---
title: "Lenny's Podcast — 2022 Q3 合集"
date: "2022-01-01"
source: "Lenny's Podcast"
url: "https://www.lennysnewsletter.com/"
---

<div v-pre>


# Lenny's Podcast - 2022 Q3 (20 episodes)

This file contains 20 articles/episodes.

---

## [1/20] Sanchan Saxena (VP of Product at Coinbase) on the inside story of how Airbnb made it through Covid; what he’s learned from Brian Chesky, Brian Armstrong, and Kevin Systrom; much more

**Lenny** (00:00:02):
I feel incredibly lucky to have gotten to work with Sanchan while I was at Airbnb. He joined Airbnb as a director of product and quickly moved up the ranks to head of product for all of Airbnb. Before Airbnb, he spent almost four years at Instagram as head of product for Instagram Ads, and then he created and led the Instagram Shopping product and team.

**Lenny** (00:00:21):
Before that he was director of product at Yahoo and a PM at Microsoft. And today he's the VP of product at Coinbase. I don't think I've worked with a harder working PM, particularly someone who's incredibly kind and nice and generous.

**Lenny** (00:00:34):
In my conversation with Sanchan, we cover what he's learned from working with some of today's best CEOs, including Brian Chesky, Brian Armstrong, Zuck and Kevin Systrom, what it was like inside Airbnb when COVID hit and how they made it through travel completely stopping, how to set up your product development process at a startup, tips for hiring amazing product managers, when to hire your first PM, when to A/B test and when not to, and so much more.

**Lenny** (00:00:59):
I hope you enjoy this episode as much as I did. So many product managers are basically treated like project managers. You get higher thinking that you'll be deep in product strategy and vision, and getting to know your customers, only to wind up organizing other people's work and finding backlogs and optimizing tiny, tiny features.

**Lenny** (00:01:21):
If this sounds familiar, you need Dovetail. Because Dovetail gets that the true heart of product management is understanding what customers want, why they want it and how to give it to them. That's why Dovetail built a suite of user research products that help you get to the core of what your customers really want and why they want it.

**Lenny** (00:01:38):
Dovetail offers a suite of powerful analysis tools to help you identify themes, patterns and insights in your customer interviews, allowing you to make better, data informed decisions about what solutions you should build next. Organizations all over the world, like Atlassian, Canva, Datadog, GitLab, Sketch, Nielsen Norman Group, and Deloitte use Dovetail to get a better understanding of their customers and build better products.

**Sanchan Saxena** (00:03:26):
Thank you, Lenny, for inviting me. Excited to be here and chat with you today.

**Lenny** (00:03:29):
Absolutely. My pleasure. I was really lucky to work with you at Airbnb for many years, where you were a beloved product leader. And then you went on to do bigger and better things now at Coinbase. And I'd love to just hear how you first got into product, and then just a little bit of your journey of how you got to where you're today, where you're basically head of product at Coinbase.

**Sanchan Saxena** (00:03:49):
Yeah, happy to answer. Maybe I'll go back in time and start from my first job. I was in my third year of engineering where the entrepreneurial bug caught me, so to say, bit me. And I took a little bit of sabbatical from my engineering, which by the way, was in aerospace engineering.

**Sanchan Saxena** (00:04:03):
I wanted to be an astronaut, go to space. Unfortunately back then, there wasn't an Elon Musk for SpaceX. If you wanted to go to space, you got to work for a government agency, which I didn't like. Fast forward that to my third year of engineering and I start my company, raised a bunch of money, hired some people.

Didn't go as planned, so I [inaudible 00:04:20], came back and finished my engineering and got a job at Microsoft, which made my mom very happy. My mom said, "My son finally has a stable job. What the heck he was doing running some companies?" But jokes aside, I got a job at Microsoft, which was a great starting position.

**Sanchan Saxena** (00:04:34):
I started in engineering. But within a year or so, I moved into product. And I moved to the Silicon Valley office of Microsoft. Never worked in Seattle, but always worked in Silicon Valley at Mountain View. And I worked for this product called Hotmail. I don't know how many people know this or not, but there's an email service called Hotmail. I was one of the product people.

**Lenny** (00:04:50):
Absolutely. It's scary that people may not even know what Hotmail is at this point.

**Sanchan Saxena** (00:04:55):
Right? It's kind of crazy. Back in the day, it was pretty cool. I worked there, and then since then have been in Silicon Valley. So moved into product back in, I think, 2005 or '06, something like that, and since then been in product. I've been very lucky and fortunate to have stumbled upon incredible opportunities all the way from Facebook and Instagram to Airbnb and Coinbase.

**Sanchan Saxena** (00:05:16):
And fun fact, when I joined Instagram, it was still very small. And it was less than, I think, 50 engineers or something like that. Very tiny. It was pre-revenue. We made $0 in revenue. I still remember the day when Zuck told Kevin Systrom we got to go make revenue, and we made $0 back then.

**Sanchan Saxena** (00:05:30):
And was there till 2017. By the time it was like a billion monthly active users, multiple billion dollars in revenue, was my first hypergrowth experience as a product leader. And then in 2017, I joined Airbnb, which is where you and I worked together. There I had a dual role.

**Sanchan Saxena** (00:05:45):
I was a GM of Airbnb Plus, but also the head of product helping Brian Chesky scale the product management organization, establish the culture of it, and see how best we can build a world class part organization. And then after that, I took some time off, about six months, introspective to see what do I want to do next.

**Sanchan Saxena** (00:06:00):
And that is when I went into the Web 3.0 rabbit home, and that's when I learned more and more about Web 3.0, what's happening over there. I've always been investor in crypto since 2014, but never thought of it as a builder. I was like, "Ah, I don't know if I want to build in there. It seems cool. I can participate from the outside."

**Sanchan Saxena** (00:06:18):
But then the more I read, the more I realized, "Man, this is one of the biggest revolutions happening." And that's when I joined Coinbase and here I'm the VP product for ecosystems and a bunch of other stuff that I do here, and excited to be able to play a small role in this next revolution called Web 3.0.

**Lenny** (00:06:31):
Amazing. Just listening into that trajectory and places that you worked, I imagine people are wondering like, "Man, how do I follow a trajectory like that? How do I live a life like Sanchan?" Do you have any advice for someone that's maybe just starting out that may be wondering like, "How do I follow this sort of path? How do I work at all these incredible companies and get to maybe where you are now?"?

**Sanchan Saxena** (00:06:51):
Yeah, I look back at my career, one thing that is very true is that I never had that plan. I stumbled upon a lot of things. I mean, I wanted to be an aerospace engineer, didn't work out, pivoted. I started my own company, didn't work out, pivoted. I came to Silicon Valley, worked at Hotmail, didn't work out, pivoted.

**Sanchan Saxena** (00:07:07):
Things start to materialize when you actually take steps to do something. My biggest advice to people is, oftentimes the analysis paralysis of dotting every eye, crossing every tee sometimes chokes you out of opportunities. When you find something that gives you energy, just jump in with both feet. And try to go through that process, and pivot and learn, and pivot and learn and pivot.

**Sanchan Saxena** (00:07:29):
That's how you would create a great career as opposed to sort of a five year career plan and working backwards from that. Those things just don't work. The other thing I would say is I read this book early on in my life called the Little Bets. It actually was a reflection of whatever I did in my life. Before that I thought I was a weirdo, I don't know what I'm doing. And then I read that book and I realized, "Oh my God, there's some method to my madness. It's called little bets."

**Sanchan Saxena** (00:07:52):
You take little bets, you try them out. If they don't work out, you build rapid recovery and start to do something else. And that is the meta story connecting all the dots in my life, in all the career opportunities that I've had, just one piece of big advice I'll tell everybody. The second thing I'll say is product management is a very interesting discipline.

**Sanchan Saxena** (00:08:10):
You don't go to school for that. You don't get a degree for that. And most people that I know in product have stumbled upon product management. They were doing something else and like, "Oh my God, this seems cool. I want to do this." The advice I give early stage product people is you got to learn the art and the science of product management early on in your career.

**Sanchan Saxena** (00:08:29):
There's an art piece to it and then there's a science piece to it, and you got to be able to manage both of those things in your head. If you become too scientific, you miss out on opportunities because you can't see those opportunities using the scientific method of discovery, because they're too tiny or they're so farfetched that people cannot even understand them.

**Sanchan Saxena** (00:08:45):
And the art piece is really important for you to be able to sniff those out by being in the community, hanging out with people who are actually builders and learning where the next trends would be. My advice to people is go get a job which will make you the fastest learner in the field of product management.

**Sanchan Saxena** (00:09:00):
That is what will help you a lot. No course, no degree, none of those things will help. The most important thing will be how quickly can you jump in, learn the auto product management. Some people prefer doing that at a startup. Some people prefer doing it at a established fan company, which has processes and systems as well. It's your choice. But the fastest you learn that, the better it'll get for you.

**Lenny** (00:09:20):
Wow. I love so much about that advice. To go a little bit further on this last point. When people are looking for a company to go join to learn, to accelerate their career the way you're describing, what do you think they should be looking for? I know you said maybe a startup. Do you think they should join a startup? Do you think they should join a bigger company? What kind of things should you look for to find the best place to learn?

**Sanchan Saxena** (00:09:41):
Yeah, I think there is no right recipe for one, but it matters to the individual. I'll share both stories with you. The way to think about this is let's say you want to get to a destination, whichever destination it is, you probably want to get on the faster ship. You don't want to get on a slower ship. That's one metaphor to use in your mind.

**Sanchan Saxena** (00:09:58):
And then when you got to the ship, you know the ship will get there, but remember you are not going to get to your destination faster than the ship will. You got to understand what your destination is, then optimize the learnings from there. At a startup, you're going to learn a lot of things. There are three types of learning, a starter learning, meaning you can get started. You're a person who can get started. You see an idea, you see an opportunity, you can get started. Right?

**Sanchan Saxena** (00:10:21):
That is something that a startup will teach you a lot. You see something, you want to get started to do something about it, great, you'll learn a lot over it. And there's zero to one people who can then take what they have started and scale it to one. And then there are one and beyond people who are scalers, who will scale the system that is found product market fit.

**Sanchan Saxena** (00:10:38):
And I think depending on your journey, depending on your career, depending upon where you are, you might want to optimize for different types of learnings as well. What I advise people is there's a great way to go to Google, Facebook and Amazon and learn the scale mechanisms that these companies have built. And I look at Amazon and I get inspired by that company, because what they have figured out is how to scale innovation with 1 million employees.

**Sanchan Saxena** (00:10:59):
It's a pretty different learning. And you can't potentially find that at a startup. Similarly, the ability to just get started, the ability to see an idea, start hacking at it, start building it without the encumbrances of the processes and the system that these big organizations have, you can probably learn that in a big company as well. You got to figure out what are you optimizing for, what goes well with you.

**Sanchan Saxena** (00:11:23):
I've seen many successful leaders who will get choked up in a big company environment, and I've seen many big company successful executives who want to choke up in a very startup environment. And this is not for everybody. Both sides of the games are not for everybody. First and foremost recognizing what gives you energy, recognizing where you thrive the most is really important.

**Sanchan Saxena** (00:11:41):
For example, I am not the guy who can optimize a 100,000 employee company. I will never enjoy that kind of learning. I've done to some extent a large company thing, but I thrive in that starter to scale angle. But when it becomes too large, I start to lose interest in that kind of learning. Some people enjoy different things. You got to understand what it is and be able to optimize there.

**Lenny** (00:12:03):
Where would you say you learned the most of all the companies you worked at that helped accelerate your career most?

**Sanchan Saxena** (00:12:09):
I think I would rank Airbnb probably the place that I learned the most. And I'll share with you and your audience why I feel that way. I joined Airbnb back in 2017, making decent revenue, had good product market fit. I remember when I got there, the entire product management order was like 30 people or 40 people, something like that.

**Sanchan Saxena** (00:12:26):
You had three directors of product, very small still for a company that was generating a billion plus dollars in revenue. And then the context was there was this ambitious founder, Brian, who will never take no for an answer. And he would bend reality in many regards to make shit happen.

**Sanchan Saxena** (00:12:41):
And you are very familiar with those days as well, but you will have a practicability. You will leave the review thinking, "Shit, this is actually possible." The guy just inspired you that this is actually possible and you went in thinking it's not possible.

**Sanchan Saxena** (00:12:52):
What I found is that at Airbnb, I learned a bunch of different things. One, I learned how to build products where software is just one part of the product. Let me explain that a little bit. The product of Airbnb isn't the app. It is a means to an end. The product of Airbnb is the memories you're going to create when you sit in that Airbnb beautiful house with your family, with your friends, and you're building those memories. That's the product. It's in real world.

**Sanchan Saxena** (00:13:18):
And how you build a real world product which is of course powered by software, like the app, the website, et cetera, is different than just building a pure product that is purely software. I learned what is operations, how to scale operations, how to work with operations, how to create beautiful physical homes over there. The second thing I learned is just how to build great products.

**Sanchan Saxena** (00:13:39):
I mean, I got I think a masterclass from Chesky in how to build products by watching him act, behave, and make decisions as well. And we'll talk about it later today. But I learned some of my fundamental product principles from him, and working with him and the team that he had assembled, the design leaders, the engineering leaders, et cetera. I learned a lot over there.

**Sanchan Saxena** (00:13:59):
And last one but not least, there was still a hypergrowth thing. We were going through crazy growth. And then I learned what happens in leadership when coronavirus happens, the company starts to tank. It was a lesson in crisis management. I tell my friends I could not have gone to HBS Stanford business school to learn crisis management as much as I learned while being in the front row seat managing through that.

**Sanchan Saxena** (00:14:23):
My learning as a product leader from Brian as a hyperscaler, taking the product management organization from 30, 40 people to 200 people, and last but not the least, managing the crisis. I felt like it all compressed into three years something that you will learn in 30.

**Lenny** (00:14:38):
I imagine you had no sense of that sort of path or trajectory or learning when you joined Airbnb, it was like, "Hmm, this is going to be a great company, little [inaudible 00:14:46] things."

**Sanchan Saxena** (00:14:47):
Yeah, absolutely. And oftentimes it's a joke, but I'll say it out anyhow. Oftentimes you meet leaders who are leaving Facebook, Amazon, Google, and it's like, "Hey, here's my Excel spreadsheet. Here's how I imagine the startup that I'm joining will grow. Here's the valuation. Here's my life. Here's my compensation. That's it." None of that shit is going to happen.

**Sanchan Saxena** (00:15:05):
The companies have a different trajectory and you can't predict those things. So yeah, you're right. When I joined Airbnb, I thought it's going to be a walk in the park, just like Instagram was. I mean, Instagram wasn't a walk in the park. But relatively speaking, Instagram never experienced this kind of rapid pivoting of the reality, right?

**Sanchan Saxena** (00:15:22):
I'll share with you I was there when Instagram had less than a hundred million monthly active users, $0 in revenue, 50 engineers, till it had 1 billion monthly active users, billions of dollars in revenue and thousands of employees. And I don't remember a time where the reality got bended so badly that we had to pivot.

**Sanchan Saxena** (00:15:41):
In Airbnb's time, man, one fine morning in January, Brian and us were all talking about going IPO and taking the company public. Six weeks later, we are figuring out, "Damn, how do we make this company survive?" The revenues, if I'm not wrong, dropped to less in single digits of last year's revenue.

**Sanchan Saxena** (00:16:00):
And there is no head of product, there is no CFO, there is no COO, whoever has a business plan to say, "Hmm, what are we going to do when our revenue drops to single digits of last year's revenue?"

**Sanchan Saxena** (00:16:10):
I definitely didn't think that is what happened, but that's what ended up happening. Luckily, everything worked out, and I'm happy to share what we did and how we navigated through that with the audience, but it was some crazy, crazy times, man.

**Lenny** (00:16:21):
I was on the outside of that having left Airbnb a couple years prior and I was like, "Shit, what am I going to do now? I've been taking time off. There go all my Airbnb shares. I think I can get a job soon." And that's actually what led to the newsletter and starting to charge for the newsletter. But I'm very thankful for the turnaround that you helped create. I'd actually love to hear a bit more about what it is they did that helped them through that.

**Sanchan Saxena** (00:16:43):
I'll share with you the behind the scenes story that we went through. This is January, and Brian had this idea of taking the company public in April. And we are working on the road show deck, we are working through numbers, we were crafting the story, et cetera, everything's going well.

**Sanchan Saxena** (00:16:59):
And then we hear of this coronavirus crisis and all of a sudden countries are shutting down, one after the other. Italy shuts down. Japan shuts down. This country shuts down. And all of a sudden we can see on our travel map, we have this dashboard where you can see where people are traveling, and you can see travel goes down to zero in this country on a map. This goes down to zero in this country, and you're like, "Holy shit, what's happening over here?"

**Sanchan Saxena** (00:17:19):
I remember in all-hands where Brian stood up and said, "Look, we built this company for a crisis like this. We built this company, we have $2 billion in bank." I think something like that, some ridiculous number. "We have not used a single amount of money from our last raise," because we were profitable or growing really profitable. "And we are going to survive this."

**Sanchan Saxena** (00:17:35):
Six weeks later, he's in the same all-hands and telling people, "This is a different world we are living in." We had to lay off 1,900 employees, just 190 of those were in my organization. We had to raise $2 billion in debt, and the valuation dropped to 50% of what the valuation was. It was one of the craziest times.

**Sanchan Saxena** (00:17:53):
And Lenny, when you go through that, the loss of challenges you face, one is fine. You can cut costs by laying off employees for a little bit and create a little bit more runway. But remember, this is coronavirus time. I had to let go of people over Zoom. I couldn't even meet them in-person.

**Sanchan Saxena** (00:18:09):
I still remember when I actually finished my speech and I told them, "This is the last day," now, I literally shed a tear in front of everybody, because I was like, "Man, this is hard. This is really, really hard." And the company let go of 1900 people. I just had to let go of 190 in my organization, but it was still very painful, because remember, it is no fault of these employees. They just happen to be at the wrong side of the tornado that's hitting the world.

**Sanchan Saxena** (00:18:34):
The second equally most important thing was the people who stayed back, how do you motivate them? One is you can let go of the people, but people who stayed back, they need a light of hope that something is going to turn around. But how do you plan when data is changing every single day? And every day we will wake up, a new country will go down and say, "No, no more travels into our market".

**Sanchan Saxena** (00:18:56):
And we start predicting that our revenue will be 7, 10, some ridiculous very small percent of last years. There's panic. And this is where I would say Brian Chesky is an incredible leader. He's the Rocky Balboa of Silicon valley. You can punch him, he'll go down, he'll stand up, he'll fight again. That's the analogy. He's truly the Rocky Balboa where he took so many punches, but he stood up again and say, "One more round."

**Sanchan Saxena** (00:19:22):
And that's how the company survived. From an operating principle, we went into two week planning mode. Greg Greeley, who was the president of Airbnb used to say, "Look, can't plan for a year, can't plan for a quarter. We're going to plan every two weeks. We're going to react to every two weeks." And I think this is the lesson that I try to share with a lot of product people as well and founders as well is that things are going to go all right. Things are not going to go as you plan.

**Sanchan Saxena** (00:19:47):
The real genius isn't to dot every eye, to cross every team before you get started. The real genius is, what do you do when shit goes wrong? And I believe rapid recovery is the key to success. What you do, how quickly you can recover from failure becomes really important. Our operating model changed. We went to two weeks shipping. All right, what are we doing for the next two weeks? What is the most urgent thing for the company? For the company. Not my team, not your team, not somebody else's team.

**Sanchan Saxena** (00:20:13):
And we pivoted the entire machinery down over there. And then slowly and slowly after two or three months, we got to a place where we got semblance of what is happening. I want to tell you one story. Hotels and Airbnb are competitors, right? And when this thing happened, we had a debate, "How are we going to position Airbnb against hotels?" And actually we had to figure out what are the advantages of people staying in an Airbnb.

**Sanchan Saxena** (00:20:35):
And luckily for us, being in an Airbnb where the air you breathe is only you and your family turned out to be a huge secret sauce to compete. When you're in a hotel, there's a lobby. You get to be with other people. But when you're are in an Airbnb, you're safe. We pivoted our marketing as well and messaging as well. The entire company came together to become one.

**Sanchan Saxena** (00:20:55):
And through this, I would say Brian's leadership was just phenomenal, everything I learned about crisis management, leading with calmness. There's a very good saying in boxing. I love sports. There's a very good saying, which is, you can have all the plan. The moment you step inside the boxing and you get a punch on your face, all your plans go out the window. And you got to stay calm when you get a punch on your face.

**Sanchan Saxena** (00:21:15):
And that is what I learned from Brian, how to stay calm, how to stay composed while at the same time, deep down you know you owe a lot to these employees, you know you owe a lot to these employees to have clarity, and for them to stick around with you and believe in you that the company can turn around. It was an amazing journey, but pretty painful.

**Lenny** (00:21:32):
Wow. I haven't heard that level of detail about what went on inside, and so thank you for sharing all that. Very tactically, I'm curious, the two week planning cycles, how did that actually happen? Was there a large meeting every two weeks with the leaders and they just kind of discuss, "Here's where we're thinking for the next two weeks."?

**Sanchan Saxena** (00:21:48):
Yeah, I think so. One of the things about Airbnb, and we'll talk about it later as well, but it's a very founder-driven company. While there are leaders over there, the founder is deeply in the trenches. He really understands the customer. He's not this executive who's so far removed from reality that they can't actually create the content.

**Sanchan Saxena** (00:22:04):
Brian was living, breathing that exercise. Execs were breathing that thing. What we'll do is we'll have a bunch of things top-down. Again, this is what we need to do guys. We need to cut this feature. We need to cut this product line. We need to cut this business unit. I literally had to shut down one full business unit because we had to cut the bleeding, so to say, and let go of those many people.

**Sanchan Saxena** (00:22:24):
It was a top-down mandate, but also it was a bottom-up. The engineers, the product managers and designers are frontline. They are in connection with the CX team who's hearing what customers are complaining about. And so there was a mixture of top-down guidance to a bottoms-up things that we are seeing on the field. And every two weeks or so, the leadership, Greg in that case, for example, would make a decision on, "Here are the things we are going to go handle." And there were no teams anymore.

**Sanchan Saxena** (00:22:50):
We basically dissolved this idea that there are sub-teams. There was one team, #Airbnb. Didn't matter whether you worked in CX or Airbnb Plus or Lax, or any of those things, we're going to move engineers wherever we have to, we're going to move PMs wherever we need to, and there's no such thing as sub-team anymore.

**Sanchan Saxena** (00:23:09):
A lot of engineers on my team would go on to do marketplace dynamic stuff, like pricing and all that stuff, while some of those engineers would then go on to build CX tools or something else that was needed for survival. I felt like a 4,000 people company was operating as a four people company and a 40 people company, which is one team, no sub-teams, everybody rowing in the same direction. And that was really important.

**Sanchan Saxena** (00:23:31):
Because remember, employees who are at your company are looking for clarity. What should they work on? Is the thing that they're going to work on meaningful, right? Because nobody knows, right? And when people will ask you as a leader, like many people ask me, what does six months look like? What does a year look like? Where are we a year from now?

**Sanchan Saxena** (00:23:46):
The most honest answer you can tell them is, "I don't know." Because if you cook shit up, they're going to see through that lie. They're going to like, "Ah, this is just all marketing fluff." We would be very honest as leaders, would be very vulnerable as leaders, saying, "This is truly once in a lifetime thing. We don't know how we're going to navigate. But here's what we believe to be true."

**Sanchan Saxena** (00:24:05):
We had to get people from feature obsession, revenue obsession, to belief obsession. What is belief obsession? When we all believe that when coronavirus is over, people will want to travel. We all believe that coronavirus will be over. You start going into first principles belief-based thinking, and you'll bring stories that will make people believe that the future that we are working toward is actually possible.

**Sanchan Saxena** (00:24:28):
For example, there was a survey we did, we said, "If money wasn't a consideration, what would you do for the rest of your life?" 99.99% of the people said, "I will travel the world." Travel is in human genes. And so we had to pivot to actually making people believe why travel will be back, why Airbnb will survive, and why Airbnb will eventually thrive if the coronavirus crisis is lower.

**Lenny** (00:24:51):
These stories are incredible. I was going to ask around the morale piece. You mentioned keeping morale up. And it sounds like a big piece of that was pulling people back to the mission and the vision of Airbnb and re-inspiring them, and helping them feel like this will work out. Is that what you found to be most effective, to keep more morale up, or is there anything else that also helped keep more morale up in this very tenuous time?

**Sanchan Saxena** (00:25:11):
I think in these tenuous times you will notice that you can't pay these employees better than market. When this happened, FAANG companies were at our door trying to poach our engineers. Overnight, every engineer was pinged by Facebook, Google say, "Hey, we heard Airbnb is going down. You want to come over? We'll pay you X amount of money, and that stock is stable."

**Sanchan Saxena** (00:25:34):
You had vultures at the door, so to say, as a proverbial exercise where your top talent is getting poached, but you can't pay this top talent the best. Right? You can't. Because your financial situation doesn't allow you to do that, right? But you still give them something, right? Because it's at a lower price and you start to sell the vision that if the company turns around, this will be at a higher price and you'll have right compensation. But those were some of the challenges.

**Sanchan Saxena** (00:25:56):
The second challenge is you'll notice that people who thrive in these situations will be the one who truly believe both in the mission, but I think more importantly in the founders to make that mission come to life. Because you and I both know, right, there are many companies who have the similar mission, want to do something similar, but some succeed and some don't.

**Sanchan Saxena** (00:26:17):
And the secret sauce of that in my opinion is the founder. And if the employees do not believe in the founder, if the employees do not believe that the founder can make things happen as they talk about, and the founder is not able to connect with the employees, those companies go down in flames. The second thing I would say is the founder needs to be at the front line. And Brian Chesky was on the front line.

**Sanchan Saxena** (00:26:37):
He was literally 24/7 available, interacting, making decisions, holding all-hands, writing emails, sending messages, and assuring people that I'm in this with you. By the way, there's a proverbial thing, right? When such situations happen, all execs take a pay cut. Every company does that, right? But then still certain companies survive, certain don't, right?

**Sanchan Saxena** (00:26:58):
It's primarily because of the founder. And then the third thing I would say is somehow getting people to believe in the future that they came here to create. When drastic situations like these happens, when I joined Airbnb I had a vision of what it can become, and the reality snaps and all of a sudden like, "Holy shit. Is that even possible?"

**Sanchan Saxena** (00:27:21):
That is the real art I learned from Brian is that the power of storytelling without any data. Your data is telling you, "You're going to die." The data is telling you, you got 7%, 10% of your revenue, whatever the number was now. I forget now. Like single digit number, right?

**Sanchan Saxena** (00:27:36):
And every day you're seeing the numbers go down, right? And Brian has this incredible ability to help you see a future in a way so crystal clear that when you leave chatting with him, you're like, "Man, it's possible. We can make it happen. We can do it." That trait was really, really important that Brian invested in it, and all the three founders, by the way.

**Lenny** (00:27:59):
**Sanchan Saxena** (00:29:06):
Yeah, I think a lot of amazing things. I tell people, I learned all things about building great products, building great businesses, building great companies from founders like Kevin Systrom and Brian Chesky, Brian Armstrong and others. Well, let me go back to Instagram days. I want to paint the picture first of what it was when I got there and the journey we were on.

**Sanchan Saxena** (00:29:23):
At that time, Instagram was a highly successful app that was growing really fast, but there were many questions. Only photos, you can't share anything outside. It's only from the camera. You can't share links. At Facebook they allow you to share links. Why don't you allow that, right? There's an existential question that comes at those stages, which is who do you want to be when you grow up?

**Sanchan Saxena** (00:29:45):
When you're a startup, that's a big, important question for you to answer. And there were many debates. "Do we want to be the next Facebook? Do we want to be the first Instagram? Who do we want to be when we grow up?" Right? And that debate is really, really important. That clarity is really important for your employees.

**Sanchan Saxena** (00:30:02):
The thing that I learned from Kevin Systrom was the power of simplicity. That guy can listen to everything, hear everything, hear the noise on Twitter, here, there, all the customers complaining, and then just simplify things that makes sense for the team to operate on. That's his superpower, which is simplicity. Take all the information, but simplify your strategy, your belief, who you want to be when you grow up in a way that people can then act on it.

**Sanchan Saxena** (00:30:28):
The other thing I learned from him was intentionality. This is the story of Instagram Stories. When Snapchat came about, Snapchat was eating Facebook and Instagram as lunch in many regards, because the Snapchat Stories was crushing it. And there are lots of myths, by the way, in the media, how that happened.It was a mandate from Zuck.

**Sanchan Saxena** (00:30:47):
No, Zuck did not have a mandate. There was no such thing. It was something that people were experimenting. I want to tell you a story, two stories, which is stories in Facebook app and stories inside of Instagram app, and stories for your audience is the stuff that Snapchat invented, all credit to them. In product management, you always debate measure twice, cut once kind of a thinking. It's like measure the data, get all the data, right? Get all the analysis, ask customers, et cetera.

**Sanchan Saxena** (00:31:12):
Some of the successful founders don't do that. Some of the successful founders go off of gut and instincts more than they go off of data. And that to me is a superpower of a founder is like they have this instinct, their vision. I'll tell you a story. On Instagram side, Kevin Systrom made a decision. We're going all in on this new format. There was no A/B testing that if you add stories at the top ...

**Sanchan Saxena** (00:31:34):
I mean, there were a little bit of A/B testing, but not like, "Okay, let's go measure. If you add stories at the top, the feed will go down as a result. Engagement will drop as a result. Revenue will draw. And as a result, we should not do it." There was no such thing. The founder said, "We're going all in people. This is the future. We're not going to measure and then cut. We're going to cut. And then we are going to iterate from that new baseline. We're going to continue to iterate on that on the Facebook side."

**Sanchan Saxena** (00:31:57):
And by the way, there's a very good article that some PM inside of Facebook wrote why stories didn't survive at Facebook but thrived at Instagram is because on that side there was a mathematical modeling being created, which is what are the trade-offs. And you have a successful business. And this is the innovator's dilemma. You have a successful business called feed that is generating billions of dollars.

**Sanchan Saxena** (00:32:16):
And you got to bring in this new thing, which has zero advertisers, we don't even know if the engagement will be there or not, and you got to put those things together. There was a very different approach that Facebook took for stories versus Instagram. And by the way, there was no this rumor in the media there was a top-down man. No, these teams were just experimenting. They were just trying things out.

**Sanchan Saxena** (00:32:35):
We always want to look at our competition, be inspired by what's working, what's not. There's no harm in learning from somebody who's doing something great and experiment and see if that works for you or not. That was the story. And the thing that I learned from Systrom was intentionality. As a founder, one of the things you have to recognize, or even as a product leader, you have to recognize is that every product that you build should be intentional in nature.

**Sanchan Saxena** (00:32:57):
An intentionality doesn't come just from A/B testing. A/B testing maybe you can do that, right, as a later on, but you got to have intentionality. Where do you want to go? What is the world you want to create for your customers? And then create out A/B testing to get you the fastest route to that end state world. When I talk to product managers, oftentimes I tell them you're being either too lazy or you're trying to be too risk averse by telling me, "Here are the assumptions you have that you're going to test."

**Sanchan Saxena** (00:33:24):
First tell me the intentionality of the product that you want to create. What do you want to see come true? And then let's talk about the A/B test we can run to measure that we are headed in the right direction. And it's a flipping of the mind. And that was something that Brian also taught me. By the way, it's a joke, but some degree it's reality too. A/B testing at Airbnb is a bad word.

**Sanchan Saxena** (00:33:44):
You don't go to Brian and say, "Hey Brian, here's my Excel spreadsheet. I want to run some 10 A/B tests and come back and tell you whether we are heading in the right direction." You're going to get thrown out of the window. It's like, "No, we got to figure out what the product is." The other thing I learned with Brian Chesky was you first want to create an ideal end state of the product without any constraint.

**Sanchan Saxena** (00:34:05):
Here's a good analogy that Brian will teach people. Let's say you want to build Airbnb. What is the 15 out of 10 experience you want to create? That's where Airbnb designers and PM start by the way. In most companies, the designers and PM start by saying, "Okay, 10 is perfect. We can probably do seven. Let's start at seven." It's a very constrained minded thinking. It's like, "I got this much time. I got this many resources. I got this much budget. I can only do so much." Right?

And what Brian taught us was think unconstrained first. Think about a 15 out of 10 experience, design the ideal end state first. I'll give you a very concrete example of this. Let's say you're building Airbnb lounges. A customer's check in is at 3:00 PM, but their flight is at 6:00 AM. What are you going to do? Well, you got to build a lounge, right?

**Sanchan Saxena** (00:34:50):
If you're traditionally trained in product management, this is what you'll do, which is, look, I don't know how to build this in 120 countries. I don't know how to scale this stuff. So I'm going to ignore some ideas and I'm going to build a MVP lounge. And then I want to say, "Okay, if I add internet access to it, customer detention went up by way. If I add coffee to it, this went up by Z.If I add cheers to it, it went up by X," and hence I'm going to justify how to build a beautiful mall.

**Sanchan Saxena** (00:35:15):
That's not what you will do if you're Brian Chesky. Here's what you'll do. You will pick one location because you don't know how to scale a lounge in 120 countries. Pick one location. But you know how to get in one location a barista who can create coffee, you know in one location how to get the best seats, you know in one location how to get the best air conditioning, you know that right. Build the best possible lovable product first.

**Sanchan Saxena** (00:35:38):
And then from that point on, understand what worked, what did not, and then scale the pieces that actually worked. It's a very different way of thinking about things, doing things that don't scale it first. Those are different things I learned at Instagram and Airbnb.

**Lenny** (00:35:50):
So much good stuff there that we could do a podcast at each learning. And that point about working backwards from the ideal, that's something I've absolutely taken away also from Airbnb and news often. If folks want to learn a bit more about that, if you Google Snow White Airbnb, there's a whole story about Snow White that kind of touches on where a lot of this idea came from.

**Lenny** (00:36:08):
I want to follow up on one point you made about intentionality. See your founder or PM and you're just like, "Oh, yeah. Okay. I'm just going to figure out a vision, and this is where we need to go. And I need to be intentional, so I'm just going to tell people here's where we're going." Oftentimes you're wrong.

**Lenny** (00:36:24):
Do you have any thoughts for someone trying to decide how do I know if I'm going in the right direction, how do I know if I should trust this gut that I have versus running A/B test, because otherwise we don't know? Do you have any thoughts on that?

**Sanchan Saxena** (00:36:35):
Absolutely. I think there are lots of things to unpack there. The first and foremost thing I'd say is that when you sit in your car, you tell your GPS, "Here's where I want to go." You never go into your car and say, "Hey, GPS, tell me where I should go." Right? At least I haven't done that. And then you use the GPS to run an A/B test, say, "Look, I want to get there in the fastest way possible."

GPS then figures out the path to get there in the fastest way, or sometimes tell the GPS, "I'm low on gas. Take me a gas efficient route that I can get there, or [inaudible 00:37:07]." Those are A/B tests. But you never say to the GPS that, "I don't want to go to San Francisco. Tell me where I should go." It's a similar concept around intentionality.

**Sanchan Saxena** (00:37:19):
You got to start first and foremost with, where do you want to go? What is the true customer problem that you want to solve? And why does that matter? The second thing I'll say is, oftentimes, product leaders discount gut or intuition a lot. And the reason is it's a safe thing to do. You can always point to data and say, "Look, I did this because of this. And if I fail, here's the data. And don't fire me." I'm just joking.

**Sanchan Saxena** (00:37:44):
But you get the extreme of it, right? It's very hard to build a team and build your reputation and get an intuition. But the thing is, founders do exactly that. There was no document that said, "10 years later Facebook will make billions of dollars in revenue," or no document that said, "Coinbase one day will become a hundred billion dollar company if you invest in that at that point in time." You got to have gut and intuition. And founders have that and operators need to learn how to harness that as well.

**Sanchan Saxena** (00:38:07):
And to me, gut and intuition is data. It's just not statistically significant yet. That's all it is. You have built that intuition, that gut, because you immerse yourself in a situation, you hung out with customers, you understood what was happening. You just can't prove it that it is statistically significant yet.Don't discount your gut. That's the second point.

**Sanchan Saxena** (00:38:28):
And the third point that I'll say is, once you have figured out what that experience looks like, yes, you got to validate what's happening, you got to get feedback back from the community while launching it, and then you got to constantly iterate. My advice to people is, don't do that testing up front, start with some assumption, start with a bunch of intuition, et cetera. Create that and then have the appetite to actually persist through that.

**Sanchan Saxena** (00:38:51):
That's another thing I learned from Brian is that oftentimes these ideas, these crazy ideas, you need persistence. He used to say, "You got to have impatience with getting started, but patience for seeing them through." Because at many other companies, you can actually kill a brilliant idea early on because you just didn't have the patience to see that through.

**Sanchan Saxena** (00:39:11):
You got to start with intentionality and then you got to iterate and test, and iterate and test, and iterate and test. But don't give up too early either. And last but not the least, I'll tell a secret to all your audios.

**Lenny** (00:39:21):
Oh boy, here we go.

**Sanchan Saxena** (00:39:23):
Nobody knows everything. Right? The idea is that you can look at as much data as you want, which is still not going to feel that all the answers. What is really important? The really important thing is rapid recovery. Build a culture in your team where failure of those experiments is actually celebrated.

**Sanchan Saxena** (00:39:41):
Build a culture in the team where actually people get energized when they fail, because guess what, each failure was a learning that will avoid a mistake for them in the future. Right? And I think that is the mindset and culture you want to build. Look at data, look at all the things. But at the same time, don't just look at that and say, "Look, because the data said so, that is what I'm going to do." I'm going to use a very good analogy over here.

**Sanchan Saxena** (00:40:03):
And this story has been butchered many times, but I was right there when this happened, so my version is at least 80% accurate. There might be other versions as well. But this is Instagram Stories. Imagine you are Kevin Systrom and data science comes to you and say, "Look, I looked at data, and 99% of all photos on people's phones are actually at least a week old. Please allow Instagram Stories to let people select a photo that is at least a week or two old."

**Sanchan Saxena** (00:40:30):
Then user research comes back and says, "We talked to a bunch of people. They said, 'Yes, I would love to share a story of my birthday about a month ago.'" Right? And Kevin Systrom says, "No, my intentionality is that story should be real time news. It should be the world's largest TV channel. You open that up and you see what's happening right now. That is the intentionality I'm going towards."

**Sanchan Saxena** (00:40:51):
In the beginning, Instagram Stories did not let you pick anything that was not real time. You couldn't go back in your camera and pick something a month ago or two ago, because the intentionality of the product was to create the world's largest real time network of what's happening in the world right now. If that's the intentionality, you got to ignore the other customer needs that I want to share with the world what I did a month ago, and that changes the dynamics.

**Lenny** (00:41:14):
Essentially, intentionality is setting up vision for where you want to go, where the product's going and then working away towards it. That makes a lot of sense. An example of Instagram. It's interesting because he eventually changed his mind, because I know that you can upload old photos to stories [inaudible 00:41:28]

**Sanchan Saxena** (00:41:27):
No, that's actually after he left. But yes, you're right.

**Lenny** (00:41:29):
Okay, I see. A different intentionality appeared.

**Sanchan Saxena** (00:41:34):
And look, it's also nothing wrong with changing your mind afterwards once you push the envelope, and then you learn something new and you can pivot. And that's another beauty of founders is that they're very intentional people, very strong opinionated people, but in the face of something new, they're also the fastest to change. They don't have remorsefulness, they don't have regrets, and like, "Yeah. All right, let's pivot." And that is the culture you want to build as well as an operator.

**Lenny** (00:41:57):
I'd love to spend a little time on Coinbase and the product culture there. How A/B test driven is it at Coinbase? How do folks think about intentionally vision? And also just, what's the product development process like? I'm always curious how products is developed at different companies.

**Sanchan Saxena** (00:42:10):
I think all different companies that I've worked at have very different product development cultures. At Airbnb, for example, design and experience was super paramount, and you will not compromise over it. You won't cut design to ship. In other companies you will cut design to ship sometimes because you want to find something quickly.

**Sanchan Saxena** (00:42:26):
At Coinbase, it's slightly different as well. Every company has their nuances. Coinbase is an industry which is rapidly growing. It's Web 3.0. I mean, I have not come across a Web 3.0 expert yet. There is nobody who's an expert in Web 3.0.

**Lenny** (00:42:40):
They seem to be on Twitter.

**Sanchan Saxena** (00:42:41):
Yeah. There are lots of people who think they're experts on Twitter. But the reality is, man, the industry is so nascent, so early. You have good intentions and good intuition about where it could go, but it's very hard to be right all the time. The culture of Coinbase is to take big, bold bets, get started with very tiny teams.

**Sanchan Saxena** (00:43:00):
The Coinbase NFT marketplace that we just launched, it started with five people, one product manager, one designer and other three engineers. That's how smart it start. And of course it has grown big now as we find product market fit, etcetera, et cetera. But that's the idea is take big, bold swings, but with tiny teams that can move at lightning speed and make shit happen, because that's one aspect of it.

**Sanchan Saxena** (00:43:22):
The other culture that I love about Coinbase is this idea of how we make decisions. Emily, our COO, posted a blog. It's public. You guys can all read it. It's a very different mindset of making decisions, so let me unpack that. When I was at Facebook, Instagram and other companies, other tech companies, there's a saying around product and design, marketing. All these cross functional people need to come together to build a product.

**Sanchan Saxena** (00:43:45):
And oftentimes you will notice that the decision making process could get a little bit convoluted, not always, but a little bit convoluted. It's like, okay, what do you like? What do you don't like? You got to align influence, align influence. And next thing you know ... And again, I'm not saying always, but sometimes it can happen that the thing that ends up shipping is the least common denominator that annoyed everybody the least amount, right?

**Sanchan Saxena** (00:44:09):
Everybody said, "Yeah, I could get comfortable with that. I could get comfortable with that." And Brian has an allergic reaction to things like committees. It's like designing by committee. The idea that we have, and you can read it in her blog, is the idea of a directly responsible individual or DRI.

**Sanchan Saxena** (00:44:26):
For every project, we'll establish a DRI. It could be a person in operations, engineering, design, legal, marketing, whatever that is, depending on the nature of the project. And DRI's job is to then listen to the cross functional partners, get their input. And we have a written culture like Amazon, so every input is provided in writing. Right?

**Sanchan Saxena** (00:44:45):
You can see what head of legal is saying. You can see what your head of operations is saying, what engineering is saying in writing. And then the DRI's job is to take all that input and make a decision. Not take all that input and do necessarily what's right by everybody, right? Still do what's right by the customer. Still do what's right by the business. Still do what's right for the user in many regards.

**Sanchan Saxena** (00:45:07):
But take that input, inform yourself with all the right things, but it's your job to then make the final call. Whoever you might be, sometimes it's operations, sometimes it's engineering, sometimes it's design and product, and others then have to disagree and champion that for you. I might go in and I might write in that rapid, "I disagree with this. Here are the reasons why."

**Sanchan Saxena** (00:45:27):
But the decider the DRI has to make that decision. And once that decision is made, I got to disagree and commit to it and champion it with the rest of the team as if it was my decision. It's not just disagree and commit, it's disagree and champion. Go out there and evangelize that this is the right thing to do. Now, there are lots of advantages of that.

**Sanchan Saxena** (00:45:43):
It cuts all the passive aggressive behaviors that all of us have seen in different companies. It's like, "Ah, I got to go talk to this head of X, and I got to be nice. I got to make sure we have this relationship." And the decision gets dragged over two, three months, because the speed of decision making is directly proportional to the strength of your relationship in those companies, right?

Here, the speed of decision making is directly proportional to the person who's directly responsible from making that decision happen. And it is, of course, incumbent upon that person to listen and get unsolicited advice. But at the end of the day, they're the single [inaudible 00:46:16]. They're the final DRI. It's a very different culture than any place I've worked in. And when you join Coinbase, we have to orient you by saying, "Look, this is how you operate," very different than any other company.

**Lenny** (00:46:28):
That's so interesting. Is that how big decisions are made or does that filter down to even individual teams where a PM or whoever is a DRI in a team makes decisions this way?

**Sanchan Saxena** (00:46:37):
Individual people as well. You will see PMs writing, engineers writing, and operations and legal writing a rapid. It's called rapid. It's for rapid decision making. And it's the same format that I would use if I want Brian to make a decision. It's the same format someone will use inside their team.

Let's say you are working on a particular project, you will write that rapid. It's the same exact format, same exact mechanism, and every team uses those mechanisms to actually scale. Otherwise, decision making can actually be the [inaudible 00:47:05] of hypergrowth companies.

**Lenny** (00:47:06):
Is there anything else that's unique about how Coinbase operates that's stuck with you that you might take to a future company that you may work at if you ever leave Coinbase?

**Sanchan Saxena** (00:47:14):
Yeah. I think decision making is one. I think just the idea of how to operate in such an ambiguous industry. When I got to Airbnb, ambiguity was a lot, because it was the first time we were doing home sharing as an example, right? And it was not done before. But you had had the overall understanding of the travel industry, the customer, the regulation, et cetera, et cetera.

But I think [inaudible 00:47:35] is a very ridiculously new thing. People sometimes ask me what's the future of NFD, I say, "Ta-da! I don't know," I'll experiment, figure it out. I have an opinion. I'll take that opinion and start to execute against it, but nobody knows. How do you build conviction in a highly noisy world?

**Sanchan Saxena** (00:47:50):
I mean, Web 3.0, as you're probably on Twitter, everybody has an opinion on Twitter. X should do Y, and Y should do Z, and this is how it should be. Right?And the thing that I would take with me everywhere is, how do you build in that noise? How do you stay focused and still build what you believe is the right thing and still let the noise happen around you?

**Sanchan Saxena** (00:48:09):
And I think as Web 3.0 advances and every company becomes a Web 3.0 company, that's at least my prediction in this decade, just like every company became a mobile company, didn't have a mobile app, but became a mobile company, I think every company will become a Web 3.0 company. Everybody will have to build that muscle of operating in that level of ambiguity where there's literally no data and lot of noise.

**Lenny** (00:48:28):
Is there some way of operating at Coinbase that allows them to operate in this ambiguity and focus? Is there something that you've seen there?

**Sanchan Saxena** (00:48:36):
Yeah. I mean, we have our own flaws. I mean, no, company is perfect. We have our own flaws. But what we have figured out is how to operate, just the way I described before, which is a DRI mindset culture. Instead of having 15 people have 15 different perspectives, et cetera, it should all be amalgamated into one rapid.

**Sanchan Saxena** (00:48:51):
And we trust our leaders. We trust the DRI, whoever that DRI is, to make the decision. And then we start going towards the same direction. We ignore all the noise over there. Again, no company is perfect yet. We are still learning, but this is something I found to be very effective.

**Lenny** (00:49:03):
On the thread of Web 3.0, if someone's thinking about like, "Should I get into a Web 3.0 sort of company? Should I not?" what sort of people do you find are most successful maybe on the product side specifically, but even broadly, folks that may enjoy the world of Web 3.0 and others that maybe not?

**Sanchan Saxena** (00:49:18):
Yeah, I think Web 3.0 is definitely at a stage right now where I'm seeing a lot of influx of people from Web 2.0 world. Literally, if I look at my LinkedIn post, there's somebody saying, "Ta-da! I left X and I'm joining a Web 3.0 company." So there's already.

**Lenny** (00:49:32):
Or starters pivoting to Web 3.0 in your entire team.

**Sanchan Saxena** (00:49:35):
Exactly, starters pivoting to Web 3.0 as well. I feel like when I joined ... I mean, I joined very recently. I mean, not long time ago. When I joined, it was a very different conversation. I was still telling execs and others at Google and Facebook, "This is why you should join. This is what's happening," et cetera, but now I feel like the world is slightly different.

**Sanchan Saxena** (00:49:52):
I think the people who will thrive or who thrive in Web 3.0 are people who truly are able to understand the potential and disregard the constraints of today. And here's what I mean by that. You all have seen articles written by really influential celebrities saying, "Web 3.0 sucks." And let me tell you why, because today sucks, right? We agree with the future principles of Web 3.0 of decentralization, this and that. But look at today, everything is centralized. Everything is blah, blah, blah.

**Sanchan Saxena** (00:50:21):
I always remind those people as like the path to Web 3.0 goes, and from Web 2.0 to Web 3.0 goes through web 2.5. It doesn't go straight from Web 2.0 to Web 3.0. It goes through web 2.5. You got to go through that journey. And a lot of stuff that's happening in Web 3.0 today is web 2.5, 2.7 kind of. There's no truly decentralized stuff that is there, but the idealism is there. The closest thing is Ethereum probably, or Bitcoin.

**Sanchan Saxena** (00:50:42):
The idealism is there and we want to get to the towards that, right? The people who will thrive most are people who understand those ideals, understand the future and are builders. They want to take what it is today and then morph it into the ideals of tomorrow. I remember I'm a history buff and I love watching the history of technology.

**Sanchan Saxena** (00:51:02):
And there's a video on YouTube which describes someone playing with the internet back in 1986, '87, '89, right? And what you had to do was if I wanted to visit Lenny's website, here's what I'll do. I'll type 192. whatever the IP address was, and then I'm going to hit enter on a blue screen. And then there'll be things coming down and I'll pay $200 to just access his website.

[inaudible 00:51:23] too, right? But if you can get past that and see that someday Lenny and I will actually have a podcast, video podcast or YouTube podcast over the internet, and we'll be able to see each other and record that shit, that is powerful. We are looking for people at this stage who believe in that journey.

**Lenny** (00:51:43):
I love that. And just the idea of hiring and joining company, I wanted to touch on hiring advice. You're really good at hiring. You've hired many people, you've interviewed tons and tons of PMs, and so I just wanted to touch on this before we wrap up.

**Lenny** (00:51:56):
I find that hiring and just finding people as maybe the single biggest pain point for companies these days and startups especially. Do you have any advice for our founders or product leaders or just leaders in general for hiring, including finding people and closing them, that kind of thing?

**Sanchan Saxena** (00:52:10):
Yeah. I think maybe I can focus a little bit about what are some of the things that I believe are incredibly important for startups to get right when they're hiring. The couple of things to remember is that what really matters, what's highly code related to a startup success isn't that they used a process like scrum, like this, like that.

**Sanchan Saxena** (00:52:30):
Well, what's highly correlated is that somebody bloody knew what to do when. That is the most important thing. And I call that content. Content means what you do when. Process means how you do the thing that I just said. And I think there's a very easy love affection towards process.

**Sanchan Saxena** (00:52:50):
And I think Reed Hastings has talked about this in their culture deck. Steve jobs has also talked about in the past is that, oftentimes we gravitate towards people who know how to avoid mistakes, who know how to create a process. Here's what a typical cycle is. You get bigger and bigger, you start making mistakes, you're like, "Oh, we got to create a process so we don't make the same mistake again."

**Sanchan Saxena** (00:53:07):
And next thing you know, over a period of time, the process becomes the product. Every morning you wake up, you look at your calendar, 80% of the time as an exec you are moving the process, you are managing the process, and that process becomes the product, and you lose sight of what the real product is, who your real customers are.

**Sanchan Saxena** (00:53:24):
My advice to people, especially in early stage startups is bring in people who know content and teach them process, as opposed to bringing in people who know process and trying to teach them content, because that's a bloody hard thing to do.

**Sanchan Saxena** (00:53:36):
And this obsession about a lot of funders ask me when I consult with them is like, "Should we do scrum? Should we do X, Y, Z process?" I'm like, "You can do whatever you want. It doesn't matter. You can try any of those things. It will not be correlated to your success." And maybe to some degree, but not a lot of degree.

**Sanchan Saxena** (00:53:52):
What you really need to figure out is, who do you hire, who can actually understand what the content of your product is, what the content of your customers is? How do you win in that industry that you're operating in? And make sure that you stay obsessed over there, right, as opposed to the process. This is something that Brian Chesky has grilled in me.

**Sanchan Saxena** (00:54:09):
Hire executives who know how to execute. And his idea was, let's say Sanchan's entire team disappears, and then I go to Brian and say, "Hey, Brian, I got to hire this organization, I got to hire these people, and then I'll tell you what to build, or I'll then build." Right? Now I should be able to then crawl up my sleeve, if I'm a content kind of a leader, and I should do exactly what my team did.

**Sanchan Saxena** (00:54:29):
Maybe not with the same capacity, because if I have so many people team, I can't do so many people worth of work. But at least be able to tell you, "This is what we should build. This is when we should build. This is how we should build." Right? I shouldn't be a leader who just delegates to the extent that I forgot what content is, right? And that is a very important piece.

**Lenny** (00:54:46):
When you're looking for a leader like that, because that sounds amazing, what do you look for? How do you know if there's that sort of leader when you're interviewing or just kind of evaluating?

**Sanchan Saxena** (00:54:55):
One of the things we did at Airbnb, because this was the thesis that we had over there, we actually changed our interview process around this. We will give people a work challenge. You're very familiar with that. Most people say, "Come and do a presentation." No, we actually gave you a work challenge.

**Sanchan Saxena** (00:55:08):
We said, "This is the problem you're facing. How are you going to solve it?" Right. We're facing Airbnb Plus problem, we need to build millions of homes that are Airbnb Plus, but we don't know how to do that. What would you do? And we want to see the depth of thinking. They don't know the right answer because they don't have the right data. That's okay. Right?

**Sanchan Saxena** (00:55:24):
But they at least need to show us how they approach the problem. What are they going to do? And they need to show us the content of how they're going to do. Some people will come in and say, and have seen slides in those presentation, they'll come in and say, "Here's my process. Ideation, execution, iteration." That's okay. I want to know what you're going to do inside of ideation.

**Sanchan Saxena** (00:55:42):
Some execs will come in presenter say, "Well, the first thing I'm going to do is go out there and figure out are their third party companies who can actually scale my operations without building it in now." That is content, right? And I want to evaluate that.

**Sanchan Saxena** (00:55:53):
The second thing we will do is in our interview process as well, if it's an exec, Brian will spend time and I will spend time, anybody else will spend time, we will focus on whatever you did in the past, tell me the role that you played in that versus telling me everything that your team did. Right? To be precise, the role you played.

**Sanchan Saxena** (00:56:11):
And this is something I tell a lot of my folks at Coinbase as well is like, you got to be able to bring things to me, escalate to me when you need my help and let me help you be successful. My role is such that I have a large team and I can't do everything. But what I can do is set them up for success. How? Of course, the tactical supply of resources.

**Sanchan Saxena** (00:56:32):
But more importantly, when we are thinking about the content, when we think about what to do, when to do, how to do it, let's sit together and think about that. Escalate to me, bring things to me. I will go into the mud with you and I'll create that clay for you, with you. And that is how I stay relevant. But more importantly, that is the value that I get to help my team succeed as well.

**Lenny** (00:56:51):
I love that. I was just thinking that the fact that you call kind of the roadmap and the plan like a content, that makes you a content creator, and how does that feel?

**Sanchan Saxena** (00:57:00):
Yes, that does feel good. I mean, you should have the ability to create a roadmap and that is your creating content around that. But the thing that I want to make sure people understand is that the format of that roadmap doesn't matter. Whether you use Excel, or this, or that, it doesn't matter. That process doesn't matter.

**Sanchan Saxena** (00:57:15):
What matters is that you were able to come up with the right roadmap, which is what you're going to build, at what time you're going to build. And that is a core value set of an individual or a leader that you should absolutely look for.

**Sanchan Saxena** (00:57:26):
And so otherwise, my prediction is four or five years later or whatever the time is, that company will start to attract process people, and next thing you know, everybody in the company is a process person and nobody is a content person.

**Sanchan Saxena** (00:57:38):
And then what hands up happening is the founder ends up taking that burden of becoming the content person, and next thing you know, they can't scale. They just cannot scale. The company cannot scale.

**Lenny** (00:57:47):
Yeah, because process eventually just kind of starts to break down.

**Sanchan Saxena** (00:57:50):
Exactly. There's a very good deck. I'll encourage your audience to watch the Netflix Culture Deck. And Reed Hastings talks about this at length, better than I did. And it's a beautiful concept, it's a beautiful argument, and I think I will encourage every follower to start looking for that.

**Sanchan Saxena** (00:58:04):
And again, I'm not saying process shouldn't exist. You absolutely need some process. That's why you can scale. You can't scale without some process as well. But process is not the answer. Content is the answer.

**Lenny** (00:58:13):
I feel like I've taken enough of your time. And so we've gotten to the final part of our chat, which is the lightning round, where I'm going to ask you a few questions and then just tell me what first thing that comes to mind. If nothing comes to mind, that's totally cool too. Does that sound good?

**Sanchan Saxena** (00:58:27):
Yeah, that sounds great, man.

**Lenny** (00:58:28):
Okay. What's a book that you recommend most to other product leaders?

**Sanchan Saxena** (00:58:33):
Two books come to mind. One is The Little Bets, which is how you live your life and how you build businesses with little bets. And the other thing I would say The Innovator's Dilemma. Those are two of my favorite books and highly recommend everybody reading those.

**Lenny** (00:58:46):
Awesome. What's a company that you recommend most to PMs that are looking for a new job other than Coinbase?

**Sanchan Saxena** (00:58:53):
Yeah. I mean, I think there are tons of Web 3.0 companies or tons of other companies. I would say amongst the companies [inaudible 00:58:58], the insights say where it is. I think Airbnb is a great company. People should definitely look at that company. It is once in a lifetime kind of a company as well, and people will enjoy working over there.

**Lenny** (00:59:07):
Agreed. What's your favorite app right now?

**Sanchan Saxena** (00:59:09):
My favorite app right now, Coinbase NFT.

**Lenny** (00:59:13):
Shit, I should have said other than Coinbase. All right, you get that.

**Sanchan Saxena** (00:59:16):
I would say I love TikTok. I am on TikTok all the time. I love how entertaining it is. I love how simple it is. I'm on TikTok all the time.

**Lenny** (00:59:27):
Same. We're in trouble. Who is your favorite manager that you had?

**Sanchan Saxena** (00:59:31):
Oh, my favorite manager. It was my first manager. His name is Sashi. He was at Microsoft. And he fundamentally helped change the trajectory of my life. He believed in me. And I was just out of college at that time. And he invested in me. The most important thing was he invested in me. If any successful person you meet in your life, one thing they will all tell you is at some point in their life, somebody believed in them and somebody invested in them, and that was that manager.

**Lenny** (00:59:54):
Amazing. And then finally, what's a favorite interview question that you like to use?

**Sanchan Saxena** (00:59:59):
Tell me the story of your career and focus more on why you did what you did. And I ask this question because the resume is full of polished shit. It's like, "Oh, I did this. I did this." Right? I want to hear the story. And tell me why you did what you did. And that tells me a lot about the person when they're answering the question, not the what. Because I can see that on the LinkedIn or the resume, but why, why they chose to do what they chose to do.

**Lenny** (01:00:23):
I love that. Where can folks find you online, and then how can listeners be helpful to you?

**Sanchan Saxena** (01:00:27):
Yeah. I mean, I'm pretty active on Twitter. Now that you know, I'm also active on TikTok. But Twitter is probably the best place to follow me. And yeah, if you have any suggestion, anything you want to chat about, send me a message on Twitter, DM me, or LinkedIn. One of those places and I'll be happy to chat with you.

**Lenny** (01:00:43):
And I imagine folks should check out Coinbase NFT and Coinbase Wallet?

**Sanchan Saxena** (01:00:47):
Absolutely, man.

**Lenny** (01:00:48):
How do people find that?

**Sanchan Saxena** (01:00:50):
Nft.coinbase.com. Give it a shot and let us know what you think.

**Lenny** (01:00:52):
Amazing. Thank you so much, Sanchan, for being here. This was amazing.

**Sanchan Saxena** (01:00:55):
Thank you, Lenny, for having me.

**Lenny** (01:00:58):
That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast. You could also learn more at Lennyspodcast.com. I'll see you in the next episode.

---

## [2/20] Merci Grace (ex-Head of Growth at Slack) on PLG, interviewing, storytelling, building a diverse team, hiring salespeople, building a growth team, and much more

**Lenny** (00:00:03):
Merci Grace has been a founder, an investor, head of growth at Slack, and now a founder again. She's also one of the co-founders of Women in Product, which, if you listen to this podcast, you know I'm a huge fan of. In our conversation we cover what she's learned from her time helping Slack build a product team and figure out growth, how Slack innovated the concept of product-led growth and scale it to become one of the biggest B2B companies in the world, the most common mistakes companies make when going product-led, signs you can and should go product-led, when to hire your first head of growth and what to look for, a bunch of advice on hiring, something Merci is incredibly good at, and so much more. I hope that you enjoy this episode with Merci Grace.

**Lenny** (00:00:49):
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**Lenny** (00:01:59):
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**Lenny** (00:03:02):
Merci, thank you so much for joining me. I've always been such a fan of yours from afar through your writing and your Twitter. We've interacted a bit on Twitter. We've never really had a deep conversation. And so I'm really excited. And so, welcome.

**Merci Grace** (00:03:18):
Thank you. Excited to be here.

**Lenny** (00:03:20):
I'm excited to chat. You have this incredible background. You're a founder, you're a game designer, you're head of product, head of growth at Slack. Then you became a VC. Now you're a founder again. Such an impressive and unusual journey. I'm curious how you got into product initially, and then just how did you work your way up to head of product and the head of growth at Slack?

**Merci Grace** (00:03:42):
Yeah, I got into product accidentally. I was first a game designer and actually started a venture-backed game studio right after college when I had absolutely no idea what I was doing. I got my first term sheet as a founder before I knew what venture capital was. Purely accidental. And it's funny because my career arc went founder, game designer, product management, VC, CEO of your own startup, something that people try to do on purpose now, and I was not trying to do it on purpose at all. I was just following my curiosity and my love of how thinking works and how people make decisions. And so that really went from games, to product management, to venture, and then back into product.

**Lenny** (00:04:32):
Having been in VC now, having your own startup, what did you learn in that time that maybe surprised you now being a founder that, "Oh, wow. That was useful to learn and experience"?

**Merci Grace** (00:04:42):
Oh, yeah. So many things. I think one of the things that is quite obvious from the get-go, when you have had a few months under your belt, you've been seeing a bunch of pitches, and seeing the one-on-one pitches and then seeing the partner meeting pitches, is how different really great CEOs and startup leaders are at storytelling, at coming up with a pithy answer, at owning the room. The fundamentals of their businesses might not even look a lot better, but when you're in that room, you feel so differently about it. So I think how much really the founder matters.

**Merci Grace** (00:05:21):
And then the other thing, and this is my surprising thing about venture that I tell people that I didn't expect to learn, which is, especially on Twitter and even in the media and the press, some merger happens or doesn't happen, some deal happens or doesn't happen, and there's a lot of armchair quarterbacking where people are sort of filling in, "Oh, that happened because this fundamental shift in the market for X, Y, Z, because this research division and blah, blah, blah," a lot of things that seem really objective and really rational, but deals happen or don't happen typically because of interpersonal dynamics and sometimes even just personality clashes or petty holdouts from years before. And so I think how personal it is and how it's not always necessarily about the fundamentals of business. It's oftentimes because people just can see you as a founder, or CEO, or can see you running something like this. And so it's very subjective, more subjective than I thought it would be.

**Lenny** (00:06:32):
It's interesting. In both examples it comes back to the founder and how they present and how they behave. On the first point, presenting storytelling, being someone that VCs respect and want to invest in, is there anything that you have learned how to get better at that sort of thing, or is it just do it for a while and you'll get better? Is there something that folks can do to get stronger at that?

**Merci Grace** (00:06:54):
Yeah. When you have the opportunity to tell the story, when you have a pitch, when you're writing a blog post, when you're speaking at a conference, really, it's your stage. You get to manage the narrative and to say things in a certain way, position things in a certain way. And so that's where writing is really important. So even for a pitch or a conference talk or something like that, always start with an outline, always get really clear about, what's the arc of the story that you're telling?

**Merci Grace** (00:07:25):
And honestly, looking at things like movies and TV shows, every pitch should start in the middle of the action, like a thriller or like a drama, like Mission Impossible movies always start with Tom cruise doing some crazy shit in the middle of the job right before the job that the actual movie is about because it gets your attention. And so I think that's one of the things that people often try to fit whatever the template they think is. And often in business, it ends up being, "Oh, what's this more staid, boring way to say this?" And in truth, great storytellers are not boring and they don't seem businessy.

**Lenny** (00:08:09):
I love that very tactical piece of advice. Start with the action and the climax and work backwards from that, almost. Are there any examples of that that you recall of a founder doing that or a story that does that, just to make it even more concrete?

**Merci Grace** (00:08:21):
That is how great pitches always go. So oftentimes, and this is just every sort of mediocre pitch, mediocre pitch deck that you see will start with, "Oh, here's the market," or something like that, right? Which is like, this isn't a presentation about the market. This is a presentation about you. And so if you are going to say that you're the only founder that could start this company, or you have this really unique insight, start there. Even though it feels like you haven't built up to it yet, or anything like that, you don't have to, you'll backfill all of that later. But getting their attention so that they close the tab, they put down their phone, that's the most important thing. You can still lose them later in the narrative, but getting attention, just going to market and getting attention for a startup is the kind of P0 for any of those interactions.

**Lenny** (00:09:16):
I love that. So start with the insight. That's a really good piece of advice. I could see a lot of decks improve having done that. And I know a lot of VCs look for, "what is the unique insight this founder has?" And so that's a really good idea to start with that and blow people's minds a little bit.

**Merci Grace** (00:09:31):
Yeah.

**Lenny** (00:09:32):
Speaking of amazing founders, I want to segue a bit and to talk about Slack and your experience there with Stewart. What's something about Slack that maybe most people don't know?

**Merci Grace** (00:09:44):
Oh, yeah. It's funny, especially now, many years later, but Slack internally in 2015 kind of timeframe, it wasn't totally clear to people that the social aspect of Slack wasn't something that was important or meaningful to Slack internally. And so people would email us or talk to us at parties about, "Hey, have you seen Discord? They're coming for you." I'm like, "It's similar. It's not going after the same market." And people would actually join the company with some very concrete ideas or expectations about the social use case for Slack. And so, one of the best things, honestly, that the early founding team at Slack did and were able to give to those of us who followed them was the understanding that this is a tool for work. And that made thousands of small decisions instant and obvious.

**Merci Grace** (00:10:47):
There was this internal campaign that was very irritating to me at the time from people saying, "We absolutely need to allow people to block each other on Slack." All these people who are using open source communities, all these different sort of use cases for it. And I went on a bit of a rant, I would call it in... I think it was our culture channel, which was just its own sort of total shit show, but this channel where people would this meta thinking about Slack, and there was this consistent question about blocking. And so I went on quite a little tirade about how blocking is a tool. And so, yes, if someone is, you feel, harassing you and you would like to block them in the immediate moment, it will make you feel better. It'll make you feel a little more safe.

**Merci Grace** (00:11:41):
But businesses have an HR function and they should absolutely know. You're first of all sort of brushing it under the rug and letting this person go off and treat other people in this negative manner. And then the sort of counterpoint that I also provided is that blocking isn't always used by people to protect themselves. It could be used by people who don't like you at work to exclude you from important meetings or discussions. Your performance drops off. You eventually get put on a PIP or you have issues continuing to perform your job at work because people singled you out and multiple people blocked you and excluded you from the conversation. And I think that argument eventually made headway with people, but the fact that it was such an open conversation at the company really helped me see that it wasn't obvious to everyone that Slack was a work tool because it feels so social and it feels so fun.

**Lenny** (00:12:45):
I love that reversal and coming back to why this might hurt you versus why you may think you really need this feature. What this makes me think about is I actually use Slack for social feature in a big way. My newsletter subscribers, there's about seven, 8,000 people in a Slack.

**Merci Grace** (00:13:01):
Wow.

**Lenny** (00:13:02):
And it's the use case that you don't believe Slack should have done. I'm curious, and no hard feelings, do you feel like they will focus on this in the future? Or should they, maybe in the future? I'm guessing there's just not a lot of money to be made there. And so I could see why that's not a focus, but do you think that'll change?

**Merci Grace** (00:13:21):
Yeah, it's interesting. So you are participating in this creator economy that wasn't around at the same level in 2015. The kinds of communities that were happening on Slack would be a Burning Man community, an open source community that was massive and everyone had a weird Linux set up, and so it was usually time-consuming for our support team to help get people's machines working and things like that. So I don't know, because what you have is a little bit of a prosumer use case, right, where people have a personal but also very much a professional community with you as well. And I think that Discord is moving more in that direction. It's a little bit more of a natural step for them to take, I think. And it's funny, because for me, Slack doesn't exist anymore in the way that it did even a few years ago. It's not an independent company anymore. And so I think the question would be whether it aligns with the long-term interests of Salesforce.

**Lenny** (00:14:20):
Yep, that makes sense. We don't have to get into it too deep here, but I really like Slack for my use case because my subscribers are generally already in Slack. They're at work. Discord is just such a noisy thing and such a new product for people to use. People often love to hate on Slack because it's this big old thing and they're using it for work, but it's actually amazing for my use case, and so I'm going to keep using it. And Discord-

**Merci Grace** (00:14:44):
I know I still have the Women in Product community on Slack as well for that same reason and because it's professional and adjacent and it is tied into your professional identity as a person, but also, yeah, you're already on it. So reengaging your community is more a question of an app channel or a mention than it is having to reengage using an email campaign or something like that in order to get someone's attention.

**Lenny** (00:15:09):
Going in a slightly different direction and into growth, correct me if I'm wrong but Slack was one of the early innovators in this whole product-led growth movement. Is that accurate?

**Merci Grace** (00:15:21):
Mm-hmm.

**Lenny** (00:15:22):
Okay, cool. So what I'm curious to hear is what was it like early on helping figure out how to grow this thing that became this behemoth massively successful company and figuring out this idea of product-led growth? And then I'll ask a couple questions as we chat through this.

**Merci Grace** (00:15:37):
Yeah. So early on, I mean, I definitely got the job that I got at Slack because I had been a game designer. And Stewart Butterfield, the CEO and founder, and I knew each other from our shared time having both run, it turned out, very unsuccessful gaming committees, and being people, I think, who have the same weird taste in indie games and things like that. And so he knew, and this was part of our discussion, that I would bring a familiar sensibility to the role I was hired to, which wasn't called growth at first, it was new user experience. So it was the onboarding experience, signing up, getting started. And that's really where we started with it, was coming at it from not trying to do a specific number or anything like that but a belief that this is a great product and we had product market fit, that was pretty obvious at the time, and so how do we help clear away the fog of war and let people see the map that is, "Here's Slack, and here's where everything is, and here's how you can get started using it"?

**Lenny** (00:16:50):
That is so interesting that so much of that was rooted in game design. I had no idea. That's so interesting that you both had that experience. It definitely shows in the experience. So at that point I imagine product growth was not a thing. It was just, "How do we grow this thing?"

**Merci Grace** (00:17:04):
Yeah.

**Lenny** (00:17:05):
What did you learn from that experience of just how to grow a thing like Slack that is user first and the way that a lot of companies are trying to grow these days?

**Merci Grace** (00:17:13):
Yeah. I think one of the best things that we did is that we really started with curiosity first, and we weren't like, "Okay, here are all of our baseline metrics. We already know what's important. Let's just do this." Because April Underwood, former CPO at Slack, had this great line that she would say internally, which is, "No one has built Slack before." I really loved that as this kind of mental starting place where it's like, there isn't going to be this cookie cutter thing. And it was funny too, in the experience of building out onboarding and running all these experiments at Slack, to see people copy things from the product that we knew were not working.

**Merci Grace** (00:17:59):
And so I think when I first joined early 2015, we had an onboarding experience that had these little circles that would animate. It was very light, too light. There were too many of them. I remember my first few weeks doing customer support in Zendesk, and I would get screenshots from people reporting some unrelated bug and notice this person has been a user for six months and I can see they still have these little throbbers all over the place. Okay, this is not working. People don't understand that they're supposed to click on them. I think Discord has a similar design, but they use the little World of Warcraft style exclamation point, which I'm sure is much more effective. But it was hilarious and also kind of sad to watch people trying to replicate things in our product that actually weren't even working for us, but they had no insight into that.

**Lenny** (00:18:52):
I had the same exact experience at Airbnb. People just sit there, copy everything Airbnb's doing and have no idea. There's so many failed experiments that haven't been unlaunched, and we're just trying to figure things out.

**Merci Grace** (00:19:04):
Yeah, exactly. Yeah. We're all trying to learn. I think it is very dangerous to say this specific metric is a North Star for every business. I think one of the most surprising things, and of course when something's true it becomes obvious and not at all surprising, but we had thought of Slack as a sync but also async kind of a platform, but then over the course of a bunch of experimentation and user research saw that a bunch of the things that moved the needle for us were about getting people into their new Slack team at the same time. So, Jules Walter, PM on the GRIF team, did some experiments around push notifications on mobile, just getting people in. It's still live in the product today because it was, it turns out, massively successful. It really matters that someone is there to greet you when you join.

**Lenny** (00:19:57):
Did you have a rule of thumb how many people needed to be in a Slack for it to start to take off?

**Merci Grace** (00:20:02):
We had a activation metric that we got to through some initial regression analysis, and then we tested the hypotheses that we developed from that regression analysis and made it into the product. And so for us it was three people, real human beings, not bots, and 50 messages, real messages, not people, because that was our real messages, not bot messages. Three people ended up being the lowest number at which things do start to break. So having a one-on-one conversation is a lot easier, having one-on-one text message or email, any other thing is going to be more straightforward. There's almost nothing, and especially when we were comparing ourselves so actively and successfully at the time to email, there is nothing broken about a 35 message one-on-one email conversation. It's totally fine. It's a series of letters back and forth. As soon as you add one more person to that, it gets a lot messier.

**Lenny** (00:21:08):
I forgot about that initial vision of Slack, trying to replace email.

**Merci Grace** (00:21:13):
I know.

**Lenny** (00:21:13):
That's not even something we talk about anymore. Interesting.

**Merci Grace** (00:21:14):
We never talk about it. Yeah. And now it's funny. I'll see some of the media that gets created or the television commercials and I'm like, "What is..." Balls moving around and little grooves and stuff. And I'm like, "I'm not sure what they're supposed to be comparing themselves to. Maybe just themselves."

**Lenny** (00:21:34):
Right. I think Slack is Slack now, and you don't need to replace email. I think they found a niche.

**Merci Grace** (00:21:40):
Yeah.

**Lenny** (00:21:40):
That also reminds me, I actually tried using Slack with my wife. It was just me and my wife in Slack. We tried to use that as our main communication hub, and it was a little much. We moved away.

**Merci Grace** (00:21:50):
Yeah, it is. It's funny how it's just a little too much architecture, a little, yeah, too big of a house for two people, kind of.

**Lenny** (00:21:59):
That's right. Yeah. But it was fun. We had channels for events and love. We had a love channel. Anyway.

**Merci Grace** (00:22:05):
No.

**Lenny** (00:22:07):
So you mentioned this push notification feature being really effective. Is there anything else that just stands out to you as, these are just lessons I've learned in how to grow a product that's kind of prosumer product-led bottom-uppy, things that stick with you that you bring to future products?

**Merci Grace** (00:22:22):
Oh, yeah. One of the big ones in that regard is the understanding that there are people who are just more social, right? I'm sure you're this kind of person. You're a connector and you know a lot of people, you love introducing them, bringing them together. We are who we are, fundamentally. And so within any population, including a user base, there will be people who are more likely to invite other people to the product or to bring people around into it, especially if it's something like a collaboration product. And so I thought it was much easier to get those people to share the product with bigger groups of folks than it would be to get someone who's just not like that, who never is the host, who doesn't invite people to stuff. It's a lot easier to get someone to send more invites than it is to get someone who's a little shy to even send one.

**Lenny** (00:23:16):
So what that makes me think about is just pick the right persona, an ICP. A person, especially for a social oriented product, will invite people into the product. Is that how you think about it?

**Merci Grace** (00:23:27):
Yeah, exactly. It's knowing the persona and then it's also doing things like making sure that someone has multiple opportunities to invite, even though it's a counterintuitive thing. Across many types of products I have seen user interviews where people are going through an onboarding experience, and they come to the invite screen and they say, "Oh, I would never invite someone. I haven't seen the inside of this product. I wouldn't do this," et cetera. That is advice to not listen to. You need to have invites early and often so that you catch people who want to share it, are social people. And then for the people who would never participate in that, they can ignore it or skip it. But that doesn't mean that it shouldn't be all over the entire product.

**Lenny** (00:24:17):
And it's optional at that point, right? It's just like, if you want to invite, invite, but you don't have to.

**Merci Grace** (00:24:23):
Yeah, yeah. I'm never a dark pattern person. I think it was Marco Polo, the async video chat app, did a bunch of dark pattern stuff, I remember, maybe three or four years ago where they would auto-select a ton of people and send them a text message that looked like it was from you. It was really awful. So I'm definitely not a dark pattern growth at any cost kind of a person, but it is like have the invites there for the people who will want to and the people who, even though they sound pretty offended in their tone of voice when they talk about, it's not enough for them to not engage with your product.

**Lenny** (00:25:00):
I find the same pattern effective with credit cards for a subscription app and B2C subscription. Just like, "This is a trial. You can enter your credit card now if you want, or you could do later." I find that drives a lot of growth in revenue because a lot of people are just like, "Yeah, I'm ready. Yeah. Let's just do it."

**Merci Grace** (00:25:15):
Yeah, exactly. I think people often, and this is probably even a larger statement about human beings, but we're so focused on ourselves, right? I think that's one thing that parents tell middle schoolers is, "I know you feel really awkward right now, but so does everyone else. No one's thinking about you. They're just thinking about themselves and how they come off." And then we'll do that to our own detriment in business where you'll set up something like a timed trial and say, "Okay. Well, I want to start getting revenue as soon as possible. So we'll just let people have this for a week." But the truth is for every week that you continue to let people use it, you get incrementally more people who do convert because their timing on buying your product has nothing to do with your schedule or how quickly you want revenue and everything to do with, where in the quarter is it for them? Do they have a new project that they can use to try out your product?

**Lenny** (00:26:12):
I love that advice. Just step out of yourself and recognize people have different motivations and are in different stages of the journey and may just be ready to go. And if you give them a chance it may actually work out really well. I wanted to chat a bit about onboarding. You mentioned that you initially started working on onboarding and that kind of turned into this growth team. I find onboarding often ends up being one of the biggest levers for retention, obviously for activation, and then just broadly growth. Is there anything that you've learned over time of just how to think about onboarding and how to optimize onboarding, how to approach onboarding as a growth team and maybe just as a startup?

**Merci Grace** (00:26:49):
Yeah. My thoughts and feelings about onboarding really go back to my experience designing games where I would design the game from the onboarding experience. So there wasn't a sense of, okay, here's exactly the game and all of the game dynamics. But how you introduce something, how you frame something matters a lot. How will someone discover this? And so if you can think about even an online product that you're working on from that first introduction, "What will it be like for someone to come in here? What will I be asking them to integrate with? Will I be asking them to upload something, to invite someone else? What are the steps between the user and the full value of your app?" is something that's very useful to think about literally from the first days that you're designing the product.

**Merci Grace** (00:27:46):
Unfortunately, many people think about onboarding at the last minute and it ends up being the final piece of product work, or, and this may be a little bit controversial of an opinion, but I'm not a fan of the plug and play frameworks for onboarding for that reason. I've seen them advertised actually using, "Here's how to replicate Slack's onboarding in using our tool," and things like that. And I'm like, "Oh God, don't do that because what worked for Slack won't necessarily work for you." And it certainly won't be native and feel deeply tied into the product experience, which it absolutely should be.

**Lenny** (00:28:29):
This episode is brought to you by Whimsical. When I ask product managers and designers on Twitter what software they use most, Whimsical is always one of the most mentioned products, and the users are fanatical. Whimsical is built for collaborative thinking, combining visual, text, and data canvases into one fluid medium. Distributed teams use Whimsical for workshops, whiteboarding, wire frames, user flows, and even feature specs, and that includes thousands of built-in icons and a rich library of templates. See why product teams at leading companies call Whimsical a game changer. Visit whimsical.com/lenny to have my own templates added to your account when you sign up. That's whimsical.com/lenny. For somebody that's trying to improve their onboarding and think about onboarding, are there examples of companies and flows that you think of that are really good, maybe other than Slack?

**Merci Grace** (00:29:25):
Yeah. The ones that I really find a lot of delight in tend to be ones that are deeply intertwined with the product. So throughout the course of using the product you learn you get onboarded to the value of it. Probably the clearest tools in which you can see this dynamic are things like to-do lists, where there will be an item on the to-do list that says, "Click the square next to this to mark this task as complete." And now you've just completed your first task and it's really in there, and it doesn't feel like this fake kind of veneer on top of it. I really like something that is not pasted on top of the experience but something that uses the product to teach someone else how to use the product.

**Lenny** (00:30:13):
You're telling me there's no easy plug and play silver bullet solutions? God damn it.

**Merci Grace** (00:30:18):
Yeah, I'm sorry. It turns out it's just hard work. The other thing that people don't do enough is stay in touch with the real human experience of what onboarding is for your product. So it's very easy, especially if you work at a company that has a high volume of signups every day, to just always look at the conversion number and that anonymized pile of people winding their way through your actually made up benchmarks for them. It is messier and way more awkward to have to talk to human beings, but absolutely necessary. You want to hear the tone of voice. You want to see the expression on their face. So once a month, ideally, you should just have some sort of a schedule for yourself where if you're at a larger company and you have a user researcher who can recruit people for you, that's great, but if not, just go find people who either fit the demographic for your user or even are your user and have them sign up for an account and walking through it. And it is embarrassing, but very educational.

**Lenny** (00:31:26):
That's awesome advice. It makes me think about Teresa Torres and her framework around continuous discovery habits, where she has this whole framework of setting up count leads, where people could just book you and you automatically talk to a customer every week. And we're going to have her on a different episode, maybe before this, maybe after this. I'm not sure how it's all going to play out. But yeah, that's a great reminder to invest in actually talking to customers. And that's a good segue. I wanted to come back to the whole idea of product-led growth, especially because it's so popular and hot and everyone wants to be product-led these days because it's cheaper and grows quickly and there are big sales teams. So first question is what have you found in looking at companies, talking to companies, advising companies, what are the most common mistakes would you say startups make when they think about figuring out product-led growth?

**Merci Grace** (00:32:13):
Oh, yeah. So one of the most common things that I see folks do when they haven't had much experience really simplifying onboarding down or something like that is they'll often have an idea of, "Okay, here are the seven things that you have to know about our product." And one of those is usually some power user feature that an executive really likes or something. They'll have this idea that they want to have a carousel that meets you when you open up the product and it takes you through all of these informational panes. And what's funny is that then if you were to talk to those same people in a usability study for some other product, they'd be like, "Oh, yeah. No. Click. I'm not going to read that."

**Merci Grace** (00:32:58):
But again, that's that sort of, we have this expectation of our users that they're going to give a shit, that they're going to read the text, that they're going to be at the level of investment in our product that we are, which is just categorically false. You have to understand that people have really limited attention and no one cares about your product the way that you do. And so it can feel like you're dumbing it down or oversimplifying. And if you don't feel that way about your onboarding, about the growth work that you're doing, it's probably too complex.

**Lenny** (00:33:34):
Do you find that if you have a carousel, something's gone wrong? Or are there times when a carousel and a little guide makes sense?

**Merci Grace** (00:33:41):
If the carousel is in a product where that's the modality of the product, so I could see a carousel, honestly, working for something like Tinder, where that's basically what the product is, right, you're swiping through it, sure, you can use a carousel for that, right? But only because it matches the user experience of the core product. But most apps that use carousels at the beginning, it is actually this pane that's built to be dismissed quickly.

**Lenny** (00:34:15):
Interesting. So what should people do when they're just like, "Oh, you're going to create this whole introduction carousel"? Is your advice simplified such that you don't really need that, broadly?

**Merci Grace** (00:34:26):
If you haven't been able to talk someone out of it, you can always show them. So I'm a huge fan of learning without shipping and building paper prototypes or building prototype in Figma, or ProtoPie, or something like that, and just do a bake off and prove the point, not with you saying, "Hey, CEO, you're wrong about X, Y, Z. We shouldn't have this three image carousel." Just come up with some different alternatives, like tool tips that are embedded in product, things that are obvious next steps that you can guide people to within a sort of constrained user experience, and then you'll just be able to actually compare whether people understood it, experience A, or whether more people understood experience B. And it can be shockingly clear.

**Lenny** (00:35:18):
Awesome. Yeah. I think in that you can probably tell people aren't going to want to sit through a carousel and check every step. They're just like, "Leave me alone. I'm going to figure it out."

**Merci Grace** (00:35:26):
Yeah. Or even ask someone, "Oh, what was the last carousel that you remember?"

**Lenny** (00:35:33):
"That you finished?"

**Merci Grace** (00:35:34):
Yeah. Just like, "What was the last one?"

**Lenny** (00:35:36):
Right.

**Merci Grace** (00:35:37):
"Oh, that's right. I always close them."

**Lenny** (00:35:40):
I love that. Coming back to product-led growth and figuring out how to do that well, what are signs that your product and just general business can be product-led versus like, "Okay, we're going to try it. It's probably not going to work out. We're probably going to have to hire salespeople quickly"?

**Merci Grace** (00:35:56):
Ideally, that's something that you've thought about pretty deeply before you even started to code the product, because whether you thought about it consciously or not, you have already decided whether it is going to be product-led or sales-led. If it is the type of a solution that you need buy-in from the head of HR to use because you need to integrate with systems that have a lot of PII in them and no IC has the keys to that system at any size of a company, boom, you know have a sales-led motion. That is what it is.

**Merci Grace** (00:36:32):
And so I think just having that sort of objective distance to your own product is always a fruitful kind of place to begin. If you have a product that even if it's for a specific function but anyone at any seniority level in that function could pick it up to use it, so DevTools are probably the most successful product-led growth companies that we don't talk about being product-led, but that's totally how they grow. A junior engineer or a really senior engineer can pick up some dev tool and play around with it and start using it, decide to take it into work or not.

**Merci Grace** (00:37:09):
So anything that you can pick up without needing to have the keys to Dad's Porsche in order to test out can be product-led. More and more I'm also seeing companies that have a enterprise sales motion to capture the customer at the point of adoption, but then they want to use product-led growth frameworks or tools to expand their usage to either drive up retention or to actually expand the number of seats and the number of departments that are using that tool. And that's actually a very good use for all of the same sort of frameworks and user experience concepts.

**Lenny** (00:37:53):
We're throwing out a lot of these terms, and I realize it might be helpful just to try to set a little context. I don't know if you have a clean definition of these things, but how do you define product-led versus bottom-up versus sales-driven, I think is pretty obvious, but how do you define these terms and think about them?

**Merci Grace** (00:38:10):
Yeah. For product-led, I think about it being something that anyone can get value out of your tool immediately and that the tool doesn't need to be augmented by a conversation, or a webinar, or anything like that with someone else in order for them to get to a certain threshold of value. Often you learn a lot as a business from doing a white-glove onboarding for certain personas, and they didn't need you to do that, but you wanted to do it. So, that's still really product-led.

**Merci Grace** (00:38:46):
And then it's funny, bottoms-up is often used in exactly the same way, but I would think of bottoms-up as being not just product-led but also something that can be adopted by anyone at any level within the organization. So there's tools for people managers, like a range, and a bunch of other ones, whereas a manager is running their one-on-ones, getting feedback from their team, et cetera, using this tool. That's a product-led tool often, but that's not really bottoms-up, because in order to grow that tool, you need to do a very good job of finding where managers are in businesses, targeting them, retargeting, and doing things to specifically reach out to someone in that particular function. Whereas, bottoms-up should be literally anyone at a 500 person company could start using this.

**Lenny** (00:39:40):
Got it. That's really helpful. I imagine the Venn diagram overlap of product-led and bottom-up is very overlapped. But in theory, you could have a sales-driven bottom-up strategy or a product-led top-down strategy. Is that right?

**Merci Grace** (00:39:57):
Yeah. Mm-hmm.

**Lenny** (00:39:58):
Very cool. Okay. So we've talked through the context and just definitions of these things, when a company can be product-led. It sounds like the main thing you look for is can an individual adopt this product at a company? That's like a sign that this can be product-led.

**Merci Grace** (00:39:58):
Yeah.

**Lenny** (00:40:14):
Is there anything else that you think is important that if these things don't exist, you should probably not try to be product-led?

**Merci Grace** (00:40:23):
Yeah. The other one that I don't hear people talk about very often is whether there's really day zero value in the tool. This is something that came up for me a lot when I was looking at a lot of these sort of video apps. So both the Presence app, where you're replicating a kind of office experience, or pre-pandemic, now I think this use case is a little more obvious, but pre-pandemic, getting on video chat with someone. And what it does is creates an automatic transcript of your meeting.

**Merci Grace** (00:40:55):
There isn't necessarily a lot of day zero value from doing one meeting on a tool like that, but often the pitch would be, "Hey, in six months or three months, you'll be glad that you recorded the transcripts for all of these interviews that you did because of X, Y, Z reason." That is not something that is valuable if they've been using it for months. It is not something that can be product-led because there's product-led in one direction, there's product-led back out in that same direction. And that can be the frustrating part about product-led growth is that the easier you make it to come in, also the easier it can be to leave.

**Lenny** (00:41:37):
Got it. So you're finding that it's really important for people that adopt it to stick around. And basically, finding value immediately is a way to increase retention and keep people around. And you're finding that if people don't stick around, it's not really going to work. And you need people there, salespeople, basically, keeping them on the product and using it.

**Merci Grace** (00:41:55):
Yeah.

**Lenny** (00:41:56):
Very cool. Eventually most companies end up hiring a salesperson. I was doing some research on this, and I found 100% of product-led growth companies hire a salesperson and a massive sales team eventually, like 100%. Do you have any thoughts, insights, experience on when it might make sense to bring in that first salesperson?

**Merci Grace** (00:42:13):
Yeah. So founders are always selling. So even from the time that you have your very first alpha customers. And it's funny, because I often reference actually the post that you did about how to find your first fast B2B customers.

**Lenny** (00:42:28):
How recursive.

**Merci Grace** (00:42:29):
Yeah, I know, and here we are again. It's all in that initial network, right? So the founder is always the first salesperson. So in that way it is often the case that one of the first three or four people who work in a company is actually a salesperson. But the point at which you should start to hire someone else to do that is when you, as the founder, absolutely cannot meet the demand even though you're getting up really early and staying up really late and building your investing deck on the weekend instead so you can continue to meet with customers.

**Merci Grace** (00:43:01):
And then the other time to do that, apart from just being maxed out, is when you are moving in to and usually up to a customer that both wants and expects to meet with a salesperson. That was what we went through at Slack, was moving from that engineer-driven SMB motion to then getting adopted at companies that really wanted to have a conversation with someone before they continue to spend a lot of money on their product. I think that's one of the things that maybe younger founders or people who haven't worked at enterprise companies before can discount is the customer preference. And then actually there's a whole set of customers that literally have to talk to someone before they can buy anything or just really want to.

**Lenny** (00:43:51):
I've never heard of it put that way where the customer is looking to talk to a salesperson and pull the sales team out of you. Interesting.

**Merci Grace** (00:43:58):
Yeah. And those are, of course, the salespeople's favorite person to talk to. It's like anyone, it's like you want to talk to someone who actually wants to talk to you.

**Lenny** (00:44:07):
I like that. So the advice is high-level. Wait until you just can't do sales as a founder and/or wait for the fact that the companies you're selling to are just expecting a salesperson or a sales team to support them.

**Merci Grace** (00:44:21):
Yeah.

**Lenny** (00:44:21):
Awesome. So that reminds me of another topic I wanted to make sure we chatted about, which is hiring. We were tweeting a bit about this, about the team that you built at Slack and how epic that alumni class is. We're going to have Fareed on here, who worked for you for a while. And so I wanted to get your insights on just, what do you look for when you're hiring people? How do you find/select/keep amazing talents on a team when you're building a company like Slack?

**Merci Grace** (00:44:46):
Yeah, I think a lot of it is the approach is not an exam that I'm proctoring, right, when I'm hiring a role. I'm not sitting in an ivory tower in the seat of judgment. What I'm trying to do is to make sure that whoever I offer the role to wants to take it and will thrive at the company, that they're the right kind of person for the role, especially in product where someone who's a super successful PM at Lyst is not necessarily going to be a super successful PM at Slack, or at Airbnb, or at Pinterest, even though if you think about that class or that cohort of companies, we would've all applied to each other's companies. In fact, I think I actually got rejected by Airbnb on three different occasions throughout the course of-

**Lenny** (00:45:40):
Oh, boy.

**Merci Grace** (00:45:40):
... different years. Because I love travel and it's a great company. But I think there was just something about, I probably would not have been successful in the same way I was at Slack if I had had one of those roles. So I think understanding that it is a two-way street, and when a hiring manager has that vibe, they're going to end up, I think, hiring people who are just positioned to thrive at that company, because you're not saying, "Oh, here's someone that I can get and I can pop them into this power structure that means something to me." It's finding someone like Fareed and saying, "Okay, I could see you having a long and really successful career at this company because of your curiosity, because you're a great communicator, because anyone who's ever worked with you would immediately work with you again." And those are things that I think if you're like, "Let's do this whiteboarding exercise and I'm going to talk down to you," you never end up finding out about someone.

**Lenny** (00:46:38):
Got it. So a lot of it is particular to the company, understanding the culture, how they work and finding that fit for person, like person, company, product market fit.

**Merci Grace** (00:46:46):
Yeah.

**Lenny** (00:46:47):
Are there any universal things that you look for that maybe other people may not look for, things that you've learned of just like, "Oh, I'm going to make sure these habits/traits/behaviors exist?"

**Merci Grace** (00:46:58):
Yeah. I always ask people to do, for an ICPM... World's different if you're hiring a director or a VP. For a standard PM role, I always make people do work. I think we've gone back and forth on Twitter about this. And it's funny, it's definitely something that it's just in the last, I don't know, five or six years, I feel like people are really pushing back on doing what they I think unfairly characterize as free work for a company. I treated this out, but I mean, if you don't want to even do three hours of free work for a company, you probably don't want to work at that company. It's this weird, if you need to be paid for every second of effort that you're putting in, I mean, you probably shouldn't be near a startup in that case because, I hate to break it to you, but the startup that you're at might not be successful and then you will have done all of this work for "nothing."

**Merci Grace** (00:47:57):
And so I really use that as a way to see into how someone thinks, the quality of the solutions that they bring, how they communicate. There's just so much bundled up in giving someone an actual problem, ideally to pick, not one that's assigned to them, but, "Here's three different problems." Because you learn a lot about someone from every choice that they make. I think that's probably my most controversial hiring topic, but I've found a very direct relationship between the people who just really kicked ass on this, went on to be very successful and lead organizations at Slack.

**Lenny** (00:48:32):
And you're specifically referring to the project that they do, right, on their own time?

**Merci Grace** (00:48:35):
Yeah.

**Lenny** (00:48:36):
What did you look for in their results of their project?

**Merci Grace** (00:48:40):
The quality of the solution. Something like Slack is not a deeply technical product, but I was a little bit surprised to see a number of smart people who'd worked at good companies who decided that, "Okay, it's magic wand time." And now assuming that, for instance, Slack bot was a state machine that had a bunch of contacts and would have this almost NLP-driven conversation with you. So that was a big red flag to me, for someone just not... And it's funny because I'm not like an engineer and I wouldn't even think of myself as a "technical PM." But PMs have to know basics of how the tools work and what would work in the tool. So, that's a big one.

**Merci Grace** (00:49:34):
Whether someone was able to tell a compelling story was huge, especially at Slack, which was a very product-driven company, a very narrative-driven company. If you were going to present data, it needed to be within a very specific context. And it wasn't a company where the number always won. It was a company where the story always won. And so if someone did a great job of structuring a narrative, they had technically possible but also creative solutions and they picked one for good reasons, they would know how to measure it and how to build something like that, they were just going to be much better than someone who didn't hit literally every single one of those things at a high-level.

**Lenny** (00:50:21):
I like your point about Slack being story-driven and how people with a great story often win. Is that a part of the Slack culture and how Slack works?

**Merci Grace** (00:50:31):
I think it's still probably that way. It was a huge part of the culture when I was there, when it was the initial founding team and an independent company as well. So who knows what will be successful for them within Salesforce? I think it's quite literally a different company now.

**Lenny** (00:50:49):
Whoever has the best CRM wins. That's really the point.

**Merci Grace** (00:50:54):
Yeah, exactly. The good leads.

**Lenny** (00:50:55):
Yeah. So we've been talking about hiring, and I want to come back to the growth element. So you built the growth team at Slack. How did you think about building out a growth team? And I'm also curious, just when should a company bring in a first head of growth?

**Merci Grace** (00:51:13):
Yeah, yeah. It is time to start working on growth when you feel like you have product market fit. It doesn't have to be totally perfect because you absolutely use a growth team to really accelerate and improve your product market fit. That is a part of the value of the growth team. But you do need to feel like, "Okay, once we..." Even if it's do a white-glove onboarding with people, if I spend 20 minutes with you and I show you my tool and I explain how it works, wow, you really get it. You want to pay me money for it. You're still using it six months later, you're ready for a GRIF team. You don't have to have all of your ducks in a row. You don't have to have everything instrumented.

**Merci Grace** (00:51:59):
And then what I often tell people is that, "Your first PM to touch growth or just engineer or PMM to work on, it should be someone who has a lot of trust at the company and who really loves and understands your customer." Because a lot of the growth stuff is pretty straightforward. It's a funnel, right? There's a lot of fantastic classes like Reforge. There's a lot of writing on the internet about how to do it. But to a certain extent, everyone is inventing the specific things that work really well for their customer and their product.

**Lenny** (00:52:35):
So you co-founded Women in Product, which is an organization as an outsider I've been incredibly impressed with, and I'm trying as often as possible to collaborate with the community. There's all these local chapters, and everyone I've ever met that's in the community has been incredible. And so I'm curious as a product leader, as a founder looking to bring in more women and have a more diverse product management org, or just org in general, what are one to two things that folks can do? The obvious answer, I imagine, is hire more women. Is there other advice you could share with folks that are trying to have a more diverse company and product team?

**Merci Grace** (00:53:08):
Yeah, it's funny, I don't think it's always hiring more women because not all women are friends to other women, and they may in fact relish their position as the only girl. I think on Reddit it's like the, "I'm not like the other girl's name," or whatever. You could easily get someone in like that and she can actually actively turn off other women.

**Lenny** (00:53:31):
Oh, wow.

**Merci Grace** (00:53:31):
One of the interesting things that I've seen about hiring women is that women do tend to be less aggressive and risk seeking than men do. I really didn't want that to be true, and I think I'm an outlier in being a multiple time founder and things like that. I have a risk profile that I have been bummed to see is not something that's widely shared by other women. And so I think part of it is that you, if you're just looking at passive inbound or through referrals or things like that, you're just going to end up with fewer women in your pipeline and you are going to close women, I think, at a lower conversion rate than you close men, especially if you're an earlier or riskier business.

**Merci Grace** (00:54:21):
And so in order to offset that, you just need to go interview a lot of women and not blame it on the pipeline. You need to actually go seek them out and find them. And then once you do, it can be this really self-reinforcing mechanism. The way that a lot of diversity initiatives that companies work is that it's one thing to have a team of all white men, but if you have two African American people in your first 20 people, you could have a lot more diversity and not even amongst just that one group. Women want to work with other women, but men of all races I think look at an organization, but let's say it's all white people, but there's a few women, they may look at it as just a more diverse, more friendly place and be less intimidated to be, for instance, the first person of color who works there.

**Lenny** (00:55:16):
That makes me think about Slack. Early on, it was one of the most diverse teams that I'd seen. Is that relatively accurate?

**Merci Grace** (00:55:22):
Yeah. We spent a lot of time on that pipeline, making sure that there were a lot of people who got interviewed. And it was never like an excuse as to not find someone. Then that kind of inertia that can make you end up with a company of 50 white men because they referred their friends, the people who they naturally feel comfortable with and things like that, that can also work in your favor if early on you just hire more women and you hire more people of color. They'll feel more comfortable because they're not the only one, and then they'll refer their friends as well.

**Lenny** (00:56:01):
So especially important when you're just starting out to put a lot of time into this. It sounds like that's the core of this is prioritize it, put in the time, especially early on, because that'll create this flywheel.

**Merci Grace** (00:56:12):
Yeah. It's funny, I've often been the only woman on a team at a startup or literally at the startup entirely. And there is a huge difference, I've found, between being the only woman and being one of even two women. The tone really changes. People then are like, "Oh, now we have women coworkers." It's not just Merci who also plays D&D and curses at the office or whatever. It is women as this more general class. And so they start to honestly be more respectful and kinder to each other and treat each other better too. And so I think that's like the other thing. It's not like it's better for anyone to be in a homogenous group. I think it's actually better for everyone to be in a more diverse group because the sort of baseline for how you treat each other goes up.

**Lenny** (00:57:07):
Speaking of founders and startups, you're working on something now. For people maybe interested in working with you or maybe even potential customers, is there anything that you want to share about what you're working on, where it's going, anything there?

**Merci Grace** (00:57:20):
Yeah. So we're really early, and I'm not exactly sure when this podcast is coming out, but if you go to panobi.com, it's P-A-N-O-B-I .com, there is either a real landing page there, or today there is just a Google form for you to fill out that will ask you a few questions about product-led growth, which is the area that we're building in. And if you're someone who is curious about product-led growth, if you're head of growth at a company, if you're a CEO, or a founder, or an investor who's interested in finding out more, picking up maybe even a tool to help you be successful at it, go to panobi.com, and you can also just DM me on Twitter.

**Lenny** (00:58:02):
Speaking of that, where can folks find you online? How do they reach out? And then also just how can the audience be useful to you?

**Merci Grace** (00:58:11):
Oh, that's nice. So you can find me online. On Twitter, I think, is probably my best sort of public inbox. My DMs are open. I do respond to them, especially if it's something direct that I can be helpful with. If you are a woman in product management, go to womeninproduct.com and you can apply to join our community. We've been going since 2015, and there's many people who are in it as well. And then, yeah, if you're interested in growth more generally go to panobi.com.

**Lenny** (00:58:40):
Amazing. Merci, thank you so much for joining me. I had a ton of fun. I learned a ton, and thank you.

**Merci Grace** (00:58:46):
Likewise, Lenny. Thank you.

**Lenny** (00:58:50):
That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast. You can also learn more at lennyspodcast.com. I'll see you in the next episode.

---

## [3/20] Manik Gupta (ex-CPO Uber, Google Maps) on how to build consumer apps, why it’s useful to be optimistic about technology, creating inflections in your PM career, the changing CPO role, and more

**Lenny** (00:00:03):
Manik Gupta has led two of the most successful consumer products in history: Google Maps, where he was director of product for the Maps team, and Uber where he was Chief Product Officer. After leaving Uber, he spent most of his time working on a product to help people avoid getting COVID, called CVKey, and most recently he took on a role at Microsoft as Corporate Vice President leading many of their consumer efforts.

**Lenny** (00:00:25):
In our conversation, we cover what he's learned about building successful consumer products, how to structure and higher product teams, building consumer apps, a concept called the consumer stack, company market fit versus product market fit, what it's like to be CPO, what he learned working at Microsoft versus Uber versus Google, and also a ton of career advice for anyone thinking about becoming a CPO someday. I hope that you enjoy this episode with Manik Gupta.

**Casey Winters** (00:02:00):
Coda is a company that's actually near and dear to my heart, because I got to work on their launch when I was at Greylock. But in terms of what I love about it, you know I love loops and Coda has some of the coolest and most useful content loops I've seen. How the loop works is someone can create a Coda and share it publicly for the world. This can be how you create OKRs, run annual planning, build your roadmap, whatever. Every one of those Codas can then be easily copied and adapted to your organization without knowing who originally even wrote it. They're embedding the sharing of best practices of scaling companies into their core product and growth loops, which is something I'm personally passionate about.

**Lenny** (00:02:36):
I actually use Coda myself every day. It's kind of the center of my writing and podcasting operation. I use it for first drafts, organize my content calendar, to plan each podcast episode, and so many more things. Coda's giving listeners this podcast $1,000 in free credit off their first statement. Just go to coda.io/lenny. That's coda.io/lenny.

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

**Manik Gupta** (00:03:06):
Thank you, Lenny. It's great to be here, man.

**Lenny** (00:03:08):
I don't know if it's obvious, but I am quite honored to have you on this podcast. You've had such an illustrious career as a founder leading the Google Maps team, as CPO at Uber for, I believe, four years. Now you're kind of a fancy VP at Microsoft on consumer stuff. It's this incredible career and trajectory. My first question is, looking back at your career, what would you say is maybe the one or two main things that you did that helped you get to where you are today? For folks that are maybe earlier in the career, of what they should be focusing on.

**Manik Gupta** (00:03:39):
Yeah. Thanks, Lenny, for having me. I'm also a big fan of yours, by the way. I love your newsletter and it's been incredible to just see how you have also grown both the set of topics that you cover and this podcast. Just really a big fan, so again, thanks for having me.

**Lenny** (00:03:54):
Appreciate that.

**Manik Gupta** (00:03:55):
Let me start by telling you a little bit about my philosophy of this. I'm maybe a little bit late to the party, but I recently read this book from Morgan Hausel on Psychology of Money. And I highly recommend your listeners read it if they get a chance. There's a chapter in there, he talks about luck and risk. What he says is, when you look at individuals and you think about, or you ask them, or you think about what they have done that have made them successful, we tend to put a greater amount of emphasis on effort and a little less emphasis on luck and risk. I think I strongly subscribe to that. The important thing when you look back is how much luck played a big part, and of course the risk that somebody took played a big part.

**Manik Gupta** (00:04:45):
This is something that I've been thinking a lot about myself, which is what are some of the patterns of people who have had multiple careers and have gone through a journey where they've learned a lot and they've contributed and things like that? I think there are two patterns that stand out, both when I look at myself in terms of what I've been through, and also when I talk to a lot of my friends who have also gone on and done interesting things, and I wanted to cover both of that. The first one is really about people. It's about surrounding yourself with the best people you can find.

**Manik Gupta** (00:05:16):
It was so funny. I was watching the Warriors game last night, and yeah Warriors, we won the NBA championship. That's great.

**Lenny** (00:05:22):
Go Warriors.

**Manik Gupta** (00:05:24):
One of the reporters, I think she asked Steve Kerr, the coach, "What's the secret?" And he goes, "Well just hang around superstars." That's what he said and he just passed the mic over to somebody else and said, "Look, this is a team that's hanging around superstars." And that's exactly what it is. If you're create enough opportunities, especially early on in your career as you asked, around hanging around people who are doing interesting things and they're doing things which really are different, or they're doing things in a different manner and it's exciting, the right things will happen.

**Manik Gupta** (00:05:55):
I was lucky in a way that I caught myself in that situation. I grew up in India and when I was 16 I got a scholarship to move to Singapore to do my high school and then my undergrad studies. It just turned out that during those days, Singapore... I mean it still is, but it was a melting pot for the best and brightest folks that you can get from all over the Asia diaspora if you will. Among my colleagues and my fellow students there were a bunch of really, really smart people, so I just learned a lot from them and that gave me a great start to just go on and do something interesting. Right out of college, I started my own company and I did that with two of my classmates. One of them happens to be one of my best friends whom I grew up with who also came on the same scholarship with me to Singapore. We were just part of that ecosystem and it gave me a lot of opportunities to try out different things in college and so on and so forth.

**Manik Gupta** (00:06:44):
I think the main thing that I would say here for people who are early in career is just surround yourself with people who are really good at what they do. Learn from them. And by the way, play the long game. Once you find someone like that, stick to them. As long as they want to hang out with you, but just stick to them. Because you will go on to do multiple things over your career with the same set of people. And the shared trust and experience that you build with A plus people is just going to go a long way. Anyway, that's pattern number one. I think that has helped me a lot and I also see a lot of that in other folks whom I talk to.

**Manik Gupta** (00:07:19):
Then the second pattern is... This is something I resonate a lot with personally, is I'm a strong technology optimist. There's always a lot of narrative these days around technology and maybe a little bit more pessimism, and I find that bizarre. I'm just such a strong technology advocate and optimist, because I feel technology's such a strong force for good. I grew up as an engineer myself, and I've always been attracted to projects where we can use technology to solve a real human need. I did that with my startup, I did that at Hewlett-Packard, I did that at Google and at Uber as well. The passion that you get if you're a strong advocate of technology and how it can really help, it just gets you to choose a set of things that you want to do at scale.

**Manik Gupta** (00:08:06):
For instance, when I joined Google in India to work on Maps, it was all about helping millions of users, around Asia particularly, navigate their world. There wasn't a good solution like that, so how can you bring technology to really solve those problems?

**Manik Gupta** (00:08:21):
I think those are the two patterns, Lenny. One is surrounding yourself with A plus people, and the second is just having very strong optimism and passion about technology. At least if I connect their dots looking backwards, those are the things that have really helped me and a bunch of other folks that I see in a similar situation. I'm hoping that folks early in their career thing through that.

**Lenny** (00:08:40):
I bet there's a big overlap between those two points, technology optimist and just superstars. That's interesting.

**Manik Gupta** (00:08:46):
Yeah, there definitely is. That's actually really good. I hadn't thought about that. You're right. I think there's definitely that overlap, because folks who are in that mode, they really get around more together. I'm also an angel investor and an investor in a bunch of companies. Lenny, you and I have invested in a bunch of companies together as well. And it's like that. It's really about people who have the same kind of frequency in terms of thinking about the world outlook and they want to go on to do interesting things. I think that's really what drives the narrative forward.

**Lenny** (00:09:14):
Speaking of technology optimism and technology in general, of the things that you've worked on, what would you say you're most proud of project wise, product wise, feature wise?

**Manik Gupta** (00:09:23):
Yeah. Again, I've had just the incredible opportunity to be part of phenomenal companies that have created world changing products. I had a small, small, small part to play in that. I always emphasize that. It's not me, it was a team. And I really mean it. I'm not just saying it because I'm on your podcast, but it truly is. I'm particularly proud of the work that I did both at Google and at Uber. I'll give you a couple of examples to illustrate that point.

**Manik Gupta** (00:09:47):
When I joined Google in India in 2008, I started off working on Google Maps and I remember how counterintuitive it was for anybody; my friends and family, a bunch of other folks whom I talked to. Counterintuitive in terms of why would anybody ever use maps on their mobile phone in India? The reason was because the norm was that, firstly, the country's unmappable because there's no good addressing system. So how do you even look at places? Then the second one was there were always people around that you can just roll down your car window and just ask people, "Hey, I'm going here and can you just give me guidance or directions?" That was the norm. That's how people navigated for a really long time.

**Manik Gupta** (00:10:32):
When I started working on it, I think for me, my belief was, again going back to the tech optimism aspect, is why can't we in India have the same quality maps like we have in the United States? Why not? Why shouldn't we do it? Why are users here not getting the same benefit and same productivity gain, if you will, and less stress in their daily commute and things like that?

**Manik Gupta** (00:10:55):
So we started building it. We started building the data. We went ahead and really mapped the country as much as we could. Both ourselves and through a lot of amazing work from our users who co-mapped the world with us. Over time, India became, I think, the second largest country for Google Maps in the world in terms of users. Of course, a lot of that happened because of Android. Android took off and Android had Google Maps on it. But it's just incredible to see how, in a short span of a few years, it just went up to becoming so useful. It's not that we were just distributing Google Maps on Android, people were using it. People were actually using it to go from point A to point B.

**Manik Gupta** (00:11:35):
I feel really proud about that. I think the team did an incredible effort. It wasn't even a big team. It was a relatively small team, very passionate about going and doing this, and we made that happen.

**Manik Gupta** (00:11:43):
Then at Uber, initially, before I took on the CPO role, I was leading maps and marketplace. When I was doing maps and marketplace, again, how do you get the ETA that you see on Uber when you open the Uber app and you request a car... The average ETA's went down to less than five minutes globally. Just think about that for a minute. In fact, it was 75 countries, more than 300 cities, if I remember correctly, where you could just open the Uber app and get an Uber in, average, less than five minutes. A lot of operational work need to happen for sure, but the technology, the marketplace technology especially to be able to connect the right rider to the right driver, have the mapping infrastructure underneath it to ensure that the car actually reaches you in that amount of time; I just feel very proud of all the work that happened during that time to make Uber really successful in terms of providing that kind of a service.

**Manik Gupta** (00:12:37):
One fun anecdote I'll give you where my world came together and it just blows my mind even today, I remember I joined Uber in late 2015 and I made a trip to India to see my parents in sometime around 2016, 2017. I forget. It was around that time. And I was at home in Bangalore and I ordered an Uber. And the guy shows up, the driver comes in, and I sit in the back of the car. He starts the trip using the Uber app, and then he clicks Navigate and he goes to Google Maps. And I was sitting there. I was like, "Man, I built these two to a certain extent." It was just crazy to think about how two of my worlds came together at that point. I still vividly remember that moment where I felt really proud that I had a little bit of a part to play in both those products.

**Lenny** (00:13:26):
That is some unbelievable impact. It boggles my mind how many people have been impacted by the work that you've done on the teams that you've been on. Like a billion people in India and everyone in the world using Uber. It's unreal. I would feel very proud myself, watching that experience.

**Lenny** (00:13:41):
Something people may feel when they see a career like yours, they're like, "Man, Manik's just killing it. He's done everything. Everything just is clicking, always winning." I imagine there's been a few times when you've made mistakes or things have been really challenging. What would you say has been one of the more challenging projects or points in your career?

**Manik Gupta** (00:13:59):
Yeah. No, absolutely. This is really important to talk about as well, because we glamorize successes and we don't talk enough about challenges. I'm really happy that you're asking this. I would give you two times which... I had a lot of learning from both of them, but they were pretty tough times for me. The first time was, I had started my own company at the height of the dotcom boom. We incorporated our company in June '99, and then in March of 2000 we sold our company to another company from Norway. That was the peak of the dotcom boom. Then within a few months right after that, we had the dotcom bust and it was terrible. Terrible. I know we have a pretty bad economy right now. There's a lot of stuff going on. It was really bad, because people around me, my friends, were losing their jobs.

**Manik Gupta** (00:14:52):
Luckily we had some funding. We had secured some of our funding and we had had an acquisition. The parent company was pretty strong in terms of their balance sheet, so we could continue to do it. But things didn't get better, Lenny. 2000 went by, 2001 came in. We kept waiting for things to improve, but they never improved. So we had to pivot. We had to pivot as a company. My co-founders actually left the company at that point. I still wanted to be there, because I really believed that I can keep moving this company forward. Then I was working with the founders of the parent company. We pivoted multiple times, we tried a few things. I even relocated back from Singapore back to India to set up an engineering office so that we can get into a SaaS kind of a model versus an eCommerce company that we were.

**Manik Gupta** (00:15:35):
I tried many things over those two or three years. And remember, this was my first, quote unquote, "job" out of college. I was doing a lot of that and it was a very tough time. But at the same time I learned a lot. I learned a lot about myself, I learned a lot about managing ambiguity and just keeping people motivated through a tough time. A lot of that also has to come from keeping yourself motivated, because people can smell fear and pessimism from far. Just like optimism is infectious, so is pessimism. If you're not feeling great as a leader, people will see it. Absolutely. People are not stupid. You have to not fake it. You have to really be motivated to stick it out, and that's what I tried to do at least, and I learned a lot in that. That was one really challenging time for me.

**Manik Gupta** (00:16:21):
Then the second one was, man, during Uber. 2017, 2018 was crazy at Uber. Oh my God. There were just so much going on with leadership changes, with the brand issues we were getting. For me, there were times when I would commute up from my house to the office, and while I'm in the car I will be listening to some news or whatever and I'll hear about things that happened at Uber that day from the news before I got to hear it from within the company. It was that crazy during that time. So again, a lot of chaos, a lot of churn at the company as well. It was something where you just had to keep your head down and just keep staying focused on what the core is.

**Manik Gupta** (00:17:03):
I think that is where, Lenny, the optimism in me in terms of, what am I really doing? Is this a service that really benefits millions of people around the world? Are we creating true change? Those are things that I just have to dig deep into to make sure that I stay grounded on why am I here and why I remain to be here and then at the same time motivate my team. But yeah, those were the two really challenging times that I have encountered, at least in my career.

**Lenny** (00:17:26):
Those are awesome examples. I imagine a lot of founders are going through a lot of challenging times right now with the market, and imagine these experiences for you were really important and impacted your ability to take on bigger roles and bigger challenges in the future. Is that how you see it? These are important experiences to have over time as a product leader and just leader in general?

**Manik Gupta** (00:17:46):
Oh, absolutely. Because like I said, you learn a lot about yourself when you go through a situation like this. You learn both things that bother you or bring you down, and things that give you energy. It's sometimes counterintuitive to think about this. When you're going through a bad time, often then people will say, "Well, during a bad time I only learned things which are bad." But you also learn things that are good. Which is, maybe during a bad time you did something and you suddenly felt relieved or energized, and then you look at that and say, "Wait, I should do more of that even during a good time, because can you imagine the compounding power that I would get? Because stuff is good and I'm doing this and I'll feel even better."

**Manik Gupta** (00:18:26):
I learned a lot in terms of my own personal energy, things that get me going, things that really stop me in my tracks. And at the same time, how do you work with a team? How do you motivate them? How do you keep your head down and focus, versus getting distracted? What are some of the decisions you make around your product roadmap?

**Manik Gupta** (00:18:47):
I'll give you an example. During my startup, when we were going through that, in order to motivate the team, one of the best tricks that I came up with, and I learned this from a bunch of other people also, is you just give a team a win. Winning really, really drives a lot of energy. We had a choice to make between launching something which will take six months, versus launching something that we can launch in a very small-ish kind of way, but launch it in a month. And we chose the latter, because when we did that, I remember people were giving high five to each other, people were saying, "Hey, you know what? This is great. We put something in front of customers." We had, I think, 10 customers who used it or something, because we were so soft-scaling that feature. But that didn't really matter. The point was that you get confidence from getting things out, putting it out there, and you feel good about being a builder and being someone who is actually creating a difference. That really grounds the team and focuses the team that there is some real value here.

**Manik Gupta** (00:19:45):
Some of those things I picked up. Both going through that turbulent time, I picked up. And I have used that even in good times to make sure that we keep building good products.

**Lenny** (00:19:56):
That's such a good tactical tip. Find a win. Keep people motivated. Speaking of wins, coming back to Google Maps and Uber, they're probably two of the most widely used, successful consumer products in the world. I don't know if I can think of other products that are used by more people for this long. Then now at Microsoft you're helping Microsoft get more into consumer on the communications side. I imagine you know a thing or two about building successful consumer apps, and so I want to ask a couple questions along those lines. What are two or three surprising or counterintuitive things that you've learned about building consumer products?

**Manik Gupta** (00:20:32):
The good news is that there's just... Because of Twitter and a bunch of other channels, including your newsletter by the way, I feel like people are very well informed these days. And I love that.

**Manik Gupta** (00:20:43):
Let me digress for a second and then I'll come back to your question. One thing that I'm observing a lot, Lenny, which I feel very, very happy about, is the quality of learning and insights and frameworks and best practices is so universal at this point. It used to be that you had to be in the Valley or being part of a small group of folks who are doing things at the cutting edge to have those crazy insights about how do you find product market fit and do all that kind of stuff. Today I talk to people from all over the world for various reasons, and it's incredible how fast people pick up all these insights and frameworks and then they apply them to their local setting and so on. I find that to be one of the most wonderful things ever.

**Manik Gupta** (00:21:32):
I think folks like you have obviously played a big part, because you have global subscribers and you share some of the best practices. But just generally, that's actually a really good thing for the world, that people have so much access to clarity of thinking. And the best people are actually putting themselves out there, which is great.

**Manik Gupta** (00:21:47):
In terms of the counterintuitive stuff, I think two things. One is building consumer products is very hard. I think people think it's easy, because each of us is a consumer. We think of ourselves as a good user, we think of our friends as users, we think of our family as users. And we say, "Well, if we just build it for ourselves and for our family and friends..." By the way, a lot of great consumer products started that way, so I'm not saying don't do that. But man, it's hard. It takes a long time to get things right. Because you're essentially trying to get so many things right when you're building a successful consumer product. You have to be able to reach out to a vast, heterogeneous set of users who have different needs, who have different perspectives. The go to market is always very interesting, because you can't force people to use your product. People have to choose you, you don't choose them. That's the part where... How do you drive virality? How do you drive that real love for a consumer product? And it has to create real value.

**Manik Gupta** (00:22:52):
The other thing about time is that, in order for you to find product market fit and then scale from there, you just have to try a lot of different things. There are theoretical playbooks around it, but you got to just get into it. Going back to the point I was making earlier about wins, get some wins and see the results and then iterate from there. I think it's just hard and it takes a lot longer than what people imagine consumer products do. Versus, let's say, enterprise products or products of other nature. That's one counterintuitive thing that at least I've learned.

**Manik Gupta** (00:23:21):
The second one is the global patterns that you see in consumer products in terms of the user interface; the core things that people do or expect. At this point along of that is pretty universal. There's always this debate where people would say, "Well, need to have one product for the U.S., another different type of product for Asia, another different type of product for Africa. I think we are past that point. That's again another counterintuitive thing, where people spend a little too much... I've seen this in many companies. People spend too much time debating that, "Oh, the users in market X are different." Well yes, they're different, but they use the product the same way.

**Manik Gupta** (00:24:02):
That's the part which I think... And I'm not making an argument against localization. Of course you need localization around language, pricing. There are some legal requirements, all of that stuff. Obviously you have to do that, otherwise you don't even have a right to exist in that market. But by and large the patterns are very similar. You look at global products, even like Facebook or Google Search or Maps or Twitter or TikTok and so on, all of them have a similar pattern or similar app for the entire world, and they keep on innovating or localizing at the edges.

**Manik Gupta** (00:24:33):
That's the other counterintuitive thing that people should know about consumer products. Build for the world from day one. Understand that there are going to be some nuances that you'll have to solve as you drive adoption in certain markets, but don't over index on building market specific solutions, because consumers have moved on from that kind of a model. Those are the two, in terms of product building, counterintuitive trends at least I have picked up over the years.

**Lenny** (00:25:02):
**Manik Gupta** (00:26:17):
Yeah, absolutely. I've been noodling a lot on this, especially since I took on my role at Microsoft as well. And prior to that, even at Google, this was always an interesting discussion. Let's say you are building a new product or leading a new project, if you will, at a larger company. In fact, this also applies to medium-sized companies. I wouldn't say for startups, but medium-sized companies. Usually the narrative in the room when you're discussing this with your team and with your leadership team would be, "Okay, we got to go find product market fit." Absolutely. Yeah. We have to do a bunch of stuff, as we just talked about. Consumer products take time. All of that stuff.

**Manik Gupta** (00:26:57):
But I think there's a question before that question, which is how do you find company product fit? What I define as company product fit. Which is a company essentially is a portfolio of products, and every large company, medium-sized company also has a portfolio. They'll have 10, 20, in some cases hundreds of products in the portfolio. Every company has unique strengths and weaknesses. This is pretty tried, but it's obvious. And I would encourage a lot of folks, when they start embarking on this journey where they're trying to really build out products and so on, is to ask that question. How does that product, assuming it's successful... If it is not successful, it doesn't matter anyway. But assuming it's successful, does it actually serve the right place in a company's product portfolio? Or not? And if it doesn't, don't do it. Why waste time?

**Manik Gupta** (00:27:57):
Oftentimes companies will be like, "I want to do this because some other company is doing it." That is not a good reason. You should only invest in products, or projects for that matter, because you can play to your strengths and you can create some unique consumer, customer value. And by the way, you can do it better than anybody else out there. That's what I mean by company product fit. Take that first step and understand does this even resonate and is it part of the portfolio? Does it make sense?

**Manik Gupta** (00:28:26):
Because if you can answer that question with enough conviction, then your road to the next step on finding product market fit becomes much easier, because you don't have distractions then. Everybody gets it. Everybody gets this is a strategic effort. You have the right sponsorship at the right levels in the company, and you're executing towards it and you're finding it out. Let's say things don't go well. That's okay. People will step in to help. A lot of that will happen, because people innately get it. That this is the right product to go after from a company product fit perspective. That's something that I've been thinking a lot about and also executing as we move forward.

**Lenny** (00:29:00):
Is there an example of that gone wrong that you can share? Whether it's a company you've worked at or a company you've seen do it badly.

**Manik Gupta** (00:29:05):
I'll have to think through specific examples, but companies do this all the time, where they do these line extensions. Where they'll say, "Well, we have a lot of traction in a particular segment. Why don't we just go to an adjacent segment? If we just add two more features, suddenly this will be appealing to an adjacent segment." A classic example would be you're doing something for, I don't know, small and medium businesses and you say, "Well, now I just have to add two more features and now I'm going to go up market and I'll get to compete in the enterprise." Or it could be the other way around too, where you have something in the enterprise business and you want to suddenly go down market to SMB.

**Manik Gupta** (00:29:44):
In my view, it's hard. Because again, the capabilities that you need, the thinking that you need, is something you have to really be clear about. This is not to say that it will not fit in the company's portfolio. It's just that when you're making a choice like that, make sure you set it up well to succeed. That's the other part of the equation as well.

**Lenny** (00:30:02):
Speaking of setting it up to succeed, you also have this idea of a consumer stack concept that I think you've been talking about at Microsoft. Can you talk about what that's all about?

**Manik Gupta** (00:30:11):
Yeah, sure. One of the things that I'm doing at Microsoft right now is, while I'm working on a lot of the consumer communication products, the other thing that I'm really helping the company think about is how do we get more at scale consumer products built at Microsoft. Part of this is just distilling some of the learnings that I've had over the years. I think there are like five things that I would talk about, which I call the consumer stack, which is essentially a set of capabilities that companies need to have a good chance of success at building a consumer product. Remember, nobody can give a playbook to build a successful consumer product. That does not exist. Because as we were discussing earlier, it's so fickle and so many things have to go right for you to build a successful consumer product. But at least you have a set of capabilities, so you set yourself up the best.

**Manik Gupta** (00:31:01):
The first one I would say is around design-led thinking to delight users. Going back to your days at Airbnb, Lenny, I'm sure this is something that resonates with you. Design for consumer products is such a critical part of how you build the right pull from consumers these days. Poorly designed products have no chance at this point. Your craftsmanship and the design capabilities have to be A plus. And if you don't have that, then you should really invest in that. This is not just about having the best designers. Of course you should. It's just the thinking. It's a attention to detail. It's the attention to how things are pixel to pixel, moving from one screen to another screen and so on. You really have to sweat it out and really be clear in terms of how it's adding value to a consumer. That is, I think, a core capability in these days to build a consumer product. That's number one.

**Manik Gupta** (00:31:54):
Number two is strong focus and prioritization. You can apply strong focus and prioritization to anything in life, but I think it's even more important for consumer products. Because oftentimes people, when they think about solving a problem, they think about coming up with 20 features at the same time, and it's not needed. You don't need 20 features to solve a problem. You just need one or two features which work really well. This whole concept of critical user journeys. How do you make sure that, if you're solving problem X, any feature that you build in the product... Firstly your product should have very few features in the beginning. But even if it has those features, it should be well designed and it should have the focus and prioritization so that you're only getting things for the critical journey so that the user can use it and not get confused. That's the second one.

**Manik Gupta** (00:32:38):
Most PMs totally understand that. That's their job description, to focus and prioritize. But I feel like a lot of times the PMs do get very confused and distracted, because the number of ideas that people have is so large that they want to just throw everything into the product, and that doesn't work. You have to keep a very high bar for focus and prioritization. That's capability number two.

**Manik Gupta** (00:33:00):
Number three is having the right metrics and instrumentation. This talks to the data aspect of the culture, which is, if you don't have the metric with regards to what you're optimizing for at the initial state of the product, middle state of the product, late stage of the product, you're just not going to choose the right things. How will you measure success? How will you convince yourself, your team, and broader stakeholders that this is actually working or not working? Having the right metrics is important, but it's incredible how many times people have the metrics but they don't instrument them. They'll have all these debates, because the product is not instrumented properly. And everybody will talk about the same metric, but they'll have different nuances in terms of, "Oh, what does it really mean? What is a daily active user? Okay, daily means... Okay, I understand it's on a daily basis. What is active?" And there'll be debates about what is active. Pick a definition, instrument it, codify it. No confusion. That's number three.

**Manik Gupta** (00:33:59):
Number four is more on the engineering side, which is how do you get to a very high ship velocity, and the ability to experiment and learn fast. At a broader level, especially during the initial phases, if you're not learning, you are really not doing anything well. You've got to be learning. You've got to be learning good things, bad things, doesn't matter. You've got to be learning. Having the experimentation velocity, having a building culture where engineers are able to check in code, see the results, and then quickly come into another release and stuff like that, I think that's really important for a consumer product.

**Manik Gupta** (00:34:29):
Finally, underpinning all of this is just having strong talent. Assess your talent; your product talent, your design talent, your data talent, your engineering talent, your marketing talent, all these functions. You just have to have a talented pool of people who like to build stuff, and they're the people who understand and have the empathy for consumers.

**Manik Gupta** (00:34:50):
To me, I think these five capabilities... And as a leader, or product leader, or an engineering leader, or anyone who's basically responsible for running products in small company, big company, medium-sized company, it doesn't matter; if you're in the consumer space, my thinking here is that if you look at these five categories and five capabilities, you should really have a report card and say, "Okay. How do I rate these?" If I were to look at my own team, what do I think about design thinking? What do I think about strong focus and prioritization? Are we doing an A job? Are we doing a B job? Are doing a C job or D job? I would argue that if you get to an A job over time, because not everybody will be at A on day one, but if you get that over time, I think you will start seeing results which are very meaningful. That's how I've been thinking about the consumer stack.

**Lenny** (00:35:34):
Awesome. I was going to ask how you operationalize this. It sounds like it's going to turn into Manik's consumer stack scorecard, and bigger companies can leverage this at their own company and show their manager, "Hey, we're moving really slowly. Maybe this is an area we should focus before we bet big on consumer."

**Manik Gupta** (00:35:50):
Yeah. I'm trying to operationalize this myself right now in my current job, and I have used some version of this. I mean, this is not something I just came up with. It's something that has been in my mind for a while. I've used it in some shape or form. But during my break, especially before I joined Microsoft, I think this came together for me as something a little bit more tangible that I can use. Then I started applying it, so I think it's been pretty interesting to see.

**Lenny** (00:36:15):
Awesome. I'm hoping that this proliferates through larger companies and becomes a thing that we can root back to this chat.

**Lenny** (00:36:23):
Shifting a little bit to the CPO role and the VP of product role that you've had at a few companies, in theory this is kind of an end state for a product leader. Every PM, if they stay down the PM career track, they'll become a CPO or VP of product or head of product somewhere. A couple of questions here. One is, do you have a sense of how many PMs actually stay on this track and end up in one of these roles, versus move on to some other role or place?

**Manik Gupta** (00:36:47):
Yeah. That's a great question. I would say that the percentage for CPO in particular, you having a C title and being a CPO, I think that percentage is still relatively small. This is just my sense. I haven't done the numbers to give you a more accurate picture here, but I think my sense is relatively smaller. Because I think a large part of it depends on how companies are organized. Companies can be organized functionally, companies can be organized through business units, and oftentimes these days it's a mix of both. If you look at any company, they'll have some C level functional executives, but underneath them they'll have GMs. The organization design is just such an evolving field always. And as they say, companies will go one... they'll swing the pendulum one way and they'll say, "Oh, over time it's not working," and then they'll swing the pendulum the other way and then they keep going back and forth. I think the percentage for CPO in particularly in my mind is probably not as big as what people think it is. Like I said, because of the way that companies are organized.

**Manik Gupta** (00:37:50):
I think the interesting thing here is I am just seeing personally, having been a CPO myself and also talking to a lot of people in my network and just observing a bunch of different companies, I think the CPO role is evolving. Or the head of product role is also evolving. I think a lot of it is morphing more into the GM model where you're running not just product management but also perhaps PM and engineering, and design to a certain extent and data science too. You're essentially becoming the overall technical product leader at the company.

**Manik Gupta** (00:38:27):
The reason why I feel that is happening is because it's all about accountability. It's about who has the single threaded leadership model where this person can make all the decisions when it comes to trade offs and running the roadmaps and all of that kind of stuff. It's not ideal, by the way, in all cases. Because what that means is, for somebody to be doing that, that person has to be really, really good at all those other functions too so that everyone who is in their organization respects that. Otherwise people feel like I'm the second class citizen in this model where this person doesn't know anything about, whatever; my function and so on. So it's harder, but I do feel that for optimization around decision making, around having a single threaded leadership and accountability, I feel like that's the direction where the product leadership role itself is going more and more. At least based on my experience.

**Lenny** (00:39:19):
Is your sense that maybe CPO might fade away as a title and GMs become the common path across companies?

**Manik Gupta** (00:39:26):
If you were to push me on this, I would say that's probably the direction we will go. I think it's interesting to also think about CTO. If you look at the CTO roles versus SVP of engineering or a VP of engineering, I think it's an interesting debate too, what's happening with CTO roles. If a company is organized purely functionally, I think that's absolutely the right call. But as companies are changing and thinking about how they drive more accountability and more business units and so on, I just feel it probably will become more GM oriented. That does not mean that the VP product is going to go away or the VP engineering is going to go away. I think those roles will still stay. But the C-level title, reporting into the CEO but you're just running that one function; if I look at over time, maybe that role is lot less prevalent than what we have right now.

**Lenny** (00:40:15):
Do you think that's partly because there's this weird overlap between CPO and CEO, and there's often tension of who's leading the product? Is that something you've seen?

**Manik Gupta** (00:40:24):
Yeah. I think that's definitely an interesting one as well. I mean, if you think about it, just based on my experience, what does the CPO really do? What is their job description? I think it's useful to think through that. Generally speaking, and again, we can always talk in generalizations because that's how you should think. And every company is unique. But generally you would say the CPO is responsible for driving the product vision for the company, and that product vision cannot be divorced from the company vision. Oftentimes this is actually what also creates conflict within the leadership team, where the product vision is... people are coming up with these grandiose plans. Like, "Oh, we'll do this, we'll do that," but then it's not really grounded in the reality of where the company is. Anyways, it's around product vision and making sure it's coherent with the company vision.

**Manik Gupta** (00:41:09):
Then the second big part of a CPO job is execution of the roadmap on the priorities. People sometimes think that, hey, I get to a C-level position. I don't have to worry about execution. Absolutely not. If you're a CPO in particular, even the CTO and the head of engineering, execution matters a lot. The operational excellence. Because things are so complex. I mean, we are in a situation where a lot of people are working remotely, there are all these different tool sets, there are all these different technologies that are coming up, you have different competitors. Execution is super important. And if people don't understand that that's a big part of their job when they get to the senior level, I think they're mistaken. The execution is another one.

**Manik Gupta** (00:41:50):
The third is, for a CPO, especially for a tech company, because you are really driving the product roadmap, it's a very leveraged job. Meaning you have to really work with all your other peers, whether the marketing person, or the sales person, or the business unit person and so on, and just make sure that you are really even deeply connected in terms of what is really needed, so that your product roadmap is how things are going to actually come to life. It's a very cross-functional, on steroids kind of job in that sense.

**Manik Gupta** (00:42:19):
In terms of the CEO, CPO, I think the important thing again is... And this is actually advice I've given to CEOs of some companies as well, when they first start looking for a VP of product or a CPO. This is almost like a questionnaire that I give them. The first question I ask the CEO is, what do you want to do? That's the most important question. Because a lot of times the CEO has either been the technical founder, or they have been the product founder. They can be a sales founder too. All that is fine. But what do you want to spend your time on? Because if you are going to get a CPO or a VP of product and then still want to own the product roadmap and own the execution, then don't do that. Because what is that person going to do? That's the first question that I tend to clarify between a CEO who's looking for a CPO or VP of product.

**Manik Gupta** (00:43:10):
Then the other thing is really about, are you trying to optimize for process? Are you optimizing for strategy? Are you optimizing for team building and attraction? I think that's a really big one. Sometimes you have to get the right level of leader to attract more talent to the team. Because people say, "Oh, this person is working there. Now I want to go work in their organization." How do you think about engineering and data science and design? How do you think about GM and operations? There are a bunch of all these things in terms of the design that you need to do before you decide whether VP of product, CPO is somebody you want to get and what kind of person you want to get.

**Manik Gupta** (00:43:43):
I think that's where the intersection of the work between this... especially for a tech company, the CEO, CPO have to be... And even the CTO I would throw in the mix. That has to be very clearly articulated, otherwise it creates a lot of confusion. Those are some of the things, at least that I observe from different patterns and different companies that I've worked with and also guided and advised, those are things that always come up.

**Lenny** (00:44:06):
It's interesting how much similarity there is to that experience as there is to the first PM at a company. It feels like they have to have the same conversations with the founder. What do you want to work on? What am I going to take on? How do we avoid stepping on each other's toes the whole time?

**Manik Gupta** (00:44:21):
That's actually a... I never thought about it that way, Lenny. I think that's a really good point. You're totally right. Obviously, if you're at a bigger company, then you're looking for a VP of product. Or if you're a super big company, then you're looking for a CPO. But you're right. The first product hire that you make as a founder, you'll pretty much have the same conversations to ensure that there are clear swim lanes and accountability for that group.

**Lenny** (00:44:39):
Interesting. I want to make sure to ask you, as kind of a big deal leader of product at larger companies, I'm curious, what do you look for in PMs that are looking to get promoted, or just deciding somebody's ready for promotion or ready for more responsibility? What do you look for and what should people focus on if they want to come across as promotion material?

**Manik Gupta** (00:45:01):
I'm a big fan of looking at both the what and the how. So what did they accomplish and how did they accomplish. Because they're a package. And if you just look at one versus the other, then I think you end up making a mistake. Usually. On the what, I think the what is usually more objective. What I look for... And again, it depends on the level of the person. Don't try to calibrate someone based early in their career. You have to think through that. That they're in learning phase. If they're more senior than you have to of course calibrate them differently. But ultimately, if I were to boil it down on the what, it's really about real demonstrated impact. An ideal example is someone who had a strong product hypothesis, they rallied a bunch of people around them. They may not have come up with the hypothesis. That's fine. Somebody else could have come up with it, it doesn't matter. But they believed in it, they rallied the team behind it, they drove towards it and created impact.

