---
title: "Lenny's Podcast — 2022 Q4 合集"
date: "2022-01-01"
source: "Lenny's Podcast"
url: "https://www.lennysnewsletter.com/"
---

<div v-pre>


# Lenny's Podcast - 2022 Q4 (20 episodes)

This file contains 20 articles/episodes.

---

## [1/20] Using behavioral science to improve your product | Kristen Berman (Irrational Labs)

**Kristen Berman** (00:00:00):
Economics says, "Look, people are rational. We make decisions with no emotion. We use lots of computational energy, weigh the pros and cons." I mean, obviously, that's just not true. It ignores the whole field of psychology. And so, in behavioral economics, you combine the field of psychology and economics and say, "Look, people make decisions with lots of emotion. We are present bias. We over-weighed our present selves. We follow social norms." But the good news is that we do these things in predictable ways. And once you understand how and why people behave, you can start to change it. And so, behavioral science and behavioral design basically uses those insights on psychology to actually apply it within real world problems.

**Lenny** (00:00:45):
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 experiences building and scaling today's most successful companies. Today, my guest is Kristen Berman. Kristen is the CEO and co-founder of Irrational Labs where she and her team use behavioral science to help companies like Google, Airbnb, PayPal, Microsoft, Fidelity, and TikTok build better and more successful products.

**Lenny** (00:01:15):
In our conversation, we cover a ton of real-life examples of product changes that have her and her team helped craft that led to significant impact at the companies. We talk about what biases and psychologies they find most commonly get in the way of people achieving what they want achieve in your product, her biggest surprises and insights about human psychology and how it relates to product design, a couple of real-life case studies including our work with TikTok and the change they made in the product as a result, and so much more. I found this conversation super fascinating and super tactical, and I can't wait for you to hear it. And so with that, I bring you Kristen Berman.

**Lenny** (00:01:55):
Hey, Ashley, head of marketing in Flatfile. How many B2B SaaS companies would you estimate need to import CSV files from their customers?

**Ashley** (00:02:02):
At least 40%.

**Lenny** (00:02:04):
And how many of them screw that up, and what happens when they do?

**Ashley** (00:02:07):
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** (00:02:26):
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** (00:02:41):
Totally. It's credible to see how our customers like Square, Spotify and Zuora are able to grow their businesses on top of Flatfile. It's because [inaudible 00:02:50] data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:02:58):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny.

**Lenny** (00:03:06):
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.

**Lenny** (00:03:54):
Kristen, welcome to the podcast.

**Kristen Berman** (00:03:57):
Thanks, Lenny. Great to be here.

**Lenny** (00:03:58):
It's great to have you. You're on something called Irrational Labs, and so, to set a little context for folks, can you just talk about what it is you all do at Irrational Labs?

**Kristen Berman** (00:04:08):
Yeah, so Irrational Labs, we are a behavioral science consulting and design shop. So, we think about all things behavior change. We work on understanding psychologies that drive users, and then designing and testing ways to change behavior and drive engagement.

**Kristen Berman** (00:04:28):
I started it in 2013 with Dan Ariely, who's a famed behavioral economist. We started just working with a handful of companies, and now we have a team of 20 behavioral scientists working on behavior change across industries.

**Lenny** (00:04:43):
Can you talk about some of the companies that you've worked with, just to give us some examples? And then, what kind of stuff have you actually helped them with?

**Kristen Berman** (00:04:50):
We started a lot of our work at Google. We were actually embedded within Google for around three years. I even had a bus pass. And we started their behavioral economics team. We worked with over 25 teams from like self-driving cars to YouTube. And so, that was a big piece of the early work. And then recently, we've done work with TikTok where we've tried to... It actually accomplished decreasing misinformation share by 24%. We worked with one medical on how to increase setting doctor's appointments right away during the onboarding, and that worked and drove it up by 20%. We worked with Credit Karma on basically helping them increase set up for reoccurring deposits. We did that and increased it by 18%. So, basically a variety of ways to drive behavior change. Done stuff with Intuit, Microsoft, LinkedIn, and obviously, a variety of startups as well.

**Lenny** (00:05:45):
Wow. Okay, we're definitely going to talk about some of those examples. I'm super curious to hear what you did with TikTok, big company and story these days. Before we get to that, what exactly is behavioral design, and can you just define this space for us?

**Kristen Berman** (00:06:00):
Let's start with what is behavioral economics? So, basically, behavioral economics is a reaction to economics. So, economics says, "Look, people are rational. We make decisions with no emotion. We use lots of computational energy, weigh the pros and cons." I mean, obviously, that's just not true. It ignores the whole field of psychology. And so, in behavioral economics, you combine the field of psychology and economics and say, "Look, people make decisions with lots of emotion. We are present bias. We over-weighed our present selves. We follow social norms." But the good news is that we do these things in predictable ways. And once you understand how and why people behave, you can start to change it. And so, behavioral science and behavioral design basically uses those insights on psychology to actually apply it within real world problems.

**Lenny** (00:06:51):
What are some of the biggest surprises, or maybe unintuitive results that you've come across working with companies using these insights in behavioral design, behavioral economics?

**Kristen Berman** (00:07:02):
Yeah, great question. One story that recently happened is actually a surprise that happened to the client. The partner was shocked. It actually didn't surprise us. And so, this was with a popular FinTech app and their most requested feature was budgeting. So, it came through all the support forums, interviews, felt like a table stakes feature; people wanted budgeting. And so, if you're the PM there, you're probably like, "You may talk to a few other users. You may get some confirmation, but you're likely building budgeting." And that's really where they were when we came and started working with them. We couldn't move them in another direction, but we did convince them to do an experiment. So, we convinced them to test, and there was three conditions. One was the control, which is just telling people how much they spend, and the other two were variations on budgeting. So, two different ways to do budgeting.

**Kristen Berman** (00:07:57):
So, big experiment. This is with 10,000 people, so we can really trust the results. And what happened? Nothing. So, they were shocked. The team was shocked. Remember, this is a big investment of time and effort, took a lot of energy to build. Zero change in average spend, zero change in spend variability. And so, the question is: Why weren't we surprised? Why were they surprised? The thinking here is if you map out every single step that it takes to do this behavior, and the behavior would be reducing your spend, it's pretty clear that budgeting just isn't going to pull the weight. And this is what we call a behavioral diagnosis, where you map out every single step. So, you'd have to know what your budget is. You'd have to know where in the month you are. You'd have to make a plan to do it. You then have to do it multiple times during the month. Incredibly difficult to do this one behavior. And once you do that behavioral diagnosis and you map out... We try to understand what people actually do versus what they say they will do. And by doing that, it becomes wildly clear that we should all be skeptical that budgeting would actually work to change the behavior that you're trying to get to.

**Lenny** (00:09:03):
Yeah, I'm also not surprised that didn't have a big impact. I have so many apps with budgeting features and I've tried many times to use them and it never sticks. It's like, "Eh, I'm just going to..." It's too much work.

**Kristen Berman** (00:09:15):
It's way too much work. And so, sometimes, any kind of work that we put on the user, we should be skeptical. We have to really prove that it's worth their time, and then measure if they actually do it.

**Lenny** (00:09:26):
Is there a better approach to that specific problem that you've found, or is that too broad of a question?

**Kristen Berman** (00:09:33):
The first line of defense in any problem solving would be, how would you make it easier for somebody to do? And so, in the personal finance world, really, the answer to most things is just default. So, it worked for automatic enrollment 401(k). The reason we have retirement savings in America is because people are defaulted into saving from their paycheck. So, that would be first line of defense. Obviously, difficult for product teams to execute on, takes a lot of backend infrastructure. So, if we were just solving the personal financial management stuff of like a budgeting alternative, we'd actually go to making it not just logistically easier, but cognitively easier. So, we call them rules of thumb; instead of having to decide in the moment, do I do this thing? And you're weighing the pros and cons. It's kind of typical econ, like, how much is this $3 worth to me? You'd actually make a rule of thumb that says, "Do I do it, or not?" So, instead of deciding, do you take a Lyft when you're coming home from work, you'd have a rule of thumb that says, "I don't take Lyft on the weekdays. I take it on the weekends." Very simple now to actually make this kind of decision. It's a heuristic . It's not going to be perfect, but it's going to help you reduce your spend in an easier way, at least, in a way that you'd stayed adherent to.

**Lenny** (00:10:46):
It reminds me a bit of James Clears' idea of creating this identity for yourself where he is like, "If you're like, 'I am a person that doesn't take Lyft on the weekdays', that becomes kind of this identity component and that makes it easier for you not to do that." Is that related?

**Kristen Berman** (00:11:00):
Yeah, basically. Sometimes, we think behavior change is driven by our attitudes, our preferences like, "I really want to be a runner" or "I really like this thing." But in reality, our behavior is driven by what we do. So, in order to change behavior, you have to do something different. It's not enough to have a goal objective to do it. And I think, maybe that's the big annoying thing about the self-help industry. It kind of just tells you it's enough to have a goal. It's not enough. You actually need to redesign your environment to change your behavior.

**Lenny** (00:11:35):
Is there any other examples of big surprises or unintuitive results from work you've done?

**Kristen Berman** (00:11:40):
One big one is actually... And I'm sure people listening have worked on signup flows before. This is kind of a common question and challenge in product world. And the common thinking is, and most often correct, that if you reduce friction to the signup flow, your conversion will increase. This is kind of the law that we all live by. And yet, there is one example, one time, where this is just not true, that you can actually increase friction and increase conversion. So, actually Lenny, have I ever told you about my mother?

**Lenny** (00:12:12):
Nope.

**Kristen Berman** (00:12:13):
Okay. So, now you're thinking about my mother.

**Lenny** (00:12:16):
Oh.

**Kristen Berman** (00:12:16):
Before, you were not thinking about... There's nothing about my mother, but I just made you think about my mother by asking you a question.

**Lenny** (00:12:22):
Son of a gun.

**Kristen Berman** (00:12:23):
So, when you ask a question, you can insert an idea into someone's head, you can get them thinking about something different. And so, in a sign up flow, what would you want people to be thinking about? You probably want them to be thinking about the benefits that you offer. So, if you ask them a question they can think about the benefits, it's going to increase their motivation to get over the hump of the future friction you're going to put in front of them because now they understand the benefits. So, as an example, if you go to Apartment List, they ask you questions during the signup flow that's like: What kind of apartment do you want? Do you want a studio, or a one-bedroom, a five bedroom? Do you want a patio, a basement, a view? Now, all of a sudden, I'm thinking, I'm engaging with the benefit. I understand how much supply that they have. So, if you Stitch Fix, or... Actually, Trunk Club has come out and said they did this and it increased conversion by 133%.

**Kristen Berman** (00:13:16):
So, asking these questions can really drive conversion. We actually did something where we put a quiz on a partner's website. It's TytoCare which is basically a device that lets you remotely connect to a physician. It's a little bit hard to use, but we wanted to help people understand the device, and we asked them questions about their medical behavior, their frequency use of technology. And for people who completed a quiz, 53% of them went on to purchase versus 37% who didn't complete. So, these type of questions can have a real impact.

**Lenny** (00:13:51):
And so, very tactically, the idea here is you add a step to your flow that asks the user some question that isn't actually something you need an answer to, but may get them to be more excited by finishing. Is that right?

**Kristen Berman** (00:14:04):
Exactly, yeah. And I would say probably most teams can do this. You can replace the carousel. The carousel is something where it tells you the benefit, but we want people to actively engage with the benefit so that they're thinking about how you can improve and affect their lives.

**Lenny** (00:14:22):
So, you said it's worked a couple times. It probably isn't something that usually works. Is there experience like sometimes it may work, maybe worth trying, but usually probably won't work. Is that generally right?

**Kristen Berman** (00:14:32):
We want to remove the field that was like an open text fields where we're asking people an open-ended question and we improved conversion by 40% page over page. So, for sure, some questions are harder and you should not ask them. When questions are easier and it's a drop down multiple choice, this is when you should be trying it. But definitely, the recommendation is not to ask a hard question where people have to think about it.

**Kristen Berman** (00:14:58):
By the way, for the question that we did, that was open text, the folks on the team thought that it was an easy question. But most questions when you're asking people with an open text field, it's just not an easy question.

**Lenny** (00:15:10):
Right. I hate those open text fields. And then, just one last, because I imagine people listening to this are like, "Oh, maybe I should run this experiment." Is the general best practice to ask a question that gets you to think about something that motivates you by finishing? What's like the rough mental model there?

**Kristen Berman** (00:15:26):
I think each product, obviously, will be different. One example would be, if I'm a bill pay app, you could tell me that I could pay my bill once a week, every day, every month, I could time it, but a better approach would be to ask me, "Do you want us to pay your bills immediately, or every week, or every month?" And so, what you're doing there is engaging people in the setup and actually implicitly telling them, "We can pay your bills immediately." So, would think about combining those two is showing people the benefit, like, how fast you want us to pay your bills, which gets you to think about how fast they are, and the settings which is actually you're really doing something to help the app work.

**Lenny** (00:16:09):
Awesome. Before we dive even deeper into more examples, I wanted to zoom out for a moment and I'm curious just how did you even get into behavioral economics? You said you worked with Dan Ariely. How did all this come about?

**Kristen Berman** (00:16:22):
Yeah, great question. So, I met Dan around 2008 and if you don't know Dan Ariely, definitely worth a Google. And at that time, he had just written his first book, Predictably Irrational, and I was a product manager at Intuit working on QuickBooks online. So, first use, customer discovery, and really after reading the book, hearing the talk, it's just like this light bulb went off and it was like... I'm talking to five to 10 customers to inform a feature, a product, and trying to come up with some insight on human behavior. And yet, there's this whole field that studied this, that has papers in thinking and studies why we behave the way we do. And so, this was like, "Wow. I can't believe we're just missing out on it in the product community." And so, I started working with Dan. We started and now, 14 years later, it's what I do; bring behavioral insights to product teams.

**Lenny** (00:17:19):
And you said you were running an embedded team within Google to work on this sort of thing?

**Kristen Berman** (00:17:23):
Yeah. So, basically, Google... It was kind of our first mover in thinking about how important understanding behavioral science was to product and marketing development. And so, it was Dan and I in the beginning, and over the course of the three years we hired internal Googlers, we brought in more people on our team, and really were an internal consultant where we'd be pitched to other teams, work with them from start to end on a project. And now, Google has one of the bigger behavioral science teams that's out there.

**Lenny** (00:17:50):
Wow. Okay. So, you've worked with how many companies at this point, roughly?

**Kristen Berman** (00:17:56):
I'd say hundreds.

**Lenny** (00:17:58):
Hundreds, okay.

**Kristen Berman** (00:17:59):
I mean... Yeah, hundreds.

**Lenny** (00:17:59):
Okay. So, there's hundreds of companies. There's also, I imagine, hundreds of these kind of biases and heuristics and kind of behavioral expectations of people. I'm curious, out of the work that you've done, what are the most common biases, heuristics of people that you find most useful in improving product experiences in product design? What's kind of the handful that ends up being most useful?

**Kristen Berman** (00:18:21):
Totally. And there are so many mistakes that humans make and we can call them biases, heuristics. Our team uses psychologies. What are the psychologies that drive us? And so, to tackle this, our team basically has created a model of behavior change. We call the three Bs. And this summarizes the most important psychologies that drive user that are important to the product manager and the marketers. We've used this at Google, Microsoft, LinkedIn, so all the companies that we work with, and they now use it. And so, the three B framework, first B is actually not a psychology, but it is the most important part of behavior change, and it should be obvious if you think about behavior change, behavioral economics, it is behavior. In order to change behavior, you have to pick a behavior that you want to change. So, companies are really good at outcomes, but just not as sharp at picking the behavior.

**Kristen Berman** (00:19:13):
When I say behavior, I mean action. The thing that you want someone to do. By the way, the only wrong answer here is log in. It's not about logging in, it's about what you do after you log in. And when we're consulting teams, it would be like... We need to get uncomfortably specific, we say. Just really specific in the behavior. So, example, if I'm Peloton PM and I'm working on the app, I would say something like, "Within seven days of somebody starting the app, they do two 10-minute workouts with two different instructors." Now, obviously that is wildly specific and you'd probably be very happy if they did one workout with one instructor, but the reality is if you don't define that behavior you're going to change. You can't actually define the psychologies that affect someone's decision making when doing that behavior. So, that's the first B.

**Kristen Berman** (00:20:01):
Second B, again, is probably pretty obvious and is very critical. It's just barriers. So, we need to reduce the barriers to doing the behavior. And there are two types of barriers we look at. One is logistical. So, this is just the stuff in our way; could be entering a credit card, could be any form field. And then, the second is cognitive. So, the cognitive barriers get in our way as well. These are things like uncertainty aversion. This is optimism bias, information aversion. These are the things that would prevent... Status quo, big one. It's just you do the same thing today that you did yesterday. Your job is-

**Lenny** (00:20:37):
Please. Can you talk about those three? Just through out there, just briefly. I'm curious about the specific biases while we're there.

**Kristen Berman** (00:20:42):
Yeah. So, uncertainty aversion, when something is uncertain or we're not... I'll give you an example of your Lyft. There's logistical friction which is wait time. But then, there's also this uncertainty of is it going to come on time? When is it going to come? And with this uncertainty, you're probably going to look for other options. You're going to open up Uber and say like, "Maybe it'll come faster." And so, when there is uncertainty in our life, we either look for other options, or we just don't make a decision at all. Right? This is, by the way, very big in healthcare where when you're very uncertain about something, you may not even go to the doctor, or you may just make the wrong decision.

**Lenny** (00:21:22):
Got it.

**Kristen Berman** (00:21:23):
And same with status quo effect where... Underlying status quo effect is this idea that we always take the path... Not always, but majority. You don't really say always when you're talking about human behavior. Human behavior is very complex. More often than not, we take the path of least resistant, that we do the thing that's easiest, and typically, the thing that's easiest is the thing that we've done yesterday and the day before. And so, when you're asking someone to do something different, which is what most product, especially startups, are trying to do, you actually have to increase their motivation or make it easier, reduce the barriers to get them to do that. And so, status quo effect is a big, big one that folks are fighting.

**Lenny** (00:22:02):
Awesome. Thanks for sharing those. Let's keep going.

**Kristen Berman** (00:22:05):
Cool. So, the third B is benefits. This is where you want to increase the... Not just benefits, but the immediate benefits of doing something. We are all present bias, which means we prioritize our present self over our future self, so there are plenty of reasons that somebody, your customer, your user should take an action, but you actually have to give them a reason to take an action today.

**Kristen Berman** (00:22:30):
So, as an example, if you're Asana, and if you're trying to get someone to log a task, the right thing for them to do is log the task because it's going to get their project done on time. You're going to have a collaborative and communicative team that you're going to want to be on. But one of the real reasons we may log a task is because of completion bias. We want to see the checkbox. We may log it because of social desirability bias where other people see that we're getting our work done. There's a notification that goes to my teammate when I complete something. So, these are the immediate benefits that we have to build into products and features to drive use.

**Lenny** (00:23:07):
Awesome. I definitely have completion bias. I love checking those freaking checkboxes. I know Asana is famous for that little unicorn confetti thing, right? For making you feel really good when you complete something.

**Kristen Berman** (00:23:17):
Yeah. I don't know how much emphasis to put on these kind of confetti stuff. I think the idea of being done is... That psychological understanding that you completed it, confetti or not, is very powerful.

**Lenny** (00:23:33):
I love confetti. Okay, so just to recap, there's the three Bs. Behavior, what is the behavior you're trying to change? And the way you described it sounds like the activation milestone. That's the way most companies think about that. Is that right?

**Kristen Berman** (00:23:46):
Yeah. I would say the activation milestone and the novel thing here is just getting really specific about this behavior, so much that if you're not arguing with your teammates, you're doing it wrong.

**Lenny** (00:23:59):
About which behavior and...

**Kristen Berman** (00:24:01):
Yeah.

**Lenny** (00:24:01):
... I imagine this often comes... Similarly to the activation kind of moment, it comes back... Working backwards from what is most likely to keep this person around long-term, kind of to keep them retained, right?

**Kristen Berman** (00:24:12):
Yeah, exactly. So, what correlates with retention and what provides an immediate value to them by doing this behavior.

**Lenny** (00:24:18):
Awesome. Okay. So, behavior, then barriers. How do you break down barriers, logistical and cognitive. And then, benefits. The point about being an immediate benefit is a really interesting one because, yeah, you may be like, "In a year from now I might earn some money, but I'm not going to do anything hard right now if I'm not going to make any money right now."

**Kristen Berman** (00:24:36):
Exactly. And so, this is a tough one because we want to believe that people really do and use our products for the end benefit, but we really need to give people the reason to do it today.

**Lenny** (00:24:47):
Awesome. I want to dive into a of couple case studies of companies that I know you've worked with. Maybe before that, I thought it'd be good to ask this question about the dark side of this stuff. I imagine people often worry about, "Hey, are you just tricking people into doing things they don't want to do? That's not good." How do you think about that line?

**Kristen Berman** (00:25:06):
Yeah, it's a great question. I think, the answer to this really, with many things in life, comes down to incentives. So, what are the incentives of the product teams, of you, your manager, the team, working on this? I like to say we are what we measure, and it really matters what you measure. I'll give you a personal example.

**Lenny** (00:25:27):
Yeah.

**Kristen Berman** (00:25:28):
LendingClub, a while ago, hired me to increase their conversion flow for borrowers. They're a lending app and they wanted to get more borrowers in the flow. The novel thing here was that they would pay me a lot of money if I hit a bump. It was like a five-point bump and zero if I didn't hit anything. [inaudible 00:25:47]

**Lenny** (00:25:47):
That was that. That's your incentive structure.

**Kristen Berman** (00:25:50):
Right. So, my incentive structure was to increase the conversion flow, and over the course of working with them, I became a predatory lender. I was suggesting things that the legal team was like, "No, Kristen, of course you cannot do that." Setting some contacts, I was at that time leading a Duke University lab called Common Sense Lab. It was focused on low to moderate income Americans thinking about their financial health, building savings apps for them. So, here I am, this kind of do good, non-profit, very focused on financial health of Americans, and my other hat was predatory lender for LendingClub. And so, it's really about the incentives that we're giving ourselves and our team that will drive how anything is used. Much less behavioral economics of these tactics, but generally, the success of your team.

**Lenny** (00:26:46):
You may not have a clear answer to this, but any advice for setting those incentives correctly? Anything you've seen work well?

**Kristen Berman** (00:26:52):
Yeah. I think for us there's two tips. One would be to set the incentive on the behavior because the behavior is going to align more with the customer outcomes than the active use or the retention. And of course... And I'm not suggesting we don't measure active use and retention in these things, you should definitely measure them, but setting the incentive, and the KPI, and the product, and the marketing team on the behavior is going to result in a more customer-friendly product and outcome.

**Kristen Berman** (00:27:18):
And then, second would be increasing the duration of the incentive. So, if you're trying to hit a quarterly outcome, you're likely going to do things that will impact the short term to give that a bump. If you're trying to hit an annual or even longer outcome, you're going to be looking out for the best interest of the company and the consumers in a little bit different way.

**Lenny** (00:27:39):
Awesome. For the LendingClub example, what did you end up doing in the end, by the way? Did she just like, "Nah, let's not do this."

**Kristen Berman** (00:27:44):
I can't actually reveal the intervention that we did, but I did miss it. So, there was a five... Wait, by the way, point, not percentage bump, which is a lot, and we got 4.5. So, we almost hit it, but it's a clip, it doesn't work that way.

**Lenny** (00:27:59):
Almost sold your soul for that bump, and you didn't get there.

**Kristen Berman** (00:28:02):
I know.

**Lenny** (00:28:02):
It seems like [inaudible 00:28:03]

**Kristen Berman** (00:28:02):
It was a good lesson in incentive [inaudible 00:28:05]. And by the way, at that point, LendingClub was offering good rates to borrowers. There was efficacy in the idea of it, which is LendingClub lending to people who have lower FIGO and with better rate. And yet, you still want to have... You don't want to become the predatory lender in that situation.

**Lenny** (00:28:23):
Okay, awesome.

**Lenny** (00:28:25):
Are you hiring, or on the flip side, are you looking for a new opportunity? Well, either way, check out lennysjobs.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 don't find a better place to hire product managers and growth leaders. Join almost a hundred other companies who are actively hiring through this collective.

**Lenny** (00:28:55):
And if you're looking around for a new 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 any time and you'll only hear from companies that you want to hear from. Check out lennysjobs.com/talent.

**Lenny** (00:29:15):
So, there's two companies that you worked with that I use, and I'm curious what you did for them and how you worked with them. One is TikTok, and then the other's One Medical. It'd be cool to just hear what you did for them, what they wanted your help with, and then just kind of what you took away, how it went, all that.

**Kristen Berman** (00:29:32):
Great, yeah. So, TikTok is obviously a big platform, and with any big social media platform, they have misinformation on it. This is not just a problem with TikTok. Facebook and Twitter have it, and misinformation is growing. And so, they asked us to help decrease the spread of misinformation on their platform.

**Kristen Berman** (00:29:51):
There's lots of ways that we could take that, and the first thing that we did, as we kind of do with any company, is think about what is the behavior that you want to change. And so, we narrowed on decreasing shares. So, we could have said likes. We could have said comments, or general engagement which is a broad thing, but we narrowed on decreasing the shares. So, when you're actually going to see a misinformation video, we want to decrease the number of people that share it.

**Kristen Berman** (00:30:18):
So, that was the first step. The second step is, this three B model, how do we think about the barriers? With TikTok, the thing that you want to do is get people to do something less. When you want to get somebody to do something more, you make it easier. When you want someone to do something less, you make it...

**Lenny** (00:30:36):
Put up barriers.

**Kristen Berman** (00:30:38):
Put up barriers, yeah. Actually, a nice example of it's an elevator study where basically, you want people to use the stairs. And so, what the researchers did was make the elevator door close 16 seconds longer. So now, you get in the elevator, you're annoyed. It's harder to use the elevator, and people went to the stairs.

**Lenny** (00:30:55):
16 seconds, interesting number.

**Kristen Berman** (00:30:57):
16 sec... We can't wait 16. And then, it's actually kind of long, though. You're standing there [inaudible 00:31:02].

**Lenny** (00:31:01):
So long. I'd use the stairs, yeah.

**Kristen Berman** (00:31:03):
Yeah. And so, that's kind of what we did for TikTok, which is, basically, you're in a very hot state. TikTok is a very fast platform, and so we just slowed people down. Two things. There was a label on the video, which is kind of classic in the misinformation world where you tell users that it's unverified information. And the second thing was, once you click the share button, we popped up something that said, "Are you sure?" And this was basically slowing people down. So, logistical friction, and actually cognitive friction because we're asking people to reconsider a prior decision and question their self. And so with that, both those things, the label on the video and the popup, reduced shares by 24%.

**Lenny** (00:31:42):
Wow.

**Kristen Berman** (00:31:43):
And these are tactics that Facebook and Twitter are also using to slow people down. This was actually one of the first [inaudible 00:31:48] published studies that showed that this drove down misinformation.

**Lenny** (00:31:51):
Can you talk a bit about how you came to those two conclusions? I know you work really closely with the product team and there's this whole process you go through. How do you come up with these ideas? How many ideas did you test? Is there anything more you could share on that?

**Kristen Berman** (00:32:03):
Yeah. It's actually a pretty involved process. First, we did a literature review which is basically saying like, Look, we're not the first people to think about this. Let's talk to the expert and understand what has worked and what hasn't." So, with that, actually, one of the insights was that reminding people about their value of accuracy. So, most people want to be accurate. Most people actually don't want to share this information. And so, if you can remind people at the point of sharing... By the way, it doesn't work if you remind people before or after. It's at the point of sharing, that this is unverified information, studies have shown that this could decrease share. So, we took that piece. We also took the hot and cold state literature that says, "If you actually don't want to get someone to do something, how do you intervene?

**Kristen Berman** (00:32:46):
So, we did this literature review. We came up with a hypothesis, and we had probably 30 different ways to implement this because the hypothesis is just a starting point. And then, we put it into quantitative research. So, we actually put five different version of the popup in front of over a thousand users, which... We got users from Prolific, which is a platform where you can easily test things.

**Lenny** (00:33:09):
Prolific? Cool. I haven't heard that.

**Kristen Berman** (00:33:11):
We didn't measure the idea, "Do people like this?" We measured a condition against another condition. So, relatively, what condition is more likely to work than the other condition, and that would increase our intuition than it would work in market. We're not saying that studies outside of the product are end-all be-all, but it's going to drive our intuition up a lot more.

**Lenny** (00:33:34):
For the research that you did, I imagine that's a lot of the value that you and your team bring to a group. For folks that are just on their own maybe, is there any advice for how to find research on problems you're trying to solve?

**Kristen Berman** (00:33:46):
Yeah. I would say, basically, if you're looking at a new problem, it's very tempting to talk to [inaudible 00:33:53] users in the beginning. We would basically say, "Look, go spend a day on the internet googling to see what else has been done." Google Scholar is a great place to start. Hot tips would just be making sure you're searching the right keyword. So, if you're looking at something in healthcare, you'd want to know what are the buzz words for chronic care and things that would actually drive you to a meta-analysis that would summarize what's already been done. So, Google Scholar, a great place to start. And then, coming up with the hypothesis and putting them to test. We never do a UX study where we're just showing people one thing because they could really like it or hate it, but they could really like or hate all the designs. We have no idea. So, when we're doing this, we always present multiple options, and then relatively look for which one is going to drive the behavior we're intending to change.

**Lenny** (00:34:44):
Is there a reason you did UX-oriented test versus testing the product? Is it just because they weren't ready to build an experiment in product yet?

**Kristen Berman** (00:34:52):
Yeah. We actually only got two conditions in product, which for us is we would like more and it was... We don't know if we're going to get a second bat at this. So, we said, "Well, two conditions plus the control." But what should those two conditions be? So, for us, we want to de-risk the launch as much as possible.

**Lenny** (00:35:11):
Awesome. And is that feature in the product today?

**Kristen Berman** (00:35:13):
It is.

**Lenny** (00:35:14):
Amazing.

**Kristen Berman** (00:35:14):
Yes, it is in the product, and they've done more global launches as well.

**Lenny** (00:35:19):
Sweet. I am clearly not sharing misinformation because I haven't seen it yet.

**Kristen Berman** (00:35:26):
You may not be searching the right thing. If you search medical, COVID, politics, you may get it.

**Lenny** (00:35:32):
Oh, boy. Here comes the decline of me. Okay. So, next case study that I thought would be fun to talk about is One Medical which I'm a happy customer of. What did you do with them?

**Kristen Berman** (00:35:44):
Yeah. Basically, One Medical asked us to increase engagement. This is a classic question. How do you increase engagement in a product or service, right?

**Lenny** (00:35:54):
Engagement, meaning just using it more often?

**Kristen Berman** (00:35:56):
Right, exactly. That's the real question, what does engagement mean? Actually, a have fun exercise that people could do with their teams is if you ask everyone on the team what engagement means separately, you can compare answers and most likely, people are saying different things. And if you guys can't agree internally on what to do or what engagement means, it's very difficult to build a product by which your users understand what to do.

**Lenny** (00:36:19):
Yup.

**Kristen Berman** (00:36:20):
Yeah. So, after lots of debate, we came up with a key behavior to target. Basically, somebody setting up a doctor's appointment right after signing up for One Medical. This is really important because more likely than not, you're going to sign up for One Medical, six months later, you're going to get a fever and get sick, and are you going to remember this app that you signed up for six months ago? Probably not.

**Kristen Berman** (00:36:44):
You're going to do the same thing you did before, which is call the doctor that you've normally gone to. So, really important for One Medical upfront, during onboarding, to set the mental model of what they can be used for in going to that doctor's appointment. Then, we looked to the barriers. One of the barriers, like, who is going to be your provider, your doctor. Picking somebody is hard. Finding an appointment time is hard. We're all busy people. How are you going to fit it in? Knowing actually what One Medical can help you with, also difficult. Like, what is this company thing and what should I go to them for? And then, the benefits. What are the benefits? And the benefits for using One Medical is you get your questions answered immediately. It's very simple, but you can really get your health questions and issues addressed. And so, the simple intervention we did was, just during onboarding, we asked people a few questions about their health; mental, sleep, physical. We then recommended a provider. So, instead of having lots of choice, we decreased the choice, recommended them one provider, told them why, and then recommended appointment times. And limited the amount of appointment times. It was for tomorrow. We recommended a virtual appointment so it'd be a quick thing that you could do from your home. And then, that intervention, the onboarding intervention, increased bookings by 20% during onboarding.

**Lenny** (00:38:06):
Of appointments?

**Kristen Berman** (00:38:07):
Of appointments, yeah.

**Lenny** (00:38:08):
With this-

**Kristen Berman** (00:38:11):
Onboarding. I don't know if I went through that when I joined One Medical.

**Kristen Berman** (00:38:13):
This is recent.

**Lenny** (00:38:14):
Okay, cool. Yeah. By the way, One Medical's awesome. As you're talking, I'm thinking if you could think about what are the five most commonly successful changes to a flow. One right now you just shared was reducing options, which is interesting.

**Kristen Berman** (00:38:31):
Yep.

**Lenny** (00:38:31):
And then, another you mentioned earlier is just reminding you of maybe what you're going to get out of it at the end. I don't know. Is there anything that comes to mind of here's a subset of things that seems to often work when you're trying to improve, say, activation or conversion of a flow?

**Kristen Berman** (00:38:46):
I would caveat all this with behavior is contextual. Why we are religious about testing is because it's hard to drag and drop from different contents. So, I'd caveat with that. And of course, there are some rules of thumb. So, one thing, really, is about showing people the benefit right away, really not under or overestimating that people understand the benefit of your app. So, how do you get them to experience it immediately? I would say that that's one.

**Kristen Berman** (00:39:17):
And then, the other is really just the reducing... I hate to sound so simplistic, but a lot of it is about making things easier logistically and cognitively, and making the benefit much more clear, salient. We say moving it from abstract to concrete. You really want to move something from the world of people can't really imagine how it would fit in their life to how does it actually fit in their life and keeping them going.

**Kristen Berman** (00:39:45):
If it's a long signup flow and people need to drop out, how do you send them reminders to pull them back in, and then when they are back in, land them on the spot that they were at. So, Wealthfront has said one of their key insights was when people dropped out of the flow, normally they would just put people back at the beginning. That's really frustrating. If you can put people back where they landed, they're more likely to continue.

**Lenny** (00:40:11):
That makes sense. Reduces barriers. I'm learning.

**Kristen Berman** (00:40:13):
Exactly.

**Lenny** (00:40:14):
So, there's two really interesting things you just said that I'd love to dive into a little bit. One is showing the benefit of something right away. Is there an example of that that comes to mind where you did that and it worked out really well? What's an example of showing a benefit?

**Kristen Berman** (00:40:30):
There's two ways to do benefits. One is the actual one that a consumer has. So, Asana and the collaborative communicator versus maybe one that's more immediate. When we're thinking about more immediate benefits, this could actually be things like social norms where you're telling people everybody else is doing something, and to them the benefit of doing this is following the herd. We all, by the way, don't like to think that we're part of the herd, but we all will succumb to this at some point in our lives.

**Kristen Berman** (00:41:00):
And so, one example is where we worked with a company called Study. This was a FinTech app and we're helping people to sign up or sync their bank account. Syncing their bank account is a required step in any kind of FinTech app, and yet so difficult, big drop off point. Just by reframing the choices of getting someone to think about completing a step versus the benefit that would come to them after... So, the benefit of syncing their bank account was actually huge. You'd get to see your income. You're really actually changing someone's financial picture by doing it, and they're signing up for it. They know it. But the small immediate benefit is how you're framing each step. Each step is going to give you the immediate benefit. So, for this one, it was a completion bias thing again where people are motivated to complete something. Sometimes we'll do an error message if it's really important for the app to work. And again, you shouldn't do that all the time, but if it's really important, the benefit is actually decreasing that error message on the screen. We call this Right for Wrong, doing the right thing for the wrong reason, where the right thing may be completing the flow, but the wrong reason is seeing that error message go away. Again, I would use that with caution. People will not use and love your app if you're putting error messages all over it.

**Lenny** (00:42:17):
That makes sense. I think you mentioned this. I haven't mentioned, but you wrote a guest post for my newsletter. It's one of the most read posts of the newsletter on just using...

**Kristen Berman** (00:42:25):
Cool.

**Lenny** (00:42:26):
... a lot of the... Yeah. I don't know if I told you that.

**Kristen Berman** (00:42:27):
Yeah. That's awesome.

**Lenny** (00:42:29):
And it's about using these insights to improve conversion in general. So, we'll link to that in the show notes. And I think, in that post, you mentioned this concept of Right for Wrong. It might be worth spending a little more time on this, just like what does that mean and what's an example that?

**Kristen Berman** (00:42:42):
When we think about Right For Wrong, we're helping people again do the right thing... So, this is a behavior that they want to do, but the reason is actually probably not related. So, if you think about just vaccines and what we saw here, the reason to get a vaccine is to help my neighbor and prevent them from getting sick. And yet, what happened? We gave people donut, give people free pot or marijuana. There were lottery tickets in Ohio. So, this is the Right for Wrong idea where you're really substituting... By the way, one of the bigger voting interventions is just having pizza show up at the poll line. You're motivating people to go vote not because they want to contribute to democracy, but because there's pizza in the poll line. So, at some level, we're pretty simple human where we want an immediate benefit. Clubhouse actually was an interesting example of this at some level where you saw two levels of status in Clubhouse. There were the people who were friends with the people on stage, and then there was everyone else. So, that was a motivator to be friends with more people and start following people so that you could be in that little bucket of friends with other people.

**Kristen Berman** (00:43:56):
So, we're giving people kind of some other reasons to do a thing that they may want to do, but they don't necessarily have the motivation to do it right away. If you think about Peloton, yes, I want to work out. Yes, I want to have a healthy person, but maybe I want to go to the class because the instructor making a shout out, or there's some streak that I'm trying to continue. So, their right for wrong here is the real reason to work out is to improve my physical health, but while I just want that instructor to give me a shout out.

**Lenny** (00:44:29):
So, the key there, just to kind of come back to the dark side of some of this stuff, is you want to make sure the end mean is good and right, whatever it is.

**Kristen Berman** (00:44:38):
Exactly, yeah. And so, again, all these things... The possibility of using anything for negative outcomes exist, and really it's about the incentives. It's what is your incentive to drive the customer benefit, and that's really where we say you have to be measuring the customer outcomes. You have to be focused on the customer outcomes.

**Kristen Berman** (00:44:58):
Some of the toughest teams we have understanding this are non-profits. We worked with one company a while ago. We tried to get them to add a deadline because they were trying to help people sign up for interviews. So, they were basically filtering people before Staples would get them for an interview. They'd do the interview prep. They'd help them show up for the interview. But the reality is that sometimes people miss this stuff. It takes a long time to get to the interview. And so, our push to them was to add a deadline to help people show up. Sometimes we say deadlines are a gift. You're just helping people kind of prioritize this. And they said, "No. Absolutely not. We cannot add a deadline. This is just too hurtful." And the reality is when you add deadlines, and we've done this in multiple companies, where you add a deadline, more people do the thing, right? Because you're helping kind of create the right for wrong reason, giving people the wrong reason to do the behavior that they actually want to do. We added a deadline to Kiva's flow for when their borrowers were signing up and we increased their conversion. So, obviously, you can use this in ways that are unintended and it really has some upside to help people.

**Lenny** (00:46:07):
I imagine you're building this just like toolbox of ideas that end up working often at flow. I know you said that you can't just copy and paste. Rarely is it just like, "Oh, this worked at 10 other companies, it'll probably work here." But that's kind of a cool thing that your team's probably doing just making this big list of here's 10, 20 things that we could start with these ideas and talk about them.

**Kristen Berman** (00:46:27):
Yeah. Once you understand the psychology of human behavior, you really start to understand and see patterns. We started with the idea that behavioral economics shows that people act in irrational ways, but we do it in predictable ways. And so, once you start understanding this, you can really start designing for the behavior change at this kind of predictable level.

**Lenny** (00:46:47):
For a product team that's listening to this and they're like, "Oh, we can't work with you guys right now. We can't afford it. We don't have time, just generally, but I want to think about this stuff and maybe implement it on my team." What would you suggest to say a PM leading a team that wants to implement some of these principles?

**Kristen Berman** (00:47:06):
Yeah. I would probably start from the process angle. We have the three B framework, which again, the most important step is defining the behavior. So, if you were to do a workshop with your team on what is the uncomfortably specific behavior that you want to change and you align everyone to this, it's going to be much easier for you to change that behavior because the psychology that drive that behavior will be a better conversation and more obvious.

**Kristen Berman** (00:47:31):
So, first in starting with the behavior, to get everyone in a room do a small workshop. The second would be the behavioral diagnosis. And this is the toolkit in behavioral science where we study not what people say they will do, but what they actually do. And so, the behavioral diagnosis, I'd say, it's like a journey map on steroids where you're really trying to map the steps that get people to the behavior change. And again, just doing this, teams have light bulbs. And this is one of the main things that we work with teams on; we help them do the behavioral diagnosis to have those light bulbs, and then we help diagnose and design the intervention.

**Lenny** (00:48:07):
Can you talk a bit more about this behavioral diagnosis step? What actually happens there?

**Kristen Berman** (00:48:11):
There's kind of two steps. One, you can outline the full high level flow where you're saying maybe there's 50 steps in getting to the behavior, and you can do this before they hit your product, too. But when we're working with just a very kind of... We want to help a team grow their product versus develop a new product, if it's just about growing and improving the current product, we'll do a deck of 200, 300 slides of screenshots where it's just very detailed analysis of the steps that it takes to get to the behavior change. And then, we overlay the psychologies that are driving people at each step. This actually takes a really long time, but the light bulbs of how you actually get to that beha... As I said, behavior change isn't easy. It's complex. It's hard. It's noisy. And so, you have to understand the steps that get you there before you're trying to change it.

**Lenny** (00:49:04):
Wow, that sounds really useful. So, you go through the product, make a screenshot of every little step, and then connect what barrier's keeping them from progressing. Is that roughly right?

**Kristen Berman** (00:49:15):
Exactly, yeah. So, maybe in a health app, it's information aversion. They don't actually want to see their test result. That's a step, and then we attach that psychology to that step and now we can have a brainstorm about, "Well, what would help decrease information aversion to get them over the next hump?"

**Lenny** (00:49:33):
What's cool about this is you could just... As a team, you have all these things you're trying to improve, all these flows and steps and things like that, and basically, these psychologies, as you call them, are useful to just anything you're trying to optimize. I imagine there's just like a list on Wikipedia of all these human psychologies and biases. I imagine a better way to learn about this is to take your course. So, maybe it's a good time to just chat about the course that you teach versus coming in house and working with the team. Can you talk a bit about that? Or are those the same thing?

**Kristen Berman** (00:50:02):
No, that's perfect. Yeah, so we have a... Thanks for the tee up, Lenny. Appreciate it. We have a bootcamp course, which basically is a self-paced online course that you can go in and understand. It has a lot of our case studies, many of them I didn't talk about here, and we walk you through the process. You'll have an intro call with us. There's a Slack group. There's office hours really trying to help people go through the process of behavioral design yourself, and it really brings these concepts to life and helps you apply them to your product. So, I think, starting with that bootcamp is a great place for designers, product managers, marketers, researchers to start. I can send you this. We have a Sweet 16, some of the 16 biases that we refer to most. The three Bs is an easy way to evaluate a product if you're just starting, but as you get deeper, these different psychologies will pop up.

**Lenny** (00:51:02):
Awesome. Please send that and we will link to it in the show notes. Just a couple more details in this course, how often do you run it? How long does it take generally for folks to take?

**Kristen Berman** (00:51:10):
Yeah. So, once a year we'll do a cohort course that's a little bit more in depth, but the best way is this kind of self-paced course. It's a eight-week course and we give you a month extra to go through it. There's 16 modules and there's homework throughout it that you can post in Slack and get feedback from behavioral scientists. So, a pretty interactive course, but you can go through it on your own and even share with your team. We do group things. We'll do like a team of 10, and then we can give you a private office hour where we just riff with you on your product challenges.

**Lenny** (00:51:46):
Awesome. And folks can find that at irrationallabs.com. Is that right?

**Kristen Berman** (00:51:49):
Yeah. Thanks again for this.

**Lenny** (00:51:50):
irrationallabs.

**Kristen Berman** (00:51:50):
Yeah, irrationallabs.com is the spot, and if you... Probably signing up for a newsletter is also... We publish all of our research there and other kind of fun behavioral insights.

**Lenny** (00:52:01):
Sweet. Well, with that, we've reached our exciting lightning round.

**Lenny** (00:52:05):
So, I'm just going to ask you a bunch of quick questions. Whatever comes to mind, fire away and we'll just go through them real fast. Sounds good?

**Kristen Berman** (00:52:11):
Great.

**Lenny** (00:52:12):
Okay, cool. What are two or three books that you recommend most to other people?

**Kristen Berman** (00:52:17):
I would be [inaudible 00:52:17] not to say Predictably Irrational. I think this is a great starter book for people getting interested in the field. Influence is also a great starter book for people getting interested in the field. Many times you read Influence and you change Your Career. It's a really powerful book. And then, the under-talked about one is [inaudible 00:52:35] author Robert Frank. He wrote Darwin Economy, and he talks more about kind of status, and social norms, and how this drives a lot of our behavior. So, I'd recommend Robert Frank as an author in Darwin Economy.

**Lenny** (00:52:48):
What's another favorite podcast other than the one you're currently on?

**Kristen Berman** (00:52:51):
Science of Change is my actual podcast, so a little self-promotion. We interview product leads and talk about what they've done in their product. And then, the other one is, No Stupid Question. This is by the Freakonomics. Stephen Dubner and Angela Duckworth come together and just answer questions about behavior change.

**Lenny** (00:53:11):
What's a favorite recent movie or TV show?

**Kristen Berman** (00:53:14):
I love The Rehearsal. This is-

**Lenny** (00:53:16):
I can see you loving it.

**Kristen Berman** (00:53:17):
Yeah. So, it's basically made me feel that it's rehearsing life. And I think, sports, it's so obvious you want to practice. I just started ping pong lessons actually, and I'm doing the same stroke for an hour. But in life, we don't rehearse as much. I don't write an email a hundred times, and then practice sending it. And so, I think there's probably an opportunity for us all to learn some lessons from that.

**Lenny** (00:53:42):
Have you seen Nathan For You, his other show?

**Kristen Berman** (00:53:44):
I have, yeah. The Rehearsal was just so compelling and I'm not usually somebody who watches media, so this was mind blowing. I loved it.

**Lenny** (00:53:52):
I actually like Nathan For You better.

**Kristen Berman** (00:53:54):
Oh, interesting. Okay.

**Lenny** (00:53:54):
Yeah.

**Kristen Berman** (00:53:54):
I'll give another...

**Lenny** (00:53:57):
What a weird show, but I love it. Okay, next. What is a favorite interview question that you like to ask?

**Kristen Berman** (00:54:03):
So, interview for... I'll take this as interviews for people when we're hiring. I would caveat to say, interviews, actually we know, don't predict job performance. So, very little to no evidence would say interviews will predict how I perform on the job.

**Lenny** (00:54:19):
Shush. Just kidding.

**Kristen Berman** (00:54:20):
We use skill assessments and trials as ways to predict job performance, but interviews are good at predicting affinity and culture fit. And so, if you want to ask a question about that, one of my favorite questions is just, what is a personality trait that defines you? So, really, one that you are filled with strength, but that also can be seen as something you're working to improve. So, for me, I may be confident, but that may mean that I'm not listening. And so, we have really strong personality. People are really quick at answering this question. They really know the thing that they do good but also could hurt them, and I find that it helps understand a person a little bit easier and faster.

**Lenny** (00:55:04):
Last question, who else in the industry do you most respect as a thought leader?

**Kristen Berman** (00:55:08):
I don't know if people will know him, but Chris York. He is a behavioral scientist, designer. I would go to Chris and ask him a question, and just accidentally, in the last year, had done full research on the question and has a very thoughtful answer. Chris York wins for me.

**Lenny** (00:55:32):
Amazing. Have not heard of him. We'll look him up. Kristen, thank you so much for being here. I feel like you're going to change a lot of people's behaviors. You're going to break barriers for a lot of products. And there'll be many benefits that come out of our chat. Thank you again for doing this.

**Kristen Berman** (00:55:47):
Wonderful. Thanks for having me, Lenny. This is super fun.

**Lenny** (00:55:50):
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.

---

## [2/20] Developing a growth model + marketplace growth strategy | Dan Hockenmaier (Faire, Thumbtack, Reforge)

**Dan Hockenmaier** (00:00:00):
One lesson I learned the hard way a bunch of times on this is that if you think about running a marketplace, you're basically like a gardener. You have to have a very light touch. If you're building a SaaS business, you're a construction worker, you're building the product and the features and selling it, and it's this very linear thing. For a marketplace, you're like messing with this ecosystem that you don't actually really understand how it works. And sometimes you might do something over here which drives this long-term effect two months later, and then you're going to be pulling your hair out two months later trying to figure out what you did over here that made that thing happen. So I think that the main advice is like to tread lightly. When you're messing with the core incentives or mechanisms of a marketplace, be very careful, particularly if you've got something that's working on playing with those variables.

**Dan Hockenmaier** (00:00:45):
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 Dan Hockenmaier. I venture to say that Dan has worked on more marketplace startups than anyone else in the world, including helping scale Thumbtack in the early days, currently working at Faire where he is head of strategy and analytics and, through his consulting business, Faces One, where he's helped dozens of startups figure out their growth models and growth strategies.

**Dan Hockenmaier** (00:01:20):
**Dan Hockenmaier** (00:01:45):
I'm excited to chat with my friend, John Cutler, from Podcast Sponsor Amplitude. Hey John.

**John Cutler** (00:01:49):
Hey Lenny. Excited to be here.

**Lenny** (00:01:51):
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** (00:02:02):
Well, we've always thought of Amplitude as being about supporting the full product loop, think collect data, inform [inaudible 00:02:08] 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** (00:02:23):
Supporting growth and learning has always been Amplitude's core focus, right?

**John Cutler** (00:02:27):
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** (00:02:36):
Absolutely agree. Thanks for joining us, John, and head to amplitude.com to get started.

**Lenny** (00:02:43):
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** (00:02:51):
At least 40%.

**Lenny** (00:02:52):
And how many of them screw that up and what happens when they do?

**Ashley** (00:02:56):
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** (00:03:15):
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** (00:03:30):
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, this because flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:03:47):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny.

**Lenny** (00:03:56):
Dan Hockenmaier, welcome to the podcast.

**Dan Hockenmaier** (00:03:59):
It's great to be here.

**Lenny** (00:04:01):
It's great to have you here. So we are actual real life friends and we've collaborated on a number of writing projects, including the race car growth framework and a whole thing on consumer growth strategy. But there's a couple topics that we've never actually dug deep into and that you haven't written about. So I'm really excited to dig into two specific things in our chat today.

**Lenny** (00:04:23):
One is growth models and two is just marketplace growth strategy and all things around marketplace growth. But before we get into all that, can you just give us a 55 second background on all of the wonderful things that you've done in your career?

**Dan Hockenmaier** (00:04:36):
Yeah, absolutely. So I feel very fortunate being able to work on a bunch of consumer and marketplace businesses for a long time. I started in consulting at BCG and then in private equity. I don't think I learned much about how to actually run a business at those places, but I did learn a lot about how to think about them. I think my real education on this began at Thumbtack. So I joined when there were about 30 people and we just had to figure it out. I was there for a little over three years and we more than 10Xed the business in that time.

**Dan Hockenmaier** (00:05:02):
From there I built a strategy consulting firm where we worked with a bunch of the top gross stage marketplaces on a range of topics, and ultimately that firm was acquired by Faire where I am today. So I lead the strategy analytics team at Faire. I think this is probably the most fun I've ever had in my career. It's just the incredible mix of the team. The business is really strong and I love the customers we're serving. So it's a marketplace connecting local retailers and independent brands, and I just think that's a really fun group of customers to build for.

**Lenn** (00:05:31):
Awesome. And we're going to chat a bit about the stuff that you do there and marketplaces. But before we get into marketplaces, I wanted to start with our first topic, which is around growth models. So people may have heard this term, this general idea. Just to set the stage, can you just describe what is a growth model and why is it useful to think about your business through the lens of a growth model?

**Dan Hockenmaier** (00:05:54):
So I think it's useful in many contexts. If I apply it to the current work that I'm doing, the strategy analytics team at Faire does a bunch of work to help our other teams make better decisions. So we're typically diving really deep into a bunch of topics across the business. I think it's really easy to make that work kind of go off the rails or go too deep unless you have a conceptual understanding of how the whole business that it comes together. And that's how I think about a growth model, so the analytical representation of how the business grows and it's typically built in a spreadsheet which has a really nice feature of being very hard to fake. You can talk about a business conceptually, but when you actually have to get it to line up and link in a model, it's very hard to not force yourself to understand how the business works. So I think it's very valuable for that.

**Dan Hockenmaier** (00:06:37):
I think 50% of the value you get from it is simply building the model. It forces you to understand it and then you get this artifact which you can use to understand how to weigh different opportunities or understand the benefit of working on different things. I think importantly it is not a forecasting tool, so it's not going to replace what your finance team is building to project the business. In fact, often the output can be highly variable because you're playing with lots of these assumptions, but it is a great tool for kind of opportunity assessment for the business.

**Lenny** (00:07:05):
Awesome. So maybe a simple way to think about it, just summarizing, is it's essentially a formula for your business that often lives in Excel that kind of summarizes and puts together all the things that can drive your business. Is that a simple way [inaudible 00:07:19]?

**Dan Hockenmaier** (00:07:18):
Yeah. That's exactly right.

**Lenny** (00:07:20):
Sweet. So we're going to go through examples of these growth models and how you've thought about this in actual potential formulas for companies. But first, just broadly, how would someone approach figuring this out for themselves? How would you build a growth model for your own business?

**Dan Hockenmaier** (00:07:35):
So if you think about some of the basic building blocks and probably the simplest use case would be a SaaS business, there's really three components that you need to build for that. One is to understand your acquisition channels. Are you looking at paid marketing or sales or viral kind of customer referrals? And for each of those you have some different assumptions around traffic or spend or conversion rate, those kind of things. So that's the first section. Second would be retention. So at what rate are these customers activating? And then have some kind of basic monthly retention curve. So how long are they staying around? What's the survival rate in each of these? And those kind of stack over time. And then you have monetization. So in the simplest example, they might be paying you some monthly or annual fee and so that translates in monetization.

**Dan Hockenmaier** (00:08:13):
So actually if you're modeling a relatively simple SaaS business, those are the only core building blocks you need and you add a lot more complexity on it based on your kind of individual business that you're building. If you then are trying to build this for more of a transactional business, you need to layer on the way that your current kind of retained customers start to transact. So how many transactions per month? What's the AOV? And then you're also going to typically need to build unit economics because those businesses often have higher costs. And so you're going to be thinking about cogs or other major costs that you build into it.

**Dan Hockenmaier** (00:08:39):
And then one click beyond that would be to build this for marketplace business. So now what we've talked about is mostly modeling like the demand side of a business. So now you'd also need to think about supply acquisition and retention and how these two sides interact. So as we add supply, what's going to happen to demand? But those are the basic pieces. I think you can start pretty linear like acquiring customers, they're activating, retaining and generating contribution margin typically would be the output. But where it gets really interesting is we start making it non-linear. So the most basic example of this would be virality. Your existing customers are referring new customers and those go on to refer new customers. Based on that coefficient, it has a lot to do with how fast your business grows.

**Dan Hockenmaier** (00:09:17):
And similarly with paid marketing, as you generate contribution margin, you can reinvest that and grow and actually if you link those two up explicitly, it makes it really clear why thinking about something like payback period is a much better measure of paid marketing performance than LTV to CAC because the speed at which you get enough money back to then go acquire another customer has much more bearing on how fast your business can grow than just the raw kind of [inaudible 00:09:39]. This is where it gets really interesting where you get some variables to play with.

**Lenny** (00:09:43):
Okay. So let's unpack a bit of the stuff you just talked about. There's a whole decade of knowledge that you just I think collapsed into a couple of minutes. So just to spend a little more time there. So the core three kind of variables to a SaaS business, if you're thinking about the growth model of a SaaS business, for example, you said acquisition channels, where's traffic coming from, and that's essentially how much traffic are you getting, how is it converting and things like that.

**Dan Hockenmaier** (00:10:07):
Exactly.

**Lenny** (00:10:07):
And then there's retention and then there's monetization and multiplying all that together you end up with here's how much revenue you're making as a business. Is that roughly how to think about it?

**Dan Hockenmaier** (00:10:14):
Yeah, it's roughly right. And those three building blocks are true for here in most businesses. Most of what we're talking about is then nuance on top of that that makes the business unique.

**Lenny** (00:10:22):
Cool. So if someone was just starting the spreadsheet for their SaaS business, and we'll talk about even more examples, but if someone was like, "Here, I'm going to try to figure out my growth model," it's create a row for acquisition channels and traffic you're getting, then a row for roughly your retention rate and then how much you're making per customer. Very high level, is that to think about this?

**Dan Hockenmaier** (00:10:42):
Yeah, exactly.

**Lenny** (00:10:43):
Okay, sweet. And then marketplaces, I think you said that it's transaction over time and average order value. So it's like how many people are buying stuff, how much are they paying each time? And then unit economics per transaction, how much they're making profit per [inaudible 00:10:58].

**Dan Hockenmaier** (00:10:57):
Yeah, exactly. And the critical distinction there is for a SaaS business, your marginal costs are often very low. And so it's not an important part to model. But for transactional business, you typically have very high cost or something else that you need to model so [inaudible 00:11:09].

**Lenny** (00:11:08):
Right, because you're just taking a cut and you're not selling software. And then the acquisition channels, retention, monetization, marketplace have those three things just broadly and then plus these additional two elements.

**Dan Hockenmaier** (00:11:19):
Yeah. I think one warning I would give ... so I built these for many businesses. I built them for Thumbtack, at Faire. Many of the companies I worked with, at my consulting firm, they break down in a few places. As soon as you start stacking assumptions, you're highly sensitive to how many assumptions do you have to make and do you know how to make that assumption. And marketplaces kind of create complexity on both of those because for the first piece you're modeling both sides of the business. There's a lot of assumptions. And second, there's a few pieces which are very hard to understand how they work. So the interaction between supply and demand is a big one. Take Amazon as an example. There's a category manager at Amazon who's running their pets business and he decides that he wants to go add a bunch more pet supply to the business. So he's going to go find pet food brands, pet toy brands. Those businesses will generate a bunch of revenue on the Amazon marketplace.

**Dan Hockenmaier** (00:12:03):
But how much of that was actually incremental? Maybe there's a bunch of existing pet supply that customers would've bought anyway. And does having a bunch more supply create a happier customer who retains longer and drives those cohorts up? These things are very hard to decide, something we've spent a lot of time thinking about in various marketplace businesses. And so if you're not careful, you can have a junk in, junk out problem with marketplaces. So the thing that I have gravitated to more as I've done more of this is one very basic high level conceptual model, so that's like the building blocks you talked about, which as simply as possible describes how the whole system works. And so you start to get a feel for which levers are important.

**Dan Hockenmaier** (00:12:39):
And then for each area of the business, so each product pod, each go to market team, they should have their own kind of mini model which describes the piece of the business they're working on. So that team typically has a north star and they should know what are all the inputs that drive that and a little model to articulate how that works. And you'll never kind of stitch this up into one master thing. I think that's a very difficult task. But you have the dual benefit of understanding how the business works broadly and then understanding if you zoom in on this piece, what are the levers i need to be pulling to move my metric.

**Lenny** (00:13:07):
To make that last point a little more concrete, what's an example of that? What's a team that would have their little model? I imagine every team has their own understanding of how the lever works, but what's an example?

**Dan Hockenmaier** (00:13:17):
I think there's probably two core archetypes for this. So if you have something that's more like a growth team, it's a little bit simpler. They're typically managing some kind of funnel and they can understand do I want to work on driving more traffic, more conversion, more retention. Typically, that's a somewhat linear relationship.

**Dan Hockenmaier** (00:13:32):
But then you have all these teams that are really managing some tension in the business, which is totally different than a funnel. So say if you have a marketplace quality team, what they care about is driving some standard for quality for the suppliers on a marketplace, but there's not a linear kind of relationship between working on that kind of problem. So if I let on a bunch of new supply to a marketplace, probably the first thing that happens is our GMV or our revenue goes up because we have all these new suppliers which can transact demand, but if those are on average lower quality, it's going to degrade the kind of customer experience and reduce retention over time. And so the model that they're trying to build is how to manage that tension.

**Dan Hockenmaier** (00:14:08):
Similarly in a FinTech business or many marketplaces now have FinTech elements, you're often underwriting the transaction. That team is thinking about the tension between extending more credit and driving higher spend versus defaults on the other side, like what's the contribution margin maximizing point at which we could offer credit. And so their models are going to look pretty different than what a growth team is managing.

**Lenny** (00:14:29):
Got it. So you mentioned this idea of archetypes and I was going to ask you when you think about developing a growth model for a company and with Basis One, the company that you ran before Faire, you basically developed these things for startups and how many companies would you say you helped through this process and helped develop growth models for just to [inaudible 00:14:47]?

**Dan Hockenmaier** (00:14:47):
We probably built 20 or 30 these in my time at Basis One.

**Lenny** (00:14:49):
Awesome. It's probably more than anyone out there. So I think that's a context to set. You've had more experience doing this than maybe anyone else out there, but we won't compare.

**Lenny** (00:14:58):
Are there archetypes/templates/tools that you have found useful to think about, I'm coming in fresh to think about the growth model for a company. What have you found helpful to get started to lay the groundwork?

**Dan Hockenmaier** (00:15:11):
One thing I'll say is going back to 50% of the value being figuring it out, that actually negates the value of templates in some way. You kind of want to build it up for yourself from first principles to understand how the business works. So the more painful the process of building it is, probably the more you're learning. But I do think there's been a lot written on this that you can find online and I think the building blocks I talked about are a useful starting place for how to put these together. I also think Reforge, which is a product in growth school, which we both know has done I think probably the most work to build this into a discipline. And so if you want to go really deep on this, my top recommendation would be to start with Reforge.

**Lenny** (00:15:45):
Okay. So getting even more concrete, you've built a lot of these growth models. What's an actual example of growth model you've built and more specifically what have you learned from the experience of building that growth model at either, I guess, I was going to say a fictional company but let's go with a real company?

**Dan Hockenmaier** (00:16:00):
One of the immediate things that you see when you build these is that your growth is much more sensitive to customer retention than you can ever intuit because there's a lot of interaction between having a healthy retained customer base and everything else you care about, which is the rate at which they're referring new customers, generating content, generating contribution margin. And so it quickly makes it clear that actually getting a smaller percentage gain on retention is often much more valuable than making a bigger change in some other area. And as a result you may be misallocating your product and growth resources in a pretty significant way.

**Lenny** (00:16:35):
So your point there is really important that the more you work on this stuff, the more you will learn what actually is movable and the expected ROI on investments. For founders that are just getting started on this sort of stuff, do you have any just general advice or guidance on okay, retention is probably going to be very hard to move, don't expect that metric even though it's your point that it's often the biggest lever? Any just general guidance of here's where you probably will see impact, maybe you should now count on a ton. How do you think about that?

**Dan Hockenmaier** (00:17:04):
I think one tactical piece of advice, I think the best way to start this is to find a smart analyst or smart finance person often is the right type of person to partner with and just start building it. So you may have some intuition around this for the core operating model the business is running. This is a little bit different. You need to start building in more variables but I would start there and start iterating on the model. And I think this process of where you have leverage to move it is very hard to intuit. So I think you just have to start and there's a feedback loop between what kind of gains the team is putting up and how that impacts your model and over the course of multiple quarters of iterating on this, you build much more intuition for what works.

**Lenny** (00:17:41):
Awesome. So say that somebody has been listening to this episode, maybe they've heard it, they've listened to it three times now and they're just like, "Hey, I got a model that kind of feels like the beginnings of something." What do you do once you have a growth model? How does it actually inform what you do as a startup?

**Dan Hockenmaier** (00:17:56):
It's very helpful input into a quarterly or annual planning process. It depends a little bit on the stage of the company, but say you're at the stage where you have maybe 10 or 20 product pods which are allocated across various parts of the business and you're going through annual planning. Often you want to do a zero based accounting exercise where we say we want to from the ground up decide how those people should spend their time and there's some kind of pod allocation exercise where we're deciding which places those go to. The most difficult thing about making that kind of effort is developing a common currency by which you can trade off their efforts. So this team is saying they can move this metric by X and this team is moving this metric by Y. I have no way to make those two things comparable. The growth model is the function that lets you do that.

**Dan Hockenmaier** (00:18:36):
And so you can have this analyst or this finance person we talked about who is operating this model work with the product managers to run those scenarios through this model and generate it into a common currency. So now we have a spreadsheet that says these are the things we could work on. This is roughly how it will impact our short or long-term growth. Now you have the ability to make much better kind of allocation decisions. So that would be at the most macro level. And I think the more micro one is for an individual product pod, I have this north star goal, which levers should I be pulling? They should be using their mini models to make that assessment. If you look at the strategy doc for a product group or team, I think that having a model like this should be a core part of that because that way they can articulate what it is they actually [inaudible 00:19:18].

**Lenny** (00:19:18):
Have you found a model doing this exercise, coming up with a growth model for a company or a startup you've worked with, radically shifted the way they think? Is there an example that comes to mind of, "Oh wow, we came up with this," and they're like they didn't even know this was a huge lever and that changed the way they approached growth.

**Dan Hockenmaier** (00:19:32):
I mean the first time this was very eye-opening to me and probably the first one I built was the one we built at Thumbtack in partnership with our finance team, and it made it so immediately obvious that we were exceptionally sensitive to the repeat rate of new customers. If you think about Thumbtack, we offered a thousand categories. This is a local services marketplace for people to hire electricians or plumbers or wedding planners. Almost all the traffic came from a very targeted SEM or SEO on a specific thing. So they hired [inaudible 00:20:01].

**Dan Hockenmaier** (00:20:01):
Initially, it was very hard for us to then go upsell you into something else, but the rate at which we did that made all the difference because it radically changed the LTV of that customer, which then fed back into how much we could go pay to acquire new customers. And so we had a team that was primarily focused on optimizing that initial flow. So SEO and conversion rate. We shipped hundreds of experiments to increase our conversion rate. We had done much less on the life cycle piece like how do we cross sell you into these other things. Building this model helped us internalize that we needed to shift a bunch of resources from top of funnel to deeper in the stack and that ultimately let us build a much better customer journey.

**Lenny** (00:20:36):
Awesome. Your point about retention being one of the biggest levers reminds me at Airbnb there's like a data dive once where a data scientist found that same conclusion. "Man, if we move retention by 1%, we're going to hit all our goals." And we tried and it was just very hard. And I'm curious, how often do you find that you can actually meaningfully move retention or is there anything that you've found to be effective in increasing retention for many of the companies that you've worked at?

**Dan Hockenmaier** (00:21:04):
Retention is a tough measure to work on because it is the culmination of the entire product experience. Whether people come back or not has to do with everything that they experienced along the way. And so I think that the primary advice is actually if you were trying to remove a retention style metric, rarely should you go right to the source and send them more email or push notification or something like that. It's really actually about understanding what is the customer experience and what matters to them. And in a marketplace context, it's often depth of supply or the interaction they have with supply. So you actually should be working more on core product levers than you are on, call it, growth product levers to move retention. So it's a deep understanding of that customer journey and where you actually have the opportunity to improve it.

**Lenny** (00:21:43):
If you can share any idea or any example comes to mind, what's one of the biggest successes you've seen in increasing retention?

**Dan Hockenmaier** (00:21:49):
Very often I think the biggest wins in retention come from inflecting the early user experience. So if you're at three, six, twelve months out, usually a customer has formed a pretty strong opinion about whether or not they like this product and they have a pretty good understanding of it. But in that very first experience, you have a lot of opportunity to teach them about why this is a valuable product and kind of prove to them that it's valuable. So the experiments that have been most effective have been typically focused on very early life cycle, and one really valuable lens is to look for variability in that experience. So for the first week or month, which customers are having a bad experience but shouldn't be.

**Dan Hockenmaier** (00:22:27):
So if you take Lyft or Uber, for example, an Uber driver signs up for the service. Some of them just by luck of the draw are going to make a pretty bad hourly rate because a customer canceled on them or they were just in a low density area, and there was some problem with their experience. That driver doesn't know that's not how it works. They might think, "I just make $3 an hour on this platform," and they're never going to come back. And so if you can target streamlining that experience or homogenizing that experience, it's typically very helpful. This is why you see both of those companies dueling it out to guarantee the highest first first week or first month earning. What they're trying to do is prove to you that this is what the experience is going to be like longer term, and you pull up all those below average first experiences to average and drive much better retention curves going forward.

**Lenny** (00:23:12):
Amazing. Such a great example and story. It makes me think about this work that I imagine every company ends up doing, which is what are leading indicators of future retention. I'm curious if you've had success doing that. I find there's always these obvious things that you can't do much about to increase retention down the road and there's always this idea of building some ML model that's like anticipating retention based on some behaviors that someone takes. Have you had any experience, any success with those sorts of investments?

**Dan Hockenmaier** (00:23:41):
I think one of the most common analytical failure modes is this pattern, which is our best users do X, so why can't we make other users do that same thing and then drive future attention. It almost never works that way because there's something unique about that customer and their experience which is driving it. And so these correlational exercises, I put very little weight in because I've rarely been able to move Bucket B into the better Bucket A, for example. So I think it's much more about understanding where the real drivers of value are, how to create that really good first round experience to prove to them.

**Lenny** (00:24:12):
Awesome. And it's interesting that onboarding comes up a lot on these conversations, just the power of onboarding and how much effect that has down the road.

**Lenny** (00:24:20):
To your point, people often want to increase retention by focusing on people about to turn and this is a great reminder that your biggest lever is early on when they're just experiencing for the first time.

**Dan Hockenmaier** (00:24:30):
So yeah, the flip side is absolutely true, right? Working on early user experience is highly impactful. You often see product teams say we should work on resurrection because we have this huge pool of users that is churned out. If we get just 1% of those people back, it's going to be such a big lift. The problem is that pool of users is the group of people who has tried the product and decided they don't want to use it and so it's very hard to convince them otherwise. It's usually much higher leverage to focus on new users and, as a result, typically you want to wait to spin up resurrection efforts until you've exhausted some of these earlier funnel efforts.

**Lenny** (00:25:02):
So I want to transition a bit to talking about marketplaces. I honestly can't think of anyone that's worked on more marketplace companies than you. Maybe Jeff Jordan at a16z who's invested in Airbnb and worked at eBay and OpenTable and these companies. But I feel you have so much insight into how to grow and run a marketplace and so I'm really excited to dig in to stuff here.

**Lenny** (00:25:23):
My first question, just why are you excited about marketplaces? What gets you continuously interested in working on marketplaces and why are they such interesting and good businesses?

**Dan Hockenmaier** (00:25:32):
Why is a marketplace a good business? The first thing is it's like a perfect fit for the venture model, which is why everybody's so interested in them, right? They're very hard to get started, super capital intensive to get started, but once they're rolling, they're very hard to stop. You get this kind of compounding defensibility and gains that makes them very hard to stop. And, as a result, as a marketplace grows, you see these crazy things in the metrics which you don't see for most other businesses. So typically, as you acquire more and more customers, you're acquiring the marginally good fit customer over time and your CACs go up, your LTVs go down, it gets harder and harder.

**Dan Hockenmaier** (00:26:08):
Marketplace is actually the inverse. The supply liquidity is improving, the experience is improving. So often actually as you see later cohorts in marketplaces, CAC goes down, LTV goes up. You see this crazy inversion where the business gets better and better over time. And so that's I think one of the reasons they're such great businesses. I think to your question on why they're fun to work on, I think everything is just harder. Every question is more complex and so that's made them I think really fun to work on for me.

**Lenny** (00:26:37):
And that's interesting coming back to your first point about marketplaces are hard to start, but once they're started they become cheaper to grow and you build moats and work effects. It feels like you as a advisor and person that works on marketplaces, the same thing happens. The fact that you've worked at so many marketplaces makes it more interesting and fun I imagine because you've seen so much of this and so many people haven't experienced this, and so there's almost a Dan Hockenmaier network effect.

**Dan Hockenmaier** (00:27:02):
I appreciate that. I mean I think there's a few folks in this community who've worked with a bunch of marketplace, and you start to see the same topics over and over. So it's really fun to riff with that group on these topics.

**Lenny** (00:27:12):
**Dan Hockenmaier** (00:28:36):
I can give you a couple of pretty obvious ones or basic ones and a couple that are a little bit more nuanced. So that in that first bucket, certainly you need to look at some measure of GMV or transactions. You need something that brings together both the supply and demand side to make sure it's working and that's typically your ultimate north star of which everything else ladders up to.

**Dan Hockenmaier** (00:28:54):
I think the second would be a deep understanding of unit economics because the dynamic I talked about where they're hard to get started means that most marketplace in the early days have pretty poor or maybe even negative unit economics. Instacart famously was losing the money on every order. Uber was losing money on every drive. And so I think understanding that and the components that lead up to it is a very important part of understanding your marketable. So those would be the two kind of obvious ones.

**Dan Hockenmaier** (00:29:19):
I think other two that I would look at beyond that, number one is liquidity. And this is a really broad term that people define in a bunch of different ways. The definition I would give is how reliable is the marketplace? If the consumer is looking for something or supplier is looking to sell something, how often can they do that thing that they're trying to do? And ideally you want to express this metric in the form of a dimension or a type of product experience that a customer really cares about. So for Uber or Lyft, wait time is a classic example. As you add more supply, the average wait time for a customer goes down and there's some magic moment around four or five minutes where it really clicks and is now just a much better service than calling a traditional taxi or something else.

**Dan Hockenmaier** (00:30:01):
For a commerce market, typically it's some form of conversion rate or search to fail metrics. So if I go look for this thing on Amazon, how often can I find it and convert? And so by articulating what the customer cares about and where this threshold is, you can tell when you have a liquid marketplace and essentially until you have a liquid marketplace, really nothing else matters. So this should be the primary thing you're focused on defining and then building towards, and this is why you hear a lot of advice to marketplaces to basically cut scope down to a specific geography or a specific category so you can focus on generating liquidity in that area before you can then scale it elsewhere. So this is the number one, I think, metric for a marketplace.

**Dan Hockenmaier** (00:30:41):
And then the last one I'll give is share of wallet. So this is effectively for your buyer, how much of their total spend are you getting on your marketplaces versus the alternatives. For your seller, how much of the business that they're doing is you versus others? So for Uber drivers, if they spend X amount of hours driving per week, how much are you getting versus Lyft or Door Dash or something else? For a retailer on Faire, if they're buying to stock their store, how much of the product on their shelf came from Faire versus from somewhere else? These are very important metrics for us to understand.

**Dan Hockenmaier** (00:31:11):
One, for the obvious reason that as it goes up, your LTVs go up and you have a much better business. But probably more importantly than that, the higher it is, the less likely a customer is to multi-tenant, meaning use another marketplace or another service. And ideally you want that customer to commit to using just this marketplace and the higher share of wallet is the more likely that is. But I will say that it's very hard typically to get this to happen on both sides of the marketplace simultaneously. So often you have to pick your leverage point, which one do you think you can actually drive very high share of wallet on.

**Lenny** (00:31:41):
Awesome. Okay. So just to summarize, the metrics that you find to be most helpful in tracking marketplace health, there's these two that are just general business health metrics, GMV and unit economics. Then I think what's most unique to marketplaces, which is liquidity and essentially it's just like how often are people having a good time on both sides of the marketplace? And I love the way you broke it up like for Uber it would be how quickly do you get a car. For most marketplaces, it's just like what percentage of the time do you get something that you want, fill rate basically. And then share a wallet, which to me feels like ... even again going back to the first kind of bucket of just broadly this business going well, do you think about that separately versus just business growth and how much we're making, do you feel like share of wallet is a different category of metric?

**Dan Hockenmaier** (00:32:30):
I do think share of wallet is different for this reason. If you could tell me we could grow GMV 10% by getting 10% more customers or by getting 10% more of our current customers' wallet, I would take the latter because you now have a deeper relationship with them, which tells you something more about the future retention and defensibility of the marketplace. So I think it's basically a measure of depth rather than breadth. And I will take depth every time in a marketplace.

**Lenny** (00:32:57):
Awesome. You worked on consumer and B2B marketplaces and so I'm curious, do you find share of wallet is important on both types of marketplaces or is it a lot more important in B2B?

**Dan Hockenmaier** (00:33:06):
So you typically have some form of business on the supply side of a marketplace. Maybe it's a pseudo business that's effectively a consumer, but you can almost always measure some form of share of wallet on the supply side of a marketplace no matter what. On the consumer side, if you're a B2B marketplace, you typically have a cleaner share of wallet metric, but it's not always the case for consumer businesses.

**Lenny** (00:33:25):
Sweet. And again, just to clarify share of wallet, it's essentially percentage of spend in, say, a problem space that they're giving to you. So for Faire, it'd be like the retailers, what percentage of their vendors come through Faire?

**Dan Hockenmaier** (00:33:39):
Exactly. If you look at their shelf in their store, what percentage of that shelf came from Faire versus something else?

**Lenny** (00:33:45):
Awesome. Another constant question marketplace founders have is whether they should focus on supply or demand. And I know it's never black and white, but do you have any general advice on where to focus?

**Dan Hockenmaier** (00:34:00):
Yeah. I mean the answer is obviously both to some extent. I think you can't ignore either side. I do think though that on average when you hear advice about where to focus, people over rotate on supply and actually are under focused on demand. And I think there's a couple of reasons for this. One is supply is disproportionately important early on because it is the product. Until you have enough supply, you don't have anything and so you do have to focus on it to a high degree early on. And two is often the supply side of marketplace is using the product more deeply. There's more product surface area and you need more product resources on the supply side.

**Dan Hockenmaier** (00:34:35):
However, I think this tricks people into thinking that that's the optimization function or you think you should think more about supply. I think ultimately demand is the only thing that matters. If you are successful at aggregating the demand in your industry, you will have the winning marketplace. Because if you go to a supplier, a restaurant or an electrician or a driver and say, "I have this customer for you that I can give to you at a rate that's going to make you money," they're always going to say yes. And so demand is the currency. And so when you think about trade-offs or how to optimize a business, I think taking the perspective of the customer or the demand side is always the right one.

**Lenny** (00:35:11):
I think there's a really important nuance here, and there's actually a little mini Twitter debate with Bill Gurley I think a while ago where he made the same point that in the end, the most important thing you got to get right is aggregate all the demand. You need to become the place people come to transact in that space. But oftentimes the way you do that is acquire supply that is hard to acquire. And so would you agree with that? Often it's just, yes, prioritize the customer experience, but that may be you need to spend most of your time acquiring supply so that they're happy.

**Dan Hockenmaier** (00:35:40):
Absolutely. And the culmination of those two points is you only should acquire supply to the extent you understand how it impacts demand. So, for example, if we go back to this liquidity metric, there is some point for a market for Uber where you don't want more supply because you're no longer reducing wait times or doing something that improves the customer experience in a meaningful way. And similarly to the kind of pet store example on Amazon, there's some amount of supply where you're probably no longer incrementally improving the pet buyer's experience and so it's probably not worth investing those dollars. So supply is critically important, but it has to be framed from what is the customer benefit that I'm driving.

**Lenny** (00:36:17):
And another way to put that is what's the biggest constraint to your marketplace's growth, right?

**Dan Hockenmaier** (00:36:21):
Right.

**Lenny** (00:36:22):
While we're on that topic, do you have any just rough heuristic that you use to understand which side is most constrained? This may be a big question that isn't answerable in a short answer, but any thoughts there?

**Dan Hockenmaier** (00:36:35):
One is I've actually become less and less focused on pure marketplace balance metrics. They're important to monitor, so ratio of buyers to sellers, some of these other things. But actually the thing that matters is can you write an ROI equation for acquiring supply and demand which fully internalizes the marketplace dynamic. So what I mean by this is if you're acquiring a new customer, you need to include the CAC of acquiring that customer, but also the CAC of acquiring the supply for that customer to purchase, which is based on some ratio between the two.

**Dan Hockenmaier** (00:37:09):
And similarly on the supply side, that business can't make a sale unless you also acquire the customer to transact with them. And so if you have dual-sided ROI equations which are appropriately capturing this dynamic, actually I think you can somewhat ignore marketplace balance and just push your acquisition all the way out to the payback period that you're comfortable with on either side. I think the one exception to this would be are there externalities which you can't capture in this equation. So for example, if you have too little demand for Uber drivers, at some point do they just become disillusioned with the service, switch to Lyft, talk badly about it on social media. You do have to look out for extreme low supply or demand scenarios. But generally my view is build really strong ROI models that account for this and then just push to your threshold.

**Lenny** (00:37:57):
I like the sound of these ROI models. Do you have any guidance for folks to come up with these models in some way? Or is that a whole master class of its own?

**Dan Hockenmaier** (00:38:06):
So there's a lot of nuance by business, but the basic formulation is CAC for the side you're focused on. So let's take Uber again, as an example. CAC to acquire a rider and then an additional amount of CAC loaded on for the supply, the drivers that you're acquiring, times the ratio of drivers to supply you're acquiring at that time. So basically, do I need one driver for every 10 passengers? We then take the CAC of that passenger times 10% of a driver. That gives you CAC and then you compare that to the LTV of the customer, and that allows you to calculate payback period.

