrote that one, was carbon removal specifically focused on. And then naturally the people that apply with climate tech ideas get in my reading queue of applications and I read them and I interview them. Not all of them, but many of them. I think today we funded over 130 plus companies that are focused on climate tech in some way or another.

**Lenny** (00:59:53):
Wow.

**Gustaf Alströmer** (00:59:54):
The trend line is that really ambitious people who want to start companies in this area. Some of them want to start the companies because the climate tech is the number one problem, but they don't view this as a nonprofit. Now I want to really make this as a distinction. People somehow think that starting a climate tech company is doing good for the world, but it probably doesn't have a lot more than that. The truth is that the world have decided. Because climate is one of the biggest problems that we're facing, if not the biggest, we've decided that we are going to stop doing the things that we're doing and we're going to change our entire energy system and change all the things that we do that emits carbon. And we have just decided, governments have decided this. The question is how it's going to happen, but this decision has been made.

**Lenny** (01:00:42):
In that transition, we're talking about trillions of dollars of money moving from things that cause climate change to things that don't. The scale of this transition is not something we've seen recently. Like software is not that big in comparison. It actually is much smaller than this transition. So I think if you look at something like Tesla, which now has, I don't know, $600, $700 billion market cap, that's just one company that currently provides a couple percent of all the cars in the United States, new cars sold. And that is already one of the biggest companies in the world and has now the biggest, richest person in the world. We've only seen the beginning of this. The economical motivation be behind the decisions that people are making are just as strong as I want to fix climate change because this is just a really good business. This change have attracted a large set of software founders that you and me know that listen to this podcast that said, "My skills is relevant here. There are a lot of things that I can do. And if not, I can learn those things."

**Lenny** (01:01:43):
But most importantly, the skills of working for startups is really, really critical to join this transition. A lot of them have started companies or joining companies. I still get an email every week from some accomplished software engineer who asked me "Which software companies should I work for to fix climate change?" And I've gotten those emails for two or three years now. This thing just attracts really, really ambitious people. It's not stopping. It's accelerating. I feel lucky to work with so many of these great founders because they are uniquely interesting people.

**Lenny** (01:02:16):
I've noticed exactly the same thing of just how many smart, driven, amazing people are like, "I just want to move to a climate tech company. That's all I'm looking for now." Just to give you credit, I feel like you are ahead of the curve on the shift that's started to happen and pushed YC to focus on this really early. I always think like, "Man, I know Gustaf and I feel like Gustaf has made such a massive impact on the investment and focus in startups on climate." And so I just want to give you huge props for doing that and being so at the forefront of a lot of this.

**Gustaf Alströmer** (01:02:50):
Thank you. I mean, sometimes I'd say that it matters to someone who has the credibility of YC to start accepting these companies. It does matter. I remember when I spoke to Diego from Pachama in 2018 when he was starting Pachama, we were whiteboarding in YC. He was a YC alumni starting a different company. The word climate tech did not exist. People were unsure if investors would fund companies like these. Pachama's raised $60 million to have, I don't know, lots of big customers, lots of employees and it's clearly doing really well. But I think at the time of 2018 it was kind of unknown. One of the reasons it was unknown is we had this previous bubble, clean tech bubble, in 2008, 2009, 2010 that didn't work out because of a number of specific reasons and investors were just afraid of funding things because they had some scar tissue or scars from this previous thing that happened.

**Lenny** (01:03:46):
Now that turned out upside down. The number of new investors that are investing in climate tech is as big of a trend as any other trend we've seen in the last decade or two decades. There's just an enormous focus on the investing side. Most recently, me and another guy, David Rusenko, wrote this request for startup, a new updated, very detailed list of... I hope we can post it in the show notes, a very detailed list of ideas or areas where we think it might be worth looking If you want to start a company.

**Lenny** (01:04:18):
Now, we don't know what good ideas look like. We don't know. But we can tell you where all the areas of opportunity exist. We should go and look for good ideas. We wrote this because in response to all these people that come to us and say, "I want to work on climate tech. I don't have a good idea because I don't have any specific experience in this stuff." And then we're just like, "Don't work on these three things but go and work on any of these 25 directions." It already has generate a good response. I think it'll generate more response. But I think it's important for YC to tell the world that we look and fund these things. And that's always been the reasons we had requests for startups, is to let people know that these are things that we actually want to fund.

**Lenny** (01:04:58):
I actually moderated a panel a couple weeks ago. This organization called the Climate Draft put together PMs that are in climate tech. A lot of the questions were just like, "What kind of background do I need to move into climate tech startup to start a climate tech company?" It's interesting, every single one again and again just said like, "Your actual regular PM skills is all we need." There's a lot of people already at the company that are experts in the science and that's okay if you have no experience. They just need the business experience, how to operate, how to execute, standard stuff that PMs learn. And so would you agree with that that you don't need to have this deep background in science and climate to move into the space?

**Gustaf Alströmer** (01:05:41):
Yeah, I would say if you were working on a software company and even some of the hardware companies, that's probably generally true. Absolutely. It's much more valuable to have that background than to have this specific domain expertise background. Those are complimentary. But as a PM, having the solid PM background is the more valuable piece I would say. Being a competitive PM, coming from a really good culture of product management, knowing what good looks like, that's invaluable to some of these companies because in the past they weren't able to hire these people. So I agree with that 100%.

**Lenny** (01:06:14):
In terms of founders, I've seen everything, right? I've seen people having some domain expertise starting a company and really succeeding. I've seen people who had no domain expertise and learned everything they need to know. Maybe they partnered up with someone who had a domain expertise and then succeeded. I've seen all of it and I actually think that you can succeed in either of these categories. You don't need the deep expertise. It depends really on all the area you're in. But someone like Pachama, Diego and Tomas did not have expertise in forests besides the personal experience. They just had a willingness to solve the problem and it really worked out for them.

**Lenny** (01:06:51):
You mentioned you have this list of areas you're excited about. I know we'll share in the show notes, but is there any you want to highlight, just like here's areas you're most excited about and want to fund and/or are there companies you want to mention that are super interesting and super cool in the space that people should know about?

**Gustaf Alströmer** (01:07:04):
We wrote the list and we are highlighting companies in each of the categories. I don't know if I want to highlight any specific categories, but I can talk about some of the things that we've funded in the past that has real legs. So here's how I generally think about climate tech. So we have to decarbonize all the things we do that emits emissions. That means we have to change a bunch of things in the world, change transportation, change energy, change homes, all of these things, or change how we heat homes for example.

**Lenny** (01:07:35):
And then there is carbon removal. Carbon removal is sort of like, well even if we do all of this stuff really well, it's probably not going to be enough. And because there's an opportunity and there's some evidence to suggests that we can actually remove carbon from atmosphere in some way or another, a lot of companies are also working on this at the same time. I would say we need to do both and they're not in conflict. We probably are going to need to do both. Well, we certainly need to do the first one.

**Lenny** (01:08:02):
On the decarbonization side, there's infinite number of categories of our society where we met a lot of carbon, right? So I'll give you an example. Shipping is a really big deal. A lot of carbon emissions come from freight ships around the world. That's not obvious solution how you would solve that because the kind of oil that they run on is really cheap and it's a very low margin business and they don't have a whole lot of incentives to change besides what is coming down regulatory. So it's not a national solution where someone to be a cool, someone will build a test off ships and it just work out. But the two companies to be funded in that area, one of them is Seabound who is building carbon capture and removal for ships.

**Lenny** (01:08:41):
The other one is Fleetzero who build electrical ships. Electrification is on and again and again and again and again and whenever it's being applied, turn out to be a more efficient way of doing whatever thing that you were previous doing with the combustion industry. It is almost no maintenance. It's cheaper to build. The batteries are more expensive, it's cleaner and it fits the carbon coal you have. There's just a bunch of benefits there, but there has limitations. Usually the limitations on electrification has to do with batteries. It's like how far can you go? Now that category is what I call the... Which is a very important kind of critical one, which is the carbon accounting and sort of the recommendation systems that help big company account for the carbon that they have and they are giving some recommendations of what you do.

**Lenny** (01:09:25):
So I'll give you three examples. We funded Unravel Carbon, which is carbon counting software in Singapore, focusing on Asia, probably the leading one there. There's company called Carbon Chain, which is focused specifically on supply chain and shipping and raw materials, stuff like that out of UK. And then there's ANAI here in the Bay area. Who knows how this market is going to play out, but this market has carbon accounting customer demand right now, right? So all the large companies of the world have other either promised the government, promised their shareholders or promised the public, or maybe even the employees, they go into decarbonize. They don't always have an idea how to do it. These software platforms is like the plug and play "This is how you do it."

**Lenny** (01:10:07):
And then I'll give you two examples of things you can go into if you don't have any specific domain expertise and just a good software engineer. There's a company called Enode. They are basically building Plaid for EV chargers and Plaid for home energy system. So if we imagine that the future of all homes or future of all charging of EVs is going to be a bunch of energy appliances that are run by small computers, they're all wifi connected, you can connect to them and do things, tell them to turn on, turn off, turn on when it's cheap, turn off when it's whatever, all these different things that are valuable for the energy grid. Then you need a software platform to connect with all of them. And that's what Enode has been building.

**Lenny** (01:10:48):
Another related company is called Static. Static is the Airbnb for EV charging in India. The reason that you need something like that is you don't have Tesla charging. You don't really have public charting in general. People don't have outlets in their garage and they don't have garages. So you need to build a new bottom up EV charging system or platform, and that's what Static has been doing. They're actually building out public charging infrastructure as well, but they have their own app. So if you use a Static app, they'll direct you to all the Static chargers. I believe that they're the biggest or the fastest growing EV charging network in India, which is the second-biggest country, if not the biggest country in the world right now.

**Lenny** (01:11:25):
So the potential of these ideas, even that they're doing well now is just infinite, such an enormous market. If you succeed in one of these things, I don't think we are going to have as many gas stations as we have today and different networks. We're not going to have the same in EV charging. It's going to be a lot more consolidated around the use experience of the end user and the app they open to do this stuff. So I'm pretty convinced that there's real big opportunities for software entrepreneurs to figure this out. There's some companies in the current batch that are focused on this too.

**Lenny** (01:11:59):
The final one I would mention is Heart Aerospace. We have a Heart Aerospace and the Right Electric and a few others focused on aviation. Aviation is another big difficult to decarbonize. Heart and Right are focusing on battery electric planes. So they're basically making commercial airplanes that fly on batteries and flying electric motors and it's incredible to see.

**Lenny** (01:12:22):
What a killer list. We're definitely going to include links to all these companies in the show notes. Something I was thinking about is, so one narrative violation you mentioned is that there's actually money to be made in climate tech. It's not impact-oriented market anymore. It might be worth chatting about why that happened, but the question I want to get to is also things are going well. A lot of progress is being made. People see climate change and it's like we're dead, it's game over. But it feels like battery prices are coming down, solar's coming down, wind powers ramping up, all these startups are investing. So it'd be fun to just hear what's going well and maybe what is there to be optimistic about, but then also, "Okay, yeah, things are going well, but there's still things that are not going so great and where we need to double down."

**Gustaf Alströmer** (01:13:10):
Two specific things that went well in the last say 12 or 24 months. First one was politics. So in the United States we got the IRA, which is like it's called the Inflation Reduction Act. It makes sense because shift into greener energy is going to actually reduce inflation because it reduces energy costs. But it's really a climate bill, right? It really is a bill that is focusing on onshoring, a lot of supply chain for the green economy and incentivizing a lot of this change that we just talked about. Whether it's carbon removal or home energy or home heating, whatever it might be, this bill addresses all of it and is massive. So that's one really good news. Politics didn't have a lot of good news in the US for a long time on this. Maybe not ever actually.

**Lenny** (01:13:52):
The second good news, and it's such a good news that Europe is now trying to conquer. They're not trying to counter the IRA with their bill because they're seeing some of the battery companies saying, "Well, I'll actually going to build the next factor in US, not Europe anymore. I changed my mind."

**Lenny** (01:14:05):
Oh, wow.

**Gustaf Alströmer** (01:14:05):
So Europe now has to counter with their incentives as well. The second good news is corporations are now customers. So maybe three or four years ago you went to a Fortune 100 company and you're like, "Hey, do you want to buy my XYZ decarbonation solution?" What it's like? The software platform or EVs or whatever it might be. They're like, "Well, talk to this person on this floor. Maybe they can help you." And this person was not really empowered to make decisions. That has changed. Now they're like, "Actually, we promised our shareholders to reduce emissions by 2% every year and we also promised the government and we promised whatever publicly to do that. So we got to do that." They're like, "Where do we start? What's the first 2% that we got to decarbonize? Maybe that starts with energy. Oh, we'll change our energy providers." But they are now showing up as customers, not just with LOIs but paying actual for contracts, right? Doing investments in these companies because they've all see the future and they don't want to be behind.

**Lenny** (01:15:02):
There's financials motivations for this. They want to get access to capital that has some strings attached to some of these things, but they don't want to fall behind. And then they don't want to be the Toyota to Tesla, where Toyota said, "We are not going to do battery electric." It's just like they're still saying that sometimes and everybody else is like, "Tesla is the one we got to copy because that's the one that's winning." All these corporations are really afraid of being the Toyota. They're really afraid of being the last one who's not changing and then the world will move past them and then they're going to die. So I think the motivation here is intrinsically survival and it's really about sort of adopting this because this is where the world is going.

**Lenny** (01:15:39):
I think these are the two best news. The thing that I think what... We also wrote about this in the request for startups. This is not a thing where you can convince everybody to just agree with you. And even if you did, people wouldn't know what to do. So you have to view this as an economical opportunity and say... We can't convince everybody that this is going to be the thing that's going to happen. It doesn't actually matter if you convince everybody. What matters is that sufficient amount of corporations are convinced that they change their habits. And then you can sell the things you're building to them.

**Lenny** (01:16:09):
As sort of founder, just focus on your customers and focus on B2B. That's what most people I recommend to do here because that's where most of the change is going to happen. That's why I'm really optimistic about these startups and these founders. What they're doing is, in my opinion, more impactful than someone running a campaign trying to convince some other people that this is a big problem. Even when people know that climate change is problem, they don't know exactly what to do about it. But the startup founders, they know.

**Lenny** (01:16:37):
You touched on this, but it feels like one of the biggest shifts is capitalism is kicked in and is now leaning into climate tech startups and that's-

**Gustaf Alströmer** (01:16:46):
Yes. Absolutely. Absolutely.

**Lenny** (01:16:48):
... making a big dent. Well, with that, we've reached the final part of our chat, which is the very exciting lightning round. I've got six questions for you. Are you ready?

**Gustaf Alströmer** (01:16:58):
Yeah.

**Lenny** (01:16:59):
What are two or three books that you recommend most to other people?

**Gustaf Alströmer** (01:17:04):
The first one I recommend, I think I have it here. Yeah, this one. It's called The 100% Solution. It's written by Solomon Goldstein-Rose. It's for people who think climate change is a problem but don't know what to do about it, or they're just kind of in despair or think they're like, "Ah, everyone are going to die," right? There are some books written where the outcome of the book is like, "We're all going to die," but the truth is that we're not all going to die. This book is trying to cover the 100% of all the solutions in detail, kind of much more detailed version of the request of Sharp that we wrote. It gets you freely optimistic. And I give that to anybody who's cared about climate change because it really lays out this from a very optimistic way of looking at the world. And that's why I recommend that book more than almost anything else. That's probably my number one book.

**Lenny** (01:18:00):
Amazing. I love that if just a one book, here's the book you got to read. I like that approach. What's a favorite recent movie or TV show that you've really enjoyed?

**Gustaf Alströmer** (01:18:10):
Oh, I watched so much. I don't know. I love Emily in Paris on Netflix. I think I have TV serves different purpose for me these days. It's just like entertainment.

**Lenny** (01:18:22):
Yeah, I get that.

**Gustaf Alströmer** (01:18:24):
But what else movie do I watch? We watch the Everything All at Once. I thought that was a really good movie. That was-

**Lenny** (01:18:30):
Yeah, it might win Best Picture.

**Gustaf Alströmer** (01:18:32):
Yeah.

**Lenny** (01:18:32):
We have a drinking game here. People say White Lotus, we drink. And so you did not, that's probably for the best. Favorite interview question that you like to ask YC founders when you're interviewing them?

**Gustaf Alströmer** (01:18:43):
What have you done since you applied to YC on your product? What are specific things that you've accomplished since you applied? Because that usually is a month or two month months ago.

**Lenny** (01:18:51):
That's awesome. It connects so much with what you said earlier.

**Gustaf Alströmer** (01:18:55):
I hope the answer is like, "Here are all the things that we did."

**Lenny** (01:18:59):
Versus we just prepared for this interview.

**Gustaf Alströmer** (01:19:01):
Exactly. Exactly.

**Lenny** (01:19:02):
Most out there wild startup you have funded?

**Gustaf Alströmer** (01:19:07):
I think I would say when I stepped onto the hangar floor of Heart Aerospace. I can send you a photo. Literally, I am looking at an airplane that's being made and I'm like there's no SaaS company's office you can walk into and you just open your mouth and you're like, "What the hell is this?" There are a few of those companies that are space companies or airspace companies or something like that where it's just a different feeling that you fund them and you can touch it. I have a lot of appreciation for things like that now because they're much harder to do, but when you succeed, they're much more tangible and you can be like, "I have a tiny little piece in this space rocket or this airplane that we funded or this satellite above us." I really think that that's in some way a strong legacy compared to some other things that exist and just replace other softwares. And all these are better businesses, but there are strong legacies.

**Lenny** (01:20:06):
What's a pro tip for applying to YC?

**Gustaf Alströmer** (01:20:09):
Pro tip. Number one thing is go to YouTube and type in like... I think there's a video that we've recorded which is about how you succeed with your application [inaudible 01:20:18]. It's an hour long video that gives you all the pro tips on how to do it. We told people in advance, "Once you've watched that video, then see if you know anybody who've done YC and then reach out to them and maybe ask them if YC is right for you, but also ask them what's important for you to, as you kind of approaching applying to YC, writing the application, during the interview, what were the things that matter?" Those are probably the two things I would do.

**Lenny** (01:20:46):
Final question, what's one pro tip for visiting Sweden?

**Gustaf Alströmer** (01:20:49):
First of all, you should visit in the summer. It's a really good time to be there. It's a very different country in the winter. Try to go outside the cities into the nature and then prepare yourself for Swedes not all being Americans. They're a little bit more colder and have a little bit more distance to you and they don't randomly talk to you like I've learned to do here in America. I think you just have to go along with a little bit different of a vibe than you have here in the US. Most people actually love it. Most people who have just been, they love it, but most of them go in the summer.

**Lenny** (01:21:23):
This reminds me, I wanted to close it, but there's a tweet once about how in Sweden when you go to someone's house, they don't feed you. It's not expected that you will have food. You have to bring your own food. Is that true? And what's that about?

**Gustaf Alströmer** (01:21:35):
It's absolutely true. I actually gave an unconference talk about this topic. The unconference talk was all of the strange things to Swedish people do and why. If i would summarize it, yes, we do that. I actually experienced that. I went to a friend's house and they had dinner and I waited in my friend's room while they had dinner. That was just normal. And why did that happen? I think there's a strong sense of individual responsibility in Sweden, which kind of reaches over to unfriendliness, [inaudible 01:22:10] from an American or foreign lens because this is so crazy. But in Sweden it's just like, "Well, you take care of your kids. I'll take care of my kids." And it's not really a question.

**Lenny** (01:22:18):
I think that a lot of the motivations of why Swedes are strange, one of them is we don't want to be indebted to someone else. So we never want to feel like... Which is why you wouldn't... For example, if you go to a bar in Sweden, you don't buy a round, you buy your own beer because maybe you have to figure out the money at the end of the day, things like that. I think it's just actually quite individualistic society, but it's individualistic with heart I would say. There's a warmth to it, but it will definitely be appeared strange to people who don't really understand this. They think people are cold and they're just like they don't understand that there's actually a heart behind this stuff.

**Lenny** (01:23:00):
That sounds really smart, to be honest, the system. I would be into it, but I can see how people are very confused. Gustaf, I can't thank you enough for doing this. This was incredible. I know that people listening to this are going to leave informed, inspired, motivated, hopefully motivated to move faster and make more progress. Two final questions. Where can folks find you online if they want to learn more or ask you may be follow up questions? And two, how can listeners be useful to you?

**Gustaf Alströmer** (01:23:27):
I tweet sometimes on twitter.com/gustaf. The most useful things that I put out is probably on the YC's YouTube channel. So I record a couple videos on growth, on sales, on how to talk to customers. I actually send them to people all day long because the Start School videos that we made are a lot of preparation went into it and it answers most of the questions that people have. So watch those first, I would say. But yeah, sometimes I tweet other stuff that people can follow. That's fine. How can people be useful to me? I love hearing feedback from founders, what they're working on. I want to hear kind of questions they have about their companies. But I want to also really emphasize that to apply to YC, you don't need to know any of us. You don't need to reach out to us. It doesn't make any specific difference.

**Lenny** (01:24:15):
The principles in YC is that you should be able to become an insider in YC in Silicon Valley without knowing anybody. That's kind of what the application process is about. So feel free to reach out to us if you have questions, but don't feel like that's required to be a good YC applicant. It's actually the opposite in that we read and treat all the applications equally. Thank you so much for listening to this podcast. I mean, it made me happy you made all the way to the end.

**Lenny** (01:24:44):
Yeah, extra credit for listening to the end. I also just want to say while you're saying that, it feels like YC is such a good force for the world. It just enables so much innovation and progress. And if technology is what drives the world forward, IC is so at the center of a lot of that. So just huge props to what YC is doing and what you're doing, Gustaf.

**Gustaf Alströmer** (01:25:02):
We feel a lot of responsibility towards that. That's for sure.

**Lenny** (01:25:05):
All right, I'll let you go. Again, Gustaf, thank you for doing this.

**Gustaf Alströmer** (01:25:09):
Thank you so much.

**Lenny** (01:25:12):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [16/22] Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe)

**Claire Hughes Johnson** (00:00:00):
What I say to people at Stripe... In our onboarding, I used to run a session. I was like, "If you're not sure who the decision maker is, one, it's probably you. And I'd rather you act that way than not because you're going to like slow the whole company down. Follow a process and get it done, and don't forget to actually make a decision. And if you don't know who the decision maker is and you're worried it's not, you just ask. Don't get stuck." Too many people get stuck and it makes your work terrible, right? What do we all care about? Progress, impact, momentum. If anything I would say about advice to people generally is be a force for positive momentum and it will be actually a real career maker.
**Lenny** (00:00:50):
Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard one experiences building and growing today's most successful products. Today, my guest is Claire Hughes Johnson. Claire was most recently chief operating officer at Stripe for the past seven years, where she helped scale them from a small startup to the legendary company that it is today. Before that, she spent about 10 years at Google where she was VP of self-driving cars, VP of global online sales, director of sales and ops for Gmail, YouTube, Google Apps, and AdWords. Before that, she was in politics. She's also on the board of HubSpot and the Atlantic. And this week, she's releasing an incredible book called Scaling People, which in my opinion should be and likely will be on every founder's bookshelf. In our conversation, we dig into many of the meaty topics that her book covers, including building your operational cadence, defining your company and personal operating principles, your company's operating system.
**Claire Hughes Johnson** (00:04:49):
Thank you, Lenny.
**Lenny** (00:04:51):
So you wrote this book. It's called Scaling People. It's coming out this week. I actually read a preview copy, and it's incredible. Everyone listening to this should buy it, especially if you're a fan of this podcast. It's full of frameworks and templates and guides and all these things that I try to do with my newsletter and podcast. And so if you like what I do, you're going to love this book. And I can't imagine how much work it must have taken to write a book like this. So my first question just have relieved are you that you're done with this book and you can move on with your life?
**Claire Hughes Johnson** (00:05:21):
I am so relieved, Lenny. Writing this book was not my idea. Patrick and John Collison, Stripe's co-founders, really sort of pushed me into it. And I'm glad they did. I will admit that, as I am with most things they pushed me into, but it was a lot more work than I thought it would be, and it's very rewarding to have it done. Of course, though I've been re-looking at it and realizing there are things I want to add information or tweak what I originally said, but maybe we'll have to do a second edition. We'll see.
**Lenny** (00:05:55):
That's the benefit of a newsletter. I can just edit things and they're immediately live.
**Claire Hughes Johnson** (00:05:59):
Yes.
**Lenny** (00:06:01):
I want to talk about John and Patrick a little bit. But before that, something I wanted to ask is I find that when I write stuff, I am able to better understand and crystallize my own thinking. And I'm curious, having written this book, what is it that you were able to better understand and crystallize in your own thinking through that process?
**Claire Hughes Johnson** (00:06:20):
It's true, and it's funny, because if you asked me, I would've said I crystallize more by talking and speaking. But whenever I do write something down, I'm glad I did. So I probably do more crystallizing by writing than I would admit, but maybe I'm just lazy and I just like to talk. There's a part of the book, I think it's toward the end of the third chapter, which is about hiring, and that's a really long chapter. Turns out I had a lot to say about hiring and hiring leaders and processes and what you need want to set up. And as I got toward the end of the chapter, I found myself saying to the reader... You maybe have read this and thought, is she for real? You need to do all this work? You need to put all of this in? And I had to say, well, look... I started the chapter saying, if you believe that talent is everything, then your hiring process is everything.
**Claire Hughes Johnson** (00:07:11):
And so yes, you do need to put that work in. But I think, Lenny, to your point, when you see all the templates and the frameworks and the examples and the advice from my career... And I was at Google for almost 11 years, I joined Google when it was about 1800 people pre IPO and left when it was about 60,000. I had eight different jobs while I was there. And then joining Stripe when it was about 160 people, and now we're over 7,000 people. Yeah, I have a lot of examples, but really what's crystallized is how much work it is to build, to build a company. You know this. And I hope this book is a bit of a shortcut, but there are no shortcuts. I hope it will accelerate people's knowledge so that they can get down to work with our product and with our customers.
**Lenny** (00:07:58):
There's a story you share at the end of the book, I think it's in acknowledgements, about how people went and took John Collison out for dinner and were just picking his brain, and "How did you scale Stripe? How did you build this amazing machine of a company?" And he often came back from these dinners, and he's just like, "Claire, they just want to talk to you. You did all these things, not me." And it sounds like that kind of encouraged you to write things down, and then led to this book. One, is that true? And then two, I'm curious, what else did you learn from John and Patrick Collison that have stuck with you? I imagine there's a lot, but kind of what stands out?
**Claire Hughes Johnson** (00:08:31):
Yeah, no, absolutely. I think it is true that at Stripe, we're fortunate where we have so many users, customers who are themselves founders or interesting companies growing up around the world, whether at scale like Amazon or scaling. I've spent time with Discord and Toast and all kinds of interesting companies that are growing up around us. And a lot of their questions are not necessarily about Stripe's products always. They're really about, "Well, how do you guys do this thing?" Or "We're having this challenge. Are you having this challenge?" And John, yeah, would often come back from trips. He would travel more, and he is often probably meets with more customers than anyone in the Stripe leadership team, maybe other than our sales leaders. And they would ask about scaling, and he would joke. He's like, "We need Claire in a box." So I think the book is Claire in a box, I guess.
**Claire Hughes Johnson** (00:09:23):
But Patrick also would have that same experience. And when I contributed a chapter to Elad Gil's High Growth Handbook, even though if you look at High Growth Handbook, which I also really do recommend not just because I'm in it, I'm probably the least, I don't know, celebrity participant in his chapters, and my chapter got a lot of traction because I think it was very specific. It was very tactical. And Elad actually helped me to realize, look, examples and details and frameworks, my working with Claire document is in there, is like... He said it's catnip. And I think that is also what inspired Patrick to push me to do basically a longer version of that chapter that I did with Elad. But I've learned a lot from both of them. I used to think that I was... My parents are teachers, Lenny. I used to think I was very curious, and I'm a learner and I'll seek out information.
**Claire Hughes Johnson** (00:10:21):
And I grew up in a very educatory environment, right? Well, once I met the Collisons, the two of them are huge sponges, seeking out knowledge constantly. But also, anytime we were confronted with anything, even things I felt I'd done before, that I had the experience and we were going to build it, they were like, "Well, who have you talked to?" Or "What have you read?" And it was really good. I don't think I made enough phone calls in my earlier career and asked people's advice and asked for help and found the person who did that thing five years ago and found out what they learned. And I think that's probably my biggest lesson from working with both of them, is how much it pays to seek out knowledge from others because we're all just learning all the time.
**Lenny** (00:11:11):
Is there a story or example of that comes to mind that was really beneficial where you actually ended up follow that advice and reached out to someone, talked to someone, and that changed the way you think, changed the way you operate?
**Claire Hughes Johnson** (00:11:21):
There are two things that just jumped into my mind. The first one is early on at Stripe... When I joined, we were about 160 people. I started bringing in some leaders. We were building out go to market, we were starting to stabilize our support operations, building out recruiting and HR, all the things. We were really growing. And it became very apparent that we needed to put in some kind of job structure. Levels and ladders is what you would call it, which is there are different levels of pay, and they have to do with your experience and your impact and their expectations of those different levels, right? There's an engineering ladder. And this stuff is probably making some people listening like their skin start to crawl because it's never fun or easy to define all that, and it's not perfect. You're immediately getting into something that feels pretty suboptimal, but it is worse to have nothing because it starts to feel very unfair in the environment, especially if you have to start to change up compensation and reward or reward systems, right?
**Claire Hughes Johnson** (00:12:24):
So I realized, oh my gosh, we're going to have to put this in place. We didn't know HR people, so I basically ran a project. And the first thing I did though, thanks to Patrick and John, is I talked to Square, I talked to Airbnb, and I talked to two or three other companies. But those two conversations, I'm not going to say who said this, but one of them, the person said, "Oh, that's a blood bath." They were not encouraging about what we were about to go through. And another one said, "You know what? I'm so impressed that you're doing that so early. We waited too long." And actually, that's what a lot of my book. It's about is when should you start to think about this thing that you might need, right? And it's sooner than you think. And so putting in levels of ladders felt like ripping the off, honestly, but I was glad. One company I talked to waited until they were like 800 people, and it was apparently not fun because people don't like to be... Who likes to be categorized?
**Lenny** (00:13:26):
Yeah, and put it at a level that maybe they're not happy with, right? They're like, "Oh, I thought I was a lot more senior than that."
**Claire Hughes Johnson** (00:13:32):
Yep. Yeah, exactly. It's not easy. It's a form of change challenging. And I would not say we did it perfectly, but I'm glad we did it. I think that example was definitely one of them. Another was like we were really... We wanted to roll out 24/7 support in multiple channels, email, phone, chat in multiple languages and getting from where we were to where we wanted to be as quickly as possible. Not many companies have done at the scale, because Stripe has millions of customers. We're B2B, but we're B2B at a very high scale, which actually Google was as well. And so that was beneficial to me coming into the Stripe environment because I'd done parts of that for Google. And again, that's an example of something I thought I knew how to do, sort of, but we certainly didn't do it perfectly, and it's certainly different when you're talking about payments.
**Claire Hughes Johnson** (00:14:24):
That's people's money. That is a business'... If they don't know how to contact you and they have a problem, that is a huge issue. And so I did seek out a lot of advice. And I would say... Did anything change dramatically what we did? I think if anything, the advice pushed me to go faster on some of my intuitions about, for example, using vendors and outsourcing parts of the model. And I realized we're not going to scale all this internally, especially not at the speed that we're going, but it's hard to start to use outside sort of contractors if you haven't filled figured out all your tools and processes. So that balance was sort of freaking me out, but you just got to push through it.
**Lenny** (00:15:15):
There's a couple directions I want to go, but I'll go in an unexpected direction. At Stripe, you're kind of infamous for your titles. When I created this career ladder document.
**Claire Hughes Johnson** (00:15:24):
[inaudible 00:15:24].
**Lenny** (00:15:24):
Yeah, it's like everyone's product manager., They're like a VP of product potential and it's like product manager. What's the rationale behind that? I guess, and what's the benefit of that? But, we don't have to go too far down the road. I'm just curious.
**Claire Hughes Johnson** (00:15:37):
So this is something that Patrick and I actually really agreed on without a lot of discussion, which is not always the case. It has to do with a combination of optionality as you scale and grow, and also culture, right? And so the minute you start titling a lot, you're signaling hierarchy and authority. And the culture piece to Stripe still today, which is I think we could use more, at least more overt trappings of structure because it can get confusing. And I'll be the first to tell you that, and I admit that this might have carried on too far. But early on, at Stripe, there's a real belief. It's not a particularly hierarchical company. And if you're the person who has the knowledge, you are the expert on the thing, you better be, one, in the room helping make the decision, and two, driving, helping to drive the decision. And I don't care how senior you are, right? And that was the cultural signal that was important, which was about mutual ownership, and also expertise not sitting in hierarchy.
**Claire Hughes Johnson** (00:16:43):
And then the optionality thing is probably a little more obvious, which is don't make somebody the CMO, or even the head of marketing, if you're marketing team is two people, right? Yeah, you might make the right choice, but two years later, your marketing team's probably going to be more than two people, say it's 20. And are you going to have to layer somebody or have too many titles? And then someone feels like they're losing something, right? It goes back to the levels and ladder saying, but it's worse because you've given something, and then you're sort of taking it away, and that's just not... Organizationally, you want more flexibility. Honestly, I'll say my final thing, which is I have a little bit of a knit where you meet a company. I get what's happened, which is in order to hire this person, they had to sort of say, "I'll make you the VP of sales or the VP of this," but the company's like 25 people and there's seven VPs.
**Claire Hughes Johnson** (00:17:40):
If you're a customer or you're evaluating it, you're kind of like, "Really?" It's a little incongruous with the scale. So we kind of more flexible. We had a lot of growth, head of this or growth lead. I know you're all about growth, Lenny. Well, we definitely took growth and find that very broadly. But the other thing I've said to people internally... Sorry, you can really get me going on this one. I bet you didn't think that. If you are a stripe and you're going out into the market, actually it speaks to the same thing, which is you're going and trying to sell to a customer who's a lot bigger than you. I'm not saying make up a title. Don't say you're the VP of sales, but you can be creative about how you represent your scope because you probably have really big scope because you're one of the only people helping to sell the product. And that will help you because a lot of more established mature companies are trying to do that hierarchy match, where "Well, bring your SVP because my SVP is coming to the meeting."
**Claire Hughes Johnson** (00:18:42):
And we could be like, we don't really have that. It just gives you a little more selling flexibility too.
**Lenny** (00:18:48):
I like that. I like combo where you can just say something that fits in this situation, even though that's not your technical title.
**Claire Hughes Johnson** (00:18:53):
Yes, you can say, "Oh yeah, I actually am in charge of optimization for our payments product." I'm sure you are. I'm sure that's what you
**Lenny** (00:19:01):
Do. Coming back to something you talked about with the career ladder, and I had a question around this, you talked about how oftentimes people do it too late, and I'm curious why it's so important to think about the stuff that you wrote about in this book so early in your company's life cycle. I think in the book you mentioned that it's oftentimes as important to get your operational structure and cultural structures in place incorrect as finding product market fit or finding your first few customers, which I think would surprised a lot of people. Can you talk about why you found that to be so important?
**Claire Hughes Johnson** (00:19:35):
Not only can I talk about it, I wrote a whole book about it, so let's try to restrain me. But here's what I would say. Obviously product market fit is the most important. And what I do say in the book is focus on that and don't get too far. My book is definitely not zero to one. It's more like maybe 0.5 to 1.5 or one to two. Because I do think when you're smaller and focused on product market fit and finding your user and getting that traction, that shapes a lot of how you work and your goals and who you hire, and that all makes sense. I think the thing that happens though is, one, some companies don't quite realize they're hitting it and they start to get behind on actually building the company part. Because guess what?
**Claire Hughes Johnson** (00:20:23):
It turns out product market fit is just the product, and that is not a company, and that will not scale, to point. You see these companies that sort of fall over and there's sort of a bad article about them, and often it's not the product, it's the fact that they didn't actually build the company very well, and that started to harm, in fact harm the product and harm the mission. You have this vision, you're going to solve this problem with this product. And all of a sudden you can't solve it because you didn't scale the org properly. You didn't keep the cultural fabric strong as you grew, right? And so that's why I think it's so important. And so let's say you are hitting traction, and hopefully you do notice it. Because I think a lot of founders, you're kind of paranoid.
**Claire Hughes Johnson** (00:21:08):
Like Stripe, I don't think Patrick and John fully embraced that they needed to start scaling maybe until I showed up, and that was part of hiring me. I was like, yeah, this is it. It's happening. It's not just look at the numbers. It's like look at the inbound support demand, look at the inbound sales leads. I just did the math, and I was like, this company should be probably twice the number of people it is right now, which of course freaked everybody out, but it was very obvious to me because I was coming in outside with that perspective. But more importantly, not just scaling things like sales and support... And as you probably know, if you work in payments, you've got a lot of other functions that are very important around risk and compliance and you name it, or the machine learning models and that help you do those things.
**Claire Hughes Johnson** (00:21:55):
But for the sort of structures and operating processes that I talk about in the book, I do have this analogy which I think you picked up on to building a house, which is you have the supporting beam. Say it's a post and beam structure. You need the posts and the beams, and then you're going to have to do the mechanicals, right? There's going to have to be some amount of wiring in order for you. I don't know if you have your solar panels, but you got to bring in the heat, you got to bring in the cooling and plumbing, and then you have foundational stuff that you have to build or the whole structure will fall over. And I think of putting in the posts and beams and the mechanicals and the foundation as actually essential to scale. Because if you do those things well, you build them in such a way. This is almost like a Russian doll kind of thing, but you build them so that they're replicable, right?
**Claire Hughes Johnson** (00:22:49):
So the way that you do goals as a company can start at the company level, and this is how OKRs were so beautiful for Google and they can replicate down to the individual. And the same common structure allows that to happen at really different levels of scale. And that's what you're looking for, is what are these common things? We do not a lot of them, by the way. You don't want to mandate a lot, you don't want to put too much structure in place, but enough that everyone can play with it up and down what I would think of as the stack of the company. And if you don't start putting those things in early, people will just invent those things. And then you'll have... Picture a house that got added on to 17 times and it's not even two years old. It looks not super stable. And then you're going to find yourself having to do a tear down, which I think we've all seen companies do that.
**Lenny** (00:23:40):
I definitely want to get into that house structure and all the components of it. But before we get there, if you're a early stage founder just looking for product market fit, maybe the skipping ahead a little bit, but which elements do you think are the most important that they need to do now? Because they're going to read your book, which gives them so much advice on all the things you can do.
**Claire Hughes Johnson** (00:24:01):
Yeah.
**Lenny** (00:24:02):
If you have to pick a couple things that you have to nail when you're just starting out before product market fit, what do you think is most important?
**Claire Hughes Johnson** (00:24:08):
I think really that early, keeping it very simple and being focused on that goal of product market, which is like what is the problem you're trying to solve? What's your vision?Everything you have to do for an investor pitch deck matters not just for the investors. By the way, people forget this. A lot of the story you tell to investors, early ones especially is the story you should be telling internally to anybody you hire. Why do we exist? What problem are we trying to solve? What early customers have we attracted, and what's their feedback. That's what you mostly need, but you need to remember to share it and don't just use it for fundraising, or don't just use it for a board meeting or an investor meeting. Use it internally. And I think you can get pretty far actually with that core content. As you start to...
**Claire Hughes Johnson** (00:24:56):
The first thing you're probably putting in place is a little bit of hiring process, and I think that's going to matter sooner than you think. Don't just be tempted to hire people in your friends. Think about what you need, what capabilities you need to build even pre PMF, right? And so as I said, there's a chapter about that, but I think some of the simplest versions of it is how do we evaluate talent? What kind of talent are we looking for? Where do we go look for talent, figure that out, and sort of train people a bit internally on interviewing. I think interviewing is not a skill that comes naturally. People think it does. It does not. And there's really basic easy tips and tricks you can find even on the interwebs about interviewing. And I really recommend... And my book has examples of rubrics, questions you can use. How do you really get at... Because it's hard to really evaluate someone in 30 minutes or 45 minutes.
**Claire Hughes Johnson** (00:25:49):
So I think interviewing some of your fun fundamental early investor kind of content you need. But then when you start to get some traction, then you're showing to codify and actually document what I call more foundational content. Because if you're pre-product market fit, you're probably small enough that you just can tell everybody all the things. You don't have to send them the packet or have them sit in the onboarding. But the minute that you're starting to get any kind of hiring speed, you're going to want to document it more and you're going to want to start to put some very lightweight processes of how you get things done in place, because again, you're trying to replicate velocity. It's easy when you're all in one room and everyone knows like, "Oh, this is the most important thing to get done today," hack, hack and hacking away. But then pretty quickly, that is not going to be the case.
**Lenny** (00:26:38):
I definitely want to go one layer deeper on that, but there's this area I wanted to get to before we dive into some of the weeds around that, which is I found it really interesting that you started your book with this idea of personal operating principles versus here's how the company should work. It starts with here's how you should think about yourself. So I want to go... There's four of them... But before I get into them, can you just describe what is the idea of a personal operating principle and why is that important?
**Claire Hughes Johnson** (00:27:02):
Remember the book is about two things, company building and company structures, and all that, replicating all that good step and management. So the other thing that the book is really about is management tactical guides to... It would be easy to build companies if there weren't humans involved, right? But there's humans and they're complicated, and I'm complicated and you're complicated. And there are things that motivate us. There are things that demotivate us. They're not the same things, though Lenny and I, I think you and I have some things in common, but point is the book starts with you. And I think a lot of people think management starts with the team, or even the company. And actually, I think founders make this mistake. Founders think, well, it starts with my product. And yeah, but it actually starts with you. And so the book starts with sort of my belief system, which is self-awareness, which is the first operating principle. Self-awareness to build mutual awareness is actually the most fundamental thing you need to crack if you're going to succeed at company building or management, in my opinion.
**Claire Hughes Johnson** (00:28:08):
But I would say I'm one of those people who has strong opinions that are pretty loosely held. This one is a strong opinion strongly held, which is the more that you can seek feedback, seek to understand your motivators, your strengths, your blind spots, your tendencies, and take that on board and expose it to others, you're going to be a much more effective company builder and manager. So it starts with you. And those operating principles that I articulate are sort of mine, but they're also foundational to the content of the whole book. I do think authentic leaders tend to have their own, right? Lenny, you probably have a few that you... You maybe have not articulated them all out loud, but I do have mine and they're in the book, but I think you would also find that some of them you could adopt. If you were looking for were some to start to use as a leader, I would hope that I've put forward a couple that might be useful.
**Lenny** (00:29:04):
I want to talk about these four, but while you're on that topic, what are ways to help crystallize your own operating principles? What advice would you give people to do this? Because to your point, people probably have them in their head, but they haven't really written them out.
**Claire Hughes Johnson** (00:29:17):
That's right, they haven't. The book has an exercise that I recommend in it that's a little bit more about crystallizing your personal values, but that's kind of the place you want to start. And it's essentially there's a whole menu, and you can find these online, of say 70 or 80 different values. And by values, I mean family, ambition, impact competition. People value education. People value different things differently, by the way. And there's no judgment. You might value being a very competitive person and I might value collaboration above competitiveness, and that's fine. We probably would both be very effective in a team for different reasons, right? So basically if you take a list of values and you say, okay, if I had to pick 10 of these that matter to me, then if I had to pick five of them, and then you really force yourself if I had to only pick three of them...
**Claire Hughes Johnson** (00:30:09):
And it's actually good to have this in a dialogue with someone that you work with or well, and you sort of had to explain, well, why? Why, when I'm really pushed, do I have to hold on to say education or learning as a value? Or why do I have to hold on to integrity as a value? And I tell a story in the book about a manager I worked with where transparency was a very important value to him. And the thing is you usually have a story behind that value, right? And in the book, I use the name Eli for him. Eli ends up sharing this story at this offsite that we had. And the transparency value actually was a little bit problematic to manage because Eli would tell everyone everything, including his team, even when we weren't finished with the plan, right? But Eli got up and told a story of being younger, like seven or eight, and realizing his mother was very sick, and no one really told him what was going on.
And then unfortunately watching the process of her dying and then being taken out to lunch by his stepfather and told, "Your mother is gone." And okay, well, your whole worldview kind of explodes when you hear that, and you're like, oh, okay, this transparency thing is really real. This was a formative experience for him and it has changed how he operates, and it will probably have changed it for his whole life. And if you can get to that point on your own, of telling yourself, what was the story? What was the thing that made this so important to me? Then you're starting to be in a mode of self-discovery and then you're starting to document, okay, if these are my three top values, and here's why. And then I think what you want to look for are my, what I would call my work style tendencies? And so you get your values, and then you sort of go on a... I'm sorry, I could go on about [inaudible 00:32:08]. I warned you. I wrote a book about this.
**Claire Hughes Johnson** (00:32:09):
But basically, all these work style assessments, Myers-Briggs, DISC, Enneagram, you name it. And by the way, I would take all of them because I find that very good. I mean some of it's just data. You're just taking on data. But a lot of them come down to are you introverted or extroverted? Are you more introverted or extroverted? Where are you on that continuum? And are you more task, if you kind of picture a horizontal and a vertical, are you more task or people oriented? And so I would take your values, and then I would plot yourself. Am I a more extroverted task-oriented person, which means you're kind of a director, get what done kind of person? Or am I a more extroverted people-oriented person, which might mean actually you're probably great at being very charismatic and building some followership and maybe selling a vision? A lot of salespeople are very extroverted people oriented people.
**Claire Hughes Johnson** (00:33:03):
And then you start to see, okay, if this is my sort of tendency in my default and this is my value system, what are the ways that I operate that really make up who I am and becomes almost a belief system. And my operating principles in the book, one is to build self-awareness, to build mutual awareness. Another one is say the thing you think you cannot say. I think that I've come to believe that often your biggest strength, one, is also your weakness, but two, is something that you don't know is a big strength because it's almost like breathing. For me, saying something actually fairly openly and directly but in a non-threatening way is a thing I do. John Collison actually once said to me, he's like, "It's so interesting when you give feedback, that can be actually pretty brutal, I leave feeling really optimistic."
**Claire Hughes Johnson** (00:34:02):
But I don't mean to be brutal, but I think I can sort of unpack and say this thing, like here's my observation, here's going on, and it's not judgmental, it's not threatening, it's actually opening up an opportunity for people. So say the thing you think you cannot say. You would actually find that more of us can do that. And then I come back to distinguish between being a leader and a manager, which is something early in my career, I did not do well, Lenny.
**Lenny** (00:34:30):
Before we get to that one actually, just to briefly ask you a follow up question, because I love that you're getting through all four here. This is great. But I was going to ask, is there something.. So clearly, you're really good at saying the thing you cannot say, and I love that. Many people are not good at this.
**Claire Hughes Johnson** (00:34:30):
No.
**Lenny** (00:34:45):
Do you have any tactical advice for someone that is not good at this for how to actually say something uncomfortable?
**Claire Hughes Johnson** (00:34:51):
I think the main thing is, and Fred Kaufman has this in his book, Conscious Business, this concept of a left hand... He calls it the left hand column, which is you're in a dialogue with me or you're watching a meeting happen, and you've got a running commentary in your head. And honestly, some of that stuff is pretty harsh, right? You do not want to open your mouth and just say that thing. But what Fred says is, learn how to detoxify the left-hand column. I would say think about a way to say that thing that you think you can't say. You've filtered yourself out, which I don't like. And I want you to think, okay, can I? And I think that the... Here are the tricks, a couple of them. One is, ask a question.Right? A question is not threatening. By the way, the question could even be, is there something we're not talking about? It feels like to me... And then you own.
**Claire Hughes Johnson** (00:35:47):
So the next trick is you own it. This is your observation, this is your perception. This is not a judgment. I am not saying, "Lenny, I think you really botched that interview." That's not useful. If I said, "Lenny, you know what? I wonder if you missed an opportunity in that interview. Did you feel like you missed an area that..." And then you're kind of curious. You're like, "What do you mean?" And I'm like, "Well, I'm kind of looking at this with you, and I'm standing next to you and I'm observing it." Right? That's less threatening. So one, ask a question. Two, make an observation that you own. So if I said, "I feel like there's something we're not talking about, and I wonder..." Oh, I own it. "I wonder if it's the fact that these two teams both seem to have the exact same project."
**Claire Hughes Johnson** (00:36:32):
I talk in the book about a meeting I was in where it was very clear that we had two teams in conflict, and no one was saying the thing that was really pretty bad. I was like, this is pretty bad. We have two teams that seem like they both own a piece of work and are in conflict with one another. But I would say if you do those two things, ask a question, own the observation yourself, don't pass a judgment, you will get way farther than you would've ever thought sharing. And by the way, that sharing, one, there's probably other people who just haven't, can't get it out of their head, and you have ar opened up a door that a lot of others can probably walk through. You're not alone.
**Lenny** (00:37:12):
You have this framework, I think you call it being explorer, not a lecturer. Is that what you just described? Is that how you describe it?
**Claire Hughes Johnson** (00:37:18):
It is. And to me, what I just talked about was more of a meeting or a conversation scenario, but I think that this... I'm glad you brought that up. I think this is actually a very fundamental management framework of mine, which is in a one-to-one interaction, your job as the manager... First of all, too many people think your job as the manager is to be the expert and tell people what to do. No, actually, your job is to enable people to be their very damn best on your team. And you have to create an environment and a context and provide them information, and then you need to provide them a form of coaching. Now, again, I think people start think coaching is lecturing, like let me coach you how to make this Excel model. And sometimes they do. Sometimes someone comes to you and says, "Can you exactly show me how to do this thing?"
**Claire Hughes Johnson** (00:38:05):
Fine. But most of management is actually exploring with someone. It is being curious. It is saying, "I have seen this pattern of your work. Have you seen this pattern? Is there something..." I have a whole other framework which is about hypothesis based coaching. I think intuition as a word gets kind of a bad rap, and I kind of get why, look, especially if you work with a lot of engineers, which I do. It's not particularly always data driven, but guess what a scientific hypothesis is? It's a well-informed piece of intuition. And I think too many managers wait until they have a million pieces of data to make an observation to someone about an area for improvement. Instead, I would say take some data, form a hypothesis, and then explore it with the person. Because if you're well intended, which I think any good manager is, I'm bringing up this thing because I'm trying to help you see it and tell me if it's true so that we can both help make it more effective, better.
**Claire Hughes Johnson** (00:39:11):
One very light example could be, "I felt like in that meeting... How did you feel that presentation went?" And the person sort of says, "It's fine. I think I got through the material." You say, "Yeah, I felt like you were maybe a little bit nervous. I'm just exploring. Were you..." And by the way, the person could say, "Oh, no, no. No, no, no, no." And then you could back off, or you could say, "Oh, well, maybe it was just me, but I noticed some physical. Your leg was shaking a little bit, your voice, you were kind of repeating yourself." And they're going like, "What?" And you're all you're doing is holding up a mirror... And you have to own it. You have to say, "My experience of you in that meeting was that you seemed nervous to me. Maybe you were not, but actually maybe this is just a physical coaching thing."
**Claire Hughes Johnson** (00:40:04):
Have you ever had that? I have a few people on my teams who do this weird thing. This is pre virtual world, but when they're sort of getting it uncomfortable in a meeting, they put back their chair up off the table, sort of exit the circle. And that is a very physically big statement. And they had no idea, Lenny. They had no idea. I'm just watching the meeting, and I'm like, oh my gosh, you're like four feet from the rest of the group because you do not like this topic. And what I need to explore with you is how do you vocalize that instead of physically exiting the room or exiting the circle? These are just examples. Sorry, I could keep going. But I really think that that attitude of exploration and mutual sort of collaborative, let's discover some things about you...
**Claire Hughes Johnson** (00:40:54):
And by the way, it can be mutual. They can go right back at you and say, "Well, I observe this." Great. Great. I've interviewed a lot of people for the book, different leaders and managers from lots of different fields, but one of them was Reid Hoffman, who's a more typical. But Reid, we were talking about the other operating principle, which is management versus leadership. And Reid was pretty honest. He's like, "Look, I'm more of a leader. I'm not a manager." He's like, "I'm not a great manager." And then he told me the story. He's like, he had in his first company that he was building, he had a guy that he'd hired who was more operational. And Reid was sort of making an observation to him about something they should do, and the guy goes to him, "Reid, I wouldn't hire you to manage McDonald's."
**Claire Hughes Johnson** (00:41:42):
And Reid was like, "Okay, good. So tell me what we need to do so we can fix this thing." But what actually Reid's operating principle, interestingly when unearthed that whole thing, was that he prides... It's very important to him to create an environment of open feedback. He said, what I love about that story, yeah, it's funny and embarrassing, but actually that guy was comfortable saying to me, "I wouldn't trust you to manage a McDonald." And I think that actually I found inspiring because I don't think everybody who founded a company or who's managing someone has created an environment with how much trust in it, right? And that's how Reid thinks he gets a lot of stuff done, is people just come right back at him with the feedback.
**Lenny** (00:42:26):
**Claire Hughes Johnson** (00:43:24):
Distinguish management and leadership is the third one, yep.
**Lenny** (00:43:28):
And then just to summarize real quick, the second one was to say the thing that you cannot say. The first one was-
**Claire Hughes Johnson** (00:43:34):
Say the thing you think you cannot say, yeah.
**Lenny** (00:43:36):
And then first, build self-awareness to build mutual awareness.
**Claire Hughes Johnson** (00:43:39):
Yeah.
**Lenny** (00:43:41):
And what's cool is you're sharing all these amazing stories and tactics. In the book, you actually have templates to do each of these things for yourself. So a lot of this is pointers too. If you actually want to do this, go check out the book and you can actually do this. It's not just in a bunch of high level stuff. And then the fourth is-
**Claire Hughes Johnson** (00:43:57):
Come back to the operating system.
**Lenny** (00:44:01):
Let's talk about it.
**Claire Hughes Johnson** (00:44:02):
So this one is, sort of like I was talking about, touchstone documents that you might create for your company. This is our operating principles, our values. This is my touchstone, which is I think that especially high growth environments, but every environment you operate in can get really chaotic, and there's a lot of ambiguity. There's a lot of stuff you don't know, and it's kind of easy to get paralyzed or to sort of give into the chaos. And you're like, oh my gosh, I don't know what this day is going to bring. I'm just going to randomly assign some stuff, and I'm just going to get through it. And all you're doing in a lot of those moments is creating more chaos. And I think a really important role of definitely managers, but some leaders too is to create a stability when there doesn't feel like there's a lot that's stable.
**Claire Hughes Johnson** (00:44:52):
And where stability comes from is in ritual and in common practices that you share. So we set quarterly goals or monthly goals. And that's a ritual, and that's a thing we do, and it's actually a source of stability. And yeah, it feels like a process. It might feel like a way of managing, but it also has a cadence to it. And I think one of the things that happened is you picture yourself sort of spinning out of control. You think, how do I come back to this is the order I do things, this is how I get decisions made, this is how we make plans, this is how we make decisions. Those touchstones are not processes to run the thing. If they're done well, they're stabilizing because they're a common way of approaching that everybody has, so they can at least hold onto that even when all the other stuff is going haywire.
**Claire Hughes Johnson** (00:45:45):
You've got a customer churning, and you've got a big launch happening the next day, like, oh my God, oh my God. Come back. What's our launch? How do we launch products? We have a way of doing that. We do not need to spin out of control and reinvent the wheel here, right? And that's a stabilizing thing. And the other thing on come back to the operating system for me was, as my career scaled, as I went from a individual contributor, to managing a small team, to managing a bigger team, to managing multiple teams, to managing managers, you get it, I realized actually, and I started to have multiple functions. So I was context switching between... At Google, there was a point where I had some product people, industrial design operations, really BD, really different functions. Actually, how I fundamentally ran them at the bare bones, at the house architecture level was the same.
**Claire Hughes Johnson** (00:46:38):
And that gave me a stability as a leader where I would dive into a meeting. I'd be like, all right, let's look at the metrics that matter. We all had... We had them for every team. Let's look at the goals we set. And that also helps you stabilize when your contact switching between seven different projects or seven different teams. And so I wouldn't say it's the operating principle that I talk about the most, but I think if you were like, "What's your sort of... How do you scale yourself?" I would say, "Well, I actually have a common operating system like a computer, and that is how I maintain a sense of stability."
**Lenny** (00:47:17):
Perfect segue to the next kind of broad area I want to spend time on, which is this house metaphor and the three components of it that you talked about. And this is like the core of the book. Can you talk about again, the three kind of pillars of this house structure? And then let's just go through each of these things.
**Claire Hughes Johnson** (00:47:33):
Yeah, it's definitely, the beginning of the book is about company building, and the company structure chapter is all about the sort of supporting beams, the mechanicals, and then the foundational stuff. And interestingly, it's sort of, well, I guess when you build a house, you build the foundation first. So one is the founding documents that you might create, which I'm happy to talk about. And then another are the supporting structures, which are some of the ways you do things we talked, like quarterly business reviews or OKRs, or how you use planning to create a structure that everyone... And then the mechanicals are what I might call the operating cadence, which is essentially the rhythm of how you work, right? The calendar, the year that we all experience tends to dictate a little bit how we work. Mondays feel different than Sundays, right? Well, companies have that same kind of a cadence, which is often also calendar driven, but also can be event driven.
**Claire Hughes Johnson** (00:48:28):
We've talked often at Stripe about how our customer event, which we have called Stripe Sessions, is as important internally as it is for the customers because it's a forcing function for our cadence, how we plan our products, what we want to have achieved by that point, what we want to demonstrate. And that's true for a lot of companies, but we actually use it in our thinking about our cadence of the year. And actually, we've built this other event that I usually help run, which is an internal event that happens generally about six months before that, which is great because you can demo the stuff you think you want to demo internally. You sort of create a cadence of we're going to push ourselves to do some crazy wild stuff, internally demonstrate it, and then see if we can externalize it by the time we hit the customer event.
**Claire Hughes Johnson** (00:49:16):
But that is a cadence. Quarterly business reviews are part of your cadence, et cetera. So that's the fundamental, but really while I'm trying to do is say, one, I don't think this stuff is super hard. You know this. It's kind of hard work. It's just putting it in place, and then actually using it. I think where a lot of leadership teams go wrong, especially of young companies, is they experiment with different vehicles to try this stuff. And then they either don't actually follow them or they throw them out the window after they haven't tried it for very long, and it creates a lot of chaos. So I would say do very few things consistently and try to do them well, and then see if they're working for you, and then once a year, maybe think about a revision. But don't keep throwing out new things you heard that other companies do. And it turns into a weird grab bag of operating stuff. You're nodding because you've seen this too lot.
**Lenny** (00:50:16):
Yeah, I think a problem I've seen is people think there's going to be this perfect system and process that's going to not have any flaws, and they're always like, "Oh, it's not perfect. We got to optimize it further." And what I find is it's always just like, this is the best one you can come up with at the time. This is the best idea you have now. There's going to be flaws. Just work around those flaws. But just know there's never going to be the one thing that works.
**Claire Hughes Johnson** (00:50:35):
There is no one. There's no perfect org structure, there's no perfect operating approach, there's no perfect, yeah, performance and management and level system. But having one and committing to it is good. And don't let the perfect be the enemy of the good.
**Lenny** (00:50:50):
There's another, you mentioned that I thought it'd be fun to talk about, that it's often chaotic at a company. I imagine people think about Stripe from the outset, like, oh, they've got it all figured out, so smooth, just runs like a machine. And I think people look at other successful companies and they're like, man, things are so crazy at our company. This isn't normal. But I think, you tell me if I'm wrong, most places are crazy and chaotic internally for a long time and often, right?
**Claire Hughes Johnson** (00:51:15):
Yeah. There are different kinds of chaos, but it's so true. What is that? There's like a saying. Don't ever believe your best press or your worst press. It's never as bad as whatever someone's saying it is never as good. It's just normal is not pretty. It's a lot. And that is true. It's happening everywhere. I used to have a friend who was building a company. We would see each other. We both were from the Boston area, and it's a long story, but we'd end up on the same flight off in Rhode Island, coming back to Boston occasionally for stuff, for family. And we'd be in getting yelled at by the passengers because we'd be in the aisle of the airplane comparing notes about stuff that was broken.
**Claire Hughes Johnson** (00:52:02):
And we had this expression, it was like, oh, and then I picked up the rock, and under that rock were some really ugly, creepy crawlies. But that's just like the way it is, is it's never perfect. But I guess I would go back to what I just said about having some stabilizing ways of doing things because that can create, I don't know, I'm not trying for a perception that the thing runs a machine, but more of a, that is a well run thing, right? And how do you create that perception? Because you adhere to some ways of running things and that are consistent, and it feels better even to the outside, even if there's a lot of chaotic stuff going on.
**Lenny** (00:52:45):
Coming back to the founding documents, could you just talk about what are in this group of founding documents? And I think even more interestingly, what's a sign that you should invest more time in this area as a startup?
**Claire Hughes Johnson** (00:52:55):
Yeah. Very classic stuff is in here, nothing that you haven't seen or examples of. So one is I think it's good to have a mission. When I joined Stripe, we did not. It came to be apparent that to increase the GDP of the internet was probably the mission, because people kept repeating that back to us, and Patrick had written it on some website copy early on. But it was interesting that candidates and customers kind of grabbed it. It was very Stripe because it's a little bit intellectual and pointy headed and aspirational, but also it is... The GDP does involve economic progress, which we're all about, right? We're building infrastructure for commerce and payments for not just the internet actually. But anyway, point is have a mission, or at least the beginning of what's your one line of what you're seeking to accomplish.
**Claire Hughes Johnson** (00:53:47):
And then I'm a big fan of writing sort of what we Stripe called our long-term goals, which were just not our short distance, but our longer distance, like why did we exist? And so the mission is one line, so you need a little more meat behind that, right? And actually, I think if you looked at our long-term goals, which by the way I thought would be a three to five year goal, I would say they're still relevant today. But one of Stripe's long term goals is to advance the state of the art and developer tools, which would not be something that everybody, especially every customer of would initially call out. But when you think about it... Lenny, you just did it. You think about it for a minute, you're like, yeah, the API and the docs and a lot of stuff that we've open sourced, Stripe cares.
**Claire Hughes Johnson** (00:54:38):
Our forever user is fundamentally a developer. It's the person who's integrating Stripe, right? By the way, simple integration, complex integration, anywhere in between, we really care about their experience, and we care that the tools are excellent, because how are you going to increase the GDP of the internet if you don't advance the state of the art of developer tools? Right? Anyway, point is articulating that, because until I said that to you and I could talk about it with you and say you came to work at Stripe, you might not understand why we invested in certain things or why it meant so much to us in terms of our user experience and the mission. So articulate those things. And some of them might be a little bit aspirational, but they should feel at least real enough that you can have that conversation about... You look at anyone who works in a company, what they choose to do all day with their time should be guided by things like, what are we trying to accomplish?
What are our long-term goals? So if they don't know them, how are they going to make the right choices? So that's one. And then another is a lot of companies write company values, or at Stripe, we wrote operating principles. I think you had [inaudible 00:55:50] on, and she talked about these, and we even sort of took a version of ours and put them out for candidates so that they could evaluate, do I want to join this company, because I kind of want to know what it's like to work there? And I think that's really valuable to do because not every company is right for every candidate, and the more you can mutually match the better. But having some operating principles matters. I think you can go farther than that, but that's where I would sort of start, is those three things.
**Lenny** (00:56:17):
Awesome, I like the simplicity of this.
**Claire Hughes Johnson** (00:56:21):
How you know is people are asking you. Especially new hires are asking you a lot of questions about what's important, or "Why do we do it this way?" You said it yourself at the beginning. Doesn't writing something down, crystallize it? Time to write it down and crystallize it for everybody who works there.
**Lenny** (00:56:40):
And just to summarize you as a mission, your operating principle/values. What was the third one?
**Claire Hughes Johnson** (00:56:45):
Yep. Long-term goals.
**Lenny** (00:56:47):
Long-term goals.
**Claire Hughes Johnson** (00:56:48):
And sort of more details on why you exist. What are you really trying to accomplish?
**Lenny** (00:56:52):
Interesting. And then are those numbers in your experience, or is that a story of what [inaudible 00:56:57]?
**Claire Hughes Johnson** (00:57:00):
Those are a little bit more, I think headlines. And I think your shorter term goals have numbers against them, right? So if you looked at your long-term goal, which might be... Another one of Stripe's is about accelerating globalization, and if you thought about what would that require, that would require us to be in a lot of markets. That would require us to have users and customers in a lot of market, and also to eliminate friction across borders. So those things, which is a very high friction thing, unfortunately in payments, and moving money, which it shouldn't be if you want to advance globalization, accelerate it, right? And so that can then become numerical goals and short term goals.
**Lenny** (00:57:41):
Basically objectives, and then-
**Claire Hughes Johnson** (00:57:43):
Yeah, it's sort of the longer term objective, and then the key results part is early is shorter term. But actually, if you're having trouble writing your company goals, actually zooming way out and being like, "If we're going to meet this mission, what do we have to accomplish in the long term?" You can then walk back from that and be like, "Oh yeah, every goal we ever have probably fits in these three to five buckets." Bam. And then you write your short term goals actually more easily because there's always going to be one about, say, international expansion. There's always going to be one about additional products because we're trying to do X, and you can't do it with one product, or whatever. You can imagine the example.
**Lenny** (00:58:22):
Awesome. And I know your book has a actual examples of a lot of this stuff.
**Claire Hughes Johnson** (00:58:25):
It does. It does.
**Lenny** (00:58:26):
So again, pointer to that. Okay, so that's the founding documents. The next piece is operating system. Maybe we go there, just what fits into an operating system for a company? What are the components of that?
**Claire Hughes Johnson** (00:58:38):
I think a lot of the components we've sort of touched on, which is do you have some sort of goals? This is now goes back what we were just talking about. For Stripe, we have an annual set of numeric targets that we put together, we have a system of goals or OKRs, objectives and key results, but sort of like what is your structure for setting milestones that you want to achieve, whether they're numeric or more like a binary, we got this thing launched, we didn't? And then QBR, so quarterly business reviews. How do we review parts of the business? What is the cadence? Well, first, what is the form by which we do that? Which would be this... I share examples in the book of this might be the template you fill out if you're a team and your reporting on how it's going and versus your strategy and your goal.
**Claire Hughes Johnson** (00:59:24):
And then there's also getting into metrics and dashboards. What are things that you look at internally to measure progress, the input metrics and the output metrics? And I give some examples of that. And then mostly, I think there are other... As I said, there could be less frequent forms you use, like a user event or a launch, a way of launching products, et cetera, but it's really simple. It's mostly goals and how do you review the business. Planning. I talk a lot about planning, which is. You said this earlier, and you and I think both agree, which is there's no perfect process to plan for the next year or the next two years, but you still need to fight your way through having something, especially after a certain stage. And every COO I meet with, we sort of ring our hands together.
**Claire Hughes Johnson** (01:00:11):
We're like, oh, planning and everyone hates us, too burdensome, but you still got to keep trying. You got to do it. And so we talk about planning processes and what they might look like and how you set them up. And then that's how you'd use goals and QBR to measure against the plan, right? So those are some of the operating systems. And then the cadence is just how often do you do these things? Actually, one of our big lessons, I think companies that are moving quickly and that are younger tend to resist some of the calendar based cadences of more mature companies because they seem slow. You're like, really? You're going to just achieve that goal in three months? Or are you artificially restricting yourself to some lowest common denominator of time? And so I get that fear, and I would say your cadence doesn't have to be one quarter or one six month, or even 12 months.
**Claire Hughes Johnson** (01:01:08):
Stripe, we did sort of six month processes for a while. So instead of a year, we did it in six months. Still, there were things that took, by the way, a year or longer, but I think that play around with the timeframe and don't feel restricted by what other companies do. But one of our lessons on the QBR was sometimes those quarterly, because that stands for quarterly, those quarterly business reviews were too infrequent, especially for new product areas. They we're still in development. They were still getting a lot of feedback, launching a lot. And so we just said, okay, they're not quarterly anymore. They're like every six week business reviews. Fine, change your cadence. The point is to have one, because then it's predictable for teams. They know what they're marching toward, they know when they're going to be reporting out, and they can set their goals in a way that makes sense to make progress in that timeframe.
**Lenny** (01:02:02):
One quick question there. What's a sign that your cadence is off? What's a flag that we should go shorter or longer?
**Claire Hughes Johnson** (01:02:10):
Well, everyone usually complains about these things, but I think if the... One, nothing, like you said, it's probably too fast if not enough progress is being made in between whatever your review or your reporting function is, and it's probably too slow if the content you're reviewing seems stale. And you're like, "Well, we knew this," or "We already did that thing," or "Yeah, we already had the meeting where we talked about that." That's another thing that's interesting, is some companies will have a pretty frequent metrics review cadence, and then an infrequent strategy review cadence. And what happens is the metrics review becomes the strategy review because you're not talking about the strategy often enough. And so you're talking about it through the data, and so then by the time you get to the strategy review, you're like, we already had this meeting. And that's just a sign that some things are just off. And to me, it's about timeliness and freshness of the content, but also that there's actually new content. If there's not new content, you're creating work for people. By the way, give them time to work.
**Claire Hughes Johnson** (01:03:12):
And so I think don't fool yourself that thinking, having more frequent checks on things is going to actually make things run faster. I would say that the opposite can be true. And so be very wary of actually slowing velocity down by creating overhead. One thing we try to do at Stripe is if we're looking at metrics, let's just look at your dashboard live. Let's not create a special presentation. I actually just share your screen please on your dashboard, right? Which is a good discipline, because one, that means you have to have a really good dashboard that's real time, that's web accessible. No one had to pull or massage the data. That's a good sign. But it's also, you're not wasting people's time prepping all that information, which happened even... By the way, at Stripe, even when we put that in place, we still ended up with versions of that problem.
**Lenny** (01:04:04):
Yeah, [inaudible 01:04:05] I think mentioned that. I think there's a term for it, data something, where you randomly get chosen every week and someone has to present your data.
**Claire Hughes Johnson** (01:04:04):
The metrics review meeting, yes.
**Lenny** (01:04:10):
And it's like the next day, you're going to have to share your meetings and [inaudible 01:04:12]
**Claire Hughes Johnson** (01:04:12):
Yes. We called it the spin the wheel, the spin wheel on who gets to present. But that has a logic in it, which is then you're not working. So just prepare it.
**Lenny** (01:04:26):
Right. That's awesome. I love that policy. There's so much more I want to chat about. There's chapters on hiring, self-development, personal development, all these things.
**Claire Hughes Johnson** (01:04:34):
Team development. Yep.
**Lenny** (01:04:36):
What was that?
**Claire Hughes Johnson** (01:04:36):
There's a, yeah, intentional. There's a team building.
**Lenny** (01:04:40):
Team building.
**Claire Hughes Johnson** (01:04:40):
And performance management.
**Lenny** (01:04:41):
Yeah. Okay, so we could go through all that stuff. Instead, I want to talk about the COO role broadly.
**Claire Hughes Johnson** (01:04:47):
Yes.
**Lenny** (01:04:48):
I asked on Twitter, preparing for this chat, what people wanted me to ask you about it. And most of the questions ended up being about the COO role and things like that. So I just have a few questions lined up here for you.
**Claire Hughes Johnson** (01:04:48):
Sure.
**Lenny** (01:04:58):
Okay. So Amir [inaudible 01:05:04], with little accent at the end there, he asked just at what point do companies need a COO, and how would you judge if someone is a fantastic COO?
**Claire Hughes Johnson** (01:05:12):
Oh yeah. Well, I would first say most companies, if you looked at the universe of all companies, do not have a COO. I think it's fewer than 20%. It's definitely fewer than 30. And I think that's something to know, that I don't think it's an automatic role to have or hire. And I think you see it in more prevalently in earlier stage or high growth companies. You also, by the way, see it in certain business models. I actually think Apple was an interesting version of this, where Steve Jobs was oriented in terms of product and design, but also that Apple has... It's very intense to manufacture software and hardware that then works together. I learned that when I worked on self-driving cars at Google, and you need a very intensely operational, detailed manufacturing, hit the marks, hit the timelines person. So I think some businesses that have a very deeply operational, say a manufacturing component, that role might be more prevalent.
**Claire Hughes Johnson** (01:06:19):
But point is, it's not an automatic. I think it's useful in a high growth... In an environment where you're having... Think about the founder/CEO of a company that is achieving product market fit and also having to build a company, and hire all the leaders. That is a lot because you are building the product and the business, you are building the company, and you are building all the people, bringing them all in. And that is where I think a COO type of role can give you leverage, which is... Essentially, it's a layer that takes some of those functions and helps build them with you and on your behalf, and also in some cases, bring some experience in maybe there's a particular function like go to market that needs to be built. And I think that's where you see it come up. What I've said to some people recently is I'm a little worried, just like there's a mythical founder, that there's some mythical silver bullet COO hire that everyone's like, "I will just find that person."
**Claire Hughes Johnson** (01:07:20):
And first of all, we're all human beings. I'm not perfect. I certainly did some things well when I joined Stripe, and other things not as well, and I'm working on my self-awareness of what those things are. But I would say one lower risk strategy could be to bring in, say, a head of business operations or a role that's sort of COO like and try a couple of functions with someone and see if they scale with the company and with the role, and then maybe you decide they're a COO. I mean, I mentioned Stripe's business operations team. You could hire a business ops leader and sort of say, "Hey, build this team to help be the Swiss Army knife to help scale the company, and then maybe that turns into more." Or there's some CFOs that are quite operational. They could take on more scope sometimes.
**Claire Hughes Johnson** (01:08:11):
But I think there are other paths to getting that leverage, and there are also ways to de-risk the hire because you could end up searching forever, right? And I worry that it's become too much of a panacea in people's minds, like somehow they're going to find... And people will call me, and they'll be like, "I just need to find you." And I'm like, "One, I may not be right for your company, but two, that was a lot of work, and I think we actually, in the end, maybe got pretty lucky." How would you know someone is fantastic? Someone said something very smart to me, which was... I was in a meeting. It was me and Patrick. So Patrick is the co-founder and CEO of Stripe. And they said that having just the right amount of tension in our relationship was how you knew it was working for the company.
**Claire Hughes Johnson** (01:09:03):
And it gave us both a little bit of pause, but we ended up having quite a good conversation after that meeting, which is there has to be mutual understanding and trust and an ability for Patrick to say, "Hey, can you go do this thing?" And then believing, I will do it at the level of quality and intensity and intentionality that he would like. But there also has to be some friction, where I would maybe say, "No, I'm not going to prioritize that. I don't think that's important for the company," or I'm going to give you feedback that I don't think we're doing this well, or he's giving me feedback. The customer experience is suffering. All your scale stuff is degrading this thing, right? So fantastic is not all hunky dory. Fantastic COO is just the right amount of friction intention with forward momentum and mutual trust, because then the whole is greater than the sum of its parts, right? That's what you're looking for.
**Lenny** (01:10:03):
I was actually going to say, I've worked with some founders, and they have this concept that they hire a COO, and they would just solve all these cultural issues they're having these relationship issues. And sounds like that's exactly what you're saying, is that that is not often the solution to some of these deeper issues.
**Claire Hughes Johnson** (01:10:18):
Well, that would be the other problem, is actually believing... I was getting recruited, Lenny, and people would... Essentially, I felt like the founders were saying to me, "I'm going to give you all of the things I don't like doing as your job." And I was like, even if I'm by the way not qualify to do all those things, number one. And two is sometimes that list would be quite long, and that would make me nervous. I was like, "Do you really not running a company actually? Is that what's going on here?" And really, I think they weren't confronting elements of their work that needed to evolve and change. And what I loved about joining Stripe was... I think people also think, "I'm just going to hand all this stuff to this person and..." I'd love to say I took all this off of the Collisons plate, and Billy and John and the other people who were there at the time, and no, we actually were more collaboratively worked together, and I think it helped...
**Claire Hughes Johnson** (01:11:18):
Well, one, you don't feel as isolated because you're in a team, but also there's more joint work than people realize, I think at least in the companies I'd like to work for.
**Lenny** (01:11:30):
For the final 10-ish minutes we have together, and you have to run-
**Claire Hughes Johnson** (01:11:33):
Yes.
**Lenny** (01:11:34):
... I was thinking I could go through just a rapid fire set of tactical questions and see maybe one piece of advice you would share with someone that's maybe struggling with this thing.
**Claire Hughes Johnson** (01:11:44):
Okay.
**Lenny** (01:11:45):
And the first is from a also Twitter person, Manuel [inaudible 01:11:52]. And he just had a question around, as you're scaling, keeping alignment strong is challenging. What would be something you'd recommend to someone that's scaling quickly and trying to keep people aligned?
**Claire Hughes Johnson** (01:12:02):
Well, a lot of what we talked about, having common codified documents of what we believe in, how we work, and then using communication practices very intelligently. Never think that one communication, meaning an email or an all hands, reaches the audience. You have to be smart about how you communicate.
**Lenny** (01:12:23):
Awesome. Amazing. On a different podcast, we talked about how the leaders are often the repeater in chief, just having to repeat the same thing again and again.
**Claire Hughes Johnson** (01:12:30):
Yes. And just like a marketer, use different channels. Some people read emails, some people watch videos, some people attend the meeting. Repeat.
**Lenny** (01:12:40):
Love it. That'll be our clip to take away from this. I was watching an interview with you, and you talked about the value of offsites for creating cohesion within a team. Can you just talk about why offsites are so important to a company and a team?
**Claire Hughes Johnson** (01:12:53):
I think offsite is really a vehicle. The concept is the following, which is when you yank people out of their day-to-day routine, you create space, and also you imprint memory. And so if you say, "We're going to do a very different thing with your time today or the next two days, we're not going to do our emails, we're not going to do our regular meetings, we are going to sit and work together, we're going to brainstorm," you're basically activating new parts of their brain, and then you're also having a group experience that cements a belief system usually, or a set of plans. And it also helps bring people along. We formed this thing together, it's not effective if I say, "I locked myself in a room for three hours, and then I came out and here's the plan." You want to lock yourselves as a group, as a team in a room for three hours. How do you do that? And so that's why I think it's valuable. It's just out of time, in a way. You're taking it out of your day-to-day time, and I can't not found a good substitute for that.
**Lenny** (01:13:56):
On a different topic, one of the most common questions I get from product managers and just founders that I haven't tackled yet, and I'm curious what your take is, is around just keeping the company updated on what's happening broadly.
**Claire Hughes Johnson** (01:14:07):
Yes.
**Lenny** (01:14:07):
What have you found works for just keeping people informed on what's happening across the company and-
**Claire Hughes Johnson** (01:14:12):
Having really smart communication practices is something that I think a lot of companies don't invest in early, and it's partly because it feels like extraneous, but it's a lot of time. If you're going to communicate well, you have to invest in your intranet site and what's on it. Ideally, everyone logs in and sees information on the homepage of your company internally. Do you have a newsletter? Do you have founders do like a message or a quick video, whether that's on Slack or email. There's a lot of smart tools. You can learn a lot from social media in some ways, but you actually need a strategy for it, and you need a set of people who help make sure it happens so that again, it creates stability and cadence. And if I want to find information about X, this is where I go. And I think there's also that if you do it well, it can replicate down to teams, which is, oh, we have our weekly snippet stock that everybody can see the important news or whatever it is.
**Claire Hughes Johnson** (01:15:09):
But you need to create those things because they'll start to spring up, but then you'll have a million of them, and you won't be able to point people to the core messages. But it is not a thing to be taken lightly. And I think having someone who really not focuses on internal marketing, I'm talking about just good, "Here's what's important. Here's what you need to know." Sales teams actually do this really well, because they have to, because they have to keep the sellers up to date on the product and up to date on how to pitch it. And so it actually is worth talking to smart sort of sales leaders who've scaled and saying, what do you do that keeps everyone on the same page
**Lenny** (01:15:48):
As you're talking, I realized [inaudible 01:15:49], who we mentioned a couple times, she left Retool, and she's working at a startup that has trying to solve this problem, I think it's called. It
**Claire Hughes Johnson** (01:15:56):
Is a lot about what they're working on. And it's because it is, again, an unsung thing that is critical and that I don't think people naturally come to.
**Lenny** (01:16:03):
Next question, what are one to two, or maybe three things that people can do to run more effective meetings? I say give this masterclass on running more effective meetings. And just to boil down, what are a couple things people could probably change?
**Claire Hughes Johnson** (01:16:16):
I do have a video on YouTube about running an effective meeting, but I think the number one thing is the work of a meeting is not calling the meeting. Calling a meeting is easy. In fact, that is a problem. The barrier is very low, and it should be higher. What you really want to know... People need to know why are we meeting, and what is the point, what's the objective of this meeting? Is it to make a decision? Is it to share information? Who needs to be here? One of my favorite things to say is make the thing that's implicit explicit. Too many meetings are implicitly about something and not explicit enough. And I'm like, "No, no, no. I want to know why I'm here. Are we making the decision? Who's making the decision? And how?" Even better, you say, "Does anyone not need to be here? Because we'll just send you a note afterwards about what happened? Right? Make it more efficient, but be really explicit about the point of the meeting, and really do some inquiry on whether it's important, whether it's needed.
**Lenny** (01:17:17):
Maybe a final question is around decision making. So product managers who are, a lot of the audience of this podcast, have to, one, make a lot of decisions, get people to alignment, but they also don't classically have authority over anyone. What advice do you have for aligning and decision making?
**Claire Hughes Johnson** (01:17:34):
I love product management, so much accountability. So little authority. Such a hard job.
**Lenny** (01:17:39):
What a fun [inaudible 01:17:41].
**Claire Hughes Johnson** (01:17:41):
Everyone's like, "I want to be a product manager." I'm like, man, that is one of the hardest jobs in tech.
**Lenny** (01:17:45):
Yeah.
**Claire Hughes Johnson** (01:17:46):
But anyway, how do you get people to a decision?
**Lenny** (01:17:48):
Yeah.
**Claire Hughes Johnson** (01:17:50):
Actually, it's exactly... And I mentioned in my book, Gokul's SPADE Framework, which you can look up. He has a coda on it. But actually, it's the same thing that I said about meetings, which is making it very explicit, that there is a decision to be made, who is making the decision, the criteria by which the decision's going to be made, who will be informed. There's all these models. There's racy and radar, and there's a million different decision models. Just pick one, make it explicit, explain that's what's happening, and get people through it. Follow the model and do it. And by the way, you can always have an asterisk, which is if we want to revisit this decision, this is what we do. But I think too many teams get paralyzed because they're afraid, like, well, maybe they're not the decision maker, or maybe... When I say to people at Stripe in our onboarding, I used to run a session, I was like, if you're not sure who the decision maker is, one, it's probably you, and I'd rather you act that way than not because you're going to slow the whole company down.
**Claire Hughes Johnson** (01:18:52):
But really, I think the other thing is, in the book, I talk about this framework that Bezos uses, type one, type two decisions. Is it high impact? Is it irreversible? Is it not? Really evaluate, what kind of decision is this? How hard is it? And then follow a process and get it done. And don't forget to actually make a decision. And if you don't know who the decision maker is and you're worried it's not you, just ask. Don't get stuck. Too many people get stuck, and it makes your work terrible, right? What do we all care about? Progress, impact, momentum. If anything I would say about advice to people generally is be a force for positive momentum, and it will be actually a real career maker.
**Lenny** (01:19:41):
I love that. Maybe we'll make that the title of this interview. With that, Claire, I know you have to run. Anyone listening, you got to buy this book. Like I've said at the beginning, if you like my newsletter, it's exactly my newsletter, but as a book about operations.
**Claire Hughes Johnson** (01:19:54):
Thank you. Scaling People.
**Lenny** (01:19:56):
Scaling People. Is there a website they can go to to check it out on Amazon, or is there-
**Claire Hughes Johnson** (01:20:00):
They can go to press.stripe.com/scaling-people.
**Lenny** (01:20:00):
Amazing.
**Claire Hughes Johnson** (01:20:06):
Or Amazon. Just search scaling people on Amazon.
**Lenny** (01:20:08):
Cool.
**Claire Hughes Johnson** (01:20:09):
But thank you, Lenny. I appreciate it.
**Lenny** (01:20:12):
Absolutely. Just two final questions. Where can folks find you if they want to maybe ask you questions, follow up, reach out? And then two, any other way people can be helpful to you, other than maybe pre-ordering the book?
**Claire Hughes Johnson** (01:20:20):
Well, definitely pre-ordering the book and giving me feedback on that. I guess Twitter is probably the best place to find me. I'm @chughesjohnson on Twitter. But honestly, I do hope you'll consume the book in some form and interact with it because the goal is to make it useful. We talked about this, Lenny, your podcast for my book is just trying to be of use, and I hope it is a positive force for positive momentum. And I really appreciate the opportunity.
**Lenny** (01:20:49):
Absolutely. Thanks for making time for this.
**Claire Hughes Johnson** (01:20:53):
Thank you.
**Lenny** (01:20:53):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [17/22] Career frameworks, A/B testing mistakes, counterintuitive onboarding tips, selling to developers | Laura Schaffer (VP of Growth at Amplitude)