**Manik Gupta** (00:45:58):
The impact not necessarily always has to be positive. It could also be a lot of stuff that we learned, but we learned from it and then we moved on and we did the next rev. By the time we did the next rev, we were smarter about it. Clear demonstrated impact from an end to end product cycle to me is probably one of the better indicators of readiness for someone to take on more. And you basically want to give them more, because now they have a pattern of doing things properly. That's one.

**Manik Gupta** (00:46:23):
On the how, I just love people who are able to create both energy and create clarity. Think of the flip side. PMs who don't create clarity is such a time sink and the teams struggle so much. I'm sure all of us, when we think about back in the day, maybe we were in that position at some point. But we also worked with folks who were always confused and didn't really summarize, or didn't really follow up, or didn't really create that level of clarity in terms of what we need to do and so on, and how broken that felt. People who can create the clarity and then have the energy around them to get things done, I think that's the how in my opinion. Which is really important for determining somebody's career trajectory.

**Manik Gupta** (00:47:11):
Then the last thing I would say is followership. Really important for PMs. Do people want to work with them? Do people at some point, as they go up and become more senior, do people want to work for them? Ultimately people make choices. And if you have a bunch of smart people and they're making smart choices and they're choosing this person to follow or to be with and work with them and reach out to them, and you keep hearing things about, hey, so and so wants to work with this person because this person is amazing; there is a ton of value in that.

**Manik Gupta** (00:47:45):
Those are the three things that, if I were to really boil it down, not looking at a certain level, I think I always look for those attributes.

**Lenny** (00:47:51):
Those are awesome. So simple and clear and succinct. I like the way that you framed it as followership versus leadership. There's a lot of PM attributes leadership, and there's something really nice about just a way to understand that as how many people are following you and excited to work on the things that you're trying to get them to work on. That's very cool.

**Lenny** (00:48:11):
Along the same lines, when you think about PMs that had an inflection point in their career, do you find that there's anything correlated with something that leads to a large inflection in the progress of someone's career where they all of a sudden started doing incredibly better?

**Manik Gupta** (00:48:24):
I've gone through a few inflection points myself, and almost always they've happened because something in the organization changed, so I got a shot. There's always that luck factor, going back to the first question that we discussed.

**Manik Gupta** (00:48:37):
But generally speaking, I think the inflection points happen in two places. One is when someone has really successfully changed the dynamic, or the trajectory rather, of a particular product. That's a huge inflection point. That doesn't happen very often, to be fair. But when it happens, you know it. You know, as a leader, this person worked on this and they actually led this change and now we are playing a different game. We are playing a bigger game, we are playing a different game, all of that kind of stuff.

**Manik Gupta** (00:49:16):
In other words, what I'm saying is the inflection point for a career is correlated strongly with the inflection point in the product. If you can connect those, the cause and effect... If there's causality and not just correlation, if there's causality in that, I think that absolutely means that you've got a winner. And you really want to bet on them and you have to give them a lot more to do, because they have the ability to do it. That's one.

**Manik Gupta** (00:49:38):
The second is, oftentimes as people go up in their career, they start managing teams. They become a manager, and then you become a manager of managers, and then you become more senior. I mean, that's the organizational trajectory that happens. One inflection point that I've seen is, when you go from being a manager, a first line manager, to becoming a manager of managers, and if you're able to navigate that with very strong effectiveness, then you know. If you're their manager or if you're their leader you know this person has got their act together. Because managing ICs is so different from managing managers, because then you now need to create a structure. You need to be able to determine how much you delegate. How do you coach? How do coach your managers to do the right thing? If you see somebody making that transition effectively... And you have to give them some time, but if you see that and you know that they're actually doing it, and again, a lot of followership, a lot of other things are happening, good things are happening, then you know they're at that inflection point where they're ready to take on more.

**Manik Gupta** (00:50:41):
Both product inflection in terms of real output and this management prowess inflection in terms of being able to effectively lead going from one step to another, a manager to becoming a manager of managers; I think those are the two places where I feel like, if I see somebody doing well, I know they're ready to put more onto them.

**Lenny** (00:51:00):
Do you find that second piece is this filter for PMs that do well in this manager manager role and go on to do better and better and then a lot just fall away because they can't handle that?

**Manik Gupta** (00:51:12):
Yeah, I think so. Maybe I'm a little bit more traditionist on this point. I know there are other schools of thought on this, which I respect. Which is there are a lot of times where people are like, "Well, oftentimes the best PMs are PMs who are IC PMs. They have this crazy, incredible, unbounded energy and they don't want to waste their time on management and whatnot and do that. Because a large part of a PM's job, by the way, is managing by influence. PMs typically don't have large organizations. In fact, one of the most leveraged teams in almost every company... Because you talk about PM manage ratios, PM design ratios, they're never one-ish to one, or one-ish to five, or one-ish to six. Sometimes it' going to be one-ish to 10. At Google it used to be one-ish to eight to one-ish to 10.

**Manik Gupta** (00:51:52):
I personally see that transition... If somebody's making that transition successfully and they're getting good scores out of it and delivering the product and the output of the team is significant, I definitely see that as a good filter criteria for someone whom we can bet on.

**Lenny** (00:52:06):
Do you find there's common habits or pitfalls PMs make to shoot themselves in the foot in their career, especially early on?

**Manik Gupta** (00:52:14):
Oh, I see that all the time. There's a few of the things that I have picked up. And by the way, I was doing this too early on and I learned the hard way. The first one I would talk about is you are early in your career and everyone expects you to just manage things and manage the process and all of that. Make sure that trains are running on time and all of that. Which, by the way, is really important for an early in career PM to understand. That that's actually a big part of your job. Let's not over glamorize a PM. A large part of being a PM initially is just basically doing whatever the team needs you to do. But I think one of the pitfalls of that is, if you start putting process over progress, that's a problem.

**Manik Gupta** (00:52:58):
What I mean by that is, you want to introduce process into almost everything that the team does and not be flexible on shipping things out there and all the things that can come in the way of progress. If process is helping progress, great. But if process is hurting progress, you should not be the person saying, "No, no, no, no. We can't do it, because I'm just so married to the process. Because as a PM, that's what I own." I mean, as a PM you don't write code typically, you don't write design specs, you write product specs. Sometimes you feel like, what is the set of attributes that I own? Especially early in career PMs. And you're like, "I own this process. I own this weekly standup meeting, or I own this sprint planning, or whatever." And then you get so married to it that you forget the fact that that's just a means to an end and the end is what you're going to be actually measured on. That's one mistake that I see people making early on.

**Manik Gupta** (00:53:48):
The second one is becoming really too self-centered. It's all about me, not the team. I'm the PM. There's this myth that keeps going around. The PM is the CEO of the product. That's one of the most incorrect things in the world. The PM is an enabler. I said earlier, it's a leverage job. Your job is to really make the team successful. Of course you have to have the product thinking and the roadmap and all of that, but sometimes this can go to their head. Then people become too self-centered and that's a red flag.

**Manik Gupta** (00:54:21):
Then the third one would be just not admitting your mistakes or learning from them. Early in career, the only thing you should optimize for is learning. Sure, you'll make a lot of mistakes. You don't know much yet. You're just coming into this journey and you should be humble and you should be learning and you should be saying, "Oops, I screwed up over here." And that's okay. That's fine. And by the way, if you work in a company where that is not accepted, you should not work in that company. What's the point? You should really be optimizing for learning and learning from other people. And people should be saying, "Yeah, don't worry. It's okay. You made the mistake. Learn from it. Don't make the mistake again. That's fine." But that's the kind of culture you want to choose for yourself.

**Manik Gupta** (00:55:01):
Those are the three pitfalls that I see people get into, especially early on in their career.

**Lenny** (00:55:05):
You touched on how different companies work in different ways and look for different things in different PMs. And something I wanted to ask you is just to chat a bit about the difference between working at Google versus Uber versus Microsoft as a PM, and also just generally how product is built differently at these companies. It's something I'm trying to do with this podcast as much as possible. Just give an overview of what product is like at different companies. You've worked at three of the biggest, and so I'm curious to hear what you can share around that.

**Manik Gupta** (00:55:32):
Yeah. It's actually really interesting. I mean, all the three companies are so different. Google, the core DNA of the company was very much engineering. In fact, there used to be a framework which was around technology insights drive innovation. It was always about what is the best tech we can come up with, which is going to indeed drive innovation, and have a longish view so that the market will get there. That was the Google philosophy always. As a PM, your job at Google... It might have changed in the last six, seven years that I've not been there, but at least when I was there from 2008 to 2015, especially working on Google Maps, it was all about how do you take good long-term bets grounded in strong technical insights, and then use the power of Google Search distribution to really get your product out there. That was it.

**Manik Gupta** (00:56:33):
On the Maps team, our innovation was pretty much around crowdsourcing everyone's location signals for traffic. Huge, huge accomplishment. We had the best traffic models in the world. And then being able to do this crazy route optimization for driving directions. Then on top of that, we had the search stack, which came from Google Search anyway. So that you can search for any address, any business and so on.

**Manik Gupta** (00:56:55):
Anyway, as a PM it was partnering very closely with engineers and really amplifying the engineer's ideas and so on. I think at that point also a lot of Google PMs were very technical. Very, very technical. Because that was just part for the course. It was expected that you will be able to at least have engineering discussions. A large part of what I did as a PM at Google, especially initially, was getting into the technical details with my engineers and really geeking out on what we can do. That was the Google model.

**Manik Gupta** (00:57:25):
By the way, one thing I should say about Google before I go to... At Google as a PM, at least all the way up to the time even when I became a director, I never had to think about business models, man. Never. It was fascinating. You were in this weird state where you could just build and have the consumer traction and all of that, but you never thought about P&L, never thought about revenue and so on.

**Manik Gupta** (00:57:48):
Then I landed at Uber, which was very different. Uber was very operations, very business driven, very P&L. In fact, one of the most incredible things that Uber did was they had a dashboard which every employee in the company could look at, and it had last week's revenue, last week's number of trips that we did, and you could slice and dice it and all of that. I think that changed over time as we became a public company and so on. But the point was that it was really in your face all the time. When there were weekly newsletters sent out, it was all about growth, it was all about business, all of that kind of stuff. It was very operational and business, so as a PM over there it was a lot about managing a bunch more stakeholders. The operations teams, the marketing teams, the policy teams and so on. And how do you work with them to deploy your product into each of these markets. Of course then a large chunk of your work was still working with the engineering team. It was different in that sense.

**Manik Gupta** (00:58:47):
I think at Uber the other thing was it was also much more of a real time business. I mean, Google was also real time. Google Maps was real time. Billions of users were using it. But Uber was... every day there was something going on in the market and you had to keep on that hustle in terms of how do you make sure that your staying competitive, your product is working well, there are no outages. All of that kind of stuff was really important.

**Manik Gupta** (00:59:09):
Then finally, on Microsoft... I mean, Microsoft has been around for quite a while. The company went through so many different things and then over the last several years, especially under Satya's leadership, it has done so well. Incredibly well in terms of how the company has changed the culture, the kind of products that they have in the market, the traction they have in the market.

**Manik Gupta** (00:59:29):
I think I would describe Microsoft as both... first and foremost, it's a very strong tech company. The engineers here are incredible. Oh my God. I am so privileged to work with some of the best engineers that I've worked with in my career. At the same time there's a lot of legacy. There are a lot of products that have been around for a really long time, which is good and bad. The good part is that they have seen pretty much every pattern there is to see. In fact, they came up with a lot of those patterns themselves. The bad part sometimes can be that change is hard. How do you convince people that we're going to go down a different path? As a PM, a lot of it is around bringing outside in perspective, bringing clarity of like, "Hey, this is how it has actually worked somewhere else." Bring a specific example. Let's try it out and see how that works.

**Manik Gupta** (01:00:13):
The final thing I would say about it is the company is so grounded in trust. If there's one word that I would say about Microsoft is trust. They really care a lot about customers. Customers trust Microsoft a lot. I've been in some of the customer meetings myself and I can totally hear what customers say. It's all about trust. They expect resilience, they expect the products to work, and they expect that when they have a problem on the surface, that Microsoft will take care of it. They built that over time. A lot of that goes into your mind as a PM when you're working in that company, that a lot of the stuff that we are doing here is to really help our customers.

**Lenny** (01:00:48):
Going back to your point about company-product fit, these cultures and the way they work just fits perfectly with the thing they end up building. I wonder which one comes first.

**Manik Gupta** (01:00:57):
It's true. That's a whole nother conversation we can have at some point. I have a lot of thoughts on that. But I'll just echo what you just said, which is that's the reason why it's so important for companies, when they embark on new initiatives, to be really, really thoughtful. Is this the right area for us to get into? Or rather, what are the conditions and the reasons why we are getting into something? We have to be super clear on that. Because if the starting conditions are not right, then you will just trash the team. The team will keep working on something and people will never find the right internal fit. So that's super important.

**Lenny** (01:01:35):
You worked on Google Maps and Uber, which I imagine you still use often and maybe billions of people use every day. Is there a feature that you wish that you built back when you were on the team, or that you think should be killed, that annoys you about either of those products?

**Manik Gupta** (01:01:50):
Wow. Okay. This is a super interesting one. I don't know if that's something that I could have built at Google Maps, but one of the things that's interesting is the self-driving technology has just not gotten there fast enough. I feel like the best and brightest actually worked on it and are still working on it and it will get there. I'm a big believer. But of course the timelines have shifted for various reasons, because it is a really hard problem. It's actually really interesting to see what Cruise is doing right now in SF. They have started the pilots and so on, so I'm really happy to see some progress happening. I know Waymo's been doing a bunch of this already.

**Manik Gupta** (01:02:29):
But it would've been amazing. One of the things that we used to talk about all the time at Google on Maps was how would we design a navigation product when people are in self-driving cars? We had some really interesting ideas at that point, but we never got to it. Not because we didn't prioritize it, but the technology isn't there. I still keep a close watch on that and see at what point are we going to get there. It's going to take years, but it is just such a different paradigm. It's like computers talking to computers, algorithms talking to other algorithms. Then there's a human in the mix in terms of serving the human at the end, but it's like the human is not initiating that much. It's just, stuff is happening around it.

**Manik Gupta** (01:03:08):
Anyway, that's one thing that is unfinished business, if you will, in my mind. And hopefully, as the technology comes together, that will happen.

**Lenny** (01:03:16):
Amazing. Manik, you've been extremely generous with your time. Just two last quick questions. Where can folks find you online if they want to reach out maybe, or learn more about what you're doing? And then how can listeners be useful to you?

**Manik Gupta** (01:03:28):
Yeah. You can find me on Twitter, you can find me on LinkedIn. Those are the two places. I have not been very active on both those recently. I've not been active as a contributor, but I'm very active on those two platforms as a consumer. If you have any questions, if you have any thoughts, would love to hear from you, so please send me a note.

**Manik Gupta** (01:03:47):
In terms of how listeners can be helpful, I just want to learn what's new and what's out there. I've had the privilege of being in these incredible companies. The reason why I'm still doing what I'm doing is because I still want to learn. If there are better patterns out there that you're seeing, particularly around how to build products, would love to know if there are other ways people think about finding product market fit. Because that's such an elusive thing that I just keep thinking a lot about. If you have some techniques, some tips, some best practices that you have learned and it has worked for you, please, please, please reach out to me. I would love to learn that, because it's so important for us to keep having that conversation.

**Lenny** (01:04:24):
Awesome. It's always such a pleasure chatting. I always learn a ton. And this did not disappoint, so thank you again for being here.

**Manik Gupta** (01:04:30):
Lenny, thank you so much for asking all these questions and giving me the opportunity to share my learnings over the years. Thank you.

**Lenny** (01:04:36):
Absolutely my pleasure. That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast. You could also learn more at lennyspodcast.com. I'll see you in the next episode.

---

## [4/20] Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more

**Lenny** (00:00:04):
When I asked in my newsletter Slack community who I should have on the podcast who's a bit under the radar, but amazing, Nickey Skarstad was the first name that I heard. And I was not surprised. I actually overlapped with Nickey at Airbnb, where she had a legendary reputation as a PM who everyone loved, but got shit done. Before Airbnb, Nickey worked at Etsy for over seven years where she went from being a forum moderator to director of product management. Then she went on to work at Airbnb for a couple years.

**Lenny** (00:00:31):
After leaving, she went on to be VP product at The Wing, and is currently a director of product management at Duolingo. In our conversation, we cover how to set vision, translate that into goals, and then how to execute on it, making your strategy actionable, and keeping your teams aligned and focused, designing your product review sessions, how to maintain product quality, and what skills have most contributed to her success in her career. I hope that you enjoy this conversation with Nickey Skarstad.

**Nickey Skarstad** (00:03:28):
Thank you. Thanks for having me.

**Lenny** (00:03:30):
My pleasure. Today, you are director of product at Duolingo, which is an awesome product, and something that I used to use. I'm not learning a language currently, but I know where to go if I were to. Can you just talk about how you got into product, and then a bit about just your journey from that point to where you are today?

**Nickey Skarstad** (00:03:48):
Yeah, so it's been a long, meandering journey, which is fun. And so I've been in technology roles now for 12 years. I've been in PM roles, actually product roles, for 10. I'm starting to be the person with experience in the room, which is really fun and kind of daunting at times. But how I got my first role in product was I was at Etsy in 2010 is when I joined. And I joined them, I'd say it was post-product market fit, but before they truly started to really grow and scale. And I actually joined them on their community team. So I worked as a forums moderator, and then as a seller education specialist. Yeah. Spent a couple years doing that. And then through that process became sort of one of the internal voices that had a really good understanding of how their customer, one of their core customers, their sellers, were actually using their product.

**Nickey Skarstad** (00:04:38):
And the VP product at the time, his name's Mark Headland. Hey Mark, if you're listening. Was like, "Hey, Nickey, you're in all these product meetings. Have you thought about being a product manager?" And at the time I was like, "Oh God, no. Never." I was like, "No. Technology what? Engineering? I'd have to work with engineers? I know nothing about engineering." And so I was very imposter syndrome-y about it. And he gave me a little nudge, and was like, "I think you'd be really good at it."

**Nickey Skarstad** (00:04:59):
And so I tried it. And I started as an APM. And I was at Etsy for around, I think, it was seven years total, and spent the majority of time actually in PM product roles. So I left as a director of product. And for most of my time there, I worked on the seller side. So it was all seller tooling, working with sellers to figure out how they could grow and scale their businesses. And it was an awesome, wild ride. But that was my first role in product. And then I went on after that into several other product roles as well.

**Lenny** (00:05:27):
Yeah, let's get into it. Where'd you go next?

**Nickey Skarstad** (00:05:29):
So after seven years at Etsy, I was kind of getting the itch to try something new. When I took a step back and was like, all right, what do I want to do next? I really loved the marketplace component at Etsy. And I don't know if this is just says something about my personality, or actually probably your personality too, is marketplace product is really hard, right? You have this constant balancing of both buyer and seller sides or both sides of the marketplace. And I really liked that. And it was something that I was good at.

**Nickey Skarstad** (00:05:54):
And so I was like, all right, where else could I go that's interesting or having a moment? And I was like, Airbnb. Has to be Airbnb. I was a huge fan of their product. They were also post-product market fit. But sniffed around, ended up basically getting an opportunity to join the experiences team. And I joined that team when the product had just launched. So they had done sort of their early thinking, the existential thinking. Had a brand new product in market, and then I joined the team.

**Nickey Skarstad** (00:06:18):
And so I was the first boots on the ground product manager, and really helped that team figure out how do we get product market fit? And then how do we start to think about how to scale it, which was, you can imagine, experiences is interesting because it is a very nuanced product in that, and this is similar to Airbnb if you work on homes as well, but part of it is building the digital experience that someone will interact with when they're booking an Airbnb experience. And the other part is actually influencing the live event experience that you will experience when you actually join an event or an experience.

**Nickey Skarstad** (00:06:52):
And I think that layer of abstraction for me was really fascinating, and something I've learned a ton about is it's not just influencing the digital product, but it's actually the consumer experience when their boots around the ground. And that is another layer of complexity. And so that was super fun. I was there for about, I think, a little over two and a half years. Started as a PM. I think I got promoted a couple times. Left as senior product lead, I believe was my title. And forever grateful for that experience because I learned a ton about product market fit and also product quality.

**Lenny** (00:07:23):
Is there anything else you took away from that experience? Because I was at Airbnb at the same time. We never really got to work together. But I just heard amazing things about you on the experiences team. And experiences was a wild ride, from what I understand. Is there anything that you took away from that experience that kind of has stuck with you as a PM?

**Nickey Skarstad** (00:07:39):
Yeah. So part of it is more of just the way Airbnb works is something that I think I use every day in my job, which is just truly thinking about product quality and the end consumer experience. And Airbnb does not ship product if it is not good. And even if they're trying new things, they are obsessed with the end consumer experience. And I learned so much from that line of thinking because just, if it shipped, it was really high quality. All the edge cases had been thought through. And the experience I had before that was definitely we were shipping things more quickly, things weren't always perfect. And it's not to say that everything Airbnb ships is perfect, but I think that obsession with the end consumer experience really influences the quality of their product suite and is something I try to bring to my job today because no one does it better, in my personal opinion.

**Lenny** (00:08:28):
I'd love to unpack that a little bit. There's kind of two questions in my mind. Is there an example of that at Airbnb where it's just like, okay, here's how they keep quality so high? And then do you have any advice for just how to do that as a company?

**Nickey Skarstad** (00:08:40):
Yeah. So I don't think that's easy for sure. One of the things Airbnb did for experiences is we had this balancing metric, which was basically using the review rate as sort our end all, be all top line goal. So you can imagine a business like that. Obviously we needed to have revenue kind of moving through the platform, and we cared about high level bookings. But really at the end of the day in the beginning, we were obsessed with making sure every person who booked actually had a good experience when they showed up to experiences.

**Nickey Skarstad** (00:09:08):
And so especially if you are building early product, really thinking about how can you pick some good quality metrics that might actually balance or conflate with growth metrics, and use that as sort of your north star because it really helped the whole team to understand what they were actually trying to do at the end of the day. Growth was important, sure. Obviously we needed to grow for a lot of reasons. But the most important thing was that the actual customer experience was great. And I know Airbnb does that in other places too, but that really was experience's top line goal was our review rate and quality and it trickled down for sure.

**Lenny** (00:09:43):
How did they operationalize that? Because it sounds great. Cool, let's make sure everything, all the reviews are five star. How do you build that into the way the team operates and tracks their success?

**Nickey Skarstad** (00:09:53):
Yeah. So a big part of that was actually operational, which was just making sure that hosts who weren't meeting those specific rigorous standards. There was a lot of coaching and education that was happening. Some of that was in the product and some of it wasn't. It was something that was discussed at all of the meetings that we had across everyone's teams, right? Everyone understood that it was important. And so I think that really impacted both the ops team as well as the product team who are literally building the product that would bring that to life. And I think just thinking from, especially if you're a founder and you're thinking about building your sort of early metrics, there's a lot of ways to really make sure your team really understands what that means.

**Nickey Skarstad** (00:10:33):
Another thing we did a lot on the experiences team is we just dogfooded all the time. And so we were lucky in that it's a really fun product to dogfood. We were taking experiences all over the world all the time. But it really helped because you would know right away when you showed up to an event, if you were going to have a five star experience or if it was not going to be great. I mean that really helped us too because then we would go back to the teams and be like, "All right, we were just in San Francisco. We were on an experience last night, and it did not go well. What do we do about it?" So there's lots of ways to do it. But dogfooding is a good one.

**Lenny** (00:11:02):
I know Brian is infamous for texting the team anytime anything isn't working right in the product. And I know he was very intimately involved in experiences. Is that something you've learned to do just to kind of like, "Hey team, I found a big problem. Let's fix it." Or do you try to avoid that and not create that stress?

**Nickey Skarstad** (00:11:20):
I mean I think sometimes that can be a healthy stress if you do it in the right way. The nice thing I think is just making autonomous teams that feel like it is their goal to bring that quality experience to life can help you avoid some of that. But I do think that pushing teams to use the product so they firsthand experience when it is not great is a really good way to give teams sort of the motivation to act on fixing things like that. But I don't know that I text people, but I'm on Slack all the time. So if anything, I'm going to Slack you.

**Lenny** (00:11:49):
Great. Okay. Maybe one more question on this topic because it's so interesting. So on experiences you measured, I imagine, percentage of trips that were five star. Are there other quality metrics that you've used at other companies that you found helpful for keeping track of product quality and maintaining product quality?

**Nickey Skarstad** (00:12:03):
Yeah. So another one that we used at Etsy, which was an interesting one, is we realized that, so one of the pieces of product that I owned was the onboarding flow. So it was onboarding new sellers specifically. And you can imagine if you're owning that flow, you're just going to be like, all right, we just need a ton of sellers, and we need them to open their shops right away. So we started and we went down that path. And then we realized we actually tanked a couple of downstream metrics that we didn't really understand at first. And those metrics were basically getting sellers to a first sale. So we opened up a lot of shops, but they actually weren't successful when they were on the platform, and they weren't successful in a certain amount of time.

**Nickey Skarstad** (00:12:37):
So we did a lot of unpacking of what happened there, why did we do that, and actually does that matter? And the end answer was, yes, it matters greatly. When Etsy sellers are opening their shop, it's really important that you get them a sale right away because it's a huge motivator, right? If you make a sale in your first day, you're like, "Oh wow. Okay, this is a thing. I could make money doing this. This is exciting. I get to ship something to my buyer." If it takes you seven days, you start to be like, "Oh no. I'm not good enough. I'm terrible at this." 10 days, into 30 days, it really impacts people.

**Nickey Skarstad** (00:13:06):
And so we actually put more friction in the onboarding flow to help to start to solve for that. So we actually slowed you down. We made you be more thoughtful about what you were listing. And by doing that, we actually helped you get to a first sale faster. And so that was another good example of a quality metric that we used, which was, I think it was first sale in seven days. I might be wrong. But something along those lines. And it actually conflated with the high level growth metrics, but it was a huge quality predictor, and it was really important for long term seller success.

**Lenny** (00:13:32):
So interesting. That's such a good topic. And I feel like we could explore that for an hour, but maybe for a little bit longer. Was that metric the metric that you used to measure supply growth at that point? Or was it alongside just general growth?

**Nickey Skarstad** (00:13:45):
Yeah, it was alongside general growth. It wasn't our top, top OKR. But it mattered because, again, it's sort of like you think about these things a bit as a seesaw, right? We basically were balancing our growth with making sure people were successful. And the more equilibrium you had there, the better it was for their overarching marketplace. And it's similar if you think about experiences too, right? Where, all right, you could just be growing, but people are having a terrible experience. So how do you balance those two things? And if you can get those two things in balance, you're going to cruise, and you're going to be more successful longer term.

**Lenny** (00:14:14):
Got it. At Airbnb when I was working on supply growth, our main goal for the supply growth team was similar. And that was actually the goal we had, which is new listings that got their first booking. We only counted listings that had one booking as new supply. Everything else didn't really count. Because we knew that if it got booked at least once, at least it's got some level of quality and people want that place, and it's valuable to the marketplace. Okay. So you were at Airbnb, and where'd you go next?

**Nickey Skarstad** (00:14:40):
Yeah. So I went to a startup. And for lack of a better way to describe this, they were basically kind of building a marketplace as well, but it was more of a marketplace of ideas. And I hate when people say that, because I think it's cheesy, but it's true. They had physical co-working spaces, and they were trying to take some of the magic that was happening in their spaces. So people meeting each other, networking, people getting funding for their startups, et cetera. And they wanted to bring it online and they wanted to try to scale it so it wasn't constrained inside of their four walls. So I helped them basically come up with a longer term strategy, start to figure out how to unpack that, and get product market fit. And then also just build a technology team around trying to solve that.

**Nickey Skarstad** (00:15:16):
And so that started late 2019. And then I was out for a bit, had a baby. And came back and then COVID happened. And they were a physical co-working business. That was where their majority revenue came from. And so COVID was pretty horrible for what they were trying to do. They also had some other cultural issues, and so the whole thing kind of paused/fell over. So I actually spent a year hiring a team and then had to lay them off, which was a great lesson in leadership. I'm not going to lie. I learned a lot about how to lead in that experience.

**Nickey Skarstad** (00:15:49):
But after that, and it was COVID, I had a eight month old, and so I spent time actually just vibing with my kids, which was kind of fun. And then ended up going to Shopify after that. And so I was looking for a more bigger scaled, not startup, and was trying to find something a little bit more something where I could be longer term and was more excited about, and took a platform role at Shopify. And so that was really interesting in that I had, honestly, for the most part spent the majority of my career in super consumer facing roles. And the role that I took was more platform.

**Nickey Skarstad** (00:16:20):
And I realized that, honestly, pretty quickly after I took the role, I was like, oh, good to know. I didn't really understand what this job was and now I know what it is, but it does not give me energy. And so I felt like I had a lot of red energy every day. And so I made a call pretty quickly to bounce, which was actually another good learning experience. I think I've gotten a lot. As I've advanced through my career, have learned a lot about what gives me Nickey Skarstad energy and have been really prioritizing that, especially in a post-COVID world.

**Nickey Skarstad** (00:16:46):
And so left Shopify, and made my way to Duolingo. And so Duolingo has been super fun. I've been there since September of 2021. And in the process of helping them kind of think through a zero to one product challenge, something that's newer. Can't really talk about it unfortunately, but has been another sort of product market fit thinking exercise. It reminds me a little bit of some of the work that I did on experiences. And so it's been actually pretty challenging. It's super fun. So I'm also having a great time here as well.

**Lenny** (00:17:12):
Amazing. The companies you worked at is incredible and there's so much I want to explore there. Going back to Shopify briefly, a lot of PMs, I imagine, are trying to decide should they stay where they're at? Should they go explore other places? So you said the thing that kind of pulled you out there was just the platform role didn't feel like a fit for you. Do you have any advice for folks on just how to know if a role or a company isn't a fit for them?

**Nickey Skarstad** (00:17:37):
Yeah. So I think I really learned that while I was there, and also I want to make sure I actually had a great experience at Shopify and I think it is an awesome company. I would highly recommend people work there, especially if they like platform product work. One of the things I did when I was like, I don't know if I love this is I actually went through my calendar and I changed the colors of all of the meetings on my calendar to red, yellow, and green after I had the meeting. And I looked. And basically if it was yellow, I was like, okay. It was a fine meeting. My energy was baseline. If it was red, I was either bored or I was stressed, or I was not having a good time. And if it was green, it gave me energy and I felt excited and I wanted to keep working on that.

**Nickey Skarstad** (00:18:17):
And when I looked back at the last few weeks, it was almost all red and yellow. And I was like, okay, this is really from an energy standpoint, I don't think I love this. And so I would say think about the work that you're doing and that lens. Get really good at figuring out what are the things that you love most about being a product person, and how can you optimize your next role for those things that you love?

**Nickey Skarstad** (00:18:39):
We should talk a little bit more about this, but each company has a very different product org. And the day to day of your job as a product manager, depending on where you go in the product that you're building, is very different. And so really thinking through what that work looks like, what their process is, who your end consumer is, what will the actual work you be doing every day, what will that be? And if you can get really clear on that, and then get clear on what gives you energy and what you love, it makes it a lot easier to figure out where you should go next.

**Lenny** (00:19:04):
Wow. I love that tactic. I've never heard of that. Just going back to the meetings that you have in measuring, just reflecting on how much energy that meeting gave you. Great tip. Thank you for sharing that. And I'll also double down on Shopify is an amazing place to work. Just to make that clear. It's probably one of the few places I recommend PMs go try to work at.

**Nickey Skarstad** (00:19:23):
Yeah. I think especially if you're newer in your PM career, they just have a really great organization. And I think it's a great place to learn how to PM. Also their product, it's a huge scaled product. And so it's complicated to build in. So I think it's a great place to really understand second order systems and systems thinking. And especially if that type of work gives you energy, I would recommend that people look for jobs there. But again, get really good at what you love. And I think what I've realized longer term is I really like the zero to one early stage. How do we get product market fit? And how do we really think through the early experience? And Shopify is at a very different stage than that. They're doing that in a couple places for sure, but that's not their day to day. And so that was interesting.

**Lenny** (00:20:06):
Yeah. That makes a lot of sense. Going back to what you just touched on, the idea of product org and structure and how different companies build product, there's kind of two ways to approach this and take whichever direction you want. Which of the companies you've worked at did you enjoy most, and that's kind of stuck with you as a way you want to build product? Or just like, how would you approach building a product org in cross-functional teams versus not, and reporting lines, things like that? What do you recommend there?

**Nickey Skarstad** (00:20:34):
Yeah. So I feel like you're asking me to pick a favorite child, which especially as a mother, that's hard to do. But no, I don't know. I feel like I've learned things from a lot of these different places and it's hard to choose. I think some of my early work at Etsy was very formative, and it was where I learned how to be a product manager. And so I feel very proud of that. I also think Etsy was out there building in public. I'm literally doing air quotes right now. I know you can't see me.

**Lenny** (00:20:57):
I can see them.

**Nickey Skarstad** (00:20:58):
But they were doing that because they had such a passionate, involved, engaged early community that they could not just ship things and have them land well if they did not involve their community early. So they were doing prototyping, beta testing, and basically getting people to try things and give feedback on things. I honestly, I think before a lot of people were, and that was something at the time that was really interesting and has really stayed with me, it's how to work with community and how to build community around the product that you're building.

**Nickey Skarstad** (00:21:25):
Because at the end of the day, especially when it's early days, it really helps scale, get people to evangelize what you're building, help teach other people how to use it, things like that. And so I learned how to do that at Etsy. And I think that was super formative. And then also just Airbnb, what we talked about before, and just deeply baking in product quality and the end consumer experience into everything that you're building is also something I literally apply every day. So if I had to choose, it would be those two places, but I plan on continuing to learn.

**Lenny** (00:21:54):
Interesting. Both very community driven businesses.

**Nickey Skarstad** (00:21:57):
True.

**Lenny** (00:21:58):
And then in terms of how they structured their org, is there anything there about just here's what I've learned works best for how to build product teams, structure product teams, that stuck with you?

**Nickey Skarstad** (00:22:07):
Yeah. So I think there's kind of two overarching popular organizational modes for product org specifically. There's either the functional organization where everyone in the product team will report up through either a VP product, or a chief product officer, or something along those lines. And I think that actually really works in certain circumstances and is great. And typically how that works is you'll have your product partners, your trifecta, if you will, you have your design partner and your engineering partner, they will typically also report up into functional leadership. I think in bigger organizations that really works well, especially when you have orgs that need a lot of development in the function. So you'll have a lot of either APMs or product managers who are newer in their career and need a lot of support in development. And I think those functional ways of building makes sense. When I was at Etsy, that was the way that the reporting structure was and it made a lot of sense.

**Nickey Skarstad** (00:23:00):
And then on the flip side, actually, when I was at Airbnb, because experiences was this new pretty nascent business opportunity, it had a GM structure. And so basically the whole product org that worked on experiences laddered up into a business leader and that business leader managed all of the functions. So they were the manager of the operations team, the marketing folks, product, and whatever. And I actually think that really worked for team like experiences at a company like Airbnb because what it did is it gave the leader of that business a ton of autonomy to really figure out what does this business need to be successful? And they didn't have to rely on, I guess they did in some ways, but not 100% rely on the larger company's resources to get the work that they needed done.

**Nickey Skarstad** (00:23:44):
And I actually think that had they launched experiences inside of the Etsy style of organizational structure, it never would've succeeded because it had such a unique business need, and it needed its own process and ways of building product, et cetera. And because they sort of, hate to say wall it off, because it wasn't fully walled off, but because they gave it its own space and its own structure, it allowed it to succeed because they were able to fund it in the right way, give it the resources that it needed, et cetera.

**Nickey Skarstad** (00:24:14):
So I've seen those two types of models work. And I think if I was a founder and I was building my initial product org, how I would think about it was basically what are we trying to build? What is the product? And then what type of process do we need to put in place for us to figure out how do we build it? And then what type of people do we need? And then really taking a step back to really figure out, all right, organizationally, how do we shape this so we can make sure that those people have autonomy and they have what they need to just be able to cruise? So I honestly don't think there's a right way. I know that's a non-answer. I think it really depends on what you're trying to build and the stage at which you're at.

**Lenny** (00:24:48):
Is there a default approach you'd suggest, just like most often you should go to the GM model, or most often you should just go with this cross-functional team?

**Nickey Skarstad** (00:24:58):
Yeah. I mean, I think especially if your business is new, going functional makes sense because you don't necessarily have a lot of organizational complexity. Airbnb at the time we were there, Lenny, was a huge company, right? It had tons of different teams that were trying to tackle many different problems. So that GM model made a lot of sense because it again was able to take a specific business opportunity, give it the resources that it need, and give it space to run. When your company's smaller stage, I think that matters less. Typically, especially if you're working on solving similar problems as an organization, functional makes a ton of sense. Because then you're also thinking more holistically about, all right, how do we build the right product development process across different functions to make sure that we are, to use a bad metaphor, it's like the symphony metaphor. You have all these different instruments that need to figure out how do we play together at the right times? And I think that functional way of working actually allows you to do that really well.

**Lenny** (00:25:52):
**Nickey Skarstad** (00:27:43):
Yeah. Well one, I want to know who you talked to. That's terrifying. Hopefully they said good things. You don't have to out them.

**Lenny** (00:27:49):
Unnamed sources. Unnamed sources.

**Nickey Skarstad** (00:27:51):
Yes. Well I'm glad to hear that because that actually is some of the work that I honestly love the most. And when I look at my calendar, those are moments where I am green energy. And so I have some first principles that I like to apply when I'm thinking about setting high level vision and strategy. And the first is make sure that you pull in your people and your team. I've seen a lot of director level people through my career who will try to work on strategy in a vacuum alone. They'll write a document and they'll be like, "Okay, team. Here's what we're doing. Here's our strategy." And it never goes well. And it doesn't go well. It might be the right strategy, but because you did not bring people along on that journey to come up with it, they did not feel like they had a hand in crafting it themselves. They are often not bought in, and getting people to buy in when they haven't been involved is very challenging and time consuming. We don't got time, right?

**Nickey Skarstad** (00:28:40):
And so I think that's my first principle is just bring along the team. And I think there are ways to do that where you're not voting on strategy. You should not be voting. I think good product work is often not democratic, right? You need a clear leader who understands a lot of the signals and understands the larger competitive marketplace that can make decisions. And I think, especially when you're thinking about strategy, it's great to get input, but ultimately at the end of the day, you should have one person who is responsible for it.

**Nickey Skarstad** (00:29:06):
And the other thing is a lot of times people don't really talk to leadership or the larger business leaders to get organizational context that helps them come up with the right strategy. They'll sort of build something in a vacuum, and then they'll come up with it and they'll get a ton of feedback from people across the org that were like, "Oh, this conflates with our strategy. We're doing this, and it's very similar." Or, "Our structural platform actually does not have the capability for us to do that thing." Whatever. And so just make sure that you're talking to people. And also all the way up to the CEO, and making sure the founder and the CEO is very bought in because ultimately, at the end of the day, they're choosing to resource what you're working on and are going to help you meet what you need. So those are some of the foundations for good vision and strategy work.

**Nickey Skarstad** (00:29:51):
And then kind of zooming down into the weeds, I really like the vision mission strategy pyramid. I think might be a little tired. I like to think it's wired. But yeah. So if you just think about a pyramid shape, at the top is vision. Below it is mission and strategy, and then objectives. And this is a very simple framework. You honestly just Google vision mission strategy objectives, and you'll see it in Google image results. And all it is really is thinking about hitting those specific notes and thinking about them top down. So where do you need to go long term? What is the long term vision of what you're trying to do? In 10 years, if you could zoom up and look at what an ideal path for you would be, what is that? Write it down.

**Nickey Skarstad** (00:30:32):
And then you start, as you go down the pyramid, you get clearer and basically you bring things down to your moment in time more clearly. So if you're thinking about your mission, all right, it's another level of abstraction of how do we make our vision come to life. And then you get into strategy. All right, how do we actually pick apart what we think is going to need to happen for us to actually be able to execute on that vision? And then your objectives can be OKRs, or whatever sort of goal setting model that you use to really one level get clear on, all right, in the next three to six months, what are the actual notes that we need to hit to be able to sing that beautiful symphony, is a terrible metaphor. And now I'm open to say it. But whatever.

**Lenny** (00:30:32):
I get it. I get it.

**Nickey Skarstad** (00:31:15):
Dang it. Love a bad metaphor.

**Lenny** (00:31:16):
That's evocative. While we're on that topic, actually just to interrupt briefly, how are you very practically doing this for say vision and mission? Are you starting a Google doc and writing it out, are you using Miro or FigJam, or something like that?

**Nickey Skarstad** (00:31:30):
Yeah, so I think visioning exercise is a great moment to pull in your larger team. Because I'm remote now, I would use Miro or FigJam. Duolingo, we use FigJam typically because we are super embedded in Figma. In the past I've used MURAL. I actually personally like MURAL's whiteboarding product better. So I would open that up and I would walk through a number of things with the team and do a brainstorm literally. All right. Where do you all see us going in 10 years? What do we think what is the larger competitive landscape going to do in the next 10 years that could need to influence the work that we're doing? What are their ideas, and get everyone thinking.

**Nickey Skarstad** (00:32:05):
Good brainstorm are often cross-functional. So go outside of your own team. Can you pull in somebody from marketing? Can somebody from the larger policy team sit in? How do you make it really cross-functional and really zoom up and give everyone the space and the freedom to think existential and to frame it that way,?we are going to be thinking in a five to 10 year timeline. Do not worry about what's happening today. And honestly, if you do that right, those are super fun exercises.

**Lenny** (00:32:30):
And you're doing this remotely, I imagine.

**Nickey Skarstad** (00:32:32):
Yep.

**Lenny** (00:32:33):
And so do you just kind of schedule a meeting, kick it off, point everyone to this Miro doc, for example, with a bunch of prompts and sticky notes and things like that? How do you actually practically do that?

**Nickey Skarstad** (00:32:44):
So I would pre-fill out the Miro beforehand. So figure out what are the things you want to discuss with your team, create them as headers in the Miro document. So when everyone lands in there, you have a very clear here's what we're talking about today. You can put that into the agenda on your calendar invite. I've actually been to some really good strategic brainstorms that will attach some kind of competitive thinking landscape in advance. So people could have a little bit of a pre-read.

**Nickey Skarstad** (00:33:06):
And then when you get into the actual session, you already have the time allotments scheduled and thought through. And both Miro and FigJam have really awesome timer, and it'll play music while everyone is working. It's pretty cute. FigJam's sounds are really well done. Whoever their sound architect is, bravo. And it'll ding after, give them 10 minutes and it'll give you a nice chime, and then you can review them together and you can go through each touchpoint that you want to talk about.

**Nickey Skarstad** (00:33:33):
After it's done, I like to do some synthesis together in the meeting. So basically grab ideas that are similar, bucket things into concepts that are alike. And then I will take it later and spend more time thinking about it. I think a lot of people think you have to actually come away with a vision together in a meeting that's very clear, and you don't. You can just come up with ideas, take a stab at drafting it, and get some more feedback before it's final.

**Lenny** (00:33:56):
One last question on this thread, which also could be an entire hour of discussion, are there any examples of prompts or things you ideated that you could share? I know you can't talk about what you're doing at Duolingo, but just to make it a little more concrete for people, what are some examples of things that you brainstormed?

**Nickey Skarstad** (00:34:11):
Yeah. I mean, so to take it back to experiences, because we've talked about that a lot, so people have some baseline context. Some of the early experiences visioning was really interesting because it was all about what type of experience can we create. And really thinking through when you've traveled in the past, what has brought you joy? Or what were the moments in your travel journey that have been really interesting, provocative, basically you remember the most, and why? And thinking through some of those things as a group. And those are good group exercises, because you're like, wow, I got to know a lot about Lenny by that crazy travel experience that he had. And so really kind of thinking through about how you craft really meaningful prompts that, again, connect to your strategy. So how does that ladder up into strategy? Obviously thinking through the experience that you're creating is going to help you come up with the right vision and fill out your pyramid in the right way, right?

**Lenny** (00:34:57):
Okay. So we went on kind of on a tangent around brainstorming. Did you want to share more around just going from vision to goals to execution?

**Nickey Skarstad** (00:35:04):
Yeah. So I think just generally, as you walk down that strategy pyramid, really getting down into the OKRs. And I think it's important because sometimes strategy is too abstract and too high level. And it's hard for people to take the step on how do I walk up that pyramid? And that to me is where having good strategy and having good OKRs help your team do that. And so good OKRs to me are just clear articulations of your strategy, whatever it is that are important to you, and it boils it down into the next three months, here's what we're working on. And I think that is just really good for teams because, again, if you're always in the clouds, it starts to get hard to really bring things down to the feature level of we're going to create a Jira ticket for this specific thing that we need to build. It needs to connect up to a strategy and back down.

**Lenny** (00:35:53):
Got it. Where do you put, say, these OKRs? Do you just brainstorm, come up with vision and rough strategy, that translates into goals? Where do you do this? And then also just how long do you usually spend on this overall process?

**Nickey Skarstad** (00:36:06):
Yeah. So the way that we do it at Duolingo now is we work on quarterly OKRs. And so that process will kick off usually the third month in the quarter. Really thinking through, all right, how are we trending on our OKRs this quarter? Did we commit to the right number of things? How are we doing? And then it is going, all right, so what do we need to do next quarter? And ideally, again, that's going to plug into a longer term plan. Otherwise it feels a little messy, and it feels not grounded in a long term plan or strategy in any way, shape, or form.

**Nickey Skarstad** (00:36:36):
And then, so what we'll do is spend a few weeks as a team coming up with, all right, what could the next quarter look like? What is going to add the most impact and help us execute on that long term strategy? And then how do we make sure that we're setting the right objectives and KRs below them? And then usually there's some sort of leadership review. I actually forget, Lenny, how did goal setting go at Airbnb? I honestly don't remember. It sounds terrible, but it was a while ago. I can't even remember if Airbnb used OKRs.

**Lenny** (00:37:03):
There was a long period where OKRs were a very big deal. Our head of product was really gungho on OKRs. And I think for a couple years, we were very strict OKR culture. And then it kind of evolved into just rough-

**Nickey Skarstad** (00:37:15):
Goals.

**Lenny** (00:37:16):
... interpretation of OKRs. Yeah, goals and strategy and mission and vision. And so it's kind of this morphed version at this point, as far as I know.

**Nickey Skarstad** (00:37:23):
Gotcha. Yeah. And I will say OKR frameworks might not be the best for every single team, but having some sort of goal framework that is shared across functions is useful no matter the size or the scale of your business. I think a lot of times people get hung up and they want to nitpick OKRs specifically. And I think some of those criticisms are very fair. But you should have some sort of framework that's shared from a process standpoint across your team that everyone can use and work on together. Because again, it takes your strategy and it brings it down into the now. So you can act on, in the next three months, you can bring something to life, and you're very clear on what that looks like.

**Lenny** (00:37:57):
I'm going to pull out a thread of something you mentioned earlier of how to finally make decisions. And how in your experience the PM kind of is often sort of a final decision maker. I'd love to hear any advice you have of how to set that up on a team where it's either clear the PMs have a little bit more say and/or just bring people along to a final conclusion. Is there any advice on tips and tactics used to help with that?

**Nickey Skarstad** (00:38:22):
Yeah. So I actually just read this really great book that is slightly tangential, but I thought it really applied to this type of basically getting people to align on decisions. It's by Chris Voss. He is this famous FBI negotiator. I think it's called Split the Difference: Negotiating As if Your Life Depends on It. Don't quote me on that.

**Lenny** (00:38:38):
I think it's Never Split the Difference, right? And then I think he's also got a masterclass which I've watched, which is really good.

**Nickey Skarstad** (00:38:43):
I actually haven't watched the masterclass yet, but it's on my list after reading the book. And a lot of it, I think, especially because he's an FBI person, I thought it was going to be very much, "You're going to do this." And it's all basically his whole approach is empathy, and it's repeating things back to you, making people feel heard, making sure that you're hearing why they maybe don't like your strategy, or why they think that's a bad OKR. And I think if you can spend some time just listening to your team and really understanding why is this not resonating, you can help guide people on the right path. Or you realize you're wrong. Good PMs are humble people, right? You're not always right. Not always going to be right. So how do you know when you're right and wrong is another good podcast that you should do with somebody else cause I'm probably not very at it. Yeah.

**Lenny** (00:38:43):
Good tip. I really like that.

**Nickey Skarstad** (00:39:28):
Yeah. But I think that helps. And the other thing is I love the concept of one way versus two way door decision making, right? If your team is making a really critical long-term decision that's going to be limiting to a lot of the future things that you could want or need to do, that is a one way door decision. And you should spend time really thinking about discussing it, getting feedback and buy-in from your larger community, from your leadership team, et cetera. If it is a two-way door decision, it's not going to make a huge impact, you can change it later if you need to, let your team cruise on those things. Because it gives people autonomy. It helps you move fast. And then it just makes sure that when it does come down to decisions that are harder to change longer term, then those are the moments you should spend time and really think about and discuss and debate, et cetera.

**Lenny** (00:40:09):
Do you have any examples or stories that come to mind of those sorts of decisions that you kind of help people just go for it, even though I may not necessarily agree?

**Nickey Skarstad** (00:40:17):
Let's see. Yeah. So one big one that we made at Airbnb that was pretty formative in early days was we came up with basically an articulation of what we thought a good experience was, and the standards that an experience needed to meet for it to be considered a good experience for us. And that was a many month long term project. And it was so important because we ended up building the product around it, building our policies around it, building how we educated our hosts around it. We had one moment in time to figure it out and get it right until it scaled everywhere. And so that was a true one way door decision where it was really hard to change later because we literally needed it to be relatively final.

**Nickey Skarstad** (00:40:53):
On Etsy, there was some big decisions that were made at certain points in time around what can be sold in the marketplace, and how to think through what constitutes something that is hand made. Those were one way door decisions, right? It's really hard to change that later because it's going to influence all of the listings that you have in your ecosystem. And so I think really thinking through those types of things are important and really setting teams up to be able to pause and spend some time to get it right because it will influence the end product in a very real way.

**Lenny** (00:41:23):
How do you know if it's a one way or a two way door decision? Do you find that it's generally pretty obvious when you're making the decision, or is it sometimes like, oh shit, we should have thought about that more?

**Nickey Skarstad** (00:41:34):
Yeah. I would say I think I'm good at this 80% of the time these days, just because I've seen it done wrong in a lot of ways. But I think it's a muscle that you build honestly, and you get better over time about thinking about second order thinking. And so it's starting to understand, all right, if I make this decision today, it's going to impact this next level of decisions and the next level after that. And that will cascade through our larger system.

**Nickey Skarstad** (00:41:56):
A great book to read if you are a product person is Thinking in Systems by Donella Meadows. It's just about really thinking through how systems work, and then you can start to extrapolate what is the second order effect of the system. And if you think about that through your own ecosystem, it starts to help you understand, all right, this is a linchpin in our larger ecosystem that we got to be really careful about if we're going to touch it or change it longer term. But I do think some of that it's muscle, you build it over time. You make a couple of mistakes sometimes, and then you have to realize the true consequences of those mistakes and you don't make it again.

**Lenny** (00:42:29):
Can we talk a bit more about the second order decision framework? I know you have a awesome newsletter post about this, and it was something I wanted to chat about. Is this a framework that PMs can use to make better decisions? And I guess how could they do that? And then maybe just describe a little bit more about just this concept of second order decisions, because it sounds really important.

**Nickey Skarstad** (00:42:50):
Yeah. Basically what second order thinking is is you being able to think beyond the decisions that you're making today. The decisions you make today will affect tomorrow's decisions and your ability to build on your decisions that you made today. And this feels very existential and meta, but why it's important is that, especially when you're building product, is there's a cost associated with your time of everything you build. Especially when you're building marketplaces or anything with UGC content. When you make a change today, and it impacts every single user in your ecosystem that then is going to act on that change, it's really hard to make those changes later.

**Nickey Skarstad** (00:43:23):
Let's talk about Airbnb home listing as an example. Really thinking through what are the pieces of data or all the pieces of data in the system that we need to actually list a home. And then how do we use those throughout our whole system in different ways? And then anytime you have to change those things. So that could be little simple things like truncating the length of the title of an Airbnb home when it's listed on the platform. You're going to have mad hosts, you're going to have design changes that need to be made to make sure that they can actually display something in a different way. It gets just inherently more complex the more complex your system is. So that is probably a terribly described way of describing second order thinking.

**Lenny** (00:44:01):
That makes total sense. And that's something we dealt with it, sorry to interrupt, but that's like on the host team, we dealt with this question often of just any change you make and the listing flow is going to impact so much of the experience of a host and a guest. And so that makes total sense. Sorry, keep going.

**Nickey Skarstad** (00:44:16):
Yeah. No, and I think that forcing yourself and your team to think in that way is just a really good thinking exercise because it will save you time and it will save you money, a lot of money later, if you don't constantly have to rebuild things when you want to make changes to your system later. And that ladders up again into having a very clear vision and a strategy. Because what you're doing is you're starting to think on the long horizon. And so the decisions that you're making today are in service of that long horizon. So you can actually build in that direction and you don't constantly have to rebuild every time you're trying to change something.

**Lenny** (00:44:50):
On the second order thinking, sorry, I called it second order decision, but in this framework that you spoke of, how do you actually operationalize this concept? When you're planning, do you write out in the document second order impact that we should be thinking about, or do you do something else?

**Nickey Skarstad** (00:45:05):
Yeah. So I think there's many ways to do this. If you have a spec-ed template or a piece of documentation that your team typically use when they're writing out product strategy or product requirements, et cetera, you can put a line in here to force people to think about it. I also think thinking about first principles and writing out first principles for the changes that you're making often are in service of second order thinking. Where it's like here are the things that we care about. Here's why these things are important. And we want to make sure these are baked into what we're building. Typically you'll write those through the lens of second order thinking.

**Nickey Skarstad** (00:45:36):
Shopify uses first principles a lot in everything that they build. And this is something I took away from that way of working because it's extremely effective. If you can get teams to align on first principles early on, it saves you a lot of heartache later because you've got people to align way early days before you even got into the design process, or before you had to start thinking about how do we actually technically implement this.

**Nickey Skarstad** (00:45:56):
And then the other way I would say is there's ways to structure or have thoughtful discussion around second order effects. That could be a brainstorm. You could use Miro to think about that. We're going to make these changes today. How do they cascade through our ecosystem? What are the gotchas or the things we need to worry about? And again, I think the more complex your ecosystem is, the more you are forced to do this. A lot of founders in early stage products don't think like this because they're so focused on the product market fit. We need to just get something that people are using. That then when they get product market fit, they realize when they get into scale mode, they didn't build something scalable, and they have to rebuild things which can actually really hurt them when they're trying to grow really quickly later on.

**Lenny** (00:46:35):
Yeah. Absolutely. Happens all the time. For principles, do you put those in to say the team strategy, like the quarterly strategy document? Like here's our principles for the quarter? Is that how you generally do that?

**Nickey Skarstad** (00:46:47):
Yeah. I think that is a great place to put it. You can write them on the feature level too. So something that you're building, just getting clearer on here are the things that matter to us. Here's what we care about. We're going to design in service of these things. And here are the things that aren't that important. And again, those are the types of places in a product requirements doc where people will argue the most, which is a good thing because you're basically discussing and debating sort of foundations of what you're going to build before you get into the work of building it. And so those exercises are always a good idea.

**Lenny** (00:47:16):
Awesome. I love that. Okay. So going back, because I wanted to close this thread, you've come up with your vision, your mission, your strategy, your goals as a team. People start to align around it. What do you do to kick it off and get people on board and aware of the plan, and then to stay on plan with that strategy and not kind of be distracted by new priorities and shiny objects?

**Nickey Skarstad** (00:47:38):
Yes. Oh, the shiny object thing is very real. Good question. So for example, I just did this recently where I brought my team along through the OKR process for Q2 planning. They had a say in basically what we decided we were going to work on. It went up for leadership approval. We got approval. And my process was I used Loom, which is another one of my favorite products. It's just a really easy screen share and video recording tool that you can share with teams. And so I just recapped, "All right, here's what I presented to leadership. Here are the feedback that we got. Here's the strategic feedback that we got. And here are the changes we're going to make. Any questions, let me know." And I posted it in Slack.

**Nickey Skarstad** (00:48:10):
So I was just trying to keep the feedback loop really quick and tight with teams rather than wait till the next meeting you have with them a week later. I was like, all right, I'm going to just try to spend five minutes recording this and get it out ASAP. And that helps because then it gets people excited. Okay, cool. This thing that I worked on got really great feedback from leadership, and now we're working on it. I'm excited to get going.

**Nickey Skarstad** (00:48:29):
And then it depends. Usually depending on the project, I have some sort of kickoff. I don't usually do a quarterly kickoff or anything like that because I think there's usually disparate teams owning different parts of strategy. But usually having a good weekly team meeting where you're really thoughtful about cascading feedback down from leadership, constantly checking in on what are we trying to do here? What is our strategy? How are these goals that we set laddering up? Are we achieving it? Are we not? Whatever. Having a meeting like that where you're kind of constantly talking about it each week also helps people feel bought in and not get distracted.

**Nickey Skarstad** (00:48:59):
And actually I found that teams who are very bought to your vision and strategy are less distractable. Where I usually have more trouble is with leadership that aren't necessarily in the weeds with your team every day. And I'll get an idea. "Have you thought about doing this one random obscure thing?" "Yes. However, it's not in service of this long term plan, so we don't want to do that right now because we don't think it's the best use of our time."

**Lenny** (00:49:23):
Got it. And the way you're describing it, this is as a manager of product managers-

**Nickey Skarstad** (00:49:27):
Yep.

**Lenny** (00:49:28):
... versus an ICPM? Cool. So as an ICPM, I imagine you would do a quarterly kickoff, or whatever your cycle length. You kick off with the team. Here's what we're doing. Any questions?

**Nickey Skarstad** (00:49:38):
Totally.

**Lenny** (00:49:40):
Okay. Another thing I wanted to make sure we have time to chat about is product review meetings and process. Just kind of like how do you, as a product leader, make sure that you're shipping great stuff that you're proud of and that your leaders aren't surprised by? How do you design just a product review and design process.

**Nickey Skarstad** (00:49:56):
Yeah. So I have a lot of strong feelings on product reviews. And it's because I've been in a lot of different organizations and I've seen a lot of bad ways of doing this honestly. And I think it also depends on the product that you're building and the team that you've created. So I don't think that there's one right or wrong way to do this.

**Nickey Skarstad** (00:50:12):
Where I've seen them fail is when they happen at the function level, and they're not done or shared as a team. Typically it's normal to have a design review or to have some sort of technical review. And the more you can try to bring those different review processes into one central moment to check in, the better it tends to go. Because what happens is you'll have feedback in a vacuum. The design leader will give the designer feedback, and then you don't hear about it. Or there'll be some technical flaw that happens in a very specific technical review that doesn't get back to the larger team.

**Nickey Skarstad** (00:50:43):
So finding ways to make sure that those parts of your process are shared across each function, and you attend them and prepare for them as a team, I think really helps a lot of that. I'm not saying that you shouldn't have a design review. Of course you should. I mean, you should just be really thoughtful about having moments, especially if there are moments where you're blessing something to move forward, to making sure the whole team is there. And that there's a very strategic check-in process to get those things approved that everyone knows about and is a part of.

**Lenny** (00:51:11):
Is that a meeting that you do weekly and you invite the designer and the engineer? Who do you invite, I guess, and what is the goal of that meeting? The goal of that meeting, I imagine, is approved the product to go launch and build.

**Nickey Skarstad** (00:51:23):
Yeah. And I think especially going back to the one way, two way door moment, giving teams autonomy to ship some things that you think are two way doors and aren't necessarily mission critical are important to your vision, but aren't going to conflate with the larger system, I think trying to keep things quick and not have too many barriers for people to ship is incredibly important. So you'll have to figure that out for your own org and it's nuances, but that is something that is important.

**Nickey Skarstad** (00:51:49):
But when there are moments where you think it is basically a feedback gate, where it's a gate you need to walk through and a specific moment in time where you've gotten feedback, I think having a cross-functional meeting where there's a clear pre-read or something that's sent before. It's like, here's what we're talking about today. And then aligning on, do we think this meets our goals and does this meet our quality bar? And doing that in a really thoughtful way just so the team gets feedback. So the leadership is plugged in, but also so you're not standing the way of people shipping their products.

**Lenny** (00:52:17):
And then do you check in throughout the process of the product being built, or do you kind of encourage teams to get to a point where it's basically ready for approval?

**Nickey Skarstad** (00:52:26):
Yeah. Ideally in a perfect world, there's three check-in moments. There is the first principles check-in. What are you trying to build, or what are you trying to do? What are the sort of foundations that you're going to build on? What is the most important thing? What are you solving for? Getting approval on that, weirdly, is almost the most important thing. Because it saves a lot of teams a lot of time when they get later in their feedback review process and people are like, "You're not solving for the right thing." So that's important.

**Nickey Skarstad** (00:52:49):
Once you've aligned on that, then it's like, all right, what approach are we going to use? What are we going to build? And that's sort of how we solve the problem. Making sure that there is a technical component there too so there's some sort of infrastructure review or architecture review, or whatever you want to call it. And then it's like, all right, this is ready to ship. Let's check in again. Do we think it's ready? And I think that, again, it depends on your organization. If you have a very small team, you might be very plugged in and these things might not need to happen. But in bigger organizations, especially where leadership isn't always able to be in the room, making sure that you have a clear checking in a few times to make sure that everyone is moving in the right direction and everyone feels good is, I think, a worthwhile exercise.

**Lenny** (00:53:27):
I love that. Such a simple framework. And then one last question along those lines, do you leave it up to the team to schedule these meetings, or are you pulling it out of them and making sure they schedule it?

**Nickey Skarstad** (00:53:36):
Today, because the team that I'm working on is pretty small, and we're pretty pre-product market fit, we're not doing a ton of very formal check-in moments because we don't need to be. Because it's a small team and we're all cruising together. But in bigger orgs that I've worked in, for Shopify, for example, there was a process around having these meetings and who would be there. And so those would kind of be scheduled through the larger processor system that they were working in, which really worked for them actually. And I think it allowed teams to be pretty autonomous on the day to day, but just making sure that there was feedback coming of from their users as well as from leadership.

**Lenny** (00:54:08):
Got it. One last question before we get to our exciting lightning round. And it's something that I've been thinking a lot about recently, which is around remote work as a product manager. I left Airbnb before COVID, and so I never lived in this world of everything is remote and product managing remotely. Is there anything you've picked up or learned that has been really helpful to being a product leader in a remote world?

**Nickey Skarstad** (00:54:30):
Yeah. I would say last couple years have just been a huge shift in my ways of working. I sort of grew up as a PM in IRL environments where we did the majority of our work together in the same room. So that was whiteboarding, having a quick sync after you had an in person meeting to finalize some details or keep hashing out a problem. It's so cheesy and overhyped, but the proverbial water cooler moment where you see somebody, and you're like, "Hey, how are you doing, Hey, did you hear about this thing?" All of those things literally went away overnight.

**Nickey Skarstad** (00:55:01):
And I think especially the job of a PM, it's hard under normal times because you are doing so much labor to make sure people are informed and give feedback, et cetera. And then overnight you took away a lot of the methods that they were using to do it. And so I think that has been a pretty profound shift for a lot of people working in product roles.

**Nickey Skarstad** (00:55:21):
The good news is there's a ton of new tools and new technology that's actually being built right now that's majorly helpful for this. So I use Slack in very new ways today than I did two years ago. Things like just making sure to post more asynchronous updates. Trying to actually take the burden off of an IRL or a Zoom meeting. Can we talk about this asynchronously and do it in Slack? Slack has this really great feature called huddles where you can just quickly get on. It's just audio. So there's no video. And you can just have a 30 second conversation. It's good for standups and things like that. Suggest you try it if you haven't yet.

**Nickey Skarstad** (00:55:56):
And then a lot of the old in person whiteboarding, things like that, you can do those now using awesome tools like Miro and FigJam. And I feel like, especially at Airbnb, we had such an international team that there was always somebody who was remote typically. And I think we never really got the remote experience right. And now that the majority of our teams are remote, I'm a fully remote person, I've been a lot more thoughtful about making sure we're creating a really good experience of how we're working for the larger team. And so I think you have to hack on this with your team. Different teams have different ways of working, but trying to be a synchronous, using Slack, making sure you're following up in very visible ways where people can see. Don't rely on Zoom meetings to fill all of your time. Otherwise people will literally hate you. And things like that really make a huge difference.

**Lenny** (00:56:43):
Awesome. Super helpful. All right. Nickey, are you ready for the lightning round?

**Nickey Skarstad** (00:56:48):
I'm ready. Let's do this.

**Lenny** (00:56:49):
What's a book that you recommend most to other product managers?

**Nickey Skarstad** (00:56:53):
I love Thinking in Systems by Donella Meadows.

**Lenny** (00:56:57):
Awesome. Okay. We're going to link to that in the description. Other than Duolingo, what's another company that you recommend the PMs go work at or explore when they're looking for a new gig?

**Nickey Skarstad** (00:57:07):
Yeah, I would say Etsy hands down.

**Lenny** (00:57:09):
And why is that?

**Nickey Skarstad** (00:57:10):
I think it's a great place to learn how to be a PM. Data driven, really supportive, product leadership, and a super fun product to build.

**Lenny** (00:57:18):
Awesome. Love that. What's the current favorite kind of app or piece of software that helps you do your work better?

**Nickey Skarstad** (00:57:25):
I'm obsessed with Superhuman, which is a email productivity app, which once you start using it, you can't not use it. You basically have to use it for the rest of your days. I also am obsessed with Loom, which is a video recording tool that makes it really easy to share really quick video updates.

**Lenny** (00:57:41):
Awesome, great choices. And then outside of work, what's a current favorite app or just piece of software that you love?

**Nickey Skarstad** (00:57:47):
Definitely TikTok. Short form video is very fun and entertaining. Can't get enough of it, and have been creating some myself. So I'm definitely hooked.

**Lenny** (00:57:56):
While we're on that topic, how do people find you on TikTok?

**Nickey Skarstad** (00:57:58):
Yeah, it's just my name. It's Nickey Skarstad, and give me a follow.

**Lenny** (00:58:03):
I'm a very happy follower. And then I'll link to that in description too. Who's a favorite person that you like to follow on either Twitter, or Instagram, or even TikTok?

**Nickey Skarstad** (00:58:12):
Yeah, so I love, she is a cultural journalist, her name is Anne Helen Petersen. And she's really plugged into sort of the larger cultural zeitgeist of the time. And I always give people, when people ask me my top advice for new PMs, it's just to be a consumer. To download new products, to try them out, to use all the things and try them because I think it actually makes you a better product builder. And follow people that are not just tech people on Twitter. You are doing yourself a disservice if your entire feed is tech people. So find people that are plugged into cultural zeitgeist because it helps you also understand the moment in which you are shipping, and it'll make sure that you're acing your product marketing and your messaging and you're building the right thing.

**Lenny** (00:58:53):
What's her name again?

**Nickey Skarstad** (00:58:54):
Her name is Anne Helen Petersen.

**Lenny** (00:58:56):
Anne Helen Petersen. Love it. Okay. And then final question. Who's been your favorite manager?

**Nickey Skarstad** (00:59:01):
Yeah, so I couldn't pick one person here, so don't be mad. But it's actually a lot of women that I worked for at Etsy. The majority of my entire reporting line the time that I was there was all women, which has never happened to me again. So shout out to Kruti Patel, who is their current chief product officer, a woman named Heather Jassy, who ran the community team at Etsy long ago, who was a true delight to work for. And then Linda Findley, who is now the CEO of Blue Apron, but she was the chief operating officer at my time at Etsy. And she was my boss for a bit. And she was wonderful.

**Lenny** (00:59:31):
Amazing. Thank you for sharing all that. And thank you so much for joining me, Nickey, for doing this. Where can people find you online? And then just generally, how can people that are listening to this be helpful to you?

**Nickey Skarstad** (00:59:43):
Yeah, so I have newly become obsessed with TikTok, like I said before. I've been creating some fun, little short form videos. One of my regrets as a long time product builder is it's very time consuming to write down the stories of building products and to share them. But I found TikTok actually really easy to do that. So I'm going to try to experiment there a little bit more.

**Nickey Skarstad** (01:00:01):
So you can follow me, I'm @NickeySkarstad on TikTok. And then I have a newsletter. I call it Builders. It's nickey.substack.com. Nickey is spelled like Mickey Mouse, but with an N. N-I-C-K-E-Y, .substack.com. And I publish their occasionally. I need to get it going again. But again, trying to write down more of the stories of actually being a builder who's been doing this for a long time. Because a lot of us don't have a lot of time to actually talk about it, but it's really interesting work and I want to share it more.

**Lenny** (01:00:29):
Awesome. I'm a follower and a subscriber to both. So highly recommend that.

**Nickey Skarstad** (01:00:29):
I love it.

**Lenny** (01:00:33):
And thank you so much, Nickey.

**Nickey Skarstad** (01:00:34):
Yeah. Thank you, Lenny.

**Lenny** (01:00:35):
That was awesome. Thank you for listening. If you enjoy the chat, don't forget to subscribe to the podcast. You could also learn more at lennyspodcast.com. I'll see you in the next episode.

---

## [5/20] How to sell your ideas and rise within your company | Casey Winters, Eventbrite

**Casey Winters** (00:00:00):
The goal of your Kindle strategies, these like non-scalable hacks, they only exist to unlock the fire strategies, to unlock the things that could take you to millions of users.

**Lenny** (00:00:12):
Pinterest, Airbnb, Reddit, Canva, Hipcamp, Thumbtack, Fair, Tinder, Eventbrite. What do these companies have in common? Casey Winters, Casey has worked with and advised more consumer companies on their product and growth strategy than anyone in the world. He's also very generous with his time and often sets time aside to help founders and product leaders. I always learned so much talking to Casey, and I'm excited for you to hear this episode. In our chat we covered Casey's advice on making trade offs as a product leader, justifying non-sexy product investments, the spectrum of product people and how to level up your skills, new growth trends and tactics that he's seeing, when to focus on growth, and a bunch of advice on growth strategy, and so many other things. As a bonus, we're going to be doing a live AMA with Casey in my newsletter Slack community on August 5th at 10:00 AM Pacific time, so if you'd like to ask Casey any questions, make sure to get there. Until then enjoy this episode with Casey Winters. Hey Casey Winters, what do you love about Coda?

**Casey Winters** (00:01:19):
Coda's a company that's actually near and dear to my heart because I got to work on their launch when I was at Greylock. But in terms of what I love about it, I love loops and Coda has some of the coolest and most useful content loops I've seen. How the loop works is someone can create a Coda and share it publicly for the world. This can be how you create LKRs, run annual planning, build your roadmap, whatever. Every one of those codas can then be easily copied and adapted to your organization without knowing who originally even wrote it, so they're embedding the sharing of best practices of scaling companies into their core product and growth loops, which is something I'm personally passionate about.

**Lenny** (00:01:56):
I actually use Coda myself every day, it's kind of the center of my writing and podcasting operation. I use it for first drafts, to organize my content calendar, to plan each podcast episode, and so many more things. Coda's giving listeners of this podcast $1,000 in free credit off their first statement, just go to coda.io/lenny. That's coda.io/lenny.

**Lenny** (00:02:22):
This episode is brought to you by Mixpanel, offering powerful self-serve product analytics. Something we talk a lot about on the show is how startups can build successful and amazing products. And relying on gut feeling is a really expensive way to find out if you're heading in the right direction, especially when you're raising money, because VCs don't want to pay the price for these kinds of mistakes. That's why Mixpanel will give you $50,000 in credits when you join their startup program. With Mixpanel, startups find product market fit faster, helping you take your company from minimal viable product to the next unicorn. Access realtime insights with the help of their pre-built templates, and know that at every stage Mixpanel is helping you build with confidence and curiosity for free. Apply for the startup program today to claim your $50,000 in credits at mixpanel.com/startups with an S, and even if you're not a startup Mixpanel has pricing plans for teams of every size. Grow your business like you've always imagined with Mixpanel.

**Lenny** (00:03:26):
Casey, welcome to the pod. I feel like every time that we chat, I leave with at least one new perspective that kind of blew my mind on product, or growth, or even just the world. And so I'm really excited to have this conversation mostly to selfishly extract as much knowledge out of your head as I can in the hour that we have together. And so with that welcome.

**Casey Winters** (00:03:50):
Very kind, happy to be here.

**Lenny** (00:03:52):
You've worked at so many iconic companies and worked with so many iconic companies. It almost boggles the mind just looking at your LinkedIn, trying to scroll through LinkedIn and you have to click on, see additional experiences. And there's just so many places you've worked, so many companies you've worked with. Could you just give listeners maybe a 10,000 foot view of your career arc through product and growth?

**Casey Winters** (00:04:15):
Well, I started my career as an analyst at apartments.com on the marketing side, so it was my job to measure every channel for effectiveness in driving leads. These are things like SEO, AdWords, affiliate marketing email, so once I got good at measuring that I naturally started working on optimizing those channels directly. And then I started going to do user research and understand how the product could be better so that we could convert leads better. And it was at that point that I got the feedback from the company that I was this weird marketing and product hybrid, and they didn't really know what to do with that, because those were two totally separate departments. It wasn't until I got to GrubHub and I was the 15th employee and they were like, dude, we don't care.

**Casey Winters** (00:05:01):
As long as you grow how many people order food, I don't care if you work on marketing, I don't care if you change the product, do whatever we'll have results. And we now call these roles growth, but that term didn't exist at the time, so I basically worked on growing the demand side of that business from Series A to IPO. We ended up creating a product management function out of my team there, but for the first four years we didn't have product titles either. That was kind of a newer idea, also. It wasn't until I went to Pinterest that I was actually formally labeled a product person.

**Casey Winters** (00:05:37):
I ended up leading the growth product team there. We basically had to rebuild the growth model of the business to reignite growth, so I was there from 40 million MAU to 150 million MAU. And it was around that time that I started doing some more advising with Airbnb on the demand side, with Pocket. And then I went to a VC named Greylock Partners and worked with their companies on growth and scaling. And then I just independently started working as a full-time advisor with companies like Eventbrite, Tinder, Thumbtack, Canva. And after doing that for a couple years, Eventbrite opened this chief product officer role and they asked me to take it, so now I've been doing that for three years now.

**Lenny** (00:06:18):
That's an excellent segue to our next little segment that I want to get into, which is partly your CPO role and the work that you do there. And also touching a bit on a bit of the writing that you've done. You're currently a chief product officer at Eventbrite, which is a company that I love, I have so many friends there and they're all amazing, such a big fan of the company. And I know a lot of listeners are maybe thinking about becoming CPO someday as a goal.

**Casey Winters** (00:06:18):
Yep.

**Lenny** (00:06:43):
And so I thought it'd be cool to chat through some of the challenges that you're having and some of the things you've learned in the role.

**Casey Winters** (00:06:49):
Sure.

**Lenny** (00:06:50):
Cool.

**Casey Winters** (00:06:50):
Yeah.

**Lenny** (00:06:51):
I'll be more specific, so one of the things that you mentioned that you're working on is thinking about trade offs and being very explicit about trade offs you're making, communicating why you made certain trade offs and then just generally communicating that upward to executives and then across the company, so I'm curious just to hear what you've learned around how to communicate trade offs and internal communication?

**Casey Winters** (00:07:11):
Yeah, one of the things I found, especially during the pandemic at Eventbrite, where we weren't obviously hiring a lot of people and we had lots of various issues come up, is that a lot of managers and leaders would just try to deal with issues on their own and not raise them or escalate them with me in particular. And some of these were really tough situations, so then later on, I'd ask why something went wrong or why we didn't achieve a goal. And I get some feedback from my team of like, Hey, you don't understand the situation. This is really impossible. There's all these things going wrong. And then I respond. Yeah, of course I don't understand this situation because you haven't told me about it. How am I supposed to evaluate things fairly if you don't let me know what's really going on, so these people on my team thought that being a leader was handling it the best they could given the circumstances when in many cases the right way is to escalate the issue so that perhaps I could help them change the circumstances, so the circumstances aren't as dire.

**Casey Winters** (00:08:14):
And if I can't change the circumstances, I'm at least aware of the circumstances and the explicit trade off we've made to deal with that situation. And then I can help communicate that better to others across the company, and I can help evaluate the results with the proper context and do it more fairly. I find that in general people just way under communicate upward inside of companies. And then they'll complain that executives are out of touch when they aren't telling executives what the executives need to know. Then when people inside a company do try to communicate upward a lot of times they're so in the weeds that as an executive, I just don't understand what they're saying. And then when I ask questions it's like as an exec, I'm asking a question in another language. It's like I don't know if you've ever seen Ocean's Twelve, but as a joke, they invite Matt Damon to this business meeting and they just talk in code as a prank on him.

**Casey Winters** (00:09:14):
And that's what a lot of people on my team feel sometimes when they're talking to the executives of like, I don't even understand what these questions mean. It's like you're speaking another language. One of the ways I try to frame it to my team is if you're not an executive, whatever you're working on, you're basically writing and telling a story. And when you talk to an exec about that story, you have to start with chapter one, which is what part of the company strategy are you working on? What metrics are you trying to improve? What assumptions are you making that are guiding what you're building? And I find that many times when non-executives are presenting to execs, they'll start on like chapter six, so even if that part of the story is right, it's like a good story. You haven't earned the right to tell that part of the story yet because you skipped the first five chapters. And I've definitely seen people with the opposite problem as well, which I call starting at the beginning of the time where you come into a meeting with the CEO or with the CFO or something.

**Casey Winters** (00:10:20):
And you basically spend the first 20 minutes, re-explaining the company strategy or who our customer is or something that everyone already knows. And then by the time you get to explaining new information, you've used up your allotted time, so I try to coach my team to be in the middle. Like don't start on chapter six of the story, but also don't start with a textbook on the English language either. You want to find the last point in your story, that would be completely obvious to the person you're telling the story to, and then go from there to things that would be less obvious, but that they can follow along with. And it's a lot of work to really dial that in across different types of people you're trying to communicate that story to because of course, upward communication isn't all that you're doing, right? You're trying to communicate that down to your team, to individual engineers and designers, and they're going to need to hear some very different things then say the CPO of the company, or the CEO of the company, so it's a challenge I see quite frequently.

**Lenny** (00:11:19):
Can you talk a bit about how you actually coach PMs on this? Is this like in one-on-ones you revisit a presentation they gave that could have been better? Is it after a presentation, you pull them aside and talk through what they could have done better. How do you approach that?

**Casey Winters** (00:11:33):
Well, I think the best way to coach is actually to do it before the meeting, so I think there's a tendency in product management and product design to want to do meetings where there's kind of this big reveal and an aha to the audience. And it's kind of the opposite of how you want to handle most of these situations. You want to de-risk that meeting not make it a big success or fail moment, so there's a few things that I do. One is if there is a big presentation coming up or something like that, I try to run through it with the team, pretending to be the other members of the audience that are going to be there, so I'll say, okay, well, what the CFO's going to ask about here is X. And you want to answer that question before it gets asked. What Julia, our CEO is going to ask about is why, so you want to weave that into the early story and not wait for her to ask.

**Casey Winters** (00:12:28):
You kind of role play the entire thing based on the different people that they're going to be communicating with. Something I commonly say is that executive communication is actually executives communication. You're communicating with individual executives that all have different styles and different concerns about the business or about the particular problem you're working on. And you want to anticipate that, and if you don't have enough experience say presenting to the CFO or the CEO, I as the chief product officer do, so I can impersonate them and help you understand what they're going to care most about. The other thing that I push a lot of my team to do is have pre-meetings with some of those key individuals, so that they're going to be less surprised in the meeting about what you're talking about, that you've gotten any major concerns brought to your attention before the big meeting.

**Casey Winters** (00:13:18):
And that helps de-risk how poorly a meeting like that can go, so definitely at the individual presentation level, doing that pre-meeting. What I'm working on a lot now is trying to have more of a scaled approach to training this type of upward communication. And what types of frameworks, what types of structure tend to work for Eventbrite and making sure that everyone on my team is just really well versed in that and comfortable in it because of course, confidence projection is a key part of these types of meetings as well.

**Lenny** (00:13:54):
This is such important advice that I think a lot of PMs don't recognize how important it is to prepare for important meetings like this. Just to give folks context, maybe that aren't doing this sort of thing when they're working at a larger company, how much time do you spend or an ICPM should spend on preparing for these things just to set a little bit of a reference point?

**Casey Winters** (00:14:13):
Well, it's an interesting question because I think different people have different styles on how they want to handle this. I'd say the way my brain works in these situations which I think is a little bit atypical, is I'm actually a little bit better if I am free forming a lot of elements and just speaking from confidence in areas I know versus specifically trying to lay out every exact bullet point I want to hit. I'm going to show up as more comfortable, I'm going to show up as more dynamic, and I'm going to be able to engage in a more thoughtful conversation, so for me, my approach to these sorts of things is I write a lot. I write a lot of notes. I write a lot of documents. And then in general, for any of these types of communications, I am just pulling from things I know deeply because I've written them down, I've thought a lot about them.

**Casey Winters** (00:15:10):
For a lot of other people they really just need to spend a lot of time on prep to make sure they nail the communication they want to nail. And I found it requires a different amount of investment for different people on my team, so the point is not as much how much time you spend, it's how well do you really know the material, and how well do you really know what your audience is going to care about with that material so that you are prepared for every question you might get. I'll give an example from my Pinterest days, the primary way with which you interfaced on any key strategic topic was product review, right? You'd go in and you talk to Ben, our CEO and Jack our head of product. And Ben and Jack had very different styles of communication. Jack in particular would very early on ask a few different data questions to get context on the problem. And if you, as a product leader or an individual PM or an individual designer didn't know the answers to any of those, it cast doubt on the entire rest of that meeting.

**Casey Winters** (00:16:17):
Because, the team wouldn't be confident that you had all the right context to understand the problem, so a lot of what I would coach my team on is, okay, I'm pretty confident Jack's going to ask this question, then this question, then this question. Based on the material I'm seeing from you, how well are you prepared to answer those questions? Different execs might be somewhat different in that regard, but if you haven't thought through all the questions that might be asked from the document that you're sharing or the presentation you're about to present, you're not prepared enough, right. You need to know the entire universe of how that meeting can go. And that may take you dozens of hours, it might take you three hours, but the most important thing is that you've asked what possible questions can be asked and am I prepared to answer all of those? Do I have all the data in front of me to answer all of those? But because if I don't the chances of the meeting you're having a negative outcome just increased dramatically.

**Lenny** (00:17:17):
I imagine some people are listening to this and they're like, holy shit, I need to spend this much time on preparing for meetings like this, but in my experience, that's exactly what you do need to do to be successful. And so this is real good, real talk about how long it takes to prepare for important meetings like the ones you're talking about.

**Casey Winters** (00:17:33):
Absolutely. I mean, for better or worse, the way that a lot of key decisions are made inside companies are through these types of forums and meetings. And it's an extremely high leverage piece of time for a product manager or a product designer in terms of how much impact they can have. And if you are under preparing for those sorts of things, the chances of you being able to have the type of impact you want, to have the type of career growth you want just go down dramatically. And I'm sure, you and I have definitely made mistakes in our career in important meetings in the past, but I think one of the things that I really try to do is learn from each one of those and make sure those types of issues wouldn't happen again. And now I feel like I have a pulse on, I know if I haven't done the work going into a meeting, that's going to make it have a more negative result.

**Casey Winters** (00:18:26):
And now I'm pretty accurate. And look sometimes you just didn't have enough time and it is what it is. But now I know, okay, I know I'm not quite prepared for this and it can go poorly as a result. And I know also when I've done the right prep and I'm ready for anything, whether it's a board meeting, or a meeting with the executive team, or a meeting with an external partner, right? And I think that's what you're trying to build as any sort of product leader, or PM, or product designer, or researcher, is that intuition of like I'm ready for this, I know everything that's going to come at me, I'm prepared for any eventual outcome. And if you're not, then probably the answer is spend more time to get ready.

**Lenny** (00:19:09):
Speaking of spending more time, another topic that you shared with me that you're thinking a lot about as a CPO is keeping the Eventbrite product simple while adding more and more functionality to make it more usable by more people and more use cases. And so I'd love to hear how you're approaching that because I know that's something every single product faces eventually assuming they keep growing, and survive, and keep adding more power.

**Casey Winters** (00:19:34):
Yeah, Scott Belsky who's the chief product officer of Adobe. He has this concept of the product life cycle you're probably familiar with, but I'll explain it to your listeners, which is users flock to a simple product. The product takes users for granted and adds more features for power users and then users flock to the next simple product as a result. And I've done a lot of research and work on this problem. And I found that there are a few different design hacks, essentially that companies use to try to avoid this cycle. One is okay if you build out more complex functionality, un-bundle it over time, like Facebook Messenger, Uber Eats have done, right? At Pinterest, we did a heavy investment in progressive disclosure, which is let's hide a lot of the more complex functionality until we make sure our users learn the really critical functionality. And then we can open up more of the full suite of the product.

**Casey Winters** (00:20:34):
Then there's just proactive training. You can get on a video call with your customers or a phone call, much more common in enterprise, obviously, or you might have a custom UI that goes away over time. That's giving you the training wheels. You can also segment experiences based on different user types, so certain users might get a very simple user experience and then some users might get the more complex one, and there's different packages and interfaces that cleanly separate the two, maybe that more complex experience also bundles in training. What I found is that just none of these really worked that well for the Eventbrite scenario, because we have different types of event creators across every possible level of complexity and sophistication. We have people that are putting on their first event and they expect five people to show up. We have people putting on a hundred events per year that really know what they're doing.

**Casey Winters** (00:21:32):
And then users also shift from one of those categories to another over time. They can get more sophisticated as they build up their business, so segmentation doesn't really work that well. Progressive disclosure doesn't work that well either because in many of these cases, we never want certain types of users to find the more advanced stuff, it's just going to confuse them. We strive for this concept of what we call perceived simplicity, which is there are advanced features in the product and they are easily discoverable when you look for them, but they're effectively hidden if you're not looking for them. And of course the majority of users aren't going to ever look for them, so the advanced more complex areas of the product don't make the product harder to use for the majority who will never need that level of complexity. And there are areas where we do this well and areas where we're still working on getting better, but that's really our aspiration.

**Casey Winters** (00:22:26):
The company that I feel like has always done the best job of this is WhatsApp, where at its core, it's a chat app and it's really good at being a chat app. But I remember when I went to Brazil, all of a sudden I started receiving voice messages and it was really easy to figure out how to use them and how to do them myself. When I needed to learn how to do video calls or phone calls, it would take less than a second to figure out how to use the more advanced stuff, but it's effectively kind of hidden if you're not looking for it. That's what we aspire to at Eventbrite. And in some cases we're doing well. And in some cases, we definitely have some work to do.

**Lenny** (00:22:59):
Is there an example of a win in that direction in the Eventbrite product that you're proud of using this model or even something that's like, oh man, this is really broken?

**Casey Winters** (00:23:08):
Yeah, we've definitely had some wins here on the marketing side of our products, so one of the bigger investments we've made recently is our creators do a lot of their own marketing to try to get people to come to their events and transact on Eventbrite in the process. But our event creators, they're not professional marketers, they try to figure these tools out, so we built a product that allows them to automate their Facebook advertising to get better results, supercharged by our data. And the product's working really well, but we found is that there are certain segments that, I want to geek out on this a little bit, right.

**Casey Winters** (00:23:47):
They want to figure out all the different target segments and optimize their creative, and then there are many creators who just want it done for them. We've been able to build some interfaces where the default is super simple, we'll handle the targeting for you, we'll handle the creative and then, Hey, here's an on-ramp if you want to get a little bit more sophisticated and do more of this yourself, so that's an area where I wouldn't say we've perfected it, but we've now really understood those different types of users and a have easy pass for both of them to be successful, so I'm really happy with that.

**Lenny** (00:24:22):
Awesome. Another topic that you wrote about that kind of touches on the stuff we were just talking about is justify non-sexy product improvements, things like stability, performance, developer velocity, things that as a PM leader, you're just like, no, no, no, let's just... The default is let's do that later, we got to hit our fricking metrics, we've got to drive growth. And you had some really interesting insights on how you think about justifying these sorts of things. And so I'd love to hear that from you?

**Casey Winters** (00:24:49):
The idea is that some of the most impactful projects that product teams can work on at scale, not early stage startups per se, but at scale are the hardest to measure. And because of that, they just get chronically underfunded. It's that old adage, what gets measured gets managed, right? For things like user experience, or performance, or developer velocity, or just a product area that's deemed un-sexy, like growth used to be back in the day, I walk through some examples of a few tactics that work to get around this problem, building custom metrics to show the value, being able to run small tests that prove the worthwhile-ness of the investment, creating some team principles that make sure you don't ever kind of forget about these important elements that can hurt you in the long run. And also just how to use experiments to build buy-in at the broader level.

**Casey Winters** (00:25:41):
And one of the main takeaways besides some of those tactics in being successful here is that you have to get a team to buy-in to this. You can't really do a lot of this work alone, right? If you're a PM, you want to be approaching this from a well, my engineering manager and my design leader also bought in that we need to work on performance or we've all aligned that the user experience is not going in quite the direction we want, and we want to head some problems off that may not improve metrics today, but could certainly decline metrics tomorrow. And if you can get a small team, what two, three people aligned on the importance of something that's deemed un-sexy. It's a lot easier to start to build this game plan around metrics or running small tests or structuring OKRs to not only prioritize this work, but to show some really massive impact. Which could then get the rest of the company much more excited to make investments themselves.

**Lenny** (00:26:48):
What I'm hearing is step one is just get your kind of peer leaders aligned behind something that may not obviously be something your leaders want you to do, is that right?

**Casey Winters** (00:26:59):
Absolutely, yep.

**Lenny** (00:27:01):
This episode is brought to you by Whimsical. When I asked product managers and designers on Twitter, what software do they use most? Whimsical is always one of the most mentioned products, and the users are fanatical. Whimsical is built for collaborative thinking, combining visual, text, and data canvases into one fluid medium. Distributed teams use Whimsical for workshops, white boarding, wire frames, user flows, and even feature specs. And that includes thousands of built in icons and a rich library of templates. See why product teams at leading companies call Whimsical a game changer, visit whimsical.com/lenny to have my own templates added to your account when you sign up, that's whimsical.com/lenny.

**Lenny** (00:27:47):
Is there anything else that you think is really valuable, powerful, effective in just getting folks to getting your leaders to basically go along with some that maybe isn't going to move metrics or is that the core of it?

**Casey Winters** (00:27:57):
Well, yeah. I mean, definitely it's hard when you can't create a metric that they can understand. I think the other area to think about is when you're an early stage company, everything you're doing is trying to drive upside, like trying to drive growth in some way, it could be short term or long term, but you're trying to drive real growth for the business. But then when you've actually built a real business, a lot of times people are still in that same mode, which is everything is trying to add more growth on top of what we've already got. But when you're at scale, you can actually lose what you've built, so trying to help whether it's executives or just your manager, understand that this thing we've got, whether it's a high conversion rate or good engagement on this feature, it could go away if we don't do these other things.

**Casey Winters** (00:28:48):
And here's what it would look like if that goes away, that can be incredibly powerful. I think we were fortunate at Pinterest in this regard, in that we were a fast growing startup that stopped growing due to some changes in the market related to Facebook. And then actually once we had switched to growing primarily through SEO, there was an algorithm change that severely impacted our growth at one point in time, so that helped the company build more intuition of like we're not guaranteed the gains from all the things we've built in the past. We need to do things to protect them and protecting what we've got actually is increasingly important once you build scale, because now you've built something really valuable already. And yes, we want to make it more valuable of course, but it's hard to make it more valuable if you're eroding some of the gains you've already built, so that's another element that I think can be pretty impactful.

**Lenny** (00:29:41):
In your post on this topic you have an awesome chart of product market fit over time, illustrating the point you just made that it doesn't last and you have to keep iterating to keep your product market fit like you're by default falling behind if you're not continuing to push there, right?

**Casey Winters** (00:29:54):
Yeah. I think the concept is user expectations just continue to go up every day in terms of their expectations on user experience, on the value that they expect your product to provide, but also the competitive landscape in the market continues to get better. Yeah, if you're not continually pushing to make your product better, your user experience better, your latency better, then you're eventually not necessarily tomorrow, but maybe in a year, maybe in five years, you might find yourself fall out of product market fit entirely. And that's a really dangerous place to be, because then it's going to take a long time to figure that out and make adjustments. And then you probably have more technical debt to clean up, to be able to get back to where you need to be, where the market has reached in terms of expectations, so just doing work to make sure you never get in that situation is extremely valuable, in my opinion. It's something that I think a lot of teams forget about.

**Lenny** (00:30:54):
I think you're going to create nightmares for a lot of founders listening to this right now.

**Casey Winters** (00:30:59):
That's not the intention, but-

**Lenny** (00:31:02):
No, it's a kick in the butt. Another post that I definitely wanted to chat about. Maybe your SPST post, maybe I'm curious if there are others is around operations team, product ops and generally ops people.

**Casey Winters** (00:31:12):
Yep.

**Lenny** (00:31:13):
And this point that you made that ops is often a sign of inefficiency on a product team because in theory, a lot of the roles should be done by software, eventually. I'd love to unpack this and hear your take on this?

**Casey Winters** (00:31:26):
I think I originally got the idea for the post in that I had written another essay on MarTech. And how MarTech to be really successful, it's really got a target engineers more so than marketers. And that a lot of MarTech businesses just aren't very good businesses. And I think I got an invite to speak at a MarTech conference to a bunch of marketers about this post. And it's like, well, that sounds like a terrible idea. I'm basically telling a bunch of marketers that what they're investing in isn't that important, and that they're not the most important target customer. And I remember reading something about the conference that was like a conference for the growth of the marketing operations professional. And then I was like, oh no, that's not what I want in the industry at all. Like having marketing ops means you suck at marketing.

**Casey Winters** (00:32:18):
And obviously that's a bit of hyperbole. I'm not against the concept of a marketing ops role or a product ops role, we have a product ops team at Eventbrite, but as someone who ran a double digit million marketing budget at GrubHub without marketing ops, because we invested in automation and we invested in process, it scares me when the first tactic people go to is to add people to help scale. There's nothing wrong with people obviously, there's nothing wrong with operations people. The thing I have a problem with is normalizing ops as a distinct stable function where operations rules are amazing and how we utilize them at Eventbrite is their explicit job is to go find inefficiencies and build process or software to root out that inefficiency, so then they can go find other places to be more valuable. When you say, oh, their job is to do this manual process long term.

**Casey Winters** (00:33:16):
That's where I get super concerned because you're not rooting out efficiency in how you build your company. And that's where I feel like a lot of this can go if you're not careful, Intercom has a really good blog post on this from a while back around their business operations team. And they basically up front in that post say the goal of business operations is to not exist, and I definitely very much agree with that. I think in general functional ops roles, whether it's product ops or marketing ops or whatever, they're a hack to deal with some sort of functional issue on your team. And it's totally okay to have functional issues. Startups are going to have functional issues all over the place, but if the way they deal with that functional issue is by building larger and larger operations teams and roles. That's basically exacerbating an inefficiency issue, a functional issue, it's not fixing it. It's a form of empire building and in general empire building is something I don't have a lot of tolerance for.

**Casey Winters** (00:34:16):
You're making more of a function unable to operate without human intervention by saying the goal is to scale up marketing ops or product ops. Whereas what the goal should be is let's use our brains to run experiments, to make us more functional with less people. We're more efficient, we could add more value to the customer, and to the business. And if that means I don't actually need to have this product operations job in a year. That's awesome. And guess what, if you've shown you've done a really great job at rooting out inefficiencies. Every part of the company's going to want you to do some other job if that job is no longer valuable, because you've done such good job eliminating the need for it. There isn't this real concern that I'm going to lose my job by being too effective at it. It's like, no, you're going to show that you're just awesome at many types of jobs that product leaders or marketing leaders care about, so that's my perspective.

**Lenny** (00:35:09):
I love that. And this happened a lot at Airbnb, a lot of amazing office people ended up moving into other roles once the role was not necessary or they just wanted to do something else. And clearly people wanted them on their team because they were killing it.

**Casey Winters** (00:35:20):
Indeed.

**Lenny** (00:35:21):
One last question about the CPO role, and then I want to shift a bit to just product management and growth. What is the job of a CPO for folks that are just like, what the heck, what is this thing? What do you do all day?

**Casey Winters** (00:35:32):
Yeah.

**Lenny** (00:35:32):
And then what does it take to get there? Just like what should people work on most if they're trying to get to CPO someday?

**Casey Winters** (00:35:39):
First off, when you think about what's the job, the way I think about it is I'm responsible for leading and facilitating the development of products and features that deliver value for Eventbrite's customers that will translate into value for the business. And each of those words were chosen pretty carefully. Now in terms of the scope of the function, a CPO role can lead a few different sub-functions. In my case, I lead product management, product design, research, and growth marketing, but different roles have kind of some or not as many of those, it can be pretty custom depending on the size of the company and what the leader's skill sets are. To talk a little bit more depth about the role. I think it's my job to make sure Eventbrite chooses the best possible product strategy based on the information we have, that we can adjust that strategy as we learn and continue to build that feedback loop.

**Casey Winters** (00:36:35):
It's also my job to define and consistently improve the process through which we set our product strategy, how we prioritize projects, how we execute on them to make sure we're delivering that value to our customers, we're delivering those tangible business results. And to do that in a way where the rest of the company understands it and is able to participate in it as well, so this is things like identifying bottlenecks that prevent us from delivering value, or quality, or doing that at the detriment of speed, working with people across the company to remove those bottlenecks, making sure people outside of development are aware of what we're building, participating in the development and feedback of what we're building, as well as in helping deliver that for like a GTM perspective. And last but not least, and we've talked a little bit about this earlier, training the team on what it means to be an effective product manager, product designer, user research, et cetera, at Eventbrite.

**Casey Winters** (00:37:36):
And then of course hiring people who can augment our existing team on everything I just mentioned, so I'm accountable for what we build driving value for the business. And there's of course going to be many times where what we build doesn't end up driving value. It's hard to predict sometimes, but it's my job to improve that conversion rate and the magnitude of impact over time. It might not be that everything we build delivers value, but I want most of it to, and I want the impact of that value to be higher and higher over time. You also asked about what it takes to get to the CPO role. And I think my journey's been more irregular than most of the people you probably talk to. Product management when I started my career, it was all a waterfall. It was built around massive releases, it was a totally different job from what we do now. Marketing was a lot more agile in the lowercase sense of agile and it mapped to my mind better as someone who's really influenced by the book, The Goal.

**Casey Winters** (00:38:40):
I think the tangible pieces of advice to get to this level that may be helpful is I always focused on where I thought there was leverage. I wanted to learn everything I could and focus on the things that had a big impact regardless of the org structure or the career path that meant, I wanted to really have a deep understanding of the entire business so I knew just what was worth focusing on to help the business. I think one of the things that's different about being a chief product officer versus other product roles is how much of a company leadership role it is versus a functional leadership role. You're expected in this role to optimize for the entire company, even at the expense of what's good for your team, so you really have to learn how to optimize for company first. That's like a key thing to learn that I think new executives can struggle with. And what advantage I think I had is I've basically been working with executives since my first job at apartments.com, so I learned to speak their language and understood what they cared about pretty early in my career.

**Casey Winters** (00:39:47):
And this is a really important element, assume that questions from them are them trying to learn versus them assuming you don't know something and testing you about it. I find that a lot of people get intimidated by executive questions when the executive is just trying to understand things. And then that changes the interaction you can have. The other element that served me well was just refusing to specialize. I thought if I could learn all the skills that would allow me to combine them to work on the most important things versus only work on the thing I knew how to work on. And that definitely led to slower visible progress in terms of career growth or titles, but it was a much faster path to the true executive role because I could speak better with CEOs about more topics than most of my peers. Obviously this is all my individual experience there are many paths to get to this type of level, but those are some things that have worked for me.

**Lenny** (00:40:45):
That was such an incredible definition and so much good advice there. And this is a good segue to another area that you have a really interesting insight on around the spectrum of product people. When I think of you, I think of two by twos and this is I think just a spectrum, which is unusual for Casey framework.

**Casey Winters** (00:41:01):
Yeah.

**Lenny** (00:41:01):
I'd love to hear your take on how you think about the spectrum and around up-scaling PMs to move along that spectrum?

**Casey Winters** (00:41:06):
The idea is, and this is something I was inspired from talking with Omar who runs product at Cambly. He used to run core product at Pinterest. It's this idea of any product team is like a gang of misfits, they all come from different backgrounds. Most people didn't start as a product manager, their first job, they might have been in sales, or in marketing, or analytics, or engineering, right. Everyone's bringing these different skill sets to the table. But the main spectrum that I've observed in product teams of any decent size is that you have two extreme types of product managers per se, and on perhaps the left side of the spectrum you have the crazy innovator types, they have so many different ideas, they pay attention to every single change in the industry, they all know all about the latest Apple API or Snapchat's latest product feature.

**Casey Winters** (00:42:06):
Those people are going to have ideas all the time. Actually, probably most of those ideas are going to be bad, but one out of ten's going to be just a game changer and they're generally not super great at turning that idea into action. And then on the extreme right side of the spectrum will be your typical executional focused PM, and they can do a really good job of taking a strong strategy and turning it into action that creates value for the customer, but they generally don't know what's going on in the industry. They can't think of a totally new product idea themselves. They're going to need support from above to be able to push them in the right direction and then they got it from there. When you think about recruiting, what we all want as CPOs in terms of people we bring into our team is we want people in the middle. We want people who are strategic, they understand what's going on in the industry, they can generate some good ideas, but they can also turn it into something real that delivers value for the customer and the company.

**Casey Winters** (00:43:08):
And there just aren't a ton of those people in the world. Not as many as we would like to recruit, so as a product leader, if I'm airing on the side of which side of the spectrum I want people from, I generally will take people who are good at execution over people who are good at generating ideas, because of course there's always too many good ideas that a company need to focus and execute well on the best ones. Whereas if I were a VC, I would probably bias to the people on the left because I don't need every company to work. If I invest in 10 different entrepreneurs who have crazy ideas and one of them works and becomes the next Airbnb, turns out I've done incredibly well as a venture capitalist. The challenge you practically deal with as a product leader is you end up recruiting, and managing, and growing a lot of executional people who can get stuff done, but if they want to get to the director level or if they want to get to my level, they need to get more strategic.

**Casey Winters** (00:44:06):
And we don't have good ways to turn great executors into great strategists as in general, like a product function, so I've started investing in a lot of different things here. Obviously I've built some programs for Reforge around product strategy. A lot of my team goes to those to try to learn. I've also been doing a lot of mentorship with the team to try to teach them what it looks like to do that well. I've had people come in to speak with the team like you and many other great product folks to show my team what great looks like and how people like you developed your skills. And I'm trying lots of different things to try to move more of the team to the middle, where they can be that optimal strategist that still retains that ability to deliver great value on top of the strategy versus just have ideas that can't be executed on. And it's definitely a work in progress, it's a lot of different tactics to try to build that skill set inside the team and scale it. And definitely something I feel like I'm still working on.

**Lenny** (00:45:11):
What I'm hearing is a lot of kind of the biggest upside for PMs to develop is basically to become more strategic and all the things you've shared are just ways or a lot of ways to just become better at strategies. It's interesting that that's like what you found to be the most essential piece for PMs to often level up at.

**Casey Winters** (00:45:30):
Like you said, it depends on the level, right. Early on in your career as a PM, you're going to get the most value by showing that you can ship real things to customers and that the customers like them, like that's by far the most important thing. But if you want to start managing groups of PMs, if you want to start a running a business unit, or a pillar, or a theme. I as a chief product officer, I'm going to expect you to be able to write that strategy doc without me. And you know what I found, whether it's through the advising roles or through coming into Eventbrite is just a lot of people couldn't do that step.

**Casey Winters** (00:46:04):
And that means when you try to become a product leader at the company and the CEO expects that from you and you can't do it, you're going to set yourself up to really cap hard on how fast your career can grow. And you'll get stuck, whether it's at the senior product manager level or at the group PM level, because you can't show that you can drive decision making on your own and that you can push forward new ideas that are going to help the company, so that's definitely where I've seen the biggest bottleneck in terms of skill sets. Obviously there's lots of important skill sets you want to build as a PM, but that one to get to the top is the great filter.

**Lenny** (00:46:40):
That's awesome advice for folks listening that are trying to figure out what should I work on? It's kind of simple a lot of times just get better at strategy and it feels like it elevates you in so many other ways.

**Casey Winters** (00:46:49):
Yeah, and of course we could talk for hours about what it means to get better at strategy and some of the tactics there.

**Lenny** (00:46:54):
It could be a follow up.

**Casey Winters** (00:46:56):
Because I know some PMs who struggle with that.

**Lenny** (00:46:56):
Follow up.

**Casey Winters** (00:46:57):
Yeah.

**Lenny** (00:46:58):
Okay.

**Casey Winters** (00:46:59):
Podcast number two.

**Lenny** (00:46:59):
Podcast number two, let's book it. Okay, so I can't let you go without talking about growth. Everyone's always trying to figure out how do we grow our company?

**Casey Winters** (00:46:59):
Right.

**Lenny** (00:47:07):
What can we do to accelerate growth? I know you're modest, but I think you're one of the smartest people in the world on this stuff. And so I just want to touch on a couple things in the time that we have here. One is with paid growth becoming increasingly more expensive and difficult, especially with Apple's recent changes.

**Casey Winters** (00:47:24):
Yep.

**Lenny** (00:47:24):
SEO forever becoming more crowded, sales being always expensive. It's just tough out there for a lot of startups to grow. Are you seeing any interesting or new growth channels or tactics that folks can explore or consider that maybe work for companies that you're looking at?

**Casey Winters** (00:47:43):
It's not that there are new channels per se, unless you include tokens from like Web3, which I do not. It's more that there are ways to get leverage on your channels through better flows or lifetime value that companies are figuring out. For example, at Eventbrite, we unified what we're separate direct response and lead generation flows in our performance marketing to acquire creators. And now it just takes less effort, we're getting better CPAs and sales now has the opportunity to pick up any product qualified lead from a direct response customer who may need a little bit more help, and they have the data to now determine if there's high enough value to justify it.

**Casey Winters** (00:48:27):
This concept is being dubbed, product led sales. And it's this idea that you can unify self-service loops in a B2B business, which are typically driven by product and your sales loops into one more complex giant loop that operates more efficiently and breaks down the silos. And I think you're going to see an explosion in B2B companies that learn how to unlock that and get sales, and product, and marketing to be working as one larger cross-functional team and building an engine that optimizes all of their skill sets, so that's something I'm pretty excited about, but we're definitely in the early days there.

**Lenny** (00:49:02):
That's awesome. I was going to ask you if there's any trends you're seeing around growth and clearly that's one. Are there any other trends, just things happening in the growth world?

**Casey Winters** (00:49:12):
Yeah, sure. I think there was this conventional wisdom to just focus on building until you found product market fit and then you can worry about growth. And of course there's some truth in that statement, but now as I'm talking with more and more founders and I'm sure you're seeing this yourself, is we're seeing founders who are thinking about building growth loops into their product before they find product market fit. And it's not so that they can prematurely scale before they have product market fit. It's so that when they find product market fit, they have that built in distribution advantage to grow once they're ready. And founders are starting to intuit what I've written about a bit as well as you, which is that scalable acquisition or what we call an acquisition loop is a requirement for product market fit.

**Casey Winters** (00:49:59):
Like if you got a product that retains well and you can't find more users for it, I don't think that's product market fit, so it's really exciting to see that evolution and to see founders think about like it's not about getting a bunch of users before you have a product that works. It's about thinking strategically about how this product's going to grow itself when it's ready to do so. I'm really excited to see the next generation of founders build that muscle early on and also leverage it when they're ready instead of just like, oh, I'm going to throw a bunch of paid ads at it and it's going to work, so that's something I'm really excited about.

**Lenny** (00:50:31):
On that topic, when should companies focus on growth? And as a second question, when do you think they should hire a head of growth or someone full-time focused on growth?

**Casey Winters** (00:50:40):
Like I mentioned, well, you don't want to focus on growth before product worked fit. You want to be thinking about how your product can grow scalable pretty early on, so early growth definitely needs to be done by the founders. I tend to separate growth into two phases. I call the first phase kindle strategies, these are those non-scalable hacks to get your early users. And I think those are generally done by founders, maybe some early team members. Fire strategies are the ones that drive scale, that's what you were mentioning, content loops, sales loops, viral loops, paid acquisition. And to me, the goal of your kindle strategies, these like non scalable hacks they only exist to unlock the fire strategies, to unlock the things that could take you to millions of users.

**Casey Winters** (00:51:24):
And it's once you unlock a fire strategy, that's when I think you think about hiring someone full time on growth to fully harness that new growth loop you've built. That could be a salesperson, if it's sales. It could be growth PM, if it's viral or you just see content. Or it could be a performance marketer if it's ads, but it's once it's like, okay, we've sequenced to a growth strategy that actually scales. Let's go find someone who's awesome at that who can make it 10X better. That's how I think about it.

**Lenny** (00:51:51):
Maybe a last question, is there is kind of an underappreciated or under invested in growth strategy, growth tactic, things that you're just like, oh wow, this seems to be working better than people may think.

**Casey Winters** (00:52:03):
Yeah. Well, I still think data network effects are underrated. I think a lot of people confuse the idea of data network effects with data as a product you can charge people for, especially like businesses. And I get it a lot of businesses like you can't charge them for data because they don't know how to use data super well, especially SMBs. But what data network effects are, is leveraging product usage data to make the product value stronger and stronger over time. That could be personalized results in the case of Pinterest or in the case of Eventbrite, better targeting data for advertising to find people who are more likely to be interested in your event. And I think especially with Facebook and Apple's platform changes your product being able to generate its own data, versus just relying on the big platforms to do all the work for you. That's a real edge that companies are starting to wake up to. And it's obviously something that's worked well for me in the past at Pinterest and certainly now at Eventbrite.

**Lenny** (00:53:02):
There's a couple questions that I had at the top that I skipped that I thought I'd come back to. I know that you're a big video game guy and I love that at the bottom of your post, you always share the music that you're listening to, so I was just going to ask what's the game you're playing these days. Anything you recommend and then what are you listening to?

**Casey Winters** (00:53:18):
Yeah, I'm currently playing Cyberpunk 2077 on the PS5, which is fun. But I recently finished Horizon Forbidden West and that was excellent, really great science fiction game. On the music side, one of my favorite bands is this band called Broadcast and they never really played live a whole lot and their singer died a few years ago, but they recently came out with a recording of a bunch of their live sessions that they recorded on the BBC. And it's like getting this time capsule from the past of some of their early live sessions. That's been really great, so I've been enjoining that record quite a lot lately.

**Lenny** (00:54:02):
Awesome. Casey's picks get them here, get them here now. Casey, I feel like I was successful in extracting many nuggets in our hour together, I really appreciate your time. Where can folks find you online and how can people that are listening be helpful to you?

**Casey Winters** (00:54:17):
Blog@caseyaccidental.com, I'm semi-active on Twitter @onecaseman, and always I focus on paying it forward, like help the next generation of companies, of PMs, of marketers, get better at their craft and build better businesses. And if you're searching for a cool event, check out the Eventbrite App of course, we always would appreciate that.

**Lenny** (00:54:43):
Love it. Amazing Casey, what a great way to end it. Thank you again for being here.

**Casey Winters** (00:54:48):
Thanks so much.

**Lenny** (00:54:50):
That was awesome, thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast and even better leave a review, which helps a lot. You can also learn more at lennyspodcast.com. I'll see you in the next episode.

---

## [6/20] How to unlock your product leadership skills | Ken Norton, Ex-Google

**Ken Norton** (00:00:00):
Part of what I think is pretty exciting about product management is you are a leader from day one in product management. There's leadership all over the place, but that's your job. You're a leader. You don't have any formal authority, but you're a leader. You're expected to lead

**Lenny** (00:00:22):
Over his 14-year career at Google. Ken Norton led product teams at built Google Docs, Google Calendar, Google Maps, and even did a stint at Google Ventures. The products that he's helped craft are now used by over three billion people.

**Lenny** (00:00:37):
Today Ken is a full-time executive coach specializing at working with product leaders. In our conversation, we cover the creative versus reactive mindset, why the art of product management is much more important than the science of product management, how to get over imposter syndrome, the most common PM blind spots, how to find a coach and how to know if a coach is right for you, and so much more. I hope that you enjoy this episode with Ken Norton.

**Lenny** (00:01:05):
If you're setting up your analytics stack but you're not using Amplitude, what are you doing? Amplitude is the number one most popular analytics solution in the world, used by both big companies like Shopify, Instacart, and Atlassian, and also most tech startups. Amplitude has everything you need, including a powerful and fully self-service analytics product, an experimentation platform, and even an integrated customer data platform to help you understand your users like never before.

**Lenny** (00:01:33):
Give your teams self-service product data to understand your users, drive conversions, and increase engagement, growth, and revenue. Get your vanity metrics, trust your data, work smarter, and grow your business. Try Amplitude for free. Just visit amplitude.com to get started.

**Ken Norton** (00:02:58):
Thank you and thanks for having me. The feeling's mutual. Obviously a big fan of your work and all the things you've done for the community and this podcast, which has been fantastic. So humbled and excited to be here. Yes, I do think that I'm at least maybe partially responsible for at least a lot of consumption of donuts over these years.

**Lenny** (00:03:18):
Are you tired of people asking you about donuts?

**Ken Norton** (00:03:21):
I'll never get tired of it. Well, back when we met with people in person, people would bring me donuts, and I never got tired of it, nor did any of the people that I worked with who got to eat those donuts get tired of it. So, no, no, I'll never get tired of donuts.

**Lenny** (00:03:37):
Someone on Twitter asked what's a digital equivalent of bringing the donuts now that we're in a remote world. Do you have any advice on that?

**Ken Norton** (00:03:45):
That's a great question. I'm not even sure if the physical equivalent of donuts is donuts. I mean when I came up with that, I think it was really to be a metaphor around being a servant leader, bringing whatever needs to be done, filling the white space, filling the gaps, whatever needed to happen. So it doesn't always have to be donuts.

**Ken Norton** (00:04:07):
I did put that question out to some of the readers in my newsletter a while ago, maybe earlier in the pandemic, and got a lot of really interesting ideas. Maybe that was at a place where people had a little bit more patience for happy hours over Zoom and stuff like that. Maybe that patient set is worn out. The idea that I love the most was actual donuts. There was a PM who got DoorDash codes and found the best local donut place for each of the people on the team and basically sent them a code and said, "Click here and order the donuts to come to your house whenever you want them." So maybe at least partially the digital equivalent of donuts might be actual donuts.

**Lenny** (00:04:40):
Decentralized donuts.

**Ken Norton** (00:04:42):
Decentralized donuts, on the blockchain.

**Lenny** (00:04:46):
Oh boy, let's not go there.

**Ken Norton** (00:04:48):
I don't know what that is.

**Lenny** (00:04:50):
So I was perusing your career path ahead of this chat. You had this pretty wild career. You were an engineer initially, and then you were CTO at a part of NBC. Then you're a founder. Then you spent 14 years at Google working on products that folks may have heard of, like Google Docs and Google Calendar and Google Maps. You've also done a bunch of writing. Then more recently, you've become a full-time executive coach focusing on product people.

**Lenny** (00:05:17):
I have so many questions I'd love to ask you about your career and learnings along the way, and the writing. But I'd actually like to spend most of our time talking about the coaching and things that you've learned through that experience. And so, I have a couple questions just off the bat. What does an executive coach actually do? What kinds of things are you helping people with? What does a session look like? Then, two, just how did you decide you wanted to be a coach full time after leaving Google?

**Ken Norton** (00:05:40):
Yeah, that's a great question. I think coaching does mean a lot of different things. I mean it depends on who you talk to. It is a little bit of who you are, your style, your approach. Some people are calling themselves coaches, doing more mentoring, more advice. Other people are maybe more like me, more peer coaching.

**Ken Norton** (00:06:01):
To me, I see executive coaching as a partnership or creative partnership. It's all about helping my client reach their goals, their potential, whatever that means to them. So an important thing about coaching is the definition of success does belong to the client. I don't have an agenda. I don't have a set of things I'm trying to share, teach, learn. It really is fundamentally up to them, which means every client is completely different. They have different sense of where they want to go. Different barriers that might be standing in their way.

**Ken Norton** (00:06:35):
My coaching practice, I coach the whole person. So there is no restriction on what we might talk on, what we might work on together. It's not limited to product. It's not even limited to work or even leadership. It's wherever they want to go, whatever change, transformation means to them.

**Ken Norton** (00:06:52):
As coaches, we bring a bunch of tools to the conversation. The most important ones, honestly, are probably listening and curiosity, intuition, open-mindedness, really there to help challenge them to see things in different ways, help them tap into their imagination, figure out when there might be underlying beliefs, help them connect dots that need to be connected, help them disconnect things that feel connected. There's a lot of exploration to it.

**Ken Norton** (00:07:20):
It's very jazz-like. My love of jazz has been shared before, but there is an improvisation to it. What coaching is really powerful is you may not necessarily know where you're going when you start and you follow wherever there is meaning and change for that individual, wherever is they want to go.

**Ken Norton** (00:07:38):
The question around what brought me into it was actually interesting. I, honestly working with my own executive coach, started to figure out what it is that mattered to me, what I liked, what my values were, what my purpose was, started to unpack that I love deeply connecting with people and I love helping people change and grow.

**Ken Norton** (00:08:01):
The moments when I had the opportunity to do that as a manager, as a product leader were the most fulfilling parts of my career. And so, I started to unpack that and figure out what would it look like if that was what I did.

**Ken Norton** (00:08:15):
The other part of the journey was, for several years at Google, I worked at GV. It's Google Ventures, Google's venture capital arm. I had the opportunity to work with founders and product leaders in the portfolio. I started to simultaneously recognize the shortcomings of giving advice, because it seemed like, well, I can meet with these folks, I could tell them what I did, I could tell them what Google did, and that'll answer all their questions.

**Ken Norton** (00:08:41):
You start to realize advice is not as powerful as you might think it is. It's a little bit like cotton candy. Doesn't have a lot of nutrition. You get a nice sugar high. You feel great, both sides feel happy, but then a couple weeks later, a couple months later, nothing's really changed.

**Ken Norton** (00:08:57):
That's because it doesn't often confront the real problem. It often isn't relevant. Like what worked for us at Google may not have worked anywhere else. It may not even have worked at Google for all I know. I feel like there were years at Google where all we were doing was making things worse by showing up and we should just all have gone sat on a beach somewhere, and the company would've grown even faster. So who knows?

**Ken Norton** (00:09:20):
I mean so it was these just twin pillars of wanting to figure out where I could do what I like the most, and then also recognizing that where growth comes from is less around advice and telling people what to do and more about helping them figure out their own path, their own way. Then that ultimately you brought me into, hey, I want to do this full time, and that's what I've been doing ever since.

**Lenny** (00:09:46):
When do you find people come to you to get advice and coaching? What kind of clients do you find you end up working with?

**Ken Norton** (00:09:53):
That's a great question. Generally speaking, I work with senior product leaders, however you want to define that. Typically, these are chief product officers, VPs of product at startups, largely director level and above at bigger tech companies, some CEOs, other C-level execs in there. I think really anyone that considers themselves in a product leadership role.

**Ken Norton** (00:10:15):
Often they come to me because there's a career milestone or a crossroads, and it could be that they now find themselves in the position of being a CPO for the first time. Maybe there's a new industry change, or they've gone from a big company to a startup and a have this sense of what got me here isn't going to get me there. That's oftentimes when they reach out for coaching.

**Ken Norton** (00:10:41):
I think my clients are also very introspective and surrounded by great mentors and advisors and have all sorts of people in their life who can help them, but are realizing that a lot of the work is going to be internal work that's going to get them to the next level. And so, this transformation is going to be just as much what I need to do as who I am. That's often when people come to me.

**Lenny** (00:11:08):
You said that the way you coach is about the whole person. I'm curious ... I don't know if there's an answer to this, but when people come to get help and coaching, how much of their blocks, I guess, are rooted in their regular life versus skills, technical skills, and more like the PME, product leadership side, if that makes sense?

**Ken Norton** (00:11:31):
Yeah, I think ... Well, let me maybe try to illustrate this with an example from my life right now. Indulge me, I'm going to go a little bit left field here, but I promise [inaudible 00:11:45].

**Lenny** (00:11:45):
Let's do it.

**Ken Norton** (00:11:46):
So we are teaching our 16-year-old son how to drive. So he just got his driver's permit. Do you remember when you learned how to drive, Lenny?

**Lenny** (00:11:56):
I do. Yup.

**Ken Norton** (00:11:58):
Yeah. Yeah. So it's scary. I don't know if you know how your parents might have felt, but-

**Lenny** (00:12:04):
Nope, [inaudible 00:12:06].

**Ken Norton** (00:12:06):
... [inaudible 00:12:06] on the other side of it. It's a whole new journey. Look, he's a smart kid. He's going to do great. But it helped me actually think back to when I learned how to drive. Actually, what I think is maybe a little bit more important here is before you learn to drive. And so, if you think about it as a ... When you're a kid, cars just go places. You get strapped in and you just wait and you get impatient. Then eventually you go somewhere. You're not even consciously aware of the concept of driving. Just cars just happen and you're not even aware of it.

**Ken Norton** (00:12:41):
As you get a little bit older, you start to become curious. You start to figure out, oh, that wheel has something to do with it. You turn the wheel. Maybe you start to understand there's pedals. But it also just seems really simple. Just like you get in the car and you drive it and you go somewhere. Maybe as you get older, you end up maybe even being a little bit of a smart Alec about how easy it looks and you start talking to your parents about, like, "It doesn't look hard. I can do this."

**Ken Norton** (00:13:07):
Now suddenly you're behind the wheel of the car. This is what my son is doing. Wow. Is it different than you thought it was going to be? Is it way more complicated? You have to remember check your mirrors. You've got to look before you turn. You didn't even know what that sign meant. You didn't know what those stripes meant. It is just overloading with complication and your internal mindset for confronting this challenge is not going to suit you the way you used to approach the world.

Maybe to put it in product leadership, product terms, everyone around you has got some real pithy advice about the things you're forgetting to do. It's like, "Hey, don't forget to check your mirror." Everyone's got a framework. It's like, "Ah, do you know about the 10:00 and 2:00 framework?" "Wait, what's the 10:00 and 2:00 framework?" "Oh, you just put your left hand on the 10:00, your right hand on the 2:00. That's the only thing you're missing. Here's a great medium post about that." Then you're like, "This is a problem is I have not adapted to the complexity of the world around me."

**Ken Norton** (00:14:19):
And so, there is this sense that what is interesting about driving is the world hasn't gotten any more complex. Driving's always been driving. But now your place in the world has shifted such that the internal meaning-making and self-complexity that is required requires a complete reboot of the internal operating system in order to allow you to thrive there.

**Ken Norton** (00:14:41):
And so, when you talk about this question of how much of this is skills, how much of this is tactics, how much of this is learning versus how much is internal growth, the answer is it's both, but the shift that is required is very much around how your inner self can make meaning and respond to the demands of the world around you so that you can succeed and thrive in this mindset shift that happens.

**Ken Norton** (00:15:09):
The skills matter, but by this point, you're beyond the place where you've learned the skills. There's mastering the skills, but there is this sense of what developmental psychologists call self-complexity, the ability to respond and adapt to that.

**Ken Norton** (00:15:24):
And so, I think we go through a lot of those shifts in our career. The driving example is simple. Actually, probably too simple, because the world is actually getting more complex for those of us that work in product. I mean every day something changes. It forces us to respond and adapt. So there aren't even rules of the road in product.

**Ken Norton** (00:15:42):
But I think this is what we're talking about, this question of the internal operating system I develop my ability to restructure it such that I can succeed given the demands that have been placed upon me.

**Lenny** (00:15:57):
What an amazing analogy. Totally hits home in a good and bad way. It's a really good segue to something I wanted to chat about, something that we talked about before the recording, which is what you're finding to be one of the bigger unlocks for your clients. It's also a concept that you've been spending a lot of time refining and you're finding is helping people shift, and specifically shift their leadership mindset. And so, I'd love to just hear you talk through your thinking there.

**Ken Norton** (00:16:24):
Yeah, it does sort lead into this. Maybe another analogy that might work for your listeners, if you think about product management, your career arc and where you are challenged from a mindset perspective, in some ways it does feel like the early part of your career. You're learning to play a video game. Hopefully there's a tutorial. Your first job is learning the ropes, somebody's teaching you. You maybe have managers that are giving you simple little missions that you can succeed at and if you fail, the consequences aren't bad.

**Ken Norton** (00:17:03):
It does feel like a little bit ... And I felt this way, and I talked to a lot of people earlier in their career. It does feel like you're trying to learn the rules of the game, trying to figure out the physics. You want to run up the score.

**Ken Norton** (00:17:15):
You get better at playing the game. You fail, but you start to develop some confidence that when you fail, you'll learn from it. You'll get better. You get really good at the game. You get promoted, you get rewarded, you unlock new levels, teach other people how to play the game. You start to feel really awesome about yourself.

**Ken Norton** (00:17:32):
But then suddenly you're put in a place where you realize that the rules of the game aren't so black and white. Maybe there's a long delay now between when you get to see what you did and the score of it. Things start to behave in unexpected ways. The physics start to get weird. You're on a level where you're floating. I don't know what the right metaphor is here.

**Ken Norton** (00:17:52):
But you start to recognize that there's been this huge change. The most frightening part about it is you look around and everyone is looking at you like you're the designer of the game, and you thought you were playing. That's often what it feels like when you move into a leadership role, to come back to this sense of what got me here is not going to get me there.

**Ken Norton** (00:18:17):
I work with a lot of leaders and sometimes that's come with a pretty significant cost, this juxtaposition, maybe your happiness, your health, your marriage. There's been this existential crisis of I don't know if I love this anymore. Maybe it leads to burnout. Maybe it's not even that dire. It's just a sense of, well, I'm looking around and I need to be something. I need to unlock something else to continue on this path. There is a sense of stuckness that comes from that.

**Ken Norton** (00:18:45):
What I've come to realize is this is the precipice of, I think, this pretty fundamental concept in leadership. I'm not the originator of this, so this has come up again and again and again. It's not new. It's going to sound familiar. It's like the flood myth from Gilgamesh showing up in all this oral histories of the world. It's not new.

**Ken Norton** (00:19:10):
Conscious Leadership Group, an organization that I'm big fan of, they call it above the line versus below the line. Brene Brown calls it daring versus armored leadership, sage versus warrior. Even in the world of sports, there's playing to win versus playing not to lose. It's this concept that's come up again and again. Leadership Circle calls it creative versus reactive, and that's the term I'm going to use. I like that.

**Ken Norton** (00:19:35):
Here's the distinction. Very simple. Are you responding to the world from a place of fear, where you see problems and threats, you want to be right, you want to be liked, you're defensive as an inward approach, or are you responding to the world from a place of openness, possibility, curiosity, passion, growth, purpose? Very simple concept. Pretty much everyone understands what I mean. It makes sense.

**Ken Norton** (00:20:11):
Everyone also then immediately says a couple of different things. "That sounds amazing. I'd rather have that," or, "Here are moments when I've felt that," but that's usually followed up by a couple of questions. "I don't know if that works. It doesn't sound very effective. Is it possible?" Then how do you that?

**Ken Norton** (00:20:38):
The effective part is actually a question we can answer, which is, yes, it is more effective. Bob Anderson, Bill Adams are two management scientists who've written extensively, done a whole bunch of research, and they have looked at every possible dimension you can imagine of success, both leadership capability, they've looked at revenue, brand, profitability, everything, and it's shown, yes, this creative form of leadership is in every possible way positively correlated with success and reactive leadership is negatively correlated. So, yes, it works yet.

**Ken Norton** (00:21:17):
Yet, according to their research, some 75% of leaders are primarily operating reactively. So most leaders are operating from a place of fear, reacting, seeing problems, and threats. That's because that other question of how do you do it is such a hard one to answer. It's not an easy thing that you flip the switch of. It goes back to this notion of redesigning that internal operating system, so how you confront the world, what underlying belief systems and assumptions you have that are causing you to operate from that place.

**Lenny** (00:21:55):
Can I ask you a quick question? Just to clarify the two sides, what's a sign that you're in the reactive side of things? I think one thing you said is you're worrying a lot about how people think about you and make sure that they like you. Is there anything else that's going to tell a listener, "Oh, maybe I'm falling into this trap"?

**Ken Norton** (00:22:13):
Yeah, you've nailed it, which is that fear, like operating from a place of anxiety. There are different ways, depending on our mindsets, our approaches. I like the word postures because it seems to click different ways that we retreat into this reactive mode. Fear and anxiety is the way. That's how you know. You're just like, "Ugh, I'm below the line." I'm just like I'm seeing problems. I'm seeing threats.

**Ken Norton** (00:22:43):
Our brains are hardwired to do that, so it's not like that's wrong. These are brains that learn to do that, I don't know, on the tundra being chased by wild animals. So this is our normal way of being. There might be different desires and needs that force you to operate that way. We think there's really three of these postures.

**Ken Norton** (00:23:11):
Anybody is probably more than one of them, so this is not pathologizing. This isn't putting you in a box. But probably one of these will resonate more than the others. Wanting to be approved, wanting to be loved, wanting other people to like you. This was me in my early part of my career.

**Lenny** (00:23:28):
Same.

**Ken Norton** (00:23:29):
Yeah. So you're kind of like the heart type. It's sometimes called move toward other people. A lot of that came from my environment. I was coming up with product management. No one necessarily knew what the job even was. I had no authority and most people could just ignore me if they wanted to. And so, I had to meet other people's expectations, please them, want to be accepted by them, seek their approval. It was this what we call a complying approach.

**Ken Norton** (00:23:58):
Here, this is why this is so vexing is it actually worked really well. It was pretty effective. Other people liked working with me. I listened to them and I considered everyone's needs and made sure everyone felt heard. But there came a point where I gave away so much power that it was hurting me when it came to purpose and execution and decisiveness.

**Ken Norton** (00:24:22):
And so, again, these aren't bad. There's usually underlying tendencies that are very good. It just starts to have a cost as you become more senior. It's like the gears start to grind to a halt a little bit.

**Ken Norton** (00:24:35):
Another way is more of a needing to be right head type, protecting one's own ideas, sometimes called a move away from type, distance, arrogance, criticism, retreating into your own ideas and head. Then the other will not be a surprise, is the more controlling, my way or the highway, autocratic will move against wanting to win, wanting to be number one, wanting to excel, wanting dominance, wanting control, this would be another tendency.

**Ken Norton** (00:25:10):
Often one of those feels natural to you and another one feels just so incredibly distasteful that you can't imagine possibly operating that way. This goes into the underlying beliefs part. If you had told me early in my career, when you saw me being passive and people-pleasing like that, "You've just got to stop caring what other people think, Ken. You've got to be more pushy."

**Ken Norton** (00:25:41):
People did say that to me. That was pretty common probably in my performance review. It was very common. Even people who worked for me were like, "You need to push back." My only archetype for doing that was the autocratic, controlling type. I was like, "I don't want to be like that. That guy's a jerk. That's a fascist. I don't want to be a fascist. I do care about other people."

**Ken Norton** (00:26:04):
And so, many of our examples and archetypes are these equally ineffective reactive ways of being. And so, no wonder I didn't want to be like that, because that's also not very effective either. But there was a sense for me of redefining ... This is where coaching is powerful is this what are the underlying assumptions and beliefs that you have that are causing you to fall back on some of these fundamental ways of operating and not let go of them?

**Ken Norton** (00:26:35):
Because the answer for me wasn't stop caring about other people. I wasn't going to do that. That's a value of mine. It's part of who I am. But take the caring about other people, the empathy, the connection, and direct it in a more creative way where you're operating now from a place of purpose and vision and not reacting and protecting and defending and wanting to be.

**Ken Norton** (00:26:56):
For me, the key to that was letting go of needing to be liked and redefining it as an admiration that takes place over time. So rather than I want to leave this room with everyone liking me, I started to realize I want to be the type of leader where, a decade later, people say, "I would work with that guy again in a heartbeat." That was part of the unlock for me.

**Ken Norton** (00:27:25):
Again, I care about other people. That's a natural gift that underlines it. But it's a redefinition of how that serves me, if that makes sense.

**Lenny** (00:27:34):
Say someone's in that first bucket ... And I was definitely in that first bucket. I still want people to like me and I still probably have flaws there. But say you're a PM and you're like, "Oh, man. That's exactly how I am acting right now." It sounds like is the core of it just a mindset shift, going from I need people to like me to what you just talked about of, okay, I'm going to shift to I just want them to respect me over time? Is that the core of it? I know it's probably not that easy, but how should someone behave during that bucket right now?

**Ken Norton** (00:28:03):
Yeah. It sounds easy, right? This is part of what's hard about this, is it always sounds easy when you describe it, having gone through the journey. It's sort of like talk to somebody on the summit of Mount Everest and they'll be like, "Yeah. Well, I could just climb this mountain. That's how I got here." You're like, "Okay, wait, that's not that easy." Again, it is very individualized.

**Ken Norton** (00:28:21):
I think there's an appreciation that you have to understand what is holding you back. This is a lot of the work that I'll do with my clients is what is those underlying expectations? What are these underlying beliefs?

**Ken Norton** (00:28:40):
I Believe that my style was incompatible with being the leader. I would've said I can't be a CEO because I'm not tough enough. I'm not strong enough. I'm not commanding enough. I can't command a room. It's like, okay, what is the underlying belief I'm making about what leadership is there? There's an archetype that I have in my mind that is incompatible with this this way.

**Ken Norton** (00:29:10):
And so, there's a need to confront that. Okay, what makes you believe the only type of leader is the leader that orders people around? Maybe that's all I've ever seen. Maybe I don't believe it's possible to be another type of leader. Maybe there's an inner critic that is convincing me that that's not who I am, because a part of it is redefinition of what does leadership need for you, for you authentically? What would it be like, in my case, to lead with purpose and be decisive and lead with vision and to have other people felt like they're being brought along and listened to and participated and create safe spaces for other people? That was the question there.

**Ken Norton** (00:29:47):
It took people challenging my point of view. It took working with a coach, asking me questions, forcing me to see places I'd made connections, that the connections don't really need to be made. There's a lot of instruments and tools we work with in coaching. There's 360-degree assessments that are very helpful here that will start to help you understand, hey, here are places where you're operating actively. Here are places where you're operating really creatively, because, by the way, most people are partially somewhere in that journey. It's a developmental process.

**Ken Norton** (00:30:17):
And to start to be able to get the feedback, the dopamine hit of seeing when I do it this way, actually it's more effective and it doesn't cost me as much. I'm happier and I'm enjoying it, I'm seeing that it's working, is oftentimes a big part of this because there is this belief that it won't work. The number of times when I'm with a client in coaching and say, "Well, what if you did do that?" and they go, "It just won't work." You realize that there is this wiring in there that needs ... And this is what I talk about, this operating system that needs to be rejiggered to start to make sense of what if it did and how might you know.

**Lenny** (00:30:55):
The point you just made about how you can realize that you can be successful in a lot of different ways and you don't have to be this one archetype of a leader really resonates with my experience. I actually had an executive coach for a few months, and that was probably the biggest unlock for me. We did the strengths exercise, which a lot of people do. The main thing that she helped me see is you can do all the things that you want to do through the lens of the strengths that you have and not have to force yourself to be good at these other things, because there's many ways to accomplish the same outcomes.

**Ken Norton** (00:31:29):
That's exactly right. Then once you start to understand that, you start to develop a better way of finding the right place, the right environment, the right role. When we began the conversation, you asked me what brought me into executive coaching. I would feel these ... I would describe it as flying too close to the sun in my career, where I would have a team. I'd be managing a small team. I would love it. I would enjoy it. Then suddenly my team would grow.

**Ken Norton** (00:31:57):
I'd become more senior than I felt comfortable being. Then I felt like I wasn't getting to do the "real" work anymore. Then I would be just completely disheveled and dissatisfied. Then I'd go try to go find a smaller team or even stop being a manager. It was a very meandering, reactive path. It was like every so often I was catching a wave, and I knew what it felt like to be on the wave, but I didn't know what the characteristics of the wave were.

**Ken Norton** (00:32:23):
Then through coaching, I was like I love connecting with other people. I like helping people grow. I like helping challenge people. I like helping. Then I was like what are those parts? What if I unpack those? Oh, that's why I loved managing that team of five because I got to do a lot of it. That's why I hated managing a team of 35 because there's no time for it.

**Ken Norton** (00:32:44):
Then you start to say, okay, well, what if rather than just randomly meandering through my career, I actually elevated needing to connect, wanting to be helpful? Then you're like what would it be like if I wanted the helping professions? It's just a reframing of move through your career in a way that seems externally to fit some definition of success and to start to define that internally.

**Ken Norton** (00:33:11):
That is the very definition of the reactive versus creative mindset. Reactive, allowing the world to set the expectations and try to meet them versus tap into what your real, true sense of purpose and vision is. Then use that to navigate the world.

**Lenny** (00:33:28):
It's interesting that so much of this is just mindset. It's not like learning a new skill as a leader or a product manager. It's just seeing yourself in the world differently. All of a sudden you unlock your career. Is that what you find?

**Ken Norton** (00:33:40):
Absolutely. That's why I think so much of the focus on the skills, the frameworks, it can be limited as you develop these capabilities, because it's inner work. Where we're talking about is this is all me.