**Dan Hockenmaier** (00:38:44):
Now there's a lot of nuance when you get into an actual marketplace because often they're referring other sides of the marketplace or other things are happening. But that's the basic formulation.

**Lenny** (00:38:53):
Wow. Okay. We should do an actual master class on this formula concoction.

**Lenny** (00:38:57):
A question I wanted to cover also is I find that for early stage marketplaces, founders sometimes over focus on the theory of marketplaces and how all this stuff that people have put out, including yourself and others, about just how to think about marketplace, all the complexity there. But I find that oftentimes it's simpler just to think of a marketplace like 90 something percent of your success is going to be the same things that any business will have to deal with, growth and profit and retention, all these things. And then there's these additional layers that make a marketplace more complicated. And so just to double click on that last piece, what have you found to be most different about working on a marketplace business versus non-marketplace business?

**Dan Hockenmaier** (00:39:43):
Yeah, it's a good question. So I think that effectively every decision you make in a marketplace has a second order consequence that you need to think through and maybe third and fourth order consequences at that. Take something like pricing. It's like this is a pretty complicated topic no matter what, but if you're looking at a SaaS business and you're trying to figure out how to price your subscription, theoretically you can draw a curve which says, "As my price goes up, fewer are going to convert," and so just find the optimal point on that curve where we're managing the tangent between more customers versus more revenue per customer.

**Dan Hockenmaier** (00:40:15):
But if you take a marketplace, typically you're charging commission on the supply side and their sensitivity to that commission is much harder to understand because, theoretically, if they can transact at a rate that makes them money, they'll sign up all the way to that highest possible commission you could charge. The more you charge, the more you can fund benefits for your customers. So if Amazon charges a higher commission, they can fund more returns and faster shipping for their customers. And so what's the right balance between charging more and maybe kind of discouraging supply from signing up to giving more benefits to demand and encouraging them to sign up?

**Dan Hockenmaier** (00:40:52):
So it's very hard to model that kind of relationship. There's not a simple curve that describes it and so many decisions follow this same pattern. And one lesson I've learned the hard way a bunch of times on this is that if you think about running a marketplace, you're basically a gardener. You have to have a very light touch. If you're building a SaaS business, you're a construction worker, you're building the product and the features and selling it, and it's this very linear thing. For a marketplace, you're messing with this ecosystem that you don't actually really understand how it works. Sometimes you might do something over here which drives this long-term effect two months later and then you're going to be pulling your hair out two months later trying to figure out what you did over here that made that thing happen.

**Dan Hockenmaier** (00:41:30):
And so I think that the main advice is to tread lightly. When you're messing with the core incentives or mechanisms of a marketplace, be very careful, particularly if you got something that's working on playing with those variables.

**Lenny** (00:41:42):
I love that metaphor and your point about pricing reminds me ... Your colleague at Faire, Carla Pellicano, she led the pricing recommendations team at Airbnb. It was a team of, I don't know, probably a hundred people that were just dedicated to pricing, figuring out what prices to recommend to hosts, how to get them to adopt these recommendations, building a model to actually come up with the recommendations. And so to your point, pricing is such a complex beast and especially in a marketplace.

**Dan Hockenmaier** (00:42:09):
Absolutely. And in general, Carla's been such an incredible force in growing our team and helping us think more rigorously about marketplaces. This is one of the things I mentioned at the start that makes Faire so fun is we've got a lot of people like this that are just so fun to riff with on marketplace problems.

**Lenny** (00:42:23):
There's so many ex-Airbnb people at Faire. It seems to be a magnet for the Airbnb alumni. So whatever you're doing, keep that up.

**Lenny** (00:42:30):
Another topic that I wanted to chat about is expanding marketplaces and just the idea of thinking about where you expand to with new markets, new verticals, and then also horizontal versus vertical marketplaces. But first, how do you think about the idea of expanding your marketplace once you've got a foothold in a specific area?

**Dan Hockenmaier** (00:42:48):
I've been fortunate to work on marketplaces that are in these massive, massive industries, which is actually true for a lot of marketplaces because they tend to have winner take all dynamics in really big markets. And so you get these really huge [inaudible 00:42:59].

**Dan Hockenmaier** (00:42:59):
So the local services industry for Thumbtack or the global wholesale industry for Faire, these are meaningful percentages of global GDP. They're huge markets and, as a result, they're really frustrating to work on and also really fun to work on because you have this thing where there's 10 big opportunities that are just one click away from your core business and they all seem really good ideas to do. So how do you actually prioritize between doing those different things? And one thing I've learned here is that actually beyond a certain point, TAM or the size of the market actually matters very little because these are all big enough that they would dramatically inflect the curve of the business if you make them work.

**Dan Hockenmaier** (00:43:35):
It's much more relevant to focus on a couple things. One is how adjacent is that to the business as a proxy for can we actually go get it? So if you think about Instacart's setup options, it makes much more sense for them to expand into convenience stores which they have than into traditional retailers because the convenience store looks much more like their current model. The high frequency, shipping speed matters a lot, fulfillment speed matters a lot. And so it's much more likely their current model's going to work there than trying to expand into something else. And that's the right prioritization function for them to think about versus as retail is a slightly bigger market that could be in stores.

**Dan Hockenmaier** (00:44:09):
And the second thing is are there places that you can accentuate your network effect by expanding into new markets. And what I mean by that is are there places where you can use the same supplier or a consumer has demand for multiple things and so it makes your marketplace stronger versus trying to spin up a new network. So for Uber, it makes all the sense in the world to have Uber Eats because, one, they're the same drivers in many cases, but two, the customer wants rides and meals. And so you automatically have this built-in supply base where if they try to do something that was one click further away from this, it would be much less important to them. And so I think that's the way to prioritize new bets.

**Lenny** (00:44:46):
That is such an interesting point that basically if you're thinking about the upside of a marketplace, think less about just the total TAM of all the adjacent marketplace opportunities in the markets around them and more about how easily it'll be for you to expand into them even if they're smaller.

**Dan Hockenmaier** (00:45:01):
Exactly.

**Lenny** (00:45:02):
Awesome.

**Dan Hockenmaier** (00:45:04):
There's one other lesson here which I've learned a few times, which is that product is the thing that matters when expanding. So because of this dynamic we talked about where liquidity is so important and there's a race to get there, like the first person, the liquidity wins, you often see this arms race where people will spend a huge amount of money on go to market and incentives to bootstrap the market. And that is an important part of the strategy because it actually does matter who drives liquidity faster.

**Dan Hockenmaier** (00:45:33):
But I've learned over and over and over that that's actually not the main thing. It's who can deliver an incredible end-to-end customer experience first, even if for a smaller number of customers. Because that's what creates the flame where actually customers are really loving it, retained, talking about it, and you can then expand from there. So the other big learning from expanding a marketplace is don't let go to market get too far ahead of product. You need to keep those two pieces in lockstep as you're expanding.

**Lenny** (00:46:01):
This touches on a really common piece of advice for marketplaces, which is don't focus on GMV and growth rates and just expansion early on, but instead focus on getting a flywheel going even if it's small, to show that you can make people happy and you can give people what they're looking for. Is there anything you can add there or talk about?

**Dan Hockenmaier** (00:46:20):
Yeah, I think that's exactly right. And the reason this is the right advice is because everything else follows proving you have a good customer experience. Even if you have a very few customers, if your cohorts look really good, they're retaining or even kind of like the classic smiling curve where you see more in engagement later in the life cycle than you do earlier, that's the thing that gives the company conviction to invest resources against it. That's the reason that VCs are going to want to invest rather than a bunch of low quality GMV in a market.

**Lenny** (00:46:49):
Awesome. Speaking of VCs, investing and expanding marketplaces, something that I've noticed is a lot of marketplaces try to find a SaaS business to build on top of their marketplace and find some kind of recurring revenue component and then, in reverse, a lot of SaaS businesses look for how do we add a marketplace to what we're doing. I'm curious how often you find that this actually works out and what do you have to get right to add this other type of business model on top of something that's working.

**Dan Hockenmaier** (00:47:17):
So broadly, I will say I think it's easier for a marketplace to go SaaS than it is the other direction and the reason for that is two things. One is it's a new capability to generate demand, which is fundamentally what a marketplace has to do, and it's a higher value activity. This is why the effective commission of a marketplace, often 10, 15, 20% is much higher than the effective commission of a SaaS business in the 2% to 3% range. So you're just doing much more of the value chain in the marketplace. And second is the marketplace by definition starts with relationships on both sides. But the SaaS business does not have any relationships with the demand side customer. And so they have to acquire a whole new type of demand to make this work.

**Dan Hockenmaier** (00:47:58):
It's not to say it can't work. There's actually a classic kind of SaaS bootstrap to marketplace playbook. This is what OpenTable did. I think we've actually seen some new examples of companies doing this. One in the healthcare space is Solve. They built some interesting products for healthcare clinics that they're now bootstrapping into marketplace. And so I think it's possible, but I think it's very difficult. And then for a marketplace, the lens you should take is much less about how to drive more monetization, but just how do we create a much better experience for our customers because there's some painful thing that they're doing today that we can build for them instead. And so how do we better integrate with the way that they're running their back office or accounting systems is a classic example of where you can make it much better.

**Dan Hockenmaier** (00:48:42):
In the process, you're often making their lives easier, but you're also making your product much stickier. Your retention will go up as a result of this. And so I think if you take the lens of what's the customer pain we're solving, you'll be much more effective than how do we get a few more points of margin out of this customer.

**Lenny** (00:48:57):
If a founder was coming to you and they're like, "Hey Dan, we are a marketplace and we're thinking about adding a SaaS product on top, would you, one, try to discourage them from that? And if, two, that doesn't work, what would you suggest that they focus on most?

**Dan Hockenmaier** (00:49:12):
I mean I think the first thing is looking at those core metrics we talked about, do they have a really liquid high performance marketplace first. That has to be the optimization function. And before you're there, I don't think you should be thinking about some of these expansion levers.

**Dan Hockenmaier** (00:49:27):
The second would be show me the customer problem or the reason it's so hard to engage with this marketplace today that we need to build a deep set of tools or products for this customer to solve. And if both of those things are true, then I think maybe it's quite interesting. But I think more often than not, it's better to focus on the core marketplace.

**Lenny** (00:49:46):
Awesome. Another common question that marketplace founders have is should I go vertical or should I go horizontal? So thinking about eBay as an example, they are very horizontal. You could buy anything you want on eBay. And then there's all these spinoffs that emerged, just classic cars, eBay for classic cars, eBay for guitars. And I'm curious if you have any advice there for either an early stage founder trying to decide should I go horizontal or vertical and/or where do you find the biggest opportunities to slice off a piece of a successful horizontal marketplace?

**Dan Hockenmaier** (00:50:18):
Yeah, absolutely. And in that eBay example, there are now a few quite successful examples of this like [inaudible 00:50:23] and StockX are two where they carved out the sneaker category and the key insight was you couldn't trust the inventory you were getting on eBay. So there's a lot of work you need to do to verify, and those businesses just did it much better than eBay. Broadly though, I think that we over hyped the idea of unbundling. So I think every six months I'm seeing an article where somebody wrote, "This is the unbundling of Reddit, the unbundling of LinkedIn, the unbundling of Facebook." We're going to take all those blue links that you saw on another site and they're all going to become new businesses. And very rarely that thesis plays out. I think the core logical error in the argument for unbundling is that they over focus on one type of improvement, which is user experience and they under focus on the things that make scale businesses have better economics.

**Dan Hockenmaier** (00:51:07):
And so to unpack that, if you look at UX, like if you built a LinkedIn just for construction workers or just for architects or just for investment bankers, you could definitely build some set of features that group liked better than the core LinkedIn experience. But then you have to weigh that against all of the benefits of being broader. And so the two big pieces of where you get benefits from scale are in your customer LTV and then I think the network effect you can build. So if you go back to that Thumbtack example, we had a spreadsheet which tracked hundreds of verticalized competitors where somebody would try to pick off the electricians category, the wedding category, the lessons category, and very few of them got traction for the simple reason that we could upsell customers into a thousand things.

**Dan Hockenmaier** (00:51:48):
And so our customer LTV was always higher and we would always win when we were bidding against those other customers on SEM keywords that were relevant to that category. So it becomes very hard to compete if you're picking off this kind of narrow thing unless you find something which that sub-segment is itself very high frequency or very high dollar value. So Airbnb's an example. They unbundled from Craigslist because they picked off this massive high frequency, high dollar value category [inaudible 00:52:16] but there's not that many of those examples.

**Dan Hockenmaier** (00:52:18):
And then I think the other source of benefit would be the network effect. So if you go back to LinkedIn, for example, I think actually there's an opportunity and we see some successful businesses picking off now blue collar work. So there's a company called Workrise. I think they used to be called Rigup where they're basically building like a LinkedIn but for blue collar work. And that works really well because it's a huge segment and it's somewhat self-contained.

**Dan Hockenmaier** (00:52:39):
But for most other things there's a lot of fluidity between the employers and the employees in terms of who wants to transact with one another. And so if you're an investment banker, you don't really want to be on the LinkedIn investment banker because you're probably in the future going to want some other job. So you want to be in the biggest network that's relevant to you and so this is why you can complain about LinkedIn's UI all day, but they have a very strong place in the market because of that network effect. So broadly, I think there are some pretty interesting examples, places where you can unbundle but they're rarer than people think.

**Lenny** (00:53:10):
That is amazing. There's so much value in what you just shared. So one takeaway I have here is you have an opportunity to unbundle/split off into a vertical marketplace potentially if there's high order value and high frequency. And the third piece is there's almost a self-contained network that doesn't benefit significantly from the rest of the network. For example, I love the Rigup example, like I doubt oil rig operators are on LinkedIn and when something comes around that's like, "Oh, all my buddies are on this thing, I'm going to be on there," you don't need the rest of LinkedIn.

**Lenny** (00:53:40):
The first piece, though, is interesting. So Airbnb I wouldn't say is high frequency. I'd say it's just very large high order value. And so I wonder if you just need one or the other really in a big way. Really high order value or really high frequency?

**Dan Hockenmaier** (00:53:51):
This is a good point. Probably what you're solving for is customer LTV and you can get that in multiple places. There's not that many things which are both high frequency and high dollar value so you can do both. I do think if you go to a place that is low frequency, it comes with all kinds of new challenges because, without frequency, customers forget about you. And so what is the hook to get them to come back? Do you have to reacquire traffic? It creates a whole other set of problems. But if you can get it right like in the Airbnb case, it can work really well.

**Lenny** (00:54:17):
Yeah, Thumbtack is a classic example of how often you need a plumber. And even with the thousands of services that you all had, from what I understand, it's still a struggle to get people to come back often. And remember Thumbtack when they had, "Oh, they have an electrician. Oh yeah, Thumbtack."

**Dan Hockenmaier** (00:54:30):
That's right. Initially, it was very difficult. I mean the average person hires eight or ten new professionals a year, the average homeowner. And so that's decently high frequency, but it's not food delivery or a ride sharing or something like that.

**Lenny** (00:54:42):
Coming back to Faire, so Faire is one of the maybe few really successful B2B marketplaces and it's always felt like there's this gap in B2B marketplaces. You always feel like there should be many more. Like why are there so many consumer marketplaces but so few B2B, and I'm curious what's your take there. Do you think there's a rising trend to B2B marketplaces? Do you think this is always going to be a smaller collection? What's your feeling?

**Dan Hockenmaier** (00:55:07):
So I do think we'll see more of them. Part of the reason we've seen fewer is there are fewer potential founders who understand B2B problems because most of them are consumers and so the consumer use cases are more obvious. So if you take Faire, for example, when I met the founders, which is probably five years ago now, I immediately understood what they were talking about, but only because I had run an e-commerce business in the past and I had the experience of dealing with a hundred suppliers and line sheets and PDFs going back and forth and pricing not being right and just how painful it is to be a retail buyer. And they had a solution which was much better and that clicked.

**Dan Hockenmaier** (00:55:44):
But had I had the same conversation five or 10 years ago with the team at Convoy like I don't know anything about trucking, I probably wouldn't have understood why that business was going to work. And so I think there's partly that. Just the discovery process takes longer for that reason. But I think the reason we won't see a huge explosion in this area is that B2B also comes with something else, which is much lower fragmentation in many cases and you need fragmentation for a good marketplace. The more concentrated either side of your market is, the more leverage they have, the less likely they are to need you and the less likely they are to be willing to pay a high commission.

**Lenny** (00:56:20):
You made that point to me once when we were talking about marketplaces years ago, and that's so stuck with me that when evaluating marketplaces in B2B especially, usually the reason it's not going to work is just it's not fragmented enough. And just to double click there, can you explain what that means? What does fragmentation mean in a marketplace context? And then are there any examples of really low fragmentation of this will never work as a marketplace? And then here it's really high and this is why it's working?

**Dan Hockenmaier** (00:56:45):
Fragmentation is basically just a measure of how many total businesses are there in the space relative to the transaction volume in that space. And if you took the top 5% of suppliers in the space, what percentage of the total volume are they doing? And the higher that percentage is, the less fragmented you are. The challenge that creates for a marketplace is if there's 10 companies in a space that are doing 80% of the volume, it's very important for me to have a relationship with those 10 companies. But those 10 companies are also big enough to have their own sales teams, have their own internal operations. They just need less from a marketplace and, as a result, they're going to be willing to pay less. And you're also probably going to see many more problems with disintermediation, which is when the supplier and the customer go around the marketplace because they can just transact themselves.

**Dan Hockenmaier** (00:57:27):
One principle to use here is how many total dollars are attached to each transaction in the marketplace. When it goes above a certain amount, it becomes much more attractive to figure out how to go around the marketplace. With ride sharing, for example, the absolute dollars of commission on a ride is $2 or $3. Is it worth it for the driver to figure out how to call the passenger two minutes in advance, go around Uber and pick them up? Maybe. You probably see some of that happening, but usually not.

**Dan Hockenmaier** (00:57:55):
But now take there's a bunch of people in the kind of material space within B2B marketplaces, you have manufacturers of say beauty products who need to source aerosol cans and all the inputs into making beauty products. There's not that many of these big suppliers and each of their transactions may be tens of thousands of dollars, hundreds of thousands of dollars, millions of dollars. The commission you would charge on that order is too high because a supplier would rather just pick up the phone and call this person and save those tens of thousands of dollars. And so you just run into these kind of fundamental problems where a marketplace doesn't work anymore.

**Lenny** (00:58:29):
That makes sense. Basically, how much value are you bringing to this market? And if it's not enough where you can charge anything meaningful to run a business is just not going to work. And so that's a really good way of framing it.

**Lenny** (00:58:41):
Final question around marketplaces and, broadly, and I'll let you go. You've spent a lot of time on marketplaces. You've seen their evolution. You've worked on this maybe for the past decade. Where do you see the future of marketplaces going?

**Dan Hockenmaier** (00:58:54):
I actually wrote a blog post on this where we charted the commission that a marketplace charges and the year they were founded. And if you put those on the x and y axis, there's this very clear up into the right trend. Newer marketplaces are charging higher commissions and they're doing more work to justify those commissions. So broadly the evolution looks like kind of Marketplace 1.0, which is all they're doing is aggregating demand. So that's Zillow and Home Advisor. They're basically like lead gen and their commission rate is often pretty low. It's like 5%, maybe 10%.

**Dan Hockenmaier** (00:59:24):
Then you have a managed marketplace like Airbnb or Etsy, which did something really fundamental on top of that, which is generated trust. So they deadhead supply ... You could probably tell me more about what Airbnb did in this space, but they made it a safe transaction and there's a lot of work it takes to make that transaction trustworthy and safe and so they charge a higher commission as a result.

**Dan Hockenmaier** (00:59:48):
There's then one click beyond that which, for lack of a better term, you could call it a heavily managed marketplace, but now they're typically doing some work in the value chain, which is distinct from just aggregating demand. So DoorDash and Instacart own logistics. They took over logistics and, as a result, DoorDash did a much better job than the previous model of Seamless of being able to bring on a lot more restaurants and make it much more reliable for the customer. As a result, they could charge more to the restaurant. Similarly, Faire, we actually underwrite the transaction. We take the risk. If that transaction falls through or the retailer defaults, Faire eats that. And so we are playing a much more fundamental place in that transaction.

**Dan Hockenmaier** (01:00:25):
But as you play this out, what happens at the end of this continuum? Ultimately, you're charging a hundred percent commission and you're not a marketplace anymore. So I think, as we think about the future of marketplaces, one important question is which marketplaces are going to tend towards evolving out of the marketplace model altogether and which will stay in marketplace mode in equilibrium? And you see these examples already like people talk about Opendoor as a marketplace, but it's not. It's an e-commerce website which has the highest price points you can imagine because you're buying houses, but there's no supplier on the other side. They've already bought the house so it's just e-commerce. And I think many marketplaces will go that way. And I think the variable to me that matters in deciding which case you're going to have, whether they consolidate or not, is how much creativity there is in the space. So how much do you need the supplier to be coming up with interesting new things for your customers to buy.

**Dan Hockenmaier** (01:01:18):
What the customer cares about is actually commoditization. They want the same experience every time. Then you're ultimately going to evolve away from marketplaces I think. With ride sharing, basically what I want is a clean car that shows up on time and gets me there every time. So as soon as autonomous vehicles arrive, we're going to fully consolidate that industry and it's not going to be marketplace model any more. On the other end, you have Etsy and Amazon. I think Faire's in this bucket. Steam, the video game marketplace, is in this bucket where the thing you care about is suppliers bringing you amazing creative new things. And that's something that big companies are really bad at doing. So they need the marketplace suppliers to supply this. And so I think those businesses stay in marketplace mode longer term.

**Dan Hockenmaier** (01:02:02):
And then the middle, I don't exactly know how to call what happens in food delivery. You do want some standardization elements, but you also want the local restaurants and so does DoorDash win or the Cloud Kitchen model win? I think it's a little bit harder to understand, but I do think that's kind of the variable that's determining where the future of marketplaces are going.

**Lenny** (01:02:19):
It's interesting to think about this event horizon for when a marketplace is no longer a marketplace. Is a simple way to think about that being when you own the supply, you're no longer a marketplace. When you don't own the supply, you are. Is that how you think about that?

**Dan Hockenmaier** (01:02:34):
Yeah, that's a good mental [inaudible 01:02:37]. Perhaps another way to say owning a supply is when there's no longer a direct transaction between supply and demand. That's what Opendoor took out, for example. You're not transacting with the home seller. You're transacting with Open Door and so that's, in my mind, no longer a marketplace because you also eliminate some of the marketplace mechanics we were talking about a bit.

**Lenny** (01:02:55):
Awesome. Dan, this has been incredible. I feel like we've achieved our goal of getting really deep into the weeds on growth models and marketplaces. Two final questions for you.

**Lenny** (01:03:06):
Where can folks find you online if they want to learn more, reach out and how can listeners be useful to you?

**Dan Hockenmaier** (01:03:11):
Yeah, so I'm on Twitter at Dan Hockenmaier and then LinkedIn. People should feel free to reach out. I think the most useful thing is we're always growing our team at Faire. And so for folks who are interested in this space, I would love to connect with them.

**Lenny** (01:03:26):
Where do they go to learn more and apply for Faire?

**Dan Hockenmaier** (01:03:29):
Just faire.com or faire.com/careers.

**Lenny** (01:03:32):
And that's Faire with an "e" at the end?

**Dan Hockenmaier** (01:03:34):
That's correct, yes.

**Lenny** (01:03:36):
Awesome. All right, Dan, thank you for being here.

**Dan Hockenmaier** (01:03:38):
Thank you so much for the time.

**Lenny** (01:03:41):
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.

---

## [3/20] How to build a high-performing growth team | Adam Fishman (Patreon, Lyft, Imperfect Foods)

**Adam Fishman** (00:00:00):
Onboarding is the only part of your product experience that a hundred percent of people are ever going to touch. Good luck getting a hundred percent feature adoption of anything else in your product, right? But onboarding is the thing that you have to go through in order to use the product. It's also the first opportunity that you have as a company to deliver on the promise that you made out in the marketplace. So I like to think of your brand is the promise that you're making and your product experience is your delivery of that promise. And those two things have to be in lockstep with each other, or you're going to have mismatched expectations and some really disappointed customers. So this is the first chance that a customer has to be really excited or really disappointed in what they thought they were getting. So don't mess that up.

**Lenny** (00:00:55):
Adam Fishman was the first growth and marketing hire at Lyft where he spent two and a half years leading their growth efforts. Then he went on to lead product and growth at Patreon, where he spent over four years building one of the most successful and lasting created platforms out there. And most recently, he was CPO at Imperfect Foods. Today he spends his time advising companies on product and growth, and he's also doing a lot more writing.

**Lenny** (00:01:19):
**Adam Fishman** (00:04:30):
Thanks for having me, Lenny. Super excited to be here. It's a pleasure to be on chatting with you today.

**Lenny** (00:04:36):
It's even more my pleasure. Thank you for being here. To set a little context for listeners that don't know too much about you yet, can you spend 45 seconds giving us a little overview of all of the wonderful things that you've done in your career?

**Adam Fishman** (00:04:50):
Sure. I'm setting my timer for 45 seconds.

**Lenny** (00:04:53):
And, start.

**Adam Fishman** (00:04:55):
So I've been the Chief Product Officer and VP of Growth and Product at a bunch of different companies Imperfect Foods, Patreon, Lyft, the precursor to Lyft which was Zimride to name a few. Now, I do three things primarily, I'm an EIR at Reforge and a program partner, which means I create courses. I run an advisory practice on growth and product strategy, which keeps me pretty busy, and then I recently started a newsletter which was pretty much inspired by your work in this area over the last several years. Those are the three pillars of my life these days, my professional life at least.

**Lenny** (00:05:31):
Nailed it. Wow, that was very contained and clear. Let's plug the newsletter real quick. What's the URL? Is it fishmanafnewsletter.com?

**Adam Fishman** (00:05:39):
It is fishmanafnewsletter.com. I am blessed with great initials that allow me to have that name for a newsletter.

**Lenny** (00:05:47):
It's not obvious. Adam Fishman AF. There you go. That's the acronym. And then in terms of the advising, just to set this expectation, are you looking for more clients or are you capped out? How should people think about that as they listen?

**Adam Fishman** (00:05:58):
Well, I'm pretty busy, but it is a bit of a revolving door, so there's always some pipeline. So even if I can't work with folks right now, sometimes it makes sense for me to work with them a few months down the road. So always open to new interest and learning about new companies.

**Lenny** (00:06:12):
All right, great. We'll share how to contact you at the end of this and it will be in the show notes.

**Adam Fishman** (00:06:15):
Awesome.

**Lenny** (00:06:17):
One question I wanted to ask off the bat is, Lyft, you were there super early. I imagine it was an incredibly wild ride. I'm curious, what's the most tangible memory you have of your time at Lyft?

**Adam Fishman** (00:06:29):
I have a ton of memories from the almost three years that I was there, but I think the biggest one, and probably the most tactile or memorable thing was when we launched Lyft, when we were bringing it out of private beta, we had this press event at the office, which is in Soma, and it had these doors, these big huge garage style doors. And so we opened them up and we actually drove a car into the office with a pink mustache on the front of it, and then a bunch of drivers piled out of it and met the press members and were high fiving people and stuff like that. And then we also served a giant pink mustache cake at this event. So of all of the things there, that one sticks in my head the most.

**Lenny** (00:07:14):
I love that. I hope there was no hair in this mustache cake.

**Adam Fishman** (00:07:18):
No, no, there was not. It was delicious.

**Lenny** (00:07:21):
Okay, awesome. Another question I always have for folks that worked at Lyft or at Uber is how they feel about Super Pumped and what it is like watching that, if you've seen it, what it's like watching the story of Uber and especially working for Lyft.

**Adam Fishman** (00:07:35):
Yeah, I have seen it. I actually read the book first. I've been a pretty big fan of Mike Isaac, who's the New York Times reporter who wrote it. So I've been a big fan of his reporting for a long time. I connected with him a bit while he was writing the book, and I would say, there were parts of it that were painful. It was like renavigating, relitigating a history that I had lived through already. And so much of that story was stuff that I had experienced pretty regularly while I was at Lyft battling against Uber.

**Adam Fishman** (00:08:04):
So one part of me was like, "I remember that. God, that was hard." Another part of me was happy to see that all of the things were out in the open finally, things that were hard to talk about about competitive practices and stuff like that and just shady things. And some part of me was happy that it was out there. And then one other thing separately, so I actually was interviewing with Joseph Gordon-Levitt to be an advisor with his company HitRecord while he was filming Super Bumped.

**Adam Fishman** (00:08:35):
And we had this conversation over Zoom when he was on break in between scenes of filming the show. And for those who don't know, he's the guy that plays Travis Kalanick, the CEO and founder of Uber. So he did this interview with me and he was in his trailer on set, fully decked out as TK in his look with his hair slicked back. And it was really funny and also cool to see him in this context. And he is probably the polar opposite from Travis Kalanick. Obviously they're both super successful, but JGL is a really down to earth, nice, very family-oriented calm guy. So anyways, this is a funny story of my time meeting and interviewing with him.

**Lenny** (00:09:19):
That is amazing. Did you slip in a couple Lyft facts to help Lyft look a little happier and better?

**Adam Fishman** (00:09:26):
I did. We talked a bit about that journey and I asked him some questions about how he prepared for the role and stuff like that. And so yeah, it was pretty fun. We swapped some stories and stuff. So yeah, it was neat.

**Lenny** (00:09:37):
Fun fact, my mom wanted me to dress like Joseph Gordon-Levitt and I was like, "I should look like this guy. Wear some vests. This guy's looking good. Looks like you a little bit."

**Adam Fishman** (00:09:48):
I see that. I do see that. That's awesome. Way to go, mom.

**Lenny** (00:09:51):
Yeah. Then I'll follow her advice. Maybe I should have.

**Adam Fishman** (00:09:54):
It didn't work out so well.

**Lenny** (00:09:56):
Yeah. Okay. So transitioning to the meat of our chat, there's three things I wanted to spend our time chatting about. One is your growth competency model, which essentially is this post you wrote recently that tells founders how to hire and how to evaluate growth people. Two, I want to chat about onboarding flows. You have a lot of really interesting experience optimizing onboarding flows and the impact that's had. And then three is how to choose a company to work out. You've chosen a lot of really interesting companies and you have some cool insights around how to think about that. Does that sound good?

**Adam Fishman** (00:10:27):
Yeah, it sounds great. I've also chosen some bad companies in my time too, so we can talk about the good, the bad and the ugly.

**Lenny** (00:10:32):
Okay, excited to hear about that. So first we talked about this briefly. You've started to do a lot more writing. You have this newsletter at fishmanafnewsletter.com, and you recently wrote this really epic piece called the Growth Competency Model, which essentially lays out what to look for in a growth leader, how to hire, how to evaluate, what to concentrate skills on? Things like that. First question, just what made you feel like you had to write this? What mistakes have you found founders make when hiring and evaluating growth leaders?

**Adam Fishman** (00:10:59):
Yeah, so first I'm going to put up my new background here, which is my growth competency model background. For those watching on YouTube, I have a funny graphic in the background for this. So I guess the reason that I wrote this, there were a few reasons that I wrote it. One is it really felt necessary to write it. And at first it's, I don't think I've ever come across this type of canonical reference before around how to hire and plan for growth. So that's number one. I didn't think it existed. It needed to exist.

**Adam Fishman** (00:11:32):
Two, as an advisor and someone who has held the head of growth role many times, I get asked this question a lot. I get asked all the time about how do you hire growth people? And it's usually something like, "Hey, how do we find you but 10 years earlier in your career?" And it feels like that question is missing the first principles approach to hiring a growth person. And if you're doing that, you're just pattern matching to me. And I may not be the best person, right, or somebody who looks like me may not be the best person. So I think we're missing that.

**Adam Fishman** (00:12:09):
And then third, one of the programs that I'm currently creating is around growth leadership. And so I've been thinking a lot about what it takes to be an exceptional growth leader, how you hire other people onto your team and create balanced teams. And this is going to be a really important component of that program. So it was just really top of mind. So yeah, that's why I wrote it.

**Lenny** (00:12:30):
Let me ask one quick question and I think you were about to start answering one mistakes founders make, but I guess it's less of a question. I know this was built on another model for product management, which is really awesome. And I love that there's this growing fountain of career ladders, competencies per function. And so I don't know if there's been one that's really great for design and engineering, but I love that this is happening. And so first of all, I just want to say I appreciate that you put in the time to think this through.

**Adam Fishman** (00:12:54):
Cool. Thank you. Yeah, and I do think we need more of these. I think we need one for marketers, I think we need one for engineers, designers, research probably, there's probably a bunch of functions that could benefit from some canonicalized resource around this stuff. So yeah, some myths and mistakes that I think founders made and that I've made. I've definitely lived through some mistakes. A few experiences where I was hired into a company where the founder had really messed up expectations of what a growth person should be doing, what I should be doing. And I wanted to set the record straight for founders because they are the folks who hire for this and other leaders.

**Adam Fishman** (00:13:34):
So one example that comes to mind is, I did a very brief stint at a company called Wyzant, in between Lyft and Patreon. And the founders of that company, so Wyzant was a tutoring marketplace. It was acquired by a company not too long ago, so it's now part of a bigger learning company. And the founders of that company we're looking for what I would call a silver bullet strategy to their growth challenges. And what they really needed, and I was naive and didn't think about asking these questions or about evaluating this properly, what they really needed was to create a strategy to add on new growth loops and a system for how to execute against that strategy.

**Adam Fishman** (00:14:13):
If we had talked about that as part of evaluating each other, as part of them evaluating me, it would've given me a lot of confidence that it was the right hire to make. But the problem was they didn't approach it that way. They didn't ask me those questions and I was too naive to recognize that, "Hey, they're not actually evaluating this with the competencies that you would expect for a growth leader." Executing a growth strategy takes time and patience, and they didn't really have it. And overall it ended rather unsuccessfully. I helped them build this office in San Francisco, hired a bunch of folks, we actually closed down the office. I had to lay off a bunch of the people that I'd hired, including myself, which wasn't particularly fun. And I think all of it comes back to that they didn't have a really strong set of criteria on what it meant to hire a great growth person. And so if I can help even just a little bit with founders making that decision better, it'll lead to fewer mismatches I think in the hiring process.

**Lenny** (00:15:11):
Awesome. Let's get into it. What are the components of this model? And you can put it back up again for folks to follow along in the background.

**Adam Fishman** (00:15:18):
It's coming back.

**Lenny** (00:15:18):
It's like a TikTok.

**Adam Fishman** (00:15:19):
The whole thing looks like a big circle and there's four wedges in that circle, four equal parts. And I think that answer of what are the components, what should people look for, really, I'll give the PM answer, which is it depends. And what does it depend on? It depends on the state of the team and where the skill gaps are. So the goal of the competency model is not to find a unicorn human being that is an 11 out of 10 on every one of these things, because frankly, that person doesn't exist. I am not an 11 out of 10 on these skills and I have been a growth executive at many companies. I consider myself to be pretty good at the job. The goal is to create a well-rounded team so that you're hiring and balancing skills across your team and that you don't have any gaps in your portfolio.

**Adam Fishman** (00:16:06):
And so when you think about it, there are four main components to the growth competency model. And the four big components or buckets are growth execution, customer knowledge, growth strategy, and then the last one is communication and influence. And each of those has three really specific skills. And so to give an example, let's break down growth execution for example, which is one of the very first ones that you should be good at if you're a growth practitioner. Within this competency grouping, there's three individual competencies that are channel fluency, experimentation, and what I'd call productizing learnings. And so you can evaluate and ask questions to understand how good people are at these different things and what their experience has been with them.

**Adam Fishman** (00:16:54):
So in productizing learnings for example, one of the key things that a growth person has to do is generate hypotheses, learn from those hypotheses and then translate that into changes that they're making in the product. And you want to find somebody who has a track record of at least understanding how to take something they have learned that might be an experiment or something that's very NVP and turn that into something that has hooks into different areas of the product. And so that's a critical skill to evaluate. And one of an example, the overall set of competencies.

**Lenny** (00:17:26):
To throw in a question real quick, is one way to use this model, coming back to your Wyzant example where there's of course misalignment between you and the founder to sit down and look at this circle here and be like, "Here's where I'm strong, here's where maybe we need to hire someone to take over."

**Adam Fishman** (00:17:41):
Yeah, absolutely. You can almost use it as a reverse interviewing characteristic and say, "What are the competencies you, founder, CEO, care about? What's really important to you for the first person in this role? Or the expectations that you have of what I will bring to the table." And then you can be really candid about what you're good at and what you're not good at, where you're developing. So yeah, I agree with that for sure.

**Lenny** (00:18:06):
Awesome. I know this also plays into evaluating your performance and it could be like, "Hey Adam, here's the three things that we want to focus on in the next cycle."

**Adam Fishman** (00:18:13):
For sure. Yeah. It's really a good foundational framework for being really concrete and specific in the feedback that you provide someone. So rather than saying, "Adam, you really need to be more strategic." Everybody's heard that at some point and it's like, "Well, what do you mean?" You can say, "Hey, we need to work on the area of growth strategy and that means I need to see better modeling of loops out of you, better understanding communication of what those loops are." And you can give really concrete feedback.

**Lenny** (00:18:44):
Awesome. So we've talked about growth execution, What's next?

**Adam Fishman** (00:18:47):
The next one is what I would call customer knowledge. And within customer knowledge there's a set of things and really this is about data fluency and instrumentation, understanding user psychology, which is a big one, and then this idea of being able to experiment and learn over time and how you develop your narrative and your creative approach to talking to customers. I love user psychology and it's one of the things that I think attracted me to growth and to product. I studied consumer psychology when I was in college and I'm just probably would've been a psychologist if not for a growth practitioner, which is a weird other approach I could have taken in my career. But-

**Lenny** (00:19:35):
It's not too late to pivot.

**Adam Fishman** (00:19:37):
... Second career. Yeah, actually, announcing today I'm pivoting the newsletter to just talk about therapy and psychology.

**Lenny** (00:19:43):
Yes. This is going to be the title of the podcast.

**Adam Fishman** (00:19:47):
Awesome. So like user psychology, I think one of the things that people don't easily understand is that most people come to your product with an emotional frame and a lot of people want to appeal to their logical brain right away. And the reality is, don't do that. And so you have to understand the mindset that people are in. How low are their lows? How high are their highs? Why are they seeking out your product? And it often, as I mentioned, stems from some emotional challenge that they're having or something that they're seeking. And it's not because your product is the best chat bot or because it gives the best answers. There's a different thing that they're trying to solve. And only when you address that can you move on to those other things. So that's the second competency is, customer knowledge.

**Lenny** (00:20:34):
It reminds me of something I mentioned on some podcast recently, this tweet that one of the Collison brothers tweeted about how user research is often misunderstood in that people think you do user research and that informs what you build. And instead the way you think about it is user research informs your model of your customer and that model informs what you build.

**Adam Fishman** (00:20:56):
Exactly.

**Lenny** (00:20:56):
And the more user research you do, the more your model evolves to help you understand the customer. And that's been really helpful for me because I never thought of it that way.

**Adam Fishman** (00:21:04):
Yeah. I think that's a great example. Seeking the solution in a customer interview is never going to work, right? You seek to understand and then you take that away and you can think through what the model should look like and how things should change as a result. Yeah. That's great. I can cover the third and fourth competency-

**Lenny** (00:21:24):
That's good.

**Adam Fishman** (00:21:25):
... and I'll try to be a little more brief on that.

**Lenny** (00:21:27):
No, no. It's good.

**Adam Fishman** (00:21:28):
The third competency is growth strategy. And now the third and fourth competencies I would say are a bit more advanced topics. And again, remember when I said people index higher or lower on these as they go across their career, I would expect a more junior growth person to not necessarily be a 10 out of 10 on strategy and communication. These are things that you really have to work at a long time. They tend to be softer skills in a lot of cases and you learn best by either getting it very right or getting it very wrong. And so you've got to put in the time to develop these. But in growth strategy, there's three. The first one is growth loop modeling. So really understanding how you grow and where you should be spending your time. What acquires users? What retains them? What monetizes them?

**Adam Fishman** (00:22:18):
The second one is capital allocation and forecasting. This is basically where are you deploying either your money, your people, how are you managing the portfolio and how are you projecting that out into the future? And that's a really hard one. You have to become best buddies with your finance friends in order to do that. And so anyways, that's capital allocation and forecasting. And then the third one is prioritization and road mapping. So you have to be able to sequence the work much like in building a product, right? Building your growth strategy, you have to sequence it. That sequence has to make sense based on your growth models. You have to have the capital or the people to allocate to that stuff. And you have to be able to build a series of hypotheses in a series of solutions to test against those hypotheses so that you can learn and then productize to those learnings.

**Adam Fishman** (00:23:09):
And there's a lot of ways to test this stuff. Situational, behavioral, interviewing, I talk a lot about this in my post on hiring growth. There's like very specific questions you can ask to understand what people have done or what they might do in different situations. There's case studies and things like that. So that's the third one. And then the fourth one is communication and influence.

**Adam Fishman** (00:23:29):
And I would say, I think you probably know this as a PM, influence is one of the biggest and hardest skills to develop. It's no different in a growth practitioner and in some cases it can even be harder because sometimes people come in with a preconceived notion of what growth is and isn't and you have to change their mind. And so within communication and influence, there's strategic communication. So how do a series of experiments and a series of things that you're trying, fit into the overall picture of a bigger bet that you're taking?

**Adam Fishman** (00:24:06):
How do you lead a team? So team leadership is a big part of communication and influence. And then how do you manage stakeholders? And this is hard in growth because often growth can be viewed as at odds with really thoughtful and quality craftsmanship and product building, but it's not. Those things go hand in hand. And so you really have to win people over on what it means to do growth. And I would say, this is the pinnacle, right? This is the hardest one. It's a lifelong journey. It relies very extensively on understanding people and who you're talking to. And those people can be very different from company to company and the currency that they trade in can be really different. And so this one is one where you have to go back to square one and relearn who the people are that you're working with every time you step into a new role or a new company or get a new leader or something like that. So it can be really challenging and it's never done.

**Lenny** (00:25:03):
That component of the competency models, we're the PM of the growth PM role feels like if you were to do these Venn diagram of the two roles, feels like that's a big part of the overlap.

**Adam Fishman** (00:25:13):
Yep, absolutely. There's a lot of overlap between exceptional product managers and exceptional growth practitioners. I think sometimes they just use the skills in different ways. So you need to be great at product strategy to be a product leader, you need to be great at growth strategy to be a growth leader. Just what those things look like can be different between the two. But they're both required skills, required competencies to be exceptional at the role.

**Lenny** (00:25:38):
So just to rehash, the four categories are communication influence, growth execution, customer knowledge and growth strategy. You mentioned earlier that people often come to you and they're like, "How do we find another Adam?" And your feedback is one, how do you know that's exactly what you need? And then two, find someone that's up and coming more because it's so hard to find folks like you that are actually ready to take on a head of growth role.

**Adam Fishman** (00:26:03):
Yeah.

**Lenny** (00:26:03):
So a question for you is, one is, do you recommend founders focus on finding someone that's more up and coming and fast learning with a high trajectory? And if so, which of these components would you suggest they look for most?

**Adam Fishman** (00:26:19):
One of the challenges of hiring a senior person is that they're all off writing newsletters and making podcast.

**Lenny** (00:26:25):
Right.

**Adam Fishman** (00:26:25):
Not that we know anybody who does that or anything, but-

**Lenny** (00:26:28):
No. That's bullshit. What is that?

**Adam Fishman** (00:26:29):
Yeah. So I don't want to right now go back and work at a company again. I'm enjoying what I'm doing and so it's hard to get me, right? But also you don't want me, I think, when you're doing this for the first time. So I think the key there is smart and driven people for sure. Age and youth is a bit relative I'd say. So I would think about hiring somebody who you might say is less experienced in growth, but they could be very senior in another aspect of their career. You can also benefit from hiring somebody internally who wants to branch out into growth. And one of the benefits that you get from that is a lot of time they have one of those competencies really nailed already. Could be like customer knowledge. They might understand your customer base super well because they're already inside the company.

**Adam Fishman** (00:27:15):
So if you're going to hire a junior person, the key is, how do you help them learn? And I think if you don't know what you're doing as the founder or the leader, it's hard. You're not going to be able to help them yourself. So you've got to be willing to invest in advisors like me, outside education, mentorship, coaching, otherwise, what's going to happen is that very driven, hungry and enthusiastic person is going to run through a lot of brick walls, which is great, except they're going to miss the fact that the door was standing right next to the wall that they just ran through and you're going to end up with a lot of bricks on the ground.

**Lenny** (00:27:54):
Excellent metaphor.

**Adam Fishman** (00:27:56):
Yeah, thank you. And so I have some examples of both hiring people and moving people over in my career. So I think tangible examples are really helpful here. So when I was at Lyft, I had the privilege of hiring that young, smart and driven person a bunch of times, but one of the people who comes to mind is a guy named Ben Lauzier. You should have him on the podcast at some point. He's French, he's very nice to listen to you. He was most recently a VP of product at Thumbtack, but he was definitely not that when I hired him, he was a jack of all trades marketer working at a corporate catering startup when I hired him at Lyft. And he had nailed most of the growth execution and the customer knowledge competencies.

**Adam Fishman** (00:28:38):
One was, he was an avid Lyft user himself, so he really understood the product really well. And also, he was just very thoughtful about how he executed, how he experimented. He had done a lot of it and he was very skilled at pulling them off in a very small environment because he had just had to be. And those are the two most important competencies when you're bringing in a younger, earlier stage person because teaching somebody how to execute is not that fun, right? That's a hard skill. The ability to execute is something like executive function skills and things like that. If you haven't developed those by the time you are an adult, I don't know that I'm going to be able to teach you and I'm certainly probably not the right person to teach you. You should definitely get some outside assistance with that. And so I like to get those types of people that have those things if I'm hiring that generally inexperienced growth practitioner.

**Lenny** (00:29:42):
And the two things you said are customer knowledge and execution. Is that the two you said?

**Adam Fishman** (00:29:46):
Yes. Customer knowledge and growth execution. And so let me tell you an execution story about Ben really quick. This comes also down to work ethic too. So we interviewed Ben and it was a long day of interviews in a tiny glass conference room and Lyft was, I don't know, 30 people or something at the time. At one of the interview breaks, Ben had come over and he didn't have his computer and anything like that. And so he was ducking out of work to do the interview. And he actually came out of the office and he's like, "Hey, does anybody have a computer that I can borrow?" And so we gave him this old crappy Chromebook and I was like, "Why do you need a computer?" And he's like, "I have to go edit this file and do this thing and check something in at work and deploy this thing or whatever."

**Adam Fishman** (00:30:32):
And I'm like, "Wow, this is a guy that really knows how to get stuff done and is so much so that he's pausing his interview process so that he could go get a thing done for his company that he's actively trying to leave, but he's got this work ethic and this execution." And that really stuck with me. And he probably would remember this story if we brought it up. So the time he borrowed a crappy Chromebook laptop to do work at the job that he was trying to leave.

**Lenny** (00:31:00):
What are the chances that was staged?

**Adam Fishman** (00:31:01):
He seemed very innocent. So I think not staged.

**Lenny** (00:31:06):
Okay, great.

**Adam Fishman** (00:31:06):
But I could be wrong. But now everyone that interviews that is going to ask to borrow a laptop and-

**Lenny** (00:31:10):
That's right.

**Adam Fishman** (00:31:10):
... check in some work.

**Lenny** (00:31:11):
The phone call.

**Adam Fishman** (00:31:13):
Yeah.

**Lenny** (00:31:13):
"Adam, I need to fix something."

**Adam Fishman** (00:31:15):
That's right. So that's Ben. And then on the other side, and I'll cover this one really quickly, and the other side of moving somebody over internally, I had equally great success with that. So there was another person named Sean at Patreon who was a marketer, again, a jack of all trades marketer. And I think I have a propensity and a bias towards folks like that because that's one of the ways that I started my career was in marketing. But anyways, I moved him over from marketing to being a growth PM, an entry level growth PM.

**Adam Fishman** (00:31:47):
And he had a ton of the execution skills, ability to prioritize really well and customer knowledge skills as well, more so on the customer side because he was an internal transfer, so he really knew our customers. He'd spent tons of time talking to people, studying data and things like that. And he had really great fluency with data and a drive to continue improving his ability to access and pull out insights and information. And so he turned out to be really great, but just a very different profile of a person than Ben was. And here's an internal hire versus an external hire.

**Adam Fishman** (00:32:23):
So you can have success with both, but I think you really have to make sure that there's some foundational things that are in place like that ability to get customer knowledge and execute.

**Lenny** (00:32:34):
If a founder is listening and trying to decide or hiring a head of growth or a new growth person, would you push them one way or the other, internal hire versus finding someone up and coming and smart?

**Adam Fishman** (00:32:44):
I tend to skew more towards internal hire to be perfectly honest, because I believe in creating opportunity inside a company. I think it's not done often enough. And I also believe that helping people transition into new roles is a way to get more people into the practice. And one of the ways that can happen is if you take a chance on somebody who has demonstrated a good track record in some other aspect of your business. So I tend to recommend internal. I think you have faster time to results. I think you know what you're getting better and in much less likelihood of making the wrong hire there. So I bias towards internal hires.

**Lenny** (00:33:25):
Awesome. And I think partly, I feel that too because there's so much content and training for growth these days that somebody has that background in your company and is already motivated and excited and then can just learn, go to Reforge course, read certain newsletters, feels like it's a lot easier to ramp up. Except, I always feel like if you need someone for SEO or paid growth, that's a hard thing to learn. What's your take there?

**Adam Fishman** (00:33:51):
I would bucket that type of person into a specialist. And one of the archetypes that I talk about is this idea of the painter versus the architect versus the surgeon. And the surgeon is your precision person. I don't actually recommend hiring that as your first hire, but when you are onto something and you really need expertise and you don't have that expertise internally, yes, I think hiring externally is the right thing to do at that point because those are really specific skills that some people have taken years to learn. And I can't just teach someone SEO over the course of a weekend and expect that they're really going to get it. In those cases, I think hiring that specialist or that surgeon is the right approach, once you've got some of the foundational stuff in place.

**Lenny** (00:34:41):
Awesome. Great. Yeah, it feels like there's still a lot of dark art in those two specialties that take years of experience.

**Lenny** (00:34:49):
**Adam Fishman** (00:36:13):
I love onboarding. I probably do at least an onboarding project to at least one with every company that I've worked for and a lot that I advise. The first thing I would say is, onboarding is the only part of your product experience that a hundred percent of people are ever going to touch. Good luck getting a hundred percent feature adoption of anything else in your product right? But onboarding is the thing that you have to go through in order to use the product. It's also the first opportunity that you have as a company to deliver on the promise that you made out in the marketplace.

**Adam Fishman** (00:36:53):
So I like to think of your brand is the promise that you're making and your product experience is your delivery of that promise. And those two things have to be in lockstep with each other or you're going to have mismatched expectations and some really disappointed customers. So this is the first chance that a customer has to be really excited or really disappointed in what they thought they were getting. So don't mess that up.

**Adam Fishman** (00:37:17):
And the third thing I would say is it's also probably the most motivated that someone is going to be about your product since they're typically starting their onboarding journey with you at a time where they're like, "I need this thing really badly that you're selling." And so they're really motivated, right? And so it's an opportunity for you to put some friction in place and learn a lot about them because they will knock down doors to get to your product. So that's why I think it's a super powerful lever for growth. And we worked on this extensively at Lyft, at Patreon, Wyzant, Imperfect Foods just released some onboarding improvements that we had created when I was there, which was nice to see that finally come to light. So yeah, I've done this pretty much everywhere at some point.

**Lenny** (00:38:07):
What impact have you seen from working on onboarding to give people a sense of like, "Wow, this is what I can get if I put some time here."

**Adam Fishman** (00:38:15):
Yeah. One of the things that onboarding really drives is habit formation with the product, which leads to retention. And so you should expect to improve your overall cohort retention curves by focusing on the onboarding and activation experience. I have seen companies shift their curve outward by 10, 15, 20 percentage points from making those changes, especially when you consider that churn is most likely to happen in the very earliest usage of the product. If you can get people past that hump, it's a really invaluable part of the product to work on.

**Adam Fishman** (00:38:51):
So I'll give you a really concrete example. At Patreon, one of the places we worked on onboarding really extensively and the onboarding experience was one of the teams that we had on growth at Patreon. We did a lot of experimentation around the earliest, what we would call product led sales now, when do you connect a human being with a creator and the onboarding experience and what is that impact and how do you connect them with the right person or with the right creator when there are tens of thousands going through that onboarding journey every week?

**Adam Fishman** (00:39:25):
What we realized through a lot of experimentation was the idea of connecting someone with a human being the right person at the right time would improve the first month of revenue or the second month of revenue that a creator made on the platform by 25%. Why that mattered is because the second month that you processed payments on the platform was a key input into your LTV on the platform. So by improving a creator's first and second month revenue by 25%, we were then able to improve their overall value on Patreon by an equivalent amount, which is pretty massive. Moving anything by 25% is really impressive.

**Adam Fishman** (00:40:09):
And so that was human intervention, and then we actually started to productize the stuff that the humans were doing. And so what is not scalable when you're using people becomes very scalable if you can replicate components of that with technology. And so that was the next phase, so we get back to that growth execution thing that I talked about and productizing learnings. That is an example of how you go from, we've learned some things by humans that have made a 25% impact to now we're building these into the product. And so that's a really good example I think, of Patreon and one of the impacts that we had on creator, earnings, retention and their overall success on the platform.

**Lenny** (00:40:50):
That's an amazing example, in case it's useful to a person working on the onboarding. Can you share any more about what you actually did there? You create some algorithm of this type of person, we'll connect them to a person and then you productize it. Is there anything more you could share there that might be useful to folks?

**Adam Fishman** (00:41:06):
Gosh, we did so much. So I'll try to pull out a couple of example. So one of the things that we did, and again, I spoke to the fact that people are really motivated in your onboarding experience, one of the first things we did was we tried to identify better who a creator was in the onboarding experience. And who they were meant how big is their audience on a bunch of the channels where they managed communities, Twitter, Facebook, Instagram, Discord, YouTube, et cetera. And then how engaged was that audience? It's one thing if you make crazy cat videos on YouTube and you have a million subscribers, it's another thing if every time you publish a video, all million of those people watch it, comment on it, share it, et cetera.

**Adam Fishman** (00:41:49):
And so we would ask creators to connect various accounts to Patreon, maybe through authoring with YouTube or Spotify or Instagram or Facebook or something like that, Twitter, and then we would pull in the data into our backend and identify people who had large followings and also heavily engaged followings, based on a set of criteria per channel. And again, this was not just like me inventing this. We had a data scientist team that we worked very closely with to figure out what was important and what wasn't in this model. And then if you were one of those people that had a high propensity for success, high potential creators, we would siphon them off from the regular self-guided onboarding and basically land them in the lap of a human being who could engage with them, reach out, get them even more excited and start talking to them about the best things to do.

**Adam Fishman** (00:42:46):
And then the productization of that, the best things to do turned out to be things like one of our product principles, which became opinionated defaults, which is basically making it hard to do the wrong thing when you're setting up your Patreon page and easy to do the right thing but not eliminating choice.

**Adam Fishman** (00:43:07):
So the creator could still make the choice to do the wrong thing. They could still set up a single tier when we knew that a three-tiered pricing model actually would work better for them, or they could choose to set up 40 tiers when we knew that the sweet spot was three to five or perhaps make their lowest price tier a dollar instead of what we recommended, which was like three or $5 entry points. So they could do all that stuff, but we made it difficult for them to do it. We put more friction in place when they were trying to change some of those defaults because we had learned across a universe of creators, hundreds of thousands of people what worked best.

**Adam Fishman** (00:43:52):
And so putting in those guardrails and those default things was a huge lever for us to drive the behavior that we wanted. And again, we learned that from human intervention with the right types of creators, then detecting those people and putting in the guardrails in the product themselves and making those recommendations inside the product experience. And they were pricing tier structure, how you actually write your page, all of that stuff.

**Lenny** (00:44:18):
Such a great example. It reminds me we had exactly the same situation at Airbnb that you just made me think about. We called it smart defaults. What was your term? Opinionated defaults?

**Adam Fishman** (00:44:29):
Opinionated defaults. Yeah.

**Lenny** (00:44:30):
Yeah, I like that. So at Airbnb we had a bunch of calendar settings when a host signs up, on the host side is where I spent a lot of my time, we had instant book, which is basically you sign up as a host and people can book you instantly. That became the default for Airbnb. And so to make that successful, hosts had to have their calendar be accurate from the beginning. And so what we got to eventually, is we tried to figure out, are you a professional host that knows what you're doing? Are you a mom and pop that's just trying this out? And then based on that, either block your entire calendar, keep it all open, or somewhere in between.

**Lenny** (00:45:03):
And it's interesting that it connects to your point about, and I was going to come back to this that, a lot of people think of onboarding as a conversion opportunity and it definitely is. But to your point, even more interestingly, it's a retention opportunity because in the Airbnb case, hosts sign up, they get booked for a day, they don't want to host, they're like, "Shit, what the hell's going on here? I'm out."

**Adam Fishman** (00:45:22):
Yeah.

**Lenny** (00:45:22):
And so, I wanted to ask you, how should folks think about onboarding conversion versus retention, and why is it so powerful for retention?

**Adam Fishman** (00:45:32):
I actually think if you're doing it right, sometimes conversion should actually decrease a little bit. So you might actually have fewer people getting all the way through successfully, but I think that's okay because a lot of those people were probably not the right people for your product, which means they wouldn't have been engaged customers, they probably would have churned. So just by the nature of actually weeding out some people, you're going to improve retention because the people who are going through are the people who are much more highly qualified. And so I think that's also why onboarding is so challenging because you have to figure out what that sweet spot is, right?

**Adam Fishman** (00:46:17):
You could actually reduce conversion to a point where it's not offset by improvements in retention and you'd be doing the wrong thing. So when you're experimenting, you have to look at these push and pull metrics of these opposing metrics. But overall, I find that the biggest impact that you'll have is on retaining users because you are trying to connect them to the value that your product offers and form a habit. And if you form that habit early on, they're going to stick around because they're going to get it, they're going to get the benefit of the product, and they're going to be excited to stay and then tell more people about it. So that's why I think it's a much bigger impact on retention than conversion.

**Lenny** (00:47:01):
Obviously retention is a longer tail metric and conversion is immediate.

**Adam Fishman** (00:47:06):
Yeah.

**Lenny** (00:47:07):
Do you have any tips for folks that are like, "Oh my God, how do I know if this conversion hit is worth retention increasing potentially?"

**Adam Fishman** (00:47:13):
Yeah. I think the answer is not wait 90 days to find out, right? Nobody has that time. And so what I tend to do is look at proxy metrics. So there are proxies for things like 90 day retention. As an example at Patreon, one of our proxies around the eventual success of a creator was how quickly they would reach certain dollar thresholds once they launched. And so your velocity to get to your first patron, your first a hundred dollars processed on the platform and that thing had a lot to do with how big and successful you would be, and therefore how well you would retain.

**Adam Fishman** (00:47:52):
And so we looked at very early signals to understand and evaluate how good someone was going to be. We also did a lot of qualitative screening in the beginning. So as people went through, we would take samplings of creators who were onboarding and signing up and launching their pages, and we would actually look at who the creator was and what they were doing. And then we would be able to run it through our model to say, "It looks like we're getting a lot of the right people going through and doing the right behaviors, therefore, we're very confident that they're going to retain better and do the right things." So yeah, proxy metrics are the key there.

**Lenny** (00:48:32):
Awesome. So part of this is find this leading indicator proxy metric, and then to your point, maybe build a little bit of a heuristic that's like, okay, this is qualitatively looking like it's doing the right things to our new users.

**Adam Fishman** (00:48:45):
Yep.

**Lenny** (00:48:46):
Maybe our last question on onboarding is, at Airbnb and I imagine many companies, there's this constant desire to, "Let's just redo this whole thing. Let's just redesign it. Let's start again." And my question to you is just, how much is too much on redoing, rethinking, onboarding, optimizing, micro-optimizing? Any answers there?

**Adam Fishman** (00:49:05):
Yeah. I would say first, I very strongly dislike the idea of redesigning something for redesigning sake. So I think that it is true that you should spend a lot of time on onboarding, and you should regularly revisit it as you learn new things about your users. So even at Patreon, we would work on onboarding and then we take a beat, we'd let it go for a while, improved, and then as we learn new things, we would find ways to fold those back into onboarding. So I find that it's acceptable to revisit when you are learning net new principles about your customers or something new about your growth model where onboarding can directly influence.

**Adam Fishman** (00:49:51):
So as we learned at Patreon what the right tier construction was, or the right way to talk about your Patreon page or the right way to message it in the beginning, we would go back and say, "How do we build this newfound knowledge into an experience that sets someone up for success?" But if we weren't gaining new insights, we weren't just tweaking the onboarding experience and trying to tune it in a very micro way, because the reality is, that doesn't really move the needle that often, especially once you've got it in a pretty good foundational place. And only when you discover something really fundamentally net new, will it have an outsized impact on retention or the success of early users. So don't just redesign for redesign sake, make sure there's a new hard earned insight that you've got before you do it.

**Lenny** (00:50:50):
Do you think at scale companies, I don't know, maybe after hundreds of people, they should have a team, like an onboarding optimization team? I find that often is true. And I guess, do you think that makes sense?

**Adam Fishman** (00:51:03):
Yeah. I think it's very helpful. And the reason I think it's helpful is because I do think it's easy to walk away from onboarding because there's so many other things to work on and to lose sight of the fact this is such a critical part of the experience. And I don't know how many times I've come into a company and they're like, "Yeah, we built that a long time ago and we've never looked at it again. It's been a few years, but we're really having a real problem with retention and people dropping off in the first seven days." And I'm like, "Yeah, I think it's time we take another look at the onboarding experience. Products change quite a bit. Maybe people are getting something that's different than they expect, or maybe we know a lot more that we can use to influence decisions that they make."

**Adam Fishman** (00:51:50):
So I do think it is beneficial to have that team, or at least a team, that part of their job is the activation experience and therefore some part of their roadmap is working on onboarding and then other aspects of activation. So it may not be what they work on 12 months out of the year, but maybe for a quarter or two in a given year.

**Lenny** (00:52:13):
Cool. And there's a LinkedIn post you wrote with a bunch of examples of onboarding work you've done. So we're going to include them in the show notes for folks that are-

**Adam Fishman** (00:52:20):
Nice.

**Lenny** (00:52:20):
... hoping for more examples. Yeah. Okay. Third topic, final topic is around company selection and evaluating where to work. And you have this really cool framework that I think you call PMF for candidates. Can you talk about what that is and then we'll get into it a little bit?

**Adam Fishman** (00:52:34):
Yeah. I somehow stumbled on that name and it just made sense because of the acronym. But I think I was really motivated to revisit this because as we know in tech there's been a ton of layoffs and very public layoffs because of the economy, the state of funding, things like that. And I don't think we're done yet. I think we're pretty far from being done. But it's really important, and I've been burned by this a few times, to put some power back in the hands of the people who are actually seeking the jobs to understand what are some criteria that are important and these are the criteria that are important to me that help you make decisions about which company I should join, assuming they'll have me. And so the PMF acronym, and we're all familiar with product-market fit, right?

**Adam Fishman** (00:53:23):
So in a way it's both the product-market fit for as a candidate with the company, but then also PMF stands for people, mission and financials. And these are my three criteria. They may not be yours, Lenny, or they might not be the average person on the street, but the point is that you should have a set of criteria that you are unapologetically rigorous around and you should learn how to evaluate companies against that set of criteria. First, I guess I'll tell you what by people, mission and financials.

**Adam Fishman** (00:53:56):
So people are these folks that I am going to enjoy working with everyday that I'm going to be able to have hard conversations with, that I'm going to be able to disagree with and work through those disagreements and feel better on the other side of that productive disagreement, for example, and get to resolutions. What do I think about my peer set, the leaders, the people below me, if that's the role I'm stepping into, et cetera. So that's the people dimension.

**Adam Fishman** (00:54:30):
Mission, which is critically important for me, is that if I join a company and I do my job, which often involves growing that company really big, getting a lot of customers, generating a lot of demand and retention and stuff, I want to make sure that a lot of people have a better outcome in life because of that company's existence. And I don't just mean employees and founders having a good financial outcome, which I think is important. But I also mean in the case of creators on Patreon, we were building a new way for creators to make money, which they could then use to hire people, create more jobs, make better content, and live their life in a sustainable way so that they weren't a starving artist and they weren't living paycheck to paycheck. So that's really important, the mission aspect, that's got to exist.

**Adam Fishman** (00:55:19):
And then the third one is, and I think really important now is this idea of financials or fiscal discipline. You've got a lot of companies who raised boatloads of money or did financial planning during the peak of the pandemic and assumed that their business was going to continue operating at the pace that it was operating forever. A lot of those companies are running out of money, they've seen a hit to demand and they've had to lay people off as a result or make really big strategic swings.

**Adam Fishman** (00:55:53):
There are plenty of companies that you're not really hearing about that were more conservative in their approach, that understood and were able to look into the future and be really responsible with their money. And those people are not laying off employees. And so they're not all over LinkedIn talking about it because they're not laying people off. There's no hashtag layoff for them. So that's what by financials. And so that's the PMF framework and evaluating across those dimensions is super important. I've done it two times in the last 10 to 15 years, and I've done it poorly, two times in the last 15 years. And Lyft and Patreon are two times where I've done it really well. Wyzant and Imperfect Foods are two times where I personally don't think I've done a good enough job evaluating.

**Adam Fishman** (00:56:41):
Any time where I've shortcutted my criteria, where I've settled for two out of three, or thought one was great, when really it wasn't, has not ended well for me, for the company, it's not that the company imploded, but I found myself out of a job or really frustrated and burned out or something like that. I already talked about the Wyzant example where we had to lay off a bunch of people because the founders expected something very different than what I expected to be able to deliver, that's a big people miss. And Imperfect Foods was somewhat similar, amazing mission, really great financial strategy, fantastic CFO, but a lot of infighting at the C-suite. And it made it really difficult for us to plan and move the company forward together because people were at odds with each other all the time and not resolving disagreements productively. And when that happens, it's hard to be a product or a growth leader because you bear the brunt of the angst that people have. So anyway, so those are a couple examples and some of the characteristics of PMF.

**Lenny** (00:57:57):
In the case of Imperfect Foods, what could you have done to have avoided that issue and seen if it was true PMF?

**Adam Fishman** (00:58:04):
I would have tried to observe the inner workings of the C-Suite a little bit more closely before I accepted an offer to join the company. I would've attended an executive meeting or joined them on an offsite. And I think, too often, candidates don't feel like they can ask for those things. And it's true, if you're entering the C-suite, you're going to ask for more stuff, you're more experienced. But I also think that's true of a junior employee. You can observe a team meeting, you can observe a product review and understand, you sign an NDA, you promise you won't tell anybody about it, but observe what is happening and the dynamics of that room. Who's doing the talking? How feedback is delivered, is it constructive? Is it antagonistic, et cetera. So you can observe and then you can also ask questions.

**Adam Fishman** (00:59:00):
So questions that I like to ask are, tell me about the last strategic offsite that you had as a leadership team. Where do people disagree? What was one thing that they disagreed on and where did you end up on that point and how did you get there? And I actually ask them to tell me, it's like a reverse behavioral interview question. I ask them to tell me how they navigated it, and I will ask the CEO that and really dig in on that particular set of questions. Those are the things that I do to evaluate the people dimension, which is one of the hardest, I will say. Financials and mission a little easier to evaluate, but people really require getting to know teams. So it is hard.

**Lenny** (00:59:43):
That's such a good question to ask. And your point is you can ask that even if you're not a senior leader, you're just ICPM joining a team. Is there anything else you think folks can do? So you said, join some offsites maybe, ask this question that you shared, any other tips for folks just to understand if the people are a good fit? Because it's pretty wild. You're going to spend so much time with these people and you meet them once in a half hour interview and then you have to decide if that's your life for the next four or five, 10 years.

**Adam Fishman** (01:00:09):
Well, one thing that I would say is, you're an investor, right? You invest in a lot of companies, you're an angel investor and you have the Airbnb syndicate and things like that. You evaluate companies when you're making an investment decision, right? Because you're investing a sum of money into that company. And so as a result, you do a lot of diligence on companies or read other people's diligence, something like that. When you're interviewing at a company, you are actually investing an even more scarce resource. You're investing your time. There is no way to get more time. We're all on a finite clock. You can always get more money. If you make a bad investment decision, "Okay, we lost there." Provided you didn't bankrupt yourself. Even if you did, you can climb out of bankruptcy. There are things that you can do, but time is fleeting.

**Adam Fishman** (01:00:56):
And so one of the other things, and this is a thing that you do when you're an investor, is you do back channel references, right? A company is going to back channel, you the employee, if they're a good company, they're going to talk, if you and I had worked together, Lenny, they might say, "Hey, let me get in touch with Lenny and see what it was really like working with Adam instead of what Adam tells me in the interview process." And you're going to do this as an investor in a company. "Let me talk to some people who passed on investing in this company. What did they see that I don't see?"

**Adam Fishman** (01:01:29):
And so in this case, you can talk to current or former employees who are not on the interview circuit. And because they are not on the interview circuit, their role as a salesperson in the process is greatly diminished. And they can, especially if they're not at the company anymore, give you some pretty candid feedback on what it's like to work there. So I'll give you a really good example. That was super impressive. A PM who worked for me at Patreon, who you know Tal Raviv-

**Lenny** (01:02:00):
Shout out Tal.

**Adam Fishman** (01:02:01):
Shout out to Tal, who works on this product that we're recording on right now-

**Lenny** (01:02:06):
Shout out Riverside.

**Adam Fishman** (01:02:08):
... when he interviewed at Patreon, he asked me for a list of people who I had managed in the past, and he contacted them to talk to them about what it was like to work for me. That was the first time that had actually ever happened in my career. And I was happy to share that with him. And it represented to me a great level of thoughtfulness and insight around him evaluating what he was getting himself into. And he was an ICPM and he asked that of me, who was a VP executive level person at the company.

**Adam Fishman** (01:02:44):
So you can do that. And if a company says no or a person says no, I think that actually says a bit more about them than anything else. If they're trying to withhold that from you. Because why would you? If I'm a great manager, I'm happy to have you talk to people who I've managed before, even people maybe who I had to let go or something like that, right? I'm confident that those were the right decisions and that those people ended up in a better place and they were taken care of with great care. I would actually make a reference of somebody who I have let go before just so that someone could get a real honest truth of what it was like working with me. So anyways, that's my take on PMF and questions to ask.

**Lenny** (01:03:30):
I imagine you have PMF with your current world, so maybe just to close, can you just remind folks what you're up to now and where they can find you online and also how listeners can be useful to you?

**Adam Fishman** (01:03:42):
First, thanks for having me on, Lenny. This was super fun. I love talking about this stuff and it was great chatting with you. So thanks again for having me.

**Lenny** (01:03:50):
My pleasure.

**Adam Fishman** (01:03:51):
There are a few ways to get in touch with me. You can follow me and communicate with me on Twitter. My Twitter handle is Fishman, F-I-S-H-M-A-N AF. And I do respond to messages provided that they're polite. And you can also find me on LinkedIn. Those are the two platforms I live on most frequently, for better or for worse. And then I now have this newsletter, fishmanafnewsletter.com. And a lot of what we talked about today are things that I am publishing in written form on that newsletter and plan to continue publishing going forward. And again, it was inspired by the work that you're doing, Lenny.

**Adam Fishman** (01:04:29):
So how can people be helpful to me? I think certainly subscribing to the newsletter and joining that community, telling me about the things that are challenging to them so that I can find ways of finding how they meet up with my interests and translating them into written pieces. And then if you're ever interested in exploring an advisory relationship with me or learning more what that looks like, reach out. I'd love to meet you. Advisory work is what pays the bills right now, and my kids need to eat. I probably need to eat a little less, but my kids need to eat. So reach out about an advisory relationship if you're looking for some help on growth or product or general company building. It's what I do.

**Lenny** (01:05:08):
Adam, you're so full of insights and lessons, and I'm so happy that you've started writing and sharing a lot of these things. Folks should definitely subscribe. Fishmanafnewsletter.com. Adam, thank you for being here.

**Adam Fishman** (01:05:18):
Yeah, thanks a lot, Lenny. This was awesome.

**Lenny** (01:05:21):
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.

---

## [4/20] Building better product roadmaps | Janna Bastow (Mind the Product, ProdPad)

**Janna Bastow** (00:00:00):
The whole point about a roadmap is that it's not designed to be your plan. I think about it as being a prototype for your strategy. What I mean by that is we talk about prototyping all the time in the lean world and a prototype is essentially a way of checking your assumptions. Generally, we think about it in terms of a design or like a model, but think about it at the strategy level.

**Janna Bastow** (00:00:22):
So at the feature level, you'd prototype by doing a design, a mockup, and you'd take that mockup and you'd share it with somebody and say, "Here's a mockup of the feature that I'm trying to build. What do you think?" And they'd tell you what's right or wrong, and you'd add some new copy or a button to make it more clear, and you'd throw out the original prototype, because it wasn't very good and you'd make a new one. So the value isn't the prototype, the value is in the prototyping process.

**Janna Bastow** (00:00:47):
The value isn't in your roadmap, the value is in the roadmapping process. What you're actually doing is laying out your assumptions of the problems that you're solving. So you're saying, "I think we have this problem, then this problem. What do you think?" The whole point is that you just share your early assumptions with other people on the team, with customers, even, like anybody who will listen and just check that you're on the right path.

**Lenny** (00:01:11):
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 your own 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 Janna Bastow. Janna co-founded Mind the Product, which I believe is the largest community of product people anywhere. She's also the inventor of the roadmapping framework, Now, Next, Later, and the founder of ProdPad, which makes it easy for you to do your roadmapping in this new simpler way. In our chat, we talk about public speaking, community building, roadmapping, vision, and going from product manager to founder. With that, I bring you Janna Bastow.

**Lenny** (00:01:58):
This episode is brought to you by Formsort the leading low-code form builder for product teams. If you work at a startup, you've probably experienced the pain of building forms. Product managers come up with an idea for a new onboarding flow, and then engineers have to build it and then maintain these flows forever. Even tiny changes to the flow can take weeks to get implemented, slowing down your team's experimentation cycle. Formsort removes the engineering bottleneck and gives product managers and marketers full control over the form building lifecycle. With Formsort, anyone can build highly customizable forms, implement complex logic, and send data to destinations like Postgres, BigQuery, and Segment.

**Lenny** (00:02:38):
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**Lenny** (00:03:15):
This episode is brought to you by Coda. Coda's an all in one doc that combines the best of documents, spreadsheets, and apps in one place. I actually use Coda every single day. It's my home base for organizing my newsletter writing. It's where I plan my content calendar, capture my research, and write the first drafts of each and every post. It's also where I curate my private knowledge repository for paid newsletter subscribers. And it's also how I manage the workflow for this very podcast.

**Lenny** (00:03:42):
Over the years I've seen Coda evolve from being a tool that makes teams more productive to one that also helps bring the best practices across the tech industry to life. With an incredibly rich collection of templates and guides in the Coda doc gallery, including resources from many guests on this podcast, including Shreyas, Gokul, and Shishir, the CEO of Coda.Some of the best teams out there like Pinterest, Spotify, Square and Uber, use Coda to run effectively and have published their templates for anyone to use. If you're ping ponging between lots of documents and spreadsheets, make your life better and start using Coda. You can take advantage of a special limited time offer just for startups. Head over coda.io/lenny to sign up and get a $1,000 credit on your first statement. That's C-O-D-A.io/lenny to sign up and get a $1,000 in credit on your account.

**Lenny** (00:04:44):
Janna, welcome to the podcast.

**Janna Bastow** (00:04:45):
Hi, thanks so much for having me.

**Lenny** (00:04:47):
It's my pleasure. Just to start off and set a little context for folks, could you give listeners a 55 second background on what you've been up to in your career?

**Janna Bastow** (00:04:57):
Yeah, absolutely. So I'm a product manager by background. I started my career falling into product management like a lot of people do, accidentally. I worked my way up to be head of product at a startup in London. And then saw the need for product management tools, because there wasn't really anything like that out there. So started building ProdPad. One of my co-founders, who I also happened to start Mind the Product with, and Mind the Product turned into the world's largest community of product managers. So I ended up founding two things at the same time, and that's what kept me busy for the last decade or so.

**Lenny** (00:05:28):
And currently you have a company, maybe just mentioned that, before we move on, because I think it'll be important.

**Janna Bastow** (00:05:33):
Yep, absolutely. So that tool that I was talking about turned into ProdPad, which is software for product people. So it's a tool that allows you to build roadmaps and do your OKRs and capture ideas from your team and feedback from your customer and just organize all your product managements stuff in one space.

**Lenny** (00:05:47):
Awesome. So you mentioned Mind the Product and ProductTank, which is kind of this associated component. I'm not exactly sure the difference, but I know they're related. One's a community component, right? Is that right?

**Janna Bastow** (00:05:57):
Yeah.

**Lenny** (00:05:57):
Yeah. So I think you mentioned it's probably the biggest product community in the world, both online and offline. And as someone that's building their own community around the newsletter and the podcast that I have, I'm always curious just to learn what folks have learned about building communities, especially for product people. So question on my mind is, what do you think has been most important in getting Mind the Product community right early on, and then also just maintaining the quality of the community?

**Janna Bastow** (00:06:23):
Honestly, it wasn't so much that we set out to build a community, it was that we got together with some product people with the idea that we didn't know what we were doing. And so we figured if we got together with some other product people and started chatting it through, we'd all learn together. And so it was just the sense of sharing and collaborating and learning from each other and just keeping it as grassroots as possible as it grew. And consistency as well, just always being there, every month, holding a ProductTank, every year of holding an event. But just being there, whenever there was a chance to be there.

**Lenny** (00:06:56):
So I'm hearing is just putting in the time, doing it consistently. I imagine a big part of it was having the right sort of people involved early on that are maybe the right exemplars of the type of community you want to build. Is that roughly right?

**Janna Bastow** (00:07:09):
Yeah, absolutely. I mean surround yourself with the people who are going to help you continue that community and are going to help you with that consistency, and going to help you surround you with more and more of the right people. One of the things we learned really early on was that we only had so wide of a network. And so being able to get other people to help us curate and bring in other smart people to help find other speakers outside of our network, and help find people to write on the blog when we'd run out things to rant about. Similar to what you do, Lenny, you've got people from all over your community helping to contribute to the wider picture.

**Lenny** (00:07:42):
Awesome. What's the scale of the community at this point?

**Janna Bastow** (00:07:45):
That's a good question. I don't have the exact number. What you might not know or what you might know is that Mind the Product was actually sold earlier this year, so I don't have-

**Lenny** (00:07:51):
Mm-hmm. I did know that.

**Janna Bastow** (00:07:52):
... a handle on the exact numbers now. And it did go influx when COVID hit. I know at one point in time the ProductTank was like 200 going on almost 300 cities around the world. I don't know what that number is today. I know that it sort of went up and then down and then back up again. Some of those are digital still, some of those are back in-person. I know that there's thousands and thousands of product people around the world who are taking part in the community in one way, shape, or form or the other. And, of course, some people take part in the big conferences as well.

**Lenny** (00:08:22):
I imagine there were some mistakes that you made along the way building this community.

**Janna Bastow** (00:08:26):
Oh God.

**Lenny** (00:08:26):
Is there anything that stands out as, "Oh, man, we shouldn't have done that"? For folks that are thinking about building communities these days,

**Janna Bastow** (00:08:32):
When running a conference, it's one of the most expensive and unleanest things you can possibly do. It's really difficult as a product person to pull that off, because it pulls at your heart. You want to do something that's lean iterative, but you can't. If something screws up with the lunch order, for example, you can't fix it. You have to wait until the next year and you just have to pull out whatever you can to make it good enough for that particular year. There was a year once when we ordered food and it didn't turn out to be enough, because the caters under delivered, and we ended up having to get all our volunteers to go to the local sandwich shops and buy all the food up and bring it in.It was stuff like that that was difficult at the time, but we made do with what we could and we ended up sending cash cards to our attendee saying, "Here, let's make it up to you." Stuff like that, that just becomes logistically really, really difficult when you're just thinking, "Oh, we just pay a supplier and they make it happen." It's not that simple.

**Lenny** (00:09:29):
Got it. Okay. But that's a plus one for me to never run a conference, something I never want to do. And this is a reminder of all the pain that goes into them.

**Janna Bastow** (00:09:38):
Conferences are ridiculously hard. I mean the thing that I've learned is when something goes wrong in a conference, it doesn't happen in the hundreds of dollars of cost, it happens in the thousands of dollars of cost. A speaker who decides they can't make it for one reason or the other, totally legitimate reason, sure, but you've already paid for their business class flights, and so you've got to find another speaker last minute and get them over. That's thousands of pounds in the hole. It could be things like the printing went wrong and you found out the day before, that's more dollars gone. There's lots of things that could go wrong. Our venue once went bust, the after party venue once went bust three weeks before the conference. That was year one.

**Lenny** (00:10:19):
Super.

**Janna Bastow** (00:10:19):
All of these things, yeah, that's what we said, "Super, what are we supposed to do?" We ended up having to just make do and found somewhere else and roll with it. So lots of things that go wrong at that sort of level. But the thing is that we built up a lot of goodwill with the community and were able to get help from people around us, get suggestions from people around us. And when things ended up, actually it turns out we ended up with a smaller venue than we expected, or this was slightly different or whatever else, we had people forgive us. It worked out okay, in our favor.