**Laura Schaffer** (00:00:00):
... Like the dead of the night. And by that, I mean 7:00 PM or something on. I'm pretty sure it was a Friday. We just asked for forgiveness and put these questions into the silent flow and ran as Navy test with a small group. And I'm fully expecting, "Okay, this is going to hurt our numbers, but maybe it won't be so bad and I'm going to be prepared to advocate the power of this data that we're getting." And I was totally geared up thinking about written, started to write the framework for how I wanted to surface this. And we start to get the data for this thing. I'm not kidding, an improved conversion. There's no personalization, nothing past it, just the questions. An improved conversion by like 5%, just improved signups. And it was one of those like, "What? Okay, what is going on here?"

**Lenny** (00:00:50):
**Laura Schaffer** (00:04:18):
Thanks, Lenny, it is so great to be here. Thanks for having me.

**Lenny** (00:04:21):
It's great to have you. So I asked Elena Elena, Elena, I'm not even sure how to pronounce her name, maybe. What is it?

**Laura Schaffer** (00:04:21):
Elena. You got it.

**Lenny** (00:04:27):
Elena. Okay. Okay. I think I've said it wrong all the time. All this time. Okay, Elena. So I asked Elena Ferna, who's a popular guest on this podcast who I should have on this podcast and you are the first person that immediately came to mind. And so I'm really excited that we're doing this and that you agreed to be on.

**Laura Schaffer** (00:04:42):
Well, she's the best and I'm really happy that she referred me because I'm just stoked to be here. So thanks for listening to her guidance.

**Lenny** (00:04:50):
Absolutely. And it's a cool time to be chatting. You're the newly minted head of growth at Amplitude and so congrats, first of all.

**Laura Schaffer** (00:04:57):
Thank you. Appreciate that. Yeah, this is my day two and a half here. So very [inaudible 00:05:04].

**Lenny** (00:05:06):
Wow, you're a veteran.

**Laura Schaffer** (00:05:06):
Yeah, right.

**Lenny** (00:05:06):
I love it. Some companies, there's a little percentage of that shows you how many people have joined before you and I wonder what that percentage already is [inaudible 00:05:12].

**Laura Schaffer** (00:05:12):
We had that in Twilio and I got pretty, pretty high up there after a while. We had a stack rank and a spreadsheet. Yeah, but it is funny. So wherever that thing exists in Amplitude, I am right fresh there at the very bottom.

**Lenny** (00:05:25):
So what was the number you got to Twilio? Any, do you remember?

**Laura Schaffer** (00:05:28):
Yeah, no, I was very proud to crack the top 50. That was my claim the same because as people left, you move up. Right?

**Lenny** (00:05:36):
Right. Yeah, it's bittersweet.

**Laura Schaffer** (00:05:39):
Well, yeah, right. On one hand it's like, "Ooh, very cool." And one of the OGs on the other hand, it's like, "Oh my gosh, this person's [inaudible 00:05:47]. Bummer." It's a shift, but I'm excited about it for sure.

**Lenny** (00:05:51):
So you have this new exciting role and I thought it'd be fun to start to chat about career growth and just how you think about career growth. I know you have a framework of how you think about your own career growth and clearly it's worked out, so I'm curious to hear about it and see how it could be helpful to folks that are listening. So yeah, can you just tell us about how you think about career growth?

**Laura Schaffer** (00:06:11):
Career growth is definitely not a straight lineup, but there's definitely some frameworks and methods that have worked really well for me. And I think to dive into it, it's first good to just talk about the one that I most typically see people use to try to grow their career and why that can be a little problematic, which is that I see most people try to work really hard the job that they have within the role that they have at a company. Do whatever you can to grow there, show your manager all these things. I see people keep spreadsheets, it wins. So it can come up with performance reviews. Maybe you try to get better advocating for yourself, maybe try to get peers to notice or your manager's peers. And that's all good. It's all stuff.

**Laura Schaffer** (00:06:52):
But the problem with it is that you're limited to what your manager's ability is to advocate for you, to promote you. And you're also limited by the explicit trajectory of your role at that company and where the there's room for that or not at the company. And then often that perception can sometimes be a little bit in contrast to what your perception is. And also other things that happen, your manager leaves and then you have to restart with someone else. So the method that I use tries to take that power back a little bit. And something that I learned really early on in my career, I was very lucky to learn by accident, was at a company called Bandwidth, which is my first real job. And Bandwidth is now a public company and they've done all kinds of crazy amazing things.

But I joined when it was just 50 people and I actually joined in sales and I was just hungry to make it succeed and grow and bright eyes and everything, first real job. But I realized after a few months of being in sales that I was often repeating the same thing over again, using the same thing to sell over and over again. And it's like, gosh, this isn't ideal for the customer because [inaudible 00:08:04] call me and ask these questions and get these answers and all this stuff. And it's not ideal for the company because they're paying commission on this every time. That's not going to be efficient for our growth. And because we were small, I was able to catch our GM and I was just like, "Hey, I've noticed this pattern where I'm repeating things over and over again and they're asking the same thing.

I think we should put that online. I think we should make that available so they can just see it and then buy it," because we had an online checkout process. And I was expecting him to be like, "Oh, well, I know it's important but for this [inaudible 00:08:46] another, we need to do it this way, and obviously you've thought all about it." And thinking, "Oh, I'm going to come in this new person, he's just going to help me understand what I'm missing here." There's a little bit of that that I was expecting. And he goes, "Wait a minute, tell me more about that. What do you mean?" And by the end of the conversation he was like, "Hey, why don't you go do that? Why don't you go build that experience? Why don't you put that stuff in a self-serve flow?"

**Laura Schaffer** (00:09:06):
And we called it e-commerce manager and it was like got a growth before this growth, this is like 2010. And that moved me into a totally new position. And the main learning that I had from that was, which really took life at Twilio and absolutely worked for me there and I'm happy to talk about that too. But the core that learning was, your executive team and executive teams at companies are often very sharp, but the nature of their day-to-day just does not link them with customers.

**Laura Schaffer** (00:09:34):
And that means that over time, especially as a company grows, they often lose access to some of the best insights and in the heartbeat of the people who they're providing value to in contrast to folks that are closer to the problem. And so that means that your superpower is in really pulling those insights in and bringing them to life, staying close to the customer. There's not a single leader or executive that isn't going to be stoked to hear about valuable customer insights that highlight problems they might not be seeing. And there's a lot of those. So especially when they align to North Star metrics, those ones are the powerful ones. That was the way that I grew my career at Phil and I'm happy to share that journey too.

**Lenny** (00:10:18):
Yeah, it'd actually be cool to hear maybe another example of that. But I think an interesting thing that comes up for me here is sometimes you may have an awesome idea and it may not immediately happen. It may not be like, yes or let's move on, that's right, immediately. And I think it's important to just recognize they're not going to follow all your ideas, but they're always looking for better ideas. And to your point, they may not have the information that will lead to an idea that you will have because you're on the ground dealing with real problems, day-to-day. So I think it's important to recognize you're not going to always get your way and that's normal.

**Laura Schaffer** (00:10:52):
Yeah, totally. And it's almost like building up your individual brand a little bit. And I think one of the most powerful and accessible ways is learning about your customers. There's always those people at companies who's like, "Oh, well, she just knows our customers or he just knows our customers, they just know our customers. They just know." And it's like, "Well, how?" "They just know. Let's ask that person. Let's get their feedback." And those people often have a good amount of brand recognition of powers within the company and they're often thought of when the company needs to do something new or different or if someone is hiring, maybe they're thinking about that person for a cross team thing.

**Laura Schaffer** (00:11:31):
So it's one of the ways that you can build that brand. And again, I think it's a sweet spot because it's something that is very valuable to everyone, all the way up to the most senior leaders, which we can talk about here in a minute. And so it's going to be valuable for you in a valuable tool no matter where you're at in your career. And that's not always an immediate payoff, but it often does give you a trajectory outside of just your role and just your manager. It gives you something a little bit broader.

**Lenny** (00:12:05):
So maybe a simple way of describing to mirror back what you're saying is carve your own path. Don't necessarily assume your managers will give you the path that makes most sense for you or even give you the biggest opportunity. Just propose, "Hey, I think this might be a better opportunity and I'd love to pursue it." I'd love to hear the Twilio example if that's generally-

**Laura Schaffer** (00:12:25):
Yeah. So when I joined Twilio, there was no growth team at all, not even a breath of it. I joined in product marketing and I was leading our product marketing for our messaging lines, but I followed the same guy that I just mentioned. I made it my own personal policy to like, hey, I'm going to do my job. And I'm going to do well, I'm going to keep notes of things I'm doing well and all that stuff because it's good, but I'm also going to get to know our customers. And I'm going to get to know our customers really well and I'm going to pay attention when I'm connecting with them, not just about the space I'm in, but just broadly what are some of the pain points and things they're articulating that are relevant to the business and what we're trying to get done.

**Laura Schaffer** (00:13:00):
And one of the things that came up was that users were struggling and folks were struggling to get started and use Twilio. And that contrasted so deeply to some of the things that our executive team was saying and had high conviction in our company had high conviction, which is that Twilio was so easy to use. In fact, it was top three things about Twilio that we were really trying to get out of their brand. Were so easy. Developers love us, they say we're so easy. And there were tweets coming all the time, developers saying like, "Oh my gosh, they got started in a couple of minutes." So there's all these things that made that compound and made that conviction stick. But as I was talking to customers, I was hearing a very different story and it made sense as we were penetrating new markets, adding more products, we were adding complexity and we were pulling in folks who were a little bit less motivated and those things contributed to people saying this is difficult.

**Laura Schaffer** (00:13:55):
And so at the time, this wasn't a 50 person in where I could just go to the floor and go to someone and be like, "Hey, there's this thing I heard about, I think we should do something." But there was another tactic that I could take, and I just started sharing a voice of the customer report. I started sharing my insights, started writing down and just sharing them. And it became with digest and eventually people were like, "Hey, can you share it with me? Can you share with me? Can you get on your list? Can share with me?" And this was in a few months of me joining, I was doing this. And then that turned into, "Hey, you should host a quarterly voice to the customer session or for all of product." And this was a request that was coming from some of the senior leaders at the company.

**Laura Schaffer** (00:14:33):
And when our Jeff Lawson is our CEO at the time heard about, he started attending too. So now in the session I started pulling in other people's insights too, because now they had a forum for this. I could do that and have people send that to me and I could compile it and all of these things. So then this established me as that person who knows about the customer even after short tenure. And then when came time to do annual planning that year, and I joined in 2014 at the end, so this is 2015, I pitched this idea, "Hey, we think that it's easy. It is not. Here's data that I have, the information that I have and I think that we need to start a growth team here and that needs to be a core focus." And I was able to bring in a really critical partner to that and other folks who could support that because I had built up some of that trust.

**Laura Schaffer** (00:15:28):
So by the time I was making that pitch, I had someone on Andre Crow who was the seventh hire at Twilio and got to number three on that spreadsheet or whatever who was really close to the CEO being like, "Yeah, we desperately need this." I'm seeing this. He led a website, he basically created the Twilio brand and he led all the website stuff and he is like, "Yeah, we definitely need this." So not only did I have that little bit of trust from the executive team, but I also had folks who were just trusted on their own advocating and supporting this that I was doing. And so it was approved just almost very easily. I put stuff together for it, but it was the meeting before the meeting had already been done by this other thing. So it helped me create the growth engineering, growth product team at Twilio.

**Lenny** (00:16:14):
I love just how proactive your advice is here. There's a lot of people that don't do well and then just like, "Oh, I never had the opportunity or I kept got looked over all this time." And I love that there's all this just like, here's things you can be doing to get in front of people to provide value, to just create opportunity for yourself. Any other advice along the lines of just like, here's the things you could do for yourself versus waiting for someone to come and give you opportunity?

**Laura Schaffer** (00:16:42):
Yeah, I think that's the most easily actual because to do all of our jobs, we need to know customers, we need to know about customer insights, product, we need to know. But then also customer facing teams, social, those want to crack into product. Your insights are extremely valuable. You're talking to customers every day more about their problems and their pain than a lot of other people do. And so that is by far and away to me the most powerful and accessible by anyone in any role in any space. But I'll also say that that broader concept of just, hey, there's things that, and things of value that you know that others can benefit from at your company and building your brand as someone that is supportive, smart, creative, able to solve problems, make sure that you're sharing that. And so maybe you're really freaking good at communicating with brevity.

**Laura Schaffer** (00:17:35):
I suck at that by the way. So more powered anyone that can do that, I'm actively working on it. So share that. Go to your general Slack channel or whatever and just be like, "Hey, just wrote some tips for how to do it, some ways that I am good at this." And those kinds of things can really go a long way towards people starting to view you as an SME and not just the space that you're in, but in broader areas. And that can always present open doors for you and other people are looking up to you and seeing you, someone who's strong in ways outside of just the role that you're in.

**Lenny** (00:18:07):
SME is a Subject Matter Expert, is that right?

**Laura Schaffer** (00:18:10):
Yes. Thank you for unpacking my acronyms. That's another thing that I am actively working on.

**Lenny** (00:18:16):
I got you. I'll be on the lookout.

**Laura Schaffer** (00:18:16):
Yes.

**Lenny** (00:18:19):
Maybe one last question along these lines is do you have any advice for framing the proposal, framing an opportunity to your manager, higher ups that you see has worked best broadly?

**Laura Schaffer** (00:18:34):
Yeah. Yeah. And one thing I want to say too is with this stuff, I don't think that it necessarily does counter to what your manager's doing. It's more supporting them. I've done this stuff and then it's helped my manager promote me. So it's not necessarily, "Oh, we'll do this if your manager's failing you." Or they are not the boarding you or they can't support you. It's more like do this because this is going to be an accelerator for yourself irrespective of your manager.

**Laura Schaffer** (00:18:55):
But then also it'll be an accelerator for your manager in supporting you because one of the things that comes into play a lot when managers figure out promotions and doing those things is they'll sit in a room, often calibrations and with a bunch of people, and it makes it a lot easier when those people have had some access or exposure or whatever to you in a positive light. So these things can all run with your manager and not against, but it's just another way of you taking back the ability to build that momentum instead of relying on all of that going through one single other person.

**Lenny** (00:19:33):
And what I like about your second example is you just did it. You just started doing that tenant report for the company. It wasn't like, "Hey, I have a proposal, here's what I think you should do. Should we do it?"

**Laura Schaffer** (00:19:42):
Exactly.

**Lenny** (00:19:42):
It's just like, yeah, just do it.

**Laura Schaffer** (00:19:44):
Yeah, ungate your knowledge I think is the buzzword that I'm hearing.

**Lenny** (00:19:52):
Mm. Never heard that.

**Laura Schaffer** (00:19:52):
I think that's an Elena, see how many times we can bring her up. But you can do that within your own company. Everybody is skilled at things that they aren't explicit to their role or their space. And I think that ungating that opens opportunities. And if you're not sure, then go to my favorite go-to, which is talk to customers, get insights. Those are incredibly valuable. So rarely do people share those when they find them. So be the person that does that.

**Lenny** (00:20:21):
Another area I want to chat about is experimentation and growth and data, which makes sense if strong perspectives is on being the new head of growth amplitude. So maybe we start with experimentation. You mentioned that there's a really interesting surprising result in an experiment you ran at Twilio that maybe changed your perspective on experimentation and what you think might work and not work.

**Laura Schaffer** (00:20:45):
A hundred percent. Yeah, I'm through a fortune of two mind-blowing experiments that really shifted the way that I think about growth. So one of them, one of my favorite ones happened very early on at Twilio. So after I created this growth team, one of the things that I saw as to me an issue was that under signup flow, we just asked people for a username and an e-mail, like a password, and that was it. And that's actually relatively common at the time. This is a while ago now, everybody is [inaudible 00:21:16]. But we didn't, and actually there was a lot of existing conviction around that. I was like, "Hey, we retarding developers. Developers, they just want to do, they just want to get their hands on things. Don't put anything in their way, it's going to be disastrous. We don't want any shenanigans here with these folks, let's just let them in the gates."

**Laura Schaffer** (00:21:33):
But to me this was a really big assumption to make and a very costly one. It's like, okay, if that's the case, we're not going to know anything about anyone. And we didn't know who was signing up, we didn't know what they wanted to do. And that hurt our ability to understand how people were performing from a quantitative perspective. We were a little bit lost with prioritization. There's a number of implications here, but it's obviously a very contentious space. So this is the very first thing that I did and the first experiment that I ran. I did some research to understand say, okay, what are the most important questions to answer? What would I do really, really need to know? And it was stuff like what language are you coding in, what's your use case? What product you want to use?

And then there's one around, are you developer at all or were you use something else? Because there is rumors that we're having, not just developers sign up, which is this whole other interesting story. And I think of these questions that would also potentially be things that our developers signing up would understand why we're asking that it would feel natural. But anyway, again, adding anything to the signup was very contentious, but I really just wanted to get a little bit of data on it. So I wanted to run a test. I didn't have a team, I didn't have an engineering team yet and none of that stuff had built out. It was just me, myself and I. But like I said, I had started to build a little bit of trust and [inaudible 00:22:50], Andre, who I mentioned earlier who, because he was early employee and he had access to everything, one of those people, and he also was supportive of this and had similar haunches.

And so like the dead of the night, and by that, I mean 7:00 PM or something, I'm pretty sure it was a Friday. We just asked for forgiveness and put these questions into the signup flow and ran as Navy test with a small group. And I'm fully expecting, "Okay, this is going to hurt our numbers, but maybe it won't be so bad and I'm going to be prepared to advocate the power of this data that we're getting." I was totally thinking with written... Started to write the framework for how I wanted to surface this. And we start to get the data for this thing. I'm not kidding, an improved conversion. There's no personalization, nothing past it, just the questions. It improved conversion by 5%, just improved signups. And it was one of those like, "What? Okay, what is going on here?" And I actually dug into it, and what I found from just talking to a few customers once through the flow, I'm just learning about [inaudible 00:24:00] about it.

**Laura Schaffer** (00:24:01):
It was actually for folks, it was comforting. When you think about it, when users are signing up for your product for the very first time, it's new. This is new, that means it's scary. They're expecting it to be difficult. They're anticipating that there's going to be friction and challenges and that they're not going to figure it out. Almost like looking for the bogeyman. And that's the headspace. It's often the headspace that any of us are in when we're doing something new for the first time like ooh, this could be very challenging. And so by putting in these questions it's like, what's your language? It's like, "Oh, I do. I code a JavaScript and I can select that." Well, that's something I'm uncomfortable with. That would make my journey easier. Like "Yeah, bingo. That's my use case. Okay, I'm in the right place here."

**Laura Schaffer** (00:24:51):
It was actually giving folks something comforting and challenging the notion that this was going to be difficult, just the questions because it was aligning to some of the things that they were organically thinking about, which is what if they don't support my language? Or can I even do this use case I want to do? And so it was just a really interesting, the takeaway for me for this, the really interest takeaway was the psyche of the user is so, so critical. That's just as important as understanding your product and the broader market you're applying to and all those things. Just the psyche of users, new people doing things for the first time in your user flow, understanding that is powerful. And the simple catchy thing I say is that ultimately the learning here is, bad friction is bad, and good friction is good. There's no such thing as it being simple. It's just all friction is bad, which is what I had assumed going into this.

**Lenny** (00:25:50):
I love that you were new to Twilio and you just year-load an experiment to production.

**Laura Schaffer** (00:25:55):
Year-load. Yeah.

**Lenny** (00:25:56):
That's a big move.

**Laura Schaffer** (00:25:58):
It ended up being very helpful for everyone. I shared the insights from it and all these things. I've shared the [inaudible 00:26:05].

**Lenny** (00:26:05):
And [inaudible 00:26:05] conversion.

**Laura Schaffer** (00:26:08):
But for sure, use such processes with caution for sure. Yeah.

**Lenny** (00:26:08):
I love it. It's amazing.

**Laura Schaffer** (00:26:15):
That the right way to do [inaudible 00:26:15] advocating for the engineers here is the right way to make any changes in production is through or with the approval of engineering, but it was the right move overall and definitely helped business, so yeah.

**Lenny** (00:26:33):
Yeah, I love it. No, that's great. I like that move. I think we need more of that probably. I want to dig into what you actually... So what is it you changed, you added how many questions and then what were the questions?

**Laura Schaffer** (00:26:37):
There was a question around what language are you coding in? And then as an option to that, it was like, "Oh, I'm actually not coding, I'm not a developer." So for us, it actually gave us two really, really interesting data points. One was how many developers versus people who are not coding or in our flow? And then what language of the coding, which was massively helpful not just for growth and onboarding, but our documentation team, dos team. Would that end up being a critical way for us to gauge trends over time and catch things before whatever reports would come out at the end of the year, what people are doing, you start to see it. And then also product. What product are you interested in using? That was very critical for knowing the basics of how to organize someone's onboarding. Are you doing SMS? You're doing voice? To 281 or whatever. And then use case in use cases, you're doing a appointment reminders or are you doing a autoresponder or are you doing anonymous communications for a dating app or something. Right? So those were the very first questions.

**Lenny** (00:27:39):
Wow, okay. So it was four dropdown questions and that increased conversion. I love these examples where friction and increased conversion... There's so few of them. You hear about this could work and it's rare. And so what did you take away? What's the pattern you took from this? There's the idea, it's good friction, but is there something that you're like, what is a sign of this is going to be good friction?

**Laura Schaffer** (00:28:02):
There's still alleviated a problem. They alleviated the problem they had where they're coming in and worried that it was going to be difficult or that they weren't going to be able to figure it out, they weren't going to be able to get their footing. And I'd say that that's not unique to Twilio. That's something that I think users experience at any front door, at any company, any signup beginning the signup loads, it's like, "Here we go, buckle up." Especially when it's in a work context and there might be extra pressure on you to succeed or for you to make as an accurate assessment. So I think that psyche of, "Okay, am I in the right place? Is it's going to do what I need it to do? Can I figure it out? Am I capable?" These are extremely common things for people to feel when they're signing up.

**Laura Schaffer** (00:28:48):
And so certainly, that I think can carry out to any place. I'd encourage absolutely everybody to be putting those experiences within their early onboarding, not just for you selfishly, so you can learn and segment them appropriately, but also so the user can feel more confident as they get going and like, "Hey, I'm in the right place. This is going to do what I needed to do." But I think that the carry over there is just the psyche of the user and just being so aware that it's not so cookie cutter as, "What is the problem my market experience is and what can my product do to help them?" There's also this other thing in the room which is so important to people's success, their ability to succeed with your products and your self-serve experiences, which is, what is the mentality and the psyche of the person at the various stages in your journey?

And if you're not incorporating that or addressing that, you will absolutely miss things or things will fail and you'll be very confused as to why. We had a great experiment that I'm happy to talk about where same concept, a totally different situation, which is later in onboarding. One of the things that we tried to do over time to make Twilio less complex was to offer steps like, [inaudible 00:30:08] onboarding, welcome step one, here's what you want to build. Great, we all know that now, "Okay, step one, go do this thing. Step two, go to this thing. Three, this thing. Four, this thing. Five, bam, you're live, congratulations, aha," all these things. So we shipped that, got that out there and I was like, yeah, it was improved conversion. It wasn't like that great. It's like, man. We went from there being absolutely nothing, "Choose you're adventure, figure it out, go figure it out. Good luck." To this prescriptive thing. And it wasn't converting [inaudible 00:30:37].

**Laura Schaffer** (00:30:38):
So to talk to some users and there wasn't anything particularly obvious that was coming out as to what the issue was. It was like, "Oh yeah, Let's go to step one." And we did mock the people. "Okay, now I know, I do step two." But there was one thing that I was hearing that was coming out that feels like something, and that was the telephone number, the telecom part. Developers when they were coming into Twilio, it was things that were familiar to them. APIs, the language they're coding in, code samples, documentation, things like the bogeyman, the things that would psychologically trip them up, telecom, phone numbers. These things that just were completely out of the zone of anything that they'd ever worked with before, especially earlier on in Twilio's journey.

**Laura Schaffer** (00:31:28):
But even now, right? Telecom's very different beast for most developers. And guess what was step one? Get a phone number because that's step one. Anytime that anyone's trying to teach one to use Twilio one-on-one, always going to sit down, ask and be like, "Okay, here we're going to go get a phone number and configure it." And that's what anyone every time will do. However, in a self-serve experience, when you don't have that safe person sitting next to you being like, "Don't worry, it's going to be okay, I'm going to take you through this crazy telecom journey." They're on their own, but that's psyche telling is them like, "Oh my god, telecom. Well, I can't do that. That sounds scary. We're getting a phone number configured. Whoa, I'm out of my debt."