**Ken Norton** (00:33:57):
Now that's empowering. There's empowerment to be able to say I want to change something and it doesn't involve a whole bunch of other people convincing and persuading them, getting into an executive ... This is all me. But it also, in some ways, makes it harder because it is all you. In coaching, it's all about you. It's all about that. Who am I and what matters to me? What underlying belief systems, inner voices are challenging me in ways that I want to be challenged? What is my unique ...

**Ken Norton** (00:34:31):
I love the word authenticity. It's, like you were just talking about, like what is my authentic way to lead, and then how do I center that rather than trying to fit into someone else's definition of what leadership might be?

**Ken Norton** (00:34:43):
You may recognize I can't be that authentic way of leader at this place or in this place type of company, but I know how to find it and I'm going to go find it.

**Lenny** (00:34:55):
Do you have any more examples of either someone uncovering this about themselves, or another mindset shift that you can make in one of these other buckets, similar to the idea of I'll think about people over the long term versus immediately?

**Ken Norton** (00:35:10):
Yeah. It really does vary. You start to pick up on that shift when it's less of the goals being defined externally and more of the goals being defined internally. So you'll have a conversation with somebody who's new to coaching and you'll say, "What do you want?" They'll be like, "Well, I want to get promoted to VP." "Why?" "Because I want to be a VP." It's like, "Well, what's important about being VP?" "Well, because ... " Eventually the answer is, well, because it's there and that's the thing that I'm supposed to do.

**Ken Norton** (00:35:45):
Then you start to notice the shift and it starts to become more of, "Well, because really what's important to me is creativity. I want more creativity in my life. I want more ability to challenge other people." And so, you start to just sense that's more from in than from out. That's where that shift is.

**Ken Norton** (00:36:06):
The journey is different for everyone. I think ultimately this is part of why, quite frankly, coaching may not be right for everyone. If we go back to that video game analogy, if you're looking for someone to just teach you the tutorial so you can learn how to play the video game and there's this jackass like me sitting next to you and saying, "What's important to you about playing this video game?" you're going to be like, "Just can you tell me how to hold the controller? Can you stop?"

**Ken Norton** (00:36:31):
So it's not always right. It's a place where I think oftentimes people recognize that they've gotten all the advice, all the frameworks, all the rules, all the tricks, all the tips. They've learned that, they've mastered it, they've tweaked it, they've optimized it, they've recognized the shortcomings, they've customized it. The emergence that's required for them to get to the next level is just going to come just as much from inside them as it is from outside, if not more. That's when that shift is made.

**Lenny** (00:36:58):
That's called mentorship, I think, for people that are just looking for actual concrete advice on how to do a thing, is that right, versus coaching?

**Ken Norton** (00:37:05):
I think so. This is where the words are squishy because there are a lot of people who are mentoring, who are also stepping into a coach role occasionally. There are plenty of managers who are great at coaching as necessary. So skills run the gamut, but it's a question of how much are you looking for someone to tell you the right way versus how much do you believe that there even is no right way? It's ultimately going to have to be your way.

**Ken Norton** (00:37:33):
That's a different place, a different point in your career at different levels of journey. It's part of why I tend to work with probably more senior executives, because they're not looking to me to tell them how to do the job. They've already learned how to do the job. It's just something deeper that's going to need to break through from that.

**Lenny** (00:37:50):
**Ken Norton** (00:39:06):
Yeah, it's a great question. Here's the secret about the coaching industry. Anyone can call themselves a coach. It's very democratized. It's great. There's no gatekeepers and barriers and there's no 500 licenses you have to go through.

**Ken Norton** (00:39:22):
There are tons of great coaches who are at various different price levels, at different levels of accessibility. And so, if you say, "I can't afford a coach," I might challenge that a little bit and say have you looked?

**Ken Norton** (00:39:36):
The other thing is that you don't need a coach who's done the job before. I mean obviously I've done the job before, so I'm undermining part of my own selling point here. But coaches are trained to coach people on any topic. So when I go through coach training, I can coach you on anything. People can coach you on anything.

**Ken Norton** (00:39:52):
Sometimes even there might be power in having a coach that's never done the product management job because there won't be any cheating of starting to move into a more of advisor role or maybe as the coach either. There may be, "Well, you tell me what should I should do," and the person would be like, "I don't know. I've never done this job. Let's go back to what you want." So there could be some benefit from that. Again, you don't have to have done that.

**Ken Norton** (00:40:13):
So I would say coaching is incredibly powerful. I wish I'd had a coach much, much earlier in my career. And so, the answer may be coaching is more accessible than you thought. If not, I think the things that we're talking about here are internal understanding of what matters to you, your sense of purpose, this inner curiosity, and that could be harnessed at any age. So just wondering about yourself at any point in your career, wondering what's important to you.

**Ken Norton** (00:40:43):
I love doing values work, like, "What are your values? Okay. No. What really are your values?" That's something you can do yourself. That's something you can question. You can read about, you can start to understand.

**Ken Norton** (00:40:53):
Mentors can be great, especially mentors who are less about trying to tell you the right way and get you to follow directly their path, but are more they're applying some curiosity, asking questions, challenging you in certain ways, being a way that you can bounce ideas off of.

**Ken Norton** (00:41:09):
Great managers, I think, especially the best product leaders, understand how to put the coach hat on and when it's appropriate to put the coach hat on, and are explicit about that, are like, "Okay, let me take off my manager hat now and put the coach hat on. What do you really want to do, Lenny? What's important to you? What's your career?" And so, I think you can get coaching from everywhere.

**Ken Norton** (00:41:28):
There's a lot of self-coaching you can do. This is honestly one of the benefits for me having gone through tons of training and coaching is starting to coach myself, like feeling an emotion and asking myself coach questions. Really powerful. That's something you can do when you've had a coach. You can do it when you don't have a coach. You can explore it.

**Ken Norton** (00:41:46):
So I think this is really all about really being curious and wanting to understand who you really are at the core and what's important to you and what matters. That's something that can be done with or without a coach.

**Lenny** (00:41:58):
Are there any resources that you love for either the values work or learning these questions to ask yourself? We can put them in the show notes if nothing comes to mind immediately. But is there something you recommend people check out?

**Ken Norton** (00:42:08):
Yeah, there are some great books. Maybe I'll use this opportunity to throw out a couple suggestions.

**Lenny** (00:42:13):
Let's do it.

**Ken Norton** (00:42:14):
I guess we can link it into the show notes. Brene Brown's Dare to Lead. It's a good book. She actually even has a whole section in there around values, confronting her values. I like her approach. There's some free resources on her website.

**Ken Norton** (00:42:26):
I love Conscious Leadership Group's work here. The 15 Commitments of Conscious Leadership book is fantastic. You don't even need to buy the book. There's a ton of stuff on their website. Jim Dethmer, Diana Chapman and Kaley Warner Klemp are of the authors of that book. That's all about a lot of the stuff we've been talking about. They're the ones that have the above the line versus below the line that fits into this creative versus reactive standpoint. Those are all fantastic.

**Ken Norton** (00:42:57):
If you want to go deeper into more of the management science behind it, if you're like me and really curious about the psychology and the management science, Bob Anderson and Bill Adams's book, Mastering Leadership, creates the entire integrated system around creative versus reactive.

**Ken Norton** (00:43:19):
As a teaser, they identify five levels of leadership, of which reactive is the second, creative is the third. So beyond that, you get into integral and unitive. So if you're looking to unlock the advanced stages beyond creative, there's a lot of great stuff in there. Those are where all the research comes in as well.

**Ken Norton** (00:43:38):
From an adult development standpoint, Robert Kegan is the godfather of the adult-stage development work and the meaning-making that underlines a lot of this. He has a great book called Immunity to Change if you're curious about that.

**Lenny** (00:43:52):
Awesome. We will link to all those in the description of this podcast so folks don't have to Google around. I have a couple of more coaching questions before we move on to a few other topics. One is just what are you finding are the most common blind spots for product people in general? How are people shooting themselves in the foot most?

**Ken Norton** (00:44:11):
Oh, that's a great question. I think probably the number one category, I'm not sure it's necessarily a problem, but maybe category or problems, is ... And this is, I think, great lesson for people earlier in their career, is how much all of the challenges that senior executives are dealing with come down to people versus product. So it's like it's fun to think about designing products, optimizing, doing user discovery, and testing what, but it's like you sit down with an executive and it's all about people.

**Ken Norton** (00:44:47):
That's the hard part. It's about persuading people, getting groups of people to want to work together, trying to figure out how to deal with difficult personalities, figuring out how to set a vision and articulate a vision, create an environment where people can collaborate and play.

**Ken Norton** (00:45:01):
And so, I think this category of blind spot often is people being confronted with that without having been intentional about thinking of it as a skill or an area that they needed to work on, needed to improve.

**Ken Norton** (00:45:18):
Part of what I think is pretty exciting about product management is you are a leader from day one in product management. There's leadership all over the place, but that's your job. You're a leader. You don't have any formal authority, but you're a leader. You're expected to lead.

**Ken Norton** (00:45:39):
Guess what? The hardest part about being a leader is when you don't get to just rely on the formal authority. So you're getting to practice all the hard parts about leadership from day one, because you're nobody's boss. You get to sharpen those skills, develop those intuitions, get better and better at that, so that when you do someday, if this is right for you, become someone else's boss, you've already been able to lean into that.

**Ken Norton** (00:46:04):
And so, the people side of this is such an incredible aspect of what product management is. What I find, and this may be a category of blind spots, is people realizing that when they're put in a position where they're expected to have impact and realizing that they haven't developed the skills, they haven't developed the capability to actually be able to manage and work through all these people, which is ...

**Lenny** (00:46:33):
How do you actually get better at that or develop those skills?

**Ken Norton** (00:46:37):
Yeah. I just think recognizing it is part of the job. It's important. Maybe I came up at a certain time where it was often dismissed as soft skills. It's just like soft skills are helpful, but they're not actually something you want to work on. They're not something you train, not something you ...

**Ken Norton** (00:46:54):
And this is just as important. This is the equal ... I wrote a piece recently about the art versus the science. The art is communication, collaboration, the more fuzzy, softer skills, people stuff. It's an elevation of that being just as important, if not more important, over time, as all this skills, techniques, tactics, managing a backlog, all that kind of stuff that you have to do. You should invest in that the same way you invest in those other skills.

**Ken Norton** (00:47:25):
So if you go off to a training to learn a technique for doing, I don't know, some sort of technical dashboard analysis, why don't you go to training to learn how to have difficult conversations? Because there's some great training about having difficult conversations, or do some training about storytelling. These are all really, really important factors that start to come into play.

**Ken Norton** (00:47:54):
What I would recommend is just appreciating that these are going to really, really matter and practicing and then valuing them and not thinking of them as something that either will matter later or a distraction or not really part of the job.

**Lenny** (00:48:07):
I think the reason people don't do that work is because it's so hard. Difficult conversations are difficult. We talked about this with Trey Hass. But just like it's a rule of thumb, the thing that is hard is probably the thing you should be doing. It's like a compass point of you to the thing you should do.

**Ken Norton** (00:48:23):
Absolutely. We are all about doing hard stuff, product managers. That's what we're all about. And so, when something seems hard and it seems squishy and it seems like it's difficult to put a three-step rule around, chances are it's really going to matter. It goes back to this mindset shift. That means that there's an opportunity for you to readjust your inner complexity management system to adapt to that area of complexity that you're now seeing, because this stuff really feels squishy. And so, that's even more of a reason why you want to get your hands around it and grab onto it and value it and learn and grow from it.

**Lenny** (00:49:07):
Speaking of difficult and squishy, I'm guessing that one of the biggest challenges that people you work with face and one of the most recurring themes is imposter syndrome, people having imposter syndrome, something definitely I went through and it comes up a lot on this podcast. What do you usually advise your clients to do when they're feeling imposter syndrome?

**Ken Norton** (00:49:27):
Yeah, it's a great question. I always get corrected to say imposter phenomenon by people in the psychology community, because I guess it's not a dysfunction. And so, I've learned to use their terms. But, yeah, I think just about everyone experiences it at some point. Research shows that that definitely is born out ... It's really the moments when you're doubting your abilities or you feel like a fraud or you feel like you don't belong.

It's funny because as I'm interrogating my own inner emotional state right now, I'm feeling it a little bit, because there's a part of me right now that's just like, "You're not a trained psychologist." When I said that whole thing, well, it's technically a phenomenon, there's a voice that was like, "What are you talking about? You don't know what you're talking about. Who are you [inaudible 00:50:14] on this?"

**Lenny** (00:50:14):
We'll put a disclaimer on the episode.

**Ken Norton** (00:50:16):
Yeah, I'm not a psychologist. So, look, we all feel it. There's a part of me right now that's like I'm going to say the wrong thing and embarrass myself. Product managers, product leaders maybe more so because the role is so cross-functional and ill-defined. There's always going to be an edge of the job that you aren't as qualified as whoever you're interacting with. It's the nature of it. Look, we're never going to be as good as an engineer, as good as a designer, as good ... So there's all these opportunities for that.

**Ken Norton** (00:50:40):
I find, certainly from client work, that there is a little bit of a softening and solidarity just knowing that. I'm just like, "Oh, you have that, too? Oh, I have that. Yeah, there's some value to that."

**Ken Norton** (00:50:51):
I think it's important to pause here and say that there is the risk of dismissing or even maybe weaponizing imposter phenomenon against particular populations, particularly women, people of color of all genders, women of color especially, who are facing real external feedback and doubt about their abilities.

**Ken Norton** (00:51:15):
The environment is reinforcing and the source of a lot of this stuff, microaggressions, bias, real aggressions. And so, I think we always have to be careful in the helping professions to not dismiss it as a problem that just shifts the obligation to the person. So it's like, "Oh, that's just your imposter syndrome. Deal with it." Well, it's really easy to overlook all these systemic issues that are leading to that imposter syndrome.

**Ken Norton** (00:51:39):
So the leaders I work with, I think we have a special obligation both to confront our own inner dynamic, but also to recognize what our role is in the broader environment that might be contributing to some of this stuff. If you're a leader, you have a special obligation to dismantle those, not when you're meeting with your people, be like, "Ah, it's just your imposter syndrome. You can work through it. Hire a coach," but to be able to recognize, "Okay, wait, what signals are you getting? What issues are contributing to this? What's our role in needing to change that?" So I think that's worth pointing out.

**Ken Norton** (00:52:13):
By the way, there's a great article in Harvard Business Review from a couple of years ago. I think the title was literally Stop Telling Women They Have Imposter Syndrome. The two authors of that were Ruchika Tulshyan and Jodi-Ann Burey, if you're curious and you want to go into more depth on that.

**Ken Norton** (00:52:29):
As coaches there, there's all sorts of ways we're trained to work with this. Oftentimes as an inner critic and inner voice, we all have voices, saboteurs. They're often trying to help us, they have good intentions, but they're developed to try to protect us in certain ways. So gaining awareness of those, just sort of like, "Oh, that is an inner critic. That's what it's trying to do." There's a self-distancing that's valuable to that, really kind of ...

**Ken Norton** (00:52:54):
I like to think of it a little bit as you got inner border directors, and there's some noisy, chatty voices that every so often sit in the chairperson's seat and start taking over. If you start to recognize, "Wait, no, I'm the chairperson. I don't want to hear from you right now. We'll hear from you later," it starts to create some power and you start to notice when it's happening.

**Ken Norton** (00:53:16):
We bypass inner critic sometimes as a classic coaching technique. It's like, "Okay, I'm sounding that's your inner critic is saying that. What if we just ask it to maybe step aside? Let's keep talking here."

**Ken Norton** (00:53:28):
You can befriend it. There's a lot of practices and works just actually trying to understand what its motivations are. You can think of it as a board. Give this board member a new job, put it on a new committee, reassign it.

**Ken Norton** (00:53:41):
There's oftentimes underlying belief systems. We talked before about my impression of what a real leader was and who they had to be. And so, hey, when all those second-guessing of me not being a real leader, of me not being qualified came from some of those underlying assumptions, that that was the only type of leader that was effective, was somebody that was slamming their fist out on the table.

**Ken Norton** (00:54:02):
Okay, so what if we redefine that? I'm too kind to be a leader. I'm not dominating, commanding enough. When you hear a client say that as a coach, you recognize, okay, there's a connection being made here between what effective leadership is and isn't. Let's interrogate that connection. Is that connection actually true?

**Ken Norton** (00:54:21):
Again, it get backs to this question of you're often responding to other styles, approaches you've seen. You're comparing yourself to others. So this is the reactive mindset of I'm always comparing myself to that person, to that wave, that being, and seeing myself as lesser then. And so, the inner work of starting to see who I really am truly inside and less comparing myself to others.

**Ken Norton** (00:54:42):
But, yeah, imposter phenomenon, syndrome, whatever you want to call it, very common and very popular, I suppose. Although when I say popular, it's like popular like a play.

**Lenny** (00:54:53):
Right. Another inner critic tactic I've heard that I used for a bit that was helpful is to give your inner critic a name, like Jim. I mean like, "Jim, not right now. I don't need you right now." That kind of helps.

**Ken Norton** (00:55:06):
Yeah. There is a whole school of coaching that I've worked with that's called parts work or internal family systems. It comes from a psychologist named Richard Schwartz who determined this. It can be really, really powerful.

**Ken Norton** (00:55:19):
I'll word my clients and we will give them names. We will imagine what they look like. They will interview these parts. If you've seen the Pixar movie Inside Out, this notion that like, hey, all these different parts show up in different ways. I'm going to put myself, the real me, the real self into the chairperson's seat. When I hear these voices, I'm going to appreciate them from what they are and who they are. They're not me. They're parts of me.

**Ken Norton** (00:55:46):
There's something really powerful in that, in that sense of like ... Because, otherwise, they're all me. So I just hear this voice telling me I'm an idiot and I'm a clown and I'm not qualified to be in this room. Then when you can start to go, "Oh, yeah, there it is. That's Larry Loser. My big angry, irritating judge who's, of course ... Oh, yeah, Larry always shows up every time I do something new, because Larry doesn't want me to challenge myself. So, of course, Larry's going to pipe in. I've heard from Larry. I'm going to ask Larry to step aside. Let's go." Yeah, it can be very powerful.

**Lenny** (00:56:22):
I love that. One last question about coaching. For folks that want to find a coach, do you have any advice of just how to find a coach, and then what are a couple questions you can ask to evaluate if they're a good fit for you?

**Ken Norton** (00:56:35):
Yeah, great question. So I think, like any helping profession, finding a therapist or really anyone who you're going to have a deep and lasting relationship with, this sort of trust and authenticity is really important. I think we all, as coaches, recognize, and we feel this as well with clients, is it either has to be a fit or not. Sometimes it's hard to put your finger on it. Sometimes you meet with someone and you're like, "Yeah, it clicks. It feels right." Sometimes you're like, "Eh, it doesn't," and that's okay. And so, all coaches worth their salt will offer a free session to understand that, engage that.

**Ken Norton** (00:57:13):
I always tell everyone in that session, if you don't decide to work with me or I decide ... We don't need a reason. It's fine. It's just not a fit, and that's okay. You don't need to come up with bullet point reasons to let me down. It's part of how it goes.

**Ken Norton** (00:57:28):
You might prefer certain people, certain gender, certain backgrounds. You may feel more comfortable or less comfortable with ... Maybe you want an old guy like me. Maybe you want an old guy like me, and that's fine. It has to feel right.

**Ken Norton** (00:57:41):
I would ask them to talk to you about what coaching is to them, because, again, it might combine some of these more mentory things. It might be more tactical. Some coaches are more structured, "Week one, we're going to do this. Week two, we're going to do this. Week ... " Others are more pure coaches like me, where, look, within the first five minutes, I'm going to ask you what you want to talk about today, because you're bringing the agenda. So figure that out. Figure out what works for you.

**Ken Norton** (00:58:07):
Then I think there's a lot of great places to go. Actually, specifically where to go, the International Coaching Federation is our governing body. So those of us that are credentialed coaches you'll find there. Again, you don't have to be credentialed, but that'll be a great place to find people who are.

**Ken Norton** (00:58:23):
There are some matchmaking services, BetterUp, Torch, or some of the more accessible ones. There's one called Prismaticco. It's a little bit more higher end for more senior execs. Scale just put out a list of top coaches who work with product managers and product leaders, all sorts of great coaches. We can include that link. Lenny, I think you're involved.

**Lenny** (00:58:43):
Yeah. Congrats on winning one of their categories for best coach of ... Which category was that?

**Ken Norton** (00:58:49):
Product leaders. So, yeah, this was just a setup for you to say that. But thank you. But there's tons of great coach, and different styles, different stages of careers. I think all those folks have work with or have worked with product folks.

**Ken Norton** (00:59:03):
And so, again, just talk to a few. Reach out to a few. Ask them. If you're looking for more names, ask people who you admire, whose leadership styles you like and want to emulate, who they recommend, because oftentimes they have a better understanding of, hey, this is the type of coach that may want to work with, more of the emotional work, or this is the type of coach who actually maybe has a more compatible vision of what you're looking for, because, look, all coaches are different. You can tell I'm a touchy-feely heart coach.

**Ken Norton** (00:59:35):
There are coaches who are ... Sometimes people want a coach and they're just like, "You grab that brass ring. We're going to pound the table. I'm going to push you. I'm going to challenge you. I'm going to beat you up. I'm going to be more of a drill sergeant." That's a different style of coach that works with other people. That may be more what you're looking for.

**Ken Norton** (00:59:50):
So I would just talk to a bunch, do some free sessions, get an opportunity to explore it. I coach people in the free session. So it's not just like we're talking. We're going to talk about something. I'm going to coach you. You're going to get a sense of what this looks like. Then come away and just ask yourself, what are your goals and where was there a fit? If there's not, just keep looking.

**Lenny** (01:00:09):
Amazing. That was very tactically helpful. I really appreciate all those resources. We'll definitely link to all that in the description. I have just a couple questions I wanted to ask you outside of coaching, around some of your posts that you've written before we get to our exciting lightning round. One is around this idea of 10X versus 10%.

**Lenny** (01:00:26):
So you wrote this post about the importance of thinking 10X versus 10%. Truthfully, I actually had a post started, "10X versus 10%." I was like, "Oh, this is going to be great." Then I Googled, "Oh, Ken's already written about it." So I'm glad that you have written about it and written about it so well.

**Ken Norton** (01:00:41):
Great minds think alike, as they say.

**Lenny** (01:00:44):
Now I don't have to write it. I'd love to just hear your general take on what this idea is and how to think about 10X or 10% bets.

**Ken Norton** (01:00:53):
Again, I'm a great synthesizer of ideas. This isn't my idea. This is a lot of ... It came from some thinking at Google and some push. I think it's really the sense that we think too small sometimes. You'll see that as a theme for some of the other things I've written too. There needs to be a push. If you really want to have huge breakthrough innovation, you need to be able to try, you need to be able to fail. You need to be able to shoot for the moon is where this 10X comes from.

**Ken Norton** (01:01:22):
A lot of it is mindset, but a lot of it is also cultural. It's creating environments where ... And I had the great privilege of working at Google for 14 years. I felt like it was definitely an environment that I got to play in, of being willing to take big swings that might fail.

**Ken Norton** (01:01:36):
This doesn't mean that the company could all be out of business tomorrow. But it's like if you have a choice between trying something that could have a massive breakthrough, a massive change, and playing small ball where you're going to get a bunch of 10% improvements, you are over time, if you're willing to try, if you're willing to fail, if you're willing to push yourself, if you're willing to think bigger, if you're willing to create environments, great ideas come from places that are unexpected, you'll achieve massive, massive breakthrough.

**Ken Norton** (01:02:02):
You can find the piece on my website, because I use examples from history, but it is a little bit of being brave and trying big things. If you look at all the great technology, the huge breakthrough innovations that we've had, the coronavirus vaccine, just this ... Man, there is no small balling that. That was a big, big swing that there was no guarantee of success, but we were willing to try it. We were willing to fail knowing that failure was probably the more likely outcome in the chance that we would achieve something that would really have that level of breakthrough.

**Ken Norton** (01:02:36):
And so, I think it is what I always challenge leaders to do is create the environment where people can step in and bring those types of ideas, and not play it safe or not be like, "Ah, boy, that seems like a big one. If we bring that to the CEO, there's no way they'll take a chance. So let's ramp down our expectations. Let's bring this little idea in that is a little bit more guaranteed to work."

**Ken Norton** (01:03:01):
And so, it is the obligation of leaders to create that environment for people to be able to innovate, because the ideas are out there. I use the example of Kodak. Kodak invented the digital camera. It wasn't like, oh, people at Kodak were dumb. They didn't know digital was coming. No, they literally invented the digital camera. There just wasn't an environment created where the people who had that idea, who saw that potential, who saw that possibility could step up through the plate and try.

**Lenny** (01:03:29):
Do you have any rules of thumb of how many of your ideas/resources should go into these big ideas versus incremental 10% bets, or is the general advice just like people aren't thinking big enough, often enough, so you should always think a little bit bigger than you naturally will?

**Ken Norton** (01:03:44):
I think it depends. I mean it depends on the company. If you work in R&D, in labs, maybe everything is in that category and you build a portfolio. If you're a venture capital seed investor, or if you're working at a research lab, it's like you're building a huge portfolio of these bets. You're just assuming that maybe 99 of them will fail, but one will succeed and it'll make it all worthwhile.

**Ken Norton** (01:04:09):
Most of us aren't in those environments. We're in places where we have real customers buying our products, wanting our products, using our products. We're like, "Let's bet the entire company own 50 things that may not work out." It may not be right for you.

**Ken Norton** (01:04:20):
So I think it is a little bit of an approach. I think it needs to be thought of in a fractal way, though, because maybe at the company level, they're thinking Google once upon a time had a 70-20-10 thing, whereas 70% is our core business. It's the time we're searching ads. 20% is adjacent business, and then 10% on crazy bets that may not be anything.

**Ken Norton** (01:04:43):
But I think that's at the company level. At the individual level, at your team level, you might have your own way of thinking. You're just like, okay, I've got 12 engineers on the team. We're working on, at any time, a bunch of stuff that we know we have to do. This is a bunch of stuff that we hope is like 10%. Then we're going to create some space for some innovation. Maybe it's just one engineer every sprint, or it's like a couple of times a year.

**Ken Norton** (01:05:09):
You create that type of space in your own little air bubble that isn't necessarily at the portfolio level, to try things that may not work. But if they do, the payoff will be so substantial that it'll make the whole thing worthwhile.

**Lenny** (01:05:23):
Awesome. Very helpful. Next question is around I think your most popular post that you've ever written, and maybe the thing that put you on the radar of writing, is around how to hire a product manager. Maybe this is where you mentioned donuts the first time. Is that right, or no?

**Ken Norton** (01:05:40):
It's funny. I think that was later.

**Lenny** (01:05:42):
Okay.

**Ken Norton** (01:05:43):
Yeah, I think that was a talk that came after that.

**Lenny** (01:05:45):
Okay, cool.

**Ken Norton** (01:05:46):
Yeah, that was definitely the big one for me.

**Lenny** (01:05:48):
So here's the question, just to keep it simple, what's one piece of advice that you would give people trying to hire a product manager? What's the thing that you think is most maybe missed or useful?

**Ken Norton** (01:06:00):
Yeah, I think the intangibles. So basically I wrote that originally as an email, that it was a copy pasta thing for me, where people kept coming to me and being like, "Hey, I think we're going to try to hire a product manager or a company. Can you send over a sample job description?" I'd be like, "Yeah. Before we write the job description, let's talk about what the job is, because I'm not sure we all mean the same thing." And so, then I wrote that ... It was in 2005, so this goes back ... to try to define what the role actually is.

**Ken Norton** (01:06:31):
I actually feel like maybe the pendulum shifted way too far now where it's the interview process is so structured. Everyone's doing all these mock. They know exactly what questions they're going to get. It's SAT prep. Everyone's ready. But we've missed out with can they do the job? Because it's like they can pass the interview, but can they do the job?

**Ken Norton** (01:06:53):
And so, I think you have to be careful. This is particularly the case if you are a smaller company. You don't have a huge apparatus of Google and Meta, where you've got interviewing monolith of getting persuaded into ... Maybe this goes back a little bit to the science and the art. They passed all the technical questions. They do all this, they do all that. They do all that. But then you neglect to find out can this person show up and work with these engineers, these designers? Can they inspire them? Is this somebody that they want to follow? Do they have the right mindset for what this job entails? Do we even have an agreement on what their job is going to be?

**Ken Norton** (01:07:35):
The number of people you see earlier in their career will be like, "Well, I thought I was hiring for this, but it turns that's not even product management," or it was like, "I thought I was going to do this, but all they want me to do is build fee." It's like how'd that not come out in the group process? It's like, well, I know how it didn't come out because they answered a whole bunch of structured questions around ... They did a programming exercise and they did a presentation and nobody stopped to ask.

**Ken Norton** (01:07:55):
And so, I think that's really the big thing from an interviewer perspective. I think same thing goes for the candidate's perspective. You are interviewing a potential employer. You're interviewing a boss. You're interviewing coworkers. What do you want? What do you care about? What is the type of place you want to be in? What do you not want to be in? How are you evaluating that? How are you asking those questions?

**Ken Norton** (01:08:18):
Yeah, salary matters, title. All that kind of stuff matters. But you're interviewing a place to plop yourself into. How are you approaching that to make sure you're making the right decision?

**Lenny** (01:08:30):
Well, with that, we've reached our very exciting lightning round, where I'm going to ask you a few questions and whatever comes to mind, just give me an answer. That's it. Very simple. Does that sound good?

**Ken Norton** (01:08:43):
Yeah. Inner critic is raging right now.

**Lenny** (01:08:45):
Oh, no. Real-time imposter syndrome.

**Ken Norton** (01:08:48):
Here we go.

**Lenny** (01:08:49):
[inaudible 01:08:49].

**Ken Norton** (01:08:48):
Yeah.

**Lenny** (01:08:50):
Okay. So question one, what are two or three books that you recommend most to other people?

**Ken Norton** (01:08:55):
Oh, 15 Commitments of Conscious Leadership. Definitely on that book. I'd just add books I've never recommended before. Probably Innovators Dilemma. It's probably my number one favorite book for product managers and product leaders.

**Lenny** (01:09:09):
Amazing. What's a recent movie or TV show that you've liked?

**Ken Norton** (01:09:14):
I love Ms. Marvel. My whole family were really enjoying it. I love all the MCU stuff. We just eat it up. Ms. Marvel has been amazing. Then watching Barry, which is crazy. It's sort of like nothing else I think ever on TV. Then, over the last year, probably Severance. It's my favorite program over the last ... I'd say last year.

**Lenny** (01:09:34):
Wow. Yeah. That is a trippy show. I've watched it all. We might be severed people, we don't even know.

**Ken Norton** (01:09:39):
You won't even know.

**Lenny** (01:09:41):
Okay. What is a favorite interview question that you like to ask folks when you interview them?

**Ken Norton** (01:09:46):
Well, actually let me flip it because I just talked about interviewing as the interview ... Maybe I'll ask a favorite question for people who are being interviewed to ask the employer. Is that fair or is that turn the tables too much?

**Lenny** (01:09:58):
I love it. Yes.

**Ken Norton** (01:09:59):
I think a great question ... Actually maybe I have a couple. I think one question that I love is how does the company define a product team? Because it answers so much. It says so much about culture, collaboration, decision-making, the role of product management. If there's one question and you could figure out what is this culture like, it would be asking that.

**Ken Norton** (01:10:20):
I think another great question for candidates is to ask them to pick an example of something they've shipped recently and just talk about how it came to be. How did the bill become a law? Was it somebody in sales yelled and it got added to the backlog and it was the next thing? Is it a group of people together understanding customer user needs through discovery and ideating and trying some things and testing it? It says a lot about what it would be like to work there, particularly when it comes to empowerment and product culture. So those are probably two good questions.

**Lenny** (01:10:58):
Those are really good questions. I'm going to steal them. Final question, who else in the industry do you respect as a thought leader? I imagine this list is very long, but what comes to mind?

**Ken Norton** (01:11:06):
Well, this list is all of my fellow podcast guests on your podcast, Lenny, which is, speaking of imposter phenomenon, is just an incredible group of all the folks that I love and admire. I think, though, because ... Maybe I'll answer it a little bit outside of product, because I would worry that I would leave out too many great names.

**Ken Norton** (01:11:26):
In the realms of leadership, Amy Edmondson is somebody I really admire. She's done a lot of the work on psychological safety. I really, really value her work, her contributions. There's a guy named Tom Garrity, who has a newsletter about psychological safety. I think he's collaborated with Amy before. It's one of the best, not the best newsletter I received, Lenny, maybe the second best, about psychological safety for those of us that are wanting to create environments where people can really thrive and do their best.

**Ken Norton** (01:12:05):
In the coaching profession, I mean the coaching profession emerges from the humanist psychology traditions or the client-first work of ... Carl Rogers and Abraham Maslow are intellectual heroes of mine. They're both dead. I don't know if we're supposed to talk about living people here, but definitely as I think about in my profession, they really set the stage and created the environment that coaching could even exist. So I'll include them.

**Lenny** (01:12:36):
Amazing. Ken, this was such a special episode, unlike any other podcast that I've had so far. I can't wait for people to listen to it. Before I let you go, where can folks find you online if they want to reach out, learn more, and then how can listeners be helpful to you?

**Ken Norton** (01:12:51):
Yeah, bringthedonuts.com is my home on the worldwide web. All my writing is there. You can get in contact with me there. I have a newsletter that I am occasionally send out, but you can find all the stuff that I've ever written and get in contact with me there.

**Ken Norton** (01:13:09):
The how to help be helpful question is a really easy one to answer, but that brings me a lot of joy, which is just keep being awesome product folks. You're so much my tribe. You're so close to my heart, all the work that you do, everything you bring into the world, the amazing products that we get to use that I'm sure you're working on right now that we haven't even seen yet, that you can't wait to share with us, and the cultures and teams that you make better, so your very existence. So I would say you can be helpful to me by just keep doing what you're doing.

**Lenny** (01:13:41):
What an awesome answer. Thank you for being here, Ken.

**Ken Norton** (01:13:43):
Thanks for having me, Lenny.

**Lenny** (01:13:46):
That was awesome. Thank you for listening. If you enjoyed the chat, don't forget to subscribe to the podcast and, even better, leave a review, which helps a lot. You can also learn more at lennyspodcast.com. I'll see you in the next episode.

---

## [7/20] How to create a winning product strategy | Melissa Perri

**Lenny Rachitsky** (00:00:00):
There's this whole concept of SAFe, basically Scaled Agile, right?

**Melissa Perri** (00:00:03):
Scaled Agile Framework came out of the desire to figure out how do we scale Scrum and different processes. I do not recommend using SAFe. Every single person I have talked to who likes SAFe, found success with SAFe, they ended up ripping it up and making it into something else.

**Lenny Rachitsky** (00:00:18):
You've been up close and personal with a lot of companies working with product owners, Scaled Agile, and all these things.

**Melissa Perri** (00:00:23):
This product owner role did not emerge from product management as we know it today. It was a way to help the developers prioritize what to work on. I ended up going to a ton of Agile conferences and speaking about product management, and I started to learn that there was this product owner role in Scrum.

**Lenny Rachitsky** (00:00:39):
It feels like it's growing. More and more companies are adopting this as the way to work.

**Melissa Perri** (00:00:44):
A lot of large companies turn to Scrum or to the frameworks, and it's because they traditionally didn't grow up building software. When you look at agile methodologies, what we're really saying there is we want to be able to move quickly and deliver great value to customers. If you embrace those principles, you're going to do well.

**Lenny Rachitsky** (00:01:05):
Today my guest is Melissa Perri. Melissa is a legend in the product management community. She's the author of the foundational book Escaping the Build Trap, and her most recent book Product Operations. She's also the CEO and founder of The Product Institute, which trains product managers at all levels. She's trained PMs at almost every Fortune 500 company at this point, and in our conversation we dive deep into a topic that I don't spend a lot of time on on this podcast, product owners, Scrum, Scaled Agile, and building product at very large non-tech companies.

**Melissa Perri** (00:02:19):
Thanks, Lenny. Thanks for having me.

**Lenny Rachitsky** (00:02:21):
First, let me give a little context on this conversation that we're having. I think it's going to be a little bit unique. I was doing a deep dive on the job market in tech, and I saw something that was really surprising to me that the product owner role was the third-fastest growing role in tech, and this was just in the US, the data I was looking at, but I think it's probably true broadly. This was extremely surprising to me because I've never worked with a product owner, I don't hear anyone in my circles talking about product owners, I've never wanted to hire a product owner, and it feels like it's just this very different part of the tech ecosystem that you don't hear a lot about on podcasts like this, and it's clearly growing so I felt like it'd be really helpful to spend some time helping people and helping me understand this part of the world.

**Lenny Rachitsky** (00:03:08):
I asked you to come on to talk about this. You've been up close and personal with a lot of companies working with this way of working with product owners, Scaled Agile and all these things, so I couldn't think of a better person to have on here to help us understand what's happening here, and also just to help people do this better. Melissa, thank you again for coming on and helping us understand this.

**Melissa Perri** (00:03:28):
Yeah, I'm excited to talk about this. I have been really passionate about this topic for many years and I've been talking about it in both agile circles and product management circles, so pretty excited for the listeners to hear what else is going on out there.

**Lenny Rachitsky** (00:03:43):
**Christina Gilbert** (00:05:13):
Yes, thank you for having me on, Lenny.

**Lenny Rachitsky** (00:05:15):
What is the latest with OneSchema? I know you now work with some of my favorite companies like Ramp, [inaudible 00:05:22], and Watershed. I heard that you just launched a new product to help product teams import CSVs from especially tricky systems like ERPs.

**Christina Gilbert** (00:05:31):
Yes. We just launched OneSchema FileFeeds, which allows you to build an integration with any system in 15 minutes as long as you can export a CSV to an SFTP folder. We see our customers all the time getting stuck with hacks and workarounds, and the product teams that we work with don't have to turn down prospects because their systems are too hard to integrate with. We allow our customers to offer thousands of integrations without involving their engineering team at all.

**Lenny Rachitsky** (00:05:53):
I can tell you that if my team had to build integrations like this, how nice would it be to be able to take this off my roadmap and instead use something like OneSchema, not just to build it, but also to maintain it forever.

**Christina Gilbert** (00:06:05):
Absolutely, Lenny. We've heard so many horror stories of multi-day outages from even just a handful of ad records. We are laser-focused on integration reliability to help teams end all of those distractions that come up with integrations. We have a built-in validation layer that stops any bad data from entering your system, and OneSchema will notify your team immediately of any data that looks incorrect.

**Lenny Rachitsky** (00:06:24):
I know that importing incorrect data can cause all kinds of pain for your customers and quickly lose their trust. Christina, thank you for joining us, and if you want to learn more, head on over to oneschema.co, that's oneschema.co.

**Lenny Rachitsky** (00:06:39):
Before we get into the history, is there just anything broadly that you think might be helpful to share before we dive into the history of the product owner role and all these things?

**Melissa Perri** (00:06:46):
Maybe it'll help to set some context of where did I see all of this start emerging as well. When I started in tech, I was very much a product manager, never heard of the product owner role before in my life. In Escaping the Build Trap I talk a lot about how we used Scrum when I started working with this team in a startup, and it was the first time I ever heard of it. That was 2011. At the time, the person who was teaching me about agile was very like, "Hey, this is flexible. We're just going to break things into sprints. We're going to sit there and actually talk about the work. This is made for us to actually get better at our jobs." We were pretty sold on it and it was never dogmatic. As I worked at other companies, I found that they were being a little more dogmatic with their Scrum, with their stand-ups, how we actually run things.

**Melissa Perri** (00:07:36):
Then I started speaking at conferences, and one of the first conferences I spoke at in New York City was called Lean UX, and there was a bunch of people from the agile world there too. I learned that this was much bigger than what we were learning in my company and what we were doing in these companies. There's this whole group of people out there practicing agile, and I was like, "Oh, this is cool. I want to learn how to do things better. Teach me about your philosophies." I ended up going to a ton of agile conferences and speaking about product management.

**Melissa Perri** (00:08:04):
At the time, people were really excited to hear more about it, and I started to learn that there was this product owner role in Scrum where I was talking more about how we traditionally talk about product management, understand your customer, go out test things, make sure there's a hypothesis, don't just blindly build what you want to build. I found out that that was not the case in a lot of these companies who are adopting Scrum and introducing a product owner role, so I started doing a lot of trainings through my school product institute and I'd get called into these large companies, all these large banks, probably around 2014, 2015, to help them learn product management. I was really excited about this because before, they didn't want anything to do with it. They were like, "I don't know what product management is. I don't need this."

**Melissa Perri** (00:08:47):
I go in to train people and I found that a lot of them had been going through an agile transformation and they had all of these new product owners where they came in and they basically said, "Hey, you're a product owner now. Your whole role has changed." They came from all different backgrounds. Some were developers, so a lot were business people who worked on the banking side, a lot were business analysts, some were project managers, but they just collectively took a bunch of people and said, "Tada, today you're going to be a product owner because we're going to do agile now." I will come in and help train these people.

**Melissa Perri** (00:09:20):
What I found was that there was a really big misconception about what those people should be doing compared to what they teach in agile and Scrum versus what we all consider great product management. I've been trying to fill that gap for the last almost 10 years working with these companies here. Then I would go to their leaders and at the beginning of these agile transformations, I'd be like, "You can't just do Scrum. That's not going to make you amazing at delivering products. There's so much more to this." The leaders didn't quite understand that.

**Melissa Perri** (00:09:51):
I'm noticing this really big shift in the industry where we're finally getting there. A lot of companies are doing it well now. Capital One is a great example that took their agile transformation and started adding product management on it, and they've really turned that around in the card business. So many organizations are still at the beginning of this journey and they're at the place where I saw people 10 years ago. I think there's still a lot of companies out there. Maybe we take it for granted in tech or in Silicon Valley about how many companies are doing this and how big this scope is where they're making these roles, but they're not really doing product management end to end. That's where I've seen all of these areas and I've been trying to help organizations for the last 10 years really set up robust product management practices. It's not just one piece of development, it's how do we actually build better products?

**Lenny Rachitsky** (00:10:42):
I love this example of Capital One. It can work really well and you can get to a place where it's actually really productive. There's a few ways we can go about this. Do you think it would be helpful to talk through the history of the product owner role just like where it initially emerged?

**Melissa Perri** (00:10:56):
Yeah, I think that's a great place to start. I think it brings a lot of context too to what's happening. People forget about the history here. When I explain it to people, I say we had product managers in Silicon Valley, right? They were in Google, they were in all of these companies, Amazon, and they were born out of this business role. From a software native company, your software is the business, right? It's what you sell, it's what you actually look at. Our product managers in Silicon Valley, they're doing market research, they're talking to customers, they're working with developers, they're iterating, they're doing the end-to-end product management.

**Melissa Perri** (00:11:31):
What happened on the other side of things, especially in large companies, is the emergence of product management from Scrum, from product ownership. That's usually the first time these companies were introduced to product management was from implementing a product owner role and then going, "Hey, we're still not meeting our goals. Are we building the right thing?" Then they started thinking product management. Where that role came from is Scrum. If we go back and talk about the history of agile, agile was a movement that got started by software developers. In 2001, the Agile Manifesto was written. A bunch of developers got together in Park City, Utah, they were all skiing together and they said, "Hey, we've been independently all working on how to develop software better."

**Melissa Perri** (00:12:18):
Some people were practicing Scrum as we know it today. That was Ken Schwaber, Jeff Sutherland. There were people who were doing different types of agile frameworks as well, Kanban, where you were moving it through a Kanban board. There was behavioral-driven development, there was feature-driven development. That was the style of agile. There was XP, extreme programming, that was started by Ron Jeffries. All of these people found each other saying, "Hey, we've been trying to push the boundaries of how do we develop better software," and they got together and they wrote the Agile Manifesto as we know it today.

**Melissa Perri** (00:12:51):
The Agile Manifesto is really just a guideline on how they're striving to not just be people who code what people want, but building better products. How do we build better products through software development? The premise to remember this is, and I keep saying it, but they're all software developers. Nobody was a product manager who went to that meeting. Nobody who wrote the Agile Manifesto was actually a product manager. I've spent a long time talking to these people as well over the past 10 years just saying, "Hey, how did this come about? Where did this come from?"

**Melissa Perri** (00:13:23):
The one person who was really close to them who was a product manager was Jeff Patton, but he never signed the Agile Manifesto, he wasn't at that meeting. He talked to them a lot, he was able to see what was going on, but all of this was a purge from how do we build better products from a development perspective. That's really important to know. Two of the people who signed the Agile Manifesto, Jeff and Ken, as I was talking about, they were independently coming up with Scrum on their own in their different companies, and they got together and started to codify it and they said, "This is how I'm doing it, this is how I'm doing it." They ended up writing the Scrum Guide. The Scrum Guide is what a lot of people base their agile practices off of today. In the Scrum Guide, it outlines a bunch of roles that you would do on the development team, and then it says how you should be developing products.

**Melissa Perri** (00:14:11):
Most people out there are working in Scrum today, and what they say is, "Let's break things down into two-week sprints." You can change the length of your sprint if you want to, but two-week sprints is pretty standard at the beginning. We define what we're going to work on in the backlog. It's the product owner's responsibility to define what goes into the backlog, write down the user stories for it, do all that. Then the development team comes in, they discuss it, the product owner prioritizes it, they ask questions, and then the development team commits to what they want to build and they go out and do it. At the end, the result is a potentially shippable product, not necessarily shippable, but potentially shippable.

**Melissa Perri** (00:14:48):
They're trying to break it down into small chunks and build things instead of what they had been doing in a lot of companies, which was building stuff for three years and then releasing it in a big bang. What all of the people who signed the Agile Manifesto realized was if we do it the other way, if we do a waterfall type environment, agile waterfall, that's where we go across, there's a lot of risk because we don't test it with the customer and we don't get feedback on it if we spend three years building it and never show it to somebody. It really approached a different way of building software. It said let's chunk it down and try to get feedback faster. Really noble intention.

**Melissa Perri** (00:15:24):
In the Scrum guide though, it introduces these new roles. We have developers as we know and love them, we also have a product owner, then we have a Scrum master, and the Scrum master is in charge in Scrum of actually helping people do Scrum better. That's literally their job. How do I do Scrum better? How do I make sure that the team is working well together? They host things like retrospectives where at the end of a sprint we say what went well, what didn't go well, how should we actually inspect and adapt our process. The product owner is where things get murky.

**Melissa Perri** (00:15:57):
The product owner in general first showed up with Scrum, and if you go and you read the first Scrum guide, which I pulled up and started reading, because I've been very fascinated about how this is described, it says that the product owner is responsible for maximizing the value of work done, the team does the work. Interesting, because now the product owner is not quite part of the team. The team consists of developers with all the skills to turn the product owner's request into the potentially shippable increment each sprint. The team is usually seven plus or minus two members.

**Melissa Perri** (00:16:29):
Then when you go further into the first version of the Scrum Guide, it does say that the Scrum master works with the customers and management to identify and instantiate a product owner. The Scrum master teaches the product owner how to do his or her job in order to optimize the value of the use of Scrum. If they don't, the Scrum master is held accountable. Then it's got another tip if we go deeper into this. It says per commercial development, the product owner may be the product manager. For in-house development efforts, the product owner could be the user department manager.

**Melissa Perri** (00:17:01):
What's interesting is that that was the first version of the Scrum Guide, and I get into arguments about the Scrum Guide with people all the time. 2013's version though, the more updated one that you could go and find is the one that almost every company has run an agile transformation off of. It loses that thing that says the product manager could be the product owner. It doesn't say it anywhere in that guide. This was the first version, and you can kind of tell it was an aside. It's like, "Oh, by the way, the product owner in Scrum doesn't need to be a product manager, it could be the customer, it could be a developer." It's usually the customer.

**Melissa Perri** (00:17:34):
When they were writing this too, sometimes the customer was an internal person at a bank or somewhere where we were building software who was asking for the software. They were like, "Go build me an internal tool. Go do this." Now we're just asking for requirements inside a company, and that's where you can start to see how the product owner role kind of evolved into somebody going to ask, "Hey, what do you want me to build? What's required here?," and then just listening to somebody come back and say, "I need this feature, I need this feature, I need this feature." Scrum doesn't describe how to get the stuff into the backlog, and it didn't in the 2013 manuals. The manuals have all been a little bit better, they've all kind of been updated since then, and they do describe it has to start with the vision a little bit more, you have to break down the vision for the product and get in there, but none of that existed in the early versions of Scrum.

**Melissa Perri** (00:18:29):
When people got trained on how to be a product owner, what was happening here is, and this is the whole other world of Scrum over here, when people get trained to be a product owner, it's usually a two-day class where they teach them, "Hey, this is how you break down a backlog. This is how you do stand-ups with your teams. This is how you think about prioritizing work. This is how you manage your backlog, prioritize it for the developers. This is how you work with the retrospectives," but it doesn't teach them about experimentation, it doesn't teach them about market research, it doesn't teach them about data, it doesn't teach them about any of the things that we need to be a product manager.

**Melissa Perri** (00:19:06):
Then what happened was we went into these agile transformations at these companies and they said, "Hey, let's adopt Scrum because Scrum was built as a way to build better products faster." It's literally the tagline. Everybody was like, "Yeah, I want to build products faster. Okay, great. Let's do Scrum." All these large organizations back in the early 2010s, in the 2000s said, "Oh, we got to be better at software. How do we do this better? Otherwise, we're going to lose when it comes to innovation." They adopted Scrum as a way to build software faster.

**Melissa Perri** (00:19:42):
Now, what happened is in order to do Scrum, Scrum basically sells training. That's what Scrum does. All of these agile coaches would come in and teach the product owners, newly minted product owners, took all those people, made them into product owners, put them through a two-day class and then say, "Go." That was the beginning of all the agile transformations, and that's where a lot of companies still are today. This product owner role did not emerge from product management as we know it today, it was a way to help the developers prioritize what to work on, but that was it. The product owner was held accountable for making sure that they were working on the most pressing things or the highest value things, they do say that, but to me, if you look at it from a developer perspective, it's also the person where you can say, "Hey, well, you told me to build that, right? We didn't build it wrong. You told me to build that."

**Melissa Perri** (00:20:35):
It almost gets into consulting territory where you're like, "Okay. If the product owner prioritized all this stuff for me and told me what to do, I can't be held accountable if it was the wrong thing to build." Some of that stuff does come up in a lot of teams that struggle to adopt agile, to adopt Scrum. I feel like there's a big misunderstanding out there about what is this role and what should we be doing, but the premise of this is when we talk about Scrum, it's just one piece of the puzzle, and when people talk about agile now, they almost always associate it with Scrum.

**Melissa Perri** (00:21:10):
I was actually Googling agile methodologies, and like I said, the other ones, Kanbans is an agile methodology, XP is an agile methodology. They don't have product owners, they do not exist in those methodologies. There are four developers to work on things, or teams to work on things. XP would consider product managers in the teams as far as I know it, but Scrum kind of sees it as a separate thing.  Agile methodologies, everybody says, "Oh, they're Scrum now," so it gets a bad connotation out there about what to do with it. I think Scrum if you do it well is bad, but you have to understand that it's just one piece of building great products, it's not the whole thing, and companies will adopt it like it's going to radically transform everything. To be fair, a lot of times it's sold that way too.

**Lenny Rachitsky** (00:21:59):
There's a bigger picture question that's coming to mind as you talk about this. I'm imagining founders listening to this and smaller companies listening to this be like, "Why do we need any of this?", especially Silicon Valley startups, "We're just going to build stuff. We don't need these frameworks, we don't need a Scrum master. We just have awesome developers and product managers and we're just going to build awesome stuff." I don't know anyone that has worked this way that has built amazing things. Can you talk a bit about who ends up looking for solutions here, where this even comes from, what companies need help here versus, "I just don't need any of this?"

**Melissa Perri** (00:22:36):
A lot of large companies turn to Scrum or to the frameworks, and it's because they traditionally didn't grow up building software. They're looking at how do I implement something that has rigor at scale, and that's where you see a lot of Scrum come up. Now, I've seen startups using Scrum. Some of them do it fine, they understand that it's just more about trying to get things out the door every two weeks to test it with customers. I think if you keep that philosophy, like I said, I used it and we didn't have a lot of rigor around it, that was fine. When we were doing Scrum, when I did it with my team back in OpenSky, we got to this point where we were like, "Two weeks is too long. We're just going to ship things every week."

**Melissa Perri** (00:23:12):
We just talked to each other, we skipped stand-ups, which is sacrilege in Scrum, but we kipped daily stand-ups. We didn't need to stand around and talk about it, we talked to each other every day. For me, what was amazing and where I see teams actually thrive when they start using Scrum is when you go and talk to people. You're having the conversations about the work, you're breaking it down, you're understanding it, so the developers and the rest of the team can go hit the road running and people can ask important questions. If you're not doing that, that's where I think things like a framework help, but if you already are doing that, you don't need a framework, you don't need Scrum, you don't need to be prescribed to this two-week sprint or anything like that.

**Melissa Perri** (00:23:52):
As long as you have a methodology, it doesn't even have to be a defined methodology. As long as you have a way of working that gets things out to customers, well, who cares? Who actually cares? Where there's a lot of, I think, baggage in the industry and where I hear product managers get really frustrated and other people as well, developers too, is that when you do Scrum by the book or how people teach it and how they write about it, it's a million meetings. I know they were put in there so that people were forced to talk, but when you already know what you're supposed to work on, why do you need to keep doing meetings? Shouldn't you just go do some work?

**Melissa Perri** (00:24:28):
A lot of developers complain, a lot of product managers complain that Scrum has too many meetings and they don't actually get to do work. That's where I think you have to go back to the inspect and adapt part. A lot of people who are very religious about Scrum will come and yell at me about this. They're like, "Oh, well, that's not how it's supposed to be. You're supposed to inspect and adapt." Agree, but a lot of people aren't doing it and that's the piece where you go and you say, "Is this serving us? If not, let's get rid of it. Let's not do those types of things." When you're a small startup, I don't think you need a lot of this overhead. It's really much designed for larger scale companies, and those are the ones that you see really adopting it.

**Lenny Rachitsky** (00:25:06):
From what I've seen on the data, it's also companies that are as you I think alluded to at the beginning, not necessarily software first, product first companies. Feels like it's very common in banks and telecom companies and companies that aren't product First and software first.

**Melissa Perri** (00:25:21):
There are SaaS companies that do Scrum out there and they like it, and I don't think they're very dogmatic about it.

**Lenny Rachitsky** (00:25:27):
Got it. Yeah.

**Melissa Perri** (00:25:28):
They do it for a reason of just trying to provide some more context to their teams about how to work together at scale. I've also seen places where they don't prescribe whatever methodology you want to work with for the teams, but instead they'll spend a lot more effort breaking down the road maps, thinking about what are we going to do each quarter, trying to set those themes, and then they just let the teams run, and that works as well. I think it really depends how they adopt it, but I would say it's not a hard and fast rule that no startups are doing this. Some are doing it, I just don't know how it's going for them. To me, it might be overkill if you're doing that with a team that's pretty experienced in doing this.

**Lenny Rachitsky** (00:26:12):
What I was insinuating is less just Scrum as a general idea and more very structured rigid processes and also product owners. Then there's this whole concept of SAFe that we can talk about. Should we get into that or should we talk about product manager versus product owner and just the challenges people have there?

**Melissa Perri** (00:26:33):
Let's talk about SAFe because that's where a lot of this started to get Confusing

**Lenny Rachitsky** (00:26:33):
Okay, cool. Let's go there. Yeah.

**Melissa Perri** (00:26:37):
Scaled Agile Framework came out of the desire to figure out how do we scale Scrum and different processes and bring it to organizations at scale. It originated from a more structured approach to agile too called Rational Unified Processing. Now, SAFe wasn't the first thing that started at scale. There was also LeSS, which is a Scaled Agile Framework, and then Jeff Sutherland who did Scrum has Scrum@Scale. It's not the only scaling framework out there. There's a lot, there's actually a lot out there, but SAFe was one that was marketed the best. The way it's marketed is will tell you everything you need to do, to do all of your agile teams with Scrum and put them all together.

**Melissa Perri** (00:27:22):
The idea behind SAFe was that Dean Leffingwell came up with it. He wanted to really show how you tie multiple teams together at scale in an organization and how do you bring some rigor and process to that. The executives at really large enterprises, we're talking tens of thousands of people, they love SAFe because it prescribes a lot of an operating model of what to do when it comes to development, but it also gets billed as like, "Hey, this is the whole model for you to go do software." If you look at it, it's a big map that everybody kind of makes fun of a little bit, and it describes all different things on it if you look at the map. You can click in and you can see the definitions and you can see what's going on in the areas.

**Melissa Perri** (00:28:10):
The SAFe image has gotten bigger and bigger over time. I think, what is this? Version six. I do know a lot of people who worked on SAFe, so I know a lot of trainers and I've worked with companies. The first time I was introduced to SAFe was when I was working with a bank back in 2015. I came in to train their product managers, I'm doing my training, we're setting them up on how to go talk to customers, talk about hypotheses, MVP, and somebody came up to me and they said, "Hey, Melissa, all of this is great, but I don't have time to go talk to customers because I'm a product owner." I was like, "Well, what are you doing on a day-to-day basis? What don't you have time for it?", "I got to write my user stories." I'm like, "Okay. How many user stories do you write per day?"

**Melissa Perri** (00:28:53):
This was for the developers to have a full backlog so they could all work, right? She's like, "Oh, yeah. I spend pretty much 40 hours a day writing user stories." I'm like, "On what?" We're like, "What are you controlling?" She's like, "The login API for a bank." I'm like, "Can you log in?" She's like, "Yeah," and I'm like, "So what else are you working on? Is there a new initiative? Is there a new thing?" It's like, "No, I was reorganized into a team where I became the product owner. I have a product manager who goes and talks to customers, but then she comes and she tells me what to build, and then I write the user stories around it and I put it into the backlog for the teams." I was like, "What is this?" Then they said, "That's SAFe. This is what we're working towards."

**Melissa Perri** (00:29:34):
This was my first experience with SAFe, and then I ran into another company that did it, another company, same thing over and over and over again, where all these product owners were just basically trying to keep these backlogs full for developers, and they were working on such a narrow level. When a lot of organizations too I saw it reorganized into agile teams, they did it by component. Everybody was over every tiny little feature, and these teams were massive, super huge scope, and some of the stuff was just not prioritized. It was done, you didn't need to work on it. They were finding work to do so people wouldn't get fired. That's how the product owners operated. There was all this legacy baggage sometimes in companies where they were all re-put on things by component, and they're just making up work to do.

**Melissa Perri** (00:30:21):
SAFe introduced this kind of split between product manager and product owner, and if you look at the map, the product owner is part of the agile team where they sit with the Scrum masters, which is a team coach that they call here and the developers, and then the product manager is sitting with a system architect and what they call a release train engineer. What SAFe does is they pull a bunch of agile teams into a release train and you get on the train when you're ready to ship things and you make sure that it all goes pretty smoothly to get to that potential shippable increment or that big feature launch that you would be doing with SAFe. 

**Melissa Perri** (00:30:58):
SAFe's really good at prescribing how to do that, they're great at describing how to do the release trains, how to bring those teams together, how to put them on it. Then they do this thing called big room planning where they get the entire release train together, all these teams, they put them in a room and in every quarter you're breaking down what we're all going to work on. Where I hear frustration from teams every time I come in and train them is that when you do big room planning, a lot of times it's a commitment. You start at the quarter, they haven't been doing good discovery because remember, these people have not been trained on good discovery so they don't really know what they should be working on, they haven't been out talking to customers a lot of times. They kind of scramble, they figure out what needs to happen. Usually they have a backlog of stuff that does need to happen, it just has to get done. They map it all out in a big room together, they commit to it, and then that's the quarter.

**Melissa Perri** (00:31:47):
They ask me, "When am I supposed to do discovery?" I'm like, "Well before that ideally you should have a vision. You should be breaking it down, you should be putting discovery into that vision, talking to customers, feeding that in there." Then I hear, "We don't have time to do that because we sprint back to back." I was like, "What does that mean?", and they're like, "As a team, we go and we basically do two-week sprint into two-week sprint into two-week sprint, and I got to make sure my developers are full. I got to make sure they have things to work on. If I go take time off to go talk to customers, which also is not my job as a product owner, it's my product manager's job, they'll feed me in what the customers are saying, then I break those down into features and I can work with the developers on it." That's how all of this stuff starts going.

**Melissa Perri** (00:32:32):
What happens in organizations that they don't understand here is that it's not the most efficient way to work. I see a lot of developers out there become almost ... How do you describe it? Reliant on the product manager or product owner to tell them what to do. Even though you build them this great vision and you explain what needs to happen, they go, "Oh, I can't work on it because the product owner hasn't prioritized it." Then they asked me, "If I don't have enough for the developers to do on feature work, what are they supposed to do?" I said, "I guarantee you there's a ton of tech debt they could be working on. You don't have to scope that out. Let them choose what's the most important thing. They should be working together as developers and architects to figure out how to tackle some of that tech debt, how to get into it while you're figuring out is this the right thing to be building."

**Melissa Perri** (00:33:23):
With all of this stuff, people feel like they don't have time because they're in a million meetings, and the expectations of these companies is that every sprint, we're delivering software towards these roadmaps that we promised in the last quarter and we're not checking to see if they're right, we're not checking to see if they're actually helping us move it forward, and a lot of times the organizations are not set up with the right feedback mechanisms, the right user research and the right data to tell us if everything is working so they can feed that in to the next release planning. They're just planning, planning, planning, breaking it down into sprints and going.

**Melissa Perri** (00:33:58):
SAFe is not good at describing how you do all that other work. In a lot of this stuff too, there's pieces that they put onto this map of SAFe where they're like, "Hey, you should do OKRs," and it's like, "This is what OKRs are. You should do a roadmap. This is what a roadmap is." How all of that cycle works together where you're balancing discovery and delivery and feeding it in is really confusing in organizations. Then what it's basically saying is a lot of the discovery work goes into the product managers, and the product managers, the product owners report into the product managers. What I've seen that doesn't work here is that you're basically making these product owners order-takers. They are extremely tactical, and then when it's time to actually be more strategic, let's say you want to be promoted to a product manager, some organizations, that's not even the same business line, not even the same career path. It's product owners go over here and product managers go here and they report into different people.

**Melissa Perri** (00:34:58):
If you ever want to move from product owner to product manager, a lot of times you don't get experience with the strategy, figuring out what customers want, breaking it down, looking at the market research, determining is this valuable, is this what we should be working on. They're not even getting exposure or a chance to do that because SAFe is like, "No, that's the product manager's job. Your job is to go really deep and work with the developers."

**Lenny Rachitsky** (00:35:21):
Wow, okay. A lot of this sounds quite absurd as someone hearing all of the details and looking at this image. That being said, many companies are adopting this. It feels like it's growing. More and more companies are adopting this as the way to work. I imagine the incentive is we just want to build great software and we don't know exactly how, and there's this process we can plug in and it'll help us do it. I guess thoughts on that, and do you find it can work or often works or often doesn't work? What is your experience with people adopting this and how it goes?

**Melissa Perri** (00:35:59):
I know a ton of companies that adopted SAFe about eight years ago and have gotten rid of it. Capital One just came out and said they got rid of all their agile roles, all their Scrum roles. They were early adopter of SAFe, they don't do it anymore. They wrote about that in the newspaper. I've seen it happen more often. Now, in a lot of our organizations too I'll see parts of them do SAFe and other parts not do SAFe. It could change business line to business line. I don't think though that people grasp how much it's still out there. I get questions on SAFe every single day on the podcast. Everybody asks me, "Why are we still doing this?" It's for what you said, executives buy SAFe because it's the only framework out there that basically draws them a map and says, "Plug and play, do this."

**Melissa Perri** (00:36:50):
That's why everybody's so excited about it because it's the only thing that specifies things to this level, and they went, "Oh, it's something I can understand, it's something that actually has definitions around it." To be fair, that was a great thing for SAFe to do as a marketing tool. Bravo, they created this thing that everybody wants, a good product to sell, but it's overkill, and that's what I keep hearing from organizations is it's basically taking the responsibility away from leaders to go figure their stuff out themselves as well. If you are a new leader and you've just been dropped into this role, I have tremendous empathy for them because yeah, where do you get started? How do you try to run a technology organization?

**Melissa Perri** (00:37:33):
Somebody came and told me, the CIO came and told me I'm in charge now. I'm in charge of all of the developers, or I'm in charge of all the product managers. Now, where do you start? I can totally tell why people adopt SAFe because you're like, "Oh, I've been looking for the handbook. I've been looking for something to do here." The problem is it's only solving a little bit of the puzzle, which is bringing those teams together. People do say it does really strains well, but it doesn't tell you also how to do your job as a leader, it leaves it all out. They talk about portfolio visions and portfolio management and SAFe there too, but more often than not, I come in and I find everybody above product owners and product managers, let's talk about directors of product, VPs of product, they don't know what they should be doing as a VP of product or a director of product. It's like, "What's my role? What should I be feeding in here?"

**Melissa Perri** (00:38:23):
SAFe doesn't even have that in there, that's not even a role. Product manager going up into those levels is not really there. What do you do when you own a whole product line in an organization? What you do when you're the head of product for a credit card at a bank, right? What's my job? Doesn't say that. There's a lot of people out there in these organizations that I've been working with who I'm like, "You are supposed to be doing strategy, and this is how you do strategy. This is how you go out and talk to customers. This is the patterns that we have in software. Are you doing a platform strategy? Do you need APIs? How do you think about your app strategy, rolling it out? How do you do this here?" All of that stuff doesn't quite come from ways of working, which is what SAFe is doing. It's about how do you do your jobs in those areas?

**Melissa Perri** (00:39:12):
A lot of organizations who adopt SAFe don't realize that you need a head of product, you need somebody to actually be feeding that vision all the way down and make sure it's breaking up around the teams and controlling that portfolio vision and doing all of these things into it. I have not seen SAFe slowing down by any means out there for people adopting it, I see more and more organizations adopting it. I think we take for granted too in Silicon Valley how many people are just starting on their journey for digital transformation. There's a lot of pharmaceutical companies, banks, insurance companies, they outsource their development or they had an IT team, but they never had to really think about it before because digital wasn't as important. Now they do.

**Melissa Perri** (00:39:59):
Some of these companies, most of these companies are Fortune 50 companies, right? Fortune 100 companies. I think a lot of the ones I see, at least banks, realized early on, "Hey, when it comes to apps and how people interact with our stuff, software is important," but there's a lot of companies that did not catch that train and they're just starting, and then they turn to things like SAFe because it gives them a guideline. "Hey, I've never done this before. I've been in this bank for 40 years. All I know is waterfall type development. What do we do?" Then we'll go, "We'll go look at SAFe."

**Lenny Rachitsky** (00:40:33):
I love that we spend time on that because I think it's really important. You can be cynical about all this and be like, "What the hell are people thinking? This is crazy," but as you described, people just have a problem to solve, they've never done this before, they look for solutions, they find something that seems right, they see other people doing this and like, "Okay, let's try this thing." What you've seen is it rarely actually works out the SAFe specific approach.

**Lenny Rachitsky** (00:40:59):
There's a few ways I think we can help folks. One is someone trying to do say an agile transformation or a digital transformation, your advice for how to actually do that better. Then I want to talk about say you're a product owner or a PM within an organization that works like this. What can you do? Maybe let's start with the first. Say someone's trying to figure out, "We need to build better products. Something's not working right." SAFe is an option. Your suggestion is don't maybe do that. What should people do? I know you're not going to have the answer in a short answer, but generally, how should people approach this?

**Melissa Perri** (00:41:33):
Yeah. When I've worked with companies on digital transformations, you want a development operating model. That's where a lot of these agile methodologies came out of. You have to understand that's just the development operating model, that's not actually going to help you with go-to-market, with launching your products and with product management. What I advise for companies to do is first sit down and say, "Hey, how do we think about building our operating model?" When I think of product operating models and what I do with companies is we break out how do you determine product strategy? Do you have a good product strategy? You look at your organizational design. How are we actually organized around our products? Do we have good coverage of product managers and do we have skilled product managers up and down the organization?

**Melissa Perri** (00:42:20):
Then we want to look at product operations. Do we have the infrastructure in there to help support these teams? Can they get the data to make decisions? Can they actually be in touch with customers? A lot of these large organizations haven't actually thought through many of those steps as well that enable product managers and development teams to be successful. They don't have ways for them to go and talk to customers. That's why they're not doing it. I have a lot of empathy for people in these organizations as well who can't do product management well because of the bureaucracy or the things around it. Leaders need to solve that, right? They need to understand what the role is and they need to open it up.

**Melissa Perri** (00:42:57):
Then we got to look at our culture and incentives. Are we just rewarding people for shipping as many things as possible, which is like, "Hey, just put everything you possibly can into that release train or that backlog," or are we coming back and saying, "Hey, is this valuable? Is this tying it back to our business?" Many organizations do not have a great product strategy, many large organizations that I've worked with, and it's that tying it back to the value piece, tying it back to, is this going to reach our company goals? If you are a huge organization and let's say making billions of dollars a year, and your goal is expand geographically, what are you doing in your portfolio to actually enable that? What products are you building to expand geographically? So many organizations don't have the transparency to actually even see that.

**Melissa Perri** (00:43:50):
One crazy thing, a lot of people give large organizations a lot of flack for, and I know Marty does this too, for focusing on processes. I don't think processes are the enemy here. For example, if I hear somebody really worried about getting a roadmapping tool in there or something like that, I'm like, "Yes, you need that because you have no idea what your 4,000 teams are doing." If they're actually coming back to the business goals, you have no infrastructure in there to be able to see that transparency. Those types of blocking tackling is absolutely necessary for a transformation for a organization to be stood up around software product management. You have to have the transparency to actually see those things.

**Melissa Perri** (00:44:29):
You do need to have enough process so that you as an organization can be efficient in getting things out the door, and that's what I think SAFe was trying to do, but it's not working because it's not solving the problems of the product management and it's not solving that problem of connecting the value back to the product teams. Instead, it's seen as a role that almost babysits developers or tells everybody what to do. Where's the discovery? Where do those things come in? I know with the SAFe image that we got over here, they try to drop things like Lean UX in there, which Jeff Gothelf thinks it's hilarious, but it's not really pulling it all together of how do we do this on a cadence? How do we help people go out there and actually talk to customers? How do we enable them to do it?

**Melissa Perri** (00:45:15):
If you're starting a transformation, it's not just thinking about how do we build the product, but you should also be thinking about how do we launch the product and how do we make sure this is the right product to do. That's the big pieces of it, and that's where all that product strategy comes in. You should also look at the career paths. This is what really bothers me about agile transformations and what bothers me with Scrum and SAFe is that when we organized in these large organizations into agile teams, we made all these new roles called a product owner, and so many organizations don't have a career path for them so they email me and they go, "What's my career path? What do I do next? Where am I supposed to go?"

**Melissa Perri** (00:45:59):
I've been saying for 10 years, this is not a team role, it's not just a team role, it's a business role and it rolls all the way up to helping you further your business. You have to make sure that people on teams can be promoted to running multiple teams, can be promoted to running an entire product line. To us, that's so simple in Silicon Valley native software companies, but it's still unheard of in other organizations. What happens too, and this is where I think leadership and C-suite needs to really pay attention, because we're transforming in this way of working, what happens is some of the roles that we had before do not serve us now. Maybe we don't need a million project managers, maybe people in the business who decided what we're going to build, are they the right people to bring with us on this next phase into product management? Can they learn? Can they grok software? Do they understand those pieces? That's what we have to ask.

**Melissa Perri** (00:46:58):
Organizations are so afraid sometimes to put these career ladders in because it kind of overhauls their traditional ways of working, and then they've got people who've been in these organizations for 40 years and now you're saying, "Hey, you're actually not in charge of that, the product manager is in charge of that," and that's scary. A lot of them get in the way because of that. If you really want to transform though, the C-suite has to be like, "Hey, we're going in this direction," and just put it down because I've seen it run by a lot of middle managers, a transformation run by tons of middle managers, and those are the jobs that are usually in most jeopardy when you start transforming and you have to re-skill and you have to figure out what to do, and they don't want to do that. They're not going to be the ones who jump up and down and say, "Hey, let's do this."

**Melissa Perri** (00:47:41):
There's a lot of people out there, I think, pushing organizations to try harder and to internally as well. I've worked with a lot of people who run these transformations who just really want it to work, and I think they do it with the best of intentions, but the C-suite has to understand this is not just a transformation project, this is a whole new way of working, and if we want a whole new way of working, we have to really rise to that occasion.

**Lenny Rachitsky** (00:48:07):
**Melissa Perri** (00:49:21):
I do not recommend using SAFe. Yeah.

**Lenny Rachitsky** (00:49:24):
Great.

**Melissa Perri** (00:49:25):
There are people who like SAFe. Let me just say this, there are people who found success with SAFe. Every single person I have talked to who like SAFe found success with SAFe, they ended up ripping it up and making it into something else. It's not actually SAFe by the book. If you do that, fine, that's any process. If you ended up adopting SAFe and you want to go back and look at it and say, "Actually let's just get rid of all the stuff that's not working and keep the stuff that is," fine, but being open to understanding this is not the way that we do good product management. There's not a lot in SAFe about doing good product management. That's the stuff that we have to understand. It could help in certain areas, and I do think it does help in certain areas, bring some rigor to things, but if you take it too far, it will destroy things.

**Melissa Perri** (00:50:17):
There's actually a great story about a water company in the Netherlands and they decided to adopt SAFe, and this was on the news a couple months ago. They decided to adopt SAFe in their IT teams and start working with it. They ended up going bankrupt, and the reason they ended up going bankrupt is because the teams were learning the processes for SAFe, they were taking so long to deploy their new invoicing system and payment collections that they couldn't collect payments from customers because they got so caught up in the process.

**Melissa Perri** (00:50:53):
That's what I see happen a lot in these organizations. Instead of talking about what's really important, which is, "Hey, how are we serving our customers? How are we winning in this market? How do we stem churn? How do we do all these things?", we're talking instead about, "What stand-ups are we doing? Oh, how do we do this release planning? Oh, my God, you guys didn't sprint back to back, you did it wrong." We're talking about work about work, but we're not actually getting into what are we achieving here, and that's the part I do not like about rigid processes when it comes to this.

**Lenny Rachitsky** (00:51:28):
That touches on the other theme I wanted to bring up is it feels like the stuff is a kind of replacement for skilled, talented people, a product leader that understands how to do these things and has product taste and has organized teams to build great product. It feels like people are just, "We don't have that so we're going to create this. This process is going to fix all our problems." Can you talk about just the importance of that, the people you hire to run these things as key to this, if that's true?

**Melissa Perri** (00:52:00):
In a lot of organizations, the people who buy SAFe, they have not run large scale technology organizations before, or they're new to this way of working so they adopt SAFe and they hope it works because it looks like a nice plan, like we said, to go out and do things. When you're doing a transformation, a lot of companies are pulling people into these roles for the first time. I've said since day one that I've been working with companies, it's okay and I think it's noble to want to train people and put them in different roles. Cool. If you're going to spend money upskilling your people, do that, but you also have to intersperse people who know what they're doing. I think at leadership it's really important to bring in somebody who knows what they're doing to help run this type of thing.

**Melissa Perri** (00:52:44):
There are more people out there and more leaders who have done this before because we've been doing this for 10 years. There's Shruti Patel, she's chief product officer at US Bank for small business banking. I just had her on the podcast. She worked at Shopify, she saw how great teams worked, and then she was able to come and help apply that at a bank. She's experienced, right? She's an experienced product person who comes in to help. Melissa Douros is the CPO of Green Dot Bank and she had worked at Discover Financial leading the transformation there, did all that work, and then could bring it to Green Dot Bank. She can see what needs to happen, what needs to actually go on here.

**Melissa Perri** (00:53:23):
We've got more and more people out there who have done this before who are looking for these opportunities to do it in the bank, and I think it's important for C-suite to bring them in to actually look at that. Where I've seen transformations be the most successful in all these organizations is when you do that mix, you keep some of your people, but you also bring people in to learn. I get hired all the time to come in and train. I've worked with almost every Fortune 50 company at this point, fortune 100 company too, and I get in, I come in to train a lot of product managers. We do it through Product Institute and we'll train everybody. What used to happen about eight years ago is they train everybody and they would say, "Go." Where do you go after you bring in the consultants to do training to keep learning? How do they watch other people in the organization do great product management if there's nobody in the organization who's done it before?

**Melissa Perri** (00:54:20):
Luckily I think a lot of organizations are realizing that, so more leaders are out there who are saying, "Hey, I've got to actually intersperse skills here. I need to bring in some more directors who are experienced here, some more individual contributors who are experienced here." Those organizations I think are wildly successful because they recognize it and they say, "I've got to make sure that people can learn from others." That's how you keep developing, that's how we all keep developing, it's not just doing all external classes. That's where I think these things become powerful. You could do that at all levels. You don't have to just do it with the teams, you could do it at director level, you could do it at VP level. That's how we should be thinking about this.

**Melissa Perri** (00:54:57):
Now, there are some CPOs out there and some VPs of product in these large organizations who are new to this way of working, but they've committed themselves to learning and to trying to figure out how to do it best. They're not saying, "Hey, I'm just going to adopt SAFe or I'm just going to do whatever is over here," they're actually saying, "What don't I know?" I'm watching them go out to talk to other CPOs, do all these other things. They usually have great market knowledge, great business knowledge, and they're fantastic at strategy, and then they hire people underneath them who are great at the other pieces like the execution and getting the software at the door. I think those people are successful in it as well because they notice their skill gaps and they hire for it just like any great leader would.

**Melissa Perri** (00:55:41):
In these organizations, I do see sometimes SAFe for something being a crutch for people who don't know what they're doing to bring in. If you really think about, "Hey, how do I make this better?", and have that continuous learning mindset and that way to want to propel this forward, I think you'll consider other options and start to think about broader than just SAFe, broader than just agile, what do we need to make this successful?

**Melissa Perri** (00:56:07):
The key part of this too is recognizing that product management is not just this role in Scrum. I say this in my talk too, I say Take Scrum away. You still need product management, right? Product owner doesn't exist without Scrum, that's not a thing, but you still need product managers and that's why all product owners should be product managers, they should be fundamentally product managers. That's why I do not like these career trajectories that keep them separate. Sure, if you want to have a principal IC product manager like they do in a lot of large Silicon Valley companies, perfect, let people keep working on those things. They don't have to go into management, but that doesn't mean they're different. Between an IC product owner and an IC product manager, it shouldn't be different there.

**Lenny Rachitsky** (00:56:55):
Perfect segue to where I wanted to go next, which is say you are a product owner today listening to this and you're like, "Man, this is exactly my life. What can I do?", what's your advice to folks in that role right now about how to potentially become product managers, build the skills they need to not just be stuck in this career path that doesn't go anywhere?

**Melissa Perri** (00:57:14):
Yeah. I think the first thing is bringing awareness to that your role is more than just working with the developers. A lot of leaders argue with me that we need product owners because it just doesn't scale. You've seen massive companies at scale where they don't have any product owners. I do not understand that. It's a weak argument to me, it's a very weak argument. It just means you don't know how to distribute the work evenly and give a little bit of strategic guidance to product owners so that they can gon, or product managers, on a team so that they can go and build visions and cut down features and stuff like that. If you're a product owner and you're like, "Hey, I don't have the opportunity to talk to customers, my product manager does that. I am just working with the teams. I want to be more strategic, I want to think longer term," I'd say try to take some ownership over that and push back on the things that are being given to you.

**Melissa Perri** (00:58:04):
I was doing a workshop for Mind the Product back in the day, and I had a product owner in my workshop and she said, "I don't think that things we're working on," they were doing SAFe, "are the right things to work on." I said, "You should bring this to your manager," and she was like, "I don't know. I'm going to get fired. I don't think it's the right thing. What am I going to work on if we're not going to work on this?" I'm like, "Well, this is the beauty of product instead of project, we stay with the product." Just because your project ends doesn't mean that you lose a job. She put together this whole thing, went and said, "I don't think we should be working on this," and they promoted her. They were like, "Fantastic." She took this leap of faith and went out there and started saying, "This is more. We need to do more."

**Melissa Perri** (00:58:44):
I think if you're a product owner and there's no career path for you, start asking leaders what your career path is because it's going to make them go, "Oh, great question. What should the career path be?" There's a lot of literature out there about how we make career paths, so you can start there. Ask what's next for you after this product owner role. I would ask the product managers if they're doing all the customer research, see if you can do some customer research with them. Go sit in on this. A lot of them will say, "I don't have time. I don't have time to do this." Strip back all the user stories you're working on, stop thinking about it as a quantitative metric that needs to just go up and up. Instead, really think about the value you're delivering with your team. Is this the right thing?

**Melissa Perri** (00:59:24):
When you talk to leaders and when you present your case, you say it in a way of, "Hey, I'm working on X, Y, and Z feature. What's the goal here? When we release this, what do we hope will happen?" I think that's one of the best questions anybody can ask if they're worried their company is not focused on outcomes. What do we hope will happen when we release this? What metrics are we going to change? How do we instrument it to make sure that's true? Then we can go back and actually see if it changed. One simple question to get alignment on it, and then you can start to say, "Oh, that didn't work or this did work." Great. Why did it work? You can open up those conversations.

**Melissa Perri** (01:00:00):
I'd say there's a lot of things you can do to help move your companies forward, and I have seen in a lot of these organizations too, a groundswell of product owners and product managers saying, "Hey, what's next for me? What's going on?" That makes the organizations go and figure it out. I was working with one Fortune 10 company not too long ago, their C-suite, I've been working with them for a very long time and they're finally like, "Hey, we're going to codify the product manager role and we're going to have it all the way up and down our organization, we're going to make roles, we're going to make responsibilities." To me, that was music to my ears, but the reason they were doing it too is because they noticed there was a lot of churn in the organization in that role, and they also realized it's a critical role.

**Melissa Perri** (01:00:44):
They're losing good people because people from the outside are coming because they want to work for this great big organization that's doing super well, fantastic, but they get in there and they go, "Where's my career path? What am I supposed to do? Where am I supposed to go?" A lot of leaders are out there now realizing, "Hey, we do have to get our stuff together," and the only reason they're coming to this conclusion as well is because they're looking around seeing other people doing it and they hear it from the teams, they hear it from the product managers. I don't want people to think, "Hey, I have no power. I'm in a 10,000 person organization." The more you bring this up, the more your leaders will respect it because they don't want to lose you, they don't want to lose good people. If you want to be great at your job and you need more support there, speak up, speak up.

**Melissa Perri** (01:01:31):
At a certain point, I do tell people this. If you feel like you can't do great product management in your organization, try to find another organization. I know that is hard to say and I respect people are tied to insurances and it's hard to change jobs, but if you do have the opportunity to look for another organization that does it well, I would go there. I would also say in large corporations too, I've seen certain business lines and certain divisions do it super well and then others not. If you are in a large corporation, maybe think about moving internally, laterally to a different team and seeing if you can work there. I'd find the leaders who know what they're doing and go work for that. That's usually the best move here.

**Lenny Rachitsky** (01:02:11):
The point you made about how a lot of companies don't have any product owners and have scaled very wide, just to reinforce that in the data dive that we did on job market trends, no tech company has a product owner basically, no top tech company. I know there's an important distinction here. These are tech, software first, product first businesses where their business is the software they're building, and a lot of the companies we're talking about here are not that. They're banks and telecoms, pharmaceutical companies. I get that it's a very different world, but I think it's important to highlight, "You can become very big." Google has no product owners as far as I know, Amazon, Microsoft, Netflix, no company you've heard of that's a tech company has a product owner. They're all product managers, they're all product managers.

**Melissa Perri** (01:02:56):
Yeah. I don't want people to think that there aren't people who build great software in these large corporations too because there are. There's pockets of people who are doing it super, super well. If you are one of those people who's been pushing the boundaries, doing great work, and your title is a product owner, what I always tell people on your resume, if you're looking for your next job so that you're not pushed out, let's say, of these large corporations like a Google or somewhere like that, and that's where you want to work in a tech firm, make sure you describe how you did your job from a value perspective. Do not talk about your agile cadences. Get Scrum out of there. Talk about what value you brought to the users and what metrics you moved, and that's how your resume should be laid out.

**Melissa Perri** (01:03:40):
I do read tons of resumes to hire people, and also chief product officer, same thing. If I see immediately implemented Scrum processes across the organization, I'm like, "No, that's not what I need. That's not what I was looking for." I was looking for what are you going to do to push the strategy in that part of the organization? What are you going to do to actually build better products for customers? Then when you get into the interview, you can talk about what things you did to do that, but you want to make sure that you're focused on really understanding the customer and translating that into great products, and the outcomes that we were looking for when you do it on your resume, I think that's important.

**Lenny Rachitsky** (01:04:15):
Okay. I want to spend more time here because this is so important. This is highlighting here's the difference between a product owner and a product manager. If you want to move into product management and become a great PM, if you're a product owner today, even if you're not a product owner and just want to get into product management, can you again just highlight here's the big difference and here's the skills that people value most in a PM versus a product owner.

**Melissa Perri** (01:04:38):
Yeah. When I see product owners write out their resumes or describe their job functions, they always approach it from a process standpoint. I prioritize the backlog, I worked with the developers to break down the work, I checked the developer's work and did the acceptance criteria, I wrote the user stories, all those functions is what I see over and over and over again in product owner resume. What you want to do instead is say, "I led the," we can even do the login API,"I led the work around the login API. The problem that I was solving around it was trying to enhance security for our login protocols to meet regulatory requirements. I interviewed a bunch of users, I got up to speed on the regulatory requirements, I worked really closely with our legal teams and our compliance teams to translate that into something that was going to secure our bank, and when we launched, we were able to meet our compliance, save our bank a couple million dollars, and we smoothly transitioned into these new security requirements without disrupting any service for customers for four million customers."

**Melissa Perri** (01:05:40):
Way different story than I prioritized backlog and I shipped it off to developers. Take it a step further. If you're working on customer-facing things, who are your customers? Did you go out and talk to them? By interfacing with customers and understanding them, I was able to solve XY, and Z problem with them, which resulted in a measurable amount of XY and Z metric going up for the business. I ran this function, I ran this feature, I launched this feature, I watched it through, I iterated on it, I did the stuff that was needed to make this successful. That's what I want to see on a resume.

**Melissa Perri** (01:06:15):
Even if you have a product owner title, I'll still read the details and everybody else will too, but I will say there's sometimes a poor connotation when you have that title unfortunately because of the baggage that's associated with agile. Even just on resumes, I would say do product owner/product manager in there just to let people know that I know how to do this and I've been doing this well. If you do that in your bullet points, that shows up as well. There's also this whole concept that we didn't even get into about certifications. People keep asking me if I want to transition into product management, should I get a certification, an agile certification?" I feel like these were bigger a couple years ago, but they're still big. If you ever see somebody with a CSPO on the end of their profile, which you probably have seen on LinkedIn, it's a certified Scrum product owner.

**Melissa Perri** (01:07:05):
Now, one thing to remember, and this is about all agile stuff, is we call it the agile industrial complex, agile coaches and agile trainers, the whole Scrum team, scrum.org, Scrum Inc, SAFe, everybody, the way they make their money is through consulting to teach you these processes and by having people be trained to get these certifications. They come in and they say, "All your people need to be certified Scrum product owners. Give me 2,500 bucks per person," and then they get a certificate at the end of a two-day class that says they're a certified Scrum product owner. It doesn't necessarily mean they could do the job, it doesn't necessarily mean they could do product management, but let's think about when we're talking about too should we adopt SAFe in general, should we adopt these things, think about how these organizations make money.

**Melissa Perri** (01:07:56):
They're selling certifications. Of course they want more and more people to adopt it. That's the idea here. They're selling you this dream that you just certify all your people and then you could be working on it. They take all these people, they put them in two-day classes or whatever, and they turn them out and then they say, "Go, you're a completely new role." It doesn't work that way. That's not in the best interest of your company, that's not really what we're looking for here, and that's why all of this stuff needs to go deeper. If you've done a CSPO class and you have that certification, it may help you get hired at another large enterprise that is adopting Scrum and SAFe. That will probably help you there.

**Melissa Perri** (01:08:36):
If you want to transition into tech and go into the companies that we talk about, they're probably going to look at that and say, "This person doesn't know what they're doing. This is not here." If you do know what you're doing and you did that for a reason, because some people need that to get promoted, some companies actually require it, which is crazy, but to get promoted or be that thing, I have tremendous sympathy for that, but you're going to have to do a lot of work explaining in your resumes and stuff as you transition that you know more than that. You're not just a CSPO with a two-day class, you have done the work. That's where all of this building up on your resume becomes really, really important. It's not just about getting certified.

**Melissa Perri** (01:09:14):
I had people ask me, they're like, "Can you just certify product managers?" I'm like, "No. If people take my course, I give them a certificate of completion and as a completion." You finished a course just like any other course, but I will not certify product managers because I do not think you can ever say somebody is prepared and able to do their job from a short class. Now, there are some agile agencies that do a lot more training where you have different levels, and what they would do is they would train people, but then they would make them go do work and they had a coach that they worked with, and they go back and forth and they could demonstrate that they could do the work over time to get to the next level.

**Melissa Perri** (01:09:56):
It's almost like the PMP, the project management certification where you have to have time actually doing the job. That's different, that's a different type of skill, it's a different type of certification, but if you see any CSPOs, it's typically a two-day workshop that they went to and then got certified. That's the difference with this. I would say be careful if you are a product owner wanting to be a product manager of just certifications. All the large tech organizations I know too, they're not looking for certifications in product management or product ownership to hire people, they're looking for experience, but the organizations that might not know what they're doing, they are looking for CSPOs, they are looking for that.

**Melissa Perri** (01:10:37):
If it's required by your organization, you might have to ask, "Are we all well set up here to do our best job? Is this the place where I'm going to learn how to be a better product manager?" I also feel bad though for people because it's hard to be a product manager, it's hard to get your foot in the door. I'm so torn on it because there are organizations that hire people with a CSPO and they require it, so of course if it gets your foot in the door and it helps you do it, but if it's not going to help you and it's not going to put you on the career path you want, I don't think it's worth money.

**Lenny Rachitsky** (01:11:14):
I think one interesting thread throughout this whole conversation is rarely is a plug-in play-ish easy solution going to be the answer to your problem, whether it's plugging in SAFe and it's going to help us build great software, taking a class helping you become a great product manager, be skeptical of that.

**Melissa Perri** (01:11:31):
Yeah. There's no quick way to doing any of this, there's no fast track. You don't get to skip over all the hard things.

**Lenny Rachitsky** (01:11:39):
Yeah. Bummer.

**Melissa Perri** (01:11:41):
Yeah. I wish.

**Lenny Rachitsky** (01:11:43):
Yeah. One question I wanted to clarify. When you come into an org and they have product owners, do you encourage them to get rid of product owner as a title and role and make them product managers or do you keep product owners?

**Melissa Perri** (01:11:53):
I say that we should have a hierarchy. You would have all product managers on a team, they would be an IC, individual contributor, so they're either an associate product manager and that's if they don't have all the discovery experience or maybe they know basic Scrum, totally fine, you can be an associate product manager, but if they don't know how to talk to customers, digest what the customers are saying and turn that into a feature direction and a backlog and this is how we're going to work, all that stuff needs to be in there. If they don't know how they should be measuring things, you're not quite a product manager yet.

**Melissa Perri** (01:12:28):
Associate product manager, and then product manager, and then a senior PM. A senior PM can work on a Scrum team as well or a development team. I do encourage them, I say, "Get rid of these two different titles because it's confusing everybody." I help a lot of people with career paths too. I've seen companies with 47 different titles for product managers because somebody in this organization is called a product associate and somebody over here is a product manager and that person is a platform product manager, and that person is a platform product owner, and this person is an API product owner. You can have product manager, senior product manager, all that stuff, but I would not confuse people with the two different titles of product owner versus product manager.

**Lenny Rachitsky** (01:13:11):
But importantly, there's a bar for who is called a product manager because if you take a product owner as you've said, and say you're a product manager, they're going to be a terrible product manager. Your advice is make them an associate PM, and then once they reach a certain level, they've graduated to product manager.

**Melissa Perri** (01:13:28):
It depends. I don't say this as a hard and fast rule because there are product owners out there who've been doing their job very well. Just because they have a title of a product owner doesn't mean that somebody can't do the job of a product manager. There are plenty of people out there who were just named this because a company names them that and they know what they're doing, so don't look at that hard and fast. When we do this, we typically will say everybody's got product owner on their title, change it to product manager, but we will go back and look at what is the actual skillset.

**Melissa Perri** (01:13:56):
When I've come in to work with companies on transformations, what we typically do, the way I get introduced usually is we come in and they're looking for some kind of training for all of their product teams, and then we bring in Product Institute and we do our online training, Then afterwards I work with the organization, I say, "Now that everybody's been baselined and trained, we have to figure out who is going to be a great product manager and who's not," so there's an awareness. You know what's interesting? Once people figure out what the job's about, a lot of them opt out.

**Melissa Perri** (01:14:24):
When I did the transformation at Athenahealth, we had 365 product managers and they all had different titles too, product innovation, all over the place. We turned them into product managers, we trained everybody, we gave everybody the opportunity to learn, which I think is great, and then we gave them opportunity to practice their skills. What happened is at the end of the training, a lot of people raised their hand and said, "Oh, no, no, this is not what I wanted to do. I thought it was very different. I did not realize how much people work it was. I have to go influence these people, I have to do all this stuff. This is actually not really what I wanted to do."

**Melissa Perri** (01:14:59):
We found other roles for them that were what they wanted to do or they decided to leave. That was up to them, we didn't cut anybody, but we moved some people into operations because they wanted to be a little more heads down to find process. That was their thing. We moved people into data roles who were good with SQL and were good with data analysis. We moved people into user research roles because they wanted to talk to customers, but they didn't want the responsibility and the accountability that came with the product management piece because they realized it was so intense.

**Melissa Perri** (01:15:29):
I've seen this happen a lot in large organizations. You baseline everybody, you show them what the role is and then you let them go practice it, and then at that point some people will opt out and then you have to go back through your people and say, "Okay. How do we level-set now? Who's doing really well? Who's not doing so well? Which teams need to have more experienced people on it because they don't have anybody to learn from?" That's where we would say, "Hey, let's hire some ICs over here or a director of product management who can help train these people and help them keep growing." That's been super successful. I've seen people bring in some more directors, scattered them around, and they've leveled up these product owners who were not necessarily doing great product management and now they're doing fantastic.

**Melissa Perri** (01:16:13):
I've watched fantastic leaders in these organizations that are not software native or doing these transformations. Bringing the right person, you can make amazing product managers. Give them a year or two and completely turn it around. It's totally possible. It's totally possible to take people and train them, and I firmly believe in that, but you got to get them exposure to what good looks like. If you are in an organization and you cannot see what good looks like anywhere, that's a red flag. That's where leaders need to look at their organization and say, "Do I have people with these skills interspersed around so that everybody can start to learn, so that everybody can actually be on the uptake of this and make sure that we are well-balanced?"

**Lenny Rachitsky** (01:16:56):
That was an awesome nuance and addition. I'm just looking back at all the things we've talked about. We've covered so much ground, the history of agile and Scrum and SAFes and product owners, we've gotten into all kinds of advice on how to do this better as a company leader, as a product owner, as someone thinking about even moving through product management. Is there anything else that we have not covered that you think might be helpful to touch on or wrap up on?

**Melissa Perri** (01:17:25):
I think I would tell people to remember that when you look at agile methodologies, and if you look at it with small agile, what we are really saying there is we want to be able to move quickly and deliver great value to customers. If you embrace those principles, you're going to do well, but if you think of agile as just a defined super cut and dry process where you have to follow every single little step here and there, that's not going to serve you because you're not getting back into why are we doing this.

**Melissa Perri** (01:17:54):
There are some great agile coaches out there. There are first principle approaches to doing great product work and doing great development work. They're there because they are not just selling Scrum, they are there to make people better. Those agile coaches I think can make great fantastic teams, and I've worked with a lot of them, and I think they are really there to just make it a better environment for the people who are working and to help the company produce better products. That's their whole goal.

**Melissa Perri** (01:18:21):
Then there are people too who are wedded to this is SAFe and you will do it by the book. This is Scrum, you will do it by the book. I'd be very skeptical of that because what's the end goal? What's their end goal? Like I said, a lot of people out there get paid by certifying people and by consulting on these processes. McKinsey made a huge division to do this, and a lot of SAFe was actually introduced to organizations from McKinsey and from large organizations, consulting organizations like that. They came in and they said, "Yeah, this is what you do. I'll teach you how to do SAFe, I'll teach you how to do Scrum." They have been building those consulting agencies off of agile transformations.

**Melissa Perri** (01:19:03):
We always laugh when I talk to other people who've been doing transformations and coaches. I go, "Why is McKinsey always coming in here and doing this?" I've followed them into so many organizations and I've been like, "Oh, wow, they screwed this up. Let me go fix it." There's always a saying that nobody gets fired for hiring McKinsey. McKinsey's big, people trust their name. A lot of the people at McKinsey haven't done this before, they've never been inside the organization trying to transform it and stay there for a long time. That's why I'd be really skeptical of who's selling that.

**Melissa Perri** (01:19:37):
If you approach agile from a perspective of I want to be agile because I want to release things quickly and get feedback from customers and make sure that that's great, look at all of your processes like that and say, "Is that serving the best interest of our company and our culture and our customers? Is this making our customers proud of us? Is this helping our customers receive good value?" If your processes aren't, fix them, change them, inspect and adapt, ease a lowercase agile principle. We should be looking at every process we do and saying, "Is it working?", and not be afraid to change it.

**Lenny Rachitsky** (01:20:15):
I think it's important to highlight this can work. There are ways to reorganize the way you build product at a very large company where you can actually deliver great product consistently. You've seen that happen a lot. Anything you want to add there to give people hope?

**Melissa Perri** (01:20:30):
Yeah. The biggest pushback I hear from large organizations, especially ones that are not software native as banks or insurance companies, whatever it is, is that we're not like Google, we're not like SaaS companies. It's true, you're not a SaaS company. The way that you do it is going to be slightly different than the way that Amazon runs or the way that Google runs. I don't see many companies actually run the same, and just because it works at Google doesn't mean it's going to work at an insurance company that's a hundred years old. That's okay, but you could still learn from people who've been producing software at scale for many, many years. You can still learn what makes them successful, and then you could take some of those principles and apply them to your organization and then figure out where we need to adapt. That's what I would look at.

**Melissa Perri** (01:21:21):
I see software strategies and digital strategies becoming so intertwined into the strategies of companies in general, whether you're an insurance company or a bank or anything. They're becoming so heavily entwined in the C-suite strategies. The first thing I would say, and where I see a lot of companies struggle with this is you have to make sure that it is thought of at the C-suite. What some organizations do is go, "Oh, no, that's IT work. Let me push all the software strategy down." If you're doing that, you're missing out on innovation, and this is where the product role comes in and where I think more organizations need chief product officers because they're the person in the C-suite saying, "How can software enable us to be 10 times better and crush our competition, whether we're a bank or insurance company or a pharmaceutical company? What can we do with our software that's going to put us ahead of the competition, that's going to put us ahead of the market?"

**Melissa Perri** (01:22:16):
If you're not having those conversations when you're thinking of your long-term company strategy, you're behind, you're behind because that is what every small high-growth startup is doing that's coming out to try to disrupt these big companies. The big companies are successful, they have a lot of money so they don't have as much urgency as sometimes these smaller companies do to change or somebody who's failing to change. That's why things are going so slow, but at the same time, if we don't pay attention to that and we're not considering it, that's where the danger comes in.

**Lenny Rachitsky** (01:22:46):
I imagine people are going to have a lot of questions and hope to get even more advice. A couple of final questions. Where can folks find you online if they want to ask more questions along these lines, maybe get your help on some of this stuff? Then finally, how can listeners be useful to you, Melissa.

**Melissa Perri** (01:23:02):
You can find me on LinkedIn. If you go search for Melissa Perri with an I, P-E-R-R-I, you'll find me there. My LinkedIn is /melissajeanPerri. I'm happy to connect with people there. My school is called Product Institute, so if you're interested in doing product management training or getting help with some of this stuff, go to productinstitute.com and reach out to me. I run a podcast too called The Product Thinking Podcast. We answer questions every week, and a lot of them are around SAFe, agile and all these topics, so if you have a question and you're saying, "Hey, how do I do this?", definitely reach out and let me know.

**Lenny Rachitsky** (01:23:35):
Awesome. Melissa, I learned a lot. I feel like a lot of people who listen to this podcast, they're like, "I had no idea about any of this, and now I understand all these terms that I kind of hear occasionally." Thank you for coming and sharing all of this with us, especially the advice for folks that are in this world right now.

**Melissa Perri** (01:23:49):
Yeah. Thanks for having me.

**Lenny Rachitsky** (01:23:51):
Bye everyone.

**Melissa Perri** (01:23:52):
Bye.

**Lenny Rachitsky** (01:23:55):
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.

---

## [8/20] How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu

**Crystal Widjaja** (00:00:00):
I felt like it was a problem that was very solvable. And we ended up renting a stadium to just hire 60,000 drivers in a couple of weeks. So I think looking back, it was certainly a risk. When I got there it was in a house and I realized I've probably made a huge mistake, but we were growing very quickly already, even at that small scale of 4,000 orders per day.

**Lenny** (00:00:29):
Crystal Widjaja has been leading product and growth teams at some of the largest consumer businesses in Southeast Asia, including Kumu, where she's currently the chief product officer, and Gojek where she built and led the growth team through the early years of what is now the largest super app in Southeast Asia. To put this in context, Gojek completes more rights per day than Lyft and more food deliveries than GrubHub, Uber Eats and DoorDash combined, and it's the number one mobile wallet in Indonesia and Southeast Asia. In my opinion, American startups have a lot to learn from startups in Asia and Crystal has been at the ground floor of some of the biggest successes there.

**Ashley** (00:02:40):
At least 40%?

**Lenny** (00:02:40):
And how many of them screw that up, and what happens when they do?

**Ashley** (00:02:43):
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 CSV importer doesn't work right, which is super common, considering customer files are chalked full of unexpected data and formatting, they'll leave.

**Lenny** (00:03:02):
I am zero percent surprised to hear that. I've consistently seen that improving onboarding is one of the highest leverage opportunities for both signup conversion and increasing longterm retention, getting people to your aha moment more quickly and reliably is so incredibly important.

**Ashley** (00:03:17):
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 flawless data onboarding acts like a catalyst to get them and their customers where they need to go, faster.

**Lenny** (00:03:34):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny. Crystal, thank you so much for being here. I've read a bunch of your stuff online. We've exchanged a bunch of emails and tweets, but this is the first time that we're actually chatting for real, and so I'm really excited to, yeah I'm excited to learn from you and for folks to learn about you.

**Crystal Widjaja** (00:03:56):
We may have crossed paths on Clubhouse and the audio forums or on the Twitterverse. So it's really cool to see you.

**Lenny** (00:04:04):
Wow. I just remembered that. That is so right. I think we were talking about Reforge and Eppo. Is that right?

**Crystal Widjaja** (00:04:11):
Yes, that's right. Good times.

**Lenny** (00:04:11):
Oh my God. Clubhouse days.

**Crystal Widjaja** (00:04:13):
The days when club does was a thing. They have a thing too, to learn about exponential decay.

**Lenny** (00:04:18):
Oh man. Okay. Maybe we'll get to that. And we're going to be chatting a lot about consumer growth and a bunch of stuff along those lines. But before you get into that, you have a fairly unusual path and also geography as compared to many of my other guests. And so just to set a little context, could you just walk us through your career path and journey from, I think as an investment banker initially, and then currently as chief product officer at Kumu and then living in Singapore also? So yeah, tell us all about your path.

**Crystal Widjaja** (00:04:45):
Yeah. I think my path was certainly a nonstandard one. While I grew up in San Jose, the Bay Area, you could see companies like Lyft emerging around the year that I was graduating college. But really it was how do I graduate college as quickly as possible because this is very boring. So I took a Poli Sci major. I am not a math or a computer science major. I didn't know what a consultant was because I was just trying to get out of college. I didn't realize people start looking for jobs before they'd graduate. So the last two weeks of school I was looking on Craigslist, because I was like, "Craigslist is how everyone gets a job." I'm a first generation American student, so my parents could not help me at all with like, "You should look into this company called McKinsey," or, "Here are all of the life paths that you have ahead of you." So I ended up taking an investment banking research job.

**Crystal Widjaja** (00:05:46):
And my job there was to figure out how to call startups and analyze their potential for VC financing or M&A advisory. And I barely knew what those words meant at the time. I ended up owning a huge Excel database of 130,000 rows, 60 plus columns. And because again, I am very impatient, I was like, "This is a terrible experience. How would I create a customer database?" And so I ended up Google fooling all of the work needed to build a MySQL database, I presented a plan, and investment banking, surprise, surprise, is not very tech forward. So they looked at my plans and they're like, "What is this MySQL thing? Isn't that super expensive? What is open source?" So I ended up leaving that job because I realized that if I wanted to get into something more tech, it would probably not be at a investment bank. So I did took the investment banking strategies that I had learned there and applied the same pattern matching to companies in Southeast Asia.

**Crystal Widjaja** (00:06:55):
So my family originally is from Indonesia. I thought I have a kind of safety net, I must speak Indonesian really well just by birth, so maybe that's a great country for me to look at. So I took the approach of let's find a company that makes a lot of sense, that I feel I resonate with. And I literally cold called emails some companies. So Gojek being on that list. I literally emailed someone after Googling HR at Gojek and said, "I'm willing to move to Indonesia, take a bet on me." And they actually did. So I got extremely lucky. Five years fly by insanely fast. I went through building out the data team from scratch. When you have all of the data, you know how much fraud you have in the system. So then I ended up building out the fraud and risk team, picked up performance marketing, and then it was like, okay, now we're ready to grow. So you have all of this data now take on growth.

**Lenny** (00:07:55):
Got it. You were very modest about Gojek and the success of that company, and also Kumu where you work now. So just to set a little context for folks that aren't familiar with these companies, can you share how big they are and how big of a deal they are in Southeast Asia?

**Crystal Widjaja** (00:08:11):
Yeah. They are pretty massive. So Gojek is now called GoTo, they just merged with the largest eCommerce platform in Indonesia. So across Southeast Asia, we had about 170 million users. Southeast Asia has scale. If you ever wanted to work at scale, you would go to Southeast Asia. We had 20 plus different services from transportation to food, shopping, medicine delivery, bill pay, movie tickets. So it was like all of the startups in America in one app, all being built at the same time with the same user base. And so everything was tremendously layered, because you could fill all of these opportunity gaps in the market where a single app would probably not be as sustainable.

**Crystal Widjaja** (00:09:00):
So Gojek is massive across Indonesia, Singapore, Thailand, Vietnam. And then Kumu is kind of a super app for social. So Gojek was very transactional. It was like, "Here's a job to be done. I want to pay for something and someone delivers it to me." And with Kumu, it's more so of a, "I want to do clubhouse, Zoom, Google Hangouts gather around all in one app." So we cover social feeds, audio, video, multi seats. There's a ton of different use cases that we serve on Kumu. And Kumu is primarily in the Philippines, but ranks top 10 and a bunch of countries as a top grossing mobile app.

**Lenny** (00:09:40):
So with Kumu you joined when they're already doing fairly well. But Gojek, as you said, you joined very early. What did you see in that company that helped you decide to join such a risky, early stage company? For folks that are maybe thinking about joining a startup, what kind of things did you take away of what to look for?

**Crystal Widjaja** (00:09:58):
Honestly, it's probably a lot of luck. But also at that age I realized I have very little to lose. So with Gojek I think I felt like it was the right company because I was able to really clearly understand the value prop. Traffic in Indonesia is crazy. It takes you two hours to go 20 kilometers. So of course you want to take a motorcycle taxi to beat that traffic. Of course, you don't want to go out and get food and then have to come back this long pathway of two hours. So I think taking that Warren Buffet approach, I knew that the product made sense. The market made sense as well. So drivers, there were already a thing, but it was very hard to connect them to the consumer.

**Crystal Widjaja** (00:10:42):
It was painful to haggle prices. There were lots of restaurants scattered across Indonesia. So the value prop and the market made sense and the channel by which you would do it through this mobile app made a little bit less sense at the time because most drivers didn't have a mobile app, but I felt like it was a problem that was very solvable. And we ended up renting a stadium to just hire 60,000 drivers in a couple of weeks. So I think looking back, it was certainly a risk when I got there, it was in a house and I realized I've probably made a huge mistake. But we were growing very quickly already, even at that small scale of 4,000 orders per day.

**Lenny** (00:11:26):
I want to spend a lot of time talking about what you learned, driving growth at these companies. But one quick question. So, Gojek's the super app where you do a lot of stuff in one app. Do you have any insights into why a super app hasn't emerged in the US?

**Crystal Widjaja** (00:11:40):
Yeah. I think the sentimentality of a conglomerate is very different in Southeast Asia. So we've grown up with a specific conglomerate owning, not just the mall that you go to, but also the apartment building that you live in, and the school that you go to. And so they're very well integrated and there's this sense of trust in a conglomerate. Whereas in America we already shy away from, does Google know too much about me? There's also, I think, the second aspect of it, which is that in Asia, we've kind of leapfrogged to the computer era. So everyone has a phone, but you may not even have a computer in the entire household. And so when your phone is full, are you going to delete a photo of your kid or are you going to delete this app? You're probably going to delete the app. So for anyone to really survive, it has to be part of this super app concept.

**Lenny** (00:12:34):
Oh wow. I've never thought of it that way. That you don't have a lot of space on your phone and so you want one app to do a lot of things.

**Crystal Widjaja** (00:12:40):
That's right. So there's a decision factor that you don't really have in the US because the cloud storage and device capacity there is a little bit bigger.

**Lenny** (00:12:50):
Interesting. So in the US you can have different apps to be... Basically a super app doesn't have to be the best at everything. The fact that it does enough and everything good enough. Wow, it's fascinating.

**Crystal Widjaja** (00:12:59):
You just need to get the job done.

**Lenny** (00:13:02):
Amazing. Okay. That's super interesting. Okay. So transitioning a bit to growth and things you've learned along the way. So you talked about how, I think Gojek, you said hired tens of thousands of drivers really quickly. Are there things that startups in Asia do that you think companies in the US should do and can learn from in terms of growth?

**Crystal Widjaja** (00:13:22):
Yeah, so we did crazy things. If someone told you, in the US, that they were going to rent out a stadium, pre-load a bunch of mobile devices, market that drivers should come here in mass for a job fair. They're going to give them a phone and send them on their way, some people would say, "No. That's crazy. Won't we get in trouble." And to an extent, maybe that's true. So maybe there are some limitations there, but this concept of doing things that are somewhat crazy, but validate a point, doing stuff that don't scale, especially I think is really the bread and butter of what we did at Gojek. We were insanely scrappy.

**Crystal Widjaja** (00:14:02):
We would do things as simple as wanting to test a subscription feature, which was just released in Singapore a couple weeks ago. We ended up saying, "We have this voucher system that we can distribute vouchers in the back end. We obviously know our driver's phone numbers. Why don't we just add them to a WhatsApp group?" We'll add a hundred drivers randomly to a WhatsApp group. We'll tell them, "Every time you are on a ride with a customer, try to sell them this pitch. You are the only driver who can sell a subscription package. Have the customer give you $10. Text us when they say yes. Someone will be sitting by this phone all day, every day.

**Crystal Widjaja** (00:14:46):
We'll look up the customer that you were on a ride with in the backend, we'll give them the vouchers in the back end, and then we'll deduct $10 from your balance." It works. It's really this Wizard of Oz experience. We don't have to build anything. I coordinated with a bunch of interns and we were able to validate some of the value prop and conversion rates that we would expect in a subscription service. When we wanted to do a new onboarding screen, but turns out we have lots of engineering work to do, we took a screenshot of the screen as is, and we just had our designer put what the onboarding flow might look like if we had to overlay it on top of the screen.

**Crystal Widjaja** (00:15:27):
And we just sent that as an in-app message. And then eventually I think finding stuff that does scale intuitively. We knew that we were sending out lots of fake features through things like Typeform surveys. Things like a personality quiz can be very easily done through Typeform. And we realized that if we built in the in-app webpage and we made it easier for us to do a website deployment on our backend side, we wouldn't have to wait for a mobile app release to test some of these new features out that could be done on web. So it's really just like, what is the user experience that we want to create? How do we manifest that as quickly as possible? Let's just try that first.

**Lenny** (00:16:13):
Going back to the stadium example. I know you said that you hired a stadium full of people, I didn't realize it was actually a stadium that you-

**Crystal Widjaja** (00:16:19):
That it was literally a stadium that we rented, like a football field, a couple football fields if I'm not wrong. It was long lines, boxes of phones and SIM cards. So it was a lot of just doing really hard work to get to that scale.

**Lenny** (00:16:35):
Wow. I know you do a lot of advising too. Do you advise startups to be more scrappy and do things that don't scale? I imagine because in the US the culture is a little different.

**Crystal Widjaja** (00:16:45):
The only thing better than knowing... If you have data of what your customers are doing, that is the best data you could ever get. And so if you don't have a tested hypothesis, if you can't think of a way to run an experiment, then honestly that idea is pretty useless. Maybe it makes sense to the market, to the model, but you could have weird consumer sentiments. Not everyone is a rational actor. So testing the actual experience and seeing how people respond to it, that's the best possible data.

**Lenny** (00:17:21):
Pulling that thread a little bit, for startups, experiments are often hard because there's just not enough data and enough users. How do you think startups should approach that? Can you run experiments when you're really, really early?

**Crystal Widjaja** (00:17:32):
You should. Even if you have a sample size of 30, the data you get back, generally, does not change but its precision will. So mathematically speaking, you're going to get the same level of trends, but the precision at which you understand those trends will become more deep if you have more data. But the underlying information that you're getting out of that won't be very different at larger scales. So what's better than having 30 data points? Certainly having 100. But what's better than having zero is definitely 30.

**Lenny** (00:18:10):
Fascinating. So contrarian. Running experiments at 30 people. I love that.

**Crystal Widjaja** (00:18:14):
You have to. Every idea is so cheap at that scale. You could do things that don't scale dramatically better with 30 people than at 100 if you're testing.

**Lenny** (00:18:29):
Just to pull on that a little bit, when you're running an experiment with 30 people, what do you look for? You're looking for 20 of them to do something, a large percentage of that group does something?

**Crystal Widjaja** (00:18:39):
So everyone wants to go on retention. They want to see that users are doing this thing, and they want to get from step zero to 100 really quickly, but they don't realize that users make decisions based on succeeding events. So what's one step before the user makes that decision? What are the things that they have to do, the things that have to be done? So we're always looking for what is a specific reason that this user might have converted? For things like GoFood it would be things like when does a user try a new merchant if what people are ordering right now or just food that they already trust and know. If you need to have trust in order to purchase food from a merchant, how do we generate that trust? So we actually hacked it by connecting people's Facebook connect login.

**Crystal Widjaja** (00:19:33):
So we had already had permission to look at who they had connected with on Facebook. We actually looked at the food that their friends had purchased and used that as a data set of, "Hey, here's food that Lenny purchased and liked. Maybe you would like it too." And so that was one way to hack the trust factor. And we did find that when we told people, "This friend purchased from this merchant," you would be twice as likely to purchase from a brand new restaurant then users who did not have this feature. And that increases GMV, that eventually gets you to the conversion rate that you wanted, but it solved a different problem. Before how do I convert, it was how do I solve for trust? How do I break the barrier of facilitating that decision making process, that aha moment, by fixing the setup moment, which was trust?

**Lenny** (00:20:31):
And that's just a general rule of thumb you have. Don't use retention as a goal. I know you wrote about this somewhere. Is that a rough rule of thumb you use?

**Crystal Widjaja** (00:20:41):
I think a lot of people thought that I had meant retention sucks, don't care about it at all. But in reality it was really when you think about retention, that's just not specific enough. So there is this mental model that I use from made to stick where they'll tell you like, "Lenny, think of everything in the world that is orange." And you're like, "An orange. What else?" And then if you change that structure with sandbox to think of everything orange that's in a construction site, then you really start to realize and grasp at concrete concepts, and can actually action on them in real life.

**Lenny** (00:21:25):
Got it. Speaking of retention, where have you found products and companies have the most success increasing retention?

**Crystal Widjaja** (00:21:32):
It's usually the step right before conversion. So if they aren't sure why the user opens the app or they aren't sure why the user got to this checkout page, it's often some copy or the path has been ineffective in some way. I'd like to see founders think about the user psych model that Darius Contractor often talks about. So you need some momentum in that user journey to get them over the hump of some of these very painful user processes like typing in a credit card. That's a lot of work. How do you lower that friction? And being able to sequence the right steps effectively and just moving around screens actually can do a lot.

**Lenny** (00:22:21):
Going even deeper there. So the companies you've worked at, the companies you've advised, you're on the boards of a couple companies I noticed, what have you found to be really good uses of time in terms of growth investments, things that often work? And then a second question, what do you find is rarely successful or people invest a lot of time and ends up not being really useful for growth?

**Crystal Widjaja** (00:22:44):
Yeah. I think I see a lot of founders grasping at straws. So there'll be this brand new feature that does something different from what people are already doing on our app, like this will make things work. But they don't have any Wizard of Oz test, they haven't proven that people want to do that, they don't have any data of users currently trying to do that. And that's a sign of why this, instead of literally anything else that you could be doing. I do find if you have a lot of people landing on a webpage or an app and then not doing anything, then it's probably copy.

**Crystal Widjaja** (00:23:25):
They haven't even experienced the product, it's clearly not the product that's wrong. So how can you change the copy and resonate with the pain point rather than the solution you are offering so that users understand how to fit themselves into the use case? So copy is a big one if I see conversion rates aren't landing between app launch to some first action. But if there is conversion and they're just not as frequent, I try to look at what the most painfully long conversion events are. So users who eventually check out or eventually completed the aha moment, what are the user paths, and what is the longest one that seems like it's the most painful? Are there enough people trying to do that?

**Crystal Widjaja** (00:24:13):
And how do we shorten that cycle? So for Kumu things like users wanted to sign up and find their friends on Kumu. And so they were using search frequently, search was underutilized API, it was slow. We sped that up. Conversion rates go from 60% to 90% over the course of a few weeks of just optimizing that and putting more content there. So looking at where are people doing things and then failing, you already know this percent of people would convert if you fixed this, that's a definite potential win. So we try to layer these definite wins with crazy bets of brand new feature with no data. At least run an experiment if you can. But I always try to layer in these sure wins.

**Lenny** (00:25:01):
When you talk about conversion being good and bad, do you have a rule of thumb or of a mental model of here's a rough range of this is good and we should not really spend a lot of time on this and this is bad and we should optimize?

**Crystal Widjaja** (00:25:14):
So assuming that the frequency is correct, so you have a weekly frequency, if users are coming back, if it's a free product, 60%. It has to be at least 60%. If it's a free product, we go over a week. If it's a paid product, I usually look at that more as maybe 20 to 30%.

**Lenny** (00:25:32):
And this is retention, people coming back the next week?

**Crystal Widjaja** (00:25:34):
Exactly. Coming back in the second week or month or whenever your frequency ratio is. And this is at scale. So if you are much smaller, your friends and family that better be near close to 80% no matter what, because if you can't even convince the people who care about you to use the product, it probably isn't going to solve the job for anyone else.

**Lenny** (00:25:56):
Very handy. Very concrete numbers. And then your point is that when you're a startup, it's only going to go down because your early adopters that are more excited and they'll be more excited by coming back. So you want to start really high.

**Crystal Widjaja** (00:26:10):
Don't make the same mistake that Netflix and Spotify have made, which I guess is when they've launched, they've started international expansion and they see this very small percentage of users start to sign up for Spotify or Netflix. There are very few people though in Southeast Asia or internationally that have the types of credit cards that Spotify or Netflix would accept. And so when they launch in these markets and they see a ton of uptick in the first week, they're like, "This is only going to get better." When in reality it's like you just pulled forward everyone who could have possibly subscribed to you, now you're going to have to work a lot harder to get everyone else.

**Lenny** (00:26:47):
The 60% number. So you're saying it's then every week, 60% of the previous week come back, roughly. Is it just a rule of thumb?

**Crystal Widjaja** (00:26:54):
Yeah, exactly.

**Lenny** (00:26:55):
Is that how you think about it versus say cohort retention? Is that just because it's easier is just a simple rule of thumb?

**Crystal Widjaja** (00:27:01):
Am actually thinking of it as cohorts. So 60% should be your week one, and then it should flatten. I think I usually give teams two to three weeks or frequency periods to see things flatten, but it better flatten around 60% for a free product. That's actually what we saw at Gojek. Early days it was like 60, 70% retention rates because people were using this product that really solved a huge problem for them. And I think that's when I knew we were going to be fine. If people keep coming back, the product just needs to work.

**Lenny** (00:27:36):
Wow. So week one, 40% of people drop off week two and beyond basically nobody drops off is what you look for.

**Crystal Widjaja** (00:27:42):
Yeah.

**Lenny** (00:27:43):
Wow. What a high bar. But I like that, because-

**Crystal Widjaja** (00:27:47):
Yeah, well Gojek is a decacorn.

**Lenny** (00:27:50):
Okay. There we go. If you want to be a decacorn, there's your new benchmark. Amazing. Okay. There's a bunch of other stuff I want to dig into. One is just data modeling and thinking about growth strategy as a founder. So say a startup is just trying to think about, how do we drive growth, where do we invest, do you have a framework or a process? I know this might be a really big question, but just for founders to think about how their growth works, what their drivers might be, how would a founder approach that problem?

**Crystal Widjaja** (00:28:20):
For sure. So I thought that this was not an obvious process. It wasn't an explicit process until I worked with Reforge to build my data four PMs program. Got to get that plug there.

**Lenny** (00:28:34):
Go Reforge.

**Crystal Widjaja** (00:28:35):
I basically talked with the Reforge folks about here's what I would do in all of these scenarios. And they're like, "Oh, so you mean you're doing this step one, step two?" And I was like, "Yes, actually. How did you figure that out?" So I don't really think in-frame works, this is just a logical process to me. But I think what I've figured out is, it's step one, you have constraints. Similar to our sandbox example of everything in the world that's orange versus everything in a construction site, you have to think about the physics of the current market, the product, the model and the channels that you're using. So to use Gojek as an example, it would be market of Indonesia.

**Crystal Widjaja** (00:29:16):
Here are the consumers in this market, the driver's side supply side in this market. Here is the product, mobile app. We're able to connect drivers and consumers. There is a allocation that we create model. We charge per order, channel. We are able to do this through push notifications or in acquiring new users. It might be through Facebook ads, or, and this was a really big insight for us, it's the real world. There was a physical conception of a driver in a jacket driving around the city who was marketing Gojek for us. And word of mouth actually was primarily driven by, "I saw a driver on the street, so I knew Gojek was here."

**Crystal Widjaja** (00:29:58):
And that actually was a huge driver of all of Gojek's growth as it expanded to new cities. So step one is, what are the physics? Step two is when you think about loops and growth funnels and the quantitative inputs to each loop, does that fit into these physics or do you have to change four or five different things? So we were very careful about changing too many parameters and making too many bets on too many variables going our way. So we would always change one small thing at a time and make sure that it fit into the model.

**Lenny** (00:30:38):
**Crystal Widjaja** (00:31:58):
I think it's both figure out how you're growing and also the elements that you have at your disposal. What are the levers that you have that maybe you've never tried using? When we looked at our model this way, we actually realized we had underutilized the driver's capacity to drive our growth. Pun definitely intended. So in looking at the model this way, we had thought through what is our goal. We want GoPay to be much bigger than it really is. It's a E-wallet service, users are able to get access to this digital balance. How do we drive adoption? And so when we looked at the lever of we have a driver, we actually created an incentive model. So we built a very small service that would check when a driver got allocated to a customer, again, the product and the model, we would then check in the database, has this customer ever used our GoPay product before?

**Crystal Widjaja** (00:32:59):
Did they have a digital balance? And if the answer was no, we would message the driver immediately, "Hey, this customer hasn't done a GoPay top up before. If you get them to give you cash and we deposit it into their virtual wallet, we'll give you extra money." So using them as the salesperson. You wouldn't believe how great of a salesperson someone can be when you were literally trapped in a car with them going somewhere. And so you have this captive audience, captive attention, you have someone who has the incentive to cross pay or cross sell someone into GoPay. And customers were able to feel the benefit because the driver was explaining it to them directly. There was no change to the physics, it was a lever usage.

**Lenny** (00:33:49):
What a devious strategy.

**Crystal Widjaja** (00:33:50):
It was huge. It was 60% of acquisition once we released that.

**Lenny** (00:33:55):
Oh my God. So for thinking through your potential levers and physics of your growth, do you think about it bottoms up, here's all the things that are going on and here's areas we can invest? Or do you have a menu of options top down of here's the 10 things it could be, it's looking like for Gojek it's these four and let's focus on that?

**Crystal Widjaja** (00:34:15):
Yeah. I think you always have to start from the fact that we are not wizards. It's very hard to move the physics of a universe when you are trying these new things. So start with what currently works and currently exists and where you think the biggest constraint is or the best lever is, and then fix that one piece because the entire universe isn't exploding. The world isn't changing so dramatically that your physics change. So I think rooted in reality is very important.

**Lenny** (00:34:50):
Got it. Okay. So it's see what's working, find the constraints. And then step two is basically what can you do to the product to optimize the funnel/loop to make it go even faster?

**Crystal Widjaja** (00:35:00):
Exactly.

**Lenny** (00:35:01):
Love that. Maybe as another example, if something comes to mind, with Kumu, how do you think of Kumu through this lens?

**Crystal Widjaja** (00:35:08):
Yeah. I'm always very hesitant to talk about Kumu, because there's so much competition right now and we are on the cusp of some very interesting things. But I think for Kumu, it's actually very complex because there's a lot of human emotion that is involved. With Gojek you knew if you got the job done. You made a transaction. With Kumu, how do you know if a consumer made a friend, felt like they had a genuine friendship? So you almost have to create more friction to identify users who really got past that barrier and aren't explicit with the activity that they did. So we have features that tell us if a user is really searching for this job to be done, if they really want to be part of a community, how do they fill out this?

**Crystal Widjaja** (00:35:57):
Do they fill out the form? Do they fill out a questionnaire of many questions? Do they go through this friction just to get access to a community? So we almost create this artificial friction to help differentiate how deeply a user wants something or needs something. And if the user doesn't fill out that questionnaire, maybe they're actually looking for something else. They were looking for entertainment. They were looking for content or short form content. And so creating almost like hand razor approaches for a user to say, "I wanted this thing." We leave a lot of breadcrumbs in the app to be able to identify those paths.

**Lenny** (00:36:38):
Awesome. While we're on the topic of these two companies, just maybe for inspiration to founders who are thinking of ways to drive growth, what were a couple of the bigger unlocks growth wise for these two companies or even any other company that you've worked with that's interesting?

**Crystal Widjaja** (00:36:52):
Yeah. Definitely, in the early days it was copy. So I think if your product does something that's not super familiar, you have to tie it to something that is. So I talked about using drivers to sell GoPay. Before that, one thing that we did was to actually take someone's virtual account number and put it onto a picture of a credit card. You know what a credit card is, that's familiar to you. A lot of people didn't know what a digital wallet was. And so when they looked at this like, "Oh, okay. I have this virtual thing that acts like a credit card. It works like my debit account." Then they understood the concept a lot better.

**Crystal Widjaja** (00:37:33):
And we actually saw top ups increase based on us, literally just sending that picture with someone's virtual account number there. So they could go to an ATM and they would just type in the card number as they would a regular debit account. And they realized that they could top up through that channel. Because that was something that was pretty interesting to us, with just how do we tie the familiarity loop back into the consumer mental model of the product and drive acquisition that way?

**Lenny** (00:38:02):
And that was at Gojek?

**Crystal Widjaja** (00:38:02):
Yeah.

**Lenny** (00:38:04):
Is there anything else maybe, since you don't want to talk too much about Kumu, any other advisorships or companies, examples of something that ended up working really well to help them accelerate growth?

**Crystal Widjaja** (00:38:14):
Things that have worked really well. So for one of the companies I work with, AB&B, they run a lot of their D2C brands in South America and globally. So one of the features that we were looking at was how do we ensure that subscriptions don't actually become a canceling point for a user. So in the app you could cancel or you could resume your subscription, but you couldn't pause it. So when we looked at the cancellation reasons and we saw that their number one reason was, I still have too much fear, we actually decided, well, let's just add a pause button then.

**Crystal Widjaja** (00:38:58):
Because canceling the subscription is a permanent solution to having too much fear. How do you make a temporary solution that solves the actual problem? Adding in a pause button actually helped alleviate a lot of the churn that was becoming very hard to reacquire back. So that was one fix where we looked at the, again, physics of the model. We're not going to create new changes to the product or create one time buys or reactivation emails. We'll just solve the problem at that small constraint where everyone drops off.

**Lenny** (00:39:35):
Wait, so can you order beer as subscription? Is that a thing? Is this a consumer product or is this-

**Crystal Widjaja** (00:39:40):
It was a thing, yeah.

**Lenny** (00:39:43):
Cool. Okay. This also reminds me, at Airbnb, this was actually one of the biggest wins, is adding a snooze feature to your listing. Exactly the same thing. Yeah. All right there we go. Awesome. Tip for folks that have churn problems, snooze/pause. I want to shift a little bit to a post that you wrote that maybe is one of your more popular posts you wrote on the Reforge blog called Why Most Analytics Efforts Fail. And I'd love to hear your broad overview of why do most analytics efforts fail and then how do teams avoid this? Maybe what are two to three things they can do?

**Crystal Widjaja** (00:40:18):
Yeah, I'm actually pretty surprised at how much noise that has generated because I guess it came from a place of frustration where I kept telling people like, "You are doing this wrong. Here's how you should probably be doing it." But I think it resonated a lot with folks because they recognize all of those symptoms, but they weren't sure why it was happening. So to say, oh, this is the thing, instrumentation is what's wrong, I think it's a very actionable thing. It's probably one of the most solvable problems out there. It just takes some time and mental model shifts to do it well. So a lot of people look at tracking data as how do I track my OKR? How do I know if I'm going up or down? But they don't use it to track or identify insights. So I will use the example of using Twitter for "news" when in reality they're actually using Twitter for entertainment.

**Crystal Widjaja** (00:41:17):
Do not treat metric gathering as entertainment. It's not there for you to be like, "Oh, that's interesting, how novel," and then not act on it. So real news is information that changes what you do in the real world. And if you don't change what you're doing, what you are doing is just getting entertainment. So let's use that as the premise. The next step in instrumentation is to look at the fact that measurements do not equate to insights. A measurement would be an observation. It's a data point in your database. So the example being power users do four times more bookings, is an all observed fact because your transactional database obviously says that is the case, but it's on an insight because it doesn't have context. It doesn't give you information that lets you act on it and better understand the problem.

**Crystal Widjaja** (00:42:11):
So another example would be if I see my girlfriend hanging out with a guy I don't know, that is an observed fact that you see in the real world. Your hypothesis could be that your girlfriend is cheating on you, but the insight, the actual fact might be that she's not cheating on you, it's her cousin. And now your insight is, I am paranoid and I need to change my behavior to be less crazy. So the insight will provide value when you have this, why answered? Why is this person doing this thing? Here's why. And then you are going to act differently. So for our purposes, if we look at a GoFood user will transact and is more likely to use a voucher, that's a fact, that's an observation, but it's not an insight. An insight would be something like GoFood users who are power users are more likely to use a free shipping discount on a high GMV basket versus non-power users.

**Crystal Widjaja** (00:43:22):
And that actually tells you how to change your marketing approach. It tells you in what circumstances does someone do this. When it's a high GMV basket, give power users the ability to get a free discount, but do not do this for non-powered users because they won't convert any better than they normally would. So, that helps you change your marketing spend. It helps you understand the decision points of power users versus non-power users. The insight is instrumenting properties into an event so that you can segment who is doing what behavior and make some hypotheses on that observation. Test that hypothesis, and then you get some causal representation of whether or not that hypothesis was right.

**Lenny** (00:44:10):
So it sounds like a lot of the root of the issue is setting up the wrong metrics, the wrong... I guess there's the tracking element of just capturing the right information. And then also just not focusing on insights versus just having a bunch of information.

**Crystal Widjaja** (00:44:24):
Exactly.

**Lenny** (00:44:24):
What are signs that you're doing this? Say someone's going to go load up their dashboard and they're like, "Am I failing or not?" What should they be looking for?

**Crystal Widjaja** (00:44:33):
So I already know if a team is good at instrumentation or not just by looking at the instrumentation spec. The symptom of a bad data tracking approach is you have a ton of rows with a ton of events, but every event has one property or no property being tracked. So an example with Gojek would be when a user lands on the map to select a drop off point, the event would be drop off or map loaded, let's say. And the properties there should be things like how many drivers do they see on the screen? What is the pickup location? What city is it in? What latitude and longitude is it? Is there surge pricing? What is the current minimum fare? Do they have a voucher code?

**Crystal Widjaja** (00:45:28):
All of these characteristics of the experience and the context that can help you look at hey, when a user only sees two drivers on the screen, they're much less likely to convert than a user who sees five drivers on a screen. Now we can look at in what cities and in what latitude and longitudes do we mostly only see two drivers versus five drivers. Being able to do the second layer approach of the why and not just stop at, "That's weird. When you have two drivers you are less likely to book." But then you never ask why. That drives me crazy. Or the inability to even know that there were only two drivers on the screen. You're missing so much context of the user's experience that you're unable to make assumptions about why the user didn't convert.

**Lenny** (00:46:15):
I love this. Maybe your course is probably going to be the answer, but for folks that want to figure out how to do this taxonomy and events well, how do they go about doing that?

**Crystal Widjaja** (00:46:26):
So I think it's important to just go through examples. Yes, every product is different, but everyone has the same signup flow for the most part. So look at the signup flow examples that I have in the blog post or in, I believe Amplitude actually has a pretty good long-winded documentation on this, on how to do a event tracking. But it's really a matter of sitting down and thinking really deeply. If I were to press this button, why would I and why would I not? And am I tracking that in my user properties? So it's really just sitting down and mapping out the experience.

**Lenny** (00:47:05):
Speaking of Amplitude and other data tools, do you have a default recommended metrics stack for our founders just to start with and maybe a few other things as they evolve?

**Crystal Widjaja** (00:47:14):
That really depends on how early they are. So if they have a single data warehouse with all of their transactional data, usually I say, you can probably get by with Google Data Studio. It's free usually with whatever you're using. If not Metabase has a great open source free tool. If you have someone who can write SQL or if you have multiple databases, then Metabase is great. If you need in app mobile device event tracking, I usually recommend CleverTap because Mixpanel has unfortunately failed me a lot. And Amplitude doesn't have the CRM components that I would need all in one space.

**Crystal Widjaja** (00:47:51):
If I am much bigger and I need more analytics juice, maybe Amplitude makes sense on top of this, or something that helps me pipe data into more dashboards and do less ETL for me. Then I would get into Segment. And then once you get into experimentation, obviously I have to shout out to Eppo. I think they've really instrumented a lot of the dashboards that I would've normally had to do in experimentation projects. So I usually look at something like Eppo to just automate the decision making flow.

**Lenny** (00:48:21):
Awesome. I think we're both small investors in Eppo, big fans, a little bit of bias, but yeah's it's an excellent Airbnb team that built it, so it's cool. Shifting a bit from metrics and data to just growth teams in general, maybe first question is just, how do you recommend companies set up a growth team in the early days and then over time?

**Crystal Widjaja** (00:48:44):
Yeah. So I can talk about how growth was set up at Gojek as an example, which I think is probably the best practice. So we didn't really know what growth was at that time, but we knew there were obvious gaps to fill. So because we had grown so quickly, the core product team was still making the core product features. As simple as phone number masking. That wasn't a thing yet. You had access to your driver's phone number. It's probably not a great thing. It's probably part of the core functionality and we need to fill that gap. At the same time, growth was still necessary because you had all of these users trying to use a product that aren't quite getting there.

**Crystal Widjaja** (00:49:25):
So things like figuring out what SMS provider we should use to send the OTP to this user who is signing up from this telco provider. That was a growth objective that isn't necessarily core feature work, but was a gap to fill given the onboarding and SMS success delivery rates. Things like telling the driver if this was a brand new customer, because at this point in time, drivers had taken thousands of rides and they assumed every single customer knew how Gojek worked, when maybe they didn't. And so we knew that the protocol was that a power user would know they would make an order and they would just wait. They would wait somewhere, they would keep an eye out for a driver and then they would get on the motorcycle and go.

**Crystal Widjaja** (00:50:13):
But for a brand new user, are you supposed to walk to the driver? Are you supposed to find them? It's unclear to this brand new, uneducated new user how to use the product. And so first time user experience could have been a terrible one where they went and walked off and then the driver came to the pickup point and they couldn't find them. So it was all of these small acquisition, adoption and engagement use cases that growth was filling the gap on. And eventually we embedded our growth, I would say product managers at the time, into these teams and they ended up synthesizing what growth was as a full-time role. Eventually becoming PMs who own specific parts of the product stack.

**Lenny** (00:50:58):
So in your experience, and I hear this a lot, is your first growth person shouldn't just come in and figure out what to work on. You should understand here's where we need growth help, let's find somebody to tackle it, versus come help us figure out what to do to drive growth. Is that how you've seen it?

**Crystal Widjaja** (00:51:11):
Exactly. I think it's just setting the bar too high to expect someone to come in and model everything. Again, there are physics in place it's very hard to move everything. So it's really about having someone who already has all of this data knows where the biggest gaps are. Doesn't have to start from scratch and figure this out and then just picks some small space to work on that they know is workable.

**Lenny** (00:51:38):
Do you have strong opinions about growth being integrated? The way that you described where growth PM basically has a cross functional team basically is the PM versus a separate growth team that's off to the side.