**Lenny** (00:10:49):
Just while on this topic, I'm most curious, are conferences like a good business? Do they make a ton of money in some occasions? Is it always just super thin margin? How does that even business work?

**Janna Bastow** (00:10:59):
It's not for the faint hearted. It's hugely risky. In hindsight, I'm highly surprised we actually made it through some of those first ones. If you can do it, there are some amazing ways that you can monetize them. But it only starts making a difference at larger figures, and it takes a lot of efforts to actually get to that point. Somebody once asked me like, "Oh, we're struggling to sell tickets. How do you sell all those tickets?" We'll start a community several years before and invite people and run a thing, some sort of community meetup every month time, time again beforehand, and that's your marketing.

**Janna Bastow** (00:11:33):
Just if you undersell tickets to a conference, for example, it can absolutely break it. And you see sometimes conferences, they run one and they don't have enough people turning up and it's gone. That can just break it. It's ridiculous. Something like COVID comes by and it can break it. It's a ridiculously hard business. It's really hard to ensure against. It's really hard to think of all the things that could go wrong and protect against. So while there are some upsides, it's not for the faint hearted.

**Lenny** (00:12:01):
Okay, cool. That's another plus one. I have a friend who runs events here in San Francisco and I'm always just like, "How can someone be excited about running events over and over? It's so stressful and full of risk and there's always things going wrong. You can't ever have fun at these things." So it's always a different personality.

**Janna Bastow** (00:12:16):
Yeah, event organizer or event manager or something like that was once listed as one of the most stressful jobs out there. And you can see why. It's because it all just lands on you all at once. And once the event is over, there's the sense of [foreign language 00:12:29], as in it's over and now what? The next day you're just like, "Yay." You can look at the tweet stream of everything that happened. You can look back at the photos and then you're like, "What do we do next?"

**Lenny** (00:12:38):
Start prepping for ext year.

**Janna Bastow** (00:12:39):
You start prepping for next year, off we go again. And it's really hard work. But there again, product management was also listed as one of the toughest jobs, one of the hardest jobs out there. I'm not sure if that still stands, but I know product management as it stood 10 years ago, five, 10 years ago, certainly did have a different vibe to it, and it was a really tough job.

**Lenny** (00:12:58):
Continues to be a very tough job. On the topic of conferences and speaking, I've watched a bunch of your talks online before we started chatting today. And a couple things I noticed. One is you're just an awesome speaker, and you're also storyteller. And something that comes up a lot on this podcast is just how important communication skills are to product leaders and product managers and storytelling. And you've also seen a bunch of people do awesome talks at these conferences. So I'm just curious, whatever you have in mind, what has helped you become a better speaker and storyteller? And then also what have you seen is important to folks that are really good at storytelling and presenting at a conference, let's say?

**Janna Bastow** (00:13:37):
Right. Yeah, such a good question. I mean, I have learned by watching a lot of other people. One of the things that I have been super lucky in my career is that by being part of Mind the Product I've gotten to watch every last Mind the Product speaker, top end speakers. I've been able to see every ProductTank London speaker, and a lot of the other ProductTank speakers around the world. Been able to see what people react to, what works, what doesn't work. So I've been able to develop a taste for a good talk and a good presentation and that sort of thing.

**Janna Bastow** (00:14:06):
But also one of the things that Mind the Product has been able to provide to speakers is a speaker coach. So when I was invited to speak on the Mind the Product stage in 2017, one of the things that they provided to me was an actual speaker coach, somebody to take my talk and improve on it. And it was really nerve-wracking taking my half-written talk, which I started months and months before, it started off with just Post-It Notes scattered along the wall, which I tried to turn into something. And I think it was probably six hours worth of content. And I brought this to this speaker coach, and I had a vague script idea of what I wanted to say.

**Janna Bastow** (00:14:43):
And she said to me, one of the first things, she said, "Well, I've taken your script and I've turned it around. I've rewritten the jokes to land a little bit better." I was like, "That's great. I had jokes." And she helped turn the stories around, so that they carried through. She helped with posture. She helped with delivery. She helped with even just phrasing of words. Just making sure that everything landed in particular ways. And one of the things she did was make me listen to it and play it back, which I had not done before. And I still hate doing to this day, but am now more used to it than before.And I don't think anybody likes listening to the sound of their own voice. I don't think anybody likes doing that. But it does help with it. If you've got a large presentation, a big presentation, you've got to get up to that level. If you're nervous about doing it in front of a 1,000 people, then getting to that level that you're actually willing to, able to hear yourself do it, and you're able to do the talk flawlessly in the shower, and as you're walking to work, and as you're doing your groceries and all that sort of stuff, then it makes a big difference.

**Lenny** (00:15:47):
So one tactic that I love that you shared is record yourself, watch yourself ,keep refining, but watching your actual performance. Looking back at the lessons your coach taught you for new presentations that you do, is there anything else that sticks with you? Or just let's make sure to get X, Y, Z nailed because that'll help make this talk better.

**Janna Bastow** (00:16:06):
One of the things that I've stopped doing is I used to sit down with a PowerPoint and start writing my deck in PowerPoint or Slides, now. What I now do is I start with my story points. I start with my narratives. I try to figure out what I'm actually trying to say, and then I fit it into the deck. Because what I was doing before, I would get stuck in this mode of the presentation mode, and trying to make the presentation, the slides fit my narrative as opposed to the opposite way around. Having a great narrative, and the slides should follow more naturally.

**Lenny** (00:16:43):
What about just the presenting, the physical anxiety of presenting?, Is there anything you've done there to get better with that and feel-

**Janna Bastow** (00:16:51):
Oh, yes.

**Lenny** (00:16:51):
... more comfortable?

**Janna Bastow** (00:16:51):
So one of the things that actually really does work is the power pose, standing with your hands on your hips and it really does, I'm not sure if it's adrenaline or endorphins or something, it releases some sort of chemicals that really does just help boost your confidence and make you feel better as you're getting ready to stand on stage. And it something that's me and other Mind the Product speakers, and I've done behind all the big stages that I've done in recent years. Stand there with your hands on your hips and just feel better about it as opposed to sitting there balling up in that tense pile of stress.

**Janna Bastow** (00:17:25):
One of the other things that I always do, if I get a chance to, is get out onto the stage sooner rather later. So when they do the tech check, just walk out onto the stage and just wonder back and forth and look out to the audience and greet it. There's no one there. It's the day before, it's completely empty. But look up at the audience and just enjoy that sweep of the audience, and just get used to it. And imagine it full of people. Don't imagine them naked, that doesn't matter. But just imagine them there, so that when you actually do see them the next day, it's not so stressful.

**Janna Bastow** (00:17:56):
One of the other things I try to do is find the people in the audience who are your fans. And you'll find them in the course of your talk. There's always going to be some people in the audience who just look bored and they're on your phone, just ignore them. They're always going to be there. Find the people who are nodding along and smiling and going, "Yeah, yeah, that's me. That's me." And just speak to them. And if you find one up there and one over there and one down there, no one's going to notice that you're doing your talk just to them. And just keep delivering your talk around the room to these few key people. They're having a great time, you're having a great time, and you're doing a great talk as a result.

**Lenny** (00:18:30):
That's such good advice. The power pose piece, you said that it's hands on hips. I think there's also when we raise your hands up and you're like Superman or something. I think there's-

**Janna Bastow** (00:18:38):
That could work, yeah.

**Lenny** (00:18:38):
Yeah. I think people have different ones. Also, I've seen that, there's like all the science that showed that was effective and then I think it was one of those experiments that wasn't replicatable. People are kind of worried that there's not real science backing that up. But I've done that myself and it actually works. And so it doesn't matter ,if it works for you, just do it.

**Janna Bastow** (00:18:57):
Yeah. If it's a placebo, hey, don't tell me that, it works. Honestly, I feel better at the end of it, and get on stage and do a better job.

**Lenny** (00:19:05):
Someone made this point, placebo is this magical thing that we have in our brains that gets things to change by not having anything go. You just change things. It's amazing. It's magical.

**Janna Bastow** (00:19:15):
Yeah. Placebos are as effective as the actual drug, whatever. I'm happy with a placebo. Just don't break the placebo effect for me. That would be fine, right?

**Lenny** (00:19:23):
Yeah. That's right. One last question on the speaking stuff. How bad were you initially? Just because folks probably see you, see some of your talks and they're like, "Oh, my god, I'm never going to be this good. I'm screwed."

**Janna Bastow** (00:19:34):
Yeah, I used to be shaky, little fawn, shaky voice, terrified at the front. Okay. So it was one of the first ever ProductCamp events that we were running. And the first one I think I did okay at, but it was a smaller group, it who's only like 50 or so people. And the second one it had ballooned to 200 people. This is more product people than I'd ever known. And they were all super professional, and they're all looking at me. And I stood at the front of this group and I was supposed to just, I don't know, tell them what they were supposed to be doing that day. And I had it all half written down, and I started talking and then I sort just tripped up over what I was saying and forgot everything and blanked. And I just looked up and I went, "I'm really sorry everybody. I'm just going to start again."

**Janna Bastow** (00:20:19):
And I started again. I said, "Hi everybody, I'm Janna and welcome to ProductCamp." And I just started again and they were just totally fine with it. Honestly, it was fine. And this is the thing that I've learned since then is people in the audience are rooting for you. They were totally cool with this. They didn't think anything of it and they just rolled with it, as did I. And so whenever I see somebody who's struggling on stage, just give them a nod, a smile, clap them along, give them reassuring looks, and hopefully they'll just pull through.

**Janna Bastow** (00:20:48):
And if you ever feel like you're shaking, you're corpsing on stage, you're falling apart, honestly, just take a deep breath and just pick up where you last remembered you were and just keep going. Honestly, no one is rooting for you to fall over and have a bad time. Everyone's rooting for you to finish your point and get on with it.

**Lenny** (00:21:05):
That's such a great story and it's a good example of people have this fear of the worst case scenario. Everything's going to fall apart. They're going to be seen as idiots, they don't know what they're doing. It's all going to be revealed on stage, because you screw up in how you're talking. And the worst case scenario never happens, in my experience. And two,, if it does, just do exactly what you said, just try to start again. It's easy to say, hard to do. This isn't a conscious thing that people can get over. It's like your body's just doing crazy shit and you're so nervous sometimes and can't just rationalize it to like, "Nah, it'll be fine." But, yeah, it's fine. To your point, people want you to be awesome and succeed. They're not there to like, "Ha, ha, you stopped. You screwed up."

**Janna Bastow** (00:21:47):
And it's humanizing when you screw up, right? People don't like people who are perfectly perfect and don't mess up, and it makes them feel like they can't go up and go do their talk. I mean I think that right there showed everybody else that they could go up on the little ProductCamp stages that day and go do their own talks. And they certainly wouldn't be any worse than that. As long as I just remembered their name, they'd be fine. Crack on, they got it.

**Lenny** (00:22:12):
Speaking of screwing up, you have some very spicy takes on roadmap and roadmaps.

**Janna Bastow** (00:22:16):
Ooh, yes, I do.

**Lenny** (00:22:20):
And then generally the mistakes people make in organizing the roadmap. So I definitely want to spend some time here. So first of all, you have some strong feelings against Gantt based road mapping. Can you talk about that?

**Janna Bastow** (00:22:31):
Yeah, sure. I used to do timeline roadmapping. The first version of ProdPad was actually a timeline roadmap. So to take you back, when I was a junior product manager, mid-level product manager, I used to do my roadmap like everyone else was doing the road, as in I looked up what a roadmap was, and it looked like a colorful Gantt chart. I knew what a Gantt chart was. And so I started putting one together, which is where I'd take the features that I was working on and line them up against their due dates. And I would get a little pat on the head from my boss, and they'd say, "Good job, now go deliver it," basically.

**Janna Bastow** (00:23:05):
And I would do my best with delivery, and I'd never quite be able to deliver everything. Something would always get in the way. But I sort of assumed that was my fault. I just wasn't great at delivery, and I just had to get a little bit better at adding enough buffer and setting expectations and doing a roadmap slightly better. But I figured that this is how everyone was doing the roadmaps, and it was just me who wasn't finishing the stuff on the roadmap quite right.

**Janna Bastow** (00:23:29):
And when it came to creating the first tools for roadmap, I'd envision something that would actually help me manage this format of a roadmap more easily. Which I ended up creating the very early version of ProdPad, which was a digitized version of this, where you could drag and drop ideas onto the roadmap and stretch and squeeze them, and pan the roadmap back and forth. And I shared this with some early product people that I knew, some early users, and they gave me some feedback and some of them absolutely loved it.

**Janna Bastow** (00:23:56):
They're like, "Yeah, this is great. Now I can stop using PowerPoints or whatever tool I'm using or drawing it up in whatever I can now start using this digitized tool." But one of the things that we started hearing from early customers is about a month later they said, "Great, but I want to take this, and move all these things here over by a month in the field." We're like, "Oh, that's interesting. We've heard that from a bunch of other people too. Now why is that?" Because had we just asked our customers, had we just built what our customers wanted, we would've just ended up with a multi-select drag and drop. But this was all built in jQuery and it was a little bit difficult to build that.

**Janna Bastow** (00:24:35):
So we sort of asked the five whys, we dug in to why people wanted this thing, and we found out that no one was actually delivering the roadmap in the timeframe that they were saying they were. So we're like, "Wait, if it's not just us who's not living the roadmap and none of these better than us roadmap product managers are building the roadmap on time, what's the point of a roadmap? Why are we giving them a roadmap?" So that's when we sat down, it was myself and Simon, my co-founder at ProdPad, and we sat down and we came up with a three column roadmap, current, near term, future, which became now, next, later.

**Janna Bastow** (00:25:08):
And it took away the simple concept of a timeline at the top. Now, the problem with the timeline is that as soon as you have a timeline, it turns it into a math chart sort of thing, where you've got time on the X axis and things to do on the Y axis and you basically end up with everything underneath is assigned a due date or a iteration. And it seems that everything that you do has a due date, an iteration just by the format of the roadmap, which is painful. It's just wrong, because we don't have that. The further out you plan, the more you're making it up. We know this.

**Janna Bastow** (00:25:45):
And so we wanted more flexibility and we knew that other product managers wanted that flexibility, because we kept asking what they were up to. So we decided to break it down into these three buckets, and provided that as an option and people loved it. It became this first bump in our usage of ProdPad, because people went, "Oh, wait, I can just say what's happening now, what's happening next, and what's happening later? And if I want to, I can add a date to the specific thing, but I don't have to. And I can be less and less granular about that as I go forwards. Yeah."

**Janna Bastow** (00:26:18):
So it's taking from the concept of the cone of uncertainty, taking from the idea that things get less certain as they get further away, which is kind of how reality works. So the whole beef with the timeline roadmap is just taking apart the concept of the timeline. It doesn't mean we live in la la land. It doesn't mean that we don't believe in having dates on the roadmap, if there is a date that we have to work towards. It just means not penalizing ourselves by having a date on everything on the roadmap.

**Lenny** (00:26:49):
Got it. Okay. I didn't know that you could put dates on some of the things that's interesting, because I was trying to understand exactly how this approach works. We should also mentioned, you came up with this whole idea of now, next, later, which a lot of people use now. Is that right?

**Janna Bastow** (00:27:01):
Yeah.

**Lenny** (00:27:02):
Awesome. Okay. So as someone that's been using Gantt timelines his whole career, I'm really curious to dig into these ideas and challenge the default assumption.

**Lenny** (00:27:12):
I'm excited to chat with my friend John Cutler from podcast sponsor Amplitude. Hey, John.

**John Cutler** (00:27:17):
Hey, Lenny. Excited to be here.

**Lenny** (00:27:18):
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** (00:27:30):
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** (00:27:51):
And supporting growth and learning has always been Amplitude's core focus, right?

**John Cutler** (00:27:55):
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 growing.

**Lenny** (00:28:04):
Absolutely agree. Thanks for joining us, John. And head to amplitude.com to get started.

**Lenny** (00:28:09):
There's two questions that this brings up, and you may have answered them in part. One is just without dates on things, how do you make sure marketing and sales and your CEO has things that they need for promising or at least giving a sense of when a product will come out? And the other is just aligning internally with engineers, design being done on a certain date, engineers being done on a certain date, PMs being done a certain day, [inaudible 00:28:32]. How do you deal with those in this format?

**Janna Bastow** (00:28:36):
There's a couple ways that you can turn that around. So one is you should still be having regular communication, so they can still see what's coming up in the now call them. So they have a sense of what the order of things are and that things that are in the now column are probably weeks away, not months and months away. You should probably have launch readiness meetings so people understand this is the stuff that's going through testing, and that's likely to be coming out now.

**Janna Bastow** (00:28:59):
But one of the other things that you can be doing for your marketing and sales teams is separating your hard launch from your soft launch. So what you should be doing is basically saying your developers are able to launch something on a particular date and it's the date that's convenient for them, right? Let's say they think that they can get something out for end of September. Now, that might be pushed to made October because things go wrong.

**Janna Bastow** (00:29:23):
Now at that point, whether it's end of September or mid-October, it doesn't really matter to the marketers because they're busy talking about the stuff that was launched in August. They've got lots of stuff to work on. They're selling and marketing the stuff that's already live and out there. When this new thing comes out, that's a soft launch. As soon as that soft launch is out, great, let's kick off this launch meeting with launch steps. Now you've got something else to go do. And it's so much better for marketing anyways because they're not setting up their launch steps based on something that they don't have eyes on. There's nothing worse than the marketers trying to market something based on pictures from the designers that have vastly changed by the time they go out or that they don't know whether it's going to come out on the right day or not.

**Janna Bastow** (00:30:07):
So they've actually got a functional working version that they can share with some customers. They can start getting videos of it working. They can get testimonials from early beta users. And then they can spend, whether it's two days or six days or six weeks or six months planning the biggest, bangest launch they want. They can then spend the next however long they want to launch their hard launch, and then that goes out. And in that period that they're doing that hard launch development is cracking on with their next thing.

**Janna Bastow** (00:30:41):
And by the time that they're done that marketing is then, "Okay, great, what have you built? We're ready to work on the next thing." So you're just separating soft launch from hard launch, so that you don't have this stress of trying to line up to completely different types of projects, your marketing projects and your development projects, which is where a lot of those things fall apart.

**Lenny** (00:31:00):
Got it. So kind of the basic premise is roadmaps or timelines sound great and awesome. Everyone would love to know when things are going to be done and if it worked it'd be great. Oftentimes, they're all made up, they don't work, you don't hit deadlines, they're always missed. So instead of promising dates for everything you're doing, you're better off generally just giving a sense of, "Here's what we're going to work on now. Here's what's coming up next." And then for the things that really need a date, we're going to put dates on those things and give it our best shot. Is that [inaudible 00:31:29]-

**Janna Bastow** (00:31:29):
Yeah. That's absolutely right. If something does have to have a date, we don't live in la la land, if something has a regulatory date, when GDPR came down, everyone had a due date on the roadmap, because if you didn't hit that date then you were going to be in trouble. Sometimes you might have dates that are tied to things like the Christmas rush, or if you're in education it might be like has to be out by the school year.

**Janna Bastow** (00:31:50):
At which point, in order to reach something by that date you have to put in more project planning work, as in you have to plan out ahead of time, you have to put in more buffer time to do that. And generally you have to plan to get that thing done well before, so that you can have a soft launch before and make sure it works and do some iteration and fix it before the actual full-on launch happens. Because if you leave it too late, it's going to go wrong and you're going to miss the deadline.

**Janna Bastow** (00:32:16):
If you did that for all of your launches, you're just going to end up either cutting quality, because everything's just going to be big crap cause it's going to be pushing it out the door last minute. Or you're just going to end up spending so much time trying to plan things to the nth degree that you're just going to move super slow. This is why you end up with teams who are really big but can't deliver worth anything. Where compared to these tiny teams, who are just out delivering them and just spinning things out the door, they're the ones who aren't spending all their time going, "Are we certain this is going to deliver? And how many hours is this going to take you? And let me go talk to this person, find out how many days it's going to take him," and back and forth and back and forth. They're just building, and it goes faster.

**Lenny** (00:32:57):
I'd love to pull on that thread. I was thinking about the fact that you're building software for product teams and so you have a really unique perspective on product teams and you've seen a lot of product teams a lot more than a lot of other folks. And so I was curious what percentage of teams that you see are what you'd call like top notch, highly functional product teams?

**Janna Bastow** (00:33:18):
That's a good question. I don't think I've got an answer there because it's going to be biased, because we naturally attract companies who self-select our way of working. We put on our site, no timelines come for the now, next, later. So it's going to be a much higher percentage. People don't sign up for demos with us if they know that they want a timeline nowadays, because we make it really clear. So I would say like 70% of them are like we want now, next, later. And I know that's not real. I know that's not the real state of people, of product teams out there.

**Lenny** (00:33:48):
Cool. So yeah, that makes sense.

**Janna Bastow** (00:33:49):
I do have a sense that it's increasing. So what I have found is years ago when we first started this thing off, no one was talking this way. It was a whole new concept and people are like, "No, this is crazy doc, you can't do it this way." Then over the years it has just become the natural way that people are working on it. People are going, "Of course this is the way that it works. Why would it work any other way?" It's becoming the expected way. Definitely changed the discourse and changed the expectations of the audience, I guess.

**Lenny** (00:34:13):
Putting the now next later piece to the site for one moment. I'm curious what else have you seen separates the best product teams from mediocre product teams? In terms of how they execute, the people they hire, processes, is there anything else that you've noticed of just like this team, when I think of teams that are functioning super well? Other than implementing this process you're recommending, is there anything else that often comes up?

**Janna Bastow** (00:34:37):
Yeah, a couple things. A focus on discovery. So this ability to spend time in discovery and asking questions of customers and constantly being able to iterate based on that. And psychological safety, so teams who are able to question each other, speak up when they see that things are wrong, question what's going on at the senior level, question what's going on at different team levels, and generally just have the good sense of what's going on across their business because they're allowed to ask those questions, less silos.

**Lenny** (00:35:05):
Thanks. What's a lasting change that a team has made that made them significantly better at building product? Is it these two things, doing more discovery and maybe more safety? I imagine part of your answer will be implementing this way of working of now, next, later. Is there anything else that comes to mind? "Wow, wow, this one team did this one thing and it made things so much better for them."

**Janna Bastow** (00:35:24):
Like retrospectives. Retrospectives make such a big difference because they are indicative of psychological safety, which underpins so much, right? Once you start building in this psychological safety, the ability to ask questions and to start saying, "What are we doing that's working? What are we doing that's not working? Okay, determine that something doesn't work. Are we allowed to go change it? Okay, we are allowed to go change it." Okay, this is a team who's now changing their situation. They're talking to each other, they're learning from each other, and they're making a concerted effort to do so. And so these are the teams who are constantly learning, iterating, and moving forwards.

**Janna Bastow** (00:36:03):
And they naturally move towards things like now, next, later. They naturally move towards things like doing discovery, because these are just, I don't know, they're kind of common sense. They're not setting in stone expectations of what's going to be done and when. Because that was really only done because some head honcho wanted to see that information. That wasn't psychological safety. That was somebody pinning them down by the neck saying, "Tell me what's going to be done and when." Psychological safety is just saying, "Hey, tell me as much information as you know and then do discovery to learn as much as you can, so that we can move forward with this." It's all about just talking to your teammates and getting the most information as you can from the resources you have, making the most of the collective intelligence that you have within your company.

**Lenny** (00:36:46):
Coming back to the now, next, later approach, you're often doing something really hard at companies, which is changing their way of working and changing their product culture. And I'm curious what you've learned about what it takes to change product development culture and product culture and the way of working at larger companies.

**Janna Bastow** (00:37:04):
Larger companies are tough. They're tougher. I think of culture as calcification. So calcification being the limestone that is built up as watered run over and that sort of thing. And in order to fix it, you can kind of chip it off over time. You can't just fix it all in one go. And so in order to fix it, you've got to chip away at it. You've got to find a small pocket somewhere. You've got to make use of the tools that you've got. So sometimes it might be finding a small subset of the company and saying, 'Hey, here's the startup lab within the business. Let's let them run off and go do something." Because changing the mindset of the whole company is just too difficult. It's set in stone, and it's stuck where it is and can't change them all at once. But we can change this one little space right here, because we've got a shit hot leader who knows what they're doing and we can take this pocket of people and go do something here.

**Janna Bastow** (00:38:00):
And then they're going to teach the rest of the company. They're going to teach this section and then this section and then this section. You don't have to go and change the whole company all at once, but it does take buy-in from above. And sometimes that can be really difficult to take, because the incentives from above are often misaligned with the incentives that it takes to get a company moving this direction.

**Janna Bastow** (00:38:21):
Ultimately, a lot of these larger companies, they're incentivized to keep the company as stable as possible, to keep the company just growing quarter on quarter. Which is great for the stock market, they love that stability, they love that quarter on quarter growth. But if the company is actually under threat from startups, if you're a big bank, you're in health tech, something like that, you almost certainly have startups nipping at your heels. And the reality is that you probably have enough cash to make it for the next 20 years or so, but over time it's going to get bitten away at.

**Janna Bastow** (00:38:58):
And you've got smaller startups who are going to take the juicier, more interesting parts of your business and leave you with the tougher parts of your business. Take HSBC versus all the companies who are coming out with got a Starling account here and I've got a mortgage with somebody else and you've got your savings account somewhere else. You've got all these smaller startups nipping at their heels. These companies are going to nip away at these larger businesses and if these larger companies don't actually do something with it, they're actually going to end up losing this ability to innovate themselves. And so these companies are essentially stuck in this pattern where they want to continue growing and yet they're not going to, they're going to end up not being willing to take the dip to move upwards.

**Lenny** (00:39:42):
What's the biggest company that you've implemented this new way of building? And is that how you approached it, you found a team within the larger company to roll out this new-

**Janna Bastow** (00:39:53):
Yes.

**Lenny** (00:39:53):
... yeah, this framework?

**Janna Bastow** (00:39:54):
Yeah. So that's how it generally works with the way that we work with our enterprise rollouts is like we worked with large enterprises of governments as well. It generally starts with an advocate, somebody who gets the way that we're working, a division, a department, and then it starts from there. Sometimes what we'll find is that we'll get one or two, sometimes three or four many groups starting and then they'll start banding together and saying, "Hey, no, we're starting a thing here." Once that starts happening, it's easier to start that conversation saying, "Okay, yeah, we've got a whole thing going here. Let's talk to the person who is the VP of strategy, or who owns the tech area," and then we can have a bigger conversation.

**Lenny** (00:40:33):
What's the impact that you saw at that company having taken on this new way of building product?

**Janna Bastow** (00:40:39):
So we're in the middle of a key tool in the middle of transformations right now, which is fascinating to see. These are multi-year pieces of work where you're seeing it being used for ongoing products that are being used and delivered as we speak, as well as part of a mindset shift within the business. Because one of the things about ProdPad is that it's not just a tool to help you deliver your products, it's actually a tool that helps you become a better product manager. It sets in stone better product management practices. Once you start using it, it makes it difficult to go back to bad product management practices.

**Janna Bastow** (00:41:15):
When you create a roadmap in ProdPad, it makes difficult to add features and dates to the roadmap. It makes it difficult to make a timeline based roadmap. It makes it difficult to add ideas to the backlog that are not thought through, because it asks questions, thoughtful questions, like what problem does this solve? And why would you want to solve it? And what are the outcomes? And what did you get?So it makes it difficult to fall into a build trap with just saying, "Here's stuff to build," and we built it, and move on to the next thing, like a lot of dev tools are designed to do. Because it has spaces in there to say, "Did you measure success? And was it successful or not successful? This roadmap thing is completed, what was the outcome of it?" So by creating all these spaces, it creates all these reminders for the team to go back and think about this stuff before they do work and after they do work. So it actually actively helps them become better product teams and more cognizant of this sort of work.

**Lenny** (00:42:05):
If someone wanted to experiment with now, next, later, what would be a good place to go and just start to play around with it?

**Janna Bastow** (00:42:12):
I mean, you can start a free trial in ProdPad, you can start playing around with it. We even have a sandbox mode. You just go to sandbox.prodpad.com where it's got example versions of roadmaps, best practice roadmaps that you can just start playing with. You don't even need a login or a credit card. It's got OKRs and roadmaps and ideas and experiments, feedback. You see how it all sort of fits together. But honestly, a now, next, later roadmap can be done with Post-It Notes on the wall. It's just about saying, "What problems do you have? Let's lay them out in order and just check them with other people."

**Janna Bastow** (00:42:45):
So the whole point about a roadmap is that it's not designed to be your plan. I think about it as being a prototype for your strategy. What I mean by that is we talk about prototyping all the time in the lean world and a prototype is essentially a way of checking your assumptions. Generally, we think about it in terms of a design or like a model, but think about it at the strategy level. So at the feature level, you'd prototype by doing a design, a mockup, and you take that mockup and you'd share it with somebody, and say, "Here's a mockup of the feature that I'm trying to build. What do you think?" And they tell you what's right or wrong, and you'd add some new copy or a button to make it more clear, and you throw out the original prototype, because it wasn't very good and you make a new one.

**Janna Bastow** (00:43:27):
So the value isn't the prototype, the value is in the prototyping process. The value isn't in your roadmap, The value is in the roadmapping process. What you're actually doing is laying out your assumptions of the problems that you're solving. So you're saying, "I think we have this problem then this problem. What do you think?" The whole point is that you just share your early assumptions with other people on the team, with customers, even, like anybody, who will listen. And just check that you're on the right path. And if they say, "Oh, actually I thought that it was going to go this way, this way, then this way, or that way, then the other way, and what about this problem?" You've actually learned something. You can adjust your prototype for your strategy, you can adjust your roadmap there and your roadmap all of a sudden becomes stronger, becomes better there.

**Lenny** (00:44:11):
For folks that are listening and they're just like, "Nah, this is never going to work where I work. It's just too out there, too radical. No deadlines, that's crazy." I know you're not saying no deadlines, but less deadlines. What are the most powerful three bullet points you could share with listeners that are just like, :Here's why you should have confidence this might actually work at your company."

**Janna Bastow** (00:44:32):
Other teams are already working this way. Product people are the only ones who seem to be pinned down to be required to give concrete dates as to when things are going to be delivered in this way. Your sales team isn't asked to give exact delivery dates on their work. They work in a very experimentation led way as well. You are VP sales or VP revenue or whoever doesn't go to a board meeting and say, "We're going to close the Acme deal at the end of October for a million pounds." They don't know that. What they do know is that they have a process by which they're going to fill a pipeline, and almost certainly they're going to be able to close a million pounds or a million dollars worth of sales, but they can't tell you who it's going to come from or how that's going to work.

**Janna Bastow** (00:45:19):
What they're going to say is, "Give me a quarter million dollars worth of investment into my team, which I'm going to spend that on my account executives, my sales team. They're going to pick up the phone and do a bunch of calls." Think of these calls as experiments. These calls, some of them are going to work, some of them are going to fail. They don't know which ones are going to work and which ones are going to fail. What they do know is that by using a script and by picking up the phone and calling people, some are going to work. And by the end of the quarter someone's going to buy. And they know this because last quarter someone bought and the quarter before that someone bought, they just don't know who's going to buy. If they did know who's going to buy, then they would just call those people and not everybody else.

**Janna Bastow** (00:45:59):
Same thing. You're not asking for any more leeway than your sales team. You're saying that you want a quarter million dollars worth of investment, and you're going to spend it on your team who's going to run experiments, right? It's going to be trying this change on the interface or that tweak to the pricing or that change to the positioning or whatever you're going to do. Some of these experiments are going to fail and some are going to succeed. You don't know which ones. But that's okay, you know that by the end of the quarter, enough are going to succeed that you're probably going to move the right numbers in the right direction.

**Janna Bastow** (00:46:30):
So you're not asking for any more leeway than your salesperson. What you should be able to do is point at how many experiments you ran the previous quarter, and what numbers moved in the right direction. You should be accountable for your experiments and how you're spending the money and what you're doing. But you shouldn't be accountable for saying what is going to work before you know what's going to work yet. And that's the problem with this timeline delivery, Magic 8 Ball that we're asked to give.

**Lenny** (00:46:58):
I like that. Two last questions before we get to a very exciting lightning round, which I didn't tell you about. We'll see how that goes. So one is you have an interesting framework for coming up with a product vision, and I don't know if you have this in your head loaded up, but I'm curious how you think about coming up with a product vision. You have this really handy little framework, and vision is always this thing that people are like, "Man, how do I come up with a vision? How do I phrase a vision? How do I even visualize my team's mission?" Can you share that with us, if you have that in your head?

**Janna Bastow** (00:47:30):
The product vision template, you might actually recognize it from the Geoffrey Moore's Crossing the Chasm book. It's the elevator pitch template. But I like it because it answers the same sort of questions that you need to answer for a product vision template. So it asks things like, for your target customer, who the statement of need or the opportunity. The product name is a product category. What's the reason to buy? And then say, unlike this alternative our product, and then say what this statement of differentiation is. So it's actually a template that we have available on our site, and you can actually fill out as part of our product canvas in ProdPad. So happy to share that link with you, so you can link it up and send it to your audience here, Lenny.

**Lenny** (00:48:17):
Cool. Yeah, we'll put that in the show notes. I think that's the same framework as the positioning exercise. I might be wrong, but if so, that's cool. So basically you could use your positioning work to help figure out your vision. And just like a vision, it's basically a vision statement, it's not necessarily the vision for your product, it's just kind of how you think about where it's going to go.

**Janna Bastow** (00:48:35):
Yeah.

**Lenny** (00:48:36):
Okay, cool. The last question, you were a PM now you're founder, so you moved from PM to founder, and a lot of PMs, imagine being founders someday. I'm curious if you have any advice for folks that are currently PMs that may want to be founders in the future. What do you think they should be working on, focusing on, skills, vision rebuilding, things they should be doing to help them in that future career?

**Janna Bastow** (00:48:58):
Being a PM actually provides you with a lot of the skills and background to be a founder, to be a CEO. It gives you a lot of chance to work with a lot of the different teams and see a lot of the underpinnings of how business works. I was really lucky in previous roles where I got to work very closely with leadership in a few different roles before I took the step up to take on my own thing. So I felt as if I'd seen it in a few different ways, done well and done badly, and so I got a chance to sort of say, "Ah, I think I could do this. Yeah, go on."

**Janna Bastow** (00:49:32):
One of the things that struck me is it's not as hard as it looks, and it's also harder than it looks. There's things that you get started and you go, oh, no one's going to stop you from doing this. You've got lots of leeway. You can just do it, and you've got lots of freedom to run your business how you want to do it. There's lots of resource out there. As long as you surround yourself with people, you're always going to be able to find people to advise you and to help you along the way. And there's always going to be bumps. You don't know what they're going to be yet. There's always going to be things that are going to come by and side swipe you, but that's always the case that you had when you are product manager as well.

**Janna Bastow** (00:50:11):
And just be ready for those and be ready to take it on the chin and deal with them as they come. Best thing you can do is surround yourself with people so that you've got somebody to go to for each thing. Going, "Oh, when I run into a problem that has to do with this, I can talk to this person. When I run into a problem that has to do with this, I talked to one of these people." And figure it out as you go. Take each thing a day at time. Certainly, don't stop yourself from starting a business or starting your own thing, just because you don't think that you know how to do it yet. You will figure it out as you go ahead. People less capable than you have figured it out.

**Lenny** (00:50:46):
Awesome. Okay. We've reached our lightning round. The way it's going to work, I'm going to ask you five questions real quick. Whatever comes to mind, share an answer.

**Janna Bastow** (00:50:55):
Cool.

**Lenny** (00:50:56):
If nothing comes to mind, that's also cool. Sound good?

**Janna Bastow** (00:50:58):
Mm-hmm.

**Lenny** (00:50:59):
What are two or three books that you've most recommended to other people, whether they're product leaders or just generally?

**Janna Bastow** (00:51:06):
Art of Profitability, I thought was a really good one.

**Lenny** (00:51:09):
What's a favorite recent movie or a TV show that you've watched?

**Janna Bastow** (00:51:13):
Oh, Sandman.

**Lenny** (00:51:14):
Ooh, and that's-

**Janna Bastow** (00:51:16):
Sandman is-

**Lenny** (00:51:16):
... like a British show, right?

**Janna Bastow** (00:51:17):
Oh, it is British. Yes, by Neil Gaiman. Yeah, very good. Definitely, not for children. Thought it might be, definitely not.

**Lenny** (00:51:25):
Noted. What's another favorite podcast of yours other than the one you're currently on?

**Janna Bastow** (00:51:31):
Ooh, Startups For the Rest Of Us.

**Lenny** (00:51:33):
Wow, I haven't heard of that one. Tell us more.

**Janna Bastow** (00:51:36):
Basically, it's Rob Walling's podcast and it's for startups that are either bootstrapped or alt funded. Basically, the startups that aren't the one percent top end funded, unicorns, but the startups for the rest of us.

**Lenny** (00:51:52):
Awesome. What's a favorite interview question of yours that you like to ask?

**Janna Bastow** (00:51:57):
I like asking people what problems that they're looking to solve. Why are they coming to this table?

**Lenny** (00:52:03):
Very PMy question.

**Janna Bastow** (00:52:05):
Yes.

**Lenny** (00:52:05):
Who else in the industry do you most respect as a thought leader? Who comes to mind?

**Janna Bastow** (00:52:10):
I've got to give a shout out to Christina Wodtke. I had a great conversation with her yesterday, and I've had a chance to chat with her a number of times over the years, but she's just got this illustrious career. She's been part of so many amazing teams, built some amazing things, written some amazing books, and is also just an all round amazing product person and amazing person all in one.

**Lenny** (00:52:32):
Janna, this has been amazing. I think we covered a lot of different topics, more than we often cover in a podcast like this. Two final questions, where can folks find you online if they'd like to reach out and learn more? And how can listeners be useful to you?

**Janna Bastow** (00:52:45):
Wonderful. Hi, I'm Janna Bastow. You can find me all on Twitter, I'm simplybastow there. Or come find me on LinkedIn, connect with me, I'm Janna Bastow. I'm easy to find there. And come check out ProdPad. It'd be wonderful to get your feedback on it, because we are a team of product people and we love hearing what other product people think of the product. We're always open to feedback. We're constantly pushing new releases. So check it out, try the sandbox. We'd love to hear from you.

**Lenny** (00:53:11):
Amazing. Thank you for being here, Janna.

**Janna Bastow** (00:53:13):
Of course, thanks so much.

**Lenny** (00:53:16):
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 a leaving review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [5/20] Humanizing product development | Adriel Frederick (Reddit, Lyft, Facebook)

**Adriel Frederick**:
There are probably, I call them techno utopians who would say, feed all data to the algorithm, give it an objective, and it will do the right thing. And I was like yeah, the reason that falls down is the algorithms don't understand long term effects often, nor do they understand how people might respond to it, nor do they understand your intent for the product, and I think it's really important for product managers to play that role. That is our job. When you are working on algorithmic heavy products, your job is figuring out what the algorithm should be responsible for, what people are responsible for, and the framework for making decisions.

**Lenny**:
Welcome to Lenny's Podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products. Today my guest is Adriel Fredrick. Adriel is a VP product at Reddit where he focuses on incubating and scaling new products within Reddit. Before that, he was director of product at Lyft where he led the marketplace teams and the pricing teams over the course of five years, and before that, he was an early PM at Facebook where he spent four years leading the user acquisition team. Adriel is one of these incredible product leaders who's way too under the radar because he doesn't spend all day on Twitter and instead is executing and building great products. One of the goals of this podcast is to highlight incredible product leaders who you may not be aware of. And Adriel is a great example.

**Lenny**:
In our chat we talk about the origins of growth hacking, how to get better as a product leader, ways to increase diversity at your company, what it was like to work on Facebook's growth team early on, the future of AI and a lot more. It was such a joy chatting with Adriel and I am really excited to share this episode with you. With that, I bring you Adriel Frederick.

**Lenny**:
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**Lenny**:
Hey Ashley, head of marketing at Flatfile. How many B2B SaaS companies would you estimate need to import CSV files from their customers?

**Ashley**:
At least 40%.

**Lenny**:
And how many of them screw that up and what happens when they do?

**Ashley**:
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 chop full of unexpected data and formatting, they'll leave.

**Lenny**:
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**:
Totally. It's incredible to see how our customers like Square, Spotify and Zoro 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**:
If you'd like to learn more, get started, check out Flatfile at flat file.com/lenny.

**Lenny**:
Adriel, welcome to the podcast.

**Adriel Frederick**:
It's good to be here, Lenny. Thanks for having me, man.

**Lenny**:
It's absolutely my pleasure. I actually found out about you through a guy named Jules Walter who we both know.

**Adriel Frederick**:
Yeah.

**Lenny**:
He's a PM at YouTube and I actually asked him, who should I have on this podcast that is maybe a little bit under the radar that is just amazing and immediately he suggested you. And so I'm really excited to be chatting.

**Adriel Frederick**:
Man, that is hype praise coming from Jules. Jules is my boy. I love him. He's such a great guy. Awesome product manager and dedicated to the craft that I just like being in his presence.

**Lenny**:
Yeah, and we're going to get him on this podcast at some point. He's busy with some kind of secretive project that we can't talk about. He's scheduled, I could talk about Jules all day, but he actually has the 10th most popular guest post on my newsletter still. How about that?

**Adriel Frederick**:
Wow. Yep, he's awesome.

**Lenny**:
Anyway, enough about Jules. So to give listeners a little bit of context on yourself, can you just give us a 55 second overview of all of the wonderful things that you've done in your career?

**Adriel Frederick**:
Ooh, we'll do real fast. So big highlight about me is I'm originally from Trinidad and Tobago, an island in the Caribbean. Came to the US for college, double E, got seduced by consulting and did that for a couple years, worked in oil and gas, electric power, heavy industries, loved that stuff, but also liked writing code on the weekends for fun. So I thought I should move into tech and I did. Worked at Intuit and helped develop their first iPhone app, which was a thing back in the day. Worked at a startup growth team at Facebook for four years working on user acquisition, which was really fun and a good kind of strong formative experience. I had. Quick stint in biotech and then worked on marketplace at Lyft. So rider pricing, realtime driver incentives, matching rider with drivers, and then a lot of the operational tools that we use to manage our marketplace. And so that's a bit of my journey in maybe 45 seconds.

**Lenny**:
That was great. I don't have a timer for these, but that sounded right. So we're going to talk about a lot of the things that you've learned along the way at all those places. Can you also share what you do now?

**Adriel Frederick**:
Awesome. Yes. So I'm the Vice President of Product Management for Reddit X, which sounds like we're out launching balloons into space, but that's not exactly what we're doing. We're more of a team at Reddit that's thinking about the evolving the modes of interaction with Reddit. So content, temporality, the audience that you're talking to, if you think about it, Reddit is primarily about asynchronous conversations between anonymous strangers about shared interests. Sometimes other people find answers to their questions on Reddit, but we're looking into and on the X team, evolving that to look at problems like helping people communicate fast during easier about shared interests, perhaps changing who they're having conversations with. Maybe it's about something other than a shared interest or maybe they have something else in common that brings them together. Maybe bringing video, audio, and other media into being a part of the product and playing with permanence and things like that.

**Lenny**:
Whoa, I felt like you were going to go into a metaverse direction. Is there metaverse angles to this?

**Adriel Frederick**:
Not really. I think we look at that as a potential technology, but our primary focus is a lot more on, I see modes of interaction and platforms that are a lot more at scale today.

**Lenny**:
Got it. Is there anything coming out in the near future we should be looking forward to? I imagine you can't talk about too much of what you're actually working on more concretely.

**Adriel Frederick**:
I think there's a few things that we've done recently that have been fun. We have an avatar marketplace that we've been working on recently where creators have been able to make art, put it up for sale on Reddit and make that available for other folks to buy and use. And that's been performing amazingly well. The underlying technology behind it is NFTs and we thought that technology was really important to use because it gives a creator a public way of acknowledging their rights to a piece of content. And so they have some form of IP protection, especially in a marketplace where you're doing something like selling digital art, we felt like that was incredibly important. I think the technology behind NFTs has been used for some really nefarious things, but I think we're still in the infancy of using these technologies appropriately. There's a lot of terrible use and a lot of uses that are wastes, but I think there's some gems in there and we're hoping to find some of those.

**Lenny**:
Sweet. I will avoid getting pulled into a web3 rabbit hole here, but that is very cool. Something I wasn't planning to ask about, but I'm curious because I was just talking to some other guest about this topic is the idea of these kind of R and D ish teams at larger companies and companies that have been around for a while. I know you're relatively new there and that's kind of maybe a new thing, but I'm curious, is there anything you've learned about how to set up teams like this and investments like this, these kind of long term horizon bets R and D teams?

**Adriel Frederick**:
Yeah, I think it's really good coming to this from being on the other side of it. If you think about where I've been, I've been on growth and on marketplace, which is as far as you get from seeing where on the new stuff kind of team and what I've seen happen a lot is organ rejection, that this thing looks so different to the rest of the body and the rest of the organization that you get some form of rejection of the ideas entirely. So I think what I've learned is a few things.

**Adriel Frederick**:
First is the rest of the company needs to see what you're doing as being core and critical to the mission. It can't seem like these guys are just playing off in a corner on something that isn't related to what we are doing every day. Because I think that leads to some of the resentment because you can imagine any team internally is fighting for resources and they look at this group as having resources that they can't get. They're like, Oh we got to get rid of that because they're not helping us do what we are here to do. So you have to be part of the core mission, otherwise you're going to have problems culturally with that. So I think that's one thing.

**Adriel Frederick**:
The second is it has to be everyone's success. So if you end up doing something on one of these R and D teams, it shouldn't just be the R and D team that wins. Everyone should feel like they win. And that is kind of relates to that first goal I was talking about. I think the third is you have to set up the work that these teams are doing such that people don't believe all innovation is going to happen on that team. It can like, okay, we're just stuck with the operational stuff and they're getting to have all the fun. Other teams are still going to innovate, but maybe we're taking on something that other teams don't have capacity for, that the organization needs and it's part of the core mission. And so I think that's been a lot of what I think about when working on and setting up these teams is to make sure that we are part of the organization and everyone wants to hug us as being, yes, you are one of us not, you kind of need to go off in your little corner and behave.

**Lenny**:
Amazing. That is really helpful. So just to kind of recap, you want it to feel like it's core and critical to the company. You want it to feel like it's everyone's success. It's not just, oh, Adriel over there is doing great, but we're stuck with these terrible hard problems. And then this idea of not all innovation's going to be just coming from that. We can all innovate but they're just working on this one specific innovation.

**Adriel Frederick**:
Yeah.

**Lenny**:
Awesome. Okay, great. Another question I definitely wanted to ask you. So you said you were born in Trinidad and Tobago, not something that you hear very often in tech. I'm curious your background and your journey to what you do now, how does that impact the way you lead, the way you build product, the way you just think about your career broadly?

**Adriel Frederick**:
Yeah, it's not something that I really think about consciously, but it affects me every day and it's tough not to see it in retrospect. I was the first Black product manager at Facebook.

**Lenny**:
Oh wow.

**Adriel Frederick**:
And so it's tough for me to not see that having some effect on what was built or how things were built or on me. So it's pretty meaningful. But I think one of the ways to see how it effects things is actually just to understand a little bit about Trinidad. It's kind of its own little unique animal. So Trinidad is an island in the southern Caribbean all the way up bottom next to Venezuela. It's a really diverse place. So ethnically it's 35% Indian, like from East India, 35% African, 25% mixed, and that last 5% is everything under the sun. European, Chinese, Arab, et cetera.

**Adriel Frederick**:
And then for religions it's about 60% Christian, but then that's a lot of different forms of Christianity in that 60%, 20% Hindu, 7% Islam. The media diet is a mix of British and American TV. You have a really broad range of incomes, but then schools are a melting pot, so you don't have as much of the kind of class and income segregation with schools that you get in most of the west. And so when you have that kind of a melting pot of ethnicities, religions, media consumption and kind of socioeconomic status in one place, you learn a lot of them because in school you're mixing up with everyone. One of the jokes we have is Trinidad probably has the most public holidays of any country because you have to celebrate everyone's holidays from Diwali for Hindus, Eid al-Fitr, to Christmas, I have friends who were fasting for Ramadan. I know a lot of the names of Hindu gods and I always love shocking my coworkers with my knowledge of this stuff. So that gives me this really different perspective that shows up at work.

**Adriel Frederick**:
So I'll give you an example. Something I've noticed in almost everybody I worked with in tech, as we work on mobile devices, people make an assumption that one phone number plus one device tied to one person. And growing up in Trinidad, I just knew that wasn't true. Someone who is using a prepaid phone could have their number change all the time, so that one person could have multiple phone numbers just because they were using prepaid. You have phones for two sim cards, that was pretty common. And a phone is and definitely was a really expensive digital device. It's a computer. So it was often shared and people couldn't just have one for themselves.

**Adriel Frederick**:
So when I was working on user acquisition and designing registration for Facebook, that knowledge was incorporated into the design of the product in ways that I think other companies not caught onto yet. And I know for a fact that a lot of that thinking that went into designing how you think about a phone number and a device and it's use among one, it's how to say pairing with an individual, has been helpful for Facebook's growth back then and even after I left, I know that's still been providing benefit. So that's a simple example of how just being in that environment and soaking up information could help product design in a way that I think wouldn't have happened if I and others like me weren't there.

**Lenny**:
You said you were the first Black PM at Facebook. I didn't realize that. How many PMs were there at that point when you joined?

**Adriel Frederick**:
Oh man. I remember we all fit into this conference room called Canada and that was probably my second week. It was probably about maybe 30 of us in there.

**Lenny**:
Wow. Yeah. Is there anything that you learned from that experience about just how to help with diversity at a company? Did Facebook do this well? Have you seen other companies do this better? Is there something you could share there for folks that are trying to work on this?

**Adriel Frederick**:
Man, that's a tricky one. So there's two parts of that, what was that like for me? I think it went quickly from being a little bit of imposter syndrome, like that day when I was sitting in that group was like, Dude, I'm one of 30 people working on Facebook. What am I doing? I'll belong in this group. This is crazy. And then I recognized after talking to a lot of the other PMs and the engineers, it's like no, no, no, they want me for what I know from my perspective because they're really trying to grow this product globally. And being this guy from Trinidad working on growth with the perspectives I just mentioned was appreciated. I think I was lucky enough to be on the growth team and having leaders on that team really valued diversity. I think about some of the teams I was on and they were awesome. I joke about them sometimes.

**Adriel Frederick**:
I remember being on a team where I was a Black Trinidadian product manager with a female Israeli engineering manager, a female Brazilian tech lead, then the rest of the engineering and design team was from all over the world. We had Russians, Chinese, some folks from Slavic countries and it made designing products fun because a lot of times when you're building a product and you want to think and get into your head of your customer, you have to go out and talk because you don't necessarily get them really well. Man, we didn't need to on that team. We would just argue with each other. We would think about how our friends would use it, how our cousins would use it, and we are covering a broad swath of the world when we were arguing about how to design a product. But I think the original leadership of the growth team, I think starting with Chima but then followed up with Javi.

**Adriel Frederick**:
[inaudible 00:16:51] that and kept bringing in that diversity of, again, ethnicities, religions, cultures from all over the world so that you could actually build a product that way. And it just makes you so efficient because an argument that might take two weeks to resolve because you have to go recruit a panel of users and talk to them and figure out what's going on. We kind of knock out in 15 minutes just throwing it back and forth with each other. And I can't stress how much that's important for building products that you want people across the world to use. You got to have your teams look like the world, it just makes you so much faster. It's not perfect. You still have to go out and talk to folks because we still have our own kind of monocultures that form that we need to get out of. But it helps a lot.

**Adriel Frederick**:
To your second point about diversity and how to foster it, man, from the beginning of my career at McKinsey to today at Reddit, I've been in rooms where everyone's asking the same questions about how to fix it and here's what I've seen work. When you recognize that you get business value from it, then it all of a sudden becomes something that you look out for and you take care of. That's it. And there's definitely a lot more to it, but I think when it goes from frankly something people feel they need to do to be PC or for cultural reasons or because they're getting social pressure to do it to something that you really recognize concretely, no, I get value from this and you are willing to take the other steps to have a culture at your company that utilizes it, then it becomes easy because when you bring folks in from diverse backgrounds, they retain and that's always the number one step to growth as you will know.

**Lenny**:
Retention.

**Adriel Frederick**:
You have to retain them, you have to retain diverse talent. And so you have to have an environment that values it, cares about it and uses it and rewards it because it's part of the core system of the company. Then once you have that working, it becomes a lot easier to recruit because people see you valuing it and bringing it in and wanting it. And it's not just lip service that you're paying. That's been what I've seen to be true in all the conversations I've had on the topic.

**Lenny**:
That first piece is interesting that it answers the second piece, which is the point you made about how having a large diverse global group of employees early on, especially for a company that's trying to go global and international is so powerful, you just save all this time. You don't have to necessarily interview people that you don't already have.

**Adriel Frederick**:
Yeah, there's something that feels like the approach to not doing it that way feels colonial. It almost feels like we're a group of people sitting down in this tower in this country, in this relatively sterile environment and don't worry, we know exactly what you need and these are the parts of the world. It just doesn't work well. So doesn't feel right to me also.

**Lenny**:
Yeah. Awesome. Thanks for sharing all that, that was really helpful. There's another topic I definitely wanted to spend a little time on, which is this interesting trend that I noticed when I was looking at your LinkedIn and your background. You worked at Facebook, Lyft, Reddit, and interestingly, they're all very in the news full of controversy type places. People like to tear them down and show all the reasons that they're doing bad things to the world. And I imagine as a PM that's just a challenging place to be and the fact that you've been at three different places. I imagine you've learned some stuff about how to operate as a product leader at companies full of chaos and fires and bad PR and things like that. So is there anything to share about what you've learned there?

**Adriel Frederick**:
I think the biggest thing is that as a PM you are a leader. You have to provide a buffering or damping effect on the team, and that goes two weeks. Sometimes we're doing stuff that everybody thought was amazing, this is the best thing we've ever seen, and you kind of got to bring people back down to earth and go, Look, that was cool, but we got a lot more stuff to do. We are really not there on providing the value that we want to provide to people in the real world, so slow your role and recognize that there's a lot more to do. And then when it's terrible and the press is telling you that you're the worst thing to ever happen in the world, you kind of have to also go back and say, Guys, slow down. We're not anywhere near as bad as what they think you see and know what we're doing and they're going to misunderstand us sometimes. And so pull your team up at this point in time and keep charging forward with the mission.

**Adriel Frederick**:
I think some controversy is necessary and so I may be at a different point on that one. I don't think you're going to have any meaningful influence on the world without changing some pattern of behavior. And if you're changing a pattern of behavior, there's somebody who's invested in that pattern of behavior and that's going to create some conflict. The most fun news stories to read involve conflict, so that's always going to make for a great story and put you in the press. For Facebook, it was traditional media and other social networks were one side of the fight and then Facebook was the other side of the fight and then it became other tech companies now and that always makes for a great story. With Lyft it was taxis and unions, and so you have to recognize that you're always going to have some bit of a challenge.

**Adriel Frederick**:
Now, the really hard part about dealing with this is understanding what criticism is valid and how much of it is just because the source of power is being changed. So I'll give you an example. Let's say with Lyft, rich medallion owners in New York, I had no sympathy for them when they were complaining about trying to ban Lyft because when I was in New York City putting my hand out to get a cab, they were tried right by my Black ass. So I'm sorry, I'm like, I do not feel that much empathy for them, but I think there were really legitimate complaints about the structure of driver pay that were coming up and that were behind I think some of the complaints and some of the big stories in the press and some of the big kind of legal action that was taken. Paying for pickup time when a driver's on their way to pick you up or when they drive somebody far out of town and they have a dead head to come back into a place where they can work, that's real.

**Adriel Frederick**:
That's a real problem that I think we got called out for that we weren't paying enough attention to and it got us off our ass to go fix it. I don't think we've, and I say we, but I'm not there, I don't think the problem has been fully solved, but I think as a PM listening to this, you kind of have to find the truth behind it and try to find a way to work on that and not get too lost in responding to the specific criticism. And so to walk this line between kind of going, yeah, some of this controversy is just part of the game, versus like, nah, this is really valid. Dude, to figure out where that is, you got to do what is so cliche, but you got to stay close to your users. And so to give you an example of how I did that, when a lot of the complaints were happening about driving on Lyft, I drove, I would just pick up the car and I would get out and I'd go drive and I'm like, let me me go feel this for myself. Let me go see what these guys are talking about.

**Adriel Frederick**:
But I can give you a story about Rick. I still remember this drive I did with Rick in Berkeley. So I'm at home, I just get in the car, I turn on the app, it's time to go driving. I get up ping 15 minutes away and I'm thinking do this, I go do this right now, this guy might cancel on me, I'm not really getting paid for this, but maybe the ride is worth it. So I drive on over, I'm dodging traffic, pedestrians, drunk college kids, stop signs, I make my way over to Rick, he's coming out Chez Panisse, and he's about 80 years old, jumps in the car and then I pushed the button to figure out the destination and it says the ETA to the destination is two minutes. So I was like, "Hey Rick, you get this right? What's going on?"He's like, "Hey, I had a little bit too much to drink. I'm worried about breaking my hip, so that's why I called a ride." And so I went from wanting to curse Rick out for making me drive 15 minutes to come pick him up to feeling like, all right, no, no, no, there's real value I'm providing you in driving him just two minutes. But I recognized that wasn't embedded in the structure of paying. Rick would've been happy to pee for my 15 minutes to come pick him up, but we weren't one, giving drivers compensation for that, nor were we finding a way to pass that through into pricing for Rick. It's a much more difficult problem than it seems from that simple example. But it clued me into why drivers were complaining. So then I went, got it. I understand what we need to do. So when there were all the PR was going on about AB5 and prop 22, I was out driving and I was out sitting with the team trying to figure out how we're going to design our product that helps pay a driver for this.

**Adriel Frederick**:
It still keeps prices reasonable for users, doesn't create bad incentives where you end up with riders not getting picked up when they really need a ride because I didn't want Rick to break his hip. He still needs a price that makes him feel like it's okay for him to take that ride, and finding a way to balance this out is actually more complex than you might think. And that's what I stayed focused on whether prop 22 passed or not, I was ready for either side with a solution that was going to work for rider and drivers. That was the job. And so I think for PMs it was so easy to get sucked into the press and it's like, Yo, plan the work, work the plan, go back to your job. That's what you're supposed to do. Solve for customers in the middle of this. And then you figure out how to communicate it well.

**Lenny**:
What I love about that strategy is it also helps you see that it's not everybody that is worried about something. I think of Airbnb, like all hosts are pissed off about this one feature, there's going to be a revolt. And then to your point, you talk to some, like nobody even knows about it. Nobody cares. Everyone's fine.

**Adriel Frederick**:
Yeah.

**Lenny**:
And so this, there's so many benefits to what you're talking about doing, which is talking to customers, not just paying attention to the loud voices.

**Adriel Frederick**:
Absolutely. I also have empathy for reporters too. The story that with the headline, some Airbnb hosts are annoyed by the-

**Lenny**:
Right.

**Adriel Frederick**:
I mean, come on, this is not a great headline. I recognize that they have a job to do and sometimes they hold people accountable and sometimes they're getting people to read a story that maybe has a bit of hyperbole in it. And so they have to do their job and I have to do mine too.

**Lenny**:
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**Lenny**:
Well you shared this really heartfelt story about Rick, what's your most stressful memory of working at Lyft?

**Adriel Frederick**:
I think the most stressful time was when I had to unwind a bad product I did and actually make a better version of it. It was really a pricing algorithm change, it was something behind the scenes that nobody would really see, but this was a fairly big initiative that we worked on. We had experts in revenue management to work like PhDs and the people who wrote the textbook on the subject helping advise us on this. We build this model, you launch it and you're expecting this big change. And it goes poof, just does a little bit. And then we work at it and we work at it and we work at it and eventually we get it to be good and it works really well in three cities. We start rolling it out to more cities and it's a pain in the butt to roll it out to more cities because it's super complex.

**Adriel Frederick**:
And eventually we get it rolled out to maybe a hundred cities and then someone says, "All right, cool, I want to change prices." And oh, we struggled for months to implement price changes and man, the sentiment around this product was just rough for a while. And I remember being on our walk after a particularly bad week of this and trying to figure out what I was going to do about this thing. Do we stay the course? After a while, the answer was kind of simple even though it was emotionally difficult. And the answer was like, Yo, we got to rebuild it. There was no answer where we couldn't have a product like this. We needed some ability to be able to influence prices so that we could actually run an effective marketplace. The current solution didn't work. It wasn't as operationally flexible as we needed it to be because we didn't consider that requirement when we were building it and we got caught up in the kind of algorithmic complexity and sweet sauce of it.

**Adriel Frederick**:
And so I recognized that we just needed to own up to it, tell everyone we didn't get it right and we needed to come at it in a different approach that was actually more flexible operationally. And we did. I think the big learning, at least in that business was you have to think about operational requirements and operational control as a first order requirement. And I think when a lot of us were building product at a lot of the other consumer internet companies, you didn't have to think about operational control. You gave the algorithms an objective, you feed them some data, you let it run, you observe it and make sure it's doing nothing crazy and you tweak it, but you didn't need to have day to day operational and strategic control over the product and we just needed to snap our brains into being able to put people in the loop with the algorithm.

**Lenny**:
For folks that haven't worked at a company with this kind of on the ground ops team, can you just unpack what that is? Like operational control, what does that actually mean in practical terms?

**Adriel Frederick**:
Okay, so I'll give you an example. So back in the days Lyft is in 300 cities, probably roughly across the US, and in every single one of those cities you don't have exactly the same pricing. It's a little bit different. And so sometimes you might need to make a change seasonally because traffic gets worse or because fuel prices were different or because there's a new tax or because your competitor did something that you need to respond to and your algorithm cannot see this. It has zero visibility into this. And so you need a person in the loop to not only give that visibility but also to make a decision about how you respond. Because I think also, let's say you're in Chicago and there is a snowstorm and you need to change the way, let's say you need to update pricing so that it handles the increases in driver pay that you need to create to get people out during a snowstorm. You don't know exactly how you want to respond, every snow storm's different and a person has to make that judgment call and provide the right information to the product to be able to get to utilize it. Now algorithms were handing a lot of that and they could generally respond, but to be a lot more precise and needed a person to help handle that, to make that call.

**Lenny**:
Got it. Cool. Thanks for sharing that. So you're making this point about when you're at a company that has a big operations component and obviously the core central product team, you were sharing some learnings about what you've learned to work in that environment. So yeah, I just wanted to come back to that.

**Adriel Frederick**:
For sure. For sure.

**Lenny**:
So the main thing you said is just ops as a first order component when you're designing the software. Is that the big learning?

**Adriel Frederick**:
I think it's not just treating ops as the kind of first order requirement. The bigger picture for me was when I look across my career is the algorithms need people to help make judgment calls. And so I saw it really, I got a heavy lesson in it at Lyft, but when I look back I recognized it was there at Facebook too. It just wasn't in my domain. There is always a judgment call that has to be made between how often are there going to be ads versus how often are we going to show organic stories from your friends and family? How often are we going to show content that you might be interested in that's not quite in that group? How often might be want to show you things that help you find your friends or help other people find their friends? And that is a judgment call that varies for different markets and different situations and there may be algorithms behind the scene that are making that call for every single person in real time, but there still have to be people applying some strategic judgment to that.

**Adriel Frederick**:
And I wasn't in the position of needing to do that at Facebook, but once I saw how much I needed to do it at Lyft and I kind of looked back at history, I saw that it was there too. But I think there are too many people who don't see this and believe that there's an algorithmic solution to everything. I think as a product manager and especially product managers working on systems that are heavy on machine learning or operations research and optimization, to think about where you want a person to make a decision and where you want the machine to be off to the races and to think about that as a product design problem because there actually is actually a computer interface that you have to think about there. You need information about what's going on, let's say at Lyft, what's going on with my market? How long does it take for somebody to get picked up? How expensive am I versus the competition? What are my goals in this market and how am I performing today with that? Give somebody information, but also give them the tools to execute the right decisions without creating trouble. And that's like a product design problem, that's a first order product design problem like anything else that you have to think about. And I'm not privy to it, but I would guarantee that there are people thinking about those same kinds of problems at other companies.

**Lenny**:
That reminds me, I was just listening to Zuck on Joe Rogan and he made this point that when you look at a post, you can add a little emoji reaction and you can have a little angry emoji reaction. And he made the call that we're not going to use the angry emoji reaction in our algorithm in any way, we're just going to ignore that because naturally you'd be like, okay, people are angry, that's interesting. Let's show that because it's interesting to people. But he specifically wants to avoid anger and facilitating anger probably because a lot of the feedback that they've gotten.

**Adriel Frederick**:
Exactly. And I think they're probably, I'd call them techno utopians who would say feed all data to the algorithm, give it an objective and it will do the right thing. And I was like, yeah, the reason that falls down is the algorithms don't understand long term effects often, nor do they understand how people might respond to it, nor do they understand your intent for the product. And I think it's really important for product managers to play that role. That is our job. When you are working on algorithmic heavy products, your job is figuring out what the algorithm should be responsible for, what people are responsible for and the framework for making decisions.

**Lenny**:
Is there an example that comes to mind where you did that or didn't do that well or someone on your team should have? Just something to make it a little more concrete even.

**Adriel Frederick**:
Let's assume that you are a person working on pricing and you say like, great, I have an objective that is I would like to win market share in a region. And you left that to an algorithm to say I need you to optimize prices such that you maximize market share, but what would the algorithm do? Drop your prices to the floor. All the way to the floor, and then you don't make any money. Okay great. So then you say, okay, what's the next step of that? Let's give it a constraint. Let's set some target that we might want to have for how little profit that you might be willing to take. Okay, go do it now.

**Adriel Frederick**:
What if the guy on the other side is doing the exact same thing? Both of you will hit your constraints and then the game will stop. Okay great. So now it then flips to, oh we have to choose where we want to win. And so I think one of the things we did that I'm particularly proud of is building products that help people see and understand that game a little bit more and decide where they want to. I think the first few pieces of that are not shockers, but that conclusion at the end where you get to, oh wait, I need to create a tool that gives people information to then decide how to play this game is actually what's critical.

**Lenny**:
Interesting. So kind of what I'm hearing is a lot of the work is giving humans more information versus giving machine learning algorithms more information and there's a lot more leverage potentially there, giving humans more ways to tweak and dial.

**Adriel Frederick**:
Let me refine that a little bit more. It's more about giving people the information that they can use for decisions that they alone are good at and giving machines the power to amplify a person's intent. So one of the ways I like to think about it is all software in any form including ML, is just a tool like a screwdriver and you could try to put a flat head into a Phillips and maybe it'll work a little bit but it's better to use a Phillips screwdriver. And we're tool designers generally and especially in part development function, you figure out how much do I put into the tool and how much do I leave it up to the person and I give the person the ability to choose what they want to do. I give them a screwdriver, a flathead, a Phillips, a torques and you let them decide how they want to use the tool for the application at hand.

**Adriel Frederick**:
And so going from that analogy to concretely with ML you say look, machine learning's going to be amazing at optimizing for a given objective, but it's not going to understand the constraints or strategic choices I need to make. The constraints and strategic choices that we need in the external world are always going to have to be decided by a person. You make that incredibly easy for people to do and intuitive for them to do and then you go that algorithm can then amplify their effect by making decisions on hundreds of thousands, potentially millions of individual decisions to take that person's intent and amplify it given all the information that they can learn in that single context. So I think about it as designing an interface and make it an extension of yourself rather than a black box on its own that you just need more information to. Is that helpful?

**Lenny**:
Yeah, it makes me think about a neural link and what Elon's trying to do, I don't know if this is how he thinks about it, but the [inaudible 00:39:56] guy described it as Elon's worried that AI will take over at some point and so he wants to build a tool that connects straights our brain that can access the power of AI to kind of have a chance against just a rogue computer in the future.

**Adriel Frederick**:
Even then you've got to make sure the person is still in control. I hear that thought and I go, okay, you build the interface but then who's in control? Is the person still in control or did they become a slave to the machine and you just made a better interface to make them a slave?

**Lenny**:
Oh shit, we're in trouble.

**Adriel Frederick**:
I am not yet as worried about these visions of them taking over. Thus far and maybe I haven't fathomed what they can do, they still seem like tools that need our guidance to be useful. Even the most amazing, we've been seeing the image generation and I've seen the cutting edge like text generation stuff. They can fool you into believing that they're like near human capability, but there is a lack of decision making and judgment that I see coming out of them. I see them as being again, extensions and useful like text generation algorithms. A lot of them can't write a paper for you and that's what I think people are scared of because it still requires your judgment to decide. Now when you decide what the salient topics are in something you've read, let's say you're doing a book report, you've decided what the topics are, it can help you write the paper faster for sure, but it can't write the paper for you. It can't choose the topics that your background and history and interest find useful or compelling to tease out.

**Lenny**:
This isn't where I was expecting our conversation to go, but I'll add another thought here because it's interesting, the way I think about it is there's nothing magical about our brain and so if that's true, why isn't there a world where we could just completely simulate it? Sam Harris talks about this a lot that it feels like once you get close then it could just accelerate so quickly beyond human potential. It'll start from 20% as good as a human to 40, 50, 60 and then it goes to a million times better. It can move so fast beyond us very quickly. So I think that's where a lot of the, not that I'm afraid of this, but I feel like that's where a lot of fear comes from. It could just dolly coming out and co-pilot just like holy shit.

**Adriel Frederick**:
Yeah, our brains are good with linear thinking, not exponential. So I've heard that argument that like, yes, this is increasing exponentially and you can't fathom it. I'm like, yes, that is definitely potentially true. Completely see that possibility and recognize that I have that cognitive defect in being able to understand it and even if it's a remote possibility, we should be paying attention to it. So I'm all for paying attention to it given the, let's just say the high cost of a low probability outcome is still a high cost and so it's still worth paying attention to.

**Lenny**:
Yep. Okay, good tangent, I wanted to chat about your learnings at Facebook. We've been chatting about all these other places and especially about growth, just stuff you've learned about growth and growth hacking and I was thinking about this interesting world that Facebook is in slash Meta where on the one hand when they started, and I'm talking about growth hacking, like Facebook did a lot of growth hacks, emailed all of Harvard, he had all these interesting dating thing happening and got a lot of controversy and it was all these interesting tactics to start Facebook, but now people use Facebook to growth hack and grow like Zenga famously, a few other places. So all that to say, I'm curious, what have you learned about growth slash growth hacking from your time at Facebook and other places?

**Adriel Frederick**:
I think growth hacking as traditionally assigned, finding those small changes you can make to a product to give you outsized impact, that is absolutely valuable. Where I've seen people get lost is they assume that if you do that alone, it will work. You can grow your way into something successful if you just find those few hacks and patch them together. And there's something about that that I find disrespectful to the people using the product. It's like you assume that they have no intelligence and they won't catch on to what you're doing eventually. The old saying fool me once, fool me twice, it kind of applies. So if you don't have a product that's providing real fundamental value to people, you can be a one hit wonder and have a flash in the pan and growth hack your way into something that might last for a few months but people will catch on it and then it'll disappear.

**Adriel Frederick**:
So I think that stuff is helpful, especially early on to get your initial traction. But you got to have something people and want to continue using. And when I think back over the products we did that really moved the needle, they were all things that just focus on the marginal user and figured out to make the product easier. It's easy to get seduced to thinking that there is a fast secret way to do it. And I'm like, no. The vast majority of it was just hard work and finding ways to solve the real problems. And what are those real problems? They were pretty damn simple but we just grinded on them for a long time it just stayed on it. One, make it easy to find the product. Number two, make it easy to get into the product. Three, stupid easy to find your friends. And then once you did that you were off the races and those were the things we were doing over and over again.

**Adriel Frederick**:
I think another big piece of it is reminding people that there's something interesting here and building the habit of coming back to the product and it was also part of it, but we just grinded on those few things over and over again. And some of the really big wins weren't hacks, they were just paying attention to little details. I'll give you an example. I remember sitting one day thinking about how to help people find their first few friends and we would do this thing where we'd have recommendations, if you could get one or two friends, you'd be off to the races and we could find you more people that were in that same friend group. So I thought about the way the people you may know algorithm worked, I get one or two friends, they would find your mutual friends and then would help find you more of those kinds of folks.

**Adriel Frederick**:
And I was like, you know what that does is it spirals you down one friend group but it doesn't get you all your other friends. I remember just looking at somebody using the product and recognizing that we were only taking them down this one path. So I was like, man, how do I see all your friend groups? And so we had this idea that we came up with that would do it. I'm not going to let that one out. And it was like game changer, like absolute game changer. Especially for users helping them find those first few friends in a few different friend groups, which then meant we could get you down one group and another and just continue building out that graph just by using recommendations. Because we had a great tool for seating it and that was not easy. That was not a hack. That was hard work.

**Adriel Frederick**:
I also remember one of my favorites is something Tom Allison did, Tom Allison I think now is responsible for the Facebook App, and when he was working on the engineering manager for one of those teams, there was a change we wanted to do to one of these algorithms and it was a bitch, it wasn't a hack and it was going to take a few months to pull off and Tom just hit it in a corner. He just let everybody know that we were really going to change the way this product worked. He had a really smart guy working on it, [inaudible 00:47:03], and they just hid off in a corner, rebuilt the product in the way it needed to be built to make it easier for us to operate it and scale it and then put it up there. I know of course they crushed it and they were incredibly modest about it, but it was not a hack. And it came from them looking at this deep problem of finding that thing that mattered and then saying, we need to make a fundamental change to make it easier to recommend friends to folks and just grinding on it.And so one of the things I recommend for people when they're thinking about growth for their product is figure out what the core actions are and then grind on them. Think about removing them, removing friction and some of them. But just keep staying at it and as you grind on it, you'll do little hacks. You got to figure out how to put the right text in the button and get it above the fold, create the right copy. All the things that we traditionally associate with growth marketing, you got to do those things. But to me that's stable stakes and just doing good product communication with your user, but then you got to think about this person who can't yet figure out your product and it's trying to take this action and making it stupid easy for them. I got a million more examples of that one, but that's the game. It's not just finding some trick to [inaudible 00:48:18] a site.

**Lenny**:
I love that. The way I think about this that I've heard well described is just there's no silver bullets, just many lead bullets.

**Adriel Frederick**:
Yes. And a few massive cannonballs every now and then. Every now and then there's some cannonballs.

**Lenny**:
What's an example of a cannonball as you think about that?

**Adriel Frederick**:
Sign up with phone numbers, which is now par for the course, that was a cannonball. Getting SMSs delivered to people all over the world. Doesn't sound glamorous, really hard to do. That was cannonball. Good friend recommendations, another big one. There's more, I'm not going to go into all of them. What I mean by cannonball here is that there was sometimes some really big fundamental changes you needed to make to the product to make these things work.

**Lenny**:
Got it. So you think about that in terms of investment, not necessarily the impact-

**Adriel Frederick**:
Investment.

**Lenny**:
Impact plus massive investment. Cool. I have so many questions along these lines. Okay, I'm going to pick a couple. One is Facebook is famous for this kind of activation milestone of getting 10 friends or seven friends, whatever it was, like there's some number friends you got to get and the good things will happen. Were you involved in that? Do you have any insight into how that came to be? Is that real?

**Adriel Frederick**:
That decision came before me. I saw it. I understood the data and I worked on this problem. What I thought was brilliant about that was not the metric, it was the designing it to be understood and communicated. What I think is fabulous about it is that you are talking about it now because it's memorable and it got people to take the right actions to start chasing the goal. There was literally nothing magic about the number or the date, but basically it was a way of saying like get people as many friends as possible as fast as possible. And if you said that generically to someone, they'd be like, Yeah, I kind of get it, but yeah, I'll go do that.

**Adriel Frederick**:
When you create a discreet number and a discreet time and there is a concrete goal to chase and there's a number and a graph that everybody can look at and see, we are going to go make that thing go up, the organizational effect of that is galvanizing. So what I thought was brilliant about it is, and as I've heard the stories, this is all secondhand. There was a lot of debate about what the number should be, what timeframe should be, and at some point Zuck just said 10 friends, 14 days, go. And it just got people past the academic debate of like, All right, got it. As many friends as possible, the fast as possible, let's go.

**Lenny**:
I love that. That's exactly how I've always thought about it, that it's not the number exactly, it's just a rallying cry that everyone can just get around and just go, doesn't need to be this perfect number that has incredibly correlated link to retention or anything like that. It's just like, this is good enough. It's directionally I'll just try to do this. Let's just go.

**Lenny**:
There are downsides of it. Some of them are really funny. I remember looking at a graph of retention versus number of friends and what actually dropped with 11 or 12 versus 10 because somewhere in code, somebody had done something with 10 friends is the limit to help improve retention. And it shut off at 11 or 12 and it came back up, but I was like, You know what, that's fine. That's completely fine. Because if we didn't get that organizational momentum, that graph would've just been lower. So I could take the kink where it drops, it's fine.

**Lenny**:
You also mentioned this term marginal user and I thought it'd be helpful just to unpack what you mean by that.

**Adriel Frederick**:
For me, it's a person who is just on the cusp of taking the action you want to take. I'll give you the concrete example. When working on registration, I would try to find a country where we had a lot of growth, but for some reason our conversion rates were terrible. So we had a lot of traffic, but conversion rates were terrible. And I was like, okay, that's the marginal user. This is the person who is just on the cusp of coming in, wants to come in as you can see by the traffic, but we can't get them in. So why? And when you go to the extreme and you find that person who's the worst, and most likely it was a person on a feature phone on edge, trying to access Facebook in a country that was far from one of our data centers. And then you go like, All right, what's wrong with this person's experience?

**Adriel Frederick**:
Let's go check it out. And you're like, Oh, you see everything that's wrong with the product. So then it gives you your list. Okay, the language is probably wrong. We didn't get that. Are we detecting the country properly so that we can actually get their phone number formatted properly? Probably not. Oh man, it's far from the data center, so that connection's slow and they're on edge. Oh, that's terrible. And you just see and package up all those, it gives everything that's wrong and they can just start figuring out what to do with them. Something I caution people against though is don't use the data alone to figure out who the marginal user is. It'll give you a clue where they are and what might be wrong, will give you some hints. It's not going to give you the answer. You have to go watch them to find the answer.

**Adriel Frederick**:
Because I think in a lot of these data driven places, somebody will say, Great, just create a funnel. Figure out all this drop offs of the steps in the funnel, Look at it yourself and then figure out what might be wrong and go fix those things. But what I think happens is often there's a problem that's orthogonal to that funnel that you can't see from looking at the data. And you have to go look at the person and talk to them. I remember one example we had is was watching someone sign up up for the very first time for Facebook in India and they're about to put their name in it and they ask them, So what name are you going to put in? They're like, Okay, my full legal name. All right, cool. Does anybody in the real world call you that? No. And I was like, Oh dude, we're screwed.

**Adriel Frederick**:
If you send out friend requests, it's not going to get accepted because nobody knows who this person is, and then the reverse, if they find you, they don't know who this is. And so it was like, Yo, you're going to look at some problem deeper in the funnel, yo, what's going on my accept rate? And then you're going to go tear I that little mini funnel and then recognize that you had a problem that happened ways back. And so when you thinking about that marginal user, you got to go out and look at them, talk to them, watch them use it, try to get into their shoes yourself as much as you can, and then make the call from there from what you do. But that data isn't going to tell you, it's going to give you the answer. I'll just tell you how bad.

**Lenny**:
Wow. I love that connects back to the same advice you gave in all these other contexts of just talked to people. Don't rely on just this aggregate data.

**Adriel Frederick**:
Now, don't get me wrong, I've built the experimentation platform at Lyft. I'm a guy who loves data and loves using it and looking at experiments. I think it's just too easy to try to sit in your laptop, pull up a funnel or pull up some charts or look at an experiment results and think that's going to give you the clue to what to build. It's a compliment. It's not the only thing. And I watch people fall into that trap of assuming, especially when you're working at companies with lots and lots of data, you fall into the trap of thinking that you're swimming in answers because you have all this data and just need to tease it up. Just go out and talk, you'll find it faster.

**Lenny**:
I really like this advice of when you're trying to optimize things, focus on your marginal user. And there's two parts to it that you talked about. There's the next most likely person to sign up and then there's the worst case and going to like them to see all the things that are wrong and that be your north star, make this person successful and make so many more people successful. Is that how you think about it?

**Adriel Frederick**:
Yeah, I do. So marginal user I think is the fun word to think about because you think of families, think about children, the person who's right on the cusp. But I like to go to the worst. It shows me everything that's wrong, but the marginal user thinking helps you prioritize what thing to do next. So that person, that example marginal user I was talking about, they're on a future phone with edge too. There's a lot wrong that's just going to be tough. But I might look at that experience and go, All right, let's say somebody was perfectly equipped the best phone and a great internet connection in that country. What would still be wrong? I was like, Oh, language is still wrong and the latency to their phone is actually still pretty high to our data centers, which is why it's taking a long time to sign up. I could still fix that. So that's how you can see the worst case to tell you everything, but then decide what is marginal by removing a few of the barriers that you know are difficult for you to attack and then see which ones are closer to being resolved.

**Lenny**:
Awesome. I wanted to ask one more question about experiments at Facebook back in the day. So we talked about there's all these lead bullets or some cannonballs, maybe a silver bullet somewhere. In your experience, what percentage of experiments end up being impactful and successful?