**Laura Schaffer** (00:32:01):
And so what did we do to test this out? Test out whether that was the issue? Actually, and it's first we're in the MVP. They kicked them out of the portal entirely and put them into a docs page where we could manufacture an experience where the first thing they saw was code and they're in the docs safe place, the language that they're coding in and then snuck in there.

**Laura Schaffer** (00:32:26):
It was like, "Oh, get a phone number, let's go configure it." Not as step one, not as the leading thing, but embedded. And the analogy I have for this is pilling a hot dog. So if anyone's got a dog or an animal you have to feed a pill to, it's like you can't just feed the pill to the animal, it's never going to happen. But if you shove it inside of a hot dog, which looks good and that's exciting, then you can get them to consume it more easily. And so this was-

**Lenny** (00:32:53):
Yeah. We do peanut butter, that's [inaudible 00:32:55].

**Laura Schaffer** (00:32:55):
Yeah, exactly, right? Yeah, hot hotdog, peanut butter, all that. You bury it. You embed the scary unpleasant thing. And so that's what you said with the phone number stuff, that telecom stuff. And guess what? Even though we're a good amount of the console and they're going off and we had no easy return button, it converted better because we were addressing the big problem that was there at the time, which is their psyche. They were not ready to come in and immediately thrown into a phone number experience. That was letting the bogeyman and out to party and that's not what was going to work. We needed to put that bogeyman pill and the hotdog.

**Laura Schaffer** (00:33:31):
And so then once that validated, then we can actually go through the business of putting that into the onboarding float correctly and then that could be even better. But so again, the psyche of your user is such a critical thing to be thinking about. And if something very logical isn't converting well sometimes, it means that you're battling against the psyche of a user and you want to take a step back and think about and learn about where someone is psychologically in your space.

**Lenny** (00:33:59):
Feels like you had this experiment that was a complete redesign of the onboarding flow and that didn't work. And then your second attempt was a different approach that's like a full onboarding flow. And I'm curious, do you have a take on just when you run experiments? And it's something we dealt with a lot at Airbnb in other places is like, do you just redesign the whole thing or is it better to iteratively work from where you're today and just experiment piece by piece towards some future much better experience?

**Laura Schaffer** (00:34:26):
Here's what I would say to this is that from a high level, it's always going to be better to be iterative. And the reason that it's better is that roughly 80% of the times, ORs in the time are hypotheses and the things that we believe will be true [inaudible 00:34:42]. And this is amazing. There's an amazing article out there I'm happy to share with you so you can put in the show notes.

**Lenny** (00:34:48):
Yeah, absolutely.

**Laura Schaffer** (00:34:49):
That really takes a scientific approach to proving that out. Companies like Netflix and Microsoft, there's over and over again 80 plus percent. Some companies say 90% of things fail. And so the closer you get to something that you go bear your head in the sand or go into an attic and build something for six months and ship it, the more likely it is that you are going to ship the 80% wrong stuff.

**Laura Schaffer** (00:35:17):
Whereas the more iterative you are, the more likely that you're going to catch it sooner. And failure doesn't have to be a wall, it can be a compass, it can be the thing that leads you to the right thing. And so you always want to as best you can, get stuff in front of customers so that you can get that compass and get that compass activated, know where to go.

**Laura Schaffer** (00:35:40):
So that means doing ugly things. I tell my teams all the time, if it's not embarrassing, you've gone too far. Got to be embarrassing. The first thing, that was embarrassing, kicking people out, onboarding, spend all this money and whatever to get them into your center flow, and then the first thing we do, get out of here. That's nuts. But if it hadn't validated, that would've been a very cheap but very valuable learning. Instead, it was a very powerful cheap learning in the other direction. Okay, now we know we can invest in it. We know that's the right thing to do. So always better to be iterative so that you are letting failure work for you instead of having it be a trap that you fall into.

**Lenny** (00:36:22):
I know that you just shared as per experiment, you're probably wrong 80% of the time. In my experience, launching a halt redesign is as negative a hundred percent of the time. I've grown weary to avoid that as much as possible, which is like, you know that, you're taught that as you go into growth and product, but you're just like, "Nah, come on, let's just make it awesome. Just redesign this whole thing." Especially your designers is always like, "No, let's start again. Let's make it amazing." But it always ends up being negative and you're like, "Okay, well, it's too late now we got to launch this thing, we don't have time to start again."

**Laura Schaffer** (00:36:52):
Well, it's funny, in the articles, and you'll see it was written by somebody from Microsoft who built Implementation platform and did all these cool things, as he went into actually trying to apply a scientific method of figuring out how often people are wrong about their hypotheses and what they're planning to do. He's like, "I wonder if that applies to us here at Microsoft." Even for him, that question of [inaudible 00:37:16]. And I think it's challenging when there's a lot of smart people in this space doing things and it's very difficult to think, "Gosh, am I really wrong? 80 plus, 90% of the time?" But when you think about it, makes total sense because what has to happen for something to be successful? You have to understand the problem perfectly. You have to then understand who's having the problem perfectly, the customer. At what time they're having the problem.

**Laura Schaffer** (00:37:43):
Then you've got to put the right solution in front of them to solve that problem. Maybe you've got the problem, all that stuff, but your solution something off. Or maybe your solution is right, but maybe it's just not presented, it communicated in the right way. You could have any one of those things off and it's not going to succeed. It's not going to have the metric impact you're expecting it to have. So in that context, it's almost like incredible. We do succeed 20 to 10% of the time given everything that has to line up. And so I think it's one of those things where you really want to go into it embracing that, "Okay, this isn't about how smart I am or how good my team is or any of that stuff. It's just the logic of this is challenging to get it right and let's embrace that and let's lean into that knowledge and make it a part of our strategy," instead of finding against it.

**Lenny** (00:38:39):
Have you found anything that helps you increase those odds or is just, this is the way of the world and you probably can't significantly increase the chances your experiment works out?

**Laura Schaffer** (00:38:51):
So here's the thing, I think there's very little that we can do to make that space easier. All those things have to be figured out. And so I definitely think that everybody is going to be in a space where their original ideas, untested ideas are going to be around that hit rate. However, the way that you go about validating those can be totally different and you can be very fast about validating those ideas and that's the key. And AB testing is one of the most expensive kinds of ways to validate an experiment. It often requires design and engineering and the PM or growth person or marketing person who's crafting it. All these things are investments that take a lot of time even for simple thing. And then you have the time factor, how long's the thing I have to run to have an impact?

So all of that is extremely expensive. And so I think the key is to just think through, "Okay, what are the things I can do to quickly validate what these ideas are that we [inaudible 00:39:59]?" And you can do that with painted doors, which is where you test rate the concept and the idea before it exists versus the actual experience. You can do mocks. If you've got a designer, create those mocks for that experience, put it in front of people, see how they engage with it. That can be so powerful.

**Laura Schaffer** (00:40:16):
You could invalidate tons of hypotheses at that state. The only things you want to get to that deep AB testing environment or ones that have been vetted along the way. And that way, you reduce your fail rate, because you're failing faster by using other methods. So I think I more advocate for that side. Let's fail fast by using those tools rather than figuring out a way that you can rise above where everyone else is operating and figure out ways to solve all that complex stuff better because that's going to be challenging, but you can always get better at experimenting and validating things faster.

**Lenny** (00:40:59):
**Laura Schaffer** (00:42:15):
I'm a very data-driven person. I self-describe and think of myself that way. In large part because of that, I feel you have to be constantly checking yourself and data is a really great way to do that. But I definitely think that I would be described as someone who's going more by their gut when looking at date end results just because of the way that I approach it, which is I'm very comfortable and very common in using qualitative responses and things like that and supplement to quantitative data to make a decision and that puts less of a burden on the quantitative to really make an assessment of whether something was working or not.

**Laura Schaffer** (00:42:51):
One of the things I see, I think sometimes goes against what other folks do, although I'm seeing things shift a little, is that 95% confidence rate. My background in college, I was in a lab running experiments or really publishing two journal and stuff and we had to have that 95% confidence rate, had to because the things that were coming out of the lab and being published were influencing things like how we do education and how we understand how bias works and when it shows up and therefore how we can combat it.

**Laura Schaffer** (00:43:23):
Things were wrong. And sending a bunch of bologna, that can cause some significantly bad things like false positive, false negatives in that context can be very dangerous, for lack of a better word. And you think of other pharmaceuticals, the 95% confidence rate belongs in some companies and some industries because the risk of failure on the impact of a false success is very high.

**Laura Schaffer** (00:43:47):
But those of us converting users and trying to upsell folks, we are very fortunate to not have that level of burden on us and we can take advantage of that. And so there are definitely times where I will advocate for and I will push for and I will myself use lower confidence intervals and 95%, especially if that doubles amount of experiments that you can run in a year. End of the day, these are all methods that we use to try to validate the hypotheses that we have. And if you're doing a 95% confidence in a role, you're still accepting a 5%, some amount of false success, do that a little bit more, challenge you to do that a little bit more. And then run way more experience. If you look at the net of what your team is doing over the course of year, what you're doing over the course of a year, you will be positive.

**Lenny** (00:44:42):
Wow, that is a big idea. Idea of releasing the P-value confidence interval for experimentation and data teams. Everyone would be excited about this. Probably maybe not some data scientists on teams. Do you do that? How do you act? Is that how you operate on your teams? Just like we don't need 95% competence?

**Laura Schaffer** (00:45:03):
So I'll say this, this is actually very critically important. You must have this game plan set before you run something. Failure mode that I see so many teams fall into is they'll run the experiment or whatever it is and then they'll make the data fit the hypothesis. Or sometimes they'll go without a hypothesis and just be like, "This is going to do better things for our metrics," but not a core reason as to why or what exactly are we testing here. And so this is another area we could absolutely fall into that trap. "Let's [inaudible 00:45:36] on good 80. I think it's good. That Laura person said it was cool. So I think that that's fine." That will always be a trap. So it needs to be very deliberately thought of in advance as a way of like, "Hey, here's how we're going to validate this." And always, always, always, if you're going to accept more risk of a false success or false positive, false negative, you want to then be really thinking about how you're going to harden your validation of a hypothesis.

For example, let's take that when we talked about with Twilio where we are kicking people out and we're sending them to the pilling hotdog experiment, and we're sending people to that experience to hide the phone number. Now in that case, let's say that we were going to accept a lower confidence interval. I would very much want to see qualitative feedback to confirm that that hypothesis was true. I want to be looking at the qualitative data from the ones where people were thrown into the existing flow and one's put into the dogs that one of them felt more confident and more like this was really easy to get through and they felt out of a territory and things like that. And I'd be wanting to hear from the ones who were in the other one, things like, "Oh, I got stuck on that [inaudible 00:46:48]." Like, "Figure this out, but it feels like it's that amount of my depth."

**Laura Schaffer** (00:46:52):
I would want to be looking for other things to corroborate the hard data that I'm seeing. And yes, it opens the door to whenever you open the door to more risk acceptance, you are going to have some false successes there. But all of these things together can overall make it more likely that you're shipping more things that are going to positively influence the customer. And again, I can't say it enough. It is a huge risk in and of itself to not ship as much as you possibly could in a year. That is a huge risk given that very high fail rate. So to those data scientists, and I've chatted with a few of my time, what I try to explain is that that article, that data that the 80%, that's hard data about what a detriment it can be if you don't run an enough experiments.

**Laura Schaffer** (00:47:51):
If you just run 10 in a year on there, maybe two around impact, two of a course of an entire year if you take that approach. So data scientists can understand, "Hey, if we do this, if we run this down, we can double or triple whatever it is, the number of experiments where we can run and overall net that's going to result in more successes that will overall net us to a positive place." You can still tell a data story to the data scientist about why you're doing this. Again, this is why when you asked that question identify, as a very data-driven person. But I think some of the methods that I use can sound at the service level as more like, "Oh, I'm going by my gut." But again, very data driven is just embracing the reality of some of the hard data that I don't think we all embrace or are even aware of sometimes about that fail rate.

**Lenny** (00:48:42):
This is awesome. This is a big idea. Have you written about this anywhere for folks that maybe want to try this approach at their company? And if not, you should.

**Laura Schaffer** (00:48:50):
I appreciate that. It's funny, it's like all my general life to do is just start writing some of this down. I have three children, one of whom is five months old, and then I have two and four. And so sometimes I'll start to write and then one of them will crawl across the keyboard. And by one of them, I mean all of multiple times. But eventually, yeah, I'll be very happy to do that if folks would be interested. I'm always happy to do whatever I can to help folks, help empower folks with knowledge to do better because none of this is secret sauce really. It's just learn from experience and it's always better to learn from others' experience than your own. It's faster. So yeah, I would definitely [inaudible 00:49:35] is that, I think that's the best that I can say, but eventually my kids will get older. I hear this and maybe I can do so.

**Lenny** (00:49:42):
Hopefully. Cool. So maybe if you're watching us on YouTube, leave a comment and if you want Laura to write in depth about this idea and spread it to your company. Okay, I want to talk about growth, but I have one last question just along the lines of experimentation. Is there any other just, I don't know, big lessons or takeaways of running experiments that would be interesting to share?

**Laura Schaffer** (00:50:02):
I think we got into this one a little bit, but I just really want to exclamation point, underline it, which is that notion of making the data wrap to fit a concept. I think a lot of teams feel and are under a lot of pressure to show progress and, "What did you do this month? Where did the metrics move?" And it can cause folks to feel like they have to do that, where it's like, "Oh gosh, this experiment." Everyone's got the experience where you run an experiment and you're like looking at the data, refresh, refresh, refresh, oh my gosh, and actually perform worse. Or it's not the same and, "Gosh, we got everyone really excited about this thing that we all worked on really hard. Like, oh my god, what are we going to say in the QBR or the monthly report?" Whatever it is that the results come to light.

**Laura Schaffer** (00:50:55):
And to this, I'd say this, that it's incredibly important for growth teams to educate out and for folks outside of growth and leading growth, especially to understand that the best way for a growth team to succeed, the only way really for them to succeed is to embrace the fact that they're there to validate, to understand what the biggest opportunities are and to go after them.

And that is not something that can be done on a weekly timeline, sometimes even a monthly, depending on the space you're in and what's known and unknown. And so any growth team that's beholden to short timeline wins and improvement is always going to be dangerous. That's an environment that's conducive to vanity Metric usage and massaging the data [inaudible 00:51:47]. And ones that are more successful are ones that are reporting over longer periods of time. Because I think growth team, given enough time to fail, enough time to learn the right thing to do is absolutely going to show success, real success. Not that, "Okay, we're going to make this data fit." But real moving the metrics success.

**Laura Schaffer** (00:52:03):
And so definitely educating out. If you find yourself in a position where you are beholden to that, share that 80% fail rate. Just math, statistics, data. You cannot be successful in an environment, but over time you can be. And so that's one thing I definitely would draw on. I end up spending a decent amount of my pie chart at Twilio and then also at Rapid where I was after that and I'm sure I'll spend some time at Amplitude as well. Just helping folks understand what is the healthiest ecosystem, most powerful ecosystem for a growth team to operate in. And time and expectations over time is a big part of that.

**Lenny** (00:52:46):
When you say pie chart, it's like the pie chart of your time like a big chunk of your time goes to this?

**Laura Schaffer** (00:52:46):
Yeah.

**Lenny** (00:52:50):
That's awesome. I like that. I use white charts a lot as to describe that same idea. Just to be a little more concrete there, what is the timeframe you think is the minimum for a growth team to be thinking across?

**Laura Schaffer** (00:53:01):
I think it's good, especially for newer teams, but even teams in general. Commit to something that you can do over the course of a year and low, medium, high is always helpful in that space. A lot times-

**Lenny** (00:53:01):
What do you mean by that, by low, medium, high?

**Laura Schaffer** (00:53:17):
Low, medium high, more like, "Hey we've got a few bets that we have or few core hypotheses." And if they take off that's going to be our high bucket like, wow [inaudible 00:53:26]. We think these things could become lightening on a bottle here, but they could also be a bunch of [inaudible 00:53:31] missed. But until we run in, we're not going to know. And if those bear out though, then yeah, that's our high. And hey, we've got a few things that we think are safer. Maybe it was validated a bit in the previous year, what have you. And these looking really the metrics this amount.

**Laura Schaffer** (00:53:45):
So it's helpful to give people though that construct, it deviates from it very hard deviates from this notion of like, here's the single number that we're going to hit. Just things that help people understand that space a little bit better and what to expect. And because of that it can be a little bit lumpy. There were some things that you released. Truly for the most number of years, can be easiest to talk about in this construct here, but there's one thing that we did that generated tens of millions of dollars in the pipeline, was really, really powerful and took, sometimes navigate and validate. Other times we did that onboarding stuff that I was talking about catching those things. That could happen on a little bit of a faster clip but still took some time to validate and understand. But yeah, over the course of a year you should generally be able to commit to movement. But help people understand the methods there so that they're not coming at you on a weekly basis being like, "And what did you do these past couple days?"

**Lenny** (00:54:44):
Okay, I got to follow up on a couple of these things. What was that big change of Twilio that lead to tens of millions of dollars?

**Laura Schaffer** (00:54:50):
This is part of the course that I teach at Reforge.

**Lenny** (00:54:55):
Oh, amazing. You get to work for Reforge with [inaudible 00:54:57].

**Laura Schaffer** (00:55:04):
I'm actually interested in retention, I think is my part. Right now, I'll give you links so we can [inaudible 00:55:05] in the show notes. But yeah, the high level version, this was deeper into my journey at Twilio. This is fast-forward a few years, build up this team and some cool things going on. But I was really looking for what's the next big thing for us to do? What could that be? And I noticed, remember that question very back of the day when I asked about the developer versus not developer folks [inaudible 00:55:34]?

**Lenny** (00:55:33):
Mm. Yeah.

**Laura Schaffer** (00:55:35):
We saw that little non-developer little dude ad was growing. We were actually the number of people in the ecosystem who were identifying themselves as not a developer were in the space.

But very interestingly they were, as we got more refined in our understanding of those folks, a lot of them wanted to build with Twilio. There was a hypothesis of like, "Oh well maybe they're lost, maybe this want pricing, maybe they [inaudible 00:56:00] mistake." And I was like, "Nope, they're here to build, they won't build." And they struggled through the developer on onboarding and some of them would succeed and some would... But anyway, it was all about identifying what did they need to succeed. If we were made them successful, could it contribute to dollars? One of the core learnings I'd heard from sales at the time was, "Hey, it's very challenging for us to get the folks when a developer's not involved yet to go from zero to one to get something off the ground. But man, if we can get them to do that, if I can get them in $1 and spend, I can get them to five. If I get them to five, and get them to 50, like 10,000, then I can get them to hundred thousand."

**Laura Schaffer** (00:56:39):
This whole long journey like, "Hey, Laura, if your team could just get them off the ground, man, we can do so much." So yeah, the journey is all about, okay, what were the things that were missing in the experience we were offering and ultimately was they couldn't write code from scratch. That was really difficult. And also we're going to stand up a server. That was difficult. But we ended up iteratively experiencing a way to validate those hypotheses and what's the right way to do this and yeah, that was great. It's called quick deploy on code exchange. Anyone can go there and deploy an app without having to write code and get an aha moment there with Twilio.

**Lenny** (00:57:16):
That is awesome. So basically it's like a low code Twilio app?

**Laura Schaffer** (00:57:20):
Yeah, it ended up being, we had a lot of pet names, nicknames for it. I think probably the one that most succinctly describes it as just, it ended up being a create your own demo experience which made you talk about the psyche of people. We talked about how developers telecom until can be intimidating. We'll talk about the non-development, sometimes the buyers or the people who are instantly buying decisions, for them, it was not only was it telco, but it was the developer stuff was inaccessible but they still wanted to jump in and they wanted to have that experience. And so this was a way for us to give them momentum, give them comfortable. Geez, I can get this running my development team, I'd definitely do it. And so it was a very powerful moment where we could really address the psyche of those users, get them excited about Twilio, and then give sales the ability to give something powerful to those non-engineering buyers and folks they're talking to.

**Lenny** (00:58:17):
So genius, looking back seems like an obvious win. One of my readers suggested that I start a series of the story of a feature and walk through the discovery ideation development iteration and this feels like a really interesting example of that. But anyway. I got just a couple more questions. I know we've been going for an hour now. But I have questions, I don't want to let you go just yet, and they're on growth. So one question is just you worked at Twilio, which is very product led growth. You're now Amplitude, which is more sales driven and I know you're trying to go more product led. I know Elena talks a lot about this, how every company needs to have product led motions, otherwise they're going to be disrupted by someone that comes product led. And I don't know what hires, which blanket would they fall into?

**Laura Schaffer** (00:59:05):
Between the AI like SLG and PLG. Yeah, for me they're two sides of the same coin. Product growth and sales. It's all to me, very thematically the same stuff. The difference is that with growth, you are selling with your product, and with sales you're selling with person like one-to-one. And so companies need to be employing both of those forces to optimally convert their audience. We're in a world where people are expecting both. They're expecting to be sold by your product and sold at the enterprise level. And large companies buy by human beings. It's going to listen to their specific needs and really break it off for them. And if you only have one, you're going to miss stuff. So absolutely, I think you want those two forces together working well. And obviously there's different stages, things work differently in different spaces, but I think when it comes to Amplitude, I think there's a huge opportunity here.

I think the key is, and that the challenge for companies that have done the sales thing and are trying to crack into the PLG thing really comes down to how you fundamentally are approaching that space. And again, your users and where they're at and the psyche of where they're at, I think a lot of companies will say, "Well okay, hey, we're going to do this PLG stuff. Let's take that sales enterprise whatever offering that we have and let's chop it up a bit and cut access here and cut out this feature here and we're going to slap this plan out and we're going to put a price on it and we'll maybe have hours of debates over whether it's like 10 99 or $104 or 75, and eventually someone will win that battle and slap it on and then [inaudible 01:00:54]." And anyway, the discussion of the focus is a lot around the product.

**Laura Schaffer** (01:00:58):
What are we going to do with this product? How are we going to crack it open and shift shift it in and then give it to these people, these users, these visitors? And what it's missing, I think is, and a lot of times it's easy to miss, is that when we're doing PLG and we're shifting from sales to PLG, we need to reset. We need to recognize that, again, this is sales, sales via the product. What does a good sales rep do when they're engaging? They understand what the problem is of the person in the space they're talking to. So we need the same thing here. What are the unique problems of people who are coming into our self-serve space? And I think when it comes to a company like Amplitude, a lot of the folks that will be looking to address via the PLG motion, there's a number of things we want to achieve there, but one of the primary things is to tap into the SMV market market and really give them a really startups and give them a space to land and to grow.

**Laura Schaffer** (01:01:57):
And again, you have to think what are the challenges and unique problems that they have because we're going to be using our product to settle them. We need to meet them where they're at with the problems that they've got. And I think one of the things that I've observed from being in all these startups and advising some startups is I very rarely... I don't think I've ever come across a startup where they have the right number of analysts for their needs. In fact, a lot of them don't have any. And so what that means is that the CEO is being an analyst to create their dashboards for the board and the product manager is being an analyst to figure out what the heck's going on and creating their boards for their product.

**Laura Schaffer** (01:02:34):
And that's happening all over the place is that people are in their roles and they have to be an analysts too. And I think that that's a problem that especially younger companies and early stage companies have. And so when they connect their psyche, what are they caring about? What are they thinking about when they're sending it for product analytic product or something? They're looking for something that's going to help them feel reassured they're going to be able to actually get to the bottom of the right metrics, create the reports that show things the right way. What's the best way to show churn? There's got to be a best way so many people are doing it. Guess what? Yes, there are some really good ways to do it and there are some really successful ways to set up dashboards for the board. People have done that too.

**Laura Schaffer** (01:03:16):
There's a lot of that knowledge that exists in one of those frameworks that exist, benchmarking. Are these numbers even good? And so, one of the hypotheses that I have is that if we take that perspective and we understand that that is the problem, that there's a number of things that we can do to really change the way that self-serve experience works to help convert people and show them how Amplitude can make them that powerful. But the thing that I think sticks across all companies, not just amplitude making the shift, is just that, that when you're doing this, do not think this is a copy paste, but chop it for parts thing. Don't start with your product when you're building at your strategy, start with your customers, your users, your prospects, the people who are going to be coming into yourself or flow. Make sure you are understanding how their problems differ because they do from the people that you're addressing at the sales led side. And then make sure that you're orienting your experience of product around those people.

**Lenny** (01:04:12):
It's interesting that you almost have to start again as a product company, as a product because you may need to solve completely different problems that eventually lead to the same place. But it's interesting what you're saying that you may end up targeting analysts or PMs. I know Amplitude or has always focused on PMs, but-

**Laura Schaffer** (01:04:32):
Yeah, it's right. And there's always nice thing about it is it's in some ways, it does feel like you're starting fresh because you do need to start with the customer again and what's their problem. But in a lot of ways, you can carry over a lot of the same knowledge. At that point you know what's working well. Amplitude for example, does have a ton of knowledge around what some of the best ways artists set up reports. There's a lot of things that they have the momentum going, like where do you choose that momentum and how do you put that and curate that in front of users and make sure that they're getting the right things. There's a ton of momentum already there. It's just a little bit about harnessing it and understanding like, yeah, where are the gaps because there are going to be gaps.

**Laura Schaffer** (01:05:08):
But anchoring in a customer problem as I think the way that you start any new product, any new thing that you're releasing, should always think about the customer and the pain point. So no different than when you're doing PLG for the first time or cracking into it. You need to be thinking again, starting again with the problem, the problems they have, the psyche that they have coming to your space so that you can build something that is going to effectively make them feel like, "Oh you can solve my problem, you get me." And show them how your product's going to do that.

**Lenny** (01:05:42):
Final question, and this is around developers. You worked at Twilio, obviously Twilio sold developers. I think Rapid where you work right before Amplitude also sold developers. Selling to developers feels like such a hot space right now. There's so many startups that are just building developer tools, such a huge market. Used to be not. Used to be like there's not a market in developers. They're not going to spend money, there's not enough of them. And now it is a big popular spot. And so I'm curious, what have you learned about building a startup and a product that sells to developers? I imagine a lot of founders building search tools would be really curious.

**Laura Schaffer** (01:06:16):
The first is that developers are just a very different audience from any others. I've seen so many people who have come in strong on growth really well or product really well with other audiences and like, "Oh, I'm going to take all those learnings, I'll pivot into serving developers." And as it being a very steep climb because developers are so different. And let me give you a couple just fun facts that make them really different. And some of these have some interesting stories. One is developers, almost two, one, do not look at your marketing website at all. They go straight to your signup flow. So what that means is all that beautiful context that you're setting and the product aid pricing, all that stuff, very often they're skipping all of it context free and going straight to your signup. And so anytime you make an assumption like, "Oh, well, they probably know this coming in to signup." Or like, "Well, we don't need to include, that's on the marketing website." None of that's going to apply to this group of people.

**Laura Schaffer** (01:07:15):
They're there. The analogy I have for this group is they're the IKEA buyers who when IKEA package comes, they're not opening up the instruction manual and reading in and then starting to go through, they're in there tearing open the bags and starting to pull the pieces together and trying to build it. They'll come up for context and steps and such when they get stuck if they're motivated. So that's one thing. And then another one is just the aversion to talking to sales. And I think hearing that, some they're like, "Oh yeah, well, I hate sales too." When I'm sent out and get bombarded by sales, that's the worst. I totally get that. But developers are on this whole other level. There was a fang company sign up for Twilio, built a POC, launched to production, all this, and operated in that space for months without engaging once with sales.

**Laura Schaffer** (01:08:12):
I was trying to reach them and I ended up being the one that talked to them first because they reached out to support because there was something about their delivery that was off ,there missing a feature and they did not want to talk to sales. They ended up talking to me when I was in product marketing. And that was my first exposure of like, these people not want to talk to sales. And then there's another one where a giant retail company where the engineering team signed up with their personal e-mail addresses so they wouldn't get bombarded by sales. It was only later that we found out. Anyway. But the thing that's most important, these are fun facts, but the thing that I would say is the most important, the thing to leave with listeners here is what makes them so different?

**Laura Schaffer** (01:08:54):
Why? What's the deal here? And it stems from their charter and their responsibility. So if we put ourselves in developer's shoes for a minute, a developer, if a developer is required to use your product, especially if they're the primary user, the primary builder, it's really important to recognize that they're responsible for that. If your service goes down, that's their responsibility. Not just for themselves but their team. If the pager wakes up someone because the service they bought from you goes down, that's on them. If, oh, it turns out that doesn't work with the systems that they said it was, well, that's on them. Doesn't integrate with the data the way that everyone wanted it to? That's on them. Everyone lives to developer when it's not working right and it cannot work right. In so many ways, that's their failure, it can cost them their job, it could cost them the trust to their team.

**Laura Schaffer** (01:09:50):
It cost them their reputation. And that means that the stakes are very high for them every time that they're adopting something new. So they can't afford to take someone's word for it. Especially a sales rep who might have some other motivations from their perspective, they can't afford to trust your content or someone's word. They must do it. They must prove it themselves. And so that's why, for developers to be bought in, they need to do something, build something, a proof of concept at the very least, if not moving further than that. And so that means they're going to be pretty darn deep in their self-serve experience with you before they're ready to commit. And so if you are a company that is providing, that requires developers to build, you must invest in self-serve experiences in order to effectively convert your audience. And you should be thinking of them. Something akin your self-serve function and growth folks, someone akin to Salesforce because your developers are not going to accept sales coming in and trying to convert them at that stage.

**Lenny** (01:11:00):
I love that you always come back to the psyche of the user and how in this case, developers like, here's why they're responsible for this thing. Salespeople are going to convince them this is going to work. And it's not. That's a really interesting tool and that's a really cool takeaway.

**Lenny** (01:11:16):
Is there anything else that we didn't cover before we get to our very exciting lightning round?

**Laura Schaffer** (01:11:20):
Plenty. I think we covered it all, man.

**Lenny** (01:11:22):
You got all my questions and more. So with that, welcome to the very exciting lightning round. I've got six questions for you. Are you ready?

**Laura Schaffer** (01:11:30):
I am so ready.

**Lenny** (01:11:31):
What are two or three books that you recommend most to other people?

**Laura Schaffer** (01:11:35):
I'm a big believer in happiness. Not just being crunchy or we should all be happy, but also because it helps us do our best work and we're more creative and all this. So one is Simple Path to Wealth by JL Collins. I don't ignore the data, that money is something that often gets in the way of our happiness. I know so many smart people that just have not figured out the whole managing their finances thing. And this book will cover all of your basics. It's very easy to read. He's got an audiobook that he narrates himself. Simple Path to Wealth by JL Collins, he's fantastic.

**Lenny** (01:12:12):
What's a recent movie... Oh wait, wait, there's more?

**Laura Schaffer** (01:12:12):
Oh, there's one more.

**Lenny** (01:12:18):
Oh, let's do it. Let's do it.

**Laura Schaffer** (01:12:18):
[inaudible 01:12:18] Happiness, which is Atomic Habits by James Clear. If you ever want to change something about yourself or something's not quite working for you, this guy will give you a framework to change it. Guaranteed.

**Lenny** (01:12:30):
I really enjoyed that book. That guy's killing it. He was on Tim Ferris, he had a great interview. Folks that don't want to read it, they could listen to that. There's a lot of cool tips there. Favorite recent movie or TV show?

**Laura Schaffer** (01:12:39):
Unabashedly, the Great British Baking Show. I love that show. I love that show for all the reasons everyone loves that show. It's heartwarming and makes you feel good and uplifts you. But also because it is a competitive show. They're trying to be the best baker and they're out there helping each other. They're like a big family. Most reality competitive TV shows that I see, all of them are like cutthroat, they're sabotaging. So I'm just endlessly fascinated also by the psychology of what's happening here. I want somebody to do a research paper on it, get to the bottom of why they're all helping each other. It's wonderful though. Wonderful to watch.

**Lenny** (01:13:18):
Interesting. I always comes back to psychology with you.

**Laura Schaffer** (01:13:24):
I know. I know. I feel like I'm really, really sinking deep in there. And it's true though. It's very interesting to me, and I love that show.

**Lenny** (01:13:30):
What's a favorite interview question that you like to ask in interviews?

**Laura Schaffer** (01:13:34):
I love asking about a ship or release that is not cherry-picked by the person you're talking to. You can get it a lot of different ways. The thing is, everyone has a big success story. Everyone does. It really doesn't actually tell you very much to ask someone like, "What's a great thing you released?" Because everyone could tell that. Instead, take that away. What's the most recent ship is a really easy one because recency, time. But there's other things you can do to take that out. Just give them specific parameters for a ship that they've shared or whatever, and that will allow you to listen more and learn more about their frameworks versus the outcomes. Because if you're picking a random ship, odds are it probably wasn't fantastic. So they're going to want to talk more about how they approach getting there and that's what you want to know about to know if they're going to succeed, what their frameworks to how they approach things.

**Lenny** (01:14:24):
That is cool. I've never heard that one. That is a really clever idea. What are five SaaS products that you use in your day-to-day work? Can't say Amplitude.

**Laura Schaffer** (01:14:33):
I know, right? Still learning which ones we have here. But yeah, I'll just share the ones that I like a lot that I've used elsewhere. So one is Hotjar. Hot Jar [inaudible 01:14:44] also works. Just anything that allows you to put some quick little thing in front of customers, get that qualitative feedback we talked about. It's a critical, critical supplement to quantitative data to understand what's really causing the change or not causing the change [inaudible 01:14:58]. So that's important. I will say Amplitude is a fantastic tool that I have used and I would've said that if I hadn't just joined Amplitude so I got to use it... I know. I got to use it for the first time at Amplitude and it was awesome. So again, like asterisk, because I'm like working there now, but I do actually like it. And Slack, it's boring, everyone says Slack, but I just have to hand it to them.

It makes life so much easier and just nod their way. And then Builder, which I'll also put in asterisk on that one, but I really want to serve this. A lot of people don't know about it and it's really helpful. I do advise them so I'm in their corner. But this is another one I also say would be a powerful one. I think a lot of team gets stuck. They're relying on too much in their engineers to make changes. Again, we talk about rapid experimentation, getting these out, out, out. And Builder makes it really easy for folks to do that. Also, a headless CMS, you can drag and drop headless CMS so they do make it easy for non-engineers to make changes. So especially if you're trying to figure out how to get around that 80% [inaudible 01:16:11] that I mentioned, this builder would be a good way.

And then yeah, if you want one more, I'll give you Chat GPT, which is really boring and everyone's saying that, but I think I'll just say I don't have any crazy things to say about it except that I do think we all need to figure out how we pull that in to [inaudible 01:16:28] put people who don't do that are probably going to lose out or smart AI whatever bots. But that would be it for you, Lenny. But if you ask me in a few months after I've actually been an Amplitude for a bit, I'm sure I'd give you a different answer.

**Lenny** (01:16:42):
That's a good time to plug lennybot.com. And I wrote a newsletter or Dan Shipper who created the bot wrote a newsletter post about how he built this thing. And so you could go ask me questions using the content of my newsletter as answers. And it's very cool. Lennybot.com or lennysbot.com.

**Laura Schaffer** (01:17:00):
Amazing.

**Lenny** (01:17:01):
There we go.

**Laura Schaffer** (01:17:03):
I didn't know about that. Well, there you go. I've changed my answer. It's that.

**Lenny** (01:17:05):
Yeah, there we go. That's all I need.

**Lenny** (01:17:09):
Two more questions. What is something relatively minor you've changed in your product development process that has had a lot of impact on your team's ability to execute?

**Laura Schaffer** (01:17:17):
Yeah, the be embarrassed thing, like I mentioned earlier, be Embarrassed by the first iteration. If you are not embarrassed, you've gone too far. That really speeds up ships and helps people celebrate the unpolished as opposed to feel embarrassed about it. So just embracing that.

**Lenny** (01:17:35):
Awesome. And final question. I know you just started Amplitude, but do you have a favorite pro-tip for how to use Amplitude or maybe Hidden Feature people may not know about?

**Laura Schaffer** (01:17:44):
You tell me [inaudible 01:17:45], but I'll say one thing that was super cool actually that someone put together on my team at Rapid, literally before I left, he put together a video of how powerful Amplitude could be when linked up and integrated with other things like in this case Hotjar and Segment. There was a Amplitude report that someone had created and there was something that was an anomaly happening there. Users were using something in a way we didn't expect and Amplitude one of the reports surface it, but Al Kirsten, we want to know why is that happening. And so we could find out what the event is and then using by Segment, find out what that name was and look at Hotjar and actually go in and get screencasts of people doing that exact event.

**Laura Schaffer** (01:18:30):
And from that, we were able to form some really concrete hypotheses about what actually was causing it. And so obviously talking to customers is very powerful, but in this case, just that simple use of connecting and threading those technologies together could really get a good picture of that without needing to engage customers. So the tip would be how you can really amplify when you get an amplitude when you use it with.

**Lenny** (01:18:59):
Amazing. Laura, we covered a lot of ground, career experimentation, growth, embarrassment, psychology. Thank you so much for being here. Two final questions, where can folks finding online if they want to reach out, learn more, maybe send you an appreciation or two? And two, how can listeners be useful to you?

**Laura Schaffer** (01:19:17):
Yeah, find me on LinkedIn. I don't post a lot. Yeah, I'll blame my three children. Eventually, I promise that I will. But I'm pretty good about responding to messages, so definitely link with me there.

**Laura Schaffer** (01:19:29):
And then what listeners can do, I think I'm always happy to hear feedback, suggestion, all that, but I'll just say I also know that it's a little bit crazy out there right now, especially folks working in tech. So I'm also cognizant what I might be able to do to help all of you. I know there's a few places I advise and rapids hiring. I know of a few folks that are hiring growth, strong growth people and product folks. So if you are interested in learning more about that, don't hesitate to hit me up. I want to make sure that I help as many people as I can in that respect because it's trying times and I'm sure you've heard it and read it, but if you're laid off, this is not about you, it's not your fault. It's this crazy world we're in. Things will get better. And I would be feel very lucky if I could help even one person land. So feel free to hit me up about that too.

**Lenny** (01:20:21):
Awesome. And maybe if you share some links, we could include links to open roles in the show notes.

**Laura Schaffer** (01:20:26):
Yes. I know there's a few that don't have JDs open yet. They're that hot off the press, but I'm happy to surface a few things there for sure because I know that makes it easier for people to know.

**Lenny** (01:20:37):
Awesome. We will do our best with the show notes then. Laura, thank you again for being here.

**Laura Schaffer** (01:20:43):
Yeah, thanks so much for having me. This was awesome and so much fun.

**Lenny** (01:20:47):
Bye everyone.

**Lenny** (01:20:49):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

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## [18/22] Hot takes and techno-optimism from tech’s top power couple | Sriram and Aarthi

**Sriram Krishnan** (00:00:00):
I hate Jobs-to-be-Done, I think it is a terrible framework, I think no successful company has ever been built on top of JTBD and if you pick JTBD, you're probably doomed and I'll give you an example. When you sign up for Instagram right now, when you sign up for Facebook for many, many years, Facebook knew that it needed to get you to 10 friends in 14 days. If you got your 10 friends in 14 days, you were probably going to use Facebook. So it'd be like, "Well, we're going to throw every tool we have at our disposal to get you to 10 friends and 14 days."

**Sriram Krishnan** (00:00:23):
So if you signed up for Facebook for many, many years, you'll get this little thing called People You May Know. Then you'll have this person who just signed up for Facebook, you go, "Why I'm seeing this person?" It's not because you need a friend, because they need a friend. So what Facebook did was it made your experience slightly worse to make that person's experience slightly better. This was performing no job for you, it was trying to perform a job for them.

**Lenny** (00:00:49):
Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hardware and experiences building and growing today's most successful products. Today for the first time ever, I've got two guests, Aarthi Ramamurthy and Sriram Krishnan, both former product managers who between them worked at basically every major tech company including Netflix, Meta, Snap, Twitter, Microsoft, even Clubhouse. Sriram is now a partner at a16z. They're actually married and both individually amazing. Together they host the Aarthi and Sriram Good Time Show, which started on Clubhouse, it's now on YouTube and famously they had Elon Musk on back in the day, which led to Clubhouse's crazy rocket ship growth, which we definitely touch on.

**Aarthi Ramamurthy** (00:04:20):
Thank you. Thanks so much for having us, Lenny. This is a bucket list thing because we are on Lenny's Podcast.

**Sriram Krishnan** (00:04:27):
I know. Longtime subscriber, listener and now here. Wow. I don't want to screw this up.

**Aarthi Ramamurthy** (00:04:36):
First time caller.

**Sriram Krishnan** (00:04:37):
Yeah, first time caller. Yeah, let's not screw this up.

**Lenny** (00:04:39):
You guys are hilarious. I appreciate it and feel very flattered. You two are the first duo on this podcast and I couldn't think of a better two people to start this podcast with. I have so much stuff I want to dig into. I think we're going to have a lot of fun, so again, thanks for joining me here.

**Aarthi Ramamurthy** (00:04:54):
It's awesome. Big fan. Yeah, honestly, this just... I'm excited.

**Lenny** (00:05:00):
So I don't know if you remember this, I was thinking about this story, back when you were doing the Good Time Show, you invited me on the Good Time Show and I was thinking, hesitating, like, "I don't know, that's kind of scary." And then the next day, Elon came on and then it just blew up and I was like, "Shit, I missed my chance." And then became really fancy people and I was like, "I'm not ever going to make it back on there." And so I look back at that as like, "Oh, I hesitated too long. That's a lesson."

**Sriram Krishnan** (00:05:22):
Well, the way you should interpret that is, "They couldn't get me on, so their backup choice was Elon. I would've been the main event and they were like, 'Well, oh, we couldn't get Lenny, we'll get... No, but seriously, we've been a huge fan and those are just the fun times. We used to do the show obviously on just Clubhouse and now we do the show on YouTube, wherever you can listen to our podcast. And a lot of people remember us for the Elon episode, but I will tell you this, it is often the folks who were working technology, who were not as famous, you're obviously very famous now, but who really connected with the audience. But you know what, that's why we have you back on the show now [inaudible 00:06:02].

**Lenny** (00:05:22):
There we go. It all worked out.

**Aarthi Ramamurthy** (00:06:01):
Opening act, yeah.

**Lenny** (00:06:07):
Speaking of Elon, I was always curious, how did you actually get him on the show? I remember that was back before he was very vocal in the world and he was hard to learn from and hear from. How did you actually pull that off?

**Sriram Krishnan** (00:06:18):
Well, I think it's actually similar to how a lot of good things in my career have happened, which is I just had a conversation on the internet. I have this whole thing where I do think a lot of people trying to get ahead in their career, especially in technology, should just write cold emails, cold DMs, notes, put out content, et cetera and that leads to good things.

In Elon's case actually, what wound up happening was a few years ago, he DMed me out of the blue. At the time, I was working at Twitter and I think he saw something I'd written and wanted something from the company and I think he went through the org chart and he DMed me. And I was like, "Well, I'd love to help you," and he sent me his phone number. And I called him and I was like, "Is this [inaudible 00:07:00] and we had a conversation and we built up a relationship after that. This was when Clubhouse first came on the scene and I was like, "Well, who do we get on?" and Elon hadn't done a lot of press appearances, I think he's done a lot more since then obviously, and I texted him and he was like, "I'm game," and the rest is history.

**Lenny** (00:07:20):
Amazing. I love that Elon just DMed you. Sriram-

**Aarthi Ramamurthy** (00:07:25):
Slid into his DMs [inaudible 00:07:25].

**Sriram Krishnan** (00:07:26):
The crazy part of that story was I had texted him saying, "You should come on the show," and he said, "Sure," and then he tweeted about it. And I will tell you that when Elon tweets about you and well, even maybe more so now, your phone just melts. And then for the entire afternoon, I had hundred thousands of people asking me what's going to happen, the Clubhouse people-

**Aarthi Ramamurthy** (00:07:46):
But also on Clubhouse, if you open the Clubhouse app that day, there were so many rooms that were trying to collect questions for us and help us prepare. There was so much pressure just scrolling through the hallway and trying to look through, it's like, "Oh my God, is this real? We are the people that they're talking about here. This is crazy." I don't know if you've listened to the actual thing, but it was pretty cool because we got to ask him questions we've always wanted to ask on like, "When do we get to Mars?" it was kind of fun. And then after that, again it was this, we got a bunch of people reaching out and being like, "You should have asked this question. You guys are not professional journalists." And we are like, "No, we're not. What gave it away?" We are just random two people who are just talking to this guy, so it was really fun.

**Lenny** (00:08:33):
Yeah, I remember that. I remember journalists were like, "They're not actually asking him hard questions. How dare they have him on, give him a platform to share things without any criticism?"

**Aarthi Ramamurthy** (00:08:39):
And we were like, "We are not those people that you think we are, that's just never been our job."

**Lenny** (00:08:46):
Yeah. I have so many questions that spiral from this discussion, but I want to ask one quick Clubhouse question. So Aarthi, you worked at Clubhouse for a while. Very tactically, I feel like they're really smart initially with their growth strategy of just getting fancy, smart people in there talking and pontificating. They had Naval and Marc Andreessen and then eventually, you want other people. And that was such a smart way to get people to get in there and want to get in there to listen to them, to engage with them. What's your take on that as just a growth strategy to get a social network bootstrapped? And then just generally, I guess any thoughts on the journey of Clubhouse? It's had a big rise, it's kind of [inaudible 00:09:22].

**Aarthi Ramamurthy** (00:09:21):
Yeah. I mean, all good questions here. I think growth strategy, that's a great way to acquire people right at the top of the funnel. Once you've done this a few times, you kind of see everything as a funnel and you're like, "Well, are you retaining people? Are you not? Is it top of the funnel impressions or do they stick around?" So I think having people like Marc Andreessen and people like Naval and they were not doing this out of any... they were really, really interested. When we got invited by Marc and Marc was like, "Check out... this was way before a16z even invested in it, was like, "This product is amazing. These folks are doing something really cool, this is going to be the future, it's amazing." So it gave them a platform to go speak out and live social audio just made a ton of sense. I will say, Clubhouse, I feel like they get this unfair attention and criticism. It's a what, three-year-old startup?

**Lenny** (00:10:17):
Mm-hmm.

**Aarthi Ramamurthy** (00:10:18):
And I've done two startups. The second one I did, three years in, we still sort of were struggling and trying to figure out what we were doing. So I mean, I feel like founders just need some time to breathe in and figure out what to go do. So I'm bullish on Clubhouse, I think they'll figure it out and Paul and Rohan are great founders. They've been doing social stuff for over a decade plus and so they've got to figure it out. And I know that it's like, they get this thing on, "Oh, they were really hot during the pandemic. Is this a pandemic fad versus not?" I don't know, it's a product at the end of the day and you're going to have to find product market fit and I think they'll figure it out.

**Sriram Krishnan** (00:10:56):
Yeah. The broader question of how do social products acquire the users is super interesting. One of my favorite pieces written on this is Eugene Wei's Status as a Service. Eugene should absolutely be on your podcast someday. It's a 10,000 word piece, which is amazing and highly suggest people read it. But one of the key takeaways from that piece is the idea that when you have a new network, think of it as a new country, you want the high status people and high status mean they're interesting, people want to be where they are in some shape or form because they have money, they're smart, they're cool, they're good-looking, whatever it may be and you want to get them onto your network. And there's exactly an interesting corollary that they're often underserved by other existing platforms. And because if they're already well-served, they wouldn't want to move to you.

**Sriram Krishnan** (00:11:43):
And Eugene doesn't talk about it, but if I look at say the history of all the three, four large social media companies, you've seen this pattern. For example, they've often each had a breakout set of stars who are unique to the platform. For example, if you look at say Snapchat, you had folks like Kylie Jenner who really broke out first. If you look at Instagram, I would think The Rock, Cristiano Ronaldo, a lot of others are organic to Instagram. But let's say you get to TikTok. One of the things you'll see is a lot of the folks from the Instagram world rarely move to TikTok and there's a couple of reasons. One, they didn't really need to because they were already popular on some of these other existing platforms, but two, TikTok actually took advantage of a different set of skillsets. People who are really good on video, people who could dance, be funny. And so you saw the rise of Charli D'Amelio and Addison and so many others who are different.

**Sriram Krishnan** (00:12:31):
So every single time, I think you need to go after a set of people who are high status who are also underserved. So coming back to Clubhouse, I think one of the interesting things is I think these celebrities are super interesting, but what is more interesting for me is all the homegrown folks. I actually consider us as a part of that, we would not be here doing the show if it wasn't for Clubhouse. There are many folks who had that original launch using the platform, so I think for folks here who are thinking about social platforms, it's interesting about okay, you need interesting people from elsewhere, but you also need homegrown talent. And by the way, you are a perfect example of this phenomenon because you are Substack's homegrown talent and I think you bring a lot of value to Substack. And there are a lot of people with huge newsletters, et cetera, but I think your rise and your popularity is so tied to Substack now and that's actually a great example of all of this.

**Lenny** (00:13:25):
Yeah. It reminds me, the founder of Musical.ly who turned into TikTok has a great story. I think you've heard his talk about this, how the way he thought about it is there's all these successful people on Instagram, that's Europe, and the people you can convince to come to America are not the kings of Europe, but they're the peasants that are like, "Oh, we have a new opportunity to rise and become a king or a queen." And so those are the people you pull in, the people not doing well on another platform that want to do well versus the people already killing it.

**Aarthi Ramamurthy** (00:13:53):
Yeah, [inaudible 00:13:53].

**Sriram Krishnan** (00:13:53):
Lenny just called himself the king of Substack right there.

**Aarthi Ramamurthy** (00:13:55):
Yes, I know. You're the king, you're the king of Americas.

**Sriram Krishnan** (00:13:58):
I'm just trying to give you clippable moments on video.

**Lenny** (00:14:00):
I did just find out that I think I have the fourth-largest Substack newsletter on all of Substack which is ridiculous-

**Aarthi Ramamurthy** (00:14:05):
That's amazing, wow. That's amazing.

**Lenny** (00:14:05):
Their recent number.

**Sriram Krishnan** (00:14:08):
Yeah. Number three, number two, number one, Lenny is coming after you, better watch out.

**Aarthi Ramamurthy** (00:14:08):
Take them out.

**Lenny** (00:14:12):
Yeah. They're up there. So you mentioned the chat with Elon and how you're very tech positive and I think that's something that you two are at the forefront of, is this trend, I don't know if it's called techno-optimism or maybe there's another term for it and I'd love to hear just like why? Because I know that's important to you too, why that's important to you and just what is this movement of techno-optimism-

**Aarthi Ramamurthy** (00:14:32):
Let me take a small stab at it. Look, I think it's also very personal to our context and our upbringing. For us, Sriram and I came from a fairly middle class family in India, this city in India that most people here won't probably know. And we grew up really liking computers but didn't have access to a computer for a longest time. In both our cases, our parents bought us our first computers after saving money for it and it was a hard thing. And when we eventually got onto it and started learning to write code, we met each other online. We're dating ourselves now, but we met on Yahoo Messenger back in the day and we worked on this nerdy coding project, that's how we connected. So technology and computers have given us everything.

**Aarthi Ramamurthy** (00:15:19):
Our first jobs were at Microsoft, we built developer tools and platforms. If you were in our shoes, you would feel the same way too. Tech has given us so much. And so for us to come here all the way from India, through multiple cities, we lived in Seattle and then here, the Bay Area, I've started tech companies, it is a bit frustrating to see the other viewpoint because you can see how much it has uplifted people, careers, lives, but also just from what we've been able to work on, what we've seen our friends work on and ship and put out there, it has dramatically moved the needle. And so for us, we are the living testament of tech actually helping us and help us do better, so I don't even see the other viewpoint from like, why wouldn't you be optimistic about technology? I don't get it.

**Sriram Krishnan** (00:16:10):
Yeah. I think the personal part was really core. I think there's generally two schools of thought. One school of thought, I would broadly write up as things are getting worse, technology is making things worse and we should all do less, build less. And then the other school of thought, which I think I subscribe to, is technology is not perfect, the impact technology is definitely uneven, but pretty much most of the good things in the world over the last 100, 200 years are responsible for it. And we can have a whole long discussion about the evidence why and we have lots of very fancy sounding intellectual theories as to why, but at the heart of it is what Aarthi said, if it wasn't for tech, we wouldn't be here, we wouldn't be doing this.

**Sriram Krishnan** (00:16:45):
I suspect a lot of folks who are listening to this wouldn't be able to listen to it, wouldn't have the opportunities they have or have the opportunities we have. It is a great level up. My dad pretty much had the same job for his entire life, essentially from age 25 till the time he retired and there was really no easy path out for him. And I imagine like, "Hey, if he was born 40 years later and he had a laptop and an internet connection and could get on GitHub, here are opportunities that would be just impossible, even 30, 40 years ago and that's all from technology." So I think that's at the heart of it, it's the best thing we have of getting ahead.

**Lenny** (00:17:21):
It's such a refreshing perspective on tech. In traditional media, all you ever hear about is all the problems that tech is causing and all the dangers and how we're all screwed. And so it's like you almost forget that there could be really positive stories about what's happening with tech and it feels like there's a small number of people that are doing this at scale and-

**Sriram Krishnan** (00:17:40):
Oh, yeah. I'll give you one small example. You made a joke about kings from Europe, et cetera. If we just go back 100 years, the piece of hardware that a king or a royalty would use or a rich person would use would be so different from what a peasant would use, but you know what? I suspect the phone that you and I have is probably the same phone that... actually I know it's the same phone that Elon Musk uses, the richest person in the world. I know a lot of folks in India who have very high end Android device, they have access to the same internet. You go to google.com, google.com doesn't know your net worth, it gives you the same results. Chat GPT doesn't know how rich you are. It may not like you, but it doesn't know how rich you are. If you just think of all these constructs, they're were just impossible technology. But anyway, that's a whole other conversation.

**Lenny** (00:18:24):
Yeah, I love that the richest people have the same phone as me and nothing they can do about it. Something else you two are really good at is building a network, building community, building personal brands. I know a lot of people listening are either often told, "You need to build a audience online, you build a brand, you got to build a network," and all these things. So I guess I'd love to know just what advice do you give people that come to you and like, "Hey, I want to build a personal brand, I want to build the network"? Just how to go about doing that, what's worked well for you two?

**Aarthi Ramamurthy** (00:18:54):
Sriram has way more structured thoughts on this and honestly, he's way better at this than I've ever been. He's basically slowly corrupted me and brought me to the dark side. But what I have come to believe and this differs from what I used to believe is especially if you're working in a big company, you are one of the many thousands of employees in there. Generally what you get told is, "Hey, just ship really good products, put your head down, go to work. The products will speak for themselves. That's just how it's going to work. Don't do this whole personal branding and all of that stuff. It's such a distraction," and that's generally what you're told.