**Crystal Widjaja** (00:51:50):
Yeah. I think it can work as a separate growth team to the side if the company is truly head over heels, tripping on insane product market fit, if there's insane, product market fit and you are really scrambling to do core feature stacks, then maybe a growth team to come and be clean up is fine. We're the cleanup crew. We pick up the pieces that were left behind, we connect the dots. You forgot to plug this in, we'll plug it in for you. But we were a team of lots of stats heavy people. So a lot of my team were statistics graduates. We cared a lot about looking at numbers and odds and probabilities because it really is a numbers game at that scale. You could work on anything and everything would probably do something. But what was the thing that would make the most impact now and unlock us for the future.

**Lenny** (00:52:44):
I was going to ask you folks to look for when they're hiring an early growth person, is that what you find, just stats, data kind of person?

**Crystal Widjaja** (00:52:49):
You have to have someone who knows how to run the numbers. If you're looking at ratios of conversion rates, but you don't realize that this ratio is of a much smaller base size, you're going to make the wrong decision. So someone who is intuitively good at statistics, they know how to do sampling appropriately. They know what selection bias is. The worst possible thing is to have a growth person who thinks they are doing the right thing and is measuring things wrong and then focusing on the wrong areas.

**Lenny** (00:53:24):
Do you find that it's often easier or better to hire a young up and coming person or find someone that's got a bunch of experience for your first growth hire?

**Crystal Widjaja** (00:53:34):
I would hire someone who is willing to take intro to statistics course. And it doesn't matter if they've had the experience to go wild or not. I think it really is, can they focus on the right opportunity rather than the most flashy thing? And I think both profiles can come under that.

**Lenny** (00:53:54):
Got it. And then what do you do in a hiring process for someone like this? What kind of things do you suggest founders look for?

**Crystal Widjaja** (00:54:01):
Yeah. I actually look for that first principle bias. So I'll give people case studies of here's what we see, how do you know that this is true? And then I have them set up an experiment design. I want to see that they are sampling randomly. Not that they're like, "I'm going to build this feature and launch it, and of course it's going to work." I want to see that they're taking a measured deliberate approach to considering why someone might do this or what tools are available. A growth team can go terribly wrong when they just try to onboard a bunch of brand new tools that don't integrate well and it takes six months to integrate fully, and then they get nothing done for six months. Everything in growth is an opportunity cost of time, trade off with what you could have been doing to the product in that time.

**Crystal Widjaja** (00:54:50):
So we biased towards really quick hacky things. Like in the early days of Gojek growth, I think our first real growth experiment, we were actually still the data team at this time, was to connect a quick Python script to the Twilio API that we had access to. And we SMSd a bunch of drivers through a CSV that we uploaded that said like, "Hey, your acceptance rate is really low. You're not supposed to do that. Please accept all the rides that you are getting." And that actually increased acceptance rates by 2% across the board. And when we looked deeper into that data, it did even more so for brand new drivers. And so we then worked with the data driver onboarding team so that they could better facilitate the onboarding experience for their drivers.

**Lenny** (00:55:38):
For the interview question that you described, an experiment design question, do you give that as a project where they have time to work on it or is it a live thing?

**Crystal Widjaja** (00:55:46):
Yes. Yeah. I don't think live works really well for these case studies. I want to see people put in the time and the work to do something to the best of their ability. And of course we ask them like, "Hey, you have five days. We expect you to spend probably four hours on this, so if you don't have four hours within these five days, let us know." So we're pretty careful about giving them the appropriate amount of time to do it at the level of quality that we would've expected if they were to work here full-time. So give them those four hours, we want to see do they Google. If they can't figure it out right now, let's see them Google it. We'll ask them what approaches they took, how did they figure this out. And we like to hear people say that they literally had to Google this and read a bunch of white papers. I do that as well.

**Lenny** (00:56:39):
For people trying to design one of these for themselves, do you have a question that you've retired that you could share or something that would help somebody design their own prompt?

**Crystal Widjaja** (00:56:49):
Yeah. I can give you a template after this call.

**Lenny** (00:56:51):
Amazing. We'll include that in the show notes. Easy peasy. Amazing. Okay. A last topic that I wanted to cover is a very cool thing that you were involved in. It's a nonprofit that you started called Generation Girl. And I think the mission is to help women and young girls get into STEM. So I'd love to hear about this program, how you got into it, what it's all about, and then also just how listeners can help support what you're doing.

**Crystal Widjaja** (00:57:15):
Absolutely. Yes. Generation Girl is very near and dear to my heart. So I co-founded this with a couple of amazing women who were also at Gojek, but are now full-time at Generation Girl. So this really stemmed from us repeatedly getting annoying comments about working in STEM. So things like, "You can't possibly be the engineer on this project. You look like you like makeup and stuff." And we were like, "Yes, I absolutely love makeup, but I also am badass at writing SWIFT code, so step aside." So having experienced a lot of the misrepresentation of what an engineer should look like or should like, I think we really look to Legally Blonde, is one of my favorite movies that represents you can take the powers that you have, whether you like engineering or design or data, and you can be whoever you want and still kick ass at it.

**Crystal Widjaja** (00:58:14):
So a lot of the women that we support, we're actually happy if they go into one of our classes and they say, "Actually, I don't like engineering." That's great. That's agency and empowerment that they got to make that decision for themselves without any cultural biases or social pressure telling them that they should feel this way. And so we offer free classes for girls 12 to 17. We have college classes. We partner with teachers about how to teach STEM topics, especially in areas where they don't have laptops for every student. How do you teach how to use Figma and things like that? So people can definitely support us and reach out to us. We have a PayPal on our website, take a look.

**Lenny** (00:58:59):
Can you share some of the impact that you've seen from this? Are there numbers you can share or anything that you can share around what the organizations have done.

**Crystal Widjaja** (00:59:05):
So we've already had several thousand students go through Generation Girl, summer clubs and programs and classes. So we have an event every week. We have a full summer club that's every single day for two weeks, every summer and every winter. We have partnerships with some of the biggest tech companies in Indonesia, where we partner students with engineers and they work on projects together. And most recently we're part of the MIT solve program with our new initiative Class. So Class, we're creating a free to use site for teachers.

**Crystal Widjaja** (00:59:40):
So right now we have partnered with a handful of universities in Indonesia, both in rural and city of Jakarta where teachers can now have the knowledge and material to explain newer concepts that maybe they're less familiar with, because startup world changes rapidly, how you develop changes rapidly. So this is one thing that we are most excited about because every teacher impacts thousands of students a year. And being able to teach the teachers and give them the resources that they need is something that's really important.

**Lenny** (01:00:11):
That's incredible. It's currently just in Southeast Asia, is that right?

**Crystal Widjaja** (01:00:15):
Only in Indonesia, because frankly, this is where everyone needs the most support. Globally STEM is not well received or welcoming at all to women. I think it's gotten worse over the past few decades. Below 18% of college graduates are women in computer science. So we're really trying to reach the youngest generation because that's when you are told or informed that computer science is for specific types of people.

**Lenny** (01:00:46):
It's really sad to hear that it's heading in the wrong direction. What do you think is contributing to that?

**Crystal Widjaja** (01:00:52):
I think there is still a lot of this mental model of what a computer scientist is able to do and how much support they're given. So it's been shown in studies that at the youngest generation middle school, high school, you are more likely to be given introductory STEM classes as a male than as a female. So women just aren't targeted for STEM at that younger age. And so when they enter the high school or college classes for computer science, they're way behind. And that does not feel good. No one likes to be the worst in the class. And so it's more likely that you'll drop out. We've seen studies at Carnegie Mellon that actually would create introductory computer science classes before the college class starts. And for the women who did join those classes, they actually graduated at similar rates as their male counterparts. So it's really setting them up for success.

**Lenny** (01:01:52):
If folks want to help. You said that there's a PayPal page. Is there any other sort of action people can take?

**Crystal Widjaja** (01:01:58):
Yes. Enterprise software. We love to teach iOS development, licensed software. We have hundreds of students a year, so let us know.

**Lenny** (01:02:07):
Awesome. And they can reach you on generationgirl.com?

**Crystal Widjaja** (01:02:10):
Generationgirl.org.

**Lenny** (01:02:12):
Crystal, thank you so much for being here. I've taken enough of your time. Two last quick questions. Where can folks find you online if they want to reach out? And then other than the Generation Girl chat we just had, is there any other way folks can be helpful to you?

**Crystal Widjaja** (01:02:25):
Yes. Please find me at crystalwidjaja.com. You can reach out to me and my email is there. Listeners, please do instrumentation correctly. Please don't track your KPIs. Please track your user journeys and experiences. We'll have much funner things to talk about if you do that.

**Lenny** (01:02:43):
Amazing PSA. Thank you so much, Crystal.

**Crystal Widjaja** (01:02:46):
Thanks Lenny. This was a blast.

**Lenny** (01:02:48):
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.

---

## [9/20] How to own your career growth and become a powerful product leader | Deb Liu, Ancestry (ex-Facebook, PayPal)

**Lenny Rachitsky** (00:00:00):
You're VP of product at Facebook. You're director at eBay and PayPal. You're on the board of Intuit. You've been the CEO of Ancestry now for the past three and a half years. This is a career path that a lot of people dream of.

**Deb Liu** (00:00:11):
Some of the best PMs I have ever worked with are terrible PMs for their career. They just drift from job to job. "Hey, should I take this role or this role? How do I think about this?" But if I said you had to write a spec for your career, what does success look like? How are you going to get there?

**Lenny Rachitsky** (00:00:24):
You wrote this awesome post about introverts and how hard it is to be successful as an introvert.

**Deb Liu** (00:00:28):
The workplace is really favoring people who can speak up. It looks like self-promotion. I wouldn't want to do that because it's self-promotion. But instead, what if I called it educating about all the great work your team has been doing? Helping people see why your team should get more resources, you have to actually share what you do.

**Lenny Rachitsky** (00:00:45):
Is there something that you believe that you think most other people don't believe?

**Deb Liu** (00:00:49):
The most important career decision you make is who you marry. Is this person lifting you up or pushing you back? You will have a much more successful career if your home life is in balance. It's like a yin and a yang.

**Lenny Rachitsky** (00:01:03):
Today, my guest is Deb Liu. Deb was VP of product at Facebook where she spent over 11 years and while they're created and led Facebook marketplace, which is now used by over 1 billion people monthly, she also led the development of Facebook's first mobile ad product for apps and its mobile ad network. Also built the company's games business and payments platform, including Facebook Pay.

**Lenny Rachitsky** (00:01:23):
Prior to Facebook, she was director at both PayPal and eBay. She's on the board of Intuit and for the past three and a half years, she's been the CEO of Ancestry. I actually generally have a rule of no CEOs on this podcast, but to me, Deb is a great exception because she's a product person at heart. In our conversation, Deb shares a ton of tactical career advice, including why resilience is so key to career success, how to PM your career like you PM your product, how to be successful in business as an introvert, what she's learned about building multiple billion dollars zero to one businesses within a large company like Facebook and so much more.

**Deb Liu** (00:02:21):
It's wonderful to be here, Lenny.

**Lenny Rachitsky** (00:02:23):
It's wonderful to have you here. You have had such an incredible career. You're VP of product at Facebook. You're director at eBay and PayPal. You're on the board of Intuit. You've been the CEO of Ancestry now for the past three and a half years. This is a career path that a lot of people dream of and honestly just like one of those roles is a dream for a lot of people. And so I wanted to start with just this question and I want to see where the conversation takes us. If you could give one specific piece of advice to someone that's looking to do well in their career or to do better in their career based on what has worked well for you, what would that be?

**Deb Liu** (00:03:02):
Always be learning, and I tell this to everybody, so I often tell people, someone who's always learning is always going to exceed someone who's the expert today. You're going to find people... The one thing about school is that we go to school and there's such a thing as getting a hundred on the test, a perfect score on the SAT, graduating with a 4.0. Well, there's nothing like that in careers, right? We think it's actually a non-linear experience and there's always something better than you at speaking or presenting or strategy or execution. But if you're always learning, learning from the best, getting feedback, you're always going to get better every single day.

**Deb Liu** (00:03:35):
And that's what I have always held, which is each job I took, I didn't necessarily qualify for it. I wasn't necessarily the very best at it, and so it became the student of being better at that job. And once I mastered that, I was a student for something else, something else and something else. And so I always balanced learning and impact, which was you can have the most impact, the job you know the best, but then you stop learning. And if you're learning all the time, you're not necessarily having impact.

**Deb Liu** (00:04:00):
So how do you keep going back and forth and back and forth so that you're not going straight up a lot or you're actually laddering back and forth into different things where you're having an amazing time where you know everything and then you're the newbie again and learning new things, and you're incorporating what you used to know into what you're learning and the impact that you have today and so on and so forth.

**Lenny Rachitsky** (00:04:21):
**MUSIC** (00:05:40):
Pendo.

**Lenny Rachitsky** (00:05:44):
**Deb Liu** (00:07:14):
We'll start with my career in tech. So I had worked in consulting before business school. I went to Stanford for business school, came out to California, didn't know that much about tech, but I really loved using eBay. So I interned there my first year in business school and then when it came to finding a job, I really wasn't sure what we wanted to do, but we wanted to move back to the East Coast. And so I wasn't looking and I couldn't find a job. I think it was really hard. It was 2002. And so I ran into Tim Wenzel and Catherine Wu. So Catherine Wu was from Airbnb as you might know her. And Tim Wenzel put together the PayPal Mafia. He was the recruiter for PayPal.

**Deb Liu** (00:07:51):
Went to this table and I said, "Absolutely love PayPal, use it all the time. I'm a big seller on eBay," and he's like, "Do you want a job?" I'm like, "No, I'm actually going back east. "And he's like, "Just come in and talk to us." And so I said, "Okay. Well, what kind of jobs do you have?" And he's like, "I have jobs in product and I have jobs in marketing." Now, I've taken marketing class obviously in business school, and I said, "I wonder what this other product job is."

**Deb Liu** (00:08:12):
So I look over at Catherine and I've seen her around Stanford before, so she was a year ahead of me and I said, "Well, what do you do?" She said, "Product." I'm like, "That sounds good. I'll do that." And that's actually how I fell into product management. Well, I actually, and I'm embarrassed to say faked my way through those interviews, because during the interviews they're like, "Well, what would you build?" And since I was an avid user of both products, I could really richly say, "Here's the product feedback I have. Here are the new products you should build. Here's my feedback on things that we should be doing differently."

**Deb Liu** (00:08:39):
And they said, "Congratulations." And they gave me the job. And embarrassingly I went to the first day of work and I said to Amy Clement, who was the VP of product at the time, and I said, "Okay, I literally have no idea what this product job is."

**Deb Liu** (00:08:54):
She showed me the ropes and she was so incredible. She actually showed me, she said, "All those ideas you had, all that energy you've had around building these things, we go do that. Let's go do it." And I said, "Well, how do you do that?" And she said, "Well, you write down what you want to build and you work with the engineers to do it." And I just remember thinking, "This is crazy. I have no idea what I'm doing."

**Deb Liu** (00:09:14):
It was such an incredible adventure though. Those first few years, I just learned so much about the craft of building, how to really think through product use cases, how to think through what customers wanted, not just the customer of one, myself, but really what true customers and customer cohorts wanted. And so it was really a time when I felt like I was really blossoming, but I didn't come in with mastery. I came with a curiosity and I think that's what made me a great product manager was that I didn't have a set way of doing things. There wasn't some playbook I was trying to play. There wasn't some framework, but instead I was willing to learn.

**Lenny Rachitsky** (00:09:46):
So one takeaway might be from this, the phrase, fake it till you make it. Any thoughts on just how to... I imagine many people right now are like, "Oh, I'm trying to get a job as a pm. How do I do this? That sounds great. I'm going to pass this interview, figure out the job after I joined."

**Deb Liu** (00:10:02):
Coming in with humbleness was really important, but during the interview process, actually, I didn't realize this, but they asked me questions as if I was a product manager, as if I knew what I was doing. I think when you have passion around a product or passion around a company or around a business model or around something, it shows. And so it's not necessarily faking the enthusiasm or faking the idea that you want to work there, but you don't have to know how to write this spec or PRD or briefings or anything like that. You don't know how to do customer research or do data analytics or read reports, but instead show your passion around the product itself, around the use case, around the customer.

**Deb Liu** (00:10:41):
Show who you are and why you care. I think sometimes people just say, "I want a product job." But you have to be able to fall in love with the problem. You have to fall in love, not with the product, but I said the problem, right? The use case. What problem are you trying to solve? And if you can do that, you can be a great product manager even without a lot of experience.

**Lenny Rachitsky** (00:11:00):
That's an awesome piece of advice. So just lean into the passion. First of all, part of it is you have to be excited about the thing you're trying to work on or thinking about the company you're thinking about joining. Sounds like that's a prerequisite here. We have a podcast episode with Uri Levine who has a whole book called Fall in Love with the Problem, which is all about that same idea actually for startup founders.

**Deb Liu** (00:11:20):
I'll have to read it.

**Lenny Rachitsky** (00:11:20):
Yeah, he always wears a shirt, fall in love with the problem, not the solution.

**Deb Liu** (00:11:23):
Yes, is absolutely the most important skill for a product leader.

**Lenny Rachitsky** (00:11:27):
Something else I've heard you talk about in terms of something that contributed to your success is being okay with failure and just bouncing back quickly versus avoiding failure. Is that something that you can come back to a lot?

**Deb Liu** (00:11:40):
Well, here's what I noticed about everybody. I've coached a ton of people in my life. I have managed big teens and the people who are most successful are not the people who had no failures, who were lived charm lives, head up into the right careers and got promoted every cycle. The people who were most successful were the ones who actually through adversity, learned to turn stumbling blocks into stepping stones. They were the ones who got hard feedback and then came back stronger because now they learned what to do differently.

**Deb Liu** (00:12:09):
They were the ones who products failed, but they said, "You know what? I'm going to turn this failure into success. I'm going to take those lessons and make this company stronger." When you live a charmed product life, you always work on everything that's easy. You don't actually... Trees are strong because they bend in the wind, because they're tested, because it's cold, because it's windy, because there's conditions.

**Deb Liu** (00:12:31):
And that's how a tree goes grow strong and tall over many generations. And I think sometimes we think, "Oh yeah, I wish I lived a charm life." And that is not what we want. You want to have enough adversity that you learn to overcome so that you can build stronger over time and build resilience in your career.

**Deb Liu** (00:12:50):
I've seen that so much, which is the best product leaders I ever worked with are the ones that have the toughest stories, that had the hardest feedback, but also the ones who were able to bounce back quickly and make it happen.

**Lenny Rachitsky** (00:13:02):
We have a segment on this podcast called Failure Corner where people share a failure they went through kind of along the same lines and something we learned from that experience. Is there an example of that from your career where a failure made you stronger?

**Deb Liu** (00:13:13):
Yeah. I remember there was a job that I really wanted at Facebook and I'd been there for a long time. I had been leading different teams. I was a VP of product and then GM. There was one job that I never got to do, so I got to do all the jobs I wanted and Mark gave it to someone else. I told him at the time when he gave it to the first person who was amazing at it, I said, "If this job were open, I'd like to be considered for it."

**Deb Liu** (00:13:37):
The job opened up later, gave it to someone else. And I said to Mark, again, "I really wanted that job." And he said, "Not only will I not give you that job, you'll never have that job at this company."

**Lenny Rachitsky** (00:13:49):
What?

**Deb Liu** (00:13:51):
He didn't say it harshly. But he was giving me feedback about something which he did not see me in that role, in a role that I really wanted. And I had to decide each time like, "What do I do with this information?" This is my dream job. Actually, I decided I was going to turn the job I had and the job I wanted, and that's a choice. I could have said, you know what? I can't have that job. I could go do something else, but I didn't. I took the job I had with the team I had and I turned it into this thing that was going to be something we wanted.

**Deb Liu** (00:14:20):
And so I think sometimes it's not... I think that that experience was a very humbling experience because to be told no and then to say that this will never happen was really hard. But at the same time it was a reminder that you're not right for every job even if you think you are. And that you can take the raw materials of what you have and turn it into what you want.

**Lenny Rachitsky** (00:14:40):
Are you able to share what those jobs were that you wanted to get that you never got?

**Deb Liu** (00:14:44):
I never actually shared it publicly, but it's something which I had always had a role where I did new things for the company and there was a role where it was running something which more of an existing business, but I had always been kind of the innovator, the new stuff person. I had taken over so many new things. And so maybe that wasn't the right thing at the right time for me, but it was something that was really incredible and a turning point for me.

**Lenny Rachitsky** (00:15:08):
Great segue to an area I wanted to spend some time on which is building zero to one stuff within a larger company. So from what I can tell you built 2 billion businesses within a large company, Facebook marketplace, and then the ads platform within Facebook and maybe more. I don't know, the payments stuff, the games. I don't know. Maybe there's billions of dollars there I don't even know about. And this is very rare and very hard, and it's something we talk a little bit on this podcast, just the skills to build something new.

**Lenny Rachitsky** (00:15:38):
I know with marketplace it was not something people believed in for a long time. It took a lot of work to convince people to actually give it a shot. So I guess the question here is just what have you found are key tactics to start something new and allow it to continue to exist and get to a place where people start to believe it? What has worked for you?

**Deb Liu** (00:15:57):
So first, I didn't build the ads platform. I actually built the first direct response ad product company ever had. But we'll talk about how that led to why direct response is a vast majority of the ads revenue for the company. But one thing that it was really interesting is that I really saw my opportunity in Facebook to be somebody that zigged when other people zagged. There were amazing people who did a lot of the really core products working on feed, photos, videos.

**Deb Liu** (00:16:25):
I came in actually on the payments team and we worked on payments and eventually built games, which was the first billion dollar business. It was very successful. We worked with the likes of all the game companies that were on the Canvas games platform. And it was just an incredible opportunity to start from scratch and built something really cool. We built Facebook credits, which eventually became the Facebook payment system.

**Deb Liu** (00:16:47):
And then from there on I built the first direct response ads product. And again, leveraging the skills that we had, we had a lot of relationships with game companies because of my time and payments. And so we just said, "Hey look, what ad product do you want?" And they said, "Actually, your biggest challenge is the shift to mobile. Build us a mobile acquisition engine." And we said, "That's doable."

**Deb Liu** (00:17:09):
At the time the company was very brand oriented. Most of the ads... Actually almost all the ads on the platform were brand and we were not even on the ads team. So we actually worked on this team called the platform team. We said, "Okay, we'll build an ads product for the Facebook feed, the new mobile Facebook feed." And suddenly it became a billion dollar business within about 18 months, which was such an incredible journey.

**Deb Liu** (00:17:30):
We worked on the mobile advertising platform, so basically the mobile ads network. That was a great experience. And so each time I worked on something, it was just... The thing that you have to remember is the failure rate for something like this is very high. You start something and the amount of iteration... People think, "Oh yeah, it's easy." You start something and it's linear because you have all the resources of this company behind you. But actually everything in the company is like, "Let's do the most important thing."

**Deb Liu** (00:17:58):
These are seeds and we'll just let them... And so if you do that, you have to know that you don't get a lot of resources, you get a lot of attention. And I appreciated that because I think I work best when people aren't... There is not a lot of scrutiny. I think sometimes large companies, they say, "Well this innovation team," and then they check in on them way too much. They're like, "Week to week progress, where are you going? What's your strategy?" But so much as you know of building something new is the iteration process. It's the failing a lot.

**Deb Liu** (00:18:27):
We actually tested five or six versions of the ads product before we got it to take off and it took months, and then we were on the verge of death multiple times. In fact, I actually went back to run the payments team while I was working on that product because the team we had gathered still want to continue working on it, but I needed a second job back on the payments team because they asked me, "We don't think this thing is going to work. You should go run your old team again." And I thought, "Well, I will do both."

**Deb Liu** (00:18:52):
And so I did both for a while until it really took off. The thing that I think a lot of large companies don't realize is that you can love something to death. And so with every new product, I'd rather do it out of the limelight, do it with the minimal resources and have the freedom to fail because success and failure really is... In startups, failing fast is really important or succeeding fast.

**Deb Liu** (00:19:18):
It's the long slog that makes it really hard. In a company, you end up getting cut if you're the long slog product. And so being able to just say, "You know what? We're pruning this. We're doing the next thing, the next thing." And then having the time to iterate and grow is really critical.

**Lenny Rachitsky** (00:19:33):
So as a leader trying to do this and create space for this, is there something you've learned about how to allow for, "Don't over scrutinize us, don't look at us too carefully. We don't want to be in the limelight. Don't put too many resources on this yet." Is it just like, "Hey, Mark. Here's what I think." I imagine it's not as easy as that. There's a lot of influence and that kind of work. Is there any tactics that you could share to create this sort of environment?

**Deb Liu** (00:19:59):
I think the most important part of the environment is really patience. And again, this is a portfolio strategy and I tell every PM who... I used to do a new hire PM class and I say, "Look, a lot of you are going to go into the core product and your job is to grow X by 3 to 5% every six months. Growing engagement or growing sessions or maybe growing video views or whatever your metric is, you're trying to grow something 5% and then you exceed expectations."

**Deb Liu** (00:20:27):
And I said, "And then a bunch of you are like, 'I want to do something new. I want to build something from scratch.'" And I said, "By the way, a very, very successful company for a new set of products has a 50% hit rate. So half of you are going to come back in a year and have a different job because that did not work out. Do you have the resilience to do that?" And I think somebody, you enter a large company... By the way, you can have an amazing career building core products because that is an incredible journey within... Because you learn so much about the mechanics of what that takes.

**Deb Liu** (00:20:59):
And yet at the same time, I found a lot of energy from doing something that someone hasn't done before. And so I really enjoyed the, "Hey, this thing could fail. Let's pivot. Let's try to figure out. Let's prune this. Let's try that." And not everything I did there succeeded, but a lot of the things that are the lasting products are once that gotten really big. And so for me it was a greater reward and it made a journey so much more interesting.

**Deb Liu** (00:21:24):
But for others, I think work on the core product, learn the skills. It is absolutely respectable as well. But if you choose to be the person who works on innovation new products, expect in a year, you might literally have nothing to show for it, but the lessons that you learned. And I think those lessons are really precious and we often underestimate that too.

**Lenny Rachitsky** (00:21:42):
Along those lines, do you think it's a good career move to do a zero to one thing within a bigger company? Or is it often a bad idea? Do you have any advice there for folks?

**Deb Liu** (00:21:52):
It depends. It depends on your personality in the company. So the one thing I realized about my role was that I did a lot of... I had five different careers at the company over 11 years. And so most people don't realize that when you work on new things, you're constantly adding to your portfolio, subtracting from it, growing things, pruning them. And so you could just work on so many cool things except everything has similar... It's like it rhymes, but it's not exactly the same.

**Deb Liu** (00:22:19):
So you learn the lessons of how to get things done, how to get resource, how to get support when the product is not working, how to not get prunes in the next culling. And those are really, really important skills. But I think for people who are just starting out of the career, it is a very high risk thing to do. So if you're very early in the career, I encourage people just learn the core skills first. You can learn the core skills when there's a lot of stability. This product is growing X percent, like 5%, and you're going to grow at 10. That's amazing.

**Deb Liu** (00:22:47):
That is because you are there, you're going to change your trajectory of the product, or this thing has a hundred thousand users, you're going to get it to 200,000. Those are the kinds of things that are going to be successful for you and you can put on your resume. But I think it reaches a point in your career where you have to decide, when am I going to take the big swing? Because the big swings are the things that you write your career stories about. They're not just, I moved this metric X, but I changed your trajectory in this way.

**Deb Liu** (00:23:17):
And so the big swings though have a lot of failures along the way. And so you have to understand you're making trade-offs in that. I encourage everybody to take some time, two, three years in their career when they're ready for the big swing, where if it doesn't work... If it works, you run the team, you run this amazing product. It doesn't work, you can always go back and go back to the core products.

**Lenny Rachitsky** (00:23:39):
It's interesting how your strategy here is very similar to a product portfolio strategy where as a team should have a few big bets and then a lot of incremental stuff. And it reminds me about this awesome post called You Are in Control of Your Career. And the argument in your post is you should PM your career the way you PM your product. So there's a lot of synergy here. So maybe just diving into this post and advice around this, how should someone be PMing their career, the way they PM a product? What's your take there?

**Deb Liu** (00:24:05):
By the way, for your PM audience, I want to say this, which is a lot of the greatest PMs are the worst PMs of their careers. They love products. They love the crafts. They love the customer research, the data. They have plans, they have timelines. And then when it comes to career, they have none of those things. They just drift from job to job. "Hey, should I take this role or this role? How do I think about this?" But if I said you had to write a spec for your career, what's in there? What are your milestones? What are the skills? What are the features that you want to have of your career? How are you going to get there? What does success look like?

**Deb Liu** (00:24:41):
You actually have metrics for your product, and yet you don't have metrics for your career. I coach a lot of people and when I coach them, I ask them, "Well, where do you want to see yourself in five years? Where do you want to go?" And half the people have no idea. I think that's really tragic because when you PM your career, it's about intentionality. But I'll tell you the story of my career and how I was the accidental PM and then eventually... I told you how I accidentally fell into PM, but also fell into so many of the things that happened in my PM career.

**Deb Liu** (00:25:10):
And if I had to go back, I would think much more deeply about what I want to accomplish. So I ended up at PayPal working for a guy named Dave Lee who reported to Amy Clement, and then he left. And so she offered me his role. I had only managed people for, I don't know, 15 seconds. I was two years out of business school and I was definitely not qualified to do his job. He was the director of product. I wasn't even a director and I was running the team for eBay.

**Deb Liu** (00:25:34):
So basically the PayPal part of eBay, which was basically half the company's revenues and profits. Totally unqualified. I ended up in this job and I do a good job. I ended up doing it for several years. I built up the team and we have a great relationship with eBay. Our team was very close and we were able to actually build something really lasting that worked really well. And then I had a baby. And so this happens in a lot of women's careers. I was turning 30, I had my son, and I had to leave for six months.

**Deb Liu** (00:26:08):
So I handed my product to my successor, Mike Woo and he ended up taking over. He did such a good job while I was gone, I didn't want to displace him when I got back. And so I thought, "Well, I'll go and look for another role." I couldn't really find a product role I liked, I mean, because there weren't that many product director roles. And so I ended up in corporate strategy. So I worked for the amazing Rajiv who was CEO at the time. He since passed and I wrote his speeches, worked on strategies, I worked on digital goods and charity, and ended up building that into a vertical for the company. So charity, social commerce and digital goods.

**Deb Liu** (00:26:40):
And I thought, "Okay, this is an interesting job." So I create the job, have a couple product managers, wasn't really sure where this was going, and then one day I was like, "You know what? I'm not feeling this. I have a child at home." I had gotten into what Cheryl Sandberg calls that kind of between kids situation where I was bored of my job.

**Deb Liu** (00:26:59):
I was working one of the VPs I worked with and I resigned. I said, "I'm leaving tech, just I'm going to stay home and maybe start something small." He convinced me to hold off and he said, I'll find you a job. He calls me a week later and he said, "Found you a job with Stephanie Tilenius leading the buyer experience at eBay product." And I said, "Oh, that sounds interesting." So I said, "Sure, as you notice, I do not have a plan. I'm just drifting. I'm so fortunate that I had amazing mentors who gave me opportunities, but end up working for Greg Fant and Stephanie Tilenius at eBay for two years.

**Deb Liu** (00:27:34):
I led the buyer experience. We did some really good work there. And then went on maternity leave again. And I get a call from a friend, my old engineering manager from PayPal, "Hey, I'm at Facebook. Do you want to come? You can't come into product. You need a CS degree for that, but we have a product marketing job open." I was like, "Sounds good." Drop into Facebook. And so again, no idea what I'm doing back in product marketing. So I spent a few years doing that. Eventually was invited into product and so on and so forth.

**Deb Liu** (00:28:02):
And each job that came along was organic, but also kind of accidental. I see that happen in a lot of careers, which is my story when you look back, looks great. It looks like it all worked out, but I had almost zero intentionality in any of these. And I think that had I had more agency and I thought about what I wanted, I could actually measure is this the thing that would get me further or not?

**Deb Liu** (00:28:24):
I ended up extremely lucky, but not everybody does. And so I think having a plan allows you to compare every decision. It's not like when you're offered an admission to college, we're looking at three different offers maybe with financial aid or not, and you can make a decision, "Oh, they're offering me this department, but I can't get into this department." This is how far it is from home. But jobs and roles or nothing like that. Someone calls you one day, "Hey, I'm at Facebook. Do you want to come? I'm actually on maternity leave." And he's like, "Just come talk to me." I'm like, "Why not."

**Deb Liu** (00:29:00):
And you end up dropping into different parts of your life and I think sometimes by saying, "Here's where I want to go and here's how I want to get there," you can have such a better career. And so I do encourage everybody to do this and to think about what does success look like in five years and how far am I from that and am I heading in the right direction?

**Lenny Rachitsky** (00:29:20):
What's interesting is I also had a similar path to you where I had zero plan or intention or goal and also just follow things and things worked out. I wonder how often that happens and I wonder if this idea of having intention and planning a roadmap is something you do if things aren't working out because maybe there's some good to not overthinking it and just following pull. I don't know.

**Deb Liu** (00:29:45):
Well, I think the problem is this with you and me, Lenny, is that hindsight bias is a problem. We made it because we weren't intentional in a lot of ways, but for how many people, is that true? For how many people who aren't... You don't have a plan and you get there. I always tell people, if you are sure what your destination is, that's definitely where you're going to end up. But if you actually aim in the right direction, you can shape your learnings, you can shape your roles you take, you can shape your skills towards the place that you want to go.

**Lenny Rachitsky** (00:30:16):
When you talk about getting this offer from Facebook, usually those are like you have three days to decide.

**Deb Liu** (00:30:21):
Yes.

**Lenny Rachitsky** (00:30:22):
And it feels like that's when the things you've done ahead of time of here's what I want would be most helpful.

**Deb Liu** (00:30:29):
Also, I think the thing about job opportunities in particular is they tend to come serially. It's only you presented these offers. It's like one role is so different from another and they often don't happen at the same time. They might say, "Well, you have to decide in two weeks." And then you say, "Well, there's this other company I'm talking to and you get a lot of pressure to say yes to this versus this."

**Deb Liu** (00:30:49):
And to really having a measuring stick is this getting me closer or further away from where I go? Can allow you to actually take serial decision making to a place where you're measuring against a long-term goal.

**Lenny Rachitsky** (00:31:01):
I did a meditation retreat once and when you're meditating, there's this kind of guidance of don't try too hard, don't push yourself to go into a direction, "Oh, I'm not doing a good job. I need to get to this enlightened state." And instead their advice is just push your cart in a direction and think about that's the direction you want head, but you don't need to grasp on to here's where I need to land, here's where I need to go. And I wonder if just having a thought of here's where I want my career to go. I want to be on boards in the future. I want to start a company in the future. I want to become a designer in the future. At least start there maybe just like a direction that you're heading.

**Deb Liu** (00:31:40):
Yeah. There's a woman who I worked with in product and now she's the founder, very successful founder, and she said to me, "I want to join the board of this Fortune 100 company." She told me the company, and I said, "Okay, that's a lot." So she said, "How can I get there?" And I said, "First, it's probably going to take you 10 years because look at who's on the board. I happen to know a couple people on the board." And I said, "Why don't I introduce you to one of them? And they can tell you how to get there.

**Deb Liu** (00:32:04):
But the point is she knew where she wanted to go and she said, "I'm willing to take it first step today." And I said, "First, you've never been on a board. You were very successful, but this is not... There's so many steps before you get there. It's like before you go to Harvard, you have to graduate from elementary school to middle school. You have to take the SAT, you have to apply. I said, "Let's start from the first step and let's break this problem down."

**Deb Liu** (00:32:29):
But I love that she knew where she wanted to go and she's like, "Even if I don't make it there, I'll be happier having made this journey." And I love that for her. And I think she's still earlier in her career, she has so much time ahead of her, but it's really incredible to see her kind of on this path and to know that that's her dream, and that I can help her a little bit along the way.

**Lenny Rachitsky** (00:32:48):
It also relates very much to your idea of thinking of your career like a PM thinks about their product where one of the tactics is to imagine the ideal scenario and work backwards from that versus incrementally what's the next thing? What's the next thing? So in this case, she was thinking, "Here's where I want to head. Okay, what's the next thing to get to that direction?" I love that.

**Deb Liu** (00:34:22):
Well, first, I love the book, Quiet by Susan Cain. She talks about the power of introverts. Unfortunately, the world doesn't see the way the world the way she does. I wrote this post. It was the secret bias no one talks about, which is the workplace is really favoring people who can speak up. And I tell the story of somebody on my team who's just an amazing product manager, and yet every time she came up for promotion or calibration, people were like, "Oh, what does she do?" And it was because she was not good at broadcasting or explaining what she does.

**Deb Liu** (00:34:54):
I would take her to executive meetings and she was really bad at answering questions or talking. And so we would prep and prep and prep. I just knew her skills and I could see her every day moving the product forward. But for some reason people... Because your peers also have influence over people's ratings and their promotions, and I was constantly just trying to figure out how to get them to see her brilliance. I asked her once, I said, "I noticed that you never answer questions when we do these presentations." She's like, "Yeah, because I'm a processor. And by the time I process, I feel like the conversation has moved on."

**Deb Liu** (00:35:28):
And so I really feel like the world, it's not built for somebody like her who's a brilliant product leader, but people couldn't see it. And I realized that so much of what products and just general leadership is, is not just doing the work, but actually... It's not just having the product, it's having great product marketing to go with it. Let's call it that. Okay, so I've been in product and I've been product marketing. You make a light bulb, but you're selling light.

**Deb Liu** (00:35:53):
I really think about how that she was making amazing number of light bulbs. She was lighting up all the houses, but she was not marketing the light. And I think that was the thing that was really missing. Is that fair? Absolutely not. There are a lot of people who are born introverted. Is it fair that a product manager who isn't introverted, isn't extroverted is struggling with that? No, but that's the world we live in. And so it's one of those things where you get to choose what you do.

**Deb Liu** (00:36:21):
First, I think for the individual is realizing that you are your own best marketer. You have to actually share what you do. If a great product is out in the world, but no one is told about it, did it exist? And so one of the things that's very important is really to get that product marketing.

**Deb Liu** (00:36:39):
The second part is we should change our workplaces so everyone can be successful. And I think that that's a really important skill. As more introverts get into leadership, they need to actually change the world to make more space for people like them as well. So one of the things that I found was in my leadership teams over the last several years, we had this thing where we all vote, but we vote offline in a document and we put a number in and then we put our comments in.

**Deb Liu** (00:37:05):
And that way everyone has an equal voice in this document. And then when we talk about it, usually, of course the extroverts speak first, but everyone has a vote and we can actually see what people's point of views are. And I love that. I love that when there's something we used to do at Facebook is we used to go around in a circle and everybody would give their opinion in a meeting. I do that still today. I ask every single person as a business leader at this company, would you do this?

**Deb Liu** (00:37:30):
And even I joke with our chief legal officer, Greg, I say, "You are a business leader and the lawyer. You can't just say, well, legal advises X." I'm like, "But what would you do?" And so nobody can take a backseat to decision making. Everybody has a voice. So there's so many of these kind of bias interrupters, things that we can do to actually make the world easier for those who weren't speaking up and taking 80% of the air in the room. And I do think that we have to craft a workplace where everyone can be their best.

**Lenny Rachitsky** (00:37:59):
In the post, you also talk about as much as we want to change the way people run their companies and think. I love your advice of you also still have to learn how to speak up and act more extroverted even though it's not natural to you. Is that right?

**Deb Liu** (00:38:14):
I think we do a disservice when we say we're not good at speaking up because it's a skill like any other. And if I told you the difference between your product being successful and not being successful is you giving this presentation, they're going to kill your product if you don't sell this to the executives. You would figure out a way to stand in front of those executives and defend the freaking heck out of your product. But why aren't you doing that every day?

**Deb Liu** (00:38:35):
And I think sometimes we forget that not everything is as essential as they're going to cut your product if you can't convince them to keep it. But every day you're actually building credibility for your team, getting more resources, getting more people to talk about your product inside your company, getting more press for the product outside. All of those things combined into momentum for your product. And don't you want the best thing for your product and your customers?

**Deb Liu** (00:38:58):
So if you think about it that way, it's not, well, I'm uncomfortable. I hear this a lot where people say, "Well, you wouldn't understand. I'm an introvert." And I'm like, "So was I." But instead I just said, "Okay, this is a necessary skill and it's a learnable skill. You don't have to be comfortable with it. You don't have to love it, but you just have to do it."

**Lenny Rachitsky** (00:39:19):
What about from another perspective of why people don't do this, which is it feels like self-promotion and it feels like icky like, "I'm just sitting around promoting myself. I don't want to be doing that." Anything there that helps people get over that piece?

**Deb Liu** (00:39:31):
Well, I just remember I was talking to this ERG group and I was asking about... There was an upcoming calibration and self reviews were due in a couple of days. And I said, "Well, what are you doing for your self-review?" And somebody raised their hand and said, "Well, I'm really bad at self-promotion. What advice would you have for me?" And I said, "If you think your self-review is self-promotion, you're just not going to do a great job at it."

**Deb Liu** (00:39:56):
What if I called it educating your manager about all the great work your team has been doing? What if I called it helping people see why your team should get more resources? Suddenly you're cracking open, you're changing the question right from, "Oh, I was self-promoting to actually I'm helping my team get more resources and support." And suddenly she was like, "Oh yeah, I never thought about it that way."

**Deb Liu** (00:40:22):
But I think often if you frame it one way, it looks like self-promotion. I wouldn't want to do that because of self-promotion. But at the same time, if it's education, what if I said, "I was talking to a PM who's really incredible. I've mentored him and sponsored him for a long time." And I said, "I don't understand why you don't have more of a voice. You've learned so much about the craft. You've done this at multiple companies." And he said exactly what you said which is I'm not really self-promoting.

**Deb Liu** (00:40:46):
And I said, "If you see it as self-promoting, you will never do it." And so let's talk about why you don't actually do this. And he said, "I've seen a lot of people who are really great on LinkedIn write these articles, but they have nothing to back it up." And I don't want to be like them. And I said, "Okay. Well, you read my blog, you follow me on LinkedIn, do you think I have nothing to black back it up?" And he's like, "No, of course not."

**Deb Liu** (00:41:07):
And I said, "Well, then why do you put yourself in his category instead of mine?" And I think it was just a moment where we just came to an understanding where he in his mind was like, "I don't want to be that person. It's an empty vessel that has no substance behind it." And I said, "Do you think the things I write have no substance?" But it was an interesting conversation because he had taken this mantle that it was self-promotion and that behind what if people think I'm nothing behind it?"

**Deb Liu** (00:41:32):
I'm like, "I know you have something behind this. I have been your manager. I have worked with you for many years, but you see how just reframing it has really changed his way of thinking about it." Still working on him. But I actually think he has so much to give and I think he has learned so much about the craft, and I wish that more product managers feel comfortable that they have something to give to the world.

**Lenny Rachitsky** (00:41:53):
I think what you're saying right now will resonate with a lot of people when they see people posting. I feel the still of just like, "I don't want to be this guy that's just posting nonsense on LinkedIn just to get likes," even though it's kind of what I do now full time. Hopefully it's not nonsense.

**Deb Liu** (00:42:08):
But it is all substance. So, Lenny, we know the substance behind it.

**Lenny Rachitsky** (00:42:11):
I tried, but I think there's posting on LinkedIn, posting on Twitter. There's like an innate just doing this because I want to get attention when often... And the way I started this is just like things I've learned that I think are useful, I'm just going to put them out there. So just to double click a little bit, I think this is a really powerful point. What actually have you found helps people get over that? Is it someone like you and his corner being like, "You have really great stuff to share, you should actually do it. Don't be as worried as you are, as you think you might be." Is there anything else that works there?

**Deb Liu** (00:42:41):
Actually what worked for me was I was working with Bos and I talk about our relationship in my book, but we made a contract when I started reporting to him. And Bos, for those of you don't know, is currently the CTO of Meta. At the time he was the head of ads and then our team moved into his team. And so I was reorged into his organization. And as I said we did not have the best relationship before that. And so we made a contract to work together and I had written like, "Here's how I want you to take care of my team. Here's how I want you to support our products." And I wrote them this long, my part of the commitment.

**Deb Liu** (00:43:13):
Then he wrote back, "Here's what I'm asking of you. I want you to write and publish something every month." I was like, "What are you talking about? Why would you say that?" He said, "You have so much to teach people. Just do it." I said, "I don't really have that much to say." And he's like, "Just trust me on this. You'll figure it out." His advice was write what you repeat. If you say something more than once, just write it down. And then the next time someone asks you, you can just hand them.

**Deb Liu** (00:43:40):
He has a great blog if you have read it. I just normally thinking that is a weird thing for your new manager to say after you had a lot of conflict together before that. But he took my contract, which was... By the way, he's like, "Oh, do you want to codify this in some way?" I'm like, "No, I just..." But every month from then on, I would literally just write something and it was my promise to him. And I did it faithfully and I published it internally. So I didn't publish it externally for a long time.

**Deb Liu** (00:44:04):
And then sometimes they would ask me if I want to publish it externally for the company and I would say yes. And so I did it for years. I reported to him for years. And then we switched managers. He moved over to Reality Labs and then I had a new manager and I continued and I continued this. Then I started doing a publicly, and then obviously I wrote a book. Because of him and his encouragement, it got me to a totally different place. And part of it was just the commitment. I now had accountability because I knew he was watching. I'm not actually sure if he was actually watching every month. But I felt the accountability to do this and I've done it every single month since.

**Lenny Rachitsky** (00:44:37):
So it's interesting that that's another example of your manager giving you the space slash forcing you to share publicly being a really good lever to get someone over this fear.

**Deb Liu** (00:44:48):
I think sometimes just doing it gets you over the hump. For example, my friend, Ami Vora. She writes an incredible blog. You have not read her Substack, you should. But she's an incredible writer. She'd write all these things internally and I said, "You should publish this externally." Now she does that and it's really great. And I think part of it was just seeing her just put it out there because she is one of the wisest career coaches that I have and managers that I have ever worked with. And so I'm like, "You have so much to say and to share."

**Deb Liu** (00:45:16):
So to see it out there, I feel like for years we all got the benefit of it because we knew her. But the world was not getting the benefit. So in some ways just having accountability. So we created a little accountability group to help each other write, and it was just a reminder, "Hey, did you do it?" And so I think it's sometimes what's necessary to get over that hump is either having someone forcing you, like your manager who you made a commitment to, or just having a friend to say, "Hey, by the way, where's this month's post?"

**Deb Liu** (00:45:41):
Those things matter because now you got over the hump of, "I have to do it." And now it's just about how good you're going to make it and how much time you're going to put into it.

**Lenny Rachitsky** (00:45:49):
Awesome advice. And by the way, folks don't know we've had both Bos and Ami on the podcast in the past.

**Deb Liu** (00:45:55):
Aren't they both amazing?

**Lenny Rachitsky** (00:45:56):
Amazing. And Ami's episode is one of the most popular episodes. More popular than Bos, CTO of Meta.

**Deb Liu** (00:45:56):
I know.

**Lenny Rachitsky** (00:45:56):
Who would've thought?

**Deb Liu** (00:46:06):
She has a lot of coaching wisdom I think that everyone should hear.

**Lenny Rachitsky** (00:46:08):
Yeah, she's amazing. She has a great Substack. We'll link to it again in the show notes. We'll link to your Substack as well.

**Deb Liu** (00:46:13):
Yeah, please do.

**Lenny Rachitsky** (00:46:15):
Go Substack. I want to move in a slightly different direction. Talk about growth for a little bit. You have a really nice perspective on how to think about growth. I think a lot of people think of growth as like, "Here's a magic bullet. We're going to do this thing. It's going to go, "Wow, we're going to win." And your approach is, you talk about it, it's a game of inches. Growth is a game of inches. Can you talk about your perspective there?

**Deb Liu** (00:46:34):
Yeah. Sometimes we think it's like what is the huge step function? But actually most companies are like... We call it points of growth, right? It's like if you can move things 1% a little bit faster every single week, think about the amount of growth you get at the end. And so it's not just, "Okay, what's going to get you the 3X? You can get to 3X 1% at a time, 5% at a time. Single digit growth. And sometimes it is the small things that matter the most. And so we think about product-led growth, it's really about finding the aha moments, the opportunities. And sometimes opportunities are things that seem really silly.

**Deb Liu** (00:47:10):
I heard the story at Facebook that one of the big things was just adding the, next to ads, they put the word create an ad, was one of the biggest growth drivers. And that was it just putting a link because people just didn't know how to get to the ads flow. It was things like that where you can actually bend the curve of choices that you make. Same thing, each of the growth teams I've ever worked on, it's like really the small things adding up. It is a list we used to work on payments growth and we had a list of a hundred things we were working on hypotheses.

**Deb Liu** (00:47:42):
And then we would pick and we would grow them by picking the first 10 and we would start working on them, the next 10, the next 10, and we would go through these sprint cycles. And the same thing when we were growing the ads product as well. Marketplace, each of them were just like, "What are the small things that add up to big things?" And I think sometimes we overthink it.

**Deb Liu** (00:48:00):
Instead, you probably have a hundred ideas. And by the way, it is absolutely okay if the 80% of them don't work. I tell people sometimes we overthink as product manager if we just had the perfect plan, the perfect battle plan, but instead imagine you're a team and you can ship, I don't know, let's say four things. But what if you're a team that can ship 20 things with the same with a 20% success. You get just as much output and yet you know what doesn't work also.

**Deb Liu** (00:48:30):
What if you can move it from 20% to 30%? Suddenly six things work, not just four things. And so in the same amount of time you have all the lessons of what didn't work, plus you're getting 50% more output. And so you thinking about growth as this engine of, it's a learning machine of what doesn't work, what you reiterate on, what you change, and you're constantly getting better and better and better.

**Lenny Rachitsky** (00:48:50):
I think what you're saying will resonate with a lot of product people where there's always this like, "We're just doing a bunch of optimization, incremental work. Still sucks, boring. Let's take some big bets." And in my experience, and sounds like in your experience, a lot of the wins actually... And Facebook is famous for this, just relentlessly looking for ways to grow, optimize, optimize, optimize because that's where a lot of growth comes from.

**Lenny Rachitsky** (00:49:14):
At the same time, obviously you need to take some big bets and take some swings and look for step function changes. But I guess for someone that's just like... I don't know. Is there any advice on just creating that culture of like, "It's okay to optimize for a long time, there's a lot of opportunity optimizing"? Is there anything you've learned there or is it just bringing in a Deb and it has to be a top down?

**Deb Liu** (00:49:32):
I treat growth like, let's say, a product marketing team. It is an augmentation for a product that works. So if you have a core product that works, you have a team that's working on... So for us at Ancestry, it's like search and hints of the core. What is the mechanics? You want people to add people to their family tree. You want them to add stories, okay? There's teams that make sure that the uptime is good, that the hints are working, the search delivers results.

**Deb Liu** (00:49:57):
And you need those teams, you need those core teams kind of functioning. But growth is actually optimization on top. It is making it so that you get to the search flow faster. The hints are surfacing better, that people are accepting them, that if we put the button here versus here, that people are going to discover things faster. And so it's really taking the core engine and actually wrapping it around the user interface around the experience, around the flows so that people can get to it faster, they can have more satisfaction, they can have more impact. And that's what I see growth as. It's not the core product. It is the cherry on top, making that product more accessible and more usable and better every single day.

**Lenny Rachitsky** (00:50:37):
Along these lines, I think it surprised people to learn. There's at least a hundred people at our Airbnb just working on pricing, optimizing pricing recommendations. There's endless opportunity to just make all these core components of an experience better and better and better over time. Okay. Last thing I want to talk about, and this is completely unrelated to everything we've been talking about mostly, which is your 30, 60, 90-day plan.

**Lenny Rachitsky** (00:51:00):
So you wrote this post a while ago, just like, here's a great 30, 60, 90-day plan when you join a company. I've heard that many people use this. It's really effective for helping someone onboard and be successful. And I think it's mostly for execs or is this for just anyone joining a company?

**Deb Liu** (00:51:16):
It's for anyone.

**Lenny Rachitsky** (00:51:17):
Okay, anyone.

**Deb Liu** (00:51:18):
I created, it's actually when I joined Ancestry because I hadn't started a real new job in 11 years. And I thought, I'm going to be a student of how to land well. So I read a bunch of things, I read and I decided I was going to adapt all of those things into a summary and then I was going to try it real time in my blog.

**Deb Liu** (00:51:38):
So in my blog I write, "Here's what I'm going to do," and then I tell you what I did and how it worked and some things. And then I actually do a look back as to all the mistakes I made. And so I did this live. It was not planned quite as well as I would thought, but I put it together and I wrote the 30, 60, 90-day plan and I have a template. I always tell people it's focused on listening and learning first and then doing. So that's the crux of it, which is in those 90-days it's like you got to get used to the environment. You want to have some impact at the start. You want to have a couple quick wins, but you want to understand the lay of the land and you want to listen because you have something to contribute.

**Deb Liu** (00:52:19):
But if you don't understand the language, you don't understand the culture, you might actually make huge mistakes. And so for the first 30 days, I did a listening tour. I talked to over 60 people in 30 days and then I summarized a state of the union. Here's what I'm hearing, here are the challenges people feel like we're facing. Here's what people's wishlists are. And by the way, one person sent me a wishlist of five things and at that year, I think it took me till year two to finish his five things. And then I sent him a note. I said, "By the way, the first time we met, these five things you wanted to see, we just finished the last one."

**Deb Liu** (00:52:50):
And he's like, "I can't believe you remember." I took extensive notes and I summarized it. I think it's important because people want to hear that you hear them. And you don't have to be a manager or CEO to do that. I think people on teams often feel like there's no outlet for the things that they want to say. I encourage, especially product leaders, especially if you're joining an existing team, to listen really behind what people are saying and then offer to help them do one thing.

**Deb Liu** (00:53:17):
So especially when you're meeting with a new engineering team for the first time, actually ask them, what is one thing I can do to help you this week? I always say one thing, it's limited. This week, so getting 15 new headcount. Probably not going to happen. And it's like, how can I give back? And suddenly you're building a reciprocal relationship. And so a lot of this 30, 60, 90-day plan is really to help you find your footing and then to start having impact immediately.

**Lenny Rachitsky** (00:53:43):
Say you join a company and you're like, "I'm going to do 30 days listening," and then your boss is like, "No, we need to ship stuff. Get on it, ship this stuff." Is there any advice for trying to push back on that, create space for listening when there's deadlines, things aren't [inaudible 00:53:56]?

**Deb Liu** (00:53:57):
I encourage everybody to get on the same page on this 30, 60, 90-day plan with their manager. So actually don't just keep it to yourself. Share it with as many people as you can. So I think it's very important that everyone sees what you're trying to accomplish and what your output is going to be. Because if you don't know the output, is success there? The second part is with your manager say, "Okay. I would like to carve 20% of my time listening and I'm happy to do this work 80% of the time." Therefore every morning from nine to 10, I want to talk to somebody in the organization.

**Deb Liu** (00:54:28):
Just make sure you say, "I will do a better job and have more impact if I have this time to make sure that I'm not accidentally making mistake or I don't get a chance, I'm asking something of somebody, but I've never met them." And to really carve out space because it's really important. Once you're in it, people give you the new person card for maybe a month or two and then suddenly it's all the problems are your problems.

**Deb Liu** (00:54:53):
But what if you don't know what the problems are? And so I always say diagnose before you treat. So make sure you understand so that you can help and deliver what your manager is actually expecting of you.

**Lenny Rachitsky** (00:55:04):
I'm looking at your template. So just to share the bucket. So first 30 days learning focus, second 30 days is aligning on vision for the future, and the last 30 days of the 90 days is executing, setting up, actually starting to get stuff done. Awesome. Anything else along these lines of this?

**Deb Liu** (00:55:23):
The one thing about having a plan also is that you don't feel rushed to do something that you're not ready for because I do think sometimes you feel like you need to have impact. I always tell people, "Do something small, give back in some ways that people see you making." But when you actually reflect, one of the biggest things I could do was actually reflect back to the organization, "Here's what I heard from all of you. I'm listening, I hear this and here's what I want to do about it."

**Deb Liu** (00:55:53):
And then in aligning it's like, "Do we agree this is a set of problems we want to tackle?" And then an execution is like, "Do we agree that this is how we want to move forward?" And I think that is such an important part of building into a team. When you enter an organization, you're also entering a team and you're part of a dance that's going around. What role do you play? And people are dancing around you and if you actually make a mistake, you could trip other people up as well. So really finding your place in the dance is really important.

**Lenny Rachitsky** (00:56:21):
And as a PM, the way I always think about is people won't assume they should trust you. You're just this person that's coming in to tell them what to do and so much of your first month, two, three is building that trust with people so that they can actually feel comfortable listening to your guidance and not just like, "Oh my god. This person is getting in my way."

**Deb Liu** (00:56:40):
And earning that trust, sometimes people really... You'd be really surprised, a lot of people feel like they're not heard and even just coming in and listening is a trust building exercise.

**Lenny Rachitsky** (00:56:51):
Such a good point. As we wrap up our conversation, just a couple more questions here. So first is I want to take us to Contrarian Corner, which is a segment on this podcast. And my question is there something that you believe that you think most other people don't believe? Something that you think is a contrarian perspective?

**Deb Liu** (00:57:10):
I don't know if this is a contrarian perspective, but I go to speak in a lot of universities. So I speak at Stanford and I'm going to speak at Duke. And I always tell people, especially young people, the most important career decision you make is who you marry. And it's not something we think that much about, especially I started dating... I met my husband when I was 18, my first weekend in college. Started dating when I was 19. We had no idea what our life was going to be like and yet every single day like this week we had our board meeting, I was in Utah the whole week. I come home and he's taking care of everything.

**Deb Liu** (00:57:43):
You will have a much more successful career if your home life is in balance. It's like a yin and a yang. If something is out of balance, it engulfs the other side. Both your job and your home life. And especially, we have three kids. Really balancing that is very hard over both of us having demanding careers. It's not something that's contrarian, but it's something which we don't think about at all when we make that decision. We think is this person fun to be with? Is this person somebody we see ourselves with? But my question is what is the impact of this relationship on your career?

**Deb Liu** (00:58:14):
Is this person lifting you up or pushing you back? Is this person someone who's going to be your greatest cheerleader or are they going to be the greatest weight on you? How do you think that that's going to manifest itself 20 years, 30 years from now? And I think it's just something I wish we thought about more and I encourage especially young people to think about that.

**Lenny Rachitsky** (00:58:33):
Such a great point. What I want now is a guide for vetting these things when you're dating. Deb's guide to dating.

**Deb Liu** (00:58:44):
I need to write that. Although I've only really dated him, the one person, so maybe I am like the worst person to tell.

**Lenny Rachitsky** (00:58:49):
But it worked, so you're maybe the best person and now you look back.

**Deb Liu** (00:58:49):
That's right. That's right.

**Lenny Rachitsky** (00:58:53):
And here's the questions I asked that worked. That's so funny. Okay, so before we get to our very exciting lightning round, is there anything else that you think might be helpful to share, something you might want to leave listeners with? Any other nuggets of wisdom or advice?

**Deb Liu** (00:59:08):
Well, there's one quote which I share, I thought about when you were speaking earlier, which is about people who are resilient, which is life... This is a quote from Chuck Swindoll, he's a Christian writer I used to read a lot and it was, "Life is 10% what happens to you and 90% how you react to it." And I just looked him up recently and he actually published a book with that quote. He actually had that quote in a previous book from 20 years ago.

**Deb Liu** (00:59:34):
And I just think that's so important. You don't get to choose everything that happens in your life. So much is just, it just happens, but it's the people who choose a way forward to turn stumbling blocks and the stepping stones. As I said, "Somebody who actually says, 'you know what? I didn't get the job that I wanted and I'm just going to figure out another path,' those are the people who have the most successful and satisfying careers." They're thinking when other people are zagging vice versa. And I think that there are the ones who are the most resilient and happy in the long term.

**Lenny Rachitsky** (01:00:06):
It's such a good circle back to one of your first pieces of advice of just most successful people are people that are resilient and don't avoid failure, but embrace it and find a way to turn that around. I think it's such an important point. It's so hard to do. I guess just, I don't know, just to follow this thread a little bit, is there anything that has helped you build that? Has that always been the way your mind worked? I imagine coaching helps this, helps people with this." Is there anything just like that?

**Deb Liu** (01:00:29):
Coaching is incredible for that. We joke it's work therapy, but really I think it's... For a long time I saw failure as this catastrophic thing. I was one of those kids who's like, "You never got a B until..." Then I got to college and I was like, "Wow, this is harder than I thought." And so I got two B's in college and I'm like, "I'm never doing that again." But I was that kid who always got the A, who got the great scores. I just thought that my life would end if I got a B which by the way is super unhealthy.

**Deb Liu** (01:01:00):
And looking back, I realized that work is not like that at all. And every time I got bad feedback I'm like, "This is catastrophic." But if you look at feedback as an opportunity, then it's very different. It's like this is a gift. I would be crushed. Every time I get a review no matter what rating I got, I would read the things that people would say and I was like, "Oh my gosh, I'm a terrible person." And I had to really rethink that. And I think coaching, leadership coaching has really helped me through that to say, "No, how do you process this and how do you get to the other side?"

**Deb Liu** (01:01:33):
And that has been so transformative for me is to have that outlet to actually talk through. No, no, no. What they're saying is not that you're a bad product person, it's that you need to do a better job communicating or connecting. And I really struggled with that. I was very transactional. I was not a connector. I was not warm. I really struggled with relationships. And a lot of the feedback I received for many years is this relationship issue. And it took me a long time to realize that people aren't saying this because I'm a bad person or that they hate me, but because they want to connect.

**Deb Liu** (01:02:03):
I was actually making it hard. And I think sometimes we take things so personally that it becomes kind of this thing. It is your white whale. It's like the thing you're chasing, but then what if you say, "You know what, I don't need to do that. I don't need to chase that. Instead I need to figure out what's behind the feedback and what are they trying to say?" And then actually change yourself over a long period of time towards that.

**Lenny Rachitsky** (01:02:26):
I had similar challenges where I had this pretty real imposter syndrome for a while when I started doing well. And a coach was the key for me to help me get over that and see that if I made a mistake. Things wouldn't crumble. And that it's very normal to make mistakes. Nobody will-

**Deb Liu** (01:02:43):
And by the way, I think perfectionism is a curse we place on ourselves. And it's a very dangerous thing, particularly for product leaders because product managers, you know things are going to go wrong. That's literally part of your job. And yet when we have perfectionism, it is a lack of trust in our ability to bounce back and our ability to actually adapt. But the more adaptable you are, the less you have to be perfect every single time.

**Lenny Rachitsky** (01:03:09):
Just to leave people with a tactical piece of advice, say they are like, "Oh man, I need a coach," do you have any advice for how to find a coach? How to explore that route?

**Deb Liu** (01:03:17):
So I actually wrote an article, because one of the things I struggle with coaching is very expensive often, and not every company provides it. My husband actually works at a coaching company called Sounding Board to make it more accessible. But one of the things I encourage people to do is there are other ways to get coaches. I'm in a lean-in group and we are just like, we support each other. I'm in a coaching circle in YPO, so that's a group of CEOs. And I'm in a number of these coaching circles, which give you an opportunity to learn from each other and to get pure coaching. And I think that's a great place to start, especially early in your career when you're seeing the same people making the same mistakes.

**Deb Liu** (01:03:54):
I think as you get more senior, having an individual coach helps because the situations are so much more unique. But I do think that having that outlet, having a place to say, "Hey, is it me or is this situation not right? And how should I think through this?" That's so incredibly important.

**Lenny Rachitsky** (01:04:10):
I'm listening to this book, or reading a book called Listen right now that a previous guest recommended. It's a parenting book and it's about just the power of listening and how much that solves many problems with your challenges or with your child. When your child is having a problem just listening to them. There's a lot of power. This came from a coach that was on the podcast recently. [inaudible 01:04:31]

**Deb Liu** (01:04:30):
Sounds great. I'll definitely, I'll read it or listen to it.

**Lenny Rachitsky** (01:04:34):
I know it's weird. I'm like reading, it's called Listen. He's like, "This is the only parenting book you need really. It solves all the problems that we deal with." So anyway, that was an awesome final nugget that I'm glad we got there. With that though, we've reached our very exciting lightning round. Are you ready?

**Deb Liu** (01:04:52):
Let's do it.

**Lenny Rachitsky** (01:04:53):
Let's do it. First question, what are two or three books that you've most recommended to other people?

**Deb Liu** (01:04:59):
So I love the book from Professor Jeffrey Pfeffer. I speak in his class now that I read it way before that, it's called Power: Who Has It and Why. I love the book. He actually has the more practical one, 7 Rules of Power, which came out more recently. And so it's a book that reminds us that power is not accidental, that people often get it for different reasons and how you should think about the playing field.

**Deb Liu** (01:05:23):
Another book is The Conversation, Dr. Livingston wrote that about race in America, and I just love that it's a very honest assessment of race in America. It's hard to have that conversation and I love that he uses a lot of facts and encourages people to open up and have conversations around it. And then the last one I would say is, well, Susan Cain's Quiet. I adore the book because I do have introverted kids. I myself am introverted and just to read the power of introverts as a reminder that we do have amazing people who don't communicate the same way.

**Deb Liu** (01:05:59):
I love that it's a tribute to the success of those. Even if our workplace is not adapted to it, I do think we need to adapt to it so that we can bring the best in everybody. But her book is a reminder that there's so much power even in silence.

**Lenny Rachitsky** (01:06:13):
The first book you mentioned Jeffrey Pfeffer, he's been on the podcast. I think he may have mentioned you in our conversation or-

**Deb Liu** (01:06:17):
I love Professor Pfeffer.

**Lenny Rachitsky** (01:06:19):
That was a fun conversation because I came into it very nervous for what his advice would be and then came up with it being like, "This is great. This is-"

**Deb Liu** (01:06:28):
He is very wise,

**Lenny Rachitsky** (01:06:29):
He's very wise and just very, "I don't care what you think, I'm just going to tell you the reality of the world." Oh man. Okay. Next question. Do you have a favorite recent movie or TV show that you've really enjoyed?

**Deb Liu** (01:06:41):
Okay. I know this is a fandom thing, but I love Fallout. So I played the game Fallout 4 last year, and then the show came out and it was amazing. And I know that sounds so nerdy, but it was incredible. And I know that video game movie annotations tend to be terrible, but it was so great and having played the game it was even better. Is that super nerdy?

**Lenny Rachitsky** (01:07:06):
No, I watched Fallout. I don't know anything about the game, but the show itself was really fun. Just I had no idea what I was even getting into. So no. Acceptable nerdy level. I don't know if you can get too nerdy on this show. Next question, do you have a favorite product you recently discovered that you just really like?

**Deb Liu** (01:07:26):
Well, so actually what's really interesting is I never got into Twitter. I just couldn't figure it out. Recently I really got into Threads and I didn't think I would. I was like, "Well, just post some stuff on it," but really I just love... I could never figure out Twitter. You follow the wrong person and the whole thing, it's terrible. If somebody is posting too much or too little, but there's something about the Threads algorithm that's really worked. The first few months wasn't quite there, but I just feel like it's spot on and now I see the magic of it.

**Lenny Rachitsky** (01:07:59):
That's so interesting. I've seen some stats that it's bigger than X now slash Twitter and I wonder if that's true. I got to look that up, but I've seen more activity on Threads. So maybe I need to go back there. I spent some time around-

**Deb Liu** (01:08:10):
Cheering from the sidelines that it's successful because I use it a lot now. And I guess I had never had a place for realtime news and it's not exactly meant to be newsy, but maybe it's just who I follow, but I love just seeing like, "Here's five headlines you probably missed." And I was like, "Oh." I know they're trying to downplay politics, but I just love that it feels like you get a glimpse of what's going on in the world in five minutes."

**Lenny Rachitsky** (01:08:35):
Okay. Two more questions. Do you have a favorite life motto that you often think about, come back to, share with friends or family find useful in work or in life?

**Deb Liu** (01:08:42):
Ooh, that's a good question. Well, actually, I would say that it's very similar to the Chuck Swindoll one about life. So we can use that.

**Lenny Rachitsky** (01:08:52):
Great. That's what I imagined because you shared that one early on. And I imagine that was going to be your answer. Final question, you started Facebook Marketplace, you built it. Now, it has a billion users, more than that. What's the most interesting thing that you have bought or sold on Facebook Marketplace?

**Deb Liu** (01:09:07):
The best thing I ever sold on there was I sold my minivan on it and in four days. I made my husband do it because I wanted him to test the product. We were selling our minivan and I'm like, "Just try Facebook Marketplace." He's like, "I don't know about this." And he's like, "There's too many people contacting me. I needed it to stop." So it worked really well for us. I think I have bought so many things on there. It's actually sort of embarrassing.

**Deb Liu** (01:09:30):
Recently, my daughter wanted the same desk as I had for her new room and they no longer sell it at Costco. And I found it for half the price from a woman who was moving and she's like, "Here," and I love it. So I bought probably way too many things on Facebook Marketplace actually. But it's a great thing. I actually use it as a great rental for kid stuff because you buy a kid's bike and then when they outgrow it, you sell it back.

**Deb Liu** (01:09:56):
And the rental fee is almost free and I don't have the store all of it. So I love every part of it. I still am an admin user and I send a lot of feedback back to that team still.

**Lenny Rachitsky** (01:10:06):
That's amazing. Deb, this was amazing. I'm so happy we made time for this. Thank you so much for coming on. Two final questions. Where can folks find you if they want to reach out, maybe read about stuff you're doing? Where's your Substack and anything else people can check out?

**Deb Liu** (01:10:18):
Yeah, so debliu.substack if you want to look. I post probably about once a week. I'm on LinkedIn, I'm on Threads, so please do find me.

**Lenny Rachitsky** (01:10:27):
And then the actual final question, how can listeners be useful to you?

**Deb Liu** (01:10:33):
Well, I would just love to hear what you heard from today that resonated with you and what you're going to do with it.

**Lenny Rachitsky** (01:10:37):
And how would they share that LinkedIn or at Threads?

**Deb Liu** (01:10:41):
I'm happy to read your comments or send it if you want to-

**Lenny Rachitsky** (01:10:41):
There we go.

**Deb Liu** (01:10:43):
... send it to me. If you've actually subscribed to my Substack, you can just reply to the first email and then I get it.

**Lenny Rachitsky** (01:10:48):
Awesome. But the easy way, as you said, are replying to YouTube comments. There we go. Get people to YouTube, click that subscribe button. Deb, thank you so much for being here and thank you.

**Deb Liu** (01:10:59):
Thank you so much, Lenny. It's great.

**Lenny Rachitsky** (01:11:00):
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.

---

## [10/20] How to launch and grow your product | Ryan Hoover of Product Hunt and Weekend Fund

**Ryan** (00:00:00):
I don't know how to articulate that- that feeling, but that flutter in your stomach that you wake up with in the morning of just anxiety and stress and- and worry. Um, being a CEO or founder makes it slightly harder, uh, in some ways, because you still have to put on this mask. You have to put on this space of confidence externally and- and internally as well, where people need to trust you. You also don't want to subject them to the same anxiety that you're feeling and be a 100% transparent.
**Lenny** (00:00:28):
Ryan Hoover is the founder of Product Hunt, which you already know. He's also former product manager, which I did not know. Currently, he's a full-time investor with his fund, the Weekend Fund. He's also an author of a bunch of great block posts and an actual book, called Hooked. He's also really good on Twitter and in my opinion, a very special human being. Ryan Hoover, welcome to the podcast.
**Ryan** (00:00:52):
Hey, Lenny. Thanks for having me. I've been reading a lot of your blog posts over, I don't know, past two or three years now, and I'm glad to- to see you do the podcast now. It's cool.
**Lenny** (00:01:01):
Thank you, man. That compliment will go straight to my heart. And I will think about it often. I appreciate that.
**Ryan** (00:01:07):
Cut- cut that and put it on Twitter. There you go. Yeah. [laughs]
**Lenny** (00:01:09):
[That's the clip, we're done. [laughs]
**Ryan** (00:01:10):
Yeah. Done, over. [laughs]
**Lenny** (00:01:14):
[laughs] This episode's brought to you by RevenueCat. RevenueCat makes it easy to build, analyze, and grow in-app subscriptions on iOS, Android, and the web. Their platform lets you focus on growth rather than getting bogged down in subscription infrastructure. RevenueCat provides a backend and wrapper around Apple StoreKit and Google Play billing to handle the implementation and upkeep of in app purchases. RevenueCat is your source of truth for customer status across platforms and provides out of the box analytics for key subscription metrics like monthly recurring revenue, lifetime value, retention, and more. With RevenueCat, you also get pre-built integrations with best-in-class tools like Amplitude, AppsFlyer and Firebase. That means reliable, consistent data synced to your entire product and growth stack in minutes. UA companies like Notion, VSCO, and Life360 use RevenueCat to power in-app subscriptions. Learn more at revenuecat.com.
**Lenny** (00:02:12):
Hey Ashley, head of marketing and Flatfile, how many B2B SaaS companies would you estimate need to import CSB files from their customers?
**Ashley** (00:02:22):
At least 40%.
**Lenny** (00:02:23):
And how many of them screw that up? And what happens when they do?
**Ashley** (00:02:26):
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 CMC importer doesn't work right, which is super common, considering customer files are chock-full of unexpected data and formatting, they'll leave.
**Lenny** (00:02:43):
I am 0% surprised to hear that. I've consistently seen that improving onboarding is one of the highest leverage opportunities for both sign-up conversion and increasing longterm retention. Getting people to your aha moment more quickly and reliably is so incredibly important.
**Ashley** (00:03:01):
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 flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster.
**Lenny** (00:03:17):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny.
**Lenny** (00:03:23):
You're such a tech celebrity; everybody knows Product Hunt. Everybody knows Ryan Hoover, at least in tech. And I'm curious, how often are you recognized walking around the street, in life, and has there ever been like a super awkward or super hilarious moment of that?
**Ryan** (00:03:37):
Yeah, so t- Product Hunt started in late 2013 and quickly got a lot of traction in- in the tech- tech sphere. So, yeah, people in tech, um, might recognize me. People outside of tech, doubt- doubt they recognized me. Um, I actually do wonder subconsciously if I grew my hair out to avoid being recognized.
Um, I'm not sure if it's true or not, but anyway, it's been a couple years or so growing my hair out and I'm like, ah, I just kinda wanna like disappear sometimes. But, you know, in San Francisco, where everybody's in tech, um, there was a lot of that. And probably the- the, the moment where I was like, "Oh, this is- this is like a thing," uh, it was probably early Product Hunt, uh, I was at- do you remember... I don't know if you know this. Do you know a club, um, called DNA Lounge, and they did something-
**Lenny** (00:04:19):
Mm-hmm.
**Ryan** (00:04:20):
... Called Bootie every Saturday-
**Lenny** (00:04:20):
Mm-hmm.
**Ryan** (00:04:21):
... It was like a mash-up dance party.
**Lenny** (00:04:22):
Yeah.
**Ryan** (00:04:23):
Yeah. Super well known in the Bay Area. Really fun, fun, uh, kind of experience. Anyway, I remember being with friends and drinking, like- like one does and somebody turns around and says, “Is that the Product Hunt guy?”
**Lenny** (00:04:33):
[laughs]
**Ryan** (00:04:33):
And that was the first time that sort of happened in that setting where I was like, oh gosh, now I have to like, think about my actions. And I can't just like, be entirely like loose and, you know, relax with my friends. And, um, so anyway, there- there's always pros and cons to those types of things. Um, but you know, it- it definitely is makes me more aware of, I'm already a very, like sometimes anxious and like self-aware person in terms of like my surroundings.
And so when you combine that with, “Oh, these strangers might be watching me,” is not the best thing in the world, but it's okay.
**Lenny** (00:05:04):
I've actually gone a little bit through that same experience recently in my, like a much smaller sense where I- with this newsletter and the growth of this thing, there’s been like meetups happening all over the world. And so I've been going to the SF meetups here and there, and it feels very strange to be like, known and people get- they’re like taken pictures with me, like what the- what the hell's going on.
‘Cause I started this thing as, uh, COVID hit and it was like- everyone's at home, I was just typing on my computer, didn’t have to go anywhere. And as the world has emerged, it's become a new- a new thing I'm dealing with, on a much smaller scale.
**Ryan** (00:05:35):
Yeah. Yeah. Events are events are fun. Um, we threw a bunch of them at- at Product Hunt. Uh, yeah, you- you do a lot of selfies and a lot of like, handshakes and it’s- there's, there's some energy there. I'm an introvert though. So by hour, like three or four, I'm just like, ugh… uh… I need to use the restroom cause I haven't been able to escape and I'm socially exhausted, so, but they are fun.
**Lenny** (00:05:55):
I know, uh, exactly what you mean. I am also an introvert and I get so drained doing things like that. I was gonna ask you about that. So yeah. Um, along the same lines, you’re- you're a very public person. You tweet a lot, you share a lot, you do a lot of podcasts and things like that. What's something that people don't know about you?
**Ryan** (00:06:12):
Yeah. Um, you're right. I- I probably sh- maybe overshare, uh, on Twitter and other things…
**Lenny** (00:06:17):
No, that, that is not what-
**Ryan** (00:06:18):
Um, there is a list of [laughs] no, no, I know. I know what you're saying. Um, but there's also a whole series of things that I don't talk about. Um, some of them- well, anyway, I won't, I won't talk about the things I can't talk about.
Uh, but one thing that, um, one thing that most people don't know about- I know there- there's certain juicy things, uh, like everybody has in their life. Um, I recently moved to- well, I guess it's been a year. Um, I moved to Miami about a year ago and, uh, I haven't been talking about it publicly, primarily because I just didn't want to be lumped into, oh, another person moving to Miami.
Like, I, I don't know. I just, there's no benefit or like, reason for me to do so. Uh, I want my friends there in Miami to know I'm there, but otherwise I don't need the world to know. I guess now they will. Um, that said in Miami, you know, we’re- we're there about two thirds of the year, so I'm actually in California right now.
Um, as you know, the summer humidity come- comes through Miami and hurricane season. We’re- we're planning to do more of, um- I wouldn't call it nomadic and I wouldn't call it bicoastal per se, but something like that. Where two thirds of the year we’re Miami and then maybe a third were in New York, or LA, or someplace else.
Um, and I love that. Um, fortunately we have the flexibility, uh, when I say we, my girlfriend, Susie, and I, to just carry our laptops and work anywhere. So it's been- it's been a nice lifestyle kinda shift.
**Lenny** (00:07:33):
I did not know that, that is very interesting. Why did you get pulled into Miami? What pulls you there?
**Ryan** (00:07:39):
Yeah. You know? Um, so the way I describe ci- cities are kinda like a product. So if you're in the supermarket or- supermarket, I sound like an, old- old person. Ha, if- if you're at a store, you're looking at different products, or if you're online, you're evaluating different products, and they each have like a cost and they have some benefits, um, or values or whatever you- you want to use to describe it.
And for me, each city is kind of like that. And so, you know, in terms of costs, there's cost of living in terms of housing, uh, food, taxes, a bunch of things that go into the cost of living in the city. And then the city provides a lot of benefits and- and things like that. And so in LA- so I was in bay area for ten years, LA for two Miami for one.
Now, they each have their own pros and cons. They each cost effectively different prices. And so we visited Miami a year and a half ago and we just fell in love with lot- lots of it. Um, we also- it's just cheaper. It's cheaper than the Bay Area. It's cheaper than LA. Um, when- when you kind of count, kinda like all in costs, um, and we had a bunch of friends move there, so we enjoyed the city.
We're like, this is good., strong ROI. Uh, this is a good product. Let’s- let's move there. Um, but at the same time, as I mentioned, like- we are traveling and, and exploring other cities. So it’s- it's kind of the best of both worlds for us.
**Lenny** (00:08:53):
Very cool. Um, curious how long you last there and how you like it over time. I love Miami. I always have a good time when I go there. And I have many friends living there. Changing topics, a little bit, something that I've noticed you do recently, which is super cool is you offer people the chance to DM you questions that they have about their startup or their journey as a founder.
And you just offer to give 'em free advice. And then sometimes you, tweet the DMs to share that with more folks. I'm curious just how many people have DM’d you because this is such a cool offer, and what have you learned going through this and kind of hearing people's questions?
**Ryan** (00:09:26):
I first opened up my DMs- I had 'em closed, which is like traditionally the default on Twitter for a long time. ‘Cause I was like, “Oh, if I open them up, I'll just get a bunch of spam and I don't need another inbox to- to call through.” I opened it up quietly and, um, actually didn't get a lot of spam, uh, surprisingly. Like yeah, people would shill something or promote something, but it wasn't too bad.
So I- I left it open and then I forget, one day I was maybe I was like- on the elliptical, bike or the recumbent bike or something. And I was just… I- I tend to get on the bike and just hold my phone up and just do emails and work. And so, um, I just said, “Hey, DM me if you have any questions, any founders, and I'll try and like answer as many as I can.”
And, um, part of my motivation for that was… I don't know, I was just killing time. And the other was, I used to blog a lot. I used to write a lot, um, I don't know, I've written hundreds of blog posts, but not so much anymore. I rarely write anymore. And part of it's because it just takes so long to write.
And sometimes I don't feel like inspired by any topic. It’s- it's sort of like a writer's block. And so I found this also kind of as a means to like, do micro- almost like micro blog posts in a way, uh, where the prompt is the question from somebody else. I don't have to think about the pr- prompt. And then the answer is- is in some ways, a way for me to actually think about that- that topic, almost like refine my own thinking in, in some sense.
And so I started doing that and then I realized, “Well, maybe other people have similar questions, and maybe other people have other answers and other ideas too,” so I would just take a screenshot of my answer and kind of summarize their answer, of course, keeping it anonymous, not sharing anything that would be sensitive. Um, and just put it on Twitter and- you know, it's been fun.
I do that maybe once every three or four days, I share a new question and answer and, sort of like a… It's like micro blogging in a way, I guess that’s what Twitter is, but like it's a kind of like a real micro-blogging kind of like, uh, um, activity for me.
**Lenny** (00:11:15):
Is there anything that's kind of surprised you, or that you've learned from founders? What they ask you about? Like, “Wow, I didn't expect this was gonna be such a common problem or question.”
**Ryan** (00:11:24):
I wouldn't say anything like super surprising. However, a lot of people… So, you could do the same thing on Twitter and say, “Hey, AMA, ask me anything in public,” the thing is people are not gonna ask certain things, um, for a lot of reasons. And maybe the biggest surprise was a lot of people are pretty vulnerable.
These are strangers, founders who DM me saying, “Hey, I’m- we have three months runway left. We’re running out of money. Here's a situation. What advice do you have?” Or just things that, you know, everyone has to wear this unfortunate mask is kind of the way I- what I used to describe it. This mask in life, in business, where everything is going great.
And you know, you're super confident, there are no problems. You got it all under control. And so the reality is that's not the case. Like [laughs] if you peered inside of almost every single company, it probably looks chaotic in- in different ways. And so I guess- I guess maybe the biggest surprise or thing that I value the most is the authenticity of people willing to share some of these, um, vulnerable moments and questions.
**Lenny** (00:12:17):
Awesome. What's interesting about your format is as you were talking, I kind of realized it's very similar to my newsletter format, which I- which I think is part of the reason it worked is it's based on people asking me a question, and then I answer the question, and then-
**Ryan** (00:12:28):
It's true.
**Lenny** (00:12:29):
… And that ends up forcing you to have like concrete, actionable advice.
So you've kind of developed even more interesting way of doing it on Twitter, where it's more focused. So, very smart.
**Ryan** (00:12:39):
I've always liked your format by the way, in that you are, um- you're a curator in many sense. Like- yeah, you have a lot of experience and good ideas, but you're not trying to answer all the questions in that you are really pulling in experts in their domain expertise to like find answers or inspiration.
And I've always liked that format because one; it, I think leads to a better- better results, better content, better answers, but also it's arguably easier. Um, like imagine if- if you tried to like write, well, you you're shaking your head almost like it’s-
**Lenny** (00:13:10):
Like if I had the answers, I'd be like, “Oh, here you go. I'm done.” You know, the research takes a lot of work and time, but- but I do agree. It ends up being a lot more useful and, and- and valuable. And the reason I did that, just to kind of explain that briefly, is when I left Airbnb, people kept coming to me and asking me like, “Hey, how did Airbnb do this thing?
How'd they do that thing.” And I was just like- like, they, they don't know what they're doing. They just did this thing, and who knows if that was the thing that helped them, or if that was the right way of approaching it. So I wanted to do this, like, “What does everyone do? And what seems to be the pattern of the things that work?” And that kind of led to this approach.
And it takes a lot of time. Especially this new series that we're gonna chat a bit about that I worked on where it's just like endless interviews and chats and researchers and watching interviews. But yeah, it works out.
**Ryan** (00:13:54):
Yeah, yeah. You- you, how many hours actually, do you put into like a typical essay?
**Lenny** (00:13:59):
Oh, a reverse question. Uh, I would say the-
**Ryan** (00:14:02):
Yeah, I don’t know if I'm supposed to ask you questions, [laughs] but I'm curious.
**Lenny** (00:14:04):
This is banned. [laughs] No, it's cool. I say- I'd say the, uh, median post is about 10 hours. It's like, maybe I kind of work on it through the week. So maybe, like a few days through the week, but the most epic posts take hundreds and hundreds of hours that I kind of work on behind the scenes as I work on the weekly posts.
So there's a wide range. Some posts take like three hours and sometimes those do very well, much better than expected.
**Ryan** (00:14:30):
Yeah. Yeah. I- that's exactly going back to my, my point about like- it takes a long time to write content that you're proud of. Um, I’m also just very particular about words, uh, for better or worse. And so I- the first draft actually is maybe like 20 or 30% of the time. And then the rest is refining it and getting feedback and everything else.
**Lenny** (00:14:48):
That's exactly how I find it. The question I wanted to ask is, startups are so freaking hard… they almost always fail. It's always just like, “Oh my God, this is… Why am I doing this to myself?? My general advice to founders is like, don't start a company, unless you just like, can't not start a company because it's so hard.
What's your take there? What do you think? What do you advise founders for when they're thinking about, should I start a company? Should I not start a company? Which- how should I approach this?
**Ryan** (00:15:15):
I do- I do spend time, ironically, like. challenging founders sometimes when they're thinking about raising or thinking about an idea to- to not raise. Um, people who are in tech, uh, especially, are certain bubbles [laughs] of tech, that’s the default. It's like, “The first thing I do, I have an idea, now let's go raise money.”
And we've gone through some like pretty massive bull cycles where that- that was possible for a lot of people. But it's a huge decision. So with- with Product Hunt, it was a side project in the beginning. It wasn't actually intended to be a startup at all, but in the beginning, you know, it was a newsletter, then it was a website and it was about four to five months before we even incorporated.And we got a lot of traction. 
So, it was during that time, I was really just thoughtful around, "Should we raise? Do I wanna work on this for many, many years? What's the opportunity? Is this even a venture backable like idea?" Like all those questions were circulating in my mind for a while. And this is also in a time when the market was pretty, was similarly bullish. This is, uh, end of 2013, early 2014. And investors were- were using Product Hunt to reach out to me, and they were sort courting- courting me, and um, kinda doing that whole song and dance to invest, but I- I just wasn't sure if I wanted to. And so, I don't know, I think a lot of the- those decisions, they're very personal and contextual. However, I think it's super important that founders see a line of sight to work on this for ... I think my rule of thumb is a decade, just do you see yourself working on this for a decade?
And maybe it's not a decade that you actually work on it. It probably won’t, it either, it'll probably fail before then as most startups do, but I think it's a good litmus test for yourself to be like, “Do I actually care about this enough? Am I, am I really stoked to work on this for many, many years?” But then, you know, the other thing is, I think a lot of people also think “I need to start a company. I need to start a startup.” 
And they skip to that step without just tinkering and building and, you know, Product Hunt, we called it, not even a side project, we called it an experiment. And that framing I think, is for me, has always been helpful because it's an experiment is really not about success. Of course you want it to be successful, but the goal is not success.
I put that in quotes, it's really to learn and, you know, see if people want this thing and then kind of adapt. And so like an experimental mindset is helpful and I think a valuable way to start. It even goes back to like, why I named the fund Weekend Fund. It's like, what are you tinkering with on the weekends?
You know? And how can you be more curious and experimental and kind of your exploration of new startup ideas?
**Lenny** (00:17:43):
I didn't know that's why it was called the Weekend Fund. I thought it's because you worked on it on the weekends, or is it both?
**Ryan** (00:17:48):
[laughs] It had like multiple meetings. Yeah, it was- three meanings: One was- was that I started Weekend Fund when I was building Product Hunt. So it took a lot of pitch- pitches and calls with founders on the weekends. Two, I think a lot of great ideas start by like metaphorically speaking, nights and weekends, um, kind of side projects or ideation.
And then the third reason was it was like more friendly. I don't know, I didn't wanna name it. Hoover capital or something like sterile, wanted it to be -
**Lenny** (00:18:14):
Wait, that's an awesome name. Hoover capital. Wow.
**Ryan** (00:18:18):
…Capital. Uh I don't know. I, I feel well.
**Lenny** (00:18:23):
Yeah, it's not on brand,
**Ryan** (00:18:24):
Yeah.
**Lenny** (00:18:25):
But it’s powerful-
**Ryan** (00:18:25):
Um, yeah. [laughs]
**Lenny** (00:18:28):
As you know, I asked people on Twitter what questions they would want to ask you. And so I'm gonna inter splice these questions as we go through this. And, you just touched on Product Hunt and fundraising, and I'm curious if you were to go back and- and do it again.
Would you raise money for Product Hunt, or would you not?
**Ryan** (00:18:44):
Great question. So at the time, this is also the thing I ask [laughs] founders is why do you need to raise money? Like, what is it for? Surprisingly, some people like- I don't know, like they don't have a clear answer. For me, It was pretty obvious. Like we needed- we needed to hire, we needed people. Like, I- I didn't have personal capital to- to pay people.
There was an alternative, uh, reality where we actually built an open source. I was thinking like, “Is that possible?” Like we're building something for the tech community. I'm sure a lot of people would love to work on this. Could we build it in an open source way, but that like- that's really hard to do.
And when you're building a company, you probably don't want to innovate on too many things, um, including like essentially how to build a product and build a team. Anyway, to answer your question, if I- I don't, I don't know what the right at the time raising money was the right decision because I- I wanted to hire and I didn't have personal capital.
There really weren't any other realistic options. I don't think. Today I could get further with my own- I'm not super wealthy and I'm super illiquid, but I have at least enough money where I could have funded, you know, maybe a year of development with this very small team. So today it might be a little bit different in which I might not raise venture capital because Product Hunt isn't the type of company that needs to raise a ton of money.
It's also one which is not, um, doesn't have like direct competitors in the sense of like an Uber and Lyft situation where raising is actually like kind of mandatory and you sort of have to build a massive war chest to compete. So there- there is a scenario where if I had more money, then maybe I wouldn't have raised venture capital. But yeah… there- there's a lot of other like decisions and other things that probably, uh, bigger mistakes I think I made. Um, not that raising money was a mistake by any means. It was, I think the right decision then, but yeah- there's a lot of learnings in hindsight's 2020.
**Lenny** (00:20:31):
The point you made about like, you just needed money to like run the thing. I think that's so, so overlooked when people bash the idea of fundraising for a startup that maybe didn't need it. Like you just need money. Like you don't have just money to burn and go into debt. That makes sense to raise some money and see where this thing goes without really knowing where it's gonna go.
**Ryan** (00:20:49):
Mm-hmm .Yeah, especially if it’s… I mean, I think it's very important to raise- raise from people who are aligned with you too. Meaning like, “Why does this person want to, whether it's an angel or a fund, invest in your fund?” Um, sorry, not fund… your company. When you go down a certain path, when you raise a series A, B, C, like you have different expectations and when you raise your proceed or seed round. So I think also understanding like, you know, what you're signing up for is super important.
**Lenny** (00:21:16):
What kind of treadmill you’re- you're getting on.
**Ryan** (00:21:18):
Yes. Yeah. ‘Cause you can't get off. I mean you can, but it's not like a company… I always say like when you're at a company, you can put in two weeks, notice one month notice. You can move on. As- as a founder or CEO, you can’t. Like, you really can't. Um, now you technically can… But you can’t, it- it's really, hard, um, to, to exit.
**Lenny** (00:21:38):
Yeah. I look at the Airbnb founders. Who've been doing this for 15 years. Like, you know, they're doing well in life, but they also… it's very hard to leave.
**Ryan** (00:21:46):
Mm-hmm.
**Lenny** (00:21:38):
Yeah. Coming back to Product Hunt, people launch their product on Product Hunt, that's the thing, and I'm curious; founders are always so obsessed with launching and the power of a launch, and "We gotta launch.” Do you think launches are worth it for a company? Is that something founders should be spending time on or is it often better just to not even spend time on that and just build slowly?
**Ryan** (00:22:07):
Yeah, I- I always kinda ... Whenever I share like my perspective on stuff, I- I always enforce it always like it kinda depends, which is kinda like it sounds like a cop-out answer. So, it's- it's more ... My answers are usually more nuanced, and the thing about launching is- is going back to why are you raising money. What's the goal? Same thing. Why are you launching? And the the- a lot of people default to things like customer acquisition, "Oh, I wanna acquire customers." But sometimes that's actually not- it's not useful. Launch sometimes doesn't help with that, but there are many other reasons why you might wanna launch.
So, customer acquisition one, to get the word out. Another can be recruiting. So, by, you know, sharing your story, getting people excited, it might make it easier to recruit and get people excited about, you know, what you're building. Another is fundraising. Sometimes it can create momentum, you know, as- as other investors, they do read the news and they know that, you know, when this company is more public, they're might be more heat around it- a particular deal. Feedback is one. Um, the feedback from users, feedback just serendipitously and- and sort of another one is partnership. So, as you launch, you might also encounter more partnerships, more opportunities. I think there's a serendipitous effect of launching. So, I think understanding like what are the priorities of the business. Like if you- it might not be customer acquisition at all, it might be, "We need to recruit and hire. Let's launch, so we can get the word out. Hopefully that will help land, you know, our next, you know, engineers, designers, or whoever." 
And then I also see there's like these little ti- side benefits too of launching that we see a lot through Product Hunt. One of them is team morale. And this- this might- I think this is overlooked. And I- I would also encourage [laughs] founders not to get their team too, um, I would say- you- you shouldn't be motivated to launch a product just to get like the likes on Twitter and the upvotes on Product Hunt, but there is a gr- like a powerful team morale and kinda building moment there where you can all celebrate what you've accomplished and what you built and put it out to the world. And, you know, somebody on the team can share, you know, the- the- the Product Hunt launch or, you know, some Tech Crunch article with their- their mom. And, you know, like that seems like a trivial kind of meaningless thing, but it actually matters for a lot of people. And then the other thing is SEO. So, if SEO's like a part of your strategy, having articles, positive articles, having a- a positive Product Hunt launch, things like that can also be helpful.
**Lenny** (00:24:21):
That's awesome. I love that last point about morale. I- I hadn't thought about that. You've seen probably more launches than other person out there. How many launches of startups would you estimate you've kind of like seen or been [laughs], I don't know, an observer of? If that makes any sense.
**Ryan** (00:24:38):
Um, I should look at our database on Product Hunt and see how many launches we've had 'cause it's gonna be a subset of that. I mean by seen, I- I- some of it's very high-level, but tens of thousands over the years.
**Lenny** (00:24:48):
Okay, so when you think about that, do you have any sense of what correlates with a great launch versus just like an okay launch? What- what do founders miss with how they launch?
**Ryan** (00:25:01):
Yeah, I mean the- this goes back to college and- and the a- you know, I won't go on my own rant about education, but in, uh, you know, English class and writing class, a lot of teachers teach people to write with big words and fill pages of content and basically not speak like a human. And so, one- one thing I've noticed among founders and just people in general is they tend to write like a- a PR person and not like a human and not like, you know, the- the way that I kind of describe kind of a frame of- of writing, maybe your tagline for Product Hunt, um, or for your launch in general is like how- how do your customers or your users describe your product to other people? Or another frame is how do you describe it to your friends? Like when you're just, you know, hanging out, like how do you describe what you do, what you built, what it's for? And that language, I think, resonates with people because it feels way more authentic.
And the people that use buzzwords and- and vague language, it just doesn't click. People see right- people are sick of the PR [laughs] speech. And so, I think the language and the microcopy, copyrighting matters so much. And then there's a lot of other things around like we should go more to the product and less about the launch. Like do you really understand who you're building for? And do you understand how to communicate the value prop- like what is it in the mind of user? There's sort of a lot of, I guess, more strategic kinda like decisions that go into that- that, uh, before the launch.
**Lenny** (00:26:22):
Imagine each of those, uh, points can be its own podcast and block post. [laughs] One of the questions that people asked me on Twitter was the classic, "How do I get to number one on Product Hunt?" So, my question to you is I know that's like ... There's not gonna be a silver bullet. Is there like a guide that you point people to that's like, "Here, just follow this advice," and/or, I don't know, two or three key things that you just gotta get right.
**Ryan** (00:26:44):
Yeah. Yeah, so in the posts below, there's actually a link- links to a bunch of guides and FAQs and things like that. So, it's really easy to find like sort of the best practices there. The team also has like this checklist. So, once you launch, there's like a checklist of things, recommendations or tips. And I'm actually forgetting like what each of them are specifically right now, but some of the things that I've noticed that make a big difference is we've already talked about the tagline copy, that goes to, not only the post, but also the maker. Usually people tend to add like some introduction, some context. Uh, generally a lot of people will, they- they manufacture PR speak there too, and so speaking like a human, I think, is important. Also keeping it a little brief. Some people write essays, which might be interesting, but the reality is most consumers, especially people on Product Hunt, you know, they're- they're flipping through a bunch of ideas. They're looking for things that spark their curiosity and interest.
And they probably not particularly interested in reading like an [laughs] essay, you know, from- from the makers. So, keeping that short, I think, is helpful. And then another big one is the gallery is- is often the first thing that someone is gonna see once they land on the page. And so, just naturally our eyes gravitate towards visuals. And some of the most interesting presentations I've seen is people use the gallery almost like a slideshow, um, like telling a story, where each slide is- is communicating like a different- well, a story of some sort. It could be like, "Here's the before and after with our product," or "Here's the evolution of what this product can do." There's many different ways to approach it, but like a really clean, you know, visually interesting story, um, can also be a great way to like capture people's interest in what you built.
**Lenny** (00:28:21):
Awesome. That was very tactical and helpful. If you were to launch something on Product Hunt yourself, and it wasn't like hunted by Ryan Hoover, do you think you would get to the top?
**Ryan** (00:28:30):
[laughs] I- I mean I don't know. It's- it's funny because if you ... We should do some like historical analysis on Product Hunt 'cause I'd be curious to know the actual numbers, but it varies all over the board. So, some people, they ask me, "Hey, like I don't know, is Product Hunt like ... Do B2B companies do well there?" And I'm like, "Yeah, like a lo- m- probably more B2B companies than B2C companies actually," and so you see, you know, seemingly boring companies that tap into something that- that- that people find useful or resonate- resonates with them, um, can go to the top. And then you also see the weird, wacky stuff, you know, the- the silly apps also hit the top. So, I don't know, it really varies.
And sometimes it's also driven by like the almost like the zeitgeist, like what do people find interesting right now? Like what's sparking people's interest? Because Product Hunt, on one side, you are potentially attracting people who might be future users and customers, partners, and so on, but it's also just a general kind of like zeitgeist of the early adopter tech community. Like what are they interested in? What do they find compelling in general?
**Lenny** (00:29:34):
Got it. Okay, so I have a bunch of questions from Twitter that people [laughs] wanted to ask you. And so, let me ask you a few of those, and they're kind of a little bit all over the place, but we'll see- we'll see where this goes. Jessica Toye, who's a- she's a PM at Angel List, she's actually a friend. We were together at Airbnb. She asked a great question.
**Ryan** (00:29:53):
Yeah. Jess- Jess is awesome. She- shout-out to Jess, she's like been super helpful on the Angel List side, so she's awesome.
**Lenny** (00:29:59):
Amazing. Okay, she's the best. She asked what you learned as a PM that has helped you in your venture career.
**Ryan** (00:30:06):
Yeah, um, yeah, so my- my background is, uh, marketing and then product management. Pretty quickly, uh, used to work in the gaming industry, which is like, I think, an- an awesome industry. Really hard to make it in that industry, but like amazing place to learn, and no, no, uh, I have so many biases, so I have to like be cautious of that, but I- I- having a product background, I think, is one of the most important aspects of early stage startup investing, meaning oftentimes, when you're building a new company, there are a lot of risks and there's a lot of important things to- to nail, but it all ultimately comes down to the product that you're building. And so, I think having a product management or a product background is helpful. And one, having more, I guess, perspective in evaluating different ideas and- and arguably more important, uh, how the founder thinks about things. So, it might be less about me evaluating the- the- the market need for this particular idea, but it's what's the thought process and how did this founder come to these product ideas and these insights. And so, I think having a product management background is helpful for that, and I don't know, I also just find it really fun to jam on product with founders. And when it's early, early days, there- there's more opportunity to create some sort of impact or, you know, help shape the product in- in a slight way.[00:31:20]
**Lenny**:
Awesome. Basically if you're a PM, you've got a lot of the skills that you need to be a founder.
**Ryan** (00:31:24):
Founder and- and arguably, investor, um, as well.
**Lenny** (00:31:27):
Oh, and that's right. Okay. So, uh, Leo of Sousa Ventures, who's also an awesome dude, uh, he asked if you could go back and-
**Ryan** (00:31:35):
I saw Leo in, uh, Miami, uh, not long ago.
**Lenny** (00:31:39):
Oh yeah. He moved to Miami too. Oh my God. Everyone's over there. Okay, so [laughs], uh, he asked if you could go back and build Product Hunt again, what would you do differently? We talked a bit about this, but anything else?
**Ryan** (00:31:50):
Yeah. Um, I've been thinking a lot about this actually lately. And, um, yeah, I mean there's a few things. Uh, one, Product Hunt, in the very beginning, and still today, is very much focused on tech, and there was, at one point, ambition to expand beyond tech into all different types of, you know, categories of products. So, you know, we experimented with podcasts actually, podcast discovery.
We experimented in video game discovery, we experimented with book discovery, and the thesis there was, "Okay, this could be actually discovery platform for all of these communities to discover all these different products," and I think there was a lot of good ideas in that. However, I severely underestimated how difficult it would be to do two things: one, the product experience on Product Hunt is very different than how you would wanna discover video games or maybe, in the future, fashion and a bunch of other types of products out there.
And two, it's really difficult to translate a community and expand into other communities. Like some- some have done it. Like Reddit is maybe a great example, where Reddit has this massive [laughs] long tail of, you know, every kinda community you can imagine, but very few companies and platforms can actually do that. So, that's one- one regret is we should not have tried to expand horizontally. We should've just focused entirely vertically and- and served the tech community, you know, better and- and with more things, which is effectively what we're doing now. Another regret, another thing I would've changed is I would've- I would've actually tried to monetize and generated revenue sooner. We- we raised a seed in a series A and we had capital to grow, and we didn't actually try to make money until after we required Angel List.
And my thinking at the time was, and to some extent, there's some truth to this, is like everything you prioritize is at the cost of something else. You know, you- you're essentially taking focus from one thing and directing it to something else. And what mattered most was growth and to grow the community, but what I really should've done is dedicated maybe 10% of our focus on revenue generation because, you know, it was- once we started generating revenue, we- we did so very quickly, and we go to cashflow, break even, I wanna say a year, maybe 12 months after we started generating revenue. So, if we would've started in 2014 to make some money, we coulda been cashflow, break even, you know, maybe 2015, 2016, which would've just given us a lot of flexibility in kind of owning your own destiny and proving out some of the business model itself. 
And then like the last thing, uh, I've been thinking about this lately is- is delegation is- is a classic founder challenge. You know, I- I'm just generally a controlling person. That's something I'm working on. And it's really hard sometimes when I have such strong opinions, and I'm very particular about certain things, uh, fully delegate and fully trust everybody. Not necessarily- we have an amazing team. Like I worked with some amazing people, still people that are Product Hunt today like six, seven years later. It wasn't anything about the skills of the team. It was just my own trust and my own delegation, and what I should've done is, you know, up until shortly before I left, I was editing the newsletter every morning, for example, like every morning. I was waking up, you know, 5 a.m., 5:30 a.m., editing the newsletter. I mean that's just kinda silly, you know, to be doing that so many years later after starting.
**Lenny** (00:35:02):
I totally get that drive to just make sure everything you're putting out and that your company's putting out is topnotch. I- I have the same feeling, and it is hard to [laughs] let go and just like, "That's not perfect, but I'm gonna- I'm gonna be okay with that, a few other things."
**Ryan** (00:35:16):
Mm-hmm. Yeah. It's- it's really hard, and I think it's a tendency that is, uh, in some ways, it's- it's good in that you care so much about the product as a founder. You care so much about what you're building. You care so much about the details, uh, and you need that kind of like almost OCD-like, uh, behavior, however, you also just can't scale yourself nor are you the best person at everything. So, I- I don't know. With hindsight I'm like, "All right, I should've delegated more. I should've trusted people more." And yeah, they'll- there will be more mistakes. I make mistakes all the time, but at the end, it's gonna be way net positive because you kind of have to [inaudible 00:31:30] your company anyway.
**Lenny** (00:35:54):
It’s a good segue to a question Harry Stubbings asked that he finds interesting always. What's the most painful lesson that you've learned and, but that you're also happy about to have gone through?
**Ryan** (00:36:05):
Yeah, yeah, there's ... I actually- I recently in the past couple weeks, wrote a blog post, that I'm not really able to publish 'cause it's- it's basically when you- there's certain things I wanna share that it- it- it can make things challenging and complicated for others. So, I didn't wanna put anyone else in- in a pickle. So, someday maybe I'll publish this post, but to speak more vaguely about it, like there's some hard- really hard times in Product Hunt, like we- we have all faced in- in different ways as founders, not even just as founders [laughs], just as people. Oh, yeah, there's some times where I felt physically ill, many different moments in- in Product Hunt. And um, it was just really tough, and you know, you- I don't know if- I don't know how to articulate that- that feeling but that flutter in your stomach that you wake up with in the morning of just anxiety and stress and- and worry.
Being a CEO or a founder makes it slightly harder in some ways because you still have to put on this mask. You have to put on this face of confidence externally and- and internally as well, where people need to trust you. You- you also don't wanna subject them to the same anxiety that you're feeling and be 100% transparent. So, it's- it's a struggle because, I think, I h- I don't know, I value authenticity so much, and I- I kinda like thrive around people who are authentic, however, there's this like tension with- with being a founder or CEO where you can necessarily share everything. So, anyway, everyone's gone through hardship building a company. You know, the positive aspect of that is like if- I- I think, hopefully growing some empathy for founders who are going through hard situations. I think it's made me a little bit stronger, maybe thicker-skinned for certain things. It just provided more- more perspective, you know, into the company kind of like building journey.
**Lenny** (00:37:41):
Okay, listen to this. If you can take 15 seconds to leave this podcast a rating on Apple Podcast or Spotify or any of your favorite podcasting apps, you could enter to win $1000 in cash, plus other fabulous prizes, including a one-hour coaching call with me, a box of custom swag that I've just created that's full of really good stuff, like an awesome water bottle and a hat with socks and a few other things. And you also get a one-year free subscription to my newsletter and even a goody box for Athletic Greens. It's a giveaway bonanza, and all you have to do is go to lennyspodcast.com/bonanza to learn more and enter the contest. Just make sure you apply by August 14th, 2022. Again, the URL is lennyspodcast.com/bonanaza.
**Lenny** (00:38:29):
We talked about how hard startups are and how many people should not start a company, but at the same time, part of this question, which I think you would agree with, is you're probably very happy you went through all that and- and wouldn't change, wouldn't like undo that, right?
**Ryan** (00:38:43):
Yeah. Yeah. It's kind of y- y- like a lot of things, you know, uh, what doesn't break you makes you stronger to some extent. So, it didn't break me, uh, it just scarred me a little bit but didn't break me. [laughs]
**Lenny** (00:38:52):
And turned you into the Ryan Hoover that we- that we have today.
**Ryan** (00:38:55):
Yeah. For better or worse.
**Lenny** (00:38:57):
[laughs] Maybe one last question from- from Twitter, Twitteratis. From Sandeep. He just wanted to know what- what have you found matters most to you or mattered most to you in life and in business versus what you thought would matter most?
**Ryan** (00:39:09):
Yeah, um, still figuring it out. I'm- I'm- I'm still asking the- the old stereotypical questions like, "What- what the heck is the meaning of life? Like what am I here for?" [laughs] All those things.
**Lenny** (00:39:19):
Let me know when you figured it out.
**Ryan** (00:39:20):
Yeah. And maybe, maybe there is no answer. Maybe the question is, is actually, um, doesn't matter. So I mean, if I'm honest, I'm still figuring all those things out.
Yeah. And maybe- maybe there is no answer. Um, maybe the question is- is actually it doesn't matter. Um, so I mean if I'm honest, I'm still figuring all those things out. I mean I think in- in life, some of the things that I've reflected on is, uh, so damn cliché, but sometimes when cliches are true is like friends and authentic relationships have been, I don't know, they just matter so much, I think. And the older I get too, it's less about, I don't know, I care less about having a lot of friends and more about a few deep, close relationships. And I don't know, I feel like that's very different than like middle school Ryan or like, you know, when you're in- on the playground metaphorically speaking, like where everyone's tryin' to be popular and, you know, meet a lot of people. And even- even joining and- and being, you know, uh, in San Francisco in the tech community, you wanna meet a lot of people and network and all- do all those things, that- that's less interesting to me and less important.
And then, more on the business side, the thing I've been thinking about is like, and I think this is obvious to a lot of people, but I think there's some nuances to it, which is momentum matters so much. And momentum is reflexive in that, you know, high momentum leads to more high momentum. Low momentum leads to more low momentum because there's this energy that- that kinda goes through companies where, when there is momentum, when people are shipping, when things are going well, other people feel that energy, and they wanna do the same, but in the reverse, someone who might be slowing things down, not shipping, not really performing very well, that actually does the reverse too. It- it might lead other people to- to feel less motivated or care less. And so, I don't know, momentum is- is this weird thing that, you know, you- arguably, it's one of the most important things in early-stage startups. And of course, it's an- an input to a lot of things, uh, but it's just so important to nail.
**Lenny** (00:41:00):
Mark Andreessen talks about that- that last point that ... There's like a word for it that I forget, that a company is either becoming a gravity and pulling in all resources and funding and attention or losing it. And it's really important as a company to know which one of those are you, and as an investor, you often wanna bet on the company that's just like they're just becoming the center of gravity here, and there's not a lot you can do to change that once they reach a certain point.
**Ryan** (00:41:24):
Yeah. Yeah, that's a really good point. I mean the- it also mirrors with like the power law of investing where it's- it's, in most people's situation, it's one company is returning ... You can invest in 100 companies, and one of those companies is probably gonna return three to five X in the returns of all the others, maybe combined in some cases. So, it's- it's wild.
**Lenny** (00:41:45):
On the first point that you made earlier about cliches and platitudes, it reminds me, Michael Pollan has this point that he makes that like cliches and platitudes are cliches and platitudes because we've heard 'em so many times but that- because they're true. People just say 'em because they're so true. And as much as we don't wanna hear them, like there's a reason that we hear them again and again. Uh, I had a similar recognition when I was on a little psychedelic journey where I'm just like, "Man, love is all you need. Love is all you need, man.”
**Ryan** (00:42:15):
[laughs] Yeah.
**Lenny** (00:42:16):
Okay, people have figured that out. But I was like, I feel that, I feel that right now. But it's true. That's why people- that's why f- [laughs] we're like, "Okay, shut up. I heard that. That's in a song."
**Ryan** (00:42:25):
[laughs] Yeah, it's- I was listening to- to a podcast, uh, about someone who was basically describing like psychedelics as a gateway into like meditation and- and everything and how it can be one of those things that makes people ... It- it- a lot of people who take psychedelics come across as another hippie cliché like person who like repeats the same things we've all heard many, many times, but there's a reason why there's a pattern there. And, you know, he describes like psychedelics as- as one way to feel that and learn that- that feeling that you can't achieve with- with meditation, you know, with experience.
**Lenny** (00:42:56):
Yeah, I think Sam Harris talks about this where you could either meditate for five, 10 years to work your way up the mountain towards, you know, enlightenment, or you could just take some psychedelics, visit it for a little moment, see what it's like, and then [laughs]- and then-
**Ryan** (00:43:09):
Mm-hmm.
**Lenny** (00:43:09):
be motivated to, to work on getting there more naturally
**Ryan** (00:43:12):
Yeah.
**Lenny** (00:43:13):
This is a good time to play a little game that I invented just for you. Okay, so you're the founder of Product Hunt. Okay. And, on Product Hunt, people up vote ideas that they like best. And so what I'm gonna do is I'm gonna give you two options and you tell me which you'd rather— which you'd up vote and it'll make sense once we get going. [laughs]
That sound good.
**Ryan** (00:43:33):
Okay, cool. Let's do it.
**Lenny** (00:43:35):
Okay. TikTok or Instagram Reels?
**Ryan** (00:43:38):
And, and is context setting, are these within the context of products? I, I like and know, or
**Lenny** (00:43:43):
Products you would choose to use that you like better... yeah. Not like which will do business— better business. Yeah.
**Ryan** (00:43:50):
Okay. Okay. Got it. TikTok's for me. It's funny, reels, I kind of joke with, with Susie, my girlfriend, I joke that it's like, reels is like, TikTok, but like two weeks late.
Uh, it's not entirely true, but I feel like I see a lot of TikTok videos on Instagram reels. Like after, you know, weeks after they've been published.
**Lenny** (00:44:08):
We'll see, I have some friends that work on reels and I'm excited to see where they go. Okay, next- LaCroix or Topo Chico.
**Ryan** (00:44:15):
Ooh, this is a tough because I- I- I'm generally a La Croix kinda person, but Topo Chico, I like the bottle. So, when Topo Chico's available, I'll go Topo Chico. I'm sorry, La Croix.
**Lenny** (00:44:26):
[laughs] I- I totally get that. My wife's a huge Topo Chico fan. We have many, many [laughs] bottles. They're beautiful. They've- kind of changed a bit. They're like super clear now, they used to have a little, a little tint.
**Ryan** (00:44:36):
Hmm.
**Lenny** (00:44:37):
Very important topics. Yeah. Okay. Next, next up, Bay Area or Los Angeles?
**Ryan** (00:44:43):
Uh, Los Angeles. Although, it depends on the- the, so here's my goals, if- if I was, you know, a new college grad or someone young and- and new in kind of the tech industry, definitely San Francisco. You'll create a lot of serendipity. You'll- you'll meet a lot of people, but from a lifestyle perspective, LA. Um, LA, I just find more enjoyable, weather's better, there's hiking, housing is cheaper. So, LA today, San Francisco, 10 years ago.
**Lenny** (00:45:09):
Very nuanced dancer. I knew you were gonna say LA, and so, next is East Side LA or West Side LA?
**Ryan** (00:45:16):
I don't know. We- we lived in Hollywood up in the hills for a while. So, I don't know if that's East or West, but wherever that is, big fan.
**Lenny** (00:45:24):
I guess that's West, right? It's not near the water. That's a really good question. Hollywood Hills, all right, that'll be a third [laughs] option. Okay, electric bike or regular bike.
**Ryan** (00:45:34):
Nothing against electric bikes, but I feel like if- if your goal is to get exercise, then just get a regular bike, but I don't have either. I have a- a, um, recumbent bike at home that I use for exercise. The reason why it's recumbent and not like a Peloton where you sit up is 'cause I can do emails and work [laughs] because while I'm exercising.
**Lenny** (00:45:53):
Wow. Very productive. Okay. Next, dark mode or light mode?
**Ryan** (00:45:58):
Light mode, I've never used dark mode like ever. Actually I take that back. Tweet Deck is the only dark mode kind of app that I use. But-
**Lenny** (00:46:06):
Wow.
**Ryan** (00:46:07):
I don't know. If- if a founder is prioritizing dark mode before they have product market fit too, it's like a big red flag for me. That's a little bit of a hot take. Some people are gonna hate me for that, but I don't know. I don't think dark mode matters for like 99% of people.
**Lenny** (00:46:22):
Wow. Big, big, hot take. What if they just go dark [laughs] and there's no light mode. Does that count against them?
**Ryan** (00:46:28):
Uh, Yeah, that's fine. As long as it's just one mode, um, it's the teams that prioritize all these, like small things that don't matter before the product is actually like useful for people or, or that that's, that is where I like my product manager hat comes in and I'm like, is this like the highest on your priority list?
I don't know. Now big asterisks, it's all contextual. Sometimes. Like the audience you're building for really cares about dark mode. Like if you're building for developers, maybe you need dark mode, or, or some version of it, but, but yeah, I'm, I'm light mode.
**Lenny** (00:46:57):
Awesome. Okay. [laughs] Did not expect that, love it. Okay, two more. Wash the dish right away or let it soak in the sink?
**Ryan** (00:47:04):
[laughs] Um, I'm looking at the sink over here. There might be dishes in there, so that'll be my answer. I got a bad habit.
**Lenny** (00:47:11):
No, I think there's- there's power in letting it soak. I get it. I respect that.
**Ryan** (00:47:15):
[laughs] That’s what I'll tell Susie next time. There's power. Lenny said there's power in soaked dishes.
**Lenny** (00:47:20):
There's physics. It's soaking. Okay. Last one, Web3 or Web5?
**Ryan** (00:47:25):
Mm, uh, I don't know what happened to Web4, so I don't know, maybe- maybe we'll split the difference, so I'm gonna go Web4.
**Lenny** (00:47:31):
Okay. We did it. [laughs] That was the inaugural addition of which would you rather up vote? Amazing. You killed it.
**Ryan** (00:47:38):
There you go go. I like this. All right. It's kind of a fun, this could, this could be a fun little segment, I think for a lot of things.
**Lenny** (00:47:45):
Yeah. It'll plug Product Hunt. It'll be great. We'll see [laughs] where this goes. This replaced my lightning round, which I experiment with. Okay. But actually I have other questions I want to get through before we, before I let you go. If that's cool.
There's kinda two topics. One is around consumer startups and just a few things that I've been learning there and then angel investing and then- and then we wrap.
So around consumer. By the time this post comes out, I'll have released some portions of the series that I'm working on, on kickstarting and scaling consumer business. And there's a few things I've learned there that I just wanted to get your take on. One is that, and we talked a bit about this just like 99% of consumer apps seem to just like, not work, especially if they're venture scale, if they raise money, just like just a reminder of how hard consumer is like, when is the last consumer app that really took off.
And so I just wanted to get your thoughts— is what's your take there? What should founders do that are starting a consumer company?
**Ryan** (00:48:40):
Yeah, yeah, it's tough. I mean there's- there's obviously consumer is pretty broad, so there's like different levels of difficulty, I think. Um, the consumer social or gaming, like games, building games, is probably like the- the- the hardest and the one filled with the most failures. And I think a lot of that is because, I think a few things, I think one monetization is generally harder than like a B2B company. Historically, a lot of it's been like advertising driven, and to do that, you have to first get to massive scale for advertisers to really care. And then you have to, you know, double it and double it and double it [laughs] again. So, monetization is super tough, versus a B2B company, it's like people have a problem, they have a need, they are willing to give you money, you know, on day- day one.
The other thing about consumer that's tough is you're- you're always fighting different, essentially you're fighting for attention. And so, you might be some consumer social company, but you're- you're kind of like competing with Netflix too, which isn't in your direct domain, but like people could be watching Netflix, or they could be using your product or- or your social app, let's say. So, now you're competing with so many different things. Many of those are incumbents where the consumer also has like built-in habits, routines. Like this is a big- big part about consumers too is eventually you wanna be like an internal trigger in someone's mind where they- they just, without even thinking, they go and use your product or services for some reason. Usually, you don't start that way. You need like external triggers to like pull people in, but eventually you have to get to that point. So, how do you overcome those internal triggers they have for other services, other products? It's really, really hard. 
And- and then I think a lot of it is, um, like B2B companies, usually you- you have a clear like problem that you're solving. And you could talk to customers, you could understand what are their current behaviors, what- what solutions are they using now, what do they like about them, what do they not like about them whereas, consumer, there's a little bit of that, but it's- it's fuzzier. You know, if you take, um, like Twitter and you kind of even ask someone like, "Why do you use Twitter and like w-" people will have different answers that are all kind of like fuzzy. And they ultimately tend to come down to some sort of like innate human desire. Like it could be, uh, for Twitter, it could be about like, "I wanna be informed with what's happening in the world," or it could be, "I want to feel less lonely or connected to more people," or something like that whereas, if you go to, let's say DocuSign, I think is a great example, of a B2B company, it's like super simple. [laughs] 
It's like a- a way to get legal docs signed online. That's- that's what it does. It's a thing that people have to do. It's very clear like what it solves. And so, B2B's just like easier to navigate that idea maze. And so, with consumer, you- your- your first blog post on this topic touches a lot on the idea side. And I- I, a lot of it resonated with me, especially the- the insight piece. Like what is- what is the insight that you, as a founder, have to build this thing? Because I think it's really hard to build a consumer company without some sort of unique insight, maybe impossible. And you can get that in many different ways. It could be through your own experiences. I used to write like a problem journal. Like just when things annoyed me or when things were like less efficient, I would write it down as like a note. And I didn't try to solve it. I didn't- didn't say, "Oh, here's the solution." I was just like, "This is annoying." 
Like, in San Francisco, one example is a lot of people don't have laundry like in their unit. So, I'm like, "That's kind of annoying. Like that's a problem. Maybe there's a solution out there." So, things like that. And I know, there's- there's- there's a bunch of different ways, like, uh, y- your- your blog post does a better summary, I think, of like the different ways different companies like ideated and came up with their ideas, but yeah, many different ways to navigate it but needs an insight of some sort.
**Lenny** (00:52:09):
Awesome. I hadn't heard that, u- u- uh, that pr- problem journal idea. I was gonna ask you if you have any suggestions for how to come up with a startup idea, and that's a really interesting one. Is there- yeah, so I guess it'd be cool to hear where that came from and what that led to? Or if there's anything else you found to be useful around that?
**Ryan** (00:52:23):
Yeah, yeah, the problem journal is one. And again, like I think it's helpful, not to try to come up with the solution, but just write- just simply write down the problem you- you observed or experienced. Another one I think's interesting is just to like immerse yourself in different communities. Ideally, like maybe like seemingly niche or weird long tail communities. It doesn't have to be that necessarily, but that might be where you'll see more unique insights or- or gather more insights, and you could do that through, I don't know, I'm just thinking subreddits, meeting a lot of people who are like really excited some other thing. It could be like some weird robotics like niche, hobbyist community, for example. And a lot of that, I think, will- will hone or just like create serendipity for ideas. You might see patterns, or you might see, you know, if problem statements emerge from many people in that community that are facing similar things.
And then there's like the other- other component too, which is really about like observing trends and- and changes, whether it's like a consumer behavior shift. Let's take an obvious one. Today is like distributed working. So, five- five years ago when the Weekend Fund started, that was one of our themes. It was like I- I- I think distributed working will be on the rise for a number of reasons. One, you know, i- it's harder and harder to recruit. Two, there's a subset of people who really valuable that flexibility and autonomy. And then fast forward, we had COVID, so like we had remote working, and- and now, that's a huge consumer behavior shift. Not just in how people work but also, like going to your Airbnb like world, like Airbnb has shifted their entire product to support more of this remote working kind of lifestyle, just the way that the- the homepage is now more of a catalog of places that you could explore at different times of the year versus Airbnb before was more like, "I have a very specific vacation trip that I wanna take during these days in these areas."
It's like a very different like browsing kind of experience. So, that's just one example. Consumer behavior shifts is one thing to observe. The other is technology shifts. So, what- what new thing can you build today that couldn't be built yesterday? And so, there's- there's a bunch of categories around there, like Web3, AI, you know. The biggest shift that we've seen is- is mobile in like early 2010s, um, 'ish, that unlocked a whole- whole bunch of things. So, so, yeah, I think it's observing those shifts and those changes. Last thing I'll say on that is like I think startups, since there are more and more people building companies and technology, there's essentially more efficiency. It's certainly not a- an efficient, super efficient market, but there is more efficiency in problem discovery and- and- and solution exploration. And so, for that reason, you need even more reasons for things to- sort of answers to the, "Why now?"
Like what's changed? What insight do you have? Why doesn't this exist already? 'Cause a bunch of people are trying to build something in the space most likely. Just a lot of what we think about, especially on the investing side, when we talk to founders.
**Lenny** (00:55:14):
Wow. There's s- way too much good advice there. Have you written this down anywhere? Is there a Tweet thread people can find like your kind of approach to coming up with an idea?
**Ryan** (00:55:22):
I have not, I don't think so.
**Lenny** (00:55:24):
Cool. All right. Now we have to-
**Ryan** (00:55:26):
Blog post for the future.
**Lenny** (00:55:27):
Yeah. Or this is the, uh, this is the- the- the content for people to save and use. Thanks for sharing all that. That was really helpful. One other question I wanted to ask you along these lines is around the target audience and, uh, something ... A- an insight that we both share is that it's really important to get really narrow, whatever you focus on initially, as a start up, and it's, for founders, it's often so counterintuitive, they're like, you know, it's like, "Oh my god, why should I focus on the 1000 people? Or 10000 type people-
... Versus the millions that might wanna use this thing?" What's your sense, and where have you kind of seen that become important? Just the idea of getting very narrow of how you're going after.
**Ryan** (00:56:05):
Yeah, it's, effectively, the more narrow you're- you're generally, and this is where I throw in the big asterisks, like not for everything, there's always contextual differences, but generally, the easier it is to build a great solution for those people, because now you can actually hone in the product experience, the messaging, and everything to serve exactly those people. And it can help with the product side, it can help with the marketing and go-to market where you- you're messaging ... When people land on your homepage, you don't need to create kind of a broader kind of like value prop to everybody, but really, you can focus on like what is the- the problem this particular audience or community is- is facing. And so, generally, it's just easier.
Now there is always that challenge of like, "Well, is this too small? Is it too- too much of a niche if- if my goal is to build like a massive company?" My bias is not to worry too much about that because what you probably find is, over time, opportunities to expand beyond that. You'll see parallels, maybe to other communities or to other problems. And a lot of companies, you know, eventually expand well beyond that. Like I'll go back to Airbnb, you know the story way better than I do, but you know, initially, it was just like, you know, basically couches and extra rooms in houses. And like a lot of people, most people in the US would not do that. Like my parents, not- not in a million years. Even me, like I don't wanna like stay in some stranger's like room. I want my own space, my own house. So, that- that probably at the time seemed really niche and like small, but obviously, they extended- extended well beyond that.
Now- now I view Airbnb as like housing in generally speaking. Like their- their TM is housing in- in my mind, which they haven't yet exp- expanded into like real estate sales or like longterm rentals, per se, but like that- that's a possibility.
**Lenny** (00:57:51):
This is a good segue to the last topic I wanted to touch on, investing, which I believe you do full-time. Would you say that it's- your full-time gig now?
**Ryan** (00:57:59):
Yeah, yeah, it is. Yeah, I'm spending all my time there, and yeah.
**Lenny** (00:58:02):
Cool. So, from what I can tell, the Weekend Fund is killin' it. I'm not an LP, but it feels like it's kind of this underrated juggernaut that's just doing very well. And so, I wanted to ask you a couple questions along these lines. One is what have you learned about investing, angel investing? Especially what's most surprised you?
**Ryan** (00:58:20):
I mean I feel like there's a lot ... A lot we've learned. So, there's- there's things on the operational side. Like running a fund, there's a bunch of things that go into it, from LP communications, LP fundraising. There's also like ... Vedika who works with me on the fund side, she, um, she describes it as like hygiene. There's also good hygiene when it comes to running a fund. For example, you know, when you meet a founder, you- you- you should get back to them. [laughs] Like if it's a pass, you should let them know. And then there's a lot of different ways that you can do that. Some people, you know, might just say like "pass," and that's not very encouraging to a founder if they gave you no context, no details. There's also an element of hygiene, which is you always follow up with the person that introduced us to that company. And we just feel it's kinda like that's what we appreciate.

Like we like to kinda know what happened, like s- have them close the loop. And so, there's like good hygiene, operational things that we've learned and kinda honed over- over the years. I mean the biggest surprise, the biggest surprise has probably been ... I gotta be careful of how this is interpreted in some ways, but it's ... There are cases when I didn't think the company would make it. I- uh, either the product wasn't working, and you know, many months had passed, and it was very clear that they're- they- well, to me, I thought it was clear that, okay, that this probably isn't gonna work out. In my head I kinda wrote it off. And then that company either pivoted or- or some m- like massive partnership or MMA event came through out of nowhere, and so I- I guess the learning is like never count a portfolio company out until it's over.
And, you know, uh, that relies on, of course, backing founders that are very resilient and creative and- and, you know, driven to- to create momentum, you know, out of nothing, but- but that's been surprising to me. And it makes me kind of excited because, you know, we invested in over 110 companies now and it's- it's fun to be able to kinda see behind-the-scenes a little bit how all these things kind of play out, both the good and the bad.
**Lenny** (01:00:13):
That's such an inspiring takeaway. Does that change how you invest? Like to me, that's like, "All right, I guess I should just take more bets on founders that are awesome." Although, I find just founder bets, it's like a very expensive hobby/approach because there's so there's so many great founders. How is that informed how you invest seeing that happen?
**Ryan** (01:00:33):
I would say we don't, we don't have like, um, it's again, my cop out it's contextual kind of answer. Like, you know, some people are like, "We are a team first only." Some are, "We're market first." Some are, "We're product first." And we- we look at everything kind of holistically, and I think the evaluation of the product is- is sort of a reflection on the team. So, our- our assessment of the thinking behind the product that they built today and maybe some of the traction is a reflection on like the team's abilities and like the thought processes.
So, we try to look at it holistically in, um, I mean, yeah, I mean every investor would say like, "Yeah, we wanna back, you know, resilient founders that are very driven, insightful, and all those things," of course. But it's also sometimes hard to like fully evaluate that, unless you really know that person. So, so, we try to- to- to take as much data around like how the product is working and how they made those decisions leading up to this to- to evaluate the team sort of indirectly.
**Lenny** (01:01:26):
That's kinda what I've started to do is I- I try not to invest as a founder bet unless I just know them because it's just so hard otherwise.
**Ryan** (01:01:35):
Yeah, yeah, there- there's a few founder bets that- that we've made. One, going back to the consumer social kind of thing, he's somebody I've known for many, many years. One of the most talented like designers, engineers, product builders. And I've just been waiting for him to start a company and- and so, that was- that was one of those, "I'm gonna bet on you because I believe in you. I'm not sure about this first idea, uh, you know, who am I to judge? But I don't know if that's gonna be it," but [laughs] he's probably gonna launch 10 apps, and the 11th is gonna be a massive success. And so, that's sort of the- the way I think about those consumer social founder first bets.
**Lenny** (01:02:10):
I love that. Last question along these lines, for someone that's hoping to get into investing or angel investing in the near future, do you have any advice for folks around that?
**Ryan** (01:02:20):
Yeah, actually, I wrote a tweet storm and like converted it to a blog post on this 'cause we've get- gotten a lot of ... You probably as well, get a lot of emails or people saying, "Hey, I'm thinking about raising a fund. Like how should I do that?" or "I wanna get into- to venture. I wanna start investing. Like what advice do you have?" So, yeah, I wrote a blog post on this, and there's many different ways to invest. There's, you know, angel investing is one. So, great thing about that is if you have the capital to angel invest, you can do it today, tomorrow. Like you- there- there's no- no sign-offs required. You have maximum flexibility, but of course, you need to have disposable income. You need to be able to- [laughs] be willing to lose all of it and then hopefully you, you know, you'll ma- you'll be on the other side of that and make some money in 10 years.
 It takes a long time. There's scouting; that's another option. And there are more and more scout funds probably than ever before right now, in different flavors. Some of them are like dedicated kind of scout programs where you have capital to deploy on your own, some are more like you still need approval, but you send the deals, and you get carry on those deals in many cases. Those have pros and cons too. Like they're easier to start and get into than raising a fund typically for most people, but you also are sort of reliant on that- that program or that fund. Um, you might have less autonomy in what you can invest in and what you can't. And then there's a few others; there's SPVs is- is one angle, which works really well for a lot of people. So, um, for those that maybe don't know and- and listening to this right now, SPVs are essentially like a single vehicle, um, investment into one company.
So, you raise money from LPs, from other investors, to invest in this specific company. And there are a few great things about that. Like one, you get deal-by-deal carry, meaning like the- the outcome of that company is- is you get paid when they exit essentially, assuming there's a positive outcome versus a fund, like you have to return the entire fund first. Two, it allows you to also bring in maybe very strategic, helpful people into that particular round for that company, which can actually be a- a strong value add for that founder. The biggest trade-off is it's a lot of work sometimes. You- you have to basically do a fundraiser [laughs] every couple you invest in, and that's super time-consuming for a lot of people. And then the last thing is like r- rai- raising a fund.
So, that's the decision that I decided back in 2017 is I wanted to raise a fund. It's a lot more work to raise the capital and- and- and there's a lot more responsibility in managing funds and so on and so forth, but it provided me with the most flexibility and- and a way to deploy many checks into many companies, especially when I didn't and still don't have like a ton of money to angel invest. So, yeah, those are like different options. Like I think my blog post goes into more like pros and cons for each of those things, but the last thing I'll say actually is, let's say, none of those are really an option. You- you- you don't wanna start a fund. You don't have enough relationships to do SPVs. You- for whatever reason, you can't do a scout. You don't have any money to angel invest. One thing you can also do is just like pretend angel invest. [laughs] And that doesn't mean that you're meeting the founder and like writing a check, but you can write memos, or you can like almost create a fantasy portfolio.
And this is what Vedika, before she joined- joined me, was doing to some extent. She was writing memos about companies she was excited about. And in some ways, she was like doing the job before getting the job, and anyone can do that today. And that can be helpful too if you're applying or trying to prove your- your- your abilities. You could say, "Hey, here are the memos. Here are the companies that I would have invested in, you know, if I had the opportunity, and, you know, here's my thought process behind that."
**Lenny** (01:05:49):
I love that. I'm curious about the logistics of knowing the prices of all these startups, but anyway, we don't have to get into all of [laughs] that. That's an awesome idea. I've seen people on Twitter do that too. What's- where do you think this all goes for you? Are you thinking of increasing the fund? That's basically the last question. Just, yeah, what's- what’s- the future of Ryan- Ryan Hoover at this point, as far as [laughs] you know?

**Ryan** (01:06:08):
Yeah, still- still figuring out the meaning of life, as we established earlier.
**Lenny** (01:06:12):
I thought we cracked that one.
**Ryan** (01:06:13):
Yeah, yeah. I'll let you know when I figure it out.
**Lenny** (01:06:15):
Okay.
**Ryan** (01:06:16):
Um, uh, [laughs], um, yeah, we're on our third fund right now. We're actually about 30, 35% deployed, so we have plenty of- of capital, and we're not gonna be raising any time soon. Yeah, we're just investing in early stage companies right now, but yeah, when I fast forward like longer term, I don't know. I will always be investing. I'm also more of a fan of maintaining a smaller fund. Our latest fund is 21 million, and that might ... I might change my mind on this, but that might be the biggest fund we ever raise. I might keep it around that same size for the next one because it really allows us to be f- really collaborative. We can write smaller checks. We can fit into competitive deals. I think it's a better product for founders. Like we're not tryin' to take the entire round. We can, you know, try to bring on the Lennys of the world as co-investors, things like that.
And so, investing will always be a part of my future, but I also love building. Building is- is the most fun, so creating something is- whether it's a company ... I don't know- I don't know what it is. I'm not even gonna call it a company, but building something is hopefully in my future. I just gotta figure out the right idea. And maybe, maybe reflect on your blog post too on the idea generation stuff that you shared 'cause that- that is helpful.
**Lenny** (01:07:22):
As long as you let me invest all is good.
**Ryan** (01:07:27):
[laughs] I don't know- I don't know if I'll- part of me is like, "Do I ever wanna raise from venture?" Now it depends on the idea. If- if I need it, if it's required strategically, then yes, but to be quite honest, maybe I shouldn't say this, like I'm kind of really interested in just owning something 100% and you can always raise venture later. Like it- it's a one-way door, so I kinda wanna delay that door, you know, for whatever I build next, if I can.
**Lenny** (01:07:53):
I 100% get that. That's how life is with this newsletter operation and I highly recommend it.
**Ryan** (01:07:59):
Yeah.
**Lenny** (01:07:59):
If you can pull it off. Okay. Um, that's it. Just a couple- just where can people find you online? It's kind of a dumb question 'cause you're very easy to find, but where do people go to learn more if they wanna reach out? And then- and then how can listeners be useful to you?
**Ryan** (01:08:14):
Yeah, I'm just, uh, easy to find. R- Rhoover on Twitter, Ryanhoover.me, simple website. I have a bunch of old blog posts on there, probably with a bunch of broken links and broken images, but it's there. The content's there. I don't know. We're- we're investing- we're investing in the early stage companies, B2B, B2C. If you're building something weird, I don't know, DM me, email me, I'm around.
**Lenny** (01:08:35):
Amazing. Ryan, thank you so much for being here. It's kind of a surreal experience interviewing you. And I'm really honored that you came, and I can't wait for people to hear this. I'm really happy about all the nuggets that [laughs] I was able to extract out of your head, and thank you for sharing them. Thanks for being here.
**Ryan** (01:08:52):
Yeah, thanks, Lenny. Yeah, these- these conversations are- are helpful and like reflecting on what do I actually believe anyway. So, it's- it's just like writing, it's helpful.
**Lenny** (01:09:00):
Yeah, and it is just as helpful to everybody else. So thank you again.
**Ryan** (01:09:04):
Cool. Thanks Lenny.
**Lenny** (01:09:06):
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.