**Adriel Frederick**:
Okay, that's a difficult and different question. So I'd say probably 60% successful, 40% you should turn off. But within that 60%, I think there's a hidden cost to the experiment, which is that you're futzing around with something small. You could have used your time on something bigger and more meaningful, but you're futzing around with a bunch of these small ones. Some of the small things were incredibly meaningful and you needed to do them. So I think this is actually, it's almost like the same problem about, I don't know which of my marketing is best. You have to try a bunch of stuff and then figure out what was terrible. You don't know before you do it, before you do the experiment, what the impact is. But sometimes what I've seen is let's take a bunch of them as a program and let's say you have over the course of three months, you're going to experiment with 10 things.

**Adriel Frederick**:
You might have been able to push on two really big ones. And what I've seen is there's a laziness, and this is broadly, this is not just at Facebook, it's broader. There's a laziness that can creep in where you're just finding a lot of little things because they're easier to come up with and they're easier to design and think about. It's easier to build, it's easier to talk to your boss and say, remove the number by 0.02% and you feel good about doing those few small things. And so it creates this incremental thinking where you're just trying to do a bunch of small things that just don't meaningfully add up to something big.

**Adriel Frederick**:
I think what's healthy is having a good portfolio because basically you say like look, I'm going to have, using our analogies from before, I'm going to have some cannonballs. I'm going to work on a couple cannonballs and I'm going to have a bunch of lead bullets. And maybe it's 80% of your energies on those big cannonballs, 20% on the lead bullets, and having a constraint like that forces you to choose the fewer experiments that are actually probably the really good ones and it's not just a whole bunch of crap that you're trying out.

**Lenny**:
And is that actually how you divide up those bets broadly? Is that like a rule thumb you have or is that just numbers you're putting out there?

**Adriel Frederick**:
Those are just numbers I'm putting out there. It's always going to be a gut call based on where you are. I think depending on the stage your product is at, it should be a different set, a different bite. Very early on when you're building a product, you kind of know what the big things are. You've talked enough people, you have enough, just go build it. You should not be playing around with experiments. It might be a hundred percent cannonballs. Just go knock the big pieces out, don't worry, it'll work.

**Adriel Frederick**:
Also, the cost of experimentation is time. So if you are experimenting on every little thing and waiting for the data to come in and then also screwing up some other part of the product because your experiment's on 50 50, it's just not worth it. Just bang the big things out. As you get more mature, the balance needs to switch in the portfolio. Probably not that many big cannonballs anymore, probably just one. And there's probably a lot of the refinements that you need to work on. And by then you have this scale that the time to experiment isn't as high and the cost of experimenting is lower. So it's fine. It's good to do with that way.

**Lenny**:
Okay. One last question before we get to our very exciting lightning round. So you've moved from IC a while back at this point to now VP of Product at one of the most trafficked sites on the internet. And I'm curious, what skills have you grown or had to grow most as you've gotten more senior in your career?

**Adriel Frederick**:
Organization design and empathy.

**Lenny**:
Whoa, I love that.

**Adriel Frederick**:
Oh dude, for a long time, and I think this is, I and many others had this idea that the people who are the smartest are the ones who rise. The people who are the most technically competent are the ones who rise. People who are the best individual contributors are the ones who rise. And somewhere along the way I had that idea disabused of me and I recognize the job's different. It's more about building a great team, creating the right incentives for the team on blocking them, guiding them, and helping them work efficiently. Those mattered way more than anything else. And I guess one of the ways I slowly recognize it is as I started going up in my career, I recognized that if I wanted to have more impact, I couldn't do everything myself. There was just more that needed to be done. And in today's world, you can't do anything meaningful by yourself.

**Adriel Frederick**:
You need a lot of people to do stuff with you. There's nothing meaningful that gets done by any single person, even though people like to make you think that in their hustle porn that they post online. So it may be just a step back and think about what helped me be productive in environments when I was productive and how I could do that for others because then that would just naturally help me. And so there were simple things like clear goals, helping people feel safe and understand that you got their back. Making it easy to do their jobs. But my job is to make sure the processes for you doing your work and the people who you have to interact with are just buttery smooth and everything just runs easily. And so that was lesson one. It was just designing a good organization, culture, skills, people, processes, et cetera, all necessary.

**Adriel Frederick**:
That's one piece. The second is empathy. Where a step of that was just like you have to have that as a PM for your user, but I think it's different to having it for a peer and another function or somebody else on one of your teams. And the hardest part of it is they say getting in somebody else's shoes. The hardest part is taking my own shoes off. Basically going, Yo, okay, I came into this, there's something I wanted, I wanted to get rid of that. Now just talk to this person and try to understand what's going on with them, what they care about for their life goals and motivations, what they're scared of, what they're excited by, how you might be able to help them. Once I was able to get out my shoes, clear my mind, try to get into their head, then I could be like, All right, cool, let's find a nice happy middle ground in the middle here. But that's something that works for both of us together.

**Adriel Frederick**:
And sometimes for me it was, Yo, what I care about, I'm good. I'm going to let you do your thing. I've gotten into your shoes, I need to leave you alone. Like you're good. Other times I'm ready to push. But I think once I have the empathy, I'm then able to think about what we as an organization broadly want to achieve and try to put the two shoes on at the same time and find something that works for both of us. So what's that common objective? And I think that's how I try to approach almost every conversation is, especially being a guy who looks different, talks different, comes from somewhere else, first thought they might have is and unconsciously might be like this guy isn't one of us. But then once I make it clear to them that we have the same objectives, we're about the same thing and I want to know what's going on with you so that I can help you achieve what you want to achieve. Dude, problems go away.

**Lenny**:
Okay. I know I have to let you go and you have to get back to real work. So we've reached our very exciting lightning round, the final part of our little chat.

**Adriel Frederick**:
Darn right.

**Lenny**:
Basically I'm just going to ask you five quick questions, whatever comes to mind, share it and we'll go through a pretty quick.

**Adriel Frederick**:
All right.

**Lenny**:
Sound good? Okay. What are two, three books that you recommend most to people?

**Adriel Frederick**:
The Prize and probably now The New Map by Daniel Yergin. They are books about the history of oil and the geopolitics of oil. It is a fascinating way to understand the world. It's like the best books I've seen to understand geopolitics and how they work and why they work. It does it through the lens of oil, which explains way more than you might think. And so this comes from the early part of my career working in energy.

**Lenny**:
I will link that into show notes. I've not heard of that one before. What's a favorite podcast of yours other than this one?

**Adriel Frederick**:
Oh, of course, you took the easy one away. Revisionist History with Malcolm Gladwell, just gives you a different look into things. I'm also a huge car nerd, like deep into modifying and tweaking and tuning cars. So there's this esoteric one called HP Academy that I'm into, but most of your listeners will not beat to that.

**Lenny**:
Wow. Very out there and awesome. And I think there's a new season of her Revisionist History coming out soon.

**Adriel Frederick**:
Yep.

**Lenny**:
Okay. Favorite recent movie or TV show?

**Adriel Frederick**:
Last night I discovered Mo on Netflix.

**Lenny**:
Mo.

**Adriel Frederick**:
And it's short for Mohammed. It is semi autobiographical about a Palestinian refugee living in Houston, his journey to seek asylum and live and work and date in this multicultural environment, he speaks Arabic, Spanish and English fluently. Funny as hell, but also dramatic. It is fabulous.

**Lenny**:
Amazing. Okay. Wow, these are all very unique. I love it. In a different direction, what's a favorite interview question that you like to ask?

**Adriel Frederick**:
These days at work, I have to go through the standard interview questions, but when I got to play and sometimes when I feel like playing a little bit more, I'll see something like, teach me something you don't think I know. It's a really good test of what you've heard me say a lot, empathy. I heard [inaudible 01:04:58] use it once and I kept trying it to see what it was good for and it helps you understand how good somebody is at reading you, how much knowledge they have and their ability to communicate and share knowledge. So it was like it actually could test a lot of things at once and a lot of times you learn something, it's awesome.

**Lenny**:
Okay, final question. Who else in the industry would you say that you most respect as a thought leader?

**Adriel Frederick**:
Well look on the discipline, [inaudible 01:05:24], discipline of product management, definitely [inaudible 01:05:26]. I think just in terms of technology development, it's the team behind Radiant Nuclear.

**Lenny**:
What is that?

**Adriel Frederick**:
While taking a break between jobs, I'm studying climate change and energy because of my background and I just basically became convinced that nuclear is a bigger answer than we're giving a credit for. A lot of the barriers are political, not technical, but the solution they're working on I think is a technical solution to some of the political problems we have around nuclear, which seems really interesting and I am really hoping that they pull off what they're trying to do.

**Lenny**:
Wow. I love how out there all these recommendations are. These are great. Adriel, I am so appreciative of you making time for this. I'm also really appreciative to Jules for connecting us. This was amazing. You're awesome. Two last questions. Where can folks find you online if they want to reach out, learn more, and then how can listeners be useful to you?

**Adriel Frederick**:
Awesome. Before I jump into that, thank you for having me on here. It's just good to reflect about life and work for a little bit and hopefully share some insightful stuff with the folks who listen to your podcast. So thanks for having me. You can find me on LinkedIn, Adriel Fredrick, there might be one other. Pretty sure I'm the only one. And then how can listeners be useful to me? Number one, keep listening to this podcast because if everybody keeps listening to the insights that you are teasing out, a lot of things will work well and not necessarily me. Another thing they could do to be useful to me is find somebody that's just different to you and talk to them for five minutes. That's it. I think that will come back to me eventually.

**Lenny**:
Love these and really flattered, really appreciate it. Thank you for being here.

**Adriel Frederick**:
Thanks for having me, Lenny, take it easy.

**Lenny**:
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.

---

## [6/20] How to build trust and grow as a product leader | Fareed Mosavat (Reforge, Slack, Instacart, Zynga, Pixar)

**Fareed Mosavat** (00:00:00):
You can't do homework. You can't do exercises. You can't do fake stuff. You have to work on real products at real companies with real customers, with real data to get better at product management. So any kind of training, mentorship, reading, et cetera that you do is just a layer on top of that. The real acceleration happens from doing it and getting more reps. There are ways that I think great PMs use to go faster on this loop, but you still have to do the work. At the core is you have to actually execute and deliver great products, and you have to do it over, and over, and over again.

**Lenny** (00:00:40):
**John Cutler** (00:03:03):
Hey, Lenny. Excited to be here.

**Lenny** (00:03:05):
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** (00:03:16):
Well, we've always thought of Amplitude as being about supporting the full product loop. Think collect data, inform, vet, 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 and CDP came out of listening to and observing our customers.

**Lenny** (00:03:37):
Supporting growth and learning has always been Amplitude's core focus, right?

**John Cutler** (00:03:41):
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** (00:03:50):
Absolutely agree. Thanks for joining us, John, and head to amplitude.com to get started.

**Lenny** (00:03:58):
Fareed, welcome to the podcast.

**Fareed Mosavat** (00:04:01):
Thanks for having me, Lenny. I'm super excited to be here.

**Lenny** (00:04:03):
So to set a little context for listeners that aren't super familiar with you, can you give us just a 45-second overview of your career and all the wonderful things that you've done?

**Fareed Mosavat** (00:04:14):
Great. Hi. I'm Fareed Mosavat. I live in Berkeley, California with my wonderful wife and two children, but I've been a product leader across a variety of different companies over the course of my career. Today, I am the chief development officer at Reforge where I help run all of our content teams, parts of our operations, and our partnerships with wonderful experts like yourself.

**Lenny** (00:04:33):
Awesome. What about all the other things you've done?

**Fareed Mosavat** (00:04:35):
So, previous to this, I spent almost four years as the director of product for a team called Lifecycle at Slack that is effectively a growth team. We're responsible for the self-service business at Slack all the way from first sign up, first team creation through to the first invites, activation, expansion, modernization, and even connecting the dots with our SMB sales team to help nurture some of those small self-service teams into larger commitments through our sales team.

**Fareed Mosavat** (00:05:02):
I came to that through a variety of different growth and product leadership roles at a bunch of different startups on larger companies. I built one of the first growth teams at Instacart for about a year and a half in the middle of their acceleration. I was VP of Product at a company called Runkeeper before that in Boston, health and fitness tracking company. I was a general manager at Zynga. I got there through a startup that I was an engineer at, basically started as an engineer, ended as a head of product over the course of a couple of years, and then got acquired into Zynga, and actually started my career with almost seven years at Pixar Animation Studios working on visual effects, software tools, and other creative tech to try and solve problems for a bunch of wonderful films you've probably seen or your kids have seen.

**Lenny** (00:05:45):
Please tell us the films that you worked at. I had no idea that you worked at Pixar.

**Fareed Mosavat** (00:05:48):
I am credited on Finding Nemo, Cars, Wally, and Up.

**Lenny** (00:05:55):
What? I did not know any of this.

**Fareed Mosavat** (00:05:57):
Yeah. Yeah. Basically, I started there right out of college. I was super interested in computer graphics. I'd actually been an intern there, was very lucky to be interested in that in the moment where they were really accelerating the growth of the company going from like the whole company is working on one film to like, "Okay. We're trying to release a film every 18 months." So they really scaled up, and I had been studying computer graphics, and then I was an engineer focused on computer graphics and a little bit of research on that in college, was an intern there, and joined, and just got to see a fun growth period at that company, and really, I think in a lot of ways is the root of why I love doing product management because everything I worked on was at the intersections of interesting creative problems, interesting technical problems, and interesting storytelling problems.

**Fareed Mosavat** (00:06:45):
So, in a lot of ways, it was like... I think if I connect the dots backwards to the Steve Jobsism is the beginning of how I got interested in solving high-level strategic problems across a bunch of different people doing different kinds of work and maybe how I got relatively good at it. It was because even as an engineer, I was sitting in the middle of those pieces, but I got bored, which sounds crazy, and decided to jump into a startup that nobody had ever heard of that had eight employees in 2006, and the rest is history from there.

**Lenny** (00:07:17):
Yeah. I wasn't planning to talk about Pixar, but I am so curious. One more question there. What's something that you learned from Pixar that has informed the way that you build products or think about product or your career?

**Fareed Mosavat** (00:07:28):
At the foundation of it is when I first got there, I thought what was important was modeling how things work in the real world. They're making things look right, so to speak. What I learned there is that actually, you're trying to deliver an end experience, and product, and story to your viewers, to your audience. It doesn't actually matter what's real. It matters what you see on the screen. It matters the emotion that it creates, the story that it creates, how it reinforces all of the other pieces. So the technical pieces were just a means to that end. So, of course, we used real physics and real math behind the scenes to do stuff, but if you had to box the numbers to make it look right, that's the right thing to do.

**Fareed Mosavat** (00:08:15):
So I remember as I was working on early effects, bubbles, sand, so this kind of stuff, I was trying to do things the way it would really work, and then the camel would look at it, and almost the first lesson I learned there was like, "No. What matters is the end result, the end product, the end feeling." I feel like I go back to that a lot as I think about product development not just from an engineering and technical standpoint, but from what's in your strategy doc isn't that important. It's actually just an input into the end experience that you're trying to deliver for customers. When we're thinking about content development in our programs, it's not important that all of the principles fit perfectly together into this MEC framework. It matters that you help people solve actual problems. What's the end goal that you're looking for? I feel like that's the lesson that I just keep going back to for my time there.

**Lenny** (00:09:06):
It's a great segue to Reforge, which I want to spend a little bit of time on. Folks that listen to this podcast know that I'm a huge fan, and we have a lot of Reforge alumni on this podcast.

**Fareed Mosavat** (00:09:15):
Yeah.

**Lenny** (00:09:16):
So a couple questions there. One, you said you're a chief development officer. Is that your title?

**Fareed Mosavat** (00:09:20):
Yes.

**Lenny** (00:09:21):
What is it that you do as a chief development officer?

**Fareed Mosavat** (00:09:23):
It's funny because in a lot of ways, it's not a made-up title, but trying to figure out how a role that I ended up sliding into as I grew my engagement with the company, how do we describe what it is? So I think what's unique about Reforge versus a traditional software startup, or a SaaS company, or all the other things you see is that we're not just a software company. Of course, we have a website. Go to it. You see things, you deliberate, but we also build a lot of stuff and experiences that fit into that. We build content. We build programs today. We're going to build all kinds of other content. We have live cohort experiences that are designed and thoughtful, and we build and try to make, solve certain customer problems.

**Fareed Mosavat** (00:10:08):
We have a member slack that we try to design to solve certain problems. We have the people like yourself and a lot of the guests that you've had on the podcast like Elena, or Adam Fishman, or Casey who plugged into our system to help us build all of those things because at the end of the day, our job is to help unlock the expertise that's locked in the heads of the greatest operators in the world. So who do we work with? How do we develop that content? How do we make their ideas shine? How do we solve real member problems? How do we help people do work?

**Fareed Mosavat** (00:10:38):
A lot of that is a product experience that in some ways, like a Pixar movie, there's the technical aspects and the UX aspects, but there's also all of the content, and the partners that we work with, and those pieces. I own all of that piece, like the production, content, the new product experiences, and all of the pieces that fit in there. So we have a team of really talented, amazing people that work on these things, and I lead those teams.

**Lenny** (00:11:02):
It's interesting how that comes back to your Pixar experience of the combination of intersection of art and technology.

**Fareed Mosavat** (00:11:09):
Yeah.

**Lenny** (00:11:09):
That's so interesting. Okay. Never thought about it that way. Yeah.

**Fareed Mosavat** (00:11:12):
Like we said, it's easier to connect the dots in reverse than moving forward. I have always been not that precious about titles, career roles, et cetera. I've really found myself drawn to, "Is this an interesting problem that I believe I can bring something valuable to the table? Can I help solve this in some meaningful way, and will I learn something great and new from this role?" At every step, I made those decisions. I've gone up and down the title stack from VP down to ICPM, from engineer to product, from product to this new thing and content. In every single one, I think it's a lot about, "What are you bringing to the table to help solve that problem? What are you taking away from the job and learning from it, and how do you turn that into the next step?"

**Lenny** (00:11:57):
Awesome, and we're going to chat about a lot of those learnings from your experience going through these career journeys, but one last question on Reforge. Just like how big is Reforge at this point? How many cohorts? How many students? How many people work there? What's the operation scale at this point?

**Fareed Mosavat** (00:12:11):
It's hard to count how many employees because it's growing so fast. I believe we are at just around 150 total employees across the whole company right now.

**Lenny** (00:12:19):
Wow.

**Fareed Mosavat** (00:12:20):
That doesn't include our executives and residents, subject matter experts, and the partners we work with. That's full-time employees working on the business. Of course, we have a large product development, product design, engineering, and data teams, but also the teams that I run. We call them strategy leads, content producers, content strategists, content designers, building all of that content as well as our partners team and operations team. So it's a relatively large company at this point. When I first started working with it, it was a scrappy operation of just a handful of folks, but we've grown quite a bit of over the last year.

**Fareed Mosavat** (00:12:51):
With that, we support, I believe, now 19 total cohort-based programs across product, engineering, marketing, and growth-related topics as well as a bunch of new experiences that we're working on for the coming future here in the next year. We have well over 10,000 active members on the platform, about a dozen executives and residents that work to help us deliver those programs, and hundreds of partners. We call them experts and operators in the space who contribute to our programs in different ways either as guests or as mentors, or helping us develop content behind the scenes.

**Lenny** (00:13:25):
Awesome, and I taught a couple guest lectures this past cohort. I think my second ever lesson was with you. You were the teacher?

**Fareed Mosavat** (00:13:32):
Yes. Yeah. We talked about instant buy, I think they're called, but I can't remember the name.

**Lenny** (00:13:37):
Instant book. Close, close.

**Fareed Mosavat** (00:13:38):
Instant book, sorry.

**Lenny** (00:13:38):
Yeah.

**Fareed Mosavat** (00:13:38):
On the Reforge platform for experimentation and testing program, which was, yeah, actually, also my first program that I helped lead at Reforge, and I think you were my first guest.

**Lenny** (00:13:47):
Oh my god.

**Fareed Mosavat** (00:13:47):
So, thanks. Thanks for not making me look bad.

**Lenny** (00:13:51):
Thank you. So what's cool about your background working at Reforge and all the companies you worked at is that you've seen a lot of PM careers go well and PM careers go not so well. So what I want to spend our time on is talking through just the career development journey for product managers and in particular, the challenges that PMs face trying to become better PMs and just why it's innately tricky to become better as a product manager. It's such a weird job to get better at. So my first question is actually, why is it so hard to become better as a PM? Why is it innately a tricky thing to develop as a PM?

**Fareed Mosavat** (00:14:28):
One of the trickiest bits about it is that there's no clear, obvious pre-training you can do that gives you a baseline set of understanding that you can use to be a product manager. People come from MBAs, people come from certain kinds of majors in college, et cetera, but it's not engineering where like, "Okay. With a couple of weeks of bootcamp or a couple of years of a computer science education, I have some foundational knowledge that helps me go from zero to one in my first job." Not only does it help me break in because I have a credential that helps me land that job, and we can talk about why landing your first PM job is so hard, but also, there's not a lot of stuff that one-to-one directly correlates to the work you're going do on a day-to-day basis.

**Fareed Mosavat** (00:15:11):
I think there's an idea that Naval Ravikant talked about on Twitter and in blog posts a long time ago, this concept of specific knowledge that can only be gathered by actually doing the work. A lot of product management, really, is like that. You get better by doing it, and so you start in the same place, if that makes sense. Of course, there are different skills and intellectual capacities, et cetera that help different people be more successful at it, but at the end of the day, you don't know if a PM is going to be great until they start doing that work. So I think that's one of the pieces that's very hard.

**Fareed Mosavat** (00:15:41):
The second is the thing I just alluded to, which is breaking in and getting your first role. It's just a very difficult situation for a lot of companies, and there are a couple of different paths to it, but none of them are straightforward. There's no clear linear path, except for maybe being a Stanford or Harvard grad, top-tier school grad, NCS with an internship, goes to Google to do an APM program. There are a couple of these things that are surefire, but I don't think they guarantee success, and they are actually very limited in terms of the number of people that they let into the business.

**Fareed Mosavat** (00:16:13):
So I think this is what makes it so hard is that there's not any upfront training you can really do to prepare yourself or even knock down the door to break in. But then, also, it's not clear there's a lot of training within a company that would help you be successful generally on the job of product management. You can learn how to be a good PM at Google, you can learn to be a good PM at Facebook, but it is up to each individual PM to figure out how to generalize what they're doing to move from different kinds of product across different kinds of product work as they get more senior to solve bigger problems, et cetera.

**Fareed Mosavat** (00:16:51):
So what we tried to do at Reforge is we are focused on helping people accelerate that learning loop. It's not, "Hey, if you take this class, now you're qualified to be a PM." It's not really like that. I don't know if that's possible. I hope it will be someday, but it is very difficult. I think it's more, "Hey, we want to help you when you encounter certain kinds of problems, not have to solve them from first principles, but following the footsteps of the people who have done great work in the past, generalize those lessons." But at the end of the day, you still have to get down and do the work.

**Fareed Mosavat** (00:17:25):
You can't do homework, you can't do exercises, you can't do fake stuff. You have to work on real products at real companies with real customers, with real data to get better at product management. So any kind of training, mentorship, reading, et cetera that you do is just a layer on top of that. The real acceleration happens from doing it and getting more reps. There are ways that I think great PMs use to go faster on this loop, but you still have to do the work. At the core is you have to actually execute and deliver great products, and you have to do it over, and over, and over again.

**Lenny** (00:18:03):
Yes. Let's absolutely dig into that. Let me put out a couple mental models that I'm thinking as you're talking.

**Fareed Mosavat** (00:18:07):
Sure.

**Lenny** (00:18:08):
One is just if you think about a pie chart of a great PM's career and/or investments they make along their career journey, how do you break up that pie chart? Like some percentage is doing the work, some percentage is courses, maybe some percentage is books. So just putting that out there in case that's useful to think about, and then the other is thinking about the trajectory of a PM on a line chart, and what are these inflection points that you've seen most impact the career trajectory of a PM?

**Fareed Mosavat** (00:18:34):
So let's start at the first one, the pie chart idea. What percent is spent on different things? Unsurprisingly because Reforge is all about growth loops, I think of this in terms of a loop actually, which is like, "What is that learning or career acceleration, or ability acceleration loop? At the core, again, at the top of the loop is execution. You have to have a real problem. You're working on with real customers that you want to solve in some way. So, you're executing. You're delivering. You're learning at the beginning. It's all about execution. So we'll start with the pie chart at the beginning. It's almost all execution.

**Fareed Mosavat** (00:19:06):
What are the problems you give a junior or brand new PM? Known problem, known solution. "Please work with engineering and design to deliver that thing on time, and then tell us what happened." So it's like a very tightly constrained problem. As you level up, then some of these things become more unknowns. So there's execution, but I think the next step that great product managers do is they think about how to generalize that execution a little bit. So it's not just, "Okay. Now, I know what the best settings page for Slack is." It's, "What generalizations did you make? What are the things that you can take that are applicable to other stuff?"

**Fareed Mosavat** (00:19:49):
Some of that is execution-oriented, how to best work with engineers, how to iterate on designs, what customers do and don't do, rules of thumb, those kinds of things. I think that's where reading courses, et cetera can help because sometimes by bringing other... or one-on-one conversations with experts, et cetera. There are a whole bunch of different ways, but is that the generalization step? "Hey, I did this thing. Oh, other people have done something similar. How do I connect the dots on that? How do I make this experience bigger than what I've just done and lead me to help solve other problems?"

**Lenny** (00:20:23):
These are things you're doing in your head, basically. You're just developing frameworks, mental models, things that you're just taking with you to the next project in your mind.

**Fareed Mosavat** (00:20:31):
Exactly. So, to use an example, there was a time at Instacart where we were working on onboarding, brand new onboarding and activation flow for customers. We tried a lot of different stuff. We tried the slimmest, fastest, lowest friction, least number of steps path in, and then we had this hypothesis about helping people get set up. So we took the opposite approach, which was a really long onboarding with a bunch of different steps and wanted to see, "Was that more effective or less effective?"

**Fareed Mosavat** (00:20:59):
The generalization is, "Oh, for products that had a high bar to activation, sometimes more set up and higher friction, good friction could actually help those customers be successful. There are other kinds of products that are high-intent where they know what they need to do to have simple actions where lowering friction might be the right thing." So, that's a generalization. It's a generalization of, "Oh, I learned a thing." It's a hypothesis about how that might generalize other kinds of products or other kinds of problems that you approach. I think some of that can come from seeing it from the outside, listening to a podcast, hearing you say it, taking a course, et cetera. But at the end of the day, you have to experience it to see how it applies to the world.

**Fareed Mosavat** (00:21:42):
Then, the next bit is communication, and I think this is a bit that a lot of product managers, obviously, and any job miss, but you can't just do the work. You have to actually communicate the work. You have to talk about what you're doing, what you've generalized, what you've learned so that you can hit the next step, which is scale your opportunities. Go from smaller known problem, known solution to maybe known problem, unknown solution type of work, which is the next step.

**Fareed Mosavat** (00:22:08):
Then, eventually, to where you want to be as a senior, great, high-level individual contributor PM to the not quite known problem, maybe a goal with a set of problems and unknown solutions, unknown problems, unknown solutions, where you're actually identifying customer problems and moving towards on that. So scaling up your opportunity, and then executing again. I think of this as a loop of learning, and so of course, the percentages change over time as you move more senior in your career, but also, depending on where you're at in the step that the percentages change.

**Lenny** (00:22:40):
Got it. So, just to recap, execute, just do the work, just ship.

**Fareed Mosavat** (00:22:44):
Yeah.

**Lenny** (00:22:44):
Generalize learnings from shipping to build up your gut feeling of what will work and not work.

**Fareed Mosavat** (00:22:49):
Exactly.

**Lenny** (00:22:50):
Learn to communicate things you're doing, and then scale the things that you're executing based on this gut feeling you're building, and communicate that out, and just continue. Do you think scaling take on more scope or have more impact? Is that how you think about scaling, that last piece?

**Fareed Mosavat** (00:23:06):
Yeah. I think it's one moving from knowns to unknowns.

**Lenny** (00:23:08):
Great.

**Fareed Mosavat** (00:23:09):
So like you're being given a hairier, harder to untangle types of problems with more unknowns and more autonomy. I think the second is, yeah, of course, with... although I think for the beginning of your career, you tend to go deeper. So it's like, "Okay. I'm going to work on growth, let's say, or core product, or zero-to-one products, or technical scaling, whatever it is. I'm going to go deeper on that," and then over time, that turns into width, but this is why the generalization step is important.

**Fareed Mosavat** (00:23:39):
If you want to be a product leader, you cannot be seen solely as a specialist in that certain kind of product work, and so the generalization step is really important. If you want to move from growth to core product, you need to show that you're not just running experiments and driving numbers up. You need to show and communicate that you're learning deeper lessons about how customer psychology works, and what products people resonate with, and how to think about the business more holistically, and then communication. No one knows what you're thinking if you don't tell them. So if you don't communicate, you don't have control over those scaled opportunities. Usually, your manager, or the organization, or the company does. Maybe by switching jobs, you have some control, but you need to earn that right. You need to communicate. That's why I think there's pieces of the loop you can control and pieces that are externalized.

**Lenny** (00:24:25):
I'm curious, in your own career, what the biggest inflections of growth have been either in terms of learning, or impact, or just opportunity?

**Fareed Mosavat** (00:24:33):
The first big one was when I switched from being an engineer to being a product... I didn't even know it was product management, but a product leader of some kind. I think there are two things that happen. One is you got to be doing this stuff, but often, somebody needs to see it. The scale opportunity piece of the step often requires someone from outside to notice that you're doing something really well and trust you with a bigger opportunity. I think of this as sponsorship, not mentorship. I don't necessarily find that in my career. I've had a lot of managers where I'm like, "Wow, their day-to-day help was super awesome at helping me be a better leader."

**Fareed Mosavat** (00:25:10):
I hope that I've been that for some people, but I don't have a ton of examples of that in my career. But what I do have is a couple examples of people who deeply trusted me to solve big problems, and I don't know. I'm lucky to have had that or otherwise, but one was a CEO of that startup who's now a venture capitalist. His name is Nabeel Hyatt. I was like, "Hey, you seem to understand the data better than anybody here. You're solving these problems. Help us figure out what we're going to do next," which now we call product management.

**Lenny** (00:25:36):
But he was at, by the way?

**Fareed Mosavat** (00:25:38):
it was called Conduit Labs.

**Lenny** (00:25:39):
Okay. Yeah.

**Fareed Mosavat** (00:25:39):
It's a game company. Then, eventually, I was the director of product for our Boston studio. The next was at Slack. I was an ICPM working on activation and growth on a team of three or four other PMs, and there were a couple of moments where by communicating my work and talking through how I was solving problems, people noticed that I knew what I was doing and gave me bigger and bigger opportunities. One of those was Merci Grace, who I think has been on your pod and was a wonderful sponsor for me. Then, again, when Merci left, April Underwood, who's the CPO, said, "It seems like you have a handle on this. I'd like you to take on a bigger range of problems across all of this growth and not just the modernization piece that I've been working on before." So I think in each of those steps it's about creating trust and knowing that you have a sponsor there, someone who's going to go to bat for you.

**Lenny** (00:26:25):
I really love this point of sponsorship. We haven't talked a lot about this on the podcast. There's a lot of talk of finding a coach or having a manager that teaches you how to do the job, but this idea of just getting to a place where someone gives you an opportunity to shine, and that's been really big in my career just like certain managers just, "Here, Lenny. You take this, and let's see what you can do."

**Fareed Mosavat** (00:26:44):
Yeah.

**Lenny** (00:26:45):
Is there anything else you can recommend to folks to create opportunities for sponsorship? You talked about communication, executing well. Is that just the core of it, like doing a great job and communicating the great job you're doing?

**Fareed Mosavat** (00:26:57):
This idea that it's what you do and that's multiplied by your ability to show that work and communicate it, and that's the impact that you can have, but you have to have not just impact on the customers, but also on the organization. I think it is impact on the organization, changing the way people think about problems, helping generalize what works and what doesn't work, bringing learnings to the table.

**Fareed Mosavat** (00:27:18):
For me, I've worked a lot on growth, and I've treated a huge part of my job as not just moving the numbers, but also teaching the organization how our growth model works, how the pieces fit together, what our customers care about, what's working, what's not working, and that creates a lot of, A, leverage in other parts of the organization because they can do better work by having more information, but also, B, trust. Trust from leadership, trust from your peers, and otherwise.

**Fareed Mosavat** (00:27:44):
So, now, how do you get to that? Some of it is just luck. Someone has got to believe in you. You can create your luck by being good at communicating and solving hard problems. I think the other piece is knowing when you go into an organization, "Is this a role that's important to the company? Is it on the list?" I think it is easier to find sponsors, communicate, and create leverage if the thing you're working on is in the top four or five most important things the company is working on. I find myself drawn to those kinds of problems, and I think that's one way because then, all of a sudden, CEOs notice what you're working on, heads of product notice what you're working on, and your peers notice what you're working on.

**Fareed Mosavat** (00:28:22):
The other bit is curiosity. I think to be in the seat where people want to sponsor you, I think you have to show a handle on not just what you're doing, but how that relates to all of the things around you. So I call this going two stack levels up, two stack levels down in terms of your curiosity and what you understand, and also, knowing what's to the left and what's to the right. So let's use the example of if I'm working on activation on growth, let's say, or monetization. It doesn't matter. One of those two pieces. When I say two stack levels down, I like to understand how we build customers, how it works in Stripe, what are our dunning policies, what are the technical things that work and don't work in the pieces maybe down to the database. Right?

**Fareed Mosavat** (00:29:08):
It's like technical curiosity, those kinds of things, but also mental models for what's above you. How do we grow? How does modernization fit into that? What are the trade-offs versus free growth versus paid growth? How important is this to the company? How does it fit into our long-term strategy? Those kinds of things. So it's like the strategic things above you. I like two stack levels because it's like you should understand your boss's priorities and your boss's boss's priorities. Eventually, that means you have to know what the board is thinking, right? Then, left and right is, "What are the core product teams working on that I could help advise on in terms of modernization or they could advise me on what they're thinking and what might be coming next? How do we fit together with the enterprise part of the business even though I'm working on self-serve? How do I think about sales? Do they have input, like interesting customer conversations or input?

**Fareed Mosavat** (00:29:58):
It's this curiosity like walking around, getting to know what people are doing, and being seen as an expert. Are you the desk people go to when they have questions? Are you a person that people ask the opinion when you're trying to figure out how the dots connect? I have found for me, maybe this is just because this is a strength of mine, that connecting the dots of how the whole company works and how all the pieces fit together has been one of the ways that I've driven that sponsorship. I think for each individual, you have to figure out what your superpower is and where you can be actually top 10%, and then lean into opportunities and also problems that help you show that and shine it that way.

**Lenny** (00:30:34):
That is such cool advice. I think what's cool about that is I imagine you just go to your manager and even just ask, "Hey, I'd love to understand just what are your highest priorities, and then what are your manager's?" Just ask these questions. Just that alone I think communicates a lot about how much you care and your interest there, and that creates trust, even if you don't do a ton with it, and knowing what your manager cares about is just going to help in so many other ways just like, "Okay. This matters to them. I'm going to make sure to do a good job there."

**Fareed Mosavat** (00:31:00):
Absolutely.

**Lenny** (00:31:01):
So that is a really cool framework.

**Fareed Mosavat** (00:31:02):
Not only do a good job there, but I'm going to figure out how to communicate what I'm doing to be only the parts that are important and matter to them. I'm going to know that when I hit a certain decision that needs to be made, whether I need their input or not. There are all these different pieces like understanding when to be heads-down, when to be heads-up, when to communicate, when not to, but I think understanding how all the pieces fit together, you really just try, and I always think of it as trying to build a mental model of how the company works, and what's important to it, and what's the equation, so to speak, or what are all the boxes, and then figure out like, "How is my work creating leverage in that?" I find that when you are thinking at that level, people tend to trust you.

**Lenny** (00:31:44):
The core of trust is people. Your manager and their leaders need to feel like you will do a good job and a bigger responsibility, and what gives them trust? Oh, they do a good job, or they're curious, and excited, and understand all these things that they need to understand. So it all makes sense, and I'm always weary of asking PMs to do more work. It's such a busy, long hours job already, and what's cool about these things you're talking about is it's not necessarily a lot more work. It's just a little bit of research and a little bit of digging and thinking.

**Fareed Mosavat** (00:32:12):
Yeah. I think the hard part of this is I have not figured out how to do this well in a remote environment without throwing a lot of one-on-ones on people's calendars because sometimes you figured this out just by hearing conversations, hang out at lunch, and asking questions, and those kinds of things, but it's certainly not impossible. You just have to work out a little more,

**Lenny** (00:32:31):
Just more Zooms.

**Fareed Mosavat** (00:32:32):
Yeah.

**Lenny** (00:32:33):
**Fareed Mosavat** (00:34:08):
Yeah. We talked a little bit about the first of very hard part in product management career development, which is like, "How do I land my first job?" Not a pro at that. We can talk about that more, but then this path from IC to more senior IC working on bigger problems that have more business impact, et cetera, it's a relatively straightforward path. We just talked about some of the ways that you do that. You get a deeper understanding across a wider range of business problems. You solve more unknowns versus being handed problems to solve, et cetera, and you do that by being good at your job. You do that by being good at your job basically as a solo product manager on an island.

**Fareed Mosavat** (00:34:48):
We talked about communication and those kinds of things, but at the end of the day, like we described, most of the work is execution. Most of the work is partnering with your engineering manager, partnering with your designer and your team to build stuff and deliver stuff. You've gotten there by being really good at that. Right? You've gotten there by getting in the weeds, getting in the details, sweating what matters, working hard at it. So someone says, "We'd love for you to lead this team." Great. It's really easy to look at that and say, "Okay. Now, instead of owning free to paid conversion, I own growth overall."

**Fareed Mosavat** (00:35:28):
The first thing you do is start to figure out, "What are the most interesting and valuable projects that I can work on? As an IC, I can only have one person on my team to go dive in and work on those things to make a lot of leverage." This can create a little bit of a spiral of failure because it's the hard job. The IC part of the job is really hard. So, now, I gave you more work across more things, and you're already working 56 hours a week. Now, you got to keep track of more projects across more teams and more people, and maybe you kept the two or three most critical ones to yourself.

**Fareed Mosavat** (00:36:04):
So that's one angle is learning about, yes, it's probably the right thing in the near term for you to focus, and work on this, and be really directive about what to do, and get in every single detail, and make sure you deliver the best product. But long run, you've taken a learning opportunity away from someone else, and you've taken the opportunity for you to be a leveraged person that is more valuable than just their time away as well. So I think that's one piece that drives a lot of failures, just this like, "Okay. Now, I have more problems to work on. I'm going to go deeper on it," and handing the people on your team the least interesting, least leveraged, least fun stuff to do, thinking that's how you get to like, "Oh, now, I get to work on the fun projects, and the interesting and high-leverage ones, and I'll leave all the other ones to other people."

**Lenny** (00:36:51):
I think you call this the manager death spiral. Is that the same?

**Fareed Mosavat** (00:36:55):
Yeah. Yeah, manager death spiral.

**Lenny** (00:36:56):
Yeah.

**Fareed Mosavat** (00:36:56):
This is not unique to product management. This happens in almost every leadership role. You're in a position. You have broader responsibility. You got there by being the best IC on the team probably, so your instincts are to, "I see a bunch of important stuff," and do management stuff too. Right?

**Lenny** (00:37:15):
People may be like, "Oh, shit. How do I avoid this death spiral?" Do you have any advice? Maybe you'll get there, but just how do you avoid this death spiral of keeping all the good stuff and just not scaling yourself?

**Fareed Mosavat** (00:37:24):
I think the first is, honestly, just you have to start trusting other people, which is not common to where you've been till today, but you have to start trusting. You have to shift from doer to editor is the way I think about it. You have to shift from, "My job is to do the work," to, "My job is to make the work better. My job is to plus the work, to review the work, to help other people solve problem." Sometimes that's by being directive. Right?

**Fareed Mosavat** (00:37:51):
Sometimes that's by letting them run because you're like, "Lenny, you're great. Please go solve this problem. Call me when you have a problem." If you have people that are in that upper quadrant of like they understand the problem, they have the level of experience to solve it, it's maybe not 100% important. Maybe it is. That kind of thing. Then, there's the coach in the middle, which is like, "How do I help make that work better?" They have to start figuring out like, "Where is each person on your team in their expertise, and what level of input is the highest leverage for me?"

**Fareed Mosavat** (00:38:24):
I actually think of it as start thinking in terms of being lazy, "What's the least amount of work I could do to make this thing as good as possible?" versus, "How do I do as much work as possible to make sure it's great?" So it's like looking in terms of ROI. The other is just hiring, bringing on great people you trust, making sure you're staffed appropriately, and there's just a second bit. I think one of the bigger mistakes that new ICs make on teams, that they still treat problems the same way they did as ICs, which normally, when you run a pod, basically, your job is, "How do I deliver the most value with the resources I have?"

**Fareed Mosavat** (00:38:57):
When you're a leader, it's now your job to propose, "What are the resources we need to have the most impact on this problem?" I think I personally have messed this up a bunch of times where at the end of the core, I'll be like, "Yeah, but we only had four engineers, and this is what we could do." I'm like, "That wasn't what we asked you to do. We asked you to solve this problem. So adding four more people was what you needed or you needed the marketing team to do X, Y, and Z." You need to go out and do that work now. It is not just your job to get what you can get done with the resources in front of you. It's your job to marshal resources both inside your org and across your organization. I think that's another big area that's related to the trust bit because, again, it's this habit of, "Oh, I got here by doing everything myself." You have to start realizing that your job is to convince other people to do work too.

**Lenny** (00:39:49):
Awesome. So, going back to the canyon. So the first piece was essentially over-focusing on just being too good at the thing you're already doing versus going broader, is that right?

**Fareed Mosavat** (00:39:59):
Mm-hmm. Yeah. So it's like, "Hey, how do I maximize my output? I can do this myself faster than I can explain it to someone else, so I'll just do it," and then finding that you're blocking your team because you're in the middle of every single decision, finding that you're totally overworked, and finding that people aren't learning or growing because those opportunities have been taken from them. So what do you do to break that? You have to just slowly start to give up, trust, do that. So I think that's the one bit is that death spiral of what's getting stuff done.

**Lenny** (00:40:31):
No, no. You can curse all you want. That's all good.

**Fareed Mosavat** (00:40:33):
Okay. Great. Oh, you've just... Well, be careful with "all you want."

**Lenny** (00:40:36):
Nobody has cursed yet on this podcast, and it's all allowed.

**Fareed Mosavat** (00:40:40):
Okay.

**Lenny** (00:40:41):
It's the internet. I don't know.

**Fareed Mosavat** (00:40:41):
We'll solve that.

**Lenny** (00:40:42):
Okay.

**Fareed Mosavat** (00:40:43):
Don't worry. I think the other is what I call the four types of product work, and I think this is not always right at the manager stage. But for every great product leader, you go from being an expert in some type of product work, and I'll describe what those are, to now owning a portfolio of work across a bunch of different dimensions. So the way I think about product work, and Casey Winters and I worked on this framework together, a lot of it comes from him. So I don't want to oversay it, but it's all part of our product strategy program at Reforge is first, feature work, adding new features, product experiences, et cetera into a product in order to drive engagement with your existing customer base and solve a wider range of problems.

**Fareed Mosavat** (00:41:24):
The second is growth work. "How do I help my customers or a broader range of customers connect with the experiences we already have, and drive acceleration and either top-line growth, or modernization, or whatever the most important metrics are. I think you've had many guests on to talk about growth type work. The third is related to growth, but I think is slightly different, which is what we call product market fit expansion. So it's not exactly feature work, which is like, "Hey, now that I use your product more, I have this thing I need in order to keep using it because I'm a power seller," those kinds of things. But instead, we want to attract a whole new sub-segments of markets to the product by adding something.

**Fareed Mosavat** (00:42:05):
There are two forms of product market fit expansion. There's either taking the same product and finding a new audience. Things like internationalization or vertical like, "I'm going to sell the same product to a different vertical because we're a verticalized product." The other is selling a different product to the same audience. This is what bundling strategies basically look like. Right? So adding new marketing tools to a marketing suite, et cetera that attract a different kind of customer and that either drive upsell or drive new audiences to come to that.

**Fareed Mosavat** (00:42:34):
So that's the third kind of product work, and then there's the fourth that is always forgotten by a lot of PMs which is scaling work. So what is the stuff we're doing that is because we are growing, there's new product work we need to do? Most people think of this as technical scaling, but I actually put things like trust, and safety, and other kinds of what we call user scaling problems in this as well. There are a lot of problems that come up at Airbnb just because instead of having 10 hosts, you have 10,000 hosts. Right? There are a lot of problems at Twitter and Facebook that are well puzzle-sized that are a result of their scale, and I think that's a chunk of work that I put in the same category as technical scaling, which is like, "How do we make sure the product continues to work for the people who are using it?"

**Fareed Mosavat** (00:43:15):
So the challenge of the four kinds of product work. "Okay. Great. We have a framework. How is that useful, Fareed?" It's not that useful. It is to know what kind you're doing, but I think as you go up the stack of product leadership, you are going from being probably an expert in one of these, so for me, growth, to needing to think about all these other ones, and you've probably never done them before. Right? Maybe you've done two, but how do you lead across a bunch of different things, and how do you make sure not to be over-focused on the one that you care the most about?

**Fareed Mosavat** (00:43:46):
We've all seen this. Right? It's like growth leader takes over, and everything is a growth problem. Everything is an experiment. Everything should be measured. That's not necessarily true for some of these other kinds of work, and so how do you start to lead, and grow, and build a portfolio across those? I think that's where some of the stuff we talked about before, deep curiosity, looking across, asking a lot of questions, getting to a foundational understanding of what's important there, et cetera is really important.

**Lenny** (00:44:14):
Got it. So part of this is learning new types of product work. So we're talking about trying to move from IC to manager and the things that get in the way, and so is the advice there just start to learn and understand... Maybe, say, you're doing feature work. You're just building a dashboard for your users. Is your advice there like start thinking about how growth works and understand the growth strategy of the company so that people give you this opportunity of, "Okay. Let's put Fareed on maybe a couple other things here because he already understands a little bit more about growth?"

**Fareed Mosavat** (00:44:45):
Yeah. I think there's a framework thing, and then there's like, "What practical advice?" So from a framework perspective, I think it's important to ask the question, "For each of the things that I am responsible for, what category does this fall into? What's important about it? What are the right ways to think about building that, given that it is different than what I've built before?" So, some of this, you can do within an org. If you're working on core product stuff, you probably have an adoption problem on one of your products, and there's growth work associated with driving usage of that thing.

**Fareed Mosavat** (00:45:18):
So I think there's a piece at which even within a certain sub-segment that this can be valuable. You could be working on enterprise, which looks a lot like a lot of scaling work, right, and a lot of feature work, "Get me the right administrative dashboards and these kinds of things," but also, maybe you have a problem that's a growth problem. "How do I drive adoption? How do I actually drive usage? How do I make sure that our new enterprise customers are activated and retained?"

**Fareed Mosavat** (00:45:43):
So I think at scale, any product leadership work has some pieces of these different kinds, and I think building a mental model for, "What are the other things we need to do? What's the right portfolio allocation across these different types of product work, and do I have enough of a baseline understanding of the different ways to evaluate and think about those and what the goals are in order to drive leadership across work I might not be able to do myself very well?" I am not a good technical PM despite having an engineering background. It's been too long, but I hope that I can lead technical scaling, technical debt restructure on my team or at least understand whether it's important to do or not.

**Lenny** (00:46:20):
So if you think about this concept of getting through this canyon broadly, it boils down to more scope. Maybe that's the way to think about it. It's like more scope of product work that you work on, being better at different types of work, scaling yourself so that other people can do work on your behalf or within your umbrella, and the point you made about not being satisfied with the resources you have and in helping people understand, "Here's what we could do if we had this many resources," and making the case for that feels like that's the overview. Is that how you think about it?

**Fareed Mosavat** (00:46:49):
Yeah. I think that's exactly right, and the last one is really important because now, you have moved to owning the impact. As a leader, you now own the business outcome, the impact, the delivery, not some sub-problem or known answer. You have to define the solutions. You have to talk about how many people you need to do them, and you need to figure out what do you need from the rest of the organization to do that. So, yeah. I think those are the three big buckets of things that I see trip people up.

**Lenny** (00:47:14):
Awesome, and just add plus one to that last point. Just like a lot of PMs end up being victims of the resources they get and like, "Oh, how could I have possibly had this impact with the resources you gave me?" versus, "How do I avoid that and empower myself to help people understand, 'Here's what I need to do this thing that you want me to do. If you think this is important, here's what we need,' and put it on other people's plate?" It doesn't mean you'll get it, but it's important to put that up front.

**Fareed Mosavat** (00:47:38):
Yeah, and that goes from a "would be nice" and makes you a better... more junior or even senior PM makes you a more effective one. It's extra credit. At the leadership level, it's baseline. The baseline is, "Okay. I believe this is the outcome we need to get to by this time, and this is what it's going to take. Here are the trade-offs. Here's what I need. Here's what I can get you if I can't do that." The reason I drum this one home is I feel like this is the mistake I have made now multiple times in my career, and I can't... At this point, I'm embarrassed to have seen it happen over and over again because you just get caught up in like, "Okay. Here's the team I have. I've got to build a roadmap. I've got to make sure everybody's got work to do," and you say focused on feeding that beast, and you forget to ask, "Is this even the right group to solve this?" Maybe you need a smaller team even, maybe you need a bigger team, or maybe you need different people. I think often, you find yourself victim of the circumstances instead of owning the situation.

**Lenny** (00:48:39):
I love that. When did you realize this was something you should be doing?

**Fareed Mosavat** (00:48:42):
I've learned different versions of this lesson now multiple times. I learned it at Instacart. I had a very small team, and we've got a lot done. But honestly, I think I failed to make the case that we should grow it faster and only... It was only when someone was like, "We should add more people." I was like, "Great. Yeah. Let's do that." I don't think I was hurt by that, but I think it was a, "Oh, you have permission. You should have asked," kind of thing. I think at Slack, the lesson I learned was about cross-functional. I think we did a good job of making the case for why we needed new teams or add more things to drive more impact, but I still took a very product approach to solving activation and monetization expansion type problems.

**Fareed Mosavat** (00:49:25):
What I think is I look at what could have moved the needle more and what it could have made me a more successful leader at that company. It would've been partnering more closely with marketing, for instance, to figure out how we could be working on things together, helping drive their roadmap, and vice versa. Same with sales. Same with the data org. Same with finance. Those kinds of things where I don't think I was driving enough of the high-level outcome I owned, which is driving growth in the self-service business across the other parts of the company that needed to do that. I was a product leader, so I did product work, and I... Lesson learned.

**Lenny** (00:50:05):
Yeah. Thanks for sharing that. So we've been talking a lot about the regular path, and getting better and accelerating your path as a product leader, and staying on this track. There's also this alternative track that I know you're passionate about, and Reforge just become a beacon, it feels like, of folks that are moving away from working at one company to working at many companies and scaling their impact. I'm curious to hear your thoughts on what you've seen there. There's this large trend of just senior people becoming advisors, writing things, newsletters, for example. I'm curious what you think is happening there and how you think about that.

**Fareed Mosavat** (00:50:41):
It's interesting. The whys are hard to pin down, but it's definitely happening. I think some of it is maybe COVID-induced, some of it is remote work driving these trends, and some of it is just like there are a lot more leaders who are a lot more in demand. So, just to recap, a trend that I think we are seeing and that has been really interesting is a trend of senior leaders, people with meaningful operating experience, first, diversifying their impact maybe while they're still at a full-time role. Someone like yourself, Lenny, maybe was full-time at Airbnb or a similar company and said, "Hey, I'd like to do some advising, some angel investing, some speaking. Maybe I'll start writing a newsletter on the side," and then moving to this new category that I don't feel like really existed. Maybe it did in certain pockets of executive leadership around tech and startups, but really seeing it in product management of a shift towards, "The best use of my time and my career is to work across a portfolio of problems that a variety of different companies."

**Fareed Mosavat** (00:51:47):
So we are seeing a larger percentage of our executive network. It's still small, but working on things like newsletters, podcasts, those and the like at the edge of the content creator side, but also, full-time advisors, fractional heads of growth, fractional heads of product one day a week, et cetera. Long-term advisory relationships, running workshops. These kinds of things that are more like a la carte. I think they love it because of the flexibility that it creates for them. They love it because of the high upside and non-linearity of possibility of results now instead of having equity in one company for four years of 100% of my time. It's a portfolio approach to not just the time and energy, but also the upside and opportunities that are there as well as the fact that they're just so in demand.

**Fareed Mosavat** (00:52:41):
For senior leaders who have been in meaningful seats at well-known companies, you're getting hit up by recruiters all day long, and the decision, "What do I want to spend the next four or five, six years of my life on if it's just one thing?" is a very difficult one. So what we're finding is people seeing, "Hey, you don't need me full-time. What you need is me here a day a week to help your up and coming leaders be awesome." We're just seeing more and more of that in the industry, and it's been a really interesting trend to observe. Of our executives and residents, I would say most now are exploring this kind of advisory, fractional, or otherwise portfolio-based approach to their futures. Whereas most of them came from full-time roles beforehand.

**Lenny** (00:53:24):
Yeah. A program at Reforge is designed for that. The idea there is, "You don't know what you're going to do next? Come teach a class at Reforge to help some folks out, and then use that as the time to explore what you're going to do next." Right?

**Fareed Mosavat** (00:53:35):
Yeah. Yeah, it is, and the hypothesis... I was one of the first EIR, so I started as an EIR at the company, and then ended up joining full-time as an executive. The hypothesis was, "Hey, let's give people six months to a year so that they don't just hop from one really high-stress, really difficult job into the next one. We also want great operators teaching and meeting our programs. How do we build a win-win situation?" So what we did was we created the Executive in Residence program as a way to help top operators have a transition point, but I think the hypothesis was that most of them would take on the next VP product role, or CPO role, or CMO type role, and what we're finding is that more and more of them are using that space and time.

**Fareed Mosavat** (00:54:17):
They are building up their understanding of where they're experts and what their real TEDx value is, and then finding ways to do that across a variety of different companies and organizations versus just the single one, one, because they want to try before they buy, so to speak, in terms of of like even if you do end up somewhere full-time, it's nice to be able to really work with them and get to know them because at the executive level in particular, it's a really high level of commitment, and you have a lot of opportunities, so you want to be really careful about it. But also, two, because it may not be the best use of your energy. When you have a lot of frameworks and you have a lot of broad understanding, you have a lot of examples, your value to the ecosystem is often by helping lots of companies be successful, not just one. I suspect that's how you feel about what you're doing as well.

**Lenny** (00:55:07):
Yeah. When I started down this path of experimenting with a newsletter back in the day, I called it Project Avoid Getting a Real Job, and what I was trying to do is figure out, "Can I make a living doing this thing even though I don't know if there's any way to make money writing a thing?" My wife is always like, "There's no money in writing. What are you doing? I thought you wanted to start a company, that you wanted to do some advising."

**Fareed Mosavat** (00:55:28):
Yeah. Well, let me talk about why I think the generalization there's no money in writing is true, but I think it's true because it's... In general, maybe not, but what's happening, I think, is people are figuring out, "What is my specific knowledge," just to tie the knots back to the thing we started at the beginning, "that because I've taken so many reps at this is actually not easily replaceable in a focused area?" So modernization or building zero-to-one paid channels as a marketer, or whatever it is. Just narrow enough that I know I'm one of the five best in the world at or I can make the case that I'm one of the five best in the world at it. You as a company probably can't hire that person because you're too early, don't have enough money, don't have enough clout, et cetera, and that I have generalized enough in my mind that I can actually be really effective in a small amount of time.

**Fareed Mosavat** (00:56:25):
So what works for you, I don't know a lot about the mechanics of your newsletter, but it's not just writing. You're writing about a very specific set of topics that you have unique experience in that has harnessed a very focused community, and I think we're seeing this across a bunch of different things that there's a lot of sub-expertise. No one can be an expert at company. Some people claim to be, but when you get down to it, I feel like an expert on bottoms-up SaaS activation strategy is like, "I can speak pretty confidently about that. Somebody has a problem in that space, I can usually at an hour accelerate their learning pretty dramatically." I think as we're finding what these things are and people are getting smarter about what they're looking for, I think it opened up this space where you can be the best in the world at a relatively narrow topic and make a real meaningful living out of it.

**Lenny** (00:57:19):
There's two thoughts I want to go into here, and then I think we should probably wrap up, but one is I do worry there's like... everyone that gets to a certain point, it just exits the career track, and who's left to build things? I worry that just everyone is trying to become an influencer/creator person. So what I wanted to chat about briefly is just downsides of this path in life.

**Fareed Mosavat** (00:57:41):
Sure.

**Lenny** (00:57:41):
The other pieces is for folks listening that want to pursue this direction, what could they do to set themselves up? So the first piece is just like, what are the downsides? I'll share a few already. So in this life that I lead now, I get no health insurance benefits. I get no time off. I get no 401(k) matching. None of that. I have to basically pay an absurd amount of money for health insurance and find ways to take time off, invent PTO policies for myself, and all these sorts of things. I've gotten used to it, but it is weird. My wife is also an independent self-employed person, so we both don't have... If we have a child, we have no mat leave, pat leave. We just have to figure that out. I don't know how I would do that. So that comes to mind for me. What else have you seen as the downside of this path?

**Fareed Mosavat** (00:58:25):
Yeah, the second is it's unclear what the longevity is. How far can you be removed from your full-time experience and still be valuable? This is why I actually think this is a better path than what used to happen, which is all the great operators turned into VCs, venture capitalists. Right? In there, you're pretty disconnected from the ops. I think this advisory type path, I'll leave the creator piece alone because I'm not as familiar with it. But in the advisor path, you are still maybe spending a day a week with these companies. You are still doing. You are helping grow the next generation. I don't like to say generation, but next crop of up and coming leaders. So the question mark for me is longevity. Is it possible to build more and more amazing companies if more and more amazing operators are leaving the full-time workforce?

**Fareed Mosavat** (00:59:20):
I don't know, but I hope that it's better than what it's been because actually, they're building and doing, et cetera. So I think that's the other question mark and downside, and I think we think about this as part of our ecosystem. I think as long as people are doing, and generalizing, and executing, as I talked about it at the beginning, I think they can still be valuable in a meaningful way and maybe provide access to that kind of knowledge for a broader range of companies. The other is just like if everybody does it, then maybe it's not so unique anymore. So I think there's a question there as well.

**Lenny** (00:59:55):
The other piece is like you're constantly having to do sales and BD as an advisor like, "Who's the next company?" You're always wondering if there will be more, if they stopped. It's a real part of it.

**Fareed Mosavat** (01:00:03):
That's why it has not been attractive to me personally, I will say. I like being focused on a singular problem for some amount of time. I do a lot of portfolio-type stuff outside. I advise casually. I do some coaching. Not coaching exactly, but mentorship for a couple of different up and coming product leaders. I do some angel investing, those kinds of things. I like to see what's happening around me, but I do like having an anchor. That's like my main thing, and I don't like selling. It turns out I don't, and so you have to like that, I think, to do some of this stuff. But I think there are things our platform at Reforge will be able to do for these kinds of offers. There's a long period of time to make that easier and easier. No promises, but stay tuned.

**Lenny** (01:00:46):
Okay, okay. So then, going back maybe as a final question. For folks that are just like, "That sounds great. Maybe in the future, I want to become a full-time advisor, EIR person, writer person," what advice do you have for folks to set their career up for a place where they can get to a place where they can become full-time advisors, let's say?

**Fareed Mosavat** (01:01:04):
This is this generalized step I talked about in the learn loop. It becomes even more important if what you want to do is not just do your current job well, but be able to communicate why that expertise is valuable to other people, other companies across a wide range of things. So I would say choose your opportunities carefully to be building the right balance of depth and breadth across different things. You need to connect dots, so you do need different data points from different types of product work and different types of organizations because you don't want to be so narrow that only DDC eCommerce company that sell once-a-year purchases or whatever is the only thing you can work on. That's just an example. I could have come up with a bunch of others.

**Fareed Mosavat** (01:01:51):
You need to have some breadth, right, but it's like same problem, different industry. It's one way to think about depth that's focused. Different problem, same industry is another way to think about it, but you have to come up with a unique intersection that is clearly you are in the top tier of the people who know how to do that. That's a little bit nuanced. There's an art to it I think in some respects, but I think that's an important piece of the puzzle.

**Fareed Mosavat** (01:02:14):
Second, work at great places. I think this is good advice for almost all product managers in particular, but really, anybody working in tech, for better or for worse, where you worked matters to people for two reasons. One, it's easier to do great work at a place that is fundamentally working. When the tide is rising, there are tons of opportunities to make meaningful, deep, awesome impact. The second is what you talked about. You're going to be in the sales business eventually, and it's a lot easier to sell experience at places people have heard of than places nobody has heard of. Unfortunately, that's I think a big piece of this puzzle as well. I don't have to spend a lot of time talking about what Slack is. You probably don't have to spend a lot of time talking about what Airbnb is. I think that helps, and it is a meaningful piece of the puzzle.

**Lenny** (01:03:04):
Absolutely. Fareed, I feel like anybody that listen to this episode is going to be a better product manager. I'm very confident of that, and I'm really appreciative.

**Fareed Mosavat** (01:03:13):
I hope so.

**Lenny** (01:03:14):
I'm sure of it. So, just to close, where can folks find you online if they want to reach out, learn more, and how can listeners be useful to you?

**Fareed Mosavat** (01:03:21):
You can find me on Twitter almost most days, F-A-R-3-3-D. That's been my handle since I was a young man.

**Lenny** (01:03:29):
So complicated.

**Fareed Mosavat** (01:03:30):
So check me out there. It's just threes instead at Es, right? That's probably my social network of choice and best place to communicate or hear what I'm thinking about or what I'm doing. Obviously, I do a ton of work at Reforge. On our events, I toast a bunch of different things, do a lot of stuff. If you're interested in these kinds of topics, please, I don't want to make this a sales pitch, but we have a lot of programs that are dedicated to deep dives into the problems that we've talked about here. I'm dedicating this next chapter of my career to helping a wider range of product leaders be great at their jobs, and that's what we do for a living. I hope that we can help folks there.

**Fareed Mosavat** (01:04:06):
As to what people can help me with, I don't know. I'm always looking for people working on interesting stuff or with interesting, unique problems. If you're a founder working on something interesting and you're looking for an advisor, practical advisor, not for me, but we have a wide range of network experts that I'd be happy to connect folks with. If you're a product manager on a team that's looking to figure out how to break through on certain problems, reach out. Maybe we can help with Reforge or maybe I can help individually.

**Lenny** (01:04:35):
Thanks for being here, Fareed.

**Fareed Mosavat** (01:04:36):
Yeah. Cheers. Thanks for having me, Lenny. I think what you're doing is wonderful and making a big difference for PMs everywhere, so thank you.

**Lenny** (01:04:44):
Same. Thanks, man.

**Fareed Mosavat** (01:04:45):
Cheers.

**Lenny** (01:04:47):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [7/20] Category creation and brand building | Barbra Gago (Pando, Miro, Greenhouse, Culture Amp)

**Barbra Gago** (00:00:00):
When you're building a category, you need to make sure that there is a category that's validated by analysts and directory sites and things like that. But also, you want to have a lot of traction in terms of thought leadership like why is this the category? What are the unique value propositions of this particular thing? What are the pain points it solves? And then of course, getting a lot of content around because when you're generating a new category, you're also needing to educate buyers that there is a category that they can now budget for and why they should allocate budget for that.

**Lenny** (00:00:40):
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 learned experiences, building and scaling today's most successful companies.

**Lenny** (00:00:54):
Today, my guest is Barbra Gago. Barbra was chief marketing officer and global head of Marketing at Miro where she helped build their global brand and create a whole new software category for the space. Before that, she was VP of marketing at Greenhouse where she brought the product to market and led their go-to market strategy. And she was also head of marketing at CultureAmp where she helped build their go-to market plan and close their first 50 customers.

**Lenny** (00:01:18):
In our conversation, we focus on three topics: creating your own category, when it makes sense to explore that, when to avoid it and how to go about it; building your brand and rebranding when it makes sense to, and building opinionated software. I've never seen a post or a podcast get as deep into category creation or rebranding, and I'm confident that you will learn something valuable from this podcast. With that, I bring you Barbra Gago.

**Lenny** (00:01:46):
This episode is brought to you by AssemblyAI. If you're looking to build powerful AI-powered features in your audio or video products, then you need to know about AssemblyAI. AssemblyAI is the API platform for state-of-the-art AI models that thousands of product-led growth companies like Spotify, Loom and CallRail are using to infuse AI into their products. With simple APIs, developers and PMs can get access to powerful AI models for transcription, summarization and dozens of other tasks that are fast, secure and production ready. All of their models are researched and trained in-house and continuously updated by their team of AI experts, which for a PM makes it easy to build and ship new AI-powered features.

**Lenny** (00:02:30):
Product teams of startups and enterprises are using AssemblyAI to automatically transcribe and summarize phone calls and virtual meetings, detect topics and podcasts, pinpoint when sensitive content is spoken, redact PII from audio videos and way more. Visit assemblyai.com to try AssemblyAI's API for free and start testing their models in their no code playground. That's assemblyai.com.

**Lenny** (00:02:57):
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**Lenny** (00:03:27):
Stitch customers have been able to increase conversion by over 60% after spending just one day integrating. And with their API and SDKs, you can improve user conversion and retention and security, all while saving valuable engineering time. Your engineers will come and thank you for using Stych because Stych keeps you from having to build authentication in-house and the integration process is super fast and super smooth. To get $1,000 in free credits, just go to stytch.com/lenny to sign up, and that's stitch with a Y.

**Lenny** (00:04:05):
Barbra, welcome to the podcast.

**Barbra Gago** (00:04:07):
Thanks, Lenny. Excited to be here.

**Lenny** (00:04:10):
Just to start off and set a little context for our listeners, can you give us a 55-second background on some of the wonderful things you've done in your career and what you're up to now?

**Barbra Gago** (00:04:21):
Definitely. So I've spent pretty much my entire career in B2B SaaS tech, building and scaling through hyper growth, oftentimes with disruptive technologies at the center of people, tech, future of work. I would say I helped bring products like CultureAmp and Greenhouse to market in the people space. Before that, I did some work in enterprise social networking in the Yammer days. And most recently, I was the CMO at Miro where I also led the rebrand and introduced that product to the world, which was very exciting.

**Lenny** (00:05:01):
And you've got a startup now, so maybe you just mention that briefly and then we'll talk about it at the end again. Yeah. What are you working on now?

**Barbra Gago** (00:05:08):
Yeah. And now, I'm building a product which we'll see about the category what it ends up being, but it's what we call an employee progression platform. So basically, from the work that I've done as a leader, building and scaling teams and also the exposure I've had in the people tech space, I just have found that there's been a lot of tools lacking for leaders to really coach and develop their team in the right way, creating enough structure and transparency into the process that creates accountability on both sides. So yeah, we're taking on the big goal of killing performance reviews.

**Lenny** (00:05:49):
Holy moly. Cool.

**Barbra Gago** (00:05:50):
Very exciting

**Lenny** (00:05:51):
Performance reviews. Very exciting. It's true. We'll talk about that a bit at the end more. And there's a bunch of stuff I want to dig into. You have such a cool background on so many interesting experiences. The first is something that you mentioned just now, which is category and category creation, which I know is near and dear to your heart. I was reading a bit about your background, and I learned that at Miro, you invented this category that's now called visual collaboration. And at CultureAmp, I think you helped lead the creation of this category, employee experience. I imagine at Greenhouse, you did something similar. And I know startups are often trying to decide, should I create my own category? Should I try to win in an existing category? And so I want to spend some time talking through your experience there.

**Lenny** (00:06:32):
And so the first question is just say at Miro or Greenhouse, can you just talk through your thought process of trying to decide, should we invent a whole new category that we're going to win or should we just try to win an existing category and how did that go?

**Barbra Gago** (00:06:45):
They're both great examples because in one, we did create a new category and in the other, we tried and abandoned ship. With Miro, I think when I joined the company, there was this concept of an online whiteboard, which also is a category, but it's a much smaller category and it wasn't something that a lot of people searched for. And I think the biggest motivating factor of thinking about category creation at Miro was how do we become something really big and needed by every company and not just this little thing that maybe product teams would use or maybe engineering teams or schools or something like that.

**Barbra Gago** (00:07:26):
When you're thinking about category creation, it's really, for us, it was really about the scope of what we're trying to do and not wanting to be in something too small. And I think with Miro, the platform that it is, there is so much possibility. I used to joke that it was, even as a company, we were the ever expanding universe. There's just so much to do there, but online whiteboard was really small.

**Barbra Gago** (00:07:52):
Greenhouse is in the ATS category, which is applicant tracking system. And at the time, applicant tracking systems had a really bad name. I don't know if folks that listen to this know of Jobvite or remember Jobvite, and there were a lot of systems before that. Jobvite had come in the mid-2000s as the new and improved ATS and it was all about social recruiting, but it was very transactional and it wasn't very strategic. And so we wanted to steer clear of the ATS space even though we were an ATS. We can talk more about what we tried and what we ended up doing, but I think the main factors when you're thinking about category creation is really what budget companies have, if they have a budget, if they don't have a budget. Companies did have a budget for ATS, for example. Until now, I don't think companies had a budget for visual collaboration. For example, what's the language and the words that people use to describe their pain points and their situation, the things that they need? And then is their competition?

**Barbra Gago** (00:08:59):
And sometimes, competition, you would think like, "Oh, we want to not have competition, so let's build a new category." But ultimately, you're not building a category until there is competition. It's not officially actually a category until there's more companies that do that. And that was a big learning for me in this whole process of category creation, is that it's actually okay when new companies come in that say they're that category because it's just validating the fact that there is a new category. So I think it's really ... If and when is really about what the overall objective is and also what the current situation is with competitors and the space. The ATS market is still the ATS market, for example, and Miro has created visual collaboration as a category but also ticks off boxes for other categories as well.

**Lenny** (00:09:53):
I have a thousand questions I want to ask to dig deeper. Before we get in there, can you just define, well, what is a category? Folks that are just like, what the hell have you been talking about? What is a product category? What's the high level way to think about this?

**Barbra Gago** (00:10:04):
When we talk about category, I think it's really what would be a good way to explore your space and your relevant categories would be to go to G2 Crowd or Software Advice or any of those type of review sites or directory sites and learn about how they've categorized products based on feature sets. And so within each industry, there's going to be a bunch of different types of categories. Those categories are typically products that solve, at least in B2B products, that solve a certain pain point or a set of pain points, and they can be very wide like all in one and big solutions or they can be narrow. There's this all in one versus best in class, for example. And I think that's where the granularity of category comes into play and then how big the market is. Obviously, maps to granularity versus more broad and when are you granular versus when do you go broad? But I think ultimately, it's just a set of features or products that are solving a specific pain point that customers most likely have a budget allocated for.

**Lenny** (00:11:17):
And then the category ends up, the way you use it is it's the way you pitch your product often. It's like the big part of the headline, part of the way you sell it. It's like you come back to this we're the leader in visual collaboration, for example, or that's how it practically ends up being used.

**Barbra Gago** (00:11:31):
Exactly. It's interesting because I would say that if you're building a category as well, you can sometimes be selling into a category while you're still building the appetite for a different category, which is a nuance, which is all about where's the budget and how do customers describe their pain points?

**Lenny** (00:11:53):
This reminds me, I was just trying to pitch my podcast in this little dock I'm writing. And initially, I was like, "Oh, it's like a top hundred business podcast." And I'm like, "No, it's the number one product and growth podcast in the world," which is true, but I created my own category. How about that?

**Barbra Gago** (00:12:09):
There you go.

**Lenny** (00:12:10):
Was that a good idea?

**Barbra Gago** (00:12:11):
I think so. The thing is it's like when you talk about ICP for how you're going to sell your product and really build a repeatable sales process to scale that piece of your business. And the more specific the thing is that you're selling initially, obviously you're going to have more relevant users. They're going to spread word of mouth, etc. You could always expand that scope later. The category can also evolve. You mentioned CultureAmp earlier. The category now is people experience. Actually, when I was there, it was more about people analytics platform or people intelligence platform because we were providing a deep set of data that companies didn't have before, but that category has since evolved as their go-to market has changed, as they've added new products to their platform and new features and things like that.

**Lenny** (00:13:06):
To make it even more concrete for people, what are other examples of categories that come to mind that are either invented recently or just generally?

**Barbra Gago** (00:13:14):
In the early days, I was working on market automation, for example, so Marketo, now HubSpot, fits into that, even though back then, they were more of this inbound marketing platform/category performance management, which is the area of Pando. We've talked a lot about people, products. I think Gainsight did a great job with the customer success platform, so this is a different problem that they were solving within the organization for a group. The customer success team, basically how are they going to make their customers successful?

**Lenny** (00:13:49):
Awesome.

**Barbra Gago** (00:13:50):
Okay.

**Lenny** (00:13:51):
Yeah, customer success. It's a well name.

**Barbra Gago** (00:13:53):
Yes.

**Lenny** (00:13:55):
Okay. There's many benefits to try to create your own category, right? We're number one. That's one main category. Two is you can lead the charge on understanding or just defining what's important. I imagine there's other benefits maybe you could share, but there's also probably a lot of downsides. You mentioned oftentimes, it doesn't work and it just ends up being a lot of wasted money. Maybe just talk about what are the reasons to pursue trying to create your own category and then some of the reasons you maybe shouldn't.

**Barbra Gago** (00:14:20):
Greenhouse is a great example to talk about a failed approach at creating a category. So I mentioned before the ATS or the applicant tracking system category at the time was just, it carried so much disdain. People had such bad experiences with that whole category of products. No matter what, they weren't strategic. They didn't help people be good at recruiting. It was just a pretty terrible, very transactional experience. And I came in and it was like, "Okay, let's reposition ourselves. We're going to create a new category." We tried several things.

**Barbra Gago** (00:14:57):
One of the main things that we zeroed in on was recruiting optimization platform, and it was really like we are doing that. We're helping companies really structure the process, identify where they have gaps, where people are falling through the cracks, where they're flying through the process and really tweak and iterate it and improve it. And we spent time getting content out there, talking to press about it, positioning it in this way. And ultimately, at the end of the day, the budget that customers had and the way that customers talked about what we did, no matter what we called it, was applicant tracking.

**Barbra Gago** (00:15:33):
So it didn't really make sense to continue to go against the grain of, no, we're going to be this new thing or we're going to call it this if everybody, even seeing the value and seeing the differentiation of our platform to others, still called it an ATS. We abandoned that process. But I think the main thing that we understood then was instead of spending the time and money to build a new category, we were going to spend the time and money to elevate the value of this category. So rather than changing the category to something else which we could value at whatever it was, we were just going to spend all of our resources to make this whole category much more valuable to the users, to companies. And that really was, along with what CultureAmp was doing at the time in the same space, what set off this whole trajectory of really good, strong people practices and people organizations that were really doing cool stuff on the recruiting side as well as employee engagement.

**Lenny** (00:16:35):
You mentioned a few components of when it makes sense to come up with a category. One is there's budget already against it. Two is people use the words associated with that category. I imagine with Miro and this idea of, what was it, visual collaboration, there wasn't budget for that yet. So how does that work?

**Barbra Gago** (00:16:53):
No. That is more of the vision piece, I would say. Sometimes you can have a vision that customers, they don't have it yet or they don't share it, but they can grow to share it and they did in that case. And I think that with Miro, we still worked to optimize where we could in terms of the categories that we did fit into or how people talked about us, but it was also such a new format and it was really a disruptive product that didn't exist before in the enterprise so that it was called a lot of different things. So it was much more fluid and people talked about it in different ways, and this was our way of hearing the feedback about how people talked about it as online whiteboard or lots of jobs to be done were framed, mind mapping platform or diagramming or whatever, all of these little things.

**Barbra Gago** (00:17:52):
And so visual collaboration was our way of putting a nice bow around this thing that could then be an enterprise product that solves a lot of different problems for a lot of different use cases and different types of users. We started out selling and having a lot of users that were in product and in engineering and teams that were used to using whiteboards anyway and then needed to do it in a distributed way, but very quickly packaged different types of jobs for HR teams or marketing teams or design teams and pretty much anybody in the organization. But it needed to all come together cohesively; otherwise, it was like everybody in the org just calls it a different thing because they use it in a different way.

**Lenny** (00:18:37):
Part of what I'm hearing is that you don't stop working on the other categories that it already sits within and just keep optimizing those but in parallel, start to try to pull together, hey, there's this bigger vision of where this could be. Does that sound right?

**Barbra Gago** (00:18:50):
I think so. And it's really where you get the inputs from your customers and your users. We heard all these things. Miro, we did a lot of content marketing. That's a big piece of doing category creation generally I would say. But there's a lot of different ways that people talked about it, and so that's an opportunity to actually come and say, okay, here's what it is because no one knows, and it's all of these things and all of these things together equals this now. And then that created momentum where other companies started thinking like that and then they started tagging themselves as that category as well, and then you had a category of multiple companies now that were doing similar stuff.

**Lenny** (00:19:35):
Yeah, absolutely. How do you know when it's probably a bad idea to try to create your own category?

**Barbra Gago** (00:19:41):
The sooner, the better if you're going to try and fail and iterate. I think if you already are well established, I don't think category creation is really a meaningful effort if you already have ... It's not going to be necessarily a way to just all of a sudden generate new business by creating Q&A new category once you've already gone far enough down the path. I think that if you're not getting ... With the Greenhouse situation, as much as we used this other language and it did get picked up a bit in terms of context that people would use to talk about Greenhouse, it really just wasn't sticking. And so I think it's good to try things and also abandon them and that's okay. You can always sit back into the category. If you really don't fit into any other category, then you probably do need to figure out what the category is and package that. And that's going to be done mostly by continuing to talk to customers and listening to how they talk about things. It all comes from what you hear from them ultimately and what will resonate.

**Barbra Gago** (00:20:49):
So I think, yeah, if you're already established, if you really aren't differentiated from other categories in your space, then you probably are in that category. And doing category creation is a lot of work that is not going to be fruitful if you're pretty squarely in something already. And then if you really aren't but you need to figure it out, you're just going to have to keep iterating until you figure out what makes sense to your customers.

**Lenny** (00:21:15):
For founders who are listening to this and they're just like, "Oh, this sounds interesting. I want to try to think about a new category maybe for my product." Can you just talk about the mechanics of going through this process of trying to decide what category it should be called, how to roll it out, anything you could share by just the tactics of creating a category?

**Barbra Gago** (00:21:36):
The main thing which we've talked a little bit about already is really understanding your customers and their pain points and how they talk about things. All of my best marketing and positioning literally comes from having a million conversations with customers and listening to how they solve problems and how our system helps them solve problems and what they're doing and how they talk about stuff. I think that's step one, is really understanding who those buyers are, how they talk about the product, what's the unique differentiator and selling points?

**Barbra Gago** (00:22:10):
One thing that's really important in category creation as well is actually PR. You need to get this category and positioning out there at a high level in order to test it out and see if it makes sense and if it's resonating. And then the other piece is really those directory sites, which the analysts like Gartner and Forrester and all these guys, at least in B2B and enterprise, they really shape for customers what the categories are. And you need to build relationships with them. You need to work with them to create your category as well. So with the visual collaboration, for example, we weren't ranking, we weren't categorized in visual collaboration on G2 Crowd, and we had to meet with them and explain what it was and talk to them about the differentiation of this category versus other categories in terms of features and all of that stuff so that they could understand how they would differentiate this category from another category.

**Barbra Gago** (00:23:15):
So I think those are really good channels to look at. And then tactically, it's a lot of content marketing and a lot of thought leadership. When you're building a category, you need to make sure that there is a category that's validated by analysts and directory sites and things like that. But also, you want to have a lot of traction in terms of thought leadership like why is this the category? What are the unique value propositions of this particular thing? What are the pain points it solves? And then of course, getting a lot of content around because when you're generating a new category, you're also needing to educate buyers that there is a category that they can now budget for and why they should allocate budget for that.

**Lenny** (00:24:02):
Sounds like a hell of a lot of work.

**Barbra Gago** (00:24:03):
It's a lot.

**Lenny** (00:24:05):
I'm curious. What percentage of say B2B companies do you think should pursue creating a category? Is it almost none or is it a meaningful percentage?

**Barbra Gago** (00:24:13):
It goes in waves with the tech innovations. So for example, when there was the whole first web wave and then there was this whole social enterprise and consumerization of IT was a big change in how technology occurred in the workplace and a lot of new categories came at that point. So I feel like it's less about the raw percentage and more about general inflection points that are happening that are causing the need for this.

**Barbra Gago** (00:24:44):
And I take COVID for example and this very quick shift to distributed work was one of those type of inflection points that has changed a lot. A new category that has grown extremely fast is, and I don't even know exactly what they call it, but it's these employment platforms like Deel and Oyster that have cropped up and grown significantly fast and also have created a new category where there was already the ability to hire people in all of these distributed places, but you had to find a company in that place that would then hire the people. And then of course, they created these platforms where, hey, here's a system, you can manage it all here, we'll go and build all those relationships on the ground. And Nayya is a new set of a new category with four or five companies just in the last three years that have cropped up. So I think it's more about what the market demands and what's happening in the market rather than whether or not one company it makes sense for, if that makes sense.