**Aarthi Ramamurthy** (00:19:34):
Most of my career I was like, "Yeah, of course that makes sense, that's kind of what you do." But I've come to realize that that is just not true and this might be a controversial opinion, but you have to get out there and build your own brand. You have to figure out what you stand for, what your core values are, what you believe in, what you think you want to do, what your next career trajectory is going to look like. All of that is just up to you. It's not up to the company to figure it out for you, it's not up to anybody else, it's just up to you.

**Aarthi Ramamurthy** (00:20:05):
And I think building a personal brand is looked down upon so much that people think of it as a dirty word. It's like, "No, you can't do that." "Oh, look at this person who's branding themselves," kind of thing. But I almost see it as what distinguishes you from everybody else and that is not so much saying something that you're not good at or touting yourself more, it's really about highlighting, "I'm really good at this thing and I want to talk about this thing and I want to do videos about it or write about it or tweet about it." Whatever is your forum, you have to put yourself out there.

**Sriram Krishnan** (00:20:43):
I mean this is probably one of the most important things that somebody can do and I spent... no, we spent years slowly climbing the corporate ranks. We were junior product managers, IC product managers, senior product managers, slowly climbed the ranks and ran teams, et cetera. And I spent years just thinking that all I need to do is put my head down, do my job really well and that was it. But then I looked around and I suspect a lot of listeners here probably have the same feeling that some sort of people were getting way more opportunities, some sort of people are way farther ahead even though I was mostly sure that somebody else was doing a better job and I was trying to understand why. And I think building a network, which I'll try and define because I think a lot of people have assumption of what it is, is at the heart of this. So building a network is very simply having relationships with human beings. And let's start off by saying first of all, these have to be authentic, genuine relationships.

**Sriram Krishnan** (00:21:29):
One thing, it drives me crazy when somebody will come and say, "I'm here to network." I'm like, "I don't know what that word means." So all you're trying to do is have authentic, genuine relationship with people and expecting nothing in return, so that's great. And then people are like, "Oh, well that's awesome, but I'm a senior... for example, I was a senior PM at Microsoft for a bunch of time and then kind of similar at Facebook for a bunch of time, you're like, "Well, what does it mean? I'm here, I'm going to my meetings, I'm doing my day, its only so many hours." I'll be like, "Well, let's start off with go and meet every single peer that you have you don't directly meet with. Go get coffee with them and ask them, 'Hey.' Have no agenda. Just ask them what's going on in their life, who are they, what their life story is and then who are a couple of interesting people that you should meet with? Go talk to your manager and go talk to their peers."

**Sriram Krishnan** (00:22:14):
Super important, by the way, your manager, peer relations are super important. Go have a coffee with them and they'd be like, "Great, I'm love to meet this person." Then when I joined at Facebook, I was notorious for being the person who sent a cold email to every single Facebook leader. And I'd be like, "Hey, I'm new here, I want to meet. Let's grab coffee," and everybody will say as everyone is a new person and always asking the same thing, which I'll be like, I show up, I'll tell them my story, I'll ask for their story. I'll be like, "What are you folks focused on? How can I help?" Again, no expectation of anything in return. And then I'll be like, "Who else should I talk to?"

**Sriram Krishnan** (00:22:42):
You do this, you do two coffees a week and literally just ask me two hours a week, everyone has two hours a week, it'll start compounding over overtime and time. And then as the years go by, you keep in touch with the people you used to work with you, these folks will go to other places, five years, six years go by, you start in your mid-20s or late 20s and you know hundreds of people all over. And the important thing about this is that it is a resource in so many different places. For example, one, if you ever need help, you're trying to look for a new role or you're trying to be like, "Hey, I want to hire this person, who knows something about this person?" or, "I want a new role. Who's looking for something?" that network becomes your key resource.

**Sriram Krishnan** (00:23:21):
Now what I think a lot of people don't do, it's just simple things. Number one is often people just have a great meeting with a peer and then they will never ever follow up. I'm sure a lot of us have the amazing first introduction email they never followed up, don't do that. I try and make it a point to make sure I always meet them once a year, once every six months. I'll just leave a note, "Hey, what's up?" And the other key part is expecting nothing in return. And generally people are very good at reading other people and if you go and being like, "Hey, I just want to meet you because I want a job or I'm here to network," whatever that means, they don't want to meet you. Just go and be very curious about who they are and try and help them. And you'll be surprised wherever you start, within a year, two years, you'll know hundreds of people who you can tap into, so I think that is super powerful. That's just building relationships.

**Sriram Krishnan** (00:24:05):
The other part is brand building. Both Aarthi and I at different points in our career have gotten feedback in our job saying, "Oh, with Sriram and Aarthi, it's brand build too much, et cetera." I have learned that that is terrible feedback and to totally ignore that and if anybody hears anything like that, just totally ignore that. The things that work well for me and a lot of others is putting yourself out there and that can be anything. That can be like you make a presentation internally, you write tweets, you're prolific on GitHub, you make a YouTube video, it doesn't really matter, but put yourself out there because the internet rewards people being out there. And what happens when you put yourself out there? It's a Bat-Signal. It's telling people that, "Hey, I'm here, this is my body of work," and you know what the internet does? It'll send amazing people to you.

**Sriram Krishnan** (00:24:45):
You'd be amazed how often somebody just have a random great Twitter thread with no followers and somebody super interesting will email them and that leads to amazing things happening, it encourages serendipity. So over the years, I wish I had listened less to people who said I should not do this and listened more to the people who said I should do this more.

**Aarthi Ramamurthy** (00:25:02):
I also think, Sriram keeps saying, "Expect nothing in return," I think the other way I see it is this is again an extension of optimism for us. Generally, we think people like to help each other out, that is just in their true nature. It's not meant to be transactional, it's not meant to be, "If I know them, they will somehow do something for me down the road," it's not that. Just the way we are all building communities and are a part of this broader community, the way we work is we all want to help each other and help them be successful. And if that is in your nature, it's hard to not feel like, "Yeah, of course I want to reach out to them. I want to see what I can do to help them. Maybe something good will happen, we'll collaborate on a project together," whatever. The core tenant being don't expect stuff in return, don't do it on a transactional basis, I think is really important.

**Lenny** (00:25:53):
What this reminds me of is Naval has this tweet that proved to be so true, which is don't network, instead create amazing things, create value, do good work and then people will want to network with you. And that's really stuck with me and it saves you from going to network events. Instead just go work hard, do awesome stuff and people are going to want to meet you.

**Aarthi Ramamurthy** (00:26:12):
I mean you will not believe the number of times I've shown up to some meetup or some founder thing or something and then somebody would come up and be like, "I'm here to network, what's your name?" And I'm like, "What? No, you can't do that. Not how that works."

**Sriram Krishnan** (00:26:26):
I actually say I disagree with Naval on this because often, when you're part of a large organization, it's really hard to do great work and get recognized for it. You're part of a team, which is great, but it's not the same as saying having a newsletter by yourself or having a piece of content by yourself. So when I was younger, I'd be like, "Great, I'm part of a large part-

**Aarthi Ramamurthy** (00:26:48):
I don't know, I mean you guys are saying the same thing, he's just saying create value and put it out there. I don't think it's-

**Sriram Krishnan** (00:26:53):
Yeah, I think the putting it out there part is super interesting. And also I would just say, don't wait to create amazing things. Often just the act of putting yourself out there can just spur amazing things in itself.

**Lenny** (00:27:05):
Yeah. And I think especially early in your career, you're not going to create amazing things immediately, so there's a lot of value to reaching out and meeting people. There's a couple of directions I want to go here. One is, so you gave this, I don't know, just mini masterclass on building a network and networking and things like that. I think what'll get people to rewind and listen to that again is I don't think people realize just how connected you two are. You're at the center of so many micro communities of the most incredible people. I don't know if you talk about this, but you run all these micro communities of incredible people in, I don't know, creator land and investors and product people and all these people and so it actually has worked. You may be the most networked person there is and I don't know if people know that.

**Sriram Krishnan** (00:27:47):
Oh, wow. Is that a good thing? I don't know. Is that-

**Aarthi Ramamurthy** (00:27:47):
It's a good thing.

**Sriram Krishnan** (00:27:51):
It's a good thing. Okay, I like that, I'll go with that.

**Aarthi Ramamurthy** (00:27:53):
I think the thing that, well at least with Sriram, outside of all of the masterclass stuff which I think he's particularly good at, I think the thing that Sriram, people don't realize about him is he's just inherently incredibly curious about people. He's just really just wants to know what somebody else does, who they are, what their story is. And this is not some like, "Oh, I'm going to spend 10 minutes letting them talk, I'm going to spend... he often never lets the other person talk, but when he does, he's truly-

**Sriram Krishnan** (00:27:53):
Hold on a second right there.

**Aarthi Ramamurthy** (00:28:26):
... but he is truly curious about who they are, what their story is. By now, we've known each other for 20-ish years and this is every dinner, every event, this is just how he's wired and so you just can't fake that in building out a network. He builds a network by just wanting to know who these people are.

**Sriram Krishnan** (00:28:49):
Thank you.

**Lenny** (00:28:50):
That's beautiful.

**Sriram Krishnan** (00:28:51):
The woman I married, ladies and gentlemen, right there. You marry the right person, everything else becomes [inaudible 00:28:56]. I haven't really talked about this before and I'll keep some of this slightly hidden, but I think the heart of it is I'm just curious about people, I'm just dumb about a lot of things. And I don't mean it as this false modesty way, I know a lot of folks are smarter than me. Lenny obviously is so much smarter than me at writing a Substack newsletter, it's just evident, Andrew Huberman is great at... Brian Armstrong great at building a crypto company, all these folks just evident. But what I realized is a lot of folks sometimes just want to be with other amazing peers. And one sort of hack I built over the years, I was like, "All right, let me just bring interesting people together."

**Sriram Krishnan** (00:29:34):
So I bring them in, let's just say various kinds of online communities, they're probably over 100 at this point. And I say, "Okay. You trust me, you trust me and I make the rules." Everyone keeps some level of confidence, everyone is a peer, they're all accomplished in their own way, no one is rude or mean or goes off the rails. So I'm a party host, so I'm like, "Okay listen, nobody is going to get super crazy over here," but I'm also curating. I'm like, "Well, I need somebody super thoughtful, I need somebody who's a little controversial, I need somebody who's funny, I need somebody who's like the celebrity... I'm trying to put together, engineer the right vibe or the right atmosphere, but digitally, I'm very anti-social in person. And some of these just happen over time. You put together the group of people and they hang out online and over times, you have a very famous CEO becoming best friends with somebody in their early 20s who's just getting started just because they're in the same space together.

**Sriram Krishnan** (00:30:35):
So I love creating those online spaces and I think it's something anybody here listening can do. Just take some of your favorite people, stick them in a WhatsApp group or a Telegram group or a Slack channel... which is by the way, Lenny's Slack, highly, highly recommend it. Lenny is great at that. But yours has hundreds of thousands of people and I think sometimes there's an intimacy from having smaller groups, like 5 people, 10 people like a shared space and then kick it off. And you'll be amazed of after a year or two, of how much intimacy and how much connection where sometimes people open up about losing their jobs or having a divorce or something really personal and intense just because of the shared trust. And I think there's something very heartwarming and fulfilling about being able to facilitate some of that.

**Lenny** (00:31:22):
I want to dig into that a little bit more. You've built these incredible communities and you talked about a couple, and Aarthi, I know you also built Facebook's early community products and Clubhouse. Obviously if you had to pick one or two things you got to get right with a new community that you're just forming, what do you think those two things are or one or two things?

**Aarthi Ramamurthy** (00:31:38):
Find the niche, start really small and find the niche. I think oftentimes I've seen other startup founders and I invest and advise in a lot of early stage companies. I went through Y Combinator, so I go back to YC as much as I can and go help out folks. But oftentimes I'll see people starting companies or founders coming in and being like, "I'm going to build this product that is going to cater to this community. I'm going to build this world's largest community off this kind of thing," and it almost starts at this super scaled version and then they set themselves up for failure.

**Aarthi Ramamurthy** (00:32:14):
You're almost better off doing these small, niche, non-scalable things to go find these oddball set of people who are doing this, who are really interested in this one thing and kind of scale from there and grow from there. And I think that's one big thing that when you're starting to build a community, don't start to build this super scaled community. Start with few people who are passionate about a particular problem and want to get together kind of thing. Start there. Two, I think people, and this might be a controversial thing, but I often think people don't think through monetization. If you're a community builder early on, start thinking about, if you're truly focused on this as a business, how would you actually make money off of it?

**Aarthi Ramamurthy** (00:32:55):
Oftentimes they hit some sort of scale and be like, "Crap, now what do I do? And then they're try all these options, they will have some churn and then they're like, "Oh no, but I thought this was a very sticky community." I'm like, "Yes, but it's not as sticky as this particular price tag." And so you have to start thinking through, if we hit a particular velocity, what is that going to look like? What are the things that I'm going to unlock. And think through monetization a little bit ahead of time before it comes in and becomes a crutch rather than a weapon that you can go leverage.

**Sriram Krishnan** (00:33:24):
But I want to say, Aarthi is kind of the creator of Facebook Stars and of so much of the thinking there and I can see her go super deep on this. Of course on everything she said, I have a slightly different framework. First of all, I really don't like the word community because the word community, the word networking, the word platform is a little abstract and it can mean a lot of things. And I like to think of things like a dinner party or church or things that seem more tangible and people know, "Okay, I know exactly what that is." So when I think of a community or starting one, I think first of all, it's a party. And you're first starting off, you're like, "All right, what is a vibe?"

**Sriram Krishnan** (00:33:57):
For example and this is also true for every social media platform where if you can be a crazy, people are dancing on bars, having a great time, getting really drunk party or you can have a really formal dinner where everyone is seated, there is plates with name tags and there's a clinking of glasses and you have to dress up. And they're both fine, they're both fun in their own way, but you need to tell people, as the host, which one it is. And by the way, I think one of the things that Twitter didn't get right in the original days which some of the other apps did, it never told people what kind of party it was. It like, "Are we going to Michelin star restaurant where sit down or it's a sports bar after the Super Bowl and you can go crazy?" And if you don't do that, people make up their own rules. That's number one.

**Sriram Krishnan** (00:34:37):
The second part is as the host, you have to curate the original set of people and you need a mix, this is super important. I think sometimes people do this thing where they either optimize for "interesting famous people" or they get the most talkative lot of people. And I actually read a bunch of books on hosting great dinner parties, I actually have some interesting suggestions there and it'll say like, "Well, you need a mix." For example, in any organization, let's say you're the VP that everyone knows about, but that VP doesn't have the time to maybe participate on a WhatsApp channel or a Slack channel and chit-chat all the time or show up for everything. And then maybe you need the really boisterous young BD exec who's out and about and meeting everybody. You need that person, you need somebody who's quiet and thoughtful. You need to merge different kinds of energy and that's almost an alchemy and that's more art than science. You have to start there.

Third I think is as the host, you have to have a sixth sense of how is a community feeling at any given point in time? Are two people dominating the conversation? That person hasn't said anything in a while. One of the things I like to when somebody joins a group or one of these places, I try and get them into a question which they will feel happy about because you know what happens the very first time you walk into a party? You look around, you're like, "I don't know anybody here. Oh gosh, okay. I know this one person and I'm going to go talk to them," and you just feel nervous. I'm trying to break that. For example, if you walk in a place and you didn't know anybody, Lenny is actually very good at being social, but I'd be like, "Hey. Lenny has one of the most popular things on Substack and he just wrote [inaudible 00:36:04]. I'm just giving you an opening, you to feel comfortable and that's another part.

**Sriram Krishnan** (00:36:08):
The third part I love is rituals and religions do a great job of this, which is do something every month. There's a little group I hosted some of my friends and during all of COVID, we did a Zoom meeting every Tuesday evening. And that was a ritual, it had nothing, it's just Zoom meeting with a bunch of friends, people can share-

**Aarthi Ramamurthy** (00:36:23):
And people would just bring their glass of wine or bring their kids in and there's no structured agenda. But people started looking forward to it through the pandemic and stuff and we would be like, "Oh my God, it's Tuesday. You know this evening, we are going to go do this thing." And it was a really great way to go build that community and I totally agree with that.

**Sriram Krishnan** (00:36:43):
Yeah, well Lenny has done an amazing job on it on his Slack, I see it.

**Lenny** (00:36:46):
You're so sweet.

**Sriram Krishnan** (00:36:47):
The other interesting tension and challenge is how to grow it because I think there are... Interesting point, a four person dinner, very different from an eight person dinner, very different from a 20 person thing where people hang out, very different from, once you start getting hundreds of thousands, the things you're willing to share, worrying about being judged. So I'm always trying to create more intimate different spaces and that's a whole other topic. So I think if you're trying to start a community though, I would say picking the right people, setting the tone, being really part of it yourself, that's most of it.

**Lenny** (00:37:21):
**Sriram Krishnan** (00:39:14):
I actually disagree with you and I actually think everyone should... well disclaimer, I work for firm which has invested in Twitter, but I swear that's not why I'm saying this, people have heard me say this for years-

**Lenny** (00:39:24):
And Substack.

**Sriram Krishnan** (00:39:25):
Yup. Everyone should tweet or everyone should post on YouTube or post Instagram and it doesn't matter how young you are. Because I actually disagree with the few things, which actually is a great point which I think a lot of people feel this, one is that you need to have hit a certain bar of accomplishment or interestingness to say something, strongly disagree with that. Second, that things are cringey. I don't think anything is cringey, I strongly disagree with that too. And I think these are both interesting-

**Lenny** (00:39:51):
Aarthi's face is great.

**Aarthi Ramamurthy** (00:39:53):
Wait, I feel like Sriram's bar is so low for-

**Sriram Krishnan** (00:39:55):
Dude, no, this is really important because I think what stops a lot of people is, I've had probably 100 plus conversations where somebody who's incredibly accomplished will come to me and they'll be like, "Hey, I want to get on Twitter, I want write content or I want to Substack or I want to do a podcast." I'm like, "Great." They're like, "But I don't know what to say, I look dumb, I don't want to get judged." But I'm like, "No, you're so accomplished," and it is the fear of being judged that so often stops people. So whenever I hear that word cringe, I'm like, "No, no, no, that's actually fine, you're fine. You'll figure it out," and here's why I say that.

**Sriram Krishnan** (00:40:30):
Number one is what the most important thing and even, listen, if you just remember one thing from this whole thing is just get started and do something every single day. And this sounds so basic, like Aarthi and I have is a running joke where it's like it's diet and exercise is what we say. It's like we are talking to people about how do you get healthy and you have the 100 different things you can do or podcasts you can listen to, but most of it's like, "Well, diet and exercise." And with creating content, diet and exercise, you just write a piece of content every single day because what's going to happen is it builds muscle, it gets you familiar with the medium and you start understanding what works in that medium and what doesn't and you start building reps.

**Sriram Krishnan** (00:41:08):
You know who never works out in my opinion? Is somebody who'll think for weeks, build up an amazing tweetstorm, blog post, newsletter, whatever it may be and then stops because the effort is so high. So I'm like, "One, do something every single day." The second part of it is, I actually think you don't have to talk about what you accomplish, you only have to talk about you. And by the way, this is going to sound very froufrou, but you are the best you out there. So for example-

**Aarthi Ramamurthy** (00:41:33):
Wow, okay.

**Lenny** (00:41:36):
[inaudible 00:41:36].

**Sriram Krishnan** (00:41:36):
... let's say you are a 21-year-old PM, fresh out of school, first year... by the way, we were all that. I was a 21-year-old PM at one time, Lenny would've been too, lots of others. First you'll see a lot of people who have been through journey and there are others like you. Second is you just talk about your journey, talk about what you're doing, talk about what you're learning. Because what often you're trying to do when you're creating content is to build a relationship with people. So when Charli D'Amelio dances on TikTok, she's not saying she's a professional dancer, she's saying, "I'm relatable, I'm just like somebody you would be friends with next door, I'm just like you." And so then people start connecting with you on that front, if you're authentic and you're doing a good job, and so everybody listening to this should be able to create content.

**Aarthi Ramamurthy** (00:42:17):
Okay, so the only place where I disagree, I think this is all right, but this is a bit like, we are Asian, we have this very Asian parent thinking, there are no participation trophies, so if it is cringey, you should at least acknowledge that it is cringey. I think at the end of the day, you have to persevere, I think I give a lot more words to people who are just persevering and showing up every day, but I do think there should be a level of self-awareness for people where it's like, "Man, this is not great. I'm not getting any traction. I need to improve on things and keep building on it," as opposed to being like, "I am the best me ever," and just keep putting out garbage, don't do that. Improve on stuff because there is such a thing as bad content-

**Sriram Krishnan** (00:43:03):
I agree with you, but I think when people mean cringey... okay, I'll see this. What people think they say cringey, it's like our peer group thinks that this content is too basic-

**Aarthi Ramamurthy** (00:43:11):
But everybody has that, whether you say it out loud or not.

**Sriram Krishnan** (00:43:15):
Well, I'll give you a story. So I spent years, I'd be like, "I'm a PM leader, I run organization, I should write smart PM things. I should write the kinds of things that Lenny writes." For example, I'll say that, "Lenny's Post the other week from Duolingo is... I was so jealous. I was like, "Man, this is the kind of content... I would be like, "It's amazing, banger post." But the problem was when you start doing that, you start censoring yourself. And I'll say, I've written a lot of posts over the years and I'll try and sound smart, I have a great intellectual framework in some of this work, but you know what my most popular post and tweetstorm of all time is? It is how to write a cold email.

**Sriram Krishnan** (00:43:48):
And when I wrote that tweetstorm, I was like, "Man, I'm going to sound so dumb," because Lenny doesn't need to know how to write a cold email and neither does the VCs I work with, everyone knows that. But the thing is, what is obvious to you and may seem cringey to your peers is definitely not obvious to a lot of people and they will connect to you, they will relate to you. When somebody says like, "Well, is it too basic? How do I get started with my job?" I'm like, "No, there's a lot of people who this is not obvious to," and I'll just put myself out there and what's the worst thing? Somebody thinks you're moron? That's fine. You put some new piece of content out there the next day and they'll fix it or you can just ignore that.

**Lenny** (00:44:23):
I think there's a lot of really good nuggets here. I think the only area maybe we disagree and we should move on, but this is [inaudible 00:44:29].

**Sriram Krishnan** (00:44:30):
Listen to me, Lenny, come on. Your podcast is too friendly otherwise, let's listen.

**Lenny** (00:44:34):
My feeling is I think for helping you do better work kind of content, like entertainment anyone could do no problem, you could be awesome at it, is I feel like you need to do something in your career first before you can start speaking to, "Here's things I've learned and here's what works and here's what doesn't work." I think I wouldn't spend a lot of time sharing all your wisdom before you've done a thing and been successful in some way.

**Sriram Krishnan** (00:44:53):
Yeah. I actually think you make a very interesting point, which is I think a lot of people online LARP, live action role-play, as somebody else which is like you trying to project a persona or a career point that you are not at and you know it, we know it, you probably admit you know it-

**Aarthi Ramamurthy** (00:45:14):
And also for that kind of content, everyone can tell. I think it just comes off as not authentic. I mean I feel like the universe figures itself out over time, but I do think there is a level of, just because Sriram thinks no content is cringey does not mean people all feel that way. You can't just magically just wipe that out. I feel like everyone just feels that way, whether or not you say it out loud. I do think there is a process of iteration and acknowledging that, "Yeah, okay, this is bad, but I'm going to put this out there anyway and we'll just keep working on this," and coming back to it.

**Aarthi Ramamurthy** (00:45:46):
I really appreciate people who would just do that and just keep coming back to it every day and like Rocky style, chip away at things. I really have appreciation for those folks because it's hard. I've realized over time that everyone is deeply feeling as if they're imposters and we talked about this. Imposter syndrome is so real, it is so gut-wrenchingly real that it's not just every one person, it's most people I think. So to be able to overcome that threshold and look at your amazing peers and your seniors and everybody else and then still be able to put yourself out there, I think we have to really appreciate that and help them go iterate and just get better over time.

**Sriram Krishnan** (00:46:27):
Yeah, I agree. One tiny story before we wrap on this topic, which is I was talking to somebody who's four or five years into their career as a PM and they'd written this post on LinkedIn which is full of cringey content, by the way. Okay, let me say it, LinkedIn has a lot of cringey PM content-

**Aarthi Ramamurthy** (00:46:27):
Wow, look at Sriram.

**Sriram Krishnan** (00:46:42):
... I'm sorry LinkedIn folks. And it was one of the things about how do you set product strategy as an organization and I was like, I called them, I was like, "Dude, come on. You're four years into your role, nobody believes that you actually are driving this from a place of actually really knowing it. And that is fine if you're learning, but you are trying to project this person you're not." But the thing which I was talking to him, I was like, "I know you've done this amazing deep dive on this other niche topic. You've gone out, you read all the posts, go write about that because you are an expert legitimately in something you think is niche, as opposed to a fake expert on this other thing you want to be."

**Sriram Krishnan** (00:47:17):
He went and wrote this follow-up post on something very niche and that went really popular because the truth is, there's not a lot of great content out there, especially great content from people who actually done the thing. You'd be surprised how niche you can be, but if you actually done the work, talk to a people, aggregated some posts, people come seek you out and you don't have to do it. So anyway, so lots of LARPing, lots of cringey LinkedIn content for sure.

**Lenny** (00:47:43):
Just to close this out, I 100% agree with the idea that people should be just trying stuff, writing, sharing stuff on Twitter, LinkedIn, just get it out of there, don't be afraid because that's how you start down this road. I was going to go in a different direction, but you mentioned imposter syndrome and I'm curious, have you two dealt with imposter syndrome and-

**Aarthi Ramamurthy** (00:48:01):
Oh, yeah. We have and I still, I don't know about Sriram. Sriram comes off as so much more confident and has so much gravitas that nobody ever thinks of it, but we both do, we both deeply have imposter syndrome. Every single day, anything we do, we look at ourselves, we are creators, we have this show on YouTube and then we look around at everybody else who have millions of subscribers and followers and everything and we are like, "Why are we creators? This is not a thing. We should not be doing this stuff. I just think people haven't been honest with us on how much we suck." It's like you have these loops in your head and then every once in a while, you'll see a comment being like, "This was amazing. I just had to stop doing what I was doing to listen to this whole thing. It was so valuable for me." And you're like, "Oh, okay. We are not all the bad. That's, I think, okay."

**Aarthi Ramamurthy** (00:48:48):
So we go through this a lot. For the longest time, I had really severe imposter syndrome through school, college, getting into Microsoft. Even after I got through the Microsoft, which we were one of the youngest product managers there, I still was like, "Oh, someday they're going to figure out that this was all... they'll know the real me and they'll be like, 'Oh man, we made this mistake with her.'" And it was just such a real crippling thing for me. Even now I feel like maybe it's not 100% true, but I can kind of see the gradients there, so very real thing.

**Sriram Krishnan** (00:49:27):
Yeah, it's so true. I have a hack or a technique of how to get over imposter syndrome. But I'll just say, and this is just if folks here feel it, every new job I've been in, I have always felt that I didn't deserve to be there and I mean I genuinely. When I joined Microsoft, I was a young student, I was like, "I don't know anything. These folks are professional, they've been doing this job for years." When I moved to the US I said, "Look, my accent is super intense, I'm Indian, these folks have been doing this for many years, they have very different lifestyles, I don't know what I'm doing here." When I move to Silicon Valley, I got no hired by probably four or five different companies and one of them told me, "You work for Microsoft so you can't really cut it in Silicon Valley because you're from Seattle," which I'll never forget.

**Sriram Krishnan** (00:50:07):
And I look at the person from LinkedIn from time to time, I'm very typically like, "Well, I've cut it now," and I'm very petty that way. And then of course and then when I start running large organizations, several hundred people or more, I was like, "I've never done this before." I'm in a meeting, everyone is looking to me, "Do they know that I've not done this before? Because I haven't done this before and can they tell?" And it's every step of the way. So it just pushes every step of the way and in the beginning, it was quite crippling, but over time, you build things to help you. And I think for those listening, if you feel this way, the thing I've learned to do is you have to retreat to a place where you feel real mastery of. So for example, when I was at Microsoft, I was like, "Well, I don't speak the language very well, English," and I had an accent, et cetera, but I knew that I was the most online developer person out there.

**Sriram Krishnan** (00:50:57):
I knew every single online community, I was very plugged into open source, so in every meeting when the topic would come to, "Hey, what is happening with Ruby on Rails?" I was like, "I know this better than everybody else," and I learned to put together a presentation. Because then you start with the base of something that you feel super comfortable in and you build from that. And what you realize when you build from that is you are like, "Oh, actually you know what? People really respect that and they react to that." And I also learned not to do other things. For example, for them for years where I would listen to people from a certain academic background or I'll be like, "I wish I could do slide decks like they could," or, "I wish I could have these intentional... but I was like, "That doesn't really matter. You just need to come from a place where you are confident you've done the work."

So if you folks are listening and you feel imposter syndrome, next time you walk into a meeting, just think about, "Okay, this is a place where I know I spend so many nights and weekends," and it can be super tiny, it can be one little button, one customer, but you've done the work, you've had multiple conversations, it is [inaudible 00:51:54]. And you start from there, you talk about that and you build out from that and you will feel comfortable. So I've done that in pretty much every role now and I still catch myself doing-

**Aarthi Ramamurthy** (00:52:03):
Yeah, I think for me, when I was a first time founder, I definitely felt that way and there was all this, at that time, which was conventional wisdom. Nobody we knew at that time were founders, it's not our friend circle, they all worked in medium to big companies. My family, nobody has ever been a founder, entrepreneur, it's not a thing. And so when I started this I was like, "Oh my God, I'm making a mistake." But then you read all these people tweeting or writing posts, being like, "If you're a founder you'll be really good at fundraising. Best founders learn how to... I sucked at fundraising. I was so bad at it. It was just like, "Oh, you have to be able to tell your story."

**Aarthi Ramamurthy** (00:52:41):
I tried. I email like 250 founders, took 85 meetings and 50 plus second meetings and then got 30 checks. This was my seed round which took eight months to close or something and I was like, "Oh my God, I'm so bad at this. I should just give up right now." And then I started building this startup and I was like, "Actually I'm really, really good at understanding customer acquisition and really trying to find creative ways to cheaply acquire customers." And I kind of started putting together playbooks on it, what I can go do there and I tried this, I tried this, then I started talking to few for our own investors and I'm like, "I don't know if your portfolio companies are finding this useful, but I tried these tactics." And they were like, "Oh my God, I'd never heard of that."

**Aarthi Ramamurthy** (00:53:28):
And so I realized that that's the one place I could be really good at and I can grow my business in a really profitable way very quickly. And then investors started talking to me about other companies and all of that stuff and it became a thing and that helped me get more confidence over time. It was like, who cares if I can't do these other things? I can do these few things and this is really, really important to build a sustainable business and I think I can do that. And that for me kind of helped me get over it. It's not anyone telling me, "Don't worry, you'll be good at it," that never helped, it was just I had to do it myself to figure it out.

**Lenny** (00:54:02):
It's interesting both of your pieces of advice is find the thing you're actually good at and then just lean into that as much as possible. That's something I learned from an executive coach I worked with once that you have strengths, you have weaknesses, you can accomplish almost all the things you want accomplish through the lens of the strengths without using those weaknesses as much and that really was pretty transformative.

**Sriram Krishnan** (00:54:21):
That's actually such a profound point and I wish somebody had told me that earlier in my career because early in my career, I would get all this advice like, "Oh, Sriram is too loud and too boisterous." And the thing is, nobody I know has ever become successful by trying to fix their weaknesses, it's just impossible. The only way you succeed is one, you might need to mitigate some of them, especially if they're really, really holding you back. But you have to lean into your strengths, which is a weird thing because I think when we do performance feedback, it's feedback and so much time we are like, "Well, these are all the good things and then let's talk about the ways you know can improve."

**Sriram Krishnan** (00:54:53):
It's almost the flip time and I think if you're doing performance feedback, you'll be like, "Well, these are things you're really good at, let's make you even much better at that. Let's make you fly faster, run harder, close the deal, write better code." Oh yeah, and some people are mad at you for these things. You should watch it and maybe fix some if it's really bad, but that's not what's going to pull you ahead. It's the superpowers that's going to really pull you ahead, so let's focus on that.

**Lenny** (00:55:15):
Yeah. The way I think about that is the weaknesses can't be liabilities, you can't just get on stage and melt and explode, but you don't have to be amazing. As long as you can email really well, write documents really well, communicate in other ways if that's a strength. One last trick while we're on this topic, I was just reading Hunter Walk's blog and he shared a cool trick for imposter syndrome where you just have to ask yourself, "Am I so good at pretending that people don't see what's actually happening? Am I actually that good to being this imposter? Probably not, the people can tell," and it's really unlikely you're actually an imposter.

**Sriram Krishnan** (00:55:46):
Also, by the way, the reality is and this a cliche is people are just not thinking about you.

**Lenny** (00:55:51):
Right.

**Aarthi Ramamurthy** (00:55:52):
That's true. Yeah, you're giving other people too much credit that they're focused on somebody else. Everyone is so busy focusing on themselves and their own insecurities and fear and just living life. And think about ourselves, when was the last time we thought about somebody else and were like, "That person, probably an imposter"? We just don't have the time for it.

**Sriram Krishnan** (00:55:52):
Yeah, I've been thinking about me this whole time.

**Aarthi Ramamurthy** (00:55:52):
I am not surprised.

**Lenny** (00:56:20):
You guys are hilarious. There's something I actually along these lines I was going to ask about. I remember, Sriram, when you were just getting out of the companies you worked at, you made this point that you were an IC and you were in these meetings where people are reviewing your work and they're making decisions and you're the person presenting. And then all of a sudden, you're the person reviewing all their work and making the decisions and no one trained you to be that person where you're like, "Oh my God, I'm that person they're all looking for for all these answers?" And I'm curious just how you worked through that and what advice you'd have for people that are maybe going through that transition?

**Sriram Krishnan** (00:56:49):
Yeah, it's a good question. First of all, it's kind of a jarring change because you realize, "Well, I have power, but I'm also called upon to do a bunch of things," because no meeting, let's call it an exec review, let's say and you're the exec they're presenting too. It doesn't really matter what your title is. All of a sudden, you're having to do a bunch of things. You're making decisions, but you're also providing feedback, sometimes explicitly, sometimes implicitly.

**Sriram Krishnan** (00:57:10):
You might piss off somebody by naming somebody and not naming the other person, you might piss off somebody by not inviting them to the meeting. You might have to feel like, "Well, I really want to overrule this person, but if I do, they might get mad at me." And there are so many different things which you have to keep in your head as well as like, "Is this the right path for the team, for the company," or whatever the situation is and it can be really overwhelming. And I learned a lot of how to do great exec reviews from my time at Facebook, from Zuck and from Andrew Bosworth. Andrew Bosworth, Boz, has some great posts on his site, boz.com, about how to do reviews and-

**Lenny** (00:57:40):
I'm trying to get him on this podcast by the way.

**Aarthi Ramamurthy** (00:57:42):
Oh, that sounds good. He's great.

**Sriram Krishnan** (00:57:43):
He's great, he's fantastic. Let me know when you have him, I have some questions I want to get you to ask him. But Boz had a few ways of thinking. First of all, let's start with Zuck. Thing I loved about Zuck's exec reviews was that it was clear when you walked into the room that you are talking to one of the most powerful people on the planet. But what he did which not a lot of other people in this position do, is he would tell you what the rules of engagement were for every meeting or [inaudible 00:58:08]. He'd be like, "Look, I'm going to give you a spectrum of A, how much I care about this topic. Everything from I don't care, I don't know why you're talking to me, do I care kind of care little? I kind of care so I'm happy you're getting this update, do I really want you to do this? But you know what, if you overrule me, that's fine. All the way to I'm the founder, I'm the CEO, just do this." But he will make it clear where he stood on the spectrum.

**Sriram Krishnan** (00:58:27):
The second thing he would make clear is why he believed the things he did. For example, the very first time I pitched him on what is the Facebook Audience Network which grew into probably one of the largest ad networks on mobile, he had all these sort of ideas, he was like, "We shouldn't do an ad network because," and he had all these opinions on, "Well, mobile ads all look terrible, they are spammy, X, Y and Z." But he was really good at articulating those to you and also saying, "Well, if you can prove me wrong on these legs of my logic tree, I will let you overrule me, unless I have a strong opinion." So when you walk in a meeting, you're like, "Well, I know the framework, I know what the dance is, do you convince him?" Or maybe there's no shot to convince him and that's fine. He's the CEO and that's fine too.

**Sriram Krishnan** (00:59:10):
So I really learnt that it's so important to clarify for your team the framework you're operating in with you. And it's also maybe a clarifying function for yourself as so how do you actually feel about this and why do you feel like that? That's number one. The second part of it is inside a meeting, there's a few things I think you need to do which is clarify what kind of meeting is it. Is it just an update? "Great. We're just going to get an update? I'm going to listen to you, I'm going to applaud you for a job well done, I'm going to send you on your way." Or is it a decision in which case, what are the pros, cons, et cetera? There are some real big failure modes where one kind of meeting slides into another kind of meeting where somebody is like, "Why are we doing that? Is that a thing?"

And then somebody will start fighting on and people are like, "Oh gosh, we shouldn't have brought this topic at all." And everyone listening to this has probably been to one of those meetings. There's also something else which teams sometimes like to do, which is they'd be like, "Hey, we have a hard problem. We don't know what to do." They're trying to kind of push the responsibility of the [inaudible 01:00:02] from them to you which may be fine, but you should be like, "Hey, are you saying that you can't make up your mind and you want me to make up your mind for you?" You want to be very explicit because often I've seen this when there are hard decisions, teams are like, "The exec feels strongly, we don't want to know what to do," and they kind of want to push the accountability to you and here, we watch out for that a lot.

**Sriram Krishnan** (01:00:25):
There are a lot of hygiene things we think are very important. For example, send out a pre-read before, make sure it's the right people in the room, not everybody, but not missing out key people. Make sure you're paying complete attention, make sure everyone gets a chance to talk which by the way, I was really bad at. And those things go a really long way. Oh, and one final thing, have a regular rhythm to those, so you're doing this every month, et cetera. What I hate, I stole this line from Gokul Rajaram, is the phrase, "Hero meetings." All of us have been this which is there's a big thing, there's a big review, it's probably a go/no-go, maybe it's career limiting, maybe it'll get our team funded and everyone is stressed out. You spent two weeks working on a deck and the first 20 minutes of conversation goes totally sideways because the exec thought of something. Every one of us has been one of those. Those are bad.

**Sriram Krishnan** (01:01:11):
The way to fix that is to have a regular check in, so you have meeting every single week and becomes like you're not spending weeks, it a muscle, it's a rhythm of what you do and those are reason. Sorry, I went on a bit of a speech there.

**Lenny** (01:01:21):
What I was thinking about is you two have worked at basically all the big consumer companies and coming back to imposter syndrome briefly, what's the worst product you've built or the biggest failure you've each built and what did you learn?

**Aarthi Ramamurthy** (01:01:34):
Oh, man. At a startup, I tried all kinds of things. We kind of grasp at straws and build whatever. And also I think I fell victim to, a lot of startups do this where they'll see some theme that has become a meme with investors and they'll be like, "I'm going to go build that company. I'm just going to take that technology, adopt it." You're kind of start of seeing that with AI now where it's like everything is now an AI company. Of course everyone has incorporated AI part of it is you get it, you kind of want to be in the game and be cool, but if it doesn't really fit with your product hypothesis and thesis and what your customers are asking for, don't fall for that fad.

**Aarthi Ramamurthy** (01:02:18):
And I did stuff where I totally fell for the fad. I think I had a consumer electronics e-commerce, like a machine learning model where we rent and then recommend the right things to go buy. But then we were like, "Oh, Uber is doing this whole UberX thing where it was people having their cars and they could do this thing." And at that time, I think this whole shared ownership of stuff became such a big thing and I was like, "Oh, I'm going to do that exact thing where it's like it's less-

**Lenny** (01:02:51):
[inaudible 01:02:51].

**Aarthi Ramamurthy** (01:02:51):
At that time, we were partnering with Best Buy and we were like, "Well, we should do this other side product," which is people's own stuff that they could put up on the site. Total disaster because there is a lot totally different company logistics, everything. You could build it out as a different business, but we had a small team which was heavily focused on this business, was already doing pretty well and then we had to fork all of that effort to go build this other thing which required different skillset, different fulfillment technology and all of that. And so we were like, "Okay, disaster." So we pull the plug on it many months in, but we should have done it a lot sooner.

**Lenny** (01:03:26):
What you learn from that experience other than pulling the plug sooner?

**Aarthi Ramamurthy** (01:03:30):
Yeah, don't fall for fads. It's do the thing that your customers are asking for and are willing to pay for. Or not even what your customers are asking for, but if you have something that is working, don't get distracted. It's very easy to be like, "I'm going to build this five other things and it's all going to accrue value." And I literally talked to another founder last week where they're like, "But I'm building this consumer thing, but I'm also going to do this SDK so I can go partner with these other companies and do this B2B thing." And I'm like, "But you are four people. Why are you doing that? That's crazy." "But imagine catering to 10X the market." I'm like, "Well, but you're going from a consumer payments thing to something like Stripe and that's a very different business, so do you want to go do that and go have that trade-off conversation?" So that was one big learning. At Netflix, we tried this out, we knew it was an experiment. This was before Netflix was cool like 10, 11 years ago, where [inaudible 01:04:27].

**Lenny** (01:04:27):
Like DVD place?

**Aarthi Ramamurthy** (01:04:28):
Yeah. So my job was to build the streaming player software that goes-

**Lenny** (01:04:34):
No big deal.

**Aarthi Ramamurthy** (01:04:36):
Yeah. My job was to go partner with Samsung and Sony and Panasonic and build a software, the SDK that goes into TVs and set-top boxes and Blu-ray players. This is before international, Netflix and original content like House of Cards and all of that, but one of the experiments we tried back then was Netflix 3D. Total disaster [inaudible 01:04:57].

**Lenny** (01:04:36):
Like on 3D TVs? That was another fad issue. Oh, no.

**Aarthi Ramamurthy** (01:05:02):
Exactly, yeah. But we had a lot of OEMs who were like, "3D is going to be really big and you have to go invest in that." So I spent months trying to do this left eye, right eye codec and trying to make this whole thing work with these odd glasses, sitting in your living room trying to do 3D content, which is really hard. I think we tried seven movie titles over, imported it over to 3D and they're like, "I don't think this is such a great experience," and we ended up pulling the plug on it. We knew it was an experiment going in, we knew there was a good exit criteria, but it was kind of a failure.

**Lenny** (01:05:35):
Sriram, I bet you're going to have a really good one?

**Sriram Krishnan** (01:05:37):
All my products were huge successes, so I have nothing.

**Lenny** (01:05:40):
Okay, [inaudible 01:05:40] other way it's going to go.

**Sriram Krishnan** (01:05:41):
Yeah, what are you talking about? No, I'll say part of the very first thing I worked on and it's complicated because I love the team and I think we did some great work, was we work on something called Visual Studio for Devices. And the idea was-

**Lenny** (01:05:52):
What was it? Wishlist for what?

**Sriram Krishnan** (01:05:54):
Oh, sorry. Visual Studio for Devices. This was in 2005-

**Lenny** (01:05:58):
Oh, like coding on your phone?

**Aarthi Ramamurthy** (01:05:59):
No, no.

**Sriram Krishnan** (01:05:59):
Well, coding for your phone. And the idea was this was before iPhone it, this was the era of Windows Mobile Pocket PCs and Windows Mobile smartphones, so-

**Aarthi Ramamurthy** (01:06:08):
Man, the kids listening to this like, "What's he talking about? What was before iPhone?"

**Sriram Krishnan** (01:06:14):
Yeah. And this was 2005/2006, so right before the iPhone came out, the two years and we were fresh out of school, both of us worked on this. And there was basically an ID, Visual Studio, and we had an extension where you could write code on a slimmed down version of the .NET Framework and you would run apps on these small phones and these small Pocket PCs. And the team was fantastic, we're all still friends and without that, we wouldn't have our jobs or careers, so that's not the point. The point is we all knew these phones were terrible and slow and awful, but what we were told all the time was, "Listen, nobody can change this because the carriers control this market. They determined what software goes on a phone, goes on a device, so this entire ecosystem is all about competing with Blackberry."

In fact, the codename for Windows Mobile 5.0 was Crossbow and kind of a little secret which I think is kind of public now, Crossbow was a weed killer, it killed blackberries. And so the whole idea was how do you kind go after the enterprise market Blackberry and work with the carriers? And then in 2007, Steve Jobs comes out and says, "I have three launches for you, actually it's one thing." I remember texting my manager, I was like, "You have to see this keynote," because it was so obvious that this thing was going to change everybody. And everyone in Microsoft was like, "No, it's the carriers who have all the control. They will never let these devices [inaudible 01:07:32]. But actually, it turns out that's not true.

**Sriram Krishnan** (01:07:34):
I learned two lessons from that. One is the market is bigger than all of you. You can work with the amazing team, you can work with the A plus team, A plus company, but if the market shifts, you can't overcome a bad market or a bad space. The second part is at the heart of it, if you feel some product is bad and if you feel like this new thing, it's just better to use and you can just feel it instinctly, you have to follow the instinct. Because I remember being like, "Yeah, the iPhone is cool, it feels so much better, but okay, maybe they're right, maybe it is the-

**Aarthi Ramamurthy** (01:08:04):
All these people are so much more senior than us, clearly they've put so much more thought into this, clearly what do I know kind of thing. And you realize that now, I think over, what, we've done product for 15, 16 years now, and we look at it and go, "We now have these patterns to go match against." We know when something is better, when something is working, when something feels like it's intuitive, you follow that intuition now then and not try and fight it and be like, "But here are all these things where this is not going to get there," kind of thing. It just doesn't work that way, the market ultimately wins.

**Sriram Krishnan** (01:08:40):
And I think when you're younger, you should really trust your instincts. And instincts can mean, "I just hear people talking about this other thing a lot," or, "I hear that other company's name come up a lot," or, "I tried this thing and... And you may not have the framework to articulate it and you may not trust your instincts, but there's something there and you should learn to listen to that voice. You're like, "Why is that? Why are we talking about it? Maybe they're doing better marketing, maybe their CEO is better on Twitter or they have Lenny Rachitsky as an angel investor or they advertise on your podcast," there we go. I tried to get a plug in there, Lenny. But you have to listen to your instinct because there's usually something there to follow.

**Lenny** (01:09:22):
I only have two more questions, one is you mentioned framework. I know you have strong opinions on a very specific framework, Jobs-to-be-Done and I know you're not a fan. What do you want to share about why you don't like Jobs-to-be-Done as a framework?

**Sriram Krishnan** (01:09:37):
All right, I knew you were going to ask me this and I was thinking how do I be kind of balanced in-

**Aarthi Ramamurthy** (01:09:46):
Bombastic?

**Sriram Krishnan** (01:09:47):
No, balanced and give measured answer and say, "Well, every framework has good and bad ways and there are good things and bad things," and I could probably given one of those answers. No, I actually think the more fun thing to do is I'm going to say I hate Jobs-to-be-Done, I think it's a terrible framework, I think no successful company has ever been built on top of JTBD and if you pick JTBD, you're probably doomed and here's why. Let's go back to the canonical example. And there's nothing Clayton Christensen who was a legend, amazing, the milkshake, what is the idea of being the milkshake? You are a person, you go into a commute and you're like, "Hey, I'm going to get this milkshake because it's the exact right quantity and save me on my commute." But they changed it up and all of a sudden, boom, it was not serving the job and look into the thing that actually it is serving the customer for.

**Sriram Krishnan** (01:10:39):
I'll tell you that's not how actual real companies work because in real companies there are so many different parameters. For example, maybe it is really, really hard to go build that milkshake. Maybe there's another person who opens up across the street who builds a better milkshake than you do. Maybe the cup configuration in the car changes, maybe the supply chain for milkshake changes. But in my world, let me make this more concrete, when you work in social media, there are often so many other agents in the system where you can't focus on one person's equation. I'll give you an example. When you sign up for Instagram right now, when you sign up for Facebook for many, many years, Facebook knew that it needed to get you to 10 friends in 14 days.

**Sriram Krishnan** (01:11:14):
If you got your 10 friends in 14 days, you were probably going to use Facebook. So it'd be like, "Well, we're going to throw every tool we have at our disposal to get you to 10 friends and 14 days." So if you signed up for Facebook for many, many years, you'll get this little thing called People You May Know. Then you'll have this person who just signed up for Facebook, you go, "Why I'm seeing this person?" It's not because you need a friend, because they need a friend. So what Facebook did was it made your experience slightly worse to make that person's experience slightly better. This was performing no job for you, it was trying to perform a job for them. Was the right trade-off or not? I don't know. We had this problem at Twitter. The single best product launched for the last five years at Twitter was the introduction of the algorithmic ranking and-

**Aarthi Ramamurthy** (01:11:53):
God, hearsay. Oh my God.

**Sriram Krishnan** (01:11:53):
... and it saved the company and power users hated it. They're like, "I know how to control my timeline, I know who to follow," et cetera, et cetera. It turns out though, this is not built for power users. It was really built for a regular person when they sign up for Twitter to be able to give them a great experience because we knew the power users, they already have. And by the way, TikTok really great example of that. So how do you make the trade-off? Do you pick power users or do you pick a regular person? What is the trade-off between them? Jobs-to-be-Done does not tell you that.

Let me tell you this. If you go order a package from Amazon right now, five years ago or three years ago, you would've gotten an email, it'll tell you what is that package, what is in it and when it's showing up doorstep. Last couple of years, it doesn't, why? Because Amazon doesn't want Google to have that data inside Gmail system. So it is, for very, very valid competitive reasons, made your experience worse because that's the right thing do for a company. So real life and real product is all about these trade-offs and whenever I've seen people trot out JTBD, it's a tell that they actually haven't dealt with a trade-off, where you have to make one person's life slightly worse in one situation for some other interesting dynamic. Okay, I'll stop with my mini speech [inaudible 01:13:02].

**Lenny** (01:13:02):
This is my favorite part of the podcast so far. I'm hoping people listen to the end here because this is-

**Aarthi Ramamurthy** (01:13:07):
Yeah, I think JTPD, the problem with that is it's just too idealistic. And most frameworks are, but this one just takes it up a notch where it's like it's almost meant for people who are so naive about product building and especially product building at scale. I think it might work for the V1 or just a hypothesis that you're trying to go test out, where it's like, "What is the core value that we are trying to serve for this user," kind of thing. But really V2, V3, it kind of falls apart because you have these super hard trade-offs that you have to make and every company goes through that. So it's almost a little too idealistic in its thinking. I think that's the biggest problem with it.

**Sriram Krishnan** (01:13:44):
Yeah, and look, I was being a bit bombastic obviously and it does have some [inaudible 01:13:48].

**Lenny** (01:13:47):
We're going to edit this part out. This is [inaudible 01:13:49].

**Sriram Krishnan** (01:13:50):
Yeah, blah, blah, blah, blah, blah, blah. It's may be useful in some niche case which nobody has ever heard about-

**Aarthi Ramamurthy** (01:13:55):
For milkshakes.

**Sriram Krishnan** (01:13:55):
Right, for milkshakes. Yeah, if you're starting a milkshake company, go for it. But I'll say, so people have good [inaudible 01:14:01] what is the alternate, would involve not JTBD, how do we actually figure this out? And I think a much better way and I really understand the early Facebook years, which is systems thinking. Think of all the players in the system, think of all of their incentives and how they interact with each other. So in that milkshake example, your car, the person, the competitor across the road, the supply chain, the profit margin of each person, the podcast they have to listen to, what is each person's incentives that you're trying to drive and look at how they all work together.

**Sriram Krishnan** (01:14:31):
So for example, so then when you look at the algorithmic rankings case, sure it kind of deprioritized a certain set of people, but it prioritized the other set of people and you could then have a much more rational discussion about whether that trade-off is worth it. Maybe it is, maybe it's not, but it's a much better discussion that, "Well, that person wanted milkshake, we're not giving them milkshake," what do you do? That doesn't help you at all. And yes, it may be a good tool in ways that I absolutely have not seen so far, but-

**Aarthi Ramamurthy** (01:14:55):
Yeah, also the other tool I think I really like is first principles thinking. Everyone throws it out there, it's kind of become this cliche now, but really think about it as if your product didn't exist and if you had to start over from scratch, would you build it the exact same way for these set of customers? How would you think about it? Oftentimes people hyper-focused on competition and what other company is doing. That almost never matters. Other companies are probably looking at you and going, "What are these guys doing?" And you have to look at it as all of these systems, as Sriram said, but also really think about it as if you had to do this all over again, how would you do this? Is this the right way or are you just inheriting decisions over time and just trying to make incremental changes and trade-offs and stuff like that? I like that way more than trying to think of it as a job that a customer hires you to go do. It just sounds like really naive.

**Sriram Krishnan** (01:15:51):
It makes you sound smart, I think. But I'll give you an example. Sorry, I have to-

**Aarthi Ramamurthy** (01:15:55):
Stop. You just gave so many examples.

**Sriram Krishnan** (01:15:55):
No, one last thing.

**Lenny** (01:15:55):
Examples is good. Let's do one more example.

**Sriram Krishnan** (01:16:00):
One last example, okay. One of my favorite posts from Lenny in the recent times, I don't know when this episode going to go out, is the Duolingo growth post. I've been sharing it all the time, it's exactly one of the best posts I've seen recently. What is the job that people are hiring Duolingo to go do? Help teach them a new language, right? That sounds about right, some version of that. But if you look at that post, what actually saved the company?

So they tried dozens of different things, found their North Star metric, the current user retention rate, then they tried leaderboards, realized why leaderboards don't work. Then ultimately, it is streaks that worked up. Tell me how do you use Jobs-to-be-Done to get to a world where, "Hey, we really going to show these fire emojis and you need to kind of get that fire emoji every day. Because what it's really getting at is the sense of [inaudible 01:16:45] so there is no JTBD brainstorming offsite that'll ever get you there. What I've seen quickly, is almost always when you get a great product breakthrough like that, it comes from one person usually having a product intuition about something, about the psychological thing the product delivers and systems thinking. Those are the only two places I've ever seen it up. Okay, I'll stop now.

**Lenny** (01:17:08):
No, that example is amazing. I was going to talk about how I've actually found it a little useful in my life, but I think that's just going to keep us going-

**Aarthi Ramamurthy** (01:17:16):
I was just going to ask you, are you now convinced Lenny, because Sriram has spent 45,000 minutes just trying to tell you why you should not be using JTBD-

**Sriram Krishnan** (01:17:24):
I'm just going to get canceled by Lenny's audience. Lenny's audience is like, "This is a reasonable podcast." They're like, "I now hate this guy." [inaudible 01:17:30].