---

## [11/20] The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft

**Lenny Rachitsky** (00:00:00):
I generally value the reference check over interview signals. If I had to stack rank in interviews, what is the best signal? The reference check is the top of the list. Those people, they worked with this person sometimes for years, their knowledge, what you're going to get out of 30 minutes of artificial scenarios it's just like never going to compare what a good reference check will give you.

**Lenny Rachitsky** (00:00:25):
Shishir Mehrotra is the co-founder and CEO of Coda. Before starting Coda Shishir led the YouTube product engineering and design teams at Google, where he spent over six years. Before that, he spent six years at Microsoft. He's also on the board of Spotify. As you'll hear in this episode, Shishir is an incredibly deep and very first principles thinker on all kinds of topics. And in this episode we cover growth strategy, specifically a framework that he calls Blue Loops and Black Loops.

**Casey** (00:01:29):
Coda is a company that's actually near and dear to my heart because I got to work on their launch when I was at Greylock. But in terms of what I love about it, I love loops and Coda has some of the coolest and most useful content loops I've seen. How the loop works is someone can create a coda and share it publicly for the world. This can be how you create OKRs, run annual planning, build your roadmap, whatever. Every one of those codas can then be easily copied and adapted to your organization without knowing who originally even wrote it. So they're embedding the sharing of best practices of scaling companies into their core product and growth loops, which is something I'm personally passionate about.

**Lenny Rachitsky** (00:02:05):
I actually use Coda myself every day. It's the center of my writing and podcasting operation. I use it for first drafts to organize my content calendar, to plan each podcast episode on so many more things. Coda is giving listeners this podcast, $1,000 in free credit off their first statement. Just go to coda.io/lenny. That's coda.io/lenny. Hey Ashley, head of marketing and flat file. How many B2B SaaS companies would you estimate need to import CSV files from their customers?

**Ashley** (00:02:38):
At least 40%.

**Lenny Rachitsky** (00:02:40):
And how many of them screw that up and what happens when they do?

**Ashley** (00:02:43):
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 CSV importer doesn't work right, which is super common considering customer files are chock-full of unexpected and formatting, they'll leave.

**Lenny Rachitsky** (00:03:02):
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 aha moment more quickly and reliably is so incredibly important.

**Ashley** (00:03:17):
Totally. It's incredible to see how our customers like Square, Spotify and Zuora are able to grow their businesses on top of flat file. It's because flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny Rachitsky** (00:03:34):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny. Shishir, welcome to the podcast.

**Shishir Mehrotra** (00:03:48):
Thank you for having me.

**Lenny Rachitsky** (00:03:49):
I don't think I've actually shared this with you, but you're actually the very first CEO that I've had on this podcast. I actually have a rule of no founders or CEOs on the podcast, at least at this point. And you're the first person that I've let break this rule. And so how does that feel?

**Shishir Mehrotra** (00:04:04):
I've always been a rule breaker.

**Lenny Rachitsky** (00:04:08):
Perfect. So bio for listeners just briefly. So you're the founder and CEO of Coda. You spend six years at Google where you're a VP of product and engineering for YouTube, basically leading the YouTube product team. Spent six years at Microsoft, you're on Spotify as board of directors, you're also a prolific online writer. And that leads to my first question, which is I hear that at Coda there's a contest internally for people who actually... So maybe a little context, you encourage people to write a lot of stuff externally within Coda. You want people to be writing and you have this contest of who gets the most views and likes of people internally. And so is that true and who's winning?

**Shishir Mehrotra** (00:04:47):
By the way, yes, it's true. We did a similar thing at YouTube and YouTube creators. I mean obviously kicked our butts, but we made a good way to make sure we understood our tools and learned how it worked. And I think for a while at YouTube I had one of the top videos, it was a really cute video of my daughter taking everybody's orders when she was like three or four years old.

**Lenny Rachitsky** (00:05:11):
That's not fair.

**Shishir Mehrotra** (00:05:12):
Yeah, super cute kid is an easy trick for YouTube, but I get to learn all the tools and so on here, the equivalent at Coda is you can publish Coda Docs, they show up in the gallery coda.com/gallery, you can see lots of them. And at this point, thousands of docs when published from lots of different people, it gets millions of views. And like at YouTube, the most popular ones are not ours, but it is sometimes helpful for us to make sure that we understand how the whole system works in order to do it. So I think that the current winning doc at Coda is one in a pretty deep niche. It's from a guy named Kenny Wong on our data team, and it's an orange theory workout doc. So it turns that orange theory has this deep subculture that they all hang out together on Reddit and so on. And this doc just took off as... I don't really understand the doc, I'm not in that subculture, but it's similar to YouTube in some ways. It's like the niches are actually much bigger than people think.

**Shishir Mehrotra** (00:06:17):
Of the ones that are more work related, I think Lane Stock on two-way writeup still outranks all of mine, but I have a couple of good ones on there too. And I would say this competition exists in my family too. I don't usually even win with that in my own family, my older daughter, Annika, who also had that great video on YouTube has two docs that do really well. One is Family Quarantine Olympics, which is a thing she put together at the beginning of COVID, like a fun game for families to play. And the other one is a score tracker for a game called Ticket to Ride, which I don't know if you've ever played the game, but it's...

**Lenny Rachitsky** (00:06:51):
Heard of it.

**Shishir Mehrotra** (00:06:51):
It's about the most complicated scoring system on the planet because you play the whole game and you spend 10 minutes scoring it. And she built this whole scoring calculator and that turns out to be super popular too. Anyway, but my docs do okay. But yeah, the interesting variety of what people end up doing.

**Lenny Rachitsky** (00:07:07):
I love that. Which of your docs has been the most successful? Hopefully we end up talking about it.

**Shishir Mehrotra** (00:07:12):
I think it goes back and forth between two docs I've written one called Eigenquestions, which I think you intend to talk about, so we will get back to that.

**Lenny Rachitsky** (00:07:20):
Yeah, absolutely.

**Shishir Mehrotra** (00:07:21):
And the other one is one I wrote a while back called Four Mitzvot Bundling. That's all about how subscriptions work and it's how I ended up on the board of Spotify with Daniel and I geeking out on bundling theory, which is a super weird hobby, but I have normal hobbies too. But I liked it. I like to explore bundling as a fun hobby and people enjoy that doc as well.

**Lenny Rachitsky** (00:07:41):
Yeah, you've shared a lot of good thoughts on that and we're not going to cover that because covered that in depth in many places. But just to clarify, did you write that doc and then led you to being on the board of Spotify or is that after the fact?

**Shishir Mehrotra** (00:07:52):
The conversation led to... It was a napkin sketch at YouTube that turned into a really fun lunch I had with Daniel, Daniel at the Spotify founder and CEO. And then he encouraged me to write it down. And for me, you write prolifically and writing for me is actually surprisingly hard. I feel like I have to think about it.

**Shishir Mehrotra** (00:08:22):
You make it seem really easy. For me he's like, "Could you write that down?" It's like, "Great. Now I'm going to take a year to write this thing down." Because you think through each part of it and you kind of come up with the right framing. I have a little review process I use for my docs that allows other people to help me make it better, which is always really helpful. But yeah, so that's how that started. So it got written down after. Yeah.

**Lenny Rachitsky** (00:08:47):
So we were talking about writing and content and things like that, and that's a really good segue to the first thing I wanted to talk about, which is Black Loops and Blue Loops, which to folks that haven't heard this before might sound like some ultimate fighting nightmare scenario, but it's something that is really important to you and Coda. And so to set it up, can you just talk about what Black Loops and Blue Loops are?

**Shishir Mehrotra** (00:09:08):
Yeah, and it's probably worth mentioning. I think a lot of businesses have a diagram that describes their ecosystem and how it works. Sometimes it happens a little later in a company's journey. For us, we're probably three or four years in before Matt Hudson's runs our data finance teams here. He came up with this diagram and it really stuck for people. But I highly encourage drawing a diagram like this for your business. I'll flash it up on screen for a second and I'll describe it, but this is what the diagram looks like, black loop, blue loop, and it's basically the two different ways that our product spreads. The Black Loop is someone comes in, they make a doc, they share with a group of people, some subset of the people turn around and make another doc, and the process repeats itself over and over again.

**Shishir Mehrotra** (00:09:53):
The blue loop is someone comes in, makes a doc, and instead of sharing it with a team or with the collaborators, they publish it to the world. And in that process expose it to, they can choose how it should appear. What publishing in Coda is a lot like building a website. So you pick a URL, you tell us whether or not Google should be able to find it show up in the gallery and so on. And what ends up happening from that is they turn into broad promotion of Coda, but really it's about that person what they're trying to get done. And I'll stop sharing so I can talk a little about the dynamics. So I sometimes refer to them as the Microsoft Loop and the YouTube Loop because those are two inspirations for it. The Black Loop feels a lot like how documents naturally spread.

**Shishir Mehrotra** (00:10:36):
The viral actions of a document platform are shared, create, share, create. It happens over and over and over again. The best way you learn about Office or Google Docs or so on is somebody shares one with you and you're like, "Oh, that's pretty cool. I bet I could create one." And that loop can happen very, very quickly and it really drives for us a lot of how we think about how we work mostly within companies and teams, but sometimes across them as well. And so for an example, it led to our pricing model. So our pricing model is a little different than most companies in the space that we do a thing called Maker Billing. So basically all document products, all products with the document metaphor have three personas, people who can see things, people who can change things, and people who can create new things.

**Shishir Mehrotra** (00:11:18):
Basically everybody charges for the top two. They charge for editors and makers. If you can make changes then you have to pay. And that's like every document product you can think of, including ones do drawing or so on. They all do the same thing. And we decided that we're only going to chart for people when they make a document. So you think about it, you get a Coda doc, you only need one If you are using any of our paid features, you only need one paid license for doing it. And the reason we do that in terms of that diagram is I wanted no friction on the share edge. I mean the share edge for us is like that's the moment of, "Hey look, I'm doing this thing, it's so cool." And that's the moment where the line I gave to the team is I want no dollar signs in the share dial going into that, every product has its moment of how he's for growth.

**Shishir Mehrotra** (00:12:04):
And going back to YouTube, imagine you had to pay for people you shared with. Nobody would ever share anything. But that's how basically every productivity product works is the moment they charge you is when you share with somebody. The Blue Loop, I often call the YouTube loop because the emotions of publishing a doc are incredibly close to that of publishing a YouTube video. And people have all sorts of reasons why they do it. I mean sometimes people do it, there are people who do it for money, but a lot of people do it for exposure, for brand building. They just want to get an idea out in the world. They want to get feedback. Some people do it for fun, some people do it as a charitable contribution. There's lots of reasons why people do it, but the net effect of what happens is for YouTube, the vast majority of how people found out about YouTube was through a video that was shared with them.

**Shishir Mehrotra** (00:12:51):
That's sort of the impact, but it changes the dynamic that allows everyone who publishes a Coda doc, now it's a very natural incentive to go share it with the right population. If you're an orange theory, you share it with the orange theory population. If you're into plane ticket to ride, you share it with the ticket to ride population. But if you're into bundling, you try to find a small group of people that care about bundling, tell them all about that. And what happens for us is that then becomes a loop. That means that most people's exposure and almost a third of our users come through this loop. They're not actually exposed to Coda, they're exposed to a great idea for how to run an offsite or how to win ticket to ride or whatever it might be. And in that process, they learn about the product. And so then they come in through this vehicle.

**Shishir Mehrotra** (00:13:45):
And one reason it's very important is because for products like ours that are very horizontal, you get different types of users. There's some users that I call the building block thinkers, they like to build up from scratch and the blank surface of Coda is really amazing for them, but for most people that's intimidating. I don't really know what to do. Most people in the world are problem solvers. And so they start not by, "Do I need a new document?" They start with, "I've got a problem, we don't make decisions fast enough at our company," or, "My family can't figure out what to do on the weekend," or whatever it might be. And then when they find a solution to that problem, they then pick the right tool. And so the blue Loop allows us to go after that and it changes how the motion of the ecosystem works as well. But that's what Blue Loop and Blue Loop is.

**Lenny Rachitsky** (00:14:31):
Awesome. I have a bunch of questions I want to ask. The first is for founder listening to this and they're like, "Oh man, what am I loops? What's my flywheel? How do I think about my business?" Can you talk a bit about how you came upon this way of thinking about the company? And then also how do you structure your teams to work in this way if this is the way you're thinking about growth?

**Shishir Mehrotra** (00:14:50):
Maybe on the first part, and I think you just hosted Casey Winters, he is pretty famous for talking about loops, not funnels. And I do think there's a very natural thing when you're building a product or building a business to think about your funnel and you think about things as being linear, that somebody comes in, they go up to your signup process and then they see your onboarding and then they get exposed to the first magic moment in your product and the second magic moment, so on.

**Shishir Mehrotra** (00:15:13):
But the truth is, it doesn't really work that way. Almost all products have some form of loop. That person turns around and maybe sharing is built right in your product or maybe it's not, or maybe there's a way that it happens through advocacy, but understanding that the way products actually grow and spread happen through some type of loop not funnel, is I think pretty fundamental. So first piece of advice I'd give is you probably do have a loop. Whatever the product is, there's probably something about it that causes that loop and understanding how that works really important. I mean in terms of what it is. In our case, I'd say if you take Black Loop and Blue Loop, the Black Loop is every product in our category has that. We didn't invent it. You build a document, you put a share button on it, every product has that.

**Shishir Mehrotra** (00:16:01):
Sometimes it's just recognizing what's there. It's not that interesting. The Blue Loop on the other hand, is not something that every product in our category has. It's not really a thing that you expect to do with Google Docs or Office or so on. It's our unique take on, "Hey, we're going to build a publishing platform that isn't just for sharing ideas and building things with your team, therefore putting things out in the world." I mean, one of the best compliments we hear about the Coda Gallery is I had this user tell me, this line I really love is said that the Coda Gallery feels halfway between Medium and an app store. And you can come and you can read about anything interesting in the world and you can go shopping and say, "I need one of those. I need one of those and I need one of those."

**Shishir Mehrotra** (00:16:40):
And it's my view that this category, we call the all-in-one doc category, I think this is going to be critical. I don't think that there's enough people out there that are looking for a horizontal new blinking cursor. I mean, they exist and you can get through your first million users that way. But I think to get to the level of impact we want to have, we've got to find this problem, see here. So you probably have a loop, not a funnel, and it might be hiding in plain sight or it might require invention. That's the bounder dance and the fun of it, but finding it, writing it down I think is really helpful. Second part... Oh, how do we organize team?

**Lenny Rachitsky** (00:17:18):
Yeah, but let me ask one quick question. You said this, I think it was a data scientist that first imagined and diagram this out because I'm curious, as a founder listening, they're like, "Oh, how do I find something like this?" I imagined part of this was, "Oh, this person brought you this interesting way of thinking." And there's this process of, "Oh wow, this is cool. Let's think about this." What was that like? Just over high level, that process.

**Shishir Mehrotra** (00:17:41):
He currently runs data and finance for us. He's actually one of the early founding members of the team, Matt Hudson. So he is getting every job here around the go to market team. Very insightful. But honestly, the idea can come from anywhere. I mean there's a really famous loop diagram for Uber that I think one of the board members drew it or Travis drew it.

**Lenny Rachitsky** (00:17:59):
Built early.

**Shishir Mehrotra** (00:18:01):
Yeah, right. Yeah, that napkin sketch, who knows how true that is. Probably lots of dispute on that. I think Airbnb had a similar diagram. I'm trying to remember.

**Lenny Rachitsky** (00:18:12):
We tried, we had some sketches.

**Shishir Mehrotra** (00:18:15):
Right. So it can come from anywhere. I do find that the most natural place to see it is just when you're talking about your business to someone, when you're pitching a customer or a candidate, I actually think candidate... I think we're going to talk a little bit about energy, but I think talking to candidates is one of the best ways to hone what your business is about. Because those people are in some ways even more critical than investors. I mean they're investing their time, not just their money. And so your ability to get across to them why this thing is going to be interesting and how it'll grow.

**Shishir Mehrotra** (00:18:50):
And they're the most discerning investors out there in a lot of ways. And they're actually not that easily confused by metrics and so on that could be temporary. And they put themselves in that picture like, "Can I see that happening?" And so for us, the black loop part is pretty obvious, but the blue loop part, you had to squint a little bit to think, "Will people really do that? Will people come and publish these documents like some hybrid between websites and blog posts and templates? What are they going to going to do and why?" And so it required a little bit of creativity, which forced me to get better and better at pitching why that's going to happen and what that role is going to feel like. And this analogy of halfway between Medium and an app store is that helped people crystallize what that promise has to feel like. So I think that... And this idea can come from anywhere, but if you want mine for your own loops, go look at what you told the last few candidates you talked to.

**Lenny Rachitsky** (00:19:48):
I like that. And then just take some attempts at drawing some kind of diagrams. That's how I thought about that when I was thinking about it. Do you find that the quality of user is different amongst the loops? I imagine one is like 80% of the growth, but maybe the other is a different type of user, maybe higher quality. I think about a little bit with Airbnb referrals drove higher quality hosts, even though it was still a small portion of all hosts. And so it was a really lucrative and interesting channel. Do you find anything like that?

**Shishir Mehrotra** (00:20:14):
So I mean quality and activation are a little bit different. I mean the Blue Loop definitely, there's actually three entry points on that diagram. Those people come through the Blue Loop, those people get shared through the Black Loop and those people come through the top of the funnel. There has to be like your seat population, somebody starts with blinking cursor. Nobody shared anything with them. Either a Blue Loop, a template to document or Black Loop a way the team is running. If you look at activation, retention, so on, certainly the highest is the black share. Somebody shares the document and says, "Hey, this is how we're running the staff meeting." You're just going to use it. So the job or retention there is a all different, and actually one thing that is... Actually, let me come back to that evolution. Second best is through the blue loop and then the third, the worst, the hardest is activating through the very top. And from there, roughly one in five people make it to what we think of as our activation moment, which is hard.

**Shishir Mehrotra** (00:21:14):
It's like you're going to hand somebody a new product that they didn't start with a problem on and nobody handed them a document to say, "Just work in." That's hard now. Now all our flows are really important and so on. But if you think about these three different dynamics from how you asked about how you struck your team, they're incredibly different mindsets. Because coming to the top of that diagram, we get to own the conversation. We have our opportunity to tell you what the product's about, what you should do with it, here's the minimal set of things you need to know in order to be productive and gradually reveal the other things that you might need to know, meaning the order of those things wrong, real trouble. But it's actually a minority of how people get exposed to Coda because in the black loop, the person who owns that conversation, the person sharing the document with you. If that person does it and mispositions it or doesn't just makes a crappy document or so we have to help them onboard their users, which become our users.

**Shishir Mehrotra** (00:22:11):
Same thing in the Blue Loop, that conversation is now owned by the publisher. They're really not that interested in teaching anybody about Coda. They're mostly interested in here's this really cool way to do Orange Theory, or here's this interesting way to run a meeting. And so, one of the interesting things about building platforms, which I think is a little bit different than products that get to be direct. For better or worse, most of the products I've gotten to work on are platform products. And I find that there's two very different kinds of people that like that challenge. So some people, and I think Steve Jobs was the quintessential example, if he didn't really like being a platform, the iPhone ship without an app store, they locked down the screws on the back on all the devices that nobody could open them. And his viewpoint was, " I'm going to control every element of what my users see." And on...

**Shishir Mehrotra** (00:23:00):
I'm going to control every element of what my users see. And on the other hand, platform thinkers, you sort of assume that my connection to my eventual user is through someone else. Like YouTube, regularly they come to work at YouTube and somebody would say, "Well, here's what happened last night." And sometimes it's heartwarming, like, oh, my gosh, this kid bit this other kid's finger and it took off like crazy and this Korean pop star just broke through the billion view mark before everybody else did. And sometimes it was not heartwarming and you don't get to control that because that's part of being a platform.

**Shishir Mehrotra** (00:23:37):
And so it does change how you think about the way you run the team because if you have a loop where your community ecosystem users on control that narrative, then you have to incorporate that. Another close analogy I think is Airbnb and the famous story of them taking pictures of people's apartments. It's like they had to reach out and try to control that and eventually you can't do that. You had to sit back and let people market their hotels. And thankfully the ecosystem got good at it, but they kind of had a similar dynamic, I think.

**Lenny Rachitsky** (00:24:12):
Absolutely. With Airbnb, pricing is even more of a challenge where a lot of hosts don't really know what to price. They think their place is worth a lot more and we can't tell them the price. There's laws around that. And so it's like, hey, maybe you want to price it at this rate if you know what's good for you. So it's a lot of encouraging. So yeah, I've seen that in action. So you talked about teams and how you think about structuring them a bit and that's a good segue to our second topic, which is around a book that I hear you're writing called The Rituals of Great Teams.

**Lenny Rachitsky** (00:24:40):
And I think what you're doing there is exploring rituals that have emerged at some of the more successful companies. And so just a question there, one, how'd you get interested in rituals, so much so that you decided to write a book, which is such a trudge and endless amount of work? And just yeah, where is it at, how's it going? And then I'll ask you a few more questions there.

**Shishir Mehrotra** (00:24:59):
The writing a book, so I'm writing this book, it's called Rituals of Great Teams. And when I signed up to do it, I thought it was going to take six months. I'm now almost two years in [inaudible 00:25:11] my manuscript in four months and I am probably half done. So there's a lot of work ahead of us in building, but it's one of the most fun projects I've ever done. So the history behind this was, as in many cases, is a lot of sort of odd luck and happenstance. I got hosted right at the start of the pandemic. I was interviewed for a different podcast called Masters of Scale by Reid Hoffman. And the way Reid records, which I'm not sure I would recommend this, but he does it a little bit differently than you do. You sit down with no idea what you're going to talk about and you talk for three hours.

**Shishir Mehrotra** (00:25:49):
And then he has a group of editors, the same group that actually at its head, and they come in and they pick 20 minutes of it and they turn and one episode. And you have no idea what it's going to be, so you talk and talk and talk and gets 20 minutes out and they're pretty good at getting to a nugget. So they picked out of this whole discussion this part that I thought was really small and it was Reid had asked me for one of my favorite quotes and I talked about this quote from a guy named Bing Gordon. People don't know Bing. Bing was one of the founders of Electronic Arts. He's a famous investor, Amazon, Zynga, so owns lots of great companies. And I happened to sit on a board with Bing and he used this line. I think Bing's one of the best non-linear thinkers in The Valley. Always learned something with Bing.

**Shishir Mehrotra** (00:26:29):
And he used this line that really stuck with me. He said great companies has a very small list of golden rituals. And there are three rules of golden rituals. Number one, they're named. Number two, every employee knows them by their first Friday and, number three, they're templated. And he has great examples. Amazon has six pagers and Google has OKRs and Salesforce has V2MOM and there's all these different rituals that people do. And I ended up sharing on the podcast a little bit about what Coda's golden ritual is. If you were to ask a set of Coda employees on their first Friday what Coda's golden ritual is, they would almost certainly tell you about this thing we do called Dory/Pulse. It's sort of the key of how we run meetings and do write-ups and so on. It's a pretty simple idea, is that in our write-ups and in our meetings, instead of going around the room and hearing what everybody thinks, we do this thing called Pulse.

**Shishir Mehrotra** (00:27:26):
Everybody writes down what they think and we hide everybody else's until you're done writing. So you force yourself to be eloquent about your opinion, on the record about it, and unbiased. And then the second thing we do is called Dory, which is instead of randomly asking questions, we ask people to put the questions on the table and then we take a round of up quoting and down voting them to actually figure out what we're going to talk about. Dory's named after the fish who asks all the questions. It's a tool we use a lot at Google that we kind of turned into this mini tool. If you were to ask a set of Coda employees on the first Friday about Coda's golden rituals with Bing's three tests, they'll certainly talk about Dory and Pulse. And it's not because they're meeting wonks. It's because it's indicative of the culture of the team.

**Shishir Mehrotra** (00:28:08):
And so I'll regularly hear employees say things like, "I just joined Coda. It's been a week. It's amazing. The culture is so open that I got to ask a question in a meeting and it outvoted the CEOs." Or they'll say, "I got asked for my contribution to this really hard decision we're making and it was thoughtfully presented. I had space to be able to do it well without bias and it was actually read and considered as part of the decision making process." Reid's podcast did pretty well and I got all these questions about rituals and so I decided to do a dinner which turned into a dinner series. And basically every third Wednesday we would host a group of people to share the rituals with each other. And I learned a bunch of stuff in this process.

**Shishir Mehrotra** (00:28:54):
I've now interviewed over 1,000 people for this book and There's lots of really interesting rituals that come out of it, but first thing I learned is people love sharing their rituals. I've interviewed people from many companies that everybody's heard of, Nike, Disney, New York Times. It's all the way down to many startups that maybe people haven't heard of or companies in industries that people don't talk a lot about. Book authors, pundits, lots of different people that have come through this process. Everybody loves sharing their rituals. Everybody has little secrets to how they run their business, but for some reason the how we work part everybody's very willing to share. People also love hearing about them. And I was like, "Is this going to be interesting for a dinner, geeking out about how a team works?" And it turns out not only do people like hearing about it, it's the littlest details that matter. It's like, yeah, we kind of do that, too, but we have this issue.

**Shishir Mehrotra** (00:29:46):
How'd you get past this? And you start discovering that actually those little details are what would make or break a thing, that you can't quite do it the exact same way. And then the other thing I realized, which is probably the most important point, is that rituals are, I like to say that they are, a mirror of culture. That one of the attendees, Dharmesh Shah, founder of HubSpot and very thoughtful person, he talked a lot about this thing that is virtually presented as something called flash tags, which is a really cool example. But Dharmesh talked about how when we're building companies, we actually build two products. We build one for our customers and we build another one for our employees. That's actually how we work part of it. That's the term he uses for that, is culture. That's the product we build for our employees.

**Shishir Mehrotra** (00:30:29):
I think it's a very interesting way to define what culture is. Interestingly, when you ask people about their culture, hey, what's the culture of Google, or Airbnb, or so on, the way they'll answer the question is through rituals. They'll say here's what we do and the way you know this is what we do is through this ritual that's in place. So I thought that was pretty interesting. Started off just building a little listicle of here's all the great rituals and then I started realizing that actually the comparison between them is kind of interesting. And so I started sort of filling in the gaps between them of like when would you do X versus Y and what did I learn through that process? Publisher asked if I would turn it into a book and I agreed without really contemplating how hard it would be. And it's become what most of my evenings end up being on this.

**Shishir Mehrotra** (00:31:17):
I have a wonderful co-writer, Erin Dame, who's incredibly gracious with her time and helping me sort through the best ideas and the worst ideas, but it's a really fun project.

**Lenny Rachitsky** (00:31:29):
What are some of the more wacky and/or impactful rituals that you've come across that you can share?

**Shishir Mehrotra** (00:31:36):
Boy. I'd sort it down the list. I'll tell you some that are interesting and recognizable. One of the most fun ones is from Arianna Huffington and she shared a ritual called Reset. And there's a bit of background on Arianna, she's well known for Huffington Post. She now runs Thrive. She had an accident a few years back and ended up going through a period of doing a lot of research on how the brain works and ended up coming to this set of conclusions about how you can affect your own brain chemistry. And one of the things she does as a sort of personal ritual is I think called a reset.

**Shishir Mehrotra** (00:32:13):
It's basically the ritual is you make a one minute video that is personal. And they have a little template for doing it, but it's a breathing exercise. It's like you are supposed to play it while you do this breathing exercise, but it's personal. So it's like her video, you go search YouTube for Arianna's reset, you'll find it. It has pictures of her kids, it has quotes she loves, it has videos of her hometown in Greece and so on, but the way she brought it to the team was they start meetings by randomly picking someone. They call it spin the wheel. They randomly pick someone and they play their reset. And the idea is you get this two for one where everybody gets a little bit the brain chemistry rewiring of 60 second breathing exercise. Everybody gets back into that sort of zen state a little bit and you learn a little bit about each other.

**Shishir Mehrotra** (00:33:05):
And she was saying that the pictures people pick and so are interesting, but actually the music people pick is probably the most interesting. A lot of people pick calm music, some people will pick something they rock out to, but everybody does their reset a little bit differently. So that was a really fun one. Another really fun one that I was surprised by, Gusto does this thing in their hiring calls. So you get an offer from Gusto and apparently when you get on the offer call of congratulations, you got an offer, instead of just meeting the recruiter, which is what most companies do, they have the entire group of people that interviewed you join the call and they all say something about why you're amazing and you should join Gusto.

**Shishir Mehrotra** (00:33:46):
And it's such an interesting ritual in so many ways. For the candidate, obviously what an amazing experience. To use an Airbnb term, that's like a level 11 experience of what that feels like, but also for the company. One of the questions I get asked, "What if I voted no? What if I'd said this person is a no hire?" And I said, "It doesn't matter. You're on the call, you're going to work with this person, you're going to help them feel welcome and you're going to help them understand where they stand." I think it obviously takes a bunch of time, but it also is a signal to the company of how important hiring is and something that obviously we all prioritize. Those are maybe a couple of the maybe different ones that people might not have heard of before.

**Lenny Rachitsky** (00:34:31):
Those are amazing examples. Have you integrated any of these rituals from other companies doing this research into Coda?

**Shishir Mehrotra** (00:34:37):
All the time and it's the cheapest form of research. I mean, I get to borrow all these great ideas from all these companies. We just added one to our decision making process. This is a good example of a little detail that really matters, is Coinbase has a ritual that's formed around ... This is a decision-making ritual they call ... It's actually amazing how many companies have a decision-making ritual with a name, with a bur. So at Square, Vocal called them Spades. He kind of verbified it. There's a template, but you use Bing's three tenants. It's got to be named, every employee knows it by the first Friday and it's templated.

**Shishir Mehrotra** (00:35:18):
So Coinbase does a thing they call rapids and rapid is a framing around what the roles in it are, the responsible approver, participating, informed and decider, but their technique of doing it was really interesting. They have this subtle nudge thing that we weren't doing that I've now incorporated at Coda. So at Coda we have Dory and Pulse, like a very common ritual. It spread through a lot of different companies that use Coda. You don't really have to use Coda to do it, but I think Coda is pretty good at it. But one of the things we were facing was that you would do this pulse and so you'd have a meeting. And if you did it wrong, it could feel like voting and it could feel like consensus building.

**Shishir Mehrotra** (00:36:04):
And so we would get this, people would talk about it and every ritual has its pro and con, but people would look at it and say very open culture, you're allowed to share whatever you want. But on the other side for the person that's trying to make a decision, it can feel like, oh, my God, I now have 30 pieces of feedback. Am I supposed to wait for all 30 of them to be yes? Am I supposed to wait for it to be a majority and how do I know? What am I supposed to do here? And so Coinbase had this really simple idea that we sort of smushed together, which was at the top of their rapids they named who all the people were and then next to each one they put a little box that said what is the decision from that person?

**Shishir Mehrotra** (00:36:44):
They just organized. It's very similar to Pulse, but they kind of organized them and said everybody that's in the inform bucket, they can comment, that's totally fine, but we really care about the approvers, the responsible and then of course the decider, the one that really matters. And so we just added a column to our Pulse, which is what is the role? And we grouped the table by that. And the other thing that Coinbase does, which it sounds really subtle and small, but really in detail it really matters, is the person running the meeting pre-fills that with what they want from that person. You are an approver. Maybe I have three approvers because I have a budget approver and I have a marketing approver and I have a sales approver, whatever it might be, and I need you to give me this answer. I don't need you to comment on everything I'm doing, but I need you to tell me do we have the budget or not?

**Shishir Mehrotra** (00:37:31):
Or I need you to tell me am I authorized to make this change in this part of the product that we generally don't change, or can I change the onboarding flow, or whatever it might be? And we took a process that I think was doing a pretty good job of getting rid of groupthink, which is really the heart of what we were doing with Pulse, but had this danger of being overly leaning towards consensus building to a fault. I think consensus building is a good thing, but consensus building to a fault is not. And we sort of stole this one from Coinbase and we switched it in and it got better. And that's a good example very recently.

**Lenny Rachitsky** (00:38:05):
I feel like you have a clear bestseller on your hands here and I can't wait to read this. I almost feel like you have an unfair advantage right now having all these insights before you share them, being able to execute so much more efficiently.

**Shishir Mehrotra** (00:38:17):
Well, yeah, it's interesting. I'm obviously not trying to keep any of it a secret, so the whole point of publishing it is because I think other people will enjoy it and can get benefit out of it. But if people are interested, one of the other choices I made in writing this book is I decided to do it somewhat in the open. So there's what I call the rituals of great teams brain trust. And so if you just search for me and Rituals of Great Teams, you'll find it. And I'm sure we can add the link to the show notes, but you can sign up. And basically, as I finish a chapter, I put it out to the group and there's now a few hundred people that are helping me co-edit this thing.

**Shishir Mehrotra** (00:38:55):
Some of them just because some of them come in and give me help on storytelling, grammar, so on, but a lot of them are contributing where they show up and they say, "Hey, you missed this one. We actually do that, but we do this other thing a little bit differently and you should really talk about that." Because I kind of view it as it started as a dinner series. It started with everybody's going to give to each other. And so I kind of wanted to bring that into the writing process. It's also a cheap way to get some pretty good editors and it pretty helpful.

**Lenny Rachitsky** (00:39:23):
**Shishir Mehrotra** (00:40:53):
There's a whole section of the book on ... I get this question a lot of how do I find the rituals we have? How do I adjust the rituals to match? Are they supposed to change? There's lots of things you see because some rituals are great when you're 100 people and they're terrible when you're 1,000. And you should actively change those things. Some are great in what sometimes people call peacetime versus wartime. You should do this during this time, but you should actively not do it when you're in this other time. And actually, that in itself is a ritual. I mean, every company has some form of a war room ritual that is ... I guess Facebook I was learning. We did a dinner last night, so I learned a little bit about it. Facebook apparently calls them lockdowns, which is a term I hadn't heard before, but apparently it's well understood. When they say lockdown, everybody knows exactly what it means.

**Shishir Mehrotra** (00:41:37):
It's like we no longer do the goal setting process, you drop this type of work and everybody just knows this is what it means. But I would say that when we talk to people about rituals, a set of rituals that happen organically. I mean, those are the easiest. Dory and Pulse for us was one of the product managers running a meeting just thought it was we're a distributed first culture, but hadn't really adapted to it properly. And this product manager is just annoyed at waiting around on Zoom for everybody to go around and say their piece and it just took forever. And by the end everybody's like, "Can we just pause? Everybody just write down what you think." And he just happened to do it in this thoughtful way and it just took off. And so some rituals grow organically and you just got to wait for them to do it.

**Shishir Mehrotra** (00:42:24):
But there are cases where companies actively form a ritual to drive a certain behavior. And the best advice I've given on this topic is to read one of my other favorite books. It's a book called Switch. It's by Chip and Dan Heath. All their books are amazing, but they also wrote Decisive and Made to Stick and Moments and so on. But this one is, if I could recommend five books, this would take two slots on the list. And the subtitle of the book is How to Change Things When Change is Hard. And the basic idea of the book is they use this analogy of a writer on an elephant on a path. And when you're trying to change things, you have three options for what you can do and it actually kind of maps to Bing's analogy. So you can direct the writer, so you can tell people what to do.

**Shishir Mehrotra** (00:43:13):
You can motivate the elephant, so you can give this thing a kick in the butt and it's going to move. You don't know exactly where it's going to move, but it's going to move. And you can shape the path. Shape the path is I'm going to set this way up so that you can only do these things. The way I think about it is direct the writer, tell people what to do. That's why if you look at Bing's tests, that's why you teach employees this before the first writing. You tell people this is what we do. And so some rituals, how do you get this ritual to work? You put it in your new hire onboarding and you make it work that way. Motivate the elephant, a lot of that's about branding. So what do you do with rituals? It's an amazing number of rituals where I'll tell people that seems like a great ritual.

**Shishir Mehrotra** (00:43:51):
I would highly encourage you to give it a name. Give it something that lets people anchor ideas to. Names a very powerful thing. If I said, "Yeah, at Coda we do voting and sentiment writing or something," I don't even know what you would say. It would sound boring. It wouldn't sound like something you could brag about, something you could form identity around. And so it's very important to give it a name. And then finally, why do you shape the path or you set things up? You templatize, make it as easy as possible to follow this ritual. And make it just a part of what we do enough, then if you're at Gusto and you're like, "I don't really understand that hiring cult thing," where it's like guess what? You're going to be invited to one soon.

**Shishir Mehrotra** (00:44:28):
You're going to see it and then you're going to have to do it. Or if you're at Square, you're going to see the spade template and you're going to learn how to do it. So I think Switch is ... I recommend this book for lots of purposes, but as you're thinking about rituals for your teams, it's a particularly relevant frame.

**Lenny Rachitsky** (00:44:45):
Awesome. By the way, that's a little plug for the YouTube version of this podcast, which is now a thing we do. So if you're like, hey, I don't see what you're talking about, just search for Lenny's podcast, YouTube, and I think you'll find it and we'll probably link to the ad in the show notes. I'm also reminded of Airbnb's rituals, which you probably already know about, but they're kind of all hilarious and weird. One is formal Friday, where people dress up in suits and gowns on Fridays. Another is a human tunnel for all new employees, where every new employee has to run through a human tunnel and jump into a beanbag or something. And then there's a new hire tea time, where new hires drink some tea with some veterans and chat about where they're from and things like that. There's a bunch more, but those are the ones that are my favorite.

**Shishir Mehrotra** (00:45:27):
Those are great. I also included some of the level 11 thinking as well. I think that's also a good Chesky favorite. Brian also has another one that's in the book that's about how to rank your to-do list by finding leverage. That's a really fun one as well. They're like don't rank your to-do list, but a lot of people do importance versus urgency or so on. And I guess he sorts his by which of these is most likely to create leverage of getting rid of the rest of my lists, which I thought was very ... I started doing that in my to- do list and it's very interesting and impactful.

**Lenny Rachitsky** (00:46:02):
That's actually an incredible segue ...

**Shishir Mehrotra** (00:46:00):
... you listen, it's very interesting and impactful.

**Lenny Rachitsky** (00:46:02):
That's actually an incredible segue to our next topic, which are eigenquestions.

**Shishir Mehrotra** (00:46:06):
Ah, yes.

**Lenny Rachitsky** (00:46:08):
And so eigenquestions, one of your most classic posts, you mentioned this at the top, maybe your one of the most liked posts, other than maybe bundling. It sounds like some kind of German game show, eigenquestions. Can you tell us what eigenquestions are, and then I'm going to ask you a few more questions around that?

**Shishir Mehrotra** (00:46:22):
I've thought about the German game question.

**Lenny Rachitsky** (00:46:26):
Yeah, sorry [inaudible 00:46:27].

**Shishir Mehrotra** (00:46:29):
I didn't know this would be a very interesting game, but we could try to create one. Okay, so I'll describe what eigenquestions are, but maybe I'll start by telling you a little bit about where the concept came from. And, this is actually a YouTube-ism that... Maybe just to place ourselves in history, so in 2008 I joined YouTube. And many people don't remember this, but YouTube at the time was seen as a mistake. It was seen as Google's first bad acquisition, everything else had worked, but this thing kind of seemed like a disaster. It was grainy videos, we were losing lots of money, we had billions of dollars in lawsuits, none of it really seemed that obvious. There's lots of discussion on how to reorient it, fix it, and so on. And so everybody outside, that's what they saw.

**Shishir Mehrotra** (00:47:14):
If you stepped inside a YouTube staff meeting in 2008, actually one of the toughest questions we were answering was this question we called the Modern Family question. And it may sound small, but it actually was very perplexing. And the question was pretty simple, the question was if you looked at our search traffic at YouTube, one of the top five queries basically every week was for a show called Modern Family. And Modern Family was number one show on television at the time, by far the most popular. And we were second-biggest search engine in the world behind our parent company Google, so search traffic was very important. There was one big problem, people would come search for Modern Family, one big problem, we didn't have Modern Family on YouTube. And so we'd give them some pretty crappy responses. And the question was... And by the way, ABC.com had decided to post every episode of Modern Family live on their website.

**Shishir Mehrotra** (00:48:06):
Which nowadays is kind of typical, but in 2008 that was not typical, no is it kind of a big gamble they made, and they're going to post all these shows. So the question was, should we answer the query Modern Family by linking off to ABC.com? Do we link out or not? And the company basically divided. And so there's half the company, mostly the product team, vantage team and so on kind of aligned around a viewpoint that was, "That's what the user wants, link them off to ABC.com. We're not owned by Google, Google tries hard to prioritize, do right by the user, the rest will follow. That seems like the right thing to do, so let's do that." And then the other half of the company, most of the business function, sales, marketing, especially content partnership said, "Please, please, please don't do that. If you do that and you start linking off to all these other places, nobody's ever going to put good content on YouTube, and we're just going to get the stuff that doesn't deserve to live anywhere else. And that's not a very good path to be."

**Shishir Mehrotra** (00:48:59):
And you can imagine that those two mindsets, it's almost like it was good versus evil debate, which is do right by the user or the business. These are all almost impossible to solve problems. And this would happen meeting after meeting after meeting, did we make a decision yet? Modern Family, what are we going to do? So we had this offsite, we said we're going to spend the whole day, and we're going to figure this problem. And we went up to this hotel in Half Moon Bay, and the executive team all sat down, and I was asked to frame the discussion, go collect everybody's opinions, and collect all the data, and just ground it all in facts. And then we're going to have a discussion, we're going to reach a decision. And so the night before I'm sitting and thinking about, how the hell we going to have this discussion not just be a shouting match of this good versus evil position?

**Shishir Mehrotra** (00:49:46):
And I happened to read a analysis that was being done by a different team at Google, the Google shopping team, where they were facing this interesting challenge of they were in this deep fight with Amazon, and they were getting their butts kicked, and they were trying to figure out why. And the walking in theory was, the Google shopping team's view was why would anybody ever go in to Amazon? You could come to Google, and we had indexed all of Amazon and the entire internet, why would you ever pick Amazon? And the feedback that was coming back from users was they'd say, "I picked Amazon because I value consistency over comprehensiveness." They would say things like, "I really value that I go to amazon.com and I understand how the reviews work and how the ratings work, and I know that the returns work the way I want and I understand the shipping is going to work. And it just felt consistent. I know it doesn't have everything, but it has enough. And I value consistency over comprehensiveness."

**Shishir Mehrotra** (00:50:43):
And so the night before this YouTube meeting, I decided to reframe the question and say, let's not have the discussion about linking out at all. We're going to start by having a theoretical discussion about, in a decade from now, is the online video market more likely to be about consistency or about comprehensiveness? And that is a question that you can have a very reasonable debater. What are the reasons why a market evolves towards consistency over comprehensiveness? And we basically have this discussion and we all came to the conclusion this market is going to value consistency over comprehensiveness.

**Shishir Mehrotra** (00:51:17):
And by the way, I think, I mean now almost 15 years later, I think we're right. If you go look at video market obviously it exploded. There's so many great video properties out there, none of them are comprehensive. There is no one-stop shop or a place where all the video exists. And so I think we were right. But what happened was by answering that question, the link out question all of a sudden became super easy. We value consistency over comprehensive. We definitely don't need to link out. In fact, we should make a whole bunch of other decisions as well. So we went and at the time we used to, this was the days of flashed players and so on, we embedded other people's players on YouTube. We stopped doing that as well. Probably the most famous decision we made was with the iPhone.

**Shishir Mehrotra** (00:51:56):
As I mentioned earlier, the iPhone when it first shipped had no app store. And so they built all the first few apps including YouTube. And so here we were a few years later, iPhone the most popular phone on the planet and the YouTube app on the iPhone was built by a team at Apple and they had not been able to keep up with what we were doing. Almost half the catalog didn't play back on the iPhone, they were missing a bunch of features and so on.

**Shishir Mehrotra** (00:52:17):
So I drove down to Cupertino and I sat down with Scott and Phil and said, "Hey, we're going to have to take back the YouTube app." And they said, "I don't understand. Why would you do that? You have default distribution on, as far as they were concerned, the most important operating system in the world. Why would you do that? You're going to have to rebuild all this from scratch and it just seems like a really bad choice." And I said, "No, no, it's actually quite an easy choice. We value consistency over comprehensiveness. We would much rather be on fewer phones with a more consistent experience than be on all of them with an inconsistent experience." So what, this is a choice we're making and it worked out fairly well.

**Shishir Mehrotra** (00:52:51):
So this decision, the Modern Family question ended up becoming named as the example for a term called eigenquestion. So eigenquestions, it's not a German game show, it is a made up word and it's named after a math concept called eigenvectors. And the math is not really necessary, but for people who are curious, go back to linear algebra, eigenvectors are in a multidimensional space. They're the most discriminating vectors of the vectors in that space, the dimensions of that space, it's a concept that gets used a lot in machine learning and so on, but actually the math doesn't really matter. The eigenquestion, the simplest definition of eigenquestion, it's the question that when answered also answers the most subsequent questions.

And it's a very simple idea that when you sit down and you say, hey, here's all these questions we ought to answer, how do we all usually rank them? Sometimes we rank them just by what order we came up with them. Sometimes we rank them by importance, which is the most impactful decision we're going to make. But this methodology says don't rank them that way. Rank them, like you said, [inaudible 00:53:53] thing about about leverage, same idea, rank them by which ones would eliminate the most other questions of the list. So you take that list and you said, should we link out to Modern Family? Should we own the YouTube iPhone app? Should we do... mind you, those were really hard questions to answer. But turns out if you answered just one question, do we value consistency over comprehensiveness, you answer all the others. They all of a sudden become very simple.

**Shishir Mehrotra** (00:54:13):
And so this idea of eigenquestion became part of our vocabulary, became a clear ritual for YouTube, that is, what is the eigenquestion, here at Dish for Coda as well, it sort of spread through other places, but that's the basic idea.

**Lenny Rachitsky** (00:54:26):
Amazing. What a baller move with Apple.

**Shishir Mehrotra** (00:54:30):
Pretty scary move, yeah.

**Lenny Rachitsky** (00:54:31):
Yeah. But I was just going to say, I think YouTube's probably in the top five, 10 most downloaded apps. So it worked out.

**Shishir Mehrotra** (00:54:38):
We'd go for that meeting and I bring along the product manager for the iPhone app named Andrey Doronichev, and he's the one having to explain what we're going to do and so on. And it's a hard contentious meeting. And as we're leaving the meeting, he says, "Hey, can I get a selfie with Bill and Scott?" Andrey, what are you doing? There's this great picture of him with us asking for, take this back. And clearly he's very starstruck. There's a lot of people with view as like, Apple would do a better job of building the YouTube app than us. Who are we to tell them to not do that? Of course, in retrospect, that was a silly way to think about it.

**Lenny Rachitsky** (00:55:17):
Wow. I would do the same thing. That's amazing. Who's this person? Because that's awesome. I love that as a leader you bring the PM of the team working on it versus just the big shots at the top.

**Shishir Mehrotra** (00:55:29):
Yeah, Andrey, he's now a founder. He started a company called OPTIC, basically building content ID for NFTs, which is a much needed thing in the Web3 world. But yeah, I mean the team building it, I mean, that meeting I brought my partnerships lead and I brought the ENCH lead that was covering the area too. And yeah, I think that some of it is, if I had to be honest, some of it is like they really wanted to come and meet with Apple. Some of it is like, for my own sake, I kind of wanted some backup. I'm about to make this kind of bold ass... And to Apple's credit, I mean they could have been pretty bad about it. I mean they could have not allowed us on the store and so on.

**Shishir Mehrotra** (00:56:09):
And they said, "Okay, well we don't like it, but we understand your choice. You have to know that you're going to start from zero. We're not giving you a single download for free. You're going to have to start from zero and we will brick the current app right on the agreed upon date." And the negotiation was can you please just tell those people that there's a new app? And so that's what we negotiated out of it and they eventually did that and that was fine. And in the end, YouTube is now one of the top downloaded apps on iPhones I think. I mean, it was like six months after launch, we had like 80% share. Everybody downloaded the app. And so it kind of ended up not being that much of a comprehensiveness choice, but it was a clearly hard decision made much easier by asking the right eigenquestion first.

**Lenny Rachitsky** (00:56:55):
Wow. Speaking of eigenquestions, are there other examples of eigenquestions that come to mind to make this even more concrete in people's minds? I don't know if that's the right way to frame it or is it more just when you have a list of questions, look for the one that'll answer the most. How do you operationalize this concept?

**Shishir Mehrotra** (00:57:13):
There's lots of them. I mean for Coda, the sort of most conceptual eigenquestion for Coda was, we use a line a lot for Coda, that Coda allows anyone to make a doc as powerful as an app. You can reverse that statement and say, allow anyone to make an app as easily as a doc. And those two sound similar, but they're not. They're actually quite different statements. And so our most commonly debated eigenquestion is, are we more committed to being a doc or being an app? And which way do we want people, if people are going to misunderstand Coda, would we rather them perceive it as a document or perceive it as an app? And we decided on doc, which is actually... And the way I cemented that decision when we made it was I named the company that way, where Coda is a doc backwards.

**Shishir Mehrotra** (00:57:56):
I said, "Well, we're definitely not revisiting this one. Coda is a doc first." That's a good example. I mean, another one, by the way, I would say eigenquestions is a term that a guy could resonance itself, but it's a hard technique. It's not always easy to know how to do it. And one of the things I get asked a lot it's like, is it a skill you can learn? I absolutely think it's a skill you can learn. It's a thing that once you observe it, you get better at it, you can learn it, but it's not easy to learn it. And one of my observations by learning skills like these is, you want to learn them in non-pressure filled environment. To use an analogy, if you were trying to learn a sport or learn an instrument or so on, imagine if you never did practice, every time you played basketball was in a real basketball game and every time you played the piano was in a recital, you probably would never get better.

**Shishir Mehrotra** (00:58:50):
And I think one of the troubles with the concept like eigenquestions is, we tend to only practice it in real world scenarios that are high stakes. And so one of the things I encourage people to do is to practice eigenquestion in completely almost frivolous situations. So I have an interview question I ask, which I think, and maybe we'll get to this a little bit later as well, but it's a very simple question and it's a coded eigenquestion test. And the question is, a group of scientists have invented a teleportation device. They've hired you, Lenny, to be their sort of business counterpart, bring this to market product... Well, this question actually worked well for any role. But say you could be a product manager for this thing, bring it to market and what do you do? That's the whole question.

**Shishir Mehrotra** (00:59:40):
Usually people will start asking a bunch of questions and say, "Well, tell me more about this device. What does it do? How does it work? And is it big? Is it small? Is it vast? Does it disintegrate things or not? Does it need a receiver and a sender? It's safe?" And all these different questions come out and at some point I'll just let those questions come out and at some point I'll say, " Okay, nice job generating all the questions." Turns out these scientists, they kind of hate talking to people and they're kind of annoyed by all your questions. And so they've decided that they will answer only two of your questions and after that they expect a plan. What two questions do you ask?

**Shishir Mehrotra** (01:00:16):
And interestingly, all of a sudden the sharp product managers, engineers, so basically every role, they very quickly find what are the one or two eigenquestions on this topic. And there's no right answer, but I'll tell you one of my favorite ones is as a product manager said, "Okay, if I had to ask two questions, the two question I would ask, one is, is it safe enough for humans or not?"

**Shishir Mehrotra** (01:00:39):
And I would say a very crisp way to get to just safety, how reliable it is, they didn't ask how reliable it is, how many bits in middle, just tell me is it safe enough for humans or not? And the second one is, is it more expensive CapEx or OpEx? Is it more expensive to buy them or to run them? And then he took those two questions and he said, "Just with those two questions, I can form these quadrants." And you can say, oh, it's safe enough for humans and they're very cheap to buy, but expensive to run. Then you probably run them like human fax machines. You put them everywhere you can and you say, "Hey look, it's expensive to use, but you'll have the ability to teleport anywhere you want and this is how we're going to run it."

**Shishir Mehrotra** (01:01:17):
On the other hand, they're very expensive to buy, but cheap to run. You probably have to place them very strategically, in which case what you'd probably do is replace airports. Because airports are pretty strategically placed in places where people are trying to get around places. If it's not safe enough for humans, then you've got a whole different class of use cases where you go value what goods are transported in very costly ways. And people come up with, do you do the most expensive things or is teleporting people's replacement hearts, is that a really demanding thing? But these two questions kind of get to the heart of it. The question's totally made up. No teleportation device exists, at least not yet. And I find that people's ability to learn the method is significantly higher if it's low stakes.

**Shishir Mehrotra** (01:02:05):
That question by the way, if you ask a kid that question, the hey new teleportation device, you get to ask two questions, almost every kid will quickly get to two pretty good eigenquestions. Again, kids are incredibly good at simplifying these things down. It's actually a skill we remove from ourselves. I'll hear candidates tell me things like, well, I guess I would ask them what size it is. And they're like, "Why would you ask them what size, what decision is that going to allow you to make, to know what size it is?" And sometimes I can explain it, but sometimes not, don't get hired.

**Shishir Mehrotra** (01:02:36):
But then actually the thing I'd say about it is there are eigenquestions everywhere. You can take any product out there. I'll do it with my kids a lot and they'll say, I was just riding with my younger daughter and she said, "How come there's three gas stations in the same corner? Why do people do that?" That's a really insightful observation. What's the eigenquestion? How do you place a gas station? And it's like a bread nose. And you can almost take anything and say, what is the question that really drives this answer?

**Lenny Rachitsky** (01:03:08):
I love that. Do you actually still ask this question because you're sharing it in all the answers?

**Shishir Mehrotra** (01:03:13):
No, I don't. And I have a new one that I can't share, but we've written about it. In fact, one of big debates about publishing the eigenquestions thing is, in order to bring this to life, I needed to answer your question, how do I test this? How do I practice this? And it is much easier, nobody can repeat the YouTube one. Nobody has that choice sitting in front of them. So it's kind of a useless, it's entertaining, but as a teaching tool, it's kind of useless because you can't really go reinvent history and decide consistent versus comprehensive.

**Lenny Rachitsky** (01:03:40):
Yeah, had to sacrifice one.

**Shishir Mehrotra** (01:03:42):
We sacrifice one, yeah.

**Lenny Rachitsky** (01:03:44):
So pull on that threat further and dive a little deeper into evaluating talent and product talent. I hear this is one of your superpowers and so I'd love to learn from you and what you've seen around how to evaluate talent. So you talked a little about interview questions you ask, so maybe we could either go in that direction or just what do you look for in people that you're hiring, interviewing that maybe other people aren't?

**Shishir Mehrotra** (01:04:05):
I have a technique for it. I'll show a quick picture.

**Lenny Rachitsky** (01:04:09):
YouTube plug?

**Shishir Mehrotra** (01:04:10):
Yeah, YouTube plug. I mentioned it before the call, you can put video on Spotify now too, but the-

**Lenny Rachitsky** (01:04:16):
Spotify plug. All your platforms that you've worked on now can plug my videos.

**Shishir Mehrotra** (01:04:21):
That's right. So I'll talk through this diagram that has two axes scope, this acronym, PSHE, and this line. So I'll stop sharing and describe it and we can come back to it. But I'll tell a little bit of this technique sort of changed how I think about evaluating not only product talent, but it actually turns out you can use the same set of rules for evaluating basically every role. But I'll tell it from how you asked it about product talent.

**Shishir Mehrotra** (01:04:44):
So 2011, Larry Page took over at Google and he made a bunch of changes to the company, mostly quite positive. And one of the ones he did was he moved us from being a functional organization to being a business unit organization. We call them product units, but roughly the same thing. And there were eight product units set at Google, YouTube and Search and Ads and Chrome and Maps and so on. And that's very positive. It's hard to believe that we were already like 20,000 people were still functional, like all of engineering, all the products on reported into the CEO just seems like totally crazy with the breadth of products that we covered.

**Shishir Mehrotra** (01:05:16):
One of the downsides of it was, like in any functional to business unit switch, as you lose some of that what does the function mean. And in particular things like what is a good product manager was a question we were at risk of losing. So at the time I was running product for YouTube, the group of the eight product leaders around the company got together and said, "Hey, we need to keep some level of consistency amongst how we think about what's a great product manager or it's all going to diverge and it's not going to mean anything anymore."

Actually, as a fun aside, we did a ritual that I've repeated a few times, but it isn't done often enough is, we said, "So who's going to drive this process?" And we did it in an election. I don't know why we do elections in the public world, but not in the private world, but it's actually quite effective. We used to do them on YouTube where we would elect into certain roles and you got a one-year term, you gave a little speech you like [inaudible 01:06:08]. We did an election. Anyway, so I got chosen to be the first sort of leader of this challenge, keeping the product management function together at Google. And the most obvious job we had to do was come up with a speech for the Calibration Committee. So Google does calibration a little bit different or promotion a little bit different than most companies.

**Shishir Mehrotra** (01:06:32):
Most companies your boss decides you get promoted or not. At Google, there's a committee that decides, and it's supposed to be a committee that doesn't actually work directly with the person, so it can be a little unbiased and so on. And it gets done. The ritual was to do it in a hotel near the airport here in San Francisco and everybody get in these different rooms. And there was always a speech given at the beginning that used to be given by Jonathan Rosenberg who ran product for Google for many years. And now it had to be given by somebody. So I'm going to give this speech, now I've got to figure out what the hell am I going to say, what's a good product manager.

**Shishir Mehrotra** (01:07:02):
And as I was going through this, I decided to run this little exercise. So this group of eight product leaders, we took the level guides, we had a level guide for product managers, every company does, and we took it, we printed out a sheet of paper, cut it into little slices, one per level, and we cut off the title and the number and I handed them out and I said, "Can you reverse identify what level you're holding?"

**Shishir Mehrotra** (01:07:22):
Then turns out nobody could do it. And it's not easy to do. The level guide had been kind of added to over time and not really that refined. And so it's full of all sorts of things that were whatever at that time was the priority of the team, they stuck it in a level guide. And so it would say things like, this person can manage a medium-sized project and they interview at least three people a week and they always send the notes out on time and their expense reports are always filed. And it'd be like, oh, that's a director. And it's just whatever we were trying to incent was sort of stuck in this thing. But we noticed that if you took all these sheets of paper and laid them out side by side, you could order them by exactly one statement, which was one that corresponded to scope.

**Shishir Mehrotra** (01:08:12):
And so there's some word in there that was an escalating adjective that mostly correlated to how big is the thing you run. And so we decided, okay, well we're going to standardize. We're just going to focus on making that clear. And so we said we're going to define scope and so that we all use it the same way. And we came up with some stopping points and basically said, you own a feature, you own a group of features, you own a sub area of a product. You own multiple sub areas of product, you own an entire product, or you own multiple products, you own a product line. And that's going to be how we think about scope, go forth and evaluate your teams. We had the next meeting a couple weeks later and everybody comes back upset. It's like, this didn't work at all. Why? What happened? And said, "Well, the search team is super mad at the ads team because search is one product, the entire thing is one product. The ads team, they went and invented all these products, because it's like every little thing.

**Shishir Mehrotra** (01:09:00):
... the ads team, they went and invented all these products, because it's like every little thing you do in the ads platform has a SKU, has a P&L, has a... Because you have lots of products, so [inaudible 01:09:11] worked. The second issue was they said the scope is actually an input, not an output. We're talking to our manager and said, "Well, this person should get promoted. They've managed this huge scope." And then they would say, "But you gave them that scope. We should be judging you, not the person. How do we judge what they're doing with the scope?" It's actually very different. And the third issue was in almost every team, some of our best people were working on things with odd scope. They were risky projects. We didn't yet know is this thing going to work or not work, is Mike canceled. And if we put in place a system that only rewarded scope, we would heavily disincent people from working on these riskier, more creative things.

So we were stuck. And then we ended up set... We went through lots of frameworks. We ended up settling on this one called PSHE, and it comes from old mentor of mine, [inaudible 01:10:01] Clark, who's my boss at Microsoft for a number of years. And it stands for Problem, Solution, How, Execution, PSHE. And I will say it's a... I've tried many times to come up with a better acronym and I have not been able to come up with one. So it's push. That's the word. That's as good as I can get. But here's how... It works good enough. So push, that's all you have to remember. It doesn't roll off the tongue, but maybe... I did better with [inaudible 01:10:28] questions I think, but... So here's how it works. So if you're a junior product manager, what happens? You get handed a problem. You get handed a solution. You get handed the how. "Go talk to this person. Write this document. Run this meeting," so on. And all you have to do is execute, run that playbook, and that's all we expect out of you. You can become a little more senior. We hand you a problem. We hand you a rough solution. You figure out the how. You figure out the, "How are we going to organize this? What are the milestones? How are we going to get it to market? How are we going to do the meetings? What are the rituals?" All those things show up in the H.

**Shishir Mehrotra** (01:11:03):
At some point you become a little more senior. We hand you a problem and you come back with the solutions. You come up and we judge you on the creativity and the effectiveness of the solutions. And at some point you're senior enough that you tell us the problems and you say, "Hey. I know you told me to go work on activation, but actually I think our issue is brand," or, "I think our issue is quality," or, "I think our issue is..." whatever it might be. And that's the pinnacle of this way of thinking about it.

**Shishir Mehrotra** (01:11:27):
Now just back to this picture for a moment, one of the interesting things that happened was that the teams went and they evaluated their teams on these two axes and they end up with this curved line between them. It's not linear as you work your way through. And what happens is early in people's career, they mostly sit at that E point. You get handed a problem and handed a solution, handed a how and you just execute, and they gradually grow in scope. Later in people's careers, similarly, you're at that P level. You just do bigger and bigger products. And the job of being an entrepreneur or CEO or an owner or so on is just do bigger and bigger projects. But in the middle, the slope changes and all of a sudden, it's not really about scope. It's about PSHE. And there's a circle drawing in here for what I like to call the trough of dissolution.

**Shishir Mehrotra** (01:12:14):
And the reason... I'll stop sharing so we can talk about it, but what happens in that phase, and I was talking to the calibration committees about this, the reason we call it the trough of dissolution meant is for the employee, for the person, this is a confusing time. Everything about leading up to this moment from high school and college has been about scope. And at this point you're all of a sudden told, "We're not judging you on scope anymore. We're judging you on this PSHE thing that's very confusing." To the calibrator or to the manager, it's also very confusing because all of a sudden, the difference... The way I would put it is the difference between a level three and a level seven may not be scope. They may do the exact same job. It's how they do the job that matters and here's some language for how they do the job.

**Shishir Mehrotra** (01:12:56):
And so PSHE became a very sticky way of thinking about it. It turns out that this way of evaluating people is actually not that specific to product management. It's really easy to see why you do the exact same thing for engineers and designers and so on, but to pick one that may not be as obvious, I'll pick salespeople. A very common thing people do with salespeople is they evaluate them based on quota attainment. It's the easiest thing to do is take the salespeople and rank them by who hit their quota and who didn't. You go ask the sales team who's the best salesperson, and what you'll realize is they'll say quota attainment is just a signal for how good you negotiated your quota and picked the right territory. Really, you want to know who's a best salesperson, they say, "Well, so and so, I mean she can sell anything and she can be in the region that's growing or the region that's shrinking or the new product or the old product or..."

And if you think about that terminology, it's very similar to PSHE thinking. This is the person who can come into a new space, identify the right problems and solve them. That's what makes a really great salesperson. So it could become my framework for evaluating talent in all sorts of ways. And you might recognize a pattern of being a great P thinker is very correlated with being good with [inaudible 01:14:06] questions. Can you spot the right problems? It's very similar to can you spot the right questions? Can you decide what's important? And so that's been my main framework for value.

**Lenny Rachitsky** (01:14:15):
Wow. There's so much there. A couple quick questions. Is this basically your calibration ladder framework for PMs at this point? And then is this also just like your interview guide, just interview at each of these pieces to level the person?

**Shishir Mehrotra** (01:14:29):
Yeah. So it's definitely how we do. Our version of leveling is PSHE, and we use a set of Radford levels. Radford has this really interesting way of describing that as you grow in a profession... He uses the analogy of someone, of a sailor and that a junior sailor is learning to tie knots and then you gradually can tie all the standard knots and then you can tie the advanced knots and so on, and so you work your way up and at some point the way you're judged is you invented nylon and there's list between there. It's like a way to evaluate every role. It's very similar to PSHE. And so we look at a similar list. But yeah, basically all of our roles are evaluated on something that corresponds with PSHE.

**Shishir Mehrotra** (01:15:17):
And in terms of interviews, yeah, you look for the same thing. And by the way, I should say interviewing is one part of this. And you talk about interviewing. You talk about calibration. There's one other really important one which is reference checking. And I think the best way to assess PSHE is actually through references. And so the most important guide we write isn't the interview guide. When we call this person's references, what do you ask to actually get at these questions? Because people can often confuse them.

Just to pick product managers as an example. We all know some really amazing H level product managers. And one of the reasons, one of the hallmarks, of an H level product manager is that their counterparts usually love them and they'll say things like, "Oh, my gosh. The person runs such efficient meetings and all the communication is always clear. [inaudible 01:16:07] always buttoned up. Execs know what we're doing. The market knows what we're doing. Sales team know what we're doing." That's great H. And then you'll ask them a question about, "Okay. So when you're deciding which problem to solve, who is the leader of that? And are they picking the right problems? Or when there's a hard problem, who is regularly coming up with the best solutions for them? Who do you turn to? Who is the most obvious person to turn to say, 'This is really hard problem. What's the right solution?'?"

**Shishir Mehrotra** (01:16:31):
An amazing number of people will tell you, "No, they run a great meeting but actually solving the problem, designer does that," or, "What are the problems? No. The CEO tells us what to do. That's not what this person's really good at. Yeah. I'm not sure we're solving the right problem, but boy, we run a great meeting." And it's not meant to diminish any of that. I mean, we spent a while talking about rituals, which mostly happen at that H level, so I don't think it's unimportant, but it's actually quite hard to assess in an interview but incredibly easy to assess in a reference check. And I think getting good at that is really important.

**Lenny Rachitsky** (01:17:01):
You may have mentioned this, but what's the question there? Is there a question that you could recommend?

**Shishir Mehrotra** (01:17:05):
The absolute ideal case is you get to the person that you're doing the reference check with and you don't even tell them who you're asking about and you just say, "When you think of your teams, who is best at..." And this obviously only works in cases where you have a pretty deep relationship with the person you're getting referenced from and so on. So you can't always do that. But ideally you want to mimic that behavior. One of the things I think that's hard about reference checks is people have... They have perverse incentives in a reference check. They're not really... Some of it is for good reason. Some of it is for bad reason. People generally don't like criticizing people and they also feel judged themselves and they don't want... There's legal reasons that things can blow back and so on.

**Shishir Mehrotra** (01:17:55):
And so what I try really hard to do is to draw contrasts. So you try to say things... There's a couple of techniques I've used for this. In the best case you say, "I'm not going to even tell you who I'm asking about, but when you think about this team who regularly identifies what problems they should focus on? Who is most reliable at coming up with the solutions to the hardest problems?" And you work your way through it. The other way I like to do it is to provide contrast to give the person an out to not make it obvious to them that I have this ranking. And so I'll say things like, "When you think about this person, and I'll give you four different personas. Someone who's regularly coming up with the problems that the team should be focused on. Someone who given a set of problems is constantly solving them in this really creative way. The person that is just really good at getting a team moving. Or the person who can take a playbook and execute it with high precision and high quality and stuff."

**Shishir Mehrotra** (01:18:47):
And I won't tell them that I have a qualitative judgment that one is better than the other, but you want them... Because you just want your reference check to talk and you want them to say what's on their mind of... You want to give them an opening to not feel like they're judging. Obviously, another question I always ask people is, "Would you hire this person again? Or how excitedly would you hire this person again?" I always ask them, "What questions should I have asked that I didn't?" Another key technique for reference checks is you just need people to... Once they start talking, they'll reveal what they really feel and often the little things will come out. But for this particular thing, if I want to know where they stand on this axis, don't tell people what you value. By the way, I will say I value P over S over H over E. I've seen many companies that would reverse that scale. And by the way, there's industries where it's very required. You don't want a bunch of people running around and constantly telling you to solve some different problem. I just need people that can do this job that we give them super, super well. And it depends a bit what your personality is and what your company's culture is and so on. So it's not actually that unbelievable that I might value the E over the P. Anybody who knows me, that's probably not true, but for a reference check, you can probably not give that away.

**Lenny Rachitsky** (01:20:04):
Wow. That was gold. I hadn't heard these reference check insights. And so I'm really happy we got to that. Maybe one last question on reference checks. How often do you find that a reference check leads to you not hiring someone, just ballpark? Or is that hard to say?

**Shishir Mehrotra** (01:20:19):
All the time. And I will say I try to do them as early in the process as practical if it's possible. Because I think it's actually the worst feeling for an interviewee to go through a process and then get dinged at the reference check stage. It's a really crappy experience for the candidate. And obviously you have to be careful about not ruining anything for them. You can't always do the reference check as early as you can. When you're inside a company, when you're inside Google or Facebook or so on, you can generally do them even before you enter. It's an expectation of we're going to hear a little bit about people in that process. And I generally value the reference check over interview signals. If I had to stack rank in interviews what is the best signal, the reference check is the top of the list. Those people, they worked with this person sometimes for years, their knowledge, what you're going to get out of 30 minutes of artificial scenarios, it's just never going to compare with what a good reference check will give you.

**Shishir Mehrotra** (01:21:12):
And then the second best thing I value is anything that feels like a real work exercise, which is also... Even that is hard because some people, their skillset doesn't naturally lead to a compressed time work exercise. But we do a thing for basically all our roles where at the start of the interview loop, the candidate presents to everyone on the loop and we invite some other people in the company to attend too. For a while it was open the whole company. Now we're big enough where that's not practical. But the original is very simple. At the beginning of the loop, the person presents. And generally for most roles, there's a exercise that they do, but about half the time is spent on them presenting whatever they want. They can talk about themselves. They can teach us something and then another half is we've given them a prompt, something that we want to direct.

**Shishir Mehrotra** (01:21:58):
One of the things that I think when you're doing interviewing, one way to think about it, I call it home court, away court, neutral court, you want interviews to balance in all those different spheres. So a common mistake people make is they do all questions in home court. "Hey. If you're joining Airbnb, what would you do about X?" And what is the candidate going to say? They clearly can't be as thoughtful as you. They haven't thought about it nearly as much as you have. So really what you're testing is, "Did they come to the same answer that we did?" which is a pretty crappy way to judge someone. Home court questions tend to be tough. You have to be very careful about how you do them. Away court questions can also be tough. This person, you say, "How did you solve this problem?" And they say, "Well, we did this thing." And you don't really know was that problem actually hard? Was it somebody else was telling them what to do? Are they just not telling you the whole story of what happened and so on?

So you try really hard to make... Most of our interviews are done neutral court. So the vast majority [inaudible 01:22:54] teleporter question is a very neutral question. You don't have to know anything about Coda. I don't have to know anything about Airbnb or wherever. I can just ask you this question. But this one thing, the presentation is the away court question. You now have an opportunity to talk about yourself in this new way. And it's super interesting what people do. I mean, I've seen people use that time... I often tell people it's the brag session, but this is like... And for product managers... We do it for every role, but it's like recruiters, salespeople, marketers.

**Shishir Mehrotra** (01:23:23):
We tell them, "We're going to go through this whole interview process. And at most companies you talk to six different people and six little segments. And at the end of the day you say, 'Gosh. I really wish they had learned this about me.'" And I tell them, "Don't leave this with that feeling. What do you want us to know about you? All our questions are... In some cases we're trying to lower bound you, like, 'How bad could this be?' I want you to upper bound us. I want you to tell us what's really amazing here." And so we'll have the presenter go through that process. And what they choose to talk about is very important. How they choose to present it is very important. But I do it as upper bounding. But if I had to stack rank in interviewing, what do I look for? Reference check at the top, work, product and presentation next, and then all the interviews. When they disagree, that's the order we judge.

**Lenny Rachitsky** (01:24:12):
Shishir, I feel like you have five books in you that you need to write on so many of these topics. This is such good stuff. I wish I could keep going. I know you have to run. So we have this final lightning round. So I'm going to ask you five questions. There's one at the end I didn't tell you about ahead of time, so it's going to be a surprise. And so I'm just going to ask you these quick questions. Let me know what comes to mind. Okay. First question, just what are two, three books that you find that you recommend most to other people? Oh, pulling out the bookshelf.

**Shishir Mehrotra** (01:24:40):
Pull up [inaudible 01:24:40]. One I already said and we talked about. So this would take two of the slots. The next one on my list is Switch by Chip and Dan Heath, How to Change Things When Change Is Hard. The other one, this is probably a surprising one, it's called Understanding Comics by Scott McCloud.

**Lenny Rachitsky** (01:24:53):
Wow.

**Shishir Mehrotra** (01:24:54):
Super fun book. It's a comic book about comic books and you don't have to like comic books at all to love this book. It's basically... The starting point is over time communication has drifted at two extremes. So one is we've gotten very good at written form and the other is we've gotten very good at art, single pieces of art. And comics are the hybrid. They are drawing mixed with writing. Sometimes I think he calls it... Oh, God. He had a good term for it that I'm now forgetting, but he describes comics really well and he goes through the actual reasoning of why comics are structured the way they are. And one of the reasons it's so important to me is, and you could probably tell from how we talked about different things, is often a diagram that crystallizes something. The art of storytelling, diagramming, so on, I think is so critical for basically any part of life. And this book, it's so thought-provoking on how to do it. Understanding Comics by Scott McCloud.

**Lenny Rachitsky** (01:25:48):
Understanding Comics. Wow. Good choice. Okay. Favorite recent movie or TV show?

**Shishir Mehrotra** (01:25:52):
Okay. Couple that come to mind. Only Murders in the Building is a really fun one. And my family got really into the Marvel series during the pandemic. And so WandaVision, if anybody hasn't seen that. If you're not into superhero stuff and so on, which I'm not really that... I'm actually more of a DC comics person. I like Superman. But WandaVision is one of the best pieces of art that I've seen done in a very long time. Very well done show.

**Lenny Rachitsky** (01:26:19):
I feel with that show I had to... I gave up initially. I'm like, "What the hell is this? What is going on?"

**Shishir Mehrotra** (01:26:19):
I know.

**Lenny Rachitsky** (01:26:23):
And then it gets good.

**Shishir Mehrotra** (01:26:24):
It gets good. Yeah.

**Lenny Rachitsky** (01:26:25):
And on the flip side, Only Murders in the Building. I don't know if you've seen the second season yet, but I'm just like... I'm done with it. I'm just tired of it now. I don't know what they're doing.

**Shishir Mehrotra** (01:26:33):
Oh, yeah? We're only one episode into the second season, so we'll see. Maybe we'll give up too.

**Lenny Rachitsky** (01:26:33):
Good luck. Okay.

**Shishir Mehrotra** (01:26:40):
The preseason was so good. [inaudible 01:26:43]. And it's all about podcasters.

**Lenny Rachitsky** (01:26:45):
It's like so meta around podcasters. Oh, man. Okay. Good segue. Okay. Favorite interview question/ you may have already answered this.

**Shishir Mehrotra** (01:26:53):
The teleporter one is definitely my favorite. My second favorite one, if I was going to give you a different one, is I have a series of questions around... Let me pull it here so I give you what the real question is, but is basically around a dashboard prompt. And the starting point of the question is, "Pick a product." I [inaudible 01:27:15] say, "Your favorite technical product." And the constraint is, "It can't be something that you built, worked on or competed with. It's got to be in the space that you're not an expert in." And I generally ask people why, which is actually a really interesting passion test. And then I'll ask people, "Design the one- page dashboard for that product. If you're the CEO, general manager, whatever, you run that product, what's on the dashboard? Why?" It's an interesting [inaudible 01:27:39] question, E type question of like, "Can you tell what's important for this product or not?"

**Shishir Mehrotra** (01:27:43):
And then I ask them to basically redesign the product. And the way I do it is, "You've been hired by a competitor to design a me too version of product. I'm going to leave aside for a moment that why you would want to build a me too version. What is the bare minimum of what you need to build?" And then I tell them, "You ran out of resources. You get a quarter of the scope and a quarter of the..." Or, "You get quarter of the time and a quarter of the team. What do you actually build?" And then I get down to the other side of, "You've decided you can differentiate in only one place. What do you do to differentiate?" And so there are a series of questions that are basically a form of PSHE, but just formed around a new problem space that lets people wander a little bit. I've seen some really amazing answers to that.

**Lenny Rachitsky** (01:28:27):
There's also a lot of [inaudible 01:28:28] question elements to this sequence. Wow. Excellent. Okay. Who else in the industry do you respect as a thought leader? Who comes to mind?

**Shishir Mehrotra** (01:28:37):
Other than you? I have to ask. Present company excluded?

**Lenny Rachitsky** (01:28:40):
Yeah. That's great. [inaudible 01:28:41].

**Shishir Mehrotra** (01:28:43):
By the way, your newsletter is one of my top reads.

**Lenny Rachitsky** (01:28:45):
Oh, wow.

**Shishir Mehrotra** (01:28:45):
I think that yours and Ben Thompson from Stratechery are two of the ones that... I think you both have a very natural instinct for writing and synthesizing things that people are feeling with a clarity that's really helpful. So I really appreciate that.

**Lenny Rachitsky** (01:29:05):
Appreciate that.

**Shishir Mehrotra** (01:29:06):
I mean, I think the rituals process has exposed me to some really amazing leaders. Talked about Ariana. I always learn a lot when I talk to Ariana. [inaudible 01:29:14] has contributed a bunch. I think he's really helpful and is... And I can't believe he basically had no Twitter followers at the beginning of the pandemic. And his tweet are just total gold and so insightful and well put together. Fidji Simo is someone that I learned a lot from. She now runs Instacart. Daniel from Spotify, Daniel Ek. I think he's got this really unique way of thinking about the world, and he's also one of the few people that can hold a very long-term view and a very short-term view at the same time. Fantastic ethics. I'd also say my entire board, Reid, Reid Hoffman, [inaudible 01:29:51], Mamoon Hamid, Quentin Clark, Sarah Guo. I think they're all amazing and I'm super lucky to have a group of people I can call with questions.

**Lenny Rachitsky** (01:30:00):
Awesome. Someone's going to have a lot of work on these show notes. That list. Okay. Final question. What's your go-to karaoke song or dance move at a wedding?

**Shishir Mehrotra** (01:30:09):
Karaoke song is If I Had $1000000 by the Barenaked Ladies, and it's a... If people don't remember the song, part of the reason it's my favorite is I'm a very mediocre singer and you don't have to be that good a singer and everybody can sing along so you can bring everybody into it. And it's just such a fun song, If I Had $1000000.

**Lenny Rachitsky** (01:30:28):
You're as thoughtful about your karaoke songs as you are about everything else you're doing. Shishir, thank you so much for being on this podcast. You've set a really high bar for CO guests, so we'll see who comes up next. Two final questions. Where can folks find you online if they want to reach out or learn more? And how can listeners be useful to you?

**Shishir Mehrotra** (01:30:44):
Okay. I'll give the same answer to both. Well, I'm easy to find, one of the benefits of having a not very common name. It's easy to find me on basically every platform so you can find me on Twitter. It's easy to DM me, Shishir@Coda.io. It'll get to right to me. But in terms of being useful to me and also finding me, I would highly recommend joining the Rituals of Great Teams Braintrust. And I think it's a pretty fun experience to get a chance to contribute to a book like that. And hopefully if you've made it this far in the episode, then you probably are interested. And so I think you'll find it interesting. And I'm having a lot of fun with the people in that Braintrust.

**Lenny Rachitsky** (01:31:18):
Amazing. I'm definitely going to join. Thank you, Shishir.

**Shishir Mehrotra** (01:31:22):
Yeah. All right. Thank you so much, Lenny. That was really fun.

**Lenny Rachitsky** (01:31:24):
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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## [12/20] The art of building legendary brands | Arielle Jackson (Google, Square, Marketer in Residence at First Round Capital)

**Arielle Jackson** (00:00:00):
So over time, a word can come to mean something that is beyond what that actual word means. Like Disney means magic today. Volvo means safety. Those names are not good. If I just put it in a spreadsheet or one of those lists, no one would pick it. So that's kind of what I mean, that the name is just part of the overall marketing or the overall brand and a bad name with a really great company with great company strategy, great marketing is going to be great over time. And a good name is just going to help you, but I don't think a bad name is going to kill a good company.

**Lenny** (00:00:42):
Arielle Jackson spent nine years at Google, where she helped grow Gmail in its early days, taking it from just a side project to a product that is now used by hundreds of millions of people all over the world. Then she went on to Square, where she was one of the first marketers and helped launch and scale the growth of Square reader. She's also worked with over 100 early stage companies, helping them nail their brand and marketing efforts, including Patreon, Loom, Front, Eero, Maven, Sprig, just to name a few.

**Lenny** (00:01:12):
**Ashley** (00:01:49):
At least 40%.

**Lenny** (00:01:51):
And how many of them screw that up? And what happens when they do?

**Ashley** (00:01:54):
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 CSV importer doesn't work right, which is super common, considering customer files are chock-full of unexpected data and formatting, they'll leave.

**Lenny** (00:02:13):
I am 0% surprised to hear that. I'm consistently seeing that improving onboarding is one of the highest leverage opportunities for both signup conversion and increasing long-term retention. Getting people to your aha moment more quickly and reliably is so incredibly important.

**Ashley** (00:02:28):
Totally. It's incredible to see how our customers like Square, Spotify and Zuora are able to grow their businesses on top of Flatfile. It's because [inaudible 00:02:38] data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:02:45):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny.

**Lenny** (00:02:53):
**Arielle Jackson** (00:04:01):
Thanks so much for having me. It's great to be here.

**Lenny** (00:04:03):
It's absolutely my pleasure. I've read so much of your writing online. You've done a lot of writing, which I found really helpful. And so I'm really jazzed to be digging into all kinds of really good stuff. Before we get into some of the meat, just a couple questions that I had in my mind. You've worked with so many amazing companies, Google, Square, Loom, Patreon, Front. So many others. I don't want to keep going. What's been either your favorite or most unusual project that you've worked on?

**Arielle Jackson** (00:04:35):
Gosh, it's like asking me to choose my favorite son. I'm like, gosh, I can't really like pick one.

**Lenny** (00:04:40):
That'll be the next question.

**Arielle Jackson** (00:04:41):
I would probably say that my favorite project, and this is because they get reminded of it on a daily basis was working at on the Square stand at Square. It was the first time I ever worked on hardware and our joint Square was 140 people. We had no marketing function. We had a couple marketing people. We had no product managers and the hardware team was running the show on launching this new product that was supposed to get us up market into brick and mortar.

**Arielle Jackson** (00:05:05):
And anyway, I was running event marketing at the time and giving away a bunch of those readers that you stick into a phone for free and having a lot of small merchants use. I volunteered to run the launch of this product as a product marketer for the first time. And it was just so fun, doing everything from positioning it, figuring out how we were going to talk about this beautiful new piece of hardware that would turn your iPad into a real point of sale.

**Arielle Jackson** (00:05:31):
We had people fly around the country and get cool coffee shops and brick and mortar businesses seeding it so that they would all use it. We had I think 15 Metro areas covered with the coolest coffee shops and donut shops and everything at launch. And you know, there was a lot of fake it till you make it. I was negotiating a deal with Best Buy in the Apple store. Never done anything like that before.

**Arielle Jackson** (00:05:53):
Designing packaging was really awesome. There was just so much to it launching a physical product. And at the time it was at a pretty high price point for a company that had always had one free product and helping that company go up market. And I remember I was 30 something weeks pregnant when we launched. We got all the blue bottle stores to use it. And we had this launch event where Jack, our head of hardware, Jesse unveiled this product at the blue bottle in Mint Plaza. And I was super pregnant and super proud. And I still get kind of excited every time I pay on one of those, which is all the time.

**Lenny** (00:06:30):
Super pregnant and super proud. I love it. And that product that was the POS stand, the iPad thing that you kind of swivel and sign.

**Arielle Jackson** (00:06:39):
Yeah. And there's been new versions of it since, there's a contactless version of it, and there's one with an integrated screen that I think is Android based, which you don't have to have an iPad, but that product's still around. I still pay on that original Square stand all the time. I drink a lot of coffee. Those independent coffee shops around LA. So they're all still using it.

**Lenny** (00:07:01):
We're going to talk about positioning a bunch, but while we're on the topic, what was the positioning of that product while we're talking about it?

**Arielle Jackson** (00:07:07):
Yeah, so at the time Square was mostly used by farmer's market vendors and event vendors. I made jewelry in a past life and that's how I got to Square was being one of those vendors. And the positioning was really that it was for brick and mortar businesses, particularly quick serve coffee, donuts, sandwich shops that kind of quick serve brick and mortars. And it was up against your ugly old point of sale. Your cash register effectively. That was our foil. And the benefit was turn your iPad into a point of sale. And the differentiator was about one unified experience that you can do everything you can on your cash register and more, and you'd be proud to have it out on your counter.

**Lenny** (00:08:01):
So you said that you were creating jewelry and that's how you got into Square to work on this product. I need to hear more about that.

**Arielle Jackson** (00:08:08):
Yeah, sure. So I was working at Google before Square and I'd always had this hobby of making jewelry and I used to sell my jewelry in a few different like boutiques around San Francisco and LA. It was a very small side hustle, but it was my creative outlet. And I sold at craft fairs around Hanukah/Christmas time. So I used to sell and just take cash. And then I got a Square reader and I sold at a craft fair that year. And it was awesome. That Square reader, it helped people buy more, it helped me sort of look cool. It was just really great to accept credit cards. I'd never done it before.

**Arielle Jackson** (00:08:49):
I used to take PayPal invoices and be on my computer and send someone an invoice and they'd get it. It was painful. All the reasons that people use Square, I experienced it. And two people I knew from Google, Megan Quinn and Kyle Dink had gone to Square from Google. And so after I had that experience, I think I sent them both an email just being like, this thing's fucking awesome. I make jewelry. It was great. I sold I think it was 50% more than I did last year because I accepted credit cards and I can't remember which of them wrote back first, but they were like, come interview. And so that was basically how I ended up at Square.

**Lenny** (00:09:27):
Wow. I bet that helped you a lot through the interview, actual have personal experience.

**Arielle Jackson** (00:09:32):
Having been a merchant, I think it helped me understand the small merchant that initially we were marketing to.

**Lenny** (00:09:38):
And so today you are marketing expert in residence at [inaudible 00:09:45] capital. I was going to ask what does that mean and what is it that you do day to day these days?

**Arielle Jackson** (00:09:51):
Sure. So after I left Square, I went to a tiny startup that was seven people. They were funded by First Round and I helped them with everything that a tiny startup that's trying to grow needs.

**Lenny** (00:10:06):
What startup was that?

**Arielle Jackson** (00:10:06):
It was called Cover. They were acquired by Twitter. It was an Android app that could get you the right apps at the right time based on where you were by changing the lock screen on your phone. And so that company and that experience of working at this tiny startup that was seven people, I really liked it. And then they got acquired by Twitter, but I had just left Square. So I decided not to join Twitter with the rest of the team. And instead I just decided I was going to help a bunch of other small startups. And I emailed a few friends from past lives who had small startups, which was like, Hey, I'm not going to Twitter with the rest of the team. You do need marketing help. And every single person wrote back and said, yes. And that's basically how I started consulting.

**Arielle Jackson** (00:10:49):
I guess it was about eight or nine years ago. At the same time, First Round had reached out and said, hey, who did you use for marketing comps for cover? And I got connected with Brett from First Round and he's like, would you help our companies? And we did a three month project for one day a week, nine years ago. And I'm still there. I work halftime at First Round. So I do everything I do for other companies, but for First Round companies on First Rounds time.

**Arielle Jackson** (00:11:17):
So the way it works is if you're funded by First Round and as part of your onboarding, we offer a lot of value add services and I'm one of them. And those services can be everything from, we have someone who's really good at compensation and HR stuff and we have someone who will help you with pricing and I'll help you with marketing. And what that means when you're a seed stage startup is everything from naming to positioning, to developing a brand identity, a website and your initial launch, and eventually hiring a marketer. So that's sort of the bread and butter. That's what I like working on anyway. So it's a good fit because we invest in a lot of seed stage companies at First Round, I get to help almost all of them.

**Lenny** (00:11:58):
That's an excellent segue to what I wanted to get to next. What I want to do in our chat is cover three broad topics. Things that I know are very near and dear to your heart, naming for products and startups, your brand development framework and how to hire marketers. Does that sound good?

**Arielle Jackson** (00:12:15):
Awesome. That's what I like to talk about. So yeah, let's do it.

**Lenny** (00:12:19):
Let's do it. Surprise, surprise. Okay. So with naming, I've actually heard from a few founders that you were really helpful to them in naming their startups. Folks that have maybe been on this podcast that will go unnamed. So for founders trying to come up with a name for their company or their product, two questions. What makes a good name for a product or a startup, and then just how do you come up with a great name?

**Arielle Jackson** (00:12:44):
I love naming. I think I've named just over 30 companies at this point. And actually when I mention how I got into consulting when I emailed some friends and asked them if they needed marketing help, I think I'm allowed to talk about this one. So one of those companies was some friends from Google, Adrian and Carl. They had left Google, gone to Facebook and then started a company it's now called Seesaw. It's an ed tech company. That was the first company I named post Google Square, all of that.

**Lenny** (00:13:09):
It's an awesome name.

**Arielle Jackson** (00:13:10):
It is an awesome name and I'll use it as an example. So seesaw is a ed tech company. They had a really bad name before that and we did this whole naming process and ended with that name and why I think that's a good name is when I say Seesaw, you don't really know what it is, but when I tell you, oh, it's this ed tech company and it's an iPad app and it helps the work that elementary school students do go between the teacher, the parents and the student. And you're like, oh, well, Seesaw makes sense for elementary school, it's something that goes back and forth. It has that sort of nostalgic feel. And it makes sense that it's an ed tech company.

**Arielle Jackson** (00:13:48):
And I personally tend to like those kinds of names that are suggestive or evocative, where when I tell you what the company does, you're like, oh, that makes sense. But it's not that what the name is tells you exactly what the company does. So that's an example, I think of a good name. I don't know, during COVID and when my older son's school was closed and they all used Seesaw and I got to tell my son, oh, that's my friend's company and we named it back in the day. And he was like, oh, that's cool. That name makes sense.

**Arielle Jackson** (00:14:21):
That's the reaction you want. It also has a little bit of emotion to it. It has some nostalgia. It's fun to say it's short, it's memorable. I think all of those things make a good name. Another company that has a good name that you and I have both worked with is Maven. So they're a First Round company. Gogan has talked about this publicly. We named that company together. Maven is a Yiddish word that means one who understands and it means specifically one who understands because they've done something, they've acquired the skills or knowledge over time.

**Arielle Jackson** (00:14:58):
And I just think that's such a cool name for a platform that allows X operators or current operators to teach their skills to other people through cohort based classes. You want to be a Maven, instructors are Maven's, it's short, it's easy to say, when I tell you what that company does, that name makes perfect sense. So I tend to like those [inaudible 00:15:17] of names myself, but I also, I don't know, I like other kinds of names for other kinds of products too. I think it really comes down to what is your product? What is your company? What is the name trying to achieve and really getting clearer with those criteria. So we can talk about the criteria that always apply, the criteria you might add and a process to get there.

**Lenny** (00:15:38):
That sounds great. Yeah. I'm really curious about a process. If one exists, that'd be really cool. So another question in my mind is just some names are just nonsense words like Yahoo and I don't know Google, I guess. What's your take on that as a name, that approach?

**Arielle Jackson** (00:15:51):
Yeah. So words like that are empty vessels, they really don't mean anything. If you think about the name Yahoo, it's actually like really silly. It's like Yahoo. I always hear it like that. Google has a meaning for people in the know with the one followed by as many zeros. It's like a big number and it's a misspelling of that. So that one's a little less silly to me than Yahoo. My take on empty vessel names is they can be really memorable and they can be evocative of the emotion, but you have to do a lot more marketing work over time to make it mean something.

**Arielle Jackson** (00:16:25):
So if I say Yahoo today, we know it's that search engine we use before we all switch to Google and we have the purple color in our head, and we think about what it meant at the time that we might have used it, but it took a lot of marketing dollars and a lot of time for that word to be in that. So they're doable. I worked on a company Eero. That has kind of what is almost an empty vessel name. Eero is for Eero Saarinen who was a designer. He did like these really beautiful buildings, architectural buildings. And then also some tables. You can get a Saarinen and table at Design Within Reach, but that name, nobody knows that unless you're in the design community. And so that name is effectively an empty vessel and they have to spend a lot and be consistent about making that [inaudible 00:17:16] mean a wifi system.

**Lenny** (00:17:17):
I want to get to the process, but another question is why is it important for the name to kind of connect to the company and what they do? Is that just it feels nice to people or is there some kind of a bigger reason?

**Arielle Jackson** (00:17:30):
Yeah. So it doesn't have to, and examples like Eero and Yahoo, it doesn't. Even if you think about Apple, it doesn't. Apple has nothing to do with Apple computers. It's a word we all know. There's a lot of words where there's no meaning behind it. If there is a meaning behind your name, your name is doing a little bit more of your marketing work for you. So if your name is Internet Explorer, RIP, I know exactly what you do.

**Arielle Jackson** (00:17:56):
If your name is Chrome and you're a designer on the web, you kind of might be like, oh, that makes sense. That's the area around the browsing window. If your name is Firefox, I have no idea what you did. You just took two words and put them together and made something up. And now you have to spend, and you have to be consistent over time in making that word mean something for people. But all three of those browsers were successful at a time. And I don't think the name had anything to do with Internet Explorer's demise.

**Lenny** (00:18:25):
Got it. So it's kind of ideally you can find an easy mode. If that doesn't work, then you go hard mode. You come up with your empty vessel name and then you just have to do a lot of work.

**Arielle Jackson** (00:18:33):
That's my personal preference.

**Lenny** (00:18:35):
Okay, cool. That makes sense.

**Arielle Jackson** (00:18:37):
My personal preference is if you think about there's descriptive names, the Internet Explorer, there's suggestive names like Chrome, then there's evocative names, which I would say Seesaw and Maven fit into there where they're like in between suggestive and evocative, and then there's empty vessel names or fanciful names. There's a spectrum. And when you do your brainstorm, we can talk about this in the process, you want to think across all of them, but you might have in your naming brief, we want a suggestive name, or we want a descriptive name. You might go into it with that. And so there's times and places for all of those names across the spectrum. My personal bias is I tend to like suggestive names.

**Lenny** (00:19:16):
Makes sense. Okay, let's get into it. What should teams do when they're trying to name something?

**Arielle Jackson** (00:19:22):
Yeah. So the first thing is to do your product positioning. I really believe that positioning dictates so much of your marketing and should always be the first thing you do. I had a student in my last class that I taught through Maven. I teach a class on brand strategy and he was I think a second or third time founder, who had never taken a class on brand strategy. He worked really hard. He was awesome. Anyway, at the end of the class and you kind of do this closing thing. And he goes, I'll never write a line of code without doing positioning first. And that was music to my ears. I think positioning comes first, but in any case, you do that first, and we'll talk about that in a little bit. And then you write a naming brief and it's really simple.

**Arielle Jackson** (00:20:07):
What are you naming? Are you naming a company? Are you naming the product? Are you naming both? Usually if you're early stage company, you're naming both and they're going to have one name because you don't want people to have to remember two things. What do you want the name to communicate? So in that example of Seesaw, we wanted it to communicate young childhood. In the example of Eero, we wanted it to communicate design, being designed forward. It can be whatever you want it to communicate. What do you want to avoid? We don't want it to sound like this competitor, or we hate this word or whatever you want to avoid. What are the names of competitive and related products? And then are there other considerations? I worked with another First Round company that was operating in China.

**Arielle Jackson** (00:20:53):
And one of the considerations was this has to be pronounceable for a native Chinese speaker. That's a very valid, additional consideration. And then there are seven criteria for names that always apply in my opinion. And you could add additional ones, like that Chinese speaking one would be an additional one. The seven are trademark, which is kind of obvious, can you use this? Are you violating someone else's trademark? And the second step with trademark is, do you need to proactively protect the name? Domain availability, so everyone gets hung up on getting a.com like maven.com got maven.com. It was an arduous process that Gogan wrote about on Twitter. But these days, you don't necessarily need the.com. Square operated on SquareUp for very, very long time. Lots of companies are operating on variants of a .com. So domain availability, distinctiveness. Is it memorable?

**Arielle Jackson** (00:21:51):
Is it sound like someone else's name? That's I think one of the most important ones, just is it different and distinctive? Is it timeless? So there's a lot of naming trends. If you tell me Optimizely I could tell you what year was the company formed when it ends in LY. If you tell me a word like Flicker, I can tell you what year it was, because that was the naming trend to remove vowels. So I generally stay away from naming trends, because I want your company named not to sound dated in 10 or 20 years. The last one is it's kind of related to that. What we talked about in the brief, what do you want the name to communicate? Which is the name reflective of your key messaging or does it somehow suggest an emotion or feeling that you're trying to convey, and then sound and ease of pronunciation.

**Arielle Jackson** (00:22:44):
Is it fun to say, is it easy to say, how is it to spell? We almost named a First Round company a while ago Lattice which is now a different company that's doing quite well, but we didn't name it that because this was a company that was B2B sales was going to be their main channel. So they're going to be people on the phone being like, hey, I'm calling from Lattice and we went through this exercise and we're like lettuce? It's not so easy to say and spell. So we actually didn't name the company that and went with something else. But there's a company now doing quite well.

**Lenny** (00:23:16):
You think that was the right move?

**Arielle Jackson** (00:23:18):
I don't know. I always say a good name is only going to help you, but a bad name won't hurt a good company. So I don't really feel-

**Lenny** (00:23:25):
Interesting. Good to know. Yeah. Keep going.

**Arielle Jackson** (00:23:27):
And then the last two are appearance. So there are some names that just lend themselves really nicely to visual design and they have to do with how tall the letters are and is their symmetry and if you give this to designer, making a logo just so awesome and cool and fun and then length. So a lot of people, they want to name like Square and Stripe and these one syllable names, but a two syllable or even a three syllable name can often be more memorable.

**Lenny** (00:23:57):
lennysnewsletter.com. Shoot.

**Arielle Jackson** (00:24:00):
Yeah. Well, so you got the Lenny part with the two syllables is generally a nice sweet spot.

**Lenny** (00:24:07):
Sweet. Have you put out a template or anything that folks can find to do this? Or should they kind of listen here and take notes?

**Arielle Jackson** (00:24:15):
Yeah, there's an article on the First Round review called Positioning Your Startup is Vital, Here's How to Nail It and all those criteria and how to do naming is actually in that article.

**Lenny** (00:24:27):
Awesome. We'll put that in our little show notes. And then as you go through this, is this a binary thing or you kind of rate each of these categories one to five?

**Arielle Jackson** (00:24:36):
Yeah. So the way I do it is I apply the criteria after we do the brainstorm. And then we do red, yellow, green on each of those criteria just to weed out ones that are not doing well on any of those. Got it. And then you add your own criteria. So the next steps the brainstorm. I'm going to go fast through this.

**Lenny** (00:24:55):
Yeah. I was going to ask you about the brainstorm. I'm excited to hear this.

**Arielle Jackson** (00:24:57):
Yeah. So the way that I run a naming process is I like to first do positioning and then I set up an hour with the founders and me and ideally a couple other people who are interested, but disinterested. So I'll bring a writer from the First Round team or the founder has a friend who's a linguist or the founder has a friend who speaks four languages. We like those kind of people to be in it if possible. And it's generally five to seven people in a brainstorm. And the idea is we spend one hour, I set it up beforehand and we try to come up with hundreds and hundreds of bad ideas and a couple decent ones that are worth exploring more. And the brainstorm is two parts. The first part is based on words in your positioning statement.

**Arielle Jackson** (00:25:40):
So we take all the meaningful words out of your positioning statement is the warmup and we run synonyms, antonyms, free associations, other languages, whatever we can do off of those words. And so if your words in your positioning statement are related to what that you do, which they very well should be, that's a great way to just come up with hundreds of words really quickly. And then the second step is a thematic brainstorm. So I pick between seven and 10 themes, you can think of them like Jeopardy themes. So it's like, I don't know, okay, so there was an-

**Lenny** (00:26:11):
Source.

**Arielle Jackson** (00:26:11):
... AI. Yeah. It was like an AI tool for strawberry picking and the themes would be the history of strawberry farming or botany 101, things that are related. You could do like last names of famous farmers, think about how did Tesla get their name? They probably did last names of people related to electricity, and that's such a great name, so thematic brainstorm. And then that's usually a little more fruitful. And we do the same thing, free association, all that.

**Arielle Jackson** (00:26:40):
I spend some time afterwards on Wikipedia and the internet and actually finding words words. Also love the library, check out books sometimes and just read books on the topic and just write down the interesting words that come up. And anyway, so then I give them back a short list. The short list is around 10 to 25 concepts that are ideas that are worth looking at further. And from there narrow it down based on the criteria and the red, yellow, green, we come up with three to five, don't come up with one because you might not get it for trademark, and it's really sad when you get really attached to one and then you can't use it. So yeah, three to five top contenders. And then you go through trademark process domain and kind of go from there.

**Lenny** (00:27:23):
That was amazing. If you're doing a startup name versus a product, is the process any different or is it basically the same?

**Arielle Jackson** (00:27:29):
No, same. The only difference is if you have a lot of equity in your company name... Square is a good example. Square had a lot of equity. Google is a perfect example. A lot of equity in the company name, you often don't want to name your products something really creative and different because you actually want the equity in the master brand to come through. So if you think about Square's names, they have other ones, when they diverge from the Square brand like cash or when they want something new or Google, when they came out with Android and they wanted to diverge from the master brand. But think about all the products. Square Register, Square Stand, Square App, Google Maps, they're really boring and it's because the equity is in the company name and the product name can actually be boring and descriptive.

**Lenny** (00:28:20):
That makes sense. I want to come back to a point you made that a great name will help a startup and a bad name is not going to hurt you or I forget the word to use. I'd love to hear that because that's that's really interesting.

**Arielle Jackson** (00:28:33):
Yeah. So if your company has a great name and the name is remarkable, people will be like, oh, that's a great name, or it just makes sense. In the case of Seesaw like, that's a good name for that company. That good name is just going to help people talk about it. It's going to spread word of mouth. People are going to like to talk about the company. If you think about there's a lot of companies with bad names that we use all the time or even quite boring names that we now love. So if you think about Disney, Walt Disney's last name, it didn't mean anything, but over time that's such a good company and it got imbued with all this meaning and now it stands for magic and stands for so much, but it was just the dude's last name. So over time a word can come to mean something that is beyond what that actual word means.

**Arielle Jackson** (00:29:21):
Disney means magic today. Volvo means safety. Those names are not good. If I just put it in a spreadsheet or one of those lists, no one would pick it. So that's kind of what I mean that the name is just part of the overall marketing or the overall brand and a bad name with a really great company with great company strategy, great marketing is going to be great over time. And a good name is just going to help you, but I don't think a bad name is going to kill a good company.

**Lenny** (00:29:51):
So interesting. So basically your goal is to help find a name that will help. Worst case, you're going to be okay if your product is awesome.

**Arielle Jackson** (00:29:59):
I think so. Yeah. I mean it also takes a little of the pressure off to be honest. Everyone wants to find that perfect name. If you actually think about it, this happens a lot. You give someone a list of 10 names or 15 names and they're just cells in the spreadsheet these days, we're doing most of this virtually. You give people a name like that and it's like, you have to imagine what it could be. You think about Apple or Disney or Nike or Volvo, Lego, any of these brands, in a cell spreadsheet in plain Arial in 10 point, they're just okay, you have to grow them over time. You just hear about I think Phil Nate with Nike, when he was given that name as an option, he was like, that's okay. Yeah. I'll sleep on it. Such a great name.

**Lenny** (00:30:50):
This makes me think about my startup back in the day, it was called Local Mind, and we went through an exercise similar to this. Not nearly as in depth and well run, but I remember our designer was the person that helped us nail the name. He's just like, oh, I could do so much with this name. Let's just see where this one can go. Is that something you find?

**Arielle Jackson** (00:31:10):
Yeah. There's definitely been bad names. I helped a company rebrand recently that they had a bad name. It just looked dated. It didn't fit any of those. It wasn't distinctive. It wasn't timeless. It had one of those like naming trends. Those are not good. You want to avoid those, but if you come up with something that is pretty good and you can make up something beautiful out of it and it fits your company, it does some of the marketing work for you and people like to say it and ideally it's memorable and it has some emotion to it, go, go for it.

**Lenny** (00:31:39):
Awesome. One last question about naming. What's a common mistake that people make going through this process coming up with a name?

**Arielle Jackson** (00:31:47):
Yeah, a really funny one is if you have a code name for your product or at First Round, a lot of the companies we invest in, they raise their seed round with one name. They may or may not be attached to it, but then they work with me and I'm like, yeah, your name's not that good, and here's why, we should probably change it or they say, we can't use this name. We found out we have a trademark conflict. I really believe in using a code name that's so ridiculous that you won't ever launch a product like that if you're just trying to incorporate and go really quick.

**Arielle Jackson** (00:32:18):
So for example, a lot of people, they need their name for their corporation. And so they are filing all the steps to creating a business and they just like pick something, but then they end up getting attached to it and then they want to actually launch under that name. And it's like, well, that's not so great and here's why I think you should change it. If you pick something so ridiculous that you would never launch, it's actually helpful because then you can go through a process and find a name that will do more of your work for you and you won't be attached to something crappy.

**Lenny** (00:32:50):
Such a good point an idea. And by the way, so if you're a First Round company, you get this naming service for free and all these other things we're going to talk about just to be clear.

**Arielle Jackson** (00:32:59):
Yes, that's right.

**Lenny** (00:33:00):
Oh my God. I could do a whole episode about how much I love First Round, but I will say I'm a huge fan. I think I've participated in every program that First Round offers. The First Round review is actually one of the first pieces of writing that kind of helped spur my now career. And so I'm really-

**Arielle Jackson** (00:33:15):
I remember that article, was awesome.

**Lenny** (00:33:17):
Yeah. And I did two more after that. So much work, but yeah, that was a big deal. So I'm really appreciative to First Round. And we could talk about First Round a bit at the end, too.

**Arielle Jackson** (00:33:26):
Sure. Yeah. Everything we're talking about that you've asked me so far, I think that you're going to ask me about positioning and [inaudible 00:33:33] your marketing person, and all of that is stuff we offer to First Round company, we offer my services as part of the investment. There are times when we might get stuck and we have to bring in an outside person to help us with something, but for the most part, it's all included and you'd pay a lot of money... The naming firm I like the best when I get stuck, it's called A Hundred Monkeys. They're awesome. A long time ago, I used to be like, oh yeah, it's about $25,000. And I recently couldn't take on an outsider First Round project and referred it to them. It's $47,000 for a name.

**Lenny** (00:34:04):
Wow.

**Arielle Jackson** (00:34:05):
So yeah, it's gotten expensive, but if you have the means, it's nice to get some outside help.

**Lenny** (00:34:12):
#valueadd. Okay. I want to transition to your brand development framework, which I read a bunch about. And I know you teach a course about this, which we could also chat a bit about, but first I'm curious, just practically, why is a brand useful? Why is it even something people should spend time investing in? Why does it matter?

**Arielle Jackson** (00:34:33):
Okay. So a lot of founders may think that when we say your brand, we mean your logo and your font and your colors, and that is a visual expression of your brand, but it's not actually your brand, your brand is who people think you are. And so why is it important for people to think what you want them to think? That really comes down to people's understanding and particularly your target audience's understanding of what your company and your product is. And I don't really think there's anything else more important than that if I was building a company.

**Arielle Jackson** (00:35:08):
So your brand is who people think you are and developing a brand strategy is what do you want to be? What do you want people to think you are? And what are you going to do to help shape that perception? So when I work on a company, there's a lot of steps to this, but I kind of have this nice little process that's right sized for early stage startups. And I like to start with, why do you do what you do? Just having a really clear understanding of that. That's your purpose. The second part is your product positioning. So meaning how do you want people to understand your product and what role it plays in their lives? And then the last part is your personality, which is how do you show up in the world? What do you like? If your brand was a person, would I want to hang out with them? Would someone else want to hang out with them?

**Lenny** (00:36:02):
We're going to get into each of these three pieces, but before we get in there, as a founder, how do you know when you're done with your brand development? I know it's a never ending ongoing process, but at the end of a process, you figure out your purpose, positioning, and personality, and then there's logo and colors, when you think about just here's the brand package, what are all the little pieces of it? And then we'll dive into these three elements.

**Arielle Jackson** (00:36:30):
I think what you said is right. You get those three components, your purpose, your positioning, your personality, you use that as an informant to your visual design and also to your tone of voice. So the way your copy sounds, the way you show up in written copy. A lot of companies have what they call like a style guide or a brand style guide and it really only covers logo, fonts, colors, like don't put our logo and blue, don't tilt it on an angle, here's what it looks like in white, here's what it looks like in black, here's the favicon, but they don't have that for here's who we are, here's 10 lines that could be ad copy for us, here is why we do what we do.

**Arielle Jackson** (00:37:14):
This is the personality of our brand. Here are five attributes. We are playful, but not silly. We can talk about that a little bit more. But I think all of that belongs in the style guide, not just logo, font colors, which is really just a visual articulation that feeds into your brand. I'm a big Volvo fan. I'm on my fourth Volvo right now. So I'm super brand loyal. And I always use them as an example, because if you can picture the Volvo logo in your head right now, it kind of looks like the male symbol, it's like a circle with an arrow coming off the side.

**Arielle Jackson** (00:37:48):
There's nothing about that logo that means all the things I like about Volvo, all the things that the Volvo brand has come to mean to me and they're colors, they're like black and white and a little blue. There's nothing more boring than their color palette. And so it's not the logo and the font and the colors of Volvo that has made them mean... They literally own the word safety in cars right now. It's other stuff. And if you looked at their style guide actually, looked at their style guide recently and it's just like, here's our black and our white and our blue and here's our tertiary colors and here's our logo. It would not help you understand Volvo as a brand.

**Lenny** (00:38:29):
I'm guessing some of that happened because they've evolved over the years and it's probably a very different initial brand. So it kind of tells me that it's more important to have a logo and a brand that can kind of represent many things that isn't so stuck in a certain positioning, maybe. Does that resonate at all?

**Arielle Jackson** (00:38:44):
Yeah. Their logo has to do with a very early history. I researched this because I was a nerd out on this stuff. They had some early history as a ball bearings company. And so I guess that logo had some meaning then, but it wasn't so descriptive to being a ball bearing company that they were able to keep it as they evolved into a car company.

**Arielle Jackson** (00:39:05):
But if you look at their early writing, it's so cool. It's so cool. Long, long time ago they would talk about cars are driven by humans. And our job as a car manufacturer is to protect the humans who drive the cars. That was fundamental formation of the company. So they really knew why they existed. And then they did stuff in I think it was the 1950s when everyone just wore lap bands in the car and they came out with the three point safety harness and instead of patenting it and licensing it, they gave that away for free for everyone because that would make all the world's cars safer and those kinds of company decisions. That's what made Volvo stand for safety. It's not the logo.

**Lenny** (00:39:48):
Very interesting.

**Lenny** (00:39:50):
**Arielle Jackson** (00:41:45):
Yeah. It depends on the stage of your company and how much you have already that you have to kind of... It's hard for people to scrap up what they already have. There's a lot of sunk cost fallacy type stuff going on. If you're starting from nothing, I think you can do this in three weeks. The naming process itself because of trademark and domains can take a little longer. When I name companies, it usually takes about a month just for naming, but the whole brand strategy process you could do, if you're a really early stage company in a matter of weeks.

**Arielle Jackson** (00:42:15):
And I think whatever time it takes you actually is going to save you so much time down the road. It's going to help you save time on company decision making. It's going to help you save time, writing your website. Literally your web copy almost writes itself, if you get this all done right. So it's a small investment of time up front that actually saves you a lot of time down the road is how I would sell it to a skeptical PM.

**Lenny** (00:42:40):
You've sold it. That sounds very high ROI. Let's get into it.

**Arielle Jackson** (00:42:43):
High ROI.

**Lenny** (00:42:43):
So purpose is the first piece. What is that? And then what are some examples of really good executions of purpose that you've seen?

**Arielle Jackson** (00:42:50):
Sure. So your purpose is why you do what you do. It makes people want to root for you. And it has a big role in aligning people to come want to work for you and to have employees all feel like they're part of something. I like to think of it as we exist to blank. And whatever that blank is your purpose. Do you want to hear about examples or do you want to hear about what makes a good purpose?

**Lenny** (00:43:14):
Both would be most excellent.

**Arielle Jackson** (00:43:16):
So a good purpose, it explains the change you want to see in the world irrespective of financial gain. So people often get hung up on mission and vision and values and all this stuff. And values are fine. They're internal. I'm not going to talk about those today, but I don't care about mission and vision. I just want one thing because people can only remember one thing and it's your purpose and it's why you do what you do. And when you articulate this really well, it helps you make company decisions, it exists on a 10 year frame. So everything we talk about with product positioning, it's pretty malleable. It exists on an 18 month frame if you're a early stage company, so it can evolve, whereas your purpose is pretty much going to stay the same for 10 years. It's that north star.

**Arielle Jackson** (00:44:03):
And it helps align people in the company and it helps the public want you to win. I worked at Google right out of grad school and Google's purpose was to organize the world's information and make it universally accessible and useful. And I thought every company had a purpose that everyone at the company knew. I just thought that was my first real job. It turns out that's not true. And Google's actually been amazing at this. I had a person in my last cohort who had recently left Google when they were like, I don't know, 80 or a hundred thousand people. He said everyone still can say that. That's amazing. But I joined, it was like 1400 people. And by the time of your first day, you already knew that. It was part of your hiring process.

**Arielle Jackson** (00:44:51):
It was part of your onboarding. It was in your offer letter. It was everywhere. And I just thought that was really cool and a good purpose. One that is kind of related to financial gain, but I still think is cool is Stripe's, which is to increase the GDP of the internet. I think that's really well said and cool and just gets you thinking about the internet as a country. I don't know. If you're an internet person, it makes you want to root for them.

**Arielle Jackson** (00:45:21):
Nike's is awesome. I wrote Nike's down because I don't remember it, to bring inspiration and innovation to every athlete in the world. And if you have a body, you are an athlete. It's not just about LeBron it's about me and how was my Peloton ride this morning too? So those are some famous companies. I could tell you a little bit about some that I've worked on that I think are pretty cool that are companies you may not have heard of yet, just because sometimes we get hung up in like thinking Stripe and Nike and Google are awesome names because of all the meaning we have behind them. And I want to talk about some companies you may not have heard of because you can have a good purpose and not be Stripe and Nike and Google.

**Lenny** (00:46:07):
Yeah. That'd be awesome. And by the way, the purpose, should it be a sentence? Is that the general-

**Arielle Jackson** (00:46:08):
Yes.

**Lenny** (00:46:08):
... guideline. Great.

**Arielle Jackson** (00:46:09):
So you can introduce yourself at a conference. You're the keynote speaker at a conference and I want you to introduce yourself and I want you to go, hi, I'm Lenny, I'm the founder of the company X, and we exist to blah and say it and have that feel natural.

**Lenny** (00:46:21):
Awesome.

**Arielle Jackson** (00:46:22):
And it should make people want to hear what else you have to say. And the other thing it should be able to do is be the header for your about page. So meaning we exist to blah, blah, blah, blah, blah. But you would just take out the we exist and say the verb and start there. That could be the header for your about page. So one company I worked on, First Round company, they're called LogicLoop and it's an operations automation company.

**Arielle Jackson** (00:46:48):
You can think of it almost stuff like a no code, low code platform to automate a lot of the operations data based work that people have to do. And we did this whole brainstorm and I really liked their purpose. You can look at their about page. It will be right there it's to make operations data work harder than operations people. And if you ever have worked in operations or have friends who have, they work really, really hard and it can be kind of thankless. So it gets anyone in that field to root for you. Your data should be working harder than your operations people.

**Lenny** (00:47:21):
Disclaimer, I'm an investor in LogicLoop, and I love that you worked with them.

**Arielle Jackson** (00:47:24):
Cool. Awesome. And then another one that I worked on of another First Round company, they're called Woolf. They're informed by the UC model where there's a bunch of individual schools that all exist by themselves, but they get something from being part of a larger organization. And what they do is they provide accreditation through being part of the larger Woolf University, but every individual college can still operate as their own independent college.

**Arielle Jackson** (00:47:52):
And so their purpose is to increase access to world class higher education and ensure that it is globally recognized and transferable. So this idea of you should be able to take a class from the best instructor online and then go travel to Australia and take a class there and then go to China and take a class there and get the best education that the world can offer.

**Arielle Jackson** (00:48:15):
Another one that I worked on a while ago is Alt. I think they've recently gone through a little bit of like a rebranding, but theirs was to increase the transparency and liquidity of alternative assets. And in their case, the product positioning was really about making sports cards as easy to invest in as stocks. So the idea of alternative assets in this case are not private equity and hedge funds in real estate, but alternatives to alternatives, like sports cards and Pokemon cards and art.

**Lenny** (00:48:45):
Awesome. Those are so many awesome examples. That's going to be useful for people to wrap their head around what a purpose might be. Execution wise, do you just kind of open up a Google doc and just start writing out ideas and brainstorm a little bit and just kind of keep refining with your team?

**Arielle Jackson** (00:48:58):
I actually stole this exercise or borrowed it from [inaudible 00:49:03] that I actually think adds some structure to that. If you do it that way and it works for you, that's awesome. But if you want to go in and go through a process to get there, what I like to do is list all of the cultural tensions that are happening in the world that are relevant to your business first. And so for Alt, that would be things like there's an increase in interest in alternatives. People who are now in their 30s are nostalgic for things that happened in the '90s There is at the time really low interest rates and people are not getting any sort of edge off of investing in the things that their parents used to invest in. So those would be examples of cultural tensions. Cultural tensions are zeitgeist, their things that your audience might be thinking of.

**Arielle Jackson** (00:49:51):
They're things that they may be even subconscious to them, their current events. So you make a long list of all of those. Then you make a long list of all the ways that you might describe your brand's best self. And this is related to your product positioning, but let's say you haven't done yet, so just think of it as your brand's best self. How would we want someone to describe us? When everything works perfectly, and our product really delivers, what does it deliver? And again, bullets, just ways that you would talk about that. And then you pick one from each side, that's really the best articulation of what's happening in the world, what your product delivers, and with that context, now you're primed.

**Arielle Jackson** (00:50:30):
With that context in mind, now you do the brainstorm of, we exist to let me finish this sentence, and even before you get there, sometimes it's helpful to do the world would be a better place if. So for my company, the world would be a better place if, and finish that sentence and then go into the we exist to.

**Lenny** (00:50:49):
Wow. I'm so happy I asked that question. By the way, is there also a place we can point people to that want to do this exercise? Is there another First Round interview post, or I know you have a course on this too.

**Arielle Jackson** (00:50:59):
Yeah. There's another First Round review article it's called Three Moves Every Startup Founder Should Make, something like that

**Lenny** (00:51:07):
Great. I will find it and I'll add it.

**Arielle Jackson** (00:51:09):
Yeah. Okay. Awesome.

**Lenny** (00:51:10):
Amazing. Okay. Let's move on to the next part, which is around positioning, which is a big deal. First, just what is positioning? And then I'd love to know just what tells you may have a positioning problem, that's something you should really focus on?

**Arielle Jackson** (00:51:23):
Okay. So positioning is the space that you occupy in your target customer's mind and everything you can do to influence how they describe your product. You have a positioning problem if I ask 10 of your customers or 10 of your employees what the company does or what the product does. And I get multiple answers. And unfortunately that's the case for most companies. It's okay if the answers are tiny slight variance on the same thing, but I have actually done this with some later stage companies [inaudible 00:52:01] my first step is often I go in and I interview 10 people, and the 10 people are everyone from execs to people who talk to customers to a few customers. And when you get 10 people saying 10 wildly different things, you have a positioning problem. Other ways you might know that if you have a positioning problem is if you can't explain what you do to me in a sentence that's, you have a positioning problem.

**Lenny** (00:52:25):
That's a high bar.

**Arielle Jackson** (00:52:26):
Yeah, it is. And when I first started consulting, I would spend the first meeting with a founder, just totally cold. Hey, tell me about your company. And they would take 30 minutes to tell me about their company. And at the end of 30 minutes, I would pretty much get it, but it always took the first 30 minutes. So now when I engage with a new company, I have them fill out this little worksheet beforehand. And one of the questions is what do you do? And they have to write in a box that's kind of paragraph length.

**Lenny** (00:52:55):
Clever.

**Arielle Jackson** (00:52:56):
And then I go in and I ask questions about that. And ultimately we get it to sentence length.

**Lenny** (00:53:00):
Amazing. Okay. How do you go about figuring out your positioning? Big question.

**Arielle Jackson** (00:53:05):
Yeah. So I start with your audience. Who's this for? And we really think about what's the broadest set of customers or users that you might have and narrow in from there to a target audience, which is who are you outwardly going to try to acquire for the next 18 months?

**Arielle Jackson** (00:53:25):
You can think of it like concentric circles. The biggest circle is your TAM. As you get smaller, there's five parts to it. So the biggest circle is circle one, circle two, circle three, circle four is your target audience. All of the circles have to be contained within the bigger circle. And then the dot in the middle is your model persona. So this is actually like a person with a name and an age and a location and a job and feelings and priorities and interests and all of that.

**Arielle Jackson** (00:53:54):
And so we talk about the model user and the target audience, the target audience again is who will you outwardly try to acquire for the next 18 months? If you're an early stage company, it's very possible that you're going to acquire people outside of that circle, in the next circle or even the bigger circle, but they're not who you're actively going out to try to acquire.

**Lenny** (00:54:15):
Can I ask you a couple questions on the person?

**Arielle Jackson** (00:54:17):
Yeah.

**Lenny** (00:54:18):
I'm doing some writing and research into this stuff. How specific do you suggest people get with this person right at the middle? I love that it's an actual person, I guess not a real person, but a very descriptive [crosstalk 00:54:29]

**Arielle Jackson** (00:54:29):
Can be a real person or an amalgamation of not real people. So with the target audience, I like to think of it as something you could name. So with Eero, it was tech savvy dads. It's a category of people. And then the model persona, or that individual user who represents a tech savvy dad for them was this guy who had teenage kids lived in suburban St. Louis, had a 2,800 Square foot house that was made of brick, worked at home on Fridays. His kids were into gaming. He was the VP of sales at a company that was tech adjacent, but not tech. He was more of like a tech enthusiast than an actual software engineer. We knew a lot about him. I could tell you a lot about him. It's kind of robust, but tech savvy dads was the way to represent him and other people like him, that would be their target audience.

**Lenny** (00:55:22):
A lot of founders have trouble recognizing that going very focused and niche is a good idea versus man, I'm just going to have these 10 people in the world that really want what I want. What have you found to be the reason it's very powerful and important to start really focused?

**Arielle Jackson** (00:55:37):
Yeah. So when you are an early stage company, the worst thing you can do is try to be everything to everyone because you don't have enough runway. You just don't have enough of anything to do that successfully. The best thing you can do is find an audience that is big enough, that if you got your significant market share among that audience, you'd be a giant business. And tech savvy dads is a pretty big audience. Also that's just who your outbound going to try to acquire for the next 18 months. I'm a tech savvy mom. I live with a tech savvy dad. I have an Eero system. It doesn't mean everyone you'll ever acquire must be in that audience, it means that is who we're focused on acquiring.

**Lenny** (00:56:24):
Awesome. I took us off course around the positioning process. I think we kind of went off course with concentric circles model. So I'll give it back to you to keep going.

**Arielle Jackson** (00:56:36):
Yeah. Okay. So the way that I like to run positioning exercise is to start with who is this for? And then what is the problem that they have? There's some problem usually that these people have, they may not even be aware it's a problem, or they may not be experiencing the problem as particularly troubling, but there's something going on for these people. And then how do they address that problem today? So they do something, they're buying something, they're have a workaround, they're doing something today. And that something might not be another startup or your direct competitor. It might be the old way of doing things, but they're doing something. So we go through who is it for? What's their problem? How do they address it? And then what do you make?

**Arielle Jackson** (00:57:20):
How does it work? And what would you want a user of your product or service to tell another? And that's kind of if you answer all of those questions, it ultimately leads into this classic four statement, which is not something I invented, it's something that's been around for 40 or 50 years. And I learned it when I was 22. And I think it's one of the most powerful tools in marketing. It can feel like mad libs if you just approach it cold. But if you've gone through that work of defining who is it and what's their problem, all it is a distillation of that. So that statement is for target audience who there's a statement of need or opportunity. And then you say our product name is a category that has a benefit, unlike the old thing they were doing, our product works this other way.

**Lenny** (00:58:10):
Awesome. And we'll link to the post that actually has that so people don't have to write this all down. That last piece you mentioned, I hadn't heard before, the idea of what will they tell other people or how will they describe it to other people? Is that right?

**Arielle Jackson** (00:58:22):
Yeah. So I believe that great benefits if you've defined your benefit really, really well will actually be the thing that will be the H1 on your homepage and will be the thing that you want someone to tell someone else. Think about Square Stand and turn your iPad into a point of sale. Turn your iPad into a point of sale. Yeah. If I went to a small business owner and they were having drinks with a friend, who's also a small business owner, what would I want them to say about the Square Stand? Oh yeah. I just got the Square Stand. It's this really cool new register that turns my iPad into a point of sale. That's pretty much exactly what I want them to say. And so if you can write that line, that is your ideal benefit, what you want people to say, and it's something that your target audience would actually say, that's great.

**Lenny** (00:59:12):
Interesting. I love that. That makes a lot of sense. For people trying to go through this exercise, you always have such a good answers to how actually the process of coming up with say you're positioning this case, is it again, you pull up a doc and start writing things or is there something even more structured?

**Arielle Jackson** (00:59:28):
Yeah. There's something more structured. I have kind of a worksheet that goes through all those things we just talked about. So it's like, who is it for? What are they doing today? All those questions we just talked about, it's more like a structured brainstorm. There's an exercise I really love that I've called the bar test that is helping you get everything you've written into human language because one of the really big pitfalls I see, especially for B2B companies, but really for everyone is they write in a way that people don't talk. So the document, when I get the first draft back from founders often has things like leverages and empowers and nobody talks like that. And so getting this into turns your iPad into a point of sale blankets your home in fast, reliable wifi, records your screen and cam at the same time, really basic stuff that it describes your product in a way that someone would actually say that's the type of language that I think people want to use.

**Arielle Jackson** (01:00:28):
First of all, you defined your target. Now you pretend to be someone in your target, having drinks with someone else in your target at a bar and you have to be able to say, hey, I just started using product name. It's this really great category, that benefit. And the other person goes, hm, tell me more or that's cool, what do you mean? Or some other similar prompts. And then you have to say your differentiator. You actually have to say it out loud. And if you run through that test and it's actually stuff people would say out loud, then you've done a pretty good job and you can start using that copy publicly.

**Lenny** (01:01:07):
That is very cool. I have not heard this bar test before and I like that it might happen at an actual bar. Is that also something people can find online or is that they write it down right now?

**Arielle Jackson** (01:01:18):
Ooh, I don't know if that's online.

**Lenny** (01:01:20):
Okay, cool. This is it. Exclusive.

**Arielle Jackson** (01:01:22):
Yeah, that's in my course, and we talk a lot about that and we go through the exercise like a real role play in the course, but yeah, take some notes.

**Lenny** (01:01:31):
I like that a lot.

**Arielle Jackson** (01:01:33):
Thanks.

**Lenny** (01:01:33):
Your point reminded me of an email I just pulled up that I got from ADP, your point about just you want to make sure you're branding is something that feels like something you would say to a person. So it's like ADP, which is a security service for fire, like alarms. I got this email, summer's on with fun or our free secure app and more. And then it's like make summer safer and more fun at home or away. ADP, you're not going to make it more fun. What are you talking about?

**Arielle Jackson** (01:02:01):
See, that's an example of trying too hard. They tried too hard to make it sound colloquial and fun. They're a security system, it should be more like secure your home while you're away. Feel safe when you're on your summer trip. Stuff like that.

**Lenny** (01:02:16):
They even included a gif of this TikTok'er being like ADP is my MVP.

**Arielle Jackson** (01:02:21):
Yeah. This kind of relates to brand personality where the brand personality for ADP, I don't know, it's pretty not fun. And so for them, when they put on fun hat, it seems awkward and forced.

**Lenny** (01:02:36):
That's exactly the feeling I got. And so, yeah, personality, that's our next topic. It's not something I you think about when you think about brand and marketing and plans and so I'm really curious to hear why I think that's important then how to figure out your own personality for your brand.

**Arielle Jackson** (01:02:51):
So I think personality is one of those inputs that will help define your visual design and it will definitely help define your written copy. And it really comes from this idea of brands are like people. And if you start thinking of your brand more like a person, it's quite obvious that it needs a personality, because all people have personalities. And these days, especially when brands show up in places where people show up, like TikTok and Instagram, your brand certainly needs a personality or else you end up like ADP trying to be fun for the summer, which just feels really off and weird. So personality is one of those things that it's actually the easiest part. I think it's the fastest part. It often ends up an hour and you can get it done. But I have some frameworks I like to use that really just get at are you Mountain Dew or are you Rolex or are you somewhere in between?

**Arielle Jackson** (01:03:46):
And when you think about brands that have a lot of equity, they really do have a personality. I often talk about Mountain Dew marketing as that marketing that's like trying really hard to be cool and rugged and edgy and fast and kind of teen and Rolex, it's very like Gray Poupon, oh, roll down your window and do you have any Gray Poupon, it's fancy and sophisticated and a little bit aspirational and maybe even a little British. And those two things are really, really, really different. And there's a lot in the middle and not everyone's going to be a Mountain Dew or Rolex, but where are you? And so you can just write it down. I think a lot of these answers come back to like, if you are good with just opening a blank Google doc and like writing down who you are by all means, go for it.

**Arielle Jackson** (01:04:35):
And if that feels daunting and hard for you, use a framework. And the framework that I like to use has two parts. The first part is based on some academic research by Jennifer Aker and it basically analyzed the top brands in the world and figured out that all brands can be segmented into five dimensions of brand personality. And that really strong brand spike in two of the five. So the five dimensions that she found were sincerity, so this is like, is it down to earth and honest, excitement, it's spirited, this is a Mountain Dew thing, competence, reliable and intelligent, sophisticated, sophistication, which is a charming and upper class and rugged outdoorsy and tough. So sincerity, excitement, competence, sophistication, and ruggedness. And going back to those two brands we just discussed Mountain Dew is rugged and exciting, Rolex is sophisticated and competent and you can do this with any brand who admire or just think about brands you like and kind of deduce them to their two of those five.

**Arielle Jackson** (01:05:39):
So that's the first step. Which two of those five are you going to spike in? And it turns out a lot of tech companies end up spiking in sincerity and competence just usually does happen that way. Amazon is sincere and competent. Google is sincere and competent. Apple is not, Apple has a little more of that sophistication to it. But in any case, if you just did that, we would end in a world where everyone's sincere and competent or maybe sophisticated and competent. It's like a really boring world. So the next step after you do that is to define five attributes, five brand personalities, thinking about those two dimensions. I like to think about this as a star, five point star and brands need tension to be interesting. So if you tell me we're helpful, we're nice, we're approachable, we're competent, and we're reliable.

**Arielle Jackson** (01:06:37):
You basically haven't told me anything because you just use three words to say one thing and two words to say another thing. Whereas if you tell me, oh, well we're really savvy, but we're also really approachable. That's kind of cool. Because people who are expert are always approachable. They have to have a little tension and then you want to write them as statements that say we are X, but not Y, where Y is taking X too far. So in the example Google is playful but not silly, so they would say we are playful, but not silly, or maybe Mountain Dew would say we are daring, but not stupid. So taking that attribute a little too far. And so yeah, then you end up with these five statements that are we are X, but not Y. And those are really useful in informing how you write and maybe even what your visual design would look like, and certainly what your illustration style photography style ad copy will be like.

**Lenny** (01:07:39):
Once you've gone through that exercise and in maybe the other two pieces, where do you put this? Is this just like in a doc that's like here's our brand overview, here's our personality, here's our positioning, here's our purpose. And then you refer back to that whenever you're designing and putting together strategies? Is that how it works?

**Arielle Jackson** (01:08:00):
Yeah, you could do it that way. That's definitely one way of doing it. That's a good start. I think that one other place where it shows up, like we talked about that visual style guide that everyone has, that they give to an agency or copywriter who's writing on their behalf. I think these should all be inputs into that doc that you end up sharing. I think it should go into any onboarding you do for new employees so that they understand who the company is. Any partners that you're marketing with, co-branding, all of that, it should really be think of it as your little brand Bible about who you are. And also it should be revisited when you're doing, let's say a new product or to make sure does this need to be updated or does this new product need to fit into who we are?

**Lenny** (01:08:40):
What do you call this document/place?

**Arielle Jackson** (01:08:44):
When I take all those three components and then add a bunch of other stuff, I call it a creative brief, which is the thing you would hand to an agency or a writer who's writing on your behalf. It would include some other things too, that we didn't talk about, like creative inspiration direction. So picking visual clips and written clips and all these things that you like and that you don't like, so you can show both positive examples and counter examples to the thing you're looking for.

**Lenny** (01:09:09):
Awesome. Thank you for all of that. There's so much juice there. I think people are going to have to listen to this a couple times to get all the learnings. Before I let you go, there's two other areas I wanted to dive into. But I'll keep them brief because I know we're going long. One is about getting PR and just a question I wanted to ask you while I had you, founders and even bigger companies, they're always like, how do I get PR? How do I get press for my product, even though it's sometimes a waste of time. Do you have just any tactical advice for startups hoping to get some PR?

**Arielle Jackson** (01:09:43):
You mean initial coverage around a launch or ongoing?

**Lenny** (01:09:47):
I'd say early on, yeah, before the launch.

**Arielle Jackson** (01:09:49):
Sure. So the first one is to get your story straight. So, so many times I have founders come to me and they're like, hey, we need help with this announcement. I'm like, cool. What's the announcement? And back to the 30 minutes until I understand what the company is, so if you can't describe it to me in a sentence, your reporter is certainly not going to understand in a sentence and they won't be able to describe it to their audience in a sentence. And so really getting your story straight, all the stuff we talked about specifically around product positioning is so key. Almost always when someone comes to me and says, I'm ready to announce, we go back to positioning first. Also make sure that your website is ready for the traffic you're going to drive to it, that you're not driving traffic to a name that you're going to later scrap.

**Arielle Jackson** (01:10:32):
Are you really ready for this? So go back to all the other things we discussed first and then having realistic expectations about the outlets that will cover you and the time it will take to get them. So a lot of people will be like, I'm launching next week. And it's like, well, cool that you're doing that, but no reporters going to cover you next week. It just doesn't work like that anymore. Five years ago, eight years ago, founders could really dictate the date of a launch announcement, they could brief three to five outlets under embargo, which means like you all can't tell our secret news until we tell you at this time you can publish. And at that time, three of the five would all file a story and write, and it just doesn't work like that anymore. These days for early stage startups, we're almost always running the launch announcement as an exclusive, which means you give the news to a single outlet.

**Arielle Jackson** (01:11:19):
And they're the only ones who get to write about it. You can obviously still do all your owned and operated stuff, your blog, your social, your investors, your friends and family, but they're the only like news outlet who gets to write about it. So having an expectation that this is probably going to be an exclusive, it's harder than ever to secure funding for a seed stage company and funding in and of itself is not that interesting anymore. There's so many bad companies getting funding. There's so many good companies getting funding too just more than ever. And the number of reporters and the number of outlets that are covering it is just less than it used to be. So really just thinking about like, well, who writes about this space? Do they write about company's at my stage?

**Arielle Jackson** (01:12:08):
That's another really big one is, hey, we want the New York Times. It's like, cool, no one's at the New York Times has ever covered a seed stage startup unless it's crazy for the last five years. Who do you think is going to write about you? But there are still outlets that do. The other one is don't do a straight funding announcement. A lot of founders raise money and they're like, cool, let's announce. It's like, no, we'll use that funding announcement as a news hook to tell a larger story and a larger story might be your products available. You have reference customers, you have momentum, you have some great partnership that you're announcing. There's something else going on, not just your funding and using your funding as part of that initial launch is great, but what else are you announcing?

**Arielle Jackson** (01:12:55):
The last thing is really about making what you do interesting and relevant so that it's not just interesting and relevant to you and the three other people who worked there at the time, but interesting to all the readers of whatever outlet you're trying to target. And so an example of that is I worked on this company, Vitable Health and the founder, Joseph, he created a product for hourly workers that their employer would buy and it costs like $50 per person per month. And what it does is it provides urgent care and primary care. So these hourly workers who make too much to qualify for Medicaid and too little to pay their health insurance premiums, and so primary and urgent care for hourly workers. And we tied it into this idea of the great resignation and small businesses not being able to hire hourly workers, which was like a big trend end of 2021, and the company operates in Philadelphia and Delaware, and we were actually able to get him the Sunday after Christmas, Philadelphia Inquirer story.

**Arielle Jackson** (01:13:57):
But it was all about making this daycare and this restaurant in Philadelphia into heroes because they offered this cool benefit to their hourly workers. And so the headline was perfect for them, but it wasn't like here's Vitable and here's what they announced and here's, it was like, hey, look at this cool new thing that local businesses are doing to attract hourly workers. And so think about your company in a way to make it interesting and relevant and don't sleep on local preps.

**Arielle Jackson** (01:14:23):
If you have a local business or a local story or local customers, this was a huge thing at Square. We turned all of our customers into heroes and went after local press. Most PR firms that service the tech community aren't experts in local press, but if you have a way to make some connections with some local press, they are the ones hungry for these stories more than the New York Times and the Wall Street Journal.

**Lenny** (01:14:50):
What a good tip and most likely they're much more open to writing about you versus New York Times or Wall Street Journal. Cool. Okay. So I want to ask you one question about hiring marketing real quick and I'll keep it short just because I know we're going to run out of time. When should a startup hire a full-time marketing person in your experience?