**Lenny** (00:25:48):
Yeah, makes sense. It depends on where the tide is pulling everyone. I think that makes a lot of sense.

**Barbra Gago** (00:25:52):
Exactly. Yeah.

**Lenny** (00:25:53):
Maybe one last question about category creation. So on the surface, there's this binary choice. Either try to become the best ATS platform or we're not ATS, we're employee recruiting automation. Is there a middle ground? Do you have to go one or the other or is there some in between route, maybe positioning a little bit differently or how do you think about that?

**Barbra Gago** (00:26:13):
There could be some middle ground. I would say for Pando, for example, performance management is a very established category that we technically fit into, and also there's a line item on the budget and people have money to pay for performance management. But we're introducing this concept of employee progression, which is more of a long tail strategy. So while we want to educate the market and build this new category of employee progression because it's related to the differences between what we're doing and traditional performance management, we're still going to rate ourselves in directory sites, for example, or categorize ourselves as performance management and talk about performance management and sell to companies that are looking for performance management. But ultimately, we want to shift everybody's mindset and change the category.

**Barbra Gago** (00:27:09):
So it's not necessarily one or the other, but I do think the investment is high if you want to build a new category, and we're committed to an investment of time and thought leadership and content and all of that stuff, but it's also not our strategy right now to go and create employee progression and own and dominate this. We're going to work our way up to that over time.

**Lenny** (00:27:34):
Got it. That connects to what you talked about with Miro. It wasn't like we're switching, we're now visual collaboration. It's like we're still whiteboards, we're the best white boarding tool, but let's also start building this brand of visual collaboration so that people start to learn.

**Barbra Gago** (00:27:48):
Exactly. And I think it's a bottoms up mentality much like our business model was there because with marketing automation, it wasn't a progressive buildup. It was marketing automation. That's what the category was. I was working for a company that was doing marketing automation. There was Eloqua and Marketo and several others and we all were just telling everybody, educating the market on what that was, and that was very top down.

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**Lenny** (00:29:38):
I know another area that you spend a lot of time thinking about and you've done a lot of work around is branding, rebranding even and just go to market in general. I know at Miro, you led the charge on rebranding Miro. It used to be called I think RealtimeBoard, the little two capital letters and no space.

**Barbra Gago** (00:29:52):
Yeah.

**Lenny** (00:29:53):
And with Greenhouse, you basically led the go-to market plan. And so I want to spend a little time here I guess just around rebranding. At Miro, it's a rebrand. How do you know it's time to rebrand your product and it's worth investing there?

**Barbra Gago** (00:30:06):
RealtimeBoard was interesting. I almost didn't join because it was called RealtimeBoard. Honestly, I was like, "Oh my, god. This is so literal." While I was walking the dogs with my husband, I'm like, "Am I really going to join a company called RealtimeBoard" Can this be a big company with that name?" I was really concerned about it and ultimately, I spent more time with the leaders there and I was like, "Okay, I think they'll be open to changing the name." So I think there's a maturity piece. A lot of companies are started and you just come up with a name and you don't put a lot of thought into it and then you grow to a certain level. At that time, I think we were a million users, maybe a couple of million in revenue so it was very early days. You had a name, you came up with it, you got the website and then the business grew, and at some point, can it be as big as we want it to be, as we think it can be with that name? And I think that was my biggest thing.

**Barbra Gago** (00:31:08):
With RealtimeBoard specifically, it was so literal and matter of fact and the product itself had so much more potential than the name was doing justice for. So I think at some point, it's common for companies to do a rebrand once they go into scale mode before you have too many people and before you invest too much obviously in building that brand. So I think the sooner, the better like rebrand before I even joined. Will they let me change the name was my criteria for joining. And I would say in general, the sooner, the better, but obviously after you know that you have product market fit and you have something to scale, so you don't want to invest too much in a brand that isn't going to get you as far as you want to get if you're going to obviously scale.

**Lenny** (00:31:58):
I was going to ask you what it took to convince the founders to rebrand because that's often a big challenge, but it sounds like that's part of your employee agreement. I will join if you give me the right to explore this.

**Barbra Gago** (00:32:08):
They were pretty receptive to it. The company was not US-based. I had spent my whole career in Silicon Valley a lot of time with brand and inbound and community-focused brands. So they were pretty receptive. It was not that hard to convince them, which was great. I think the scary part for them and many people was just there was some equity. They did have advocates like how would this impact the people who really loved the product right now? And so one of the things that was really important as we transitioned was that we kept as much of the essence of the initial brand. Before, the logo was like a Post-it and then RealtimeBoard. And so that Post-it, for example, that yellow became the new M that we used, and we actually proposed a hot pink M initially and the yellow M was the, okay, we don't want to go too far from the RealtimeBoard with the yellow Post-it and this was a way to nob to the early base of customers and keep something that was pretty standard and pretty core to the initial brand and name.

**Lenny** (00:33:25):
Looking back, do you think that was worth the effort and time to worry about those folks?

**Barbra Gago** (00:33:29):
Oh yeah.

**Lenny** (00:33:30):
Yeah. Okay.

**Barbra Gago** (00:33:31):
Oh, the early folk, we definitely got feedback from along the way. We did case studies throughout the process. We got feedback on logos. We got feedback on brand and designs, and there were plenty of people who were like, "Oh, I like RealtimeBoard. It's straightforward." They loved their product, but ultimately, we kept many of them informed and we really involved them in the process to the degree of not slowing us down but still getting feedback, because we did all of this in a very short period of time on top of it. And I think it was worth it because they felt really good about the outcome as well.

**Barbra Gago** (00:34:09):
And a big part of rebranding also means that you have to bring the whole company along too and make sure they feel really good about the outcome. And that was probably one of my big takeaways, is just at that time, we were already about a hundred people, so it wasn't a super small company, and everybody had thoughts and feelings and the company had been around for quite a long time before that. So it was a big change for many people.

**Lenny** (00:34:38):
Any other learnings from that experience about just going through a branding or rebranding? Maybe just focusing on rebranding. Any other learnings for future rebranding efforts?

**Barbra Gago** (00:34:46):
So rebranding is just the visual aesthetic, and I think that's important to make sure you can transition in a way that you're still nodding to the original things but you've reinvented it or transformed it in a way that makes more sense for where you're at and where you're going. If you're changing the name, it's way more complicated because everybody has to be involved, legal, all the contracts, the website, the product, all the links. We changed our URL. Everything changed. And so I think it's really important that you have to mobilize and align and have a very clear vision about the process and the steps and be very transparent about it. I think a lot of times, marketing teams just go and do their thing and come back and it's like, "Here we go."

**Barbra Gago** (00:35:34):
With the rebrand at Miro, it was very much rebrand as a product approach. It was very much a product development process with sprint teams and agile, coming back, and you had owners for different parts of things and all reporting back and it really required everybody in some way to be involved. As I mentioned, we did it in a very condensed period of time. I think we kicked off the naming process in end of October and we launched publicly at South by Southwest with a fully three dimensional booth in March. So it was very short to get a name, and then once we had the name, to do all the actual brand and then not only that but produce an entire booth and event collateral and all of that stuff. So I think mobilizing, having a really strong clear process and delegating and letting go in the marketing role, not trying to own everything. It has to be owned by everybody else because you need sales decks and it's just everything.

**Barbra Gago** (00:36:39):
I think there's also luck involved with any success and also in rebrands because a million things could go wrong. We got our domain name changed to miro.com, I think it was 48 hours before the event.

**Lenny** (00:36:54):
Oh damn.

**Barbra Gago** (00:36:54):
All the material had been printed with the new URL. We had to just make a leap of faith, super stressful, but thankfully, we had luck on our side. But ultimately, team process, clear structure, transparent for everybody, getting feedback from customers and making sure stakeholders feel like they're involved. I think ultimately, it's a really powerful way to create defensibility for a product and a brand in the market, but it's also a lot of work related to category creation.

**Lenny** (00:37:29):
I was just going to say that. It sounds like everything you do is just a hell of a lot of work. The rest [inaudible 00:37:34].

**Barbra Gago** (00:37:35):
It's fun. I love work.

**Lenny** (00:37:36):
Me too. I always joke that I work for a workaholic, which is myself.

**Barbra Gago** (00:37:40):
Yeah, I do. I know. I just love it. So I get into this stuff and I think rebranding and category creation and brand in general, I think what our goal with Miro was to create ... There's this concept of a love mark rather than a straight mark. It's like how do you build a brand? I think Airbnb has done a great job with that as well, but how do you build a brand that people really love and so committed to and invested in? And that you have to put a lot of thought into it, and it needs to be authentic for it to really work, but if it does, it's super, super powerful.

**Lenny** (00:38:22):
Yeah. I was there during the Airbnb rebrand. It took I think a year and a half for them from start to finish to get to something they were really excited about ready to launch. And there's also actually a similar story to the domain story shared with the font. I don't know how much I could share, but they didn't have the right to use the font until the last day or something. It was a close call.

**Barbra Gago** (00:38:43):
Yeah, but you have to just like, "It's going to happen." There's some blind faith.

**Lenny** (00:38:47):
Right. It helps close it. We're launching. I wanted to talk about just branding in general. You've worked on such great, big, successful brands and you've helped craft these brands, and I'm just curious what advice you have around just building a brand, a lasting brand, a global brand. What's important when you think about creating a brand for your startup?

**Barbra Gago** (00:39:06):
I think it's something that companies should think about as early as possible and have it not be an afterthought. The product and the brand are the main things that will get customers and keep them and also keep them loyal and engaged. So I think you have to have both. You can't have one or the other. You could have a great brand and if the product sucks, there's only so far a brand can go. And you also can have a great product and maybe not that thoughtful of a brand, but what I've found is that the more the brand is interchangeable with the people at the company and the company itself, the stronger it is, the more authentic it is. When you talk about Google, you also talk about its people. They're one and the same Googlers. And a lot of companies have that same approach.

**Barbra Gago** (00:39:55):
And I think with Miro, we definitely incorporate our values into the brand. Our whole mission was to help companies build the next big thing. This is what we want to do. We want to be the platform that helps companies build the next big thing. We also had to be a big thing. We need to show what big things are. And so your company values, for example, can shape how big and how deep you go with your brand, how authentic it is to the experiences that people have because ultimately, values play a big part because values are foundational to how people behave at the organization, how they work together, how they work with one another, how they work with customers, how they talk to customers.

**Barbra Gago** (00:40:40):
The best way to incorporate your brand and how people are interacting with people that you are selling to, customers or whoever, partners, is to have those values incorporated because then it's every touchpoint isn't something that you have to train people, okay, these are all the touch points and this is how the brand needs to manifest. It already will because it's part of the DNA of the company. So I think really integrating the values can help with that and also, of course, make the brand itself human and authentic and something that people really feel emotional connection to.

**Lenny** (00:41:18):
What's an example of value informing the brand or change or helping you make a different decision maybe at Miro or CultureAmp or Greenhouse to make that a little more concrete?

**Barbra Gago** (00:41:27):
Authenticity as a value. Candor as a value. Thoughtfulness as a value. If you have a value around a bias for action or something like that, these things can translate to how the brand manifests in terms of the language that's used, the colors, the objects. With Miro, for example, we had each character of the word Miro in a different shape, and each shape had different characteristics and those were tied back to different values so they each represented something different.

**Lenny** (00:42:02):
What's an example of that? What were Miro's values while we're diving into there?

**Barbra Gago** (00:42:06):
One of them was around agility. And so, one, I don't remember which letter it was. Maybe the I. It was shaped wiggly, and then we also had a visual manifestation of it so they all behaved differently. They all had their own behavior. And one of the things that was really important to us is that we were creating a visual system or a visual language so that people that were from different parts of the world, working together could understand each other without necessarily speaking the same language. And so this was a way to invoke this connection of different perspectives and different languages in a way that got all pulled together.

**Lenny** (00:42:47):
Got it. Cool. There's a lot there. The way you all visualized the values were using the name Miro. I imagine there's four values then.

**Barbra Gago** (00:42:53):
Yeah.

**Lenny** (00:42:54):
And then Agility as a value informed the product. It needs to be agile and make sure people can be flexible in how they use it.

**Barbra Gago** (00:43:01):
Definitely. How we build the product, how people around the product act, and then that shape itself was agile and moved and agiley.

**Lenny** (00:43:10):
That's awesome. I love that. Were you there for coming up with the values? People are always wondering, just how do we come up with our company values? Do you have any insights into just developing company values?

**Barbra Gago** (00:43:20):
We did iterations of it while I was there. They already had a stake in the ground. What I have done in the past with values is we just did an exercise with my leadership team, for example, where we did a workshop format. We actually used Miro where everybody just brain dumped their ideas around values, and then it was, okay, from there, let's group them into themes. And then from there, let's vote on the most important things. And then from there, how do we start to articulate and define these things? Ultimately, coming up with the definitions is not really something you can do as a group because it's just not very productive. It's better if somebody who knows how to write well can come up with the first stab of the sentences, if it's operating principles, if it's values, and then get feedback on it. But you can get everybody's input and make the process pretty structured by doing something like that where it's like brain dump, group, vote, and then you have your short list of things that you can then work to define.

**Lenny** (00:44:23):
Awesome. Maybe one last question around brand. People that aren't in, say, marketing hear brand and it's, okay, it's this fuzzy thing that I feel about our company. When you think about creating a brand, what are the bullet point things that you come up with? There's a logo. There's color palette. Can you just talk through, what is a brand when you're creating a brand and building a brand, what are the elements of it?

**Barbra Gago** (00:44:47):
So all of those things that you mentioned. I would say the logo, the colors, the fonts, all the general aesthetic. Do you have photography? Do you use illustrations? Is it all illustrations, all graphics, whatever? You decide those things. You need to understand what the voice is of the brand, how the brand sounds when you write things, when you market it, how people talk. All of that stuff is part of the brand. If you want to build a brand that's really scalable, you think about it more as a system like a brand system. So this is creating things that ... With Miro, for example, we had the letters and we had the colors and we had these concepts of agility. I don't remember all of them off the top of my head, but all of these different concepts that then were represented by different shapes or different colors that could be used in various forms. So it's really like how does it become an extension of all of the different things that you're going to be doing visually or when you talk to customers or how you present the product, etc.?

**Lenny** (00:45:50):
And all of that combines to this feeling you get eventually from the brand. All these things create that fuzzy feeling.

**Barbra Gago** (00:45:56):
Yes.

**Lenny** (00:45:57):
Yeah. It's interesting you don't remember all the values at Miro. With Airbnb, I'm just like, I will never forget the Airbnb values. They've been so drilled into our heads.

**Barbra Gago** (00:46:05):
Yeah, it's because they were too long. It was something that we were constantly working on because they were too long and there were too many things in them to remember. That was the problem.

**Lenny** (00:46:17):
That's a great learning there. Make them simple, but also don't make them generic.

**Barbra Gago** (00:46:21):
Yeah, it can't be generic, but it also can't be too much that nobody knows what they are. They need to be simple and straightforward and easy to remember.

**Lenny** (00:46:32):
And potentially, illustrated with your company name. That's a really cool idea.

**Barbra Gago** (00:46:36):
Exactly. Yeah.

**Lenny** (00:46:37):
Last topic I want to spend a little time on is something that I know you're really passionate about, which is this idea of creating opinionated software that has clear opinions about how you should be using it and how you should be doing your work. And so maybe as a first question, just what is opinionated software? What's important about it?

**Barbra Gago** (00:46:54):
Opinionated software is basically software platforms that essentially have either best practices or maybe some rules integrated into the system. You have systems that you can customize any which way and however you want and then you have other systems that enforce a certain way of behaving or doing work, as you said. And so I think probably a pretty well known example for your audience especially is Atlassian really building tools for agile workflows and agile teams.

**Barbra Gago** (00:47:27):
And Greenhouse is another example from a recruiting perspective in terms of what we called structured recruiting. There was a very specific way to create a pipeline, build an interview kit, and all of that was important because it made recruiting better and more transparent and obviously less bias and all of those things. So it's principled, I would say. It's anchored in some values. And because of those values, there will be certain rules that are built in that you can't really work around.

**Lenny** (00:47:58):
Do you have any advice for when it makes sense to be very opinionated about how you make people use your product and do the thing they're trying to do versus just optimize for flexibility?

**Barbra Gago** (00:48:11):
I think Atlassian built around a process that was already happening and growing momentum and it was like, okay, let's build a solution to enable companies to do this with technology. So there was already a process that didn't have a technology integrated, and then with Greenhouse it was like, there's a better way to do it and this is how it should be done. So I think there's two different approaches. Either find a process that just doesn't have technology that is a best practice or growing best practice. I think the same thing happened in DevOps with many different tools. And then Greenhouse, which is more like, what are companies missing? How can they do it better? How can we train them and teach them a better way? And then by the way, our software helps you do that.

**Lenny** (00:48:56):
With the product and company you're building now, are you looking to make it very opinionated and here's how you should be doing performance reviews or how are you thinking about it?

**Barbra Gago** (00:49:03):
Yes, we are. It is opinionated, and it's opinionated because the current way that performance reviews happen are full of bias and there's a lot of problems with it. It's like the best thing that companies can do and therefore, they continue to do it, but that just perpetuates a lot of issues. The reason that companies have to go and look at compensation data and fix pay gaps is because they have systemic problems with how people are promoted and progressed in the organization. So if they're recruited in a certain way, they may or may not be developed and then they're evaluated on their performance, which ultimately results in compensation and what people are paid, and that as we know, there's plenty of problems.

**Barbra Gago** (00:49:47):
So companies are fixing this compensation issue by updating the comp every year, but that doesn't fix the systemic problem. And so yes, we have opinions about how to fix the problem and therefore, our building a system that when it comes to performance evaluation, employee progression, we require companies to be more transparent about the levels at the company, the expectations for different levels and competencies, and we create accountability both on the employee and the manager side, but it's also the right thing to do. Employees should feel that they're evaluated fairly, and without a system enforcing some of these things, there's too much subjectivity in the process to make it good, unless you really do a lot of work, which most companies don't do to create the right system. You don't have to use a platform to do it, but if you don't do the work anyway, you won't have the outcome that you want, which is people feeling good about their career and paid fairly.

**Lenny** (00:50:59):
Yeah. I found performance reviews to be one of maybe the most powerful tool as a manager to change the way people operate, help them improve, make them fulfilled and happy with where things are going. It feels like that's the core of management, is the performance review cycle and giving people feedback on how they're doing it and then continuing to come back to here's where you're underperforming, here's what it'll take to get to the next level. So I'm excited about what you're working on.

**Barbra Gago** (00:51:22):
Thank you.

**Lenny** (00:51:23):
We've reached our very exciting lightning round where I'm going to ask you five rapid fire questions and you just tell me what comes to mind. We'll go through it pretty fast. Does that sound good?

**Barbra Gago** (00:51:34):
Yes.

**Lenny** (00:51:34):
Okay. Awesome. First question, what are two or three books that you recommend most to other people?

**Barbra Gago** (00:51:41):
Definitely Radical Candor. We give this out to customers. It's really good for management and best practices around giving feedback. I love the Art of War just as strategic thinking. And then not work related, a book called Kafka on the Shore. It's one of my favorite Murakami books that I highly recommend.

**Lenny** (00:52:00):
What is that one again?

**Barbra Gago** (00:52:01):
Kafka on the Shore.

**Lenny** (00:52:03):
Kafka on the Shore. Wow, cool. I haven't heard of that.

**Barbra Gago** (00:52:05):
Yeah.

**Lenny** (00:52:06):
Awesome. Going to use these in the show notes. What's a favorite other podcast than the one you're currently on?

**Barbra Gago** (00:52:13):
I love Cautionary Tales. I don't know if you know this one, but it's a great podcast that basically identifies and tells stories about the mental mindsets that we're in and the biases that we have and then historic events that have happened and just crazy things that have resulted from things that we do as humans because we're biased.

**Lenny** (00:52:36):
Irrational humans.

**Barbra Gago** (00:52:37):
It's really good. Yeah.

**Lenny** (00:52:38):
What's a favorite recent movie or a TV show that you watched?

**Barbra Gago** (00:52:42):
I watched Sandman. I don't know if you've heard of this.

**Lenny** (00:52:46):
I've heard of it. I haven't seen it.

**Barbra Gago** (00:52:49):
It's based off of an eight-part graphic novel series by Neil Gaiman. It's really good. The TV version of it isn't exactly about the books, but it's about the characters, and I feel like the way that they portrayed the characters was really interesting and super diverse. It's a great show.

**Lenny** (00:53:09):
Awesome. That's more plus one for that show. What's a favorite interview question that you like to ask when you're interviewing people?

**Barbra Gago** (00:53:17):
Everybody hates it, but I like asking what someone's top 10 accomplishments are. They hate it because it's like, "Oh, God. Ugh." But it's really interesting to understand the level of quantitative versus qualitative in their accomplishments, what they value. And also if it's a, "Oh, I ran a hundred miles or I have a great family," whatever it is, it's really interesting to get to know somebody and also what they value.

**Lenny** (00:53:46):
Who else in the industry do you respect most as a thought leader or just influence on your career life?

**Barbra Gago** (00:53:52):
Early days, I really appreciated Nancy Duarte. She is based in the Bay Area. She has an agency called Duarte Agency. She does a lot around storytelling and visual communication. She's been really great for me just in my career as a mentor. I've worked with her a couple of times, but also just following all the work that she does. She's amazing.

**Lenny** (00:54:13):
Awesome. I remember learning about her when Al Gore gave his TED Talk and her whole agency was a-

**Barbra Gago** (00:54:17):
Yes. She's done an incredible thing with her agency because they started as making presentations more visually appealing, and then it migrated to storytelling, and then it's evolved to change management and how to use story for driving change. And she's also evolved the agency so much over the years as well. She's done a lot of impressive work.

**Lenny** (00:54:42):
Barbra, thank you so much for being here. This was amazing. Two last questions. Where can folks find you online if they want to reach out and learn more, and how can listeners be useful to you?

**Barbra Gago** (00:54:52):
LinkedIn is probably the easiest place to find me /BarbraGago. And for me, we're building a product in employee progression, so anybody who wants to share their stories or feedback, our insights around their experiences there or if they're interested in getting product feedback, we're really interested in actual user feedback, even though we're selling to HR teams.

**Lenny** (00:55:16):
And what's the URL?

**Barbra Gago** (00:55:18):
Pando.com.

**Lenny** (00:55:19):
Awesome. Barbra, thank you for being here.

**Barbra Gago** (00:55:20):
Thank you so much, Lenny.

**Lenny** (00:55:24):
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.

---

## [8/20] Building Substack | Sachin Monga (Substack, Facebook)

**Sachin Monga** (00:00:00):
I really think that we're just starting into this golden era of what it might mean to be a writer on the internet. The economic model for supporting great writing on the internet has been generally pretty terrible for the entirety of the internet's history. In the early days of Substack, there's a couple of these glimmers of hope where you'd have people like Matt Taibbi or Bill Bishop, some of the early writers on Substack that were really well established writers who were clearly just being undervalued and now could come to Substack and see their true value.

**Sachin Monga** (00:00:33):
And that was awesome. That was really cool to see. But in the last year or so, even in the last few months, I think there's been so many really interesting success stories now from writers who might not even consider themselves writers. People who are able to make a living, maybe even make a fortune just doing great work and not needing to have millions and millions of viewers or play the attention games of other networks, but just do really high quality work and have a relatively small number of people value it highly enough to pay for it.

**Lenny** (00:01:07):
Welcome to Lenny's Podcast. I'm Lenny, and my goal here is to help you get better at the craft of building and growing products. Today, my guest is Sachin Monga, who is currently the head of product at Substack. Before Substack, he had a startup called Cocoon that he sold to Substack. And before that, he spent over seven years at Facebook working on the video and camera products, building out the developer platform, and leading the ads growth team. In our conversation, we dig into all things Substack, what it's like to build product at Substack, how different it is to work at a startup versus a big company like Facebook, the future of the Substack product.

**Lenny** (00:01:42):
**Sachin Monga** (00:04:36):
Thanks for having me.

**Lenny** (00:04:37):
I'm actually really excited to have you on. I've told you this before, I've told the founders before, Substack has changed my life in so many ways. There's no way that I would be doing what I'm doing now if not for Substack and just like the magical combination of features that you all built. I'm also just really curious about how you all build the platform, where it's going, how it all works behind the scenes. Again, thank you for being here.

**Sachin Monga** (00:05:01):
I'm so happy to be here, and that's so great to hear.

**Lenny** (00:05:03):
Just to set a little context for folks, can you just talk about how you got to Substack? You're currently head of product at Substack. What was that journey to Substack?

**Sachin Monga** (00:05:12):
I joined Substack around a year ago now exactly through an acquisition. I'd started a company called Cocoon about three years prior to that with my good friend Alex Cornell. Cocoon is not like Substack. It was essentially a little photo sharing app for close friends and family, but there is a common thread which led us to Substack, which was prior to starting Cocoon, Alex and I had both worked at Facebook for a number of years and had worked on effectively the same problem of helping people share more with their friends and family and had all these ideas for what an idealized experience might look like.We just kept running into the wall that you run into when ultimately advertising is the business model that is powering this whole thing, and what that means is you need to accumulate a lot of time spent and attention and convert that into basically sellable eyeballs. But it's not that hard to imagine what a better solution would be. It's just that ads as the business model made it really hard to pull that off. Cocoon was in a lot of ways like a journey to explore what that might look like for this one particular use case of just helping you feel close to a handful of people.

**Sachin Monga** (00:06:14):
We always looked up to Substack as a really good example of basically that same principle, which is if you imagine rewiring the internet around paid subscriptions, direct subscriptions between, in Substack's case, readers and writers, what could that unlock and could it unlock a clearly better user experience? We looked at Substack as a real inspiration and an example of that really working out and got to know the founders pretty well and had a few conversations and realized that even though the blogging software and the photo sharing app are pretty different, our underlying motivations were really consistent.

**Sachin Monga** (00:06:46):
It was a bit of a match made in heaven and the whole team joined Substack a year ago. I've been privileged enough to get to lead the product and design teams, and it's been a blast so far.

**Lenny** (00:06:57):
Before your startup, you're at Facebook for a number of years, is that right?

**Sachin Monga** (00:07:00):
Yes. I started in 2011 there on the growth team and had the chance to work on a bunch of different teams there, growth, platform, ads, and then eventually the team we called Sharing, which was helping people share more in the main Facebook app.

**Lenny** (00:07:12):
Sweet. I want to spend a little time on that, but coming back to Substack, I'm curious just how the product team runs. How many PMs do y'all have? How is it structured? How are you thinking it'll evolve as you scale? What can you share there?

**Sachin Monga** (00:07:25):
Sure. Maybe to start from when I started at Substack, we had zero PMs. We had a handful of designers. We had maybe 15 or so engineers. I think we're coming to the close of this kind of one-time inflection point of becoming a product driven company and having a product process and structure and PMs and full stack product teams. When I started at Substack, there was really not much of this. We're still pretty early, but we have something going now.

**Sachin Monga** (00:07:51):
We have four product managers in addition to myself, and we have three essentially kind of full stack product teams now that have a PM and an engineering manager, a data person or a designer, engineers and things are starting to roll. We're finally emerging from this transition phase and it's been super fun.

**Lenny** (00:08:10):
What are these three teams?

**Sachin Monga** (00:08:11):
The three teams are: we have a writer team that serves writers, we have a reader team that serves readers, and we have a growth team that does growthy things. I should mention, we have a fourth engineering team that's like the systems team that doesn't have a product manager on it, but is keeping the lights on and helping us scale.

**Lenny** (00:08:28):
Awesome. That makes sense. You currently align it around the type of user plus the platform stuff. Do you have a sense of where this might evolve over the next few years just structure wise? Do you think it'll stick to that? Do you have a plan of how this might radically shift as you grow?

**Sachin Monga** (00:08:43):
Yeah. I'm actually kind of shocked that it's lasted this long and stayed consistent. I remember at Facebook, we would change our team structure what felt like every three months or six months and just have a reorg every once in a while. Part of why I think it's remained pretty consistent is exactly what you mentioned, which is the teams aren't oriented around product surfaces. We don't have a team that's like the app team or a team that's like the dashboard team or the podcasting team. We have teams that are oriented around customers and solving bit of a timeless customer problem. We'll never be done serving writers.

**Sachin Monga** (00:09:16):
We just started honestly having a concerted focus on serving readers. Growth is never a problem that you check the box off on. I hope that we are able to maintain this general structure. I think as Substack grows and expands, I'm sure we'll have more than three teams. This is where we're at right now, but I really like the focus on a customer and a timeless mission really rather than orienting around what might be a bit more of an ephemeral surface area or product de jour.

**Lenny** (00:09:46):
Awesome. Shout out to the writer team. Thanks for building all the awesome stuff that I get to use. It makes sense why you are more recently investing in the reader team because Substack has this magical advantage platforms have where your supply drives all your demand. I go out and promote my newsletter, people sign up for Substack. It makes sense why there's not initially a huge focus on the demand growth, but makes sense to get there. It sounds like your app is awesome.

**Lenny** (00:10:11):
One thing I wanted to touch on is you're kind of in this interesting position as a head of product at a small-ish company with a founder who's very product sense strong, and that's a classic challenge for a product leader to be in, where it's a smallish company, either a first PM or even a head of product, where the founder's very opinionated about the product. I'm curious what you've learned about how to work in that environment as a PM.

**Sachin Monga** (00:10:36):
That's a great question. I don't know if I have the recipe for this, but I can just maybe share a few of the things that come to mind. I think the first thing was really treating my role in the beginning more as a facilitator than a decision maker when it comes to product. I think the team was also small enough that everyone in theory could have a good sense of what everyone else was up to. A specific problem we had I think when I joined was that we were just getting to the point where we wouldn't have one weekly meeting where Chris could be in the room, Chris is the CEO of Substack and the person you're mentioning, and decide what we're doing in the next two weeks.

**Sachin Monga** (00:11:13):
We were just emerging from that phase. We had this problem which was all of a sudden, Chris didn't really know what all the teams were doing and the teams didn't really know what Chris had in mind for what they should do and what the vision was. We were hiring really quickly and hiring people who might not have all of the context of being in the room with him for years and being in all of the all-hands meetings. When I first joined, I felt like my main role was actually just solving that. And if nothing else, if Chris could have a really good sense of what all the teams are doing and if the teams knew where he was coming from and could start to get better at modeling him and his vision, that would be a win.

**Sachin Monga** (00:11:43):
For the first couple months I'd say, that was all I tried to do. I think now Chris and I have some reps under our belt and the teams have some reps under their belts too, and that trust just starts to form. We start the week, Chris and I, we sit down for an hour. We go through what do we feel like are the big problems to focus on this week, what are the things we're worried about. We sit down at the end of the week and we check in again. There's just a lot of open communication. I think that helps a lot.

**Lenny** (00:12:07):
Got it. It sounds like the core of this is building trust, which makes sense. The way that you've been building trust, one is just do it again and again and then Chris starts to trust, "Okay, Sachin's going to do the things that I think are probably the right things." And then you said you have this weekly meeting. Is there anything else that either tactically you find as a really important component of this relationship or any other lessons you've learned about just how to keep this relationship healthy and constructive?

**Sachin Monga** (00:12:34):
One thing that I think about a little bit because like any startup, there's going to be times that are really difficult, times that are really fun. Substack is certainly going through this really transformative time, but we're really evolving in a lot of ways from a tool into a network. We're in the thick of seeing this vision through in a lot of ways Chris has had in his mind for five years. We did a thing at an all-hands a little while ago where Substack went through Y Combinator I think it was maybe now six years ago and we watched the 60 second demo they pitched from 2017.

**Sachin Monga** (00:13:04):
What was so cool about that was we're actually doing all those things now that Chris got up on stage and talked about like, "One day in the future, Substack is going to get into podcasting, and we're going to have this network effect that helps writers grow by virtue of there being other writers in the platform." There's all these things that we kind of couldn't do until we earned our place at the table and the right to be able to do those things that we're doing now. To go back to your question, I think a thing that I really try to be mindful of right now is, how do I catch up?

**Sachin Monga** (00:13:35):
Chris has been thinking about this problem for five times as long as I have. If I can get a good sense of where his vision starts from and catch up those few years and help the teams do the same, that'll go a long way. Because at the same time, everyone now is coming at it from a different perspective. We've a lot more data and evidence. It's really good to have people on the team that have come from other companies and comply that perspective. It's a lot of, again, facilitation and I view that as a big part of my role.

**Lenny** (00:14:01):
Awesome. I'm curious, what are the biggest challenges with being in the position you're in? Are there any examples of a man that sucked? Or if you want to go in a different direction, is there a certain type of person that just isn't a good fit for this kind of role, had a product at a smallish company with a very product minded founder?

**Sachin Monga** (00:14:19):
Oh, let's start with the first one. I think the biggest challenge with this role/company phase, like I mentioned, we're going through this one-time transition from not really having a product function or a product process to having one, is almost by definition any time you figure out how to do a thing, you'll now reach this next phase of growth and it'll be obsolete. Something that I've repeated a bunch of the teams is I'm never too worried if we have the perfect planning process or the perfect execution cadence or the perfect communication process, whatever our process is, we're never going to have a perfect one.

**Sachin Monga** (00:14:52):
And even if we did, it would soon be obsolete because we did a really good job and now we've grown 2X or something and we have more people and the process needs to change. The main thing I care about is are we just getting better every week, every month, certainly every year. I think that's easier said than done. It sounds good in theory, but then when you're in the thick of it. you're constantly basically feeling like you don't know how to do the thing. Because as soon as you figure it out, it's obsolete. It's just really hard. I think that's true of basically just startups in general, high growth companies. Doing the thing well means that you're not going to know what you're doing.

**Sachin Monga** (00:15:24):
Maybe that leads into my answer to the second question, which is that's not really for everyone. I think there's almost like a personality type that has to be okay with being humbled all the time and feeling like you don't know what you're doing. I think you could be an amazing product manager at a company that is a bit more stable and consistent and get really good at what you're doing and someone who's going to be really good at a company that is on a bit of this trajectory, for folks who aren't watching the video, making a motion with my hand, that's not growing too fast, it's kind of a different job. The rate of change is a huge factor.

**Lenny** (00:16:03):
The point you made about how things are going to keep changing as you grow is such an important point that I don't feel like comes up as much as I thought would come up on this podcast. People are always asking me for advice. How do I structure my product team? How do I prioritize? How do I do planning? The main thing I've learned is no matter what you end up with, it's going to change in three to six months anyway because you'll learn more. The advice is just do the best thing you can think of right now. Don't assume this will last anyway, and that's good enough. There's never the perfect way to do it. It's always the best way you could do it at this moment, and then you learn how to evolve it.

**Sachin Monga** (00:16:35):
100% agree.

**Lenny** (00:16:37):
You worked at Facebook for I think it was seven years. I'm curious what were you able to take from that experience about how Facebook, in a massive company like that, builds product to a smaller company like Substack. What translates well and then what just doesn't?

**Sachin Monga** (00:16:51):
Over time, I'm finding that less translates than I thought. I don't know how much of that has to do with Facebook specifically though. I'll maybe mention one thing. Working on the core Facebook app, which was what I was working on for the bulk of my time there, Facebook may be the most extreme example of trying to solve so many different problems for so many different people in one tiny rectangle basically, that a big part of the product manager's job in a situation like that is going to be managing trade-offs. It's a super fascinating intellectual problem.

**Sachin Monga** (00:17:22):
I think going back to the previous point, a lot of people really thrive in that kind of environment, where if we do this thing really well, it is going to directly trade-off against doing this other thing. It's not even a sequencing thing. When you think about prioritization, sometimes you think, we will do this, and then we'll do this, and then we'll do this. In Facebook's case, sometimes it's, "Oh, if we do this, we just can't do this. It's going to be bad for this other thing. If we put a watch tab at the bottom, will that mean that people don't get a marketplace tab? What does that mean for this whole org and what the product is?" I think when it comes to something like prioritization, it's a very different ballgame.

**Sachin Monga** (00:17:56):
There's certainly some things that are consistent. You generally want to prioritize things that are going to be high impact, low effort. These types of product management frameworks, I think a lot of it can hold constant. But when you really get into the object level like what does your day look like, I think being a PM at a high growth... I can't generalize this, but the job at Substack right now, it looks quite different than what I recognized as my job from Facebook circa 2018. I think it's maybe even gotten more the case that the PM's job in a situation like that will be navigating these types of internal trade-offs. I think on something like prioritization, very different.

**Lenny** (00:18:31):
Just to double click on that a little bit, the main difference you're saying is that at a Facebook, it's not like whether we do a thing, it's just like what comes first, second, third. At a Substack, it's like we probably won't get to this for a year if we don't prioritize it now. Is that how you think about it, just like the time scale on your trade-offs?

**Sachin Monga** (00:18:46):
No. I think actually at Facebook, it's not necessarily whether we do a thing. It's not like we do this now or we do this later. It's doing this thing might mean we can't do this other thing at all, or it'll mean that instead of that chart being steady until we make the number go up, it might go down. By doing A, it might mean B is harder to do forever. Whereas at a startup, a lot of it is time. Time is the main variable. We can do this now and that means that we can't do this other thing until later. There's also an element of sequencing that matters I think a lot at a company like Substack that is in this formative stage of becoming an entirely new thing in a lot of ways.

**Sachin Monga** (00:19:21):
Substack started off like a single player tool for writers. It was like software for writers. If you describe Substack now as simply a newsletter tool, that would be reductive. It's really now much more of this ecosystem that's evolving in all sorts of interesting ways. There is a bit of an order of operations at play here where doing something right now might unlock our ability to do something later. That matters a lot in a situation like we're in at Substack.

**Lenny** (00:19:49):
Got it. Essentially there's a lot more one-way doors at a larger company. Here, you can make decisions more quickly partly, but also you can go back and there's not all these second order effects of decision you're making.

**Sachin Monga** (00:20:00):
I think that's right, or at least there are different types of second order effects.

**Lenny** (00:20:03):
Got it. I know at Substack writers are like the beacon and the vision of making writers successful, helping people make a living writing. I imagine writers are the North Star or helping writers be successful, but is there anything where you can share about how you prioritize things that you work on within Substack? How do you think about the North Star?

**Sachin Monga** (00:20:20):
Going back to your question about Chris too, I think Chris and Hamish and Jay, the founders I think really start from a place of principle in a lot of ways. Why are we even doing this thing? It's not just to help writers make money. It's not just to unlock these cool things. It starts with an opinion for how the internet should work, where people should be in control over their destiny to a much greater extent than has ever really been the case over at least the last 10, 15 years, where all of a sudden, everyone just started spending all of their time in a handful of these public squares that were powered by ads.

**Sachin Monga** (00:20:57):
When you think about what that means for Substack right now, that that means writers are in control over being able to deliver their best work on their terms to their audience, make money directly from their subscribers, and also that readers should be in control over their experience. When you show up to Substack.com, that experience should be something that you have a much greater degree of agency over or if you download the app than if you maybe opened up TikTok or something.

**Sachin Monga** (00:21:20):
I think where that leads you down from a prioritization standpoint is often starting from, okay, if we could do something in a bunch of different ways, is there a way that provides more control to the writer or more control over the experience that the reader has to them? Is there a way that provides much less control? All things equal, do the one that holds constant this principle of control. We could talk about a few other examples like this, but I think from a prioritization standpoint and from a strategic standpoint, Substack is a pretty principled company, and I think it's been really fun and interesting to get to work in an environment like this and also see how it actually can work.

**Sachin Monga** (00:21:57):
You are excited about recommendations, the recommendations feature, and we can talk about that in more detail. I think that's a good example where there's certainly a way to do that where writers have the max amount of control. We picked that way even if it might seem harder to pull off. And then that feedback loop of, "Oh, that actually worked," is really awesome to get to experience.

**Lenny** (00:22:17):
Yes, I definitely wanted to talk about this recommendation feature. I feel like it's maybe the most underappreciated radical shift in Substack and just platforms in general. I think this is going to go down as one of the most legendary impactful features of any platform or marketplace. I'm just putting this out there. It's such a huge deal and I don't think people appreciate this. Just to quickly summarize what this is, essentially you allowed writers like me to recommend other newsletters that I specifically pick. I pick 10 newsletters that I think are awesome. Once someone subscribes to my newsletter, they see these 10 as, "Hey, you should check these out. I think these are awesome."

**Lenny** (00:22:55):
It's very curated. There's no algorithm involved, which to your point is Substack's I think vision and mission is just avoid algorithms as much as possible. The reason I think this is crazy and amazing is at this point, 70% of my growth is coming from this one feature. There's something like 500 other newsletters recommending me. As soon as the feature launched and you look at my growth chart, it's just a hockey stick starting that day. I don't think people appreciate this enough, and I'm really excited to just chat about how this feature came to be.

**Lenny** (00:23:26):
Coming back to a point we talked about earlier of Chris having a very strong opinion about how to build product, something I heard through a birdie is that Chris was not excited about this feature when it was proposed and it took a bit of pushing to get it out. Maybe we start there. How did this come to be?

**Sachin Monga** (00:23:39):
Sure. The way it came to be was that we noticed this organic behavior emerging, which was that a lot of readers of Substacks were starting to discover Substacks, but the way that was happening was typically through the lens of that original writer. This could happen in a bunch of different ways, right? I think you've used the guest post feature to have guests write post on your newsletter. Obviously that is a really good way for your readers to go and discover some of these other writers in a way that you're curating. There's some less obvious ways that this happens too.

**Sachin Monga** (00:24:10):
If you have comments on, which I think you do, if I scroll down and click on the profile of someone who's commenting on your post, it'll show me the other Substack that person reads too. Again, this is a very personalized and very writer centric way of doing discovery. At the same time, we talked about the supply and demand side of the marketplace. The supply side of Substack has just grown over time consistently to the point where now there's a huge amount of amazing writers on the platform and a huge number of collective readers on the platform too that we knew that this sort of like cross-pollination, this discovery loop could be a really powerful thing.

**Sachin Monga** (00:24:47):
If you'd start from the first principles, you're like, "All right, how do we help readers discover more things?' The most obvious way to do this would be something like, "Here are some Substacks you might. Based on what we know about your reading habits, here's like a few that Substack is just going to recommend you." This is the thing that worked really well. At Facebook in particular, I think when I joined in 2011, it was definitely still during the era... I think Facebook maybe had just over 500 million users and was on this path to a billion and beyond.

**Sachin Monga** (00:25:13):
This thing that we called PYMK, which was People You May Know, this little unit that would show up in the newsfeed and it would just tell you that eight other people that you obviously know because you have million mutual friends. That kind of thing drove a very non-trivial amount of Facebook growth in the early days. Of course, lots of other products have done things like this. We could have done something like that.

**Sachin Monga** (00:25:32):
But then going back to that principle of like, okay, well, if we were to do that, let's say we were to insert it at the bottom of our post or in an email or something, it's clearly a thing now where the writer who owns that space is not really in control over what the experiences that they're offering their readers. The reader who signed up for Lenny is now seeing these other things that have nothing to do with Lenny. Does that break this control principle, like putting writers in charge, putting readers in charge? Okay, so then back to the drawing board, what would be the most obvious maximal way to just put writers in control? What is the simplest version of this?

**Sachin Monga** (00:26:05):
What if we just ask writers, who do you recommend? What if we just put that in the subscribe flow and just made it as simple as possible? I think Chris' reaction to that originally when that idea came up was that's probably just going to be really hard to pull off. There's a lot more things that have to be true. You need writers to opt in. You need to pick good people. You need to find a way to surface those recommendations to the readers in a way that's going to generate a good amount of surface area. I think it was a bit of skepticism that something like that could work, but we tried it and it took off really quickly.

**Sachin Monga** (00:26:39):
There was this virality at play now where when you recommend a bunch of people, those people will get an email that say, "Hey, Lenny's recommending you and here's all the readers that he's sending you." It created this goodwill viral loop, which was really interesting to see play out. I think there was a bunch of interesting lessons in there. We could stick into anything that seems interesting, but I think Chris' skepticism was not, should we do cross-pollination discovery? Clearly this is something that's working, but is this kind of thing going to work given how many steps are required for it to be true that this becomes really impactful? It turned out that it took off way faster than I think we had imagined.

**Lenny** (00:27:13):
Is there any stats you can share about just the impact it's having, what it's done to Substack?

**Sachin Monga** (00:27:17):
Yeah, sure. Recommendations specifically now have driven in the millions of new subscriptions for writers across the board, across I think like tens of thousands of unique writers that have received subscriptions from the recommendations feature. Of course, recommendations in particular are still just one component in this broader basket of network driven discovery.

**Sachin Monga** (00:27:39):
I think we recently shared the stat, more than one in three new subscriptions across Substack are coming from the Substack network and around one in 10 paid subscriptions now too. But these numbers are just, as you can imagine, growing up and to the right, getting stronger every day, and I think we'll have some more interesting stats to share on that soon.

**Lenny** (00:27:58):
Awesome. One thing I wanted to acknowledge, I think some people worry about this feature that it drives lower intent users. I find that not to be true. They're definitely lower intent, but it's not meaningfully and significantly. The fact that 70% of my user growth comes from this feature and my open rates have only come down a little bit, it says a lot about it. It's like useful really in tenfold people as much as it can be from someone that hasn't actually been planning to subscribe and just recently found out about it. It's really impressive how high intent they are all things considered.

**Sachin Monga** (00:28:31):
You bring up a point too that leads into some of the next things we're thinking about here, which is that right now most of the subscriptions that come from recommendations are coming from one particular flow in the product, which is when someone subscribes to someone else on Substack, they will then see a recommendation for Lenny. It's being serviced to people at a moment where not only are they just hearing about you for the first time, but they might just be hearing about the recommending writer for the first time too. They are new subscribers. They don't have this long standing trusted relationship built up yet.

**Sachin Monga** (00:29:04):
Of course, you have people now who've been subscribing to you for years and who trust you greatly and would probably take your recommendation very seriously, but the people that you're recommending are only getting these subscribers at the first moment that someone finds out about Lenny in many cases. A big part of the next step of this product now is thinking about recommendations less as a step of the flow and more like a really interesting social graph that is being built of goodwill and of influence. You now recommend a bunch of other writers. There's much more that could be done in the network than just show some of those writers in the subscribe flow of lennysnewsletter.com.

**Sachin Monga** (00:29:43):
There's a lot more we could do there. I'm curious if you have any ideas, but we've got a bunch of ideas that we're cooking up that I think will not only drive more subscriptions, but also probably higher intent ones as well, because these are going to be people that might already have been reading you for years who never right now would know who you're recommending.

**Lenny** (00:29:58):
No great ideas to share. I do find since it's only free subscribers, I have to do more work to upsell them to try paid. On the other hand, having a huge pool of interested people that aren't ready to convert yet is only beneficial. When I send a free post and mention, "Hey, I have a paid subscription. You can get more," it works really well.

**Lenny** (00:30:17):
**Sachin Monga** (00:32:12):
The Robin Hood of Substack.

**Lenny** (00:32:14):
Yeah, now I'm going to get all these DMs to recommend people. If I'm unable to, I'm sorry. You talked about how Chris was worried that this would not work. That's interesting. His point of there's so many steps that have to happen for this to be adopted is such a good one. In my experience, getting users to do anything is so hard. To get them to click some buttons and fill things out, that rarely works. It's cool that it really did work.

**Lenny** (00:32:38):
I think it was part of the early beta, and I found that it was a really thoughtful approach to how it was all rolled out where there was a small group of users and writers that tried it out, see how went, see what the impact was, see if there was any negative impact. Is there anything you could share by just the way this was rolled out that you've learned about how to do this sort of thing?

**Sachin Monga** (00:32:56):
I mentioned that we're going through this one-time transition of figuring out how to become a product driven company and how to ship products faster, better, et cetera. One of the principles I guess in this playbook that we're trying to write is we call it build with writers, build with readers. In some ways now that I think about it, it's almost like a sub principle of the put readers in charge, put writers in charge. How do you build product responsibly if you care deeply about that? One way to do it would be to almost as a strong default, anytime we're going to make a fundamental change to how Substack works, do it in a way where we bring writers along.

**Sachin Monga** (00:33:32):
This is still an optional thing. This isn't changing how Substack works for everyone, but this is we think a potentially profound enough thing that the way we did this was not just roll it out for everyone, put a little dialogue in the dashboard that says, "Hey, everyone, now go do this thing," it was like, okay, why don't we call up 10 writers who we think might be interested in this." It's not that hard to just mock up what this could look like, get some feedback. This is the kind of thing that I think a lot of product teams would do. But then maybe a lot of product teams would be like, "Okay, we got good feedback. Let's just build the thing, ship the thing."

**Sachin Monga** (00:33:59):
Instead, we just ran a little pilot. You and a few other writers were gracious enough to lend your time and talk us through how you would see this working and what you would want. We actually have now we've set up something called the Product Lab, which I'm really excited about. I think you're a part of it. I hope we asked you.

**Lenny** (00:34:16):
I'm curious to see where this all goes.

**Sachin Monga** (00:34:19):
This is just an invite only little group of a hundred or so writers that we know are interested in being on the bleeding edge of what Substack is becoming. We're investing a lot in just tools to help writers grow. Now we've got this little lab where we can take a feature recommendations to writers and get quick feedback and ensure that we're never just rolling something out to everyone without going through this step first. It's just been super helpful to have a bit of this infrastructure in place. Often the thing that we end up shipping on day one tends to be pretty different from what we had in mind before we went through this process.

**Lenny** (00:34:54):
I've been through a bunch of those experiences and it always goes super well. I've been through a few features that just didn't go anywhere and then they, "Nope, we're going to move on and not try this thing." Something else that always comes to mind with Substack is it's often in the news. Substack is a very popular topic amongst reporters.

**Sachin Monga** (00:35:10):
Writers like to talk about writers.

**Lenny** (00:35:11):
That's right, especially a platform that might disrupt them someday or friends have gone on and they're maybe jealous about. I'm curious, as a product leader, how you deal with bad press, angry attention, things like that, just keeping people focused, keeping people motivated. Do you discuss stuff? How do you approach stuff that comes out of like, "Oh man," and keep people excited?

**Sachin Monga** (00:35:33):
The whole thing here is just parsing out the signal from the noise. There's very little chatter in the blogosphere media sphere that would actually impact our day-to-day when I think about it. It's not zero, right? Sometimes there'll be something that ends up blowing up or that people are talking about that we should really take seriously and see how that might impact our strategy. But I'd say 90% of the chatter about Substack is going to probably ultimately just be a distraction to our product team at the end of the day that should just be focused on executing on the vision.

**Sachin Monga** (00:36:02):
Maybe my skin got thickened from working at Facebook during a bunch of years that... Actually when I started at Facebook, generally things were quite rosy in the press, but we certainly went through a bunch of different phases and a lot of the stuff. I worked on myself that Facebook ended up getting talked about a ton in the press negatively most of the time. You just learn to just keep your heads down and keep shipping. Ultimately, that's all that matters. I feel proud of the way that I think our culture is internally being formed right now. We tend to not get distracted.

**Lenny** (00:36:37):
It seems to be the case. I'm curious where you see Substack going as a product long-term. What are you excited about? Where are things heading?

**Sachin Monga** (00:36:45):
Maybe I'll answer that in two parts, one from a writer centric lens and one from a reader centric lens, which I mentioned is a bit of a newer thing for us. From a writer centric lens, I really think that we're just starting into this golden era of what it might mean to be a writer on the internet. Like I mentioned before, the economic model for supporting great writing on the internet has been generally pretty terrible for the entirety of the internet's history.

**Sachin Monga** (00:37:13):
In the early days of Substack, there's a couple of these glimmers of hope where you'd have people like Matt Taibbi or Bill Bishop, some of the early writers on Substack that were really well established writers who were clearly just being undervalued and now could come to Substack and see their true value. That was awesome. That was really cool to see. But in the last year or so, even in the last few months, I think there's been so many really interesting success stories now from writers who might not even consider themselves writers, let alone well established writers like Matt Taibbi or someone like that.

**Sachin Monga** (00:37:46):
People who are able to make a living, maybe even make a fortune just doing great work and not needing to have millions and millions of viewers or play the attention games of other networks, but just do really high quality work and have a relatively small number of people value it highly enough to pay for it. That's like a new thing. When I see the next one to two years play out for the writer side of the equation, a lot of what we're going to try to do is just make it much simpler to get started, to have your Substack.

**Sachin Monga** (00:38:15):
If you have an audience anywhere, Substack's never going to be the place where have the biggest audience probably, but it certainly should be the place where your most valuable audience comes home to, where they get your best work. We're seeing a lot of really interesting success stories now of people that might have a big Instagram following or YouTube following and certainly Twitter following were able to use Substack now as this home base, this place to try to accumulate their most valuable audience that they own in the sense that they get their email address, they can export them at any time, and just build really simple tools to just help them deliver their best work.

**Sachin Monga** (00:38:47):
It could be writing, could be a podcast, could be video. We're investing a lot in some really interesting community features as well. You're a great example of this. To call Lenny's Newsletter simply a newsletter would be hilariously wrong at this point, right? I think you mentioned to me you had 30 meetups around the world last month or something like that.

**Lenny** (00:39:03):
That's right.

**Sachin Monga** (00:39:04):
It's an impressive of run rate of meetups. I think seeing that unfold and seeing how the platform can support that type of community behavior as well is a big thing that I'm excited about. Just more. On the reader's side, I think maybe to segue into that, I think we're again entering this little potential golden age of the internet for how you experience it as a consumer. Where instead of just having a handful of feeds that are basically the same, that you could just scroll through and consume videos of random people doing random things. Not to say that's bad and that should go away.

**Sachin Monga** (00:39:37):
I do my fair share of just scrolling through my phone and watching random videos too, but it'd be kind of nice to have another place you could go to as well where the best culture is being made and you have an extreme degree of control over what you see and who you choose to lead into that space. You might not spend two hours a day in there, and that's fine, but it might be the first place you go because it's where all the best stuff is and it's where your best communities are going to live too. We kind of see Substack evolving not as some new type of social media, but true alternative to how you might spend that most valuable slice of your time.

**Sachin Monga** (00:40:13):
We just launched an iPhone app, I guess now it's been six months ago, and it's going really well. We're going to launch an Android app very shortly. We're pushing really hard on this reader experience as well. I think it'll be radically different and much better one or two years from now too.

**Lenny** (00:40:28):
It's been interesting to see a growing percentage of the great content that I come across be on Substack, and so I think that's a cool trend for y'all. For writers that are thinking about starting a newsletter, thinking about joining Substack, what sorts of advice, tips, guidance do you have for folks that are thinking about getting into the Substack world?

**Sachin Monga** (00:40:50):
My first piece of advice would be to just start it and see what happens. Start it. Have a way to start gathering subscribers. Put a link to it somewhere. Write one or two things. If you're not much of a writer, try posting a video, recording some audio, turn into a little podcast. Just start basically and see what happens and see what kind of interest there might be out there for what you have to say, especially if you already have a following on other platforms as well.

**Sachin Monga** (00:41:17):
I think that there's a real risk that if your entire following is locked into one platform where you don't have a ton of control over, your ability to reach those people deterministically and certainly to monetize that in some way, it seems like it's a tenuous place to be in the current age of the internet. I'd say just start. It should be really easy. Go to Substack.com, press the start your Substack button, and see what happens.

**Lenny** (00:41:41):
That advice may sound to people like, "Oh yeah, that's not actual advice." But I will say that is exactly what I did and that's exactly how I got to what I do now. I had zero intention of ever doing this. Charging for writing that I'm writing, that's crazy. Just the fact that Substack existed and let me try stuff out for free. You sign up. You start it. My newsletter, it's called Lenny's Newsletter because that was like the default recommendation when I signed up, because I told them my name's Lenny and it's like Lenny's Newsletter, because I had no plan to do this. It was just like, let me just sign up and try blogging here for a little bit and that little path.

**Lenny** (00:42:21):
I think about Chris and Hamish and the founders mapping out a user journey of a vision of how somebody onboards to Substack, to go from never writing to doing it full-time. I feel like I went through that exactly, if they even had that, where I sign up just to try it out. I start writing consistently. It starts going well, then I think about charging, and then I launch the paid plan, and then that goes well. It keeps growing, and then I do it full-time. That's exactly what I went down and there's no world where I would've done this if not for those magical combination of features of just a really simple blog a d newsletter and collecting emails and maybe monetizing down the road.

**Sachin Monga** (00:43:01):
Yeah, that's amazing to hear.

**Lenny** (00:43:03):
I think that just start advice is really spot on. Just try it out, see if it's something you want to do. I will say, it's easy to start a newsletter, it's hard to continue a newsletter. The continuing is the most important part, as Seinfeld would say in that clip, who rings the bell.

**Sachin Monga** (00:43:17):
I will say though to that point too that I'm really excited for what Substack can do in the product to make that easier in a way that doesn't cheapen the experience. There's a bunch of things we could do to. We could automatically post stuff to your readers. We could do a lot of things. Going back to the how do we do discovery, there's a bunch of things that would probably just work, but they would eventually kill what Substack is or have all these nasty second order effects and ruin this promise of putting writers in charge, putting readers in charge.

**Sachin Monga** (00:43:45):
I'm really excited and I actually view your Substack as a vanguard, as a very leading edge example of this, of you have turned your Substack into not just this thriving community of readers, but also of contributors and creators. You've got these amazing people coming and doing guest posts. You've got the podcast going. You've got these meetups. You've I think in a lot of ways alleviated the burden of how hard it would be to just be writing a long form thing every day and doing that for the rest of your life. That would be really hard. That would make it certainly much harder to keep going.

**Sachin Monga** (00:44:19):
Not to say that it's easy now, I know how hard it is to do what you do. But I think Substack can do more to turn this ecosystem to funnel this energy into ways for people like you to feel more like a leader of a space and a curator in a lot of ways and still deliver this really valuable service to your audience without having to do all the work yourself. I think we can do a lot more to support that kind of thing.

**Lenny** (00:44:45):
Is there anything you could share about what sorts of things you're thinking there and what might be possible?

**Sachin Monga** (00:44:49):
Let's see. Guest posts are working really well, and I'll say that we have a bunch of ideas for how to make guest posts a much bigger thing. Right now, the way guest posts work, kind of like an op-ed or something, like you invite someone to come and just write a post on your Substack. I think there's much more we can do without getting into some of the specifics and scooping the product team that we're working on that I think could make it feel more like you've got a bunch of people who are somewhat more fluidly able to contribute to your Substack and deliver value to your audience.

**Sachin Monga** (00:45:18):
I've teased this community stuff that we're working on a little bit, but we're piloting a feature right now that's been working really well where writers can get a little bit of like a... We view it as the pub at the back of your Substack where people can hang out and chat and the writer is still in control and sets the tone and sets the rules and norms for the space, but can create space for their subscribers to participate and hang out themselves too. Those are two areas that we're investing in a fair bit right now.

**Lenny** (00:45:45):
Something that I imagine somebody suggested that I'd suggest you all look into a little bit is open AI assisted writing. I was playing with this product that is called Jasper and there's also Copy.ai. I put in the title of the post I was about to write and it just generated a pretty good paragraph summary of what it could have been. They have this whole feature where you just start typing and it autocompletes things smartly.

**Sachin Monga** (00:46:11):
That's crazy.

**Lenny** (00:46:11):
That would be cool. I don't know if you want to go there, but it's pretty good.

**Sachin Monga** (00:46:15):
That seems like an interesting can of worms.

**Lenny** (00:46:17):
Right, an interesting can of worms.

**Sachin Monga** (00:46:18):
We did talk about whether we should change our default publication. You know how your default name was just like Lenny's Newsletter and we probably gave you a little red square or something as your default publication logo originally. A DALL-E generated publication logo service would be pretty cool.

**Lenny** (00:46:33):
That would be cool. If nothing else, it's just for ideas, but I would love that. Coming back to the idea of someone starting a Substack, we talked about advice, which is the core advice is just start and see how you like it. A big part of this is like, do you want to keep doing this? Because again, it's easy to start, hard to keep going, and also you may realize, "I've created this job for myself I don't like." That's something they should be thoughtful about. But on the flip side, do you see any common mistakes people make when they're starting on Substack that you suggest they try to avoid?

**Sachin Monga** (00:47:02):
One thing that's interesting here that I think we have a big opportunity to improve in the product is that there's going to be obviously varying levels of intent that people have when they hit that start your Substack button. Some people might come in being like, "This is going to be my full-time job. I want to make this work. I want to not just be a full-time writer, I want to build a media empire on Substack." There's certainly examples of that happening now. You can imagine a version of our onboarding and set up flow that's like the media empire version of it.

**Sachin Monga** (00:47:28):
You could also imagine the version that's just, "Let me just write one thing. Don't make me make all these decisions. I just want to get in the game." I think that in general, a mistake that people might make is... I'll maybe flip it back to an anecdote related to what I heard from Chris when I was chatting with him the other day, that he had to convince you pretty hard to turn on payments at all. Correct me if I'm spreading misinformation, but is that right?

**Lenny** (00:47:51):
Yeah. And Hamish too. Especially on how often I can take a break, he's always given me advice of, "You can take a break more often than you think," because I feel like I can never not do a week. Both those pieces of advice. It took me a while to get over, maybe I could charge for this and then maybe I could take some weeks off.

**Sachin Monga** (00:48:10):
Right, right. I think there's a generalizable piece of advice here that might be my answer to the question of what's a common pitfall, which is people are really worried about how their audience will perceive them and really ultimately their own worth, right? Should I send a newsletter three times a week into people's inbox? Is that too much? Should I ask anyone to pay me ever? Is that crazy? Am I allowed to take a vacation ever given that I've got people paying on an ongoing basis? And is that a bad service to provide if I'm taking a two week summer vacation?

**Sachin Monga** (00:48:42):
I think almost in all of those cases, and then you could imagine five more things like that, readers, especially the people that are subscribed to you who are paying you, are pretty forgiving and are really there to support you and want you to take that vacation. There's probably more people who would want to pay for you that just don't even know about you that would totally pay if they could. Go back to that spectrum of, am I just trying to write a blog post? Am I trying to start a media empire? It's kind of like many people won't know yet. Just open up optionality for yourself and see what happens. Maybe don't be too worried about what your audience might think.

**Sachin Monga** (00:49:20):
I think that maybe is one difference between Substack than something like Twitter or Instagram or something. Subscribe as an action is pretty heavyweight. It's like a costly signal, right? It's not as easy as just matching the follow button on a bunch of accounts on Twitter or something like that. If someone is subscribed to you, they're granting you write access to their brain is maybe the way I view it in a nerdy sense. What that means is not just like, "I'll let you write your one long form thing once a week," but, "hey, you've got this other person that you think might have something interesting to say? Cool, let me know. I'm here for it." I think writers underestimate that.

**Lenny** (00:49:57):
Maybe three things I'll add to this just for folks that are thinking about, should I try this out? Should I not? One, when I joined Substack, I already felt like it was too late, and this was three years ago. I was like, "Nah, it's too late. Everyone's already got their big newsletters. There's no way I'm going to make any dent." I think people feel that now, and I think it's also not true. I think there's so much opportunity.

**Sachin Monga** (00:50:18):
100%.

**Lenny** (00:50:19):
Two, when I got to a thousand paid subscribers, which feels very doable, I was making around a 100K, which is exactly... I think it was Kevin Kelly's 1000 True Fans. It was exactly like, "Oh wow! I could make a living with a thousand true fans for real." It's shocking how much you could make with so few people that really care about what you're doing. Think about is there a niche or something you're excited about that you can find a thousand people to pay you 10 bucks a month.

**Sachin Monga** (00:50:52):
What's cool about that I think now with Substack and with the network effect is if there's a thousand people who are going to pay you 10 bucks a month, there's probably 2,000 and 5,000 and 10,000.

**Lenny** (00:50:58):
That's exactly what happened to me. I'm like, "If I hit a 100K, holy moly, I am good," and then it just kept growing. That's exactly right. You think there's an out, but the markets for these things are huge. The last point maybe is it took me nine months of doing it every week for free to get to a point where I felt like I can keep doing this. I enjoy doing this. People continue to value it, where I decided to turn on paid. It's a very slow and steady thing initially.

**Lenny** (00:51:24):
Don't expect it to just blow up. Just do it every week. See how it goes. See if you like it. See people like it. And if they do, keep going. If not, you can stop. When I launched my newsletter, I tweeted. I'm just going to experiment this thing. No idea where it's going to go. Just try it out, so you don't have to set the stakes high when you're starting out.

**Sachin Monga** (00:51:41):
I think that's exactly right. You mentioned Kevin Kelly's 1000 True Fans, which has become this canonical piece of writing on the internet now. My favorite Kevin Kelly blog post, that's my second favorite, my first favorite is a post that he wrote called You Are Not Late, which is exactly what you... You can probably picture what he says, but it's such a compelling, persuasive argument for the thing you mentioned, which is like... Obviously he wasn't talking about Substack in his post, but he was talking about the internet and how in the grand scheme of things, how lucky we are to...

**Sachin Monga** (00:52:13):
I don't even know when he wrote it, maybe it was probably 10 years ago at this point, but certainly at a time where a lot of people were feeling, "Oh, Facebook and Google and the internet's done. The battles have been won. I wish I was coming of age. I wish I had graduated from Harvard in 2004 or something." It's just so wrong. We are so early when it comes to how the internet will play out that I think getting to work on that in any capacity right now, getting to shape how the internet is going to play out over the next 10, 20 years is so fun because we are not late.

**Lenny** (00:52:40):
Here, here. I know Marc Andreessen mentioned those too when he moved to Silicon Valley in the '80s, "It's all over. It's too late. I missed the gold rush of tech," and it was just the beginning. Well, we've reached our very exciting lightning round where I'm just going to ask you a bunch of questions real quick, share whatever comes up. Sound good?

**Sachin Monga** (00:52:59):
Sure, let's do it.

**Lenny** (00:53:00):
What are two or three books that you recommend most to other people?

**Sachin Monga** (00:53:04):
I will plug some books that have nothing to do with the internet or software or tech, but have been the most informative or instructive books for me I think in my career as a product person working on software, which are books about architecture and urban planning. The reason why I find this field so fascinating is because for thousands of years, people have been figuring out how to build spaces that help people interact with each other and build good spaces to occupy. We've only been doing this for, going back to the Kevin Kelly thing, for basically the blink of an eye on the internet and in the digital realm.

**Sachin Monga** (00:53:35):
There's one book in particular by an architect named Christopher Alexander who sadly just passed away earlier this year. He wrote this book in the '70s. It's called The Timeless Way of Building. This is the book that I recommend to the most people I have. I buy it in bulk and I just give it away to people. The basic premise of the book is that in the '70s, we had just gone through a couple of decades of just mass produced cookie cutter suburban house development in the US. His premise was like we've basically just lost the plot on this. No one likes living in these houses.

**Sachin Monga** (00:54:06):
If you think about why these houses all feel bad to live in, it's because the people building the houses now for the first time ever are different than the people living in the house. It's these developers, these real estate developers, these big companies, mass producing these houses. But for thousands of years, we've figured out what makes a good house. The people building the house are the people living in it and they get that, but now the incentive structure got changed and they messed everything up.

**Sachin Monga** (00:54:27):
I think there's a really interesting parallel there with the internet, specifically how the last decade or so has played out, where the people building the spaces that we occupy are operating under a very complicated incentive structure and it's leading to these suboptimal user experiences. This is what we work on at Substack. This is what I think is fun to work on right now. If you're working on something like this, I would highly recommend The Timeless Way of Building by Christopher Alexander.

**Lenny** (00:54:51):
Awesome. We're going to include that in the show notes for sure. What are two or three Substacks that you recommend most speaking of recommendation features?

**Sachin Monga** (00:54:59):
I was just thinking about this as I don't write on stack certainly frequently, and so I don't use the recommendations feature, but who would I recommend if I did besides Lenny, of course? I'll share a couple of random examples maybe, again, outside of maybe the tech product world. There's this guy named Darryl Cooper who has a podcast on Substack called The Martyr Made Podcast that I've gone super deep into lately. It's hard to describe. He basically takes a topic and he will produce the single best explanation of that topic you will ever find, because you'll spend an insane amount, probably 10,000 hours per topic, figuring out getting to the bottom of this story.

**Sachin Monga** (00:55:38):
He's doing a series right now in the labor movement in America. It sounds like a boring topic maybe, but he's just such an amazing storyteller. He's I think a good example too of this could only really work if he finds his thousand true fans as people who are just like, "Yeah, I'll just pay for this." It would be a very bad advertising business for sure. He publishes pretty infrequently, inconsistently, but it's just the highest quality stuff. That's The Martyr Made Podcast. Since I know this is supposed to be a lightning round and I spent too much time on that, the two others that I'll just quickly throw out there, Colin Meloy is one of my favorite musicians.

**Sachin Monga** (00:56:10):
He's the lead singer of The Decemberists. He's doing a really cool thing on his Substack right now of just a lot of interesting behind the scenes stuff on tour, publishing, audio and video. It's been really good. If you're a fan of The Decemberists, I highly recommend. One more, let's see, I have been really excited about Ethan Strauss lately. He writes a Substack called the House of Strauss. He's a basketball writer, but I think it's a cool example of like he just has subscribers now. He can write whatever he wants. He writes about a wide range of topics and they're all just really fascinating. I love to see that kind of thing happen on Substack and in general.

**Lenny** (00:56:41):
That's just reminding me, Kareem Abdul-Jabbar just recommended my newsletter in his Substack.

**Sachin Monga** (00:56:45):
Oh man, congrats! That must be a life achievement right there.

**Lenny** (00:56:50):
Yeah. I'm like, what the hell?

**Sachin Monga** (00:56:52):
Congrats!

**Lenny** (00:56:53):
Thank you.

**Sachin Monga** (00:56:54):
He's a great writer. .

**Lenny** (00:56:54):
I don't know if he reads it. I don't know. I don't know what's going on. I love it. He has got a great Substack, by the way. I think if you just Google Kareem Abdul-Jabbar Substack, you'll find it. On the recommendation feature, I was just thinking, do you want to shout out the folks that built it, the team?

**Sachin Monga** (00:57:07):
I would love to.

**Lenny** (00:57:08):
Let's do it.

**Sachin Monga** (00:57:09):
It's too many. It ended up being a company wide effort, but the product manager on my team, Dayne Rathbone, was specifically I think the spearhead behind the way that we built it, like you mentioned, that we went into. He was a really big proponent for that. Gabriel on our design team designed it and many engineers worked on it. It'll be hard to shout them all out, but I'd shout out Dayne on my team because he ensured that we built it in the way that we ultimately needed to build it for it to work.

**Lenny** (00:57:36):
Thank you, Dayne and Gabriel. Two final questions. Do you have any favorite recent movies or TV shows that you watched that you love?

**Sachin Monga** (00:57:44):
Yeah. I just finished the latest season of For All Mankind and loved it.

**Lenny** (00:57:49):
So good.

**Sachin Monga** (00:57:50):
Did you watch it all?

**Lenny** (00:57:52):
Yes. Oh my God! The last couple episodes, you're sitting on the edge of your seat.

**Sachin Monga** (00:57:55):
I feel like in this season, every episode was like its own standalone movie or something. It started slow the whole show. I think the first season was a bit slow. When I recommend it to people, I'm like, "Just power through it," but they really found their groove. I don't know. I'm stoked for the next season.

**Lenny** (00:58:10):
Same. Final question, what's a favorite interview question you like to ask folks when you're interviewing them?

**Sachin Monga** (00:58:16):
I have a tough time answering this question because I have found that there's not one question that will get me the signal I actually want given how diverse the candidate's experiences might be in their context. If you're coming from a Facebook type place or coming from a startup, I might need to ask different questions in order to get the signal I want. Maybe I'll answer it in that way, which is like these days, especially for Substack, what is the signal that I'm trying to get?

**Sachin Monga** (00:58:43):
I think really for early stage, fast growing startup, we talked so much about how different that is, we just need people who can run through walls to accomplish big goals. Maybe grit and endurance in some ways and drive are the words I would throw out there. I find it's really hard to have one question that will get that signal. We need to tailor it to that person's background.

**Lenny** (00:59:07):
All right, I'll accept that meta answer. Sachin, thank you so much for being here. As you I've shared, Substack is very near and dear to my heart, and I'm really thankful that you spent the time to dig into a lot of these things that have been on my mind. I imagine it will be helpful to a lot of other people. Two final questions. Where can folks find you online if they want to reach out, learn more? Are y'all hiring? And then how can listeners be useful to you?

**Sachin Monga** (00:59:31):
First of all, thank you, Lenny, for being such an amazing Substack example setter. We talk about you all the time, as you can imagine internally, and you've been so helpful to the company and to our product team. It's been a real honor to get to come onto the pod and keep doing what you're doing. You can find me on all the various social media platforms. I'm not super active on them, I must admit, but maybe Twitter would be the one where I spend the most time, which is just Sachin Monga, my first name and last name, is my handle.

**Sachin Monga** (00:59:58):
I'll make one plug for a role that we're hiring for right at Substack, which is a senior data role with a product and growth analytics bent would be the specific archetype we're looking for in this role. If you are listening to the pod and feel like that might be you, I would love to chat. I think my email address too, I don't know if it would get shared, but it's just Sachin, my first name, @substackinc.com. Feel free to send me a note anytime.

**Lenny** (01:00:24):
Awesome. We'll include that in the show notes. Sounds like y'all are building some cool analytics features maybe based on that role. I'm excited for that. Awesome, man. Thank you for being here.

**Sachin Monga** (01:00:33):
My pleasure. Thank you so much for having me.

**Lenny** (01:00:37):
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] Lessons from one of the world’s top executive recruiters | Lauren Ipsen (Daversa Partners, General Catalyst)

**Lauren Ipsen** (00:00:00):
Regardless of whether or not you're hiring, you should always be keeping a pulse on the market. That is the most important thing. And I think that should be the case for both candidates and folks that are hiring. Like, you never want to put yourself in a position where you have no idea what good looks like, whether that's from a company standpoint or from a candidate standpoint. So, both parties should always be having a good understanding of which companies are thriving, which individuals are building great things and are well known commodities in their organizations and get great references.

**Lauren Ipsen** (00:00:35):
Oftentimes, I encourage founders to simply chat with what good looks like and get a really good sense of what benchmark candidate profiles could be, and who knows where that person will be in a year or what have you, but staying really, really close to really great people and using them from an advising capacity or getting them ingrained in some type of involvement in the product prior to actually having that specific need, I think, is really important.

**Lenny** (00:01:05):
Welcome to Lenny's Podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. Today my guest is Lauren Ipsen.

**Lenny** (00:01:15):
One of the most important skills for founders and senior product leaders to develop is the ability to hire great people. You won't be able to build the best company or the best product if you can't hire the best people. And Lauren is one of the most experienced and successful people in the world when it comes to hiring product leaders. She's placed over 80 senior product leaders across tech companies and has worked with some of the biggest companies out there. When I asked a bunch of really smart product leaders who their favorite product recruiter was, Lauren's name came up a ton.

**Lenny** (00:01:46):
**Lauren Ipsen** (00:04:47):
Thanks so much. It's great to be here.

**Lenny** (00:04:50):
I've been meeting to do an episode on product hiring and recruiting product people for a while, and when I asked a bunch of smart friends who should I have on to talk about this stuff, your name came up a bunch, and so I'm really happy that we're finally doing this.

**Lauren Ipsen** (00:05:03):
Me too. Absolutely. I'm grateful that you asked.

**Lenny** (00:05:07):
So, to help listeners get a sense of just your background and kind of the journey you've been on to get to where you are now, can you just spend maybe just a minute kind of talking through the wonderful things you've done in your career and what you're doing now?

**Lauren Ipsen** (00:05:19):
Yeah, absolutely. So I started my career in broadcast. I originally thought that I wanted to be on the news and quickly realized I didn't necessarily want to be the face of sadness. There's a ton of that happening in the world.

**Lauren Ipsen** (00:05:36):
So, made a pivot pretty early on and thought, where could I use the communication skills that I've been working so hard on and do something that's impactful in a big way, but maybe just with a little bit of a different angle? And stumbled across executive search.

**Lauren Ipsen** (00:05:52):
Exec search is not really something that people major in college by any means or think they're going to end up doing. So it was something I found fascinating. I had applied to all of these different companies like Twitter and Snap and Pinterest, hadn't heard back from any of them, was a name in the resumes, and thought, well, how cool would it be if I could work with all of them and have an opportunity to play a part from a different lens?

**Lauren Ipsen** (00:06:18):
So, got into exec search, was really focused early on on consumer mobile build outs. Was doing a lot of work with Twitter and Reddit and TaskRabbit and Nextdoor, Postmates, you name it, and that was probably 85% of the work I was doing. And then as, on the agency side, 15% was obscure, autonomous helicopters selling into the Department of Defense and then retail and robotics, and it was all very fascinating, but for me, who has wicked bad ADD, it was amazing to be able to be so stimulated by so many different industries and feel like I couldn't really master this.

**Lauren Ipsen** (00:06:57):
So, long story short, had an awesome career at Daversa Partners, which is a boutique executive search firm, and thought I was going to be there potentially forever. Was tapped by a awesome individual, Abe Shafi, who was founding a company. I had been doing a lot of work for them. They were a client of mine at the time. Placed a couple great hires and they said, "We're either going to kick off a head of talent search with you or you can come over and join us." So I was the first recruiting hire over there, built out the talent function in its entirety.

**Lauren Ipsen** (00:07:27):
I definitely think there was a part of me that I loved the operating experience, learned a ton, worked side by side some amazing people, but was really missing working with founders, and lots of them, and keeping a pulse on the market. So General Catalyst tapped me most recently, and been working here for the past couple months, and it's been great thus far, and I'm specializing in our consumer and crypto investments.

**Lenny** (00:07:51):
Awesome. The fact that you're at GC now makes me think about another recruiter that I know who's awesome, Austin Brizendine, and it's interesting that a lot of the best recruiters seem to be heading to VC funds, and I'm curious why that is happening. Is it like a comp thing? Is it other things that are pulling everyone away into funds?

**Lauren Ipsen** (00:08:09):
It's a great question. It's definitely not a comp thing. I'll say that. I think it could be a stability of life thing. Search is incredibly volatile, and you have to hustle so hard, and as soon as you have three wins, you've got four more things to execute on. And so, there's aspects of it that can be tough, especially in a market like right now where you really do have to chase business and you can't be selective about what you take on, so you could be pitching things that maybe you don't necessarily believe in in its entirety or what have you. So, I think that's one component.

**Lauren Ipsen** (00:08:39):
In house is obviously difficult right now as well for talent leaders. It's really scary to take a bet on one single company right now and know what it's going to look like six months from now. And so I think those things combined might be the reason for an influx in folks leaning more towards venture, and I think it's just timeliness.

**Lenny** (00:08:59):
Got it. That makes sense. The downside is it's hard for people to find awesome recruiters because once you're in a fund, you're just going to help those startups. And so we're going to talk later about just how do people find awesome recruiters, what do you look for? But there's roughly three things I want to spend our time chatting through today. One is for founders and hiring managers, just how to find the best talent and what they could do to be successful finding the best talent. Two is for product leaders and PMs, how to give themselves the most opportunity from the flip side. And then third is just for recruiters, what do they often do wrong? How do they miss out on the best product talent? Does that sound good?

**Lauren Ipsen** (00:09:37):
Yeah, that sounds great.

**Lenny** (00:09:39):
Okay, cool. So on the hiring front, just diving in, say you are a founder, you're someone really early at a company, and maybe you've got a couple PMs and you're starting to think about we need to hire a really senior product leader or first senior product leader.

**Lauren Ipsen** (00:09:52):
Sure.

**Lenny** (00:09:53):
What do you find is often the biggest mistake that founders make when they're trying to hire their first senior product leader?

**Lauren Ipsen** (00:09:59):
I think especially for founders that haven't hired for this caliber of talent in the past, it's really easy to be distracted by shiny objects and look at huge names. You want to find the CPOs of Google and YouTube or what have you because that seems like it would be such an incredible opportunity for brand recognition. And to an extent, it is. But the fact of the matter is, oftentimes those individuals are pretty far from the work and have a great team of executors that they've put into place that are actually the ones that are in the weeds.

**Lauren Ipsen** (00:10:33):
And so I think that's the biggest mistake I see people make, especially on the hiring front where they have limited resources, and maybe they're an early stage company and trying so hard to bring in big names is not always the best way to go about it because the fact of the matter is they need to go then hire a team. So, I think looking for someone that's a little closer to the work, maybe someone that can step up into that type of role and do so in a way where some days they might actually be operating like a PM and then other days they might be able to build from a leadership perspective, that's more of the DNA that people should be targeting.

**Lenny** (00:11:09):
Do you think the source of the issue with that going wrong, that they no longer can do that work as well because they've been shielded away from the tactical day to day? Or is it that they're not as hungry as they used to be and they're just like, "I already, I'm a YouTube 10 year super success, I don't need to prove myself anymore," and they're just not as hungry, or something else?

**Lauren Ipsen** (00:11:29):
I mean, I'm not going to sit here and say that all senior leaders aren't hungry. I think that there's some folks that really lean into the work in a different way and miss that, and often go to startups because they crave building.

**Lauren Ipsen** (00:11:41):
So it's not necessarily that, but I do tend to lean towards folks that have a chip on their shoulder or have something to prove and want to build a name for themselves. All of that to say, there's a reason that a lot of those people got to where they are, and some of the best talent are some of the senior folks, but just maybe not necessarily the best talent for where this company is today. Right? It could be great for 10 years down the road, but the past five years of that individual's career could have been far more focused on camaraderie, team building, operational components, performance reviews, and then aspects of product vision, which just might not be the innovative AB testing type of profile that you typically look for in these pre-IPO companies.