**Lenny** (01:17:30):
It. I think the JTBD industrial complex is going to come after you.

**Sriram Krishnan** (01:17:35):
It's all mafia.

**Aarthi Ramamurthy** (01:17:36):
I think if you see a bunch of mass unsubscribes, I just want to say this is not on Lenny, this is on Sriram.

**Lenny** (01:17:41):
[inaudible 01:17:41] from your podcast.

**Sriram Krishnan** (01:17:43):
Yeah, I'm going to get attacked by a bunch of people who are really good at holding offsites and framework thinking.

**Lenny** (01:17:50):
Yeah. I find it useful in specific cases, not as a scaled product development process, I think which you've run into or just the whole company is run by Job-to-be-Done. One paper was like, "What is the job?" And you're like, "The job is to get them to open that up three times more each day." Yeah. Okay, I know you guys have to run so I have one more question. I have this saying in my family that whenever we do something well, I'm like, "We're making it in America," because we also immigrated from the Ukraine. And as immigrants, you talked about your story of coming to America and clearly making it. You're both at the center of, I don't know, what's happening in tech, which is also at the center of the world in many ways. I'm curious what advice you would give to immigrants and people that have moved here recently or even a while ago, just how to make it and be successful in the US, especially in tech?

**Aarthi Ramamurthy** (01:18:38):
Some of it Sriram covered before, it's put yourself out there, don't be afraid to put yourself out there. Oftentimes, for us, it took us a decade plus to feel comfortable doing that because we came in, we look different, we sound different, we have strong accents, the number of times I got told at both startups and before then, "Oh my God, your accent, it's so difficult, I can't hear you," or, "I don't understand what you're saying." I got told before fundraising that nobody will be able to invest in my company because the accent is too strong. You already have these virtual barriers in your own head and then you have people coming and telling you actively that you are different and you can't succeed.

**Aarthi Ramamurthy** (01:19:24):
Now if I had to do it all over again, I almost think these differences are what sets us apart and makes us unique. And you can do really interesting things with them because you are going to a place where you are rare and that's, I think, a really good thing. So you should sharpen that rareness and do really interesting things with it, whatever that might be. We have this show called Good Time Show, it's Aarthi and Sriram's Good Time Show and we focus a lot on outsiders being insiders or how you started out as... For us, we are quintessential examples of that where we're outsiders to tech, to Silicon Valley, to being in this world and we kind of "made it" to being here. And we often talk about what it takes to do that and whatever your version of being outsider and becoming an insider means. And for us, part of it is not being afraid to put yourself out there, power of cold emails, networking and being really proactive about that. What would you add to that or how do you think about it?

**Sriram Krishnan** (01:20:25):
I think everything Aarthi said, I don't have much to add. I'll just say if you're listening to this and you're immigrant, A, you're in the right place, B, you're listening to this podcast, reading this newsletter which is probably not your day-to-day today job, so you're already doing something right, so you're going to make it. You're already putting yourself out, you're doing the right things, you're going to make it.

**Lenny** (01:20:42):
What a beautiful way to end it. Two final questions, where can folks find you online, the Good Time Show, when you on Twitter, wherever? And then how can listeners be useful to you too?

**Sriram Krishnan** (01:20:51):
They can find us online on JTBD sucks... No, sorry. That's my alt account. Well, we are on pretty much every platform. We are aarthiandsriram.com. That's kind of a home for our podcast, our show, so go subscribe there, but you can find us everywhere. We are on YouTube at again, Aarthi and Sriram, you can find us on Spotify podcast, wherever you get your daily milkshake/podcast and also on Twitter @aarthir and sriramk.

**Lenny** (01:21:24):
Amazing.

**Aarthi Ramamurthy** (01:21:25):
And how can people be useful [inaudible 01:21:26].

**Lenny** (01:21:26):
Yeah.

**Sriram Krishnan** (01:21:28):
I would say, this is going to sound like a cliche, but my job is fantastic in a way where if people are building amazing things, I benefit. Because if you build amazing things, odds are you're going to build a great company and then odds are that I'll have the chance to maybe invest or one of my partners will have the chance to invest and hopefully you make a bunch of money out of it. So just go out there and build things, tell me about the things you're building and also just reach out-

**Aarthi Ramamurthy** (01:21:55):
Yeah, just reach out, say hi.

**Sriram Krishnan** (01:21:58):
Okay, let me put it, if you listen to this, send me a DM, send us a DM and send us an email and we will respond and-

**Aarthi Ramamurthy** (01:22:04):
If it is JTPD hate, just send it to him, not me. Just keep me out of it. But for everything else, if it's a nice note especially, send it to me, I will read it.

**Sriram Krishnan** (01:22:12):
Yeah.

**Lenny** (01:22:13):
All right. I hope you're ready for some DMs, both of you. Thank you again for being here. You've set the bar high for our first duo guest. Thank you again and goodbye everyone.

**Aarthi Ramamurthy** (01:22:24):
Thank you.

**Sriram Krishnan** (01:22:24):
Thank you.

**Lenny** (01:22:27):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify or your favorite podcast app. Also, please consider giving us a rating or a leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [19/22] The ultimate guide to OKRs | Christina Wodtke (Stanford)

**Christina Wodtke** (00:00:00):
... people do not value celebrations enough. I've had CEOs who said, "Well, it was the middle of the quarter, so we didn't start OKRs, but we did start Friday celebrations and oh my God, things are already changing. Things are already getting better." The simple act of getting together and saying, "What was the most awesome thing that happened to you this week? What's the most awesome thing that happened in marketing? What's the most awesome thing that design did this week?" It makes people feel like they're part of something really special, and it's super exciting.

**Lenny** (00:00:30):
Welcome to Lenny's Podcast, where I interview world class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Christina Wodtke. Christina is a multi-time author, speaker, and lecturer at Stanford where she teaches product management, game design, and a few other topics. She also consults with companies on their product development processes, and in particular, their OKR process. Before getting into teaching and consulting, she was a product leader at LinkedIn, MySpace, Zynga, and Yahoo, as well as a founder of three different companies, plus an online magazine called Boxes and Arrows. In our conversation, we go deep into OKRs. What is the atomic unit of an OKR? What might be broken about your OKR process? Why you may want to roll out OKRs or change how you approach them. 

**Lenny** (00:01:20):
Also, how the best companies leverage OKRs, the most common root causes of OKRs going wrong, the elements of a healthy OKR cadence, how OKRs fit with mission, vision, strategy, and roadmaps. We also touch on the skill of storytelling. And she also shares her most contrarian perspective on what new product managers should be focusing on. Christina is a wealth of knowledge and super interesting and fun, and I know you'll learn a lot from her. 

**Christina Wodtke** (00:03:55):
Thanks, Lenny. I'm really excited to be here. I've been hearing about you forever. It's so cool to be here in person.

**Lenny** (00:04:00):
I'm more excited for you to be on the podcast. I kind of see you as the queen of OKRs. I don't know if you like that title or not, but in my mind that's where you sit currently, and partly because from what I can tell, you've done more to help people with OKRs and understand OKRs and fix their OKR process than most anyone else I know. As I'm sure you know, a lot of people just don't like OKRs, are kind of anti-OKR and have had bad experiences with OKRs. And what I want to try to do with our chat today is to try to change people's mind, who are maybe anti-OKR and to help people optimize their OKR process if they're having an okay time with OKRs. How does that sound?

**Christina Wodtke** (00:04:39):
That sounds just fine, although I have to say in the tech industry, it's a little too easy to be clean. Maybe when I'm a emperor for life, that might be my title.

**Lenny** (00:04:48):
That might be by the end of this podcast, we will crown you emperor for life. 

**Christina Wodtke** (00:04:52):
Excellent. 

**Lenny** (00:04:54):
Okay. That'll be our goal. So, as maybe a first question, I want to give people kind of this confidence that OKRs can lead to great product, great success. What can you share, just to give people a sense of, "Here's how many companies who are having a great time with OKRs, here's the impact OKRs can have on your company if you roll it out or make it more optimal."

**Christina Wodtke** (00:05:15):
I've seen so many companies do extremely well with it, and I would say that not all companies will be successful, period. Companies are really successful with it are companies that... I think I can swear a little, they have their shit together.

**Lenny** (00:05:27):
Absolutely. 100%. 

**Christina Wodtke** (00:05:29):
And the first step is, get your shit together. They have strategy, they have empowered teams, they have psychological safety, and then the OKRs are that extra layer that supercharges them. So, I say OKRs are more of a vitamin, they're not a medicine. So, if you take OKRs and you're like, "Oh, this will fix everything that's wrong with you." No, that's not going to happen. It's just going to reveal everything that's wrong with your company. But if you've done the hard work of getting your company to be strong, it's amazing how well it works. It works really well with startups. It works really well with multidisciplinary product teams. I've seen it over and over. I don't really have permission to talk about all my clients, but I have one client that I'm just working with right now, and it's a purpose built company. So, in other words, they exist in order to make the lives of their customers better, healthier, wellness.

**Christina Wodtke** (00:06:20):
And so, they used OKRs to really create this amazing focus on, what does it mean to make everybody's life healthier? And one thing that came out of applying OKRs was this wonderful idea, they're bringing robots into their warehouses, not to replace their humans, they're keeping all the humans, but to reduce the amount of back problems their humans have. So, the humans are doing much more complex tasks, thinking about inventory and how to be more efficient. And the robots are doing the heavy lifting. 

**Christina Wodtke** (00:06:51):
They've been growing and growing like crazy. And the OKRs are this very simple way of allowing you to focus on what actually matters and making sure you don't forget in the chaos of everyday life. So, if you know what you're trying to do, then the OKRs just help that happen. It aligns the company. And I think they're a lot like dieting advice, in that they say, "Eat less and exercise more." Well, that's really simple. It's worked for me. I've lost 25 pounds doing eat less and exercise more. But wow, it's hard. It's really hard to do. And I think about OKRs that way. You have to just stay with it and be strong and committed, and that will help.

**Lenny** (00:07:36):
There's a number of things I want to follow up on in what you said. 

**Christina Wodtke** (00:07:39):
Sure. 

**Lenny** (00:07:39):
So, I'll start with, you talked about the benefits of OKR. If you had to just boil down, here's what OKRs can do for you as a company, as an organization, what would that be? What's just the main benefit of OKRs at your company?

**Christina Wodtke** (00:07:51):
The main benefit is that there's a lot of concrete action through a OKR that you don't always get from strategy. Strategy tends to be a little longer, a little more Muji Muji. And then when you get the OKR, you say, "This quarter is what we're actually going to be doing, and these are the numbers we're actually going to be pushing further." So, that's really good. It creates a cadence of progress, which is incredibly valuable. It creates alignment. There's no question what the single most important thing to do in the company is, assuming you're doing radical focus and you don't have 20 OKRs every quarter. Ugh, don't like to think about that. And last of all, the thing that I don't see a lot of people talking about that I think is really amazing, is because an OKR focuses you for one quarter and at the end of the quarter you grade your OKRs.

**Christina Wodtke** (00:08:40):
How well did we do? What got in our way? It creates this learning cycle. So, then you can take that information and say, "Next quarter, what should we try next?" And I think the time is the thing that a lot of leaders really struggle to think about. But if you've been really focusing on say, retention for one quarter, two quarters, and then you go over and say, "Okay, let's work on acquisition." You don't forget all the things you learned about retention. No, you're just building knowledge and building knowledge and building knowledge, which means your company will constantly get smarter and more effective.

**Lenny** (00:09:13):
I love this. So, just to summarize, the main benefits are focuses you, lines, creates a cadence and creates a learning cycle. And maybe a simple way to think about it is, it's like a plug-and-play product development process. You don't have to invent everything from scratch. There's this thing that exists. I know it's not the whole piece of it, but yeah, maybe... You're nodding and I'm curious, when I say that, what comes to mind?

**Christina Wodtke** (00:09:36):
Yeah, I guess you have to have a product development process, because obviously otherwise you're just running around chickens with your heads cut off, but it keeps you from making the same stupid mistake over and over and over again, which has been a goal in my life. My motto is, "Make new mistakes." So, by having this focus on really important things, not to spread yourself too thin, like the famous peanut butter memo from Yahoo, which I guess was long ago enough, not everybody remembers it. But companies have a tendency to try to do everything all at this exact moment. And so, everybody's working with 1% on this, 1% on that and 1% on the other. And instead you use the OKRs and say, "Okay, this is the big rock we're going to move. This is the big thing that's going to happen this quarter, and you can fiddle around with all the other stuff if you want, but this one has to move."

**Christina Wodtke** (00:10:27):
And then the next quarter, the next thing gets moved and so on. And it just accelerates the speed of your accomplishments so much. It's kind of mind-blowing. I've actually been running my life for the last eight, 10 years on OKRs as well because I'm ADHD and I'm all over the place. And so, looking at my OKRs every single Monday and saying, "Well, am I going to work on a book? Am I going to work on my teaching? Am I going to work... Where do I want to put that attention?" It changes me personally, just like it changes my clients.

**Lenny** (00:11:00):
What's an example of your personal care? You said writing a book maybe could be one?

**Christina Wodtke** (00:11:03):
Well, I wish, but no, it's actually been health. One of the great things about managing my OKRs for so long is I discovered this pattern, which is that anytime things get busy, I just stop taking care of myself completely. And that's really bad because if I'm healthy, I can be there for my kid, I can be there for my students, I can be there for my colleagues. So, this quarter's been about setting up habits of well-being and like I said, I've been really pleased at how it's been going.

**Lenny** (00:11:30):
Amazing. I haven't heard that before. What would you say is kind of the atomic unit of an OKR? So, people talk about, "We're doing OKRs, we're not doing OKRs". What's the line between we have goals and a plan, and we're actually doing OKRs as a concept?

**Christina Wodtke** (00:11:44):
Gosh, what is the atomic unit? That's a really lovely question. I would say, "What am I doing this week to get closer to our goals?" If you could answer that question, you could give up all the OKR stuff, but if you just asked the question, "What are we doing this week to get closer to our strategic goals, our longer term goals?" That is the very heart of it, because there's the tomorrow problem, like my kid will do his homework tomorrow, and tomorrow never comes. It's always tomorrow, tomorrow, tomorrow. So, what are we doing right now? And I find that it's really useful to tie it into temporal landmarks. 

**Christina Wodtke** (00:12:21):
By that I mean that there are things like birthdays or New Year's or Mondays or quarters that are already built into the world. And so, we piggyback onto them and we say, "Okay, it's Q1, boom, we're going to stop. We're going to take a breath, we're going to look at everything and we're going to say, 'What do we actually have to do?'" Raising your head above the noise is really vital. "And then this quarter, remember we have a mission over here and we have a vision and we have a strategy. Okay, this quarter's all about, what?" And you move towards that. 

**Christina Wodtke** (00:12:52):
I know there's a lot of talk about outcomes and I think that's absolutely right. It's really critical to think about outcomes because that gives you flexibility on how to attack the problem. But the biggest question is, why? Why do we get up in the morning? What are we trying to actually do? Are we making a difference at all? And if you can say, "This week I'm going to do this," and then at the end of the week you say, "Oh, that worked or that didn't work," and you can try something new or keep going. That's just invaluable.

**Lenny** (00:13:18):
That is really interesting that your answer wasn't like its outcome or some key results and 70% of success is goal, that there's something more fundamental, which is just being very clear on what you should be doing next week and we should be focusing on now. And that translates into what kind of the OKR process ends up being.

**Christina Wodtke** (00:13:34):
Oh, yeah. Can I tell you a little story?

**Lenny** (00:13:37):
Absolutely.

**Christina Wodtke** (00:13:37):
So, this is personal OKRs, but it works for everything else. It's always easier to talk about personal OKRs because I don't have to do an NDA with myself, so I apologize. But I've had this accountability group with these three women for at least five years, and every Monday we send our OKRs to each other, and I do it the way I do it in the book. Another woman, she had the getting things done approach where it was like, "How percentage did I make and what am I trying to do?" And exactly, super detailed. 

**Christina Wodtke** (00:14:06):
And then another woman was like, "Ah, I don't know. I guess I'm trying to think about... What am I trying to think about? Oh, maybe I should think about if I have to get out of product management or not." Well, now the woman who was very precise has kind of disappeared. I think it was just something that she couldn't keep up that level of diligence. While the woman who was hand-waving, she actually has gone from a product manager to a consultant to a life coach, and she's making so much money, and she is so damn happy, and she has a new house. And so, I really do think that the heart of everything is answering that question.

**Lenny** (00:14:44):
And what is that question?

**Christina Wodtke** (00:14:46):
What am I doing this week to get to the outcome I really want? Her outcome was to not worry about money and be joyful with what she was doing. And she got that just by every Monday saying, "What the fuck am I doing here? What am I trying to do again?" And it worked.

**Lenny** (00:15:03):
That is a really cool framework. So, the question you ask yourself every week is, "What am I doing today that's helping me get closer to my outcomes?" Is that the word to use outcome?

**Christina Wodtke** (00:15:12):
Yeah, yeah, exactly. And it is an outcome. In her case, it was not worrying about money, having a house, having joy in her work. I think a lot of us get caught up in, do I want to be a writer? Do I want to be this thing? When the reality is, we just want to be satisfied and happy. And with a business, it's the same thing. We get caught up in this or that little details, but you need to go back and say, "What was our mission?" I mean, think about it. How often do companies ever talk about their mission? It's like they set it, they forget it, it's super vague, it's useless. 

**Christina Wodtke** (00:15:42):
Instead, it's good to think, "Okay, when we started this company or when we changed this company or grew this company," or whatever you want to go to, there's always these various points in time. "Why? What did we think would work? And let's go back to that moment of meaning and reconnect with it and then make it real in the activities we take every week." And I like every week rather than every day. Because the reality is we still have to do progress reviews and we still have to do accounting and whatnot, but if we just push a little bit each week, over time amazing things happen.

**Lenny** (00:16:15):
So, I want to drill into some of these things, of just how mission, vision, roadmap and OKRs kind of fit together, just to be pretty tactical. So, as a PM say, or founder, what is the process you recommend for working through mission, vision, and then OKRs, and then roadmap?

**Christina Wodtke** (00:16:33):
I think it's really important to have a mission, and people get freaked out because they think the mission's forever. And so, they make them super vague so they can do anything. But instead, if you think about it, if the mission lasts for five years, what would you like to see happen in five years? And it might be, "We're going to bring amazing games that delight our users and we're proud to ship into the world." That could be a mission. And it's like, "Okay, I could do that over the next five years." And then, there'll be a point where you probably want to change again. So, you're bringing, what does it mean? What does it mean to be proud? What does it mean to delight people? Really talk about that and get into the nitty-gritty. And then out of that would come your strategy, which is this is going to be our year of exploration, if you have enough money for such a thing.

**Christina Wodtke** (00:17:18):
Or this is going to be our year of making our current games a little bit better. I'm in a very game mindset today because I was talking to a client. So, you get into that. Okay, now we have this sort of idea of what we're doing with our year. Now, let's talk about the quarter. And you can use OKRs for the year, but the quarter is where they have the most impact, I believe. Spotify talked about doing quarterly performance reviews because it's long enough to get something done and short enough to not forget what you did. And I think that sums it up perfectly for OKRs as well. So, once you know where you're trying to be, and once you know what you want to do with your year, you can say, "What are the things we want to see happen across these four quarters?"

**Christina Wodtke** (00:18:01):
I call it sort of a half-built strategy because too much strategy ties you down and too little strategy, you're too responsive to everything. So, you say, "Okay." Let's say you're building a new game. So, Q1 is about figuring out what it is and what's going to be interesting to users. And then Q2 is going to be about getting some early prototypes out and validating those concepts. And Q3 is about building extensive, and Q4 is about marketing and throwing it out, something like that. And you could venture them into your outcomes. A lot of people who are very venture driven don't understand outcomes, objectives, excuse me, objectives, outcomes, potato, potato.

**Lenny** (00:18:39):
And they sound horrid.

**Christina Wodtke** (00:18:39):
It's really something inspiring. Q1, we have a vision for this game that will drive us forward. I don't know, I'm making stuff up, which just means it's going to be imperfect. Although I do warn people not to get too caught up in wordsmithing. We can spend hours doing that. And then, you get to ask my favorite question, how do we know? I love, how do we know? That's how you get to outcomes. So, what does it mean to have a vision for a product we believe will be successful and meet our mission, whatnot? Well, what would it be? How are we going to figure this out? So, something about user testing, probably. Maybe we do a landing page, see how many people are excited by the concept. Maybe we do some technical builds to see if it's actually buildable. What are the sort of things that would tell us, yes, please go forward? We might be excited about VR. Well, how do we know that VR would be profitable for us? 

**Christina Wodtke** (00:19:35):
So, once we answer those three, how would we know, then we can know that by March we have the results we need. And we're always going to try to think about the best possible future, the whole moonshot thing, which I'm a fan of, but the reality is, the reason we do that estimating is so we get good at estimating. Everybody sucks at estimating when you first start, and a lot of people think it's like black magic or something you're born with. But no, it's a learned skill. You practice estimating, you get good at estimating, you get better and better and better. And being good at estimating is incredibly valuable as a business skill. So, there's your OKRs, right? And then for Q2, we don't know how Q1 is going to go, so we're just going to leave the objective there, but we're not going to get into the nitty-gritty OKRs. Key results cause a lot of arguing among the team, takes forever to track them down, just wait and see how Q1 goes. And that way you have enough play within your strategy to react to new information.

**Lenny** (00:20:32):
The question you talked about of, how do we know? That's to decide the objective or the key results?

**Christina Wodtke** (00:20:39):
Key results, yeah.

**Lenny** (00:20:40):
Okay, got it. You're saying objective. Okay, cool.

**Christina Wodtke** (00:20:42):
Objective. My bad. I didn't signal when I turned. No.

**Lenny** (00:20:49):
Oh, okay, cool. That makes sense.

**Christina Wodtke** (00:20:49):
Objective is that vision for the quarter. This is what we're we're driving towards in this quarter. And then the key results, you answered the question, how do we know we succeeded?

**Lenny** (00:20:58):
And so, what was the tip you gave of turning strategy into the objective? How do you translate from strategy to deciding your objective for the core?

**Christina Wodtke** (00:21:06):
Oh, that sits between mission and OKRs. So, strategy, I've been really shocked lately. I've discovered that lots of companies don't seem to have any strategy whatsoever, which just blows my mind. So, if you think about strategy as a strongly held hypothesis about a way to win in the market and fulfill our vision, then you can say, "Well, our mission is this, or vision..." I kind of use them interchangeably because I think they are kind of interchangeable, and I'm not going to get in semantics in the bitty bits, but the strategy is really important because it says, "We think we're fulfilling our mission of connecting people, by what?"

**Christina Wodtke** (00:21:55):
I think that there are a lot of good product strategy pieces out there, but businesses have a lot of questions to answer. Are we going to ship physical products? Are we going to ship digital products? Are we going to be a service? Are we going to do a subscription? Strategy answers those questions. They say, "We're going to have a game. It's going to be an Apple Arcade. We have a hypothesis that's actually going to help us. We're going to build in there and build our customer base there in order to get name recognition, which we can then use on other platforms." That's the sort of strategic stuff. And then we're like, "Oh great, you have a vision. What are we doing? What does that actually mean for us this year, this quarter, and then eventually this week?"

**Lenny** (00:22:39):
For the actual OKRs you end up with, is it as simple as just with the template of an OKR, is it just objective three-ish key results? Is there anything more to it that you recommend folks use? 

**Christina Wodtke** (00:22:51):
No. Simple things give you a lot more room to fiddle. And I feel like every time I see people make really complicated methodologies, they get way too caught up in the rules and they don't think about, what are we actually trying to do? So, simple is better.

**Lenny** (00:23:04):
And what's your rule of thumb for number of key results?

**Christina Wodtke** (00:23:06):
I like three. I think about it as triangulating. I always like something that's really hardcore numbers. I like something that's a little squishier, like a quality, make sure you don't forget about it. And I usually like something that involves a dollar sign, but it's really going to be specific to what objective you're trying to do. Launch a new product. Well, you probably want to make a certain amount of money, well you want a certain amount of reach, and then you want that delight thing. And then when you get into the delight thing, you can say, "Well, is it going to be Metacritic? Is it going to be a survey? Is it going to be NPS?" You know, could figure out what one makes the most sense for you.

**Lenny** (00:23:45):
That's an interesting topic. Is there anything you find there to measure customer happiness, satisfaction, delight? What have you seen work best for that sort of squishy stuff?

**Christina Wodtke** (00:23:53):
I know there's a big backlash against NPS. I think it's okay. It's really funny because you can be insanely successful with a game that people feel yucky to play, and you can be incredibly successful with a product people hate using. Zoom, for example. How many times have you heard Zoom get cussed out? So, the question is, why would I care about that if I'm making money? And I would say the answer is, would you like to keep making money? It's always about retention. 

**Lenny** (00:24:23):
Right.

**Christina Wodtke** (00:24:24):
So, anytime you can get strong retention signals, I think those are good signals to get. So, that comes out of qualitative research. There's nothing better. So, if you don't have a qualitative researcher on your team, I think you should get one. You need somebody who knows how to separate what people say and what they do, and what the truth is in that. And then use that to apply to your strategic decisions, so that happy users sell your product for you, right? Happy users stay with your product. Happy users are willing to type an email telling you when you're messing up. I mean, you want committed users. They're just so important.

**Lenny** (00:24:58):
One final question around the actual OKR document. What do you find are the most one or two common mistakes people make when writing out the objective or the key result in deciding on what to go with?

**Christina Wodtke** (00:25:09):
Objectives, people make them so fluffy that they don't have any meaning. They really should be a proper goal. We're doing this because we want to see this happen, it matters. We want to delight our customers. Sometimes people make them too fluffy and sometimes they make them too boring. It's like, "Oh, we're going to ship this thing." That doesn't inspire anybody. Your objectives should make you, when your alarm goes off and you wake up, you go, "Oh yeah, I'm changing the world today, or I'm doing something really cool." It shouldn't be like, snooze. So, I think an objective should be motivating but not ridiculous. 

**Christina Wodtke** (00:25:42):
And then the key results, it's always going to be tasks. I mean, people put tasks in there all the time, and it can be tricky. Sometimes it feels like a task, like you have to get past a product review, so it's going to have a binary. They either said yes or no. But when you think about it, it is an outcome because it's really hard to get a product review group to say okay to anything. So, making sure that you have real outcomes that let you move forward, I think that's the biggest mistake people make in OKRs.

**Lenny** (00:26:13):
Yeah. I know you shared a few examples of just that came top-of-mind, but just is there any examples you can think of just, here's a really good example of an outcome? And I think your results are a lot easier, just move this metric 10% or hit-

**Christina Wodtke** (00:26:25):
Let's try to keep it fairly concrete. You're a online magazine selling interior design ideas. So, what are you trying to do? You're trying to get strong leads out to your advertisers, and that's really important, and you're doing it because you believe that people deserve to have homes that are warm and wonderful. You have this mission, and you want to make money while you do it. So, your strategy is going to be about connecting human beings with the brands that will suit their lifestyle. Okay, that's great. And then we get to the nitty-gritty, well, what does that actually mean? Are we going to really work on recommendations passionately? Are we going to really create various markets and throw down advertising where we think these people are? That's when your strategy comes into play because you're making all these interesting choices. So, let's say we're going to double down on recommendations, which has a lot of presuppositions.

**Christina Wodtke** (00:27:23):
We have to get people to like, we have to understand their patterns of behavior, and that's when we can start to go to OKRs. We can say, "Okay, so we have this online magazine, let's really work to get as many people being members rather than browsers as possible, so that we can start understanding what they like." And that's what Q1 could be really about, is starting to collect profiles of people's passions, and that sounds kind of exciting. "Okay, great. We're going to do that. We're going to create a profile of people's passions. Awesome." So, how would we know we were successful? "Oh, gosh. Well, we probably need a bunch of people to do it, but do we really need everybody? Maybe 30% of our audience flips over, and maybe that's right, maybe that's wrong." If you don't know, you just set it and you'll know by the end of Q3, whether you were stupid or not, it's fine, move on.

**Christina Wodtke** (00:28:12):
Okay, that's great. Okay, how many things should people do what with? So, they bookmark, favorite, like... How about like? Okay, so maybe they're going to like a certain number of products each week. Let's go for weekly active users. So, they're going to like three things and present it. Okay, so now we've got a couple of numbers that are pretty good. How do we know they're actually kind of liking it? Maybe you decide to do some panels, and we're going to measure using a customer panel, bring them in, have them talk to us, and we're going to do that at the end of every two weeks to hear how it's working and understand more about it. 

**Christina Wodtke** (00:28:54):
Okay, now we have some OKRs. With key results, I always recommend spending 10 minutes brainstorming every single way you could possibly measure that outcome. Because with brainstorms, you always think of all the obvious stuff first and then you have no ideas and you're just sitting there with your post notes going, "How long is 10 minutes anyway?" And then you start getting the weird ideas. And often out of those weird ideas are really good insights. So, I recommend some pretty long brainstormings on the key results, but the objective is sort of a manifestation of the strategy at a one quarter level.

**Lenny** (00:29:26):
Amazing. That was an awesome example. You talked a bit earlier about how OKRs end up being... or sorry, key results end up being tasks for a lot of people. And this reminds me, we had the CPO of Figma on this podcast, and he told the story of how they moved away from OKRs at one point because they found themselves sitting in these meetings reviewing these large spreadsheets of hundreds of tasks- 

**Christina Wodtke** (00:29:49):
Oh, god. Yeah.

**Lenny** (00:29:50):
... that were basically just tasks for ICs that they're working on, and they kind of lost sight of why does any of this matter? What are you even trying to do as a company? So, they moved away from OKRs and then they came back to them actually later and fixing some of these issues. So, maybe just as a question, what do you think is a sign that your OKR process is busted and that you need to spend some time improving and rethinking the way it works?

**Christina Wodtke** (00:30:13):
I think if those meetings are boring, that's a great example. One of the other benefits, which I didn't bring up about OKRs is that they scale really well. One of the biggest problems founders struggle with is they don't scale very well, but if you can set a good OKR and get people to work on it, then you don't have to decide all those little IC tasks. You don't want to be drug down with that. You got a job. CEOs got to figure out what's coming up down the line, not fiddling over everybody's tasks. So, you set the OKRs and then you ask in the meeting, "What are the top three initiatives that you're doing towards them?" Or two or five, whatever. It's going to vary a little bit, but you want to keep it small. You only want to look at the most important stuff and just trust your people to take care of everything else.

**Christina Wodtke** (00:30:58):
And then you can say, "Well, why do you think that's important? What do you think that's going to do?" Or, "I've been seeing that for weeks. Are you going to try something else anytime soon?" It's all about those conversations about, is our current strategy, not just at the company level, but at each departmental level, are these strategies working? Are they moving us forward, towards our goals? And so, looking through OKRs, I tell people, "When you first start, it might take a half hour, but after that it should just take 10 minutes." It's like, "I think that's stupid. We should talk about that." Or, "No, it looks fine, looks essentially correct, let's move on. Anybody got anything?" And then you can get into whatever else you do, if it's a metrics review situation or if it's talking about a new deal, the rest of the agenda.

**Christina Wodtke** (00:31:43):
But that constant checking in is like touching a lucky stone in your pocket. It reminds you, "Oh yeah, there's this thing, there's this thing." And that rhythm... I'm a teacher, I'm really into learning theory. So, there's a really big concept which is about repetition and retrieval practice. So, retrieval practice means that I put a fact in your brain and I keep asking you to go back and get it again. Qualitative research is really useful for understanding the psychology of your users.

**Christina Wodtke** (00:32:15):
I'll say, "Well, how do we understand the psychology of users?" And you'd be like, "Oh, I heard this." Okay, I bring it up. Well, it's the same thing in these weekly meetings, you're practicing retrieving what your OKRs are, and after a while they're just in that long-term memory and you don't have to struggle to think about them and you've got them. And anytime you make a decision and you're in a big rush, you don't want to go through a bunch of paper to try to find what were our OKRs? You just go, "Boo, this is what we should do. I know what we're trying to do and I know how to make a decision about that."

**Lenny** (00:32:44):
So, what I'm hearing is, a lot of this comes back to, if the meeting is not interesting and boring, change the way you run the meeting. Don't go through everything. Maybe just pick the things that are most interesting and focus on that. You don't have to review every single key result.

**Christina Wodtke** (00:32:57):
Keep the meeting level at the right place. I'm sorry, I wandered off in a different direction. I get really nerdy around learning theory.

**Lenny** (00:33:03):
No, I love it. I love learning how to learn. Feel free to share more as things come up. Okay. So, I don't know. I'm trying to think. Figma, I imagine they probably thought they could change this meeting, but I think maybe there's a more deep-rooted issue. And this is kind of where my next question is going to go, is what do you think are just the root issues of OKRs going wrong? 

**Christina Wodtke** (00:33:24):
Oh, my god.

**Lenny** (00:33:25):
Maybe that's a symptom of the meeting, they're really boring, but yeah.

**Christina Wodtke** (00:33:27):
Well, the symptom, it's really wrong. Yeah, it means that you're in the weeds, man. You're fiddling with the little tiny bits. You got to let go of those. You have to trust your people. So, if we do the five why's, okay, why don't you trust your people? Is it you or are you hiring horribly? Okay, if you're hiring horribly, why are you hiring horribly? Is it because you can't find the right people? Is it because you're rushing through it? You have to keep chasing it down. OKRs are a great diagnostic tool because they tell you something's broken. So, if your OKRs are going sideways, something's broken deeper. There's also the problem with psychological safety. You need your teams to be able to say, "This isn't working. We're doing something else." Instead of just saying, "This isn't working, tell us how to fix it."

**Christina Wodtke** (00:34:13):
People are coming to you and saying, "How do we fix this problem?" Something's broken in the company. You're doing something wrong as a leader. You have to think about, if somebody doesn't know what to do and you're like, "Well, I have a strategy. I told you what my strategy is." And they don't know how to make decisions, it means something's wrong with the strategy or you aren't being clear, because the conversation always has two people. There's an old joke that I think about a lot, which is, if during the day you meet one asshole, he's probably an asshole. But if all day long you meet nobody but assholes, you might be the asshole. And I think that's very true. If your entire company's confused, you might be the asshole. You have to think about, how can I get more clear? If people are constantly bringing you little things, it's not because they're scared, it's because you're scary.

**Christina Wodtke** (00:35:01):
So, a lot of times your OKRs breaking are speaking to something else happening, and if your OKR process isn't working, then you have to step back and go, "Okay, how far deep do I have to go before I figure out what's wrong with my management team?" And it could be the CEO, but it could actually be some weird group dynamics, and you've got to focus on that. I really love Patrick Lencioni. Five Dysfunctions of a Team is his most famous book, and I would recommend that if you like the fable style book. But it's the same thing. You got to fix things at the top, you got to do your own work, and then everything else runs a little better.

**Lenny** (00:35:40):
**Christina Wodtke** (00:36:57):
I can repeat everything I said, but instead I'll just say speed. People read, measure what matters. They get their panties in a bunch, they get really excited. They're just going to do OKRs for everybody, but they didn't really read the whole thing. You kind of skimmed it and you don't really understand how it works, and so you just implement it. Or you ask your head of HR to implement it, and it gets implemented and everybody's really happy and then they're really sad and then they spit it out. And then you say, "Okay, OKRs don't work." I mean, that's what I see over and over again. Nobody calls me for advice when they are thinking about OKRs. They call me for advice when they've done it in sales, every damn time. 

**Christina Wodtke** (00:37:32):
I think it's... What is it, the illusion of knowledge? If I asked you right now, how does a bicycle work, or how does a pen work? You'd be like, "I know how that works." And if you tried to write it out, you couldn't. Well, I couldn't. How does a ballpoint pen work? Okay, there's a spring and there's some ink. I'm not sure. So, really thinking about, how would OKRs work throughout the company, is valuable. So, because you don't have time as a leader, what you should do is just give my book to your best team and say, "We're thinking about OKRs. Can you guys see if it works?" And then three months later, check in with them. "What did you figure out, guys?" Okay. 

**Christina Wodtke** (00:38:13):
Because the best team always wants to be better. I love piloting with the best team, but they're still very imbued in your culture, so they'll figure out where OKRs in your culture don't fit. They'll figure out where it's helpful and then they can give it back to you and you have a template, and then you can take it to two more teams, and then you can take it to two more teams. And maybe you adopt it with your management team, little bit by little bit. That's how I tell people to start with OKRs. Just figure out your best multidisciplinary team team and say, "You guys start and let us know."

**Lenny** (00:38:44):
This might be a good time to talk a little bit more about your book for folks that are actually planning to roll out OKRs or trying to fix their OKRs. Can you just talk about what it is, how to find it, what it's called, anything else.

**Christina Wodtke** (00:38:54):
Yeah, it's called Radical Focus. I could have called it Guide to OKRs, but I think what's really important is to learn how to focus on the most important things and make them happen. It is a business fable, as they call it, where I tell a story about two startup founders and their struggle to find focus and how OKRs help them. And then the second half, it's the second edition that's out now, it's gotten twice as big because I started working with big companies as well as startups and had to work through, what does it mean when you have a larger company and what struggles they follow? 

**Christina Wodtke** (00:39:27):
And so, I think the first part's nice because it's fun to read stories, but I think what's really good about is what you notice, which is when I talk you through this company trying to figure out what their OKRs were, everything became a lot more clear. And I think that's one of the powers of stories, is seeing an example. And then the rest of it is really like you could almost open it to any page and look at your problem, go, "Oh my problem's with strategy or my problem's with tasks versus outcomes." And you could flip around and figure out, what's the piece I need to solve?

**Lenny** (00:39:57):
And folks can find it on Amazon if they search for Radical Focus?

**Christina Wodtke** (00:39:59):
It's everywhere, baby. 

**Lenny** (00:40:01):
Okay, great. 

**Christina Wodtke** (00:40:01):
And it's been translated into eight languages, which is pretty cool.

**Lenny** (00:40:05):
Wow. Which one's your most favorite language it's been translated into?

**Christina Wodtke** (00:40:08):
Well, Chinese, because it sells like crazy because apparently some Chinese actress said she loved it and then it's been selling bigger there than anywhere else.

**Lenny** (00:40:17):
So, Chinese actresses using OKRs, what is going on?

**Christina Wodtke** (00:40:21):
Mind blown. Once again, life is always more surprising than anything you can imagine.

**Lenny** (00:40:25):
I have more questions I want to ask you about OKRs, but you were talking about storytelling and fables and things like that. So, you also wrote a book about, not that we're going to go through all your books, but you wrote a book about drawing and the power of drawing, and also you just believe in storytelling as a really powerful tool. So, I'd love to hear just your take on why storytelling is so powerful and why skilled drawing is so important for product leaders at the [inaudible 00:40:48].

**Christina Wodtke** (00:40:48):
I think there are some things that are fundamentally human that are built into our genes. Storytelling's one. If all of human history was a clock, we started writing things down at 11:00 PM, so most of human history has been an oral tradition where we told each other stories to help pass on knowledge. And so, don't get anywhere near the big kitty with the great big teeth because you will die, or don't eat those red berries because my grandfather threw up for three days and then croaked. But we tell them better than that. Longer stories tend to have more conflicts and they tend to be seen as having more information. So, if you use storytelling, you're talking to the most ancient part of the human brain and you will get attention, you'll get comprehension and you'll get retention. The teacher's Holy Trinity, right?. So, I love stories. They work well, they catch people's attention.

**Christina Wodtke** (00:41:38):
And one thing I read that kind of blew my mind was, they said that if you tell people a bunch of facts, they'll forget most of them, especially those that don't fit into their current mental model of how the world works. But if you tell them a story that's full of facts, they will remember it. And if you look at TED, everybody loves a TED Talk. They're mostly all just stories, and facts sprinkled inside those stories. So, I think stories are very powerful. I think images are very powerful. Words are very abstract. If I say the word chair, what pops into your brain? Was it a big easy chair? Was it a hard wooden chair? We use these words as if everybody knows what we're talking about, but people don't. 

**Christina Wodtke** (00:42:22):
So, in my time in industry, because I was at, what, Yahoo, LinkedIn, Zynga, MySpace, stuff like that, I just found if I got on the whiteboard and drew really badly, and I think it's almost important to draw badly, make some marks, make some squares. Somebody else will go, "No, no, no, it doesn't work that way. Give me this pen," and start doing it. And it gets you so fast to a shared vision of what's going on. I know designers spend all this time making wireframes and I'm like, that's the lamest use of time ever. Just get some whiteboards, go into the room with your engineers and start making some marks together and that just works better. 

**Christina Wodtke** (00:42:56):
And I found that for some reason in America, people seem to think that you have to be one of the chosen few and born a drawer. But it's like anything, it's like playing piano, you just got to practice a little bit. So, the book mostly just has some really simple things you can draw, and then it tells you how to use them in business. So, I wanted to make something that was even simpler than Back of the Napkin, which is an awesome book, but gets pretty intense, pretty quickly.

**Lenny** (00:43:22):
With the storytelling piece, I feel like most people are like, "Yes, I know storytelling is powerful." But they don't know how to do it. Is there one tip you could share? Just how to get a little bit better at storytelling or integrate storytelling into your work as a product leader or founder?

**Christina Wodtke** (00:43:37):
If you say one tip, you're really holding me down. I would say-

**Lenny** (00:43:41):
You could do two tips if that makes it easier.

**Christina Wodtke** (00:43:43):
... when you finish telling a story, if you're telling it to someone you can trust, say, "What's something I could have done to make the story better?" You're going to find out, do I just blather on forever, or do I not give enough details? I mean, if you're only going to do one thing, get feedback, is always the answer. The second tip would be structurally there's a beginning, middle, and end. Intrigue people with a hook, a mystery. That's the beginning, right? A mystery, a secret, a surprise. The middle is, you can tell them a little bit about it. That's where you get your message in. If you're trying to pitch something, sneak your product in, whatever. And the end is always going to be success and celebration because you're trying to get people excited about your story or remember this information. So, just a basic structure in your head really, can kind of make a big difference.

**Lenny** (00:44:29):
Yeah, I love that. That's such a actionable, straightforward tactic for getting better, just ask people, "How could this have been a better story?" Great idea. Your second piece made me think about the Minto Pyramid. Do you know much about, do you work with that at all? The Minto Pyramid principle?

**Christina Wodtke** (00:44:45):
I had a Minto binge for a little while, but I moved onto other stuff. I do.

**Lenny** (00:44:45):
I think it was a triangle. 

**Christina Wodtke** (00:44:45):
Yes, but I can't recount it to you. I do remember it.

**Lenny** (00:44:54):
I was just going to ask because it's kind of the reverse concept, which is, you start with the conclusion and then you kind of share how you got there.

**Christina Wodtke** (00:45:01):
I think that's a good one. I mean, if you think about what's the job of a hook, a hook just gets you excited. So, how do you get people excited? You can start with a conclusion. There's going to be success. Oh, tell me more. I want to be successful. It could be a mystery. Ooh, what's happening there? I want to be part of that. It could be a secret. Something happened and I'm not going to tell anybody else, but I'm going to tell you. There's so many ways to hook people in, but they're all doing the same job because you want people to actually listen to you and not pretend and nod. So, I think you can do it backwards as well. But I bet even when Barbara Minto did it, she probably opened with a success and ended with a success, I would bet good money, to remind people that there's a happy ending and the story's worth following.

**Lenny** (00:45:42):
That's a really interesting perspective because to me, there were opposites of build tension and you reveal the answer. The Minto approach is start with the answer. Here's what we're going to do and here's why, and here's all the work I did to get there. Your point is, that's also really interesting. You're like, "Oh wow. I don't know how you got to that."

**Christina Wodtke** (00:45:56):
There's so many ways to tell a story. Just don't bore your users.

**Lenny** (00:46:00):
Great advice. Okay, I want to come back to a couple more OKR questions. It could be less fun than the story maybe, but hopefully more useful. I want to just get your take on what is the cadence of a healthy OKR process? What are the ceremonies and meetings and emails that are involved? I know you have this kind of weekly status email practice. Do you recommend... How do you describe the system of an OKR process?

**Christina Wodtke** (00:46:23):
Oh my gosh, I'm glad you asked because I think the cadence is probably the single most valuable piece of it. So, every Monday, because Monday is a great temporal landmark, look at your week, and you go, "Okay, what am I going to do to move the ball forward?" And it could be an email to your boss, it could be an email to your accountability group, could be an email out to your team, could be standing there like standup. I mean, it's very easy. OKR rituals were built on agile rituals. So, there's a lot of connections there, which is great. 

**Christina Wodtke** (00:46:52):
So, you just, Mondays you commit and Fridays you celebrate. People do not value celebrations enough. I've had CEOs who said, "Well, it was the middle of the quarter, so we didn't start OKRs, but we did start Friday celebrations. And oh my God, things are already changing. Things are already getting better." The simple act of getting together and saying, "What was the most awesome thing that happened to you this week? What's the most awesome thing that happened in marketing? What's the most awesome thing that design did this week?" It makes people feel like they're part of something really special and it's super exciting. 

So, you have these [inaudible 00:47:26] bookends and I think if you only do that, you're probably in good shape. I think status emails, I hated them so profoundly for most of my life. I had this huge team at MySpace and my project manager would gather everybody's status emails and put them together into this giant status email that I had to send to my boss. And I was so busy, I just sent it forward figuring it was fine. And then I read it and there was this really bad thing in my status email that should not have happened.

**Christina Wodtke** (00:47:51):
I was like, "Fuck." And I waited to hear back from my boss, and nothing. Apparently he wasn't reading them either. So, I was like, "What's the point of the stupid thing?" And then when I was at Zynga, we were using OKRs and they were really short. They were like, "What's your confidence level on your key results? What did you do last week? And what are you doing next week?" And the last week, next week is great because it allows you to start noting down what stops you from getting shit done. And that, I got to say, there's so much learning in that. I tried to do this, but what? Did I get sick? Did somebody get mad at me? Did somebody not want to work with me? Do we not have this critical database? The whole, I tried to do this last week and I failed, learning goes through the roof.

**Christina Wodtke** (00:48:38):
And that rhythm of just having three P1s, you can't have more than three P1s. You can have as many P2s as you want and P3s if you really think you should, but you can scam it... scam it. You can skim it, right? Go through it really quickly. And we would all send them to emails. You could subscribe to email lists, which meant I could read the status emails of most of the company, and I would know what was going on and I could quickly see who should I go over and talk to, and who should I make a connection with? So, those emails were invaluable. I think a lot of my clients are doing it in Slack now instead. And that works really well, if you have this place where you're putting your status in and people will quickly go, skim, skim, skim, skim. "Oh, okay. I got to talk to that guy." So, it's hyper valuable.

**Lenny** (00:49:20):
If you assume others, the OKR doc, you're like, "Here's our outcomes for the quarter. Here's our three key results." You make that plan once a quarter. You have any recommendation how long to spend on planning your OKR?

**Christina Wodtke** (00:49:32):
My goal is always as little as possible. Time you're planning is not the time you're shipping, and the best is the enemy of the good. So, in an ideal world, you would grade your OKRs week at the end of the quarter, maybe second to the last week of the quarter, depending on it. If it takes you a whole week to set OKRs, which I hope it doesn't, but who knows. And then the very last week you set your OKRs for the next quarter and that's it. 

**Lenny** (00:49:58):
Cool. 

**Christina Wodtke** (00:49:59):
Boom. If you can do it at in a... usually you can do it in four days total, unless you have a very hierarchal, huge deep bench. And even then, I have something, I'm going to share this with you because I don't think many people talk about this. The approval process will kill you. I've seen it happen over and over again. I was working with one of my clients and we came up with this different kind of approval process that's working really well, is that basically instead of having your boss approve it, you write your OKRs, you get three... I'm a big fan of the rule of three, because I'm a storyteller, but you could do less or more, I guess, teams that work with you enough to know what you're up to, to look them over and they just look them over, 24 hour turnaround. 

**Christina Wodtke** (00:50:43):
They say, "This looks right, but I don't think this is possible." They give you that feedback and you're done. That's it. That's the entire approval process, and it's so fast and it works so well. And that means you might have to say no to somebody if they're asking you to do more than... if you had 10 teams asking you to look over their OKRs, you have to say no. You want to keep it down to a reasonable number, but if you do one a day, it could be done in a week.

**Lenny** (00:51:09):
I'm thinking about companies the size of Airbnb when I left, trying to do it that quickly. And it's hard to imagine, partly because there's top level strategy that has to align with individual team roadmaps and dependencies, and platform teams and things like that. So, I imagine it's hard to do as the company's scales. I like the drive to make it a week and be done.

**Christina Wodtke** (00:51:29):
Well, I mean, who really has to approve it and what does it cost you if you get it wrong? And so, if tech looked at it, if somebody from strategy looked at it, if somebody from sales looked at it, whatever, the right people looked at it, you're probably fine. And if you're not right, you'll figure it out over the quarter and do better next quarter. We have to let go or we will get mired down in all this crap.

**Lenny** (00:51:57):
I love that. I went off track, but just to kind of put a ribbon on the concept of OKRs, you have this document with your object, your outcomes, your key results, and then your recommendation is do a weekly email. And is the idea everyone on the team sends this weekly email or Slacks to the rest of the team?

**Christina Wodtke** (00:52:15):
To the rest of the company if you can.

**Lenny** (00:52:18):
Wow. Okay. [inaudible 00:52:19].

**Christina Wodtke** (00:52:19):
That's the thing, is Google, even as a huge company, everybody's OKRs and their weekly updates are on their intranet. You can look stuff up, so why not?

**Lenny** (00:52:28):
Got it. And we'll link to a template that you have on your blog post. And also I think in the book, I imagine you have this template of what it is, but essentially it's your confidence level of hitting your OKR, what you did last week, what you're going to do next week.

**Christina Wodtke** (00:52:40):
And then a few notes if you need to.

**Lenny** (00:52:42):
Does this replace stand-ups in your experience?

**Christina Wodtke** (00:52:45):
It could. I never try to tell engineering how to get their shit done, but if they felt like it was doing the same job, then they could combine them.

**Lenny** (00:52:56):
Cool. Okay, great. And is there anything else? Is this the whole OKR process, in your experience?

**Christina Wodtke** (00:53:01):
The only other thing I would bring up is thinking about the word grading. So, a lot of people think about trying to make something really numerical, like 0.08, I got 80% of the way there, but a lot of times they're qualitative. So, how do you think about that getting approved by the product committee? So, it doesn't matter. It really doesn't matter. Don't get fussy. Don't try to make it really precise. Just go ahead and say, "Ah, hand wave, hand wave, 80%." What matters is, why 80%? Really focus on the learning. So, we almost got there. Well, if we would've gotten there, if we got two more days, that's fine. We basically got there. We knew what we were doing. If we didn't, if we were really far away, what went wrong? 

**Christina Wodtke** (00:53:44):
It's all about the retrospectives. Make sure your grading is secondary to retrospective, is the biggest thing I would say, because that's what's going to be valuable. And you could spend so many hours trying to come up with some fake measurement system that never is quite accurate and just wastes everybody's time when you could just be faster. I'm just obsessed with speed. You may have noticed that.

**Lenny** (00:54:03):
I thought it was 70%, is that 80% is success? Is that the rule of thumb for OKRs?

**Christina Wodtke** (00:54:07):
It's about 70%. Some people do 80%, some people do 0.075, I don't know. My feeling is, a good goal is one that makes you feel somewhat uncomfortable but not doomed. You're like, "Woo, that's kind of good, that's going to be tricky. Okay, let's go for it." That's about where I like to land with a key result.

**Lenny** (00:54:29):
I had a newsletter post with Lane Shackleton from Coda, and he made this point that OKRs were created by Google, which is the most incredible business model in history. They just print money, and for them it's okay not to hit their goals, like 70% of goal is fine, it'll be fine, we're making so much money. And so, his perspective for most companies, it doesn't make sense to set the goal to be like 70% of this goal you set is a success. Do you have a perspective on that?

**Christina Wodtke** (00:54:57):
I think you'll never know what you're capable of unless you try to do something that you're not sure you can do.

**Lenny** (00:55:01):
I agree. I find setting more ambitious goals than you think you can immediately achieve actually really pushes you to achieve them.

**Christina Wodtke** (00:55:08):
And the literature agrees. There's a lot of literature that shows ambitious goals are actually quite motivating unless you feel you're doomed, at which point then they're demotivating.

**Lenny** (00:55:16):
I've seen that too. Okay, two more OKR questions. One is, I noted this from before so I'm just going to come back to it. There's a balance with key results of, as you've talked about, being very precise and metrics-driven and focused. And then there's, you talked a bit about sometimes it's okay for them to be a little fuzzy, like quality and delight, and those latter ones are harder to measure, it's hard to keep people accountable. Do you have any advice for just how to find that right balance of, this is what will keep you accountable, and this is how we drive the business forward, and this is how we know you're doing a good job, versus here's a general thing that we think is success and it's fine. Do your best.

**Christina Wodtke** (00:55:57):
Yeah. One of the most common arguments I have with my friends is I think everything can be measured to a certain degree. Not precisely necessarily, but you can get enough of a swag to be useful. So, by trying to measure things, you'll start learning how to measure things. So, you maybe try NPS and you're like, "Wow, this is not actually accurate, or weird, or not." There's a lot of stuff we don't know until we try them. And of course, my background is in lean and agile and design and they're all iterative. They're all about, let's try something and then learn something and then do something. Which is why I'm so fanatically iterative. So, I think that when you got these fuzzy things, you just got to start trying out ways to measure it and trust the team to be able to figure out whether it's working or not.

**Christina Wodtke** (00:56:46):
Revenue, it's easy. This is what we're making now, this is what we could be making. Or you're not making anything now, so you can look up some numbers from public companies or whatnot. That's easy. DAU, it's easy. Acquisition numbers, it's easy. But when it comes to will people stay, do people actually like this? That's harder, but it's not impossible. There's a lot of user researchers who have worked hard to figure out how to measure it.

**Christina Wodtke** (00:57:15):
So, you can either buy the obvious off-the-rack package like an NPS, or you can dig a little harder and figure out what would be meaningful to your company. And I think there's a desire not to do things that are hard and take a little bit longer, but that's where you're going to get the super value. That's how you become the next Netflix or Amazon or whatnot. So, you really got to say, "How will we know about our product and what are the approaches are out there and which one makes sense for us?"

**Lenny** (00:57:47):
Final OKR-related question. Say someone's listening to this and they're like, "Wow, this is awesome. I want to do this at our company, we have a focus problem, we have alignment problems, we need to be more clear about what we're working on." Other than buying your book and reading it and sharing with everyone, what would you recommend would be the first few steps to work along that journey to rolling out an OKR process at the company?