**Arielle Jackson** (01:15:08):
When you have a lot of problems that you're trying to solve that would be better solved by someone who knew what they're doing, or when you have a bunch of freelancers and agencies that are becoming too hard to manage by yourself.

**Lenny** (01:15:21):
When do you find that usually ends up being... Is there kind of a heuristic-

**Arielle Jackson** (01:15:25):
Yeah. Ballpark, it kind of depends if you're a marketing driven business or a sales driven business. So if you're a sales driven business and you don't have a repeatable sales motion, it's not yet time to hire a marketer, get that repeatable sales motion, and marketing's job is to bring you more marketing qualified leads. So that's one, so that kind of depends. If you're a marketing driven business, it generally seems to me like it happens around 10 people, the founders doing most of this themselves, they're not doing the best job usually or they've hired agency here, a freelancer there to kind of cobble some stuff together. And they now realize like, okay, if I had a person who would be able to do all of this and manage these agencies and freelancers, this would be a lot better.

**Arielle Jackson** (01:16:13):
It also is do you have a one point in time project? Do you need to do positioning? Do you need a website? Do you need a name? Do you need to run a test of Google ads? Those things are all discreet when it becomes this is ongoing work that needs to happen over time. It's better to think about hiring a marketer and really what kind of marketer do you need? Do you need a product marketer, a performance marketer, a comms person, a creative person? Ideally everyone wants all of that. But I kind of like that idea of a T-shaped marketer who's really deep on one of those functions, but knows enough to be dangerous across all of them.

**Lenny** (01:16:48):
I think we're going to need another episode just about that one topic. I have so many questions I want to ask, but I need to let you go. That'll be V2. Before we do that, we've gotten to the very exciting lightning round where I'm just going to ask you quick questions and you just give me a quick answer and we will knock through them all. Does that sound good?

**Arielle Jackson** (01:17:06):
Sounds great.

**Lenny** (01:17:07):
What are two or three books that you recommend most to other people?

**Arielle Jackson** (01:17:09):
In marketing land, definitely the book called Positioning: The Battle for Your Mind. It's from 1980, it's still my favorite marketing book. Another recent marketing book is Alchemy by Rory Sutherland. It's like my favorite area of reading is behavioral science, psychology meets business. And that's in there. For fiction, I just read The Vanishing Half by Brit Bennett. It was awesome. I then read her other book called The Mothers, but I think The Vanishing Half's better.

**Lenny** (01:17:36):
Awesome. I will check that out. What's a favorite podcast or even newsletter on marketing?

**Arielle Jackson** (01:17:41):
I love Nick Sharma's weekly newsletter. He's a growth marketer. He started his career I think at [inaudible 01:17:48] water. So he does a lot of CPG type DTC. He has a great marketing newsletter that comes out every Sunday night. On podcasts, I love How I Built This. I know that's already really popular, but I love that one. It's not really marketing, but just general business. The First Round podcast in depth is pretty great. Lenny's podcast I've been listening to is awesome. And then my friend Jasmine from The Concept Bureau has a marketing podcast called Unseen, Unknown. And it's kind of about culture and branding and how these things and society and trends. It's not like straight marketing. It's kind of more of the culture and sociology that informs marketing.

**Lenny** (01:18:30):
Wow. That is a lot of good stuff. What's a recent movie or TV show that you've loved?

**Arielle Jackson** (01:18:35):
This is more embarrassing. How many movies have you seen in the last year? Just curious.

**Lenny** (01:18:41):
Me? A lot, on streaming services. Way too many also, if that's where you're going or have you seen none?

**Arielle Jackson** (01:18:48):
Well, I've seen maybe four and they're probably all on Disney+.

**Lenny** (01:18:53):
You're winning. That's excellent.

**Arielle Jackson** (01:18:56):
I would say I really like some of those Disney Pixar movies, Luca, Encanto. Those are all really great. I mostly only watch movies with my kids, but I'm pretty excited. I had a celebrity crush on Anthony Bourdain and I'm excited to watch his new documentary if I ever get around to it. And TV shows I'm equally bad.

**Lenny** (01:19:16):
Okay, great.

**Arielle Jackson** (01:19:16):
And there's this little Netflix show called Old Enough. It's a Japanese show with subtitles about sending toddlers on errands in Japan. They like go by themselves. It's 10 minutes. They're awesome. My whole family watched them together. It's really cute.

**Lenny** (01:19:29):
Old Enough. I'm going to check that out. Okay. Two more questions. Favorite interview question when hiring a marketing person?

**Arielle Jackson** (01:19:35):
It's probably tell me a project you're proud of. Tell me about a project you're proud of, is just really open-ended and get to hear a lot about a lot of things that way. And then maybe runner up is tell me about a campaign you recently come across that you were not involved with that you thought was cool.

**Lenny** (01:19:53):
Hmm. Love that. Okay. Final question. Who else in the industry do you most respect as a thought leader?

**Arielle Jackson** (01:20:01):
In the marketing industry?

**Lenny** (01:20:02):
In the marketing industry? Yeah, sure.

**Arielle Jackson** (01:20:04):
I guess old school thought leaders, David Ogilvy, Rory Sutherland, Seth Godin. New school thought leaders, we mentioned Nick Sharma. There's a woman named... I'm probably going to butcher her name, Anna Andjelic. She has a newsletter that I didn't mention before. It's called the Sociology of Business. That's really good. She's a CMO, chief brand officer type. She kind of turned around Banana Republic recently, which was cool. Emily Hayward from Red Antler. I also really like Ross. I don't know this guy, but Ross Simmons from Foundation, which is a content marketing agency. I'm not a content marketing expert, but he really is. And I think he puts out some good content.

**Lenny** (01:20:48):
Man, these show notes are going to be a long list of great stuff. Arielle, thank you so much for being here. There's just so much jampacked knowledge. I don't know if people were prepared when they started listening to this and so congrats on making it through and I hope you're probably going to go back and listen again and again. And so again, Arielle, thank you so much for doing this. Two last questions. Where can folks find you online if they want to reach out or ask questions and how can listeners be useful to you?

**Arielle Jackson** (01:21:14):
Sure I'm on Twitter and LinkedIn. Twitter, I'm hiimarielle. And if you're interested in this stuff, but feeling overwhelmed, I will plug my Maven course. I teach a course on startup brand strategy that covers everything we talked about in this hour, or this is more than an hour now and kind of with a little more hand holding and feedback. So it's a crash course on all this stuff. The four founders that takes two weeks and you go through all of this and that next cohort of that, I think we're on cohort four will be this fall. So you can apply for that course at maven.com/arielle/startupbrandstrategy.

**Lenny** (01:21:57):
Amazing. And I guess that's how listeners can be useful to you.

**Arielle Jackson** (01:22:00):
Yeah.

**Lenny** (01:22:01):
Excellent.

**Arielle Jackson** (01:22:01):
Exactly.

**Lenny** (01:22:02):
All right. Well great. All right, well thank you again, thank you again and [inaudible 01:22:07].

**Arielle Jackson** (01:22:07):
Thanks so much, Lenny. It was fun.

**Lenny** (01:22:09):
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.

---

## [13/20] The nature of product | Marty Cagan, Silicon Valley Product Group

**Marty Cagan** (00:00:00):
People don't buy the problem, they buy your solution. Obviously they don't buy it if it's not solving something they care about, but there are many products that are solving what they care about. The real question is, do you solve it better than everybody else so that they buy you? And that's where you need to take time. So this is more like the coaching I give the teams. I tell them, "Look, be careful. If you need to spend a little time on the problem, fine, but don't spend a lot of time because you need to save as much time as possible to come up with the winning solution."

**Lenny** (00:00:41):
What can I say about Marty Cagan that hasn't already been said? He's the author of Empowered and Inspired, two of the most widely read and influential books on product management. He's also the founder of Silicon Valley Product Group, which he started over 20 years ago. More than anyone else out there, he's been producing the most consistently great and actionable advice for product managers and leaders looking to level up their product game. Before getting into teaching, he was VP of Product at Netscape. He's also a senior VP of eBay. I am humble to have Marty on this podcast. He's an absolute legend in the PM community and I can't wait for you to hear this episode. And with that, I bring you Marty Cagan.

**Lenny** (00:01:23):
This episode is brought to you by Whimsical. When I ask product managers and designers on Twitter what software they use most, Whimsical is always one of the most mentioned products, and the users are fanatical. Whimsical is built for collaborative thinking, combining visual text and data canvases into one fluid medium. Distributed teams use Whimsical for workshops, white boarding, wire frames, user flows, and even feature specs. And that includes thousands of built in icons and a rich library of templates. See why product teams at leading companies call Whimsical a game changer. Visit whimsical.com/lenny to have my own templates added to your account when you sign up. That's whimsical.com/lenny.

**Lenny** (00:02:09):
Hey, Ashley, head of marketing at Flatfile. How many B2B SaaS companies would you estimate need to import CSV files from their customers?

**Ashley** (00:02:17):
At least 40%.

**Lenny** (00:02:19):
And how many of them screw that up, and what happens when they do?

**Ashley** (00:02:22):
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 CSV importer doesn't work right, which is super common considering customer files are chock full of unexpected data and formatting, they'll leave.

**Lenny** (00:02:41):
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 aha moment more quickly and reliably is so incredibly important.

**Ashley** (00:02:56):
Totally. It's incredible to see how our customers like Square, Spotify and Zuora are able to grow their businesses on top of flat file. It's because Wallace data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:03:13):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny. Marty Cagan, welcome to the podcast.

**Marty Cagan** (00:03:26):
Thanks for inviting me, Lenny.

**Lenny** (00:03:28):
It's absolutely my pleasure. I'm just going to jump straight in. I've noticed that you've been getting a lot more philosophical about product, especially in a lot of your recent writing, including a recent post that you call the Nature of Product, where you talk about a lot of these core misconceptions that people have about product management. Essentially how people don't really understand how different it is to build product at a company with a strong product culture versus what you'd call not such a strong product culture. And the way that you described it is that it's trying to explain to someone what the Grand Canyon is by just showing them pictures of the Grand Canyon. And so I'd love to just dive into that and just hear your take on this new philosophical bent that you've taken on product and these misconceptions that you've been seeing across product and product management.

**Marty Cagan** (00:04:16):
Yeah, sure. I mean, it's frustrating and that's what caused me, occasionally I go through these philosophical waves where I look a little harder about... It's frustrating because I really thought by the year 2022, we would not have such a chasm between how good companies work and the rest. There's such strong incentives, just the profit motive alone. Why don't more companies want to work like the best? So I find that just perplexing. And yes, it's true, and one of the funny things, and I bet you could relate to this, Lenny, I have friends on both sides. I have friends on both sides, the ones that work in not very good companies, a lot of them honestly don't believe me when I describe how good companies work. They're like, "Nobody does that." And then when I tell my friends at the good companies, they often say, "Nobody does that either, why would they do that? Are they crazy? Who would want to work that way?" And so this is mind boggling to me.

**Marty Cagan** (00:05:27):
And anyway, when I try to explain to somebody that's never actually worked on a real product team what it's like, you realize that sometimes it feels like I'm speaking a different language to them. And what I realized is that they are so ingrained in this very, very... And I don't even want to say old school because it's not the fact that it's old, it's just the fact that it's obsolete. They have this idea that a product manager does requirements in some form or another, PRDs, user stories, whatever you want. And then a designer's job is to basically make it pretty and maybe do some wire frames. And then the whole mess is taken its sprint planning to the engineers, and you say, "This is what you need to build next."

**Marty Cagan** (00:06:15):
That is so ingrained. And the quarterly roadmaps come in, it's so ingrained. And they think that the job is, "Yo, our job is to crank out features." And a lot of them don't even think twice because that's all they've ever known. And of course, I try to explain to them, "You know, that's really not how it works in any of your favorite products." Any of your favorite products or companies. It's a very different animal. You've really got true peers. The developers aren't there to just implement your dumb ideas, they are there to help you come up with a great solution. The designer's not just there to make your thing look pretty, they're there to help create a great experience. And by the way, you have a very different job as product manager. You need to bring skills to that team that the team doesn't have in design and engineering, because together you're able to really do what you need to do. So when I describe that, it's pretty different. These are not minor differences we're talking about. These are pretty dramatic differences. I really do believe at this point in time that feature teams and real product teams should not use the same string product manager. The job is so radically different, that it's misleading to call them both product manager.

**Lenny** (00:07:49):
For folks listening to this. And they're like, "Hmm, which one do I work on? I'm not even sure." What are some, maybe three to five, signs that you work at a feature factory or feature team as you describe it?

**Marty Cagan** (00:08:00):
Yeah. Well, it's not hard to tell fortunately. I mean, if you've seen both, it's not hard to tell. In a feature team, basically you are handed a typical roadmap. Almost everybody, even though I wish this wasn't the case, almost everybody to have the same thing, that it's a prioritized list of features and projects. So some stakeholders got together, usually quarterly, and they say, "Look, to run our part of the business, we need these features. It's not really complicated. We need these features." And so they're giving you these features. Now realize, these features are possible solutions. So you are being asked to do a little design and a lot of coding and then some QA and then deploy it. And more generally, you're there to serve the business. Now compare that to a real product team. In a real product team, first of all, instead of being given a roadmap of prioritized features, they're given problems to solve.

**Marty Cagan** (00:08:58):
So it might be a customer problem. It could be a company problem, it's all fair, but they're problems to solve. And the team is then given the skills so that they can come up with the best solution to that problem. I mean, that's the Netflix principle is push the decisions down to the people that actually have the knowledge to best solve the problem. The engineers are working with the enabling technology every single day, the product teams are working with the users and customers every single week. So of course, those are the ones that are closest to this, those are the ones you want to push the decision down to. Another difference is when you're given a problem to solve, that's not output, that's outcome, so you either solve it or you don't. As you probably know, most good teams today are doing continuous deployment, continuous delivery.

**Marty Cagan** (00:09:49):
They're releasing many times a day. Who cares if you make another release? If it doesn't actually solve the problem, it's nothing to brag about. It's nothing to celebrate. So in a real product team, you celebrate when you actually solve the problem, when you accomplish those results. That's why we say product teams are about outcomes, they're not about output. So feature teams and product teams, superficially, they're both squads, but they are very, very different. Now it's worth double clicking on the product manager role because fundamentally, the designer and the engineering role are not hugely different. We're asking the designer and the engineers to step up and care just as much about what you build is how you build, but they're using the skills that you learned in university or wherever. On the other hand, in a feature team, the product manager is basically there to herd the cats to get it, and that's non-trivial, but they need to get stuff organized.

**Marty Cagan** (00:10:49):
They need to get stuff gathered. These requirements, you need to document them in whatever tool you're using, in Jira or something, and then you need to get it to sprint planning. You need to make sure it comes out. That's herding cats. It's essentially a project management role. But on an empowered product team, where you're trying to come up with a solution that solves the problem you've been assigned, that's much harder because that means we have to discover a solution that's valuable, usable, feasible, viable. Now while the engineers definitely own feasible, and the designer definitely owns usable, valuable and viable, which are two of the hardest things to do, that's the product manager, and those are pretty big shoes to fill. Those are hard. That takes skill, it takes knowledge. That's why we say in order to be a product manager on a real product team, you've got to do your homework.

**Lenny** (00:11:45):
You touched on this idea that people mention this way working sounds like a dreamland to folks that haven't experienced it. And I asked folks on Twitter what questions to ask you, and that came up a couple times, is people are like, "I read your stuff." And I'm like, "Does this actually exist anywhere? I've never experienced this way of working," just to make people feel like this is possible. One, is there companies that are good examples of this way of working that you like to describe? And then two, just to reaffirm, this is possible, this happens at companies out there, correct?

**Marty Cagan** (00:12:16):
Oh, I mean, it's funny. So first of all, and I should always say this at the very beginning. Whenever I work with teams, I always try to remember to say this somewhere. Nothing I talk about, and honestly being very clear, nothing I've written about in Inspired, nothing I've written about in Empowered was invented by us. All we do is share the practices we see being used in the best teams. So the heuristic is pretty easy. If it's used by several of the best teams, we're like, "Okay, let's start recommending it. Let's see how it works there. And if it works well, we'll start advocating it." And on the other hand, somebody says, "Oh, have you heard about this process? Or have you heard about this tool?" And if none of those companies are using it, I'm like, "Don't bother me. It's either snake oil or it's not proven yet."

**Marty Cagan** (00:13:04):
We don't invent any of this stuff, we just try to share it. There's a little bit, I mean, I'd say the thing that we do is we try to untangle the company's culture from the technique, because Amazon's got their favorite cultural stuff, google does, Netflix does Stripe does. And don't get me wrong, I love those cultures, but they're all different cultures. They're very different cultures. So what we're trying to do is untangle that and share the techniques themselves. But you can read books. Working Backwards from Amazon describes what I talk about all the time, but it's using Amazon terms. You can read No Rules Rules from Netflix. You can see how that's done. You can read Build that talks about how Apple did it. It's all great, but you've got to work a little harder to see the common threads. That's really what we're trying to do.

**Marty Cagan** (00:14:03):
But all these companies Stripe, fabulous Shopify, look at what Slack has done. Even props to Spotify, they've been able to hold their own against Apple and Amazon for so many years. And of course, I'm talking about well known brands. There's countless small companies that nobody's heard of, but hopefully if they keep doing well, people will hear of them one day. But no, it's not a few companies. And there's great companies all over the world today, but it is true that it's a small fraction of total companies. And that's the part that really bothers me.

**Lenny** (00:14:42):
Do you have a sense of what that fraction is? What percentage?

**Marty Cagan** (00:14:45):
I had this conversation actually, you know Shreyas Doshi too, don't you?

**Lenny** (00:14:49):
He's on this podcast.

**Marty Cagan** (00:14:49):
He's one of my favorite thinkers. Yeah, he is one of my favorite thinkers in product. He's just terrific. Because he's also one of those people, at first he was asking me, "Do people really work like you write about? Really, they're that clueless?" And yes, they really are. That's all they know. And of course, the bigger question is, why would they really work like that? We will get to that. But anyway, I don't know. One of the things that makes it hard is there's a lot of people that write software in the world. And first of all, you can break it in half saying those that write commercial products, meant to be bought by lots, and those that just do custom solutions. For a long time, and I don't know if this is still accurate, but for a long time, the industry analyst that I read said that it was actually much bigger number of people doing custom solutions around the world. And so none of those people would really count. So it's hard to say. Does anybody know how many companies really do commercial products? And then what percentage? My purely anecdotal guess is maybe 10 to 15% are good product companies, something like that.

**Lenny** (00:16:10):
Sweet. I love that there's a number. All right.

**Marty Cagan** (00:16:14):
Who knows? It could be orders of magnitude off.

**Lenny** (00:16:17):
Seems reasonable. So a lens that I want to use for part of the rest of our chat is this documentary that you've been recommending in some of your writing that I recently watched and I'm really excited to chat about it. It's a documentary called The Lost Interview where they interview Steve jobs, after he was fired from Apple but before he came back to run Apple. And there's a ton of insights that you've been able to extract that I also loved listening to and thinking about, and I'm excited to chat through this. So first question is just, what about this interview has struck you most initially broadly?

**Marty Cagan** (00:16:53):
Yeah. Well, one of the reasons I loved it is he very rarely talked about product. He loved to talk about his products. He loved to talk about why the iPhone was awesome, why the iPod was awesome, why the Mac was awesome, but the nature of building products was not. I mean, that was his secret sauce if you will, is he had very good insights to this. And so to find this hour plus interview where he's very thoughtful. He had a chance to think through what went well, what went wrong. And to answer your question, in my own writing, and in fact in the recent book Empowered, I share my theory for why there's such a big difference between the best and the rest. In other words, why isn't every company trying to work like the best companies?

**Marty Cagan** (00:17:54):
I mean, why not? Look at the valuation they get. For money alone, you'd think it would do that. And my best theory was that, well, the biggest reason I see is that they have never worked at a company like that, so they don't know what it looks like. They don't know what good looks like. And then I watched this video, which, as you know, resurfaced recently. And Steve Jobs shared his theory from 1995, for God's sakes. And I'm listening to it and I'm going, "Oh my God, his theory is better than my theory for sure." And it's still more relevant. And he talks about product discovery, he talks about process people, he talks about all these really relevant topics. But the one that struck me the most was his theory for why there are so many bad product companies. And his theory was, and by the way, I hope everybody that's listening to your podcast, it costs $4 to rent this on Amazon Prime.

**Marty Cagan** (00:18:59):
Definitely you should watch it. The whole thing. So don't let my summary discourage you. It's worth watching. But anyway, he shares that he thinks what happens in general, as companies get bigger, obviously they wouldn't have got big if they didn't have a decent product at one point or another. But what he was talking about is the same thing I am. Why is it that so many companies lose that mojo? And his argument was because as a company gets bigger, product historically became less important. The people in a company that would be celebrated were marketing people, sales people, finance people. If a company stops innovating, these are the engines for growth. Sales, marketing, or not growth with finance, but cutting cost. And his argument was this happens over time. Pretty soon, these are your leaders. They're the ones that have been promoted. So then what happens? Good product people don't want to work there anymore and they leave and they go to a company that values product. I think that's a better explanation than any other that I've heard. And it was so prescient because when he said this, this had yet to even happen to so many other companies, but it still happens all the time. I wrote an article a while ago called Devolving from Good to Bad that was observing some of this, but he really tapped into it. And honestly I think he's spot on.

**Lenny** (00:20:43):
I like that he describes these as diseases of a company. They own enough market share. This is what happens. Growth is happening. They're winning. They don't need to keep innovating and it becomes this disease. And it's a really powerful way of thinking about it that you want to try to keep this disease from taking over your culture and product and company. And I think there's market share. And then just generally, it happens to companies just doing well. Things are going well, let's not break anything. Why launch something risky and new, and why not just keep selling this thing that everyone seems to want?

**Marty Cagan** (00:21:13):
And actually, Lenny, I think it's worth highlighting because that is an anti-pattern I see a lot, especially after the founders leave. You know how a lot of times in product, we'll talk about there's value creation activities, there's value capture activities. Discovery is all about value creation, optimization's all about value capture. And they're both great, absolutely. You should do both, but so many companies after the founders leave, they're scared. They're literally scared. The product teams are scared, the executives are scared. And the reason they're scared is because they don't know what is essential and what is incidental. They're scared they're going to hurt the thing that's fueling the business.

**Marty Cagan** (00:21:59):
Now of course, the founders knew the thing because they were there from the beginning. They have all this institutional knowledge. They know what's important, they know what's not, and they have that confidence. Sometimes we talk about the moral authority of the founder. They know and they know deeply what is essential and what's not. But when they're gone, very often we see companies that are scared. I can tell because all they're doing is little low risk, Optimizely A/B tests. They're just doing these little A/B tests. They're just tweaking the workflows, the main flows, growth, retention. They're just tweaking. And again, there's nothing wrong with that, but those things will not innovate. They will not cause major improvements to the company. So once they stop doing real discovery, to me, it's just the beginning of the end.

**Lenny** (00:22:55):
What's interesting there is if folks at the top are running it have ideas are not confident about where to go, you think they would empower their teams on the ground to figure out what to do. Instead, they turn into these top down feature teams and they tell them, "Let's just build this thing. I don't know, but it's probably the best idea and I probably know more than you do," and they don't.

**Marty Cagan** (00:23:16):
And in fact, that was one of the diseases that Steve Jobs highlighted in that interview. He called it the disease of the stakeholders, of the managers, where they think that an idea is 90% of the work. And that's how he called it out. And he's like, "They don't understand. The idea is minor. The idea is just to start." I think he said, "The whole craftsmanship of going from an idea to a product." This is what we call product discovery. He was describing product discovery and how things change constantly with every iteration. You make trade offs, it starts off one way, it ends up another way. And of course, he's pointing out that most of these executives have no idea, no appreciation for that's actually how you get a great product. It's not that a bunch of executives go in a room and they come up with their prioritized list of features and then they just tell the teams to build them.

**Marty Cagan** (00:24:18):
In fact, we know at this point only about 20% of those things will generate any positive return. So you think there's enough evidence out there that they would realize that was fatal, but I think it's a lot of arrogance because every executive thinks they're smarter than every other one, and so theirs are the better ideas. But it's really not that way. I mean, good product teams and good product companies know that an idea's just the very sparkle in the eye, it's just the start. Getting to a product is what matters, and that's work.

**Lenny** (00:24:50):
This touches on a question I definitely wanted to ask, which is sometimes leaders think they're like, "I just know what to build. Why do we need to go through this whole thing? Just build this thing. I'm very confident this is the answer." And what you talked about just now is a big reason for that, is a lot of times you don't and you think you do. And a lot of the magic happens in that process of building, iterating, learning, talking to customers. Is that how you see it?

**Marty Cagan** (00:25:15):
Absolutely. And there is one danger zone that a lot of product teams inadvertently fall into there, which is when we talk about discovery, technically there's two kinds of discovery. There's discovering the problem to solve that you should focus on, and discovering the solution that you're going to deliver that people would buy. And a lot of product teams, the founder knows the problem. In fact, most of the company knows the problem. But a lot of times, a product team thinks that they're supposed to, even if they're confident on the problem that they're supposed to go through these some number of weeks or months of problem validation, making sure that people really have that problem, enough of them have that problem. They understand that problem. And again, in an ideal world with no constraints, not really a problem. But in the real world, the clock is ticking.

**Marty Cagan** (00:26:19):
And if you use, say, two weeks of just verifying the same thing the founder already knew, that founder is probably very frustrated at this point because you haven't even got to work on the solution. And people don't buy the problem, they buy your solution. Obviously, they don't buy it if it's not solving something they care about, but there are many products that are solving what they care about. The real question is, do you solve it better than everybody else so that they buy you? And that's where you need to take time. So this is more like the coaching I give the teams. I tell them, "Look, be careful. If you need to spend a little time on the problem, fine, but don't spend a lot of time because you need to save as much time as possible to come up with the winning solution." And it's worth pointing out, since we were talking about Steve Jobs, that was solution discovery when he was describing the 5,000 things you keep in your head. That's solution discovery. So that's important. Product teams need to know that that's where they will either succeed or fail.

**Lenny** (00:27:35):
I know this point is really important to you, this idea that PMs are taught that their job is to figure out the what and not the how. And just to reinforce this point, you're a big fan of, "No that's completely wrong. PMs are very responsible for the how also."

**Marty Cagan** (00:27:51):
That one always makes me laugh because I was thinking, "Do you know how many hours a week I'd need to work if that was my only job?" Probably I'd phone it in 15 minutes a week, "I'm done. I did my part." This is ridiculous. Again, all you have to do is think through it a little deeper. When you're trying to come up with a successful solution, I mean, there are different taxonomies out there. The one I use is it's got to be valuable, usable, feasible, viable, but most products fit. Those are the risks you can call them different things, but those are the risks. And the product manager is responsible for making sure that the solution is valuable and viable, and that is hard. That is hard. That takes real work. And that's part of the how. That's a pretty integral part of the how as well.

**Marty Cagan** (00:28:48):
Now you don't tell the engineers how to code. You don't tell the designer how to design, but you do have a big part. All of us together are coming out with that how. So the how is how it all works. And obviously, how you monetize, privacy issues, security issues, how it's going to go to market, these are all how, but they're product management responsibilities. They're not more or less important than what the designer engineer does because all four of those risks, if any one of them fails, you've got a failure of a product. So those are table stakes. And that's why I laugh when I hear people say, "Oh, you just have to say, the why is so trivial." And it's just so uninformed. I just don't know where the origin is for all that stuff.

**Lenny** (00:29:45):
Makes me think about, men always joke that they're like, "Oh, I want to wear something more interesting to events. I always wear a suit. It's always got to be a suit. It's so boring." And other folks are like, "Shut up. Why would you want to complicate the life of men and having to dress more creatively? We got a good thing going with suits." And it makes me think about if the jobs of a PM are just to find the problems like, "All right. Let's go with that. Life's good." And turns out it's not. Anyway, your last point also made me think about this recent tweet by, I think it was Patrick Collison or John Collison, about how a lot of people think user research, it's like user research informs what you build. That's how people think about it. It's like user research leads to what you build. And his point is really interesting that user research informs your model of the user and the customer and that model should inform what you build. And you're constantly trying to refine this model, but you should have a model of your customer and your user in your head that you can come back to versus relying on user research to answer all your questions. What's your take on that perspective?

**Marty Cagan** (00:30:52):
Yeah. I mean, first of all, what they've done with Stripe is so awesome and that's another great example and I love what they picked and choose from great companies to create a culture for themselves. So I'd absolutely agree, but I'd go a little further. Because user research is a great topic. I mean, right there, it's a great product topic. I love it. I'm a big fanboy of user research. Well you just heard me basically arguing the same thing, don't be going out there spending all your time just validating the problem. Especially when we know, he's saying that too. He's trying to talk about building the mental model of our users, which is so important. Well designed products feed off of that. However, there's another layer around user research that I find is even a bigger source of confusion. In fact, I was just talking to a team this morning.

**Marty Cagan** (00:31:49):
That was saying that, yeah, what they do with user research is they test their prototypes. And when they get enough users saying how much they like it, they build it. And I'm like, "No, that's not why we do user research." And that is not going to fool any smart leaders. And now again, we're back to the problem discovery solution discovery, but most of our time needs to be on solution. And that's prototyping, that's testing with users, testing with customers, testing with stakeholders, testing with our developers. We're testing constantly. We are not just trying to find out if they like it. In fact, it's just the opposite. When we're doing user research, we're finding all the reasons they don't like it. In fact, that's an Elon Musk quote is when you do user a research, you should be focused on finding all the reasons they won't use your product.

**Marty Cagan** (00:32:45):
Even though Elon Musk has some issues right now, he's pretty good at product. And so he is very good at this. And that's how you want to think about that. The user researchers will talk about the difference between generative and evaluative user research. And so most of it, in terms of number of valuable things we get out of it, is evaluative. They are telling us the reasons they won't use it. The only other thing I'll add to that, you didn't ask about this, but it comes up all the time. I hate it when the user researchers go off and do the research themselves and bring back a report, not because they don't know what they're doing, they do know what they're doing. The reason is because the report is too often ignored. And so to me, the rule is, and I tell this to user researchers at the companies that I coach, if the product manager and the designer are not available to be there during their products test, cancel the test. They need to be there. This is what makes them useful to their team.

**Lenny** (00:33:48):
I 100% agree. I have this memory of going to Paris with a research team, our head of Eng, head of design on our team, at least, and I and the researcher all went to Paris to do these focus groups with AirBnb hosts. And our researcher was very adamant that we come with her, that it's not just her coming back with tons of insights. And so 100% find value there. And engineers especially being involved in that process, I find to be super important.

**Marty Cagan** (00:34:18):
That's when the magic happens.

**Lenny** (00:34:21):
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**Lenny** (00:35:21):
I want to come back to this idea of feature teams and just specifically what can people do when they're working at what you'd call a feature team or feature factory to either understand what the experience could be like or just work in a better way, even if their company's not shifting to a new way of building product broadly.

**Marty Cagan** (00:35:42):
Sure. Well, a lot of companies are intentionally trying to change to real product teams. This is what most people mean by a transformation. So a lot of them are, but even if they're not, I always encourage. And a lot of people will ask me, "Should I just give up on this company and go to a decent product company?" And I always say, "Before you give up, just give this one try. And I suggest you go to your manager and say, 'Look, what do you think about us doing an experiment? For the next quarter or two, why don't you let us try running like this?' And if it goes well, great. If it doesn't, no harm. We'll just go back to the way we were." So it's not that hard to try it on a product team by product team basis. Where it gets expensive and risky, of course is changing the whole business units. So if it's just a product team, usually they'll let them try. Especially if the person making this argument says, "I've learned that some of the companies we admire are not working the way we are, and maybe we should try this."

**Lenny** (00:36:49):
Just while we're on that topic, what is it they try or do? What are some of the things that a team could do? I know you may be getting into this, but I'm curious.

**Marty Cagan** (00:36:56):
That's exactly though what I was going to suggest. So let's say they're given thumbs up, "Go for it, give you a quarter, go for it. We'll see what it's like. People are curious." So to me, there's a few things that you want to do. First of all, you want to make sure, and the manager can help a lot, but the product team could help manage up enough to do this. The first is you need to make sure the team has a problem to solve rather than the feature to build. Now, it's not that hard to reverse engineer. So if somebody tells you, "You got to go implement by now pay later on our e-commerce site," which is on a thousand roadmaps right now. If somebody tells you that, it's not that hard to go to the stakeholder that requested that and say, "We're going to get to work on that, but can you tell me how are you measuring success? We want to make sure that what we do, you consider it successful. How are you measuring success?"

**Marty Cagan** (00:37:55):
For something like that, it's usually pretty obvious. It's conversion rate or average shopping cart value or whatever. It's just some KPIs that they care about. So you'd say, "Your belief is that if we add buy, now pay later, a lot more people will be able to buy and transact, and so it's going to pay off and it'll show here. Do I have that right?" And they'll probably say yes. And they might say, "Well, no, we're doing it for international purposes or some other thing." Good to know. Make sure you capture whatever it is. So that's the first thing. What problem are you trying to solve? Now, the hardest part is, like I said, usually we have a designer and engineers that are very up for really doing what they trained to do, but the product manager usually needs to do some work to get themselves to be able to do this.

**Marty Cagan** (00:38:55):
I hate the idea of those companies that have separate product owners because product owner is just an administrative role. Product owners almost never have the skills to be a product manager. And so that's a problem, but let's just say there's a product manager and nobody's ever coached this poor person, and so they really don't know much. So the first thing that product manager needs to do is get themselves prepared to contribute to their team the way they need to. In general, that means four things. First of all, they have to really get to know the users and customers. They have to be considered pretty much one of the experts on the users and customers. I remember when I was an engineer wanting to become a product manager, the person coaching me said explicitly that I was not allowed to make any decisions for the team until after I visited 30 customers. His number was 30. 15 in the US, 15 in Europe.

**Marty Cagan** (00:39:49):
And it was a three week business trip that he arranged that fixed that. And the funny thing was, I didn't think I needed to visit customers because I was a developer before and I was building products for developers. I'm like, "Oh man, that's the one thing I've got is I know our customer." And he said, "Well, all I know for sure is that's never true." And so I had to go visit customers. But anyway, that's the first thing. The second thing is they have to be an expert in the data. How is your product used? How is that change over time? What's the sales analytics? What's the user analytics? So you have to know how your product is actually used, which is just another way of knowing your customer, but important. The third thing is, and this is usually the hardest one and it's the one that your stakeholders will judge you on, is you have to learn the different parts of the business.

**Marty Cagan** (00:40:41):
You have to know how it's marketed, how it's sold, how it's paid for, how it monetizes. If there are any compliance, regulatory, privacy, security issues, you need to know what those are. So you have to convince those stakeholders that you understand what the issues are and you understand what to look for and that you convince them that if there's ever any question, you will bring them a prototype that they can see and make sure it's okay. So you need that trust with the different parts of the business. And the fourth area is you have to know the competitive landscape. You have to know the industry. You have to know the trends. I consider this one of the fun ones. There's some good industry, people to follow. You can do that. So those are the four things you bring to the team. Realize the designer doesn't have this info.

**Marty Cagan** (00:41:33):
The engineers don't have this info. If the team is going to be an empowered team and they're going to come up with solutions, they need somebody on the team that brings this knowledge. And that is you as product manager. That is the single biggest area empowered teams fall down. The product manager is ill-equipped, or a nice way of saying, incompetent. All right. Third, if the team is now going to make decisions, they need the strategic context. In other words, they need to know the big picture. What's the product vision? What's the product strategy? What are other teams doing? How does that relate to what we are doing? That's the strategic context. So normally, we get that from our leaders, but at the minimum, the product manager's going to have to go learn what that is, especially the product strategy. All right. And then finally, the product teams need the skills, discovery skills and techniques, which to me is the fun part.

**Marty Cagan** (00:42:38):
That's why I wrote the book Inspired was to share the most popular techniques. There are other books too that talk about those techniques for discovery. But read something, learn the techniques. There are good techniques today, better techniques than we've ever had. I mean, we've been doing product discovery for a very long time. In fact, Steve Jobs in '95 did a really good summary of it. But the techniques today are dramatically better than what they were when I first learned and what he was talking about. Dramatically better. So you need to learn the techniques. That's the tools of the trade for a product manager. So to your question, you're a feature team. You want to give it a shot, be in a real product team. These are the four things you need to go out and do. And just to be fair, they don't take long. The longest one is the product manager learning those skills if they've never learned them before. But even that typically takes two to three months.

**Lenny** (00:43:39):
Wow. That was incredibly insightful. I'm curious how a PM could set themselves up for success trying something like this because I feel like it's a high stakes experiment. If it doesn't work, the company would be, "Oh no, this sucks. Doesn't work. We're not going to do this."

**Marty Cagan** (00:43:57):
That happens.

**Lenny** (00:44:01):
Yeah. You mentioned a lot of things people can do and then you mentioned reading Inspired. Is there anything else, just things that would set people up for success in one of these experiments within their larger company?

**Marty Cagan** (00:44:12):
Well, in particular about what we're talking about now, Teresa Torres's new book, Continuous Discovery Habits. That's a very good book, it's right on point, talks very much about these skills and it will basically hold your hand through those first weeks. Another good book is Sprint, Jake Knapp's book. That also will hold your hand. Now that's a particular technique to hold 400 pages on one technique, but it is a good technique. Those will hold your hands through it as well. The other thing is you can go out, if you can find somebody who can coach or mentor you. I mean, that's how I learned it.

**Lenny** (00:44:54):
Same.

**Marty Cagan** (00:44:54):
That's how most people I know learned it is they had a manager that gave a shit about their career and they were like, "This is what you need to do." I remember when I first learned about the discovery concepts. I was an engineer and then I had been promoted to tech lead. And my manager said, "Now that you're tech lead, you have to care as much about what you build as how you build it." And he said, "That means you have to get involved in things you were never doing before as an engineer." And I had been an engineer for several years, working my way up the little ladder. And I thought that was super interesting. In fact, that was my first taste of product because I started what we call discovery today. I started getting involved. I started going out to customers. I started learning these problems. If I could change one thing in the industry, it would be everybody would have a decent manager that cared about their career and could help them get better at their job.

**Lenny** (00:45:59):
How do we make that possible?

**Marty Cagan** (00:46:01):
Because sometimes I have a tendency to be cynical, and the world has changed so little over the years, but I have been very happy lately if... Now I know what caused this. It's the great resignation that's caused this, but executives at Microsoft, Google, Netflix, Apple, they've all been bragging about how much they care about coaching. Do you notice that? I mean, literally Sundar at Google has been saying that the number one thing they look for in their leaders is a good coach. The number two thing is that they're not a micromanager and they know how to empower their teams. But at Microsoft, they have three principles for their leaders, they're managers that they've been advertising. Number one, coaching. Number two, caring. I forget what number three is. And then at Apple, they have four big responsibilities for their leaders. Coaching is one of them. So they've all been more vocal about this. Now of course, this is not an accident. They've been caring about coaching for a long time. Usually because Bill Campbell impacted the companies, but they care about coaching. But now they're talking about it a lot more. They're essentially saying, "Come work here. We care about developing you in your career."

**Lenny** (00:47:22):
Yeah. I know that you teach coaches. You have a conference, I think, recently where you're coaching coaches, is that right?

**Marty Cagan** (00:47:29):
Yeah. Not so much a conference. Our problem is, I mean, SVPG, we're very small, we're just five people. And we're booked out for nearly a year. So we are always asked who can we recommend, and the truth is we don't have that many people that we know and can recommend. I mean, there's a lot of people that do feature team stuff, but the people that ask us are because they want to become a great product company. And so we don't know that many. So we've decided to do a session in Europe and a session in the US where we invite people that are independent coaches. We don't charge them anything, this is just a way to get to know them and hopefully help them. So we did that in London a couple months ago and we're going to do it in New York in December.

**Lenny** (00:48:19):
That's definitely one of the most common questions I get is, "Where do I find a coach? Who's a good coach?" And so I really love that you're creating more coaches and helping coaches get better. Along that same line a little bit, how do you think the role of product management is changing and evolving?

**Marty Cagan** (00:48:35):
This is one of those two fork answers. At good companies, it really hasn't changed much at all. And I mean, for more than 20 years, it really hasn't changed at good product companies. Now the techniques they use have changed in some dramatic ways, but the job, the principles hasn't. However, if you look more holistically at the industry, what a cluster. What a mess. There's so many different product related titles, most of which are ridiculous. The two that really drive me nuts are all over Europe, you find product owners and those product owners are taught by Agile coaches. Most of which have never done product for a day in their life. All they know is process, so they're teaching a process. It's as ridiculous as taking somebody off the street and saying, "I'm going to teach you Scrum, and then you're going to all of a sudden be an engineer."

**Marty Cagan** (00:49:39):
How ridiculous is that? Scrum doesn't teach you how to develop just like a product owner course doesn't teach you how to be a product manager. So the result is inadvertently, the blind leading the blind, and we have never had such a high proportion of completely unqualified product people. And of course in the US, that's not as big a problem in the US. It is a problem more on the East Coast than the West, but it's not as big a problem. We have other things going on. There are some very good implementations and definitions of product ops out there, but there's also some really bad ones and those are causing the same problem. One of the things I try to tell, forget all these stupid roles and terms and all this. There's really three things that are sacred for a product manager. And I'm very flexible on everything else, but these three are sacred because they're right at the heart of what it takes to succeed at the job.

**Marty Cagan** (00:50:47):
The first is that that product manager needs unencumbered access to their users and customers. Anybody that tries to get in between of them and their customers is not helping. Even though they're often well intentioned people, they say, "Oh, it's my job and customer success to do that, or my job in sales or..." No, that is like you get cut off from your customers, you're screwed as a product manager. Second, product manager needs unencumbered access to the engineers. If you're not working every day with a set of engineers on solving problems, you are not a product manager. So again, there's these helpful people called product owners or project managers or all kinds of different variations where they think their job is to interface with the developers and to play a mediator role. And they don't understand why they haven't innovated for years.

**Marty Cagan** (00:51:49):
That's why. They've cut that critical thing. And the third is unencumbered access to the stakeholders because a good product is solving what's just now possible, that's why the engineers are so critical, for real users and customers, that's why that's so critical, in ways that work for the business, which is why the stakeholder access is so critical. If you have those three things, direct access to those three things, that's what's critical. If you have other responsibilities, well, as long as you're willing to work crazy hours, that can work. But if you want to have more of a sane life, you can take all this other stuff.

**Marty Cagan** (00:52:34):
Project management, quality assurance, product marketing, all this stuff. Runtime, production operations. Literally you can pass those to other people, but don't delegate those three things. I just keep begging companies. They think don't realize the damage they're creating when they do that. And of course why they do it is no secret. They say, "Oh, that product manage your job is too hard for one person so we're going to split it in half." And they have no idea the damage they're creating, but that's what they're doing. So pulling off other responsibilities is no problem. It's a good thing to do, especially as you grow, but never when you touch those three sacred things.

**Lenny** (00:53:23):
Awesome. I was exactly going to ask that. The PM role is so full of things to do in such an intense job with so many responsibilities. And so the intention is good. Take some things off the PM's plate. Specifically product ops I've been seeing grow, as you've said, just to double click on that, is your sense that's not a great role to have and not a productive direction or is there times when that's actually helpful?

**Marty Cagan** (00:53:48):
Well, from what I just said, if you now talk about product ops, if product ops is created to replace one of those three things, which is some of the common definitions, it's bad. I mean, there's lots of good definitions of product ops too, but some jobs, I should say some products have a big runtime responsibility, runtime production, production issues, triaging bugs, trying to figure out what's going on. A little bit of that is totally normal.

**Marty Cagan** (00:54:29):
Everybody does that in every company. But sometimes it becomes so much that there's just no time left for figuring out what should be billed next. It's just fighting fires every day. That's a good definition of product ops. Another good definition are the people who create the tools to help product managers be more productive. That's a good definition. But notice those aren't taking away any of those three things. But one of the common definitions is they're like, "Oh, well we get so much data on how our products are being used for our customers. We've created a product ops person that's going to sort through that data." And they'll tell the product manager what they think they should hear.

**Lenny** (00:55:12):
Just to reinforce this point, what are the three things again? In case folks didn't catch it all.

**Marty Cagan** (00:55:17):
Yeah. Direct access to customers, direct access to the engineers, direct access to the stakeholders.

**Lenny** (00:55:25):
Awesome. Maybe a last question is, are there other trends that you're worried about in product management where the role of PM is going?

**Marty Cagan** (00:55:33):
Well, I am very worried about the two trends I just described. I'd say the thing that has always been a risk and it's just not going away. And by the way, Steve Jobs talked about this. This was the other disease he talked about and that's the disease of process people, which by the way is another one of the bad instances of product ops is process people. And I know where this comes from, I understand it, but scaling is hard. Do you know anybody who doesn't think it's hard?

**Lenny** (00:56:07):
I do not.

**Marty Cagan** (00:56:07):
It's hard. And fundamentally, there's two ways to scale. You can scale with process or you can scale with leaders. The only way I know that leads to good outcomes is scaling with leaders, but the easier, more appealing one to so many companies is scaling with process. And that's why you see, you might look at something safe and say, "Are these people freaking crazy? Are they nuts? There is no good there. It's just repackaged waterfall. What the hell are they thinking?" Well, what they're thinking is, "Oh, we have an answer to scaling with process."

**Marty Cagan** (00:56:47):
And that is very attractive, especially to some old school CIO that doesn't even understand software. And so it grows like crazy. And that's not the only ones. There's a bunch of those processes and people are fooled. It's just marketing, so they call themselves Agile, but it has nothing to do with agile. It's the antithesis of agile. So I am very worried about that trend of thinking that process is ever the answer because it's not, it just isn't. And all the best leaders I know, whether we're talking Bezos or whether we're talking Elon Musk or anybody, Steve Jobs was saying it in the video, be careful of the disease of process people. They will destroy your company.

**Lenny** (00:57:39):
What an incredible way to wrap up. Just two last questions, where can folks find you online if they want to reach out, learn more? And how can listeners be useful to you?

**Marty Cagan** (00:57:50):
Well, I mean, all of our stuff we publish for free at svpg.com. siliconvalleyproductgroup.com. You can also find me reluctantly on social media, but I do the minimum possible. Signal to noise ratio on social media is so terrible, I try to focus on other places. But that's where you can find me for sure. Yeah, I mean, at this point in my career, I'm just having fun. I'm not looking for anything from anybody. Well, I'll tell you one thing I love, I love getting hard questions. Most of my articles are inspired by questions that I have never got before.

**Marty Cagan** (00:58:34):
And so when I hear the same question enough, I realized maybe I should write about it. And I love that. Especially even if it's something I need to go learn more about. And I do have, at this point in my career, a great Rolodex of people that I can go to and say, "Hey, Lenny, what do you think about this?" Or Shreyas or Teresa. All these people I know that are very smart and I can go to them and say, "What do you think about this?" And I put everything together and I write about it. So yeah, if you really have tried and can't find a good answer to a hard question, feel free to email me.

**Lenny** (00:59:12):
Amazing. Send your hard questions to Marty. Marty, thank you so much for doing this. This is everything I hoped it would be. I am really thankful that you joined me and thank you for being here.

**Marty Cagan** (00:59:23):
Well, thanks again for inviting me, Lenny, and good luck to everybody out there.

**Lenny** (00:59:28):
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.

---

## [14/20] How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable)

**Yuriy Timen** (00:00:00):
The only thing that's worse than a channel or a tactic that you tried not working. The only thing that's worse now is when you didn't give it the appropriate shot, right? And you prematurely were erroneously concluded that it doesn't work and it's remarkable how often you find that to be the case when I talk to companies, "Oh, YouTube, we tried it. It doesn't work." I'm like, "Okay, can I see what you've tried?" And then you look at it and you're like, "Oh, this thing was not designed to even have a shot at working from the get go."

**Lenny** (00:00:40):
Yuriy Timen is a full-time advisor to companies looking to figure out their growth strategy. He's worked with companies like Canva, Airtable, Otter, Whimsical, Hims, Flow Health, and a dozen others. I know a number of founders who have worked with Yuriy and they all tell me that he transformed how they think about their growth. Before becoming an advisor, he spent nine years at Grammarly where he led growth in marketing and helped turn that into the household name that it is today.

**Lenny** (00:01:07):
**Ashley** (00:01:44):
At least 40%?

**Lenny** (00:01:46):
And how many of them screw that up and what happens when they do?

**Ashley** (00:01:49):
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 CSV importer doesn't work right, which is super common, considering customer files are chalk full of unexpected data and formatting they'll leave.

**Lenny** (00:02:08):
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 aha moment more quickly and reliably is so incredibly important.

**Ashley** (00:02:23):
Totally. It's incredible to see how our customers like Square, Spotify, and Zuora are able to grow their businesses on top of flat file. It's because flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:02:40):
If you'd like to learn more or get started, check out Flat File at flatfile.com/lenny.

**Lenny** (00:02:47):
**Yuriy Timen** (00:03:52):
Thanks for having me man. This is great.

**Lenny** (00:03:55):
It's even better for me.

**Yuriy Timen** (00:03:57):
All right.

**Lenny** (00:03:58):
So I'm going to give a quick bio. Let me know if I missed anything really important. You were head of growth at Grammarly. You spent nine years there kind of doing all the things that helped turn that company into the killer product that it is today. You left that I think a couple years ago. Now you're advising companies mostly full-time. I think mostly on growth strategy. I think mostly consumer startups, is that about right?

**Yuriy Timen** (00:04:21):
A couple of super critical corrections. Number one, it was only eight and a half years.

**Lenny** (00:04:26):
Okay. Usually people round those up. I'm impressed that you get-

**Yuriy Timen** (00:04:31):
I think eight and a half is long enough. Yeah, not sure I want to round up. I know, but I'm kidding obviously. Yeah. That's largely it. Grammarly was a hell of a run and trying to take a step back from that, and stepping back has kind of taken on a life of its own vis a vis advising.

**Lenny** (00:04:54):
How many companies have you worked with at this point advised and what are some examples, just like companies people would know.

**Yuriy Timen** (00:05:01):
It's now been about, I guess two years and three months since my last day at Grammarly in an operating capacity. I've probably worked with maybe 15 companies in the last two and a little bit of years. Obviously, not all at once. It's usually four to five at any given point in time. But some of the ones that I've been really lucked out with in terms of getting aligned with companies like Canva, Airtable, Hims and Hers in the personal care space, there is otter.ai. Who else? Flow Health, the world's most downloaded period tracker.

**Lenny** (00:05:47):
I used that for my wife. It's handy.

**Yuriy Timen** (00:05:49):
Good, good. Yeah. I was trying to get my wife to try it out, but been unsuccessful.

**Lenny** (00:05:59):
You're failing in your growth.

**Yuriy Timen** (00:06:01):
She was like, "Are you trying to push me to having a third kid?" I was like, "No, no, I swear." This is just product testing.

**Lenny** (00:06:08):
Clever. So I've had Casey Winters on this podcast and Elena Verna. It's kind of like the three of you that it feels like have worked with the most companies as advisors. I don't know if there's some kind of contest y'all have or anything, but do you think about that at all? Is there anyone else out there that you think is in the running?

**Yuriy Timen** (00:06:26):
First of all, just being mentioned the same breath as those two is an accolade in and of itself. I mean, I look up to both of them. They've gone first. Also, I credit a lot of my getting started to both of them because they've been very generous with their time when I was just kind of considering advising, especially Casey, if they listen to this. Huge shine out to both of them, but Casey especially. He's such immense when it comes to just being generous with his time. So no, there is no competition, but had there been one, I suspect I'd be in lead right now because I've done it. I've done it in a shorter period of time. I'm much newer to advising than both of those, but no, I have a ton of aberration respect both of them. They're phenomenal what they do and I learned a ton from them.

**Lenny** (00:07:24):
I love that acceleration is fastest. Wow, sweet. So we're going to talk a lot about consumer growth strategies and your experience working with companies and a bunch of insights on things you've learned from working with companies. Before we get there just one quick question in your advising. I'm curious how many companies do you work with at once normally?

**Yuriy Timen** (00:07:43):
Yeah, so I play around with different quantities. So a couple of things. So you mentioned, you alluded to earlier that I advise full time. What I'll say is that mostly the only thing that I do right now professionally is advising, but it's not quite full time. I hard count my week at about three to three and a half days a week worth of work, which is a personal choice. And so that is a hard constraint that I'm working with. And within that constraint, I also feel like for me to do my best work and the work that I also enjoy the most and find the most fulfilling four to five companies is probably the max. If I try to go beyond that, the overhead that it creates in terms of the cost of context switching just becomes overwhelming. I feel like I'm not showing up as best as I can with each individual company.

**Lenny** (00:08:43):
As early plug or anti plug, depending on how you answer this. Are you looking for more companies to work with right now or are you just like, "Don't even try. I am so at capacity right now."?

**Yuriy Timen** (00:08:53):
I'm so at capacity right now. I've also just been very fortunate to always be at capacity. But I think for every four to five companies that I'm working with, think of it as a concentric circles, right? There are another, maybe 10 to a dozen companies that we're actively exploring if we want to work together in the future. And then there is another concentric circle so maybe 30 plus companies that I'm just friends with. So I'll take the plug. I'm always up for meeting Austin founders working on important problems.

**Lenny** (00:09:31):
Cool. Well, we're in the plug I guess. How do people find you online? What's your Twitter?

**Yuriy Timen** (00:09:34):
I mean, honestly, probably throw Lenny's podcast. That's one, but honestly LinkedIn is really the only place I'm pretty low key otherwise.

**Lenny** (00:09:45):
Okay, great. That was a lot of Meta stuff. So let's get into some meat stuff here. So you talked to a lot of consumer startups. You help them figure out how to grow, how to evolve their product, something I'm always curious about and I love your thoughts on is when you look at a consumer startup, I imagine there's a few archetypes of how they grow. I'm curious if that's a mental model you use when you're like, "Oh, I see company X. They're probably going to grow this way, and here's what they should focus on." How do you see that?

**Yuriy Timen** (00:10:11):
Great question. I think there are ways to answer that. My sweet spot is subscription properties and it's not just consumer. I do work with a lot of B2B companies. It's just that most of them, but what they all have in common is they lean into consumerized type of growth loops and growth motions. So they're very kind of self-serve nature or have meaningful self-serve engines. So if I think about subscription companies, I think there are probably a couple of buckets that I see them falling into. If you were able to nail your unit economics and you have really strong consumer LTVs, think Grammarly, think Canva. The single player LTVs for those companies are very, very high. They're kind of average S&B LTVs for B2B companies.

**Lenny** (00:11:03):
What's a number there just for folks to have a little context?

**Yuriy Timen** (00:11:06):
I'm not a liberty to speak to those, but we're talking in the hundreds of dollars. Most consumer subscription companies that are $5 to $7 a month. Their LTVs typically cap out at 50 to 60 bucks.

**Lenny** (00:11:25):
Cool.

**Yuriy Timen** (00:11:26):
And so if you have really healthy LTVs, and that usually means that you're attracting a proconsumer buyer, so they may be single player, but they're using it for work. And so maybe they're dispensing it or just the perceived value so much higher that they're willing to bear that $120 and $130 a year subscription. If I'm seeing things like that and I'm seeing that you're converting seven, like five plus percent of your free users to a paid subscriber, then there is a big opportunity to play paid and lean into paid growth loops and paid acquisition loops. There is another archetype, which is if there are network effects for instance, you don't find that as much with single player consumer subscription companies, but obviously social media, consumer companies.

**Yuriy Timen** (00:12:17):
There may be a strong referral viral loop angle if the utility increases, the utility of the product increases, the more users are using it. Another archetype I see are companies that can lead into SEO very heavily, especially if there is a long tail programmatic angle. Take Canva for instance, their biggest initial growth loop and I think this is public knowledge was their long tail SEO strategy where any kind of design project that you could think of would search for designing. It's kind of two categories of keywords, make keywords and template keywords. So if you're searching for a template of any kind, a wedding invitation, yada yada, they had incredibly strong SEO and they were just capitalizing on all the long tail traffic. Not every product is going to lend itself to that, but I always look for that early on, because you can build incredible mold with that kind of strategy.

**Lenny** (00:13:21):
That makes sense. There's kind of like these three engines that you can tap into. I imagine the preference would be word of mouth reality and then if that isn't going to work SEO, and if that is going to work paid, maybe just to simplify it for listeners, what are kind of signals you can go after virality and invest in that and think that could work because every founder would be like, "Yes, virality. That's how I'm going to grow." Yeah.

**Yuriy Timen** (00:13:47):
Yeah. Honestly, the first thing you look for is that, is there inherent product network effects? It's something that it's either there, or isn't from inception from my experience. I think it's very difficult to manufacture. You'd only study when... It's very hard to manufacture product network effects if they aren't there from the get go. So Airbnb from your days, obviously marketplace very strong product network effect dynamics. You think of collaboration tools, Airtable, monday.com, Whimsical, whom we both know very strong inherent product network effects, contrast that with a company like Grammarly. It just wasn't there. It's not an inherently multiplayer task constructed communication. And so you can try to engineer that, but from my experience, it is an uphill battle. So if you have inherent product network effects, that's when I think layering on referral loops and viral loops. You think about what Dropbox has done around file sharing. That's an iconic example.

**Yuriy Timen** (00:15:02):
Then it's really powerful. I think that there is another case where referral and viral loops could work even when there are inherent network effects. If you have a really beloved product, beloved brand. There's a company out of Australia that I have opportunity to invest it called Laika. They do fresh dog food subscriptions and incredibly beloved brand, a premium product. And so they're able to lean into a give one, get one referrals, even though there isn't inherent product network effects, they're still able to generate meaningful results off of the, and incentivize referring program.

**Lenny** (00:15:39):
When you talk about network effects, what does that mean to you? How would you define that briefly?

**Yuriy Timen** (00:15:45):
Yeah, to me, I mean, honestly I define it I think probably a pretty quintessential way, which is for every individual user, the utility that they derive from the product increases the more users there are on the platform. The expanded version of that is in a case of marketplaces. It may not be the bore users broadly speaking, but the more users in the markets that you care about, in the case of collaboration tools, it's not the more users in abstract terms. It's the more users within your team, the more users within your company, right? That correlates with your kind of the rise in your utility curve.

**Lenny** (00:16:33):
Awesome. So if you have network effects, AKA if the product becomes more useful with more people or there's amazing word of mouth already, or there's collaboration, probably a good sign that you could lean into virality or maybe referrals. What about SEO?

**Yuriy Timen** (00:16:50):
Oh, that's a good one. It's a very timely question because I actually in a process of helping a couple of my companies figure out if it's the right time to invest in SEO. So I've been sort of a forefront of taking exploratory meetings with agencies and SEO consultants and things like that. I mean, I would say the first thing to figure... I mean, there are a couple of pillars, because obviously we all know that SEO has a different return horizon than say paid acquisition. It's longer out. It's maybe six months is the earliest you can see results. Even then it's going to be a small trickle that compounds over time, if you're successful or you may spend three to six months leaning into an SEO strategy and then realize that it's not going to back out typically at least in historically a company probably isn't like Series B before it starts feeling like it passed a luxury of making these kind of medium to long term investments.

**Yuriy Timen** (00:17:58):
But I think that's shifting right now, but that's maybe a topic for later or even for another bot but a lot of the strategies that I think we're reserved for Series B are trickling down to Series A companies because they have to diversify way for pay, but maybe more on that later. So I think with SEO, it's like the first pillar I would say is, do you have a unique angle when you take a look at the SEO landscape today, you look at editorial, the landscape, which is to how to searches and who are the players there and what kind of information is being offered? Do you have something unique to contribute to that conversation? Another thing if I have to do an audit checklist, another thing is, do you have a unique programmatic angle, right? For instance, Canva did dealt with templates. Who else is programmatic?

**Yuriy Timen** (00:18:54):
CWELL, Redfit, obviously all the real estate, right? That's really strong-

**Lenny** (00:19:00):
Saint Pier.

**Yuriy Timen** (00:19:01):
Saint Pier, right. So do you have a programmatic angle and then understanding the competitive landscape or the other one is, do you have a unique data angle? So for instance, a company I work with called Monarch Money, which is in the personal finance management space. Think of it as a new and improved version of MIT. There is a lot of users are connecting accounts and you have a sense percenting patterns and things like that. Clearly there is a unique data, and so it's a question of, can you turn it into some kind of valuable organic search experience?

**Yuriy Timen** (00:19:39):
I won't go into too much detail in terms of what we're thinking of there, but that's another checkbox. If you can check two of those three boxes as a back of the envelope framework, you may be in good shape. And then it's a question of like, "How can you lower the cost of experimentation SEO as much as possible?" I think as a rule of thumb, if you can time box it to three months, what can I do at the end of three months? Is this likely to work or not?

**Lenny** (00:20:14):
Awesome. Couple follow up questions.

**Yuriy Timen** (00:20:16):
Absolutely.

**Lenny** (00:20:16):
One is SEO feels like this dark art where you need some SEO wizard to come help you through this.

**Yuriy Timen** (00:20:24):
Yeah.

**Lenny** (00:20:25):
Do you suggest companies find somebody or work with an agency or something else? What's your general feeling on SEO versus some other route?

**Yuriy Timen** (00:20:33):
I think SEO is pretty specialized skill set. There are some basic principles that always hold like best content wins and don't do shady back linking and make sure that you're on page. SEO is good and your pages are easily crawl, but I feel like everybody knows that. And where the winners are determined are between the lines. Better than a sports' analogy? Maybe you can.

**Lenny** (00:21:10):
Between the lines. I don't know what that comes from.

**Yuriy Timen** (00:21:15):
But anyway, what I mean is that there is a lot of more nuance, SEO developments and angles, where I think is where the opportunity really lies to differentiate yourself. And that requires keeping up with the latest algorithm changes. It's very hard to do that unless you are specializing in the art where the black magic of SEO, and so that's why I think getting an outside resource at least for an audit is really helpful. Now, whether it's a boutique agency or a solo consultant, I think that's more circumstantial, but I've found at least with the companies that I've worked with, if we wanted to quickly vet the SEO opportunity, I can do it in a very kind of amateur, at an amateur level.

**Yuriy Timen** (00:22:02):
Plug things into similar web and try to figure out the right option is there, but you can get these relatively inexpensive audits done from companies that you can then choose. Do I hire them to help with my SEO or not? But I think that audit is usually a very good use of time because they have templates. So what they can turn around for five to 10K would take you many, many human hours to try to pull together yourself.

**Lenny** (00:22:28):
Awesome. Are there agencies that you want to name that people can go check out or would you prefer just to keep it from having-

**Yuriy Timen** (00:22:35):
I'll give one plug.

**Lenny** (00:22:37):
Great.

**Yuriy Timen** (00:22:37):
I think one of the most innovative, disciplined first principles SEO thinkers and I have met is Ethan Smith from Graphite. It's not for everyone. It's a pretty high end SEO shell. So I wouldn't send the Series a company there, but Ethan also produces a lot of resources and what they've been focusing on at Graphite lately has been actually automating a lot of their work and turning it into SAS. So I don't know how far along they are, but you could probably already get into some of the betas from the tools that they're offering.

**Lenny** (00:23:18):
Sweet. I'm going to try to get Ethan on this podcast.

**Yuriy Timen** (00:23:20):
Yeah.

**Lenny** (00:23:21):
I've seen his stuff and it's awesome.

**Yuriy Timen** (00:23:23):
Yeah. He is a math scientist when it comes to SEO. Yeah.

**Lenny** (00:23:25):
We need those. We need math scientist on ship.

**Yuriy Timen** (00:23:28):
Right.

**Lenny** (00:23:28):
Okay. So we've talked about virality talked about SEO, paid. Imagine that's pretty straightforward if your LTV are high enough and you can pay back ads on those, then that's where you go. Imagine everyone can try it. Doesn't work for everyone. What if yeah, anything you want to add there?

**Yuriy Timen** (00:23:43):
I mean, there's a lot. There's a lot. I mean, I don't know how deep you want to go down the paid rabbit hole because it's changing. It's probably the most affected growth bucket in light of the market turbulence, the venture sentiment shifting. I've seen paying acquisition strategies at budgets. They are at the brunt of that fallout. And so the question is where do you want to go there?

**Lenny** (00:24:16):
Yeah. That's a really good topic. I was saving that for later, but let's chat it better right now.

**Yuriy Timen** (00:24:19):
Yeah.

**Lenny** (00:24:20):
I imagine part of this is Apple's tracking changes too.

**Yuriy Timen** (00:24:22):
Yeah.

**Lenny** (00:24:22):
So I guess my big question is paid still lucrative and a good path for many companies is like 50% of the time less effective. How do you see that shifting recently? And how should people think about paid in the consumer subscription startup?

**Yuriy Timen** (00:24:38):
Well, I think in the short term, let's break it down into phases. I think in the short term paid acquisition and just paid media dollars are contracted and we're seeing it already with Metas advertising revenue, Snaps advertising revenue. There's clearly a global contraction happening to paid media budgets. A big part of it is because all of a sudden the definition of efficient acquisition and good payback windows is shifting. So before for a consumer subscription company, 12 month payback was decent. Now it's like, you better pay back your paid media in six months or less. That's the sentiment.

**Yuriy Timen** (00:25:23):
So the thought is reaction is like anything that's more than six months we're well board of six months, we're cutting that and so there's that. Then there is just less tolerance for ambiguity and attribution when the sentiment is like, "Let's grow at [inaudible 00:25:38]. Grow at all costs." If you can't attribute things perfectly, that's okay. Now it's like, especially with venture back companies, you have to have two plus years of runway, managers burn a lot more diligently now. And so whatever you can't attribute to sales sue like, "That shits got to go." I don't know if we can curse on the pod or not.

**Lenny** (00:25:59):
Only available-

**Yuriy Timen** (00:26:03):
Well, I've been holding back for the last 30 minutes. No, I'm kidding.

**Lenny** (00:26:03):
At least.

**Yuriy Timen** (00:26:04):
All right.

**Lenny** (00:26:05):
We're not kid friendly, but nobody's cursed yet. So this could be okay. So you'll be the first.

**Yuriy Timen** (00:26:09):
All right. Way loud. All right. But anyways, yeah. So I think there is a short term contraction. However, that opens up an opportunity for smart kind of attribution investments. So you're seeing an emergence of some interesting attribution related attribution for incrementality related products. A couple that I personally started exploring and looking into, and then you just see a lot more heads of growth, heads of user acquisition, thinking about attribution in building their attribution stacks. And so I think that once we settle into some kind of new normal, which is going to be a combination of just better attribution stack on average for companies combined with just the level of acceptance, that attribution will never be as good as it maybe once was. We're going to probably get hit. Come out of that and you'll see paid budgets start making their way back. But even right now, during contraction, there are going to be some winners.

**Yuriy Timen** (00:27:26):
The companies that had strong cash positions, have strong unit economics, strong paid back periods already like Grammarly, Canva to name two that I know personally. A couple of others or many others probably, they're going to be winners because all of a sudden, if previously they were competing with companies who were nowhere as efficient as them, but for whatever reason had the green light to keep spending, now all of those are going to pull back their budgets. And so those that have been disciplined, have the instrumentation to track things better than average. They're going to benefit from decreased competition on app platforms, decreasing CPMs, et cetera. So they're going to do winners for sure.

**Lenny** (00:28:09):
Wow. Haven't heard this perspective. It's so interesting that the fact that it's gotten harder, it's creating new opportunities for companies to do it better and more intelligently. You said you mentioned a couple tools products that you found to be potentially helpful in this. Is there anything you could mention there?

**Yuriy Timen** (00:28:22):
Yeah. Yeah. I mentioned a couple that I've kind of connected with in the last couple of months. So first of all, Media Mix Modeling is making a comeback, which is something that kind of got popularized in the math meant kind of advertising era of the fifties, pre-digital, and that's how that was the piece of the methodology. I can't speak of the specifics there. The science is a little bit out of depth there, but it was basically a way to use some data to determine a budget allocation across channels at the time was probably newspapers and billboards, et etcetera.

**Yuriy Timen** (00:29:03):
It was leveraging data to some extent. You would were doing it maybe on a quarterly basis. And then you would only update it every quarter. There was no way with media mix modeling. There was no way to adjust budget in quarter because you weren't getting the data feedback loop that frequently. But media mix modeling is now making a comeback because there are so many offline channels that are part of folks channel portfolio today and that plus a lot of the online channels are becoming less trackable like Meta for instance, with the iOS 14 shift. And so Media Mix Modeling is going to comeback and the company that's leading the charge of bringing the Media Mix Modeling methodology of the traditional advertising era and ushering it into the digital world is a company called the Recast.

**Lenny** (00:29:48):
Recast.

**Yuriy Timen** (00:29:48):
Recast. Yeah. So I've heard really good things. I haven't tried them with any of my companies yet, but there are a couple that are on the horizon hopefully.

**Lenny** (00:29:58):
Double click there for a moment. Is that still useful if you're not doing TV and other forms of advertising?

**Yuriy Timen** (00:30:04):
I think it's still-

**Lenny** (00:30:04):
You're just doing-

**Yuriy Timen** (00:30:04):
Yeah, I think it's useful if you're spending a considerable amount, what's considerable, I'd say worth of a hundred thousand a month update media. And if you have some level of channel complexity, so you're not just like a Google Go or a Facebook, but maybe you're on three plus the channels. Then I think it still makes sense. The other ones in the incremental space, they have very different methodologists actually, because at end of the day, this might be obvious to folks, but maybe some will find value.

**Yuriy Timen** (00:30:34):
Click based attribution or the digital attribution were all fawning over cookie based and click based, a real parameter based attribution. It never demonstrated a causal relationship between our media spend and business results. It was only good for correlative insights. And the only way to determine causality is through real controlled experiments, randomized control experiments through incrementality testing, which is typically really hard to do cleanly and also companies have always been often wary about doing it because you have to turn off a channel potentially in a key demo and you're like, "Yeah." The benefit is to learning of whether it's actually incremental, but the cost or the sales that I will lose today. But the only way to really know how effective your paid media is through ongoing incrementality testing. So there are two companies that are addressing that. Two that I'm excited about. One is measured, can be found, measured.call, amazing domain name.

**Lenny** (00:31:44):
Amazing domain name, go with that.

**Yuriy Timen** (00:31:45):
And then the other one is incremental, but incremental-

**Lenny** (00:31:50):
Outcome.

**Yuriy Timen** (00:31:51):
... no vows except the last A between the T and the L.

**Lenny** (00:31:57):
Excellent, great job.

**Yuriy Timen** (00:31:58):
So many free plugs today.

**Lenny** (00:32:00):
Yeah. I love it. That's great. This is what people need. They're just like, "Okay, what do I actually do"? And so the more it's clear what to actually try and how to solve these problems. The more people can actually make change. I had a couple questions here that I wanted to follow up on. One is founders might be listening to this and they're like, "Amazing. Okay, we're going to grow. There's three ways to grow. Let's do it all. Get someone on SEO to get Jane on paid. Let's get Fred on virality."

**Yuriy Timen** (00:32:32):
Yeah.

**Lenny** (00:32:32):
So in your experience, is it smart to focus on one and then expand down the road or try them all see which one works best? How do you advise companies think about these options?

**Yuriy Timen** (00:32:44):
I would say focus paired with rapid iterations, right? With limited resources. Naturally you have to practice some form of essentialism and ruthless prioritization, but at the same time, the clock is always ticking. You can not burn. That there is a finite number of tries that you have at finding what works, right? What's going to help you unlock the next level of growth, get to the next funding round, extend your runway. And so I think either one taking to an extreme focus or trying multiple things is not a good thing. And just in case, it's not obvious if you focus on one thing and it ends up being the wrong thing, you've wasted really valuable time and now you have so much less time left to find something that does work. Spreading yourself very thin oftentimes in the early stage companies, it's one person who's in charge of all of growth, but they also have some other kind of responsibilities like maybe ops and customer success.

**Yuriy Timen** (00:33:54):
If you get them to try five different things, they may not try them anyone individually fully enough, because I like to say the only thing that's worse than a channel or a tactic that you tried not working. The only thing that's worse now is when you didn't give it the appropriate shot and you pretty much surely or erroneously concluded that it doesn't work. And it's remarkable how often you find that to be the case when I talk to companies, "Oh, YouTube, we tried it doesn't work." I'm like, "Okay, can I see what you've tried?" And then you look at it and you're like, "Oh, this thing was not designed to even have a shot at working from the get go." So to answer your question, I think it's focus with some guard rails so that you know exactly when it's time to move on to the next thing.

**Lenny** (00:34:51):
**Yuriy Timen** (00:36:12):
Love the question. It's very thought provoking. I think with some tactics and some channels you can fairly objectively create some test guard rails where it's like, if it's YouTube, we know kind of minimum number of impressions that you got to get. Try two to three creative angles. Here's the click through rates range that you're looking for. If you get within these ranges on these KPIs, keep going. If you don't, abandon.

**Yuriy Timen** (00:36:48):
I think that's important to also know that abandonment doesn't mean we will never revisit it again, right? It just means that because every time you're evaluating, the concept of sunk cost. So you have these periodic, I think periods of reevaluation where it's like, "Okay, did we try enough? Is this more art than science frankly." It's like, "What's the incremental lift for us as a team to try to experiment with the next phase of this channel or this tactic? What is the opportunity cost of that? What are the other high profile things that we could be trying?" You were right and save this topic too hard to answer in this format, but I would break things down maybe into two types. There are some channels or tactics where you can objectively figure out som guard rails for when it's showing promise or not, because you can pull benchmarks on good click through rates and things like that. Then there are other tactics where you just have to exercise more judgment outside of benchmarks.

**Lenny** (00:37:54):
Yeah. Yeah. That was actually really valuable and very challenging question to try to summarize quickly so thank you. One more quick question along these lines. So you talked about these three broad ways companies grow. Oftentimes a couple of them work, something I've seen and I'm curious if you agree, usually one is like 80% of your growth and then you layer on a couple more to optimize. Is that what you see?

**Yuriy Timen** (00:38:18):
Yes. I think companies that we know and admire and reference in case studies or in podcast, such as this one. From the outside looking in, you oftentimes assume that it's a highly diversified growth engine. I have to say it's often not the case. Definitely the 80/20 applies. There is a kind of strategy that's working overwhelmingly well, and there is a scramble internally to minimize reliance on that one thing. And on the discover slash on the walk, the next step function, the next growth horizon. In the case of Grammarly, it was performance marketing kind of over reliance on performance marketing during part of the company's life cycle. And so it was like, "Okay, this thing is working." It's efficient so you don't want to stop pouring fire on it, but you're also thinking months and years ahead, what kind of risk does it open you up to?

**Yuriy Timen** (00:39:35):
And so there is a scramble to fight and at Grammarly, it's been successful there. With Canva, it was the SEO angle. So for them, that was working really well, which is more defensible than paid. That's sort of long tail programmatic SEO angle, but look, you're always susceptible to Google algorithm updates and so how do you derisk yourself from that? But to your point, yes. And I think that surprising thing to people probably is that it's also the case with some later stage companies. It's not just early stage companies that are kind of one trick pulleys. Sometimes it's later stage companies as well.

**Lenny** (00:40:11):
This makes me think about is there's kind of these three phases to growth. There's the kickstart phase where you're just doing a bunch of stuff, trying to get things moving. Then there's that you discover your first main growth engine and then there's layer on additional engines because you want to diversify.

**Yuriy Timen** (00:40:25):
Yep. And one interesting, what I believe is an interesting period and a lot of it is gut feel, right? And I try to direct companies. I encounter sometimes early stage companies is when one thing is working well and they're already worried about over reliance and they're starting to talk about diversification and I come in all the times and I see showing up in their OKRs. I come, "No, no. Too early. I'm glad that you're such a forward thinker. Put all of your energy. Sure, this one tactic is accounting for say 80 plus percent of your new user acquisition, but your user acquisition is still small. So don't get distracted with diversification. We'll get there. Lean more into this, hit this growth rates, stand this up. Build this into a real strategic advantages thing that's working."

**Yuriy Timen** (00:41:17):
So I actually have to talk them out, focusing on diversification too early. Contrast that with some later stage companies for who are... At scale, I know 50 plus million ARR, 90 plus percent reliant on a single acquisition channel, which just mire with risk and diversification is a blind spot for them. And then with those, I have to be like, "Hey y'all. Here's the risk that you're carrying. Let's start carving out bandwidth resources to try to go and explore these other channels with tactics."

**Lenny** (00:41:49):
That's such an important point. It reminds me Casey has this hilarious line that he uses that the money's always in the banana stand or there's always more money in the banana stand from [inaudible 00:41:59] development. That basically your growth is probably going to come from the same place it's already come from.

**Yuriy Timen** (00:42:03):
Yep.

**Lenny** (00:42:04):
And that you shouldn't take that for granted. And you should put most of your efforts into continuing to optimize that versus being distracted by, "Oh, let's do SEO now."

**Yuriy Timen** (00:42:11):
I see that argument for sure.

**Lenny** (00:42:13):
So you mentioned at this point about how later stage growth strategies are starting to move earlier into growth strategy planning. I'd love to hear more on that.

**Yuriy Timen** (00:42:22):
Yeah. Let me expand on that in the world that we lived in last 18 months, or let's say up until say three to five months ago. We were living in a world where funding was abundant and plentiful, startups were conditions to think that they could raise twice a year. Valuations were quite toppling within a year. You raise in January and then you raise in November and your valuation five X. And so companies were coming off of these ridiculous Series As of 15 to 25 million dollar As and they were like, "We got to grow as quickly as possible. What can we activate to give us immediate return?" And the answer is almost always paid. That one going to give you, especially if you're think you want to go back to raising less than 12 months later, that forces you to focus on very kind of short term tactics, short payoff tactics.

**Yuriy Timen** (00:43:28):
And so things that SEO, there was no room to think about that for early stage companies. Because payoff is going to come maybe in 12 months in terms of meaningful payoff. We care about getting to the next round and maximizing our valuation between now and then. SEO is for the grown up companies. When we're that we could think about it. And they were getting the reinforcement from everywhere, from peers, from VCs. It's like it's growth, growth, growth. The growth at any cause.

**Yuriy Timen** (00:44:02):
I think what happened now and we'll see where things stabilized because I think we're still in the midst of a little bit of chaos. What's happening now is the same VCs are saying, "Okay, it's now survival." You have to extend your runway, minimize burn, high burning if you have to. And all of a sudden growth, whether explicitly or via inference becomes kind of a secondary objective, especially for all these companies that are far from being cash flow positive. They have to figure out how to stay alive, but not have to go back to the market and be sort of a victim of shitty terms. And so I feel this is me extrapolating because venture capitalist didn't actually tell me this, but I'm extrapolating that growth is a secondary objective now. It's really focusing on sustainability due to economics, accepting your runway control your destiny, getting to default life.

**Yuriy Timen** (00:45:00):
And all of a sudden it's like, "Okay. Plus paid is a lot less attractive now. Can't afford to be acquiring users at like LTV cap one to one." That's now a no-no. And so SEO is now becoming more attractive because once you got your burn under control and you're thinking, "Okay, we saved all this money by reducing our paid budget. We're cutting it entirely. How do we put some of those resources back to work?" And all of a sudden SEO starts looking a lot more lucrative because it's almost like you took the urgency of grow at any cost in the next six months, you took that out of the equation. So now it's like we're in a position where we don't have to go back to raising 12, 18, 24 months. We have 18, 24 months worth of runway and now companies are starting to think more in terms of building more sort of sustainable and defensible growth initiatives.

**Lenny** (00:46:02):
Fascinating. And as much as people may want to do SEO, like we talked about earlier, doesn't mean they will be able to pull it off because there's these things that have to be approved for your type of company and-

**Yuriy Timen** (00:46:12):
Yes.

**Lenny** (00:46:12):
Yeah. Going back to point you made earlier about paid being a really interesting opportunity right now because it's become harder. Would you say generally you're kind of like pro, tri paid, go paid be in this time because I'm finding a lot of startups are like, "Oh, we can't do paid anymore. We're trying all these other approaches to grow." Is that like alpha right now? Start thinking about paid in a creative way and maybe this is going to be a huge advantage.

**Yuriy Timen** (00:46:35):
So there are two pieces to do paid. I mean I'm oversimplifying, but I think people will hopefully appreciate the over the oversimplification. Number one, because it actually drives returns at efficient unit economic, whatever that may mean for your company, your business, your industry. The other way to do it is because it's a very quick way to get learnings on messaging and positioning on designs on features. You're thinking of launching et cetera, right? It's hard to get faster learnings at scale than A/B testing headlines, Google search or whatever. I think the problem that I find is when a company can't have which camper in or where they try to say that they're in both, but really it's like, "Okay, you're funneling a hundred K a month." It's super inefficient and they're not even running experiments to actually get the learnings. I can assess the company, even if I don't download the industry as well, based on just seeing their funnel performance, their conversion rates, their retention curves, their LTDs, understanding their churn.

**Yuriy Timen** (00:47:43):
I could say whether they stand the chance at making paid work as a former strategy. So not just the learning mechanism, not just the kind of a feedback engine, but actually a profitable at delivering acquisition channel or strategy. And if I see that they're not there because the funnel doesn't convert well, the users don't retain the LTDs are too low. Then I say, "Hey, it's not time for paid. Maybe car on a little bit of budget if you want to quickly test positioning and things like that. But it's just too soon." But instead I encounter a company that's really healthy conversion rates, strong LTDs. I do a little bit of competitor research and I can see where the opportunities are, which channels are less saturated than others. Then I may say, "Hey, it's worth it. It's worth a go." And also just seeing the bigger picture of their financial health, how much runway do you have? What does your monthly burn look like?

**Lenny** (00:48:41):
Right? Because paids like cash going out the door and it will return hopefully at some point might be six months might be a year, and so that's a real constraint. You mentioned onboarding and funnel conversion. Two questions there. One, do you have a heuristic of here's good for conversion rates? Is there something that you think about there that you could share or is it very case dependent?

**Yuriy Timen** (00:49:03):
I think it's case dependent, but yeah, it is. It's not case dependent. It's category dependent. So it's not that every company is so case, but it's like, we got to know about what buckets we're talking about. I will say that... Let's say we talk about prosumer premium SAS, ala Grammarly, ala Canva, Whimsical, InVideo, things like that. Yeah. I can confidently say a healthy website visit to a free user, a free account creation conversion rate. It's probably in that 20 to 35% range.

**Lenny** (00:49:43):
From landing on the site to signing up?

**Yuriy Timen** (00:49:45):
From landing on site to a free user at scale. Earlier stage, you have strong product market fit with some kind of small audience segment that conversion can be 40 to 50%, but as you go broader, it'll probably asymptote at like 25, 30%. What about a conversion if you're premium from a free user to a premium account or paying account? I think anything under 5% is not going to work long term, regardless of how big your top of funnel is. You may get the soft point, but for you to remain an independent company continuously growing pre IPO, I don't think it's going to happen. It's got to be north of 5%, ideally like more than 7%.

**Lenny** (00:50:39):
Wow. Super handy. On the onboarding point, what's your thoughts on investing in onboarding and that part foe of how often is that a fruitful area of investment?

**Yuriy Timen** (00:50:49):
Almost always. A lot of my work is in that sort of a prosumer space. So the products tend to be more complex. Airtable, whimsical, Canva, InVideo. They're very robust products. And so it's very easy to get lost in their editors. I think what all of those companies are trying to do for their respective verticals and use cases is they're trying to democratize access to fades that previously you have to rely on professionals for. Maybe in the case of bayer team bot, it's your engineers. In the case of PM bot, it is professional graphic designers. In the case of a video, it's professional video editors. So when they're trying to democratize access, but they're also trying to make the products robust enough to be comparable to a professional great quality. And it's a very difficult place to play it, right? It's like, how do you make it simple enough where a nonprofessional can use it, but robust enough where they go and say, "Oh yeah, this is as good as if I would've hired a professional fill in the blank."

**Yuriy Timen** (00:52:19):
And that's where onboarding, sorry for the long answer. That's where onboarding is really, really important because there's such a huge difference between landing someone on that initial editor page, be it Airtable, Canva having that left to their own devices versus getting as much information or as much relevant information front and then customizing that landing experience for them. So that if they're there to do X and we know XYZ about them, we're able to guide them and not expose them to the robustness of the product all at once. So the short answer is almost all the time onboarding is a big opportunity.

**Lenny** (00:53:04):
Awesome. That's what I was expecting to hear, to give folks some context. What's kind of an order magnitude that you've seen improvement on onboarding and maybe impact on a company improving onboarding.

**Yuriy Timen** (00:53:15):
Earlier stage companies where still haven't really approached the local maximal, but you haven't experimented with a ton of things. I mean, you can two to four X activation rates easily through onboarding. I think later stage companies like maybe Series B beyond, I think you can still probably get to 20 to 30% lift at activations. It depends on how many low hanging fruit are left to tackle.

**Lenny** (00:53:46):
That makes sense. Yeah. Till the onboarding, there's always money in the onboarding banana stand. On that kind of same idea, do you have a general feeling of investments in this stuff often pays off and helps you grow and is often higher ROI and investments in bucket B are rarely successful. What would those two buckets be?

**Yuriy Timen** (00:54:07):
So thinking of investments rawly, right? Not just monetarily.

**Lenny** (00:54:13):
Yeah. Yeah. Time and resources.

**Yuriy Timen** (00:54:15):
Yeah. I mean, I would say that getting to know your customer always pays off. So it's user interviews and getting to know your market, your customers, and your prospects always pays off. Customer research, inside surveying, interviewing panels incredibly useful. And I found that to be very especially early stages. The amount of clarity at momentum that it can create inside of a seed Series A up to Series B company when you first do some proper research push. The way it can galvanize the team and give them focus and clarity and purpose is remarkable. So that always pays off. What doesn't pay off? I mean, I think over reliance on paid, it comes to bite you in the rear end. When I think about tracking an attribution, I think it's a question of the right level of investment at the right stage.

**Yuriy Timen** (00:55:19):
Rarely do companies get it right. They usually fall into one of two buckets where they underinvest in attribution and they are now, their budgets are up high. They have a broad channel portfolio and they have a hard time figuring out what's working, what isn't and they just get into this inertia. It's like, "Well, overall, the company's been growing and it's been growing roughly over the same time that we've been increasing our spend. We're scared to break it. So we're just going to keep spending." Or companies that read horror stories about other companies overspending. They sometimes try to invest in attribution too much, believe it or not where they're trying to get everything perfect and scientifically pure. But what they don't realize is that the payoff may not always be there. And so how do I fit this into your question of, I think tracking attribution incrementality is definitely a worthwhile investment arena, but it could both be a good or bad depending on the level. So you got to make sure the level investment is appropriate for your stage when you stand to aim for-

**Lenny** (00:56:35):
Awesome. You're such a good interviewee that you come back to the question.

**Yuriy Timen** (00:56:39):
No, that I promise.

**Lenny** (00:56:40):
That was great. Okay. One last question. Before we get to our very exciting lightning round. I'd love you to get your thoughts on advertising on TikTok and YouTube and broadly is there any other tactics, avenues that you think are kind of underutilized or emerging that folks should be thinking about?

**Yuriy Timen** (00:56:58):
Yeah. So TikTok, one thing I'll say about TikTok is I'm seeing it come up more and more as a channel that works well. And sometimes even the most efficient channel, most efficient digital channel for some brands. But I think that the thing about TikTok that oftentimes I was surprised about is you often hear, "Oh, TikTok that's for the 15 to 22 year olds." I'm bad with my gens Z and oh, my audience is different. So I'm just going to ignore the champ. TikTok has so many users and it's still so relatively unsaturated with advertisers that your audience is on there. You'd be surprised.

**Yuriy Timen** (00:57:46):
I've worked with brands that their core demo is like 40 plus married making 200K plus in household annual income. And you wouldn't think that demo is on TikTok and it is. So what point about TikTok? Other channels, I think out at home is still not getting enough love. Podcasts? Okay. Yep, yep.

**Lenny** (00:58:14):
Spots through this one. I recall you heard it from Yuriy.

**Yuriy Timen** (00:58:17):
Direct mail, what has happened? They've gotten better with attribution because before a lot of those channels were written off as sort of attribution is just too hard on there and attribution is so good and reliable on digital. So that's that gap that canyon that existed in attribution capabilities of online and offline, deterred a lot of people from offline. Today offline has gotten better and actually positioning themselves as being able to do attribution, but also online attribution is deteriorated. So all of a sudden that argument kind of slimmed out a little bit and I'm seeing offline get a lot more traction and in podcasts, especially are actually very, very performant for a lot of brands. Those are a couple of things that come to mind.

**Lenny** (00:59:11):
Those are great. Happy to hear the podcast piece. Excellent. And then I actually, I'm an investor in a startup that Databig at a home campaign and they just told me that it was a 10 to one positive ROI on the deals that they got out of it. So I've been seeing that too, and that's such a good point that the measurement and attribution online has come down where it maybe makes more sense to try stuff like that. Amazing. All right. Are you ready for our very exciting lightning round? I'm going to ask you five questions I think, and then just, yeah, let's go through it quick.

**Yuriy Timen** (00:59:44):
Let's do it.

**Lenny** (00:59:45):
Let's do it. Okay. What are two or three books that you recommend most to other people?

**Yuriy Timen** (00:59:50):
Ooh, that's something that I think is very wrong to recency bias, right? It's like, what are some of the books you've read recently that you've enjoyed? But I would say there are a couple of books that stuck with me over the years. I think on the business side, where on the business side productivity side, it's a book called Essentialism. I forget the author's name. I think his last name is McKeown or something. And it's basically the book about cutting out the noise and finding a singular focus and doing that really well. It's a book that was a game changer for me at Grammarly being sort of new in my career, having really aggressive goals, not being scared to say no. Taking on a lot, just feel it thinking like, "Well, I'm only working 12 hours a day. There's 12 more left. I can do it."

**Yuriy Timen** (01:00:45):
And then when you end up stepping into a leadership role, which happened for me, I mean, that happened prior to grounded, but really I was able to grow into that role at Grammarly. That book was incredible and I used it a lot. I pretty much got copies for everybody on the team, like 40 plus people. So that is a book I swear by.

**Yuriy Timen** (01:01:06):
I read a lot outside of work and business. So I don't know if it's appropriate, but I'll say that. It's Frankl's, A Man's Search for Meaning is just a remarkable memoir on perseverance and I think that biggest takeaway is you can't control what's happening around you, but you can control your reaction to it. And then I'd say the book that I read recently, because I was very affected by the Russia invasion of Ukraine. I'm originally from Ukraine. I believe you are as well. So it hit very close to home and there have been a lot of references drawn between the President's Zelensky and his response in the war and Winston Churchill's response in 1941 when Hitler started marching through Europe. And so I read a book called I think The Splendid and the Vile by Eric Larson.

**Lenny** (01:02:02):
Yeah. I read that. I read that.

**Yuriy Timen** (01:02:03):
Did you also read it since the invasion?

**Lenny** (01:02:06):
No, it was before that, but I totally get that now.

**Yuriy Timen** (01:02:09):
Reading it right now because I've been following the conflict very closely, but for people who haven't followed the conflict or maybe have only followed the rush, the war kind of in a cursory way, you can put what's happening into historical context remarkably well. So I feel like that book accomplishes two things. Number one, it's like you learned something about not so distant history that maybe you didn't know, which was about Great Britain and Winston Churchill kind of courageous response in the face of Hitler's invasion of Europe. But you also can draw so many parallels to what's happening today. And hopefully that helps us understand what's at stake, not to end on two grandiose of a note.

**Lenny** (01:02:57):
We'll go less grandiose quickly, but I will add one thing that stood out in that book that is also true in the Ukraine is how during the fire bombing of Britain, people are just going out every day, going to clubs, still having-

**Yuriy Timen** (01:03:09):
I know. Steal them their life.

**Lenny** (01:03:11):
And same thing even today in Ukraine is.

**Yuriy Timen** (01:03:14):
And not just keep, but it's very life.

**Lenny** (01:03:17):
I love that. Okay. We'll move on to less, less serious stuff maybe. What a transition to, what's your favorite other podcast?

**Yuriy Timen** (01:03:27):
Honestly, there's only one other podcast that I'll listen to right now because I've just been so consumed. I listened to a lot of live streams and read a lot about the conflict, which has taken up so much of my head space. That's not work related, but I would say that the All in Pod. I feel like it's a cool way for me to just catch up on everything that's going on through their unique filter.

**Lenny** (01:03:50):
Yeah.

**Yuriy Timen** (01:03:50):
That's probably the-

**Lenny** (01:03:52):
Cool. Yeah. I learned a lot.

**Yuriy Timen** (01:03:53):
Yeah.

**Lenny** (01:03:53):
I learned a lot from that one. That's so much drama on that show. Okay. Great. Favorite recent movie or TV show. Anything stand out.

**Yuriy Timen** (01:04:00):
So that's another thing. Since February I've watched nothing. My Netflix skew just keeps growing because they keep emailing me saying this new season is out. I'm like, "Oh yeah. I used to that show. Let me add it to the queue." I mean, recently I had some downtime. The kids were with grandma, so I watch movie Hustle with Adam Sandler.

**Lenny** (01:04:22):
Love that. So good.

**Yuriy Timen** (01:04:23):
Yeah. It was good. It was it's very light. It's not like a movie that's going to make you think a lot, but it was just good old entertainment. Yeah.

**Lenny** (01:04:31):
I like that. I like that summary. Yeah, it was so delightful. Maybe one more question. Who else in the industry do you most respect as a thought leader? Maybe someone people may not know or if anyone else comes to mind.

**Yuriy Timen** (01:04:43):
That's a very good question. So I would say first off, I do believe that some of the brightest minds, honestly, in any craft are people that you never hear because it takes a certain personality, energy, and probably a lot of other circumstances to invest in your personal brand. And also it's very hard to do that while still staying relevant as a practitioner. I mean, when I think about myself two years ago before starting advising, I was just kind of living in my Grammarly cave. And I felt like I was probably at the top of my craft, but I didn't have time to pick my head up or not, maybe not even just tie, but I didn't know where to start to pick my head up and do something like this. I would say some people that, I mean, I mentioned Ethan in terms of SEO. SEO and just organic growth loops and content as a growth engine, he is best in class.

**Yuriy Timen** (01:05:49):
Who else? So Mark Fisk, he shows up in the Reforge chats a lot. He was leading growth and marketing at Credit Karma for a while. And right now he's an investor I think at the HRG Capital, but he is a really, really strong thought leader on all things, performance marketing attribution, and just kind of paid acquisition at large. Those are two people that I make sure I... And there are others of course, but those are two who I make sure I stay in touch with at least on a quarterly basis because any casual catch up just yield so many unique nuggets.

**Lenny** (01:06:25):
Amazing. Where can folks find you online if they want to reach out, learn more and how can listeners be useful to you?

**Yuriy Timen** (01:06:31):
Honestly, I don't have a very strong online presence. I would say LinkedIn is probably the only place where I seek things the recent, so folks can find me there. They can also find me inside of Lenny's Newsletter. I do. I do. I do, but you can appearance there once in a while and on that's odd.

**Lenny** (01:06:53):
True.

**Yuriy Timen** (01:06:54):
How folks can be helpful to me, honestly, promote and shout out of Lenny's Newsletter and Lenny's Pod and that if you're building awesome things, come talk to me. I always carve out some amount of time in my life just for noncommercial things, just to have conversations with founders and spent 30 minutes with them on a phone, expecting nothing in return and maybe save them some time from making some of the mistakes that I've made and help direct them on a more path. So it's about it.

**Lenny** (01:07:27):
Amazing. You are awesome. Thank you so much for making the time to do this. I learned a ton. I can't wait to get this episode out. There's just so much meat to this thing,

**Yuriy Timen** (01:07:36):
Dude this was good.

**Yuriy Timen** (01:07:37):
I feel like my nervousness was unfounded. This was super organic. You are just as welcoming as you are outside of the pod. So yeah. Thanks for having me.

**Lenny** (01:07:50):
Thanks Yuriy. 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.

---

## [15/20] The role of AI in product development | Ryan J. Salva (VP of Product at GitHub, Copilot)

**Ryan J. Salva** (00:00:00):
We had actually created a snapshot of GitHub's public code for what we call the Arctic Code Vault, right? Essentially, this is up in like way in the Northlands of Finland, there's a seed vault. We were like, you know what? Seed vaults are really there to preserve the diversity of the world's flora in seeds in case of some crazy either natural or manmade disaster. But another really important asset to the world is our code, our open source. This represents actually a lot of the collective, well, certainly software, if not intelligence of kind of the modern world, right?

**Ryan J. Salva** (00:00:44):
We had put this snapshot of public repositories on this silver film that would be preserved for thousands of years in this Arctic Code Vault. Well, we took that same data snapshot and we brought it to our friends over at OpenAI to see like, okay, what can we do with these large language models built on public code? Well, it turns out we can do some pretty cool things.

**Lenny** (00:01:13):
Ryan Salva is VP of product at GitHub, where, amongst other projects, he incubated and launched GitHub Copilot, which in my opinion is one of the most magical products that you'll come across. If you haven't heard of it, it uses OpenAI's machine learning engine to autocomplete code for engineers in real time as they're coding. I think it's one of the biggest advances in product development and productivity that we've seen in a while. I'm always really curious how a big product like this starts, gets buy in, build momentum, and then launches, especially at a big company like Microsoft and especially a product like Copilot that has surprising ethics challenges, scaling challenges, business model questions.

**Lenny** (00:01:55):
**Ryan J. Salva** (00:04:42):
Thank you, my friend. I am genuinely very excited to be here. Lovely to geek out with you for a little while.

**Lenny** (00:04:48):
I'm excited as well. We were chatting briefly before we started recording and you mentioned a little bit about your background, which is really unique for someone that is leading product at GitHub. Could you just share what you studied in school, and then briefly just how that led to your career in product management?

**Ryan J. Salva** (00:05:07):
Oh wow! You're going to make me remember all the way back to school. Okay. Back in school, I was not a classic software engineering, CS major. The kind of esoteric answer is philosophy of aesthetics and 20th century critical theory. The easier access answer is philosophy and English. But primarily it was really about how do we, as people, communicate with each other, how do we express ourselves through creativity. As humans since the dawn of time have been painting on cave walls and dancing around the fire and writing stories and novels and singing to each other. I was just really interested in how we convey our experience of the world to others.

**Ryan J. Salva** (00:05:58):
I got started in software development and product management because I wanted to be in the business of creativity. We're at a really, really unique time in human history where we actually get to witness the advent of a brand new medium. Software development and the worlds that it creates wasn't possible, I don't know, maybe 50, 60 years ago now. If I'd been born in the 1700s, I probably would've been the guy making, I don't know, new colors of paint and paint brushes, but I wasn't. I was born kind of at the turn of the 21st century, and so I work in engineering.

**Ryan J. Salva** (00:06:39):
That's what I've been doing for the last about a little bit more than 20 years now, working sometimes in startups, some of them other people, some of them my own, about 10 years at Microsoft and now three years at GitHub.

**Lenny** (00:06:51):
Amazing. I didn't know that was a job to make new paint colors for paint brushes. Is there a color you would come up with?

**Ryan J. Salva** (00:06:59):
Oh man! It so happens that yellow... I think I would do a really vibrant gold sunshine yellow if I was in that business.

**Lenny** (00:07:13):
Very positive, happy. I love it. That could be a new GitHub brand color. Today, you're VP of product at GitHub. Before that, you were a super senior product leader at Microsoft, and I'm always curious how that transition happens when you move from just a longtime senior product leader at a larger company to taking on something like this that was an acquisition. I'm curious what made you decide to take this leap, and then just was there anything interesting about the machination that went into just making that transition and figuring that out?

**Ryan J. Salva** (00:07:45):
Yeah, it's a good question. Like I said, I was working on development tools and developer services when I was there at Microsoft. Specifically, I was leading product for what they call One Engineering System. It's essentially the shared developer infrastructure for all Microsoft products like Windows and Office and Azure and things like that, as well as Microsoft's DevOps solution called Azure DevOps. When the acquisition happened, it was clear that so much of the energy, so much of the focus and the innovation that was going to be happening around developer tools and services was going to be happening around GitHub. I mean, that's where the community is creating.

**Ryan J. Salva** (00:08:34):
That's where people are learning, that's where so much of the mind share of just the development community is focused. Like I said, I'm motivated. What I care about is helping people create. It was very clear to me that there was no place that I could have a larger impact than working at GitHub. I really took that opportunity to make the transition out of a little bit more enterprise focused internal role at Microsoft to going where I could work on everything from, I don't know, AI technology like Copilot to a cloud hosted development environments like Codespaces, repos, which literally every single developer on the planet is participating in some way GitHub repos in a typical year.

**Ryan J. Salva** (00:09:28):
That was what I wanted to accomplish, is just like, how do I get more connected to the community, especially the community outside of what Microsoft could reach on its own. The decision to move as well, I think, was really focused not just on what GitHub was and maybe is at the time, but what GitHub also can be. I mean, GitHub has more than a decade, nearly a decade and a half of history of bringing developers together to collaborate on code through repositories. But in the last few years, we've really expanded that portfolio to include so many different parts of the developer life cycle.

**Ryan J. Salva** (00:10:13):
Again, I talked there about Codespaces and Copilot, but it's also actions for CI/CD and advanced security. As developers, we are so much more than just where we put our code. There's a whole part of the tool chain there. And to get to an opportunity to work on so many V1 products, like that is creation itself, to be able to build an entirely new product, get it out to market, test it, iterate on it, and really feed on the energy that's coming back from the community.

**Lenny** (00:10:46):
Awesome. There's definitely a lot of energy coming out of GitHub. What I want to spend most of our time chatting about is a product that your team helped launch and incubate, which is GitHub Copilot, which just from my outsider perspective feels like one of the biggest advances in software development in, I don't know, a decade, maybe more. It's definitely one of the most magical products out there and your team and you kind of led the incubation and launch of the Copilot.

**Lenny** (00:11:15):
I'd love to spend most of our time chatting through that. The first question... Okay, cool. My first question just for folks that don't know a lot about Copilot is just like, what is it? Can you just kind of briefly describe what Copilot is?

**Ryan J. Salva** (00:11:26):
Yeah, sure. Developers for the last 20 years or more have had essentially simple, intelligent autocomplete. You hit the period and you get the next variable that might come up. It's helpful for moving a little bit faster through your code, helpful sometimes for remembering what the particular syntax might look like for a method or a function. Copilot is essentially that magnified by many lines of code. It is multi-line autocomplete that is fundamentally powered by an AI model called CodeX, which is a derivative of another one that you might be familiar with, GPT-3.

**Ryan J. Salva** (00:12:15):
When you are in the editor, it could be VS Code, it could be IntelliJ, it could be them, essentially, as you are typing, Copilot will provide suggestions usually in kind of this italicized gray text that is really, to your point, kind of magical what it's able to infer. Based upon the variables around it, the class names, the method names around it, your comments, Copilot infers what you intend to create, and then hopefully does a pretty good job at nailing it by providing scaffolding code template that you can then riff on. Now, what we tend to find is that developers love it. They really enjoy it. They kind of find themselves getting a little addicted to it because it helps them stay in the flow.

**Ryan J. Salva** (00:13:08):
As developers, we love to be in that place. I love to be in that place where I'm creating things, where I'm focusing on some product, some piece of software that I'm going to give to my customers, my users. The labor of remembering what's the order of parameters that need to come into a particular API, or hey, what's the particular syntax of this thing I'm supposed to do, or oh, I've got to create a bunch of dummy data that is days of the week or months in the year. That's just labor. It's not creating. It's just typing.

**Ryan J. Salva** (00:13:47):
Copilot helps developers stay in the flow by bringing all of that information into the editor, preventing them from having to go check out documentation or watch tutorial or go to Stack Overflow and either find an answer or worse, have to ask a question and wait for an answer. It just brings all of that into the editor and gives the developer often multiple suggestions that they can choose from and just pick and choose what is the right solution to solve the problem for the thing they're trying to create.

**Lenny** (00:14:21):
Awesome. What I'm most curious about, and we're going to spend time on this, is just how a product like this comes to be at a larger company. But before we get into that, what's the craziest story of someone using Copilot to write code? And I'll share one real quick. I was watching some YouTube videos to prepare for this chat and one guy, maybe this is the Turing Test of AI writing code, is he used Copilot to center divs. He's like, "Wow! This did it right." And then another guy, he's an instructor of code.

**Lenny** (00:14:51):
He makes YouTube videos teaching people how to code and he's like, "Copilot just gives you the answer immediately, and so I can't make these videos as easily. I have to turn it off so that doesn't just give it away." I'm curious, what have you seen?

**Ryan J. Salva** (00:15:03):
There are so many of those. I'll just kind of give a couple of recent ones that I've heard. I was talking to one developer who was... He's actually an educator and he's teaching kids how to code, usually like kind of high school age, so 16, 15, that kind of thing. His experience matches my own, which is that many of us, we learn to code best not by arbitrary exercises, but by actually building something that's going to be useful solving problems.

**Ryan J. Salva** (00:15:41):
What he does is he matches small businesses and medium size businesses who need to build internal tools with essentially classes of students, like a group of maybe six or eight students, and then gives those students Copilot and says, "Here, small business, medium size business. Group of students, go build this internal tool for this business."

**Ryan J. Salva** (00:16:08):
Copilot is essentially kind of whispering in the student's ear, metaphorically speaking, "Hey, here's how you solve this problem. Here's how you do this," and students build not only the tool, the software that the business needs and then get to put that on their resume and their application for college and university, but they also get to learn by using the tools that likely are going to be part of the core DNA of the developer tool chain two, three, four years from now, as AI starts to permeate our entire stack. That was a pretty cool recent one that I talked to.

**Lenny** (00:16:48):
That is very cool. I didn't think about just the education lever here of just making it so much easier to learn to code, not even just building code.

**Ryan J. Salva** (00:16:56):
And that's the thing, Copilot is particularly good not just at taking away some of the effort, but often... There's learning a new language, and then there's also just waiting into a code base that you're not necessarily familiar with, right? I mean, heck, sometimes I don't recognize some of the code that I wrote six months ago or a year ago. It feels like I'm wading into new territory. But maybe you need to fix a bug in an app that you don't often touch, wading into that code base is kind of learning and creating a mental map for that code base.

**Ryan J. Salva** (00:17:30):
One of the really magical pieces of Copilot here is that, that AI is collecting context of the application that you're going into. It can help you build that mental map and learn the code base, even if it's a language that you're already familiar with.

**Lenny** (00:17:47):
Awesome. Going back to the beginning of Copilot and how it started, I'm always curious how a project that ends up being a huge deal to a larger company begins and especially how it builds momentum, how it gets buy in, and then just gets out the door. Can you talk about just the original seed of this idea like, who did it come from, who had the original vision, how did this idea emerge and build momentum where you put resources into it?

**Ryan J. Salva** (00:18:13):
Oh wow, what a long, and I don't know, depending upon your point of view, sorted or exciting story that is. Microsoft and OpenAI have been collaborating for quite a while now on large language models, making its way into all different experiments and different parts of both Microsoft's software portfolio, as well as just helping OpenAI by providing the compute necessary. It takes massive amounts of compute to train these models. They were mostly large language models. Couple years ago now, it kind of dawned on us that, well, language models aren't just English and Spanish and German and Korean and Japanese, but Python and JavaScript and Java and C# and Closure.

**Ryan J. Salva** (00:19:07):
All of these are languages too. In fact, they're kind of nice from an AI perspective because they're relatively constrained in terms of their semantics, right? The number of words, I put that the in scare quotes as it were, that can be expressed in Python, for example, is much smaller than the English language, which has all sorts of different grammar rules and nouns, verbs, adjectives, adverbs. We started to see what it would be like to actually bring code to these large language models. The way that I actually got introduced to it is kind of funny. Microsoft and OpenAI had this idea.

**Ryan J. Salva** (00:19:53):
At the time, one of the teams that I was responsible for was GitHub's infrastructure team, the team responsible for our data centers, our reliability, our rep time. We noticed one day that we were getting hammered, I mean absolutely hammered with a tremendous amount of clone requests. We're like, "Oh my gosh! Is this like a denial of service attack? How are we going to respond to this? What's going to happen?" We figured out pretty quickly that it was actually OpenAI. They were cloning all of our repositories to harvest the data out of GItHub.I mean, it's totally legit practice, but it does have a real consequence.

**Ryan J. Salva** (00:20:33):
We were able to step in and mitigate it very quickly. There was not a reliability kind of an uptime incident there, but we're like, "Hey, you all, cool. Love this thing. Let's see if we can get that data to you in a more responsible way, in a way that's packaged a little bit more to meet your needs." What we did is just the year before that, We had actually created a snapshot of GitHub's public code for what we call the Arctic Code Vault, right? Essentially, this is up in like way in the Northlands of Finland, there's a seed vault. We were like, you know what? Seed vaults are really there to preserve the diversity of the world's flora in seeds in case of some crazy either natural or manmade disaster.

**Ryan J. Salva** (00:21:25):
But another really important asset to the world is our code, our open source. This represents actually a lot of the collective, well, certainly software, if not intelligence of kind of the modern world, right? This represents actually a lot of the collective, well, certainly software, if not intelligence of kind of the modern world. We had put this snapshot of public repositories on this silver film that would be preserved for thousands of years in this Arctic Code Vault. Well, we took that same data snapshot and we brought it to our friends over at OpenAI to see like, okay, what can we do with these large language models built on public code?

**Ryan J. Salva** (00:22:03):
Well, it turns out we can do some pretty cool things. Just like a translation tool that goes from English to Spanish, Spanish to German, you can also go from English to Python or Python to C#. We're like, okay, this is cool. We can start to get not only translation, but a little bit of predicted text here as well. We're all I think fairly already familiar with predictive text already in our code editors as IntelliSense. But in, I don't know, you go to your favorite word processor and chances are that you've got some kind of predictive text happening there as well.

**Ryan J. Salva** (00:22:43):
We started experimenting with different user experiences, right? Do we want it so that you, I don't know, right click and get a little side panel that comes up with a bunch of different options for things that you might want here. That was nice because it would give you hold functions, but it's out of the cursor, right? You had to really... Even if you weren't switching over to a different window, you still had to switch over to a different panel, which itself was a little bit distracting. We eventually came to this idea of inline autocomplete.

**Ryan J. Salva** (00:23:20):
We were able to with the kind of partnership of some of our friends over on the Microsoft side of things, partner with our friends in Visual Studio Code, they're like, hey, there's not really an extensibility yet in your editor for this multi-line autocomplete, but we've got an idea for how this might work. Played around with the actual presentation of it. What should the key strokes be? What should the presentation layer be? The gray italicized tech seemed to be a good way of indicating that it was ephemeral, as it were. Pretty early on, we landed on this user experience that is Copilot as most developers experience it today. I want to say that was at least 16 months ago, 14, 16 months ago. Since then, we brought it to developers.

**Lenny** (00:24:15):
Just to double click on that, you're saying just less than a year and a half ago, this kind of really started as a project and now it's out to the world. Is that right?

**Ryan J. Salva** (00:24:26):
That is exactly right. That's exactly right. It's about a year and a half ago.

**Lenny** (00:24:30):
That's insane. What was that period between OpenAI almost taking down GitHub to I guess that point?

**Ryan J. Salva** (00:24:38):
The period in between kind of OpenAI almost taking down GitHub and then us really arriving at the user experience, part of that was, frankly, a lot of really smart researchers at OpenAI experimenting and doing what only world class AI researchers can do. It was a lot of them experimenting, occasionally asking for updates to the data set, tossing back to us a model that we might play with and tinker around with. These models have literally thousands of parameters that you can pass to them. When you're really thinking about GPT-3 and CodeX and then the transition from that to something like Copilot, it was not just like the model...

**Ryan J. Salva** (00:25:27):
Creating the model is one thing, but then figuring out how to use the model in terms of what parameters do you want to adjust for, what do you want to optimize for in terms of... A great example of this is performance, right? When you're in a code editor, you don't necessarily want to type, type, type and then have to wait one second, two seconds, three seconds to get a suggestion back when your entire goal is to stay in the flow. We would run experiments to see how many milliseconds are the right amount such that a developer doesn't feel like they're being interrupted by Copilot and a suggestion.

**Lenny** (00:26:06):
What's the answer to that?

**Ryan J. Salva** (00:26:09):
It seems like right now it's around 200 milliseconds. Depending upon where you're in the world, your latency can go up or down a little bit from there. But it seems like the sweet spot is somewhere around 200 milliseconds.

**Lenny** (00:26:20):
Good to know.

**Ryan J. Salva** (00:26:22):
We also experimented quite a bit. It's not just about the model, but it's also about what you feed the model. How do you prompt the model to return back a useful response? This kind of began a journey of experimentation for what we call prompt crafting.

**Lenny** (00:26:40):
Going back to the way this started, it sounds like basically it was kind of this fortunate accident where OpenAI just did something that you didn't expect. And then somebody within this PhD group that you described is like, "Oh wow. Maybe we could do something really good with this." Is that kind of how it began?

**Ryan J. Salva** (00:26:57):
That's fairly accurate. Yeah. I mean, we had a model that really was amazingly good, like a step level change in actual intelligence, right? And then marrying that up against a really good use case that actually changes developers' fundamental experience of the creation process, the creative process.

**Lenny** (00:27:25):
Was there kind of a point at which it was clear to you or leadership in general like, we should double down on this thing and go big? Or this smaller team was working on this idea and then you're like, "Oh wow, this is going to work?" Or is it always like, "We will bet on this thing, this is such a big and great idea. We're going to invest resources for sure from the beginning?"

**Ryan J. Salva** (00:27:48):
The original team that was working on Copilot at GitHub was the team that we call GitHub Next. Essentially their job is to work on second and third horizon projects. What some folks might call moonshots, right? Things that we never really expect work in the next one or two years, but might three, five years down the line actually turn into something meaningful.

**Lenny** (00:28:17):
Is there a concrete definition of horizon two and three? Is it like number of years out like Amazon style?

**Ryan J. Salva** (00:28:23):
Not necessarily a concrete definition. For me, I usually ballpark it as first horizon is the next year, second horizon, the next three years, third horizon, the next five years. But we generally think of it more as a measure of ambiguity and confidence level more than calendar dates.

**Lenny** (00:28:47):
**Ryan J. Salva** (00:29:58):
I would say it is not necessarily Microsoft thing, but is definitely at GitHub, how we have really contextualized it. Not to say that there aren't teams at Microsoft who might also use that methodology, but where we've been really maybe explicit or intentional about it is at GitHub where we've actually ring-fenced a team to think about that horizon two and horizon three work and kept them separate from EPD. EPD here being engineering, product, and design, the folks who are working on building productized operational products that we bring to market and we either give away or monetize in some way.

**Lenny** (00:30:39):
This is so interesting. There's a lot of companies that have these sorts of R&D groups, new product experience team at Facebook and Google has one. I'm not sure how many successes have come out of these teams. From what I've seen, and I'm curious, what have you... And clearly you had a huge success as far as I can tell so far. Is there anything you've learned about how to do this, where you invest in these big moonshots within a larger company?

**Ryan J. Salva** (00:31:05):
I mean, I think the first step is to invest in it. The first step is really hire really smart people, attract smart people, and give them the opportunity to be creative. Don't expect anything out of them that is going to turn into a money maker or something that is going to be beholden to fundamentals around security, privacy, uptime, accessibility, all that groovy kind of stuff upfront. They need space to create and experiment.

**Ryan J. Salva** (00:31:37):
And also, when you do get to a place where that team has an idea that is clearly connected to a representative set of customers who have a genuine problem and there is signal with at least medium confidence that this solution, whatever it is, solves it in a novel way, that's the time to start thinking about, okay, let's actually put a little bit of... I'm going to call this market testing. It's nothing so formal as market testing. It's really just like, let's start to actually bring prototypes of this in front of more and more customers to kind of test it out and see, hey, is this actually solving a problem for you? Is this something that you would use? This is where the transition between Next and EPD at GitHub really started.

**Ryan J. Salva** (00:32:35):
This is actually where my role in the product cycle kind of really started to increase. I had kind of been in tight connection and been monitoring the work and kind of consulting a little bit with the Next team prior to that. But it was that moment when we identified that, okay, this is actually something real. Customers are saying, developers are saying, "This is magical. This does something extraordinary that I could not do on my own," that we started to think about, okay, how do we transition this over? From there, we're really just like, okay, we think we've got a hit here. We think we've got something that we can actually bring to developers.

**Ryan J. Salva** (00:33:21):
We made an intentional decision to take some of the researchers who were in the Next team and for a finite period of time, move them over to create a new EPD squad. We want them to be researchers, but we need to do knowledge transfer and we needed to actually provide the seed for a team that could eventually operationalize and productize. And that kind of began the technical preview where we started to invite tens of thousands, then hundreds of thousands to the technical preview. In that technical preview, we started to see crazy mind-blown emoji tweets and threads on Hacker News about people getting really, really excited about it.

**Ryan J. Salva** (00:34:09):
That's how we knew it was time to start scaling and it was time to really start thinking about how do we do hiring so that we can build in some insulation around these researchers so that they can eventually go back to GitHub Next to do what they do best, which is be innovative and creative and think about the next moonshot. That process, that took... Well, we're actually still kind of at the tail end of it now. Here we are, like I said, roughly a year and a half after the initial creation of the product, having gone through technical preview, have achieved general availability. We've now hired in a team around them.

**Ryan J. Salva** (00:34:53):
The researchers actually as early as last month have started to gradually move back over to GitHub Next. An EPD squad, multiple EPD squads actually are now taking the product forward and starting to respond to customer feedback to think about, okay, how do we now as a product team, carry this roadmap forward from an idea that originated in GitHub Next?

**Lenny** (00:35:22):
I love that insight of bringing the people along and not just kind of like, cool, we'll take it from here. If you were to build a team like this again somewhere to this kind of R&D horizon three or two teams, is there anything else you would do differently, any lessons you take away from this experience for maybe founders or PMs working at larger companies that are like, "Hey, we should have something like this?" Is there anything else that you find is important for making something like this successful?

**Ryan J. Salva** (00:35:49):
The criteria for moving researchers back into their R&D team, whatever that happens to be for your organization, that can't be based on a calendar. It needs to be based on a replacement in seat, who's actually doing the job and has picked up all of the skills necessary, and only then can the researcher move back. Make sure that you've got continuity of expertise and sets and domain familiarity before you move over. I feel like we've managed that pretty well today. As well, it's critical that the team who is taking over from the R&D shop feels like they have control over their own future. You can't really delegate roadmap to an R&D team.

**Ryan J. Salva** (00:36:44):
The team who's responsible for maintaining the product, for building the product, who has the closest feedback loop with the end customer, they're the ones who really need to own and feel like they control the roadmap. Making sure that you're not outsourcing innovation exclusively to an R&D team, but that is happening within the product team as they take ownership over the idea and over the use case in the customer. Last I would say here is really that engineering fundamentals in a lot of ways are the contracts that differentiate an R&D team from an operational product team.

**Ryan J. Salva** (00:37:30):
Bringing that fundamentals process into it is going to feel candidly a little bit unnatural to the researchers. That takes therefore a little bit of cultural change management for everyone to just adapt their way of working and understand that we're graduating from an experiment and a research project to an operational product, and often because those researchers are... They're the first wave that come over. They're the seed of the project. It's going to feel a little bit unnatural to them and they probably won't have all the right skillsets in order to make that transition.

**Ryan J. Salva** (00:38:08):
Making sure that you've got a good mix of engineers who are comfortable maintaining a service, as well as engineers and researchers who are really thinking about, what is the idea that we've created, what is the new thing that we've brought to market, and can bring that vision to it.

**Lenny** (00:38:27):
Yeah, I can totally see the challenge that comes from... This was my thing. I've been working on this. What are you guys doing to this project? Where is this going? I'm not sure I'm feeling... And then there's all these new asks that are coming at you like, oh my God, this was so much fun and now I have to scale this freaking thing.

**Ryan J. Salva** (00:38:46):
I mean, this is the best problem in the world to have. Talk about kind of customer ask, for Copilot in particular, the amount of chatter, the amount of customer feedback that was coming in especially for us with AI, I mean, the world is still figuring out AI, candidly. I mean, we're getting a lot better at it, especially in the last couple of years with things like Dolly and Copilot. But it brings with it not only engineering challenges, but also, frankly, ethical challenges and legal challenges, like making sense of what our expectations are of AI. If AI produces something that is offensive, who's at fault?

**Ryan J. Salva** (00:39:37):
Our stance on it, what we ended up coming to is actually the framing of Copilot as an AI pair programmer I think is a useful one. Pair programmer, I suspect most of your listeners will know, but pair programmer is usually two developers sitting side by side working on a problem together. One's at the keyboard and the other one's kind of helping them talk through it, talk through the ideas and make corrections, that kind of thing. Well, if Copilot is your AI pair programmer and they're whispering crazy stuff into your ear and they're bringing politics into it or gender identity into it or, I don't know, whatever other...

**Ryan J. Salva** (00:40:19):
They're spouting off slang and slander and all that kind of stuff. You're probably not going to be able to focus on your work, right? It's going to be really distracting. Really coming down to some principles about what is the use case we're trying to solve, what is appropriate, I put this in scare quotes, behavior of the AI bot sitting side by side with you, helped us create some principles or some guidelines for the developer experience that we wanted to create.

**Lenny** (00:40:52):
Oh, I love that. Just kind of creating a persona of the thing to help you inform how the behavior of the thing should work. How do you work through these challenges? Is it discussions with you and the legal team? I don't know, these ethical things are really tricky, I imagine. How do you approach them like that as a product team?

**Ryan J. Salva** (00:41:09):
It is conversations with a very, very wide cast of characters. This product in particular, I probably spent more time with legal than any other products that I've ever kind of been responsible for. All wonderful creative people. But it's not just legal. It is also privacy and security champions. It is, frankly, developers, like the people who are using it, listening to them. Hey, what works here? What doesn't work for you here? Why is this offensive? Why is it not offensive? We'll continue on the example of the crazy pair programmer whispering crazy things into our year. When we first started out, we didn't really have any filter on Copilot whatsoever the very, very, very early days.

**Ryan J. Salva** (00:41:58):
And then eventually we're like, okay, it needs to be slightly more controlled experience. We need to edit out some of the most egregious stuff. We introduced a simple block list of words, and these block lists are always fraught with peril, like which words are okay, which words are not okay. All of a sudden, we become editors of language and that's kind of a scary place to be. I'm not comfortable with it at least. But at a certain level, it has to be done, because otherwise you're going to create a bad developer experience.

**Ryan J. Salva** (00:42:35):
Often we would get feedback from developers of like, "Hey, this particular word was blocked. That it was blocked either was offensive to me or prevented me from being able to get good value out of the product."

**Lenny** (00:42:51):
Oh man.

**Ryan J. Salva** (00:42:52):
Always kind of dancing the dance of editorial content. We're actually at a place now where we're able to partner with the Azure Department of a Responsible AI, and they've created some really extraordinary models that help detect I'll call it sentiment for lack of a better word, but basically when there is something that is patently offensive. Because there are some words that in some contexts may be offensive and in some context may be totally reasonable, especially when you get into software for medical kind of scenarios, right?

**Ryan J. Salva** (00:43:35):
Being able to start to shift a little bit to focus or to rely on AI models that can also do a better job than we could with crude or simple block lists is maybe another proof point both of how AI as a solution for common development problems is getting way better at solving more parts of our stack or filling in for more parts of our stack. At least in our case, we were pretty fortunate to be able to deliver on or depend on a parent company's contributions to solve a real acute problem that GitHub probably could not have solved on our own.

**Lenny** (00:44:16):
I never thought that Copilot would be... That you would have to worry about it saying things that are crazy. That is wild that you guys have to deal with that. Wasn't it Microsoft that had that bot that turned really negative and eventually shut down?

**Ryan J. Salva** (00:44:31):
It was.

**Lenny** (00:44:31):
There's experience there.

**Ryan J. Salva** (00:44:32):
What was its name? Talia or something like that?

**Lenny** (00:44:35):
Something like that.

**Ryan J. Salva** (00:44:36):
Yeah, something like that. We don't want another one of those incidences.

**Lenny** (00:44:40):
Wow. What this makes me think about is your team is at the forefront of AI in this applied way. I'm curious what your thinking is on just where this goes for developers especially. I saw a stat that maybe 40% of people's code is now written by Copilot. I don't know if that's right. But is the vision in the future becomes something like 90? Where do you see this all going?

**Ryan J. Salva** (00:45:02):
Just to put a fine point on that stat, it is 40% is specifically for Python developers. Candidly, it varies depending upon the language. Because as you might imagine, some languages have better representation in the public domain than others. And usually both the volume and the diversity of training data correlates with the quality of suggestions, which is then represented by either the number of lines written or the acceptance rate or any one of a number of other metrics.

**Lenny** (00:45:35):
Awesome. Thanks for clarifying.

**Ryan J. Salva** (00:45:36):
Yeah, totally. We see it range anywhere from the upper twenties to the forties across all the different languages.

**Lenny** (00:45:43):
Just to throw this out there, as a not great engineer, I used to be an engineer for about 10 years, I welcome our AI Overlords writing all my code. I'm excited for this to do more and more. And yes, I'm curious where you think this goes.

**Ryan J. Salva** (00:45:58):
It does. It enables even mediocre developers like myself to be able to do some pretty amazing things. But where's it going? First, I think, I hope it's obvious to most developers that AI is going to infuse pretty much our entire development stack in the not so distant future. Copilot is really just the very tip of the sphere for a lot of innovations and better managing maybe our build queues or helping to... Here's a great one. I don't know about you, but often the comments that I get with commit messages and PRs aren't super great. It puts a lot of effort onto the code reviewer to go figure out what the developer was actually trying to do.

**Ryan J. Salva** (00:46:55):
What if AI could summarize all of your changes with your full request and you just have to, as the contributing developer, just review it to make sure it's accurate, send it on its way, and you don't have to put in extra effort for that. There are lots and lots of different opportunities for AI to essentially be able to take some of the drudgery out of our work so that we can focus on creative acts. What I hear from developers and what I experience myself is that Copilot kind of forces me to think a little bit more about what are the design patterns I'm trying to create?

**Ryan J. Salva** (00:47:33):
What is the end user experience or the outcomes that I'm trying to drive with my code, and that I can rely on Copilot to scaffold out a lot of that so that I can focus on more creative work? That is really what I hope for our industry five, 10 years from now, is that not only will we be inviting more developers or more people to become developers by essentially providing a layer of abstraction a little bit, or at least a little bit of a hand in development, but that also the really experienced developers are focusing on much larger problems and focusing on outcomes and creativity rather than really low level difficult rote memorization of things like syntax or ordering of parameters and the like.

**Lenny** (00:48:32):
Great. If nothing else, that'll keep people from just having a tab of Stack Overflow, copy and pasting every function that they're trying to figure out.

**Ryan J. Salva** (00:48:42):
I want Stack Overflow to stay in business, but I would mind a little bit less contact switching myself.

**Lenny** (00:48:48):
In the experience of scaling this thing, what would you say has been the biggest challenge either technologically or even operationally just kind of scaling it to a real product that people are paying for?

**Ryan J. Salva** (00:49:01):
There's a few dimensions of that. One is a problem that's very much of our time in the world, namely that supply chains have been disrupted dramatically over the course of the last few years. It turns out that Copilot for both training and operating the models requires some very rare and unique GPUs that there's not a lot of global supply of. Part of it is just like, can we get enough hardware in order to run these things? We've actually earmarked quite a bit of capacity, and we are greedy, greedy, greedy for more capacity globally. As soon as we can produce those chips and get them in data centers, we do it.

**Ryan J. Salva** (00:49:50):
That's been one kind of unique challenge. I would also say here that operationally, another challenge has been, how do we create a model that the community really feels like ownership over, right? The dialogue that's had to happen as we brought an AI tool to market, especially one that is trained on public code, has required a lot of dialogue between us and our community. Every good product manager should be spending as much of their time as possible with their customers, with their potential customers.

**Ryan J. Salva** (00:50:34):
Copilot, in particular, has been a more complicated kind of rollout because we as an industry, as a society are still figuring out how to make sense of it. The amount of give and take between developers and us as a product team has really required us to scale up more of the product team than it has the engineering team.

**Lenny** (00:51:02):
Interesting. And why is that?

**Ryan J. Salva** (00:51:04):
It's a couple of different reasons. I mean, one, like I said, we are trained on public code. Not all of the community is really sure like, when is it okay to train a model on public code? When is it not okay to train a model on public code? Is Copilot producing secure suggestions? Is Copilot producing bug buggy suggestions? There's a lot of doubt. There's a lot of very healthy skepticism. Actually I mean that genuinely. I want people to be skeptical of Copilot. We owe it to ourselves as a community to be skeptical of any AI.

**Ryan J. Salva** (00:51:40):
Because just like there's great potential for benefit, there's also great potential for harm. People keeping us accountable like, how are you preventing things like model poisoning? Is there going to be a new attack vector that we just haven't really thought of yet around AI that might produce negative consequences? We think that we've done a really good and responsible job of that by making sure that first, we are very clear that Copilot is not a replacement for a developer. It will never be.

**Ryan J. Salva** (00:52:17):
We do not want Copilot auto generating code where a thinking, reasoning, breathing human being is not on the other side of that keyboard making recent decisions. We do not want Copilot to replace any other part of the stack, whether it is static analysis tools or your unit tests or whatever kind of measures you're putting in today to make sure that your humans produce good quality code. We want you to keep all of those same systems in place to make sure that humans who are leveraging tools like Copilot continue to produce that good quality code.

**Ryan J. Salva** (00:52:56):
But there's a lot of at the same time anxiety of like, where is AI stack? Is AI eventually going to be... This is back to your question about where will we be five, 10 years from now. Will it be writing 90% of the code? We don't want Copilot to be that... We don't want it to replace anything. We want it to augment. The idea here is really that AI is an enabler for developers to focus on the creative work, to stay in the flow, to be able to move faster. Working through those anxieties, working through that healthy skepticism takes conversation. It takes dialogue. And that takes us on the product side having that guided conversation with the community.

**Lenny** (00:53:50):
It feels like it connects back to your education back in the day, philosophy and literature. How convenient is that?

**Ryan J. Salva** (00:53:57):
It often feels very connect... I mean, certainly the education side of things taught me that the importance of dialogue, the importance of skepticism is valuable in so much more than esoteric armchair ponderings. It's actually applicable to the real world.

**Lenny** (00:54:17):
Maybe a final question before we get to our very exciting lightning round.

**Ryan J. Salva** (00:54:21):
Woo!

**Lenny** (00:54:23):
Just looking back at this whole experience of, one, just building, incubating, launching this big bold bet within a big company, you can go in either direction, either just any lessons on just taking a bold bet versus incremental wins and how you think about investing in these two kind of categories, or just within a large company, a lesson of just how to build something like this, like a massive new product from just a seed of an idea to a large new business line potentially.

**Ryan J. Salva** (00:54:51):
As both a product manager and a portfolio manager of multiple products, I'm responsible for multiple product lines at GitHub, the allocation of time, of focus, energy, and resources becomes a really challenging question. The answer to which isn't always the same, depending upon the time, world circumstances, organizational circumstances, technology circumstances. As a general rule, as a general principle, I certainly try to make sure that we're always reserving some capacity for bold, audacious experimental research projects. You can think of those really uncertain bets as being five to 10% of the team's capacity. About 25, maybe 30% of the team's capacity should generally be on just operations.

**Ryan J. Salva** (00:55:54):
How do we keep our in-market products meeting customer expectations? And then the remainder of it, what is that, about 60% or so, is really on incremental progress for our end market products. How do we make iterative improvements and continue to actually realize payoff for the larger bets that we made one, two, three, four years back? And from a rough distribution, that's generally how I run my larger teams. That works when you have larger teams though. At startups, where we were pretty much only a big bet, obviously your percentages get very different and it becomes a matter of you're all in for that one proverbial lottery ticket.

**Lenny** (00:56:50):
Awesome. Thanks for sharing that. I was going to ask you the percentages that you recommend. Thank you for getting to that. With that, we've gotten to our very exciting lightning round. I'm just going to ask you five questions briefly and just whatever comes to mind, whatever answer you have. Let's do it. Sound good? Okay. What are two or three books that you recommend most to other people?

**Ryan J. Salva** (00:57:13):
Oh, good question. One of them is a book on user experience called Make It So. It's a reference back to Star Trek, and the idea here is essentially that user experiences that are presented to us in sci-fi often make their way into our everyday products and tools 20, 30 years down the line. It is a great eye-opening, illuminating and just really fun book. That's one. And then completely different take, I'll go outside of tech and I'll just do entertainment value. There's a David Foster Wallace book called Brief Interviews with Hideous Men that I love. It's a collection of short stories.

**Ryan J. Salva** (00:58:04):
And essentially what it is, is it is if you're watching a movie and the villain gets their opportunity to have their big speech, which kind of explains why they are who they are, it makes them maybe a little bit vulnerable in that moment, it's that speech 10 times over for different hideous people, terrible, terrible people. Interesting read. I recommend it.

**Lenny** (00:58:31):
I love that. It reminds me of this book that is the interior design of dictators and they show you their homes of Saddam Hussein, Hitler, and all these guys.

**Ryan J. Salva** (00:58:43):
Dude! Oh my gosh, that's awesome. I got to find that one. You'll have to send it to me.

**Lenny** (00:58:47):
I found one at an old bookstore, like used bookstore. I don't know if they're around anymore, but I'll find it. Second question. What's a favorite other podcast that you like to listen to or recommend if there's any?

**Ryan J. Salva** (00:59:02):
Oh god, there's so many. I consume hundreds of hours of podcasts every month. It is crazy. I can choose many. I'll give you just one. The Memory Palace with Nate DiMeo is an excellent storytelling podcast. He does about 20 minute vignettes, usually selected from kind of American history. He also was the artist in residence at one of the museums in Washington, DC. And if you're ever at I think it's the American History Museum or something like that, if you're ever there, you can go to different rooms in the museum and he'll tell you stories about the objects or the rooms that you see there. It's a magical experience recommended to anyone.

**Lenny** (00:59:56):
Wow! I love those. What's a recent movie or TV show that you've really enjoyed?

**Ryan J. Salva** (01:00:00):
I don't know if this counts as recent, but it's one that I watched recently, which was Arrival. Yeah, that counts. Arrival. Movie ostensibly about aliens, but is really about language and memory. I found that really, really compelling.

**Lenny** (01:00:20):
Have you read Ted Chiang books and short stories?

**Ryan J. Salva** (01:00:23):
I have not. I have not.

**Lenny** (01:00:24):
Oh wow! Oh, you would love it. Arrival is from one of his story, I believe, is one of his stories and there's a whole book of many more short stories by the same guy. They're amazing.

**Ryan J. Salva** (01:00:34):
Brilliant. I've got my weekend cut out for me then.

**Lenny** (01:00:39):
There you go. Just leave work and get to reading. What's a favorite interview question that you like to ask in interviews?

**Ryan J. Salva** (01:00:46):
Let's see here. I'll give you a fun one more than it is a challenging one. This is kind of my icebreaker interview question, particularly for more early to mid career product managers. I ask them to teach me something new in one minute. Usually I'll pull up my phone and I'll start the timer. I'll give them a second to think about it and start the timer. They're graded on three different criteria. One is completeness. Did they actually finish the lesson inside of one minute? Two is complexity. It's one thing if you teach me how to, I don't know, pat my head and rub my stomach at the same time.

**Ryan J. Salva** (01:01:28):
It's another thing if you teach me something about 18th century ardent connection to religious trends at the time. And then last is really clarity. Oh yeah, clarity is the last one. Clarity is like, do I actually understand? Did I learn something by the end of the lesson? Did they convey the idea fully and wholly?

**Lenny** (01:01:52):
I have to ask, what's the most interesting thing somebody has taught in this question?

**Ryan J. Salva** (01:01:57):
My go-to kind of throwaway answer there about did they teach me something about 18th century art and its connection to religious trends at the time, someone taught me that. It was astounding. It was actually a university candidate, so someone who was still in university, and she was from Vanderbilt University.

**Lenny** (01:02:18):
And was that a strong yes hire?

**Ryan J. Salva** (01:02:20):
It was an extremely strong yes hire. She was freaking amazing. Such a smart person.

**Lenny** (01:02:28):
Amazing. Final question, who else in the industry would you say you most respect as a thought leader or just influence person?

**Ryan J. Salva** (01:02:36):
There are many, but I think for today I'd probably beat myself up if I didn't say Uga Damore. Uga is the primary researcher who really kind of is the true innovator for Copilot. He deserves credit for the initial work and is a brilliant technologist and futurists. I really, really respect him a lot.

**Lenny** (01:03:05):
Amazing. Cool call out. Ryan, this has been so fascinating. You guys are at the forefront of so much interesting work. I honestly can't wait for Copilot for my newsletter so that I can do less work. Maybe that'll come someday. But in any case, I'm excited to see where this whole thing goes. Thank you for being here. Two last questions. Where can folks find you online if they're curious to learn more, reach out? And then is there a way that listeners can be useful to you?

**Ryan J. Salva** (01:03:33):
Easy one. How can folks find me? I am Ryan J. Salva everywhere, Twitter, GitHub. Pick your choice. LinkedIn, Ryan J. Salva. And then how can folks be useful to me? Please, there is a 60 day free trial of Copilot that is there for everyone to pick up and use. Go try it out. When you do, post either on Twitter or Hacker News or on discussions, GitHub Discussions, your experience.

**Ryan J. Salva** (01:04:07):
Give us the good feedback. Give us the bad feedback. I am so hungry to see how people are using it in novel ways and where they're running up against the rough edges too. Like I said, there's lots of room for us to grow and improve from here, but I'm pretty confident that developers will be pretty freaking amazed at what it's already capable of.

**Lenny** (01:04:30):
Awesome. Thanks for being here, Ryan.

**Ryan J. Salva** (01:04:31):
Yeah, dude, thank you so much. It's been a lot, a lot of fun.

**Lenny** (01:04:35):
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.

---

## [16/20] How to build a powerful marketing machine | Emily Kramer (Asana, Carta, MKT1)

**Emily Kramer** (00:00:00):
Forget the product marketing content partner, demand and growth, forget all of it, and just think of marketing as you need a fuel and you need an engine. And goal is like all the things that you're creating. I mean this should be obvious, but it's the content, it's the word, it's the design in some regard. All the things that you're making, all the things that are going to add value. An engine is how you get it out to the right people. And all of the tracking of that and sort of the ops work I put under engine, everyone needs an engine.