**Lenny** (00:12:27):
Got it. I imagine there are stories that you can share about people you've placed like that, that have not worked out. If you can share one, that'd be awesome. But maybe a side question is the general advice, just don't assume someone that's been successful at a big company with a fancy background is going to be great. Sometimes they work out, but not always, is that kind of the takeaway?

**Lauren Ipsen** (00:12:46):
Yeah. I would say the general advice is who is going to be best for this specific role at this specific time, not necessarily who is the best talent in the world or in the market. Those are two very, very different questions to ask. And I think early on in my recruiting career, I was often just trying to recruit these whales of executives to try and prove myself and say, "Oh, I got this person to entertain this opportunity, how sick is that?" But naturally, that's not necessarily the person that actually can move the needle. And so you need to think very specifically. Just because this is the best talent, that doesn't necessarily mean they are the best talent for this role today.

**Lenny** (00:13:25):
So to double down on that, say you are hiring and you know you're going to start hiring a senior product leader, what is it that you suggest founders nail down and iron out when they're kicking off the hiring process, either on their own or with a recruiter? Like, in the job description, what else do they have to get right to find the right person?

**Lauren Ipsen** (00:13:48):
It's a number of things, like product leaders can come in a lot of different flavors, and so I think it's trying to determine where this person should major and minor, where they should spike. Is this someone that's going to really lean into the design efforts? Is it someone that actually kind of needs to just operate like a very senior PM and continue to build out a team? Is this someone that really should be focused on product vision for the long haul? And then thinking more holistically about how to build the rest of the team.

**Lauren Ipsen** (00:14:12):
There's so many different ways in which you can hire for a product leader. So I think it's trying to work a little bit backwards and think about, what is the actual outcome that we are trying to solve for with this hire? Or are we just hiring a head of product because we feel like we need to hire a head of product? That's so often what I see is the board's telling me we need to hire a head of product and I don't necessarily think that we do, or I'm not exactly sure what we need in this role. And so whenever you're starting a search in that regard, it's kind of doomed from inception, so you need to get incredibly granular on the front end around, what is this person going to be coming in to do? What's their mandate? And if we think about someone that's just absolutely hitting it out of the park and crushing it, what does that look like? So I think just trying to be really specific on the front end.

**Lenny** (00:14:59):
I love that last piece, just what does success really look like for this person? On the first piece, that's exactly the same advice I give founders when they're looking for a PM is like, what do you concretely need them to do day to day? Not like, "We need someone to help us with product." And that often helps illuminate, okay, I see. We need someone to help us ship more consistently. We need someone to help us hire engineers. Yeah, just make a list. What are they going to do in the first month or two or three?

**Lauren Ipsen** (00:15:24):
Yeah, yeah, absolutely. I think those are the most important things. Like the 90 day plan is something that's overused but so necessary, and that's just the tip of the iceberg. So that component and then, okay, a year from now, what should this person be doing? Two years from now? Do we want them to grow up into a CPO role? Do we think about that in a different way? How are we thinking about the product direction today, 12 months from now, 18 months from now, through IPO? I think it's really difficult to think about things that way, and so often you're thinking about the task in front of you and just trying to iterate quickly, but that is the type of thought process that needs to be happening from the CEOs and founders.

**Lenny** (00:16:06):
Are there archetypes of PMs, if you just bucket like here's the three maybe most common types of product leaders that founders hire, because there's an infinite list of skills and things they could do, but just to make it even simpler, like here's probably one of these three you're looking for. Do you have something like that in your head?

**Lauren Ipsen** (00:16:25):
Yeah, there's platform product leaders or folks that are kind of more indexed on the infrastructure components. There's folks that are typically focused on core product, or consumer product if it's on the consumer side of things. And then you'll have folks that are really indexed and that can include UX individuals, design folks. And then there's also typically specialists, so individuals that are really hyper-focused on growth or monetization or what have you. Those are the three buckets that I would say I see most often.

**Lenny** (00:16:57):
Do you feel like founders sometimes pick one of the wrong buckets and that's a common mistake, or is it generally it's the wrong bucket but then maybe it's not the right spikes of skills within that bucket?

**Lauren Ipsen** (00:17:08):
Well, it's kind of twofold. I think sometimes people just bring in a head of product to do everything, so that's probably not the best way to go about things. I think that ends up being a unicorn, which you hear often in the search world, and it becomes really difficult to hone in on what good looks like.

**Lauren Ipsen** (00:17:25):
And so I think again, it just comes back to having a clear org chart on the front end and determining, are we hiring someone specifically to build out our walled garden ads approach, or are we hiring someone to run product marketing, or are we hiring someone to help from a product perspective to build a better core user experience? Those are all very, very, very different roles, and if you bring in one person to try and do it all, the facts of the matter is, they're going to have to bring in some key lieutenants to help them, so is that something you want to do or are you more focused on bringing in someone imminently to help on the ad side of things, and then we can find that head of product to help them out down the road?

**Lauren Ipsen** (00:18:05):
That's kind of the way in which I would architect it and think about it, is what's most imminent, and what do you actually need to hire for today, as opposed to just hiring for the sake of hiring and bringing in that leader.

**Lenny** (00:18:17):
And part of the discussion there is maybe they grow up into this head of product long term, maybe not. Maybe we just need someone to ship the ads platform, right?

**Lauren Ipsen** (00:18:24):
That's exactly right. Yeah.

**Lenny** (00:18:26):
You mentioned this title of head of product. There's also VP of product, CPO. There's all these titles and I feel like people sometimes use them interchangeably, don't know which one to use when they're putting out a job description. Do you have any kind of heuristic rule of thumb of just, here's how to think about when to use each of these titles? Or is it not even a big deal for, say, a founder, hiring the first senior product leader?

**Lauren Ipsen** (00:18:48):
It's a great question and it definitely leads to confusion across the board because I'll have candidates come to me and they'll say, "I'm only looking for a CPO role," when I'm working with a startup where, maybe on the venture side of things, we've actually advised that startup to not hire C-level executives at this point. And so that naturally could eliminate a candidate that could be amazing for the role.

**Lauren Ipsen** (00:19:15):
Similarly, people could feel that way if it's a VP of product role, but that in their mind is the most senior product leader within the organization running everything from end to end who they intend to be the CPO down the road but are not in a position where they're ready to hire C-level execs. So, it's tough, and it really depends on the organization and the way in which they're thinking about org charts and leveling.

**Lauren Ipsen** (00:19:39):
A lot of startups at this point are almost allergic to C titles or VP titles or are just more title agnostic than I've seen in the past, so you see a lot more of these head ofs, and that is sector leaders, up until probably C plus or D stage. And then you get to D and E, and you'll see more of the VP, director, CPO type. And I think that is the way that people should be thinking about it is, if I'm joining a company very, very early days and it's called head of engineering, that is intended to be the most senior engineering leader within the organization.

**Lauren Ipsen** (00:20:19):
The fact of the matter though is there's good reason sometimes why they're not throwing out that C title, and could this person be layered down the road? Potentially, because maybe the talent they need right now is different than, just as we had spoken to earlier, is different than the talent that they might need from a massive CPO in two and a half years.

**Lauren Ipsen** (00:20:37):
And so I think that rubs people the wrong way because they want a bit of a promise that things are going to, if they join at this stage, that they'll be in it for the long haul and be that chief product officer that takes a company through an IPO. But companies are so dynamic and things change so quickly.

**Lauren Ipsen** (00:20:52):
So, I guess a long-winded way of me saying there's different breadth and depth to each role, but I think for the most part, unless it's a very siloed company with multiple different VPs, if you're coming into a company and they say this is the head of product, the VP of product, or the CPO, that all means the same thing dependent on the stage, for the most part.

**Lenny** (00:21:14):
And the other takeaway there, which is awesome, is if you're early stage startup, probably just start with head of product. Keep it simple.

**Lauren Ipsen** (00:21:19):
Yeah.

**Lenny** (00:21:19):
Don't over promise. Everyone understands.

**Lauren Ipsen** (00:21:22):
Yeah. Because the last thing you want to do is have to demote someone. But once you get to a place of having C-level executives, like that's not going to do any good, but maybe you start as a head of product, and then as the company continues to grow, you lean into the growth side of things more, and so you become that head of growth or an SVP of growth. Like things iterate and change, but you just never know and you can't predict the outcome of a company on the front end, so.

**Lenny** (00:21:49):
A lot of people listening to this probably aren't hiring senior product leaders right now, but plan to and will in the future, and so I wanted to ask, what should founders do when they know they will hire a head of product, say, in the next year, that could set them up for success down the road? What should they be doing ahead of time?

**Lauren Ipsen** (00:22:07):
Regardless of whether or not you're hiring, you should always be keeping a pulse on the market. That is the most important thing. And I think that should be the case for both candidates and folks that are hiring. Like, you never want to put yourself in a position where you have no idea what good looks like, whether that's from a company standpoint or from a candidate standpoint. So, both parties should always be having a good understanding of which companies are thriving, which individuals are building great things and are well known commodities in their organizations and get great references.

**Lauren Ipsen** (00:22:43):
Oftentimes, I encourage founders to simply chat with what good looks like and get a really good sense of what benchmark candidate profiles could be, and who knows where that person will be in a year or what have you, but staying really, really close to really great people and using them from an advising capacity or getting them ingrained in some type of involvement in the product prior to actually having that specific need, I think, is really important.

**Lenny** (00:23:11):
That sounds awesome and it makes sense. How do you, as a founder, do some of that? Do you just ask folks like, "Hey, who are some of the best product leaders you know? I just want to chat with them. I'm not hiring, just want to kind of meet people who are awesome." Is that the behavior you suggest or is there something else you can do?

**Lauren Ipsen** (00:23:27):
That's a great way to go about it. And by simply saying, "No agenda, I'm not trying to hire you tomorrow, I just want to know great people." And to be totally honest, people feel flattered by that, typically. Most of the time if you've been referred to someone and heard nothing but great things about them and you really don't have an agenda other than wanting to pick their brain, people are like, "Huh, well, this is different from the day to day. This is fulfilling," and people want to pour their knowledge, especially into companies that they believe in.

**Lauren Ipsen** (00:23:58):
So, I think more often than not you'll find that, not just products leaders, but executives across the board are actually really inclined to do so and want to help out because it's a little bit different from the day to day monotony of their work life.

**Lenny** (00:24:12):
So, the advice is keep track of companies who are killing it, who you might be able to kind of poach from in the future, and keep a list and keep warm contact with folks that are awesome.

**Lauren Ipsen** (00:24:22):
Yeah.

**Lenny** (00:24:23):
It reminds me of a founder that ... or basically all founders who are really good at hiring and how far ahead they plant seeds and how they just play the long game with the best people they meet, and they just kind of keep the conversation going until they finally convince them to join a year or two later. Do you find that the same thing?

**Lauren Ipsen** (00:24:41):
Yeah, 1000000%. Yeah. When I was on the executive recruiting side of things at Daversa, the VP of engineering candidate that we ultimately landed, it was a seven month game of courtship, and let's bring him in to help out from an advising capacity, let's ask him how he would think about structuring this organization, let's talk to him about the best talent that he would recommend that we're spending time with. No question that's invasive, but more so just collaborative and exciting, and you'll find that the founder and that leader will build a different level of rapport and trust by not going through a formal interview process and having it feel transactional. And then with that, magic can happen and you can land incredible people.

**Lenny** (00:25:24):
This all sounds like a lot of work and a lot of time. Do you have guidance on how long it should take to find, like for a early stage startup, say series A or B, to find someone awesome, and/or how much time founders should spend a week, just best practice, on hiring for someone like this?

**Lauren Ipsen** (00:25:41):
I mean, I think if you're going to search, so if you're looking for this individual, it's really so case to case. There's searches that I've been in that I call three people. I know they're amazing for this. I tell the founder and CEO, "These are the three people you should chat with, hire one of them." And it's that easy.

**Lauren Ipsen** (00:25:59):
There's others where it's a lot of trying to figure out what the person's actually looking for. If there's some ... they hit it off from an emotional standpoint. There's so many different things that come with it. I would say from a timing perspective, it's not a hard number. It's more of just put yourself in the room with great people. If you have a tremendous amount of respect for someone, continue to harvest that relationship and ask what good looks like. Find excuses to continue to touch base with people that are important in your network. If you remembered that they'd mentioned that they were going to some event and you think that you might want to hire them down the road, in a non-creepy way, show up to that event. These are things that I'm constantly doing, and I think that founders can do a better job of, but just make yourself known and relevant. And then when you reach out and timing is right, it won't feel so obscure or so transactional.

**Lenny** (00:26:55):
That reminds me of a time at Airbnb where we had these meetups for engineers every month or so where it was a tech talk, and then all the engineers get a target engineer that is coming to the event. Like they get their profile and their picture, and their job is to make sure they have a great time and try to convince them to join someday.

**Lauren Ipsen** (00:27:14):
Oh my god. But it's so real. It's similar to college trips where you're trying to get recruited for a sport, and you have to ensure that you're, yeah, just continuing to give people the best experience possible and staying top of mind for people.

**Lenny** (00:27:28):
Yeah. But I can see it being creepy, They have no idea there's this person assigned to them, but it works. It worked great. It was a great tactic.

**Lauren Ipsen** (00:27:35):
That's awesome.

**Lenny** (00:27:36):
I want to come back to a question that I asked, but I feel like you'll have an actual more concrete answer to the specific piece of just, what's your guidance per week how much time you should be spending on hiring broadly, and specifically, heads of product, if that's any different. Do you have any just advice? Because I imagine it's always spend more time than you think. It's going to take a lot of time.

**Lauren Ipsen** (00:27:54):
Yeah, it's definitely spend more time than you think. If you are in an actual search, then you should devote all of your time to it. I know that sucks to hear, but you should be really carving out concrete time.

**Lauren Ipsen** (00:28:05):
The thing that's tough though is you could spend, I guess what I was trying to say is you could spend one hour on something or you could spend 10 hours on it, but it's more so around, are you doing things to be impactful during that period of time? Are you actually doing things that are going to move the needle? Are you just blindly reaching out to people on LinkedIn? Because that's not going to be the way in which you're going to find the best of the best. Some of the greatest talent, they're not even on LinkedIn.

**Lauren Ipsen** (00:28:32):
And so I think it's building a really strong network in advance, and then once you actually get to a place where you need to hire that person, calling all of those amazing people that you've built relationships with and saying, "Now tell me who your favorite person is and who the best person you've ever worked with is, and could you put me on a thread with them?" How are you going to differentiate yourself from the rest of the market? So it's less in my mind like a quantitative number of hours and more of, how are you doing things differently than the rest of the market?

**Lenny** (00:29:01):
I want to pull on this thread. Okay, so spending one hour versus 10 hours, and your point about how you could spend one hour and get as much done maybe in those 10 hours. What sorts of behaviors and actions should folks take to make use of, say, that one hour in hiring? How do you not waste your time?

**Lauren Ipsen** (00:29:18):
I mean, I would say I've got probably five of my all time favorite product leaders in the world that I tap whenever I'm kicking off a search. And they know that whenever life brings them to an opportunity where they are going to start looking or want to lean into board opportunities, that I'm going to set them up and shout their name from the rooftop, so oftentimes they're willing to point me in the right direction of great people, make those introductions, what have you, and I'm going to know simply because of how great they are that they would never put me in touch with someone that wasn't equally as qualified.

**Lauren Ipsen** (00:29:55):
So that I think because the quality is there, so I'm not just blindly guessing on quantity, spending a ton of time on LinkedIn, and then having to call unknown entities and ask for back channel references when they also might not even feel comfortable sharing the dirt. You know? So it comes back to rapport and people that you have around you that you know you can trust and tap into and ensuring that you're spending the time in the right areas.

**Lenny** (00:30:19):
Got it. Yeah, so tapping your network makes a lot of sense. If you don't have that yet, I guess is it worth spending time on LinkedIn just cold messaging people as a founder, and any tips there for just cold outreach that you think work for a founder doing it versus you who are a professional at it?

**Lauren Ipsen** (00:30:37):
I do think it is worth that time. If you see someone that looks amazing, hell yeah, reach out to them, spend time with them, why not? And oftentimes, again, people are excited to see, oh, this CEO and founder wants to pick my brain, doesn't look like they're coming at me to try and recruit me, but rather just to have an open-ended conversation. For sure, and they can sense. You can definitely sense that type of interaction and feel comfortable with it, whereas sometimes the walls immediately go up when someone senses that they're trying to get poached.

**Lauren Ipsen** (00:31:08):
And so it's I think something that's worth them doing for sure. It's just if you are going to look for a key executive and are on a time crunch, I don't necessarily think the best use of your time is blindly reaching out to executives when you don't necessarily have the expertise in knowing which companies were thriving during that period of time, which organizations were great, and which were a little bit weaker within companies. All of those things are just the inner workings of the recruiting atmosphere and technology, and I think tapping people, if you don't have the network, talk to a great recruiter or just spend some time kind of doing some research on who's great. You can ask investors or board members in your companies as to who you should be targeting. So there's always got to be one or two people that can at least point you to another three or four.

**Lenny** (00:31:56):
That reminds me of a tactic Gokul shared on this podcast about one of his best tricks, as you think of, if you're hiring salespeople, instead of looking for who are just the best salespeople, you look for the company that is known for being really good at sales and then you go find people there and try to poach their lieutenant types, not maybe necessarily their head of sales. Do you think that's a good move?

**Lauren Ipsen** (00:32:17):
Yes and no.

**Lenny** (00:32:18):
Ooh.

**Lauren Ipsen** (00:32:19):
Yes and no, because I think if the organization is incredibly good at sales then the majority of the folks are probably amazing, but you always have weak links, and just because someone has a brand on their resume at the right time, I think oftentimes CEOs and founders will do this thing where they kind over generalize, well, Amazon's Prime team at this time was amazing or something like that. It's like, they definitely could have been, but just as any other company, there's going to be people that are breakout, top 1% type individuals, and then other individuals that get to ride the wave and reap the benefits of being at the right place at the right time. And I think that's a good starting place, but then also spending time getting a little bit deeper on who the best people are within that organization. But yeah, we always start with market mapping, so determining who the best companies are within a specific area, and then I just encourage everyone to take that a layer deeper.

**Lenny** (00:33:16):
Got it. It just comes back to your previous piece of advice. Don't assume someone that has an awesome logo is going to be great, but sometimes they are. There's a question I should have asked you at the beginning that I'm going to ask now. How many folks have you placed? How many companies have you worked with? And then also, is there a story of just your favorite person that you've placed/company you've helped hire that comes to mind?

**Lauren Ipsen** (00:33:36):
Yeah. So both great questions. I've placed probably 85 executives over the course of my career, and then lots of entry level employees when I was in house, and also some great key leaders. Yeah, probably 85 searches that I've opened and closed, so that's been incredibly fulfilling work. It's also fun too on the exec side of things because you hire the VP of engineering at Postmates and you see firsthand the product change. You know, you watch those types of things happen before your eyes, which is, it's fulfilling stuff, it's really cool.

**Lenny** (00:34:09):
And delivery gets there faster too.

**Lauren Ipsen** (00:34:10):
Yeah, yeah, exactly. So, that's really fun. Favorite placement of all time has got to be the VP of engineering that I placed at IRL, which is, to be completely honest, a big reason that I joined that company. Alex Strand is his name, and he is just the most incredible, atypical, high emotional intelligent engineering leader. Still super technical, but has managed teams in the hundreds, built out Amazon Prime Day, then went on to build the core messaging platform at Snapchat, called him and he was like, "Why would I ever leave? There's a ton of financial incentive and a team that I've built that all loves me."

**Lauren Ipsen** (00:34:54):
And we got him to ultimately make a move in two weeks, which is just kind of unheard of, although it ended up being like a seven month push for a start date, but that was a big reason why I went and joined IRL was to work side by side him and help build out his team and learn to get more deep on the technical side of things. Because oftentimes, on the executive level, as mentioned before, can be sometimes more of that people management type role. And so he just felt like this unique hybrid of an individual, and yeah, you close searches and you cross your fingers and hope for the best and feel very good about it, but he was one where I had all the confidence in the world that I could not have done better. You know? I just felt so great about that. So, that was a good one.

**Lenny** (00:35:38):
I don't know how much more confidence you could instill in a candidate joining a company than the recruiter also then joining the company.

**Lauren Ipsen** (00:35:44):
Yeah, I did say that to him. I kept saying, "And if I were to go in house, I swear this is probably the company I would do it for." And then about four weeks after he signed, I'd texted him and I said, "Well, you'll never guess."

**Lenny** (00:35:58):
Wow.

**Lauren Ipsen** (00:35:58):
Yeah.

**Lenny** (00:36:00):
Amazing. What a stamp of confidence.

**Lauren Ipsen** (00:36:02):
Yeah. And a full circle life moment. I sent him a box of cookies, he sent it back and said, "Your turn."

**Lenny** (00:36:07):
And is he still there at IRL? Awesome.

**Lauren Ipsen** (00:36:09):
Yes, he is. He's great.

**Lenny** (00:36:12):
**Lauren Ipsen** (00:37:51):
I think breadth is incredibly important. It's so critical, especially if someone has an end goal of wanting to step into a product leadership role to have been able to have touched lots of different components, as opposed to specializing in one specific thing. So I would say that's very important, to be able to make sure that you're maximizing opportunities for yourself down the road.

**Lauren Ipsen** (00:38:12):
And then as mentioned before, just always keeping a pulse on the market, regardless of how happy you are in your current company, regardless of what the project is that you're so incredibly excited about that isn't going to conclude until Q1 of next year. It's just so important that you always know the companies that are doing great things and keep those windows open for people, because you never know what the next 12 months hold, and you want to be in a position where you're never running out the door looking for what's next, but rather being able to be super selective about the things that you have in front of you. And that comes with time and network building and relationship building over years, honestly.

**Lenny** (00:38:54):
And when you say breadth, are you saying things like work on the platform team for a bit, work on the user facing team, maybe the internal tools team, like different types of product, or something else?

**Lauren Ipsen** (00:39:04):
Exactly that. Yeah. I think there's people that probably want to just be a specialist in growth, or want to get super deep on ads, and if that's the case, then by all means, do so. And I think there's something to be said about that as well because those types of skillsets will be needed. But if you're looking to diversify your skillset, continue to grow from a career trajectory perspective and think about potentially being in a head of product type role, I think it's really important that you touch all aspects of that.

**Lenny** (00:39:38):
I'm really happy to hear that because that's exactly the advice I give new PMs is that a variety of experience is one of the most powerful things you can do because you also just become a better PM because you can see how different types of products are built and how different types of teams operate and it just makes you better.

**Lauren Ipsen** (00:39:52):
Yes. Variety of experience, I think taking a bet on doing something more entrepreneurial, starting something, and then also joining things that are a little bit later and more established to get best practices. I think diversifying your skillset within an organization but also diversifying the work in which you're doing and the companies that you're spending time with is awesome.

**Lenny** (00:40:15):
Yeah. So on that, something I'm always weary of is folks jumping around between all the fancy companies to get a bunch of logos on the resume. "Oh, I worked at Snap and Facebook and Netflix," and I feel like you're just building a resume and then your life flies by, and you forget that you should enjoy the things you're doing and work on things that are fulfilling and optimized for not a great resume. And, curious your thoughts on just how often you think you should move from company to company, one to optimize for opportunities in the future, or just generally, do you recommend people try to move around or go deeper at their company? There's a bunch of questions there, but take it wherever you want to.

**Lauren Ipsen** (00:41:01):
Yeah, yeah. Okay. Sounds good. I think it's an interesting one because logo collecting is never something that you want to be known for, and the first thing you're taught, like entry level recruiting 101 is recognize patterns of candidates that jump from place to place and don't give opportunities a full chance. So, you're spot on. That is definitely not something you want to be known for if you're a prospect.

**Lauren Ipsen** (00:41:27):
There's also something to be said about staying somewhere too long though. And I will say that. I think sometimes you find people that are almost loyal to a fault, and companies have tanked and all executives have left and the writing's on the wall, and they're holding onto the fact that they were hired by a really good guy or gal and they want to make it work because they care about the human being, and I think sometimes in your career you do have to be a little bit more selfish and think about what's going to be best for you in the long haul. And so maybe that is still keeping your head down and working hard while also being thoughtful about other things that are out there and not saying hard nos to opportunities that knock on your door.

**Lauren Ipsen** (00:42:12):
So it's one where I would say it's an art and a science because you have to be thoughtful about taking on new things and knowing when it's worth taking a bet on yourself, but also you can't run as soon as things get hard because that is recognized, and if there's a riff or an internal dispute or a new leader brought in, and that is so quick as to make you run for the fences, that's not something that people look for because startup world is hard, tech is hard. Look at the crypto world right now. Things are incredibly volatile and difficult, and you want to be able to bring people in that are going to hang with you through the highs and lows.

**Lauren Ipsen** (00:42:55):
We're always looking to see where people moved the needle, especially on the product side, where their fingerprints were, what they can actually point to that they did and are proud of during their time there. And so if all that they can say that they did was onboarded and moved on, then doesn't matter where you were, but it's not going to be something that I can at least stand on to cheer you on.

**Lenny** (00:43:22):
I really like that. A lot of this comes down to, what impact have you made? And I was going to touch on that, and your point is, one, kind of heuristic for how long to stay at a place at the minimum is have some meaningful impact you can point to that you led. Does that sound right?

**Lauren Ipsen** (00:43:35):
Yeah, exactly. And have that meaningful impact be something that others can speak to. I think that's huge. If you built something within the organization that you're proud of but no one knows about it, then that's more difficult to have as your stamp of approval for what you are able to accomplish there. But if you did something that cross-functional leaders were speaking to, that your team all sings the praises of, then that is something that you can put a feather in the cap and say, "Okay, I left this place better than I found it, and that's the reason that I have decided to move forward."

**Lenny** (00:44:15):
And I imagine part of that is reference checks. People are going to check to see if you actually were successful.

**Lauren Ipsen** (00:44:20):
All the time. Yup. Whether you are exploratory, opportunistic, not looking at all, people are constantly calling each other, and the world of tech is so, so, so small, and no matter how fired up you were leaving a company or what went sideways, it is so critical that you try to leave the place better than you found it and do so as seamlessly as possible, because you want people to have nothing but positive to say. And oftentimes, that ... The thing that I always find too is if I call 10 people that were a part of the same organization as someone during a given period of time and they can't speak to anything they did, in that case, no news is not necessarily good news. You want to have an impact, you want to be able to say, "I did X, Y and Z. I'm super proud of this and the reason I moved on is because I did what I came in to accomplish."

**Lenny** (00:45:20):
It's a little bit innately tricky for product leaders. I imagine you run into this, that sometimes you have to upset people as a product leader to get stuff done that needs to get done and maybe they disagree and then later it's like, okay, I see what you did. Is that true? Do you deal with that or is it generally like, oh, yeah, they're the great people everyone knows, like a hundred percent of people will say they're awesome?

**Lauren Ipsen** (00:45:38):
It's a really good question. I think there's a way to navigate conflict without rubbing people the wrong way so that they'll say negative things. There's a way to be an impactful product leader and disagree and make change, and maybe your engineering leader and design leader and marketing leader completely disagree with the direction in which you're going, but because you have all of the data to support it and because you have gone about things in a way that feels very fact first and less emotional, it's really difficult for them to then point to why they disliked this person.

**Lenny** (00:46:19):
Yeah. This is interesting. So say you make those 10 calls, in your experience, the leaders you want to hire, are you finding 10 out of 10 are generally like, "Yes, this person's amazing, you should hire them"?

**Lauren Ipsen** (00:46:31):
There's ones that are slam dunks and no one has any negative to say. That's incredibly rare. More often you find some people like to just have something negative to say, just to have something negative to say. I also take all of my back channels with a grain of salt. Maybe the person I'm calling to back channel this person with I also haven't back channeled, right?

**Lauren Ipsen** (00:46:50):
So every single thing that you hear, you just take, make note of, and then move on and think more holistically about. But I think typically what I would say is the glaring nos are very obvious. People that are polarizing individuals or have done wrong within an organization or made bad calls across the board are, you can get that information typically pretty quick.

**Lauren Ipsen** (00:47:13):
It's the mixed ones where it's, "I think that person was decent," those are pretty tough, and you need to really find people that worked super closely with them because otherwise it's pretty difficult to say whether or not they were able to make an impact. Which again comes back to why right off the bat it's so nice to just have people that you can tap within every organization that's like an academy company or a great company and say, "Point me in the direction of the three best people." I don't want to have to go through the burden of having to try and back channel all of the maybe middle 50% or what have you.

**Lenny** (00:47:48):
Yeah, most people don't have that, which is a reason to hire, work with a recruiter. You come build in with all of that network.

**Lauren Ipsen** (00:47:55):
Totally. Totally there. Yeah.

**Lenny** (00:47:56):
There's a couple things I want to touch on that I wasn't planning to touch on, but reference calls. You do a lot of them, I imagine. And I'm curious, do you have any tips for how to ask questions on a reference call where you actually get useful advice where it's not just, "Yes, I like them, they're great. Hire them"?

**Lauren Ipsen** (00:48:11):
Especially on references, provided references, I've only had two candidates where provided references have come back negative, which that's tough. Outside of that, typically references are a standard. It is important to dig pretty deep and ask the hard questions.

**Lenny** (00:48:28):
What's the hard questions?

**Lauren Ipsen** (00:48:29):
Yeah, why would I not hire this person? What are their biggest weaknesses? And then if they give you the typical, "Oh, if they work too hard," it's like, no, tell me more. What are their actual weaknesses? What are things that we should be really cognizant of? Would you hire this person again? Would you report to this person? Would you endorse this person if you knew that your name was attached to it? Things like that I think get people thinking, and even if you just sense the slightest pause, that in itself will be enough to make you think twice. Right?

**Lauren Ipsen** (00:49:04):
So it's a lot of reading the room and probing harder than you think necessary, which is tough. But back channel references I think will always provide a greater source of truth than provided. It's similar to an Instagram Reel as opposed to the photos you're tagged in. That's the way I think of it. It's like this is what you want the world to see or think of you as, and then these are what your peers and your direct reports and the people around you actually say about the work that you did during this time.

**Lenny** (00:49:33):
Awesome. Coming back to a point you made about recruiter training 101, you learn how to find patterns and red flags in people's resume. What else is a red flag in your resume that you want to avoid/there's a rule of thumb of like, if you're at a place for less than a year, it's bad. Is that true? How do you feel about that? How do hiring managers generally feel about that?

**Lauren Ipsen** (00:49:53):
It definitely depends, with regards to being at a place less than a year. If that's a recurring theme, of course that's a big red flag. Even if it's happened two or three times, three definitely. If it's happened twice, it's like, "Huh, that feels off." You got to let people tell their story though and their side of things, and again, it comes back to reaching out to different people and understanding if what they're saying is true was actually the truth. And so when you have a really good pulse on what's happening in tech and whether there was a riff and the reason that person was let go was actually because they weren't prioritizing a certain part of the product or whatever, like those things, it happens. That's life, especially right now, right? If we were to X every single person that has a short stint that joined a new company over the course of the past year, that wouldn't do anyone any good.

**Lauren Ipsen** (00:50:44):
Another thing I've found that's pretty interesting is that people will often, because they're so afraid of that narrative, they'll often not include on their resume companies that they didn't stay for a year. And in my personal opinion, that's actually almost more of a red flag because that did happen, and you don't want to just pretend like that wasn't a decision you made in your life, and usually is handled with grace. You can speak to the reason that you decided to make a bet, the reason that you went there, and the reason that you moved on, in a way that people can typically resonate with. But I've seen executives just put that they've simply been advising for two years or something like that, when in reality they had two companies that failed.

**Lauren Ipsen** (00:51:33):
And the fact of the matter is, I have some CFO candidates I'm talking to right now and their past three years have been short stints because they were brought in to take a company through an IPO and then that changed, or they were brought in to enter into a SPAC and then that became less of the buzz. Right?

**Lauren Ipsen** (00:51:51):
So these things happen and roles change, and I think it's just allowing people to tell their story is the most important thing. So I would say red flag is, for me, just always be honest about when you started, when you left a company. If I see that someone still has present on their LinkedIn but they've been gone for two years and they kind of are acting like they're still there, that doesn't feel good. Just want people to give you the truth, the straight facts, so that you can support them and tell their story and represent them in a way that makes you feel like you have all the details.

**Lenny** (00:52:23):
Got it. So basically, don't lie. That makes sense. That reminds me a little bit of people kind of upgrade their titles a little bit because maybe they don't have an official title or they just want to sound a little important. How do you feel about when people do that on their resumes?

**Lauren Ipsen** (00:52:35):
Yeah, I don't love that. I also don't love on the resume when people, and some people do this and it's okay, but when people say silly, vague names like they'll say something along the lines of, "Whatever at Reddit," as their title or, "Master of blank at this," and it's like, okay, what were you actually doing?

**Lenny** (00:52:58):
But I think they do that to avoid recruiters reaching out to them.

**Lauren Ipsen** (00:53:00):
Exactly. As their direct target, I'm pissed. So I feel directly attacked in that regard. So that's something that throws me off, but that could definitely be a personal thing. And I think overall, for the most part, people don't have any other things that really just throw me for a loop. And the fact of the matter is, resumes we look at less and less, especially at the executive level, and it's a lot more of allowing people to tell their story, meeting in person, talking with their different people that support them, and getting kind of more of the big picture around who they are.

**Lenny** (00:53:33):
I want to talk about what recruiters often do wrong and what you've learned there. But before we get there, one last question: do you have any tips for a product manager in the interviewing process, how to be more successful interviewing?

**Lauren Ipsen** (00:53:45):
I've had this come up a few times when I've interviewed product folks that they'll speak down on their counterparts or say that the reason they weren't able to meet deadlines or push product in the right way was because of the engineering team or because of other components of the business and it wasn't them. And so I think that's never a good way to go about it. So it seems obvious, but you would be surprised how not obvious it is.

**Lauren Ipsen** (00:54:10):
So thinking about things more holistically, speaking honestly about your strengths and things that you want to continue to grow and improve upon, and then being able to tell your story, like practice telling your story. So often people don't do that, especially when they're not looking for jobs, and then it's not until their 10th interview that they know how to tell their story and what they did and what they impacted and why they were someone to be missed when they moved on. Those are things that you want to know how to speak to, and unless it's something you've been doing or practicing, it's less natural. That's some advice I think just off the top of the head.

**Lenny** (00:54:45):
Awesome. That's really good advice. One thing that makes me think about, I know I want to get to this last section, but do you think the best product leaders have their kind of story figured out in the future and work backwards from that and have a sense of where they want to end up, or just kind of take it as it goes? Because I'm the latter. I had no plan, I just went to see ... follow the path that was presented. Do you think that is generally true for folks that end up being successful, or do you recommend people think about, "Here's where I want to be in five years, here's what I need to do to get there"? Do you have any guidance there?

**Lauren Ipsen** (00:55:18):
I mean, for what it's worth, I'm definitely more with you. I don't know where I want to be in five years, so it's tough for me to say. But I do think that typically someone that has the end goal of being a CEO will put the pieces into place to try and get there, and so it's not a bad idea if you do have an end goal of wanting to run your own thing to inch towards that. So maybe you go from being a product specific leader to then operating in some type of GM of a business unit capacity and owning a P&L, and then although it's more of a product oriented role, you're still getting closer and closer to that end goal of COO or CEO.

**Lauren Ipsen** (00:55:53):
So if it's something like that, then I think that naturally makes sense. Do think people can be enticed by shiny objects, so excited because it's a step up from a title perspective and things like that, and I think that's just so not important in the grand scheme of things. You could be the VP of product or a CPO of what, you know? That's so vague. If someone just says, "I want to be a chief product officer, that's the end goal," I always say, "Of what?" You could be the chief product officer of your household. Is it of a multi-billion dollar consumer brand or ...

**Lauren Ipsen** (00:56:32):
So I guess what I'm trying to say is work backwards from a goal for sure, but don't allow titles or valuation bubbles or other things to derail something that feels good. If you're in a role and you feel like you're making an impact and you're learning and you're growing and are excited about the work you're doing, do not allow a title of some other company to make you feel like what you're doing isn't worthwhile.

**Lenny** (00:57:01):
I love that advice. So many people just chase some fancy new role, new title, new logo, and end up getting there like, "Man, this sucks."

**Lauren Ipsen** (00:57:08):
Exactly. Yeah.

**Lenny** (00:57:09):
This reminds me, I did a meditation retreat once and one of the teachings there was you don't want to be fixated with achieving a specific thing, but you want to push your cart in that direction, just like head that direction and have a general sense, but not, "I need to be that thing and that's what'll make me happy."

**Lauren Ipsen** (00:57:26):
Exactly. I think that's exactly right.

**Lenny** (00:57:27):
Awesome. Okay. Final topic is from the recruiter perspective, what do you find recruiters do wrong most often or miss when they're trying to attract great product talent to a company?

**Lauren Ipsen** (00:57:38):
Yeah, so this is one I feel especially passionate about because I do think recruiters have a bit of a reputation, and I think that it's for some good reason. There's naturally people that forget that these are human beings that we're dealing with every single day that have lives, have families, have careers, or ambitions outside of their career.

**Lauren Ipsen** (00:58:01):
So I think it's essential that you remember that this is another human being on the other end of things and that you should treat them with the same level of respect that you would expect to be treated.

**Lauren Ipsen** (00:58:15):
This has become even more apparent now that I have gone through some of my own recruiting cycles where I was looking for different jobs, and a transactional recruiting call just will rub you so the wrong way and will make you want to put things on your resume like I just alluded to that say things like, "Whatever at Reddit," or what have you because you just don't want to deal with it.

**Lauren Ipsen** (00:58:36):
And so I think you have to be a human, you have to start with a relationship, find common ground, build rapport, listen to people, like actually listen, and remember what they say. So if someone says, "I never want to do a crypto company," and I just am only shoving crypto companies down their throat, that's just insanely tone deaf. Or if they say, "I have this vest that I really want to be around for in May of next year," and I just keep hitting them up prior to that, that's just so not receptive to what they just said.

**Lauren Ipsen** (00:59:12):
Things like that, make notes if easier, because we speak to so many people all day long so it's definitely not easy to do. But I'll have a note on my calendar that John Kim's vest just happened in March, and then I'll be like, "Oh, okay, might be a good time for me to catch up." I won't say, "Congrats on the recent vest." I'll say, "You want to grab a coffee, or do you want to catch up about this?" Or, "Hey, I saw that you were speaking at this conference, love what you spoke about with regards to this." You got to find ways to connect with people outside of just shoving them into a job.

**Lauren Ipsen** (00:59:46):
And so I would say something that I've learned and become very good at is starting with a foundation of relationship building, gaining trust from people, because once you have that, then people will hear you out on jobs and people will listen to you and actually trust your advice from a career direction and perspective, but that takes time to build that, and it's definitely not going to be built by just chucking things at the wall and seeing what sticks with people and seeing where you can shove them temporarily. In fact, that will make them lose trust. And once you lose trust in a candidate, it's impossible to get it back.

**Lenny** (01:00:22):
It's interesting how one of the recurring themes of our chat so far is just play the long game in every way, which takes more time.

**Lauren Ipsen** (01:00:28):
Yes.

**Lenny** (01:00:28):
Kind of sucks that you have to put in all this time ahead of time before you really need to get something done, but what you keep coming back to is just that's how you end up being successful as a recruiter, as a product leader, as a hiring manager, as a founder.

**Lauren Ipsen** (01:00:39):
A million percent. Yeah. Yeah. And it's really easy when you've got a quota to hit and you've got people to provide for and a mortgage to just think about the numbers, but you have to play the long game because people aren't just a commodity. It's so much more.

**Lenny** (01:00:56):
And one of the perks of working with a recruiter is they have done that already for you, and so I was going to ask, when does it make sense for a founder to engage with a recruiter like yourself and when should they not?

**Lauren Ipsen** (01:01:08):
Engaging with recruiters sooner rather than later in a proactive way is always a positive thing. It's just sometimes companies aren't at the stage where they can necessarily hire a full-time recruiter because of resources and how expensive it is to bring in an exec recruiter.

**Lauren Ipsen** (01:01:26):
So having someone that you can bounce things off of in a more informal capacity, bringing in someone like a talent advisor that can help in a consultative way, those types of things, a million percent. Leaning into the venture firms that have backed you, which is a lot of what I'm doing right now, that is definitely areas in which early CEO founders should be leaning into that and trying to get as knowledgeable as possible. And then I would say typically series B feels ... series A, dependent on the check size, and then series B feels like a good time to bring in a couple key big players, if the company's well positioned to do so.

**Lenny** (01:02:06):
And bring in meaning full-time in-house recruiters or a firm?

**Lauren Ipsen** (01:02:09):
Probably bring in a firm. Yeah. That would be my recommendation. I think you can bring in one or two recruiters in the early days like seed, if it makes sense for the company and they're growing quickly, but it's all kind of case to case.

**Lenny** (01:02:22):
The fact that you're kind of off the table for most founders now that you're at GC, which is a part ... And is that true? Like you basically at this point work for General Catalyst founders, is that correct?

**Lauren Ipsen** (01:02:32):
I am supporting all of our GC founders in the consumer and crypto portfolio. That being said, I spend all day every single day networking and chatting with amazing entrepreneurs, people that could be founding a company down the road and need some advice, great people that want to help in an advising capacity. So it is, I would say, 50% networking, 50% actual parachuting into portfolio.

**Lenny** (01:03:00):
Got it. Okay.

**Lauren Ipsen** (01:03:01):
Supporting them.

**Lenny** (01:03:01):
That's cool. I didn't know that part.

**Lauren Ipsen** (01:03:03):
Yeah.

**Lenny** (01:03:03):
So outside of that, what do you suggest founders look for when they're looking for a recruiter, and the second to last question, what are signs that this is a good firm, a good recruiter? Just what should you be looking for when you're looking to hire a recruiter, either in house or a firm?

**Lauren Ipsen** (01:03:15):
I think it's important to provide them with some direction and then see if they can recite it back to you. Tell them the types of things you're looking for and then say, "Did that resonate? Because I'd love to hear from you what you took away from that and what you think we should be looking for."

**Lauren Ipsen** (01:03:32):
And then kind of off the bat, ask them for a couple candidate ideas. Don't give them time to just go call other people. In real time, ask them for some candidate ideas. Where does their brain go? Who are people they would call tomorrow on this? The more that you can get that dynamic relationship formed before you even go to search, the more you can determine whether this is someone you want to calibrate with.

**Lauren Ipsen** (01:03:54):
So yeah, I think just putting them on the spot a little bit and asking them to show their work rather than just sending over a deck of searches that could have been done by other partners or could have just been done by other people on their team. You want to actually understand who this person is. So that first question is testing their listening skills and their ability to actually hear what you're saying and what you're looking for, and then the second is, okay, now how quickly can we get calibrated on what this profile should look like.

**Lenny** (01:04:21):
Awesome. That is great advice. Very tactical. Any final words or wisdom before we get to our very exciting lightning round?

**Lauren Ipsen** (01:04:26):
This has been awesome, by the way. I think more generally, the advice is just treat people like human beings, build rapport, play the long game, and gain trust, and that takes time. And so those are the most important things from a recruiting standpoint, is being able to tap people and have them feel like you genuinely have their best interest at heart and that you care about their career and life outside their career. And so I think that's what makes for a really good recruiter.

**Lenny** (01:04:53):
Simple advice, but often forgotten and easy to overlook. Awesome. All right. We've reached our very exciting lightning round. I'm going to give you six questions, whatever comes to mind, we'll go through them real fast. Does that sound good?

**Lauren Ipsen** (01:05:08):
Okay. Yes. Let's do it.

**Lenny** (01:05:10):
Let's do it. What are two or three books that you recommend most to other people?

**Lauren Ipsen** (01:05:14):
The Power of Now and You Are Here.

**Lenny** (01:05:17):
Wow. Awesome. What are favorite other podcasts that you listen to other than this one?

**Lauren Ipsen** (01:05:22):
I mean, there's tech ones, but Your Own Backyard because I went to Cal Poly, so that one hits a little close to home.

**Lenny** (01:05:28):
Wow, I haven't heard of that. Cool. What's a recent movie or TV show that you've watched that you've enjoyed?

**Lauren Ipsen** (01:05:34):
Top Gun I've watched too many times and-

**Lenny** (01:05:39):
The new Top Gun.

**Lauren Ipsen** (01:05:39):
Yeah. And then TV show. Oh, it's all trash reality, so I just can't tell you.

**Lenny** (01:05:45):
I get that. I understand. My wife has that and she can't tell anyone. Yeah.

**Lauren Ipsen** (01:05:51):
That's my one secret.

**Lenny** (01:05:51):
All right. Okay, great. We'll move on, but that's great. What's a favorite ... Oh, this is interesting. What's a favorite interview question that you like to ask or maybe you've seen someone ask?

**Lauren Ipsen** (01:06:01):
I love the good strengths and weaknesses question. I think it's really good to see how people self-analyze themselves.

**Lenny** (01:06:06):
What do you look for in their answer that's the sign that it's well answered?

**Lauren Ipsen** (01:06:10):
Honesty, authenticity. Can read right through a, "Work too hard," answer or a perfectionist type answer. What are your weaknesses? Let's talk about it.

**Lenny** (01:06:19):
For real.

**Lauren Ipsen** (01:06:21):
So that one I think is always a really good test of character.

**Lenny** (01:06:24):
What are some favorite apps right now?

**Lauren Ipsen** (01:06:27):
I've been playing around on BeReal. I mean, I love Spotify, it's straightforward. And then I've been on Strava, I've been running, so that are the-

**Lenny** (01:06:34):
That's a good combination of apps. That's like a full life.

**Lauren Ipsen** (01:06:37):
Thank you. Thanks so much. Trying to be.

**Lenny** (01:06:41):
Final question. Who else in the industry would you say that you most respect as a leader and a thought leader influence type person?

**Lauren Ipsen** (01:06:49):
My first boss out of college, Joe Suliman, is awesome. He's always taught me to lead with that relationship-based approach and it's really so easy to say that you do that, but then to actually do it and live it out for the people that work for you, as well as the people that are in industry and speak of you, is something else. And so he's always taught me to do that, and I just learned a ton from him and he's just incredibly smart and in tune with what's happening in industry and makes great stances and opinions on how to navigate those types of things. So, he's someone that I have an immense amount of respect for.

**Lenny** (01:07:24):
Sounds like an amazing person. Lauren, this was excellent. I feel like this is going to be useful to so many people, product managers, founders, other recruiters, all kinds of other people. Thank you so much for doing this and making the time. Two final questions. Where can folks find you online if they want to reach out or maybe collaborate with you and learn more? And how can listeners be useful to you?

**Lauren Ipsen** (01:07:44):
Yes, absolutely. And also, thank you. This has been so much fun. They can reach out to me on LinkedIn. I happen to be on that one quite a bit, so definitely can DM me there, can send me an email, and I can shoot you that over as well. And then the way they can be helpful is if there's people that they think the world of, shoot them my way. If they have questions around best ways to go through an interview process or how to navigate different things, please, by all means, a huge part of my job is trying to help people that are going through this for the first time. Happy to just be a sounding board or of help in any capacity.

**Lenny** (01:08:19):
So if you're an awesome product leader, you want to see what's out there, find Lauren on LinkedIn. Is that the best place to find you?

**Lauren Ipsen** (01:08:24):
That's perfect.

**Lenny** (01:08:25):
All right. Awesome.

**Lauren Ipsen** (01:08:25):
Yep.

**Lenny** (01:08:25):
Thanks, Lauren.

**Lauren Ipsen** (01:08:26):
Thanks so much. Appreciate it.

**Lenny** (01:08:29):
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 Snyk built a product-led growth juggernaut | Ben Williams (VP of Product at Snyk)