**Christina Wodtke** (00:58:09):
I hate to say this, but there are a lot of consultants that have popped out of nowhere and it's kind of terrifying because so many of them really, really suck and they're just like, "Oh, OKR sounds like SMART goals or whatever, I'll just use that." Or it's hot, and so I'm going to figure it out by reading some articles. And so, I would ask for references. I think that's a good one.

**Lenny** (00:58:33):
So, your advice is find someone to come in and help you figure out how to do this well and find the right person.

**Christina Wodtke** (00:58:40):
Yeah, I guess I think that finding someone to coach you is really high value, but I also think it would be okay if you just read a book or read a bunch of blog posts and start experimenting. It's not rocket science. You just listened to this podcast, listen to it again. Take lots of notes, Google around, see if you can learn a little more about some of the concepts that you didn't fully understand or you want to know more about. And then just run a tiny pilot and say, "Okay, what does this mean for us?" You don't even have to call them OKRs. You can just try, "We're going to do a outcome focus this quarter and let's see where it takes us." But just try it because that's where you learn stuff. And try it at a small, safe level where you don't think it's going to hurt too many things.

**Lenny** (00:59:25):
And you said to start with a high performing team. 

**Christina Wodtke** (00:59:27):
Oh, yes.

**Lenny** (00:59:28):
[inaudible 00:59:28] point.

**Christina Wodtke** (00:59:28):
Because they're smart, they're capable, and if anybody's going to figure out how to make it work, they will. If you try to fix a bad team with OKRs, you'll make everybody hate OKRs and make the bad team worse. So, just don't do that. It's not a medicine, but that high preferring team, they're going to be the ones who go, "Oh, well, okay, our stand-up's like this, so we should add this to standup. And then instead of emails, let's just have a brag channel on our..." I've seen people do the coolest stuff with OKRs, totally changing what I recommend, doing wonderful things with it, just because they're smart and they messed with it till it worked.

**Lenny** (01:00:03):
Awesome. Final question in topic. You teach product management at Stanford. What's maybe a surprising or contrarian opinion about how to learn to do product management, how to get into product management, how to do product management, from your experience teaching young PMs?

**Christina Wodtke** (01:00:22):
I taught it and a bunch of students who thought they were going to be product managers realized that they wanted to be interaction designers and not product managers at all. I think one of the things that might be off with a lot of the product management education and conferences is, it's good that they take a lot from UX and it is important to be people-centered, but the reality is the product manager serves the business. That's their role. Teresa Torres talks about the product trio, right? Trio.

**Lenny** (01:00:52):
Trio.

**Christina Wodtke** (01:00:53):
Trio. She's talking about business and user experience and technology. So, if product's over here messing with the user experience or products over there, messing with engineering, who's taking care of the business? And I think it's absolutely critical product managers, they say they're the mini CEO, but that just means they want to be in charge and nobody's in charge. It's all about working together as a team. So, they need to understand business models, they need to understand how to do a target market, and what is a target market, why is that target market the right one to go after, and how is it going to grow, and what are the trends that are going on that's going to change the business? 

**Christina Wodtke** (01:01:29):
Product managers need to serve the business and it's not a bad thing. If you have a company, it needs to survive and all money is, is oxygen, it lets the company keep going, unless people are being greedy assholes, which definitely happens. But it's okay to care about the health and well-being of the company's ability to make money and feed itself. And don't do anything unethical, but really focus on these questions. And if you don't know business models, if you can't talk about why you might want to do a subscription or if you want to just do one-off sales, if you don't understand why you know have all these in-app purchases in your mobile devices, go learn it. I'm really shocked at how many product managers are just smart people who care about users and just showed up and said, "Yes, I will be a product manager." So, no, business is a real thing. It has a long history of knowledge and understanding, and go do that.

**Lenny** (01:02:30):
What I'm hearing is, maybe product sense is overrated in your experience.

**Christina Wodtke** (01:02:34):
Ain't none of them yet old enough to have product sense. I mean, seriously. Product sense is intuition, intuition is compressed experience, compressed experience comes from having lots of experience. And if you're young and you don't have a lot of experience, the smartest thing you could do is learn. You've got to learn what models work and why they work, and just intuition is overvalued and under-exists.

**Lenny** (01:03:01):
Imagine that's kind of freeing to a lot of people listening, where they're like, "Man, I just don't know if I have product sense. How do I learn product?" All this. Yeah, don't worry about it is what you're saying. Any other advice for just people thinking about getting into product or trying to get into product other... Many can't get to Stanford and learn product from someone like you. What else would you suggest they do to try to help them get into a product management role? What other activities or areas they should spend time, in your experience?

**Christina Wodtke** (01:03:30):
I think I agree with my friend Ken Norton on this, in that you shouldn't probably start in product. Go be an engineer or be a designer, work, get to know businesses. And I got into product from, well, I was a developer and then I was a designer, and both of those gave me a lot of knowledge. But when I moved into product, it came out of my startup where I had to learn business, and I absolutely had to learn business or else I wasn't surviving. So, I would say work for a company that's small enough that you can poke into the corners and learn from other people, and learn and then do stuff. 

**Christina Wodtke** (01:04:11):
I don't know, it's funny because I'm at Stanford, which is all fancy with a degree and stuff and I'm like, "No, no, no, just read up, go hang out with people, get a job, figure it out." Because that's very much how I did it. And I think that if people want to get into product, I'd ask, "Why? Why do you want to be in product? Do you want to be in charge?" I learned that nobody's in charge. No matter what you do, you have to use your influence, you have to use your people skills. 

**Christina Wodtke** (01:04:34):
Are you willing to work on your interpersonal dynamics? Because if you can't fire someone, if you can't tell somebody their behavior is interfering with the ability to get things done, don't be a product manager. If you can't solve the fight between two of your coworkers, don't be a product manager. If you can't go out and talk to somebody in a Starbucks line and say, "Hey, we're working on this new thing, what do you think?" Don't be a product manager. You got to have hustle. You got to talk to people. You got to always have your eye on the bottom line.

Maybe you don't want to be a product manager. Maybe it's much more fun to leave work every day at 6:00 and be a designer and think about how all the systems work and how and where the error message is going to come in, and is blue the right color, all the combinations of that, that's fun. Or you really want to be an engineer and solve puzzles all day. Product manager is probably the worst job unless you love talking to everybody and connecting them and stepping into the mess.

**Lenny** (01:05:24):
I definitely agree. There's not enough talk about how painful and hard the PM role is and how thankless it often is.

**Christina Wodtke** (01:05:29):
And I love it, but I love everything. I fell in love with the web and I haven't stopped, even though it's now mostly on phones and stuff. It's an exciting space. But yeah, you got to step up and do the hard stuff.

**Lenny** (01:05:42):
That is an awesome way to end it. And with that, we've reached our very exciting lightning round where I just have six quick questions. I don't know if you know they are, so let's just go through them and see how it goes. Are you ready?

**Christina Wodtke** (01:05:53):
I love it.

**Lenny** (01:05:54):
What are two or three books that you recommend most to other people?

**Christina Wodtke** (01:05:59):
The Fearless Organization. I think that book on psychological safety is the bomb. It's so, so, so good. For fiction, I loved The Overstory. It's about trees, and it's mind-blowing and so good. I'm going to leave it at that. Less is better.

**Lenny** (01:06:17):
I tried reading The Overstory and it's very long, but beautiful.

**Christina Wodtke** (01:06:20):
It's a lot like Cloud Atlas. If you liked Cloud Atlas, you'll like The Overstory.

**Lenny** (01:06:24):
I think I watched that movie.

**Christina Wodtke** (01:06:25):
No, a terrible movie. Only read the book.

**Lenny** (01:06:28):
I agree. Speaking of movies, what's a favorite recent movie or TV show?

**Christina Wodtke** (01:06:33):
We just saw Wakanda Forever and it's a very different movie than Black Panther, and my kid and I spent quite a bit of time talking about it and what it meant and it was a lot deeper than I expected. And I'm very passionate about the Mayan people because I live in Belize part of the year, and I don't know, the Mayans are just the OGs of everything, invented zero, writing. They're just so amazing.

**Lenny** (01:06:56):
Love it. Next question, favorite interview question that you like to ask when you're interviewing people.

**Christina Wodtke** (01:07:01):
What questions should I have asked you? I've been using that one forever, whether I am interviewing somebody or being interviewed, because the person is an expert in themselves. And if you say, "What question should I have asked you?" A lot of times they'll be like, "Oof." They'll be knocked off-base and then they'll give you a really honest answer.

**Lenny** (01:07:20):
What are five SaaS products or tools that you just love and use constantly?

**Christina Wodtke** (01:07:24):
Oh, I hate all technology. That's what the problem is, if you've been a product manager and a designer, all you can see is the flaws. But I would say I like Zoom better than you might think. It's terrible, but it's better than everything else. Slack, when I saw it, I was like, "This is not going to get rid of email. This is just going to be another channel of nonsense." And that showed up. But I do use it. God knows, I use it. 

**Christina Wodtke** (01:07:48):
The Google Suites, I got to say the Google Suite is pretty amazing. Most people think that the students who go to Stanford are all rich, but 70% of them have huge amounts of financial aid. And so, I'm always looking for things that are free and won't cost too much for these students. So many of them are first generation, the first student who's gone in their family here. So, having the Google Suite and being able to have free slides, free docs, everything interconnected, Drive is sort of a gift. So, I've got to say I love those.

**Lenny** (01:08:20):
Cool. I didn't expect the question to go in that direction, but I love it. Two more questions. What's something relatively minor that you've seen a company you've worked with change in their product development process that's had a tremendous impact on their ability to execute and ship crates?

**Christina Wodtke** (01:08:35):
I will never forget when people stopped sitting with their disciplines and started sitting with their teams. I think that we in tech want everything to be tech and be remote and everything, blah, blah, blah. And there are definitely jobs that are wonderful remote, but if you're trying to innovate, there's nothing like getting the product trio to sit together, and preferably with walls. Walls are really underrated. If you can just give them a war room where they can put stuff on the wall, or I hate to say it, cubicles, I'd rather see offices, but if you can give people walls, it becomes part of your memory. And then you're not using your short-term memory to remember stuff. You're using it to think, and so the war room becomes a living memory so you can make connections. I mean, it's one of the hardest things I have to teach my students too, is that some things are just better done analog and that's okay.

**Lenny** (01:09:27):
Reminds me of a story I just heard from a friend where there was a team sitting next to a data science team and they were one table apart. They're right next to each other. And the data team just had a lot of concerns with what that team was building. They didn't believe in what they're doing and they're just like, "Why are we wasting these resources on this thing?" And the head of data science put one of the data people on the team and had them sit just one table over with the team and everything changed. They're just like, "Okay, let's do this. This is great. We're going to build some awesome products." 

**Christina Wodtke** (01:09:55):
We're human.

**Lenny** (01:09:56):
Just that one move.

**Christina Wodtke** (01:09:58):
We are human. We are social. Yeah, and I think moving people around every year or so, everybody hates it. Nobody wants to change desks, but do it to them anyway. It always makes things better.

**Lenny** (01:10:07):
Final question. What's a company that you think has a really strong and effective product culture? If you can name one, if not, that's okay too. 

**Christina Wodtke** (01:10:14):
Well, I think of all my clients, the best cultures all seem to be very small companies working in strange little corners of the world. They're not the big, sexy guys. Everybody's there because they want to make dog food or they want to make this kind of financial software, and they're amazing. I think we treat scale like it's a virtue when it's merely a tactic, and it might be a bad tactic as well. So yeah, I think there's something really sweet around 250 people working on something that everybody agrees is important.

**Lenny** (01:10:49):
Christina, I honor you as emperor for life of OKRs. 

**Christina Wodtke** (01:10:54):
Woo.

**Lenny** (01:10:54):
You've achieved it. I'm very proud of you. I think we've made a big dent in how people perceive OKRs and will utilize OKRs. 

**Christina Wodtke** (01:10:54):
I hope so.

**Lenny** (01:11:03):
Thank you so much for being here. Two final questions. Where can folks find you online if they want to learn more, reach out? And how can listeners be useful to you?

**Christina Wodtke** (01:11:10):
If they want to learn more, I've been blogging at eleganthack.com, like a hack writer since 2000. It's where I've dumped my thoughts for a long time, so it's always a good place if you want to go spelunking about anything. If you want to attempt to hire me, cwodtke.com is not a bad place to go. I say attempt because I teach, and so I don't have a lot of time. But you know what users could do? Users could slow down. I just wish everybody would take a deep breath and think about, "Okay, we're going to adopt this thing. Let's read up on it. Let's think about it. Oh, we're going to build this new product? Let's do a literature review, let's do a competitive analysis. Let's see what's been done. Let's learn from the past."

**Christina Wodtke** (01:11:55):
I think if you could slow down, you'll end up going a lot faster. So, I would encourage people, if you're in a panic and you're in a tizzy, and I know the economics bad and the world's on fire, but just take some deep breaths before you do anything and just ask yourself, "What's a good way to do it? What's a good way for me to move forward?" I think I would like to encourage that.

**Lenny** (01:12:16):
A beautiful way to end it, but I also want to make sure you plug your books. Just say the titles of your books and where people can find them, and then we'll [inaudible 01:12:24].

**Christina Wodtke** (01:12:23):
Radical Focus. Get the second edition. The Team That Managed Itself. And Pencil Me In. Those are my three books that are out there right now. You can get them pretty much anywhere I do believe, but definitely, I mean Amazon. Amazon rules us all, so they're definitely there.

**Lenny** (01:12:40):
Amazing. Christina, again, thank you for being here. We'll all go slow down right now.

**Christina Wodtke** (01:12:44):
Thank you so much for having me here, Lenny, and sharing your audience with me. It's been an honor.

**Lenny** (01:12:47):
Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [20/22] Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO)

**Josh Miller** (00:00:00):
We want people that show up to our company with some fire in their belly, something that they are out to do. And for each person it's a little bit different. For some people it may be UI Craft details. For other people, it may be achieving double the performance with a quarter of the engineering headcount. Everyone has something, but they show up with this heartfelt intensity. And I think even relative to everything else, I'm going to say, that's it. If you have a team that has heartfelt intensity and is there for a purpose and something to prove, you get it. You give them a very exciting, ambitious product and get out of their way and they will do remarkable work.

**Lenny** (00:00:36):
Welcome to Lenny's podcast, where I interview world-class product leaders and growth experts to learn from their hard one experiences building and growing today's most successful products. Today my guest is Josh Miller. Josh is the CEO and co-founder of a company called The Browser Company, which makes a product called Arc, which has quickly become my default web browser. I fell in love with this product as soon as I started using it and wanted to get a glimpse into how Josh and his team approached the craft of product. There's this cohort of companies like the Browser Company, [inaudible 00:01:09], a few others that are just laser focused on building the best possible user experience, almost above all else. And I wanted to spend some time exploring this trend with Josh. We cover how he thinks about prioritization, team building, storytelling, company values, metrics, shipping, building in public so much more.

**Speaker 3** (00:02:01):
**Josh Miller** (00:03:59):
Thank you so much for having me, Lenny.

**Lenny** (00:04:00):
It's absolutely my pleasure. You are the CEO and co-founder of The Browser Company, which builds a product called Arc. Can you just talk about what is The Browser Company? What is Arc? And then whatever you can share about just like the scale of Arc at this point. That'd be really interesting to hear.

**Josh Miller** (00:04:15):
Sure. I hope you don't mind me doing this. I'm curious, I hear that you may, may or may not use Arc? How would you describe Arc to somebody?

**Lenny** (00:04:25):
The simple explanation is it's just the best web browser that I've used. So, to me it's a browser. I know that you have a bigger vision than that, but that's the way I see it as a layperson who hasn't seen the full vision.

**Josh Miller** (00:04:38):
Awesome. I think we can go home now. That's great. That's awesome.

**Lenny** (00:04:39):
There we go.

**Josh Miller** (00:04:39):
No. To be totally honest with you and your listeners, we have a really hard time describing Arc, which is something I'm not proud of. But it is, objectively, a replacement for your default web browser. And people who try it seem to really love it, and most people seem to have a hard time using the internet in the old way. So, that may sound like I'm being coy, but we have work shopped many a one-liners and the words have escaped us so far. So, to be honest, it is on our to-do list to get sharper about that.

**Josh Miller** (00:05:15):
And then in terms of our scale, since we have a lot of product managers listening, I'll give you the PM answer to that question, which is, we really focus on one key metric as it relates to tracking our growth or how we are doing. We call it D5, D7. A lot of other companies call it L5, L7. But the human explanation for that is how many people turn to Arc at least five days a week? That is all we obsess over from a metrics perspective, because for us it captures retention, engagement, and growth in a single metric. You can't game it. Right? So from retention perspective, it's not just opening it accidentally once a week. You need to open a tab on a day in order to count as an active for a day.

**Josh Miller** (00:06:01):
But so it tracks retention. It tracks engagement because five days a week is no joke. There are very few apps or pieces of software you actively use five days a week. And then, obviously, it tracks growth, because of we track the count. So that is what we track. And then we also don't obsess over absolute numbers, because if we're successful, if you zoom out and out and out, any point in time will be inconsequential and small. So, what we really look is growth rate week over week. So, relative to last week, what is our growth rate? And for the past eight months or so, we've been growing over 10% every single week. So very, very thrilled with that. Do not think that will continue If anyone is listening. I would be shocked if we continue like that for another eight months. But, yeah. We obsess over how many humans use Arc five out of seven days a week. And we really want that number to grow as fast as possible every single week.

**Lenny** (00:06:54):
I love that we're already talking about metrics and retention. This is off to a good start.

**Josh Miller** (00:06:57):
You got to know your audience. Lenny.

**Lenny** (00:06:59):
We're going to talk about just how public you're about everything. But would you be for sharing your retention actual numbers? The D5 and D7 you just mentioned?

**Josh Miller** (00:07:07):
Yes. With the asterisk that I didn't prepare for that. So, Rebecca correct me on Twitter after this, if this is wrong. So once again, we don't look at DAU retention. We don't look at weekly active-user retention. We really just look at D5 D7 retention. Depending on the cohort, that's somewhere between low to mid-30s and low 40s. So really, really fantastic. Again, not going to continue. If there is anyone on this call that is going to check this in a year, it will be lower I'm sure. But so far, we're really thrilled with it.

**Josh Miller** (00:07:37):
And most importantly, in the same way, we don't look at absolute gross growth number, we don't look at retention in this moment. We look at, is it improving cohort by cohort? And so, what I think I am most proud of is that, if you go back a year, by all means our retention curve, we were really proud of it. And I think one of the best in our category of software. But, what I'm really proud of is, 12 months later we've been inching it up and up and up, despite getting further away from the earliest most passionate adopters. So, our retention curve's going up and up a little bit, which is-

**Lenny** (00:08:11):
All right. All right. If you haven't shared that, that'd be cool to share on Twitter someday. I'm a retained user.

**Josh Miller** (00:08:15):
I'm going to wait and you can share this clip. We'll share this clip.

**Lenny** (00:08:18):
Okay. Okay. I love it. We're just ready. We got the marketing strategy coming together. So, I told you this ahead of the chat, but the reason I wanted to have you on this podcast, even though, as folks may know, and as I've told you, I try to actually avoid founders and CEOs on this podcast to give other folks a platform who aren't often invited on podcasts. But the reason I wanted to have you on is, I just feel like Arc is a remarkable product. It blew me away the first time I used it. I don't know if you saw it, I tweeted as soon as I signed up? I had to share how awesome it was. I was like-

**Josh Miller** (00:08:47):
Of course I saw it. It made my day.

**Lenny** (00:08:48):
Okay. Okay, great. And, also as an outside observer, it just feels like you're building remarkable culture and team that's really unique. And, so I just want to selfishly learn from how you think about product and team building and all the things that go into it. So yeah.

**Josh Miller** (00:09:03):
Thanks for saying that, Lenny. What a cool way to kick off an interview.

**Lenny** (00:09:06):
Absolutely. First question I have along those lines is, you mentioned at some point that your product building philosophy is a reaction to the traditional Silicon Valley way of building product. I'm curious to hear what led you down that road? Why did you feel like you had to react to it? And then how would you just describe your product building philosophy at The Browser Company?

**Josh Miller** (00:09:27):
I'll share this caveat once and never again in this interview. But I want anyone listening to know, I'm someone who doesn't believe there is a single right way to do things. So, what I'm sharing today is truly just what we have found works for us in this moment for what we are doing. But, I remember when I was earlier in my career, I'd listen to podcasts like this and take it as dogma, because there are these people that had done it and I respected what they'd built. So, if any of this sounds like "better than thou," it's not intended to. This is just what we found works for us and what we care about. [inaudible 00:09:59].

**Josh Miller** (00:09:58):
Okay. So early in my career started a company also with Hursh, my current co-founder and CTO. We were fortunate enough to have that company acquired or acqui-hired by Facebook and spent a number of years working at Facebook. And remarkable organization, probably the best executing I've ever seen at that period of time. And, by the way, I'd never been a PM before, so I'm not complimenting myself, I was just learning for the first time. But what struck me at Facebook in call it 2014, and I've seen through to this day, is Silicon Valley, at least the most modern version of Silicon Valley, has this obsession with graphs, and has this obsession with numbers and metrics.

**Josh Miller** (00:10:36):
I mean, you saw me in the previous answer, I'm talking about D5, D7. What's a D5, D7? And, it is an incredibly effective way to achieve certain outcomes, to focus on numbers, because it's very quantitative, it's objective. You can see the graph go up or go down, or stay flat depending on what you want. But what we've found is that optimizing for metrics leaves a lot on the table and it misses a lot. And so, what we do at The Browser Company is we talk about optimizing feelings. How do we want to make someone feel on the other end of our software? Do we want to make them feel joy? Do we want to make them feel fast? Do we want to make them feel organized? Do we want to make them feel focused? What is it the feeling we are trying to evoke in whatever we're doing on a specific project, or a specific feature, or a specific piece of storytelling content?

**Josh Miller** (00:11:31):
And I can imagine what's going through the heads of your listeners right now, which is probably a number of things. But among others, that sounds really damn romantic. If they're like, "Okay. You optimizing for feelings." But if you allow me, I would posit that actually this modern way of optimizing for numbers and graphs, especially for what we all do every day, which is make things and put in the world, is what's fairly odd. Because, if you just to yourself daydream about, what are your favorite products or product companies and brands, while it may sound cliche for me, Nike. Nike was one of the first companies that at a very deep level resonate with me as a child. Disney? Disney, same thing. Apple? Before I was a professional in an industry, these were the brands and the products that they made that really made me love something that was ostensibly a commercial product I could buy.

**Josh Miller** (00:12:29):
What do you think Walt Disney was optimizing for when he was crafting Disneyland? What do you think Phil Knight was thinking about when he made that first version of the Nike running shoe? What do you think Steve Jobs was imagining and daydreaming about when thinking about the iPhone or the Macintosh? By all means, numbers are a fantastic way to be honest with yourself about whether or not you are achieving what you aim to do. But at the moment of creation, at the stage as product people, wondering what should we do, and why, and how? We think it's much more important for us to think about the human, the person at the other end, and how we really want to make them feel.

**Josh Miller** (00:13:10):
I think one tangible example of that is when I was at Facebook, I joined in the midst of Snapchat's ascendancy. And, there was a lot of feelings about how are we doing, should we be worried? And the way that we would have that conversation would be, how many times per week do people share on Facebook? Do they post something? We even had an acronym OBPS. It's like seared into my memory. What is OBPS? And how is it trending over time? Well, I think we should have been asking, and what we at least would ask at The Browser Company and our way of product development is, "Do we think people feel closer to their friends and family?" Or something of that nature?

I think that's what Snapchat got so right. They weren't obsessing about something like, "How many people put an image into the composer and hit the plus button. And the number of times per week means success." They were thinking about something much more human and essential. And so, that is what we've [inaudible 00:14:07] The Browser Company. Don't optimize for metrics, don't optimize for graphs. Use that as a way to keep you honest, and use it as a tool in your toolkit. But fundamentally, none of us are here for that. We're there to make people feel something.

**Lenny** (00:14:19):
As you pointed out, I think a lot of the people are listening are like, "I love that. I wish I could do that. I want to optimize for feelings, but then I got to drive the business forward. I got goals to hit. I want to keep people accountable." I'm curious how you operationalize this approach? How do you actually implement this idea? I imagine you still have goals and metrics and you guys, you talked about retention and things like that.

**Josh Miller** (00:14:42):
Yeah. Obviously it's difficult to do that in the abstract for another company, and it may not work for every company and every product. But, for example, one of the reasons we found this to be so effective so far is, if you pick the right feeling, it typically tracks pretty closely with the metric you care about. So, for example, we don't have a growth team and we have no semblance of growth projects. However, in many of the new features that we put out into the world, we want people to feel surprise or joy or an emotion like that. Guess what? When people feel that way, they go, "Oh, my God, what was that?" And they start telling their friends and family about it, and they start dropping a screenshot in Slack, et cetera. So, there's one example on the consumer side. I've never built traditional enterprise software selling to CIOs, et cetera. But I can imagine maybe someone in the IT department of a large enterprise wants to feel smart, or wants to feel ahead of the curve or wants to feel secure and ease at what they're doing.

**Josh Miller** (00:15:54):
I think sometimes we just forget that whoever your buyer is, or whatever your business objective, at the end of the day we're a bunch of people in a bunch of rooms at the other side of these screens. And just thinking about that person, it could be a buyer, it could be a customer. But I think the truth is the answer to the question Lenny is, when I was earlier in my career, I was searching for the answers or the way to do things, the right, the wrong, the binary. I think anyone that's been doing this or anything for a while learns that it's all nuanced. It's a spectrum. It depends. Sometimes it works, sometimes it doesn't.

**Josh Miller** (00:16:26):
But I think the true answer, Lenny, is just optimizing for metrics so purely is deeply flawed in my opinion. Optimizing for feelings so purely is flawed as well. And it depends on what you are doing, what the project is and a lot of other things. But I think the reason we come out so strongly is, I do think Silicon Valley has tended so far towards optimizing for graphs and metrics, that if we can reel it back in a little bit, at least as just one company, I think that will be good. But the truth is, it's both. We need to use all the tools we can get, but I think hopefully that's one way that people can operationalize.

**Lenny** (00:17:05):
I'm curious, just to poke out a little bit, how you actually implement that? So maybe as an example, you recently launched this Peek feature, where you mouse over, I think, a link and it opens up in a little browser that doesn't last. Do you put together a little spec of some sort of, "We're trying to create surprise, and maybe here's a metric we think about it." What's actual day-to-day operational approach to a new feature, in terms of feelings versus metrics?

**Josh Miller** (00:17:32):
Yeah. The truth is I don't think we've operationalized it as formally as we should one day. And we'll probably need to one day. The lucky thing is we are a very tight group of individuals that have now worked together for a long time. So not so formal as there's a PRD at the top of it, we list out the emotions. It's much more, with that project, get Ben in a room and whoever else is working on it and say, "All right. So here's what we're trying to do for people. Here's the problem we're trying to solve or the way we fit in their day. And in that moment people want to feel very light and airy."

So, for the Peek feature [inaudible 00:18:07] he's referencing the use cases. You're on Hacker News and you want to probably in pretty quick succession check out five to seven URLs. And you're not really sure which one you're going to spend time on, but you're going to open a bunch of stuff really quickly. And Peek allows you to effortlessly just peek into it, without leaving Hacker News and context switching to this whole new tab and going back and forth. So in that scenario, the conversation was how do we make it feel really airy and effortless to just whoop, pop it up, pop it back down, lightness, airiness, speed, agility. So again, it's not that we have a, "What is the number one feeling and the number two feeling?" It is much more conversational at this stage, but I am actually really excited. Hopefully we got the privilege one day to have such a large team that we have to figure out a way to do it. So, that's an example of how we think about it.

**Lenny** (00:18:57):
It's a good segue to a question I wanted to touch on. So, I asked Scott Belsky what I should ask you. He's a big fan of yours. I don't know if he's an investor? But he's just like, "I love Josh." And asked him, "What should I ask Josh?" And one of his questions was about, you guys ship very quickly. You're shipping meaningful features every Friday. And you also close the loop really well with customers when they come ask for something. You're like, "Hey, here. We did it." What is it that you do, and what can people learn from the way you all operate that allows you to ship quickly?

**Josh Miller** (00:19:26):
Well, first of all, thank you Scott, if you're listening. It's somewhat of an awkward question admittedly, because it's like someone complimenting you about your product. It's always impossible to really take and accept the compliment, because you see all the blemishes. Of course we see all these ways in which we don't ship fast enough and could be doing a better job listening and building with members. But, at risk of sounding a bit cliche, I really think we ship our values. So, we thought a lot about our values as a company. You can read about them online. And I think if you examine those values and then you look at your compliment or Scott's compliment, you can see [inaudible 00:20:05] one-to-one. So the first, and I really think the most important is, we hire people that show up with heartfelt intensity.

**Josh Miller** (00:20:11):
And, a lot of companies I think obsess over craft details. They'll be a value like, "We obsess over the details." What we say is, we want people that show up to our company with some fire in their belly, something that they are out to do. And for each person it's a little bit different. For some people it may be UI Craft details, for other people it may be achieving double the performance with a quarter of the engineering head count. Everyone has something, but they show up with this heartfelt intensity. And I think even relative to everything else, I'm going to say, that's it. If you have a team that has heartfelt intensity and is there for a purpose and something to prove, you give them a very exciting, ambitious prompt and get out of their way and they will do remarkable work. So, showing up with heartfelt intensity.

**Josh Miller** (00:20:54):
Our second value is assume you don't know. Assume you don't know. And the value "assume you don't know" is, even if you're a subject matter expert. We have someone in our company that literally built the first version of Chrome and ran it for 16 years. But he more than anyone embodies this beginner's mind of, "I have no idea how this should work or what will happen." And the follow up to that value is, "So we got to get going." It's like dropping in a new city. You just got to walk out the door of your Airbnb turn left and ... Maybe you'll turn right and then you'll hop on the subway, but you just got to get going and see what you find. And so, we have this attitude of, you're showing up with this heartfelt intensity. But you start by saying, "I've no idea what I'm doing. I have no idea what's going to happen." So we've just got to get going. And that biases in a default to action.

**Josh Miller** (00:21:44):
We have another value of, start by asking, "What could be?", which is pushing ourselves to be as aspirational, ambitious as possible. So the Peek feature that you mentioned, we just didn't want to solve the problem of context switching. We wanted to almost blur the line between native and web software, and make it feel like a sheet of paper. And really pushing ourselves to be as ambitious as we can be, which is the consequence of blowing back around and more deeply motivating the people working on it.

**Josh Miller** (00:22:13):
So, I mean, I could keep going. We have a value, "You're doing it for the crew when you got to swarm. When you got to swarm," and we have value of, "make them feel something." But I think what it all adds up to is, a team that has a lot of heart, has a lot of intrinsic motivation and a, "It's the first day of my career. I wonder what's going to happen?" attitude. And I think all of those things add up to a culture which is, "Let's get something out there. Let's see what happens."

**Lenny** (00:22:46):
How did you come up with these? What was the process to come up with company values? Because I know a lot of companies are like, "We should come up with these." How do you do that?

**Josh Miller** (00:22:54):
The secret is I hate corporate values. I've never resonated with them. And I'm fortunate, we're fortunate enough, to have a lot of really spectacular, experienced leaders in our corner. And I got hammered to the first year, two years on, "Josh, where are your values? How can your team operate without values?" And I always experienced them on the other end as almost corporate propaganda, these cliche fortune cookie, Panda Express-like, "You should care about the detail." It didn't resonate with me. And the thing that clicked was maybe a year and a half, two years into working, I just kept hearing the same things from the team. And I would do things like a year into someone joining, "How's it going? What's going well? What's not?" And I realized that there are some traits that define our team, extremely organically and naturally. No one told people what our values were.

**Josh Miller** (00:23:51):
Again, because I was this naive, ignorant 31-year-old being like, "Values are a corporate, late-stage capitalism creation," and just very, very hardheaded. And it was really special two years in, hearing from the team why they love The Browser Company, why they think we're doing ... Just the passion there. And then we challenged ourselves to what became a value. Well, if something about the five one-liners on the corporate webpage feels off, start by asking what could be in dream a little bit. And what I realized was, all of the statements people would say about what they loved about The Browser Company, what they thought defined the way we work, they reminded me of how I like to take road trips. I'm a big traveler. I'm a big fan of dropping in somewhere new and just exploring. And so we just had this "Aha!" Moment. Let's, instead of having a corporate landing page with five value titles and subtitles, let's write a manual for how to take a road trip.

**Josh Miller** (00:24:54):
So we wrote an essay called "Notes on Road Trips" that use this semi-biographical, but mostly fictional, story about a person and their father taking a road trip when they're a teenager, to tell the story of how we do things at The Browser Company. And share these values, but in a way that hopefully won't feel so propagandary and feel a little more, you're reading an essay. So I say that, again, not to say there's anything wrong with traditional values. I'm actually sure I'm going to get an earful for a lot of people that coach me and give me advice that I sounded too indignant on this podcast. But I'm pretty proud of that story because it was a great example of assuming you don't know. We were sure that corporate values were not for us. And then very organically without trying it turned out, "Wait! They run through this company in a pretty profound way. We should put some words around it, because it's happening whether or not we like it, or say it is or not."

**Lenny** (00:25:49):
That's awesome. I have the page here and it's quite beautiful. And, pulling to it in the show notes just very briefly and tactically, did you just sit down and start writing this thing and then people gave you feedback? How long did this process take? Just for folks that maybe you want to go down this road?

**Josh Miller** (00:26:03):
Yeah. Warning downside of this process that it takes a lot longer than we thought it would, because we put so much heart into it. So, what it started with was again, in my natural one-year, check-in type conversation, starting to notice these patterns. And then we actually very comprehensively were like, "Okay. Let's sit down and interview everyone at The Browser Company. But no survey. One by one, talking to people, asking questions. And then we pulled out those words. So, actually what's really cool about these values, if my memory serves me, I believe every single one, with the exception of maybe a word or two, was something that someone on our team said. So we interviewed the entire team and then these are meant to be a mirror. The putting it in road trip essay form? That took a long time. That that was a lot of ... Yeah. I don't recommend the way that we did that, but-

**Lenny** (00:27:02):
How long is long?

**Josh Miller** (00:27:03):
Probably three months.

**Lenny** (00:27:06):
Oh. That does not sound that long. Okay.

**Josh Miller** (00:27:07):
Yeah. Maybe this goes back to Scott's comment that maybe our bar to how quickly we should ship stuff including values is, it's like I don't know. But, yeah. It felt like a long time. And this was not just me. Just for anyone listening, this was not CEO in a corner writing a missive. This was a team effort. There's a woman Abby on our team that did so much work on this project. The words themselves came from our team. So, it has my name I think somewhere on that webpage, but by no means was this me writing this essay in a corner with the fireplace on, or anything like that.

**Lenny** (00:27:40):
Okay. Awesome. That was really helpful. As you also saw, I asked on Twitter what to ask you, and I got a ton of questions. People have a lot of questions for how y'all do stuff. The most common question turned out was from Ched Khan who had the most likes of all the questions that people asked you. And it was around hiring, that basically you've been able to convince some of the most amazing people in the world to join The Browser Company. Like you just mentioned, you hired the guy that built Chrome, basically, to work on Arc now. What is it that you do that convinces amazing people to join? Because everyone wants to learn from you and copy you, and do that themselves.

**Josh Miller** (00:28:15):
Thank you for that question and for all the legs. I will admit, this is also a fairly awkward one to ask. I actually just came from an interview with a candidate and they asked me a fairly similar question. And I said, "You know what? You should go ask the people that work here. It's not me. I don't know why they ultimately join." But what I will tell you is, the intentionality, which is another secret, sharing a lot of secrets. This one will probably get me in trouble. I don't care about web browsers. I've never cared about web browsers. I never wanted to build a web browser. If you had told me a decade ago that I'd be working on a desktop first web browser at 32, "I'd say what in my career went horribly wrong?" The origin story of this company was Hursch, who I met when I was 20. We started a company together. Lots of mistakes, a lot of successes, a lot of growing pains and figured out who we are. And a decade later we were still friends, we went to each other's weddings.

We'd worked in all these different industries and different-stage companies and we just realized, "You know what? There are a lot of ideas that get us really excited. There are a lot of shapes and sizes." But as we were nostalgic for looking back on the decade prior, it was groups of people and moments in time with those people that were our best memories. And so, what Hursch and I decided, long before the company started was, we want to build a company, but we want to build a company where we feel like we can hire whoever we want. And I don't mean whoever we want in terms of who would dare say no. But we want to work on something where the greatest minds in our industry and adjacent would want to work on that prompt in a hypothetical sense. And then build an organization, build a team where we can work in the way that, after a decade of trying on a bunch of hats and ways of doing things and metrics this and [inaudible 00:30:04], we could do what was right for us.

**Josh Miller** (00:30:06):
And so, where we went to with a new web browser, let alone a web browser as a new form of computing, which is our true aspiration, to build an internet here. You can look up the internet computer YouTube video on our Browser Company YouTube page. But our ambition's even higher than a web browser. The intention of that is, we just want to go hire our favorite people that we know and don't know and build a team that, we'll never get bored working with this crew, because of how incredible they are and how humble they are. And so, when you think about it like that, I as the CEO as notionally the head of product, I view our product as our team. And I know a lot of companies say that. I actually think they probably all mean it. I don't think anyone's being disingenuous, but we really meet it. It is the genesis of this company.

**Josh Miller** (00:30:55):
It is not a new web browser. It is, let's build the dream team, our dream team. And let's build a way of working that is really fun for us and really speaks to our values. And let's go find people that resonate with that. And that trickles down to everything we do, whether it's our policy about this or the way we do that. I'll give you one example. Our goal of interviews is to convince people not to join The Browser Company. If I have an interview with someone, I don't pitch them and say, "What do you want to ask me? Anything you want? I'll be super honest, most people shouldn't want to work here." So I think it all starts with us viewing our product as the company, as the team, not Arc itself. And then, I think being self-aware, that that's how I think that's how we think.

**Josh Miller** (00:31:43):
But again, flying back things that I've heard, we have been fortunate. We've hired a lot of really remarkable people, especially on paper and especially off. I mean, all around. I'll just give a couple examples to share one thing that I've heard. A few recent hires, we hired someone named Darren who, as I mentioned, he co-created the first prototype of Chrome and then ran it for 16 years. I think hundreds if not thousands of people reported to him. He joined the Browser Company as an IC. We just hired a woman named Tara. She was on the original Paper by 53 team, one of my most inspiring products at the beginning of my career. Most recently she was actually, I believe, Senior SVP of product at Vimeo and a senior director of engineering. She joined our engineering team as an IC. We just hired someone named Peter Vidani. When I was 20 building consumer social software, he was the coolest, most impressive person. He was the first designer at Tumblr. Ran the design team at Tumblr for seven years and the most recently was SVP of design at Slack. Joined the team as an IC designer.

**Josh Miller** (00:32:48):
And though that sounds like I'm bragging, the thing that was really interesting and perplexing to us was, these are people that have made a lot of money, that have had really fancy titles, that have worked on transformative projects. Why are they joining this team? And I think something that people show up to The Browser Company with is, in addition to heartfelt intensity, this aspiration that their work at The Browser Company will come to define their careers. And that's coming from people that have done really remarkable things, by all accounts. And I think more than anything, we've realized that, in order for people like that to join and to show up with that, there are a number of things you have to promise and provide them, that make folks like that gravitate with the intention of doing their work of their career, ranging from an incredible and ambitious aspiration, really empowerment to act on the prompts that they're given on behalf of the team in the way that they see fit, and truly trusting and empowering them.

A very kind culture. I think if you've been doing this for a decade plus, your intolerance for bullshit is very, very low. And so, by no means do I think we're perfect. I don't think everyone shows up The Browser Company saying, "If I'm not on the equivalent of the early iPhone team, I'm going to be bummed." But I think generally speaking, Hursh and I, and everyone that was on the early team showed up with this aspiration of making The Browser Company the product. And I think that's carried forward to this tumbleweed of people saying, "[inaudible 00:34:23]. That's where I'm going to finally do the equivalent of building the iPhone." And we all know we probably won't, but there is that, "I want to give it one more shot. I want to go for it." And that just tumbleweeds, I think, at some point.

**Lenny** (00:34:37):
That tumbleweed is, I think a big part of it is, once you get amazing people, more amazing people want to join. So I think that's very much helpful. Something else this resonates a lot with is, just the mission of a company is such a powerful tool for pulling people in, the best people. I've seen that a lot with founders. If they have a meaningful mission, it's so much easier to hire, versus not. And clearly you're really good at sharing that vision and mission. And then you also have a really interesting mission and vision. I think there's also, you're just a charismatic founder and that helps a lot too. And you're a great storyteller.

**Josh Miller** (00:35:08):
Well, the other thing I want to add Lenny is, again putting myself in the listener, I imagine a lot of what I just said probably sounded a little bit ... Could come off, if you don't know me and you don't, as a little bombastic or a little again romantic. Very tactically, I'll give you something that was just who we are, but I think has helped contribute to this tumbleweed. From the very first person we hired, we celebrated them publicly. The fact that they joined. And in a very heartfelt way, telling you about them as a person and what they did. Long before we had anyone that anyone would've heard of before working at The Browser Company, just because it was earnest, we were really proud. Again, if you think of our original mandate as building the companies, the product, when our first designer joins, we want to tell everyone about it. That's a product launch. That is the product launch.

**Josh Miller** (00:35:57):
And then, whenever we ship something, we go out of our way to celebrate the people that worked on it publicly. I think there's a CEO-hero worship sometimes in Silicon Valley. I do very little at the company. Or sorry. I do very little as it relates to the thing people fall in love with Arc. I do a lot for The Browser Company, but I don't make Arc. I didn't make Peek. And again, that's just who we are, which is, "Alexandre. She killed me! Look at how cool this is!" because it's earnest and it's honest to who we are. And then I think it creates this reinforcing cycle of you're someone that's done something incredible, which is, "I'm going to be celebrated. They truly want me here. I'm going to be recognized for the work that I do.

**Josh Miller** (00:36:39):
It's not going to just accrue to this like CEO figurehead who everyone thinks is some genius visionary. And so again, by no means are we perfect. By no means do I think we get it right all the time. But, because it's such an authentic expression of who we are and what we were trying to do, I think we do little micro implementations like that, that ladder up to that principle I got so excited about but are as simple as someone tweets about some animation. They're like, "Woo! This was fun." Tag Sherry. Sherry made that, Sherry's incredible. And you don't see that that much in Silicon Valley. You see corporate blog posts and the CEOs more than anyone else. That's probably why you don't have CEOs on the podcast, because you don't want ... You know this Lenny. That is why that's your policy. You don't want to hear from the CEOs. They're not the ones building the product. You want to hear from the people actually doing it. That's why I love this podcast.

**Lenny** (00:37:26):
That's right. That's right. Thank you. I'd say just hearing everything you're saying, The Browser Company sounds like an incredible place to work. I could see why people want to go work. It's pretty simple. You touched on being public and sharing everything that's going on. And that's another area I wanted to spend a little time on. You guys are very transparent about what's going on and inside the company. You bring cameras into the board meetings. I watched a half-hour meeting you had with your head of design talking about a project that's behind scheduling. You're trying to figure out how do we get this out the door. You just share actual things you all are doing within the company, publicly. And I'm curious just, why did you start doing that? What have you seen as a good or bad that has come from that? Is there anything you've shared that maybe you regret like "Oh, maybe we shouldn't have put that out there." What's been your experience with that?

**Josh Miller** (00:38:17):
Why don't I start with the regret. It's not yet a regret, but the thing that I wonder ... Because this is very much ... I may have hopefully spoken with a lot of earnest passion to some of the questions before. This is one that I would really characterize as a prototype. We really have a prototype-driven culture. And this is one that I'd put high on the list of, "Maybe we'll regret this later." And specifically what I hope is that, I'm uncomfortable putting myself too central in our story. But, naturally, when you're doing storytelling publicly, there's a gravitational pull for the CEO and the founders to be at the center of that. And so, sometimes even this morning, we had our best-performing YouTube video ever. The first one that really broke out of people that already follow us. And it's a reaction video in classic YouTube form to MKBHD talking about our product for the first time.

**Josh Miller** (00:39:13):
And I honestly watched it right before this again, and I was like, "What the fuck am I doing? What are we doing? Why am I trying to become a YouTuber?" So, to be totally honest, I don't regret anything yet. But I wonder if we could take this too far? So if anyone's listening, if you see us starting to take this too far, especially as it relates to me, we want to hear about it, because that's keeping me up. But I do think the intentions are pure and earnest, which are ... And another thing that defines people that have joined The Browser Company, in addition to wanting to do the work that defines their careers, is I would characterize it as a little bit of hopelessness, maybe feeling jaded, questioning this industry that they've worked on or products that they've worked on and wanting to rediscover. But, at the end of the day, we are a group of idealists, of optimists, wanting to rediscover what we fell in love with when we were kids, whether it's the part of our craft or the potential of technology, the internet and software.

**Josh Miller** (00:40:19):
And, as part of that, I would view Arc and the Browser Company as an experiment in we can do it. Better is possible. And as we were thinking about better as possible, rediscovering what we love and believe in deep down and trying to express it in the world, one of it related to trust. I remember when I was a teenager using the internet for the first time and early on to college, just the hopefulness of what was possible, and the belief that these people building these tools, they were like heroes to me. Not just the leaders, but the teams, the companies, the brands. And somewhere along the way, I'm not blaming a single company, I'm not even saying that anyone did anything wrong, but culturally ... I was a sociology major. Culturally, we have lost trust in tech companies and in tech brands.

**Josh Miller** (00:41:10):
And so, building in public showing you our meetings, uncomfortably so, is an act in, "If we were them, why should they trust us? Why should anyone trust us?" We have your most sensitive personal data. We have your most sensitive professional data. Why should you trust us if we've had our trust broken again and again? And I think our hypothesis in this prototype, in this experiment is, we can have the best privacy policy in the world, but at the end of the day, again, it's just people behind the screen. And so, even if I think about ... I haven't done interviews like this, because I worry that if you don't know me, I come off the wrong way.

A lot of people tend to. I've noticed a lot of friends in my life that I know them behind the scenes, but the way that people perceive them publicly here don't know them. They interpret it the other way, because there's not that trust. And so our bet is that if you get to know us, Nash, Dina, me Hursch, and you really feel like you get to know us as person and all of our imperfections, we're average looking, we're average to all that stuff. Then when you see that we're asking for a permission, you might trust it is because we want to make you feel a certain way that's better. And if not ... I'll say someone tweeted something yesterday, who apparently we didn't earn the trust yet and they haven't gone to know us. And their interpretation of what we were doing was the worst possible interpretation you could [inaudible 00:42:40]. And, at first honestly, I felt a bit of anger, like, "Who was this person on a Thursday just saying we're doing X and Y?" And then I realized, "You know what? I'd have the same feeling because of the experiences I've had with technology in the past five to 10 years."

**Josh Miller** (00:42:53):
And so, the intention with these the building and public experiments are radical trust building. Not radical transparency, we can't share everything, but radical trust building. You get to know us as humans and I worry that we'll regret that, and that it could potentially turn into, "Oh, they're trying to be internet celebrities that they're so important, they should share everything because ... Thank you, them, for gracing us with their opinions." It's not the intention and it feels worth taking that risk. But that's the intentionality behind it.

**Lenny** (00:43:24):
That is a really interesting insight. It makes a lot of sense for a browser to find that so important, to build that trust.

**Josh Miller** (00:43:31):
I haven't done podcast interviews, I haven't done this. I really like you. I really like the feeling of your conversations, the intentions behind them, the warmth, even your intro music is a friendly jig. So, I mean, it's a great example, where I think it's one of the most wonderful things about the podcasting medium is I've had you in my ear for a year and the people on your show and you feel a sense of trust in you and your intentions here. And your intentions both in this interview, in terms of what you're trying to do for listeners. To some extent your show, and the warmth that you bring to it and the perception I have as a human being ... We've never met. We've maybe DM'd briefly, maybe five messages exchanged. But I feel like I know you and that makes me trust you. And so, in many ways this podcast, at a meta level's an inspiration for it.

**Lenny** (00:44:23):
I feel the same way in reverse. You made this point about being worried about being two front and center for your company. I have the same exact feeling. Even though my newsletter's called "Lenny's Newsletter," I only named it that because that was the default recommendation when I was signing up for Substack. I didn't want to be this, "I know it all. Come to me. Welcome to my know-it-all place." I really dislike that. And that's why I created this community that lives along the side, where people can help each other, because I'm not going to have all answers. And so, I've had to lead into that. "All right, people." They want a person to help them understand what's going on, learn about ... And in your videos you do a great job highlighting other people. I was watching your board meeting video and it's like, "Here's all team members coming along. Here they come. How are you doing?" So, anyway. All that to say, you're doing a great job finding the balance.

**Josh Miller** (00:45:14):
Oh, thank you. You as well.

**Lenny** (00:45:15):
I appreciate it. You talked about storytelling, and you mentioned that you have a whole bunch of odd teams at The Browser Company. One of them is a storytelling team. And that actually explains, I think, how you're so good at making these really amazing videos, because making great videos is hard. Can you just talk about some of these odd teams that you have, that probably other companies don't?

**Josh Miller** (00:45:34):
**Josh Miller** (00:52:12):
Yeah. We've increasingly hiring people that at other companies may have a PM title. I'd say we have two to three right now, that could have a PM title at another company. I don't think we will have a pm organization, or a PM role, because again, we believe depending on ... If you unpack the verbs that a PM does, I think those are verbs that anyone that we hire could do. And it really depends on what is the project? And what are we trying to do? I think the thing that will be unwavering is we like to hire mutts. And I haven't yet figured out a term that comes off as more endearing, because it's meant to be very endearing, but ... For example, there's a woman in a company named Rebecca.

**Josh Miller** (00:52:58):
Rebecca was a data scientist we use at Cora. She got her PhD in MIT in I think behavioral psychology or something. I'm probably going to misquote that. But, got some crazy degree at MIT, and then was a software engineer at Stripe. And I'm talking about Rebecca through her resume. There's so much about Rebecca. She plays effectively a PM role right now. She is effectively PMing our effectively our multi-player team. But what was so awesome about meeting Rebecca is her and other people at this company have the mindset of, "I make things, and I will do what I need to do to make what I want to make. Whenever that verb is, whenever that discipline is." And that requires people that are multidisciplinary in practice and multidisciplinary in approach to their work. It's not that we don't hire PMs, but we want to hire people who have a multidisciplinary approach and view things as, "I like to make things. Tell me how I contribute to making it." And sometimes they may play the verbs of a PM and sometimes it may be something else.

**Lenny** (00:54:07):
This can be a really interesting story to follow. I've seen this journey a few times at different companies. What I find is a lot of times people that are good at other things like engineering or design, for a while, they're like, "Yep. We don't need PMs. I'll do the PM job." And then eventually they're like, "This sucks. I hate doing this stuff. I want to design. Leave me alone. I don't want to sit on a [inaudible 00:54:29] all day. I don't want to be in meetings." So eventually, it turns out, they're like, "Okay. Let's find someone to do this thing that loves it." And so that's one thing that happens.

**Lenny** (00:54:36):
The other thing I find is, I'm sure you've seen this, a lot of people are wary of PMs. They come in and they're like, "Here's what we're doing," and they're just adults process complexity. What I find is those are just bad PMs. If you have an awesome PM, everything just gets better. Everyone's happier, things move faster. So I think companies often get to that stage. And then also there's just career development stuff, eventually as you scale. It's like "What happened to my career path," and they're like, "All right. Well, we got to go on one road or another." It's hard to stay in this hybrid role. But I super respect the first principal's approach of let's just-

**Josh Miller** (00:55:08):
And, for what's worth, Lenny. I think you're almost, definitely right. And I think it will almost definitely happen with us. And again, this goes back to the "assume you don't know." The "assume you don't know," is try a prototype and then assume it's not going to work. So, even in my own experience, I remember getting to know Evan from Snapchat just enough to know how he talked about PMs at Snap. And it was, "We're never going to hire PMs at Snap. Everyone's a designer." And, I have no relationship with him anymore, but you can look, there are a lot of PMs at Snapchat.

**Josh Miller** (00:55:37):
So I know from my own experience with people that I respect from a product perspective that were indignant, they would never hire PMs, their organizations now have PMs. And that's probably for a really good reason. I would tell say also on our team, if any of our designers are listening, they'll tell you these, whatever you want to call it, "These verbs are taking up a lot of my time, and I do not have as much time to think and dream and design and do user research." And so, we're already feeling it breaking into our company.

**Josh Miller** (00:56:04):
I think the intentionality, whatever comes next, whatever it is, is leaders of the project should be picked for the projects, not because they're in a certain org at our company. And, if we ever hire people to do the PM role, we want them to think of themselves as people who make things and have lots of different disciplines and tools in their toolkit, not just the PM discipline. And, of course, even that could be wrong, and maybe in a year we cave. I got it totally wrong. We got it totally wrong. So, we'll see. But I would also, that that of all the things I shared on this podcast so far, this is probably the one I'll come crawling back to your podcast in a couple years, being, "Lenny, you were right. It all blew up!"

**Lenny** (00:56:47):
But it's a fun experiment and Snap is a good example. Stripes another, where they waited a long time to hire their first PMs. And I think it's because their designers or engineers were just incredibly good at that element. And it was also very design-forward or very edge-forward, so they didn't need as much PM skill initially.

**Josh Miller** (00:57:03):
If I had to predict, I would predict that if we found that we were missing this discipline as a team, I think we would evolve Rebecca's team, which is technically the data team, and do something closer to a technical PM or data plus [inaudible 00:57:19] Again, it's all live, but the thought has even crossed our minds recently, that we may be wrong, and what org might we create if we need folks that have more of a background of [inaudible 00:57:29] like this.

**Lenny** (00:57:30):
I'm excited for the video of this discussion that might happen. It's also interesting, your PM that you mentioned, Rebecca is very data oriented. And then, the initial discussion we had around focus on feelings and that sort of thing. So, that's cool that you have this really interesting balance of people that are very data focused and then this, "Okay. But let's not obsess with that. What are the feelings we're trying to create?"

**Josh Miller** (00:57:50):
Yeah. Because again, the point of optimizing for feelings is not hire people who make feelings. It's like Rebecca's title is Data Lead. She runs our data team. But, Rebecca's one of the most humanistic people I know. You meet her and you feel the warmth that you feel when you talk to you, and you ask her what she does outside of work. And so, it's not that data doesn't have a role. Actually I'd say, for better or worse, data is part of our practice. It's more about what's that top-level intentionality? What are we trying to do here? But, yeah. We have a lot of people that, data is either a noun they've had in their resume or it's been a part of their practice a lot in the past.