**Emily Kramer** (00:00:28):
And the question is, where do you have the biggest challenge right now? Or where do you think if you did more, you would grow faster? Is it on fuel side or is on the engine side?

**Lenny** (00:00:37):
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 one experience building and scaling today's most successful products. Today my guest is Emily Kramer. Emily led and built the marketing teams at Asana, Carta, Ticketfly and Astro, which was a startup acquired by Slack. She's one of the first marketers to be hired at all four companies, and has been instrumental in helping these companies build their marketing function, grow their products, and build their brands.

**Lenny** (00:01:11):
She also writes my favorite newsletter on marketing, MKT1. And the best compliment that I can give her is that she's a marketer that thinks like a product manager. In our chat, Emily shares a ton of concrete advice on what to look for in your first marketing hire, what the different archetypes of marketers are, and who you should look for based on your business model. How to work with marketing effectively as a product team, and also what red flags to look for that tell you that your marketing team is not doing a great job.

**Lenny** (00:01:39):
**John Cutler** (00:02:01):
Hey Lenny. Excited to be here.

**Lenny** (00:02:03):
John, give us a behind the scenes at Amplitude. When most people think of Amplitude they think of product analytics, but now you're getting into experimentation and even just launch a CDP. What's the thought process there?

**John Cutler** (00:02:14):
Well, we've always thought of Amplitude as being about supporting the full product loop. Think collect data, inform that, ship experiments and learn. That's the heart of growth to us. So the big aha was seeing how many customers were using Amplitude to analyze experiments, use segments for outreach and send data to other destinations. Experiment in CDP came out of listening to and observing our customers.

**Lenny** (00:02:35):
And supporting growth and learning has always been amplitude's core focus, right?

**John Cutler** (00:02:39):
Yeah. So Amplitude tries to meet customers where they are. We just launched starter templates and have a great scholarship program for startups. There's never been a more important time for growth.

**Lenny** (00:02:48):
Absolutely agree. Thanks for joining us, John, and head to amplitude.com to get started. Are you hiring or on the flip side, are you looking for a new opportunity? Well, either way check out lenny'sjob.com/talent. If you're a hiring manager, you can sign up and get access to hundreds of hand curated people who are open to new opportunities. Thousands of people apply to join this collective and I personally review and accept just about 10% of them. You won't find a better place to hire product managers and growth leaders. Join almost 100 other companies who are actively hiring through this collective.

**Lenny** (00:03:25):
And if you're looking around for a newer opportunity, actively or passively, join the collective. It's free, you can be anonymous and you can even hide yourself from specific companies. You can also leave anytime and you'll only hear from companies that you want to hear from. Check out lenny'sjobs.com/talent. Emily, welcome to this podcast. I'm really excited to be chatting with you.

**Emily Kramer** (00:03:50):
Yeah. Thanks for having me. Looking forward to chatting with you in depth here.

**Lenny** (00:03:53):
So if I remember correctly, we first met in the first round Angel Track program maybe two years ago, and then since then we've invested in a bunch of different companies together. I'm also just a big fan of your newsletter that we're going to chat about. So just to settle little context for folks, can you just give us a quick high level overview of your illustrious career and then also just plug your newsletter so folks can find it.

**Emily Kramer** (00:04:16):
For sure. And theme of my career has been building out marketing teams at B2B startups. So early in my career I was in advertising, went to business school. But after that I started doing the startup thing and I was at Ticketfly, I was like the second marketer. And then I went to Asana where I was the first marketer when they were about 30, 35 people and built up that team and led the team for just under four years. And then I went to a small seed funded company, help them raise rates and eventually went to Carta, which was about 300 people when I joined-ish give or take, but didn't have a marketing function at the time.

**Emily Kramer** (00:04:49):
So built that function up from scratch. Much like Asana but at a very different stage in the company's life cycle. And then since then I've been advising and investing full time and now have a small fund where we invest in early stage B2B and help them build out marketing. So building marketing, that's what I do.

**Lenny** (00:05:07):
I love it. Okay, so plug your fund and your newsletter real quick just so we can cover that.

**Emily Kramer** (00:05:11):
Oh yeah, sorry about that. My newsletter is the letters mkt1.substack.com and my fund is Market 1 Capital. You can pretty much find most of these things on mkt1.co. Links to all the different various things that I'm doing so I can remember, because there's lots of iron in the fire. So got to keep the website up to date so I don't lose track of all the things that are going on. I also have a job board and a bunch of other things. You have more things going on but I have a number of set of things.

**Lenny** (00:05:42):
Awesome. And we'll link to that in the show notes and everything. I don't think I've told you this but many founders have mentioned you as one of their most helpful angel investors that they've had on their cap table. It just comes up often when we co-invest. And the things that you help them most with as far as I understand is marketing advice, go to market advice, hiring marketing people. And so, I'd love to spend most of our time chatting through, basically the advice that you give founders around marketing.

**Lenny** (00:06:09):
And the first area I wanted to dig into is hiring marketing people. To non-marketing people it's such a mystery of just like, what is a marketing person? What do I expect from them? How do I hire them? How do I find them? How do I interview them? What should I avoid? So my first question is just like what mistakes have you seen founders and teams make when they're thinking about marketing and hiring marketing people?

**Emily Kramer** (00:06:33):
And just to add to that, it's even hard for marketers to hire other marketers. It's even confusing for marketers to know where they fit in. And if they haven't been hired yet exactly what world they should be looking at or exactly who else they should be hired on the team. While it's very confusing for founders and people who haven't kind of been in a larger marketing team to understand all the different function, like also confusing for marketers. And I think that's just because there's so many different sub functions of marketing and there's so many different things that marketers could do.

**Emily Kramer** (00:07:01):
And there's such a range of being a deep specialist. You have people that are just deep SEO specialists or deep paid search specialists or writers and they love to write and they write long form content and that's definitely a part of what marketing does, but it's a specialty for sure. And then you have people that are just very much generalists and can handle all areas of marketing. So a couple of mistakes that I see is just hiring people that don't cover the area that you need most as a startup. And that kind of comes for two reasons.

**Emily Kramer** (00:07:33):
One, is like you don't know as a founder or someone else doing a marketing hiring for the first person, you don't know what you're going to be doing in marketing. You don't know what your big levers are going to be, you don't know what's going to work. And so you hire a marketer thinking they're like smart, they've done this before. But really they haven't done the thing that you need to do before. So I see that especially with business model where I think having the right business model experience is almost more important than having industry experience or experience with that audience.

**Emily Kramer** (00:08:05):
And I think often people are like, I need someone who is marketed to HR or marketed to construction or that specific. And my response is you, you're going to really narrow your set up people with that, and also it doesn't matter as much because great marketers learn the audience and learn the product quickly. And sometimes that fresh set of eyes is helpful and you have other experts in house on the audience. But the business model really dictates what marketing does in a big way. And by business model I mean more like, are you doing top down sales? Are you selling the enterprise?

**Emily Kramer** (00:08:39):
Are you doing bottom up product led growth or have a free version? Or whatever it is. Those types of things matter a lot. Because the set of marketing activities is just wildly different which I'm sure we'll go into. So to kind of summarize here, what I'd tell founders is I usually start when I talk to founders about who you need to hire in marketing. Because usually the question is, I think I need a marketer, who do I hire? And my critic question, let's try to nail this down because there isn't one answer. It very much depends.

**Emily Kramer** (00:09:10):
There's usually some common archetypes. But the first thing I say is forget all the sub-functions that you've heard about in marketing. Forget the product marketing content marketing partner, demand and growth, forget all of it and just think of marketing as you need fuel and you need an engine. And the goal is all the things that you're creating. I mean this should be obvious, but it's the content, it's the word that's the design and some regard, it's all the things you're making, all the things that are going to add value.

**Emily Kramer** (00:09:37):
An engine is how you get it out to the right people. And all of the tracking of that And of the ops work I put under engine. So you still need an engine. And the question is, where do you have the biggest challenge right now or where do you think if you did more, you would grow faster? Is it on fuel side or is on the engine side? Typically, if you just think about it logically, you kind of need the fuel first. And sometimes what I see is people just build an engine first and they're like why isn't this working we're sending so many outbound emails? And it's like, well you don't have anything valuable to put in those, you have no fuel so this isn't working.

**Emily Kramer** (00:10:07):
Or you see the flip side where they're making a whole bunch of things, they're writing a bunch of blog quotes or making a bunch of content and they're like, this content doesn't work. It's like, we'll, have you tried distributing it? Because if you're not distributing that and getting mileage out of it's a waste of time. So this is a big problem in marketing overall, getting the balance of fuel and engine rate. But I like to start from what do you think is going to help most and what skillset does your team not have? And typically, if a team is sales driven top down, they might have an SDR or at least two at this time.

**Emily Kramer** (00:10:37):
Usually that comes first in top down. And so the SDRs are kind of an engine. They're an imperfect engine, outbound shouldn't be the only thing you're doing. And if they're just reaching out and asking people to schedule meetings, it might not be that effective but you have a little engine going on. So maybe now you need some fuel first. On the other side of it, if you're a product growth or bottom up, you might have a situation where just nothing is optimized. Your website's conversion rates are terrible, people are dropping out of the funnel all over the place.

**Emily Kramer** (00:11:06):
And you really need someone who can build up these lifecycle email touches, work in product instead of work with a product or a person as well. And you really just need more engine because people are already finding out about your product or it has someone made virality and you're just not capturing enough of that. So I kind of like decode, what's going to help the most right now? And then ideally you get someone, so move back to an engine first.

**Lenny** (00:11:27):
Can I actually jump in real quick because that's a really cool framework that I haven't heard before, this idea of fuel and engine from a marketing perspective. To make it a little more concrete, what are a examples of, it doesn't have to be exhaustive, but when you think about all the things that could be fueled, and all the types of engines, what are those lists?

**Emily Kramer** (00:11:47):
For sure. Yeah, I have a diagram of this stuff in my newsletter.

**Lenny** (00:11:50):
Awesome. We'll link to that.

**Emily Kramer** (00:11:51):
So when I think about fuel and engine and what goes on either side, it's important to recognize that some things are fuel or engine and that some things are both fuel and engine. Let me start with an example of something that's fuel and engine. If done well, your community, let's just take for instance, let's keep it simple because community needs 75 things. If you have a Slack community that should be tool and engine. If you have people creating content in there that maybe you can then use in other areas. Like you do this well, you take what's going on in your community and you do your community wisdom parts of your newsletter.

**Emily Kramer** (00:12:24):
So you're using that as fuel but it's also an engine because you have people in your audience that you can distribute out content too. So there's some examples like that. But to go back to the question of what fuel and what's an engine. Fuel is like the copy on your website, it's the blog posts that you had, it's the templates that you've created. It's the video recordings of the webinars or the podcast. It's basically content, but also to include some of the copy.

**Emily Kramer** (00:12:50):
And I think people have this limited view of contents where they think blog posts and blog posts are still one part of content. Content should be tools, resource, assembled like calculators, those kind of things do better in all the cases.

**Lenny** (00:13:04):
And positioning I imagine is a fuel.

**Emily Kramer** (00:13:08):
Yeah. That's some of the product marketing steps. So product marketing is this weird thing and we'll talk about it that's kind of in the middle. But yes, product marketing, doing any positioning. Again, like the web copy which is of the first manifestation of your positioning and messaging, or it should be the source of truth for all of that. But you're positioning, you are messaging the words, the words are the things you're creating, that's the fuel, things that add value in that way. The engine side is what people tend to call marketing growth or demand jam or things of that nature.

**Emily Kramer** (00:13:37):
That's really the distribution channels. The email copy itself is fuel, but how you've set up the email and the segmentation you've used and the rules for that drip email, that's the engine. The SEO content is fuel, but your SEO sort of keyword list as a technical FTO and that kind of stuff is sort of engine. Social media, you got to have good fuel but you also have to nail it exactly what channels you're using and all that stuff. So a lot of things have both sides of it. So most projects or activities or initiative have some fuel and some engine.

**Emily Kramer** (00:14:08):
I also consider marketing ops work, the setup of HubSpot or whatever it is you might be using. That's engine. It's really instructing the engine, but I kind of put it in that bucket. Because people who are usually good at executing on email or executing on ads or things like that, usually have some working knowledge of the ops work and the reporting work because you have to be optimizing. I guess admin paid is also engine.

**Lenny** (00:14:34):
Awesome. Okay. And so coming back to your original piece of advice here is before hiring a marketing person, you want to figure out which of these buckets is the biggest constraint to your growth, right?

**Emily Kramer** (00:14:44):
Exactly.

**Lenny** (00:14:45):
You talked about this briefly, but is there any simple heuristics to give you a sense of it's probably fuel, I need more great content, maybe some website updates versus I need to figure out how to get this out. How do you think about that high level?

**Emily Kramer** (00:14:58):
Yeah, I mean, it's kind of simple. You can just ask what are your top performing pieces of content or what's the top performing page on your website or things of that feature. Who is your product for? Why is it better? What are the benefits? How does it compare to competitors? If you don't have an answer for those questions, you don't have top performing content and you don't know your positioning and all that stuff, you got a fuel problem here. Oh, you wrote this really great piece of content and I saw it on your website, how are you distributing that? What are you doing?

**Emily Kramer** (00:15:24):
And they're like, I shared it on social, they didn't really go anywhere, you got an engine problem. Or if I say, do you know what your final stages are? You have two sales people now, how does the marketing sales handoff go? They're like, they share a list and block off everyone they should reach out to. I'm like, well, you have an adventure problem if this isn't going to scale. So it's just these basic things. Are you doing these things or not? And sometimes founders are really great at making the original sort of content and writing the early positioning.

**Emily Kramer** (00:15:52):
And they're the best suited to that and they just need someone to help them get that stuff out and that's when they need an engine person. So that's basically how you figure it out. And normally when you ask vendors that question, they get it pretty quickly. They're like, "Okay, I think this is my problem, I can kind of identify it." And then it's like, okay, from here, well, what exactly do you need and what exact type of marketer do you need? And that's where everyone's answer is always, I think I heard from investors or I've been hearing from other founders that I really need a product marketer.

**Emily Kramer** (00:16:20):
And the question is, well what do you think a product marketer is? And you get a different answer every time. In fact, when I was at Asana our COO, his question that he liked to ask all the marketers or all the product marketers that we were interviewing was just, "What's product marketing?" And that's the scariest question you can ask a product marketer. It's like no scarier question for a product marketer then hey, what's a product marketer? They're like, "Oh, shit, I have no idea. Just my job, it's me. I'm a product marketer."

**Emily Kramer** (00:16:48):
But really a product marketer, they understand the product, they understand the audience and they understand the market in which you're operating. And from there they can figure out how to communicate with your audience about the right things at the right time. So they're kind of laying groundwork. And then they're also doing some work too. They're also doing a lot of the copywriting and the actual messaging and handling sort of launches and sometimes writing copy for things like emails and helping set the content strategy and things like that.

**Emily Kramer** (00:17:16):
And people think they need product marketers. One because it's like a fake people say, but two, because product marketers tend to shadow this line between fuel and engine. They're more on the fuel side, but particularly they've done a lot of launches in the past. They have a general understanding of channel strategy and what channels do at what time and that sort of end and stuff. But product marketers aren't really specialists in writing and producing content. They're not specialists in building out marketing ops or doing FDO.

**Emily Kramer** (00:17:44):
They're definitely more of the generalist function. And so sometimes that's a great answer. You need a product marketer, but sometimes you need someone that's scrappier in different areas. Another one of my frameworks is we start with doing these seal engine, what are the biggest problems? What are the biggest things that if you did, you would drive growth? And then we talk about the three typical subfunction that you would hire, which would be content, community type person, a growth demands and type person and a product marketer. And we kind of talk about what those three things mean.

**Emily Kramer** (00:18:16):
And kind of align based on what you're saying, based on the fuel engine thing, probably in this type of person. And then from there, what I tell people when you're hiring your first marketer and probably even your first several marketers, you're more want to hire generalist than specialists. This is probably true for anywhere at the early stage startup, but specialists are great to hire. It's great to hire contractors that are specialists. Like the FDO contractor, even the contractor who can write the marketing ops contractor. But you want someone who is pretty much a generalist.

**Emily Kramer** (00:18:49):
And the way I describe that within marketing, usually you you are like hire a T shape person that bites in one area and has working knowledge and try to crop all of them. But I use this thing that I made up which is you one up higher pie shaped marketers, not pie like dessert, but pie like 3.14 where the pie symbol has two vertical lines. So like a T but it has an extra line. And it's because you want the first marketer to be an expert in one of those three areas that I mentioned, product marketing, content marketing, growth marketing.

**Emily Kramer** (00:19:21):
And you want them to be proficient in another one, the second T. But you want them to be able to set strategy and know how to hire contractors across all of them. And so the promise land of hiring a first marketer, they are a pie shape marketer. And so then you could hire a content and product marketing pie shape marketer, product marketing growth pie shape marketer. But it's like what are those two spikes and what's the one that you're going to worry less about that they need to work knowledge of?

**Emily Kramer** (00:19:45):
The last thing I'll say on the pie piece is that it's really hard to find someone that's a content marketer that's also really good at growth. Like that pie shape marketer exists a lot less frequently. Maybe it's someone who is really amazing at content distribution or really amazing at FDO, but they don't really exist. Because the content side is like one side of the brain and the growth data stuff is a whole other side of the brain. You don't find those people very often. So you are usually looking for that product marketing, growth marketing pie shaped person or the product marketing content marketing pie shaped person.

**Lenny** (00:20:21):
Wow, okay. This is great. So I was going to ask you about-

**Emily Kramer** (00:20:22):
Sorry this is dense, this is a lot of marketing window, so hopefully we're breaking it down.

**Lenny** (00:20:29):
Yeah, we're getting there. So let me try to summarize and see where we go. So I was going to ask you about the archetypes of marketing people and it sounds like there's these three is the way you think about it. There's basically a content community person, there's a growth person and then there's product marketing which is kind of like in the middle. And I guess, one question I wanted to ask is there's also just the growth function, product growth, growth PMs, things like that. Do you see that as the same thing as this growth marketing person or is that a different type of person and a different role?

**Emily Kramer** (00:21:01):
In top down sales businesses it is 100% different. A growth person typically probably called a demand gen person. There's a whole other rabbit hole we can go down on what's the difference between growth marketing and demand gen. And demand gen is probably more top of funnel and growth marketing is probably more full funnel at its simplest form. But it's definitely different there. In a product led growth business, the growth marketer and the product grows sort of role or the hybrid growth role, sometimes it can be the same person depending on the skill.

**Emily Kramer** (00:21:31):
But typically the difference would be that the growth marketer is doing more of the top of funnel sort of inbound side and the product growth person is doing more once they actually get into the product, but can be collaborated with that growth marketer. So it can be the same person in extremely data driven sort of person that kind of has the working knowledge of both marketing and product stuff. It can be one person in early stage PLG companies.

**Emily Kramer** (00:21:56):
But I think typically, and I'm sure you've seen that at larger companies as you get bigger, you're going to have some people that come from more of that marketing perspective and you're going to have a little bit come from more of that product perspective. But the question is, is there ever one person that does that?

**Lenny** (00:22:09):
Okay, so to make this a little more concrete even for startups, thinking from a startup perspective, when you're just thinking about hiring your first say marketing person. When you think about this set of buckets that you talked about, there's content marketing, growth marketing, product marketing, plus to your point there's at larger companies or maybe later stages separate from a growth PM type person. What do you generally think is the right role to hire/architect to focus on? Or is it really dependent like you said on fuel versus engine versus something else?

**Emily Kramer** (00:22:45):
I mean it's highly dependent on, again the business model, what you need more of, what you already have in place, what's going on. But the most common archetype that I say you want to hire is a product marketer. Even though I joke that everyone says you need a product marketer. But it's actually understanding what that is first, that understands growth marketing as well. So they probably work somewhere early on where they've had to have some exposure to that. So they understand all the channels they're working with, understand what they can do with those channels and maybe they need to work with contractors on some of those things.

**Emily Kramer** (00:23:17):
Also product marketer needs to know how to write. All marketers should some working knowledge in writing, but they need to know how to write. They are the copywriter for a long time. Tests that they can write, make sure they can write well, short form and long form. They're not going to be necessarily as good in writing as say a content person, but they need to be able to write. And product marketers just tend to have that ability to write and that ability to understand what channels they can use to reach their audience so they're in the middle. So often that's the case.

**Emily Kramer** (00:23:44):
But I mean, sometimes I find that I'm recommending hiring that growth person first because they maybe already have a couple of really great contractors and they have a couple of really great pieces of content that can just be gifts that keep on giving if they keep distributing them and repurposing them.

**Lenny** (00:23:58):
What do you look for in this product marketing person? You mentioned ability to write is really important? What else? When someone's scanning LinkedIn or just later talking to them, what do you find is important to focus on and look for?

**Emily Kramer** (00:24:10):
This can be hard to find, but I think I want to see that they've worked on a team that's early enough where they are not siloed into their specific role. Because what happens at leader stage companies or at public companies is when you're a product marketer, you don't see what's going on in the rest of marketing at all. You have a very siloed view of it, maybe you're only working on product launches as a product marketer, which the positioning is already set, the audience research already done, they haven't done any of those things, or the channels are all built out.

**Emily Kramer** (00:24:38):
It's just different. I think that's the case in a lot of roles at startups. But building it from scratch is different. So that doesn't mean that if you're a series A company hiring your first marketer that you need to hire someone that's worked at a Series A company. But it usually means you're hiring someone that's worked at least at a growth stage company where they have exposure to a bunch of various marketing. Also looking for, have they seen what great looks like? So whether they joined us startup up early and it did really well, or whether that's they had a stint at a later stage company and then earliest in their career, they're a big company then they went to some big smaller.

**Emily Kramer** (00:25:17):
Do they know what high quality sort of great looks like? It doesn't always have to be, you don't have to have been at a startup that everyone thinks of as like, they're really great at marketing, but it is helpful. And there are some people that just have a really high quality bar and really understand what great marketing looks like even if they haven't worked in those companies. But I like to say has worked somewhere early enough that they could set strategy across all of marketing. And do they know what great looked like? That's something I'm scanning for. I'm also scanning for your first marketer, you don't want to go out, I see this mistake all the time.

**Emily Kramer** (00:25:47):
You don't want to go out and hire someone super senior who's only worked at a public company. That's the wrong person. And often VCs or sort lead investors that aren't in a certain niche. when they refer candidates to startups, usually the fail I see is they're like, here's someone great from Google. And I'm like, I'm sure they're great but they're not great for this role and that's the mistake I see all the time. Oh, we just fired our first marketer. I'm like, "where did they work?" They're like, "They only worked at Salesforce." I'm like, well, yeah.

**Lenny** (00:26:15):
Why is that not a good fit?

**Emily Kramer** (00:26:16):
Just because they don't understand how all the marketing works together and they don't understand how they built the foundation. It's much different marketing something that already everybody knows what it is or everybody knows the brand even if they don't know the product and they have a built in customer base, than building something up for scratch from scratch is just a very different marketing motion, and you need to do a lot of things. You need to do a lot of things yourself, you need to be a doer.

**Emily Kramer** (00:26:38):
So you're really looking for most roles or most lead of function roles at startups, they need to be both strategic and of scrappy enough to get the work done. You're going to be doing it all. And in marketing you're often going to be the first marketer for a little while and you're going to be doing everything. And so there has to be some sign that you're going to be comfortable with that.

**Lenny** (00:26:59):
Awesome. When do you find that it's usually best to hire your first marketing person?

**Emily Kramer** (00:27:05):
I mean stage wise you're looking at some nice people hire at seed depending on their business, but usually it's in Series A or you hire one sort of more junior person at seed when you're coming into raising or Series A and then you know have two people right after your Series A. But really, I think it's helpful to have some sort of semblance of product market fit. Maybe you're not 100% sure, but maybe you have definitely some successful customers. It's not like we're working with a design partner to build this out and we have a couple pilots. Marketing is really good at accelerating growth and doing that scale one to many.

**Emily Kramer** (00:27:46):
So if you're still in the very well spoke founder led sales, founder led marketing, like I'm doing discovery with each of these potential customers and have to modify my product for them, that kind of thing. You don't need one yet. Founders can do a fair amount of stuff and they can use some contractors. I think you need them earlier in product growth models because you're not going to hire a salesperson then. So it's more thinking about go to market holistically and saying, do I need one or two people here and why is that? And so if you're a top down model sort of enterprise sale, you're probably going to have a couple sales people before you hire marketing, but that might not be the case.

**Emily Kramer** (00:28:26):
And these are more self or product led growth models, you just don't need the sales person. So having the marketer is helpful. So again, the business model affects this a lot, but usually the general rule of thumb is, if you had a marketer what would they do? And I often help people try to figure that out. What would they do and if they stepped on the gas and did all this stuff really well, would you be able to handle all those people that came in? Is it even a good time to bring all those people in to your product?

**Emily Kramer** (00:28:52):
So are they going to be held back by where your product is or where some of the discovery on exact business model is or things like that. And that's the case. It's just not a good use money when they're kind of just sitting on their hands. I can't spend any money on paid and we don't even have any idea what to say on the website because we're selling four different things. It's just kind of hard to hire someone in that case.

**Lenny** (00:29:19):
**Emily Kramer** (00:30:53):
Sorry. Yes, mostly B2B advice. I think a lot of this holds, I think the fuel engine stuff holds for B2C. I think the roles pretty much hold, but you might hear the word brand marketing thrown out a lot more in B2C and that's what we're going to be talking about, the fuel stuff and maybe that's going to be what they hire before they hire say like a product marketer. But it's kind of the same set of functions. But most of my experience are B2B and most of the startups I work with are B2B, but some of it holds.

**Lenny** (00:31:19):
Yeah, I was going to ask about brand marketing, that's like another bucket, right? We haven't talked about that as a type of skill or does that fall into one of these that you've talked about?

**Emily Kramer** (00:31:27):
To me, brand marketing is a combination or has some of the work that happens by a product marketer and by a content and community marketer. But maybe they also are more influential on the design side of things. And so brand marketing is another one that needs 75 different things. Sometimes it means you literally manage designers or you're a trade up producer, and sometimes it means you are more doing work on what are the stories that we're trying to tell and you're doing more of the content stuff. And sometimes it means I'm doing the positioning work, sometimes it means I'm working on the website or branded paid stuff and consumer.

**Emily Kramer** (00:32:10):
So it means a lot of things too. But usually in B2B, the person that kind of owns the brand is the positioning story side of brand is owned by product marketing. And the design side of brand is either just owned by the product designer on first or working with a brand designer or if the marketer has skillset set there could be owned by them as well. So it's a little murky at first, but eventually on B2B teams when I've grown teams plus 10 to 15 people, I'll have a brand person that is working really closely with the designers and kind of making sure that everything that we're producing on the content side of things is up to... They're acting as sort an editor there.

**Emily Kramer** (00:32:58):
They're making sure everything ladders up to the overall story. So they're helping tell the story, they're helping make sure the design is right. And in some instances I'll have a brand person that's kind of working on these larger brand initiatives. We did a huge data study when I was at Carta and the person that kind of ran that whole initiative and the events and it was sort of a separate initiative that had a lot of different parts was my brand marketer. They were kind of working on these larger sort of big data project that's made across all of marketing.

**Lenny** (00:33:25):
Awesome. Well you talked about the growth PM role kind of adjacent to all this. For the typical say PLG startup, in your experience, do you find folks should hire more of a marketing person than a growth person that focuses on say, conversion or optimizing the funnel or SEO or paid or anything like that? What's your experience there?

**Emily Kramer** (00:33:47):
For PLG I think you want to have a marketer that is responsible for getting people into the product, that's a marketing profile. That's using all of these channels that's driving inbound, that's focused on web conversion, making sure your website converts, that's a marketing skillset. Because it's really likely you have to work with to get this done is really how I think about it. And you have to work with the people that own the website which is marketing for all of these sort of inbound stuff you are going to work with a lot of people on the marketing team. So that piece is really a marketing piece.

**Emily Kramer** (00:34:16):
The product experiments and the product test, that's a person with a product skill set because they know how to work with other PMs, they know how to work with engineers and marketers don't. And then there's these gray areas like the onboarding experience or when you first get into the product. And that is an area where there needs to be a ton of collaboration. So my view is that if you're going to have a growth PM, it's probably helpful for them to have EM experience or product experience, but they should be paired as soon as they can be with someone that also understands that top of model piece.

**Emily Kramer** (00:34:50):
Or maybe that person isn't in a full-time growth role, but know who on the marketing team is going to work with them on these areas of crossover like onboarding or that first use experience. And making sure that the signup flow from filling out something on the website to getting in the product is really consistent. Because that area of I'll fill out a handoff, we talk about the marketing to sales handoff all the time on the go to market side, but there's a marketing to product handoff. And that's the handoff that's really important in PLG. And that feels weird to a user, it's two different teams inside of a company.

**Emily Kramer** (00:35:24):
But if that that feels weird to a user, you're going to notice that all of a sudden feels extremely disjoined. Or if I'm getting a bunch of product transactional emails while I'm getting a bunch of marketing drip emails. So that handoff or that experience needs to be ironed out or consistent or there needs to be tons of collaboration there. So however that is done, I don't really care what the teams look like. Lots of different companies have different versions of how they do this. But the idea is that experience needs to feel consistent and you need to have collaboration across people that have those skill sets and you need to have a clear process for how that looks.

**Emily Kramer** (00:36:00):
And so it's just getting that marketing sales handoff in my opinion. It's like how do you get the marketing to product handoff right? And if it means you have someone that owns onboarding, it's in a hybrid role, then great. If it means there's a committee sort of situation with one person at the DRI, that's great too. So I think my answer is, I don't think there's one way to structure it, it's just highly dependent on the company overall. And I think you need both skill sets.

**Lenny** (00:36:22):
You touched on an area of tension that often comes up between marketing and product. I imagine many listeners hear you saying, marketing should own the website and conversion and net flow. And thinking about the idea of product led growth. The idea that is product will grow our business and oftentimes PMs do that work and oftentimes they're really good at it. And so I guess the question is, in your experience, do you find that it should be marketing more than product or product people?

**Lenny** (00:36:58):
Is it depending on the person, maybe they're called the product person, but they actually are really good at marketing. Any insights there? And then we're going to talk about just collaboration between the two functions.

**Emily Kramer** (00:37:08):
So I think that product led growth is a misnomer. I think people will do anything they can possibly do not call marketing marketing. I think we always see this. And so I think that product led growth really means not as much sales, which means product plus marketing. And so that's probably a hot take. But product led growth is just another name for what we like. I mean, product led growth is a little different than premium or sales server, these things. But you are being handheld by the product, you aren't being handheld by the sales team.

**Emily Kramer** (00:37:37):
So really to me, and you can have a sales assist with product led grow as well. But typically what's more at odds in my mind is product led growth means you are going to have a huge sales team early on. It doesn't mean you're not going to have a huge marketing team early on. In fact, to me it means you are going to have a bigger marketing team early on because you're not going to have those sales. Sales is not communicating with customers. So I think it comes back to what are these teams typically good at? And marketing is typically good at the communication piece of one to many. That's what they're good at.

**Emily Kramer** (00:38:07):
And so they're usually good. They should be good at figuring out all the channels to have a funnel to communicate with people. And product is really using product as a channel by which to communicate with customers prospects, et cetera. So that's one way of thinking about the difference. On conversion, conversion also means lots of different things. There's top of funnel conversion, getting on the website and filling out some other form. There's conversion once you're in the product becoming an active user or inviting people. So it's like, well, which part of conversion? Web conversion, I typically think of something that's owned by marketing because usually product doesn't want to own the website.

**Emily Kramer** (00:38:46):
Early on products will sometimes own the website because marketing wasn't there. But the website is something that's going to need to be updated like 5,000 times and it needs to be on Webflow preferably at this point or DMS that's easy update. And if it's built into the code base that's like it, or it's on a headless CMS or it's not touchable by marketing, that's a huge problem. When it comes to once they click the signup button, who should be mostly involved in that process? I think again, there needs to be, I think there's lots of ways to handle that.

**Emily Kramer** (00:39:15):
And I think if it's product it kind of has that skillset and the testing skillset and there's enough volume that you can be doing a bunch of tests, maybe that's the person that owns that. But I think there's still going to be a lot of collaboration on the exact words that are used and things like that. So I think it's just whatever it is, make it clear where the handoff is. And so maybe it's not marketing on the entire website because maybe they don't own those flows, but there's this gray area. And I think the other big thing is sometimes the forms, the literal forms that are used are built in your website and sometimes they're built in the product.

**Emily Kramer** (00:39:47):
And I think that also drives a lot of it because it's who do you need to help you build these things? And if they're built into the product, then the product team needs to own that. But it shouldn't to me like this, let's not argue about it, we're trying to move this and here's the things that marketing is going to do and here's the things that product is going to do, and here are the areas of overlap. But I don't think products should be in the business of owning the whole website and all the top of funnel messaging and all of that stuff. That's not the best use of anyone's time really.

**Lenny** (00:40:18):
I know you had a lot of success with marketing and product working together at Asana, and kind of double clicking on the same thread. What have you seen to be an important part of this collaboration and making one plus one equal three, when product and marketing and working together at a B2B company?

**Emily Kramer** (00:40:36):
And look like there were definitely ups and down marketing working with product at Asana as well. But I think overall we did a good job because of some of the systems that Asana had in place. Which is and we talked about this before but something that Asana did well is they had this list in Asana of course, everything at Asana was in Asana through Asana by Asana. But we had a list of areas of responsibility which is just who owns what, it's not your job title. It's what are the things that you are the DRI for? It doesn't mean you're not going to collaborate with people on those things. So what are you the directly responsible individual for?

**Emily Kramer** (00:41:11):
And this made it really easy to know who to go to. I'm just going to use DRI because I can't keep saying directly responsible individuals. So the DRI on tests on the onboarding experience is Jennifer the PM. But the copywriter for that is, I don't know, I'm sure who think of exactly who the person was, is Devin on marketing. So we broke it down that's simply so you knew who to go to. Because often what happens with product is they're like, I'm doing a launch, I don't know, especially when there's 15 marketers, I don't know if I'm supposed to go for this product launch or to figure out if this is a launchable feature, so I'm just going to skip it.

**Emily Kramer** (00:41:49):
So it's really helpful to say the product marketer owner for this part of the product is this and to just have this list. So just having clear ownership is what this comes down to. But it's one thing to have clear ownership but it's quite another to for other teams to know who that clear owner is. So I think having a clear list beyond titles and just like who owns what is really helpful. And then as you hire new people, you can break down those, the list kind of gets longer because you're going to break things down more. It goes from Emily owning all of marketing to me breaking that down and not owning all of it.

**Emily Kramer** (00:42:22):
So I found that really helpful. I also found at Asana we did something called Roadmap Week, which was before every quarter. Where we had of open meetings, sometimes they were open and sometimes they weren't. But we had cross-functional meetings to help plan for what you were going to do that quarter on your team. So I could sit in on the product road mapping for X as the head of marketing. And that was really helpful to just get a sense for what was going on. And sometimes there'd be people in those that were silent participators, and then adopting that would be made so you could see this.

**Emily Kramer** (00:42:56):
And maybe it doesn't scale forever, but it worked really well early on for people being able to be looped on things, to have these sort of out loud landing meetings where you were talking through here are our biggest decisions. Here's what we're wrestling between and getting input, kind of knowing what was going on. I think another thing that we did well was also having clear review processes. And all of this sounds like a lot of process, but once you actually make an AORs list, it kind of runs itself. Someone new gets hired, they're excited to put in their AORs or someone gets the new responsibility and they're stoked to take it over from the head of marketing or whatever it is.

**Emily Kramer** (00:43:32):
I finally have handed you the master managing editor AOR and it becomes a big deal. The other thing that I think we did well from a marketing perspective is another newsletter that I have is this framework that I use called the GACCS or the GACCS. Which GACCS sounds more fun to say than the GACCS. But this is just a marketing brief that I recommend you do before you make anything big in marketing or do any big projects. And it's just what are the goals? What's the audience? What's the creative or unique end goal? What's this thing? I guess what's going to make it different and stand out from other companies?

**Emily Kramer** (00:44:17):
The second C is the channels or how this is going to be distributed. How are you going to get the word out about this? Deep thinking there. And then the last few are the stakeholders. Who's the DRI and who needs to weigh in and who's going to be the helper? Who are the contributors? And that's where you can include some product people and you can share this before you start doing any work. So for instance, if you're doing a product launch, product manager communicates with the marketing team. Maybe you have a meeting, maybe you share some brief from the product guide or you share sort of what's being built.

**Emily Kramer** (00:44:43):
And then marketing comes back to you with the GACCS. And you can kind weigh in on, here are the channels that are going to be using. The creative C has maybe the highest level messaging. And you get buy in early on and then you can go much faster. And then you're not just sharing with product, here's a blog post that I wrote for the launch. And you're like, what? This is the wrong audience, the wrong thing. You just save so much time sharing these types of things up front. So I find there's a handful of different practices that need to be in place, but it's sharing the right information at the right level of information at the right times and having a culture of doing that.

**Emily Kramer** (00:45:21):
And it needs to go both ways. Product needs to loop marketing and they are like, here's what we're working on this quarter here are going to be some of the things that we're launching or any of these interesting that you want to double down on and do what public launch for or whatever it is. Or we really think onboarding needs to be approved. Let's put together a group that's going to work on this quarter and let's kind of have a spring plan that's cross-functional. It's a lot of that. So a lot of this happens in a planning process. So if you as a company don't have a good planning process, you're not going to have good cross-functional collaboration, especially between product and marketing.

**Emily Kramer** (00:45:54):
And I think the last thing is just a respect for the skillset. Recognizing you are good at this or you have access to engineers, you know how to get them to do things. I don't want to do that as a marketer. I'm good at storytelling and I know how to get people in the door in the funnel. And let's respect what each person is good at and let them go do their thing. So those are just some of the tactical practices and things that we did in Asana that I thought worked well. But it's hard.

**Emily Kramer** (00:46:24):
I mean, everyone wants the other team to be doing something a little bit differently and that's always going to be the case. And those tensions in some cases are good because that's why you have the benefit of having different teams and different perspectives. But it gets out of hand when people are just working in silos and aren't communicating with each other, aren't looping people in on things that they're experts on.

**Lenny** (00:46:43):
Awesome. All the templates and frameworks that you mentioned we're going to link to in the show notes. One of the things I love about is you're like a PM minded marketer where you make everything super concrete and templated and assigned.

**Emily Kramer** (00:46:56):
I like a framework, I like a framework and I like a template. And I am pretty PM minded because I'm pretty well rounded when it comes to the marketing skillset. I don't really consider myself a growth marketer or a product marketer or a content marketer. I just consider myself a marketer who builds teams and that's a different mindset. And I also love goals and planning. No, I don't love annual planning processes that companies do and overdone OKR exercise. It's where you're making this crazy cascade that then nobody can follow.

**Emily Kramer** (00:47:31):
But basic sort of simple planning so that you kind of go a little slower up front so then you can just fly out getting things out the door. That's the kind of teams I like to lead.

**Lenny** (00:47:44):
Awesome.

**Emily Kramer** (00:47:44):
It's like upfront buy in and then move back, do what you need to do.

**Lenny** (00:47:48):
I love the sound of that. We're also working on a guest post that may come out before this comes out or after around a lot of this templates. So I'm excited to get that out the door. Coming back to this kind of tension that often happens between PMs and marketing people. Tell me if you agree, but I find that product teams are always often very skeptical of marketing and find that there's just all this time, energy, resources put into marketing efforts. And it's hard to measure who knows what's happening there.

**Lenny** (00:48:19):
While the product continues to evolve, you can tell what it's doing. It's often driving most of the growth. And so my main question here is, as a product person, what tells you that the marketing person and team is good and awesome and you should trust them and they know what they're doing, versus maybe they're not amazing and we should try to push back? Any advice there?

**Emily Kramer** (00:48:45):
Yeah, I recently did a talk with my friend Jenny, who was the head of content at Asana and now is the head of content in Palms at Clear Lake. And she was sort of joking. We were coming up for the name of the talk and she was like, "I want to call it content splatergy versus content strategy." And I was like, "We'll work that in, but maybe that won't be the title, splatergy is really weird word." But it's true. But I think it's funny because a lot of what marketing is that splatergy not strategy, meaning it's just like you just throw a bunch of stuff out there.

**Emily Kramer** (00:49:17):
And if you're doing a bunch of work and it's like a lot of busy work and you want to look busy, but it's not impact focus. The best marketing teams are impact focus. They can tell you of all the things they're doing, what are the core things that are of driving that linear growth or just keeping the lights on. They can tell you what their big bets are. What are the things that we are doing right now that we believe can cause step change, top of the funnel growth? Or step change growth on signups or whatever it might be? What are those things? What are the big bets that you're taking? And then what are the foundational pieces of marketing that aren't done yet that might be taking up time?

**Emily Kramer** (00:49:54):
We would love to be able to move faster here, but we're like, we don't have a good lead scoring system or we're working on this. We need to redo our website and here's why we need to get it into Webflow and then we'll be able to move faster. So they should be able to break down. Here are the core things we have to do. We're measuring that the core work is working by these TBIs and it's sort of a full funnel view. And we are working on these big bets and here's the foundational things that are broken. So if you ask a marketing lead and you're like, What are their big bets? And they're like, I don't know.

**Emily Kramer** (00:50:26):
You can't grow at the rate of venture back startups, you grow by just continuing to do incremental things. That's the same as product I would imagine as well. So they need to have this sort of framework going on. And the other thing that I think is a sign that you're not being impact focused or you're not being effective as a marketing team is this is my favorite thing to pick on And I see it all the time. And I understand why it happens, but don't do it. If our goal is to write 10 blog posts this month. And I'm like, no, that's not a goal, that's maybe a tactic. But the goal should be traffic and the conversion rate from that traffic or the signups that come from that.

**Emily Kramer** (00:51:02):
So you shouldn't have activity goals, you should have impact goals. And so the best marketing teams are focused on these funnel metrics. They're not just focused on a certain number signups or qualified leads. They're focused on that number plus maintaining or improving the conversion rate that comes after it. So they're focused on signups with a conversion rate to activated user of the same or better than it is now. Because I can get a lot more people to sign up for a product, but they might be really shitty quality. So you need to have sort of that other threshold. So these are some of the things that I look at to say, is marketing team impact focused?

**Emily Kramer** (00:51:40):
And when I talk to companies or work with marketers and look at what are they doing and what are their projects, these are the things I usually point out. You need to be more impact focused and here's what you need to do. So that's the big thing that's like are they doing a bunch of busy work or are they doing a bunch of things that can actually lead to tangible growth and what metrics are they using to track that? The other thing is if they're not tracking to my point about not just looking at the raw numbers at each stage of the funnel, but looking at the conversion rates.

**Emily Kramer** (00:52:12):
If they're not looking at conversion anywhere at all, there's a huge problem. Because again, I can throw a bunch of people into a funnel stage but they don't convert to the next one, it might not be helping anything. So their focus on conversion not just at the stage of the funnel that they own, but throughout the entire funnel, I think also is a good indicator on if they're being successful as marketers or not.

**Lenny** (00:52:33):
Yeah, these are great. I feel like everything you're saying is music to every PM's ears. That great marketing people should be impact focused, have clear goals in KPIs. You also talked about how it's important to DRIs, like who is responsible for what, being really clear about that, communicating really clearly and often. And then there's this piece about just setting the foundations, like a strong foundation that helps make all these other things successful. This is great.

**Lenny** (00:52:57):
I imagine every PM would be like, This is exactly what I want from my marketing team. And your point here is, if your marketing team and lead is not doing these things well, maybe there's an issue and maybe it's not the right marketing person.

**Emily Kramer** (00:53:09):
Yeah. And look, if it's not the team lead, because sometimes you do have, especially at a larger company, you have a team lead that's either on the, you could have someone that's extremely sort of creative and on the brand side of things. But they need to have someone that's working with them that is really good at all of this stuff. It's almost like we need marketing PMs then those tend to be the product marketers or the lead. Because there's so many different projects going on and lots of different things happening. And it's hard to put it all together and say, what are we doing as a marketing team that's moving the needle.

**Emily Kramer** (00:53:40):
But I think the other thing about communicating often, it's also communicating at the right level. I find that marketers, even though they're often good at communicating with the audience, they're not good at communicating internally. And I think I've struggled here too as they move to leading larger teams and being on executive teams which is like, what level of information do you need to communicate? And you need to educate people about what marketing does. Because one, marketing often has a bad reputation and so you need to be like, here's what we're actually doing and moving.

**Emily Kramer** (00:54:06):
And two, there's a lot of jargon in marketing and you got to separate that out and communicate the right level of information at the right time. So I think that's hard too. And so that's why I like things like the DAXs framework and other things like that. And what exactly am I communicating about and at what level. It's hard to get right there too.

**Lenny** (00:54:25):
Amazing. One last question before we get to our very exciting lightning round.

**Emily Kramer** (00:54:30):
I can't wait.

**Lenny** (00:54:30):
You've been waiting all week. So you mentioned that you're a full-time investor basically at this point and the newsletter is a part of that. You've become a really active angel investor and it's really cool to have seen the way you've turned your experience in this really smart way of getting into great deals and supporting founders. And so I'm curious if you have any advice for folks that are thinking about becoming angel investors in the future, just how to leverage their expertise to become successful in investing.

**Emily Kramer** (00:55:03):
I think there's a big need for investors that have functional expertise. In traditional VCs. They don't necessarily, maybe they founded companies, maybe they've always been investors or sometimes VC and they really come from sales roles or PM roles. But for me and for marketing and maybe for some of the roles of other people are in, there's not a lot of investors or even advisors from that function and they need help there. And so I think more and more founders are seeing, instead of having advisors or even hiring someone at a function early, it's like, let me lean on angel investors for that.

**Emily Kramer** (00:55:37):
And so I make it very clear when I talk to founders, this is how I'm going to help. I'm going to help you build your marketing function. I'm definitely going to help you hire, or I'm going to help you shape the job description of the process. I'm probably going to refer you some candidates. I might even refer the candidate that you hire which has happened a bunch of times. And then I'm going to work with that person to make sure that they're setting the right strategy and doing the right things. And so being that clear on here's my exact value add is incredibly helpful.

**Emily Kramer** (00:56:04):
And I mean, we get into every deal that we want to. We being I have a business partner named Kathleen, that I do all this with and we can get into any deal. Which I think as an early angel investor, I'm like, why are people saying it's hard to get into a deal? I don't have this problem. And that's not me tapping myself on the shoulder. It's just showing there's huge shortage here. So your skillset might be really valuable to founders and even if you feel like, I don't understand how everything works at a company or things like that, your skillset could be really valuable and they might not see it.

**Emily Kramer** (00:56:32):
It's also when you have a unique skill set and a unique way that you help well articulated. We're going to help you build marketing, it's easy to understand. It makes me easier for other people to bring you into deals. Versus here's another generalist investor that's just going to help. So it's almost like you got to product market yourself. What's the product that you're offering? And then it's so easy, you know Lenny to bring me into deals where they might need some marketing help and there's tons of investors that do that which gets us to deal flow that we need.

**Emily Kramer** (00:57:00):
So I just think if you have a niche or you have an area where you're particularly skilled, you can really leverage that into being a sought after angle. Now, if that makes you a good investor, I'm not sure, there's lots of other things you need to get up to speed on to actually be a good investor. But from the standpoint of helping founders and getting into deals, that can be really helpful.

**Lenny** (00:57:19):
Awesome. And the other part is you actually have to deliver because then people share more deals with you. And as I said earlier, I've heard so often how helpfully you've been to founders and so that's an important element.

**Emily Kramer** (00:57:30):
Yeah, you definitely have to deliver. And again, I think that's where it's really helpful to say where you're going to deliver. So they're not necessarily expecting you to deliver on every little thing. They're expecting me to help them hire their marketer, hire contractors in marketing, fill in gaps until they have the marketing team that they need. And so they know when to come to you and then you respond. I think that's also like when people have full-time jobs, I think it's hard to be able to do that full-time jobs that aren't this, it's hard to be able to just tap in and do this kind of stuff.

**Emily Kramer** (00:58:01):
So it's like don't go overboard because your reputation really, really matters and that's how we've always seen it. We want to be the most helpful angel investors or now we have a small client, but the helpful sort of most helpful investors that you have in your cap table regardless, not just within marketing but within everything. And we do that because we can go really deep on an area and we're always responsible on those areas. And it's good to hear it's working because that's what we're trying to do is be really, really helpful.

**Emily Kramer** (00:58:27):
And the other thing too, the last thing I'll say on that is each founder probably thinks, maybe they don't, that it takes us a lot more time than it actually does to be helpful in that area. I had the same conversations over and over again about how to hire a marketer. I can do it in my sleep. So me having that conversation with you and dropping knowledge that you haven't heard, this is what I do all day. But it feels really new because they don't have a lot of people talking to them about marketing. We just have a bunch of candidates that we talk to and our newsletter generates candidates that we talk to.

**Emily Kramer** (00:58:57):
So anyone can go on our website and get on our list of candidates that we're referring. I talk to one or two candidates a week from that to just meet more marketers. So I have a list of marketers I can refer and say, it's really easy when clients ask me for referrals. So it starts to scale pretty well if you have that niche where you help.

**Lenny** (00:59:16):
Yeah, I was actually going to add that it may sound scary to feel like you commit to all these startups as an investor, you have to help founders all day. I can say I've invested over 150 companies at this point, which on the surface could feel overwhelming. Like holy shit, all these founders are probably asking you for advice all the time. But I find it's not that, most founders just leave me alone, I'm good.

**Lenny** (00:59:39):
Or maybe once a quarter, here's something I could really use help with. But it's not as much time as you think and when it is it's really powerful, but it's not an overwhelming amount of time commitment.

**Emily Kramer** (00:59:53):
The other thing there too is if you refer someone that a company hires, they're going to lobby you forever. You remember that because you sit there and you look at that, I mean, you're maybe not anymore looking at them in an office, but you see and are aware of them every day. And you remember, they came from this person. So one of the most valuable things you could do is refer candidates. And so that's where I think you can add a ton of leverage. You're just referring the right people. So if you have a network and a bunch of people that you know in a certain area like that scenario where you can really do a lot of good for a startup.

**Lenny** (01:00:25):
Absolutely. Speaking of doing good, we've reached our exciting lightning round.

**Emily Kramer** (01:00:31):
Oh, great.

**Lenny** (01:00:32):
So I'm just going to ask you five questions real quick. Whatever comes to mind, let me know. First question, what are two or three books that you've recommended most to people?

**Emily Kramer** (01:00:41):
I like the classic marketing book, maybe because I think if they're not a classic and they're recency based, marketing changes so fast, like most things in startups and technology. It changes so fast that I like the things that have stood the test of time. And those are things like The Tipping Point and Crossing The Chasm. And I like Seth Godin's Purple Cow, which is just having something that makes you stand out. So those are the classic marketing books and I think every marketer or some of them should have read at some point. I think April Dunford's Obviously Awesome is sort of becoming one of those books that every marketer should have read on positioning.

**Emily Kramer** (01:01:16):
It's really helpful even if you're not a product marketer doing positioning, I think it's really helpful. And then the book I read most recently is not related to marketing at all. I read is my partner's favorite book and she was always like, I don't think you're going to like this book, I don't think you'll like it, but it's her favorite book. And it's All The Light We Cannot See about World War II which is of a depressing topic giving all of the tumultuousness in the world. But I thought it was just a very beautifully written book.

**Emily Kramer** (01:01:42):
And when you read a lot of business writing a lot, it's kind of nice to step back and just read really beautiful pros on a really heavy topic that isn't just startup marketing. So it was kind of fun to go back and read sort of a older book that was really beautifully written. Next one, Lenny.

**Lenny** (01:01:58):
Next question, okay. What's a favorite podcast for you?

**Emily Kramer** (01:02:02):
Besides yours, obviously. No, I mean, you're doing a great job for someone who's just started off doing podcast. You go deep with people which I think is good, it's not just the service level stuff. Look like the podcast I listen to most is like every night when I go to sleep, I listen to The Daily, the New York Times Daily just gets me to know what's going on. I also like some true crime podcasts but I won't talk about that because maybe that's a little embarrassing and basic. And I think for just getting understanding founders and startups over the years, I found How I Built This to be really helpful.

**Emily Kramer** (01:02:33):
And I think the main thing I learned from How I Built This is that most startups are really happy. And so if you feel at the beginning if you feel like, we're are just a mess, we're doing everything wrong, that's kind of common. So it's helpful in that regard too. It's like, it's not just me. But I think there's really interesting founder story and hearing how things are built is always helpful. So those are some that I like.

**Lenny** (01:02:55):
Favorite recent movie or TV show?

**Emily Kramer** (01:02:57):
My favorite TV show from this year was Yellowjackets on Showtime, which is kind of Lord of the Flies, which had a bunch of women. Lord of the Flies meets lost. It's really good. So it has Christina Ricci in it, the person who was in Casper and now in [inaudible 01:03:14] if you were a girl that grew up in the late 80s and 90s, you will know who Christina Ricci is, or a guy, any gender. I really liked Yellowjackets. I think it's great.

**Emily Kramer** (01:03:24):
And it was the first show in a while that I've been watching it where I like for the first couple of episodes, I wasn't on my phone half the time. So that's like my measure for, is it good? And then the best movie I've seen recently was we watched CODA, which I think it won some Oscars or something.

**Lenny** (01:03:39):
I think it won best picture.

**Emily Kramer** (01:03:41):
Oh, okay. So it wasn't the Oscar. So I'm really original in my picks here. I'm like, I just watched the Oscar Best Picture, I thought it was great. No, but CODA was like, I think I cried, or at least I almost cried.

**Lenny** (01:03:54):
No, I actually cried. Yes.

**Emily Kramer** (01:03:55):
Yeah, it's about a family who can't hear and then their daughter can hear and they become really interested in music. And there's the story of a family and they're a family of fisherman in Massachusetts, which my brother is a clamor in Massachusetts that's his job. Not his only job, but one of his job that he clams. So he doesn't quite have that fisherman vibe, but somewhat relevant. Yeah, really, really good movie.

**Lenny** (01:04:25):
And that last scene, powerful. Too much, I'm going to start crying.

**Emily Kramer** (01:04:30):
It's a good one, it's a good family story. Lenny is crying right now. He's just in tears remembering the movie CODA. Lenny is going to spend the rest of the day weeping. You won't get a newsletter next week. It's just because he is rewatching CODA.

**Lenny** (01:04:42):
It's going to be an emotional newsletter. Speaking of that, what's a favorite interview question that you like to ask?

**Emily Kramer** (01:04:49):
Oh, there's so many interview questions that I like to ask. I mean, one of the basic interview questions in marketing that I like to ask is just the company that you're working on, what's the product? Why is it better? Who is it for? It's the most basic positioning question you can ask, but a lot of people can't answer it. So that's a good one. And also if you're writing positioning at your company or if you're on marketing your company and you can't tell me what the product is, why it's better, who it's for, go figure that out if that's what the home page of your website should cover. In fact, the hero of your website and so many don't.

**Emily Kramer** (01:05:23):
A fun question that I like to ask. It's a mix of getting to know you but also seeing how you communicate is describe something, and I didn't come up with this question, but I really like it. Describe something complicated that you know well that others don't and describe it as simply as you can. And it's just interesting to hear what people pick. Most people pick things related to cooking which is really strange. I ask that question every interview for a long time just as the final question because you learn something about people. And so many people pick cooking.

**Emily Kramer** (01:05:57):
And I'm like, that's a good choice because I find cooking really complicated and I have no idea how to do it. So describe these various aspects of cooking to me. But that's always a fun one. There's other questions that I always ask like walk me through a project you've done recently from start to finish and I'm listening for things can you tell me the goal? And can you tell the audience? But those are more boring, so I'll stop there.

**Lenny** (01:06:17):
Awesome.

**Emily Kramer** (01:06:18):
What's your favorite interview question Lenny?

**Lenny** (01:06:19):
Oh no, I'm asking you questions here.

**Emily Kramer** (01:06:22):
I know I wanted to flip the lightning round back on you. Have you ever done your own lightning round?

**Lenny** (01:06:27):
I haven't but I'll answer the question I met away. I'm finding the most popular answer to this question is that second one you just gave which is teach me something I don't know. That comes up a lot in these answers.

**Emily Kramer** (01:06:38):
Yeah. Teach me something I don't know. This is a variation on teach me something I don't know. Because it's really about how simply can you communicate it. Teach me something you don't know comes across as a little, I don't want to say pretentious, but it's like it's overwhelming.

**Lenny** (01:06:53):
Well, I'll add a little flavor to it as they often say, you have a minute to explain something I don't know, something interesting to you. And so it kind of forces you to be simple about it. But I like the framing.

**Emily Kramer** (01:07:05):
Yeah. It's a complicated framing. And then sometimes what I'll do, especially if they're going to be someone that's going to be writing is I'll be like, okay, make it simpler. And then I'll have them describe it to me again simpler. And I've probably done that in one interview, I've probably done it four times. Which that part isn't super fun but it depends on the person. If I think they can handle kind of joking around, make it simpler. And if I think the topic's interesting, of course, and I'll like want to hear about something so over and over again.

**Lenny** (01:07:32):
Awesome.

**Emily Kramer** (01:07:33):
Yeah, I mean it's good to have interview questions that maybe teach you something about how they're going to do at the job, but also learn something about the person. And in a way that's not just tell me about yourself.

**Lenny** (01:07:47):
Final question, who else in the industry do you most respect as a thought leader?

**Emily Kramer** (01:07:51):
The word thought leader here is getting me down but I'll answer the first part of your question. As marketers, we love to paint the phrase thought leader. Some of the other marketer that I think are doing interesting things beyond just marketing is Ashley Meyer is someone who is a marketer who also has a fund now. She was comms at Glossier as well as she used to be at Box and things like that. And is big on Twitter, but she's just someone else who is a marketer in return fund manager. So it's always nice to have other people like that to kind of compare notes with.

**Emily Kramer** (01:08:22):
I think that Arielle Jackson from First Round is an amazing support system to founders and marketers at startup. So if you're a first round company, she's a great resource and I think she's just a great resource in general. I also think Kevin Lee, the head of Marketing and Oyster, he's an LPN in our fund, he puts out a newsletter and has a full-time job growing a rapidly growing marketing team. So I have a lot of respect. He's coming to speak to the people in a course that I'm running next week. So he's top of mind. But those are some people that come to mind.

**Emily Kramer** (01:08:51):
But I mean, I have a lot of marketers that I admire. I'm lucky that in our fund we have over 50 marketers so I have a pretty big arsenal of people I can go to just from that as well. So I lean on the people there for a lot of different things.

**Lenny** (01:09:06):
And you're probably going to be raising another fund, and I know you try to raise from marketers and so is that true? Anything you want to add there?

**Emily Kramer** (01:09:13):
If you're a marketer, we have a fund and we allow for lower minimums for marketers. One of my goals is I don't think there are enough marketers who are investors or know how to get into investing. And I know how much founders need marketing help, so love to encourage more people to get involved in investing and can be the on-ramp for that through our fund. So if you're interested in that at all, or a marketer who's interested in angel investing, I'm always happy to have that conversation with you.

**Lenny** (01:09:39):
Emily, this was everything I was hoping it would be and more. I feel like we've helped a lot of founders understand the fog of marketing and I think we are probably going to help a lot of PMs and marketing people work together a lot more effectively.

**Emily Kramer** (01:09:55):
Hopefully. The fog of marketing, marketing is the San Francisco of functions in a company.

**Lenny** (01:10:00):
Karl the marketing fog.

**Emily Kramer** (01:10:02):
Karl the marketing fog.

**Lenny** (01:10:03):
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?

**Emily Kramer** (01:10:08):
Yeah, I am on Twitter and LinkedIn just Emily Kramer, my name, pretty simple. You can find links to the courses that I run, to the newsletter, to our job board, to talking to me about angel investing as a marketer on our website mkt1.co. And that should set you off in the right direction. And we have lots of things going on to help marketers build out their teams and help founders build out their marketing teams. So if that's you and you're in a situation where you're mostly at a B2B company trying to build out marketing, get in touch with me through my website or through Twitter.

**Lenny** (01:10:44):
Amazing. Emily, thank you for being here.

**Emily Kramer** (01:10:46):
Thanks for having me. This was really fun and I'm looking forward to also having that guest newsletter come out with you and just getting Lenny Lennyaised. It's a weird phrase, I won't use that again.

**Lenny** (01:10:58):
Let's move on.

**Emily Kramer** (01:10:59):
We're going to move on. All right. Thanks Lenny.

**Lenny** (01:11:01):
Okay, thanks Emily. 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.

---

## [17/20] When and how to invest in new acquisition channels | Adam Grenier (Uber, MasterClass)

**Adam Grenier** (00:00:00):
One of the biggest pieces of advice I'm giving to people that are like, "How should we adjust our marketing with the economic changes and things like that?" I was like, "Start by assuming you no longer have product market fit, because you had product market fit in a different market." It's a different market now, so you have to start over. And hopefully you do, or it's pretty close to it and you just have to adjust a couple things, and you could be right back on track. But if you just assume you need to launch a new channel to fix this problem, you're going to be wrong, because your entire customer base changed, not just the next 10% of customers that you're looking for.

**Lenny** (00:00:34):
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 Adam Grenier. Adam was head of Growth Marketing and Innovation at Uber where he basically built their growth marketing infrastructure and the team from the ground up. Then he went on to VP of Product and Marketing at Lambda School, and most recently he was VP of Marketing at Masterclass. These days, Adam advises companies, large and small, on growth and marketing strategy.

**Lenny** (00:01:10):
**Adam Grenier** (00:04:04):
Thank you. Thanks for having me.

**Lenny** (00:04:06):
It's my pleasure. I'm really excited to chat. So, I'm going to give a very brief overview of your very impressive career, and just let me know if I missed anything.

**Adam Grenier** (00:04:15):
All right.

**Lenny** (00:04:15):
Sound good?

**Adam Grenier** (00:04:15):
Yeah.

**Lenny** (00:04:17):
Okay, so you were most recently VP of Marketing at Masterclass, which I'm actually a happy subscriber of and I've watched many a video. Before that, you were VP of Product and Marketing at Lambda School. I don't know if that's right before, but that was something you did. Also, you were head of Growth Marketing and Innovation at Uber, which is a really cool title. And I think you spent four years there and you basically built their growth marketing infrastructure and the team. And currently you're doing a bunch of advising and exploring to see what you want to do next. Is that about right?

**Adam Grenier** (00:04:50):
Yeah, you hit most of the key points. I think pre-Uber, the first chunk of my career was on the advertising side, so worked in agency world. So, I kind of think of this as phase three of my life. Ads world was phase one, startup and growth world phase two, and now really just spending time helping entrepreneurs and founders and built companies and that type of stuff.

**Lenny** (00:05:16):
What's been your favorite phase so far?

**Adam Grenier** (00:05:18):
I mean all of them. I just embrace what gets thrown at me and allow it to organically happen. So, each phase has had its pros and cons and ups and downs, and so I think they've all fit pretty well into where I was in my career.

**Lenny** (00:05:34):
Speaking of moving and adjusting and iterating, I know you're big into improv. How serious are you about improv?

**Adam Grenier** (00:05:44):
Good question. Serious in the sense that I've done it for a very long time and I still do it and I try to do it regularly. Serious as in am I aiming to make money off of it and have a career out of it? Unfortunately not. There was a point in my life that that is what I wanted to do. I lived in Chicago, did Second City ImprovOlympic, a variety of different places, did quite a bit of performing, but also got into corporate paychecks early as well.

**Adam Grenier** (00:06:12):
And so kind of built a lifestyle that made doing improv full time probably not the best path for me at the time. And so made a pretty conscious choice early on that it was more of a hobby and if something ever came of it, cool, but if not, that's okay. It's something I keep coming back to, because it's very grounding and fulfilling in ways that work and family life and things like that don't quite hit for me.

**Lenny** (00:06:34):
Actually at Airbnb we had an improv teacher come and work with the PM team. It was for months. We did improv games once a week.

**Adam Grenier** (00:06:42):
Nice.

**Lenny** (00:06:43):
And played all these fun things. And I'm curious what you've taken away from improv that has helped you become better at your work?

**Adam Grenier** (00:06:51):
So, I think generally the whole suite of skills that you develop in improv are pretty applicable, right? Because you are getting comfortable on your feet with change, with teamwork, building off of each other, experimenting, trying new things, a little bit of everything. I think a couple of the key rules or themes of improv that I really try to hammer home with people are obviously the "Yes, and..." side of improv, which everyone's probably heard, which is in a scene the worst thing you could do is deny somebody, because you're actually just stopping progress and you're not building off of anything.

**Adam Grenier** (00:07:27):
So, the appropriate approach is to say, "Yes, that is true, and..." and add to it. So, if someone's like, "Hey, you have a chicken on your head," not saying, "No, I don't." Just kind of ruins that scene. Versus saying, "Yes, I do, and it's name is Sally. What's your chicken's name?" Builds on that and gives it more opportunity. And so I think that in growth in business is super important to be able to say, "Yes, I do see your idea," or "Yes, we did accomplish this and this is what we want to do next and this is how it's going to build on it," I think is super important.

**Adam Grenier** (00:07:59):
The other one that I think is less known or talked about is the gift of details. So, in a scene, if you give somebody really specific details about something, it gives so much more meat to be able to work off of in terms of what's coming next. So, if someone's starting a scene and they're clearly watching television and clicking through the channels and I walk up and just say like, "Oh, you're watching TV, cool." That's a yes statement. I'm not denying what they did. But if I come up and say like, "Oh cool, you're watching TV. Is that an Alf episode? I haven't seen Alf since I was a kid. It reminds me this one time I actually ate my own cat."

**Adam Grenier** (00:08:39):
Just giving those specific details of Alf and me as a kid and I had a cat, which if people don't know Alf, he ate cats.

**Lenny** (00:08:48):
I don't remember that. I remember Alf, but I don't remember he ate cats.

**Adam Grenier** (00:08:51):
He was always trying to get the family cat. So, those kinds of details add a ton of value and you take that into the business world, to use Masterclass for instance, if I say, "Yeah, Masterclass, we've got this way to build content that is both entertainment and education," that's interesting. But if I say, "We create content that is both education and entertainment to solve people's deep curiosities in the way that maybe a biography would." That just opens up the exact problem that you're trying to solve. What are other alternatives to that problem? How are people consuming that? So, I think the gift of details in good improv and learning those skills is something that I really value and look for in every aspect of my business life as well.

**Lenny** (00:09:41):
It sounds like it's really helpful, one, in marketing, creativity and positioning, and things like that you just described. Have you found it also to be helpful in collaboration like this "Yes, and..." piece? I'm curious, is there an example or story where you like "Yes, and..." someone? Do you actually say "Yes, and..." in a meeting? How do you actually find that you use it?

**Adam Grenier** (00:09:58):
I hear it every now and then. I don't usually literally say it. I think one of the areas that I've found it to be valuable is when you've got cross-functional work. So, obviously at Uber we dealt with city teams a lot, and so a lot of the times the way that the central team would scope a problem versus a local team would scope a problem, would almost feel at odds with each other. And if you approach it with that "Yes, and...", it's often still true.

**Adam Grenier** (00:10:24):
It's like, oh, both of these things can be true at once. You could have a different goal than I have, or you have a system problem local to you that is important to you and it's not important to me. That's okay, both things can exist. So, now that we accept both and can work off of each other, we're more likely to build both a better rapport and energy among ourselves because we're not just saying, "No, no, no, no, you're wrong. That's not true, that's not important to the business. Why are you doing that?" That type of energy when cross-functional work, it just kills the scene, it kills that progress. And then you don't build relationships, you don't build the right solutions, all that type of stuff.

**Lenny** (00:11:06):
It sounds really good. Everyone in theory wants to be really good at this. And I imagine just doing a bunch of improv is a really good way to get better at not getting defensive and being like, "Yes. And how do we make this idea better?" Is there something you can advise folks to work on this skill, or is it just do a bunch of improv classes and it'll kind of help build that skill?

**Adam Grenier** (00:11:25):
That's one. I would say that I'll say that all the time to people, "Do some improv classes." And I get a lot of people like, "No, I'm not funny," or, "I don't want to do improv." And I think it's still a really great class to take, even if you have zero interest in doing improv, or public speaking, or any of that kind of stuff. Because, again, improv 101 is taught everywhere. Every city has it somewhere, and it's rarely ever people that are trying to do improv professionally. It's all games, like you said. The classes that you all did at Airbnb is what improv 101 is, right?

**Adam Grenier** (00:12:00):
It's just like, "Hey, let's just have fun. Let's just get out of our skin," and things like that. So, I do think everybody should take improv classes. I think it's also something with a lot of goals or skills that you want to develop, I think being really public and open about you wanting to develop that. So, if you are managing a team and you want to sharpen the skills, make it a team goal, or have accountability and just say, "Hey guys, I know that I've been pushing back on things lately. I want to really try to embrace and grow off of ideas better, hold me accountable, call me out and be like, 'Adam, "Yes, and..." this please."

**Adam Grenier** (00:12:32):
Or giving people permission to push back on that when it doesn't happen, I think also just opens the door for more productive conversations with people and the ability to hold yourself accountable and keep trying it.

**Lenny** (00:12:47):
I love that. And such a good team bonding activity. There's like all these reasons to do this as a team. My wife actually, she's a designer, artist, writer, illustrator kind of person, and she's been taking a lot of these sorts of classes to help inspire her creativity. She never wants to be an improv person, she did stand up classes.

**Adam Grenier** (00:13:03):
That's awesome.

**Lenny** (00:13:05):
As you said, it just helps you get the juices flowing along these lines. Okay, so we're not going to talk about improv the whole time.

**Adam Grenier** (00:13:13):
We could if you want to.

**Lenny** (00:13:15):
We could. Throw me word, let's go. No, we don't want to do that. So, there's basically three things I really wanted to chat about with you. One is how to decide when to invest in an emerging acquisition channel like TikTok, VR, Clubhouse was a big thing. You have some really interesting thoughts on how to decide and approach this thing. To the growth CMR role, which is kind of this, I think emerging role, something you're really good at, and I just want to get your thoughts on what's happening there. And then, three, some real talk on burnout and depression that often comes with working in tech and stuff that we go through. Does that sound good?

**Adam Grenier** (00:13:51):
Yeah.

**Lenny** (00:13:51):
Okay, great. So, to start with in the first topic, if you think about it just every company essentially goes through this kind of S-curve of growth. They start slow, they find something that's working, then hopefully it works out and things start to grow, grow, grow, and then eventually it flattens out and you see this S-curve that happens. And every company is always trying to find the next S-curve to add this layer on the cake that keeps overall growth up while this first growth channel slows.

**Lenny** (00:14:18):
And so people are always looking for what's the next thing? "Oh man, Clubhouse is coming out. We should get on Clubhouse." "Oh, TikTok is so hot, we've got to run some TikTok ads." And there's always something new, like newsletter ads, I don't know, podcast ads, if that's new. And you have a really interesting framework for how to think about this and make decisions and experiment. So, I'd love to hear insights there.

**Adam Grenier** (00:14:38):
So, the exploring emerging channels framework that I'll take, either my teams or companies that I'm advising through, has three core ingredients that I like to spend time with. So, the first is really understanding if there is an overlap between what the customers need is, what your company's goals are, and what the channel actually does really well. So, the example I've used in the past is Spotify in the moment of things like Clubhouse and Paparazzi and stuff like that becoming really popular.

**Adam Grenier** (00:15:14):
Well, for Spotify, they're trying to get more people to consume music and be entertained by music and things like that. And it's all audio driven. And so their growth goals are probably around new customers or deeper engagement with audio. The customer's needs are discovery and more ways to maybe have deeper relationships with their music. If you're a jazz fan, can you learn new jazz artists or more about the artists that you love? Things like that. And then take those two channels. If you take something like Clubhouse, it's audio first, it's almost like live podcast radio type feel to it.

**Adam Grenier** (00:15:57):
You can get into these rooms with just people with really amazing esoteric knowledge about something. And so its strengths have a really clean overlap to me with the goals of Spotify, the needs of the customer and the strengths of that. And so that to me is great. That is probably a green light in terms of is it even worth our time? Versus Paparazzi is very photo driven and nothing really to do with music or anything like that. And so it's like even though Paparazzi might have become the best biggest channel ever, is that the thing you should be putting your time into? It would be a yellow light for me at best.

**Lenny** (00:16:36):
And how did you describe that again? It's the medium matches?

**Adam Grenier** (00:16:40):
Yeah, the strengths of the medium. So, let's take influencer right now. Actually two of the channels that a lot of people are talking about right now are streaming TV or OTT and influencer marketing. And so to me, one of the strengths of influencer marketing is hyper targeted contextual marketing. And so I can go find the five influencers that are hardcore Alf fans, and if I'm marketing Alf something, great, I can go find that specific thing. Whereas OTTs a lot harder to get that specific.

**Adam Grenier** (00:17:16):
OTT strength is broad reach and video storytelling and that type of stuff. So, it's like, okay, well maybe my medium is if I'm Masterclass and I have a ton of video content and storytelling and things like that, that channel actually makes a ton of sense probably. So, it's like what are the strengths of that channel is something that... that is actually probably the piece I see people ignore the most, which is they just want to know if a channel is hot or not. And this gets especially hairy in this world of a lot of B2B doing more consumer-esque marketing. There's so many B2B companies that just don't apply to emerging consumer channels.

**Adam Grenier** (00:18:00):
And it's just like, please just stop. I don't need a Notion Clubhouse channel this week. And maybe there's a world to do that. But I think that's kind of number one, is making sure that there's even a reason that you should be there to put it on your radar right now.

**Lenny** (00:18:19):
Awesome. What does the OTT stand for by the way?

**Adam Grenier** (00:18:22):
Oh my gosh, you're putting it on the spot.

**Lenny** (00:18:24):
It's all good.

**Adam Grenier** (00:18:25):
I'm drawing a blank on it.

**Lenny** (00:18:26):
But essentially it's a streaming platform?

**Adam Grenier** (00:18:28):
Over the top. Over the top. So, instead of it being cable TV, it's coming from a box. So, it's primarily if you think of ads on Amazon or Hulu or even if you go to cnn.com and you start streaming and you get an ad first. it's basically video ads, but a lot of them now are happening on televisions and on streaming services rather than just on websites.

**Lenny** (00:18:55):
Got it. Okay, cool. So, the first is the strength of the channel. You should look at that.

**Adam Grenier** (00:18:59):
Yep. And how that overlaps with your customer and your business needs. The second is the channel DNA. And so this is looking at things like where are they in their trajectory? So, Clubhouse is actually a perfect example, because in a weird way, so Clubhouse got hot before Facebook got cold. And I was pretty amazed how many more people were trying to crack Clubhouse than TikTok, because TikTok hadn't really released their ads solution yet, but neither had Clubhouse. But everybody was talking about Clubhouse, and TikTok is very clearly not going away anytime soon, where Clubhouse hopefully won't. Like this is an amazing product.

**Adam Grenier** (00:19:41):
I really enjoyed it and loved it, but it was clearly very early, very quickly at that point of hotness where everyone was just kind of, "That's the reason I should be there." And part of this reason is to accept the risks of going into that channel. So, if I go and dedicate two quarters of work to Clubhouse, I need to accept that they are so early in this curve that there's a good chance this is a once in a lifetime opportunity and it'll be over. It's not a repeatable action. It also is important because if you get something to work on a channel that's earlier in their growth curve, the likelihood that they will change is very high.

**Adam Grenier** (00:20:23):
You're going to need to commit a lot of cycles to keep it going, because it's like, "Okay, well, their product is going to evolve drastically very quickly over the next two years." And so a really great example is Facebook early... I was at Zoosk. And so Zoozk and companies like Zynga got tons of their early growth because of notifications on Facebook, which was one of their early features, which allowed basically anybody that took any action on Zynga, it would post on everybody else's page that you got 10 carrots, and that was a huge growth lever.

**Adam Grenier** (00:20:59):
But then Facebook just pulled the plug on that. And so it's like, well, if you put all of your energy into that and that's it, it was pretty clear that that was still an area that's like this may not last forever. The last thing on the channel DNA that I like to look at that's a little bit more, I don't know if odd or unusual is the right term, is I like to spend a lot of time thinking about how they monetize. What is the monetization strategy of the channel? And the reason is because if you, as a business, can match or support their monetization strategy, it actually gives you a really interesting leg up with that channel.

**Adam Grenier** (00:21:37):
Because the likelihood of you being able to call them up and go do custom stuff with them, or partner with them, or that your solutions will actually stick around for a while, it'd go up pretty drastically. And so my key example of this was with when Facebook started exploring mobile ads, Hotel Tonight, we were one of the alpha testers of mobile ads, because I'd been sitting here buying ad inventory on networks for the last five or six years and just waiting for Facebook to work, because it just wasn't really working for mobile installs.

**Adam Grenier** (00:22:13):
And it's like, I know this is a huge channel because I can use it on my online marketing, my web marketing, but as a mobile acquisition it's nowhere near as efficient as a lot of these other networks. And so as soon as they were doing that, I was able to basically position and say, "Look it, you want to work with us. Let me into your alpha, because I have five years of experience already buying mobile ads. I know the space. I know it'll work. And if you get us to work, we're a killer case study, because we are a non-game and a lot of money is spent on gaming, but there's these whole other major categories that you're going to need other than gaming examples within that group. So, you're going to be able to use me as a case study and a lot of different scenarios than the gaming players."

**Adam Grenier** (00:22:59):
And so I was spending a lot less than the gaming players, but because of that understanding that your goal at Facebook is to make ads work for all of travel and for all of leisure and those kinds of things, that's the value of working with me. So, that's another piece of the channel DNA I like people to focus on.

**Lenny** (00:23:18):
Awesome. That's such a good one, because to your point, if your goals are aligned, they're going to be like, "Yes, let's make this happen." And it always feels like it's this behemoth that doesn't want to talk to any new startups, but if you can make the case of this is going to help you and the way you laid out is so clear, it's such a good idea.

**Adam Grenier** (00:23:35):
And especially with emerging channels, right? Because their whole thing is that make this work for a long time. It's part of the challenge you see with some new channels flipping to the other side of growing an ads business, will gravitate towards like, "I want to get Disney on here," but Disney is very campaign driven, or they have been traditionally, where it's like you may get one big paycheck from them, but that doesn't... The way that UA driven gaming works is you get that to work, that's a gift that keeps on giving forever, right? Because there's not one of those companies, there's thousands of them and they all do the same thing. So, being able to drive that conversation is really helpful.

**Lenny** (00:24:18):
Cool.

**Adam Grenier** (00:24:18):
And then the third main ingredient is just your own company DNA. And so I think risk profile is a big one. Do you actually have comfort in being a first mover, a true first mover? Nobody knows anything, tracking's not going to work, it's not going to be programmatic. You're probably going to show up on content that's offensive. You're probably going to ask for refunds that won't happen. It's going to be really painful to be a true first mover. Do you have that appetite? Do you have the staff to actually be able to put someone on that and it not distract from everything else?

**Adam Grenier** (00:24:53):
And then the other piece on the company side is just your current channel mix. There's very few companies that I recommend saying, "Yes, go put energy on this brand new channel that you don't know how to scale yet before you've figured out some type of volume on Google and Facebook." Every now and then there may be a perfect fit where it's like, absolutely, you should be the person doing this. But if you're not at least getting something out of the basic channels that everybody else is using, it's probably not the thing you should be putting your first energy into. It should be like, "Great, I've got a good foundation." Like you said, now we're at that stage of trying to add things, tends to be a better stage to do more risky exploration into new channels.

**Lenny** (00:25:40):
What advice do you have or can you give to founders teams that are trying to test one of these in terms of just how to run these tests? How much time should they spend, would you say? What do they look for? I know that this is a hard question and super dependent on the situation, but any advice there?

**Adam Grenier** (00:25:55):
So, I think going through those three ingredients should help shape that answer, right? Because if you're like, "Okay, well, the first one is super strong, the channel DNA is maybe really early and I've got a small to mid-size team and maybe only one channel working," then it may be like, "Great. Put half of one person into this, because it's maybe interesting. But don't put any more than that into it." Versus if it's like, "Man, this is a killer fit the channel's a little further along and I have a 20 person team, so I'm going to put three dedicated people to this, because we are in prime position to be the leaders in this new channel and really push it."

**Adam Grenier** (00:26:36):
So, I think it's figuring those pieces out, because it is a very it depends answer, but rarely ever is it like, "Hey, this should be your entire team's focus for the next three sprints or five sprints." I think that if you've got that half person working on it for a while and there starts to be some magic happening, sure, put a sprint or two against it as a whole team. But generally speaking, I think keeping it minimum at first is my typical recommendation.

**Lenny** (00:27:06):
I had another guest, Yuri, who I think from former Grammarly, and he made a really good point that it's often better not to try something than to do it badly and then take away the wrong lessons. I guess, in your experience, what's a timeframe you think people should put into this stuff? You said two sprints, maybe a couple weeks. I don't know, what's the range of just maybe don't spend more than X months on something new if it's not clearly working, just based on your experience.

**Adam Grenier** (00:27:33):
Generally I wouldn't let anything bleed past a quarter. You can probably get some good signal in a month or less, what I would call fishing. It wouldn't be like you're just putting bait in the water to figure out where the fish are, not necessarily getting statistically significant repeatable solutions. The big variables that can change that timing, so if I'm exploring a new video channel, the content I need to create is if I'm going to have to create something that takes three weeks to produce and $20,000 to make, I may want to give it a little more time, because I gave it more of an upfront investment.

**Adam Grenier** (00:28:16):
Versus if it's like I want to put text ads in podcasts listings or something like that. It's like, great, I can do that by myself at midnight and it's not distracting anybody or anything. And if it doesn't work in three weeks, let's move on. But generally ideally what you're working through, and we'll touch a little bit more on this with the Growth CMO, is that this should all be part of a roadmap. It shouldn't just be randomly chosen and thrown at. This should be part of your sprint process and you should have a backlog of other things that you want to try. And so you're actually weighing that decision of how long based on what other opportunities you're missing out on by investing in that.

**Adam Grenier** (00:28:57):
But I would say most channels, especially new ones, are going to take more than a couple cycles to kind of suss out. Because there's no rules, there's no playbooks yet on how to do them well. So, give it a little bit of time, but if you're going over a quarter and you don't feel like directionally it's getting better or it's interesting, I would put it back on ice for a while.

**Lenny** (00:29:18):
Cool. And to your point, you're not going to see any statistically significant answers. Is the thing you look for just like you know it when you see it? Oh wow, qualitatively feels like it's working kind of thing? Is that what you kind of look for?

**Adam Grenier** (00:29:30):
Yeah, and I think define that going into it. What am I looking for, for this? So, something like Clubhouse I'm probably not going to see clicks. It's more about are we able to start a room and increase the size of that room by 10% every time that we run it? Okay great, that means that we're at least getting better at this and there's more reach available to us. But if we're getting 20 people every time we start a room and then it goes down to 15, then we're either not doing this well, the channel's not doing well, or there's just not enough reach for us to actually expand. Versus TikTok you might be able to say, "Great, I can actually track clicks and conversion, so let's look at it the way we would any other channel."

**Lenny** (00:30:11):
Got it. So, kind of look for momentum and that you're getting better and that it's moving somewhere. Awesome.

**Adam Grenier** (00:30:16):
Yeah. Yep.

**Lenny** (00:30:17):
Cool. So, a question that I'm sure is on many people's minds that they would want to ask is, Adam, what are emerging platforms that are interesting right now that we should experiment with? What do you feel?

**Adam Grenier** (00:30:28):
So, I mean I mentioned OTT, or basically the key thing with OTT is that it's way more trackable than traditional television, but it has similar value that traditional TV does in terms of the ability to do more long form storytelling type content, and a lot of it's not skippable if you buy it. And so those are reasons to be exploring that right now. It's hard for me to call that emerging channel, because it's been around forever. It's there's more of it and the tools and services around it are way better now than they were four years ago. And so I think the sophistication and ability to scale OTT is much higher now than ever before. Influencers probably the one that I'm most intrigued by, because similar to OTT, the scale and services and the ability to go do it is still there.

**Adam Grenier** (00:31:19):
It's also got that hyper granularity that when I get into influencer tools, it feels to me like early Facebook when I used to go be able to target Lenny, or 10 people that have exactly the same likes as Lenny. And that type of stuff where it's like you can get so specific and find exactly who you need. It's incredibly tedious and manual and it's a lot of relationship management. So, I'm also keeping an eye on the technology being built around influencer, because I think that's a huge area of opportunity for entrepreneurs right now.

**Adam Grenier** (00:31:57):
But generally speaking, the scope and opportunity there is huge and it's not going away, but it feels very new and different right now. And it supplements the ability to do some hyper level targeting that you've not been able to do, that Facebook and Google are getting less open about at the same time. I think VR is really interesting in the way that mobile was interesting before iPhone Three, where it was if you've got a VR app, it's a really interesting space, but if you don't, it's not that interesting to me yet. Any that have come up for you that you're like... what are your thoughts on this?

**Lenny** (00:32:35):
No, these are great. All I think of is TikTok.

**Adam Grenier** (00:32:38):
I feel like TikTok's crossed a chasm, whereas they actually have a formalized ad platform now, people are finding scale. There's still a ton to do there and influencers is also weird, because it crosses all of these other worlds as well. But I think TikTok is actually hyper interesting and everyone should be doing that. But I think of that less as you should be doing it as should I do it, should I not? And it's more I need to figure out how to do Facebook if I'm at least mildly appropriately should be there.

**Adam Grenier** (00:33:05):
The podcast ads I think are great. I think that I bought podcast ads 15 years ago, so it doesn't feel like an emerging channel to me. I think there's way more volume now than there's ever been before. One of the guys that was on my team at Uber has a company that's doing programmatic buying and that type of stuff. And so I think there's more opportunities on podcast. I think people want to treat it like Facebook ads or direct response ads, immediate response ads. And actually what I keep seeing as the effective strategy with podcast ads is treating them more like radio where it's more about getting on the right program, making it personal and feel like it should be part of that program, and then repeating over and over and over again.

**Adam Grenier** (00:33:53):
So, I think podcast is super interesting. I think it's just hard to scale. It's likely not going to get people the same volumes as the Googles and Facebooks of the world.

**Lenny** (00:34:01):
Cue our mid-roll ad. I'm excited to chat with my friend John Cutler from Podcast sponsor, Amplitude. Hey John.

**John Cutler** (00:34:08):
Hey, Lenny. Excited to be here.

**Lenny** (00:34:10):
John, give us a behind the scenes at Amplitude. When most people think of Amplitude, they think of product analytics, but now you're getting into experimentation and even just launched a CDP. What's the thought process there?

**John Cutler** (00:34:21):
Well, we've always thought of Amplitude as being about supporting the full product loop. Think collect data, inform bets, ship experiments and learn. That's the heart of growth to us. So, the big aha was seen how many customers were using Amplitude to analyze experiments, use segments for outreach and send data to other destinations. Experiment and CDP came out of listening to and observing our customers.

**Lenny** (00:34:42):
And supporting growth and learning has always been Amplitude's core focus, right?

**John Cutler** (00:34:46):
Yeah. So, Amplitude tries to meet customers where they are. We just launched starter templates and have a great scholarship program for startups. There's never been a more important time for growth.

**Lenny** (00:34:55):
Absolutely agree. Thanks for joining us, John, and head to amplitude.com to get started.

**Adam Grenier** (00:35:01):
I also come from a very consumer perspective. I'm actually stronger on B2B companies using podcasting, because it has that exact same value I just described, but each one of their customers is substantially more valuable. So, they don't need the scale that a consumer application or product would need.

**Lenny** (00:35:20):
Yep. That's exactly who I work with usually. One last question on this topic. What percentage of the time do you find that an emerging channel works? Is it like 20% of the time, 10%, 5%? What should people estimate, it's probably not going to work but when it does it's going to be game changing?

**Adam Grenier** (00:35:34):
Like 5% of the time. There's new things popping up all the time. I think the area that I think of as emerging that I've found more success in is taking things that exist already and make them... so the two slices of it are either it's existed for a long... like podcasting. So, it existed for a long time and now we're finally getting to a spot where it feels scalable. The other is existing channels that introduce something brand new.

**Adam Grenier** (00:36:04):
So, at the mobile ads I described on Facebook, pre mobile install ads and post. Those first 18 months of mobile install felt like an emerging channel, right? Because they were changing the product every week and tracking didn't work, and there were all these funky problems with it even though Facebook had been around forever. But brand spanking new channels, I don't know, they rarely work or are worth the effort early that you hope that they will be.

**Lenny** (00:36:35):
Cool. But when they work, it's game changing I imagine. Reminds me Apples coming out with Apple TV, I think it was, and they're just like, "Hey Airbnb, you should make it app for Apple TV. It'll be huge." And there's a team put on it. I don't know. They spent a month building this app and did a bunch of nothing as far as I understand, but it felt good. It felt good to be part of the launch. One question I wanted to come back to, are there tools that you recommend for influencer marketing that you want to plug, or point out?

**Adam Grenier** (00:37:01):
We were using Grin at Masterclass, we onboarded them. So, there's probably half a dozen companies in that same zone where they're building tools that allow you to do the discovery of influencers, the CRM of those influencers, and also often the measurement and payments and all that kind of stuff. So, it's an all in one type of management platform. That being said though, like I said, it's still super manual. It's nice to be able to go and find this list of 50 influencers that are the exact right influencer for this class launch, or whatever it might be.

**Adam Grenier** (00:37:34):
But it's still then I have to wait till they all respond to me and there's still a lot of manual back and forth. So, that's probably one of them. I'm trying to think of... There's a few other in that same category that are competitive with Grin that they all seem equally pretty good. I can't even remember the reason we chose Grin over some of the other ones.

**Lenny** (00:37:53):
It's a good name.

**Adam Grenier** (00:37:53):
It was all pretty close.

**Lenny** (00:37:55):
Sweet. Okay. If any other comes to mind, we'll throw it in the show notes. Before we get to the growth CMO discussion, there's kind of this tangential area that I wanted to spend a little time on, which is this idea of as a startup you initially should and often do start with a very narrow audience, your early adopters. I read this post about calling them your super specific who, and eventually you want to cross the chasm and go broader. And you have some interesting insights on how to think about that, and when to do that. Can you talk about that?

**Adam Grenier** (00:38:26):
Yeah. So, I think the book, Crossing the Chasm, is a great place to start in terms of thinking about the broader topic of that. What I see missed a lot of the time that I like to spend time with people on is to really understand that those early adopters are often just drastically different than the broad audience. And spending time to actually figure that out and map out what you need to see with those early adopters to have confidence that the product is actually going to have product market fit beyond them.

**Adam Grenier** (00:39:07):
So, I don't have anything hyper specific to add to that necessarily, or happy to dig in deeper to it, but it's probably the biggest challenge that I've seen with a lot of companies that I've worked with. And then as I do more investing and things like that, it's probably the biggest flag that I see with a lot of companies that claim to have product market fit, which is your TAM and your product market fit are not using the same definition. And that problem I think is often just a red flag for a lot of companies that I meet.

**Lenny** (00:39:40):
Got it. So, essentially you often underestimate how challenging it'll be to grow from your initial early adopter crowd. Is there an example of that happening where a company just got screwed because they didn't think about that enough? Or is there something someone can do early on? Is it test a little bit more broadly early? What do you recommend there?

**Adam Grenier** (00:39:59):
I mean Clubhouse might be a good example in the sense that they leaned into the broader audience maybe quicker than they should have. Their product market fit seemed to fit the moment in time and could they have built some experiments, or tools, or features that maybe stress tested will this work in an ongoing fashion? If they were on such tear, that's a pretty hard decision to make, I'm sure.

**Lenny** (00:40:29):
So hard, it's easy in hindsight.

**Adam Grenier** (00:40:33):
I think that's another piece of it is that the audience changes aren't always just literal people. Even right now, one of the biggest pieces of advice I'm giving to people that are like, "How should we adjust our marketing with the economic changes and things like that?" I was like, "Start by assuming you no longer have product market fit, because you had product market fit in a different market. It's a different market now, so you have to start over."

**Adam Grenier** (00:40:57):
And hopefully you do, or it's pretty close to it and you just have to adjust a couple things and you can be right back on track. But if you just assume you need to launch a new channel to fix this problem, you're going to be wrong, because your entire customer base changed, not just the next 10% of customers that you're looking for.

**Lenny** (00:41:14):
It's just a reminder of how freaking hard startups are. Man, we have product market fit. Okay, we're done. Let's move on.

**Adam Grenier** (00:41:21):
Not anymore.

**Lenny** (00:41:21):
Not anymore. Oh man. Okay, sweet. So, onto this next topic around the Growth CMO. So, you're this really interesting combination of marketing brain and also very analytical growth person, and I think you refer to this as Growth CMO, which I don't actually hear the term much. So, I'm curious, what is a Growth CMO? How do you define it? And why is it important?

**Adam Grenier** (00:41:43):
Yeah, so it's something I've just spent a lot of the last few years thinking about, specifically because now I've been at a handful of companies where we've brought in CMOs that in all ways are absolute world class CMOs, and they don't last, they don't fit and they don't succeed. And so I've spent a lot of time and figuring, well, why not? Some of it coming because of spending time with those people being like, "Why are you doing it this way? That's not how a company at our stage operates."

**Adam Grenier** (00:42:18):
Trying to do it the way that a traditional CMO would've done marketing for a company, et cetera. One of the key examples I like to use is brand, in that everybody when they think about brand they think of it as an action, not as a consistent ongoing investment, or they think about it as campaigns and things like that. And from planning to execution to learnings, a traditional CMO will drive learnings and identify learnings. And in my mind, I think a Growth CMO is looking at each brand investment as how do you then immediately follow that up with the next one? How do you shift to this fast product iteration mindset with even things like brand?

**Adam Grenier** (00:42:58):
It's very possible, but it's so counter to a lot of traditional marketing DNA. That, to me, means that we have a lot of mismatch marketing leadership, and that quickly eliminates trust with the marketing organization. It means that we rename everything marketing to product led growth, or growth, or referral programs. To me, it actually dilutes the value of marketing should be playing in the company. And it doesn't mean that the traditional marketing CMO isn't a good fit for some companies.

**Adam Grenier** (00:43:37):
I think the direct to consumer products are still very well suited to have a more traditional CMO. But I think product driven companies, product led companies, if you are CMO and your product leader aren't married at the hip, you're just missing out on just tons of opportunity, and the likelihood of things actually working very well consistently and compounding on each other.

**Lenny** (00:44:05):
So, what are the attributes of this person of what you call a Growth CMO? Sounds like partly it's being much more performance driven. Sounds like a big part of it is understanding product and not creating these silos. We're going to market the thing, you guys go build this thing. But also as a person, that's a great CMO. What else do you look for?

**Adam Grenier** (00:44:22):
So, I would say so data driven generally. To me performance is a very loaded word in our world, because people think, especially in marketing, think that means not brand. But they're very data driven. And so when we take things like retention and even brand and the consideration funnel and, yes, you can't measure those exactly like you can measure landing page clicks and sales, but you absolutely can measure them. And making that part of the DNA of everything that's happening, data being part of that, I think is pretty quintessential of being a growth driven CMO.

**Adam Grenier** (00:45:00):
The second, I think, is the iteration process is not thinking about things and, "Hey, we need to plan for the next 24 months," but you can still do that and you can still have a vision and everything. But having that more of a agile type approach to everything. And again, this could be the storytelling that your sales people are doing, to what are your landing pages look like, to what is the design of your logo, to the brand itself. All of those things, like being more open to everything being possibly iterated on, on a regular basis using data to validate that and challenge what has worked for you.

**Adam Grenier** (00:45:38):
We live in such a real time world now, especially with product driven companies. The things change so quickly. If you as a marketing leader aren't being iterative and thoughtful about things with it, you'll get eaten alive. And then I think experimentation is just a huge piece of it. And something that I see a lot of more traditional marketing leaders, the idea of experimentation is try a new channel. It's not like how do we experiment with our brand? How do we experiment with the funnel? The whole picture, not just the top of the funnel or the external elements of it.

**Adam Grenier** (00:46:17):
One of the things that I haven't quite figured out the right language to put against this, but the traditional model of marketing is the four P's, product, placement, promotion, pricing. And in my mind, the world that we live in now, product is no longer a part of marketing, but it's actually they're married at the hip. They're one and the same, and most companies aren't operating that way. They're still operating as if they're two wildly different things. Even if they say they're working together, it's still, there's not. And to me it's just like, no, no, the product, it is the company now.

**Adam Grenier** (00:46:59):
And the marketing is integrated with literally every single piece of it. A lot of traditional marketing got established in the 1920s and the 1950s around products that took years to develop or try, or a product team was a science group trying new flavors of cereal. And so the marketing team owned the box, where it went on the shelf and what the price was and all of those kinds of things was marketing, because product was such a wildly different part of the organization. And I think still there's just a lot of fundamental things that marketers think about that are stuck in that world, because most haven't had to grow through the true growth of a business that's just being established today.

**Lenny** (00:47:53):
And the assumption is every software company should be hiring a CMO that is of this sort, of a Growth CMO, right?

**Adam Grenier** (00:48:01):
Yeah. And I would say that my sense is that there's very few marketing leaders that can't be a Growth CMO. So, I don't think you have to have come up as a performance driven experimentation. It's more about adapting and growing. And again, the fundamentals are all the same. One of my pet projects that I haven't done anything with yet, is that every time something new comes out in the growth world, I go back in history as far as I can to try to find the earliest example of that. Just to be able to say, "Look, this isn't new, but we can learn from the way that Coca-Cola invented the coupon."

**Adam Grenier** (00:48:37):
The first known coupon was Coca-Cola giving away Coke for free, but it was actually a marketplace, because what they would do is they would go to a town and they would go to the soda fountain and they would give a free Coke syrup to that side of the market and they would give coupons to the other side of the market to spark it, to get it going. And then it's like, well, now all the customers want Coke, now you need to supply it, you'll pay for it. And learning that and understanding that is really cool. And it's just interesting to me, because I'm a huge nerd.

**Adam Grenier** (00:49:09):
But that to me is all of the things that great marketing leaders have learned are right, it's the operating aspect of those insights and those skills and understanding your customer and their psychology. All of those things have stayed the same. It's the operating of it in the way a growth organization, like a product driven growth organization operates, is very fundamentally different than the way a traditional marketing run organization had run.

**Lenny** (00:49:37):
I was going to ask you what a marketing leader can do to evolve into this where you think things are going, and your point about you're capable of it, you can iterate and adapt is really great and empowering. Is there anything specific they can do to learn how to do this better, other than is it like mentorship? Is there classes, courses? Just do the job, figure it out? Do you have anything you can suggest there to folks listening and they're like, "Oh, shit. I'm in trouble?"

**Adam Grenier** (00:50:02):
Honestly, I think learn product development. Go learn agile product development. And there's actually a book called Hacking Marketing, I think. I'll confirm. But it's essentially how to run a marketing team on Agile. That to me is just, again, any great marketing leader should be able to go and consume how to do product development, how to run a product like sprints and those types of things. And their mind, if they're great marketing CMO or a CMO, will be like, "Oh my gosh, I could do this with this big event that we want to host. I could do this with everything."

**Adam Grenier** (00:50:43):
There's nothing off the table when you actually learn those fundamentals. But as well as I know smart people can learn that stuff. There's lots of resources out there. Reforge has some classes on it, there's a bunch of new product led growth classes out in the wild, like Maven I think has a couple. And there's a variety of those types of things that just going and doing it, you don't have to go and operate it yourself. You don't have to go become a product manager. But understanding those skills and those systems will, one, I think make you think differently about how to run your marketing team and, two, make you exponentially better at working with your product organization.

**Lenny** (00:51:21):
Awesome. I'm actually hearing from folks listening to this podcast not live right now, but broadly, that this is a good way to learn how product works and how product leaders think. So, that's interesting. So, if you're listening to this, good job. You also mentioned that a lot of marketing leaders don't work out at a company, they join, they leave, things go wrong. As a hiring founder or leader, what do you look for to tell you this person's probably not what we need and not what you'd call a Growth CMO? What are flags that are like they're probably not going to adapt and evolve to the way we want to operate?

**Adam Grenier** (00:51:53):
So, I think first and foremost, it obviously depends on the stage. Anything let's say C or below, comfortable with chaos and willingness to go do something they have not done for probably 15 years are two huge signals for me, because every company I've been part of at every scale now, which is all of them basically, that's the thing that a lot of people coming from more traditional marketing environments into startup worlds, it's a pace and just the unpredictability and change and those kinds of things are just at such a higher rate than they've seen for a long time that it can be really jarring for people.

**Adam Grenier** (00:52:49):
And I think it's totally reasonable. It's crazy, right? If anybody that's had the exposure on both sides. And then the willingness to go do the work. People are churning constantly and the challenges are different every week and those types of things. And so it's like every now and then you've got to go write an email or you've got to go open up Facebook and get into the weeds with it with your team, into the data of it and that type of stuff. And that's stuff that I don't want to do, personally, me. I'm past the point where I should be in Facebook.

**Adam Grenier** (00:53:17):
But man, when I need to, I'm willing to, and I'll go get in the weeds with it and I'll use my time to just be like, "Look, we have to figure this out now." And I'm going to go do the things that I thought I was done with in my career. So, those are pretty big ones. I think then generally speaking, one of the exercises I like to take founders through when they're hiring a marketing leader is every marketer is going to have a T-shaped career.

**Adam Grenier** (00:53:41):
Everybody came from something they probably became awesome at and then over time just expanded their purview. So, for me it was mobile. I got into mobile. My first client ever was on Sun Microsystems early 2000s, getting Java developers to make apps for flip phones. So, I just knew digital mobile world really, really well before a lot of people did. But then eventually I'm like, "Great, now I'm running an entire digital marketing team. Now I'm running an entire marketing team. Now I'm getting into growth. Now I want to learn product," and I've expanded. And so typically it's going through that exercise of find out their T, find out their strength, and then spend time figuring out how they make up for those other things.

**Adam Grenier** (00:54:24):
So, for me, at Lambda school I ran our PR team for a while. I am not a PR person, but I make it a goal in my life to get to the valley of despair of the Dunning-Kruger effect, to be like, "Great, I just need to know how bad I am at PR," because if I still think I'm good at it, that's not a good place for me to be. But once I know how bad it is, I now know I need to go hire the right person to come in and I'm going to listen to them. I'm not going to assume that I'm smarter than them, and those types of things. And so I think the same thing with product questions and data questions and experimentation questions for this concept of a Growth CMO is like, well, somebody's coming from a world where they've not had to work really closely with the product team, spend time with them to figure out how they plan on adapting to that.

**Adam Grenier** (00:55:12):
My guess is most won't have thought of that. The good ones will be able to figure it out together with you in that interview, or afterwards, or whatever it might be.

**Lenny** (00:55:22):
Awesome. Maybe one day we'll do a follow-up chat just to dive into hiring a marketing person. I know that's a whole deep topic.

**Adam Grenier** (00:55:31):
Lots of thoughts.

**Lenny** (00:55:31):
Okay. Oh man. Okay. We've got to book that. But, okay. So, you mentioned the valley of despair, and that's a good segue to our next topic. So, I found this old tweet of yours where you talk about burnout and depression, and you kind of make this point that a lot of times you feel like it's burnout and it's actually depression. And just broadly mental health is just this topic that's not really spoken a lot about in tech and in business. And so I'd love to just spend a little time on this. I know you're a big proponent of talking about these sorts of things, so I'm curious, I know you've been through both these things and I'm curious just to hear your journey, what that's been like, and what you've learned about how to get through it?

**Adam Grenier** (00:56:08):
So, the two biggest inputs for me in terms of really taking the time to understand my mental health, one is my wife, who's been a very strong proponent of mental health resources for everybody since I met her. And so just being able to learn from her and get exposure to, well, why is this important? What are the values of it? And seeing it pretty regularly of family members, or coworkers. Or it's like, oh man, I bet there's something deeper here that maybe is important for them to figure out.

**Lenny** (00:56:46):
Is that just something she's good at, or is she trained in this stuff?

**Adam Grenier** (00:56:49):
No, she's good at it and she's in therapy and stuff like that. She's one of the most empathetic, passionate people I've ever met in my life. And so she just feels like poor people so much that I think it's something really important to her. And then at Uber, I got to a spot where I was incredibly exhausted and tired and just down, not excited about work and things like that, and so I started going to therapy and with this assumption that I was just working too hard.

**Adam Grenier** (00:57:20):
That was kind of my like, "Man, I need to go to therapy to figure out the tools that I need to deal with me working too hard." And I just uncovered so many interesting things that I wouldn't have expected. So, one was that I'm the youngest child in my family and I did something pretty different than a lot of my relatives and things like that. So, recognition is something I long for, and it turns out I get that at work and I just hadn't gotten that in other parts of my life. And so this thing that I'm like, "This is my problem," was actually a solution to my real problem.

**Adam Grenier** (00:57:58):
And knowing that just helped me totally just change my perspective of how hard I work. I was getting judgemental about myself around, "Man, I'm working too hard. I shouldn't be doing this, but I have to." And then I got in the spot where I'm like, "Oh, I'm working hard because I love it, because I like it, I'm having an impact and I'm working with people I like and people respect the work that I do." And that helped me identify that I can work just as hard, but I can work smarter. I can work more on the things I have impact on.

**Adam Grenier** (00:58:30):
I can work more with people that actually respected the type of work that I'm doing. And that actually just started to relax me and get me to the spot of, "Oh, okay," I still some burnout in there, and that's part of the innovation. Part of my title was that I got to a spot where I'm like, I was traveling constantly, I had teams all over the world and the structure of Uber was working where every city had a GM and I was the person they called when their spend was too high. And so 500 GMs-

**Lenny** (00:59:05):
Uber GMs especially.

**Adam Grenier** (00:59:06):
Yeah, exactly. And so I was working in a world where I was dealing with a lot of politics. I love mentoring people, and I had this massive team of 150 people that I barely know any of them. And so I'm not mentoring people either anymore. And I just felt like I'm working so hard on things that I actually don't enjoy. And so I'm like, I'm going to go work on flying cars, which is a whole other podcast too. So, that was my, okay, there was burnout in there.

**Adam Grenier** (00:59:33):
I know that was a fact, but some of those feelings or things that I felt my entire life that I uncovered that I thought was just burnt out, I was like, "Oh, actually at this point in my life, this point in my life and this point in my life, I felt this way too. And at those points I wasn't burnt out. And so I actually have deeper work to do here and deeper understanding of myself so that I can actually maximize my life and enjoy it." And because I'm going to keep working to some degree this hard. And I want to just make the most of that.

**Lenny** (01:00:03):
I don't know if you mentioned this, but I imagine parts of those points were depression, not burnout. What have you found to be that line of just like, "Oh wow, this is a lot more serious than I'm just working way too hard?"

**Adam Grenier** (01:00:14):
For me, it's hard to describe, but I personally now can pretty cleanly tell the difference between exhaustion and depression. And it tends to tie to my broader motivations, not just my motivation to work. So, when I'm exhausted, I'll still show up to work, I'll still execute, I'll still do those types of things, but I'm going to go and if I can take an improv class, it's going to be a blast. I'm going to enjoy it and I'm going to love it. If I'm depressed, I won't go to that improv class. I'll just cancel it. I won't go to it. Or if I go to it, I'll go home immediately. One of the things I love about actual improv classes, is the community. Is, "Hey, let's all go grab a drink now." And this is a totally different group of people. It's not my family, it's not my work people, it's just me.

**Adam Grenier** (01:01:17):
And I wouldn't do that. And so it's kind of noticing where else is this impacting and to what degree and why, can help me understand what's going on in my life. Because more often than not, I can then take those feelings and it'll be like, "Oh, I've felt this way for three weeks now. I should think about this and dissect it a little bit." And so again, I'll spend time with my therapist. One of the tools that my therapist has given me is to open up with my friends and have these conversations with my friends. And so now I went from five, six years ago really just having my therapist or my wife to talk about this kind of stuff to, I don't know, I have five or six different friends that we're massively transparent with each other about this stuff, because the second I shared any of this with them, they shared it with me.

**Adam Grenier** (01:02:06):
And now we've become safe places to have those conversations where I can be like, "Hey, there's this thing going on." My dad has ALS and so he's been really sick and I've got three kids and I've got jobs and work and money and the market crash. And there's so many different things. It's like, okay, let me actually figure out which one of these things is causing this energy right now. And having many years of therapy now and those resources can help me get to that solution to get to that answer so that I can figure out, okay, what do I need to do right now? Do I need to actually take time for myself and dig deeper into these personal things? Do I actually need to change something with the shape of my career? Those types of things.

**Lenny** (01:02:47):
Awesome. And it sounds like the things that have been most helpful, and I'm curious what else you'd recommend to folks that are maybe feeling some of this. So, it sounds like therapy is really powerful, your partner and being open to your partner, finding a group of friends where you could be transparent about these sorts of things. Is there anything else you suggest folks look into?

**Adam Grenier** (01:03:04):
Yeah. So, I think meditation's a good one. The startup people love to talk about meditation, and so you can find lots of ways to do that. It's kind of evolved for me. So, it's in that tweet thread and I can't remember it now. There was a meditation thing that was the first, it almost felt like Noom for me for meditation where it wasn't just-

**Lenny** (01:03:24):
Waking Up, Sam Harris's-

**Adam Grenier** (01:03:25):
Yeah, Waking Up where it's like I'm actually learning about meditation, not just learning how to meditate. And that's how my brain likes to do things. I'm a lifetime learner, I love digging into things. I learned breathing techniques and things like that, but going through that program of Waking Up was the first time I actually really appreciated when and how and where to do it. I'm still not a everyday meditate person.

**Adam Grenier** (01:03:50):
I now use, I'm an investor, so I'm biased, but Aura, A-U-R-A, which is a marketplace app. It's some of the other meditation apps, but it's a marketplace, so it's actually coaches and stuff adding content. So, I use that now as needed, which I really enjoy. The exercise and diet and those types of things definitely tie to it. It's like eating is a pretty clean signal for me, or snacking is a really clean signal, at least for me of like, okay, I'm snacking more than I should be, and eating healthy can both help me identify that I'm in those spots, but also just make me feel better.

**Adam Grenier** (01:04:29):
One thing I would say is that the therapist that I found, I found through a service that we had at Uber, and I think I was surprised how much stuff is covered by companies in terms of the ability to find a therapist, pay for a therapist or other tools. And so that's one thing I would suggest, go look through your benefits. Your healthcare provider offers a lot of that stuff too. So, those are a handful of. Listen to Lenny's podcast?

**Lenny** (01:04:58):
I hope that to be true. I don't know if that's anywhere near as powerful as these other things. One thing I'll mention is on the meditation front, there's this amazing book that kind of does exactly what you also describe where it teaches you why this works. It's called, it's kind of like a bad title, it's called Why Buddhism is True. And it's not trying to convince you to be a Buddhist, but it has a lot of incredible insights on why meditation is so powerful and how to think about it. So, I'll put that in the show notes too.

**Adam Grenier** (01:05:24):
Awesome.

**Lenny** (01:05:24):
Yeah.

**Adam Grenier** (01:05:24):
I'm going to check that out.

**Lenny** (01:05:25):
I wanted to come back to the burnout piece. I imagine some folks are listening to this and they're like, "Am I burnt out? I don't know." What are signs that you're burnt out versus just working a lot and tired?

**Adam Grenier** (01:05:37):
The one that I see the most is adaptability goes down really fast. And this is more me noticing I've managed a lot of people and coached a lot of people, so when I see that from people that I'm working with, I usually immediately bring up, I'm like, "Look, your openness to change in the business, or trying new things, or going back and trying things that maybe we tried before and didn't work has shifted from, 'Oh, here are the flags that we should be aware of, but let's give it a shot' to 'Why are we wasting our time? Let's not do this.'"

**Adam Grenier** (01:06:12):
This energy around, let's just do the thing we're supposed to do. And I think that's maybe specifically applicable to our environment, to high growth and marketing and product where it's just, that's just a key ingredient to doing this job well, is adaptability and flexibility and exploration. And if you're losing that, it's probably not because you've gotten bad at it, right? It's probably because you're just over it, right? Where you're like, "I just don't want to deal with the BS around this. I want to go do the thing that makes my job easier."

**Adam Grenier** (01:06:46):
Which again, most of the people that have chosen this career path want their jobs to be harder, because it's more fun, it's more interesting, it's more rewarding. And so when you're looking for ways to minimize the challenge or the opportunity, I think that's a pretty good signal that they may be more burnt out than just exhaustion. Because if anything, I see the opposite for people that are exhausted, where they get re-motivated by new stuff, by opportunities to go do something different and that kind of stuff.

**Lenny** (01:07:15):
Wow. Really good insight. Second to last question, I know you have to run, where are you on this journey today and then just what's next for Adam Grenier?

**Adam Grenier** (01:07:24):
Yeah, thank you. Good question. I'm constantly optimizing this matrix of what am I good at versus what do I love doing? And so what I've found is that I really love entrepreneurs and working really closely with entrepreneurs and helping them figure out all of these funky things that I've been able to see over the last 20 years and maneuver. And I've worked at a lot of places and so I'm really good at context changing and helping connect the dots for people.

**Adam Grenier** (01:07:52):
And so a couple ways I've found to be able to do that is advising companies, so working with founders and growth leaders and things like that and investing. And so I'm actually right now, I've been investing now for six, seven years. I've recently joined Andreessen's Scout fund, so I'm doing a bit more volume now. But I would say if I had to make a bet right now, I think a full-time or closer to full-time investing world is what I'd like to lean more towards. But I'm very much a let's just open up opportunities, and once the right one is in front of me, I'm going to tackle it.

**Adam Grenier** (01:08:23):
And so who knows, I may go back full time somewhere or whatnot. But right now the advising, investing, coaching kind of hybrid is the term, I think it was Behzod at Reforge used, was me as a service is my current world. But I'd be shocked if I eventually don't gravitate towards some kind of foundation, because I thrive when I've got a little bit of an anchor.

**Lenny** (01:08:46):
Amazing. A mass, me as a service.

**Adam Grenier** (01:08:49):
Yeah.

**Lenny** (01:08:49):
Okay. For folks that may want to reach out to you about taking your money in their startup, or asking whatever questions, maybe advising questions, where can folks reach you and learn more?

**Adam Grenier** (01:09:00):
Just Twitter, AKGrenier and LinkedIn as well, it's AKGrier. So, look me up, connect. I'm always open to connecting and chatting with people and I just love digging into problems. So, happy to abide.

**Lenny** (01:09:13):
Amazing. Adam, this was such an action packed chat, so many levels and layers. I can't wait for folks to listen to this. Thank you so much for joining me and being here.

**Adam Grenier** (01:09:21):
Yeah, thanks for having me.

**Lenny** (01:09:22):
My pleasure. Thanks man.

**Adam Grenier** (01:09:24):
Good stuff. Take care.

**Lenny** (01:09:26):
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.

---

## [18/20] Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)

**Jason Shah** (00:00:00):
Pushback is, I couldn't imagine a word more viscerally that makes you feel like you're sort of physically going against what somebody else wants, and it gears people into a mindset of then, well, how should I push back. It starts from a place of I need to disagree, I need to say no. It's a very negative mindset, purely based on the word that has come to label a behavior that alternatively could be about how do I shift the direction on something, or how do I help the business actually succeed when I disagree with somebody about something, and that's a very different mindset. And so, the two things that I've seen be most successful would be, I think number one is actually understanding what a goal is or what somebody's kind of issue is with something, and then actually aligning those things in some way.

**Lenny** (00:00:53):
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 Jason Shah. I was lucky to work with Jason while I was at Airbnb, and when I started working on this podcast, I knew that I wanted to have Jason on. He was actually my very first guest on this podcast when I was pre-recording some episodes, but as you'll hear in our chat, we decided to take another crack at it for reasons you'll soon understand.

**Lenny** (00:01:28):
**John Cutler** (00:03:36):
Hey, Lenny. Excited to be here.

**Lenny** (00:03:37):
John, give us a behind the scenes at Amplitude. When most people think of Amplitude, they think of product analytics, but now you're getting into experimentation and even just launched a CDP. What's the thought process there?

**John Cutler** (00:03:49):
Well, we've always thought of Amplitude as being about supporting the full product loop. Think collect data, inform bets, ship experiments and learn. That's the heart of growth to us. So, the big aha was seeing how many customers were using Amplitude to analyze experiments, use segments for outreach, and send data to other destinations. Experiment in CDP came out of listening to and observing our customers.

**Lenny** (00:04:09):
And supporting growth and learning has always been Amplitude's core focus, right?

**John Cutler** (00:04:14):
Yeah. So, Amplitude tries to meet customers where they are. We just launched starter templates and have a great scholarship program for startups. There's never been a more important time for growth.

**Lenny** (00:04:22):
Absolutely agree. Thanks for joining us, John, and head to amplitude.com to get started. Jason, welcome to the podcast.

**Jason Shah** (00:04:34):
Thanks so much, Lenny. Really excited to chat with you today.

**Lenny** (00:04:36):
Something listeners don't know that we know is that we actually recorded an episode between you and I back in April. It was actually my very first episode that I ever did for this podcast, and it was before I launched. It was kind of like a pre-launch launch episode, and interestingly enough, by the time the podcast launched and it was going to go out, well, let me also add that we chatted mostly about Web3, forgot that detail. So, most of our chat was about Web3 in the state of Web3 and PMing in Web3, and by the time the podcast's supposed to come out, Web3, things have changed in the world of Web3, and so, it kind of felt a little stale and out of touch, and so, we decided let's do it again. And so, how do you feel about that?

**Jason Shah** (00:05:15):
I appreciate that, Lenny. I'm honored that you would have me back. I'm going to count it as the personal record of two times on Lenny's Podcast, even if the world only knows it as one.

**Lenny** (00:05:26):
Wow. Good one. Okay, first ever guest and first two-time return guest. Amazing. Okay. To set a little context for folks on your background, your career, could you just give us a 60-second overview of your background and your career and how you got to what you're doing today?

**Jason Shah** (00:05:45):
Yeah, for sure. Thanks again for having me, Lenny. So, my career has all been about solving important problems in a unique way. I think the latter part is the youngest child in me who has to be special and do things different than other people, and the former is about making sure that my time is spent well since we're all limited there. So, I actually got started in a sense in tech when I was 15. I started my first company, much like a lot of teenagers, it was around test prep and getting people ready for college, and it was my first exposure to using technology at scale to help people, and I just found it addictive ever since.

**Jason Shah** (00:06:20):
And so, I ran that company for seven years through school, was lucky to do a small acquisition to a partner of ours that we had worked with throughout, and then I would just hooked, and I moved to San Francisco without a job. I was really arrogant. I said, "I'll never work for anybody else," and then lo and behold, Yammer comes along, I'm super excited about it, I had been working on a product actually in the same space. And so, that was actually my first formal product management role, and I stayed at Yammer, I stayed through the Microsoft acquisition back in 2012. Low and behold, I was at the world's largest productivity company at Microsoft, and most people there in my opinion were wildly unproductive and I wasn't shipping a lot. I got the itch again, so started another company called do.com and ran that for about four years, and then eventually, we found a better fit with Amazon. They were growing their AWS offering, SAS products. So, we partnered with them to kind of do a small acqui-hire and help build the team out and the product there for a little over a year.

**Jason Shah** (00:07:18):
And then again, to be honest, I got bored and excited about what Airbnb was doing and the mission around belonging. That's why I was lucky to meet you and so many other really wonderful product leaders and just human beings in general at their core, and then to keep things brief for now, I got to work on a lot of really exciting products and businesses there, but eventually got the itch for Web3 after being a kind of observer from afar, investor, and I wanted to be a builder in Web3 specifically, and to me, it's a new vision of a better version of the internet. I'm really excited about that. So, I've been with Alchemy which is a blockchain infrastructure company for the last year, and really excited about all the opportunities. I've gotten to work on products that have been part of most people's everyday lives, and I'm hopeful that we'll get to do that with Web3 and Alchemy as well.

**Lenny** (00:08:05):
Amazing. I just realized as you're chatting there, do.com, I'm pretty sure I used that back in the day. I think I just realized that.

**Jason Shah** (00:08:12):
I hope so. That would be a new, I'll add that to my second podcast achievement is if I got Lenny to use a product that I worked on, especially a startup.

**Lenny** (00:08:20):
Wow. Cool. Okay, so we're going to go a little bit backwards through your career and start with Web3. We're not going to spend most of the time on Web3, but just thought it'd be good to chat about some of these things, partly because you guest authored the sixth most popular post, online newsletter of all time, currently at number six, and it was about how to be a PM in Web3. Basically it's called The Product Manager's Guide to Web3. And so, a few questions there I wanted to touch on. One is just like, how would you describe the current state of Web3? We're recording this at the end of July, and so, we'll see when this comes out. But I'm just curious from someone working within it, kind of going through the boom and the busts, not the bust, the winter that we're kind of in a little bit right now. Yeah, how do you feel about it right now?

**Jason Shah** (00:09:01):
Yeah, for sure. So, as much as I'm a techno optimist, I'm also realist, and with that being said, I genuinely believe Web3 is in the strongest position that it's ever been in. I think it's important to remember that the term Web3 has barely existed in kind of popular lexicon for barely a year. We've definitely had crypto for more than a decade now as technology, arguably as a financial instrument of some sort, but specifically the number of companies that I'm seeing be formed, the number of products that are starting to actually achieve some form of early product market fit, some products that are starting to scale. There's definitely been obviously a huge drop in price. There's definitely been some huge scandals in terms of financial mismanagement and the contagion from that.

**Jason Shah** (00:09:46):
But I think it's been my experience that a lot of new technologies don't move up in a straight line, and Web3 is especially challenging here because so many things have been financialized from the outset, whereas generally speaking, you'll see startups or new technologies mature over many years, whether it's the internet itself, artificial intelligence, QR codes, all sorts of things that kind of have gone through different periods of adoption, and so, I think we're seeing things kind of record Ethereum transactions happening, new Layer 2 technologies launching all the time that are going to help scale Layer 1 Blockchains, Solana has announced its phone that's going to be the first sort of Web3 native phone out there. So, there's so many new exciting product developments and users entering the space that as much as prices have come down, I'm really optimistic about the state of Web3.

**Lenny** (00:10:32):
I think about a little bit is going through this shift in excitement about Web3 as a PM within a company working in this space, I imagine it tests some of the core skills of a PM, like keeping people focused, prioritizing effectively, keeping morale up. If people are getting like, "Oh man, all my cryptos going down," I'm curious how you've been able to leverage those skills and what you've learned going through this experience, keeping people focused, morale up, prioritizing effectively, those sorts of things.

**Jason Shah** (00:11:00):
Yeah, it's a great question. It's really important, right, because we've seen in this space that there are these cycles, and I think that morale and ability to keep building are the determinants of long-term success, and if everybody kind of takes the ball and goes home, that uncertain future won't necessarily materialize. So, in my opinion, I think that the only way to maintain moral is to make progress. I think that no speech, no sort of extrinsic motivators like we're going to give everybody some free crypto to keep motivated about it or something like that really works. I think people get really excited when they see progress.

**Jason Shah** (00:11:37):
So, for example, at Alchemy, we see more developers than we've ever had on the platform today, and then we're shipping, we just launched Solana support and people are like, "This is real." We're actually doing things, building things. We just had our team out at EthCC which is a big conference in Paris for the Ethereum community, and it was wild the number of people that were there, products being built. Pretty much every crypto conference has a hackathon, and so, it keeps the spirit of building so alive.

**Jason Shah** (00:12:03):
And so, I think it at Alchemy and just in other situations that I've been in as a leader over time, I think it's all about a focus on progress and moving forward. We saw this at Airbnb when the business had a draw down in revenue, and I know you'd covered this with Sanchan recently, right? It was 85, 90% revenue and you didn't know when it was going to turn around, right? It's not just like, "Oh yeah, this will come back in six months and we can just keep plowing forward." But I think what worked was making progress and actually focusing on product and your customers, and ultimately if you hire the right people who are motivated for the right reasons, I think that recipe keeps people highly motivated and highly effective at building for when things do eventually turn around.

**Lenny** (00:12:44):
One of the most interesting and maybe surprising points you made in the post that you wrote about being a PM in Web3 is that there's much less need for a PM, especially early stage Web3, and it feels like, the stuff you're talking about feels like a PM's really helpful along these lines. So, I'm curious, are things changing at all there? Have you changed your perspective on PMs and Web3, and then I don't know, where do you see the evolution of product management and Web3?

**Jason Shah** (00:13:09):
I actually am seeing things change a lot, and one thing in Web3, if one learns nothing is the ability to admit when they're wrong or when things change. And so, I think that that's exactly what I'm seeing. So, basically, I'm specifically noticing a lot of teams hiring product leaders, more product managers. Those product managers are actually now working kind of increasingly in sort of more traditional product management fashion, in addition to some of the differences that we discussed in the post around the community management and role in marketing and things like this, but specifically, Uniswap just made a big hire out of Meta. I saw that Gemini also did the same. We're seeing OpenSea hire a lot of talent along these lines too, even through the ups and downs that their business has seen, and at all levels. Whether it's kind of product manager, senior product manager, director, VP or CPO, you're seeing it across the board.

**Jason Shah** (00:14:03):
And so, I think that's partially happening because you're seeing a maturation of products, right, and so, maybe you can start early with a few engineers, a community manager, get the ball rolling, but eventually the product is more mature, the complexity has grown, the role of the product manager is far more useful than they can differentiate. I also think the market is getting increasingly competitive. So, there's many NFT marketplaces. There's many Layer 1 and Layer 2 blockchains. As a result, I think product is always a competitive advantage, right? If it's working, it improves strategy, it improves execution, and improves team collaboration. And so, maybe that was less of a difference maker before where these teams didn't need that competitive advantage as much because maybe they launched a token and the token was mooning, and so a bunch of people were adopting the product, but that only lasts so long, and first principles still come come in to focus, whether it's one day or one month from now.

**Jason Shah** (00:15:00):
So, I'm definitely seeing it shift. It's definitely making a huge, positive difference in the cases that I've observed, and my hunch is we're only going to continue to observe this because with more user adoption comes new challenges, and for all these players that are growing and getting some form of adoption, the product complexity is only going to grow, and having somebody to help lead teams, help prioritize between all the different products that they could build or strategies they could pursue is going to only increase in importance.

**Lenny** (00:15:27):
I know we're like we're PM people talking about the value of PM, but something I find is that people that are kind of anti having a PM or don't see why they need a PM in my experience just haven't worked with a great product manager because my experience, you find a great PM, they just make everything better, and so, it's not surprising to hear what you're sharing which is people are kind of discovering that value of bringing on a product manager, even if it's mostly engineering work. And so, that's promising, and I wonder if that's just a natural evolution of a new space where people are like, "Eh, I don't need PMs in this one," and then like, "Oh, okay, well, I see. All these things aren't happening. We need someone to help. Who can do that for us? Maybe it's a PM."

**Jason Shah** (00:16:06):
Yeah, that's a great observation. I think that combination of having a direct need for something that emerges as well as if somebody's had either a bad experience or not even had any experience with somebody who can play this role which is quite common in Web3, especially because a lot of folks are relatively early in their career, given the kind of accessibility of the space, and I think frankly the more adept understanding of the space naturally that a lot of people have when they're early in their career and less set in their ways. And so, that's a great point, and as a result, the better PMs we see in Web3, hopefully the value will prove itself out over time.

**Lenny** (00:16:41):
And hopefully they do well so people don't keep getting burned out by bad PMs.

**Jason Shah** (00:16:45):
We're rooting for all PMs, but definitely Web3 PMs too.

**Lenny** (00:16:49):
Yeah. What's surprised you most about working in Web3 as a PM?

**Jason Shah** (00:16:53):
I mean, I think that the biggest surprise to me, despite what we were just talking about, was how big some products have gotten without kind of the traditional either product manager role or without the playbooks that we're so used to from the last 20 years of the internet. And so, for example, Uniswap has done more daily volume on certain days than Coinbase, and Uniswap is about a hundred people versus 5,000-plus at Coinbase, right? So, that's astounding to me.

**Jason Shah** (00:17:21):
I think a lot of these NFT collections and communities that have grown. I met with a lot of these at NFT.NYC recently, and a lot of them, aside from the price speculation and things like this, have actually built, the Bored Ape Yacht Club is actually building a metaverse project that does look better than some of the digital games that I've used in the past of Second Life and things like this. Obviously, a lot of time has passed and so there's a greater foundation of technology to build off of and they're working with a partner on that product as well, but there's a ton of progress being made without some of the traditional product structure or individuals. And so, again, I think PMs play a really strong role, but it's been incredibly surprising to see how far products can get without the product playbooks and resources that somebody who's worked in the internet space from the last 10 or 20 years is so used to.

**Lenny** (00:18:11):
Awesome. Okay. We're going to move on from Web3 and chat a bit about some of your other career accomplishments and companies you've worked at. So, you worked at, you mentioned Yammer, Microsoft, Amazon, Airbnb. I'm curious which of those companies has most informed the way you approach product and build product and run teams because they're all so different in how they operate, and I'm always curious what company is the formative experience for you that's like, "Here's how I like to build product most." I know it's always a combination, but how do you think about that?

**Jason Shah** (00:18:39):
Yeah, it's definitely a combination, but I would say if I had to pick, Amazon, even though I was only there for about a year after the acquisition. I say that because of this blend between product and business thinking that is especially present there. And so, people say Google is an engineering culture. People said Facebook is a product culture, Airbnb or Pinterest, sometimes a design culture or things like this, and I think that Amazon was a place where you couldn't divorce business and product. You couldn't be a product manager without thinking about revenue growth, without thinking about go to market, and I really like that because as a startup founder doing product in a bigger company, it gave me the chance to exercise a lot of those skills.

**Jason Shah** (00:19:24):
It's very similar actually to how I feel at Alchemy now where I remember my first month there I was like, people ask me how's it going, I'm like, "I feel like an athlete. I feel alive again." I can do M&A one day, I can be doing product another minute. I could be figuring out, oh, we need to hire our first lawyer to write onboarding plans for employees the next minute, and it wasn't as siloed as sometimes a product role can be. So, I think Amazon, I went there to learn and understand. That was my biggest goal was this is an incredible company that's gone into... The Whole Foods acquisition happened when I was there, and I was wondering how does the same company kind of within retail win with the AWS, go create studios, and I think the Amazon culture ultimately more than anything else around ownership, being vocally self-critical is right a lot as one of the leadership principles. All these things combined I think created a really unique culture.

**Jason Shah** (00:20:12):
So, I would say Amazon's had the biggest impact on me, and there have been certain lessons that I've taken from, like you said, all these places, but Amazon was by far the place that I think left the biggest mark on my view on product and leadership.

**Lenny** (00:20:26):
That's quite amazing that you were there for a year and that's the one that's most informed and impacted you. Do you feel like people should try to go work at Amazon as a training ground as a PM? Is that something you encourage PM to try to do?

**Jason Shah** (00:20:37):
In general, I certainly had a positive experience, but I think that as you know and as I'm sure you've advised countless people, it's so context dependent. Are you learning the zero to one? Are you learning the one to scale? What's your aspiration? Is somebody trying to start a company eventually, or are they trying to work the ranks of the product leadership trajectory? And so, I definitely enjoyed it a lot, and I think to your point, there's often a non-linear sort of correlation between factors that we traditionally think are linked, right? So, my time there was one of the shortest, but my learnings were some of the greatest because I was really intentional and maybe because of the sort of moment in time and what I wanted to get out of it.

**Jason Shah** (00:21:17):
The same way for what it's worth, while we're talking about this disconnect, when I went to Yammer, I also interviewed with kind of... This was the era of TaskRabbit. I talked to Square and I remember people always say, "Well, what stage do you want to join seed, Series A, Series B?" And the crazy thing is that Yammer was, it was already passed a hundred people, it grew to 500 by the time of the acquisition, and it felt almost like the culture was so tightknit, it felt like a seed stage company at some points, even though eventually it kind of felt like... Well, once it was acquired from Microsoft, we'll just say it didn't feel like a seed stage company anymore, but it felt smaller than a lot of the actual smaller companies than I was at. So, I think that's something I've noticed a lot is that a lot of the proxies don't necessarily match the internal realities in certain cases.

**Lenny** (00:22:01):
You mentioned you picked up a bunch of tactics and kind of lessons from some of these companies. What's one concrete process or tactic that you took it away from either Amazon or one of these other companies that stuck with you that you like to kind of share with folks?

**Jason Shah** (00:22:14):
Yeah, definitely. I mean, I think one that Amazon is well-known for is the working backwards process, and for those that don't know, the idea is try to define effectively an ideal end state which funnily enough is very similar to some of what we both experienced at Airbnb and took away, and usually the mechanism for doing this is what's called a PRFAQ, and that's a press release and frequently asked questions, and it forces a certain degree of clarity to have to actually write a press release about the product that you're going to eventually launch.

**Jason Shah** (00:22:44):
Every employee goes through actually like a business writing class after they start at Amazon. They give you a little card with five tips that you're supposed to keep on your desk about concision and specificity in the words you use. For example, you should never write the word great in an Amazon press release. You should write user friendly in X, Y, Z way and will save customers time 20 minutes each day through this. It's intended to be very concrete in a way that avoids some of the fluffiness that frankly... It's funny, when people try to move from slides to docs, they really just import the same mindsets that they use in slides, but just with more words now.

**Jason Shah** (00:23:22):
And so, I think the working backwards process of establishing the long-term goal using a mechanism like a press release and the FAQs where every word matters, and even the FAQs, for what it's worth, there's a section for external FAQs that you would include for example as an appendix, but also internal FAQs that are meant to de-risk launch or raise the elephant in the room or dogs not barking as Amazon likes to call it often. So, that was a really helpful process that felt very true to me as a way I like to live my life as well, and then also very applicable.

**Lenny** (00:23:55):
The tidbit about not using the word great is so interesting. Is there anything else there that you could share about just basically just like how to write effectively and communicate and launch. Is there any other tidbits along those lines?

**Jason Shah** (00:24:07):
Yeah, that's a good question. In addition to not using the word great and words like it that are either subjective in what they mean or unclear in what they actually mean, definitely using numbers more than adjectives. Strict concision, I would go over these documents countless times, and there's a phrase, I can't remember, it's either Mark Twain or another famous writer who said kill your darlings, right? Cut, cut, cut, and just remove. And so, I think I found that really useful in emails I write or documents I write to this day is just going over, not because you're saving ink by cutting words, but because it forces clarity of thought. Fewer words means every word is 10 pounds in weight instead of one, and that means that the decisions you're making, the trade offs are far more intentional, and in the case of great, if you say something is great because we're going to deliver something in two hours versus Amazon's great because the selection is very wide, the implications on strategy are completely different. And so, that's one of the benefits of being very specific and very concrete in language.

**Lenny** (00:25:12):
I didn't intend to go too deep into this topic, but no one's ever covered this working backwards process on this podcast, so it's kind of interesting to talk about it a little bit more maybe. How does that actually work? So, you sit there and you actually write out a press release that would go out when you launch this thing. Is there like a template used? Is there anything you could share for folks that want to try this out and/or point them to a resource that will help them down this road?

**Jason Shah** (00:25:36):
Yeah, definitely. That's a great question. So, there definitely is a template, and so, it's a combination of an internal training where you have to write one of these documents. You review kind of good, bad, medium versions of this. It's generally used if there's let's say a proposal for a new product or even a proposal to buy a company. This helps really simulate what it's going to be like.

**Jason Shah** (00:25:56):
With respect to a template, what I recall is it was often sort of an introduction where you get kind of right to the point. You say what you're announcing. Then usually you would describe the problem in one paragraph and in very clear language. Again, all of the writing is this way. Then the solution, you briefly describe the product. After that, there's always a customer quote, and this is an example of this customer obsession that Amazon is so famous for that many companies like to say or emulate, but I think it really kind of may not be true if you evaluate the mechanisms that they use, for example, product specs that either don't have customer data or don't have quotes from customers, things like this. And so, there's a customer quote, and you have to literally put yourself into the shoes of... Let's say you were launching Prime. Put yourself in the shoes of Lenny from San Francisco. What exactly is he going to say when he has access to this, and how's it different than his life today, and what are the words that he's going to use?

**Lenny** (00:26:52):
You can't use great.

**Jason Shah** (00:26:53):
I mean, if great is one of your favorite words, maybe you could stretch it, but I think if you were in a room with your peers at Amazon, they might put some red pen through any greats that are used there. So, I found that really helpful, and it also helps force out of this box that product managers, product leaders tend to get into of thinking that they are always the customer and being a little sort of intellectually lazy, where I'm like, "Yeah, I would like Prime, so let me write the quote for what I would like," but maybe I'm only a small segment within our total customer addressable market.

**Jason Shah** (00:27:26):
So, anyhow, there's a customer quote, then there's one leadership quote similarly that this achieves a complimentary goal, like how does this fit into our strategy in a way that you would express to the public but is still true to what the internal sensitivities and mechanisms would be. And then a call to action towards the end, and not just download here, but this will be available to customers next month. They can go access these portals within these Whole Food stores at this state. It again forces clarity of thought with respect to not only the rollout plan, but taking a step back. When you read it, do you feel like you would actually want this product? Would you use it? So, I found that really helpful as a structure.

**Lenny** (00:28:05):
Can you just summarize those again real quick?

**Jason Shah** (00:28:07):
For sure. So the structure of the PRFAQ docs was generally an introduction where you're announced the product, problem, solution, customer quote, leadership quote, and a call to action.

**Lenny** (00:28:17):
So, interesting how similar that is to a one pager potentially. The other thought I had while you're chatting, so the Airbnb approach is work back from the ideal, Brian talks about it, the 11-star experience versus the Amazon approach which it doesn't need to be the ideal, it just needs to be an awesome launch. So, that's an interesting difference, both effective in different ways.