**Ben Williams** (00:00:00):
Being able to identify the various micro and macro loops, how they're all connected, being able to document them in a qualitative model to communicate a shared understanding of how you grow, it's really powerful. Augmenting that then with the quantitative side of things that helps guide quarter to quarter focus and ensure you can be intentional about where you're investing, that becomes a big enabler. You're never going to have a shortage of ideas in a high performing growth team. So, knowing where to focus amidst that kind of sea of ideas is a really important role of the strategy.
**Lenny** (00:00:40):
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 Ben Williams. Ben is a VP of product at Snyk which is likely one of the biggest and most interesting companies that you've never heard of. Snyk makes it easy for developers to catch security issues in their code, and there's a lot to learn from how Snyk got started. It started through product-led growth, evolved into product-led sales, was very community driven, and it was also laser-focused on developers which has become one of the most lucrative markets to go after.
**Ben Williams** (00:04:47):
Thank you very much, Lenny. Thanks first of all for inviting me. It's a pleasure to finally meet you. I've got to say that kind of what you're creating with the newsletter and now the podcast, just such awesome resources for the product growth and wider tech community, so it's real honor to be invited onto the show, and I hope there's a few useful things that people can take away.
**Lenny** (00:05:07):
Awesome, man. I really appreciate that. I have no doubt there will be many useful things people will be able to take away. I'm really excited to chat about Snyk and the things that you're building there. I feel like Snyk is this very under-talked about company and also super fascinating companies, especially in terms of how it got started, how it scaled, and it's also at the center of so many trends, product-led growth, community-led growth, focusing on developers to grow, and also just security in general is really interesting, and so, I'm really looking forward to our chat.
**Ben Williams** (00:05:36):
Me too.
**Lenny** (00:05:37):
Before we get into all of that, I'd love to spend just a minute on your background. So, you're currently VP product at Snyk, and I'm curious how you got to that role and just some of the other wonderful things you've done in your career along the way there.
**Ben Williams** (00:05:51):
I'll try to keep it reasonably short. My education is in computer science, graduated from the University of Manchester back in the late '90s. I'd already landed as a job as a developer, but ended up having a bunch of other interesting offers, one of which was to join a small startup building requirements management tooling for product and engineering folks. This was all pre-Agile, but that whole space of developer tooling, engineering tooling, it was something I just felt naturally drawn to and it's where I've really specialized through my whole career. I actually joined that company as a solutions engineer, so lots of demos and so on. I was really close to the product team, but also speaking with customers every day which as is quite common I think was my path into products there.
Several years and a few acquisitions later, I find myself in IBM with the Rational software developer tooling group. I was leading parts of the product strategy there and a bunch of initiatives. I actually, I learned a ton of useful stuff there, but also that I had a strong preference for working in smaller, fast-growing orgs verse 350,000 people [inaudible 00:06:55]. After an interesting unexpected interlude, leading a DevOps transformation at a fintech and some consulting and advising, I then joined CloudBees. They're a DevOps startup with an open-core model. I was leading product design and growth there. Stayed with them for three years through several raises and a period of really fast growth before finally joining Snyk to build out our growth organization and lead our developer experience initiatives. I have a broad remit at Snyk now than just the growth org, but yeah, that's how it started.
**Lenny** (00:07:26):
Awesome. To give folks a sense of just how successful and big Snyk has gotten, one is just what does Snyk do, we haven't even talked about that yet, and then two, just some stats about the scale of the company and the business at this point.
**Ben Williams** (00:07:40):
The developer security company, we make it ridiculously easy for developers and their teams to improve their security posture while still moving fast. So, Snyk can find and automatically fixed vulnerabilities in code, open source dependencies, containers, infrastructure and cloud configurations, and all underpinned by the best security intelligence data in the market with a laser focus on developer experiences, which is why we're, we are really different. It's also an amazingly fast-growing business with some stellar PLG-focused investors and board members from the likes of Ed Sim at boldstart to Tamar Yehoshua, Slack CPO. We were founded in 2015, last valuation after our Series F was at 8.6 billion. We're securing the software of millions of developers now, well over 2,000 paying customers, now around 1300 people of which are around 500 in R and D with nearly 70 folks in our product org. And the people here just create this amazing culture, and all in all, it's just a really exciting place to be.
**Lenny** (00:08:44):
Okay. Did you have any sense it would get to this scale when you joined early on?
**Ben Williams** (00:08:49):
Yes, I think because I wasn't looking for a new role when I ended up joining Snyk, when I was first approached by them, but everyone I spoke with along the interview process, just became more and more impressed with not only the caliber of people here, but the vision, the mission for the company, and all those things you mentioned in terms of PLG, community-led growth, focus on developers, the security space, these were all things that if you create a Venn diagram of all the things that I'm really interested in professionally, super interested in, super exciting to me, then kind of Snyk ended up in the middle of it. So, it's pretty cool.
**Lenny** (00:09:29):
Awesome. So, that's a good segue to where I wanted to start is how Snyk started and how Snyk got their first hundred users, and I know you weren't there necessarily for that, but I'm curious what you can share about how the founders found their first say a hundred users. How did they get to their initial developers and get people excited?
**Ben Williams** (00:09:47):
I think it's a really fun story. So, if you don't mind, I'll just take a moment because I think it's important to set the stage by looking back at-
**Lenny** (00:09:52):
Let's do this.
**Ben Williams** (00:09:53):
Yeah, just look back at the market in general. So, PLG or bottom up and security, these were never words that were known to have been spoken together in a single sentence, right? So, security has always been a centralized function. Security programs were historically more about audit and policing and enforcement versus developer enablement or empowerment. A sales motion you saw it was always top down. It was seen as immovable, CISOs, other AppSec leaders with the buyers. Security tooling that was out there at the time, they all catered to this dynamic and these were tools that slowed developers down. They created a lot of frustration. They were met with a lot of resistance, not the ideal recipe really for consistent adoption and strong engagement and retention, and ultimately, app security programs based around those kind of solutions just weren't effective as they really needed to be.
**Ben Williams** (00:10:46):
So, it was a realization around this, timed with adjacent market shifts happening with DevOps that sparked the ideas behind Snyks. So, the founders, Guy, Danny and Assaf, they saw a real opportunity just to do things differently. They believed that the most effective way to improve application security posture was a developer-first approach. They knew that the developers were increasingly caring about the security of their code in the same way that they cared about performance and functional quality of their code. But they also knew that to empower developers to own that security, they needed just much better tools with way less friction than they ever had before. And their approach was, I think looking back, super smart, focus on a community. It wasn't the full extent of what we'd think of as community-led growth now, but it was close.
**Ben Williams** (00:11:35):
They started with a really narrow, early focus. It was a single persona, single context, single use case, and what that meant for Snyk was developers building applications using Node.js who wanted to ensure that the open source dependencies they were pulling into their apps were secure. Now, open source software, that's a huge accelerant in building modern software. The average software application today is at least 75% of open source libraries and components. So, this was increasingly becoming a primary attack vector for malicious actors who could find a single vulnerability in an open source component and then find it and exploit it in every single application that was using that component. And at the same time, at least back then, open source software was much less tested for security vulnerabilities, and the maintainers of open source libraries were often less security aware. So, you get that context, and then at the same time, Node.js as a run time was gaining traction. So, there was this increasing adoption in the enterprise, more and more dedicated conferences and the like, but the community was still small enough that Snyk could meaningfully influence, and Guy and the others just went all out on being deeply involved in that community. They were presenting at dev conferences, meetups, they were building online content and so on. And the question that they repeatedly posed to the community was do you have known vulnerabilities in your apps, and Snyk was there to help them answer that question. And fun kind of fact on the side, if you search for Snyk in the Urban Dictionary, you'll see it's an acronym for so now you know. But all of this kind of I think really only worked because of the parallel product-led approach. So, while the answer to the question about how does your product monetize users was much less clear cut in the early days for Snyk, the answer to the questions, how does your product acquire and retain users has always been product led.
**Ben Williams** (00:13:35):
And the initial version of Snyk, it was a command line tool. It was a tool for developers, it could be run locally or easily integrated into CICD pipelines for early feedback. It allowed devs to assume more responsibility for the security of their apps, and that was just very different from the typical incumbent technologies that were run by security teams late in the dev process, long feedback loops, issues thrown over the walls, inevitably just frustrating developers. And all of this was just built on this fundamental belief that the only viable path, and by viable I really mean sustainably effective, the only sustainably effective path for software-centric organizations to meet the challenge of becoming and staying secure was for them to take this developer-led approach to that challenge. So, really kind of complete disruption of the industry and developer adoption for that reason was always a key priority for us.
**Ben Williams** (00:14:31):
So, with that in mind, Snyk has just been free to use in some capacity from day one, and the early strategy was always about creating something valuable that was readily available, something that solved a real problem in a uniquely differentiated way, and making it pervasive. So, with dev-led option, this core concern, a freemium go-to-market strategy was just the obvious approach. So, eventually, getting back to your original question, that's all of the context and where and when and how they did it, but the first hundred or so users really just came from the founders engaging with the Node.js community and the interest that drove. I think we probably had maybe around 5,000 free users before there are any attempts at monetization.
**Lenny** (00:15:13):
Awesome. There's a bunch I want to unpack there because what's interesting the way you describe it maps to the series that I recently wrote about consumer growth strategy and how the first three steps after you have an idea is to come up with your super specific who, kind of your target persona, come up with a hook that catches them and gets them excited, and then go find them where they are and pitch them your hook. So, the super specific who for Snyk was you said open source developers working on Node.js. Is that right?
**Ben Williams** (00:15:41):
Well, it was Node.js developers, and Node.js developers were building their applications using open source Node components.
**Lenny** (00:15:50):
Mm-hmm. Got it. Was there any other constraint to that, do you know, or those were the two to three attributes of a user?
**Ben Williams** (00:15:56):
That's really it. The community was growing for sure. It was big enough to have a decent opportunity there-
**Lenny** (00:16:03):
Makes sense.
**Ben Williams** (00:16:04):
... but narrow enough that technology wise, it meant that a product could be brought to market in a reasonable time.
**Lenny** (00:16:10):
Yeah, that's great. And then the hook was basically you have known vulnerabilities in your code base which if I were an engineer, like, "I don't know, shoot, I don't know. Get a find exactly. I'm scared now."
**Ben Williams** (00:16:20):
Exactly. And then so now you know. Right?
**Lenny** (00:16:22):
Yeah, exactly. Okay, cool. And then the where, so you said that they went to open source communities. Do you have any more specifics about what those were? Was it like a specific forum? Was it like GitHub somewhere? Was it Reddit? Do you know any idea where those communities lived?
**Ben Williams** (00:16:36):
Yeah, it was less about a particular place, but more about the community of developers themselves who focused on Node.js. So, a bunch of early evangelism was really at conferences. It was I think the Velocity Conference in Amsterdam where Guy and Assaf kind of first unveiled Snyk to the world, and yeah, it went from there.
**Lenny** (00:16:58):
I see. Interesting. So, it was in-person events, conferences, and meetups probably focused on Node.js developers.
**Ben Williams** (00:17:03):
Exactly. Yeah.
**Lenny** (00:17:05):
Okay, awesome. What happened after that? So, that was the first hundred. Was it just roughly the next stage of growth or did it focus on that for a long time? What was the next stage roughly?
**Ben Williams** (00:17:14):
Yeah. I think that focus was the really important kind of element there, if I can kind of latch on that. Starting with that narrow focus and building around community engagement, I think it's a well-proven playbook now, particularly in the developer tooling space like New Relic did it notably with Ruby community for example. But ultimately it was important because of this kind of depth verse breadth approach and that depth-first approach that Snyk took was important to be able to effectively validate the solution on the path to product market fit. A JavaScript developer just won't care if you support Golang or Rust, but will absolutely care if a key feature like automated package upgrades just isn't available for their ecosystem.
**Ben Williams** (00:18:04):
Of course, the bigger problem of vulnerable components in open source across all languages and all ecosystems, that's a very widespread problem. It affects the industry at large, but that just spoke to the potential opportunity that was there to be unlocked. But the key for Snyk I think was just not to go too wide, too early. So, it focused on nailing that initial use case for that specific community of Node.js devs, like I say, narrow enough to be able to really focus on quickly building a compelling solution to a real problem, but also wide enough to be something viable from a growth perspective. And even back then the NPM, the Node Package Manager hosted around 200,000 open source packages. They were downloaded something like two and a half billion times a month by over 2 million devs. And the typical node app would have hundreds of dependencies, mostly indirect and so hidden less immediately visible. But each of those dependencies brought with it some security risks. So, yeah, I think nailing that narrow and deep-use case before expanding wider was absolutely critical and generally just sound advice around finding product market fit and building solid momentum before casting a wider net. It's difficult to maintain that focus for sure as the lure of that bigger term can be really tempting, but ultimately you have to build a service and market well to capture it.
**Lenny** (00:19:23):
Do you have a sense of when that focus expanded to an adjacent group, how many years into the growth story that happened, or was there some kind of milestone there? Because I know everyone imagines, yeah, we'll expand, the question is when and when does it make sense and when is it too early. Do you have any insights into that phase?
**Ben Williams** (00:19:43):
Yeah, for sure. First, I think if we're talking about PLG and the story with Snyk, I actually like that definition of product-led acquisition from Julian Shapiro when you spoke with him, and beyond that maniacal focus on finding product market fit for your product, founders really should be thinking about how their product is going to grow, and that's important of course as you think about taking that next step. So, let's assume in a simplistic definition that you found product market fit as demonstrated by a strong retention, and then the real question is where are the new users for your product going to come from, and founders really should have, I think, strong hypothesis around this, your risk essentially, adopting an if we build it, they'll come approach.
**Ben Williams** (00:20:27):
So, if your acquisition strategy is product- led, then understanding and being intentional about your early acquisition growth loops I think is an essential founder's responsibility. Dedicating time there to design those loops into the product, it's key. And when I say product, I really mean the whole product experience considering every touchpoint in and out of the core application that your users and customers might have with you. Snyk, for example, believed very early that we could build out powerful content loops via fixed pull requests that we raise on GitHub. New users, they'll sign up for Snyk, they'll connect their GitHub accounts, Snyk will scan their code, will find vulnerabilities, will automatically create Snyk-branded pull requests to fix those vulnerabilities. Other devs in the repo will see and interact with those PRs, and some of them will follow links to Snyk, create accounts and some of them will connect their own repos, and so the loop continues. So, company generated, company distributed content loop, it's actually really powerful for us because it's both an acquisition loop and an engagement loop.
**Ben Williams** (00:21:28):
Over the course of time, we extended that loop by adding support for other source controlled systems beyond GitHub. We layered on a bunch of new loops, and I think if founders can be intentional about this as you're developing early product iterations, then you're going to have a bigger advantage when the product clicks with the market, and that was built into Snyk as we went along. So, that was kind of ready as we found product market fit. But I think to talk about specifically how Snyk took that next stage, it was a function of when we were chatting before this, we talked a little bit about some of the failed experiences spinning up a self-serve revenue channel, and-
**Lenny** (00:22:09):
Actually before we get there, which I definitely want to get into all that, I love this story you just shared. I hadn't heard of this growth tactic of basically they connect their GitHub account, you find all the vulnerabilities, push a fix, people see that Snyk did this for them and it just provides all this value, and you're saying that was really effective. It's an example of something that worked very well.
**Ben Williams** (00:22:29):
First of all, that integration in terms of connecting your code with security scanning like that was a first of a kind integration.
**Lenny** (00:22:38):
Yeah, magic.
**Ben Williams** (00:22:39):
No one had done that before. But the key was that we ultimately controlled the content. So, not only was the fixed pull request doing something useful in terms of the code, but all of the description of the pull request was explaining about the vulnerability, educating users, and it was all Snyk branded and saying, "If you find this useful, click here, come and learn more about the vulnerability. Sign up for an account if you don't have one." It kept existing users coming back.
**PART 1 OF 4 ENDS [00**:
23:04]
**Ben Williams** (00:23:03):
You sign up for an account if you don't have one, it kept existing users coming back and it brings new users, a lot of new users, in fact.
**Lenny** (00:23:06):
You'd be in there all like, "Do you have known vulnerabilities in your code base? Click here to find out." Is that responsible for much of the early growth, that loop?
**Ben Williams** (00:23:15):
I think that was one of the loops. We also have a couple of, from fairly early on as well, other content loops that are more kind of programmatic SEO assets that have both been pretty instrumental in terms of new user growth, yeah.
**Lenny** (00:23:31):
It'd be cool to hear about those if they're relatively straightforward to explain, and then we can get to the thing that didn't work, the self-serve monetization piece you were going to get to.
**Ben Williams** (00:23:40):
We have a bunch of loops actually at this point to start off.
**Lenny** (00:23:42):
Lucky you.
**Ben Williams** (00:23:44):
Yeah, I'm a big loopist, funnily enough. But yeah, we have a bunch of loops. Company generated, company distributed content loops have actually worked really well for us. We have a side car product called Snyk Advisor. Snyk Advisor, it's basically a service that developers use to search and find open source packages when they're considering integrating some within their software applications. The unique thing about it is it indexes all of the package managers. It learns about those packages. It augments the data about them with a bunch of metadata, including of course Snyk security scans, but we also find out how actively maintained the software is on the source repo on GitHub or wherever.
**Ben Williams** (00:24:31):
We build this kind of package health score, so anyone searching on Google for a package that does X, Y, Z or a specific package by name, Snyk Advisor will be right up there in terms of the search results. They'll land on there, they'll get a good idea about that package, they can look at similar packages and it's all, of course, a Snyk website and we have CTAs to say, "If you want to secure your application on a perpetual basis, then just come and join us." That's a great loop. That's all kind of a programmatic asset. There are hundreds of thousands of these package pages, but they're just automatically being generated continuously.
**Lenny** (00:25:07):
Got it. It's programmatically generated better indexing of open source libraries that you can integrate with. That is so smart. It's programmatic because you can inform on the security vulnerabilities and then the maintenance and activity. Interesting. Yeah, that makes sense. That's all data you could just gather. That's awesome. Okay, so there's that. Is there anything else that's worked really well for you guys to help you grow self-serve?
**Ben Williams** (00:25:31):
One of the recent ones that's really interesting is security education. We think of Snyk as a change agent in helping DevSecOps transformations and it's fine kind of having this capability, but what we really want to get to is this position where developers truly understand and can be better placed to prevent security vulnerabilities being injected into their code. One of the things that is, again, something that's pretty different from the industry from an incumbent perspective is that we believe it's really important to democratize security education.
**Ben Williams** (00:26:06):
We have been building this bunch of really high quality but bite size lessons about developer security that focus on developers about security issues and vulnerabilities and we surface them. Again, they're out there in the public domain. There's no paywall to get access to those. All the traditional solutions you need to sign up, you need to pay to get access beyond more than a couple. But these were just, they're all out there in the public domain. That works really well for us from a company generated company distributed loop as well.
**Lenny** (00:26:36):
So cool. SEO and then integrating to GitHub in an interesting way. Imagine there's also a lot of intra-company virality when someone uses Snyk at a company and they spread it to their colleagues?
**Ben Williams** (00:26:47):
Yeah, I mean, I didn't talk about those. I think those are pretty well understood. We have both referral loops and invite loops as well.
**Lenny** (00:26:55):
Okay, awesome. Coming back to what didn't work, and I think you mentioned that there was a monetization attempt that was self-service oriented and that had some challenges. Can you talk about that?
**Ben Williams** (00:27:06):
At the time, a few things were in place. Valuable product, check, strong developer user growth, check, strong retention, check, but the first self-serve monetization efforts only really saw traction with individual developers paying a hundred dollars a month. Or purchases in larger companies, they just didn't happen as everyone had hoped. There was a really critical part of Snyk's history. At the time a bunch of investors didn't lean in, perhaps shy away from early conviction with the founders on building strong usage without a proven path to monetization at that point. Ed at BOLDStart who I mentioned previously, he was one of the first kind of true believers and was I think really key in helping with providing runway during that time. But it was clear that there was a lot of work still to do. The team dived in, they really figured out what the constraints were and through that process really learned about the importance of catering for the broader governance needs of the enterprise buyer.
**Ben Williams** (00:28:07):
And that meant a couple of things. First, there was a need to build out table stakes features around governance at scale. Just things that companies of a certain scale and size expected reporting, robust user management and so on. And second that it was time to move beyond that depth first approach, right? That depth first approach was absolutely critical in getting to that point, but it wasn't good enough to take the next step. If you think about it, there's a point in a company scale where you start to see diversification of tech stacks and all of those tech stacks need securing. It's obvious in retrospect that only supporting developers using a narrow slice of those tech stacks wasn't going to meet the needs of the security teams who were ultimately the people who were held accountable for the security of their entire application estate. The teams worked hard over the next few months starting to build support for additional languages and ecosystems and adding those table stakes features.
**Ben Williams** (00:29:04):
I think back then Snyk were simply ahead of this inevitable curve of developer first security. At the time, the only buyers were security teams and dev first Security for the most part wasn't something that CISOs and ApSec leaders were driving. But if you look at Snyk through that lens of, as I mentioned, being a change agent, being a key piece of the transformational journey of our customers' DevSecOps journeys, you realize how important it was for us to start to build relationships with those security leaders. It was that time also that it was the right time to bring in the first sales and engineering hires as well.
**Lenny** (00:29:48):
You basically found it couldn't work self-serve, independent of sales being involved in convincing the folks at the top, which makes sense. How do you trust a company with your security if the people at the top responsible for security aren't bought in? Makes sense.
**Ben Williams** (00:30:04):
Today it's less like that. There are organizations where the buying center is still very much ApSec, but there are also many organizations where kind of technical leaders on the buying decision around security investments. What was always true though even back then was the influencing power of developers, regardless of where the buying center was.
**Lenny** (00:30:28):
And I imagine as the brand has grown, it's gotten easier to convince people like, "Oh yeah, look at all these other logos using this. It's probably going to be okay."
**Ben Williams** (00:30:33):
For sure.
**Lenny** (00:30:36):
Just to understand in your experience with Snyk, it never really worked self-served monetization. It worked as a way to get into a company and then developers started using it in small scale, but you needed sales and marketing to really grow monetization. Is that what you found?
**Ben Williams** (00:30:51):
I think back then, yes. Now it's a very different story. We have a lot of self-serve only customers scaling pretty large, so.
**Lenny** (00:30:59):
Got it. That's interesting. I rarely hear that you start out with sales being important and it becomes less important or I imagine it's still very important, but there's like a segment that has emerged that can self-serve. Fascinating.
**Ben Williams** (00:31:14):
Yeah, I think it is important to acknowledge though, that the product has always played a really key part in the sales process for sure.
**Lenny** (00:31:21):
That touches on something I wanted to ask. [inaudible 00:31:24] you've mentioned him a couple times, he's got this awesome newsletter, he talks about you guys all the time. I think he's very proud of the progress of Snyk and he talks a lot about that for developers, you got to win hearts and minds of developers to build something that works. Any lessons or pieces of advice for folks that are targeting developers to win hearts and minds and get engineers, developers excited about what you're building?
**Ben Williams** (00:31:47):
I think there's two things, right? First of all, fundamentally for someone to get excited about using a product, they've got to care enough, right? They've got to have a problem that you're solving. I think there's two things. One, there is a shift that is happening and still happening. I think there's still a long way to go for developers to really care about security as an integral part of their job in the same way they think about functional quality or performance. I think that we're still, we're making strong progress there. It's changing all the time, but there's still a long way to go there. But the reality is that I think in most companies, developers have to care about security because their companies need to be secure. The key then is how do I make the job of being secure for these developers, as painless as it absolutely needs to be?
**Ben Williams** (00:32:44):
And that means really meeting them where they are, integrating with their tools, finding ways to take security to them instead of trying to pull them out of their workflows. Flow is just this incredibly important concept for developers and you want to strive to keep them in that flow for as long as possible. The GitHub kind of pool requests are a great example of that. Someone can sign up for Snyk and they could theoretically be the only user of Snyk and connect their repos. All of a sudden we're protecting, securing those repos, a hundred, a thousand developers could be working in GitHub with that code, all benefiting from Snyk without necessarily needing to sign up. That's that example of taking the product to users without pulling them out of their workflows. I think that's absolutely critical.
**Lenny** (00:33:38):
As an outsider hearing all this, it's a product that magically helps you avoid security issues, very little work, does a lot of the work for you. It's hard to imagine it not working looking at it now, and I'm curious what it was about the early days that just felt like maybe that people didn't believe in this working. Is it just there was doubt that it would be smart enough to find your security vulnerability issues? Was it the timing wasn't right, people weren't ready, weren't concerned about security enough? What do you think it was that created challenges early on? Because looking back, it's like, of course this is going to work. How could it not? It sounds just like a magical all win product.
**Ben Williams** (00:34:16):
First of all, don't think the challenges were there in terms of the developer adoption. Even when those first kind of forays into self-serve were struggling in terms of breaking into some of the larger customers. The developer adoption, the free user base was still growing at a really good pace. That momentum was just constantly building and it's that momentum that has ultimately fueled the sales led business as we've gone through the years. But it was just those few things I think that I mentioned earlier in terms of stumbling blocks that needed to be overcome because when those first sales and marketing hires did join us and we started having conversations and we also tweaked some of the things in the product to meet, had some breadth, had some additional languages, ecosystems, building those table stakes features, then it really unlocked and it was rocket ship time from then.
**Lenny** (00:35:11):
Got it. Sounds like the biggest issue is monetization. Can we make money doing this? Developers love it, they're using it like crazy, but will people be convinced to scale this an inside an organization and pay us a bunch of money for it?
**Ben Williams** (00:35:21):
Exactly, yep.
**Lenny** (00:35:22):
Okay, got it. I want to dive a little bit deeper into your growth team and product team and how you think about organizing teams like that in a product led growth sales org. The first question, just how did the growth team start at Snyk? What was kind of the early days and then what does it look like today?
**Ben Williams** (00:35:41):
There were some ad hoc efforts happening in various places. We had a small growth marketing function, we had [inaudible 00:35:49]. We also had some ownership of key growth services in R&D. There was a team that owned the new user onboarding flows, for example. But it wasn't until I joined that we really formalized the notion of a growth team. It was very kind of ad hoc before then. When I joined, we created what we call the developer growth group now. Before then there maybe wasn't strong an understanding about what a growth team needs to look like, how they might need to work differently to the core product teams. And I'd say overall it was much later than you'd typically expect to see. And at a bigger scale. You normally are going to start growth teams, one or two people, three or four maybe, and scale out from there. But we started much bigger than that. But at the same time, this bottom up developer first approach, it was baked into the company DNA in terms of how teams think and operate. Yeah, we were growing fast even before we spun up the growth group. I think the significant change that happened there, it was a transition from a simple freemium approach to a holistic and well-coordinated PLG strategy. It's much more common to start earlier, much more common to start at a smaller scale than we did at Snyk, but it worked for us because of this kind of perfect storm of where we had a product with that bottom up growth built in from the beginning. We had founders with a deep appreciation for how the product could grow and there was strongly exec alignment and sponsorship for scaling the motion. The problem when starting the growth group, it was really for the most part more oriented to how we can get the flywheel spinning faster as opposed to getting it moving in the first place.
**Lenny** (00:37:26):
Where did you initially focus that team? Which part of the flywheel?
**Ben Williams** (00:37:30):
Right now we have dedicated teams focused on acquisition, activation and monetization along with a supporting team who own our growth platform, including all of our data and experimentation stack. But the macro structure, it's changed over time to enable us to focus on the biggest constraints in our growth model. At the beginning we just focused on acquisition and activation, intentionally deferring any investment into specific monetization initiatives around the self-serve revenue channel until we felt confident that A, we'd built the necessary growth muscles to scale, and B, we'd figured out some of the more pressing issues that were present earlier in the user journey. It was important that we felt really confident about our ability to effectively connect developers to Snyk's value in such a way that introducing and optimizing a self-serve revenue channel would make sense. I also really wanted to avoid one of the common failure modes I've seen around cross-functional collaboration and growth.
**Ben Williams** (00:38:28):
When I joined, there was an inherent tension built into the system. It was particularly noticeable between R&D and the growth marketing team. We had amazing people in both teams, a ton of really great ideas, but many of them were just not being executed on and it was leading to a lot of friction, a lot of frustration, ultimately caused by misaligned incentives between the different functions. When creating the growth group, we resolved this by ensuring that each of the growth teams were truly cross-functional in nature with everyone in each team aligned around common objectives and KPIs. Every team has engineers, an engineering manager, a product manager, a designer, a growth marketer, decision science support, and a basic shape of the growth teams that'll be familiar to most, but I spoke to a bunch of people over the last couple of years and I've actually learned to my surprise that inclusion of growth marketers in the product teams is not all that common. And I personally think there's just a lot of opportunity being missed there and I expect that to start to become the norm rather than the exception over time.
**Lenny** (00:39:32):
Okay. I want to talk about that, but before we get there, you said there's a decision science person on the team. What is that about? That's cool.
**Ben Williams** (00:39:38):
That's right. We started off from a fundamental BI data analyst perspective, but over time we wanted to apply a much deeper level of analysis on the data such that we could start to build in predictive models that could help us make better decisions and can ultimately fuel and power some of the end product experiences. Yeah, we spun up a decision science function and those folks are very smart.
**Lenny** (00:40:13):
Is that similar to data science or is that a separate ... Okay. It's cool that you call them decision science people versus data science, because that's so much more actionable.
**Ben Williams** (00:40:23):
Yeah, I think so.
**Lenny** (00:40:24):
Wow, that's cool. All right. I haven't heard that before. Makes me think of Annie Duke and all the stuff about how to make better decisions and I love ... Is this something anyone else does or is this something you came up with calling [inaudible 00:40:38]-
**Ben Williams** (00:40:37):
I'm not sure. I don't necessarily think what we are doing is revolutionary there, but maybe the name, I'm not sure.
**Lenny** (00:40:46):
Yeah, the name is cool. I haven't heard that before. It implies bias towards action versus just we're going to do a bunch of cool stuff with data. Interesting. Okay. Then you said that there's a growth marketer embedded in each team, so maybe just broadly what makes up these teams? Which you touched on briefly, then what have you learned is the value of having a growth marketer embedded within each team?
**Ben Williams** (00:41:06):
It's important to have balanced teams with strong diversity across multiple vectors. Focusing on functional diversity at the moment, which is kind of what you're asking about with having growth marketers on the team, one of the big benefits you get is a broader pallet of ideas, but also a bigger toolbox when it comes to execution, which generally translates in an ability in a growth team for them to test and learn faster with more parallel, yet at the same time, aligned threats. Perhaps I can give a recent example there. Having a growth marketer in an acquisition focused team led us to some lightweight experimentation on the website in creating an SEO optimized page. It was something that was really high performing, both from the perspective of traffic and conversion, but it didn't require any engineering resources to create. The growth marketer and the team, and they decided together this was something worth pursuing.
**Ben Williams** (00:42:01):
But the growth marketer was able to kind of execute that independently while engineers were working on other things. But then based on the success of that, the team went on to build out a functional sidecar product that allowed users to basically try Snyk without needing to sign up by simply placing their code in for us to scan and giving them some results there and then. We saw really great results with that visitor traffic, saw a significant increase, sign up rate dropped a little bit as we'd expect it would, but overall new users had a big bump and those users had much higher intent, which we saw play out with increased activation rates.
**Lenny** (00:42:37):
Awesome. Okay. And so there's essentially four teams under the growth umbrella. There's acquisition, activation, monetization, and then this kind of experimentation platform team. Is that right?
**Ben Williams** (00:42:47):
Yeah, that's right. And that team is also responsible for making that data available elsewhere in the organization as well. Product led sales is a really important motion for us, and so taking the knowledge we have, the insight we have around behavior with the users and their teams and their companies within the product, and making that available to the GTM teams outside in smart ways, allowing them to focus on the things that are most important to focus on. That's a really important part of what that team does.
**Lenny** (00:43:20):
It's interesting, you guys are the epitome of product life sales. That's this new trend of from PLG to PLS for sales. It's obvious that they're a big part of this whole process. The fact that monetization happens almost all through sales is interesting. That's interesting. Cool. Okay. That's not a question, just a thought, talking out loud. One other thought I had is, so you talked about SEO being a really important part of your growth. What is the person team like to do the SEO piece, the right content? I imagine they're on the acquisition team, there's maybe a content person that lives within that team.
**Ben Williams** (00:43:55):
We have actually one of, the smartest SEO people I've ever met within [inaudible 00:44:02].
**Lenny** (00:44:02):
What's their name? Let's give them a shout out if you want.
**Ben Williams** (00:44:03):
Anna. Yeah, cool.
**Lenny** (00:44:05):
Joanna.
**Ben Williams** (00:44:05):
Well, she's part of growth marketing, but she works extremely closely with the growth teams and she's got a few people in her organization and we bring them into specific SEO focused initiatives when we're looking to build loops around that. Incredibly important to have someone like that who understands that at a far deeper level than I could ever hope to, how SEO works. And particularly in terms of keeping on top of some of the things that Google are constantly doing in terms of their algorithm changes.
**Lenny** (00:44:37):
And does she actually do the writing for editorially, for I guess even the programmatically made pages or there's someone she outsources-
**Ben Williams** (00:44:43):
No, but what she does do a great job of is providing the kind of continuously updated guidelines on how content should be structured to lead us to good results.
**Lenny** (00:44:55):
Then it's just engineers and PMs that end up writing the things? Wow. Cool.
**Ben Williams** (00:45:00):
Yeah, that's exactly right.
**Lenny** (00:45:04):
**Ben Williams** (00:46:34):
This is a big topic. I have a lot of thoughts here based on what I've seen work well and also not so well. I think I can broadly bucket things here into maybe three main topics. So the first would be people and process. The second would be strategy, and the third would be data. Now they're all related and they all have to be working well to be effective in growth. Starting with people maybe touch the first element there in terms of balance teams, you've got to have those balance teams with diversity and ability to create great ideas, but also ability to execute. So that's the first thing.
**Ben Williams** (00:47:14):
But still on the topic of people, I have this kind of mental model, that potential that at its core is unbounded, but that a bunch of things situationally prevent people from fulfilling their potential. It might be how they're thinking about something. It might be organizational. It might be in relationships with coworkers or in broader team dynamics. It might be in them not even being in the right role even.
**Ben Williams** (00:47:37):
So fundamentally I think it's the role of managers and leaders to help them identify those things and work with them to find ways to thrive and grow. And I've seen this have particular significance in a growth org where people are just naturally less good fit. Now that doesn't mean that they're not amazing talented humans. It just means they aren't going to do their best work in a growth context.
**Ben Williams** (00:47:59):
So when you're starting a growth team, you'll often be doing so with internal moves. So this can be something that's maybe a little bit easier to miss than with external candidates where you are likely testing for those things explicitly during the hiring process. I'll share an example with developers.
**Ben Williams** (00:48:17):
So the devs that really thrive in a growth context are the ones that are motivated by moving quickly, iterating to create measurable impact. They're not attached to their work. They embrace imperfection as part of the process. They happily discard their code, their ideas even. They're curious and they're always looking for ways to be closer to their users.
**Ben Williams** (00:48:38):
Now those are the folks that generally make great growth engineers and I've also known incredible engineers that are most motivated when they're working on really deep technical challenges and love the process as much as the outcome. And they've struggled in growth. Of course it's never that simple in reality. There's nobody who's really at either extremity of that spectrum. But it's really important to try to answer the question, can this person do their best work in this environment? So I think that's a really key part of it.
**Ben Williams** (00:49:10):
And yeah, you need to also make sure they're well equipped from a kind of skills and knowledge perspective as well. So they need the right skills and knowledge to be able to do their best work in the context of your growth process. So the ideal state is that every growth team member has common vocabulary. They're comfortable with the growth process. They can work well with data and experimentation platform. They understand the data. They have the right skills and mindset.
**Ben Williams** (00:49:36):
Education I think plays a big part here. So we're big fans of Reforge, but we've also developed a bunch of internal programs to align and uplevel the teams. Something we learned, I think as an example, is the importance of starting simple and going deeper as the teams build experience. So for example, when it comes to experimentation, don't try at the beginning to introduce multivariate testing or concepts like sequential samplings and alternative evaluation approach.
**Ben Williams** (00:50:04):
Teams are still trying to just dip their toes in that... This water, it's kind of a recipe for a lot of mistakes. So that would be some advice there.
**Ben Williams** (00:50:15):
But people also need to be well aligned. I've talked about this actually on another podcast that I did recently. But what I mean by that is their execution needs to be aligned with an evolving growth strategy. The growth strategy needs to be aligned with and at the same time influence where the company's going. The growth strategy needs hooks into the product strategy and ideally there's some overlap and alignment of KPIs so that the growth teams and the core product teams are swimming in the same direction. The skills and experience in the team need to be aligned with the strategy. If you've got to focus on activation and acquisition, then someone who's a plans and pricing expert probably isn't the right set of skills at that point in time.
**Ben Williams** (00:50:57):
But you also, leaders need to plan to ensure those skills are available as focus of the growth team inevitably shifts over time. But at the end of the day, I think everyone needs to be able to easily answer the question why they're there. Why the work they're doing is important.
**Ben Williams** (00:51:14):
I don't know if it's too far off track here, but I have a vision and mission framework that I like to use that leads to I think, great simple statements of an imagined better future state and your role in getting there. So I can talk about that a little bit if it's a-
**Lenny** (00:51:28):
Yeah, let's do it. That sounds too good to pass up.
**Ben Williams** (00:51:31):
-Cool. So the vision is the nirvana state that you aim to enable for your users and customers in five to 10 years. It's something that could equally be enabled by your competitors if you don't execute effectively or efficiently or quickly enough. You can always prefix a vision statement with in the future, dot, dot dot.
**Ben Williams** (00:51:52):
Now it's something that should be bound to your target market. So not too wide and not too narrow. And critically it should not mention your company, your product, or anything solution related at all. Completely agnostic of those things.
**Ben Williams** (00:52:05):
And then the mission, that's the thing that you are going to relentlessly iterate on to take you incrementally closer to the nirvana state described in the vision. It should answer how you'll realize the vision by describing what your fundamental approach will be. In other words, what you will do and how you'll do it. It should ideally aim to encode any unique differentiating advantage you have. So if I think about Snyk at large when it comes to advantage, we might mention our unequal security intelligence and knowledge of application context.
**Ben Williams** (00:52:36):
And one of the neat things about this framework is if you find utility in doing so, you can apply it at every level from the company level all the way down to individual team. It doesn't mean the process is not difficult and you need to spend a lot of time, but it gives you this set of kind of a framework, a set of bounds that help you really come out with world crafted statements that kind of stand the test of time.
**Lenny** (00:53:00):
Is there an example you could share of the mission vision, whether it's Snyk or something else?
**Ben Williams** (00:53:03):
Yeah, yeah. I'll give you one for the growth group of Snyk. So great. The vision, every developer securely unleashes their creativity and the mission is to connect every developer and their organizations to the value of the Snyk platform with frictionless self-serve, adoption and expansion.
**Lenny** (00:53:19):
Interesting how the vision is so big beyond Snyk's current focus. And to your point, this kind of trickle down, right? There's a company vision and mission and it's the growth team's mission vision.
**Ben Williams** (00:53:32):
Yep.
**Lenny** (00:53:32):
Awesome.
**Ben Williams** (00:53:32):
Exactly.
**Lenny** (00:53:34):
I want to shift a bit and talk about your product work. So we've talked a lot about the growth org. I'm curious what the broader product org looks like. How many teams do you have? How do you structure it? Is it like product focused, user focused, outcome focused? And then just how does that team work with the growth team?
**Ben Williams** (00:53:53):
Sure. Happy to go into a bunch of that stuff. I know I'd mentioned earlier kind of three areas of building a growth team. I don't know if you want me to cover those other two. 'Cause we talked about-
**Lenny** (00:54:02):
Oh yeah, okay, let's do that. Let's finish that thread.
**Ben Williams** (00:54:05):
-Cool. So people and process was the first and we'll cover process really quickly. I think on the process side, at a minimum here you need well understood, documented growth processes, practices, working cadences. Teams in growth need to work differently in some ways from R and D teams working on core product, assuming otherwise, and just giving growth responsibility to an existing team without working with them to implement appropriate ways of working. I think it's a common track.
**Ben Williams** (00:54:31):
Ideally you get to a point there where the growth process is something that's continually refined and iterated on trying to build in more predictability. But what I've found I think most singularly most important in a growth process is facilitating a rapid learning cadence and providing the means to socialize those learnings, surfacing them in the right place at the right time so they can be leveraged and at the context. And if you think about experimentation, it's not about delivering outcomes it's about generating learnings that the organization can leverage effectively to deliver outcomes.
**Ben Williams** (00:55:05):
Might not be now, might not be tomorrow or some point in the future. But the sad reality is that without good process learnings easily end up unused and gathering dust. And you have to ask then what was the point? So as people in process and you know when that's on the right track, when you start to see enthusiastic sharing of learnings, when you see regular contribution of ideas coming from everyone in the form of well crafted hypotheses that are based on data and learnings. And when you see a wide variety of folks, just assuming end to end ownership of managing and running experiments instead of delegating that to the product manager or an engineer and tech lead. So yeah, that's people in process and strategy is-
**Lenny** (00:55:48):
Let me throw in a question real quick before we get to the last piece.
**Ben Williams** (00:55:50):
Sure.
**Lenny** (00:55:51):
So learnings, just to kind of touch on that. I've heard more and more pushback on the idea of learnings being an outcome. Because a lot of... As a leader, you're not going to be like, Cool, we learned so many things but nothing really got done. How do you think about the tension between, yeah, learnings we want to learn, but we also want to move metrics, grow the business and learnings are a way to inform decisions more than even just learn. How do you think about that kind of balance?
**Ben Williams** (00:56:17):
Ultimately you're there to create impact, right? There's no getting away from that, but learnings is the means. It's the same as, there's a quote that I love from [inaudible 00:56:27] around focus on the user's path to value not on monetization. Because if you focus on the form of the latter will follow, and that's the same thing with learnings and impact here. If you try and focus on the impact itself might struggle. If you focus on the things you need in terms of learnings to take you step by step, that will pave the path to creating impact.
**Lenny** (00:56:47):
I imagine your OKRs and goals are still like move this metrics some percentage, but you think of that as an output and the input is let's learn a bunch of stuff about what works and doesn't work and use that to inform what we're going to double down on.
**Ben Williams** (00:57:00):
Exactly. Yeah.
**Lenny** (00:57:00):
Sweet. Okay.
**Ben Williams** (00:57:02):
You got to focus on when you build a strategic opportunity, you are thinking about the outcomes, but you don't just go right to the end state. You've got to think about what's the quickest way we can test this hypothesis? And from there, what we learn from that and what do we take into the next set of the next set of experiments and it... You're paving this path along the way. You kind of that rough destination. How you get there, you don't know at the start. And that's what the path that the learnings take you on.
**Lenny** (00:57:31):
Cool. Okay. And then strategy we're talking about.
**Ben Williams** (00:57:34):
Strategy. Yeah, so strategy, it's a good one. At a very basic level, you need to be able to answer questions. How do you acquire users? How do you retain users? How do you monetize them? I know you talked with Elena on that in more depth, but from there you need more detail. It's going to guide the growth teams and where they look for strategic opportunity, how they approach that. The best way I've found to articulate a growth strategy that fulfills the promise of usefully guiding the team's execution, it's the loop based model, Reforge, as specific kind of documentation that I think is great around that.
**Ben Williams** (00:58:15):
Being able to identify the various micro and macro loops, how they're all connected, being able to document them in a qualitative model to communicate a shared understanding of how you grow. It's really powerful. Augmenting that then with the quantitative side of things, that helps guide quarter to quarter focus and ensure you can be intentional about where you're investing. That becomes a big enabler.
**Ben Williams** (00:58:40):
You're never going to have a shortage of ideas in a high performing growth team. So knowing where to focus amidst that kind of sea of ideas is a really important role of the strategy and fairly on, you'll probably have one or two core loops, but inevitably you'll need to layer on and connect new ones over time. And having a framework for doing that and having a framework for regularly revisiting that in the context of growth, team learnings, changes in broader company strategy, evolution of the product, new features being added, and so on. Market shifts, that becomes a big up level for teams to be able to create timely impact.
**Ben Williams** (00:59:19):
So the model you create there is what enables you to know at any time where the biggest constraints to your growth are and allows you to balance your growth investments accordingly. It's neat for sure. We've had times where we've focused on a broad set of constraints and opportunities and other times where we've had a much narrower focus. For example, on driving improvement to activation and engagement, even more narrowed like doing that through empty states, for example.
**Lenny** (00:59:44):
I want to unpack the strategy piece real quick. How do you operationalize this idea of you have this growth model, growth loop, you figured out here's the ways we're growing. How do you tactically connect that to a strategy? Is it, here's how we're growing, here's where we're going to focus this quarter, optimize this part of the loop, or is there some other way? You write it down, basically.
**Ben Williams** (01:00:05):
Very simply, it's first of all alignment on how you grow the different loops, how they work, the roles of different teams and the roles that they play in fueling those loops and getting them to spin faster. I think that's the first thing, having that common vocabulary and understanding.
**Ben Williams** (01:00:25):
Second is understanding the way they work in terms of what is constraining them, what are the inputs to them? What are the opportunities for making those loops spin faster? How can multiple loops work together in a macro context?
**Ben Williams** (01:00:41):
And particularly using the data there to be able to identify and understand and get alignment around where are the biggest constraints in your growth model overall and therefore where are the things that we need to focus on as a team over the next quarter or two quarters, and so on.
**Ben Williams** (01:01:01):
And that it's constantly changing. As I mentioned, there's a bunch of stuff that needs to feed back into that model in terms of growth loop performance or the learnings you're making and so on. That means it's changing and you're constantly reevaluating and it's guiding kind of quarter to quarter planning.
**Lenny** (01:01:19):
Cool. So just to make it even more concrete for folks that are listening. So one of your loops is this integration with GitHub where you automatically fix their code and create a PR. You may find at some point somebody clicking that link to becoming a user is too high friction, too many people are falling out. So one strategy for one of say the activation team could be we're going to optimize this part of the funnel. So when clicking from GitHub to sign up as a user and get them to a point where they found value, right?
**Ben Williams** (01:01:48):
Yep. That exactly that sort of thing. Or earlier on, for example, it might have been with that taken that same example of that same loop, and this is sufficiently far in the past that it's easy for me to talk about. But we start with GitHub. We want to now expand the scope of that loop. We've seen success with it. We see the performance of that loop growing, but we think there's opportunity in saying let's expand that by adding support for Bitbucket. And now all of a sudden we spin up that same loop with Bitbucket and then GitLab and so on.
**Lenny** (01:02:20):
Awesome. Okay. We could go a whole hour on just that piece, so we'll move on and we'll save that for feed two.
**Ben Williams** (01:02:26):
Data was the last thing. And growth team just can't function without data that even with early stage products, before you have the needed volume of traffic to be able to run formal tests in reasonable timeframes, you still need to have signals that help you learn and inform your decisions, both quantum and of course qu through speaking with users. My advice there is really just to invest early the infrastructure, the tooling then at a given scale, the dedicated people as well. They're going to be core to building out the growth team and they'll enable data to ultimately pretty much inform all critical decisions.
**Ben Williams** (01:03:01):
So Snyk was interesting that we didn't have a problem of not having enough data. In fact, there was an abundance of data, like too much. We collected absolutely everything. And the problem I identified very early was that we didn't have enough behavioral specific data and we weren't intentional enough about the data that we were collecting and how we were collecting it, which made the data hard to trust and that becomes a big problem.
**Ben Williams** (01:03:26):
So we invested in tooling and processes for building out event tracking plans, and now we test conformance to schema of the instrumented code in our CI processes. So we have absolute confidence in the data. So that was getting to a point of trustworthy behavioral data was absolutely key.
**Ben Williams** (01:03:43):
But the reason I say invest early here is that to remember that it also takes time to accrue enough data that you can learn about and make some key decisions around retention, for example. Also that you have enough data to run regressions on, be able to inform definition of your activation metrics or engagement states and so on. So the earlier you can start collecting the better. So yeah, people in process a strategy and data and you absolutely need all of those things to build and run an affected growth team.
**Ben Williams** (01:04:14):
When you get all of those things working, it's like rocket fuel for focus creativity, but at the same time slowing down to put the maturity in place as on all scales at the pace Snyk has it's pretty much impossible. You still have to get stuff done while you're kind of building all that stuff out. You have to accept that you're going to make a bunch of mistakes along the way. You have to be a hundred percent comfortable with that. And you have to treat those mistakes as learning opportunities that provide leaves for improvement.
**Ben Williams** (01:04:43):
And it's also useful to... You know, asked about KPIs and what the team are responsible for it. And that is one way in which a growth team absolutely needs to make impact and it's the way that primarily they're going to be held accountable. But it's also I think, useful to think about the efficacy of the growth org, not just in terms of the impact they drive our experiments and new product experiences and on core growth pick KPIs, but also how they enable and uplevel the rest of the org.
**Ben Williams** (01:05:10):
So for example, our entire product led sales process, it's powered by an evolving model that describes our understanding of users, teams, accounts, the usage and adoption patterns and signals, the best in form where and how our GTM teams focused. Insights from growth teams often have utility far beyond growth, but people can't know if something is useful to them if you haven't shared it with them. So the learnings made in the growth teams, even those from mistakes or failures, we socialize them widely and visibly.
**Ben Williams** (01:05:41):
We want every R and D team to be leveraging experimentation where appropriate to learn to create business impact. So one of the things we did here is creating a paved row for adoption of behavioral analytics and experimentation stack, coach teams on getting started to make it as easy as possible for anyone to start to reap the benefits of the platform, built out internal education programs on data driven development, on experimentation, built internal tools to help with metrics design and so on.
**Ben Williams** (01:06:08):
And then building core platform services as well that are useful for people outside of growth. So we built services that power contextual onboarding, and originally that was the intent, but now those same services can be used anywhere in the product to give contextual experiences. I know that was a bit of a ramble, but hopefully there's one or two useful things in there.
**Lenny** (01:06:29):
Yeah, there's two things I wanted to quickly follow up and then we can talk about the product team. You said you socialize learnings and experiment results. Is there anything you could share there about tips to do that? You have a tool you do use that for? Is there someone posts stuff in Slack? Is it an email that goes out? How do you actually socialize learning such that say a salesperson can do something with it?
**Ben Williams** (01:06:50):
Yes. So there's, first of all, there's a bunch of Slack channels like Synk runs on Slack basically. So there's a bunch of Slack channels. Even when we're planning experiments, those are kind of wide and in the open and we invite collaboration on those. But from a ceremony perspective, we try hard to institutionalize ways to generate and leverage learnings. It's something I feel pretty strongly about. So we have these team level impact and learnings reviews loosely modeled from a blog years back down, I don't know... Six years I want to say that Brian Balfour wrote about a similar ceremony from these HubSpot days.
**Ben Williams** (01:07:26):
And if I had to pick one meeting that as the most important in the growth team, it would be this. The teams continuously document any learnings from data exploration, from experimentation, from user research and so on. They document that in their weekly impact and learnings document.
**Ben Williams** (01:07:43):
Some teams find it better to pair up and advanced into dedicated learning sessions to deep dive on specific relevant topics. But however it comes together, it's all put into that document.
**Ben Williams** (01:07:53):
When it comes to the meeting itself, it's usually run by the pm. Most of it is spent discussing learnings that have been documented, their implications, how they can be leveraged in follow up work, where they might have relevance to other teams and so on. For relatively smaller part of the meeting is also spent looking at key metrics. Some teams have actually split that out entirely into a separate meeting. And then no time at all is spent reviewing what the team have actually been doing. It's more on kind of the outcomes and the learning. So that's at the team level.
**Ben Williams** (01:08:21):
But then we run that same meeting at the group level on a monthly basis. So that's run by the product engineering or marketing director for the growth group. And that's where all of the growth teams come together. They share some key learnings, can't share everything. Of course, what they're doing is picking specific learnings that have potential relevance in utility across the other teams. So also as a standing agenda item for our user research team to share what we call developer insights. That's one of my personal favorite meetings to attend. It's always recorded and socialize with the rest of the company afterwards. And yeah, I'd say that's really important, but there's a bunch of different ways in which we're filing out that information constantly.
**Lenny** (01:08:59):
So cool. And this is a meeting that anyone can come to like a sales person comes to.
**PART 3 OF 4 ENDS [01**:
09:04]
**Lenny** (01:09:03):
And this is a meeting that anyone can come to like a sales person comes to see what interesting stuff the product team has learned recently from experiments. How cool. Would you be able to share a template of that document that you put together that we could include in the show notes?
**Ben Williams** (01:09:13):
Yeah, for sure.
**Lenny** (01:09:14):
Sweet. And then the meeting, you said it's run by basically like some of the product functions and ideas to share things they've learned in recent experiments, say in the past month.
**Ben Williams** (01:09:25):
So typically the team level ceremony, it's PM-led. That's from more from a facilitation perspective. The learnings are all brought forward by the various folks in the team and each one of them who's contributed to learning will talk about that learning with the group and facilitate the discussion from there. And then at the group level, those are read by the directors for the growth group and each team it might be an engineering lead, it might be a tech lead, it might be a designer, it might be the product manager. We'll talk about some key learnings from that month.
**Lenny** (01:09:56):
Makes sense. If there's nothing PMs are good at, it's facilitating meetings. So that makes sense. Okay. And so that's a good segue to just chatting a bit about the product org. I'm curious just like how you structure the product team and then how that works with the growth team.
**Ben Williams** (01:10:10):
That's good. So the product org, what do you want to know?
**Lenny** (01:10:13):
Broadly, how do you structure it? Just like how many teams do you have? Do you align it across by outcome or is it by surface area of a product? And then is the growth team like adjacent to this product org? Is it like a unit within the product org or is it integrated? But I don't think it is. So what does that look like org chart wise?
**Ben Williams** (01:10:34):
I think we've got a fairly common pattern for how we structure our product and wider R&D org. So most of the org functional ownership-based, there are a lot of really complex domains in the core product. So having that localized knowledge is important to be able to own and run the code that teams ship. The growth teams, on the other hand, are structured by outcomes. We talked about that already. Owning areas like acquisition, activation, engagement, monetization. These outcomes and team remits change over time as we talked about. But the teams here are often working on areas of the product where they don't own the code, which I think is the key difference between how we structure our growth teams and product teams with some exceptions. One of the growth teams actually own the onboarding flows and so on. So that does require a lot of trust.
**Ben Williams** (01:11:25):
It requires very transparent communication mechanisms built into how we work. One of the meetings that we have regularly is experiment plan reviews. They're ad hoc meetings. They're led by the experiment lead, could be the PM, could be anyone else in the team. But the important thing is a bunch of people will be invited there, especially stakeholders from other teams where we might be experimenting on their surfaces and that won't be the first time they've learned about this. We'd like to try and actually include them in co-designing the experiment plan so they're fully on board with it. But absolutely kind of inviting them into those experiment and views really key. If we're going to run an experiment on that surface, we need to make sure that everything in that experiment plan is watertight, especially from a scheduling perspective because the last thing we want is a week and a half into an experiment for some change to happen within that surface from the product team unaware that an experiment's happening and completely invalidate the experiment.
**Lenny** (01:12:26):
Cool. And then in terms of just org wise, do you have a lieutenant that is responsible for just say the product team and then someone responsible for the growth team or the directors report up to you and you have a bunch of reports? How's that structure?
**Ben Williams** (01:12:39):
Oh, so our CPO on the exec team [inaudible 01:12:43], he runs the entire product organization. He has four, I want to say VPs, that own different areas. So there's a couple of VPs that own different areas of the product. So first of all, our application security products. Secondly, our cloud security products. Third is platform. And fourth is what we call developer journeys, which is the area I own, which has a few groups within there, one of which being the growth group.
**Lenny** (01:13:13):
Got it. Okay. Makes sense. Okay. There's just a couple more questions I want to ask that are very tactical specific before we get to a very exciting lightning round to close this out. One is with a freemium product, there's always this question of what to put into free and what to put into the paid plan. Is there anything you've learned about how to think about that? What should be in free and what should be behind a paywall?
**Ben Williams** (01:13:36):
Was it on your show with Elena that she talked about things that promote your growth model being good to land in free and things that add friction? So I really like that guidance. I'll add that for many businesses there might be some cost of service element to consider as well. Providing a feature to free users is cost prohibitive due to the volume, then that's obviously something you're going to want to reserve for paid. Ultimately, that was the whole reason cited behind Heroku, recently removing their free plain entirely. I think your plans from free to the top, they should have well defined understanding of the target customer, the use cases they should map out or you should map out the motivations for motion between each. You're really clear about what are the drivers for someone to take a step from one plan to the next. For Snyk, the real drivers to move from free to a paid plan, for example, is when you want to secure business critical code and you start having needs around governance and compliance.
**Ben Williams** (01:14:39):
I think the other interesting dimension is of how you approach trials. Like with most things. I think we're still figuring that out at Snyk. I don't know that there's ever a perfect answer or even a correct answer here. Certainly different from product to product. We have a self-serve trial to support time box evaluation of some of the capabilities that are reserved for our paid plans. But we're intentional in revisiting the model periodically. It's important I think to regularly challenge yourselves to ensure you don't fall into the trap of simply assuming what was best fit in the past is best fit now and in the future. What if the trial duration was limited by some dimension of usage instead of time? Or what if we didn't have a trial at all but put more into the free plan with appropriate limits? How might making those changes impact our growth model?
**Ben Williams** (01:15:27):
It's not always easy to answer those questions, but I think there are some ways that you could can help test there for example. You might cohort trial users and teams who have low engagement and don't convert during the trial and then when the trial ends, drop them back into a new enhanced freak plan and monitor engagement there. So there're some things you do, but I think that habit of continuously challenging yourselves and reevaluating whether the model, the specific delineations between the plans and how you support evaluation and the motion between those plans, I think it's really important to do that. And also when it comes to PLG and sales, we talked about the self-serve motion. Obviously, it's big and important for Snyk, but the sales led motion critically large as well and significantly impactful. You need to think about the plan design and those motions across both aspects of PLG and the sales led motion. When you have a strong PLG foundation that is inclusive of a product-led sales motion, you're going to be in a really powerful position from the perspective of having a significant volume of highly qualified leads that are coming from the product. We actually track a metric that we call product-driven revenue, which basically accounts for all revenue in customers where we saw meaningful value-based activity in the product before there was any sales contact. And that really tells actually a super interesting story about the PLG efficiency of your company across all revenue channels, self-serve and sales-led. And what's fascinating there is that the product-driven cohort contribute a relatively greater amount to net retention. So when you think about packaging, you know really need to think about and understand that macro level contribution of the freemium motion and know what you're trying to optimize for balancing revenue today versus potential future revenue.
**Lenny** (01:17:28):
Is that increase in net revenue retention from product-led leads mostly because they start at a cheaper price, do you think? Or is it more that they just end up being better customers?
**Ben Williams** (01:17:40):
It's a great question. I'm not sure I have a good answer for that.
**Lenny** (01:17:45):
No problem.
**Ben Williams** (01:17:46):
I'm still trying to figure that out.
**Lenny** (01:17:48):
It's a good prompt to have people adding more customers in seats. You talked about the importance to figure out the trial length and what to put in the trial and free and things like that. Is there anything that just has surprised you? Something you've learned from iterating on that comes to mind?
**Ben Williams** (01:18:04):
I wouldn't say surprised me per se, but it's something that I think it's perhaps obvious in retrospect and that is that companies of different sizes, of different complexities of different industries from those that are very highly regulated to the other end of the spectrum, they're going to take different lengths of time to need to evaluate properly. So being able to cater for those in some way, whether it might be dynamic trial lengths or whether it be trial lengths that are based on usage or things like that, I think it becomes really important. That's something to be thinking about for sure.
**Lenny** (01:18:47):
Awesome. That's a great learning. I know Elena talks a lot about how trials often, screw you because you don't give people enough time to really evaluate it a company, so that makes sense. Last tactical question that I wanted to touch on is around activation milestones. I'm doing a survey right now with Yuri that I think will come out before this episode airs. But anyway, in real time, I'm curious how you think about setting what the activation milestone is for a new Snyk user. So maybe just share briefly how you think about what is an activation milestone? Why is that important? And then how you define that for Snyk? What is the milestone of a user is activated for your product?
**Ben Williams** (01:19:28):
First of all, what is activation? So for us, activation is indicative of the team forming a habit around the usage of Snyk. And when I say the usage, I actually mean deriving core value, which is ultimately fixing vulnerabilities. It's not just logging in. It's not even just finding vulnerabilities, it's fixing vulnerabilities. So building a habit around that. And the reason I say team instead of using them is, and we actually base most of our definitions of activation engagement around teams. It's really important because ultimately security is a team sport. That team might be one person, which case a user is equivalent to team, but often a team is multiple people and we actually expect different people to fulfill different parts of the team activation journey.
**Ben Williams** (01:20:17):
We also want to enumerate aggregate level activity around fix that sometimes happens off-platform where we can't explicitly measure it at the user level. So in the activation process, we have set up moments, aha moments and habit moments and our habit moments that we define as a team being activated, it's related to fixing vulnerabilities within 30 days of team creation. And the reason that is chosen, it's because there is a significant correlation with downstream. And in that case with activation three month retention and retention again based on, again, not just coming back and logging in but still fixing. So teams, that fix of vulnerability within their first 30 days are much more likely to still be fixing three months later.
**Lenny** (01:21:09):
That's really interesting. I love that. How did you come up with that number? Was there a decision scientist that looked at some inflection of at 30 days, and it's probably not exactly 30 in real life, but it's like a nice round number that's close enough, right?
**Ben Williams** (01:21:24):
Yep, that's it. So there absolutely was a decision scientist in involved thankfully. We had to collect a lot of baseline data first. So after we built out the data platform, we needed actually to wait for bit to build a good data set. We did a huge amount of quantum analysis, a lot of splunking of the data, applying ML models along with a bunch of supporting call research as well. But we started really with identifying the corpus personas and they used cases, different roles of different users within the team based activation journey, defining our retention metric, which is still fixing. It's whether a team is fixed. Along with natural usage behavior and expected natural usage frequency. And then we found the habit moment that ultimately most strongly correlated with improved long-term retention. And most of the numbers side of things came out of our ML ops platform.
**Ben Williams** (01:22:19):
But after that, we then worked back to figure out that's the habit moment. That's what we see as activation, but there's a set of steps that teams need to get there. So what's the aha moment before that? What's the setup moment and what are the individual steps that the team needs to go through to reach that set up moment? So that's the overall process and ultimately it's a really strong model that allows us then to feed in the set of user level behaviors that we know can influence those different steps on that path to activation.
**Lenny** (01:22:50):
Awesome. I'm excited to get this post out and that's a really good anecdote of how a company comes up with it and what they set. I also just thought of another question I may start asking everybody. I know I keep saying we're going to wrap this up, but here's a question and if it doesn't work, we'll get rid of it. You mentioned a bunch of tools that you use and I'm curious, if you had to think of what are the five most important/valuable SaaS products to your organization other than the obvious ones like Salesforce? What comes to mind?
**Ben Williams** (01:23:21):
When you say organization, do you mean Snyk at large or do you mean the growth?
**Lenny** (01:23:25):
Let's say, let's start with growth and see where it goes.
**Ben Williams** (01:23:27):
Okay. So I'm going to say Amplitude, first of all. Segment as a means to be able to get our data from the products to Amplitude and to everywhere else that cares about it. Whether that be a downstream BI system, Snowflake can looker on top of that, or system marketing automation systems like Marketo and stuff like that. So I'd say Amplitude. I will next say full story, which is absolutely fantastic for session replays of course. And it bridges that gap between [inaudible 01:24:11]. I would say userinterviews.com, which is comparable to usertesting.com, both of them amazing services in terms of getting fast curated access to individuals to participate in user research. Sprig is another one. So Sprig is a fantastic in-app survey platform, which is what we primarily use it for, but it also does a bunch of other cool stuff in terms of being able to test UX designs as well in-app. How many have I said?
**Lenny** (01:24:49):
I think four. If there's anything else, you could add a fifth. If not, we can move on. That's awesome. This is a really interesting list.
**Ben Williams** (01:24:55):
I'll stick it at four.
**Lenny** (01:24:56):
Okay. Is there anything for in the wider product team that also comes to mind that you guys find useful?
**Ben Williams** (01:25:02):
Airtable. In fact, Airtable for growth and product, just so flexible. It's just you can do anything. And in fact, if we think about growth, I should have mentioned that first because that's where we keep most of our experiment plans and knowledge base and our user research base.
**Lenny** (01:25:18):
Okay. I like this question. I'm going to start asking it. This is great. Okay. That was a precursor tour, very exciting lightning round. I'm just going to ask you a bunch of rapid fire questions, just answer whatever comes to mind. We'll keep it short and quick. Question one, what are two or three books that you recommend most to other people?
**Ben Williams** (01:25:34):
I have been dreading this question as there are too many. So I'm pick a couple that I've enjoyed reading in recent months. So for product and growth geeks like me, or in fact anyone with more than a passing interest in data, I'll recommend "How to Measure Anything" by Douglas Hubbard. Second up, you had Marty Cagan and he mentioned the book "Sprint" by Jake Knapp and John Zeratsky and I love that book, but personally their "Make Time" book. It was something that radically changed my relationship with information and I recommend that to all time staff, product people out there. And for number three, I'm going to say, "This is How They Tell Me the World Ends" by Nicole Perlroth, which gives an amazing view into the world of digital espionage.
**Lenny** (01:26:22):
Oh, I read that book. Tim Ferris recommended that at one point. That is a wild ass book. Very beautiful. Cool. I love these recommendations. All right. Great choices. Favorite podcast other than the podcast you're currently on
**Ben Williams** (01:26:37):
Maybe "Acquired" with Ben Gilbert and David Rosenthal. I just wish I had enough time to listen to them all.
**Lenny** (01:26:43):
They're very long. I was just at an event where they interviewed someone live as a live podcast. That was very cool. Those guys were pros. What's a favorite recent movie or TV show?
**Ben Williams** (01:26:54):
So a movie, "Turning Red" on Disney Plus, which we love watching with our kids. It was just fun. TV show, the most recent Curb Season had me in tears as usual.
**Lenny** (01:27:03):
They haven't had a new one in a while. So that's a little bit out there.
**Ben Williams** (01:27:09):
The new one's coming.
**Lenny** (01:27:10):
Oh, it is? I don't love watching that show. My wife loves it. Cringe, painful. But watch it anyway.
**Ben Williams** (01:27:19):
And my wife's actually the same. She can't watch it because she cringes too much.
**Lenny** (01:27:23):
We're reverse.
**Ben Williams** (01:27:24):
I love the awkwardness.
**Lenny** (01:27:25):
Oh man. It's good for a product leader to have that enjoyment. Favorite interview question that you'd like to ask candidates?
**Ben Williams** (01:27:34):
Give a couple here if it's not cheating too much. First is one I like to ask when hiring for anyone actually really it's fast forward three years. What's different about you then? A lot of people will default to telling you where they aspire to be in terms of role or title, but what I'm really looking for is signals of humility, of self-awareness around areas of personal and professional growth. So people who can be open about where they think they need to work on to grow themselves as people. I love that. Also, so there's just generally throughout interviews, I'm looking for curiosity. So day-to-day good PMs will be asking why as much as my six year old son does, which is a lot. So I'll try and discern that through the course of the conversation. It's not really a question, but something I'm looking for.
**Ben Williams** (01:28:27):
And then maybe I want to flip it because building on something that Adam Fishman was saying, his theme of evaluating the people dimension of folks you are potentially going to work with when you're interviewing with a company. And this was a question I got asked myself recently by a candidate, which I just thought would brilliant, and that was, "Tell me about the diversity, equity, inclusion, and belonging initiatives that you've recently personally been involved with?" And it just felt like a really great way for them to be able to test alignment of their personal values with those of someone they'd be working with really closely. So I love that.
**Lenny** (01:29:01):
Awesome. By the way, I love how many callbacks to other episodes you're making. You're definitely a power adopter of the podcast and I really appreciate that.
**Ben Williams** (01:29:09):
Okay, there we go.
**Lenny** (01:29:11):
Last question. Who else in the industry do you most respect as a thought leader, as a leader in general?
**Ben Williams** (01:29:17):
So maybe I'll cheat on this one a bit too, and I'm not going to combine it to the, when you say industry, I think security industry, but I'm going to look at the product domain and specifically product operations. And in my mind, there's not many people who know more in this area than Christine [inaudible 01:29:34]. So if you ever get chance to talk with her, I know that would be a fun conversation. Many gems would be dropped, I think.
**Lenny** (01:29:40):
Wow. I will get her on this podcast. That is my new goal. I had not heard of her and that's awesome. Thank you for the suggestion. Ben, this has been awesome. So many nuggets and stories and insights. I so appreciate you being here. Two last questions. Where can folks find you online if they want to reach out or learn more or maybe come work at Snyk? And then how can listeners be useful to you?
**Ben Williams** (01:30:04):
Firstly, I'm of course want to say a big thanks for having me on, Lenny. I love talking about all this stuff and really appreciate you being willing to let me bend your ear a little bit. As to finding me, I'm a bit of a Twit when it comes to Twitter. I generally spend a bit more time over at LinkedIn, but you can find me on both of those platforms @SemanticBen. And in terms of how people can be useful to me, I'm starting to take on some additional clients in advisory capacity, so feel free to get in touch if you think I could help.
**Lenny** (01:30:36):
I can't not ask about Symantec Ben and what the story is there and before we let you go.
**Ben Williams** (01:30:41):
Sure. It's actually when I was at IBM, it was a focus that I had on linked data.
**Lenny** (01:30:48):
Became Semantic Ben. All right. Awesome. All right. Ben, thank you so much for being here and thanks for listening.
**Ben Williams** (01:30:56):
Thanks, Lenny. Take care.
**Lenny** (01:30:59):
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.
**PART 4 OF 4 ENDS [01**:
31:22]

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## [11/20] How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach)

**Matt Mochary** (00:00:00):
The biggest marker that I've seen between a botched layoff and a successful layoff is at the moment someone hears that they no longer have a job, did they hear it from their manager in a one-on-one? If that's when they heard it, it'll be okay. But if they heard it in an email, in a group chat, in any kind of thing where they were sitting next to or they're hearing it along with other people, it wasn't personalized, it wasn't one-on-one, that is terrible. That's when people get really angry and that's when they start going on to Twitter and going to newspapers and et cetera, because it feels dehumanizing. It feels like you didn't give a shit about me. You don't even have the courtesy to tell me to my face. And of course, there's no way to allow that person to express their emotions because they're in a group. So, that's the most important thing.

**Lenny** (00:01:08):
Welcome to Lenny's Podcast. I'm Lenny and my aim here is to help you get better at the craft of building and growing products. Today, my guest is Matt Mochary. Matt is a full-time executive coach, but not just any coach. He's worked with folks like Naval, the CEOs of OpenAI, Coinbase, Reddit, Rippling, Fair, Front, Notion, the list goes on. He's also coached partners at VCs like Sequoia, YC, Benchmark, many others.

**Lenny** (00:01:34):
We are so fortunate that Matt agreed to join me on this podcast and in our conversation we cover a lot of ground. We talk about why learning to fire people is one of the most important skills as a leader and how to do it well, why anger and fear often point you in the exact opposite direction you should be going, how to innovate within a larger company, how his coaching has evolved over the years, where the most successful founders still struggle, and so much more. This may be my new favorite episode and I bet it will be years, too. So much real talk with tactics, templates, all kind of goodness. Enjoy this conversation with Matt Mochary.

**Lenny** (00:02:12):
**Matt Mochary** (00:04:47):
Thanks for having me. I'm looking forward to it.

**Lenny** (00:04:49):
I am looking forward to it even more. The way I learned about you is back in the day I read this book called The Great CEO Within, which I have right here, and I was like, holy moly, this is the most tactical, practical, useful book I've seen for leaders. I need to tell everyone about it, and I did. Then a few weeks ago, someone shared a link in my newsletter Slack community to this document that is called the Mochary Method Curriculum Document. I was like, oh my god, this is the most practical, tactical, useful document I've seen in a long time. I got to share this with everyone, and I did. Then I realized it's the same person that wrote these two things, and so I reached out to you and you kindly agreed to join me on this podcast. And so again, really appreciate you being here.

**Matt Mochary** (00:05:30):
Thank you for having me.

**Lenny** (00:05:32):
Give folks a little bit of background on you who aren't so familiar with you, and just to help understand a little bit of a how you got so wise. Can you give folks just kind of a brief overview of some of the wonderful things you've done in your career, maybe some of the folks you've worked with and how you got to what you do now?

**Matt Mochary** (00:05:47):
Right on. I've had a very varied career. I started a company back in internet 1.0 called Totality, which was a good financial outcome. Then I went and just had fun for a long time and then I went and did social good and helped ex-convicts get and keep a job by becoming truck drivers. All that was super fun, but I realized I missed my peers and I wanted to get back into the tech world, but I didn't want to start a company because a company is a lot of work and the end result is you make a lot of money, but I didn't need money.

**Matt Mochary** (00:06:15):
And so I thought, how could I get in the tech world and not actually have to do the hard work? Oh, I could be a coach. I could coach people and then I just get to do the fun stuff and advise them and then they have to do the hard work. And so I looked around and thought, well how could I do that because I'm not a coach and so why would anyone listen to me? Then someone told me that there were students at Stanford that had started companies but no one would coach them. They couldn't get into YC because YC doesn't accept students. So, I went and started coaching them and it was super fun and very successful and then they started recommending me up the food chain and eventually, I met folks like Naval Ravikant and Sam Altman and Brian Armstrong and they recommended me around to the rest of the tech community, and ended up coaching some of the CEOs and the leaders of the biggest tech companies and biggest tech investment firms.

**Matt Mochary** (00:07:07):
It's been a ton of fun and for me, I do things for joy and each and every one of these interactions has been massively joyful for me and the people I coach become my really close friends, so it's all very selfish on my part.

**Lenny** (00:07:21):
I feel you on a lot of that. I also tried to explore starting a company again and similarly decided this is way too much stress and work, what else can I do instead? And that's what led to the work I do now, which I love.

**Matt Mochary** (00:07:33):
Right on.

**Lenny** (00:07:34):
How long have you been doing this coaching?

**Matt Mochary** (00:07:36):
That whole process started about 10 years ago, so about 10 years.

**Lenny** (00:07:40):
Awesome. You have a lot of fans on Twitter and the internet and ahead of this chat I polled folks on Twitter and asked them what they would ask you if they were chatting with you, so I thought I'd start off with asking you a few those questions and then we'll dig into a few very specific topics that I'm excited to talk about. The first question comes from Leo Polovets who's a GP at Susa Ventures, and he asked, "Matt has coached some incredible founders, what are some of the most common areas where even the most successful founders still struggle?"

**Matt Mochary** (00:08:11):
Great question. To me, the bar is fear and how strongly do people feel fear? There are few people that I coach that just don't feel fear at all. And frankly with them, we have very tactical conversations, but they're the minority. The most feel fear to some degree, some feel it a lot, some feel it less, but when they feel it grips their mind and it prevents them from seeing... It prevents them from doing the thing that is difficult but necessary, so that's a lot of what our coaching is, me pointing out to them, hey, I think you're in fear.

**Matt Mochary** (00:08:55):
What happens is very early on in coaching they'll go, yeah, okay, I'm in fear. So what? I go, great. I believe that fear is actually giving you bad advice and I think you're predicting that if you do this A will happen. Well, I'm predicting that if you do that, the exact opposite will happen. So, I'll tell you what, why don't we make a bet? This is very high stakes, why don't we pick something that's lower stakes? You make a prediction, we'll see if I make the opposite and then let's bet on it. So we pick something and then we make a bet on it, and whoever wins the bet in the future gets to determine what the actions are.

**Matt Mochary** (00:09:31):
I've made this bet hundreds of times and so far, I've never lost. It's not because I'm magician or a genius, it's because when someone's in fear, they're gripped. They can't see reality, their brain is making very exaggerated predictions. Whereas when someone is not in fear, and I'm not because it's not my situation, I am not gripped and therefore, my brain isn't making exaggerated predictions. And so, we make this bet once I win, then all of a sudden the CEO realizes, oh my God, there's something to this, fear gives bad advice. Then after that, all I need to do is remind the person that I perceive them to be in fear. That's all it takes, and they're like, oh, okay, and then they go ahead and do the thing that they feel fear about. Then of course, later they come back to me and say, Matt, that was magical. It works so well.

**Matt Mochary** (00:10:23):
I mean, I'll give you examples. The most extreme is when a CEO realizes that there's a problem in the business and they haven't told their board yet and their board doesn't know, and remember, their board is their investors, and they have another round coming up, they know they're going to have to raise money in another six to 12 months. They need their current investors to participate in the upcoming round, otherwise outside investors won't. Then they say, well, what the hell do I do? I've got this problem. Do I tell my investors? And most often, the knee jerk reaction is, no, I'm not going to tell them.

**Matt Mochary** (00:11:01):
Then I say, "Well, I think that's fear. I think if you actually tell them, tell your investors, the exact opposite of what we think is going to happen is going to happen. You think you're going to lose their trust. I think you're going to gain their trust." And so, if we've done this fear exercise before, they do it, they share transparently with their board all the problems and say, and I'm excited to tackle these problems. Every single time that's happened, the board members have said, "This is fantastic. I love this honesty. Thank you so much. This is one of the only companies that I'm on the board of that actually is transparent and honest," and they gain trust.

**Lenny** (00:11:42):
I'm glad that you brought this topic up. I wanted to spend time on it. Just to double click a little bit into it, just kind of to summarize your advice here, if you feel fear, which you may not recognize you feel, the advice is: do the opposite of what your brain is telling you to do, right?

**Matt Mochary** (00:11:57):
Generally, I mean, check with someone. Don't just randomly, I feel fear crossing the street crossing a crowded highway and then go, oh, that's fear talking. I should cross the highway anyway and then get hit by a cop. No, that's not what I mean. I don't mean physical danger, I mean things that we perceive to be danger to our egos, but that the easiest thing is just to check with somebody else who's not in fear because they will be able to see clearly when you can't.

**Lenny** (00:12:24):
I was working through your curriculum and you pointed out that you found a way to express to somebody that they are in fear. I think it was your wife that kind of iterated on how to give you feedback that you're in fear where you didn't get defensive, you got more fearful and angry and can you talk a bit about that?

**Matt Mochary** (00:12:40):
Yeah, so we iterated, I at times feel anger and I act on that anger and I don't even realize I'm in anger, so I wanted her to let me know, and so she would say, at first she said, "You're in anger," and that just made me feel accused and made me go into more anger. And then she said, "Are you in anger?" And that felt passive aggressive or indirect and that also made me go into more anger. Then finally she said, "I perceive you to be an anger." So it's an I statement and it's simply what she's perceiving. There's no judgment. That was able to punch through my anger and then I woke up and went, oh, and then I stopped and just didn't act until I was able to shift out of anger.

**Lenny** (00:13:25):
Awesome. And anger and fear, I think there's different pieces of advice for if you feel angry versus fear. Is that right?

**Matt Mochary** (00:13:32):
Yes. I mean, anger, you're just destroying and what you're doing is you're destroying relationships and so you just got to stop because you're breaking glass. Of course, you're breaking it with the people who are closest to you. They're the people who are nearest to you, which are the people you love and care about the most. They're not only people you work with, but they're the people you live with and you don't want to do that. You don't want to hurt them.

**Lenny** (00:13:59):
Yeah. Maybe one last question along these lines, why do we do this? Is this just we're trying to protect our ego and ourselves and we just want to do the safe thing?

**Matt Mochary** (00:14:06):
That's it. I mean, I just learned very recently, and this isn't written anywhere because I just learned it, someone shared with me that anger is not a base emotion. Anger is actually a cover. It's a cover for when we feel pain, and so our brain doesn't want to feel the pain, so instead it externalizes it. But the problem is it shoves that pain onto everybody else around us. The real answer here is not to have people let us know that we're in anger and then stop. The real answer is just to allow ourselves to feel the pain and it sucks by the way, it actually hurts. But then we're not... Sorry, I'm getting emotional. We're not pushing that out onto other people and I only learned this very recently and I'm just starting to practice this and I'm still not good at it, but I'm now at least sometimes not going to anger.

**Lenny** (00:15:02):
It's interesting how personal this advice is that it sounds like something that you deal with. It's not just like you're this coach that's just like, hey guys, here's all these problems you have. Here's how you fix stuff that you help yourself with.

**Matt Mochary** (00:15:15):
I'm human. Yes, and that's why I try to figure it out with me and if I can figure something out with me, then I can share it with others.

**Lenny** (00:15:24):
Amazing. That was a fruitful question from Leo, and we might come back to this topic.

**Matt Mochary** (00:15:30):
By the way, this also applies to organizations. I mean, the way that I used to get all this information about how to run organizations is I started a company, Totality, and my co-founder and I, we did a terrible job running that company. What happened was I didn't have any learnings from that which I could share with people because it was just worst practices, not best practices. But then 10 years later, I thought to myself, well, how could I have done that better? How could we have done that better?

**Matt Mochary** (00:15:55):
So, I picked up a book, a business book, it was High Output Management by Andy Grove. I read it and I was like, "Oh my God, here are all the answers." And then I read another book, The Hard Thing About Hard Things by Ben Horowitz was like, "Oh my God, there are even more answers." I just kept reading more and more business books, and every one I read, they were just chock full of answers. But then I needed to test whether or not these really worked, so that's when I started coaching and I started testing them in companies, but I had to let the people know here, do this, but they weren't going to read a 350 page book. I had to summarize it in two pages and then share it with them, and then they did, and then they implemented it and it worked.

**Matt Mochary** (00:16:29):
Then I had all these summaries, and then I started to create my own summaries of little niche cases that weren't in any book that I'd read. That's where all these writings came from. Then one day, someone that I was coaching said, "Matt, you got to take all these writings. They're a book, you got to publish them." And I said, "No, I don't." My friend said, "Well, how about I do all the work? How about I take care of the editing and the publishing?" And I was like, "Okay, if you want to do that, great." That was Alex MacCaw. Others had offered before, but he was the one that actually followed through all the way to the end. That was it. That's how the book was born.

**Matt Mochary** (00:17:06):
But I realized also, recently, that many of my most radical ideas, I can't get anyone to test them because I'll say, "Hey, I think you should do blank." And the CEO will say, "That sounds crazy. Matt, can you point me to other examples of other people that have done this and it's worked?" And I say, "No, this is an original thought that came out of my head. No one's done it before that I know of." They're like, "Okay, well I'm not going to be the first."

**Matt Mochary** (00:17:33):
Then I realized I needed an organization to test my most radical ideas, and also all of my CEOs had been asking me to create software because I have a methodology and it's step one, step two, step three, and you do it in one-on-ones and then a methodology for a team meeting and then a methodology for feedback and then a methodology for every different motion in the company. It's all in Google Docs. And they said to me, "Matt, this is amazing. I love this one-on-one process. I love your team process, but I don't want to have to teach each of my reports the way you've taught me. I'd like it just being softer. I just hit a button and boom, it happens automatically." At first, I said, "No, that's not interesting to me. I'm not a developer. You, Brian Armstrong, you're a developer and you have a thousand engineers that work for you. Why don't you go create it?"

**Matt Mochary** (00:18:21):
But in the end, I said, "Okay, this could be fun." So, I hired a team of developers and we started to create the software, and one, the product is working. But two more importantly, I now have a team of humans that we work together that I can start testing my more radical ideas out with. I would say about half of them are wildly successful and the other half complete duds. It almost seems like one are the other. But now I have my own basically laboratory to test things. Of course, when I see radical things that other people are doing, I try them in our organization, and it's phenomenal.

**Matt Mochary** (00:18:59):
I'll tell you the most radical one. I was asking one CEO, I said, "Have you ever let someone go and regretted it?" He said, "No." And I said, "Well, then you don't know what the bar is because the bar of where you should be letting people go is here, and the bar that you've let people go is here. So until you get close to that line, you don't know what that line is." He said, "Wow, that's true." Then I thought about it and I thought to myself, uh-oh, I have never let anyone go that I regret it, so I don't know where the line is.

**Matt Mochary** (00:19:34):
Then I thought, oh no, I've got to go into my team and let someone go, and here's the problem. We've already done talent density, we've already done the Netflix thing. If someone is meeting expectation, we let them go. We've already let all those folks go. So on our team, it's only outperformers. So, I thought there was one guy, he's an outperformer, no question about it, and super positive, an amazing guy and can do anything and is happy to do everything. But there wasn't much left for him to do because everything else was being covered. I talked to my number two and said, "Can you do what you're doing and what he's doing?" And she said, "Give me two weeks," and she did. She came back and said, "Yeah, I can." So, we let him go.

**Matt Mochary** (00:20:19):
Now, when I let someone go, I try to do it with a massive amount of compassion because I know it's brutal. I mean, losing your spouse, your home, and your job, these are the three most traumatic things that can happen to you. When that happens, of course you go into massive fear and the brain shuts down, so I want to be there and help them through that process and actively help them find their dream job because there is a place that absolutely needs them. So, what I do is I become their agent and I say, "I want to help you discover what it is that your ideal role is, and I want to help you create it or land it." I did that with him. Turns out, what he wanted to do was go start a company and create a new product so he could just start that day one. But, the litmus for me is that everybody I've let go, I believe anyway, that I continue to be friends with. That shows me that the process by which I let people go is a humane one.

**Matt Mochary** (00:21:17):
Here's the crazy thing, after letting this guy go, after about 30 days, I was like, ugh, did I do the wrong thing? Was that too much? But then after about two to three months, I realized, no, that actually was the right thing because my number two was able to absorb the things that he was doing and here's the crazy part, with fewer people in the organization, things work better. That's the big realization that most people never discover. they hit product market fit, they get tons of money from investors, just higher, higher, higher, higher, but every additional human you have in your organization causes extra overhead and geometrically so, because now you have to keep all those people informed, give them all context, make them all feel heard, because unless they feel like they're contributing and you understand what they're saying, then they feel ignored and they feel passed over and they feel disrespected and grumpy.

**Matt Mochary** (00:22:11):
There's this morale problem that exists. There's this friction of information flow and a morale problem that grows and grows and grows. Really, the only answer is, I mean, that's why people bring me in because they're growing, growing, growing, and things are breaking. I have a system that keeps things together, but it doesn't make it perfect. It just makes it so that the company doesn't fall apart. But really the ideal is just to keep the team super small. That's what WhatsApp did, that's what Instagram did, that's what Linear is doing right now. That's what Notion has been doing for a while. Those, to me, are the real success stories.

**Lenny** (00:22:53):
This reminds me of a story I just listened to on Lex Fridman's podcast. They were interviewing the head of AI at Tesla, or former head of AI, and Lex was asking him, "Why did you get rid of LiDAR on your cars? Like aren't more sensors good so that you can be better at self-driving?" And he's like, "If you have LiDAR, you got to think about the supply chain and getting all those parts. You got to think about all the additional data that it brings and adds more chaos to your data, and you have to think about that. Think about if that one part is gone, everything slows down, and in theory it is better, but then all these other factors end up making it worse." Talking about how Elon's philosophy is the best part is no part. It feels like that's exactly what you're saying.

**Matt Mochary** (00:23:36):
That's right.

**Lenny** (00:23:37):
You're getting to all the stuff I want to talk about, which is awesome. So firing people, this is good. We were chatting earlier and you mentioned that this is a skill that most managers are really bad at and maybe is the most important skill to develop as a leader and as a manager. People are just bad at it. You shared a few pieces of advice there, but is there anything else that you could share about just how to get better at firing people and that skill?

**Matt Mochary** (00:24:03):
Yeah, the reason people are bad at this is because they think that they're hurting the person who they're letting go. I mean, how many times have I heard from someone, "Yeah, this person's not performing, but gosh, they really need this job and their mother has cancer," and whatever personal situation they're in. Wei Deng, who is the CEO of Clipboard Health, who's one of my favorite CEOs, who frankly I learn more from her than she learns from me, she shared with me her framework for making decisions, which is she separates the decision from the implementation, meaning she thinks about who is the stakeholder here that I'm solving for? And almost always in a company, you're solving for the customer. So, what would the customer want to see happen? That's the decision. Of course, the customer would want to see only the best employees and anyone who isn't a great employee, don't be there.

**Matt Mochary** (00:24:52):
Now the implementation is, if I do this, if I let this person go, who gets hurt? Well, the employee gets hurt. Maybe I get hurt because it's a painful conversation. Maybe the rest of the team gets hurt because they're sad that their friend is leaving. Then you look at, well, what can we do? Each person who gets hurt, what is it that they really want? Let's see if we can help them get what they really want. Well, the person let go, what do they want? They want a great job where they're actually needed and they feel fulfilled, so they enjoy what they're doing and they're actually critical to the company or organization that they're with. Right now they're not, by the way, they're not critical, clearly. So you're actually holding them back from what it is that they really want.

**Matt Mochary** (00:25:36):
What you do is you help them find that place that really needs the skill or the passion that they have. Yourself, what do you really want? You want to not have a difficult conversation? Well, cognitive behavior therapy, the best way to get over that is to actually have one and realize it's not that bad. Then the rest of the team, they feel sad because their teammate left. Well, here's how you solve what they really want is they want to know that... They want to release their emotions. Okay, great. Listen to them, let them share their emotions, let them share the sadness that they feel, and then it's released out of their body.

**Matt Mochary** (00:26:12):
Decision is one thing, implementation is completely and utterly separate. That's the same thing here in letting someone go. But if you let them go kindly and humanely, the key is, in my opinion, you become their agent, like Michael Ovitz, the CAA agent. You help them find their next job actively. Michael Ovitz is the one who reaches out to employers for his clients and says, "Hey, do you have work for my client?" That's what I mean by being agent, not by, if you need a reference from me, I'll be happy to give you reference. That's bullshit, that's passive.

**Matt Mochary** (00:26:50):
I'm talking about active, and it doesn't take long. Maybe one to two hours of my time reaching out to people I know saying, "Hey, I've got this great person." Oh my God, of course they're going to pay attention. Of course, they're going to react. Now you might say, well, wait a second, what if the person isn't great? What if they're a bad performer and my posit is that they're good at something. You have to find out what it is they're good at. And really what they're good at is what they're passionate about, so find out what they're passionate about and that you can recommend them for. That's what I do.

**Matt Mochary** (00:27:25):
I think for almost all managers that aren't good at letting go, it's because A, they've never done it, or B, they've done it badly. They didn't help the person, and that person then went off and had a very painful time and now hates that manager. But if you actively help that person, they will appreciate it. Now, there are situations when a person says, "Screw you, I don't want your help." Okay, but they still recognize that you offered.

**Lenny** (00:27:56):
Who's the best person at firing that comes to mind when you think of this person's really good at this?

**Matt Mochary** (00:28:01):
Wei Deng from Clipboard Health. She's the most compassionate.

**Lenny** (00:28:07):
Awesome. The framework you shared reminds me of something my manager once taught me similarly. They missed the final piece of actually being their agent and finding their next gig, but just the idea of separate the emotion and doing the thing from, if there were no feelings involved, what would you do? And then you should do that, and that might be hard.

**Matt Mochary** (00:28:26):
That's exactly right. By the way, this whole thing about no feelings, I do have probably two CEOs that don't feel emotions. They don't feel fear, they don't feel anger. One, in particular, feels zero emotions. I have to say, he's a machine, he's an operating machine and there's zero time between ah, this is the right thing to do and doing it. It's amazing. It's an incredibly well run company and an incredibly valuable company. So yeah, emotions typically, again, typically fear and anger are the ones that derail our brains.

**Lenny** (00:29:08):
It makes me think of Alex Honnold, I think is his name, the free climber, the solo dude. His amygdala doesn't quite function so he doesn't-

**Matt Mochary** (00:29:19):
That's right.

**Lenny** (00:29:21):
That's interesting. He could be a free solo climber, he could be a CEO.

**Matt Mochary** (00:29:25):
That's right. CEO's a little safer. The prediction for Alex is that he will at some point, unfortunately die.

**Lenny** (00:29:33):
Yeah. Did you see The Alpinist? Not to spoil anything.

**Matt Mochary** (00:29:36):
Yes.

**Lenny** (00:29:38):
Okay, moving on from that, I'm curious, in a remote world, does your advice change in terms of firing? It seems like everything you shared you could do easily in person or remote, but does something change when you're doing it over Zoom?

**Matt Mochary** (00:29:51):
No, it doesn't change at all. There is one point I didn't include, which I'll include now, is there's helping the person be their agent, but there's also allowing the person, whenever I have a difficult conversation, I start it off, "Hey, this is going to be a difficult conversation. I want you to take a few seconds and prepare yourself. You are not going to enjoy this." What I found is that the way the amygdala gets triggered is often because of surprise. So, if you give someone just a few seconds to mentally prepare, then the amygdala often doesn't get triggered nearly as hard because if they're aware that they're going to go into fear, they're going to go into anger, they're going to go into sadness, then they can see it coming and they go, oh, that's what it is. But if they don't see it coming, just a surprise and all of a sudden it grips their whole brain and now they're in it and they don't even know they're in it.

**Matt Mochary** (00:30:43):
That's the first thing I do. This is going to be a difficult conversation. Are you ready? Then I share the news. I'm letting you go, here's why. Then second, I deliver the message. The third thing is now they're feeling emotions, strong ones. Even though I warned them, they're still feeling them. Now you want them to be able to release those emotions, and so I say to them, "My guess is you're feeling a lot of anger right now, fear, sadness. Is that true? And if so, would you be willing to share with me what you're feeling and what you're thinking?" Sometimes they don't answer, but many times they do and they share with me and they let it out. That's important to allow them to let it out. Then I make them feel heard and I actively listen. That makes them realize that I'm not trying to run away from the pain that they're feeling. I'm not trying to leave them alone with it. I sit with them as they have it and then I try to help them get through it.

**Lenny** (00:31:47):
That's something else I wanted to chat about is the feeling heard lesson that you have for people. I'd love to just get your advice on just how to help people feel heard. It's like, oh yeah, I know that's important. I want people to feel heard. I will listen and it'll go great. But you have some very tactical advice on how to actually make people feel heard.

**Matt Mochary** (00:32:05):
Yeah, there's sort of a few different levels of it. One way to make people feel heard is, let's assume you're talking to them because there's another way, there's an even more surface way is verbal. Sometimes what I do is I ask, if I'm in a group of people, and there's a question or a problem that we're trying to solve, instead of going around the room and hearing people's verbal opinions, which takes forever, I ask everyone at the same time to take five minutes to write down their solution. Then we all drop it in a doc and then I just read it. When I read it I say, "Thank you, Lenny." And that makes you know that I at least read it, so that's a little bit of feeling heard.

**Matt Mochary** (00:32:40):
Second, if I want to make you feel more heard, I ask you to say it verbally and then I repeat it back to you. "Lenny, I think what I heard you say is... Is that right?" And you're like, "Yes." Or you're like, "No, not quite a little bit different." Then if it's a little bit different, I repeat it again until you say, "Yes, that's it." Now you know that I understood you.

**Matt Mochary** (00:33:00):
Then there's a third way which is even deeper, which is especially if you're giving me feedback, you likely don't want to hurt my feelings. So what you're doing is you're giving me the feedback, but you're couching it, you're polishing it, you're rounding the edges, you're making it softer. It's not really what you're thinking, but it's what you're willing to say. If I want to make you really feel heard, I reflect back what I imagine are the thoughts in your head. If I think you're feeling anger, I sort of think to myself, well, what would anger feel like? I cause myself to feel that anger, then what are the thoughts that appear to me? I say something to you like, "Lenny, I think what I'm hearing you say is you're off and you're thinking, screw you, Matt. How dare you walk into the office and not even say hello to me? Is that close?" And you're like, "No, Matt."

**Matt Mochary** (00:33:49):
People either say one of two things, they say, "Yeah, that is it." Or they say "No, that's stronger than what I was thinking, but directionally that's right." What that really means is, yeah, that's what I was thinking. Almost always their thoughts are bigger than their words, but they really feel heard when I share their thoughts. Now, that's not the end of the process. I mean you actually have to then do something. Once you made them feel heard, you have to say, okay, well either I accept or don't accept this feedback and if I accept, here's what I'm going to do about it. If I don't accept, I need to explain to you why. Here's what's going on. You shared with me what's going on in your world, now let me share with you what's going on in my world. Hopefully, you can see why this thing that's going on in my world doesn't allow me to accept what it is that you shared, and hopefully now that you see what's going on in my world, your feedback changes and that's it. That's the whole process.

**Lenny** (00:34:45):
I'm listening to this advice and I'm like, yes, I will do this next time I'm talking to someone. I imagine people don't and they forget, and it takes time to actually learn these things. Like the firing advice you just shared, how do you actually get good at this and practice these things is like I have to work with a coach who will continue to reinforce these things? Is it follow these steps next time? Have them written down? What advice do you have for folks that are like, I want to get better at this. I want to start doing this stuff.

**Matt Mochary** (00:35:09):
Well, these docs are all free to the public in the curriculum. You can post them here, you can post them on Twitter, you can post the whole curriculum on Twitter, frankly, other people have. It has a step-by-step. There's a doc in there that is a step-by-step script. All you do is you read it and you follow the script in letting someone go or in making someone feel heard. My posit is once you do it one time, you're like, oh my god, that worked so well. That's the only motivation you need. And you've got the script, so you can just keep doing it. I don't think you need a coach.

**Matt Mochary** (00:35:42):
In fact, I remember one time I asked an investor who their best up and coming CEO was. The investor gave me a name. I was like, "Great, can I please get introduced to him? I want coach him." I reached out, the guy responded immediately. He's like, "Matt, I've read your book. I love your book. I read it three years ago. I've been implementing all the elements in our company. It's fantastic." When someone says that they know my work, they've already implemented it and it's worked, 10 out of 10 times, that person wants me to coach them. Then I said, "Great, that's fantastic. I'd love to coach you." And the guy said to me, "No, thanks." I was shocked. I was like, "Why?" He said, "Well, because it's all working. I don't have any problems. I don't think I need to be coached by you." I couldn't have heard a better answer. That, to me, is the ultimate answer. And he is right. He doesn't need me, doesn't need anyone.

**Lenny** (00:36:39):
I was going to ask if that's the goal of all of this writing down and systemizing is just to make yourself unnecessary.

**Matt Mochary** (00:36:45):
Totally.

**Lenny** (00:36:48):
**Matt Mochary** (00:38:16):
Ryan obviously started Product Hunt and then he sold the company to AngelList, so he was part of AngelList when I went there because I was coaching Naval. What we realized coaching Naval is that Naval did not want to be CEO and he just didn't know how to get out. So, I said there's a way and I can show you, and so I did and made Naval's life 10 times better. Frankly, made AngelList 10 times better because Naval wasn't enjoying being CEO, therefore he wasn't good at it. We ended up putting someone in who did a fine job, then put someone else in who's doing an insanely good job. Now, of course, AngelList is massively valuable.

**Matt Mochary** (00:38:53):
Ryan was there at the time, Ryan Hoover, great guy, I love Ryan. So, what has changed since then? I think what's changed is I don't think back then I had any of this fear and anger give bad advice. I think back then it was all very tactical. It was all very high up management type stuff, which is you need to have goals and at the company level, at the department level, at the individual level, you then need to track those goals. You need to track all the agreements that people make, all the actions they say they'll do. You have to put it all in Asana. Everyone has to be able to see each other's Asana board so they can see what each other is doing. I still do that, but now I've added on this piece of oh, you're in the moment and you're feeling fear? Okay, you still got to go forward. That's sort of the big change.

**Lenny** (00:39:42):
I noticed that's at the top of the curriculum. Do you find that's where a lot of the biggest transformations happen, that curriculum component?

**Matt Mochary** (00:39:49):
Absolutely. I cause people when they first start coaching, they have to read that first. There's sort of three seminal documents: on time, top goal, and fear and anger give bad advice. On time just says, hey, we're going to start our meetings on time and you're going to show up and if you don't show up on time, you're going to let me know first. That's just because I don't want to... And by the way, I showed up two minutes late for us. That's because I was on the Google Hangout for 10 minutes. I didn't realize, I thought you were-

**Lenny** (00:40:21):
I'm trying to fix that bug. Every time we send an invite, there's a Google meet button there. I think I cracked it finally. Yeah, that would've been a funny podcast where I'm just sitting here starting on time and for two minutes. Hello, we're just waiting.

**Matt Mochary** (00:40:33):
Exactly. Second one is top goal, which is this concept from McKeown, who wrote Essentialism, which is everyone is making requests of you, but if all you do is spend all day is responding to other people's requests, you never actually march towards your own priorities. You need to A, create priorities and then set aside some amount of time each day, 30 minutes, an hour, two hours that you just work on your own priority. If you do that, you'll make massive gains. And that's true. I mean, in five minutes I can change someone's life just by having them follow that practice. Then the third one is, if you're in anger, give that advice and that's what I have people read and say, "Does this resonate with you?" If it does, we can work together and if it doesn't, we shouldn't work together. So yeah, that's kind of like the crux document of whether or not people philosophically are going to resonate with what I have to share.

**Lenny** (00:41:25):
The top goal piece, I'm reading a book called Make Time right now and that's a big part of it. I actually just added top goal to my calendar every day. It's not working yet. Every time I get to it, I'm like no, I'm going to just check Twitter right now. But I'm working on it.

**Matt Mochary** (00:41:38):
That is the hardest part. Now, what I've done is I'm similar. During my top goal time, I have somebody sit with me and they prevent me from doing anything but my top goal.

**Lenny** (00:41:51):
Wait, can you talk a bit more about that? Is this like a coworker? Are you just like, "I need you here for this hour every day?"

**Matt Mochary** (00:41:56):
Yeah, I mean it's like the same idea as a trainer in a gym. A trainer in a gym, maybe they're teaching you a little bit, but more often than not they're just forcing you to do the thing that you know need to do. But if they weren't there, you would kind of go eh and not do it. That's all this is. It's what I call an accountability partner.

**Matt Mochary** (00:42:15):
There's even an app now where you can go online and you can sign up and I think it costs like $5 a month and you can sign up to meet someone else and you become accountability partners to each other. It's insanely effective. I'm not the only one that has a problem focusing on tasks that I don't love that are necessary, but I don't love. Like a meeting, I could take a meeting, I could take 20 meetings, I could take 10 hours of meetings, no problem. Especially when I'm the presenter, when I'm the active one. But doing asynchronous tasks for me because so people-oriented that when there isn't another human with me, it's painful, so I just have another human with me.

**Lenny** (00:43:04):
I love that. And that person is doing other work, I imagine they're not just watching you full-time.

**Matt Mochary** (00:43:09):
No, they can do whatever they want.

**Lenny** (00:43:12):
Is this what you recommend to leaders and CEOs? Just have someone there for an hour. Wow.

**Matt Mochary** (00:43:18):
If your personality is like mine, yes, have someone there. It can be remote, it can be in person, it doesn't matter. In person's a little bit more effective.

**Lenny** (00:43:27):
Right, there's like a little zoom window.

**Matt Mochary** (00:43:28):
I have my kids do it. They love it.

**Lenny** (00:43:32):
I love that. There's an app I use called Centered, that app that I'm an investor in, but I use it all the time and they have this buddy feature actually where you can be paired with a buddy in real time.

**Matt Mochary** (00:43:40):
Yes, yes.

**Lenny** (00:43:42):
To close a loop on the firing piece, something I was thinking about while you were talking is there's a lot of layoffs happening right now. When you're letting go of like a thousand people, you can't really be their agent unless you've seen that happen. Do you have any advice for just like there's a large layoff how you could do this?

**Matt Mochary** (00:43:58):
Absolutely you can be their agent, not you personally, but they each have a manager and the manager usually has 12 reports and they're rarely letting go more than 50% at a time. That means six people that they've got to be the agent of maximum. Yes, each manager can be the agent for six people. My companies have done a lot of layoffs and here's why. Back in March of 2020, there was a chance that the world economy was imploding. Now of course, by April and May we realized that wasn't the case, that the tech world kept going, in fact, it was even flourishing.

**Matt Mochary** (00:44:38):
But in March of 2020, we didn't know that. And so you needed, if you were being fiscally responsible, you needed to prepare for that eventuality, so you needed pare costs. 80% of costs in any tech company is payroll, is humans. If you're going to pare costs, you actually have to let go of humans. Almost every one of my companies did. Some on the low side of 5%, some on the high side. One company that is a hotel company let go of 40% because it looked like their business was about to get obliterated and the results were crazy. Within 60 days of each layoff, the CEO reported back to me: It's insane. I don't know how this happened, but the company's now operating better. I'm not talking on a relative scale, I'm talking on an absolute scale. We're putting out more features, more code. Our NPS is up, whatever it is, whatever department is performing better. The only answer for it was we've got less people, so this coordination issue is reduced.

**Matt Mochary** (00:45:49):
Then now in May, June of this year, we had this huge reset of valuations where growth tech stocks dropped by 50 to 90% value and all of a sudden, which we're still in and we don't know how long this can last, it's all based on interest rates so it's likely that growth stocks will be at these valuations until interest rates come back down again, which could be two to three years. These companies now they can go raise money, but it's going to be at a big down round and down rounds are very painful. So now these companies have to make sure that they don't need to raise money in the next three years. They've got to conserve cash once again.

**Matt Mochary** (00:46:33):
Here we are, we're in the land of layoffs again, but this time it's different. This time these CEOs know that the company actually gets better. And the CEOs that have never done this before, I simply connect them with the CEOs who have done this before and then they get convinced like, oh man, my company will be better. And now this time, people have been even more aggressive. We've had companies that have laid off 50% of the company and the results have been frankly, phenomenal.

**Matt Mochary** (00:47:02):
But the key to doing it well is there has to be a humane delivery. The biggest marker that I've seen between a botched layoff and a successful layoff is at the moment someone hears that they no longer have a job, did they hear it from their manager in a one-on-one? If that's when they heard it, it'll be okay. But if they heard it in an email, in a group chat, in any kind of thing where they were sitting next to or they're hearing it along with other people, it wasn't personalized, it wasn't one-on-one, that is terrible. That's when people get really angry and that's when they start going on Twitter and going to newspapers and et cetera because it feels dehumanizing. It feels like you didn't give a shit about me. You didn't even have the courtesy to tell me to my face. Of course, there's no way to allow that person to express their emotions because they're in a group. That's the most important thing.

**Matt Mochary** (00:48:17):
The second thing is then later, so tactically, this is how it happens. You have an inner circle. I think that inner circle should include all managers in the company and you say, this is how much we need to let go. Here's how much each of you needs to let go. First of all, you don't say to each department head or team leader, manager, tell me who you can let go because they'll all say nobody. You actually have to give them numbers. You have to let this dollar amount go or this many people go, dollar amount is better because if you say people, then they'll just let go of the cheapest people, the most junior, and often the most junior are the ones that are actually doing the most work. You want it to be dollars because that's actually really what you're trying to save. You're trying to save dollars.

**Matt Mochary** (00:49:07):
So, you say you have to save this many dollars, come up with a number, they quickly come back with a number. You don't want to have department heads choose for managers because if you have a team lead and all of a sudden they're told to let go these three people, the team lead will go, that was crazy. Those are my three best people. So you want to let each manager choose and that doesn't need to take long. That could take 48 hours.

**Matt Mochary** (00:49:29):
Then you move to implementation. At implementation, you spend the morning and have each manager reach out to people and just Slack them say, "Hey, can I talk to you for 15 minutes?" And then they have these meetings back-to-back-to-back or as close as they can and they deliver the news, the difficult conversation that we talked about before. "It's going to be a difficult conversation. I'm letting you go. I imagine this feels crappy or feels like worse than that. This is horrible. If you're willing to share your feelings and I want to be your agent now. I don't have time to do it now, but I'd like to schedule with you another hour tomorrow, the next day whenever, so that we can go and dig in and I can help be your agent."

**Matt Mochary** (00:50:12):
Then, that takes the morning. By the afternoon, you've scheduled an all hands for the stay team. With the stay team, you'd tell them what had just occurred and you answer their questions. The questions are almost always around fear. Like, "Holy shit, is this going to happen to me? Did these people even get feedback that they weren't performing? Does this mean that we're dying as a company and that we're going to implode?" You have to address each one of these questions and hopefully the answer is: no, to the first one, is this going to happen to me? No, this isn't. We cut deep so that we only cut once. The people to your left and right and you, you are the state team. This is the team that we're going to building the company with going forward. It's important to be able to say that. You actually want to cut deep because cutting two times or three times creates PTSD in an organization. It's trauma one, trauma two, trauma three. Now they're like, ah, it's just going to keep happening.

**Matt Mochary** (00:51:10):
Then, the third piece is, and this not everybody does, if you don't do this, your company within 60 days will be performing better. If you do this, your company within two weeks will be performing better because people now, the stay team, they feel sadness, they feel anger, they feel fear. Yes, you addressed their questions in the all hands, but not fully because some people didn't even talk in the all hands.

**Matt Mochary** (00:51:34):
So, what you do is with each and every person on the stay team, you have a one-on-one with their manager for one hour and all the manager does is say, "I'd like to know your thoughts and feelings," and the person shares and then all the manager does is make them feel heard. I think what you're telling me is you feel sad because your three buddies are now no longer here and you feel anger because you think this is bullshit and you think why did we hire this many people if we're going to fire them? That was just irresponsible. You feel fear because you're not sure if the company's going to implode or if your job is safe. Is that right? And they're like, "Yes."

**Matt Mochary** (00:52:11):
It doesn't take away the emotion entirely, but it knocks it down by a good 25%, which is enough that the person won't do something rash, they won't quit, they won't stop working, they won't say bad shit to other people, and it allows them to accelerates their recovery. Within two weeks, they're now seeing how the company's operating better and morale then comes up and the company's now performing better than it was before. So, three elements.

**Lenny** (00:52:44):
That was thousands of dollars of advice I think, in just five to 10 minutes.

**Matt Mochary** (00:52:50):
That's after having probably gone through this with CEOs maybe 40 times and iterating AB testing, and what's the difference, and what works well, and what didn't work well. Yeah, I can't imagine there's somewhat out there who has advised more people through a layoff process, certainly in the tech world, than I have. I'm not saying I'm proud of that, but it just is.

**Lenny** (00:53:17):
What a fun place to be. As you were talking, I was thinking a little bit about Twitter and Elon and the experience that's going through right now. It feels like on the one hand, he's letting go of a lot of people, which matches kind of your advice. On the other hand, not being handled too well. I think it's emails and just a lot of random quick things. What's your perspective on this whole thing?

**Matt Mochary** (00:53:39):
I haven't been following it directly, so I don't know how he's implementing the layoffs or how much he's doing. Frankly, just haven't been following it at all. But here's the sad reality, even if it's handled incredibly poorly, the company ends up performing better. It just takes a little longer for people to recover, for the stay team to recover emotionally. But the worst case scenario, it's handled terribly, within two months, the company will be performing better.

**Lenny** (00:54:09):
Fascinating. That's actually a good segue to this last topic I wanted to touch on, which something that I think you have a lot of thoughts on is building new products within a larger company and innovating inside of a larger kind of scaled company, and especially the challenges around that. What are your thoughts on just how to do this well, how to innovate within a larger company?

**Matt Mochary** (00:54:30):
I can tell you the short version, but I'll tell you the long version. The long version is that this was a real problem for everyone I was coaching and I didn't know the answer. But it was obvious that YC startups were crushing and just iterating so much faster. And then I had the thought, well, why not just create your own YC startup and have it crush you but you own it? It, of course, has to really look like a YC startup. It has to have a founder mentality person as the head of the team, someone who's willing to just break glass and just won't stop until they run through the brick wall. It's actually pretty easy to find founder mentality folks. You just literally go to the YC alumni list and the ones whose startups failed, perfect, they're available and they are founder types and now they want to join a company that's actually succeeding because they realize how hard it is to create something on their own, but they still have the mentality.

**Matt Mochary** (00:55:24):
Then you want to keep the team really small because then they can, again, there's no buy-in required, like everyone's on the same page with the same information. We started testing that and it worked, and then I thought, well wait a second. The reason that a big company has a hard time innovating, it's because once a product is scaled, it's now got millions of users. So you have two things that you need to make sure stay true every day: the site is up and running and there's no security breach. Every time you add code, you've got to test it thoroughly to make sure it doesn't take down either one of those. The review process is insane.

**Matt Mochary** (00:56:06):
So now you're innovating, you're writing prototype code on new features. You can't get it approved it takes so long. That's what you're trying to decouple and you're trying to create an entity that isn't touching the core code, but you also don't want to have to go through the approval process of the product team or the head of product. That takes way too long, as well. That's why it has to be a small team that reports to outside of EPD. It can't report to the head of engineering, head of product, head of design, it can't. It's got to go outside, usually directly to the CEO. That's the only other place to report that's outside.

**Matt Mochary** (00:56:48):
Then I had this idea, well wait a second, there's also a brand question and so why don't you create an entirely new name for this product that isn't the core, the base business? Why don't you actually just create its own C corp? Why don't you make it so clear that this is its own entity? So I wrote this whole thing up and created its own C corp. I shared this with a few people and one CEO said to me, "Matt, this sounds radical and sounds like it could work, but is anyone actually doing this?" I thought to myself, oh shit, no, nobody's actually doing this. Nobody that I know has created new C Corps for the entities, the new products they're developing.

**Matt Mochary** (00:57:34):
Then 30 days later, I got in a call with Wei Deng. I told you before, I'm a huge fan, and we talked about product and I shared with her this write up. She's like, "Oh yeah, that's what I do." She said, "I created five C Corps in the last two months." I was like, "What? Someone's actually doing it." I was like, "Well, what are the results?" She's like, "They're fantastic." She goes, "The team doesn't worry about trying shit because they know that it doesn't hurt our core brand, and so they're iterating fast." And she said, "Not only do I do that, I actually have two teams, independent, working on each new product. One I have is more engineering focused, they build custom code. The other is more sort of customer relationship-focused and maybe they don't even have engineers and they build a manual solution or they use off the shelf products to build a solution, and just see which one makes more progress faster." Wow, insane. That's why, again, I have so much respect for Wei.

**Lenny** (00:58:36):
When I think about these ideas, I think of the NPE team at Facebook and I think it's called Area 21 at Google, which works on new ideas and I don't know if anything amazing has come out of those groups maybe, I don't know. But it feels like the missing piece, and you didn't mention this piece, is feeling like there's a huge upside if you get something. Like founders having equity of their company feels like such a motivator. I could become a billionaire if this works out, versus I'm helping my startup in some small incremental way. Is that an important piece or do you think it's not critical?

**Matt Mochary** (00:59:09):
I'm going to be radical here. I don't think it matters at all. I think that what really motivates people is building shit that gets used in the world. I think people will say, and they'll fight for equity and money, but in the end, that's not what actually motivates them. Because I've seen this work in companies where they don't have big equity, but they have autonomy, they have ownership, not equity ownership, ownership over decision making, ownership over creation. That's what I think people want. Amazon does this. They're not giving their people... Amazon's famous for being cheap bastards, but someone has a great idea, okay, here's 5 million bucks, go do. Amazon is definitely innovating successfully.

**Lenny** (01:00:02):
What about the flip side of that of not necessarily the huge upside, but the I'm staking everything on this startup, I need this to work, this is my thing, my name's on the line. I feel like that's a big motivator also for founders, like I'm not going to give up this feeling of grit. Is that important?