**Lenny** (00:58:29):
Awesome. One very tactical question with the storytelling team makes me think about Airbnb's video team. A lot of people are joking internally for years and years that the videos Airbnb put out in the early days accounts for half their market cap, because they're so good. And you're just like, "Oh, my God, I want to go on an Airbnb." They just make you feel so much and they're soul made. So, what is the makeup of your storytelling team? Because I imagine some companies maybe listening, like maybe we should do something like this on our team.

**Josh Miller** (00:58:57):
We have a three-person storytelling team. It's run by a woman named Nash. There is a gentleman named Ellis, who is a ... Background, started as a reporter at The Verge. Maybe there was a publication before that. But I met him when he was a reporter at The Verge covering social media. And then he ran marketing strategy for Snapchat for seven years. And then we have a person named Josh Lee, who I actually met as an intern. He was an intern at Facebook as a designer, that an intern for me at the White House when I worked at the White House, and then decided that he was over product design and over design, and totally just jumped and be like, "I'm going to be a filmmaker," and has been making really fascinating indie films for a few years now. And he's our video editor on the team.

And it's so interesting. Nash's background, she had a brief stint at NBC. But again, you get to know her and she writes poems after hours and her dream is to write a fictional book. I mean, anyone that knows Nash, especially [inaudible 01:00:00] is just a force. A force. And the three of them, what's so interesting about them, which also relates to our design team ... One of the things I also found at Facebook is there was a tendency toward homogeneity. As you know, there's a stereotype of a Facebook PM for example, or a Google PM, the contrast between them and the way they work. And one of the things we also have purposely done on the storytelling team and otherwise, let's hire radically different archetypes. Ellis cannot be more different than Nash. Nash cannot be more different than Josh. There's some shared values, there's some shared beliefs, but they're very different.

**Josh Miller** (01:00:35):
Ditto on the design team. Our design team? They are all over the place in terms of who they are, what they've done, their sensibilities, their aspirations. And whether it's the storytelling team or the design team, that can be hard sometimes, just to be honest. It's a lot easier to say, "Hey, we're the Acme Co storytelling team, we're Acme Co design team. We hire designers like this and storytellers that." We hire people all over the place. We have an extremely diverse team, but in all senses of the word. But again, the no PM thing, it's not without flaws. I can see why a lot of large companies over time tend are like, "It's the Facebook way or no way," or "You're not good for here."

**Lenny** (01:01:14):
Yeah. It's actually I think, exact makeup of Airbnb video team. I forget what they were called. They didn't have a cool name, the storytelling team I think. But it was a videographer, an editor and then their producer, basically.

**Josh Miller** (01:01:26):
Yeah. I mean, I remember going to Airbnb's offices early in my career and seeing the storyboards lining the walls and just being like, "I want to work here." So, I'm actually not familiar with the ... I mean, I'm familiar with Airbnb's videos and brand marketing, fucking fantastic, excuse my language. But, yeah. I remember just walking around that office being like, "Oh, my goodness! Are they making a movie or something? I want to [inaudible 01:01:53] here."

**Lenny** (01:01:54):
Funny you say that. And for folks that want to find that, we'll link to it in show notes. But if you Google "Snow White Airbnb," you'll actually see these storyboards. They basically hired a Pixar storyboard artist to draw out key frames of the journey of a host and a guest. And that became a central element of the strategy of, let's make each of these moments as amazing as possible. And it was based on the movie Snow White. You can read about it.

**Josh Miller** (01:02:15):
For what it's worth, this is a great moment to share. All of the beliefs that I've shared here on behalf of our team, these aren't things that we just originally came up with. They're moments like when I went to Airbnb's office early in my career and saw these Snow White storyboards lining the walls. That had an impact on me. Even the idea that you would think in terms of that moment, you could actually see the lineage to, well, how do you want that person to feel when they open that door for the first time? So, I think it's just a great moment to shout out that we've accumulated a lot of doses of inspiration, like that day at Airbnb, that trickle down to us talking about optimizing for feelings. But that didn't come in a vacuum. That's our expression of what we've seen in the industry. This is building on the backs of so many people and companies that we've been fortunate to see.

**Lenny** (01:03:03):
And now the trickling is happening from your lessons and experience and your unique approach.

**Josh Miller** (01:03:07):
I hope. There's a documentary that I highly recommend called General Magic. And it's one of the best pieces of media I've seen related to technology industry. And it's really interesting. I think there are two types of people to just be very ... There are people that watch that and view it as, "Wow! What a missed opportunity," or almost like a sad story. And I view it as, "If only we could be so lucky to assemble a group of people like that." And the thing about that documentary, for anyone that hasn't listened to it is, essentially was the iPhone before the iPhone, with the most legendary group of technologists working there. And it totally failed, completely failed by all traditional business definitions.

**Josh Miller** (01:03:50):
But, what stuck with me from the documentary, how proud and nostalgic and passionate those individuals were in reminiscing about their time there. And then, what they all went on to create. And the fact that even today on this podcast, I'm sitting here talking about General Magic. So, I mean, to your point of hopefully Browser Company will have ripple effects. That to me is the ultimate goal, for me personally, at a very emotional level. If we could only be so lucky. That, to me, seems like success in many ways.

**Lenny** (01:04:24):
Yeah. What's cool is you're getting a lot of footage that will be very useful for a future documentary on the history of The Browser Company.

**Josh Miller** (01:04:30):
[inaudible 01:04:30] I didn't think about it like that, for better or worse.

**Lenny** (01:04:32):
One last thought, I was going to mention it in terms of the storytelling movie-making elements of Airbnb. Fun fact, there was a period where product managers were actually called producers, because one of the founders was like, "We don't want to manage product, we want to produce beautiful experiences," like a movie producer. And so that was a year and a half maybe of Airbnb's history, where product managers were producers. The problem is, we got a lot of job applicants from Emmy-winning producers and they're like, "oh, I want to work at Airbnb."

**Josh Miller** (01:05:01):
I know this podcast is about very tactical advice. So, one tactical piece of advice I'll give is, whether or not you like the idea of the storytelling team or something else, a byproduct of some of these experiments that we've found works really well is when you give something a new name, it sheds a lot of preconceived notions of what the thing should be. We found that even with product. So if you say you're building a browser history feature, then the benefit is everyone knows what you're talking about. And the downside is, everyone knows what you're talking about. And you show up with these preconceived notions of what it has to be. And so, if you go back again to revalue ask what could be ... In many ways the point of calling the team, the storytelling team or the membership team, or not having PMs as an organization ... All of this stuff isn't meant to be novelty for novelty's sake. It's meant to almost be a rhetorical tactic, to make people think truly first principles about what are we trying to do here?

**Josh Miller** (01:06:00):
And again, if at the end, producers are called PMs, that's fine. But I assume when it was called a producer, a much more intentionality was given to you communicating and talking and discussing, what does a producer do? What's their relationship with design? Because no one knew what the heck a producer was. And so, ultimately, that may have been failure in other ways. But that's one of the things we found tactically to be really helpful is, whether it's a product feature or a team, or whatever, give it a made up name just to really get to the root of what you're trying to do there. Or not borrow too much from wherever you worked before, whatever you've seen, popular media or whatever.

**Lenny** (01:06:36):
I love that. And it's very undo ... Like, you've got to undo it. It was-

**Josh Miller** (01:06:41):
Exactly.

**Lenny** (01:06:42):
It's a two-way door. And I like just the vision, the value you have of just prototyping things and whatever. It didn't work. Let's go back to what everyone else is doing. You mentioned great product and there was something I definitely wanted to chat a bit about, which is just, there's this group of companies who are just focused on, "Let's just build the most amazing product experience." And I feel like The Browser Company is at the forefront in a lot of this. But it's like you guys, Linear, Raycast is this product, Cron. There's probably a few more and I'd love to actually hear if there's others that I'm not thinking about. That are just obsessed with the user experience and less focused on drive metrics, drive revenue.

**Lenny** (01:07:24):
And I'm curious, just where do you think this goes? What's your take on this trend? Why isn't every company thinking this way? Or is this just like, "We don't know if this is a good idea in the end?" So what's your take on this cohort of just like, "We're just going to build the best possible product and hope it all works out,"?

**Josh Miller** (01:07:41):
Yeah. Well, I'll say first, I love those products, or many of those products you mentioned. There's some I haven't really used. But, for example, our company runs on Linear, and has run on Linear since day one. So, I'm a big fan of that. So, the way that we think about it is ... So, I actually spent two years at a venture capital firm as an investor, called Thrive Capital. They've invested in Slack and GitHub and a lot of really transformative companies. But I was an investor there. I was a venture capitalist. It even feels weird to say that. And I learned a lot. A lot. A lot. A lot from that experience. It has made me, I think, a better CEO and a better product leader. And one of the things I learned is different ideas, product ideas, business ideas, company ideas come with different attributes and things that will matter to their success.

And so, when thinking about starting The Browser Company and picking this category of software, Hursch and I were incredibly intentional about what that would mean for what would need to matter for our company. And so, if you think about the web browser category, traditionally ... I'm not saying forward facing, I'm not saying it is what we are doing. But, if you were to look backwards and take The Browser Company out of it, and look at the web browser category, you'd notice a few things. The first is, it's actually one of the most consumer pieces of software out there. People forget that. That's the opportunity to us. If you ask someone in the street, "What's your web browser? What do you think?" They either won't know or they won't care, "[inaudible 01:09:15]. I don't know."

**Josh Miller** (01:09:16):
But what pieces of software do your parents, do your little nieces and nephews and you use? What's at the center of that Venn diagram? Your parents hopefully don't use TikTok and Instagram, or probably don't. Your nieces and nephews, I hope don't have a reason for email at the tender age of 16, or a calendar. And a web browser's one of the few things in the middle. So it's an incredibly universal piece of software consumer, unlike very few other things outside of a smartphone and messaging, and maybe video calling in 2023 and a web browser. So, it's very consumer, very universal.

**Josh Miller** (01:09:52):
The second attribute is, it's a commodity. I'm not saying that Arc is a commodity or we want it to be, but objectively web browsers are interchangeable. They all do the same thing. Increasingly, they're literally just carbon copies of the exact same code chromium, with little tweaks, little tweaks around the edges. So, they're all the same. It's a commodity market. And they're unbelievably lucrative. Browsers print cash. There is a reason why they're owned primarily by Google, Apple and Microsoft. They're incredibly high margin, they're incredibly lucrative. Low marginal costs. The cost of revenue is incredibly low, et cetera, et cetera.

**Josh Miller** (01:10:30):
So we have a product that everyone in the world uses, where they're all identical, essentially, interchangeable commodities. And if you can get people to use it, you're going to print money. So, the attributes of that business and that product category mean, you have to win on how much do people love your product and feel an emotional connection to it, and choose your brand, your product over the other, almost not rationally, but emotionally. And so, if you tie that back to everything I've said before, bingo! That is what we want to work on. That's what we want. We want to create emotional connection with people. We're creating that emotional connection with as many people as possible and delighting them with surprises and animations, is the way you win. It's not romantic, it is practical. In many ways it's capitalistic. This is how we win this market if you want to think about it that way.

**Josh Miller** (01:11:30):
So, the reason I hesitate to answer your question directly is, I don't think that applies to every category of software. And to be totally honest, I don't know enough about the ticketing space or the calendaring space or the whatever other space to know, honestly, off the cuff, if that approach is good for those industries. As a human being, at the other end, I'm really grateful that they picked some reason to do it, whether or not it is part of their business strategy or not. It's a really wonderful trend as a human at the other end that cares about feelings. But I would say, we actually think about it not as a, "We're focusing on the user experience over revenue or growth." We, in fact, picked a category of software we're focusing on brand and user experience is how you get growth and revenue.

**Josh Miller** (01:12:14):
And, because we knew that this is who we are, and if we were building cybersecurity software that you sell to government agencies, they are not going to give a shit about rounded edges, or what color the button is, or how surprised you feel with every member update. So, we didn't build cybersecurity software to sell to the government. So, I hope that more people build things at the craft bar of something like Linear, but that's how we think about it, is less of a "this versus that," and more "could we pick something we're going to work on, where that's how you win."

**Lenny** (01:12:48):
I think that's a really powerful insight, that for consumer software especially, and for commoditized consumer software especially, experience is a differentiator. You need to give people a reason to even try it, and then end up sticking with it when there's awesome alternatives. And so, just an obsession with the experience is a really smart strategy. If you get that right, people use it and continue to use it and you win.

**Josh Miller** (01:13:13):
I've seen this with a lot of ... And COVID is, I'm sure everyone listening, has a lot of the remote-work collaboration tools. A lot of them obsess, to their credit, over really interesting design details and product feature concepts that were imaginative and brought people together in new ways. And then the latency of the video of the audio audio was horrible, because they relied on some third-party API that was significantly worse than Zoom. And so, that's a great example where in that market, that category software, you better nail latency. I think a great example of this ... One of my favorite products these days, but past years is Tuple. It's ostensibly a paired programming tool that just lives in your menu bar. I'm not paired program with anyone. It is the fastest way to talk to someone at your company. And they have an unbelievably simple user experience.

**Josh Miller** (01:14:00):
The designer, based in Lyon, France, is incredible. It's a beautifully designed product. And it is the best audio quality I have ever experienced in a communication tool. Better than Zoom. So, that exact same product with all their craft details, sand latency, not going to do it. But also Tuple wouldn't have beat a lot of the other competitors for me if it wasn't unbelievably beautiful and easy and simple to use as well. So again, I think it's like, what are the attributes you need to win and picking a market that the ones that you want to excel at and work on, are key to that.

**Lenny** (01:14:34):
And also how much better you need to be. Like, if there's a 20% better than Chrome product, people are just going, "That's fine. I don't need to learn something new and everyone's using something else. I'm just going to have all these problems." So, you got to be significantly better. And that's a high bar for consumer products. Final question I wanted to touch on. You talked about the big vision for Arc and The Browser Company. And you mentioned this idea of the internet computer. And this is another question Scott Belsky suggested. By the way, Scott is the CPO of Adobe and just an awesome product-thinker person. And he just wanted to make sure that we touch on this, because I think there's a big idea here that maybe people don't realize. So, if you could just give us a brief overview of, what is just the actual vision and plan for The Browser Company and Arc, long term as a final question?

**Josh Miller** (01:15:19):
Yeah. So, we call it The Browser Company of New York almost as a misdirection, because as you know from the intro, we view Arc as a replacement for your default web browser, but we're hoping it will be much more. And so, to start at the highest level and bring it down to reality, one of the things that I've done many times in my career already is underestimate pretty foundational changes in how we use technology. I've appreciated them but underestimated them. Great example is mobile. I think me and Hursh's first company would've been much more successful if we really appreciated the tidal wave that was mobile. And I think one of those macro trends we're underestimating right now is the shift to cloud computing. The shift to the internet, which may sound weird because every big public company mentions Microsoft Azure or Amazon Web Services. You hear about cloud, cloud, cloud and cloud. But again, that's this business term.

**Josh Miller** (01:16:13):
What I mean by the shift to cloud computing is, everything in our technology, in our computing lives is moving to the internet. It has been moving, but it's going to move even more. And what I mean by that is, your applications are almost all today web-based, internet-based applications. And they will all be soon. There's very, very few pieces of truly local-only software or even local-first software left. All of our files are moving to the internet, if they're not all already there. So if you really think about your files today, and again you ignore the word "files," the stuff you need for work in your personal life. They're not sitting on your desktop, they're all URLs. It may be an air quote "PDF," but that PDF is probably out on Dropbox somewhere and you're accessing it as a URL.

**Josh Miller** (01:17:03):
Your photos may seem like they're on your iPhone. They're not on your iPhone, they're on some iCloud server somewhere. When you get a new iPhone, they'll be right there. The manifestation of that actually is, if you smash your device that you're listening to this on right now, whether it's a phone or computer, other than being sad that you lost the resale value and there's a chore of replacing it and a cost of replacing it, you would not lose any of your stuff. So, imagine in five years our entire computing lives are not on our devices, on our computers, on our phones. They're out there somewhere. They're out in the internet, they're out in the cloud, which begs the question ... I remember when I was 10 and I got my first computer. It was a see-through iMac. And I wonder ... My son is two. When he's 10, what will his computer be?

**Josh Miller** (01:17:52):
And I mean computer not in the technical ... Again, going back to words and the words that we use. I don't mean computer in the literal sense of my MacBook Air, but computer in the human sense of, what you need from your computer, your stuff, your applications and tools that people ... Where is that going to be? Where is his computer going to be? I think it's obvious at this point that we're going to have airflow computers everywhere. We already do. My car has CarPlay, my TV is a computer, my laptop is a computer. I think that's going to be even more true in five years, where hardware is commoditizing. And it will commoditize even more. They're becoming empty shells that don't have anything on it. They're just vessels. They're just interfaces to viewing our real computer, which is out there on the internet somewhere. And so, our view is that what we are building at The Browser Company is an internet computer, is a air quote "computer," where the move to the internet and move to the cloud accelerates and continues the tsunami as much as we think it will.

**Josh Miller** (01:18:57):
And the way we represent that is, we say we want to be to the web browser, what the iPhone was to the cell phone. Yes. The iPhone replaced your cell phone, but it really was something much more. And so, we want Arc to be the iPhone for the internet, and that yes, it replaces your default browser. But whether or not we call it the internet computer or something else, it really is that interface, this new type of computer. If you play that one step forward, then what we're building today is, we're building our equivalent of multi-touch gestures and the first party-notes app. But, on any new computer, any computer or computing device, the developer platform itself is much more interesting and lucrative and world changing than the first-party computer itself. And so, we have no doubt that in the next decade, if we're successful, if we still exist, Arc as a development platform is going to be much more central to what we're doing, building on top of these internet computers, ours and others than anything else.

**Josh Miller** (01:20:00):
So to bring that down from reality. If you think about it, the internet, the web, is really the best development platform out there in many ways. It is accessible on every single device. It doesn't matter who makes it or the shape and size. It is free to access for individuals. You don't need money to access it. It's free for developers. You don't have to pay a license to use it. There's no 30% tax on what you make. And it's democratic. The best frameworks can win. And so, in many ways, if you were to say, "Hey, in this future we want to see, what is the platform that we should be developing on top of, what has the best attributes?" The web has that. And that's why you're seeing today. Why do you think Figma is in the web browser?

**Josh Miller** (01:20:41):
Why do you think Figma's blog post was "Meet us in the Web Browser"? Because as the development platform, developers cross platform in one click. There's no tax. Everyone should want to and wants to make for the web. The challenge, though, is there's an experience gap. Native software feels better for whatever reason. And the problem is the people that control our interfaces to this development platform that is the web, that is the internet, have incentives to keep it from being as good as local software, from truly native, immersive software. Apple? They don't want you making web apps or applications for the web. They want you making them for the Mac and the iPhone so they can taxi you when you do it through the app store. And also surprisingly, Google doesn't want you making stuff, more native and immersive for the air quote "Web," because they want it to be indexed by their search engine.

**Josh Miller** (01:21:37):
So, there's a reason that the Chrome extension platform is one of the most underutilized opportunities. They view it as a loss leader. They built chrome extensions just so they could have parity with Firefox. They don't want you making extensions, because you have some immersive extension experience that's not something that you could index in Google. And that's taking away from doing searches. And so, I think we look at this and say, everything is heading to the internet, which means we need interfaces to the internet that are truly more robust than a browser, that are more of a computer. And if we do that, then the most interesting opportunity on top of that is actually the things other people were built on top of this development platform. And if you look at this development platform, which exists today, the worldwide web, the open internet, what is missing is an interface and a set of capabilities and APIs to make web-based experiences as immersive and rich and powerful as native experiences, which require that interface to the internet to provide those.

And our interfacers to the internet today are the web browser companies. They have perverse business model incentives as big public companies that have lost the soul of the founders, that they don't want to do that. They don't want to do that. So it doesn't mean we're going to do it. And in fact one of them may win. And I actually think that this is something [inaudible 01:22:51]. We're trying to sell anyone in our vision. We feel fully confident there are going to be many types of internet computers and Arc may or may not be one of them. But we feel very confident that that is the future and the development platform on top of the web and the internet, and these new interfaces will be the most exciting opportunity.

**Lenny** (01:23:09):
My next question was going to be how do you make money with a browser, which people get for free, really well? And now it makes a lot more sense where y'all are going. And so, with that, we have reached our very exciting lightning round. I've got six questions for you. Are you ready?

**Josh Miller** (01:23:26):
Ready.

**Lenny** (01:23:27):
Okay. So, ready? What are two or three books that you recommend most to other people?

**Josh Miller** (01:23:34):
Harold and the Purple Crayon, Seeing Is Forgetting the Name of the Thing One Sees, which is a book about Robert Irwin. That's my number one PM book. So, if you're asking from the perspective of the disciplines of people listening, that book is absolutely fantastic. And then God Saved Texas by Lawrence Wright, who's one of my favorite authors, who if you're interested in road trips, politics, food, culture. So, three very different types of books.

**Lenny** (01:23:58):
What's a favorite recent movie or TV show?

**Josh Miller** (01:24:01):
The first TV show episode I've cried from in recent memories, episode three of The Last of Us. I thought I was watching a zombie violence thing and I just was sitting there bawling. So that one. And then I've been re-watching all of the Adam Curtis documentaries on YouTube. I'm a huge Adam Curtis fan.

**Lenny** (01:24:20):
I have not heard of Adam Curtis. I will have to go check that out.

**Josh Miller** (01:24:23):
Hyper-normalization is my favorite. And I would view his work as less non-fictional documentaries and more video art.

**Lenny** (01:24:32):
There's been a meme of everyone saying White Lotus is the show to watch. And I feel like it's about to transition to Last of Us. And so we will see how that goes.

**Josh Miller** (01:24:40):
Can I get it first? Was I the first guest to say it?

**Lenny** (01:24:43):
I think you might be actually. I forget, but I think you might be.

**Josh Miller** (01:24:45):
All right. Well, I'll say episode three, specifically.

**Lenny** (01:24:47):
Yeah. Yeah. Absolutely. People love that one. But every episode's awesome. Next question. Favorite interview question you like to ask people when you're interviewing them?

**Josh Miller** (01:24:56):
What would you like to ask me? That seems like a non-answer, but my interviews at Browser Company are all, "Ask me anything," and I find what people ask, and how they follow up, is as revealing about who they are and what they care about than anything I could ask them.

**Lenny** (01:25:12):
What is it that you look for in an answer that tells you, okay, this is a good candidate?

**Josh Miller** (01:25:17):
Authenticity, probably more than anything else. Do they really believe what they're saying?

**Lenny** (01:25:21):
Awesome. What are some SASS products that your company uses and loves, other than ... ? I don't know if you consider our SASS, but probably not. So, yeah.

**Josh Miller** (01:25:29):
I want to plug Tuple. I think I'm going to put everything on Tuple, relative to ... We run on Notion, we love Notion, we love Linear. But I'd say the closet hit that I just cannot believe is not a hundred times larger company is Tuple. It is ostensibly a pair programming tool, but don't go in with that mindset. Go in with, "I need to talk to a colleague right now," or "a couple of colleagues right now, to do some work together," and it is absolutely fantastic.

**Lenny** (01:25:58):
I love it. I love these products I've never heard of that are super cool. We will link to that. Next question. What's something relatively minor you've changed in how you build product, that has had a significant impact in your team's ability to ship and execute?

**Josh Miller** (01:26:11):
This past January, a couple months ago, we have started removing me from a lot of the product development process, which seems to be really healthy. So, that has been the big shift this year.

**Lenny** (01:26:22):
That's a big transition. I went through that at Airbnb and it's great. It's great for everyone. Final question. Best pro-tip for using Arc, that people may not be aware of?

**Josh Miller** (01:26:32):
Try your best to not think of it as a browser. And have a beginner's mind about how it works and how you might use the internet.

**Lenny** (01:26:40):
Whoa! Big idea.

**Josh Miller** (01:26:42):
Yeah. Big takeaway from this conversation, we got to get much better at describing what the heck we built. And why it's good for you. So, I'm not proud of my first or last answer, but it is what it is.

**Lenny** (01:26:54):
And, actually, I mentioned this in the intro and if you listen to this already, you probably heard it already, but we're going to link ... In the show notes, we'll have a link to actually get into Arc, because right now it's wait-listed and we have this link that will get you straight into Arc. And so go check it out. Josh, you've shown up with heartfelt intensity. I feel like I want to go apply for a job at The Browser Company now. But you're not hiring product managers, so I'm not going to do that. Just kidding. Thank you so much for being here, for being so genuine and insightful and warm. And thank you.

**Josh Miller** (01:27:29):
Thank you so much, Lenny. I really enjoyed this.

**Lenny** (01:27:33):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes, or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [21/22] Navigating comms and PR | Lulu Cheng Meservey (Substack, Activision Blizzard)

**Lulu Cheng Meservey** (00:00:00):
I often say to find your audience's cultural erogenous zones. So what it means is people have things that they either care about or don't, and you're not going to change that. So it's a huge lift to try to change someone's worldview or their passions. It's a light lift to take the thing you want to talk about and just shape it into, to fit into their worldview or their passions. There's not always a fit.

**Lulu Cheng Meservey** (00:00:33):
There's going to be people who are just not your natural audience, and you should know that and not waste your time. But if your natural audience cares about X and you're offering Y, then it's your job to create the API or to create the bridge from X to Y. With messaging, it's not build it and they will come. It is so hard and you'd have to be superhumanly gifted to the extent that I can't recall seeing in my entire life, where you create a message and a story so powerful that someone who didn't care at all before suddenly makes that their passion. It's so much easier to take what they're passionate about and understand it, and then convince them that if they care about that then they should care about your thing because of this connection.

**Lenny** (00:01:18):
Welcome to Lenny's Podcast where I interview world-class product leaders and growth experts to learn from their hard won experiences building and growing today's most successful products. Today, my guest is Lulu Meservey. I met Lulu while she was head of comms at Substack, where she was infamous for taking big risks and bold stands, and as a result creating a lot of attention for Substack, and other companies she's represented. Lulu is definitely the most innovative and interesting comms person I've worked with.

**Lulu Cheng Meservey** (00:04:39):
Thank you Lenny. Great to be here.

**Lenny** (00:04:41):
I am really excited to chat all things comms and PR. I've never met a founder or product leader who doesn't want to get better at spreading ideas and getting their product out there, and you're very good at this. We're going to talk about some of the things you've done in the space. But just to start maybe just broadly I'm curious to hear just what have you learned about what helps an idea spread?

**Lulu Cheng Meservey** (00:05:03):
So there's a few ways to make the idea spread, the overall principle is you have to make it memorable and you have to make people want to say it of their own volition. And so what doesn't make them want to say it is doing a favor for a corporation. What does make them want to say it is they want to bring joy to somebody else, they want to make somebody laugh, they want to appear interesting, or they want to project some part of their identity. And so a few things that you can do with an idea to make it spread better, you can make it into a joke, so you can turn it into a line that people will repeat. You can use an analogy, you can take something and just say it over and over, move fast and break things, don't be evil, build something people want.

**Lulu Cheng Meservey** (00:05:47):
You can create a mental image that is very colorful. So I have a mental image for people that I use a lot, which is put the pill in some cheese and we can talk about it later, it's about how to craft a story that will stick. But when I say put the pill in cheese, people tend to remember that and it's more easily repeatable. And then the last thing is use a story, use an anecdote instead of using adjectives because adjectives are so subjective, they're meaningless to people. So if you give them a story that's something they can repeat over the dinner table.

**Lenny** (00:06:17):
Do you have any examples of the frameworks you just shared? So you talked about maybe having an analogy or putting the pill in the cheese, which I think is referring to when you feed a dog a pill. You want to hide the pill in the cheese. Is there any stories or examples that come to mind of this in action either something you've done or other companies you've seen?

**Lulu Cheng Meservey** (00:06:34):
One example not for the better is binders of women. You remember when Mitt Romney said binders of women and it just absolutely caught on like wildfire, and it's because you can picture the binder, it's a hilarious mental image. You make lots of jokes about it. It's a very specific unusual phrasing that is very repeatable, and it lends itself so much to memeing. So it's not something that they wanted to have happen, which is a word of caution, this can backfire on you as well, but that's an example. I mentioned move fast and break things, software is eating the world, it's time to build. Those are these short phrases that take normal words and put them in an unusual order, and then especially if you repeat them a few times they just become very sticky.

**Lenny** (00:07:19):
These things sound really smart and wise after the fact, do you have any advice on just how to... So we're talking about coming up with a cool phrase that'll spread of how to do that. I don't know what have you seen work for coming up with move fast and break things, how would a founder approach that?

**Lulu Cheng Meservey** (00:07:35):
You want to make it something that a second-grader could understand. You want to minimize the cognitive burden on the recipient. So it should be something where they're not having to expend any extra energy understanding the thing, where it immediately paints a picture. Or if you were to make a joke, it has to be a joke that they immediately get, or it's a very widely understood reference. You don't want it to be this inside joke with yourself that other people might get if you explain it to them. So if you were to boil down the essence of let's say your company or your mission, get it to one sentence and then turn it into a sentence that you could explain to a second-grader, and then cleanse it of all cliches and common parlance. And if you can then turn that into an analogy or if you can make it into something that has imagery, then you're probably 80, 90% of the way there.

**Lenny** (00:08:36):
So you've definitely done this on Twitter. It might be fun just to share a tweet or something of yours that has done this that has spread like crazy. I noticed you delete your old tweets, which I think is really smart and I should probably do that. So I couldn't find any examples, but I remember just being like, "Holy shit, it's got a bazillion views." Is there there an example that comes to mind that you could share? Just share something you put out that just went crazy.

**Lulu Cheng Meservey** (00:09:00):
I actually have a negative example too. I think it's useful to share my mistakes or missteps in addition to what went right, because there's more mistakes and missteps than what goes right. In general, you try a bunch of things every once in a while they succeed. But I think it's useful to think about what didn't land. And so one of mine was when you might remember this because this was the Substack era, when we were taking a lot of incoming for not censoring enough, and we took a stand that we want to encourage free expression. I was actually on maternity leave, so I was a little bit out of the loop, but I wanted to jump in there and support the cause. And so I did a thread about why we're standing by this principle even when it's hard, and the thread was pretty well received, it traveled a lot.

**Lulu Cheng Meservey** (00:09:53):
I think it was 30 something thousand likes among people that we cared about, people who write on the internet. And then there was one tweet in the thread where I said something like, "Doing this isn't pleasant, but neither for that matter is the sea." Completely esoteric reference, it was fresh in my mind because it was from a New Yorker book review where in that context it was poetic and evocative and beautiful. And I did the thing you're not supposed to do, which is take an inside joke with yourself and release it into the world.

**Lulu Cheng Meservey** (00:10:33):
And that one tweet was a dud in the middle of the thread where you could see the likes drop off precipitously and people were like, "What are you talking about?" And then afterwards I looked at it with fresh eyes, "Yeah, this makes no sense whatsoever out of a context." And also I'm not a New York book reviewer, so that was a good don't. But the fact that it was such a colorful metaphor actually caught people's attention in an accidental way. I didn't mean for it too. I guess that's a don't, does that serve as an example?

**Lenny** (00:11:08):
Yeah, that'll work and we'll go through other examples. But that's a good segue to something I was going to save for later, but it may be a good time to chat about is just something that you're big on is this concept of taking risks as a comms person, I think you have the sense that comms people are just very conservative, and there's a big opportunity to get a little out there. And in this case maybe it didn't work out, other times you have and it has. So just talk about that philosophy you have around taking risks.

**Lulu Cheng Meservey** (00:11:34):
I think if you're a startup your enemy is the status quo. And when you don't take risks, when you minimize risk by doing nothing, the best way to minimize risk is to do nothing. You're letting the status quo win. You're letting your greatest enemy and rival and threat to your business win by default, because you're not even going to try to compete. And so I always encourage people to try to make mistakes of commission rather than omission. Because if you make a mistake of commission you can observe it, you can learn from it. You know right away that it's happened. You can move really quickly and adapt and become better.

**Lulu Cheng Meservey** (00:12:11):
Whereas if you make mistakes of omission you're letting status quo win, you're not observing, you're not learning, and you're maybe not even noticing opportunities slip by. So the example that I use, again, an analogy to make it more memorable, my analogy for this is if you are investing money in the market versus if you're just sitting in cash. If you're sitting in cash you won't lose your money and it feels safe. But over time the world moves and the market grows, and everybody else is getting richer and you're getting poorer in real terms. Whereas if you make an investment it'll go up and down, there'll be some volatility. It's not just going to go up every day, but over the long run you'll be much, much better off.

**Lenny** (00:12:54):
Is there an example of something you did that you took a risk and it worked out, or you saw someone else do this really well?

**Lulu Cheng Meservey** (00:13:00):
The stand for free speech thread would be a risk that worked out. It was a risk because it was a topic that a lot of people were already mad about, which will happen with every topic that matters. It felt a little risky for me because I was on leave, I wasn't really in the middle of things. I was addled already, so I had at least one thing in there that was nonsensical. So there was the execution risk of would I'd be able to do this well.

**Lulu Cheng Meservey** (00:13:29):
There was also the risk of you poke your head up and make a thing where there wasn't a thing, and if that were to go wrong and embarrass the company or if that had made Chris or Hamish or Jerraj upset, that would've been upsetting to me and obviously a failure of my job. So that was a risk that I took and we took and they were supportive, and it did work out because the people who were most likely to write on Substack generally appreciate that stance.

**Lulu Cheng Meservey** (00:14:00):
I actually have one more for you Lenny when you asked about what are things that help stick in people's memory, there was the fail example of the sea analogy. I think a useful example that works is I often say to find your audience's cultural erogenous zones, and it is something that you immediately know what I'm talking about. If I say know your audience's cultural erogenous zones, you know what it means, it's a shorthand that everybody understands. It's not an inside joke with myself, and it's something that is unusual and upraising that you're going to repeat it and hopefully remember it, so there's one for you.

**Lenny** (00:14:40):
You told me about that framework and I definitely wanted to hear more about it. What does that mean and is there something that you've seen someone do that's just like, "Wow, they really nailed this erogenous zone approach."

**Lulu Cheng Meservey** (00:14:54):
Yeah, they really got it in the erogenous bull bullseye. So what it means is people have things that they either care about or don't, and you're not going to change that. So it's a huge lift to try to change someone's worldview or their passions. It's a light lift to take the thing you want to talk about and just shape it into, to fit into their worldview or their passions. There's not always a fit.

**Lulu Cheng Meservey** (00:15:26):
There's going to be people who are just not your natural audience, and you should know that and not waste your time. But if your natural audience cares about X and you're offering Y, then it's your job to create the API or to create the bridge from X to Y. With messaging, it's not build it and they will come. It is so hard and you'd have to be superhumanly gifted to the extent that I can't recall seeing in my entire life, where you create a message and a story so powerful that someone who didn't care at all before suddenly makes that their passion. It's so much easier to take what they're passionate about and understand it, and then convince them that if they care about that then they should care about your thing because of this connection.

**Lenny** (00:16:09):
This makes me think about one of the other tweets that I think went crazy, which is where you share the things you're muting on Twitter. Where it's like the threads thimble and the pointing down thing, and it feels like that's exactly that where people are just like, "Yep, this is me."

**Lulu Cheng Meservey** (00:16:25):
Yeah, it is that. I have an example for you Lenny. The one that my mind goes to is when Kamala Harris was running for Senate. Put aside what anyone thinks of Kamala Harris as a politician or if you agree with her politics, it doesn't matter. When she was running for Senate, she had this example where not enough people care about K-12 education. It's not a sexy topic and only moms care about it, whereas people cared a lot and still do about national defense, national security.

**Lulu Cheng Meservey** (00:16:55):
And so she said the way to get their attention is you go to people who care about national security and you tell them, "Did you know that in order to enlist for the army you have to have a 10th grade reading level?" If you can't read at that level, you're not going to be able to read the army field manual. And so if you care about the future of national defense and being able to maintain a standing army, you need to care about middle grade reading standards. So that's a perfect example, and in fact it stuck with me such that many years later I'm still repeating it to you.

**Lenny** (00:17:28):
Something else that I think what you teach helps with is underdogs coming up against incumbent companies, giving them a chance to stand out. Like Substack I think is a good example where you just helped elevate Substack on the world stage in a lot of ways. What have you found works best for underdog startups and companies trying to get attention?

**Lulu Cheng Meservey** (00:17:49):
First, you have to acknowledge that you're the underdog, and you're not going to use the GE playbook from the 1980s or whatever. So acknowledging that means knowing that you're not going to play the game that requires you to have more resources, more and deeper relationships, and institutional backings, and to be able to draft off of the current narrative. So all of those things are going to be not in your favor. If you're a startup for example, by definition you're trying to disrupt something, you're trying to do something differently, you're fighting the status quo. And if that's the case then you can't rely on maybe the government, maybe mainstream media to support what you're doing. And so you should assume that you want to go with an approach that doesn't require a lot of money or people, that doesn't require that institutional backing and those relationships.

**Lulu Cheng Meservey** (00:18:40):
That means building your own distribution, which you can do starting from day one. You can start doing that before you even have the company. It means taking your story and winning hearts and minds. Number one, by making it a story that you shape to fit people's cultural erogenous zones of your audience. And number two, by finding the centers of gravity in society, like the influencers that are going to help spread it for you. Because you're not going to on day one call up the New York Times and get them to print the story that you want them to. So you need to figure out who are the influencers and the way to do that, I'll cut off the rabbit hole after this because you can just go deeper and deeper, but the way to do that is in concentric circles. There's a general who said if there's a problem I look for it in concentric circles going back to my own desk.

**Lulu Cheng Meservey** (00:19:33):
If you want to spread something you go out in concentric circles starting from your own desk. So you need to get first really clear with yourself about what your message is and just get really crisp with it. This is hard to do because you know too much, so out of the 1,000 facts in your head you're going to have to pick just between one and three. And then the next circle is going to be your co-founders, your executives, your employees, your investors, you go to your power users, and you go out from there, and it has to be in that sequence.

**Lulu Cheng Meservey** (00:20:06):
But once you get the sequence and you identify who the people are and you know who your audience is, and then you're able to hone in on what their cultural erogenous zones are, then you're able to craft the message, have the delivery mechanisms, and then know your target, and then you're off. But you just need to do that exercise upfront, so you don't have a lot of wasted motion.

**Lenny** (00:20:25):
I really like this concentric circle framework. I haven't heard this before. Just to make it a little more real is there something that you can share, something that comes to mind that illustrates that?

**Lulu Cheng Meservey** (00:20:36):
Well, you and I have talked a lot about Substack, so I'm speaking out of term now that I don't have the employee badge. But something that I thought the Substack founders have always done so well is propagate product updates out in concentric circles. So there's a lot of things where you're going to know about it. You, Lenny will know about it more than a new writer who just joined, because you're a power user of the product and they would want you... Now they would want to make sure that you love the thing, and that you feel maybe even a little bit invested in the thing. You've been telling people about recommendations for nearly a year. No one asked you to do that. We didn't pay you to do that. You've done it because you were brought on board early and it was something that the company made sure that you liked, and then you became the next circle out that spread it to your next circle out.

**Lenny** (00:21:33):
It's interesting because I didn't think of it as an intentional strategy to get news out, and it feels like there's a synergy with just talking to your power users. Getting feedback from your power users leads to this interesting second order effect where they also want to... they feel like they're on the inside of something, they want to share it and maybe talk about it and tell friends about, "Hey, Substack's working this cool thing." So that's kind of a cool-

**Lulu Cheng Meservey** (00:21:53):
Well, early on Lenny you asked about how do you get a message to spread? And I said you give people incentives who want to spread it. So your incentive was you helping others, you like paying it forward and helping other writers and podcasters, and you genuinely enjoy the thing. And I think there's some value to your own project that you get to show social proof that a lot of people like this thing and it's growing, and that's what you got. If it had been like, "Hey, Lenny, can you do us a favor and tweet this thing?" You might've done it, but you would've done it once and stopped and it wouldn't have been something that you organically keep doing.

**Lenny** (00:22:30):
To make this even more real I'm trying to help people understand this concentric circle idea, so first Substack is an example. What would be the few layers of the concentric circle on the middle would be maybe the power writers. What would be the next couple layers?

**Lulu Cheng Meservey** (00:22:46):
It's the employees at the middle, almost always, and then it is depending on the company. So here it would be the power writers, it's youth, a lot of the original writers. Bill Bishop comes up a lot, he was Substacker number one, he's always really meaningful. And then it's fast growing writers. It is writer influencers. There are certain members of the media that cover media and writing, and so they matter a lot. And then investors are in there just to keep close to the fold.

**Lulu Cheng Meservey** (00:23:18):
But if you're a different kind of company that might be employees board, institutional investors, government and regulators then users, just depending on how much power each group has to influence your future. And the reason I say go out in concentric circles as opposed to just hit each of these groups kind of haphazardly is that's your way to control the message. Because each circle is going to assume that the inner circle knows better than them and they're going to follow the lead of the inner circle. So an example is if you and I have a company, Lenny and Lulu, this is a DTC startup.

**Lenny** (00:24:01):
That's a great name.

**Lulu Cheng Meservey** (00:24:02):
It is, we should do it.

**Lenny** (00:24:03):
We should do this.

**Lulu Cheng Meservey** (00:24:04):
If we had a company and we were trying to put out a message to the world that our new thing works, it's really revolutionary, our genes are the best genes. If employees are not saying that, then people are going to look at employees and say, "Well, they would know, they're closer to this than we are. So if they're not excited then why would we be excited?" And so that undermines everything that we're trying to do, you can't skip a circle is my point.

**Lenny** (00:24:32):
Super interesting. And I imagine the closer they are to the employees the more time you spend with them, and the more innately they're closer and also their perspective and what they share is more powerful because they're closer to what's happening.

**Lulu Cheng Meservey** (00:24:48):
And if it goes wrong the more damage they can do. So on the spectrum it's if they are not totally on board and they're not an effective messenger, versus they're just lukewarm and they're not really sure they believe it. All the way to they actively fell off the bandwagon and you lost them, and now they're out there proactively contradicting everything you say or even trying to destroy the company, that can happen. If an early employee, for example, feels disgruntled, which is easy to do and it's easy to do through a comms mistake. If you sell them on one thing and here's a vision, and now either that's changed or you miscommunicated. If they feel like there's a bait and switch they're going to be really mad. And now you've created someone who is incredibly credible and has the same social and professional circle as you and is trying to ruin you.

**Lenny** (00:25:44):
That's such a good point. For someone that's trying to do this maybe internally they're like, "Oh, cool, we got to create these circles for our startup." What do you recommend they do? Do they make a list of here's our inner circle, here's the next circle of people.

**Lulu Cheng Meservey** (00:25:56):
Yeah, you take out your one-page Google Doc. I feel like most comms problems can be solved with one-page Google Doc. So you go to your one-page Google Doc and you take your audiences, you list them, probably stop at five or six because past that it's like way, way first world problem. You'll have more than enough work to win over the five or six inner circles, and then you have to rank them. And you rank them by how much they're able to influence your success and how much credibility other groups assign them. So then you have your inner to outer circles.

**Lulu Cheng Meservey** (00:26:32):
And then for each of them you would think about what do they care about that's their cultural erogenous zones and where do they reside intellectually? So do they listen to podcasts, if so, which ones. Do they go to in-person conferences? Are they getting all of their news from Reddit? If so, which subreddits are they on Hacker News? Once you map that out, then again you have the people you're trying to reach, the ideas and messages that resonate the most with them, and then the ways to actually reach them.

**Lenny** (00:27:04):
This is becoming a real template we can start using. In the bucket of erogenous zones what are some examples of erogenous zones for people in this context?

**Lulu Cheng Meservey** (00:27:15):
We've talked about the free expression stand from last year. A lot of people care about first amendment, protecting press freedoms and free expression. Not a lot of people care that a journalist said something mean about Substack. And so there were a few times when we did have to push back publicly against a journalist saying something mean and unfair or untrue about Substack. So obviously my and our ulterior motive is to vindicate the company and show people that this isn't true. But if we had just done that, nobody would've cared or maybe a few diehards would've cared. There are people who care deeply about Substack, but not as many people and not as deeply as the people who care about their ability to express themselves freely or their right to build their own media platform without too many controls.

**Lenny** (00:28:20):
The way you described it earlier came back to me as you were talking, which is this idea that lights people up. What lights people up within this list of people that you're making? So that's really interesting. So the idea is create this list of people across circles further and further away from your employees. Think about what lights them up, what are their erogenous zones intellectually, and then think about where they spend their time intellectually, what are they listening to? What are they reading?

**Lulu Cheng Meservey** (00:28:44):
Yeah, that's it.

**Lenny** (00:28:46):
Amazing, this is super cool.

**Lulu Cheng Meservey** (00:28:47):
It's not easy, it's hard, you have to make very difficult tactical decisions every day when you're doing that, but it is simple.

**Lenny** (00:28:54):
Yeah, it seems pretty easy. Okay, this is great. Another framework that we haven't talked about yet, do you have this math formula for how ideas spread? Does that ring a bell?

**Lulu Cheng Meservey** (00:29:04):
Yeah.

**Lenny** (00:29:05):
Okay, let's get into that.

**Lulu Cheng Meservey** (00:29:06):
I think it's useful to try to bring as much discipline as possible to comms, because you're really just measuring vibes. In a world of OKRs and data and metrics it's hard to know if you're doing the right thing with comms. And so I think whenever you're able to establish a framework its useful, so this one is kind of a mathematical formula of comms for a purpose. It assumes that you have a business goal and as a business goal, not communications goal, it's not get this many impressions or go viral or blah. It is we're going to grow our revenue by X, or we're going to make this penetration into this user base. When you have your business goal you're going to need certain people to do certain things for that goal to come true. So for example, you're going to need this type of person in this quantity to buy these sneakers in order for you to meet your revenue goal.

**Lulu Cheng Meservey** (00:30:07):
So now you know who the people are and the action they need to take. The next step is what do they need to believe in order to take that action? So they need to believe that their feet are not comfortable now, and that it's possible for their feet to be more comfortable and that'll have a positive effect on their life, and that this new sneaker technology is real, so they need to believe these things. Then it's where do they reside intellectually? How do you deliver that message to them, and that's the who do they listen to? Which accounts do they follow? Which podcast do they... what trips do they take? What newspapers, et cetera. And when you have that then you have the equation of we need to deliver this message to these people through these mediums in order to get them to do this thing with this call to action. And that way you know that you're at least pushing forward and getting something done with your comms as opposed to just saying words into the ether.

**Lenny** (00:31:11):
I think you had something like there's pressure and force and area, is that part of this or is that a different framework?

**Lulu Cheng Meservey** (00:31:17):
Different framework.

**Lenny** (00:31:18):
Oh, okay, cool.

**Lulu Cheng Meservey** (00:31:20):
Oh yeah.

**Lenny** (00:31:21):
Okay, okay, let's talk about this other framework too.

**Lulu Cheng Meservey** (00:31:24):
I've got more frameworks, Lenny.

**Lenny** (00:31:25):
I love it, this is what this podcast is all about. Let's do it.

**Lulu Cheng Meservey** (00:31:29):
This is a useful one for early stage startups especially, or anybody who's just trying to be lean and efficient, which is anyone who's an underdog like we talked about earlier, that if you decrease the surface area than with the same amount of force you can apply more pressure. So the amount of pressure is the force divided by the surface area, this is a basic equation for physics, but it's also true of communications, which is if you decrease the surface area and don't try to appeal to everybody with everything. And you're targeting exactly whom you're talking to and you are sharpening your message to a point, to get them in the bullseye of the cultural erogenous zone. Then you're able to with the same amount of effort or expense or time, you're able to make more of an impact, you're able to apply more pressure.

**Lulu Cheng Meservey** (00:32:30):
So I think of it as there's a continuum between you can either hyper-target, so the extreme of the continuum is you are becoming the life partner of one person. That's the ultra hyper targeting. And then the other end of the spectrum is you're appealing to everybody. You're appealing to a larger number of people, but with a weaker message, in a weaker way. So you could say world peace is good, nobody disagrees with that practically, but also it doesn't stick and it's not meaningful to them. So you have to choose where you're going to be along that continuum. And for most startups I would choose towards the fewer people end of it, where you choose who's going to be your diehards and then you foster them and create really deep meaningful relationships with them. And the way to do that is to decrease the surface area and apply more pressure.

**Lenny** (00:33:23):
It feels like you did that with Substack where it was focused on people writing online, or I guess tell me is that how you thought about it Substack of here's our little focused area and we'll focus target message to that.

**Lulu Cheng Meservey** (00:33:37):
That was the goal and that's actually why I started spending time on Twitter. It was a very self-loathing exercise like Hamish doesn't like the Twitter model, nor do, we would talk about this a lot and I always felt a little bit fringe being on there. And before I worked at Substack I had a sleepy account of a couple hundred followers that didn't do very much. And I realized that the people that we were trying to speak to are heavy Twitter users, whether it's media people or online writers. And so I decided I'm going to spend some time and try to build an audience and then that audience became leverage, for better or worse. I don't think we should measure people by their Twitter following, but the fact is that if you have more then journalists and writers take you a bit more seriously. And so if I was going to try to carry a message on behalf of the company, I felt like it would be more effective if I had more people.

**Lenny** (00:34:38):
**Lulu Cheng Meservey** (00:36:11):
It's the amount of effort you put into it. So it's how much you are spending on this campaign or you have a limited amount of hours in the day and dollars in the bank. And so anytime you're doing something with comms, you're either paying the dollars or you're paying the time. Sometimes you're drawing down on credibility too, you have a certain amount of credibility and there are times when you just have to say, "Please trust me." You can spend that more efficiently if you focus. So instead of if you just take a simple ad campaign, instead of spending a million dollars to reach a million people, maybe you spend a $100 to reach the hundred most important people. And focus that message exactly to them so that when they see your ad they're actually going to click on it and they're actually going to forward it, and that's a much better return. And then you might end up with a million dollars worth of return, because those people were so passionate that they then became their own messengers without you even having to be involved anymore.

**Lenny** (00:37:12):
This is a really great framework, again, is your advice that for the smaller you are just basically reduce the area?

**Lulu Cheng Meservey** (00:37:21):
Yes.

**Lenny** (00:37:22):
And the larger you are increase that over time?

**Lulu Cheng Meservey** (00:37:24):
Yes. If you're just starting out, get 10 diehards and just spend all your time... You can't start out and try to win over the general public. You start out by creating a tiny, not the best analogy is one I can think of right now, a tiny monopoly. And it's the same like succeeding on Substack or creating anything on the internet. You choose what is going to be your tiny corner of the internet that you are going to just dominate entirely. And the smaller it is, the more you can dominate it and then these people that are in it become your true believers, your diehards, and they'll expand it out to the next circle and then you go from there. But if you try to win over everybody at the same time, it's a food coloring in the ocean kind of thing as opposed to food coloring in a cup.

**Lenny** (00:38:17):
Is there an example that comes to mind of someone that did this really well? I don't know. I know it's hard to think of just an example off the top of your head, but does anything come to mind?

**Lulu Cheng Meservey** (00:38:25):
Balaji did this really well with his book The Network State, that book was super successful. He didn't do a lot of the traditional book tour New York Times stuff. He went his own route, and I think that was really smart if you're going to put it in the setting of this framework, it's he created his own distribution channels. He didn't try to compete with the roster of Harper Collins on their turf, and when he created his own distribution channels he focuses on who are the diehards and the truth fans, and these are people that he fosters. He goes on podcasts that reach these people. He doesn't deviate from messaging to try to appeal to everybody. There are people who just will never like that guy and he is totally fine with it. So he's not watering down who he is to appeal to people who will never like him, which it's tempting for companies to do.

**Lulu Cheng Meservey** (00:39:17):
You hate when people are mad at you, so you try to appeal to them and then your true fans lose their passion because the thing that made you so special has now gone milk toast. So Balaji fosters his true fans and then when the book launched they propelled him to the top of the Amazon list, because they were out there evangelizing, proselytizing. You probably saw all these tweets about his book. He didn't pay anybody as far as I know. He didn't pay anybody to do that. He just shared it with the people and they wanted to show that they were into this.

**Lenny** (00:39:46):
That's a great example. I know that founders often worry focusing too narrowly limits their market, and it's never going to grow into anything large. In your experience do you find that that's just often not true, that there's often a much bigger opportunity than they think? Or is that just a good way to start and then you expand from there?

**Lulu Cheng Meservey** (00:40:03):
It's both. If you're writing online or doing something online, the denominator is the size of the internet. You don't need to capture 80% of it. If you capture 0.01% of it, that is a great business and then you can go from there. Once you've won that then you can decide to go from there and the world is a big place. So now that everything's digital the denominator's so large that I wouldn't worry too much about the numerator. But it is also true that if you start off trying to peel to too many people, you have to water down your stuff so much that you'll never stand out. And you've written about this Lenny with how to be viral, how to be noticed, and one of the things is be remarkable. And you can't be remarkable if you're trying to appeal to so many people that you have to become the average of 500,000 people's tastes.

**Lenny** (00:40:57):
This is a good way to think about I think when something's not working, when you're trying to get a bunch of attention for your product and no one cares. Feels like this is one reason is just you're going too wide.

**Lulu Cheng Meservey** (00:41:09):
Yeah, I think that's probably the most common reason.

**Lenny** (00:41:14):
Maybe just thinking about diagnosing why your comms may not be working. This may be too big of a question, but just what other explanations could there be for why no one cares about what you're trying to put out?

**Lulu Cheng Meservey** (00:41:25):
You're doing it as a corporation instead of a person. This is another super common mistake is you're letting yourself speak like a faceless corporation because it feels like that's what you should do now. Okay, now you're a real company and now you got to do real company stuff, that means you have to issue decrees on behalf of the C corp and you don't. And it doesn't work because people don't trust institutions. People don't like corporations or at least are not passionate about them. People care about people and trust and like people, and so there's a sense of wanting to cosplay an executive and it doesn't work, it doesn't resonate. A good example of this would be Ryan Peterson at Flexport. His company, even after it got huge, he never became the generic corporate chief. He always was a person. And there are people, many, many people who became interested in Flexport because Ryan's an interesting guy. And it's not like they had a passion for logistics and freight and shipping, but he's doing something interesting. And then he became the human gateway drug for people to become interested in his company.

**Lenny** (00:42:40):
Yeah, absolutely. He had that crazy viral tweet about the ports and that's a really good example. Man, I was going to go in a different direction, but maybe we go to this idea of going direct. You're a big fan and Balaji is a really big fan of this too, speaking of just the importance of going direct. So maybe just talk about what does that mean and why is that important these days?

**Lulu Cheng Meservey** (00:42:58):
Well, Balaji is more go direct than me. He thinks that I'm soft in this area because I think that there's still a place for engaging with media and that it's just another tool. He's for just straight-up go direct undistilled. But I think that for everybody a 100% of the time you want going direct to be a part of what you're doing, whether it's all you're doing, or whether you're doing something else, you can't not have a direct channel. So what that actually looks like, and people say this all the time go direct. What does that actually look like to go direct? It means that the founder or executive for some very senior person has to be speaking from themselves. First person, may be first person plural, and speaking in a human voice authentically. You see them make mistakes, you see them be vulnerable, and they have to become an ambassador to the community.