**Jason Shah** (00:28:37):
I think people tend to, when they see that both companies have some sort of working backwards process of thought, I would say working backwards on one hand and then 11-star experience on the other. Listening to how you describe it, I want to almost frame it as working backwards from sort of a moment in time or a launch like you said with Amazon versus working backwards from a quality standard in some sense of an 11-star experience.

**Lenny** (00:28:59):
Going in a slightly different direction, one of the things I wanted to chat about is you worked at all these different companies and they have different types of leadership and different approaches to leadership. And so, I'm curious, what have you learned about effective leadership watching all these awesome operators work, and what kind of separates them in your experience from folks that maybe aren't as effective?

**Jason Shah** (00:29:18):
Yeah, it's a great question, and to briefly recap, right, I've gotten to see somebody like David Sachs who've been the CEO of PayPal and then the founder of Yammer and gone to do many more things since then. I've gotten to see sort of Jeff Bezos at a distance. I was never that close to him obviously and never got to work with him, but got to observe his impact on the organization. Obviously, I've gotten to witness Brian Chesky and his leadership in sort of the pre-IPO days as well as through the ups and downs of COVID, and then also now at Alchemy, our co-founders, Joe and Nikil are leaders that have really had an impact on me as well, and I would count myself, but I've also see myself as a bad leader in the start of [inaudible 00:29:56] and learn from that.

**Jason Shah** (00:29:57):
I think it's a really important thing to reflect on, and I think for me there are three things that have stood out the most. I think number one, nothing is above them. I've seen whether it's Brian caring about the full bleed image on the homepage, whether it's Jeff Bezos who famously would receive customer emails, read many of them, forward them, and he's famous for question mark emails where for his time's sake he would just forward an email to a leader with a question mark and you would just have to figure it out and then report back in 24 hours with the resolution thereof. But nothing's above them, and a lot of founders or a lot of CEOs or even CPOs and leaders think you get to a certain point and then I'm above a product spec, I'm above looking at the data running a sequel query, and I think that that is a mistake in a lot of ways, especially from a standpoint of who people come to respect as well as efficacy at one's job.

**Jason Shah** (00:30:51):
And then the other two things would be, I think they're in the details. So, it's less about being above something, but this is kind of Amazon's famous for auditing the details for example, and leaders are... For example, when we were going to launch Prime, order a bunch of Prime things and see what happens and really test things out, and write up a long feedback email on Saturday or something like that, and make sure that things are moving forward.

**Jason Shah** (00:31:12):
So, I think in my opinion, some of the best leaders, David Sachs would do this too. He actually ran the product reviews. It was the CEO of the company doing product reviews, not some kind of middle tier of a director of product who was just running them. They were force involved and there were things to delegate and activate around, but Sachs was in all of those details and ran those product reviews himself and would talk to the product managers directly, and I think that was really impactful, and it also, I think from an accountability and culture perspective, when you're PM and you talk to the CEO and you feel like you're presenting something at product review, it's totally different, and it creates a certain amount of responsibility and quality, frankly, that I think is really important, and it's a way to coach obviously as well for those leaders to really make a mark on the organization.

**Jason Shah** (00:31:59):
And then lastly, I think they adapt, right? I think that are a lot of leaders who are like, "I've worked 20 years to become a leader in this way and I have a playbook," either based on past experience or based on some sort of philosophy that they've developed over time that they feel committed to in some way, and I think coming back to some of these examples of watching Brian lead through COVID or watching Joe and Nikil now through this particular crypto winter shift gears and figure out exactly like we're still building the core business, but how else can we lean into this and adapt to the unique opportunities that are in front of us. I think that's really powerful. So, what I've seen is nothing is above them, they're in the details, and they adapt to new information and new situations. That's what I've seen the most that I've appreciated in the best leaders that I've gotten to either observe or work closely with.

**Lenny** (00:32:46):
Awesome. That's super interesting. The first two are kind of connected which is really interesting, and it just reminds me of Brian and how detail-oriented he was about everything. He used to review every product launch and every screen of every new product. We had to show him here's what we're launching this week, and he just kind of went through and either blew it up or let it pass. And then I just remember the founders, when they were designing the office space, just looking at pictures of listings they wanted to... Because Airbnb, the office conference rooms were modeled after Airbnb listings, and Jim just looking through hundreds of listings that the team brought him and he'd just picked the ones that he wanted to turn into conference rooms. Also, obviously Steve Jobs. This is a really interesting through line of great leaders is just this huge attention to detail, and there's probably something about once they let go that thing start to kind of diminish. Is that what you find?

**Jason Shah** (00:33:39):
Yeah, that's such a great point. You mentioned the Jobs example and there's a great book that you've probably read or in your community seen, I believe it's called Creative Selection by Ken Kocienda about the early days of the iPhone, and I think it was Project Purple or something like that, and you're absolutely right. There wasn't no slides, none of this. They brought in the prototypes for each of those reviews and things like how to do typing on a tiny screen and those early keyboards and how to do auto complete, and Jobs was totally in those details from Ken's telling in this book.

**Jason Shah** (00:34:10):
So, I couldn't agree with you more, and it's something that people miss because most of their exposure to leaders is on a YouTube video or at all hands, and so, they don't really get to see that side of leaders I think, and it's also not what I think from an ego perspective is kind of what people want it to be about. They want to be about making big decisions or commanding a large group of people, and I think it's hard to do that without these pieces.

**Jason Shah** (00:34:34):
One other thing I just wanted to briefly touch on to your point on how they're connected, it's a really good point, and at the surface it almost seems like they could potentially be the same thing. One thing worth calling out though I think is the idea of something not being above somebody or a person not being above things. I think the biggest thing I take away from that is humility is that nothing is not my job, right? Anything, could be picking up paper off the floor and putting it in the trash, or it could be reviewing a product spec, whatever it is, and then begin the details in my opinion is about craft, right, and really understanding things at a low level such that you're able to reason about it and make good decisions, like Brian with the homepage or Bezos in some cases with customer processes that he got in the weeds on. I think the two together, humility and being excellent at craft, I think is a very potent combination, especially when you throw in the last thing of being able to adapt to any situation.

**Lenny** (00:35:29):
That's really interesting. What it also makes me think about is the reason things are less good often if there isn't a person at the top that's being very detail-oriented, and I find this with the newsletter and this podcast and other stuff is no one's going to care as much about it. No one's going to be like, "Oh my god, I really need to get this right so much because I'm just like, I'm personally feeling responsible for the quality of this stuff and it's like it's on my shoulders to make this awesome." And so, I think that's probably why a lot of the best stuff is led by a singular leader or singular opinion or singular person. A lot of the best startups are just someone's vision is like, "Here, this is what we're going to do," and then the more it becomes a community-driven thing, the less often it ends up being successful.

**Lenny** (00:36:16):
**Jason Shah** (00:37:19):
I feel like you're totally right, especially, I mean this is the natural progression, but it doesn't have to be that way right? And I think to your point, I think a lot of leaders focus on accountability in an organization once they get large, and so, you see things like performance reviews and things like this. It's a very top-down approach to trying to drive results, but is opposed to a sense of accountability if you drove a sense of responsibility. If people felt like this is my company too, this is my product, this is my office floor. I don't want trash on the floor. I'm going to pick it up and throw it there. Even if we have somebody whose job it supposedly is to clean that up, it's like I take pride of ownership in this and I'm connected to it, and I think that makes all the difference in terms of... At Airbnb, I think people who felt that way were willing to push back on certain things, or they're willing to propose new ideas because they felt invested in the company.

**Jason Shah** (00:38:12):
I see it at Alchemy all the time. I see an engineer hop in and fix something at 3:00 AM because they feel committed to the code base, and it's not a thousand-person engineering organization where my only job is to make the iOS app 2% more effective at engaging users.

**Lenny** (00:38:27):
So, you touched on the skill of pushing back on a founder or CEO, and I know that's something you're really good at. I've seen you do this. I'm curious what you've learned about how to effectively do that as a PM at a company pushing back on a CEO or founder when you disagree.

**Jason Shah** (00:38:40):
I mean, I think this is one of... I actually think it's one of the most misunderstood terms in a sense because I think language like we were talking about earlier is so important, and yet what you call something ends up defining I think 90% of what people understand about a concept, right? And so, pushback is, I couldn't imagine a word more viscerally that makes you feel like you're sort physically going against what somebody else wants, and it gears people into a mindset of then, well, how should I push back. It starts from a place of I need to disagree, I need to say no. It's a very negative mindset, purely based on the word that has come to label a behavior that alternatively could be about how do I shift the direction on something, or how do I help the business actually succeed when I disagree with somebody about something, and that's a very different mindset.

**Jason Shah** (00:39:34):
And so, the two things that I've seen be most successful would be, I think number one is actually understanding what a goal is or what somebody's kind of issue is with something, and then actually aligning those things in some way. So, in coming back to Airbnb, I remember Airbnb had bought a company, Luxury Retreats. There was a goal to integrate that business and that product into the full Airbnb suite, and there was a lot of potential with that, but I remember that there was part of the product experience that was oriented around chatting with somebody and the idea that the business had had a very large team of wonderful people who helped you as concierges basically for your trip, and so, this was a team that I was on that, to be honest, had fairly low morale. It's always difficult to integrate an acquisition with a company, especially when we were based in different places, et cetera.

**Jason Shah** (00:40:26):
I remember hearing from a leader who had been at Airbnb for a while who's very effective at persuading senior leadership, and they understood why this was a problem because this chat product was growing in complexity. You'd have to build all these features into it, and nobody could successfully shift the direction, and as a result, it was just this... It was a mess as a result, and there was very low morale because we were taking on too much scope, people weren't sure it was the right product, it was being built up as one giant launch as opposed to an iterative thing. And what was really interesting was that this leader was very effective at understanding that the goal wasn't about building a bunch of features. It was about, as often discussed at Airbnb, a magical experience.

**Jason Shah** (00:41:06):
And so, when we took a step back, it was reimagined as trip designers, not concierges, and their goal was to design your trip, and part of that meant a very elegant, simple chat experience so that you could have a efficient, fast, positive experience with that trip designer and move on. And it shifted the pushback of like, "We can't build this thing, it's too many features, we don't have enough time, we don't have enough resources" to, "Oh, we all want a really elegant, really smooth, slick experience for our customers. How do we do that? What's a trip design or a new concept that is actually going to elevate things? We're not telling you we want a payback scope. We're not saying we want to settle for less. We're actually just not only going to call it something different, but also envision a simpler experience which is more elegant. It's more on brand with luxury."

**Jason Shah** (00:41:51):
Boom, all of a sudden, everybody gets what they want. It's a better customer experience, less scope, and it wasn't about saying no. It was about understanding what we're all actually sharing as a goal which was a great simple customer experience and then actually building that. So, I saw that to be really effective and I think that that's something I try to bring into my career. I have a couple other examples if it's useful, but that was a big one that I learned from Airbnb.

**Lenny** (00:42:16):
Yeah, another example would be great. One thought there though is do you think it was mostly the name and the concept or was it that it was a bigger idea? What do you think it was about reframing it that way that got people, "Oh wow, okay, now I'm really excited about it again"?

**Jason Shah** (00:42:30):
That's a great point. I think it was a big idea, right, with a good reframing, and I think it's like many things where there's the substance of something and then there's the communication of it. And so, this is true often, for example, if a company is changing strategy. Oftentimes people might walk away feeling like, "Yeah, I guess I kind of agree with the strategy, but the way was communicated was really poor," or vice versa, like, "Yeah, they told us in advance and they sat us down all hands, but I really disagree with this strategy and I'm going to be dug into my heels and not disagree and commit now."

**Jason Shah** (00:42:58):
So, in this case, I think you're totally right. If it was just window dressing of... Founders are too smart, especially at all these companies we've talked about, to be fooled with a simple renaming of something. But I think the combination of a bigger idea, more exciting idea that was at the heart of what we were all going after together, combined with a simple way of communicating it because I've also seen big ideas that are poorly communicated fall flat on their face and not achieve the intended outcome. Those two together, I think were a really potent combination.

**Lenny** (00:43:28):
Awesome. I'd love to hear another example.

**Jason Shah** (00:43:30):
Yeah, for sure. So, a recent example at Alchemy actually, right? We're growing, we're hiring, but there are a lot of roles, especially being in Web3 that are not yet created. For example, there's traditionally growth, product growth marketing, we've created new area around growth operations which I'd be happy to talk about if we want to get into it. But it's a really interest interesting area, and we were going back and forth on should we hire for this role, it's not even a real thing. We've looked at some candidates, we're not so sure about them. And when I realize with our founders who are incredibly smart, very talented, have built the company over so many years now, they want to win. That's what they care about at the end of the day. They are so driven to win at the end of the day.

**Jason Shah** (00:44:10):
And so, ultimately, it wasn't like, "Let me make some rational argument about the role of growth operations or let me defend some issues with this person's resume that maybe you're spotting when we make this hiring decision," but, "Oh, you want to win? Oh, we want to grow faster? Awesome. This is the way to do it, and that's how we're going to actually become the generational company we want to be." Again, a reframing in this case around, yeah, we might disagree or squabble about certain things at a detail level, but I understand what we all came here to do and let's focus on that and how this is a part of that versus just focusing on maybe the means to an end versus the end itself, and the end always brings a lot of clarity in my experience.

**Lenny** (00:44:49):
What's cool about both these examples, and another guest touched on this, when you're trying to influence the CEO or the founder, coming back to your working backwards concept, you almost want to work backwards from what are they excited about, how do they see the world, what's important to them, and then pitch it that way. So, in the first example, I imagine they were pitching to Brian and he's like, "Yeah, drip design, that sounds like something Brian would love." Then in the second example, "Yeah, we're going to win. Here's how we win." So, that's a really interesting takeaway there.

**Jason Shah** (00:45:15):
I mean, I think we all forget that we're all just humans, and at the end of the day, we all are busy, et cetera. It reminds me of a lot of sales, right? I was very unsuccessful when I was trying to do outbound sales in the early days of my last startup do.com because I didn't understand this. I'm a product person. I'm not a sales person. I didn't listen to what people cared about. I didn't kind of work backwards from what a CRO or head of people that we might have been selling to cared about. I was just about features and here's what we can do for you and this and that. But all they cared about were one or two things, right? Maybe the CRO's growing revenue. Maybe the head of peoples worried about culture or scaling their talent organization, and we were nowhere near that list.

**Jason Shah** (00:45:56):
And so, I think it's similar for CEOs, and there's a huge disconnect when say a PM walks into a meeting with the CEO and they're talking about something that CEO is 10 miles away from thinking about, and certainly even the mindset that they're bringing to the conversation is totally different. I think Casey made a lot of great points about this in the recent podcast as well.

**Lenny** (00:46:16):
Sweet. Casey Winters, podcast plug. Okay, so something else that you're really good at is you don't kind of focus career-wise on working your way up the ladder and being like the top PM, and you seem to be really good at kind of following with what's interesting to you and your interest and your curiosity. Is there something that you've learned there, something you could share for folks that are just like, "Oh my gosh, should I just keep in with this job and work my way up? Should I try something new?" What have you learned about that sort of thinking?

**Jason Shah** (00:46:46):
There's the framework I like is ladder versus map, and I think that you can be either person that any point in your life. Sometimes there's a bit of a set mindset that somebody might have one way or another, but I like ladder versus map. Ladder is about moving up. It's more influence, more power, a higher title, things like this, whereas map is I just want to go wherever's interesting, right? I literally think of it, I think of my career very similar to travel. I want to go to Greece. I want to be hungry, walking around in India, sweating in a hundred degree weather. I want to go to Australia and kind of get locked out of my hotel and see what that's like.

**Jason Shah** (00:47:23):
I'm okay with discomfort because it's interesting. Sometimes, for better or worse, maybe this is a privilege, it's certainly a privileged thing to say, but I care more about living a really interesting life than let's say a good or comfortable life. I think that's where the growth comes from. That's where the stories come from. That's to me the things that I'll remember the most.

**Jason Shah** (00:47:42):
And so, when I think about product and I'm on my deathbed, I'm going to care about the products I built and how they affected people. Nobody's really going to be looking at my LinkedIn, hopefully for their sake and mine, at my funeral. Sorry, it's a very morbid analogy, but I think thinking of the future provides a lot of clarity about what am I going to care about a long time from now, and I think that applies to all facets of life. That's how I thought about my life partner. That's how I think about my career. That's how I think about where I want to live, San Francisco. San Francisco, a lot of people like to talk negatively about it, but I believe in the community. I believe in the place I'm interested in the long term, even if you know the short term it has some challenges to it.

**Jason Shah** (00:48:21):
So, I personally believe really strongly in this kind of ladder versus map distinction, and I think a lot of people are very intentional in the micro. They think about their next job, their next title, how much salary and equity there is. In good ways too, they think about the team that they're going to work on next with, but they're very unintentional about the macro. What's the big picture? What do I care about as an individual? There's not a lot of classes for that. There's not a lot of blog posts in the product management field about the touchy-feely side of this, and who are you as a person, where do you get energy from. So, for me, I found that really clarifying and it makes career decisions that have seemed risky to other people seem inevitable to me.

**Lenny** (00:49:03):
Is there a story of or example of how you use this approach to make a decision at where you end up going, and/or or is there something that you maybe regret or are really happy with in terms of the kind of the fork in the road, looking back, using this way of thinking?

**Jason Shah** (00:49:18):
A few concrete examples, actually. I'll keep them brief though. One is when I first moved to San Francisco, and I had mentioned I did a small sale of that education company, and I could have done a lot of more productive things with my career in the short term. I had all my peers from college who had gone off to their great jobs at Google or whatever. I said, "I'm looking to move to San Francisco and work at my dining table, and I have a little bit of savings from this, so why not? Let's see. It's going to be super interesting." I mean, it was also very boring at times, and so, I didn't want a lot on the sort of micro level, but I built five or six products. I became much better at programming as a result.

**Jason Shah** (00:49:56):
I remember one time, it's kind of a goofy story, but I was working at my dining table, and I saw Ron Conway on the street. I was disheveled because I was just working from my apartment and I wanted to go pitch Ron Conway on this terrible idea for a startup, and so went out there, and maybe it was fortunate to not shove me to the side, and he listened to me for a minute and then I emailed him after. These are random things that happen that over time I think make us who we are. Are you the sort of person who's going to hustle and do that? When I was building that education company, I went and put flyers in people's cars in various high schools, and I was trying to get things started, and coming back to leadership, that would be below most people. It's like, "Wait, you own a company and you're sticking flyers in people's windshields?" It was like, "What's wrong with you?"

**Jason Shah** (00:50:40):
So, anyway, I think that was an example of time where it was like, "Okay, if I'm on the ladder," I'm like, "I got to get the best entry-level job or whatever." Even if I had been an entrepreneur before that, I would've thought about my structure in my career, and I was more like, "This is going to be interesting. I'll figure it out. I believe in myself enough that I'll figure it out." So, I did that. Yammer and leaving Yammer was similar where I could have stayed. My equity was finally worth something. I could have learned a lot even I'm sure from the Microsoft structure, but I was bored and I had been talking to a couple angel investors who were willing to put money into whatever the thing was going to be, and I felt like raising money's actually going to be really hard for me. This is going to make my life a lot easier and I can focus on product and so on and so forth.

**Jason Shah** (00:51:25):
That was a really hard four years. Things like an M&A offer falling through the day before your wedding, or chewing glass and submitting to the Apple iStore and being a featured app and then resubmitting because we wanted to fix a bug, and then actually now it crashes 90% of the time. It's Memorial Day weekend and you can't get in touch with the Apple business development manager who can help you out to reapprove something. It was a really stressful four years, but using the map analogy, that's like getting lost in Croatia and having to find your way out or getting lost to to your hotel in Australia or getting bitten by a dog in Thailand, which actually did happen to me. But these are interesting experiences that I think build characters.

**Jason Shah** (00:52:05):
So, I'll pause there, but I think there are a lot of career decisions I've made. Do I have regrets? At times, for sure because you see what would've happened if you had joined a different company at that time and it would've been like, "Oh, I would've met so many great people. I would've worked on these products. I mean, my equity would've been worth more," whatever. But I think you only lived once, and I think that these rare experiences have been very true to me and taught me things that I wouldn't learn otherwise.

**Lenny** (00:52:28):
What's really cool about that analogy, ladder versus map, is a lot of times you think you're climbing a ladder and you think it's innately going to be great, and sometimes that ladder falls over and the company doesn't go anywhere and/or the job sucks, your ladder's heading to some terrible place. And what I find in my experience is anytime I try something totally new and take a risk, especially following things that give me energy, and I'm just like, "Let's just take a leap on this thing," in my experience at least, it's always led to better opportunities and much more interesting work. And so, it's kind of this get off the ladder to get on a different ladder, and sometimes you think you're on a nice ladder and it's not going to get you anywhere anyway. So, explore other ladders. So, I'm kind of picturing a Chutes and Ladders.

**Jason Shah** (00:53:15):
Totally.

**Lenny** (00:53:15):
There's many ladders and you want to explore the different ladders across the map. How about that?

**Jason Shah** (00:53:20):
I mean, I think you're totally right, and the only brief thing I would add to the way that you put it which I think captures the essence here is I think we all have a lot of false precision about what we think a given career move is going to lead to or what it's going to be like, and we forget that a lot of career decisions are made out of maybe 10 hours cumulatively talking to a team and getting signals.

**Jason Shah** (00:53:44):
So, I think that that false precision sometimes gives us comfort in making certain decisions and folds us back from a bolder decision that might be better, but maybe the ladder is just hidden behind some fog if you really want that, and you can get both. Maybe you can go to the most interesting place in the world, and have the success in life and progress and so on and so forth. It's just that I think a lot of people think it's totally either/or. They think that they've already figured out the precise outcome that's going to happen, and to your point, the ladder often does fall over. If that's what all your hopes are pinned on, it's a very fragile career decision I think is really difficult to navigate.

**Lenny** (00:54:19):
The flip side, you also don't want to be bouncing around over and over and over. As much as I talked about how I shifted and tried new things, I'm a very serial monogamous in terms of work. My first job, I was there nine years, then a startup for a year and a half, and then Airbnb for seven years, and then what I'm doing now may be forever. And so, there's a lot of value to sticking around and kind of seeing things through. And so, I guess, I don't know if you'll have an answer to this, but do you have any wisdom on when to stick with it and keep exploring opportunities at a place you're at versus trying something new?

**Jason Shah** (00:54:54):
My hope is that there's a balance here in the sense that the map shouldn't give the impression of 180 countries, let's do 180 tech companies and shorten the tenure from two years down to a month, and we've just created a generation of job hoppers which is even easier because we're all on Zoom. It's a good point and I really respect people like you who have stuck it out through the ups and the downs and somebody sees seven years on paper, but I mean, seven years, I don't know. How many chapters of Airbnb, how many crises moments?

**Lenny** (00:55:26):
Felt like 300.

**Jason Shah** (00:55:27):
There you go. So, I think there's a balance, right? For example, I want to be in Web3 for more than a decade. I want to stay at Alchemy for a very long time and help build the company. So, I guess when I think of map, maybe an important way to think about it is maybe when somebody is 50 or 60 or 70 and they might choose to stop working, a lot of people when they start their career actually have 30 years to play with or 40 years or 50 if they're lucky. That's a lot of chips you can play. You could do five, 10 year rounds, right? And so, I think that in terms of sticking it out, maybe I'm biased, I think that some of the absolute sort gems, if you will, in Silicon Valley and tech are the teammates that are willing to stay around for 4, 5, 6, 7 years, and they have institutional knowledge that nobody has. They have a positive impact on the culture that is impossible if there's constant employee turnover.

**Jason Shah** (00:56:19):
So, to me, I think that you could simultaneously be somebody who's committed to companies, stays for a very meaningful amount of time, but zooms out and looks at their career. Actually, I think maybe this was even more, right? You're now a famous podcaster. You were a successful startup founder. You were a product leader. All these things form a map and I think a really interesting career and life, frankly, that's pretty full with a lot of really interesting milestones and learnings and networks and people that you get to interact with.

**Lenny** (00:56:47):
Yeah. To your point about how long a career is, when I thought about it recently, this is my fourth career. First it was an engineer, then it was a founder, then a product manager when I got to Airbnb, and now this weird thing that I do, and there's so much time to explore and try new things. I will say though, I feel like the early things you do seem really important. Airbnb for me was not early, so maybe I'm wrong, but it feels like you want to work at a company where people look at that on your resume and are like, "Oh, okay, this person's probably good." So, I feel like there's that piece you got to get right at some point.

**Jason Shah** (00:57:21):
Yeah, I totally agree with that. For example, I think for let's say a new grad who's thinking about a product career, and let's say on the spectrum there is maybe Goldman Sachs because that's what a lot of people are doing. They're like, "Yeah, I want to do product, but I also feel like I need this gold star or whatever." And then in between is you could join a hypergrowth company of some sort where they definitely have good product people you can learn from, but definitely still room for you to do more than what a very junior person would be assigned to be doing. And then on the other end of the spectrum is I'm going to have no job, I'm just going to completely bounce around from my own projects or just work with a new startup every two months.

**Jason Shah** (00:57:58):
Personally in that spectrum, I tend to be more towards the middle of that where build a track record, build a network. I mean, it's crazy. Even just this week, next week I'm seeing maybe five people that I know from my Yammer days, and to your point on formative nature, some of those people, that's how I learned how to do product. That's how I learned things like AB testing. It's how I had the first angel investors in my next company. That's how I hire. I still hire people, maybe much to their chagrin, they still get LinkedIn messages for me trying to push them for the next thing.

**Jason Shah** (00:58:27):
So, I totally agree that those early days are really formative, and there's maybe a balance between nobody wants to be a job hopper, but at the same time maybe there's ways to also not just be a career person who spends kind of 30 years working up the ladder or is fixated on I need to be CPO but is willing to give up a director title to go be a hustler at some startup because they really believe in it and they want to take a bet or risk in their career.

**Lenny** (00:58:50):
You touched on hiring, and that's something I wanted to ask you. So, you're in my Talent Collective. You're a company that's hiring, Alchemy, and I was looking at the stats recently, and you're one of the most successful companies at getting candidates to talk to you, and generally I think you're just really good at hiring. So, I'm curious what you can share with folks about hiring.

**Jason Shah** (00:59:10):
I appreciate that, and I get a lot of value out of meeting some really talented people from the Collective. I think hiring, it's funny, it reminds me of sort of push back in a sense of what you call it has such an impact on how people think about it. It's hiring, recruiting, but if people reframe it as the people you are going to work with every day or the people who make the company what it is, it shifts the mindset. It's like how is that not the most important thing to be thinking about as a leader or as a founder. A lot of people have benchmarks. I think maybe on the Google podcast I talk about 30%, 40% of a founder's time maybe spent on recruiting because I think deep down everybody understands that that's incredibly valuable.

**Jason Shah** (00:59:53):
I think that for me personally, I was reflecting ahead of the podcast on how I approach things now after different stages of hiring, and for context, for what it's worth, I've been at the zero person startup. It's just me and I'm trying to convince some Google engineer to come join us which is incredibly hard and has a low hit rate, to a place like Amazon or Airbnb where you have a large world-class recruiting organization that is effectively doing sourcing for you and setting up interviews and such things like this, and there's formal calibrations and interview panels, to a place like Alchemy where it's very sort of scrappy. We need to figure out who we even want to hire. The founders still meet with every candidate. It's a really different environment.

**Jason Shah** (01:00:34):
So, this is kind of the spectrum that I've seen, and I was reflecting what do I think works the best, and I like to think of it in very similar motions to a business where I think there is a marketing aspect to it, there was a sales aspect, and there is a product aspect to it. What I mean by that is that on a marketing level, I think what has a person heard about your company. Do they know anybody who works there? Do they read your LinkedIn post about things and already know that you're a known quantity before they even step in the door to interview? Are they even willing to interview based on what they know about the company? And so, I think that the marketing aspect in it, and I mean it's sort of lower case marketing in this sense of course because I think a hard sell of any sort or anything that's not authentic is probably going to fail ultimately, but it's about developing a really positive kind of brand and reputation for a company but also as an individual.

**Jason Shah** (01:01:26):
And then if you pass that threshold, I feel like there's a sort of a sales process, and we were talking about how bad of a salesperson I am, for example, because I didn't listen to people's pain points and understand the one or two things that were most important to them. I think similarly in this context, if they're an engineer, do they want to work in a world-class engineering organization? If they're a product person or they're just really excited about crypto and they want to find a way in, a place like Alchemy's the best place for them to learn that is how to think about it, and it's not about misdirecting on or matching whatever they say, but it's about really understanding who they are and what motivates them and what they're excited about because I'm as concerned about the kind of post-hiring step as I am the pre-hiring and want them to work out and be happy and be effective.

**Jason Shah** (01:02:12):
And then lastly, I think there's a product angle to it that not a lot of people think about or talk about a lot because I think the product, it's one of those rare cases where job descriptions are almost like product specs, right? They're here's what the responsibilities are, here's what we need you to do, here's the qualifications we're looking for. And what's really funny about that is that product is very iterative, but somehow we just write a job description, and then it's bait, it's done, it's posted, and nobody thinks about it again until the person's hired and then they take it down.

**Jason Shah** (01:02:41):
I think taking a product mindset where I meet people all the time now where I don't really know exactly what role they're necessarily going to fill, I'm not really sure about exactly their seniority, maybe they don't have a lot of experience, but maybe they would just totally be a rockstar on our product team. And looking at a product that we can mold flexibly and think of the same way if at Airbnb, if we were going to build Airbnb Plus, if we just kind of came back to the Amazon working backwards and just wrote a document and it was over, that's one thing, but we didn't do that, right? We went and actually built rooms and homes that were supposed to be Airbnb Plus, and then we iterate on it and we changed the pillows and we changed the entrance and we changed the scent that you feel when you walk in. We coach host and learned about that.

**Jason Shah** (01:03:21):
So, I think a product mindset on hiring and iterating on it based on the candidates you're meeting, the needs of the business. So this kind of marketing, sales, product combination has been what I've found to be really effective at getting people excited, understanding who they are and what they need, and then crafting a role that actually makes the person successful, rather than just checks a box in your recruiting software as some new headcount that was hired.

**Lenny** (01:03:45):
One last question before we get to our lightning round. For PMs that are listening to this maybe early in their career, what skill have you found to be most important in helping you and helping PMs in general advance in their career?

**Jason Shah** (01:03:59):
Yeah, this is a really important question, like the others, but I think that understanding and defining what problem matters is the most important skill that I think I've taken away, and it applies to so many things. It can apply to a specific product we're building. It can apply to what a company's mission is. I think I've found it really effective because it affects pretty much everything. It affects what we're going to build. It affects is the team motivated by what we're doing. So, specifically for example, at a place like Alchemy where, yeah, we're a developer platform, but should we build an SDK so there's abstraction that is easier for developers to use? Should we build an NFT API because we think that's a really important stack to move into and an important use case to support?

**Jason Shah** (01:04:45):
Well, the question is what problem are we solving? It's not this versus that just in a vacuum. It's is the problem developer experienced and we want to make things easier to develop. Is the problem that an NFT marketplace, a whole suite of them are trying to grow and need more support from us, and not understanding these problems clearly? And it goes back to my first company. It was an education company, and the problem was that low-income students didn't have access to the same resources to get into college as other students, and that guided everything. That guided the pricing model which was basically free for a long time, and then we monetize on sponsorships from colleges, right? The problem matter, whereas the problem solve was there's not a... A different problem was there's just no good college readiness program. Fine, then you focus manically on the pedagogy and the curriculum and so on and so forth, rather than say the business model and an initial product that you think can work.

**Jason Shah** (01:05:34):
So, that's what I've found to be the most useful, and I can give her other examples if it's helpful, but understanding what problem we're actually trying to solve and really getting crystal clear about it, I think has been incredibly useful to me and energizing as well.

**Lenny** (01:05:48):
It's such a good reminder, even though it's such a cliche of product managers being, "Well, what problem are we trying to solve here?" People hate that, but Michael Paul, and I mentioned this on a different podcast too, he makes this point that when you do drugs sometimes, you have these epiphanies that you come out and you're like, "Love is all you need, man." It's like, okay, yep. But it feels so right. You really feel it. The reason that it's such a cliche is because people have found it to be so true for so long that it's annoying now, but it also tells you how true it is. And so, I think it's a really good reminder of yes, it's annoying to ask that question, and people make fun of PMs for that, but that's because it's so damn important.

**Jason Shah** (01:06:28):
Just a brief kind of additional, what you share there, I mean, I completely agree. I think it's very true in life, right? It's like, well, what matters? And it's like, well, your health, your family, your sense of purpose. It's like nobody's unfamiliar with the answer, but like most things, it's about the application of it and about the nuance of it, and I think that's what product is ultimately sort of all about too.

**Lenny** (01:06:48):
Awesome. Are you ready for our lightning round where I'm just going to ask you five quick questions, tell me what comes to mind and we'll have some fun. Does that sound good?

**Jason Shah** (01:06:58):
That sounds great. Ready.

**Lenny** (01:06:59):
Okay, cool. I think I'm going to start adding music to these things. I got to figure that out. For now, no music. Okay. What book do you recommend most to other PMs?

**Jason Shah** (01:07:07):
The Hard Thing About Hard things.

**Lenny** (01:07:10):
Can you add why?

**Jason Shah** (01:07:11):
I think it teaches product managers to chew glass and care about outcomes the way that a CEO has to, and I think that's a really useful mindset to have.

**Lenny** (01:07:21):
Man, this chew glass metaphor, I don't like the sound of that.

**Jason Shah** (01:07:24):
I saw you cringe. I was a little worried about that.

**Lenny** (01:07:27):
Oh my god. What a great job we have here, chewing glass. Okay. Other than Alchemy, what's a company you recommend most to PMs to go look for new gigs if they're looking around?

**Jason Shah** (01:07:37):
I would suggest Polygon, Salon, or MoonPay. I know it's three, but I wanted to give some breath in the Web3 space that might be exciting to people.

**Lenny** (01:07:45):
Great, great choices. What's a favorite TV show or movie that you've recently watched?

**Jason Shah** (01:07:48):
The Ken Burns Vietnam War series. I'm really into documentaries and history, and it's a really kind of compelling version of history that I've never seen before.

**Lenny** (01:07:58):
Awesome. Love that. Okay. Favorite interview question that you like to ask.

**Jason Shah** (01:08:02):
What is a risk you regret not taking, why, and what did you learn about yourself?

**Lenny** (01:08:08):
What do you look for in an answer there?

**Jason Shah** (01:08:10):
I think the biggest thing I look for is a growth mindset, to be able to reflect on an experience like that and be vocally self-critical without unproductively being hard on one's self, and I think that the dimension of asking about risk gets at their psychology and how do they think about not only their career, but if they were to work with me, how would they approach problem solving and taking bets on the business.

**Lenny** (01:08:33):
Awesome. Okay, final question. What's your least favorite vegetable?

**Jason Shah** (01:08:36):
Broccoli. I just removed some from a pizza last night that I really didn't want to eat.

**Lenny** (01:08:41):
Wow. Oh wow, okay. Even like steamed, cook, all the things?

**Jason Shah** (01:08:45):
There are no circumstances under which I'm excited about broccoli.

**Lenny** (01:08:49):
Oh man, you got to eat those veggies.

**Jason Shah** (01:08:51):
I know. I'm working on it.

**Lenny** (01:08:52):
Okay, Jason, this was amazing. Lived up to what I was hoping our second episode would be. Definitely better than our first which we'll leave on the cutting room floor. Two last questions. Where can people find you online? I assume Alchemy's hiring, so maybe pointing people there. And then how can listeners be useful to you?

**Jason Shah** (01:09:08):
Yeah, definitely. So, if you're interested in Alchemy and Web3, go to alchemy.com and click through to our jobs page from there. I'm online @0xShah. That is my crypto pseudonymous handle and happy to engage with folks there. And in terms of being helpful to me, I would love any feedback on anything that came up. I would love any products that people are working on. I also invest, and we also partner with a lot of products and teams at Alchemy, and I would love to meet anybody that's listening on the podcast too because I know Lenny's all about community and has kind of given so much back over the years that I would love to meet folks that are out there and get a chance to spend time talking about the products that you're all building.

**Lenny** (01:09:46):
Awesome. Thanks, Jason.

**Jason Shah** (01:09:48):
Thanks, Lenny.

**Lenny** (01:09:50):
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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## [19/20] Growth tactics, retention strategies, and becoming a better writer | Julian Shapiro (Demand Curve, Hyper, Webflow, TechCrunch)

**Julian Shapiro** (00:00:00):
Why do good ideas arrive after the bad ideas are empty? It's because when you've gone through a bunch of bad ideas, your brain, your mind starts reflexively identifying what elements are causing the badness. Then it becomes way better at avoiding those bad elements and you become way better at pattern matching the novel ideas with way greater intuition. Most creators are resisting their bad ideas. If you sat down, scribbled a few thoughts in a blank document and just walked away because you weren't struck with gold, then you never actually finished the creative process. There's no way you would've come up with gold.

**Lenny** (00:00:37):
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 Julian Shapiro. I actually spend a bunch of time introducing the wondrous Julian at the beginning of the episode. Instead, let me just share some of the things that we talk about. We get into a framework he calls product-led acquisition, which is work that has come out of his working with thousands of companies, helping to figure out their growth strategies.

**Lenny** (00:01:10):
We get into ways to increase your product's retention. Then we talk a lot about writing, the importance of novelty in your writing, how to choose a topic when you plan to write, and then a framework that Julian calls the Creativity Faucet. Julian is such a fascinating human, and I'm really excited to bring you this episode. With that, I bring you Julian Shapiro. I'm excited to chat with my friend John Cutler from podcast sponsor Amplitude. Hey, John.

**John Cutler** (00:01:37):
Hey, Lenny. Excited to be here.

**Lenny** (00:01:39):
John, give us a behind the scenes at Amplitude. When most people think of Amplitude, they think of product analytics. But now you're getting into experimentation and even just launched a CDP. What's the thought process there?

**John Cutler** (00:01:50):
Well, we've always thought of Amplitude as being about supporting the full product loop. Think collect data, inform that, ship experiments, and learn. That's the heart of growth to us. The big aha was seeing how many customers we're using Amplitude to analyze experiments, use segments for outreach, and send data to other destinations. Experiment in CDP came out of listening to and observing our customers.

**Lenny** (00:02:11):
Supporting growth and learning has always been Amplitude's core focus, right?

**John Cutler** (00:02:15):
Yeah. Amplitude tries to meet customers where they are. We just launched starter templates and have a great scholarship program for startups. There's never been a more important time for growth.

**Lenny** (00:02:24):
Absolutely agree. Thanks for joining us, John, and head to Amplitude.com to get started. Hey, Ashley, head of marketing and Flatfile. How many B2B SaaS companies would you estimate need to import CSV files from their customers?

**Ashley** (00:02:38):
At least 40%.

**Lenny** (00:02:40):
How many of them screw that up and what happens when they do?

**Ashley** (00:02:42):
Well? Based on our data, about a third of people will consider switching to another company after just one bad experience during onboarding. If your CSV importer doesn't work right, which is super common, considering customer files are chock- full of unexpected data and formatting, they'll leave.

**Lenny** (00:03:03):
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 aha moment more quickly and reliably is so incredibly important.

**Ashley** (00:03:17):
Totally. It's incredible to see how our customers like Square, Spotify, and Zuora are able to grow their businesses on top of Flatfile. It's because flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:03:34):
If you'd like to learn more or get started, check out flat file at flatfile.com/lenny. Julian Shapiro is what I'd call a polymath of the internet. He's an amazing writer, marketer and growth mind, investor, community builder, podcaster, tweeter. He's also an expert on building muscle. He's maybe most known for being the founder of Demand Curve, a YC startup that trains people on growth and marketing. Prior to that, he was a part-time columnist at TechCrunch. He was also VP of marketing at Webflow, which I had no idea about.

**Lenny** (00:04:09):
He also created a JavaScript web animation engine that is used by Uber and WhatsApp and Samsung and thousands of companies. Currently he is a full-time investor with his own fund and as a partner at Hyper. He's also one of the most hilarious and generous humans that I know. With that, Julian, welcome to the podcast.

**Julian Shapiro** (00:04:28):
This is the greatest honor of my life. Thank you.

**Lenny** (00:04:31):
Wow!

**Julian Shapiro** (00:04:32):
I'm crying from that intro. Very nice of you.

**Lenny** (00:04:35):
That's the idea. This is the greatest honor of my life. We match.

**Julian Shapiro** (00:04:40):
Excellent. We'll cancel each other out and we'll see how interesting this is.

**Lenny** (00:04:43):
That's right. There's a lot of hype. I know you have something like 250,000 Twitter followers. You're very good at Twitter, but I've noticed that you've only tweeted three times this past year. What is going on there?

**Julian Shapiro** (00:04:58):
There's a few things in parallel. One is a lot of people are writing threads and I found this to be very cringe. They're like these fortune cookie threads like here's 21 ways to rework your startup or something. I found them all cringe. What they actually do when you write that stuff is they attract people who think that's valuable information, and then they cause people who you actually want to follow you to unfollow you. I remember just seeing people unfollow me early days of threads when no one was doing them and I was experimenting. They were pissing off people that I actually cared to have dialogue with.

**Julian Shapiro** (00:05:36):
I kind of lost the momentum and enthusiasm for writing that sort of stuff. And now I'm only writing anything when it's basically a reflection or a condensed version of a blog post that I happen to be writing from my website. I know it's high quality. I know it's original. I know it's thoughtful. It's not for the click bait. That was part of it. The other thing is that it's kind of like too... Here's a mental model for thinking about the quality of your followers. You have people who follow you for the quality of your brain, and you have people who follow you for sort of you being a glorified curator. If they're following you for being a curator, they're sort of what I call labor followers.

**Julian Shapiro** (00:06:16):
They're following you for the work that you're doing, where you're finding cool, funny memes. You're posting cool, funny jokes. You're doing these fortune cookie threads. In contrast, if they're following you for your mind, which is category one, it means they're following you for the original thoughts and insights and takes that you have on the world. Someone like Paul Graham, the founder of Y Combinator, is doing original takes. He's not trying to write threads for the sake of gaining followers. He's trying to write interesting novel ideas. When he does that, he strengthens the affinity that his followers have for him and his mind, because like, "Wow! That was an original interesting take."

**Julian Shapiro** (00:06:49):
They're following you for your mind, not for the labor you're doing, putting together a virtual Buzzfeed to count on Twitter. When people follow you for your mind, when they're mind followers, not labor followers, higher affinity means more loyalty, means they pay closer attention to what you're saying. And if you actually try to get them to do something with you, you have an event offline, there's something you're selling, there's a cause you care about, they're way more likely to indulge.

**Julian Shapiro** (00:07:12):
Whereas if they're following you for your labor, you're interchangeable with all these other meme accounts and there's no real affinity for you as the individual. I just care more about the quality of the follower than I do the volume.

**Lenny** (00:07:23):
I love that. That's such a good reminder, not to just focus on follower, follower, follower. I'm curious if someone... You have a lot of followers at this point and it's just so valuable to have Twitter followers. I've learned for me, anytime I have a question about anything, I just ask and I get so many amazing answers from people. There's this power to having a large following. I'm curious while we're on this topic, if you're just starting out on Twitter, do you have any advice for someone that's just thinking about building their following?

**Julian Shapiro** (00:07:50):
I mean, generally speaking, threads, despite everything I've said, are the primary way to get followers. There's a reason why people do threads as opposed to single tweets is because when people get exposure to a thread, they're basically getting exposure to the length of thoughts equivalent to you having sent a newsletter edition or a blog post in many cases. The more exposure, the more surface area you have, the more you give people of your brain in a single tweet, the more they're able to confirm that what you're sharing is actually a consistency from you.

**Julian Shapiro** (00:08:21):
Whereas if you just tweet one clever thing, they're like, "Oh, that's probably just a drop in the bucket. Who knows if that person can consistently generate clever stuff?" But in a long thread where it's 30 tweets and they're all good, they're like, "Whoa! This person is a machine. If I follow them reliably, I'll get more great stuff." It reaffirms to readers they should follow you, which is why threads trigger more follows. Basically you do want to do threads, frankly, and that's the backbone of it. Threads with very clickbaity opening tweets kind of how it works.

**Julian Shapiro** (00:08:52):
You can also port followers over from other places like your website and newsletter, just to start giving yourself an initial sample audience through which the threads can actually take fire pretty much.

**Lenny** (00:09:02):
Awesome. I wasn't expecting to go into Twitter as strategy, but this is interesting because you're really good at it. As you've said, your stuff is actually very thoughtful. It's not just a thirsty Twitter thread trying to find followers and retweets. Thanks for sharing that.

**Julian Shapiro** (00:09:18):
Well, it sort of started that way, because me and a few other friends of mine, I felt like we were the first people doing threads at scale. And then when we realized what it turned into, that's when we just stopped.

**Lenny** (00:09:28):
I love that. I know what you mean about these cringy Twitter threads. Anyway, what I want to do is instead of asking a bunch of random questions is to focus on five big topics and kind of go deep on these topics. These are topics that are maybe most popular of the stuff that you've put out across your handbooks and writing and courses and things like that and also things that I've found to be most interesting. Does that sound good?

**Julian Shapiro** (00:09:51):
Yeah, I would love to.

**Lenny** (00:09:53):
Cool. First, a little context, you write these super in depth handbooks on a bunch of different topics on growth and writing and muscle building and things like that. First of all, could you just explain what these handbooks are and why you create them?

**Julian Shapiro** (00:10:05):
They're forcing functions for me to hold myself accountable and to be thorough when learning something for my own benefit. That's all they are. Basically if I want to go learn growth or writing well or some other topic, I will go ahead and do a ton of research, read everything I can get my hands on, do a ton of experimentation to try to build a set of novel insights that you couldn't find from other people's research hopefully, and then the next stage is try to make it as concise and actionable as possible so that I can reference it for my own selfish benefit. Here's my guidebook for myself on writing better blog posts, for example.

**Julian Shapiro** (00:10:40):
And then by the time I've done that work, what usually happens is its only like, I'm going to make up a number here, an extra 30 hours of work to make it palatable and digestible for the public. If I've done all this work privately, why not make it accessible publicly? At that point, it winds up being acquisition fodder for essentially building an audience and distributing my thoughts further. That's why I do that. But the thing that I pride myself on with them is by no means are they thoroughly unique, but in every one there's a lot of original stuff folks on average have never heard of before.

**Julian Shapiro** (00:11:14):
And that's what I'm proud of, is coming up with those insights between the lines that make that thing, whatever the topic is, much more approachable. I've succeeded, in my view, if I've made something that people often mistakenly think of as overwhelmingly complex very simple for them to follow. I think that's where the dopamine hit comes from for them.

**Lenny** (00:11:34):
Well, my experience, you definitely hit the nail in my head with the handbooks you put out. It's an interesting middle ground between a newsletter and a book. It's cool to just have a digital way of doing that, of just kind of consolidating a bunch of ideas and going really in depth, but not having to write a book. Well, speaking of the contract there.

**Julian Shapiro** (00:11:51):
You have a very large newsletter that goes very in depth. That arguably is a more valuable asset than my handbooks for someone building an audience, because the newsletter has this built-in form of retention recurrence, where they get pinged in their inbox when you have new content, and then it becomes a referable thing and people refer each other and then they sign up for the newsletter. I do love the emphasis on longform via newsletter, but the reason I do it on the web is, and we'll talk about the trade-offs in a second, is it's much more digestible and referencable.

**Julian Shapiro** (00:12:24):
No one's going to go refer to the epic guide in their email inbox that's very hard to navigate for building muscle or something. One, it's a UX decision. Two, I get the SEO traffic, which you don't. And then three, it's basically a living asset that I can keep updating over time. It's not stuck in someone's inbox and getting printed out. One of the things that might separate me from other writers, at least many other writers online, is I'm spending as many hours going back and rewriting old blog posts and handbooks as I am writing ones.

**Julian Shapiro** (00:12:55):
If you come back to anything I've written over the course of a year or year and a half, it'll be updated, because I consider everything I write to be evergreen. I avoid writing things that I feel like are a drop in the pan, just like talking about a trend or something, something very newsy. I avoid that altogether and I'm just interested in writing stuff that'll be relevant for a long time.

**Lenny** (00:13:13):
I didn't know that. That is very cool. I love that you do that. You should make that clear. That's so interesting that this is not stale. Last updated, last week. I don't know if you already do that.

**Julian Shapiro** (00:13:21):
Yeah, no, I actually don't and I probably should. People have complained to me that I haven't, so maybe I will one day.

**Lenny** (00:13:25):
All right. We got a good idea out of this, if nothing else.

**Julian Shapiro** (00:13:28):
There you go.

**Lenny** (00:13:28):
Okay. The first idea that I want to chat about is something that you call product-led acquisition. I believe it's the most popular page in any of your handbooks. It comes from you working with thousands of companies to help them figure out their growth strategies through Demand Curve. I'm curious to hear what this concept is and how people can use it to help their products grow.

**Julian Shapiro** (00:13:51):
Product-led acquisition to your audience will be more commonly known as product-led growth, but I think product-led growth is a bit of a misnomer. It's often used, as you know, to basically refer to SaaS companies who are using self-serve sales funnels where a salesperson isn't required, right? Bypassing sales and allowing the product to grow itself. That's fine. But I think the term we really care about as growth marketers is product-led acquisition, meaning the use of the product grows the product. For example, if I'm using PayPal and I'm sending $1,000 to somebody else, there is no way they will not create a PayPal account to accept the $1,000.

**Julian Shapiro** (00:14:31):
By me trying to use PayPal in its everyday intention and me getting value out of it to settle a debt, I'm automatically enticing someone else, very strongly so, to also become a PayPal customer. That's product-led acquisition. There's a few different categories I've identified, and I think the reason why people like this part of this article I wrote is because it's, in my opinion, the absolute best way to grow any startup. If your startup can grow via product-led acquisition, not all can, maybe some are enterprise-base and all they're going to make work is sales, then it is by far the best way to grow because zero marginal cost to have users invite other users.

**Julian Shapiro** (00:15:12):
It's scalable. It creates network graphs typically and has compounding effects there in terms of both moats and the ability to acquire more customers quickly. Basically to the point I just mentioned is basically viral. The other interesting thing here is there are far fewer dependencies. Let's say your company primarily grows via content and SEO, where you're at the mercy of Google releasing an algorithmic update let's say twice a year, which occasionally will absolutely tank your traffic and most people know what I mean by that if they've experienced that. It's awful.

**Julian Shapiro** (00:15:41):
Or ff you're a paid acquisition-led company, as opposed to a content-led acquisition company, meaning you're running Facebook Ads, let's just stick a Facebook for now, Facebook and Instagram, you're also at the mercy of the volatility of CPMs and whatever weird updates Facebook introduces or whatever targeting options they suddenly remove. Your entire acquisition strategy is anchored on something that is completely out of your hands and very volatile. Product-led acquisition is like the better you craft your product and the incentive structures for existing users inviting other users, that's entirely in your control and the better you grow.

**Julian Shapiro** (00:16:19):
That's the quick context. Now, I'll go into some examples. We started with the example of... Actually one thing that came to mind that I love is Paul Graham, who we mentioned earlier, Paul Graham from YC, has this quote which is "don't start a startup where you need to go through someone else to get users." That always really resonated with me. Here are the categories of product-led acquisition that I've identified. Number one, like I mentioned, is users inviting other users to settle debts.

**Julian Shapiro** (00:16:51):
If I'm going to pay you money I owe you for splitting dinner on Venmo, or a business expense that I'm paying you, you're my vendor on PayPal, or anything that's allowing me to just pay you money I owe you and I have to use a product to do so, whoever is collecting the money from me is going to make an account on that product if necessary to claim their hard earned money. Almost guaranteed way for you to have user-led growth, product-led growth. Now, it doesn't have to be money. It can be settling a debt of like an NFT, for example.

**Julian Shapiro** (00:17:19):
Someone buys an NFT from you on OpenSea and the only way for them to receive their NFT, I'm just making this up right now, is to also have an OpenSea account or a wallet that's specific to that collection. Again, making this up. The point is if you're settling the debt of something you owe someone and they must make an account to capture the thing owed, they're going to sign up. That's category one. Category two is when you're inviting someone to join the product you're using to partake in a conversation that the otherwise cannot access. Why does Telegram, WhatsApp, iMessage, all these chat apps, Discord, grow so quickly?

**Julian Shapiro** (00:17:58):
Pretty obviously because if you and your little clique of friends are having your conversation in that app, then the person who's also in your real life friend group, but who hasn't yet installed the app has to install the app in order to have the conversation with you. Inviting people to critical, social, or business conversations in an app is the other way that you can nearly guarantee you'll grow very quickly from product-led acquisition. The business version of this is Slack. You sign up for Slack. You invite all your friends or all your coworkers. Then you even invite all your vendors via Slack Connect.

**Julian Shapiro** (00:18:34):
Slack Connect was a brilliant Slack feature where they're saying, "Hey, we're now going to encourage you to invite people who aren't using Slack who are outside of your work." I don't know how that's done for them as a feature, but in theory, it's a brilliant way to expand the surface area for inviting people via product-led acquisition. Just to recap where we are real quick, one of the ways of acquiring customers is to encourage existing users, to pay other people or to encourage them to come into your app to have conversation that's only happening on the app.

**Julian Shapiro** (00:19:04):
If I'm a product person and I'm road mapping my product, I will think, is there anything in my product conducive to either one of those two functionalities, settling debts, or can I introduce chat within my product? And if so, you might be cracking open an amazing channel. When I tell people about product-led acquisition, I'm usually doing it in the context of let's rethink your product feature roadmap to prioritize features that facilitate these things that can lead to explosive growth. I'll pause if there's anything you want to dive in there, but I have three more categories we could chat about if you want to, three more ways of doing PLA.

**Lenny** (00:19:44):
Yeah, absolutely. I just want to lob a question over there as you're going through these to maybe touch on this. Most founders would love to find a way to grow through virality and invites and all the things you're talking about. I find that it's often hard to lop onto something they're doing, if it's not a natural fit. As you're going through this, I'd love to know how often have you seen startups succeed adding something like this when their app is not a money exchange app or a chat app? I'm curious how often it works to add something like this when your app's kind of something else, if that makes sense?

**Julian Shapiro** (00:20:17):
Well, the real lesson is don't start a company if you have no idea how it's going to grow. Now, that's not categorically true for all startups. It's irrelevant for deep tech and biotech and climate tech and all that stuff, but for a lot of these people starting SaaS companies where they intend to grow very quickly among B2B customers or B2C. The real point of what I'm saying is if you have three ideas before you as a founder and one of them lends itself to product-led acquisition really beautifully, then lean in that direction perhaps if you think that growth is the key differentiator between them for what's going to lead to success.

**Julian Shapiro** (00:20:51):
It's like make life easier on yourself. Because if we're relying so heavily on SEO and content, which is extremely saturated, or paid acquisition, meaning ad channels which are extremely saturated, especially if you have low LTVs where we can't really tolerate the volatility of paid CAC or just the cost in general of those CACs, then we have to be thinking more strategically at the product level. It's less about tacking it on later, but sometimes this will work brilliantly if it's very organic. When we cover my next category, we'll actually see some examples of how you can pack it on more seamlessly.

**Julian Shapiro** (00:21:24):
But the other response to your question, which is a great question, is people mistake product-led acquisition for referral programs, which it is not. Because the referral programs are a tact on incentive trying to give people something to encourage them to invite because they otherwise are not inviting. Whereas PLA, as I've currently defined it, is through the natural use of the product, you get more value when you invite others. You settle your debt with the payment recipient. You get have a better conversation because now your friend Jack is part of the conversation. You don't have to incentivize them with anything artificial, with any rewards.

**Julian Shapiro** (00:22:00):
Referral programs generally are not exciting to me because you're usually trying to... Again, you're like self-selecting for folks who just want the reward very often. And then the people they invite might also just want the dual ended reward and they're not even here for the app really. And then they can bounce. And then they don't invite other people typicall.y. It doesn't have the same compounding sticky retentive nature of PLA. I'm not a fan of it. If you can make a work though, fantastic. Anyway, third category is what I call billboarding. Billboarding is this idea that the use of the product is inherently visible to people around you.

**Julian Shapiro** (00:22:40):
The product advertises itself. A few examples. Actually, where I got the term from is I was looking at these billboards above the highway in San Francisco, where I was seeing the company that actually hosts the billboards advertise their own logo on the billboard while also showing you whatever ad they were being paid to show. They were using their own surface area to advertise themselves. Another example is when you're seeing an ad network across the web, like Google banner ads perhaps, and it says they're brought to you by Google Ads, they're using their own surface area to advertise themselves.

**Julian Shapiro** (00:23:14):
That's billboarding. It's a brilliant free way to get a ton more exposure. There's a few ways to do billboarding. One is the classic example of Hotmail and iPhone. When you send an email via Hotmail, at the end, it pens a signature saying sent via Hotmail. Same thing, sent from my iPhone. Every single email sent from an iPhone device, unless you remove that signature, is a free billboard for Apple itself, which further furthers the brand awareness and gets more people buying.

**Julian Shapiro** (00:23:45):
For example, if you have a feature in your application where people are sending emails or communications to other users outside of the org, like it's an app for sending SMS messages or it's like a way to send invoices to your vendors, when you're facilitating that generated messaging, say brought to you by the name of your startup in the signature of it, really use your own surface area to increase your own awareness. That's billboarding in two different ways. The third way is the very obvious way of having something unmistakably recognizable out in the world.

**Julian Shapiro** (00:24:21):
If I drive a Tesla, if I wear Nike shoes, if I have Apple AirPods, all of these are immediately visible to everyone around me, which is why sometimes physical products can really explode because they're just free walking billboards all over the world. And then the sort of most topical hot example right now on Twitter is when you switch your Twitter profile to an NFT in a particular collection, you're billboarding for that NFT collection, right? Same phenomenon that occurred with the Bitcoin laser eyes.

**Lenny** (00:24:50):
And also for Twitter Blue, to be able to even do that.

**Julian Shapiro** (00:24:53):
Yes, exactly. Exactly right. Like Telegram right now, they released something like Twitter Blue. I forget, I don't know what it's called. But now when you're a Telegram premium paying user, it has a little star thing next to your name that everyone else sees. "Wait, what is that? Oh, that's Telegram Pro. Let me take a look at that." Last example, which is one of my favorites, is billboarding via the nature of your product being something people are compelled to share in order to use. If I have a Calendly account, I have to share my Calendly link with the world in order to create an event on my calendar.

**Julian Shapiro** (00:25:28):
If you're like me, you get a million Calendly links every week. That's the phenomenal form of billboarding, people are sharing it willingly. No wonder they've exploded. Same thing with Dropbox sharing file links and you're seeing the Dropbox URL, or GoFundMe, when people share the GoFundMe page. You get the gist. Billboarding costs you nothing, scales infinitely, can have compounding effects. And if your product lends itself to billboarding, it's just a phenomenal way to grow if possible. That's category three, I guess. We'll cover one last one, if you'd like me too, which is basically UGC, so user generated content.

**Julian Shapiro** (00:26:05):
Same sort of thing. Basically I hop on YouTube or TikTok or Insta or whatever. I make content. I share it with the world. In so sharing that content, the platforms brand themselves on the content. At the end of every TikTok video on Twitter that you've ever seen or Insta, at the end it'll say, "Here's the TikTok user's account." They're billboarding themselves into the content that users themselves are generating, and the users are incentivized to share that content off platform, which brings users to the platform, because users want to get customers wherever they can. They're going to cross-sell to their YouTube channel and so on.

**Julian Shapiro** (00:26:41):
If you have a marketplace like eBay or some marketplace for selling collectible shoes or something where you're encouraging users to create beautiful content of the items being sold, like these cool landing pages that show off the products, and they share it elsewhere, then that's an example of users making content they're sharing off platform that is useful for their own followers. Another example of UGC that people often overlook is Quora or Reddit or Stack Overflow or TripAdvisor, where you're encouraging users to create content in the form of conversation that then surface itself on Google and SEO.

**Julian Shapiro** (00:27:23):
Basically if you just encourage users to have conversations that are publicly indexed, that increases your surface area on Google for hitting more keywords and you get way more search traffic. Basically the question that this boils down to is to leverage UGC in your product, you ask yourself, do users use my product to make content in any way, shape, or form? If so, what type of content that they make should we encourage them to then share? And then how can we make the page that they use to share the content as appealing and as easily to consume as possible? And that's basically UGC. We'll pause there, but basically that's PLA in a nutshell.

**Julian Shapiro** (00:28:03):
The thing that all of these have in common is you're not spending a dollar. They scale super quickly. You're not reliant on, well, maybe to some extent with SEO, but you're not relying on third party volatility. It's a much healthier narrative for how you're going to grow and scale.

**Lenny** (00:28:17):
Awesome. This episode is brought to you by Eppo. Eppo is a next generation A/B testing platform built by Airbnb alums for modern growth teams. Companies like Netlify, Contentful, 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 team 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.

**Lenny** (00:28:57):
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**Lenny** (00:29:34):
We talked about acquisition, which we'll link to in the show notes, by the way, this whole post. The flip side you could say is retention. If you're a reader of my newsletter, you know how much time I spend thinking about retention and how important that is. I know that's a second topic that we wanted to chat about, because you've also helped a lot of companies think through their retention strategies and to help them retain more users. I'm curious to hear what you've found to be the best strategies for retaining users and increasing retention.

**Julian Shapiro** (00:30:01):
Yeah, sure. The way I think about retention, my favorite strategy is what I call building state. It's a concept I stole from video games, where basically the more you play any given game, the more state you're accruing. That might be your armor, your weapons, your character skins, and whatever. As a player of the game, the more state you build, the more you're compelled to stick around, because you don't want to lose everything you've worked so hard for. The more state you have, the more you can exploit that state to get more. The rich keep getting richer. The same mental models apply to let's say SaaS retention.

**Julian Shapiro** (00:30:38):
This is as old as time, or at least as old as modern capitalism. If you think of credit card rewards or frequent flyer programs, you spend money. You accrue points. You convert the points into rewards. Once users build momentum doing that, they're less likely to switch to a competitor. That's the age old example of building state. Software, it's unbelievably powerful. This building state concept is why mediocre companies like eBay or Craigslist remain completely unbeatable for decades. Even though the UX is bad, people don't like using them, they fail to innovate, no one topples them and it's because of state.

**Julian Shapiro** (00:31:16):
Let's walk through some examples. State, kind of like my PLA mega spiel, mega rant there, subdivides into a few categories, but I'll make this one shorter and less boring. The first subcategory of building state is when you're encouraging your users to accrue non-transferrable reputation, meaning they're doing stuff to build reputation on the platform and they cannot take that reputation to them off platform. They're stuck there to get the compounding advantage of that reputation. For example, let's say you've spent years getting 10,000 or more feedback ratings as an eBay seller.

**Julian Shapiro** (00:31:56):
You are not leaving eBay anytime soon, because that reputation's just too valuable. It's producing a huge boost in revenue because of the trust it engenders with buyers on eBay. It probably results in you ranking better in search results for an eBay query. Because you cannot move those 10,000 feedbacks to an eBay competitor, you're not incentivized to go use an eBay competitor. This type of stickiness, this non-transferrable reputation, basically applies to all marketplaces and directories. Same thing on Yelp. You as a restaurant build your reputation on Yelp. The momentum keeps you stuck there. You want to keep getting reviews and hone your reviews.

**Julian Shapiro** (00:32:32):
Airbnb with your properties, Etsy, for you as a seller, Alibaba, all of this stuff are examples of companies that are kind of old now, cannot be top old or haven't been yet. People are like, why? Well, because of this exact reason. This is why those companies pester you so much to leave reviews and provide feedback all the time. They want you to play into this game of in market reputation building. The second state building technique that a startup could adopt, and again, this is all under the guise of how do we maximize retention and build somewhat of a moat, for example, the second way you can do this is you encourage your users to accrue a non-transferable audience.

**Julian Shapiro** (00:33:14):
If I'm a big YouTuber and I've acquired a million subs, those subs can't be transferred anywhere else. I can't bring them to Twitter. In fact, YouTube doesn't even tell me their email, so I can't even bring them to a newsletter if I wanted to. The more subs you acquire on YouTube, the easier it is for you to go viral on YouTube. This is what I mean earlier by the rich keep getting richer. It's this momentum trap. It's very, very hard to convince any YouTuber to get off YouTube. If anything, they'll dabble with another network in parallel at best.

**Julian Shapiro** (00:33:43):
Basically if you have a startup where you're creating a marketplace or an audience graph, you want to encourage users to build a follower graph within that product that they can take advantage of by pushing their product or their content or their insights too. This is why Twitter... By the way, a big shout out to Substack, which actually allows customers to export emails off of Substack. Substack is not playing that same game, which is better for users and a very nice thing for the ecosystem. But this is why Twitch and Instagram and Twitter are just irreplaceable. I mean, not necessarily. Everything dies over time like Facebook, but they're just so darn hard to topple.

**Julian Shapiro** (00:34:26):
Let's maybe touch one more. I don't want to ramble so much about this. Well, this one's kind of similar. Basically if you spent a lot of time building a social graph in a product, like if I spent the last 10 years trying to remember the names of all my high school friends and elementary school friends and add them one at a time over the years to Facebook, or I've added all my colleagues for the last 20 years onto LinkedIn and I've built a social graph on these products where I've curated and found people, that's really sticky. You're building state in the form of taking time to expand the graph. The graph is a representative of the state, the work you've put in.

**Julian Shapiro** (00:35:04):
You don't want to lose those connections with people. That makes that product extra sticky. This is why social networks in general can be sticky. It's not just the fact that you have your audience there, it's that you've invested time. If Facebook doesn't allow you to export your graph out, then that makes it extra sticky as well, because you don't know how else to talk to old Jimmy from elementary other than Facebook. Anyway, there's actually many more of these examples of building state. I'm going to just stop with that. But the basic concept is what can you encourage users to do within your product that makes them more deeper entrenched in the product, and most apps just completely lack this.

**Lenny** (00:35:39):
I like that. It's a little bit like the concept of having skin in the game and just building more skin in the game with the product that you're using. One quick question, is there a company that you've seen do this, like add it on, and succeed and increased retention that you've worked with or out there? Just like is there a good example that comes to mind that added this piece?

**Julian Shapiro** (00:35:58):
Again, none of this is really under the context of telling people to add it on after they've decided what they're building. This is all in the DNA of the product you're choosing to build. I'm not sure. I haven't thought of those examples. I'm thinking more so in whose DNA, which company's DNA are they doing this brilliantly? For example, one form of state is... One I did not cover is when you're embedded infrastructure. If you're Twilio, Striper, AWS, it's really hard to move off or segment because it's so much work to redo your code and introduce all this risk to screwing up your code base. People have built patterns around how they work with your API.

**Julian Shapiro** (00:36:36):
A lot of modern API startups automatically capture the stickiness by virtue of being so deeply embedded into a product. Generally speaking, none of this is in the context of like, hey, add it on post hoc, pretty much.

**Lenny** (00:36:46):
Got it. I like that lens actually through a lot of these things you're talking about is maybe it's less like change your product to make this happen, and it's more idea selection. I know you're also an investor, and so it's a really good lens on how many of these things does this company have that I'm investing in.

**Julian Shapiro** (00:37:01):
Earlier I was mentioning why do I write handbooks, I wrote the handbook that PLA and state building come from to cement my diligence criteria for companies I believe might grow super fast and retain customers. You're exactly right. My investor's perspective is if you have a zero cost of acquisition mechanism for customer acquisition, such as PLA, and you can retain them through something like state building, but there are other ways to retain customers, then I lean in harder because I think you'll be more defensible as a company. Actually interesting little side note is you'll often hear retention and stickiness refer to as a moat, right?

**Julian Shapiro** (00:37:41):
But I find this term actually very misleading because very few companies have actual moats. To have a real moat, you're basically exploiting kleptocratic, meaning you're friends with the government and they're creating a literal barrier to entry for your competitors, or you have a scientific moat where you have an actual scientific breakthrough in the fusion energy space, plus protected by patents. Those are real moats. But the way most people use the word moat is wrong. In practice, your "moat" is just your mechanism for retaining users a little bit more than the average company.

**Julian Shapiro** (00:38:21):
I believe state building is one of the best ways to do exactly that. Really it just comes down to what are you doing to help users build state and get more value over time out of the product, not the same level of value over any time period.

**Lenny** (00:38:35):
Awesome. Shifting a little bit away from growth and into writing, which I know you've spent a lot of time writing about, very meta, and sharing on Twitter and all the ways, you have a handbook where you go into this concept of novelty and a framework for how to be novel and why that's important in writing. I'd love for you to talk about why novelty is important in writing and ideally share your framework for creating something novel that keeps people engaged in reading.

**Julian Shapiro** (00:39:03):
Sure. This actually goes back to your question about Twitter. What can one do to build an audience on Twitter? It often comes down to writing things that are novel. Novel is what powers click bait in most cases. The other way is via curiosity gap, where you raise a question you don't answer, but the other half is novelty is what gets people to click into a thread and read it. Novelty, I define, as new idea, so something I haven't heard of before, that's also significant, so it's not some trivial fact about Kim Kardashian, and it's something that I wouldn't have easily intuited on my own.

**Julian Shapiro** (00:39:44):
When you have those ingredients, it's new, it's significant, and you wouldn't have easily thought of it on your own, that's when you trigger that dopamine hit reaction, I'm not being scientifically accurate here, but you're going to get that dopamine hit like, "Whoa! That's super cool." The more you have readers pausing going, "Whoa! That was interesting," the more novel your writing is. My whole approach to writing is write something out, and then point out all the points of novelty. I do that by actually having 20 friends read something I've written and highlight the sentences that made them go, "Whoa."

**Julian Shapiro** (00:40:17):
And then I have this visualized map in a given blog post, where are the areas that people go, "That's really interesting," and then I can see all the white space between the interesting parts. I go in and I condense that white space. I chop it down so that the frequency of novelties as high as possible. This is how you get a blog post that just has this phenomenal momentum that gets the read to completion rate to be very high. The question is, what exactly does novelty look like? I've identified about five different categories for it, and this is the backbone of how I write in many cases.

**Julian Shapiro** (00:40:51):
The first category of novelty is what I call counterintuitive information. You tell people something and they go, "Oh wow. I never realized that the world worked that way," or different categories and you tell people counter-narrative information. That's where people respond, "Wow. That's not how I was told the world worked." Whereas counterintuitive novelty is, "That's not how I would've thought the world worked," counter-narrative novelty is, "That's not what I've been told. I've been lied to. Now you're telling me the truth." That also triggers a dopamine hit. Third category of novelty is just pure shock and awe like, "That's crazy. I would've never believed that's true."

**Julian Shapiro** (00:41:30):
For example, there's a volcano that's going to erupt the next 15 years that's going to swallow this whole island. Wow, that's shocking. Holy moly. Next category is what a lot of popular Twitter users do is what I call elegant articulation, where you're taking an idea... Naval does this, Naval on Twitter, the founder of AngelList. He'll say something that's a complicated rich thought and boil it down into a very concise sentence. And then the reader goes, "Wow, that's beautiful. I couldn't have said that any better myself."

**Julian Shapiro** (00:42:02):
That also triggers that dopamine reaction. There's a few more, but the point I want to get at here is all of these are formats for identifying the types of things you could say to get people to go, "Whoa." That's what I think of as novelty.

**Lenny** (00:42:17):
Something I've found to kind of identify something that I've written is going to be interesting is I just read it myself and I feel what I feel when I'm reading it the first time. Often I find that if I'm like, "Oh wow, this is really good and really exciting," I've learned to trust that feeling wherever that comes from. That's just like another way of knowing if your thing is interesting is like, are you excited about it? Are you interested in it as you're reading it? And that fades after you read it like 10 times and kind of edit and edit, but that's just a small tip I've learned, just kind of trust your own gut feeling when you're excited about something that you're writing about.

**Julian Shapiro** (00:42:53):
I agree. And that's why I tell people when you first encounter something that to you is novel, write down with a score, like let's say out a five, zero to five, how novel that thing was to you when you first heard it. You want to remember and capture the degree of novelty, because to your point, Lenny, it's going to become less novel over time. And then if you pull that out of your idea bank for a blog post in two years, it'll like, oh yeah, that will blow people's minds, even it doesn't blow my mind today.

**Lenny** (00:43:16):
Good tip.

**Julian Shapiro** (00:43:17):
To your point, the way you basically get novel ideas is you go live your life and write down every time you come across something that interests or surprises you, or any time you come across something that makes you think, "Well, that's obviously not true," meaning you found something that people say that you know the lie and you're about to tell people the way the world really works. Some examples of novelty... I'm scrolling through Twitter up here. This is a tweet I wrote where I wrote, "Reading many books is the most socially accepted vanity metric for adults." I give zero kudos for reading a hundred books a year, but I give you massive kudos for learning efficiently and making interesting things.

**Julian Shapiro** (00:43:59):
This tweet is an example of me using novelty. As we read the key novel part, it's where I say, "Reading many books is the most socially accepted vanity metric for adults." That is counter-narrative novelty, because the prevailing narrative is all the smart people I've ever met, they read a ton of books. They always have a book in their hand. They're reading five books a month, blah blah, blah, blah, blah. I'm saying no, that's a vanity metric how many books you read. That's counter-narrative. That gives people a dopamine hit. They lean in. They want to see what my punchline is and that tweet got a lot of engagement.

**Julian Shapiro** (00:44:33):
One more example. See if you can catch the novelty here. New tweet, "The world is not run by exceptional people. This is the hidden reason for imposter syndrome. We mistakenly think imposter syndrome is due to low confidence or low anxiety. No. It's caused by not accepting that your new world-class peers aren't that special. It's just discipline." The key statement there that has the novelty is the world is not run by exceptional people, and the type of novelty being used there is counterintuitive. Your intuition is the world's run by the best of the best or many of these experts are there for a reason.

**Julian Shapiro** (00:45:15):
I'm saying not in most cases. Anyway, those are some examples of novelty. Of course, these tweets took off largely due to that reason. People love having their eyes opened. They'll reflexively retweet you to agree with your worldview if they feel like you're finally speaking truth, the power, in some sense, if that makes sense.

**Lenny** (00:45:34):
We'll link to those in the show notes. By the way, I love your reading your own tweets voice that you have.

**Julian Shapiro** (00:45:40):
I'm adopting my... Who's the guy from Star Trek who's amazing, who reads the kids?

**Lenny** (00:45:45):
Oh yeah, LeVar Burton. Reading Rainbow.

**Julian Shapiro** (00:45:49):
There you go. That's my voice.

**Lenny** (00:45:50):
Julian Shapiro, the new LeVar Burton. I know you have to run in not too long from now. We have two more topics. How about I set up both topics and then you kind of talk through as much as you want with each? That sound good?

**Julian Shapiro** (00:46:01):
Sure.

**Lenny** (00:46:01):
Cool. The fourth topic we want to talk about is topic selection, how meta, essentially picking what to write about, and you have a bunch of great advice on what's worth writing about and the framework around that. And then the fifth idea is something you called it the Creativity Faucet, which is essentially how to get more creative. I will turn it over to you to share your thoughts on these topics.

**Julian Shapiro** (00:46:22):
Sure, sure. My pleasure. The way I think about topic selection, meaning what is it you should write about for your blog posts, for your newsletter, Twitter, company blog, whatever, books, is you choose topics based on two factors, what would you actually be able to complete so you're not going to give a pathway through and what will actually be high quality. I have a framework for helping you figure out what that is. Basically I believe that your likelihood to follow through on something you start writing is a function of the objective you have with writing that piece and how strong your motivation is for seeing that objective to fruition.

**Julian Shapiro** (00:47:00):
Here's what that looks like more specifically. Anytime that I write something, I'm first trying to identify what is my objective. Here's a few examples of objectives that I'll use before sitting down to write. Number one, I want to open people's eyes to prove the status quo wrong, or two, I want to articulate something that everyone's thinking about, but no one is saying. I want to cut through the noise. Another objective might be, I want to contribute original insights to my own research and experimentation. Hence, some of my handbooks. Another objective is just telling a suspenseful and emotional story that maybe imparts a lesson.

**Julian Shapiro** (00:47:34):
These are all clear cut objectives that give me a guidepost. I know that I'm done writing a piece if I can read the piece and say, "I've accomplished that particular objective," because people don't know when they're done writing, "Oh, I petered out here and this seems like a good place for an outro." With an objective, you know whether you should actually stop. But then the question is, how do you sustain the motivation to see through an objective? Again, an objective might be something like open people's eyes by proving the status quo wrong. To do all the work necessary to accomplish that, you need a motivation in my opinion.

**Julian Shapiro** (00:48:08):
I'll pair one of those objectives that I've selected with a motivation. Some example motivations are, does writing this piece get something off my chest that I really badly need to get off? Or does it help me solve a nagging unsolved problem that I've been dealing with and this piece is way for me to explore and find the solution? Or is it like me obsessing over a topic that I want others to also geek out about? These are all powerful motivations that I pair with an objective to guarantee my follow through to get done writing the piece.

**Julian Shapiro** (00:48:41):
By the way, everything I've mentioned in this entire chat with you, the novelty stuff, the topic selection, PLA, state building, everything we've covered, I have tons of examples on Julian.com. That's why I'm not trying to go through every single one.

**Lenny** (00:48:55):
Yeah, and we'll link to all that.

**Julian Shapiro** (00:48:57):
Absolutely.

**Lenny** (00:48:57):
Awesome.

**Julian Shapiro** (00:48:58):
The flip side I'll point out is that I think writing quality overall is... Again, these are all me being hand wavy and these are not rules. There's no right way to write, just like there's no right way to paint. These are just frameworks I've developed, that when I use them, I'm more frequently arriving at success as far as I define it. The thing I want to point out though is that very closely tied to everything I'm talking about is my framework or my equation for determining how good any piece of writing is, is novelty times resonance. Writing quality equals novelty times resonance.

**Julian Shapiro** (00:49:36):
Novelty is like we discussed, here are all these things that are giving you dopamine hits where I'm opening your eyes about how the world really works and shocking you and elegantly synthesizing things, times resonance and resonance means I can tell you the most novel thing on the planet. But if I don't wrap it in a way that resonates and really lifts off the page and into your mind and is something you remember, then it's fairly ineffective novelty. It's more like just trivia. It's bland, dry trivia. When you add resonance to the novelty, now it becomes a beautifully written piece. Resonance is a matter of including examples, analogies, metaphors, stories.

**Julian Shapiro** (00:50:14):
Really writing quality is novelty times the storytelling power you have to make the novelty resonate in the back of people's minds. The way that I structure my writing process is draft one, I'm just focused on finding my novelty, just the backbone of what makes anything interesting. And then draft two, I come back and try to increase the resonance by embedding story and analogy and examples. That's basically my process there.

**Lenny** (00:50:41):
I like that a lot. Just to add real quick, something I've learned is that if your stuff is really useful, it doesn't have to be written beautifully. A lot of people I think are afraid of writing because they think they have to write really well, like be real good writers. What I've learned is it's okay if you're not like. You just be good enough and you'll get better the more you do it. The most important thing is the content is valuable and interesting, which I think you're describing as novelty. I just want to make sure people don't get scared away and be like, "Oh my god, I need stories and metaphors and all these beautiful writing." Initially you don't is my experience, but it helps in a big way.

**Julian Shapiro** (00:51:17):
I agree. In fact, the biggest criticism of my writing is that it is too dry, it's too novelty focused, and there's a lack of the resonance, but I do that purposely because oftentimes people can over-indulge in resonance and then it really bloats the piece. As a reader myself, I like reading super concise pieces, like reference manuals almost. I'm looking for the length from personal anecdotes, personal stories of people's lives or life lessons they've learned that they want to share with me, or actual fiction. To each their own. You're spot on. Do what you would want to read to me is the golden rule.

**Lenny** (00:51:52):
Awesome, and also don't be afraid. Don't feel like the bar's that high if you want to get started.

**Julian Shapiro** (00:51:58):
What have been your frameworks for sitting down and knowing that one of your newsletter editions is where you want it to be? And what do you think is the framework justifying that a piece is or explaining why a piece is good?

**Lenny** (00:52:10):
The thing that I always strive for is this needs to be actionable and useful. It's something someone could take and do something with that day versus just a bunch of theory and pontification and philosophy. It's like, oh, here's a thing you can go do today.

**Julian Shapiro** (00:52:25):
That's kind of my bar is make it very actionable, which I think is specific to the type of newsletter I have, not necessarily broad writing the way you're describing, but that's what I try.

**Lenny** (00:52:35):
I love that. I agree with you, my rules of thumb are like it has to be actionable, concise, and novel. I'm not sure if you've seen this as well, but to make something truly actionable, I have to leave them with a cheat sheet. Because if I have all these actionable steps, but they're spread throughout a monster newsletter edition, it's too much mental work to go and make my own cheat sheet out of and have a quick to follow series of steps. I feel like compression is a key part of making something actionable as well.

**Julian Shapiro** (00:53:06):
There's a book called On Writing Well that taught me a lot about cutting two-thirds of what you've written to get to the core of it. I'm curious, what else are you doing to try to harden each newsletter edition to make sure it's good? Is it just like, hey, this is actionable and we were pretty comprehensive and I checked it past experts? Is that the extent of it, or what are you trying to do to feel like it's fantastic? What's your review process when you pass it by others as well?

**Lenny** (00:53:30):
I'm happy to answer that, but I also know you got to run soon. I guess we could touch on... We could just save the fifth topic maybe for a follow up episode is one idea, or we could touch on it.

**Julian Shapiro** (00:53:40):
Sure. Up to you. Anything you want, my friend. If you want me to cover the next topic, super happy to. Up to you. Everyone listening right now is like, "Man, Julian's just been fucking rambling for an hour." I realized we were not having a conversation. Now I feel bad because I was so in my momentum of sharing some concepts that I didn't really have a conversation with.

**Lenny** (00:53:59):
This is very normal for this podcast, so do not stress.

**Julian Shapiro** (00:54:04):
All right. Good. Actually, you should leave this all in here so they know I feel bad. I'm not cutting anything. What was the last topic again? Remind me.

**Lenny** (00:54:12):
I was just saying, I think one of the things people really like about this podcast from what I hear often is they like that I'm not talking a lot. They kind of like that I'm letting the guests speak mostly, because a lot of podcast, the guest thinks they know at all, or sorry, the host and they just talk, talk, talk.

**Julian Shapiro** (00:54:27):
Oh, got you. The thing is you are brilliant. You're an actual host who is a useful, amazing human being and we want to hear your thoughts.

**Lenny** (00:54:35):
What was the last topic again?

**Julian Shapiro** (00:54:36):
The last topic was the Creativity Faucet. We can save that for another talk, or if you want to touch on it, we can do that too.

**Lenny** (00:54:43):
Sure. Yeah, let's do it.

**Julian Shapiro** (00:54:45):
The quick version here is that this is an idea that I saw recur across three of the most prolific creators in the world, John Mayer, Ed Sheeran, Neil Gaiman. Ed Sheeran might work with other producers and so on, but the basic thing between the three is they're very independent creators who are constantly making blockbusters in large part on their own. I was curious, what on earth are those three doing that very few other people are doing? Taylor Swift also. One day I actually found the answer, what is their approach to consistently making phenomenal content? The way I found it was interesting.

**Julian Shapiro** (00:55:23):
I was watching a masterclass, like Masterclass.com, with Neil Gaman and he explained his process for writing fiction novels. And then in the same year, I watched the documentary of Ed Sheeran explaining his process for writing songs and they were identical. And then a year later, I came across a YouTube video that I posted on Twitter with John Mayer spinning his process, also identical. I'm like, fuck, there's the answer. They don't have a name for their process, so I just call it the Creativity Faucet. Very quickly, what they do is they visualize their creativity as a backed up pipe of water. The first mile is packed with wastewater, and this wastewater has to be emptied before the clear water behind it can arrive.

**Julian Shapiro** (00:56:10):
Because your creativity pipe or Creativity Faucet only has one faucet, there's no shortcut to achieving the clarity, the clear water of good ideas, until you first empty the wastewater out. If we apply that to creativity at the beginning of every writing session, write out every bad idea that comes to mind. Instead of being self-critical and resisting these bad ideas, you have to recognize bad ideas is progress. Because once they are emptied out of you, the better ideas begin to arrive. Here's the key part, why do good ideas arrive after the bad ideas are empty? It's because when you've gone through a bunch of bad ideas, your brain, your mind starts reflexively identifying what elements are causing the badness.

**Julian Shapiro** (00:56:53):
Then it becomes way better at avoiding those bad elements and you become way better at pattern matching the novel ideas with way greater intuition. Most creators are resisting their bad ideas. If you sat down, scribbled a few thoughts in a blank document, and just walked away because you weren't struck with gold, then you never actually finished the creative process. There's no way you would've come up with gold. Like Neil and Ed, for example, they know they're not superhuman. What they're doing is in every creative session, they simply have the discipline to allot time no matter how long it takes, it could be an hour, to empty all of the bad ideas.

**Julian Shapiro** (00:57:28):
And then they're not worried about whether good ideas will come after the bad ones because they know the following process. You start with a weak imitation. You identify what makes your invitation weak, and then you iterate the imitation until it's finally original. And that is the process you have to just throw yourself into.

**Lenny** (00:57:46):
I love that. I feel like I don't do that enough. I feel like when I get to writing, I'm just like, "Okay, let's make this awesome." This is a really good reminder just to get stuff out. It connects to the concept of the shitty first draft. Just write. It'll be bad. And then you edit. You asked me this question, what my process is for writing, and most of it is just refining like a thousand times. I just kind of take a first pass and then I look at it, make it better, look at it, make it better, and just kind of keep editing for days and days and days until it's not bad.

**Julian Shapiro** (00:58:15):
I love that. That's what I've always done, until one day I was like, "I need a process here." Anyway dude, pleasure chatting. You're a gent. Sorry to all the listeners for rambling so much at a high pace. Cut anything you want. You can cut all of that. I don't care. Whatever you find interesting, go with. We're just going to have this final goodbye and that's it.

**Lenny** (00:58:36):
That was very anti-climactic. Cool, man. Where can folks find you online and how can listeners be useful to you?

**Julian Shapiro** (00:58:41):
Sure. You can go to Julian.com. It has everything, Twitter, handbooks, all that good stuff. And that's it. I hope you guys find the handbooks useful.

**Lenny** (00:58:50):
Amazing, Julian. I know you don't do a lot of podcasts. I really appreciate you being here. This was awesome. I'm excited to get this out.

**Julian Shapiro** (00:58:56):
Dude, truly my pleasure. I think you're awesome and you're why I'm doing the podcast. Really my pleasure, man. Have a great day.

**Lenny** (00:59:02):
Thanks, man. 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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## [20/20] Customer-led growth | Georgiana Laudi (Forget The Funnel)

**Georgiana Laudi** (00:00:00):
The problem with funnels and pirate metrics and the favorites that I love to pick on are MQLs and SQLs is that nobody knows what those mean. It puts every customer in the same sort of buckets. It assumes that all customers and all products are the same. It puts businesses, or they, I should say, puts businesses at the center of the business versus putting customers at the center. Right? It's about the values of the business, not the value to the customer that's being measured. Also, it just kind of feels gross for people, this idea of pushing people through a funnel. And then probably a particularly relevant for SaaS companies is that recurring revenue businesses, you cannot think about marketing and growth and the business overall as ending an acquisition, otherwise you're not in business anymore. And the vast, vast majority of these models don't take post-acquisition, retention, expansion, all of that into account. So yeah, in a nutshell, funnels are bad.

**Lenny** (00:01:04):
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 Georgiana Laudi. Georgiana, aka Gia, runs a consultancy called Forget The Funnel, where she works hands on with SaaS companies to help them unlock and accelerate growth.

**Lenny** (00:01:30):
**John Cutler** (00:02:10):
Hey, Lenny. Excited to be here.

**Lenny** (00:02:11):
John, give us a behind the scenes at Amplitude. When most people think of Amplitude, they think of product analytics, but now you're getting into experimentation and even just launch a CDP. What's the thought process there?

**John Cutler** (00:02:23):
What we've always thought of Amplitude is being about supporting the full product loop, think collect data, inform bets, ship experiments, and learn. That's the heart of growth to us. So the big aha was seen how many customers were using Amplitude to analyze experiments, use segments for outreach, and send data to other destinations. Experimenting CDP came out of listening to and observing our customers.

**Lenny** (00:02:44):
Supporting growth and learning has always been Amplitude's core focus, right?

**John Cutler** (00:02:48):
Yeah. So Amplitude tries to meet customers where they are. We just launched Starter Templates and have a great scholarship program for startups. There's never been a more important time for growth.

**Lenny** (00:02:57):
Absolutely agree. Thanks for joining us, John. Head to amplitude.com to get started.

**Lenny** (00:03:03):
**Georgiana Laudi** (00:04:36):
Thanks so much for having me, Lenny.

**Lenny** (00:04:38):
It's my pleasure. So we actually met over a decade ago, I think, maybe just around a decade in Montreal. I was working on my startup. You were helping companies with their websites, optimize their websites. Then you went on to lead marketing at Unbounce and a bunch of other great stuff. So just to set a little bit of foundation for listeners, can you talk about what you've done in your career in 55 seconds? That's your time box.

**Georgiana Laudi** (00:05:03):
55 seconds. Okay. So marketing for probably about 20 or so years, which sounds completely ridiculous when I say it, but I started working for my father's retail business in the early 2000s, probably 2000 actually. Worked there for a number of years, and then eventually left and started freelancing, worked at an agency. Terrible. And then actually probably around the time I met you, I had this little catalyst moment where I joined Twitter in late 2008, and I discovered the tech scene and startups. And that was, again, probably around the time that you and I met, maybe 2010 ish. And that was-

**Lenny** (00:05:43):
2011.

**Georgiana Laudi** (00:05:43):
And then I... What's that?

**Lenny** (00:05:45):
2011.

**Georgiana Laudi** (00:05:46):
2011. See, there you go.

**Lenny** (00:05:47):
Mm-hmm.

**Georgiana Laudi** (00:05:48):
So it was right around that time, and then late 2011, I decided supporting five, six companies at a time in their marketing and stuff like that. I was starting to get burnout, I was doing a lot, and I was like, "What would it feel like to sink my teeth into one brand?" So I decided to go in-house and I moved out west, and joined the team at Unbounce. I was there for five years. And then in late 2016, early 2017, I decided it was time to move on, and so I decided to go back independent and just started working with companies and supporting them through marketing and growth and product marketing. And that's what I've been doing ever since.

**Georgiana Laudi** (00:06:27):
But in mid 2017, I actually paired up with Claire Suellentrop who led marketing at Calendly, and her and I have been working together since about mid 2017. That's when we launched Forget The Funnel, and we started pairing up on working with companies and sort of married her customer research background in my strategy, marketing background. And we developed this framework that we now use when we work with predominantly B2B SaaS companies, is who we work with right now.

**Lenny** (00:06:57):
Awesome. So we're going to spend a lot of time on what you've learned working with companies through Forget The Funnel. Why did you call it Forget The funnel?

**Georgiana Laudi** (00:07:04):
Because funnels are gross. I mean, it's a really antiquated idea. It's not just funnels that we sort of take issue with, it's buyers' journeys or even... I remember actually at Startup Fest 2012, I want to say, Dave McClure was talking about pirate metrics and I was like, "Huzzah, marketing has a role post acquisition. Everybody understands now." It was a real moment for me. But the problem with funnels and pirate metrics and the favorites that I love to pick on are MQLs and SQLs is that nobody knows what those mean. It puts every customer in the same sort of buckets. It assumes that all customers and all products are the same. It puts businesses, or they, I should say, puts businesses at the center of the business versus putting customers at the center. It's about the values of the business, not the value to the customer that's being measured.

**Georgiana Laudi** (00:08:01):
Also, it just kind of feels gross for people, this idea of pushing people through a funnel. And then probably a particularly relevant for SaaS companies is that recurring revenue businesses, you cannot think about marketing and growth and the business overall as ending at acquisition. Otherwise, you're not in business anymore. The vast, vast majority of these models don't take post-acquisition retention, expansion, all of that into account. They also leave the problem stage out. So the world that customers are living in prior to discovering you, which is a really critical, that context is unbelievably valuable, especially for marketing. So to delete that out of the equation is a big problem. So yeah, in a nutshell, funnels are bad.

**Lenny** (00:08:52):
Okay. So I'm excited to dig into a lot of stuff you've learned, but I have a couple other things I just wanted to talk about to set the foundation.

**Georgiana Laudi** (00:08:58):
Mm-hmm.

**Lenny** (00:08:58):
One is, can you talk about some of the impact that you've seen working with companies through the process that you've come up with? What kind of impact have you seen? What kind of numbers have you seen?

**Georgiana Laudi** (00:09:07):
I would say, far in a way the biggest, most immediate impact of the type of work that we do is realigning with that ideal customer. Generally, the lowest hanging fruit outcome is realigning around better positioning and messaging. And identifying more resonant positioning and messaging that speaks to that context that I was talking about before, before people discover that you even exist, have that moment where they're like, "Oh my god, this has to change. This sucks," ties that in, ties in what they care about and what is valuable about your product and then also that desired outcome. I mean, for those in the know, jobs to be done is a big sort of influence here, but if you can identify that type of information about your customers and get to know them at that level, then you are in a way better position to be able to not only position your product but also use much more powerful messaging.

**Georgiana Laudi** (00:10:06):
So typically, what we do is, we'll identify those gaps of almost, I mean I shouldn't even say nine times out of 10, 99 times out of a hundred, a company's website is not doing as much as it could do. It's not being as effective from a messaging and positioning standpoint as it could. So websites tend to get update. We will do a lot of overhauls on messaging on a website and improve performance there. One of my favorite examples of that is a social media tool that we worked with where we did really very simple research for them, honestly, identified two different jobs to be done, zeroed in on one of them, and then updated the messaging on the website.

**Georgiana Laudi** (00:10:46):
We shortened the trial from 30 days to seven. The conversion on the website went up with this new messaging by 89%. But the thing that I love the most about that particular story is that we didn't even touch anything after the signup experience. We hadn't even gotten there and the trial-to-paid conversion rate increased 40%, and we didn't touch it. It was just because a more qualified, better fit customer was coming through the door. So there was more of them and there were better qualified. So that's a really specific example that is very typical of this type of work.

**Georgiana Laudi** (00:11:19):
There's other examples, though, of product adoption and using that messaging and positioning past the website, even in the product onboarding itself, email and app, whatever, and just making sure that they're getting to and have the calms to get to the parts of the product that they care about the most, which can increase trial-to-paid or product activation. With Autobooks, the product usage of the North Star product usage jumped by 300% or something within quite a short period of time after rolling out email onboarding to support that product experience. I know SparkToro as well, which I think we might end up talking about again when we talk about the process, they doubled their trial-to-paid conversion rate when we worked with them because of post acquisition optimization to their messaging.

**Lenny** (00:12:01):
I imagine people are listening to this and they're like, "This is what I'm waiting for, some kind of huge win, some huge conversion, a success." I'm curious, how often do you find companies have something like this, like a latent opportunity to double, triple conversion? Everyone's hoping a conversion like this.

**Georgiana Laudi** (00:12:18):
Oh, boy.

**Lenny** (00:12:19):
Yeah. What's the general hit rate?

**Georgiana Laudi** (00:12:22):
So many. I mean I would say, pretty well every company we've ever worked with has... Not pretty well. Every company we've ever worked with has learned something new about their customers that they can apply at some juncture of their customer's experience, whether or not it is in campaigns to reach the right people out in the world, whether or not it's doing a better job with their messaging and positioning on their website, or their go-to market or acquisition strategy on their website using a sandbox account or getting a faux freemium account to let people kick the tires of their product prior to getting on a sales call. That's something that could potentially happen.

**Georgiana Laudi** (00:13:06):
The post-acquisition experience I'm talking about, it is so often an afterthought somehow where that additional of layer... I think part of the reason why it's an afterthought is because product onboarding in particular, and you've probably heard this too, it tends to be kind of like no man's land. Who owns that? Is it marketing? If it's freemium, in my opinion it should be marketing because freemium is a marketing tool, but not everybody subscribes to that. Not every company would necessarily agree that that's the case. A lot of companies might say, "No, it's product." So we end up seeing a messy middle there because there's no natural handoff. So pretty well, every company that we've worked with has had an opportunity to improve, especially product onboarding and product activation.

**Lenny** (00:13:53):
Awesome. So basically everybody will benefit from what we're about to talk about.

**Georgiana Laudi** (00:13:56):
A hundred percent.

**Lenny** (00:13:56):
Amazing. Great.

**Georgiana Laudi** (00:13:56):
Yes.

**Lenny** (00:14:00):
All right. We've got wrap detention as a way to maybe transition into your process. So you're visiting a site once, and I invited you to the Airbnb office we were having a happy hour, and I gave you a tour. You told me later that something you saw while you're walking around the office transformed the way you think about growth and inform the way you think about approaching this problem. Can you talk about that?

**Georgiana Laudi** (00:14:24):
Yes. This is one of my favorite... It was 2013, so you and I might have met in 2011, and then a couple years later I was in town for a conference and we toured the office, HQ and everything. Of course, it was all stars in my eyes because what a beautiful office too. So it was quite like, I would've remembered it regardless. But we went downstairs, very different from the very polished upstairs. We went downstairs to where your working area was, where the product team was, and there were sheets of paper taped to the wall, a bunch in a row. And it would've been easy to miss because it's kind of chaotic down there, but it was the customer journey of an Airbnb customer through two posts.

**Georgiana Laudi** (00:15:12):
What struck me, I was like, "Oh that's interesting. I'm in the middle of building one out for us." Leading marketing at Unbounce at the time. And I was interestingly with the customer success, he was also with me. So Ryan Engley was there with me, and it was the perfect sort of that him and I saw it together. It was a customer journey that was focused on the customer. So versus that pirate metrics problem or that the typical buyer's journey problem that I was talking about earlier, it was the complete reverse of that. It was illustrated. The emotional journey was part of it. The role that Airbnb played as a direct touchpoint and also indirect, what was going on in the person's life that had nothing to do outside of Airbnb, which I thought was really interesting.

**Georgiana Laudi** (00:16:01):
It was like, the beautiful little milestones really encapsulated in a sort of snapshot way, such that anybody walking by it or anybody being reminded that it existed could understand in a glance what the goal was at each of those milestones. I was like, "Well, shit, this is completely through the lens of the customer versus the business and the grossness of the funnel." It's just so far removed from that experience that I was like, "Ryan, look at this. We need this." He was like, "Oh yeah, this is good." I took a picture. Can't find it for the life of me.

**Georgiana Laudi** (00:16:39):
But we returned back to the office the following week, and co-founder and head of product, head of CS, so Ryan, Carter Gilchrist, who's head of product and co-founder, Ryan, and I, head of marketing, the three of us locked ourselves in the room for two days and made our own. It was a circle. I mean looking back, it's hysterical, but it was sort of democratized to the rest of the team in a way because it had that buy-in. Everybody was like, "Oh yeah. Okay, this makes sense and I understand." It made everybody feel a lot better about what they were doing because it was about value, delivering value at each of the points.

**Georgiana Laudi** (00:17:13):
So that grossness sort of goes away and we're like, "Oh cool." I don't want to be too kumbaya about it, but it was a bit of a moment. And also, it made communicating with especially the product team and the engineering team a lot easier for me. So we were using a shared language. The rest of the company who aren't necessarily customer facing really understood, I think, at a different level what we were all doing together in KPIs, yada yada yada. So it was amazing. Honestly, I mean I can't credit only that obviously to our growth, but it was a pretty impressive couple years that followed that. I think the alignment that that brought us was huge. Yeah. Anyway, that's the story. Sorry, that wasn't super short, but it was big.

**Lenny** (00:18:02):
That's great.

**Georgiana Laudi** (00:18:03):
It was a big thing. Yeah.

**Lenny** (00:18:05):
We're going to link pictures of this on the show notes. Internally, it was called Project Snow White because it was inspired by-

**Georgiana Laudi** (00:18:13):
Oh yeah, that's right.

**Lenny** (00:18:13):
Yeah. It was inspired by Brian reading the biography of Walt Disney, and they needed to create the storyboard basically to create Snow White because it was so complicated to make that movie. It might have been the first animated film with storyboards.

**Georgiana Laudi** (00:18:24):
Okay.

**Lenny** (00:18:25):
So it was basically a storyboard of a trip on Airbnb of a host and a guest.

**Georgiana Laudi** (00:18:30):
That's right.

**Lenny** (00:18:30):
And in detail, I forget if I told you this, but Airbnb hired a full-time storyboard artist from Pixar to draw these key frames.

**Georgiana Laudi** (00:18:38):
I think I did know that. I was very grateful to have seen it. I didn't realize at the time, but it changed the way, like you said at the beginning, it changed the way that I thought about marketing because it really made it obvious to not only me, of course, and to everybody, that customer experience layer, that marketers are so good at, has such an incredibly important role in driving revenue. Not just in building awareness, but in playing a major role in helping customers get value and catching them when they fall off and all that kind of stuff. So it changed a lot for us.

**Lenny** (00:19:19):
And it informed the way that you approach your consultancy with Forget The funnel. So as a transition to talk about that, the way I'm thinking we approach this is, imagine a customer, what is the process you go through? What are the steps? How do you go about helping a company figure out where they should invest, what they're doing right and wrong? I should also mention you're writing a book about this that's going to explain this whole process, that's coming out later in the year.

**Georgiana Laudi** (00:19:40):
Right. Yeah.

**Lenny** (00:19:41):
So we'll talk about that at the end as well. I'll turn over to you.

**Georgiana Laudi** (00:19:46):
Cool. I mean if I go down a rabbit hole and you want to pull me out and have me unpack something, let me know. Well, the process is pretty straightforward. At the highest level, the idea is, understand your best customers, map their experience, like we were just talking about, map their experience through the lens of delivering value to them, make it measurable, and then evaluate what you're doing today that is out of alignment with that. Pretty straightforward. I mean that doesn't sound too hard of a job, of course. But research is an really important part of that. So the story that I was going to use to illustrate this is, there's a company that we work with from time to time. We worked with them at least twice, arguably three times.

**Georgiana Laudi** (00:20:34):
So Rand Fishkin who was the founder of Moz, he's got a new product. It's an audience research tool called SparkToro. And when they first launched, actually even pre-launched, Rand and Casey came to Claire and I to help with their positioning and messaging as they were going forward to launch. I mean Rand and Casey, they're both very, very thoughtful and they take their time with stuff. So they were just looking for that extra layer of like, "Is this good enough to launch kind of thing?" So we help them with their positioning and messaging. And off they went.

**Georgiana Laudi** (00:21:08):
About a year later, they came back because though they were doing a decent job generating traffic and interest in SparkToro, I mean Rand is no small fish so he's got a good audience built in, which is fantastic, but those that were getting to the website... Those that were signing up for the product, those weren't issues. But the people that were signing up for their free product weren't converting to paid in the way that they believed they could. So we decided to work with them and basically go to the source and find out, from SparkToro's best customers, what can we learn from them that we can then reflect back in the product experience and the customer experience for them?

**Georgiana Laudi** (00:21:54):
So I mentioned it before, but we are heavy believers in the jobs-to-be-done theory, which is basically this idea that people don't buy your product, they buy the better version of themselves, yada yada. I don't need to explain any of that. But we use that to guide our research. And with SparkToro, we were in a position, and the purists will hate me saying this, but we were in a position to be able to run surveys. So yes, interviews are ideal always, but we did think that we could learn a ton from surveys to then, if needed, double down with interviews. We didn't end up actually needing to run the interviews because the surface that we ran were pretty decisive and clear in terms of what we learned. So what we did was, we identified SparkToro's best customers. Now, what I mean by best customers is those that get a ton of value from your product as of exist today, pay obviously. They're happy. They're low maintenance. And very importantly, they signed up for your product recently enough that they remember what life was like before.

**Georgiana Laudi** (00:22:57):
So generally, we say that's in the three to six-month range. Because if you go to somebody that's been your customer for two years, they're just going to fill answers with what they think might have been going on in their life. But if you ask customers who remember what life was like before, you're going to get a lot more interesting responses, a lot more accurate depiction of what was going on. So that's the criteria we went forward. Surveyed their customers. We're trying to uncover from them what was going on in their life when they were seeking out a solution, what happened, what was that trigger moment when they did start seeking a solution, what did they go to, who did they talk with, what were their influences? Which PS, that's what SparkToro does, it helps you identify those.

**Georgiana Laudi** (00:23:42):
But also, what were they looking for in a solution? What were the must-haves for them versus what were some of the anxieties that they had, some deal breakers, things like that? So basically unpacking what is it that was critical for them in their solution. And then of course, what is it they're able to do now that they weren't able to do before. So that desired outcome. So out of that, we identified a couple of different options, a couple of different jobs, customer jobs, and we have to prioritize one, of course, because if you start right off the bat with like, "Okay, we're going to solve for all of these different customers jobs," then you end up not being as resonant. You can't be as effective. So we focused in on one.

**Georgiana Laudi** (00:24:23):
And the way that you make a decision on which one you focus on is similar to best customers. So high willingness to pay. There's no question whether or not they would pay for a product like yours. The handholding that they would need would be minor or less so. And I say that understanding full well the difference between product-led and sales-led. I'm not saying that sales-led is not good, but sometimes there's a decision to be made. If you're not set up today to support a sales-led or high touch, then you may want to opt for the more product-led approach. And the reverse is also true if you've got a robust sales team, well then, you might actually be better off leveraging sales more in that scenario and might want to attend towards that. But there's that criteria that you would think through.

**Georgiana Laudi** (00:25:10):
So willingness to pay, it's really obvious. Maybe the most important one is that they have an urgent problem. So the whole pain killer versus vitamin thing, you always want to be selling a pain killer. So who has an urgent problem that needs solving, not something that they might have a problem with six months down the line? Who has a high retention or even expansion potential is also really advantageous for very obvious reasons. So customers who would have a long-term need for this type of product and even potentially have that need expand or change over time and evolve in ways that you envision the product can help them.

**Georgiana Laudi** (00:25:47):
And then there's other criteria too. So sometimes you might want to prioritize one customer job over another, if those customers congregate in a way that make them really easy to market to. That's an advantage. Or another advantage, and this was the case for SparkToro, is you have an unfair advantage with this market in some way. So there were two different customer jobs that were coming out of SparkToro. One was more focused on service providers and marketing and the other one was more focused on data. And those data purists and those that really wanted verifiable data, well, SparkToro has an advantage on the marketer side more so than on the data analyst side. So that was another thing too. So with that, we made the call to focus on one of those customer jobs.

**Lenny** (00:26:35):
Can I ask a question here?

**Georgiana Laudi** (00:26:37):
Yeah, go.

**Lenny** (00:26:37):
So there's two parts of this. There's figuring out who you're going to go after and then what problem you're solving for them. Which do you think is more important at this point? Because step one in this process, just to zoom out a little bit, is figure out your customer and what their problems are so that you can actually solve them well. Do you start with here's who we're going to go after and then here's the biggest problem? How do you think about that?

**Georgiana Laudi** (00:27:01):
They're sort of one in the same. So because we learned from SparkToro's ideal customers, we already know that they're a fit for the product. They're happy, happily paying, prime them out of their golden hands customers. They're the customers that we want more of. So we've already validated that there's a demand from that customer base. Now, what I'm describing about choosing between two different customer jobs is really just, of those ideal customers, which customer job do you want to lean into? It's not that you wouldn't necessarily still be able to solve for that other customer job, it's just not the one that you would lead with. And I always cautious around this too because sometimes with founders, what'll happen is, there's a level set that just because we were prioritizing one customer job in the short term, doesn't mean you can't serve that other customer job down the line.

**Georgiana Laudi** (00:27:57):
A classic example of that is products that serve both brands and agencies for example. So the customer job for brands will be slightly different than agencies. And if you've got an advantage with one, you would just start with one and then you would go back after it. That's a bit of a level up after the fact. It's not part of the core processes, it's what you would do after. But it doesn't mean you can't solve for the other customer jobs, it just means put one foot in front of the other, do a really good job of one thing first, and then we'll add that on later. I don't know if that a hundred percent answered your question though.

**Lenny** (00:28:32):
Yeah. Yeah.

**Georgiana Laudi** (00:28:33):
Okay.

**Lenny** (00:28:34):
The reason that you start here is... Basically what you're trying to do is help SparkToro, in this example, grow faster.

**Georgiana Laudi** (00:28:40):
I mean we're trying to help them figure out why they're free-to-paid conversion rate was lower than what they wanted. Right? That was the challenge they came to us with. Our traffic numbers are good. Even our signups on our website, our positioning and messaging on our website is clearly doing a good job. But once people get into the product, there's not enough of them getting to value quickly enough. I mean they still had healthy customer base, but they knew that that number could be increased. So we knew what we were solving for.

**Lenny** (00:29:11):
Got it. Okay. That helps.

**Georgiana Laudi** (00:29:13):
Yeah.

**Lenny** (00:29:14):
So step one here is figure out who do you want to focus on, not just... Because a lot of people would go at this problem like, "Okay, conversion is whatever, 10%, how do we increase? Let's look at this data. Let's look at it. They're bouncing. Let's look at why people are confused." And your approach is, "No, let's focus on the people we really want to get into this product and focus on making them convert, and not focus as much on the general case of conversion."

**Georgiana Laudi** (00:29:39):
Right. We would get to that though. That's a really important part of the process, but it comes after figuring out who you're even solving for. But it's definitely important to look at those numbers. I mean, I'm not saying don't look at the data. Obviously you have to. They wouldn't have identified a problem had they not been looking at the data. So the challenge that happened so, so often, and I mean this happens with a lot of teams, particularly marketers fall victim to this tactical way of approaching things and piecemealing things, piecemealing campaigns or programs to prove that we're doing something and we're driving up numbers, and they don't take big enough sort of swings. So this is like, zoom out for a second, figure out who is it that you even want coming through the front door. I mean, the social media platform tool that I mentioned, the trial-to-pay conversion rate bumped up 40% because a higher qualified person comes through the front door. So it matters.

**Georgiana Laudi** (00:30:40):
So if you can zoom out and keep in your mind's eye that ideal customer job, that thing that you're solving for. We're not at personas. We don't care about personas at all. They're important when you start talking about advertising and targeting and that demographic data that you have to know when you're doing advertising and things like that. That is not what I'm describing here at all. I find that jobs be done too helps tie and bond marketing and product and customer success together a lot more because all three of those teams, or arguably four with sales, should all be focused on this theme customer that's not revolutionary. So this is just a sort of helpful way to do that.

**Georgiana Laudi** (00:31:24):
Product teams know and subscribe for the most part to the jobs-to-be-done theory. So marketers should follow suit, and there's a lot to be gained anyway on the marketing side. So anyway, the short of it basically is that because we knew we were focused on increasing that free-to-pay conversion rate, the next step after the job is the mapping. So it's identifying, okay, for this ideal customer, what are those key milestones in their relationship with our product? What are those big of leaps of faith is how I describe it. I mean I don't need to explain. The Airbnb customer journey tells that story. Where's a value moment in this relationship? Where are they reaching value?

**Lenny** (00:32:06):
Make some examples of that for folks that are trying to do this for themselves potentially. And then also, how many of these moments would you suggest people have?

**Georgiana Laudi** (00:32:13):
Yeah. So it completely depends on the product and the customer for that matter. I shouldn't leave that part over it. Obviously that's important. In general though, what we would do is, we'd break it down into a struggle phase and evaluation phase and a growth phase. Struggle phase is, they're experiencing the problem, life sucks, they're using the old way, something's got to happen, they've got to solve this thing. In general, the struggle phase would break down between out in the world experiencing the problem for the first time. So we call that a problem. And generally there would be another one called interest, where it's like, "Okay, now they're starting to shop around. They're getting into solution seeking mode." They might be on your website. They might be on your competitor's websites. They're reading product reviews, things like that. That's interest stage.

**Georgiana Laudi** (00:33:00):
And then there's the evaluation phase, which generally breaks down, I will say two or three milestones within the evaluation phase. I say two or three because if you have a more complex product, more complex customer is the more likely scenario. There may be more leaps of faith or more milestones, heavier lift for you to take. So we have worked with companies where the evaluation phase has been three or four milestones, I would always default to as few as possible. So if I'm cutting it down to lowest common denominator, I would say a first value would be the first milestone within evaluation. So you want to get them to that product activation really, really quickly. And then value realization is the milestone where you're solving that customer job. So they reach a point with your product where they're like, "Hell yes, this is it." And for the first time, they reach this critical threshold of product engagement. Now, what that product engagement is with your unique product for that specific customer is up for debate, but there still needs to be that moment.

**Georgiana Laudi** (00:34:08):
And then there's the growth phase, which is about the continued value. So getting to frequency of usage and a healthy building of that habit, getting into a cadence that makes sense. What type of feature usage and end product usage should you want to see there and then on what frequency becomes really important. And then there's another milestone generally after that where you're like, "Okay cool, they're in. They're pro. Now, what else do they need?" What else do they need from a product? And also, how else can we amplify them or work with them to either start teaching our tool to other people? I mean there's all kinds of things that can happen about growth. That's where the promise that exponential growth assess sort of comes into play.

**Lenny** (00:34:54):
And as people listen to this, just to maybe help if it's not super obvious, what people shouldn't imagine is like a little key frame, a storyboard frame of like, "Here's something your customer is doing." Right?

**Georgiana Laudi** (00:35:04):
Yeah. We often talk about it and describe it as the story of how I met and fell in love with your product. It's like this documentary of being out in the world, finding it, realizing that like, "Hell yeah, this might actually solve a problem for us. This might be it." Getting that enough value to convince them to keep going to full value realization, to continue value-to-value growth.

**Lenny** (00:35:28):
**Georgiana Laudi** (00:36:31):
Now, again, I'm saying that as if it applies to all customers and products, and that's not actually the case. Sometimes it's more complicated than that, but in general, that is what we have found. So that's what we did for SparkToro customers based on the research that we did. The research that we do, we basically take all the responses, we identify the critical patterns, and that's how we identify the customer job. From those critical patterns, if we segment down just that customer job, we can look at responses and say, "Okay, here's what they're likely doing when they're out in the world experiencing this problem. This is how they described the pain of their current solution. And then here's what they say about how their search for a solution started. Here's what they told us about how they started to do that research or find a solution."

**Georgiana Laudi** (00:37:17):
And then there's questions that are asked in the research like, "What was the moment that convinced you that our product was going to solve this problem for you?" And the answers to that question are going to tell you what your first value should look like, which of that first product activation experience, whatever language you like to use, what should that look like for them? What parts of the product do you need to push right up to the front of that experience so they can get to it really, really quickly after they sign up?

**Georgiana Laudi** (00:37:40):
And then value realization obviously would be close to, if not, the desired outcome of that customer job where you're solving that customer job. And then you've got all kinds of... Generally, what happens when I'm going through this process with teams is, all kinds of ideas start to come up about what more they could be doing, even post solving that customer job, especially the product team gets really exciting because they've got all kinds of ideas about where the product can go. So that really helps tie everybody together too.

**Georgiana Laudi** (00:38:10):
A critical part of that process obviously is identifying we have to measure success along the way. There should be a KPI for each of those stages in that customer journey. And for the most part, they won't be a big surprise on the struggle side of things. People out in the world experience the problem, how are we going to know we're doing a good job reaching them? We bring in new unique website visitors. In general, that would be the measure of success for the problem milestone. And then next piece of the puzzle is like, okay, once they discover that we exist, even if they are visiting, reading product reviews and visiting competitor sites or whatever, we'll know we've done a good job of convincing them that we can help solve their problem and deterring the people that we don't want.

**Georgiana Laudi** (00:38:53):
We know we've done a good job when the conversion rate on whatever our primary CTA is on our website, whether or not it's start a trial or request a demo, something like that. Generally, the struggle phase is very straightforward in terms of measurement. That's like marketers' bread and butter, that's where they live and breathe all day long. Where things start to change though generally when we're working with companies is helping them figure out how should they be measuring first value or product activation and how should they be measuring actual product engagement. Generally, what we do there is, we can associate basically what they told us brings them the most amount of value with the product attribute or parts of the product that deliver that value. We try to tie the KPI obviously to some sort of meaningful product usage of that key part of the product or product attribute.

**Lenny** (00:39:49):
Can you share some examples of that? Because that's a really important piece.

**Georgiana Laudi** (00:39:52):
Yeah. I'll use SparkToro as an example just because it's the one that we started with. So for SparkToro, I don't remember the exact customer job statement necessarily, but for them, what they said were, the parts of the product that gave them a ton of value was two specific features: lists. So being able to organize their findings in a way that made it not only easy for them to organize within their own files but also share because a lot of them were with clients or stakeholders that they want to be able to share with. So lists were a specific feature that honestly, it was in there, but they weren't front loading the product experience with that. I'm not going to say it was hidden, but it wasn't front and center enough. So that was one feature that we could associate with being able to organize the data, being able to continue to build on it and make it usable over time and also share.

**Georgiana Laudi** (00:40:55):
And then there was another feature as well, which was an exporting feature. Again, it's not that it was hidden, but it wasn't front and center enough. So we tied KPIs to them making use of those features, coupled with obviously the core feature, which is searchability. It was like pairing the search functionality with the list functionality, and then pairing the search functionality with the list functionality, with the export functionality. It's a bit abstract to me just saying the words. It's easier with a visual. But the story is basically, help them use the search functionality first. Right after that, make sure that they're using lists. And if they don't use lists, let's help them get back to using it so that they get to that important critical value moment. And then the same applies for the exporting features that we were talking about.

**Lenny** (00:41:43):
Got it. And to be clear, you basically said a metric for each of these moments.

**Georgiana Laudi** (00:41:48):
Yeah, milestones.

**Lenny** (00:41:50):
Milestones. Yeah.

**Georgiana Laudi** (00:41:50):
Or just whatever. I mean you have to. I mean it always surprises me when a team is like, "Oh yeah. Yeah, you're right, we don't do that." I'm like, "What? What do you mean?" So at a given milestone, unless they've reached that value moment, you can't keep them on the train to something else. If they haven't even discovered that really, to them, most valued part of their product, you would need to focus on getting them to that value. Otherwise, you can't just keep firing off emails and hoping they're going to jump back into the product as if they're going to care. So a lot of what we'd do is actually proactive customer experiences, whether or not in app or email or whatever tool, to help them get to that moment within the product.

**Georgiana Laudi** (00:42:32):
And if they don't get to that moment, which is measurable, again, that's why it's a KPI, then we can be reactive in helping them get back in. So identifying, "Okay," not that you would say this like, "it fell off the train," but just helping them nurture them back into, the product didn't really discover that feature if they missed it the first time around. So it's proactive and pushing them forward, but then also catching them if they fall. And the only way to catch them if they fall is if you're measuring something meaningful along the way.

**Georgiana Laudi** (00:43:02):
We have that storyboard that we were talking about. We also have a map where it's the experience to get them to a certain value moment, but then that win back experience to get them back in should they fall out for any reason. I mean, people get hungry and get distracted, and there's a ton of reasons why. I mean there's a lot of stats on the percentage. I think it's like 70% of people log into an app, log into a product once and never come back. It's wild. So the fact that so many companies don't have some sort of win back or re-engagement always blows my mind.

**Lenny** (00:43:41):
So just to recap and then we'll keep going with the process. Step one, understand what your customers are going through, figure out the most important customer and their biggest problem, then map out the journey that they go through, the struggle they go through before they discover your product, the steps they go through to evaluate, decide to use your product. And then once they use your product, then continuing to use your product and using it more and more. And then once you figured out these steps... And is a rough number like 10, 12 steps? What's a good number just to put-

**Georgiana Laudi** (00:44:13):
Oh no, I would hope it's more like six.

**Lenny** (00:44:16):
Six, okay.

**Georgiana Laudi** (00:44:17):
I'm always trying to bring it down lowest, only as long as it absolutely needs to be. I mean that goes for all pages, landing pages.

**Lenny** (00:44:25):
Okay, all right.

**Georgiana Laudi** (00:44:25):
Same thing for customer journey mask.

**Lenny** (00:44:27):
Okay. Airbnb had 12, I think. So you're involved in-

**Georgiana Laudi** (00:44:29):
Yeah.

**Lenny** (00:44:29):
I liked that. Okay. And then you've come up with a metric to tell you if that step is performing well.

**Georgiana Laudi** (00:44:36):
If they'd gotten there, did they get to that value?

**Lenny** (00:44:37):
If they've gotten there. Cool. One last question before we move on to the next step. Can you give two maybe examples of an actual movement, say in SparkToro's case, and then the metric that they use to measure, if they've gotten to that point?

**Georgiana Laudi** (00:44:52):
Yes. So the measure for success at that tip somebody over into evaluation is performing their first search. So when you're on their website, you perform a search, it's not signing up for a trial or signing up for free, although it does tip you into signing up for free when you perform your first search. So signing up for getting your first search and seeing your first search results is that first measure. And then following that for first value, it is using search again. I mean this is very product specific like I said, but generally, a first search is a kind of an experiment where you're sort of trying the tool on for the first time. Generally, searches start to get better when you do your second and third. So we try to encourage at least five plus.

**Georgiana Laudi** (00:45:38):
So that first value KPI, I think it was five plus searches, plus at least one list. So it's the combination of those two things that have to happen before somebody's going to really see what this thing does. It's not that they won't get value if they don't use lists, but because we know that SparkToro's ideal customers really get a ton of value out of lists, people can hang out in that stage all day long if they want to. We're not going to worry about them. We're going to worry about the people that really want the actual functionality of the real fully featured tool. So that was the first value, that's how we would know that they got to product activation.

**Georgiana Laudi** (00:46:21):
And then the next one, as I mentioned before, is a combination of actually three things. So it is conducting a minimum amount of searches within a span of time, creating at least a certain number of lists, I can't remember exactly what it is, and then discovering exporting at least once. And then that is, they've reached a meaningful enough threshold of product engagement. And then value growth was that they do all of that on a regular enough basis so that we know they're not a flight risk basically. So that we know that they're getting continued value from the product. And if they ever fall out of that ongoing engagement measured success, then we can trigger either one-on-one outreach, an email, whatever. I mean obviously it can't be an app because if they're not logging into the app, then you can't reach them. But to help them back in and to say, "Hey, what's up? Can we help? Is there anything that we can do?" And basically be proactive in getting them back in. And then value growth, I believe I think it was expansion or upgrade in their case. I can't remember exactly.

**Lenny** (00:47:27):
Cool. So you end up with these say, six KPIs.

**Georgiana Laudi** (00:47:29):
Yeah.

**Lenny** (00:47:30):
I imagine this becomes goals you track, and then you probably pick one of these to focus on say, per year, per quarter. Awesome.

**Georgiana Laudi** (00:47:37):
Yeah, hopefully not per year.

**Lenny** (00:47:38):
Okay, per week.

**Georgiana Laudi** (00:47:40):
Hopefully short, because I mean I will say that with some of the KPIs, it's very straightforward with new unique website visitors or the website conversion rate. I mean depending on who owns the website, that's not something that should take you a year. You should never be focused on only your website's conversion rate for a year hopefully. But these other KPIs and these other milestones, I mean I have no disillusions about if it impacts the product, obviously there's a lot of implications there. So yes, generally, once you tip over into that sort of in-app and more product experience, timelines vary widely, to say the least.

**Lenny** (00:48:18):
Okay, cool. Let's move on to the next step.

**Georgiana Laudi** (00:48:21):
Okay. So after that point, we had a rich voice of customer document that came out of that research. We had a messaging guide for them to use not only in their marketing materials but also through the entire product experience, and also identifying the parts of the product that were so meaningful. Actually, their VP of marketing, the new VP of marketing, Amanda Natividad, actually rolled out checklist. They built a checklist, a product onboarding checklist and also product onboarding emails. And their trial-to-paid doubled. We were like, "Okay, cool, let us know if you need any help or whatever." And they're like, "Oh, we're good. We got this." Checked in two months later and their trial-to-paid had doubled.

**Lenny** (00:49:03):
I feel like you skipped the important staff of, "Hey, we got KPIs." And then you're like, "Oh, we gave them all this information." So I'd love to spend a little more time on there. You came up with messaging for them, positioning stuff. what happens there?

**Georgiana Laudi** (00:49:16):
Well, this is the thing. They have a team in place. They've got very highly skilled, a huge team but highly skilled marketer there at the helm. I mean not the list of which is Rand Fishkin, their CEO. So basically, what we did was we gave them, it's like a framework. So it's like, "Here are the bones of this. So got a messaging and positioning guide for you." Generally, I mean when we do them, they're five to seven pages long. They hit on the value prop. They hit on the major competitive advantages. They hit on the major value themes that you want to focus on. Those value themes can be broken down by the emotional benefits and the functional benefits tied to the product attributes that drive that value. So that document, and there's more that goes into it, but that messaging guide basically can be used as the baseline for all kinds of marketing collateral and material, but also email onboarding.

**Georgiana Laudi** (00:50:16):
So when they're writing their email sequences for whatever it is they're trying to solve for, whatever milestone they're solving for, they can use that as their baseline like, "This is what we're going for. This is the goal here." And that messaging guide rules up to the job to be done. So the job to be done is sort of like the top line. And then we've got that messaging that serves that job to be done. And then we've got the sort of operationalized customer experience with those milestones and KPIs. And then you sort of zoom in on like, where is the experience most broken right now? We already knew that for SparkToro. We knew that we wanted to influence that first early product experience. So that's where we zoomed in and decided on what programs they should roll out. And email onboarding was a natural, as was the checklist.

**Lenny** (00:51:03):
For folks that want to work on messaging, say kind of just like, "Hey, here's a bunch of messaging advice," any tips for how to message well, how to think about messaging once you have a sense of your journey, maybe some goals, any just pro tips here you could share?

**Georgiana Laudi** (00:51:21):
Oh, boy. I mean that research and the voice of customer, I mean I'm always going to go back to that. You can guess and you can do use your best judgment. You can use internal stakeholders and the internal team knowledge. And I'm not saying that that is not valuable and that you shouldn't use that at all. You can, but it should never come before learning from and listening to your best ideal customers and using the language that they use. You want to reflect them back to them. That is what is going to show them that you understand the problem that they have and that your product has exactly what it is that they need.

**Georgiana Laudi** (00:52:06):
The hierarchy of messaging is really important as well. So I mean, there's the classic, sometimes it's hard to see the label from inside the jar, so it's really helpful to get out and be like, "Okay, how do customers see us?" Generally, you can identify the hierarchy of what is important to them, what is the thing that they say is most valuable about their product? What was that aha moment or what was that first value moment? Or what is the thing that makes you stand out over everybody else? And it can literally be a numbers game. If you take a hundred or so survey responses, you can break that down like, "Here's the thing they said they cared about most. Here's the thing they said they cared about second most and third most," not to be so paint by numbers about it, but there's art in the science. But in general, you want to reflect back what they said they care about, not what you think is the coolest thing about your product. That's obviously not the best way to go.

**Georgiana Laudi** (00:53:05):
That's something that we all inherently know, but it becomes really hard when there's a lot going on and things are changing and the product is evolving and there's a lot of teens and people are coming and going. It's easy to lose sight of that, especially when you're just trying to get shit out the door. So that messaging guide is mentally like, "Okay, here we are. This is my baseline, these are my guardrails for everything that we produce." It's also really handy to hand off to copywriters when you bring in... I mean not just copywriters, lots of people, but particularly when you're producing copy, providing that messaging guide is solar platter for them.

**Lenny** (00:53:46):
Is this available anywhere, the template that you end up sharing with a customer? Just like, here's a guide, the layout, messaging, recommendations.

**Georgiana Laudi** (00:53:53):
Oh, we have so many.

**Lenny** (00:53:55):
Maybe a little-

**Georgiana Laudi** (00:53:55):
We have so many templates and stuff. Yeah, I'll include a couple links.

**Lenny** (00:54:01):
Great. I'll put it in the show notes.

**Georgiana Laudi** (00:54:02):
We got lots of stuff like that. Yeah.

**Lenny** (00:54:04):
Okay, great. A few final questions around jobs to be done.

**Georgiana Laudi** (00:54:09):
Yeah.

**Lenny** (00:54:10):
So you said that they doubled their conversion from free to paid.

**Georgiana Laudi** (00:54:13):
Yeah.

**Lenny** (00:54:13):
Amazing. What was their job to be done in the end? And then I just have a few questions about the jobs to be-

**Georgiana Laudi** (00:54:19):
I think it was when they're struggling to identify opportunities that aren't as obvious. So generally, when you're doing marketing research, you'll end up signing the same things over and over again. And if you are a service provider or if you're in-house for that matter and you're tasked with always coming up with novel and new and more and more and more, you tap that pretty quickly. So what customers were coming to them for was like, "Give me more. I need to impress here. I need more to work with. I need to identify opportunities that I wouldn't otherwise be aware of." Actually that was exactly what it was. I helped me identify opportunities as I wouldn't otherwise be aware of. So the customer job statement is, "When I am in a certain situation, help me," which is filled in by what those things that they're looking, for those motivations, "so I can," which is the desired outcome.

**Georgiana Laudi** (00:55:18):
The help me was about, I believe it was in a way that is organized and that is shareable and usable over time that I can build on and really rely on over time. And the desired outcome was about, I mean this isn't going to be surprising, but it was about getting stakeholder by hand and getting people on board with, and sharing and looking good, looking like a pro, and doing their job more effectively and driving better results for either their own team or for their clients.

**Lenny** (00:55:48):
Awesome. We got there. We gloss a little bit over jobs to be done. I imagine many people listening have no idea what this is. So maybe as our final question, can you just explain what this framework is and how folks can learn to use it, or any resources you recommend that comes to mind?

**Georgiana Laudi** (00:56:07):
Yeah. I mean a heavy influence for us definitely is Bob Moesta, who's one of the original architects of jobs to be done. There are lots of materials online for jobs. I am not the foremost authority in jobs at all. I think jtbd.info is a good website. There's a bunch. Also, Bob Moesta wrote a book called Demand-Side Sales that goes into it. There's also a lot of books written about jobs to be done. When Coffee and Kale is one that a lot of people love. I digress. Point being that what matters is identifying what it is that customers are trying to accomplish. So demographic data doesn't matter. The classic example is, if you look at... Oh, King Charles, now the example has changed. If you look at Ozzy Osbourne, and it was Prince Charles the original, but now it's King Charles, if you look at those two men, they're the exact same age and live in the same area. They both have a dog. They both love cars.

**Georgiana Laudi** (00:57:04):
From a demographic standpoint, they are identical, but they obviously lead very different lives. What motivates them is very different. So that is where typically personas sort of fall down. So what jobs to be done, to us, is help you figure out what is that desired outcome, what does that better life that customers are seeking out. You were just the vehicle to get them there. That's all it is. I mean there's so many tired analogies so I don't even want to use them but-

**Lenny** (00:57:34):
Milkshakes maybe.

**Georgiana Laudi** (00:57:36):
What's that?

**Lenny** (00:57:37):
The milkshake analogy.

**Georgiana Laudi** (00:57:38):
The milkshake one, it's not even the analogy. I think that was one of the original job stories that is the milkshake one.

**Lenny** (00:57:45):
Any other things you want to share about the process that you go through with the companies, things you've learned, before we get to a very exciting lightning round?

**Georgiana Laudi** (00:57:54):
Yeah. One of the objections that we often get to this type of work is that research takes a long time and that research can often lead to more questions and can slow everything down. You can end up in analysis paralysis, but it doesn't have to be that way. It can be very straightforward, honestly, in a survey scenario. With SparkToro, in just that scenario, I have lots of examples of companies where we ran surveys, it can be a couple of weeks. Two or three weeks, you can actually come out with something solid to move forward with, and you don't get stuck in the bickering or all those stakeholders, the too many cooks in the kitchen. You can come to something decisive. You can get value out of that.

**Georgiana Laudi** (00:58:47):
The other thing too, the other objection that we get a lot from founders in particular is because they build products to solve a problem that they had, which is cool and it definitely makes you one of the most knowledgeable people about your solution. But products change, markets change, customers change, teams change in a ball. Not everything can live inside of your head, and there's a ton of value in learning and getting inside the heads of your best customers that you may have been really close to the inception of the product. But if any span of time has changed, you'll always learn something new. I've never been in a scenario like this where a founder has not learned something new from their research and been able to leverage it in a way that makes their product experience better.

**Lenny** (00:59:35):
Awesome. We'll come back to how folks can reach out to you if they want to experience this process, could work with you, learn more. But before we get there, we've gotten into a very exciting lightning round. I've got five quick questions for you. We'll go through them quick, whatever comes to mind. That's what we're doing. Okay, sounds good?

**Georgiana Laudi** (00:59:50):
Okay.

**Lenny** (00:59:51):
Okay. What are two or three books that you recommend most to people looking to get better at marketing?

**Georgiana Laudi** (00:59:58):
I very, very, very rarely read marketing books, but there's two that I think are pretty foundational and recent. So Obviously Awesome by April Dunford. I'm sure you've heard that one a ton. It's kind of required reading, I would say, especially for founders. I told April when she first wrote, I'm like, "I'm going to require every single founder I work with to read your book before we work with them," because it's foundational, you have to know that.

**Georgiana Laudi** (01:00:23):
And then the other one that I really enjoyed flip side was Hooked by Nir Eyal. That one was great too. But like I said, I don't read many marketing books. The other one that I would be remiss not to mention is ours that we're writing about the process, which is really about the step by step how to do this thing. So as much as we love going through this process with companies, I sort of took a page from April here too, in that telling the process and having people be able to rule this out and do this internally themselves has been wildly gratifying. We do it with a training program and this is our next step in getting out into the world even more. So you absolutely can do this stuff yourself. So that process is later in that book. And then another book that I read recently, which has nothing to do with marketing at all, but was really nice was 4000 Weeks. I don't think-

**Lenny** (01:01:15):
I'm reading that right now.

**Georgiana Laudi** (01:01:15):
Oh yeah, I enjoyed it. It was a nice sort of coming back to base a bit. I don't know when I read it. I just finished it a couple of weeks ago. It was just the timing was perfect. I feel like what's going on in the world right now and how everybody's probably feeling right now, it's a good solid read for now.

**Lenny** (01:01:38):
I'm enjoying it. I just started. I'm glad to-

**Georgiana Laudi** (01:01:40):
Okay.

**Lenny** (01:01:41):
Well, you encouraged me to keep reading it.

**Georgiana Laudi** (01:01:43):
Yeah.

**Lenny** (01:01:43):
Okay. Favorite recent movie or TV show?

**Georgiana Laudi** (01:01:46):
I have young kids. I just bought a second property. We're renovating three houses right now. I do not watch movies almost ever. The only thing that I'm currently binging is YouTubers that do DIY interior design and renos. Reason being my partner and I bought a property with four very, very old cottages lakefront, almost like tiny houses, little cottages. We are slowly renovating each of them. So my sort of fill is learning about interior design and DIY home rentals. Yeah.

**Lenny** (01:02:31):
Who's had the most impact on you in your career?

**Georgiana Laudi** (01:02:31):
This is the worst question. I hate saying this, but it's probably my dad. I have to say my dad because he's an entrepreneur through and through. And I remember very vividly, I worked for him for I think eight years early in my career. One of the things that he always said was like, "It was the joy of the business." He didn't care what, he's like, "It doesn't matter what you're selling." He could be selling anything, but it was the joy of entrepreneurship. And that really stuck with me. So even when I was in house, I always knew that I needed to do something on my own and be in charge of that journey. His joy in it has impacted me a lot. He was the reason why I knew I was always going to do this.

**Georgiana Laudi** (01:03:26):
Other than that, I would say I have an incredible network of women that I have been very lucky. We're part of a group that we call Shine Crew. I think I'm supposed to copyright that or something to somebody because I think the term Shine Theory is what it's based on basically. But I'm very, very lucky to be heavily influenced by April Dunford, Tara Robertson, Joanna Wiebe, Talia Wolf. And then obviously my business partner, Claire, obviously changed everything for me. Having that partnership in business, I don't think I would've lasted this long. So yeah, definitely a huge influence for sure.

**Lenny** (01:04:10):
What's one thing that helps you stay focused and productive during the day?

**Georgiana Laudi** (01:04:15):
Definitely carving up time, like time blocking. I do a lot of time blocking in advance with a little brain emoji of safeguarding my time. Because we're a small team and we use Slack obviously, something else that we do to protect each other's time is not time stamp, but we put a little code in all of our messages that's either like, "You don't have to listen to this before the end of the day," or, "It's timely," or, "It's no rush," so that we know when we need to mentally process messages in Slack, so we can drop in there just periodically. And then the only other thing that I would say that I do maybe once a month or once a quarter is, we're pretty buttoned up about our time tracking, so we go back and it sort of keeps us honest about how our time is actually spent. And then we can sort of adjust and time block accordingly to make up for the shortcomings of our previous quarter.

**Lenny** (01:05:10):
That was really clever. I haven't heard of that trick. What's the emoji for "You can do this later"?

**Georgiana Laudi** (01:05:15):
We actually just use no rush or EOD for end of day, or timely. We do have the alarm emoji, is the "Now. This is going to be dealt with ASAP."

**Lenny** (01:05:29):
Amazing. Gia, thank you for making time. For this final question, where can folks find you online? How do they pre-order your book? How can they learn more? And then also, just how can listeners be useful to you?

**Georgiana Laudi** (01:05:39):
Thank you for asking. Twitter is probably the best way. My Twitter handle is atrocious, @ggiiaa is me on Twitter. I'm on LinkedIn every once in a while obviously. My email address is gia@forgetthefunnel.com. So if anybody has any questions, whatever, feel free to email me. If you want any templates or whatever that don't get included in the show notes, just ping me. I've no problem with that. And then forgetthefunnel.com, we've got a book page where there is a wait list for the... Well, we're going to do presale, and then the published physical book will be early in 2023. But we are going to do presale because... Get it in those hands. Why not?

**Lenny** (01:06:18):
Love it. Gia, thank you for being here.

**Georgiana Laudi** (01:06:21):
Thank you so much for having me.

**Lenny** (01:06:24):
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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