**Lulu Cheng Meservey** (00:43:55):
If you don't have that, then you don't have a direct channel even if you have a Twitter or a Substack or whatever, it's not direct if not connected to a person because if the other side of it is a corporation there's no direct connection. And then the second thing is start building your own audience as soon as possible. You can do this alongside engaging with the media or doing traditional things. To the point of focusing your energy and decreasing the surface area, for startups I would not recommend trying to do an Instagram, a Twitter, LinkedIn, YouTube, and TikTok. I would choose the thing that that person is the best at. So if your spokesman is going to be your CEO, which is a good default, they're going to have a dominant communication style where they're the best at being themselves. And that's important because if somebody else is ghost-writing all their stuff, it shows.

**Lulu Cheng Meservey** (00:44:53):
So some CEOs are better at writing long form. Some CEOs are better at doing videos. Some do better with audio or podcasts, some are better with short form. The way that Elon Musk communicates on Twitter, he's born to do Twitter. You can't picture him writing long thoughtful blog posts, it's not a thing that he does. Whereas Brian Armstrong or Hamish or Chris, they write great blog posts that are sincere and effective, and that's better than them just trying to do it only through tweets. So pick the thing that your spokesperson is the best at and then invest everything into that channel, and then build it up to a decent amount and then expand outward. Because if you try to build six or seven channels at once you're just not going to get anywhere.

**Lenny** (00:45:47):
I think that's such a important point. I feel like me choosing a newsletter was actually a really good choice. As much as you may not believe this I'm not a performer person, I just want to hide behind the computer and just type stuff. And the newsletters, especially during COIVD, I was like, "I just sit at home and share stuff and edit and think about it where it's like, 'Hello everyone.'" And it took me a while to get to this point of like, "Oh, I can maybe do a podcast because I've built up a little more confidence that this is useful." So I so agree with that and that's what I tell a lot of people. Just pick the platform that is most natural to you. Maybe you like talking, maybe you performing on video, maybe you just want to sit and type.

**Lulu Cheng Meservey** (00:46:24):
And that's a good point too, Lenny, because it changes over time. Just because you pick one thing doesn't mean that you're stuck with only that forever. Over time you might choose different things and I've seen founders become a lot more comfortable in front of the camera, for example, once they've done a few reps. And the other reason to know that you can just change it over time is otherwise it feels like a deterrent to getting started. Sometimes there's paralysis if I don't know which thing to choose, and so I'm either going to do a bunch of them or none of them. Go with your gut pick one and you're not wed to that forever, you can always change it down the road.

**Lenny** (00:46:58):
Do you think every founder needs to be on Twitter? I get this a lot from founders. Do I need to be on Twitter? I hate Twitter. What's your take?

**Lulu Cheng Meservey** (00:47:04):
No, I think a lot of founders do. If they are super mission driven, for example, that's one way that you're going to find other people that resonate with your mission and that you're going to make the case for the mission. If you're mission driven there's also a good chance that you're doing something that some people love and some people hate. And so you're going to need to be out there fighting the fight in a way. I don't mean in a pugilistic antagonistic way, but you have to defend your thing. And so I think it's important if you're mission driven. I also think it's important if your charisma is a big part of recruiting for the company. There are some companies where the founder's charisma is a big part of why people want to go work there. So Palmer Lucky and Anduril, he is magnetic to a lot of engineers and they want to go work with that guy, specifically. Whereas there are companies where people want to go work for the company and it's less important that the founder is vocal.

**Lenny** (00:48:02):
What's interesting I found recently is I get more traffic to my newsletter from LinkedIn than Twitter. Is that something you think about at all? Going to LinkedIn instead of Twitter feels so wrong to say, but what's your take there?

**Lulu Cheng Meservey** (00:48:14):
Yes, if you are career related, LinkedIn will be a lot better. One, it's better because it's not such a cesspool where anything immediately becomes controversial and people fight over it in their mentions. Two, because LinkedIn is really underutilized and founders should know this, PMs should know this. LinkedIn is super underutilized because it gets a ton of eyeballs in time, but most of the content sucks. 95% of the content this is not scientific-

**Lenny** (00:48:49):
Seems right, seems right.

**Lulu Cheng Meservey** (00:48:50):
This is my might estimate. 95% of the content is people congratulating each other on work anniversaries or people saying, "I'm so proud of my team for this thing they did." And then people react out of a sense of friendship and affection or support, but actually genuinely interesting and useful content on LinkedIn is very rare. So the ratio of your competitive set of interesting content versus how much time and attention people spend on there is excellent.

**Lenny** (00:49:24):
That is really good advice. I'm going to throw a fishing line into the pool of examples. You talked about people doing this well, going direct. Balaji talking about Ryan Peterson and Elon obviously. Is there anyone else that's just like here check out what they're doing and could be a good model to learn from?

**Lulu Cheng Meservey** (00:49:41):
I think it's really interesting to see what Mike Solana is doing with Pirate Wires. Here's an example of why it clearly makes sense to have the founder be very active on Twitter because he is his own recruiter and spokesperson. So I think the makeup industry actually is at the forefront of this. The makeup industry is smarter than all of us in how they use social media and influencers, because they caught on very early on that people don't buy makeup to subscribe to makeup brands, that they do it because a certain celebrity or influencer or Kardashian has this nice looking eyelid and they want their eyelid to look that way.

**Lulu Cheng Meservey** (00:50:25):
And so going back years before the rest of us were talking about going direct, there are makeup companies that would spend $0 on marketing, and minimal efforts on press and pour all of it decreasing the surface area. Pour all of it into fostering a small roster of influencers and having them spread the message. And so I think watch makeup companies, watch consumer companies, they're doing it right, they speak with a human voice, they speak through human beings and they're fast. If there's a trend the same day they will have hopped on the trend... within an hour they're on the trend, as opposed to other industries or more traditional companies that take a few days and they route through approvals and then the opportunity's gone.

**Lenny** (00:51:11):
What are some makeup companies for people to check out to see what they're doing?

**Lulu Cheng Meservey** (00:51:14):
So NYX, N-Y-X, it's a division of L'Oreal. NYX is wanted the makeup companies that has, as far as I know $0 spent on marketing and all of their dollars and all of their effort spent on paying influencers. And they really out punched their weight in terms of using humans to deliver a message that contains a call to action and then selling out product. And the product will be like a normal black eyeliner. It's the most fungible thing you could possibly imagine, and that one eyeliner will be sold out at CBS's across the country for a couple weeks, because they did something right with their social media using a person.

**Lenny** (00:51:57):
Just a couple more questions around this going direct concept. I don't know if you actually talked about why that's important because I think we talk about this a lot, and I think people may not recognize why people find this so important these days. What's the motivation behind that with Balaji and other founders?

**Lulu Cheng Meservey** (00:52:14):
There's two reasons it's important, there's the offense and the defense of it. The defense of it is going back to having the underdog, the insurgency mentality. If you're trying to do something different that goes against the grain, people are going to attack you. Not everyone's going to like it. And the point is that not everyone should like it, but you need a way to stand up for yourself because you don't have the big institutions and power structures that are going to do that work for you because you're going against the grain. So if you're going to stand up for yourself there's only one way to do it, which is you do it. And so building the audience and the channels and you have to prime the market. By which I mean if you're a public company, you're priming the market by getting them used to how you convey information to them.

**Lulu Cheng Meservey** (00:52:58):
If you're a small startup or a founder, you're priming the market by making your audience aware of how you normally communicate, so that when you do something it's not weird. If you never post and then suddenly you start posting, people are going to think you're having a crisis or something like what is going on? They're going to try to read into it. So you have to already have the cadence and the relationships set up so that when you need to draw on them if you're under attack then you can, that's the defense of it. The offense of it is if you're doing something new and if you're mission driven, and if what you're doing is truly unique and innovative, no one else will be to tell that as well as you. The most friendly, sympathetic reporter on Earth could not tell that as well as you because they don't understand it as well as you, and so the onus just falls on you to do it.

**Lenny** (00:53:52):
If someone listening is like, "Yep, okay, I fully agree, time to do this." What do you suggest as a next step to starting to build an audience and going direct broadly.

**Lulu Cheng Meservey** (00:54:03):
Step one would be assessing what are you good at and what do you enjoy? So that's where you decide, do I like long form writing, or do I enjoy podcasting, or what are my mediums? Step two is setting up your account on those channels. So if you enjoy long form writing then you're going to have to choose, do you do a Substack, do you do Medium or whatever else? There's a objectively right answer on that one. But if you are doing short videos you're going to choose are you going to invest in Instagram, or you're going to invest in TikTok, you set that up. And then you start building your audience. And when you start if you're actually starting from zero, get some pipeline of talent ready. Sorry, not pipeline or talent, pipeline of content. Get it ready, it's the same way as if you're launching a Substack.

**Lulu Cheng Meservey** (00:54:54):
If you're launching a Substack you want to get a week or two of posts ready to go, so that out the gate you can build a lot of momentum. With different social networks it actually helps the algorithm if you come out the gate strong and are really regular. So TikTok, for example, if you're starting at TikTok with zero followers, you want to get a week or two of solid data just in the pipeline so you can hit it, hit it because the algorithm favors you right as you're starting out because they want you to keep going, so you want to ride that as much as possible. So that's step two is just get yourself ready for launch. Don't do one post and wait, get a bunch of posts ready and then boom, boom, boom. And then three is to have an ongoing content strategy, you know who you're going to reach, you know what they care about.

**Lulu Cheng Meservey** (00:55:42):
So you have to plan out, "Here's the cadence with which I'm going to talk to them. Here's how I'm going to do community management and respond to people, and here are the ways where I'm going to do announcements." And you get into a cadence because it's the same as growing a newsletter. The regularity and the consistency is a big part of growing. And so it's the same with audience. A mistake that people make I think is just every once in a while trying to go viral as opposed to just being consistent. And then some posts do better than others organically, but that's the way to do it. I don't live that. I'm not a good example because I'm so self-loathing about being on Twitter I will go away for one or two weeks and do nothing, and then I'll come in with a bunch of posts in one day. It's not a best practice. It's not the way you're supposed to do it. Ideally, you're just there every day saying something and then it builds over time.

**Lenny** (00:56:36):
I'm actually an example of trying to focus on consistent non-viral content and it's worked out.

**Lulu Cheng Meservey** (00:56:44):
It has worked out.

**Lenny** (00:56:46):
It's worked out. It's worked out so far, but it's interesting to see how different people act and how it's like I'm trying to go viral every tweet, every post and that is hard. And it's also just like people can tell you're just trying to create some viral thing and no one cares.

**Lulu Cheng Meservey** (00:57:00):
And it's very obvious when you're just trying to go viral for the sake of it and you don't have a real message. It's like the post when people screenshot the iPhone six digit security code and they say best feature apple's ever built. A few people did that, and now I've seen it probably dozens of times. And it doesn't even help to get you followers because that's not something where people say, "Only this person could uniquely give me this kind of content in the future." If you're going to get followers with a one-off joke, it has to be an incredibly hilarious one-off joke where they say, "This person is going to keep entertaining me." But with these kind of viral baits, I don't think it's even that effective.

**Lenny** (00:57:41):
And also what I find if something does go viral, whatever the correct term is and then life goes on, nothing's going to significantly... that's just one thing, and then you have to do it again and again. That's where people don't realize like, "Oh, I went viral. I'm done. My life is good now." Nothing's going to really change most often, and you have to do it again and again.

**Lulu Cheng Meservey** (00:58:03):
I think that's true. One thing that I've noticed about your audience, Lenny, is that it's the right audience. It's the people who find value in what you do, and they're in the right place and there's a match. Sometimes in the effort to just gain followers for the sake of it or a go viral for the sake of it, you end up with a mismatch of the audience. You had this viral hamster tweet, and now they're all here expecting hamster content, and they're not engaging with you, you're not bringing value to them. It's just making the number go up, which is not that meaningful. So one example of this is there's all these threads about how to just grow on Twitter for no reason, just grow for the sake of growing.

**Lulu Cheng Meservey** (00:58:48):
And it's a lot of generic advice of make sure that you bullet point out the 10 things. But it's always pablum of make sure that you value your relationships, and make time for yourself. And things that are not enriching people's lives they get a lot of likes that are low value likes from random people about the internet. But I don't think that they're deepening a relationship with a meaningful audience, and I don't think that they're really capturing the respect and admiration of their peers. So I think it's just important to consider what trade-offs people make in their efforts to grow.

**Lenny** (00:59:28):
Well, with that we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

**Lulu Cheng Meservey** (00:59:35):
Ready.

**Lenny** (00:59:35):
First question. Great. What are two or three books you've recommended most to other people?

**Lulu Cheng Meservey** (00:59:41):
I recommend Gates of Fire, it comes off the Marine Commandants Reading List, it's on there perennially. It is about the Battle of Thermopylae, it's the 300 Spartans, but it's the whole backstory. And if you get into it's about leadership, it's about courage, it's about creativity, and it's really well-written, so that's one that I recommend a lot.

**Lenny** (01:00:00):
What's a favorite recent movie or TV show?

**Lulu Cheng Meservey** (01:00:03):
I've been watching The Last Of Us, like everybody on Earth. I've been watching it both for entertainment and for work, because it's really interesting to see how the show drives sales of the video games, and how you can use that to make the whole of the sales greater than the sum of its parts. So I'm watching that really carefully.

**Lenny** (01:00:24):
Interesting. We have a drinking game now. Every time someone says Last of us that's a new thing because it's starting to come up a lot, so everyone enjoy your drink. Favorite interview question you like to ask?

**Lulu Cheng Meservey** (01:00:36):
I like to ask people what they've been reading too. It's a good way to get good book recommendations. It's also a good way to see where their head's at when they're not working.

**Lenny** (01:00:45):
Favorite SaaS products that you use day-to-day and bonus points for something that is new or interesting that you've recently discovered?

**Lulu Cheng Meservey** (01:00:52):
I don't know that this is new or novel because I use Notion for almost everything, and I really like the new AI that they've built into it. I also have been using Lex, which is Nathan Baschez startup, where it's like the AI writing editor that you've probably seen. I'm trying to think if there's anything that I use that other people don't. I don't think I'm terribly original in that sense. I use a lot of Microsoft Excel, which I think is controversial.

**Lenny** (01:01:21):
That is, wow, that's cool, but I get it. That's when you know you're doing serious work, you got to accelerate.

**Lulu Cheng Meservey** (01:01:27):
Yeah, exactly.

**Lenny** (01:01:28):
Final question, best tip for someone trying to get attention for their product, take away tip, best takeaway tip.

**Lulu Cheng Meservey** (01:01:37):
Give it away for free to the right people. If you can choose the people who are going to love it, look at the Venn diagram of people who are going to be obsessed with this product. And people who have a large following among the other people that you want to get to, whoever falls into that sliver of the Venn diagram shower them with free product.

**Lenny** (01:01:58):
Amazing. Lulu, I think this conversation is going to lead to a lot more people going direct, taking risks and ideas spreading. Thank you for being here. Two final questions where can folks find you online if they want to learn more and reach out and how can listeners be useful to you?

**Lulu Cheng Meservey** (01:02:13):
People can find me at getflack.com, that's where I write down my ideas, hopefully more frequently in the future than in the past. But that's where they can find some of this stuff if they're interested. How can listeners be helpful to me is to give me feedback. I'm learning on the job. I don't think that there's anyone alive who's an expert in communicating in this crazy environment that we have now. I think we're all crossing the river by feeling the stones, and so your listeners have gone through this in many different ways. And I hope that if they have new ideas of feedback or objections, that they'll email me through that website or on Twitter and let me know what they think.

**Lenny** (01:02:54):
Amazing and its get flack.com.

**Lulu Cheng Meservey** (01:02:55):
Yes.

**Lenny** (01:02:55):
We'll link to it in the show notes.

**Lulu Cheng Meservey** (01:02:55):
Thank you.

**Lenny** (01:02:57):
Lulu, thank you for being here and sharing your wisdom with us.

**Lulu Cheng Meservey** (01:03:00):
Thank you, Lenny, appreciate it.

**Lenny** (01:03:03):
Thank you so much for listening. If you found this valuable you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [22/22] Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek)

**Kevin Aluwi** (00:00:00):
In the early days of Gojek, there was a lot of resistance to our services. The most common form of that resistance in the early days was actually by motorcycle taxi mafia. So you would have these areas that are essentially controlled through violence by specific area mafia. And when we start having drivers pick up orders and pick up passengers, these people would actually physically assault our drivers. We've had everything from bricks thrown at our drivers to knives and machetes being brandished at them, and I think it would've been easy for us to say like, "Hey, they're all contractors. They're third parties, let them kind of just sort it out." But instead, we actually hired private security. So we actually work with private security companies to help our drivers in those situations, to help kind of extract them out of these sticky situations. And so we actually ran a fairly big private security operation for a fairly long time.

**Lenny** (00:01:16):
Welcome to Lenny's podcast, where I interview world-class product leaders and growth experts to learn from their hard won experiences building and growing today's most successful products. Today my guest is Kevin Aluwi. Kevin is the co-founder and former CEO of a company called Gojek, which I've always been fascinated by. You may recall a former guest Crystal Widjaja, who was head of growth at Gojek, and I've always wanted to get more of the story. Gojek is infamous for their scrappiness, their unique approach to ops and growth, and as being one of the first and most successful super apps in the world. They've also long been maybe the biggest startup in Indonesia and all of Southeast Asia. Kevin and the story of Gojek have a lot to teach founders in the US and all over the world, and so I was really excited to sit down with Kevin to dig into the story, he did not disappoint.

**Kevin Aluwi** (00:05:03):
Thank you. Thanks for having me, Lenny. We've finally made it happen after a few weeks or months of going back and forth.

**Lenny** (00:05:10):
Yeah, I'm really excited to finally meet you and to dig into a bunch of stuff. I think this is going to be a really unique episode. I don't often have founders on the podcast, especially founders of companies that are not based in the US. In this case, Indonesia, Crystal Widjaja, who is on this podcast previously. One of my favorite guests is just like "Lenny, you got to get Kevin on your podcast." And so here we are.

**Kevin Aluwi** (00:05:32):
I'm glad to be in a small group of category of people that you invite. Thank you. I'm a huge fan of what you do.

**Lenny** (00:05:38):
Thanks, man, I really appreciate that. And just redirect to you, you are the co-founder of a company called Gojek. Many people listening have never heard of Gojek, especially people in the US. So just to start, can you just describe what is Gojek, what do y'all do? And then also I think more interestingly is just the scale of I think people in the US, their mind will blow once they hear the scale you've reached with this company. They probably hadn't heard of it.

**Kevin Aluwi** (00:06:03):
So Gojek started as a motorcycle taxi based service. So it's a kind of uniquely Indonesian things where we have millions of motorcycle taxi drivers in all of the urban centers in Indonesia. And so we started with a very local problem and the first product was a on-demand super app, if you will, where you could ask someone on a motorcycle to give you a ride, send a package for you or buy something and deliver it to you. This then evolved over the years into a more general on demand consumer super app that also included car drivers and other services ranging from the ones mentioned to grocery deliveries and payments and financial services.

**Kevin Aluwi** (00:06:52):
And today we took the company public about a year and a half ago after we merged with Indonesia's top e-commerce platform. And we've managed to also expand outside of just Indonesia, where today we have about 2.7 million drivers across Southeast Asia. We've completed about 3 billion orders last year, so that's 3 billion orders. So the scale of our region is often under underappreciated, where we also have about 15 million merchants doing general e-commerce, but also restaurants on our food delivery service. And on that IPO, we're pretty proud to say that it was Indonesia's largest IPO of all time, where we raised over a billion dollars at something like 27, 28 billion dollars in terms of valuation.

**Lenny** (00:07:50):
And these numbers you shared 2.7 million drivers, 30 billion orders,

**Kevin Aluwi** (00:07:55):
3 billion.

**Lenny** (00:07:57):
3 billion. How would that compare to an Uber or Lyft?

**Kevin Aluwi** (00:07:58):
I don't know what their latest numbers are, but just in terms of the numbers of people and the number of activity, I would place our scale among the largest US companies.

**Lenny** (00:08:10):
That's pretty wild that there's this company out there that a lot of people didn't know about that is basically of the scale of Uber and Lyft.

**Kevin Aluwi** (00:08:17):
In terms of volume, I would say that we're up there with Uber globally and definitely larger than Lyft. I don't remember how many drivers are in the US, but we definitely have more drivers in the region than all of America.

**Lenny** (00:08:35):
Just to kind of check this check box, you said it was a super app. What are all the things that Gojek does? Just whatever you want to share, all the things that you can do.

**Kevin Aluwi** (00:08:43):
From the point when we had the most services, we had everything from ride hailing to package delivery to food delivery, to grocery deliveries. We had moving services on trucks and vans. We had on demand massages, cleaning services. You could get your hair done on Gojek, you could order movie tickets, you could get a loan, you could pay for things. I think at our peak we had something like near 30 different services all in one app.

**Lenny** (00:09:18):
I think it's like you're officially a super app if your founder can't even remember all the things that you do right now.

**Kevin Aluwi** (00:09:25):
Yeah, definitely. I would challenge anyone within the company to be able to name all of our services that we've ever had on the app because it was pretty wild at one point. And I'd love to talk a little bit about my thoughts on super apps at some point during the session because I definitely have some mixed views over it as a product strategy as we've gone through that whole cycle.

**Lenny** (00:09:54):
It might be actually a good time just to jump into it. I know that I was actually saving that for later, but this might be a good time. And part of the reason I think this is really interesting is if you open up Uber these days, it's like 40 things that they're offering now. Elon at Twitter is talking about turning Twitter into a super app like payments, communication, messaging, all these things. So I think it's a really interesting trend that continues to pop up here in the US and I would absolutely love to hear your perspective on super apps.

**Kevin Aluwi** (00:10:19):
Okay, I'm going to come off a little strong on this, but I am kind of annoyed at how much it's being mentioned these days. It's really popular in VC-consultant-analyst circles because it sounds really great on a strategy deck because all of the things that are really appealing, we'll talk about lower customer acquisition costs, higher attach rates to different products, talk about higher retention across different services, the ease of cross-selling and upselling. All of these things sound great, but in reality, a lot of those benefits don't pan out. And one probably really good example that I like to reference is that I remember one of our products was mobile phone top up and recharge. In Southeast Asia, a majority of people are on prepaid plans instead of postpaid plans. So everyone basically buys their minutes and their data plans upfront in the beginning of the week or the beginning of the month.

**Kevin Aluwi** (00:11:27):
So we had a product which was a mobile top-up product. And so the reason I mentioned this specific product as a really illustrative point on super apps is that it's a product that 95% plus of our customers need because they're all on prepaid plans. So it's a very relevant product. And we had our UX research research team actually look into why the engagement in the product wasn't as high as we thought it should be. So one of the questions that our URX team asked our customers was like, "Hey, do you know that you could top up your mobile minutes and by data on the Gojek app?" And only about 40% of our customers, like 30 or 40% of our customers knew that this product existed. And that completely blew our minds because one, it's a product that is relevant for all of our customers.

**Kevin Aluwi** (00:12:25):
Two, it was literally there on one of the six buttons on the homepage. And I think the insight that we got here was that there kind of needs to be a unifying concept across all of your services within the app for your users to be able to think about your product in a sensible way. And for us, the way that our customers thought about us was that they thought about the driver. And so when we went from ride hailing to package delivery to food delivery, to grocery delivery, customers really understood that. And we didn't have to sell this idea to our customers that you had all of these services under one app because they thought about the Gojek driver. That made sense. You can easily cross sell somebody from a ride hailing customer to a grocery customer or a food delivery customer because they understood the unifying factor there being the driver.

**Kevin Aluwi** (00:13:24):
But then when you start doing other things that don't have that unifying factor in terms of the concept that a customer has when they think about your service, it starts breaking down. So one other fun UXR insight here was when we launched massage services. So we had at one point though we've shut it down a few years after, we had massage services where you can order a masseuse to come to your place. And a question that many of our customers asked was that, "oh, is the driver going to come into my house and give me a massage?" And for us, that was insane. Of course not, our drivers are not trained masseuses, but that was the question that people asked because they thought like, "oh, this app is an app for these driver related services, so if there was a massage service, I'm assuming it's that same man who's going to give me a massage."

**Kevin Aluwi** (00:14:17):
And so I think this kind of illustrates the importance of having these unifying concepts that are easy for customers to think about the multiple different services. It's not as simple as just saying, oh, we have a lot of engagement, we have a lot of eyeballs at a service. And then you have a super app that makes sense for customers. And so that whole nirvana of lower CAC, higher retention that are all on these great strategy decks often don't pan out because you kind of have to then resell this idea of like, oh, this is another service and that you can use. And that's a bit of investment that you have to actually put in terms of advertising and customer education that increases those customer acquisition costs.

**Kevin Aluwi** (00:15:03):
And it also leads to design constraints because there's only so many ways you can display a whole bunch of different services that actually have little to do with each other, which is why when you see super apps today, it's kind of like this giant menu or this giant grid which does limit the design decisions that you can make, which is unfortunate because if you actually, I think it's an unsolved problem at this point.

**Lenny** (00:15:28):
It's hilarious story about the massage product. Sounds like a lot of startups are going to have some issues scaling to new products and trying to become a super app. I want to shift a little bit and talk about brand. I did a little research on you ahead of this chat. I watched your Marshall graduation and speech and a few other interviews you did, and something that came out of your previous writing and talks is just how much you care about brand and how much value you put into brand. And that you just have a lot of opinions about the importance of brand. And to me and to most people, brand is this really squishy thing and it's hard to know what exactly to do to build your brand, when to prioritize it, how to prioritize it amongst other things you're doing, especially early on. So I'd love to hear your advice for founders that are listening and just like, what should I actually do around brand? What's your advice for how to tactically do something about brand and also just why do you think it's so important?

**Kevin Aluwi** (00:16:23):
I do agree with you that it is kind of this squishy thing that most people see as an afterthought, may be because it is kind of this squishy thing that it's hard to define, but I'm a very big believer that the two most important things in a consumer business are product and brand in that order. And I don't think I need to sell the idea, especially to your audience. That product is absolutely critical and probably the most important. But brand as an afterthought is definitely one of the areas where I think there's a giant missed opportunity for consumer tech businesses. And I get why we opened the session by talking about the size of the business to get an appreciation of the scale for audience members who might be unfamiliar with us or with the region.

**Kevin Aluwi** (00:17:16):
But I wish I did have to start there because we actually started as a very scrappy company where we were by far the underfunded player and without brand. We probably would've never gotten to escape velocity beyond that scrappy stage, we've maintained our leadership in Indonesia through a lot of the things that we actually did on the brand side to give you a sense of how scrappy we had to be in competition.

**Kevin Aluwi** (00:17:52):
For the first six months after launching our app, we had only raised about $2 million and our regional competitor had already raised 250. So they had literally more than a hundred times more capital than we have. So it's easy to talk about what we built as this kind of giant business, but we came from a place where we were seriously underfunded. And I think a big reason why we survived was that we built a great brand for our consumers and for our drivers and for our merchants. And I think that great brands create associations in their customer's minds that transcend the typically transactional or utilitarian one that most people have with businesses and they become part of one's identity.

**Kevin Aluwi** (00:18:42):
I think some of the best-in-class examples of these are probably all the Apple fanboys and fangirls, Nike sneakerheads, for these individuals, the brand becomes a really big part of their identity and their loyalty towards the products of the company go beyond a relationship that can easily be swayed just through discounts or other more features that other competitors might have. And so I'm a really firm believer of how important this is because you can see it if you step out of the tech bubble for a second, you can see that there's so many great companies out there that really rely on the strength of their brand to build these fantastic businesses and to create great experiences for their customers. And you ask, what are the things that one can do?

**Kevin Aluwi** (00:19:45):
I think for us, we invested a lot in our brand across multiple areas. And I think one specific area that I think is really important is that you create consistency across all customer touchpoints. And so branding is not just cool logo, cool advertising, fun imagery, but it's really about the impression that a customer or user has with your product and with your business. So having that consistency across all customer touchpoints is really important. So how you write copy and advertising and in the app, how you've even designed the app, but we were the first company of scale to have ads that don't take ourselves too seriously. We make fun of ourselves, we make fun of our cultural observations of Indonesia. And again, to just build this overall field that like, Hey, we get, we are part of the overall culture of Indonesia. And I think even going beyond the more aesthetic or communication oriented investments, we also leaned into cultural artifacts in our product features to really build this brand that is part of day-to-day culture.

**Kevin Aluwi** (00:21:09):
One of my favorite cultural artifacts is that in Asia it's fairly common to send food as gifts to your loved ones or maybe people you're interested in dating. So people would send over food as gifts to their romantic interests. And so when we launched our food delivery service, a lot of people were actually using it for this, I'm going to send it to my boyfriend or my girlfriend or the person that I'm interested in dating. And so it became this whole cultural phenomenon of sending go-food for these people and we kind of lean into it in our product feature where all of the other players in the market at the time basically only allowed you to deliver food to your home or your office, but we actually created a feature that allowed you to choose a delivery point that was far away from where you were.

**Kevin Aluwi** (00:22:04):
There was a lot of reasons why other companies didn't allow it at the time because it's like, oh, it might be used for fraud and stuff like that. But we leaned into it, we leaned into it and actually created features that allowed to put your pickup point far away from where your actual location was. And then we just had fun with this whole idea of go-food dating. And so yes, it's kind of part of branding, but thinking about branding beyond just marketing communication but actually be as being relatable and being part of the culture and being sensitive of what that culture is, I think was something that we did really well in the early days that allowed us to continue maintaining leadership in spite of the fact that our competitors had more money, which meant that they could offer more discounts, they could offer more incentives to drivers, but we really kind of lean very hard into being not just a utilitarian commodity, which is what a lot of people would say is the nature of our business to some level of accuracy.

**Lenny** (00:23:08):
So just to get even more concrete, one takeaway from what you just shared, which is interesting, is the first part of figuring out how to approach your brand is what's the personality of your product for you? You said it was like we're just of the people, we're like you, we're here to help you, make your life easier. And then that informs the copy, the messaging, be a little, I forget how you describe it, but just almost bad grammar and stuff just because it relates more to people and then some of these product launches that connect to that. So maybe if there's anything else you want to add there that'd be interesting. And then what's like, I don't know, one or two moments that most helped build the brand. I know you're kind of famous for having helmets and jackets on the drivers that help spread the Gojek brand. Is there anything else that just like, wow, this was really effective to build this brand that ended up dominating Indonesia?

**Kevin Aluwi** (00:23:58):
The jackets and helmets piece I think is really, really important for two reasons. One, the more obvious reason, which is that because they were just all over the streets of many cities in Indonesia, people were familiar with the imagery and the names, but I think it's also really important that people saw what was happening. So if we were like, I don't know, an airline and we branded a bunch of people on the streets with our brand, yeah, sure, that might help with brand recall and people might know about the name. But what was really powerful was that when people would be seeing these drivers with their jackets and helmets, they would be seeing passengers on the backseat as they were stuck in traffic. So I'm stuck in traffic and I'm seeing these people whiz past me with with this imagery on them, and immediately I get that association like, oh, I'm stuck in traffic, but I could be out there cutting through traffic on a motorcycle or you see them carrying packages or delivering food, and you immediately get like, oh, these are guys who can deliver food or deliver packages for me.

**Kevin Aluwi** (00:25:14):
And so it was like this beautiful combination of one just having that imagery and having that visual everywhere as a reminder of the brand. But more importantly, it was also a physical reminder of the service of what we do and of how we can help you. And so looking for these opportunities where again, customers can make that connection between the logo and the colors and the name with actually what the service is, I think are the opportunities that I would say people should look out for. They're admittedly quite rare, which is why in my opinion, the laziest kind of branding tends to be the most popular. Just put your name and your copy on a billboard or on a CPM or CPC campaign. But there are these opportunities I think, on being able to reinforce the value proposition of your business in a way that is beyond just visual recall. And I think that was why that specific anecdote is something I like to talk about because it was really one of those special things that reminded people on why we're here.

**Lenny** (00:26:37):
Yeah, I think you tweeted that it was one of the most important things you ever did as a company is decide to put these logos on the helmets and jackets. Reminds me of Lyft's pink mustache, which went away, but felt like a really important way for them to differentiate.

**Kevin Aluwi** (00:26:51):
No, totally.

**Lenny** (00:26:53):
You talked about how scrappy you've been, and I want to dig into that a little bit more. I think there's like US startup scrappy, and then there's like Gojek scrappy, and it'd be fun to hear maybe a story or two just to illustrate how ridiculously scrappy you were as a company early on, especially.

**Kevin Aluwi** (00:27:11):
One thing that we did in the early days that was absolutely crazy was that we were one of the pioneering companies, one of the pioneering technology companies in Indonesia and in Southeast Asia. And so we came into a environment where a lot of the things that maybe companies or people in more developed economies take for granted, for example, having electronic or digital payments, that was something that actually didn't really exist that much when we first started. And so we had a problem of actually trying to pay drivers because drivers every day we would be paying out incentives or just having customers pay with their credit cards or their store balance, and then we'd have a challenge and getting our drivers to actually be able to take that money out for their earnings. And in the early days, we actually had cash booths. So we actually had physical spaces with a vault and cash sitting in the vault where drivers can show up that, oh, this is my driver ID and this is the balance that I have with you. Please give me the cash.

**Kevin Aluwi** (00:28:31):
And so we would have these actual physical locations where there would be lions of drivers essentially taking cash. And we eventually figured this out of like, okay, we'll work with a bank and integrate with an ATM network and all that. But in the early days we just did it ourselves of building essentially a mini at ATM network, which I think even that sounds too fancy of what it was it. Because it was literally a booth with a vault with cash in it. And we had at the time already tens of thousands of drivers all across in Indonesia.

**Kevin Aluwi** (00:29:10):
Another scrappy story that actually Crystal reminded me of recently that we did was at the time there was a lot of fake driver apps out there because we didn't have all of the security investments that we eventually made, things like code obfuscation and better API security that wouldn't allow for these fraudulent driver apps, these basically third party driver apps to connect to our platform. So there were a lot of these drivers using these third party driver apps that were doing things that... So they were kind of doing unsavory things like stealing driver details, some of them even as bad as financial details so that they can then at some point drain driver funds. And the way that they did it, the way that they convinced drivers to actually use these apps was that they actually added some features that at the time we didn't allow. So things like we wanted drivers to be conscious of what was happening on the app, and so we would actually make sure that drivers would push the accept order button.

**Kevin Aluwi** (00:30:28):
We made sure that that was the only way that drivers could accept orders, but this app had a functionality that would automatically accept orders as soon as they came in. And so actually it was kind of this interesting situation where they were doing things that were fraudulent and were not safe for the integrity of the platform, but at the same time they were also providing some value to the people who were using them. And so at the time we had to make a decision of like, okay, we need to nip this in the bud and one way that we could have done it, that would've taken time was it really invest in a lot of the technical security aspects of it, but we didn't have the bandwidth to be able to do that. Engineering and security talent is actually super scarce in Southeast Asia at the time, still is today, but at that time extremely scarce.

**Kevin Aluwi** (00:31:25):
And so we ended up making the decision of actually copying those features. So we actually saw all of these third party fraudulent apps and instead of building a whole system to prevent them from being built or preventing them from working on the platform, we just said, "Hey, let's take their top two or three features and let's build them into our app." And that actually significantly reduced the number of users on these third party apps just by having this mentality of you can't beat them, then join them. And that I would say that wasn't a philosophical decision or a principal decision. Is was actually a decision made out of necessity because we simply couldn't build all the capability to combat these apps at the time?

**Lenny** (00:32:13):
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**Lenny** (00:33:03):
These are hilarious stories that you had to compete with these ripoff jail broken apps, fraudulent apps, and then you had to build a cash box network all over the country. That's amazing. I knew there would be good stories in this question and I'm glad you delivered. There's also this feeling of within Gojek of just doing the hard thing and you just shared a couple stories of this versus the simple... A lot of startups are like, let's do the simplest thing, feels like you guys lean into the hard thing. Why is that? Where'd that come from? And then is there any other story of something that you did that was like, we'll do it the hard way?

**Kevin Aluwi** (00:33:41):
I really don't like the idea of moats. Again, one of the concepts that gets thrown out a lot by strategy type folks of what's the moat of your business or your product? And usually people are looking for an answer like, oh, look at this capability or look at this feature or look at this distribution partner or all of those kind of things. And I don't believe that any moats are durable over time. Eventually with enough time all moats can be crossed. And I think one so-called moat that doesn't get talked about enough is the fact that you're able to do hard things because hard things are hard and just simply doing things that are hard, as long as they create value to your customers, actually is a position that makes it harder for your competitors to be able to win over your customers because it's hard to do those things.

**Kevin Aluwi** (00:34:52):
And probably another example of doing something that sounds very difficult was that in the early days of Gojek, there was a lot of resistance to our services and one of the forms of that resistance, one of the more most common form of that resistance in the early days was actually by motorcycle taxi mafia. So you would have these areas that are essentially controlled through violence by specific area mafia. And when we start having drivers pick up orders and pick up passengers, these people would actually physically assault our drivers. We've had everything from bricks thrown at our drivers to knives and machetes being brandished at them to just physical altercations, literally mobs of people getting into these brawls. And there was a lot of these kind of things that actually happened in the streets of Jakarta at the time. And I think it would've been easy for us to say, "Hey, they're all contractors, they're third parties, let them kind of just sort it out."

**Kevin Aluwi** (00:36:14):
But instead we actually hired private security. So we actually work with private security companies to help these situations, to help our drivers in those situations, to help extract them out of these sticky situations. And so we actually ran a fairly big private security operation for a fairly long time until it became common to have Gojek drivers do all of these things across cities. We actually ran this very operation intensive thing just to make sure that our drivers could be as safe as possible and it showed our commitment to the driver community, it showed our commitment that we cared. And again, going back to that earlier point around having that branding association, drivers knew that, hey, we weren't just a platform that didn't care. We actually cared about their safety and that helped build that goodwill even as competitors started coming in and paying more money, we still had a lot of loyalty within the driver community because of things like that.

**Lenny** (00:37:30):
How did you actually have a security person on a motorcycle? Were they pretending to be the rider and then just get out and punch them in the face?

**Kevin Aluwi** (00:37:39):
A minority of situations were like that, but a lot of that was just like, having an on-call service where they could just dial a number and somebody within a 5-10 minute distance would actually show up. And so we would have these patrols effectively in specific hotspots where if there was a situation brewing that they would instantly or almost instantly show up to the site and help diffuse it.

**Lenny** (00:38:13):
I love that you have this super app that's doing all these things for people. Plus within the company you've built all these mini businesses, like a whole bank to pay people, private security company. There's probably some other... Crystal shared a story of you guys rented out a stadium for drivers to collect all the drivers and give them phones.

**Kevin Aluwi** (00:38:33):
Yeah.

**Lenny** (00:38:34):
Okay. This is great.

**Kevin Aluwi** (00:38:34):
Yeah, that I think is probably one of the hallmarks of this region in general where I have no doubt that what we were building and what we are today is a technology company, but I do think that in the early days you do have to be a lot more operations heavy. And then I think that lends to that scrappiness because there are a lot of things that to solve elegantly and technically will take a lot of time and just kind of over focusing on those type of solutions I think would be doing your customers a disservice because there are opportunities to make things a lot better just through probably more innovation in operations to kind of kickstart things until you have the more elegant, scalable, technical or product solution.

**Lenny** (00:39:38):
That reminds me that at Gojek, you held tons of different roles throughout the time you were there. You were obviously co-founder, your Co-CEO at one point, defacto CPO at one point, CIO, CFO. I heard that you were writing like push notification copy, became a driver at one point just to keep things running. So feels like another good example of exactly what you're talking about of just doing the hard thing in the operational component.

**Kevin Aluwi** (00:40:05):
I mean, yes, actually I did have a stint as an amateur performance marketer in the early days of Gojek. I would write copy, I would upload ads onto Facebook and Google and try and do my best in optimizing our online marketing spend. But I think I did all of those things, not because I wanted to be scrappy necessarily, but I do think that as, and this is probably most relevant for founders, less for executives, but I think as a founder, I do think it's really important to understand the work that needs to be done in order to see what excellence looks like. And for us, again, we came from an ecosystem where the availability of experienced talent was relatively low. And so for me it was very hard to be able to say, "oh, let's hire person X from organization Y with job description Z," and we know that they probably can deliver because again, the talent availability was really low.

**Kevin Aluwi** (00:41:16):
And so a lot of times I felt like I needed to understand, okay, what is this job? What exactly does it entail is, and seeing how bad I am at it allowed me to understand what good looked like. And so I held a lot of those roles just because I wanted to understand every part of the business as best as I could in order to then find somebody who could do it orders of magnitude better than myself. I would say that is true for all of these roles except for being a driver. I think being a driver, I wasn't trying to understand what excellence as a driver look like. Obviously the drivers do a really challenging job and I think I just wanted to understand what that role was like to build a lot more empathy towards the job and make sure that our product was catered towards what those needs were.

**Kevin Aluwi** (00:42:12):
So when we first launched our car ride hailing services, I think I was the first actual driver on the app and I would every now and then be a driver. And I remember the early days when I actually picked up a customer. It was this lady and she put in her destination as a mall. And so I went to this house and I knew that, okay, I needed to drive to this mall, but then this lady comes out with this giant bag and so I had to hop out the car, take this giant bag, put it in my trunk, and then off we went. And in the middle of the drive she's like, "Hey, I need to drop off and do my laundry on the way to the mall." And I just had to, "okay, cool." We took a detour, I lugged this giant bag out of our trunk and helped this lady do her laundry.

**Kevin Aluwi** (00:43:17):
And then we went to the mall and I got very little money out of that experience and it wasn't instant, but this is eventually what led to, I think a lot of the support I gave to our driver teams when they were pushing for, Hey, we need more waiting fees, we need to add multiple stops in order to make sure that hey, a lot of this extra work was actually compensated. And it was something that I obviously experienced personally and it was something that I definitely was excited about as a set of product features and principles when it came to building our driver app.

**Lenny** (00:43:58):
It feels like having to do that ends up being a feature as you said, that you actually experienced a lot of these challenges and you said the really good point about knowing what to hire and what these people are going to actually do.

**Kevin Aluwi** (00:44:07):
Yeah.

**Lenny** (00:44:07):
That's interesting how that often turns into a good thing. I know you also have a pretty interesting journey into tech. What can you share around that?

**Kevin Aluwi** (00:44:18):
So I am basically a failed finance professional. I didn't really know what I wanted to do in my life. And in 2005, which is when I entered college, the hot sexy thing to do was finance. And I guess that was what I wanted to do. And I went, studied finance, and then the crash of 2008 happened and I graduated 2009, so it's probably the worst time to try and be a finance professional. And so I went through a really challenging time there, but eventually I got a job at a boutique investment banking firm. And that was, I thought like, okay, now I was set for life. I got the job that I wanted. I'm working in finance. But then long story short, I was not very good. I was not very good. My bosses thought I was underperforming. I didn't feel like I was performing, and I kind of left that field that I thought I built my entire, I guess future dreams and identity around.

**Kevin Aluwi** (00:45:32):
And after I did that, I decided to take a bet in Indonesian technology because when all of this was happening was around 2010, 2011, and it was starting to see the development of the current technology giants in the US at the time. And I thought that it would be pretty cool if Indonesia ever had a technology industry to be part of it at the ground floor. And so I moved back in 2011 and it was super early. It was really early at the time where the level of talent, the level of funding, the level of product market fit, the number of people who transacted on the internet was also still super low. People still saw the internet as a place for chat apps and social media. And so the level of belief that people had in the space at that time was pretty low.

**Kevin Aluwi** (00:46:30):
People didn't think that real businesses and real valuable products could be built, especially be built locally. And so taking that bet was something that I think it really panned out for us to be really early in the space, which today has become very vibrant to the scene. Southeast Asia has become, I think one of the most exciting spaces in technology in the world to date. But at the time it wasn't obvious. And being able to see that development I think was something that was really important to me because it really shows you what's possible in a very short time. And I think it's something that probably people in technology in the US can relate to, the people who've been working in this space for like 20, 30 years. But being able to see those early days for me was just really valuable and I think was an experience that I definitely cherish.

**Lenny** (00:47:31):
It's really hard to just build a company outside of Silicon Valley, and it was even harder back then. COVID and remote work almost made it the easiest it's ever been.

**Kevin Aluwi** (00:47:40):
Yeah.

**Lenny** (00:47:40):
Sounds like a lot of the fact that you were so far away from the Bay Area informed the way that you built this company, the scrappiness that you talked about. I'm curious if you have any advice for a founder who's trying to build a company now outside of, say the Bay Area or just US in general based on your experience.

**Kevin Aluwi** (00:47:58):
Yeah, look, it was super hard back then. It was particularly hard because Indonesia is such a valuable market, Indonesia and the rest, I would say primarily Indonesia just because of its scale. But I think overall Southeast Asia was just such a valuable market and it was interesting for global companies to want to win it. So we competed with global and regional companies, but the local talent and funding ecosystems were really underdeveloped. So that challenge of having to compete with the best in the world for customers in the market while also not having all of the resources available within the market to be able to build products and companies that can compete was I would say one of the most challenging parts of building probably in markets that are atypical or outside of Silicon Valley and maybe some of the other technology centers in the world like China and India.

**Kevin Aluwi** (00:49:01):
So some of my learnings probably there that I would take going forward is I think we talked a lot about being scrappy. In the beginning, we were a lot more ops-heavy than tech-heavy. And doing the things that don't scale through other means I think is definitely something that is absolutely necessary if you're building outside of these main technology hubs. Another thing I would say is you need to get good at remote work really early. And I think today that's kind of become a lot more prevalent as more and more people have experience with remote work. For us, we built an engineering center in Bangalore in 2015, and this allowed us to compete a lot better with the global giants because we had access to a really deep talent market in India at the time, but we were really early in this whole remote work thing because it wasn't common for people in our region, but also globally to have so much talent concentration outside of headquarters.

**Kevin Aluwi** (00:50:14):
And I do believe that companies who want to compete against world class competitors outside of these technology centers like Silicon Valley need to become good at remote work really fast because getting that talent probably means having offices or individuals who are outside of your home market or your headquarters. And probably the final I would say tip here is don't just copy, because Gojek was not an Uber clone, even though that was kind of how some investors or analysts talk about us, we were focused on a solution that was uniquely an Indonesian phenomenon, the motorcycle taxi driver. And this led to both product and branding innovation. On the product side, we were an on-demand super app because we saw that a human being on a motorcycle could do a lot of things. And so we built a product around that idea and hence we ended up with a super app even before super apps were really a thing.

**Kevin Aluwi** (00:51:24):
And then that branding point that we talked about a little earlier about giving our drivers jackets and helmets so people could see them zip around town, which actually doesn't make sense if you're a car ride hailing service because it's not very easy to brand a car and the drivers are inside the car. But all of our competitors at the time when they first entered the motorcycle ride hailing space didn't brand their drivers because they came from a car-centric view. And so again, understanding your unique market dynamics is also really important if you're building outside of these technology centers.

**Lenny** (00:52:10):
We've been chatting about Indonesia and Southeast Asia. I'd love to hear just what should people know about that market? We've chatted about what you guys have built and a few other companies here and there, but what companies should people be aware of what's happening? What's the latest, what's exciting?

**Kevin Aluwi** (00:52:24):
Yeah, I think specifically Indonesia, most people don't know that Indonesia is the fourth largest country in the world and that Southeast Asia holds almost 10% of the world's population. But beyond the macro picture, I think also we've experienced a pretty unique level of pace of adoption for products with great product market fit. So products with great product market fit grow tremendously fast in this part of the world. And in 2015, for example, when we launched our app, we grew more than a hundred percent month on month for the first 16, 18 months. So we more than doubled every month for more than a year.

**Lenny** (00:53:16):
That is insane. I've never heard of that.

**Kevin Aluwi** (00:53:19):
No, and our investors at the time, Sequoia is one of our investors at the time, told us that this was the craziest growth story that they've ever heard of in the world. And I wouldn't say because of our necessarily our brilliance, it was a combination of how in Indonesia and in Southeast Asia, there are a lot of these things that are obviously broken and could be improved with better technology and better products. But we also have in this region a very young population who are excited to try new things. And so if you find a solution that really resonates with a lot of these common day-to-day problems, the adoption curve is just absolutely insane. And I think it's one of the things that are definitely unique to developing regions like this one.

**Kevin Aluwi** (00:54:14):
One company that's really interesting for example, just to give a flavor of the type of seemingly off the wall product or company being built in this part of the world, there's a company called eFishery, and what they do is they basically create a closed loop ecosystem for fish farmers in currently, I think they're only operational Indonesia or they're recently expanding beyond Indonesia.

**Kevin Aluwi** (00:54:45):
They help farmers feed their fish through this IOT smart device that helps measure the amount of fish feed that needs to go into the ponds, but they also then help farmers do things that get financing and also sell their produce out to local or even regional or global markets. And it's a company doing something like a quarter billion dollars in revenue and it's profitable and it's basically a fish farmer, a close loop ecosystem. And it's pretty wild that something like this exists, but it does speak to, I think again earlier what I said earlier about the hunger that the population have for better solutions. And if you can find these better solutions, you can really build companies of the very meaningful scale very, very quickly.

**Lenny** (00:55:42):
So at this point, you've stepped down a CEO, you've stepped down from the board, what's next and how does it feel?

**Kevin Aluwi** (00:55:50):
Yeah, I'm still on this journey honestly, of how does it feel. I think that building Gojek is by far the most important professional experience and frankly, one of the most important life experiences I've had. It's made me a way better person actually. And now that I've stepped away, I am not as bored or as aimless as people would expect after having such a kind of all-consuming thing be part of my life experience.

**Kevin Aluwi** (00:56:37):
What's next? Honestly, Lenny, I don't know. I don't have a plan at this stage. I do some angel investing on the side. I work with other founders to be able to maybe just share some of these experiences that I shared today and just figuring out what makes me happy and what are the kind activities that I find rewarding. I don't know, maybe I'll start another company at some point. I think that's my default, but I think right now I'm just taking things easy and trying to figure out another problem I guess, that I could be obsessed about.

**Lenny** (00:57:25):
You've earned that time to explore and look for new problems. Is there anything else you wanted to touch on before we get to our very exciting lightning round?

**Kevin Aluwi** (00:57:33):
No Lenny. I think we've covered a lot today, and I just wanted to thank you for the time.

**Lenny** (00:57:41):
Amazing. It's absolutely my pleasure. And with that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

**Kevin Aluwi** (00:57:48):
Yes, let's go.

**Lenny** (00:57:50):
What are two or three books that you've recommended most to other people?

**Kevin Aluwi** (00:57:54):
What You Do Is Who You Are. I think that was the second most popular Ben Horowitz's book, but I'm really obsessed with building interesting and engaging cultures, so I think that's one. Another is a classic marketing book. Again, we talked a lot about branding today, so there's this book called How Brands Grow by Byron Sharp. I don't agree necessarily with everything in it, but I do think that it's a great primer on how to think about branding and marketing.

**Lenny** (00:58:25):
Favorite recent movie or TV show?

**Kevin Aluwi** (00:58:27):
Favorite recent movie, The Menu and favorite recent TV show? Netflix show is a Cyberpunk 2077 Edge Runners.

**Lenny** (00:58:38):
Oh, wow. I haven't heard of that one.

**Kevin Aluwi** (00:58:39):
Oh, you should check it out. It's super cool.

**Lenny** (00:58:42):
I'll go check it out.

**Kevin Aluwi** (00:58:43):
Yeah.

**Lenny** (00:58:43):
Favorite interview question that you like to ask.

**Kevin Aluwi** (00:58:46):
Tell me about a subject or activity you've been obsessed with for a long time.

**Lenny** (00:58:51):
What do you look for in an answer that's like, okay, this is good.

**Kevin Aluwi** (00:58:54):
I want somebody to basically almost pitch to me an obsession they have than makes me interested in knowing more into that subject. The more obscure, the better and the more passionate they are about an obscure thing, even better. And I think it shows people's capability to be really passionate about something and sell something and think about something in a very structured and detailed way.

**Lenny** (00:59:25):
What are some products that you love and have recently discovered?

**Kevin Aluwi** (00:59:30):
Two products, I think right now that I've found absolutely delightful. One is the ARC Browser. I know that it's gaining a lot of traction out there, but I'm a very chronic tab hoarder. My Chrome tabs are just all over the place, and I love that they've figured out I would say the best approach to kind of tab management, and there's just a ton of little delightful, awesome design details in the app that I think is just really cool. And it's a browser. When's the last time there was a really cool browser that came out? So I also love the ambition that the company has.

**Kevin Aluwi** (01:00:09):
Second product, Steam Deck. I'm a huge gamer, and I think it is probably, I would say the best game platform to actually build on the vision of truly portable mobile gaming.

**Lenny** (01:00:25):
I love your point with ARC for tab hoarders. I also used to have a lot of tabs and I love it just auto deletes stuff and just disappear, and it forces you to lose your tabs and it works out surprisingly.

**Kevin Aluwi** (01:00:38):
Final question.

**Lenny** (01:00:38):
I'm curious what comes up for this one? What's something you've recently changed or that you've heard of someone at Gojek recently changed in their product development process that was maybe minor, that had a tremendous impact on the team's ability to execute.

**Kevin Aluwi** (01:00:53):
One relatively minor thing that I thought had a lot of impact with execution is being very clear that whoever is accountable for the results should also be the decider. I found that a lot of literature out there says that product teams should be this communal best ideas come from everywhere group, which I think is well-intentioned and absolutely everyone should contribute ideas, but I think not having it be super clear who is accountable and who is deciding often slows down execution a lot. And I think when we switch to making it really clear that who was the decider for any kind of product development process, I think our execution definitely improved significantly.

**Lenny** (01:01:37):
Amazing. Kevin, thank you so much for being here. Gojek is such an interesting and important story, and I feel like most founders can learn something from the story, so I was really excited to bring you on and to hear a lot of these wild stories that you shared. Two final questions. Where can folks find your line if they want to reach out, learn more, and how can listeners be useful to you?

**Kevin Aluwi** (01:01:57):
I am @kaluwi on Twitter. That's also my email, kaluwi@gmail.com. I'll always be happy to chat about Gojek or just generally anything technology related. Again, I have nothing I'm working on at the moment, so I just would love to jam with cool people.

**Lenny** (01:02:22):
Amazing. Thank you again for being here.

**Kevin Aluwi** (01:02:25):
Thanks, Lenny.

**Lenny** (01:02:28):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

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