**Matt Mochary** (01:00:21):
Yeah, it's also fear. It's fear, which is like if this doesn't work, I'm screwed. Fear, frankly, is an excellent motivator. It gets people to move fast and move hard. The only problem with fear is it's also corrosive, so it eats out my insides as I go along. It makes it that I don't enjoy life, but it's highly motivated. Now, I think joy is actually even more motivating or they say it's as motivating, but it's noncorrosive, so I can last much longer if I'm doing something for joy. Fear is short term, extreme motivation. It's adrenaline. Joy is long term, consistent motivation that also allows me to look back on my life and go, wow, that was a great life. So yes, that is effective motivation, but I don't recommend putting oneself in that position to get motivated.

**Lenny** (01:01:14):
For companies that want to try this method that you're describing, is there a curriculum document for this approach out there?

**Matt Mochary** (01:01:21):
There is.

**Lenny** (01:01:22):
Okay, we'll link to that. Are there any other companies that are doing this well that come to mind? You mentioned Amazon, Clipboard Health.

**Matt Mochary** (01:01:29):
In my portfolio, I know Scale and Attentive Mobile are both doing this well. More and more companies that I coach are starting to do this because I have more and more examples of it working well, so more and more companies are then copying. I don't have other names offhand that I can share though.

**Lenny** (01:01:43):
What was that first company? Scale?

**Matt Mochary** (01:01:45):
Scale.

**Lenny** (01:01:46):
Cool. Is that Scale AI?

**Matt Mochary** (01:01:48):
Yeah.

**Lenny** (01:01:48):
Okay, cool. I love that. Love that founder. Maybe a last question, something that I noted just in case we had a little more time is around energy audit. This is something that you advise folks to understand what gives them energy, what zaps their energy, can you talk a bit about that?

**Matt Mochary** (01:02:06):
Sure. It turns out that what we're really good at is what we love and what we love is often space and time disappear when we do it. Therefore, we actually probably don't even value it because it comes so easily to us that we don't ascribe value. Whereas things that we don't love but we're good at, we often ascribe value there and other people want us to do those things because they're often creating value for the whole team or the family or the group.

**Matt Mochary** (01:02:39):
There are four zones I posit and I learned this from Diana Chapman at Conscious Leadership Group. I don't know where she learned it from, but almost everything that I have, I poached from somebody, but at least I tell you where I poached it from. The concept is you have four zones.

**Matt Mochary** (01:02:58):
Zone one is your incompetence, you're not good at it, someone's better at it than you. That's like fixing a car. You should let someone else do that.

**Matt Mochary** (01:03:07):
Second is your zone of competence, you're fine, you can do it fine. But so can somebody else do it fine. Like cleaning your house. Yes, you could do it, but it would take a lot of time and you're not creating that much value. You should let someone else do that.

**Matt Mochary** (01:03:22):
Third zone, your zone of excellence. This is something that you're uniquely good at, but you don't love it. This is the danger zone. This is likely what you're getting paid for and you're likely to getting paid a lot of money for it. Other people want you to do it. You are creating value, but it's also sucking the life force out of you and it doesn't allow you to become amazing and create massive value.

**Matt Mochary** (01:03:45):
Then there's your zone of genius. This is the thing you do that's uniquely good in the world and you don't even notice that you're doing it because you love it so much. The key is to go and look at your day. How do you move into the zone of genius? It's not that you figure out what it is and do more of that, it's that you figure out what it isn't and eliminate that and then naturally, you'll be drawn toward what it is that you love.

**Matt Mochary** (01:04:10):
What I do with the energy audit is you go through a calendar, two weeks of a calendar, a representative two weeks and you first look at all the meetings you have, but then you fill in there's time in between meetings. What were you actually doing? Take your best guess, write it in and then hour by hour, take a green marker and a red marker and each hour from Monday, 8:00 AM to 6:00 PM and the same thing each day for two weeks, each hour ask yourself at the end of that hour, did I have more energy or less energy?

**Matt Mochary** (01:04:41):
If it's more energy, you mark it green. If it's neutral or negative, you mark it red. Then, once you've done that for two weeks, you look at all the reds and say what's with the themes here? Oh, one on ones with people who are no longer by direct reports, team meetings where nothing was prepared in advance and everything was verbal. Recruiting meetings, interviews with people that we didn't end up hiring. Informational interviews from people that wanted to meet me and just know me but provide no value to me. These are all things that are energy draining.

**Matt Mochary** (01:05:14):
Great. Now what you do is you go through each one of them and say, one, do I need to do this at all? Does it need to be done? If the answer is no, just cancel it. Two, it needs to be done, but someone else can do it. Great, delegate it to them. Three, and this is the most common, it needs to be done and only I can do it. Great, then the question is, what would make it exquisite? Well, it's the exec team meeting. I'm the CEO, I have to be in it. Well, what would make it exquisite?

**Matt Mochary** (01:05:41):
You know what would be exquisite? It would be exquisite if everyone pre-prepared their update, which said how they're doing against their priorities, regular green, what they did last week, what they're going to do this week, and then they pre-route any problems they saw in the company and any proposed solution they had for those problems. If everyone did that, then we could spend the first 15 minutes of the meeting just reading, processing the decisions and we could take a three hour meeting down to a 45 minute meeting. Great, go write that up, share it with a group and say, hey gang, this is what would make this meaning exquisite for me. What do you guys think?

**Matt Mochary** (01:06:18):
Nine out of 10 times people look at it and go, yeah, that would be amazing because they're feeling the same way. Then you go with a new methodology and it turns out to be great. That's how you take what you do each day from a lot of energy draining things into open space or energy raising things which will then allow you to start doing more and more of the things that you love. You keep doing this energy audit repeatedly, 1, 2, 3 times until your calendar is 80% green. Once that happens, magic will occur. All of a sudden, your life will become phenomenal and you will start to create massive value. I did it. That's what happened to me.

**Lenny** (01:07:05):
I did that too actually, a simpler version where I just paid attention to what gave me energy and what didn't give me energy when I was on this journey post Airbnb and I thought I was wanted to start a company, I thought I wanted to do some advising and consulting and I realized none of that gives me energy, but writing interesting things that people like, that was fun. So I just kind of doubled down on that path and had no idea was going to make any money and it ended up making money and that's what I do now. So yeah, two thumbs up for this method and it's a more sophisticated version, which I like.

**Matt Mochary** (01:07:36):
Right on. That's also trusting that there will be, if you need to monetize, eventually you will be able to monetize, but you got to start with doing the thing you love first.

**Lenny** (01:07:51):
Right. Yeah, I feel like there's a lot of people on Twitter and newsletters that are just doing it because they think this is something they will enjoy and other people are doing it. But I find that with this content life, you get on this treadmill where you have to continue producing things and if you don't actually enjoy it and it's not interesting to you, you end up just building this job for yourself that is no fun at all. Extra important if you're kind of going down this path.

**Lenny** (01:08:19):
One quick question I had along these lines is you're talking about how you focus on yourself and your energy and what works for you or not. And I was like, do these collide with other people on your team because they maybe get energy from something you don't? But your point is that oftentimes, everyone's like, "Yes, this is good for me too. We should do this because it's going to help everybody feel better."

**Matt Mochary** (01:08:38):
That's exactly right. I remember one time we did this energy audit process, I did it with Henrique and Pedro from Brex and it was revolutionary for them. It caused them to change how the two of them operated together. They realized one really enjoyed the internal meetings and the other really enjoyed the external meetings, so well great, let's just do that. It changed the trajectory of the company so much so that they said, "Matt, would you please come in and do this energy audit with all of our managers?" And we did. We did a big group thing and what they found was that process also changes the trajectory of the company because for everything that you don't enjoy but needs to get done, there's someone out there that loves to do it. You just got to find out who it is, and that's what happened.

**Lenny** (01:09:28):
I was just talking to my mom who's a CPA and I'm like, "Do you even enjoy this job you're doing?" She's like, "I love it. I love doing taxes. It's so interesting." I'm like, I'm so happy somebody out there enjoys this. I would pay anything for someone to take this off my plate. You can charge me. Because my mom does my taxes.

**Matt Mochary** (01:09:44):
That's exactly right.

**Lenny** (01:09:45):
Matt, any final thoughts you want to share before we wrap up?

**Matt Mochary** (01:09:49):
This was fun. Thanks, Lenny. I appreciate this.

**Lenny** (01:09:52):
Super fun. I feel like a sign of a great conversation is it feels like we've been talking for maybe five minutes, but also a lifetime. Maybe we'll do this again. There's like a million other questions I'd love to get into, but until then, where can folks find you online if they want to reach out and learn more and how can listeners be useful to you?

**Matt Mochary** (01:10:07):
Where can people find me? I don't know. Don't find me. I won't be able to respond. I get too many inbounds and I can't respond to them. In terms of people helpful to me, just read the content and use it and don't pay me to coach you. Just do it on your own because you don't need to pay me to coach you.

**Lenny** (01:10:28):
I love that. It's the first time someone's like, "Do not reach out. I got it all for you online." We'll link to the show notes of the doc and everything. Matt, thank you. This was incredible.

**Matt Mochary** (01:10:39):
Thank you, Lenny. This was great. Take care.

**Lenny** (01:10:43):
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.

---

## [12/20] Alex Hardimen

**Alex Hardiman** (00:00:00):
One thing that's really interesting is that our impact and our business goals are in service of our mission, which is to seek the truth and help people understand the world, not the other way around. What it means is that the way that we think about impact is growing a giant subscription business. That business exists to strengthen an informed democracy at a time when people are struggling to understand basic facts and struggling to understand each other. That means that impact for us is growing subscribers, but it's also when a deeply reported story triggers an important policy change or a new law.

**Alex Hardiman** (00:00:40):
When you're a product manager, you're involved again in driving specific metrics like engagement or subscribers, but you're also trying to help stories find their real audience in ways that trigger just this whole different side of mission and purpose driven impact. I didn't feel that when I was at a place like Facebook.

**Lenny** (00:01:00):
Welcome to Lenny's Podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. Today, my guest is Alex Hardiman. Alex is Chief Product Officer at the New York Times where she leads teams that build the company's news, cooking, games, audio, and advertising products. Prior to this role, she was Chief Product Officer at The Atlantic, and before that, she spent two years at Facebook where she led their news product amongst other things. As you'll hear in our conversation, Alex has been at the center of the storm so many times, including at Facebook right after the 2016 election.

**Lenny** (00:01:33):
**Alex Hardiman** (00:04:52):
Thanks so much, Lenny. It's really awesome to be here with you.

**Lenny** (00:04:55):
What's interesting is I think you may be the first product leader on this podcast who doesn't work at a big tech FAANG startup, and so I'm really excited to just dig into see what it's like to build product at a company like the New York Times.

**Alex Hardiman** (00:05:08):
Thank you. No, no, that sounds awesome. Let's dive right in.

**Lenny** (00:05:12):
Okay, before we dive in, I'd love to get a little bit of background on just your career. I'm curious, what was your career path to becoming the chief product officer at the New York Times?

**Alex Hardiman** (00:05:23):
Thanks for asking. I've definitely spent most of my career right at the intersection of journalism and tech. I think in hindsight, if you were to ask my family, they probably wouldn't be that surprised, even though for me I was just rolling with it and following what felt like a really interesting set of problems to solve. But when I just look at my family, there is a ton of journalism in our DNA. My grandfather was a news anchor on the West Coast and I really revered him. My great-grandmother, she was pretty amazing. She actually started one of the first TV stations in the Midwest back in the '50s when it was still pioneering territory.

**Alex Hardiman** (00:06:01):
For me, one of my first, the dream for me was to try to find a way to build things in the new space. That's how I first ended up at The New York Times. I've had two stints at The New York Times. My first stint was for a decade, from 2000 to 2016, and it was during a really interesting time of pretty big transformation. There's so much to talk about within that decade, but I would say there are two really big things that happened in that moment. The first was really trying to work with the company to shift from being a print first product into a mobile first product. If you go back to 2006 and you think about it, the Times had no mobile presence whatsoever.

**Alex Hardiman** (00:06:40):
Even the iPhone 2G and the App Store didn't come out I think until like 2008. We just really started investing in small mobile use cases, first on the margins and then more and more aggressively until we were just leading with mobile in everything that we did. New journalism formats, new product features, new revenue opportunities, that type of thing. Then, the second big thing that marked my journey at The New York Times was the shift to a direct to consumer subscription model. This was back in 2011, and there was just a lot of skepticism, including from people at The New York Times, about whether or not people would pay for quality journalism.

**Alex Hardiman** (00:07:17):
We brought in consultants and they said, "Maybe over the course of history it'll get to one million subscribers, if you're lucky." It felt like a really big nervous [inaudible 00:07:27] at the time. But thank goodness it helped make a market for paid journalism, that has really helped a lot of news organizations find new ways to support quality coverage. But after a decade I did what I think a lot of people did, was you look around and you say, "I love what I do, but I would love to go learn how to do product in the context of a product led digital first company." That's when I went to Facebook and I left in 2016.

**Alex Hardiman** (00:07:52):
The timing is actually pretty important in terms of my experience at Facebook, because when I first joined Facebook, I totally left the media space. I was focused on building out a team that was really trying to help micro sellers in markets like India and other parts of APAC, who were coming online for the first time in really low bandwidth areas, and just wanted to sell their goods through social commerce. Really looking at what WhatsApp and Line and other regional competitors were doing. We were focused on business messaging and the interoperability of the Facebook apps from more of a small business perspective. It was really awesome work.

**Alex Hardiman** (00:08:28):
Then, the 2016 presidential election happened. I had only been there for a couple of months and as has been discussed very widely and reported widely, it was a wild time where there was just so much reckoning around misinformation, disinformation, election integrity, platform responsibility. I went over very quickly to help out on the news front where I led the product and engineering teams and it was really hard, really interesting work. I did that for a couple of years, decided-

**Lenny** (00:08:58):
Before we move on.

**Alex Hardiman** (00:09:00):
Yeah.

**Lenny** (00:09:00):
I'm curious. Okay. Wait, you were leading the news product at Facebook during the election?

**Alex Hardiman** (00:09:03):
Right after the election.

**Lenny** (00:09:05):
Right after the election, after everyone was coming after Facebook trying to tear it down?

**Alex Hardiman** (00:09:09):
Yeah.

**Lenny** (00:09:09):
Wow. What year was that?

**Alex Hardiman** (00:09:13):
I joined in early 2017 on that effort. The election was November, 2016.

**Lenny** (00:09:19):
Oh, my God. Before you move on, just what was that like? I don't know how one can describe that experience, but what do you think about when you think back to that time?

**Alex Hardiman** (00:09:28):
I think about wartime product management, right? You're coming in, and I think there was ... What I appreciated about that time inside of Facebook was that there was just this incredible humility that was needed to really understand and first diagnose what was actually happening on the platform, and the approach to content on Facebook historically it was very binary. You basically had content from friends and family and then you had public contents. Public content could come from anywhere. It could come from a reputable news organization or it could come from my younger brother posting something and declaring it to be true.

**Alex Hardiman** (00:10:06):
What we really tried to do very quickly was try to unpack the categories of public content to say that there actually is something that is factually accurate information, and that requires a certain craft from the journalistic trade. There are ways to really look at what is trusted information, how you make that a little bit more essential and visible to people on the platform, while then reducing things that are at best dubious or at worse truly misleading propaganda. It was really fascinating and really hard just because the platform hadn't been built to think about classification of coverage in that way.

**Alex Hardiman** (00:10:44):
Let alone to have the right goals and responsibilities and incentives. There was just a ton of work to figure out how to make the platform far safer and far more informative after, I would say, a pretty intense election cycle.

**Lenny** (00:10:58):
Yeah. I was going to ask you about this later, but I feel like you're drawn towards just crazy, wild and crazy center of the storm roles. I guess that one you didn't expect necessarily to become that. I imagine The New York Times has a lot of that, but maybe a quick question there. What have you learned about just living in a world of just constant chaos and stress and urgency, endless urgency?

**Alex Hardiman** (00:11:21):
I would say, if you did ask my family and my husband, he would say that I'm always attracted to the more chaotic problems. I just actually think that that's where product people thrive. The idea of being able to take all of these crazy inputs, trying to create a very structured model to figure out, "Okay, what is true? Where do we have conviction? Where do we have questions? What are the most important problems to solve? How do you prioritize? How do you get a team rallied around a shared context in one single goal? These are actually the conditions where product manager, I think, thrive.

**Alex Hardiman** (00:11:55):
For me, just having been in the journalism space for about two decades now, it's just been or the tech space around news, it's just been a constant set of upheaval and transformation. Some things within our control, some things entirely outside of our control, and so I love it. For me, there's nothing else I'd rather be doing than trying to solve these problems in the world at scale. But it does take a certain amount of just grit and resilience, and the ability to really focus on the most important problems in a given moment. Also, the ability to let other things slide when you have to.

**Alex Hardiman** (00:12:32):
But again, I feel like these are core product skills that we look for in terms of leadership and grit, and the ability to drive through really, really tough problems that there's no playbook for, nobody has ever really done before.

**Lenny** (00:12:43):
Yeah. You said PMs thrive in this. I think some do. Some are like, "No, leave me out of that."

**Alex Hardiman** (00:12:48):
I guess that's true.

**Lenny** (00:12:50):
There's a metaphor I like to use when I give PM's advice on where to work within a company, which is there's like the Eye of Sauron, which is the number one most important thing to the CEO at that time. My advice is often don't avoid that thing, usually, but work maybe to the side of that because you don't want to work on something that doesn't matter, that's like over in the shire land. You want to be something that matters but not maybe the most important thing. I feel like you're the opposite. You're like, "Where's the Eye of Sauron focused? I'm going to go there and build stuff." That's pretty awesome.

**Alex Hardiman** (00:13:20):
Awesome, sometimes, I'm sure there are moments too where it would be nice to chill, but I am drawn to those types of problems for sure. This feels like therapy, Lenny. I'm into it.

**Lenny** (00:13:31):
Tell me about your mother.

**Alex Hardiman** (00:13:34):
She's wonderful.

**Lenny** (00:13:37):
Okay, great. That's the end of that one. I'll let you finish your career overview and then-

**Alex Hardiman** (00:13:42):
I feel like we're almost at present, which is I found that there was so much incredible experience that I was able to soak up and lean at a place like Facebook. For me, I really wanted to figure out how to apply that back into organizations that just had more of a classic journalistic mission and purpose, so I went to the Atlantic for a year. They had just been purchased by the Emerson Collective, so it was a really fun moment of just investment and expansion and ambition. We launched their consumer business. Then, I came back to The New York Times in late 2019, right before the pandemic, and I've been there ever since.

**Lenny** (00:14:19):
Oh my, just your timing is impeccable every time.

**Alex Hardiman** (00:14:22):
It really is.

**Lenny** (00:14:24):
I was doing some research on you before this chat and when you came back to The New York Times, there's all these stories about how big of a deal it was. Returns to The New York Times. That must have been something coming back, because you're there for 10 years initially, and then you came back. What was that experience like just coming back to something like that after being away?

**Alex Hardiman** (00:14:43):
I felt really lucky. When I left The New York Times back in 2016, it was on really, really good terms. It almost felt as like, I'm going on an externship and I really hope that one day I'll be able to come back and just do my job better. Because I do think there's real value in being able to do product in a bunch of different contexts. You're just so much better at pattern recognition, learning how to solve a diversity of problems, learning to work through things. I had a lot of great support when I left, which was really important. I don't think everyone necessarily has the privilege of that support when they exit a company. When I came back, it was just a real moment of excitement. My interview process, I joked with my boss at the time. But it did actually feel more like therapy.

**Alex Hardiman** (00:15:30):
When you've worked with people for a decade before and you go in, the conversation isn't the normal list of interview questions. It's like, "Okay, here's what type of leader you were a couple of years ago. Here are the conditions on the ground now, how do you feel about X? How do you feel about Y? Are you still passionate about solving this? What else have you learned that's going to make you better?" It was wonderful. It was one of the best interview processes because you're talking to a bunch of people who knew what you were like when you were leading as a person at a different point in your career and they're pushing you to be better. I felt like I got the best chance of a lifetime to come back and try to do my job better than I had been able to do it before, and that's pretty cool.

**Lenny** (00:16:12):
You've been there three years at this point?

**Alex Hardiman** (00:16:14):
Yeah, three years on Halloween, so coming up very soon.

**Lenny** (00:16:18):
Oh, wow. That's three days from now when we're recording. I wonder when this comes out. I'm curious, at a company like New York Times, which is, I imagine people think when they think product, they think it's the newspaper. At Airbnb we have this challenge where when we talk to hosts, "Here's the product." You're like, "What is your product? Is it our homes?" You have to help people understand, "Okay, when we talk product, we mean the website and app." What do you think of the product at The New York Times? Then, is it a challenge to help people understand, here's what the product team does?

**Alex Hardiman** (00:16:46):
It's a really good question. At the most basic level, I would say that our product is our journalism, which we then marry with a really compelling and useful user experience, in a way that helps people really act on our journalism so that they can understand and engage with the world around them. For about 150 years, our product was pretty simple. It was a printed newspaper, which is still very beloved today, but the UX of the newspaper was, it was a predictable structure. It was a very finite amount of news. It was time bound, which I think is a really lovely thing in terms of setting expectation. It also has the packaging of the newspaper just such serendipity, where you can move across news, opinion, culture, games.

**Alex Hardiman** (00:17:31):
It's a really great bounded product in and of itself. But about 25 years ago, when we started shifting over to digital, the web, and mobile, the world just fully opened up in a way. We just saw this really tremendous disaggregation and distribution of our journalism. We really tried to meet the moment by building a wide array of products in the news space to extend our reach. Our products then, our digital products were our website, our apps, newsletters, we dabbled with a lot in the VR/AR space early on. That was, I would say, the first big extension of our products. When we then pivoted though to a subscription model, it was a really interesting moment where we actually had to take more of a destination first approach.

**Alex Hardiman** (00:18:15):
It was almost like the beginning of us rebundling all of what we did, but on our own destination again, in digital destination. Because in order to build a really thriving subscription business, you really need a direct relationship with your customer as opposed to just relying on platforms to really distribute your coverage. That's where, again, we really started rebundling the breadth and depth of value that people once found in the Sunday newspaper at digital scale. Now, today, our product bundle includes even so much more than news, which I hope we'll talk about a little bit more later. We've really scaled our products in a bunch of different categories where we feel like we can really help people understand and engage with the world.

**Alex Hardiman** (00:18:57):
We have cooking, we have games, we have sports, we have Wirecutter, which is a great innovation surface. We're playing with a new audio app all around audio journalism. We have now six fully fledged different product destinations. The next thing for us to do is to really figure out how to put those together into a bundle that really becomes the essential subscription for any curious English speaking person around the world, who really wants to know what's happening and wants to be able to, again, act and engage and make great decisions based on the products that we build.

**Lenny** (00:19:36):
Got it. It sounds like the strategy is a subscription bundle where you just keep bundling awesome stuff into this bundle. It's an obvious thing everyone has, whether you want cooking or games or The New York Times online.

**Alex Hardiman** (00:19:48):
I think that's right. We did this pretty great exercise and strategy projects over the last year. We took a look and we said, "What is the largest addressable market where The New York Times can be truly valuable every single day to a group of people?" What we found was that there are about 135 million people around the world we believe are willing to pay for the type of high quality journalism based products that the New York Times produces, in the categories of news, gameplay, cooking and recipes, sports, which is why we acquired the athletic shopping recommendations and audio. In order for us to really capture as much of that audience and really serve them well, there are really three things that we need to do to make that essential subscription work.

**Alex Hardiman** (00:20:37):
The first is we absolutely need to have the best news destination in the world. When you think about the New York Times, we actually have the solar system metaphor where for us news is the sun in the sense that it's why we exist. It is what gives us our brand heritage and reputation. It's what instills trust. It's also where we just have the largest audience when you think about a funnel for our portfolio, and it's also where we just have the most amount of high quality coverage. But then that sun helps you give birth to other satellite planets or products that have a lot of the same DNA. Again, like great trusted journalism, great journalists who just have real expertise.

**Alex Hardiman** (00:21:16):
A great product experience that allows you to really unlock that value distribution reach, and the other ingredients that you would need for successful products to work. We're really focused on building out beyond news products that really help people engage with their passions and life needs that go beyond news. Then, the third thing is what you're describing as the bundle, how do we create a connected family of products that puts all of those things together so that wherever you come into the New York Times, to news or maybe through Wordle, you know that you're having the best experience within that category.

**Alex Hardiman** (00:21:49):
But then you also can quickly experience and discover everything else that we offer. That's the strategy and the vision, and it's a huge ambition. We want to get to 15 million subscribers by 2027. We're just over 9 million today, and I really think we can do it.

**Lenny** (00:22:06):
Awesome. I actually wanted to chat about goals and how you think about success as a product team. I imagine the north star metric is what you just said, which is subscribers. If that's true, what other goals do you have across teams? Maybe even further, I'm packing a lot of questions into one question, but I'm curious just how your product team looks. How many PMs do you have? Roughly, how do you structure the teams? Then, roughly, what kind of goals do they all have to try and imagine the product team at New York Times?

**Alex Hardiman** (00:22:34):
Let's start with structure. First, I love this question talking about my team because I love hyping them. They're amazing, and our success is truly only as good as our people. Yeah, it is so true. For us, when we think about our org structure, the way to set that up so that our people can really do their best work is that we have two axis. We have functions and then we have missions. I oversee two functions, which is the functions of product and design. The functions themselves, it's normal of what you would find in terms of functional responsibilities. We focus on standards of craft and excellence, career growth, career frameworks, equitable promotion processes, community of practices, skill development, all of that.

**Alex Hardiman** (00:23:21):
But missions is where a lot of the work happens. These are cross-functional teams, very similar to what we had at a place like Facebook. These cross-functional teams are led by usually a general manager, a product leader, or an engineering leader. They're all pursuing the same high level goals and objectives. Cross-functional missions at the Times, it can include a lot of the same skill sets that you would find at a tech company, PMs, engineers, designers, data scientists, researchers, product marketers. But the big difference is we also have editors, if it's a product space that directly shapes our journalism. I can talk more about that because it's a pretty interesting differentiating factor.

**Lenny** (00:24:02):
Yeah, that's super interesting. There's a journalist within cross-functional product teams?

**Alex Hardiman** (00:24:05):
Exactly. But we have three different types of missions. We have consumer missions, we have monetization missions, and we have platform missions. Editors are embedded within consumer missions. Those are the missions that I oversee, where we're focused on creating really great products, again, in categories like news, cooking, games, audio, et cetera. That is where having editors involved, particularly like editors who are very product minded, it brings in the best of their expertise and marries it with a lot of the normal signal that you look for in terms of data research and other insights. When you're trying to make sure that you understand a consumer problem and that you're really finding the best creative solution for it.

**Lenny** (00:24:48):
Cool.

**Alex Hardiman** (00:24:49):
It is really cool. It's one of the, I think, most gratifying parts of working at a news organization like the Times. But if you work on a different mission, like a monetization mission, we have two really big ones. One is subscriber growth, the other one that's also really important is digital advertising. They build centralized commercial products that we can then scale across all of the products in our bundle. The subscriber growth team, for instance, they look at making sure that we have really great account ID management for subscribers. If you're buying a subscription through games or through news. Or, if you're on the digital advertising team, you're trying to make sure that we have a first party data program that's really privacy safe, that works as well in cooking as it does in the news space.

**Alex Hardiman** (00:25:33):
Then, there's a totally different third bucket of mission that we have, which is all of our platform teams. This is everything from monetization platforms like our commerce engine, which is so important, because we're a subscription business, to data platforms where you might have our ML platform or experimentation tooling, to just basic infrastructure. Those are shared across the bundle, which just really helps make it so much easier, more efficient for really engineers to ship code and do their best work. A lot of this actually, I think, probably is pretty familiar to how you might organize at a tech company minus the editors.

**Lenny** (00:26:14):
Awesome. On that info piece, that reminds me of something I definitely wanted to talk about, which is something New York Times is really known for is the visualizations and these immersive stories that you all put out. I'm so curious just how that gets done. I feel like if I was on a product team at a regular, like a big tech FAANG company, I'd be like, "Shit, all these ad hoc things I got to do for all these stories, such a pain in the butt." That's so important to the New York Times and the online experience. I'm curious just like what is it like to build these things, say the election widgets, and all of that stuff?

**Lenny** (00:26:47):
Then, I don't know, I was just reading a story about climate change and it's this really beautiful immersive story of just what is happening with the world. There's a bunch of questions there, but I guess roughly just how does that get done, something like that?

**Alex Hardiman** (00:27:01):
Well, first, thanks for saying that. I really appreciate it. I do think there's something really special about some of the ways that we marry the journalism and the presentation. I want to start just by giving credit where credit's due, which is I think some of the most interesting and inventive and compelling formats, they actually do start off as one-off experiments that are spun up in the newsroom by embedded teams that we have within graphics, visual journalism, interactive news teams. This is where we have editors, journalists, engineers, data scientists, designers, literally all hunkered down together focusing on how to make one story come to life in the best possible way.

**Lenny** (00:27:37):
Who has the idea usually? Is it like the journalists working on that, they're like, "Hey, I think we should make something really great."

**Alex Hardiman** (00:27:42):
Exactly. Yeah, one of the things ... We have a newsroom of over 2000 people. You basically have people who've been experts on certain beats like climate, for instance, for decades. They have the nugget of the idea. They start to do reporting and then they really pull in others from visuals, from interactive just to say, "How can I really make sure that I can tell this story with as much impact and weight as possible?" That's where the magic starts to happen, when you pull in all of those other skill sets together to help dream up how that story might be told.

**Lenny** (00:28:18):
They're like, "Alex, we need one of these for our story. Can you get us on the list?" How does that process go?

**Alex Hardiman** (00:28:26):
No, no, no. These are teams that are really autonomous in the newsroom. For one-off, truly special features, I'll give you an example of one that I found to be particularly powerful. I don't know if you read Jodi Kantor, who is one of our ... a really incredible investigative reporter. You might know for some of her work that she did around MeToo and Harvey Weinstein, in that investigation.

**Lenny** (00:28:46):
Yeah.

**Alex Hardiman** (00:28:47):
She recently did a piece on how employers are tracking and monitoring remote workers with tools like productivity scores. The story itself was designed to show a person's own productivity score in the moment as they read the article.

**Lenny** (00:29:02):
Oh, shit.

**Alex Hardiman** (00:29:02):
It was super visceral, really creepy in the most effective way. In my mind, that's the type of magical experience that only happens when you actually have dedicated designers, engineers, and others who can really sit down with a reporter to say, "Let's figure out how to shape that story in the most magical way." The speed of news is so fast that you don't have time to mess with roadmaps. We really have teams who are freed up from some of the normal processes around that, so they can really just focus on storytelling for really big stories and pieces. But on top of that, what we do have is a storytelling product team. What they do is they really take notice of things that are starting to work in more of the experimental phase, some of these one-offs.

**Alex Hardiman** (00:29:50):
Then, they work closely with editors to test and find product market fit for new formats that can actually scale across many parts of the report, so that over time when you open the app, the app is more accessible, more engaging, because we still have the traditional story based article, but we're also shifting more of the distribution of stories into video, into visuals, into live. If you even look at live, we've broken out of the tyranny of the article in many ways, where you have live reporter updates that are the size of length of tweets. People filing from the ground in Ukraine, trying to give you a sense of what's happening in a very immediate and real way.

**Alex Hardiman** (00:30:31):
That's where we do have teams, product teams who have to think in two modes. First, they have to be able to think in the moment with editors, where you might not always have all the right data at your fingertips and you just have to make a call, like, "What is the best experience to tell this story in a really truthful, accurate, accessible way?" Then, the other mode is when they're not shipping at the speed of news, they're trying to build end to end systems so that we're building the tooling to actually create the stories at the same time as the consumer experience, which is a totally different mode of system level thinking.

**Alex Hardiman** (00:31:04):
It's a very cool space. That product team is, they're pulling off some pretty incredible work because they can operate in those two modes. It's like, in the moment, in the moment of the story, but also trying to build the systems that allow you to reshape the composition of storytelling formats that we have across our products over time.

**Lenny** (00:31:23):
That is super cool. What percentage of these fancy stories are using that platform and building on something that already exists versus a one-off experiment would you say roughly?

**Alex Hardiman** (00:31:32):
The majority are on our platforms hands down. Yeah. Yeah.

**Lenny** (00:31:36):
Okay. That makes sense. Then, just so I understand, so you said Jodi was the journalist?

**Alex Hardiman** (00:31:41):
Yeah.

**Lenny** (00:31:41):
You mentioned. Does she has a product team dedicated to her work?

**Alex Hardiman** (00:31:45):
No, what we have is we have a centralized interactive news team, graphics team, data journalism team. Those editors partner with different journalists when they have really big stories to help bring their story to life.

**Lenny** (00:32:00):
I see. Do they have to come to this team and be like, "Hey, I'd love your time." How does that prioritization ... Because I imagine a lot of journalists are coming to them like, "Hey, my story is going to be awesome. We need you."

**Alex Hardiman** (00:32:10):
You know what? To be totally honest, I'm not involved. Somehow it works.

**Lenny** (00:32:19):
That's a great leadership sign. It just works and you set it up and it's working, so that's great.

**Alex Hardiman** (00:32:25):
Well, and the newsroom has set it up and something that is just, again, very interesting about the way that we are set up is that we have our newsroom and then we have our business side. The business side is where you have all of the product teams and there is intense collaboration between the two, but they do have different leadership structures because that's how we maintain the independence of our coverage. Our product teams sit within the newsroom if they're focused on storytelling, live, anything related to the coverage.

**Alex Hardiman** (00:32:54):
The only distinction really that I think I'm trying to make is that product teams really help stories find their widest audience and be as engaging and as impactful as can be. But product teams don't have any influence over the selection of the stories. That is what the newsroom retains as editorial.

**Lenny** (00:33:14):
Okay. You mentioned Wordle and you all acquired Wordle recently. I'm just curious what that was all like. I imagine it's still being integrated. Were you involved in the exploration and purchase process and what went on there?

**Alex Hardiman** (00:33:28):
Wordle has been such a fun ride. Maybe I'll first just bring you behind the scenes on how the deal came to be, and then we can talk a little bit more about what the integration process has been like.

**Lenny** (00:33:37):
Yeah, sounds great.

**Alex Hardiman** (00:33:37):
I first heard about Wordle in early January because a New York Times reporter, Daniel Victor, actually wrote a piece about Josh Wardle, who's a software engineer in Brooklyn, and how he had created the game. It really is this gesture of love for his partner, and I certainly wasn't the only person to read through that column. Everyone inside the New York Times perked up. I remember reaching out to Jonathan Knight, who's the general manager of games, he's on my team. He had already taken notice well before the piece was published, and he had already reached out to Josh to see if he would be interested in having games join our portfolio.

**Alex Hardiman** (00:34:16):
We just all loved Wordle immediately because if you've played it, it shares a lot of the DNA of other really successful word games that we have at the New York Times, like Spelling Bee or the Crossword Mini. If anything, Josh was really forthright that he created it because he was inspired by those games. Then, in the context of just our subscription strategy, games is such an important category for us. We really see games and demand for games as this, basically, it's a counterpoint to the news. It gives people a chance to actually take a break. It's fun. It doesn't feel like empty calories. It's really time well spent.

**Alex Hardiman** (00:34:54):
We were just thinking of Wordle as such a wonderful addition to our games franchise to really give people more reasons to feel like they had a relationship with the New York Times every day. The whole thesis of the acquisition just made so much sense. Our team just very quickly engaged with Josh and the acquisition talks were incredibly fast. The whole thing took place in a matter of weeks, which is way faster than any other acquisition I've been a part of. It was a very amicable process. We were just super delighted to bring Wordle on board, but it happened in record speed.

**Lenny** (00:35:27):
Well, yeah, it felt fast from the outside too. It became a huge deal. Then, "Okay, New York Times buys them." Yeah, it's impressive. You said you acquired Athletic. How often are you acquiring companies?

**Alex Hardiman** (00:35:37):
We also acquired The Athletic, and that was back in around the same time. I think for now we feel like we actually ... we have all of the major categories to make the essential subscription work. For us to get to 15 million subscribers we really feel like news, sports, games, cooking, audio and shopping, those are the categories, and we just have to make them the best possible versions of themselves, those products, so that we can really provide just tremendous value every day to people. That doesn't mean that we won't make some other acquisitions. The next Wordle would absolutely love to hear about it.

**Alex Hardiman** (00:36:14):
But I do think there's also a real lesson for a lot of companies, not only about when you acquire what's the opportunity, but also are you ready to actually integrate an acquisition? We learned a lot just around Wordle in terms of what that process is like. I just want to say I'm really proud of how thoughtful and considerate our games team was about the integration process, because Wordle players feel such connection to the game. We really wanted to make sure not to interfere with the core magic of the experience. If you are an eight-year old kid or an 88-year old adult, there's real resonance with Wordle and people just have such a connection to it. We really wanted to make sure we didn't mess it up. Do you want to go a little bit deeper, just almost what that looks like?

**Lenny** (00:37:00):
Yeah, absolutely.

**Alex Hardiman** (00:37:01):
Because we definitely learned a lot. When we acquired Wordle, it was a simple web game with no backend. That meant that people's stats and streaks, which was that was the value in terms of social currency that people were sharing after playing, those stats and streaks were stored in local browsers. It was really important for us to make sure that the game board experience in the core loop of the game remained unchanged. But we also found that because everything was stored locally and people care so much about their stats and streaks, if they got a new iPhone, if they switched browsers, all of a sudden they lost all of that history that they had with the game.

**Alex Hardiman** (00:37:39):
What we decided to do was undertake a project to connect Wordle to a New York Times account, which was free, because Wordle is a free game, just so that it knows who you are and so that your stats and streaks can be protected. Then, we could also bring Wordle to more surfaces because we wanted ... if you go to the homepage of the news app or if you go to the games app, we wanted to make it easier to find because people would come for Spelling Bee or Crosswords and they also wanted their Wordle. It was a pretty big effort to rewrite Wordle in our tech stack, give people the ability to store their stats and streaks, bring games to all of our major surfaces.

**Alex Hardiman** (00:38:16):
We just tried to do it in a thoughtful way, where we didn't break anything. The experience was hopefully seamless, and that the only thing you would notice that's changed is that the New York Times knows enough about who you are so that your stats carry over and you can play anywhere. But that doesn't mean that there aren't some surprises along the way, especially when you're doing backend work. We had this pretty crazy moment a couple months ago, right when the Supreme Court's draft ruling on Roe v. Wade leaked. An engineer on the games team happened to notice that the Wordle solution the next day was fetus. Which is just an extraordinarily bad coincidence, because the word had been loaded into the game by the game founder months beforehand.

**Alex Hardiman** (00:39:02):
It was so important for us that we didn't have ... this lovely diversion from the news feel almost like it was commentary on a very contentious story that was happening. I don't know if you caught wind of that, but you'd think that you could easily change the word on the backend, but because we were midstream on the migration process and some users were on the original Wordle game, others had migrated to the new version. It meant that we actually couldn't change the word on the backend for everyone, only for some people. This was a moment where we just had to come out and really tell the world, "We're mid integration. We're really not trying to communicate more than Wordle being a fun diversion from the news. Here's what happened, and why."

**Alex Hardiman** (00:39:50):
Everyone understood. This is where coming out being really transparent about the facts and in some cases just exposing more about the product development process really helps demystify some of the rumors that people might otherwise think. It was one of those like, "Oh, man, I couldn't have imagined that that type of terrible coincidence would happen." But you just have to be prepared for everything, even when you're integrating what should just be a fun game.

**Lenny** (00:40:16):
Imagine, no matter what you tell people, some folks are just not going to believe a very simple explanation of what was going on.

**Alex Hardiman** (00:40:23):
It's true. All you can do is be as honest and transparent. What I will say is a lot of people still think we try to make Wordle harder, we don't, I promise. It's not a thing.

**Lenny** (00:40:33):
Yeah, it's not like the crossword puzzle where it gets harder every day of the week.

**Alex Hardiman** (00:40:38):
No, no. It's not, it's not.

**Lenny** (00:40:43):
**Alex Hardiman** (00:42:12):
If we could of go back to when I started at the New York Times, because I started in late 2019, it was just right before the pandemic. It was pretty wild to come back to the company and to get shifted into this moment of needing to build products that really were trying to help people through the moment. At a time when our journalists were covering the story and all of New York Times' employees were trying to live through it. It was COVID 24/7 in terms of work and life. For me, I remember in the earliest days when we were first really reporting on COVID and learning about it, we had reporters on the ground in Wuhan even before we knew how COVID was transmitted.

**Alex Hardiman** (00:42:52):
Then, when the world shut down, for the Times, we went fully remote in March, 2020, and I remember the day so well because it was the beginning of spring break, of course, all plans were canceled. My kids, I had no idea what to do with them. My husband and I panic packed, put them in a car, drove to go see some friends in Vermont, and we decided we were going to do a kid daycare pool share just to figure out how to keep working with someone overseeing the kids. We got there late at night and I literally just went into a laundry closet and I didn't emerge for two weeks because my Slack was blowing up about all of the work that we needed to do to make our products as useful as possible.

**Alex Hardiman** (00:43:32):
The kids were being crazy and we just had to get to work. What was really stunning about this moment in time was that as people were getting sick and we were reporting about all of the trends that we were seeing, we saw that other institutions, especially the government, were not actually stepping up to help people understand the basic facts about what was happening. This is a product leader, it's a real wartime moment where you just need to blow up roadmaps, share context with everyone and say, "Okay, everyone, we have a totally different mandate than what we did a couple weeks ago." Given the needs in the world and the mission of the New York Times and our purpose, which is to help people access information to make informed decision about their lives, we're going to do a whole bunch of these things.

**Alex Hardiman** (00:44:17):
We're going to build a comprehensive public data set of COVID cases. Nobody else is doing it. We really just started scraping and pulling this together, and what was a single spreadsheet at the time. We pulled a bunch of engineers from other teams to go help build out that database. We launched entirely new formats and data tools to make our journalism a lot more easier to follow. Things like tools to be able to look up infection rates and eventually vaccination rates down at your local zip code level. We made our most important COVID coverage free to everybody. It was really important that if it was something related to public safety, we didn't put it behind a paywall.

**Alex Hardiman** (00:44:53):
Our mission is to do better than that. We really made sure that we had that information available to everyone. We also just found that for journalists who hadn't actually been in Wuhan, they just needed tips to an internal safety guidance for reporting, and so we made that publicly available. It was just one of those really interesting moments where everything felt so crazy in this moment of crisis. But building purposeful products that made a really difficult moment feel not only possible but promising, was one of the most unifying moments, I would say, for our teams.

**Alex Hardiman** (00:45:29):
Because even though people were working so hard and balancing work life and personal life, no one doubted for a second that the work they were doing was of greater good for the world. There's real privilege in being able to spend your time doing those things. But it's one of the biggest news stories of our lifetime and to be at the forefront of that, I think for all of us, was a pretty incredible and humbling experience.

**Lenny** (00:45:55):
Wow. People talk about having impact and driving impact and it's usually like, move this metric some percentage, but that is some incredible impact. Helping people avoid COVID, avoid dying, keeping their families safe. It's got to be some of the most fulfilling work that you and your team has done and ideally it wouldn't have happened, but it was also probably incredibly fulfilling.

**Alex Hardiman** (00:46:20):
Thank you for saying that. One of the most validating tricks that we did look at was we realized that at the height of the pandemic, when there was just so much confusion about literally what to do, how to live each day in March, 2020, we saw that half of the country came to the New York Times. There is something again that is just so powerful about very straightforward data journalism, deep reporting, service guidance on how to make a mask if you don't have one. Just like all of these basics. Just seeing the whole organization pivot from their normal job into this mode and was pretty incredible, and the world responded, which was really validating too.

**Lenny** (00:47:00):
I imagine there's also a bit of burnout that happens working, where it goes on and on and on. You're like, "Oh, my God, when is this going to slow down?" How do you help people avoid burnout? How do you catch burnout as a leader on a product team?

**Alex Hardiman** (00:47:15):
This is one of the most honestly, hard and important topics that I think we're always still grappling with. As a company, we really did try to lead originally with giving people more time off, more support, like financial support and other assistance with daycare, health benefits, all of the basics. I think now what we're really trying to do beyond that is be so much more focused on the things that we need to do and all of the things that we're really happy to stop doing. Because part of, I think, context switching is one of the things that is really, really difficult. It's hard to context switch in your job.

**Alex Hardiman** (00:47:53):
It's really hard to context switch across your job and your life. There are a lot of things that we as a company can't necessarily control in people's lives, but within the job, the places where we can be so much more focused and thoughtful about the small number of important things that we must do at a given point in time, that's really the place where we're really trying to come in and be as empathetic and as honest about what we need to do and what we don't need to do. A lot of it really comes down to, I think, making hard calls. We're not always perfect at it. I'm sure that there are things that we could be more diligent about.

**Alex Hardiman** (00:48:27):
But I would say over on balance, we've seen a lot of people stay at the company because they're figuring out they work remotely, maybe they come back to the office. They're figuring out how to live their life in a very different way from a couple of years ago. We're really here to try to meet them and make that as possible as possible. We need incredible people across a bunch of different skill sets, a bunch of different backgrounds. The only way to do that is to really be very flexible and accommodating in terms of trying to meet people where they are in their lives, but it's tricky.

**Alex Hardiman** (00:49:03):
There is no perfect answer for this, but we're really trying because the success of the company only works when we have people who feel valued and they can do their best work and live really rich lives on top of that. I think we're all still figuring out what that looks like now that we're starting to come out of the official pandemic and really just learning how to live with COVID.

**Lenny** (00:49:23):
Right, absolutely. You mentioned that you're all remote now. Is that the policy going forward?

**Alex Hardiman** (00:49:29):
We actually just started going back into the office a couple of days per week, which is very encouraged. We're still finding our groove. We do have a good number of people though who are fully remote as well. It's more of an evolution in terms of trying to find the right balance of taking advantage of in-person work, because there are some moments where it really does make such a difference when you have people together working through hard problems in real life. That camaraderie, those relationships really, really do matter. Also, being realistic about the fact that there are a lot of people who would love to work at the New York Times, but might not be able to live in the New York City area.

**Alex Hardiman** (00:50:11):
So, how do we make sure that we can be a remote friendly company for them too? Yeah, so we're very hybrid, we're still testing our way through it. But by and large, we're shipping so much tremendous work, which I think is a reflection of us being able to do the hybrid thing and just try to get better and better at it each day, each week.

**Lenny** (00:50:30):
Yeah, it's hard. As an outsider, I can't imagine a New York Times being all remote. It feels like that kind of company just, it's all happening in a building somewhere probably. I'm also a big fan of in-person, it feels like as a company, it feels like you have an advantage if you're working in-person generally.

**Alex Hardiman** (00:50:46):
We certainly see that, and so the center of gravity is in New York and is in the office, but again, with a lot of flexibility for people's lives. We're really trying to figure out that balance.

**Lenny** (00:50:58):
Just a couple more questions before we get to our very exciting lightning round. Where's the New York Times in the next five, 10 years as a product specifically different from other folks? Then, broadly, I don't know, if you have any insights or opinions on just what is the future of news, do share.

**Alex Hardiman** (00:51:13):
I think the New York Times is in a pretty unique spot compared to other news organizations right now. I have tremendous respect for other high quality organizations like The Journal and The Post and The FT and The Guardian. They're just doing such incredible work. But when I go back to what differentiates us, it's this idea of becoming an essential subscription that really helps people. It meets their most important news and life needs across all of the categories that we've been talking about, like news, games, audio, cooking, et cetera.

**Alex Hardiman** (00:51:44):
Up until, I would say, this year we were more of a news brand with a collection of adjacent lifestyle products, but with the acquisition of Wordle and the Athletic, along with just the continued growth of cooking and Wirecutter and some of our other offerings, I really do think that has transformed us into a brand capable of really being that essential subscription that helps every single day people with news and life needs in a way that doesn't just associate the New York Times with [inaudible 00:52:12] categories. Imagine that you open the New York Times app and you are starting with a great breaking news story. Then, you skip over to the latest coverage in China.

**Alex Hardiman** (00:52:25):
Then, you decide that you want to take a small break to play Spelling Bee, and then you want to plan a Korean dinner party with Eric Kim, who I don't know if you know has some of the best Korean recipes. He's amazing. Then, you're like, "Wow, I need a rice cooker to be able to make that recipe, so I need to go get the best recommendation from Wirecutter."

**Lenny** (00:52:43):
I just did exactly that, actually.

**Alex Hardiman** (00:52:45):
Did you?

**Lenny** (00:52:45):
Yeah.

**Alex Hardiman** (00:52:47):
Then, I would love to go watch the Britney Spears documentary, which is also part of the New York Times franchise, which is amazing. Or, I want to go listen to Kevin Roose and Casey Newton's Hard Fork podcast, which is wildly fun and just launched a couple weeks ago, if you haven't heard that. This is, I think, the future for us of being a connected family of products, where we can meet so many different needs that are first anchored in news, but then stretched into other facets of your lives. I don't really see other news organizations really operating at that scale and that ambition, and that's the future for us.

**Alex Hardiman** (00:53:24):
We really just think that the New York Times can mean so much more to so many more people. We're a journalism company, but we're building just tremendous software, and so the product ambitions are only getting bigger and bigger, and that's why I feel like I've got the luckiest job in the world right now.

**Lenny** (00:53:42):
That is a compelling vision. I feel like you can build your own metaverse in the New York Times where you just spend all of your days inside the New York Times' suite of products.

**Alex Hardiman** (00:53:52):
Can I say though, there is a big difference. I think that for us our software actually helps people with real world outcomes in a very different way. We basically help you get access to information, decide how you're going to go to the ballot box. We give you information to go cook. Actually, there's something that I think is even more of a connection to the physical world, and it is very different from what the Metaverse is doing, but that's where we feel like we can drive as much impact as possible.

**Lenny** (00:54:20):
You can have your own competing metaverse. Here's a quick Wirecutter suggest idea for you, while we're chatting. I feel like Wirecutter, I use it all the time, everything I buy is based on Wirecutter recommendations, but I feel like there's an opportunity for design oriented version of Wirecutter. I don't know if anyone's thinking about that.

**Alex Hardiman** (00:54:37):
Tell me more.

**Lenny** (00:54:38):
Just Wirecutter's functional stuff. It's like, "Here's the best, I don't know, rice cooker." But like, what's the cutest but also the best? What's the cross section of looks good in my house and is the best. I'll be okay not the best best if it looks nicer, so a design lens to Wirecutter.

**Alex Hardiman** (00:54:54):
If it's Wirecutter meets high taste, basically. I like that. I like that. Okay.

**Lenny** (00:55:02):
I think there's a market there.

**Alex Hardiman** (00:55:04):
I'll definitely bring that back to the team. That's a good one.

**Lenny** (00:55:06):
There you go. Well, we've reached our very exciting lightning round where I'm just going to ask you, I have six questions, I'll get through them pretty quick. Whatever comes to mind, fire off. We'll go through it fast and fun. Sound good?

**Alex Hardiman** (00:55:21):
Great.

**Lenny** (00:55:21):
Okay. What are two or three books that you recommend most to other people?

**Alex Hardiman** (00:55:27):
I love Stripe Press, and so I think a lot of the books that they have are just such good references, like Elad Gill's High Growth Handbook, or Will Larson's An Elegant Puzzle. Then, some of the more topical ones like Revolt of the Public. I just find that they're evergreen in terms of their utility. Anyone can find value in them. I just loved the craft of the books themselves. They are amazing products in terms of the content and the form, so those are, in the product context and work context, those are hands down I would say the places where I go first.

**Alex Hardiman** (00:56:01):
But I do think, and I know this is this humanities major in me, I also always try to balance books and my own reading time and recommendations with fiction. I just think it's actually like, sometimes some of the best ideas and inspiration come when you go one or two steps away from the core books that are related to your practice. Right now, I'm actually rereading Giovanni's Room by James Baldwin. It's just so beautiful and so lyrical and it gets at more components of the human soul that, I know it sounds crazy, but I find like those are little sparks of ideas that ultimately come back into making products, and particularly news products where they're so creative in the way that they tell stories.

**Alex Hardiman** (00:56:46):
I always try to give people one pragmatic recommendation and then one slightly more field recommendation over in the world of fiction. If you haven't read Giovanni's Room, it is incredible and devastating, and I absolutely recommend it.

**Lenny** (00:57:00):
Wow. I feel like I just keep buying books after doing these podcasts. I have so many books I got to read. I'm also feeling like the combination of books you recommended is exactly what I would imagine someone leading product at New York Times would recommend, something product tactical and then just a beautiful piece of fiction.

**Alex Hardiman** (00:57:18):
I'm the cliché. I love it.

**Lenny** (00:57:21):
Great. No, no, no. I wouldn't put it that way. Okay. What's a favorite other podcast that you like to listen to? You mentioned one already, is that the one?

**Alex Hardiman** (00:57:28):
Everyone should listen to Hard Fork. It's great. But I just think The Daily continues to be, and again, I know it sounds self-serving, but being able to just listen to Michael Barbaro and Sabrina Tavernise once a day, just bring in journalists to talk and unpack a meaningful story, it's so visceral. I just find it to be one of the daily miracles that the New York Times is able to produce.

**Lenny** (00:57:51):
Yeah, that's wild. I can't imagine a daily thing like that doing that. Impressive. What's a recent favorite movie or TV show that you've seen that you've really enjoyed?

**Alex Hardiman** (00:58:01):
I am pretty old school. I am actually rewatching The Wire for the third time.

**Lenny** (00:58:06):
Wow. That's a lot of time commitment.

**Alex Hardiman** (00:58:09):
It is. I have very little time, but every five years my husband and I, we just can't get over the characters, the storylines. It's just one of the best made series for television ever. It's a work of art, and so I am that person, that is another cliché, who is rewatching The Wire right now.

**Lenny** (00:58:27):
What's your favorite season?

**Alex Hardiman** (00:58:28):
I would probably say it's season three, but when Stringer Bell passes away, it's the culmination of just so much. I probably shouldn't say that for anyone who hasn't seen The Wire. Oh, that's like the worst thing ever.

**Lenny** (00:58:43):
Spoiler alert in reverse.

**Alex Hardiman** (00:58:45):
Spoiler alert. I'm so sorry.

**Lenny** (00:58:46):
But that's not the character name, that's the actor, right?

**Alex Hardiman** (00:58:49):
No, no, I really just totally spoiled that.

**Lenny** (00:58:51):
Okay, that's cool. If you haven't seen it at this point, it's over, your loss.

**Alex Hardiman** (00:58:56):
Oh, boy. How awful. That's like a cardinals sin. But I do think season four, when it starts to get into the school system is also just, the actors are incredible. It's some of the best acting that I think has existed over the last couple of decades. Again, if you haven't seen it, please do yourself a favor and watch it. It's worth every episode.

**Lenny** (00:59:16):
Would you agree season two is the worst?

**Alex Hardiman** (00:59:19):
I thought that until I re-watched it.

**Lenny** (00:59:22):
Interesting.

**Alex Hardiman** (00:59:22):
I actually came around and it's not at the top of my list, but there's more to it than I think I originally gave it credit for.

**Lenny** (00:59:30):
Wow. I like this. Okay, great. What are four to five SaaS products that you or company uses most that you find really useful?

**Alex Hardiman** (00:59:39):
Probably pretty classic, we use G-Suite, Slack, Figma, Mode, GitHub. Those are the ones that I think just get hands down the most amount of usage across our teams.

**Lenny** (00:59:51):
The fourth one was Mode?

**Alex Hardiman** (00:59:52):
Yeah.

**Lenny** (00:59:53):
Is there any interesting new recent one that's like top of mind while we're on this topic?

**Alex Hardiman** (00:59:58):
Not really. No.

**Lenny** (01:00:02):
Okay, great. The winners keep winning, huh? These products?

**Alex Hardiman** (01:00:07):
Yeah. If anything, it's like when you don't talk about the SaaS products you use, I feel like that's more of a success because it's just, it works behind the scenes, it blends in and it just makes everyone so much more productive.

**Lenny** (01:00:19):
Yeah. Imagine all these companies have the New York Times logo on their site of people using that.

**Alex Hardiman** (01:00:24):
Maybe.

**Lenny** (01:00:24):
That would be a big deal when you guys adopt a product. Final question. Who else in the industry do you most respect as a thought leader and thinker?

**Alex Hardiman** (01:00:32):
This is a hard question, but I would say one of the people who I find to just be a really tremendous product thinker, leader, and ally for women is Fidji Simo. I was lucky enough to work with her and for her when I was at Facebook and just watching the way that she ... what she did with Facebook, what she then is doing at Instacart and the way that she really just helps so many other women in the field figure out how to be better at their craft, how to have more opportunity. I don't know how she has these many hours in her day, but she's pretty incredible, so I would love to give a shout out to her.

**Lenny** (01:01:10):
Awesome. I will try to get her on this podcast.

**Alex Hardiman** (01:01:13):
Oh, that would be amazing. All right. She's really-

**Lenny** (01:01:15):
That's what I need to do. Awesome. Good recommendation. Alex, this was amazing. I learned so much. This is such a fun conversation. Thank you, again, for doing this. Two last questions, where can folks find you online if they want to reach out and learn more? Maybe think about working at the New York Times and otherwise, how can listeners be useful to you?

**Alex Hardiman** (01:01:32):
Thanks. You can find me on Twitter, LinkedIn, all the usual channels. I would love to hear from anyone and would be delighted to also talk about what it's like to do product at the Times. Then, the thing that would be really useful is what is the one feature that would make the New York Times more essential and more valuable to you in your daily life? I would love to hear from people on that front.

**Lenny** (01:01:53):
All right. I shared mine, a design-oriented Wirecutter. I will be looking for that.

**Alex Hardiman** (01:01:59):
Thank you.

**Lenny** (01:01:59):
Awesome. Thank you, Alex.

**Alex Hardiman** (01:02:00):
No, of course. There's just one other whole theme, and I don't know if you want to chat through it, which is, what are some of the similarities and differences between product management in news organization?

**Lenny** (01:02:14):
Let's do it.

**Alex Hardiman** (01:02:14):
It's totally up to you. But if that's something that you'd be interested in talking through.

**Lenny** (01:02:20):
Absolutely.

**Alex Hardiman** (01:02:21):
I'm going to just focus on two themes that I think are pretty interesting. The first is just how we work at the New York Times, and we talked a little bit about working with journalism, and there are some really interesting differences. The second is just on the idea of impact. I think how the definition and the understanding of impact can be pretty different. First, just on the idea of how we work, there are a lot of similarities. I would say that product managers at the Times and at tech companies, they have a lot of the same skills. Like, we look for a great product sense, great execution, great leadership and drive.

**Alex Hardiman** (01:02:59):
Any good PM needs to know their industry, their customers, their market, their business, et cetera. We actually do see a lot of crossover between product managers from tech companies who come to the New York Times or tech PMs at the Times who go over to tech companies. I think that that's wonderful, but a key difference of when you're a product manager working at the New York Times is that you work across the full stack of the product. Meaning, we own our journalism and our content. We own our distribution and we own our products. That's really different from working at a big tech platform. When I was at Facebook, we controlled the software and the distribution, but we didn't control the content.

**Alex Hardiman** (01:03:39):
We had real limitations on understanding what was passing through. Was it high quality content, low quality content? It just led to, again, a lot of challenges that we already talked about. At the Times, when I think about how our best products are born, it's when you bring journalism and product lovers together. That means that PMs at the Times really need to understand the blend of art and science. They really need to value expert editorial judgment as they're also looking at individual KPIs, customer research and insights, et cetera. An interesting example, as I was trying to think about what would feel really different doing product at the Times compared to say Facebook is like, let's say you're at the product team and you're working on the home screen.

**Alex Hardiman** (01:04:25):
We always start with expert editorial judgment to curate the most important and interesting stories. But on top of that, we're training algorithms on specific data sets, like editorial important scores that actually come from our journalists. What that allows us to do is actually scale editorial judgment to a large group of readers. Those algorithms, what I think is just really great is they're trained on editorial signal and then they can still work towards driving towards outcomes like reach, engagement, conversion, et cetera. That's just such a different way of thinking. When I was at Facebook and we were focused on news ranking and feed, all we could do was train pieces of in information based on an engagement outcome.

**Alex Hardiman** (01:05:12):
We couldn't actually train it based on the quality of that piece of information itself. At the Times you get all, you have 2000 plus journalists and you're actually trying to structure their expertise into things that can actually translate into really great algorithmic decisioning, and that's just so different. No one else is really doing something in that space. Product managers are becoming very editorially minded and we're also getting editors to become more product minded. I just think that how we work there is so different and so unique. It's just a pretty fascinating part of, I think, how the sausage is made, if that makes sense.

**Lenny** (01:05:46):
Yeah. Thanks for sharing that. I think that's really important topic of just how it's different and why it's worth considering trying something like the New York Times as a place to work. What's interesting about what you're talking about, this also reminds me ironically of Substack, where they also are anti-algorithms and are also very focused on people and people recommending other people and just like individuals. I don't know if we want to get into this, but I guess do you have a opinion of Substack as a medium? Because folks leave New York Times to work on Substack, they come back. My whole living is on Substack. Any thoughts on the world of Substack?

**Alex Hardiman** (01:06:25):
Well, a couple of things. First, it's not that we're anti-algorithm on the New York Times front, it's just that we want our algorithms to reflect editorial judgment. That's really different. When it comes to Substack, actually, I think a lot of what Substack is doing is great. The idea of writers being able to make a living individually off of their craft, I think, is fantastic. The thing that I get excited about for Substack, but also for a company like the New York Times is trust right now with institutions has been declining, with governments, with religious institutions, with news organizations.

**Alex Hardiman** (01:07:00):
But trust with individual experts, where you have a real relationship, that really matters. That I think is one of the big unlocks in terms of helping the next generation of readers really start to create more of a relationship with high quality journalists and writers who have really important things to say about the world. I think whatever is happening in the world that helps great writers find their audiences, make a living, is wonderful. At the New York Times, a lot of what we're trying to do is, it's not the Substack model, but we have a lot more that we're doing to actually help get individual journalists out there.

**Alex Hardiman** (01:07:39):
They have their own subscribe only newsletters, podcasts. We're really trying to help them find a way to create a mini platform within the means and the scale of the New York Times. It's not quite the Substack model, but I do think that there's some interesting similarities, and the more that artists and creatives can help make a living, I think, it's just fantastic.

**Lenny** (01:08:00):
I'm here for it. I love this two-part encore bonus we just did. Anything else that you want to share before we wrap up?

**Alex Hardiman** (01:08:10):
I think the only other thing that I have come to learn when you're doing product management at a news organization compared to a place like Facebook is just how different the definition of impact can be. When I was at Facebook, we were incredibly focused on scale, engagement, and revenue, which is very appropriate. At a company like the New York Times, we also have a huge ambition to grow our subscriber base. But one thing that's really interesting is that our impact and our business goals are in service of our mission, which is to seek the truth and help people understand the world, not the other way around.

**Alex Hardiman** (01:08:51):
What it means is that the way that we think about impact is growing a giant subscription business. That business exists to strengthen an informed democracy at a time when people are struggling to understand basic facts and struggling to understand each other. That means that impact for us is growing subscribers, but it's also when a deeply reported story triggers an important policy change or a new law. When you're a product manager you're involved, again, in driving specific metrics like engagement or subscribers.

**Alex Hardiman** (01:09:26):
But you're also trying to help stories find their real audience in ways that trigger just this whole different side of mission and purpose driven impact. I didn't feel that when I was at a place like Facebook, but at the Times, I think it just gives product managers a bit of a broader aperture in the ways that they think about the relationship between business goals and mission impact goals, and it's pretty cool.

**Lenny** (01:09:50):
It does feel like it would be hard to find more meaningful, impactful work, and so that really resonates.

**Alex Hardiman** (01:09:57):
Oh, thanks. There are so many other important purposeful products and problems out there to solve in the world. We've talked about this, Lenny, but I just think that product managers and product thinking in so many contexts inside and outside of tech has never been more important in the world than right now. We need product managers everywhere diagnosing key problems and issues, coming up with radically novel solutions. This is the moment. It's really great to have your podcast and so many other resources out there to help new and other PMs just do their best craft. Thank you for having all of us in here.

**Lenny** (01:10:33):
I love that as a closing thought. Alex, thank you again so much for doing this.

**Alex Hardiman** (01:10:37):
Thank you so much, Lenny. This was really fun.

**Lenny** (01:10:40):
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] Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer)

**Gergely Orosz** (00:00:00):
In my best year at Uber, I made about 320 or $330,000 in total compensation. And when I quit my job, I was actually thinking, am I crazy? Because I am leaving... Especially in Europe, this is a lot of money [inaudible 00:00:14] this will be similar to something... Someone in a similar position would've made five or 600K in total in the U.S. But now I am making more in compensation that I made at Uber. And the difference is that now my compensation... Well, my earnings keep going up as long as the newsletter is growing, so there's no theoretical cap on this. Of course there's an actual cap, there's churn, growth is slowing over time. But it's very, very strange, because I felt that I was in a really privileged position, just honestly making tons of money, doing a job that I loved. And this was at Uber or as a software engineer. And I'm now doing stuff that I love, and in some strange way, I guess it even pays better.

**Lenny** (00:00:59):
**Gergely Orosz** (00:04:35):
It's awesome. Great to be here, Lenny.

**Lenny** (00:04:36):
So I think this is going to be a pretty special and unique podcast. Your newsletter is the number one technology newsletter on Substack, called the Pragmatic Engineer, by the way. My newsletter is the number one business newsletter on Substack, and so we're connected in this really special, weird way, and I thought it would be pretty fun to just explore this weird path that we're on doing this newsletter thing, and in that, help listeners understand the pros and cons of this life, how to go down this route, what it takes to be successful, all that stuff. But before we get into all that, I'd love for you to spend maybe a minute just giving us a little overview of your career, and how you got to where you are today doing this newsletter, and what you spend your time on now.

**Gergely Orosz** (00:05:19):
My career started out as what you might consider a pretty typical software engineer career. I graduated from university, I did a computer science degree for a five year program, so I did bachelor's and master's. I worked on the side, I hacked around, built small websites here and there, and during university I worked at a small web agency. And then I worked my way up in the industry. So I started off at a consulting company, we were just building for other companies. I'm originally from Hungary, in Europe. I then moved to UK, which was a big step up for me in terms of just getting access to, I guess, more modern software development. I was at a consulting company there as well. And I moved up to London, which in Europe, I feel it's like the New York of Europe, or even the Silicon Valley, back in the day. Back before Brexit, it was the biggest tech hub.

**Gergely Orosz** (00:06:11):
I worked at an investment bank there, and then on the side I was always building mobile apps, and I got into Skype. I like to say Skype, but it was Microsoft. They just bought Skype at that point, and it was a lot more startup-y environment, a lot more fast moving. I then moved to another startup where I was a founding engineer of a acquisition. It's a startup called Skyscanner. And then I ended up at Uber at Amsterdam, where I joined as a senior software engineer, and I became a manager, and then a manager of managers, and it was just... I feel, looking back at that part of my career, I just felt really growing all the time, just taking each step one step at a time, which gave me a lot of appreciation for all these levels.

**Gergely Orosz** (00:06:51):
And then, just as I was on this really good career path, I was on the path to being a senior engineering manager, or who knows, one day I might have had a shot of being their director of engineering as well, I decided to leave Uber. And we'll talk about it a little later in the podcast, but I didn't plan like this, but I started writing a newsletter. And now here I am writing a newsletter where a bunch of people are reading it, and it's a really unexpected turn and a really cool life as well.

**Lenny** (00:07:19):
Awesome. On the newsletter, just to give people a little bit of context of how big this has gotten, can you share just a couple stats about the growth of the newsletter, the size, and anything else you want to share there?

**Gergely Orosz** (00:07:30):
Just today I checked and it said 189,000 subscribers. I think the past 90 days has been growing with 80,000 subscribers, so it's almost a thousand people per day, which is incredible. Because these numbers are huge. If you're listening, you're probably thinking, "Wow." And that's how I feel every day as well. But I've been writing a blog for many, many years, and these are numbers I never thought it would be. And the growth just seems to be accelerating. There was a tipping point in April where the newsletter was growing... In the first about nine months of the newsletter, it got to 50,000 subscribers, and then the next five months, or six or seven months, it went up by another a hundred and something thousand subscribers. This was when Substack introduced recommendations, which has been a massive growth engine, and I guess being one of the top publications, I benefited from it. But those numbers are again...

**Gergely Orosz** (00:08:26):
So this is a paid newsletter as well. So there's a free version and a paid version, and there's thousands of people paying for the newsletter. It's a single digit percentage, but it's a very, very healthy one. And again, it just beat all my expectations. And I guess we're in similar boats, because our newsletter setup, yours and mine, is somewhat similar. We have plenty of differences as well, but I make most of my revenue from subscriptions, and I don't do sponsorships or ads in the newsletter. So if people sign up for the free one, they get articles every now and then, and for the paid one, they get it a lot more and in more depth.

**Lenny** (00:08:59):
Can you give listeners a sense of just the order of magnitude income you make from this, versus your cushy tech job at Uber? You don't have to share numbers or anything like that.

**Gergely Orosz** (00:09:09):
Yeah. I'll share a little numbers of my cushy tech job at Uber. I was in Europe, and European tech salaries, or I'll say total compensation, will be lower than for example the U.S., but it'll be higher than let's say regions like India or Indonesia. There's regional differences, and this is true for big tech as well. Uber was a good example on this. But in my best year at Uber, I made about 320 or $330,000 in total compensation. This was after Uber went public, so it includes the stock, the base salary, the bonus, which was very, very good in Europe. And when I quit my job, I was actually thinking, "Am I crazy? Because I'm leaving..." Especially in Europe, this is a lot of money [inaudible 00:09:53] this will be similar to something... Someone in a similar position would've made five or 600 K in total in the U.S.

**Gergely Orosz** (00:10:00):
So I walked away from that, and I was pretty sure that I'll just [inaudible 00:10:04] a lot less, but I'll enjoy what I'm doing, or I'll have... I'll just give it a go. But now I am making more in compensation that I made at Uber. And the difference is that now my compensation, my earnings, keep going up as long as the newsletter is growing, so there's no theoretical cap on this. Of course there is an actual cap, there's churn, growth is slowing over time, but it's very, very strange, because I felt that I was in a really privileged position, just honestly making tons of money, doing a job that I loved. And this was at Uber or as a software engineer. And I'm now doing stuff that I love, and in some strange way, I guess it even pays better. Part of it is just luck, part of this is situational. I think we're going to talk a bit more about this. But this was very, very surprising and very unexpected for me.

**Lenny** (00:10:55):
Awesome. That's a great segue to the first thing I want to talk about, but just to frame what I want to spend our time on today, there's these four areas I want to explore. One is your decision to leave and start this life of writing, which is a very non-traditional life. Two is what the life of a paid newsletter person is like. What do you do all day? How do you find time to do this? How do you produce so much content? Three, what it takes to be successful at this. A lot of people... I always say it's easy to start a newsletter, hard to keep it going, and I'm curious what you find is important to be successful. And then four, how do you get started if you want to start your own newsletter?

**Lenny** (00:11:30):
But before I get into that, I just wanted to add a thought that I had. The way I think about this life in terms of comparing to the old job is, one, it feels instead of one boss, I have thousands of micro bosses, and one of them can fire me and many do every day, but it feels safer than at a tech job where one person can decide. And then the other piece is, assuming it keeps growing, you're getting a raise almost every day, every week, depending on the growth rate, and that's cool.

**Gergely Orosz** (00:11:57):
That is really cool. I had a spreadsheet that I maintained for the first year of the publication, where I listed, for every article, how much did my annual revenue go up a week later. So tracking what was the impact. And the crazy thing was that, when I wrote a really good article that resonated with people, sometimes it was an article that I thought was mediocre and people still loved it [inaudible 00:12:20] it was a really good article that I put tons of work in, I saw myself getting a raise. And this is just something you just don't get in corporate. I mean, it's by design, and there's a lot of good stuff about it, but I feel that this life, and we'll touch more on this, but there's a lot of surprising things, both good and bad, but this is a really good one. So for doing something awesome, you can just give yourself a raise, especially because this is just like you, mine is also a one person business right now.

**Lenny** (00:12:49):
Yeah. Okay. So you're at Uber, you're making hundreds of thousands of dollars writing code, it's pretty sweet. Uber's growing. You probably got all these RSUs that are going to keep accumulating. It's pretty good. And you decide, "I'm going to try to make money on the internet writing," which is an obvious way to make a lot of money. Not. And so I'm curious, what got you to leave that job and explore writing and get to this writing path?

**Gergely Orosz** (00:13:20):
The short of it is, it was a promise to myself, and COVID, and Uber doing layoffs. And the longer version is that, when I joined Uber, before Uber I was... Now we're talking numbers on my old job, but I was working in London as a principal engineer at Skyscanner. Skyscanner was a unicorn, one of the few unicorns in the UK, UK headquartered and all that, and I was making like 90-something thousand pounds in base salary, which is maybe a 120, 130, or $140,000, depends on how the pound is doing, or sometimes these days it's almost just the same. But back then that was a really good... And this was most of it. I got some stock as well. And I thought I was close to the top of the market in London. I knew people, and it seemed this was a really good compensation package.

**Gergely Orosz** (00:14:05):
And then Uber called me up saying, "Do you want to interview?" I interviewed with them, they gave me an offer, and I negotiated, and they basically doubled my compensation. I was like, wow, this is [inaudible 00:14:16] I knew about Silicon Valley compensation, but I assumed that [inaudible 00:14:20] you're not going to get this, but Uber was getting something closer to that. So I told myself, all right, so I'm getting a really good deal, and most of it is stock, which is... Uber [inaudible 00:14:32] 2016, no-one knew if Uber will go public, although I suspected, because they contacted me to build a payments team so do a SOX compliant payment system. And you need a SOX compliant payment system if you want to go IPO.

**Lenny** (00:14:44):
That's funny. It reminds me at Airbnb, there's all these people trying to figure out, when are we going to go public? And then there's the team working on SOX stuff and Sarbanes-Oxley, this is good.

**Gergely Orosz** (00:14:55):
Yeah. So anyway, I said, all right, this is a massive lottery ticket. If it goes in, every year I make two years of salary, pretty much. That's how I was thinking. But if not, again, don't forget I'm in Europe where we're used to not seeing any returns on stock. So European software engineers will not value stock as much, because they just haven't seen success stories. So I told myself, if four years later Uber exits and I make a bunch of money, I owe it to myself to take a risk, because then I'll have four years of savings in my bank, which... Back then I had maybe six months of savings or something. So this was the promise to myself.

**Gergely Orosz** (00:15:32):
And then I probably would've forgotten about this, but four years later, almost on the dot, COVID starts, and it really hit super hard. We're laying off people, we had to lay off 20% of the engineers. I was already managing a group of about 30 people, I had managers under me, and 20% of the people or 15% had to be let go. And I was thinking to myself, what am I doing here? I looked ahead, Uber was going to have a really bad year, I'm going to have to manage morale. Up to then, I'd helped put together this team, and we had a really good charter, and we had to throw that charter out the window, because it made no sense with the economic reality. So I thought back, and I told myself, if I'll be here, I'll take a risk, and I'll try to do something else. So I was like, all right, let me pull this trigger.

**Gergely Orosz** (00:16:18):
And my plan was very simple. Leave Uber and start a startup, raise venture capital, because I haven't done that before but it kind of runs in the family. My brother's on his second startup, and he sold his first one to Skyscanner, and now he's building this startup called Craft Docs. It's a really slick document editing system, they just raised their series B. So through him I know [inaudible 00:16:42] startup life is, and I felt I never did that, I always worked at big companies.

**Gergely Orosz** (00:16:45):
So my plan was [inaudible 00:16:47] leave Uber, raise money, and do something on platform engineering. A classic way that Uber alumni start businesses is, Uber has invested silly amounts of money to build everything custom internally. Everything that you can think of. Our [inaudible 00:17:02] system was custom, our experimentation system, our container, the way we automatically set that up, a lot of the engineering stuff. So a lot of Uber alumni just leave, and whatever they saw there, they just build it for the world to use, because no other company really does what Uber does, because it makes no sense, but a lot of them will pay for.

**Gergely Orosz** (00:17:20):
That was the plan. But before [inaudible 00:17:22] I wanted to finish a book. I'd been writing this book for, it was coming up to a year, called the Software Engineer's Guidebook, which is just my advice for people to grow professionally in the field. And I figured, all right, let me leave the company, in six months I'll write the book, I'll just use my savings to take a break, and then I'll raise the venture capital. And what happened was, I started to write this book, but I got sidetracked, I started to have fun online in terms of... I was writing on Twitter, on my blog. I accidentally published a book called Building Mobile Apps at Scale. I just did it for a few months.

**Gergely Orosz** (00:17:58):
And the weird thing was that my plan was that I'm going to just not make any money, and this book, Building Mobile Apps at Scale, and another book that I published about tech resumes, I just wrote these in a few months, they started making money. They made about $100,000 in the first year. And I was like, "That's interesting. People are buying my books." And I self-published it through Gumroad or places where I get to keep I think 90% of the revenue, but still, this was really interesting. And I got to the point where, all right, I should now start a startup. I should do fundraising and do all that. And then I asked myself, why do I really want to do that?

**Gergely Orosz** (00:18:34):
And the answer was two reasons. One is, I love working in small teams at Uber. I'll be honest, I didn't really enjoy being a manager of managers. It felt a bit too abstract. I didn't like being in the meetings, not doing the work. What I really liked is when we had a small team, and we had this really big vision, and it was us against the world. We were like ten of us, and we were just getting stuff done, we were putting out fires, it was so much fun. So that was one of the reasons I wanted to do startup. I was hoping to recreate this feeling.

**Gergely Orosz** (00:19:05):
And the other thing, honestly, was money. This was in 2021 before the market crashed. Just doing the maths, if you found a company, and I'll be a CEO and the founder, maybe I'll have a co-founder, this becomes a unicorn, by that time we will have raised five rounds of funding or six, I'll be diluted as hell, but I'll still have let's say 5%. 5% of the billion is still $50 million, after you pay taxes [inaudible 00:19:30] I can buy a bunch of stuff that I don't need. And I was asking myself, all right, and then what? And I was like, after I've bought everything that I don't need, I probably want to share what I know with people, do YouTube videos and write books.

**Gergely Orosz** (00:19:43):
And I was thinking to myself, so hold on. I would go off and do this for like ten years, because that's how much you need to plan to do it. I need to stop doing what I'm doing right now, because I would owe it to my investors and my team to not spend all day on the internet writing about stuff. And then I want to do it again. So it's reminding me of the story of this fisherman. There's one that goes [inaudible 00:20:08] there's the same thing of, you work really hard to do what you're doing right now. So I decided, let me just try giving this a go. [inaudible 00:20:14]

**Lenny** (00:20:14):
Wait, what's the story of the fisherman? I think I know what you're talking about, but... [inaudible 00:20:18]

**Gergely Orosz** (00:20:17):
The story of the fisherman is that, in Mexico, an American businessman sees a fisherman who's just chilling, fishing. And he asks him, "What are you doing all day?" He's like, "I fish for three hours, I hang out with my family, I [inaudible 00:20:32] chill and I sleep in every Saturday and Sunday." He says, "All right, here's what you should be doing. You should fish not three hours, but you should fish five days a week, eight hours a day, sell that fish, turn over a profit, hire more people to do it, then start to be head of all those people, then sell your fishing company." He's like, "Okay. And then what?" "And then you can actually buy an island, and you can just fish for three hours, you can sleep in on Saturdays and sleep on Sundays."

**Gergely Orosz** (00:21:00):
So I was thinking, look, I have savings. I don't have huge, but I have it for... I can still take a risk. So let me take a risk on writing. And I was thinking originally of just spending more time to finish my book. But what I didn't like about books, even though I was making money, is they're really... It's hard to predict if you're going to be making a living, or there's some people who actually like this excitement, but I didn't like it. I didn't know if today I'm going to be making like 50 bucks or 10 bucks or 300 bucks. So I was like, interesting. There's these paid newsletters which I've been thinking about, and you were one of the few people who shared some of your early numbers, and I figured this could be interesting, because it's recurring revenue.

**Gergely Orosz** (00:21:41):
And the only reason I was really hesitant to start a paid newsletter, I was thinking about doing so for at least 6 to 12 months, is I was worried about writing every single week something really, really worthwhile reading, and it's a lot of work. But then I looked back and I saw that I wrote three books. [inaudible 00:21:58] I told you I wrote two books, but there was a third one that I also published in a year, and I was like, I'm pretty sure I can write. So for two weeks I collected ideas of what I would write about, and I had this super long list. So I was like, okay, ideas also check.

**Gergely Orosz** (00:22:10):
And then I just said, screw it, I'm going to take a risk. It's a bit of a more professional risk, and maybe a financial one as well. I'll announce that I'm going to start a paid newsletter. Every week, I'm going to write something really in depth about software engineering. It's going to start next week. And I told myself that I'll... I told my wife as well that I'll do this for six months, and I'll see what happens. If there's traction, it's great. I might have found myself a new job, basically. If not, I'll just refund people. Everyone who bought an annual subscription... I didn't tell this to people, obviously, but for six months I'm going to give it my all. It's basically like a startup. So I told her and my family that it's going to be a lot of work and I might not be around as much, and they supported me, and I took a plunge. I took a big breath and started off. And that's how it went from leaving Uber to starting a venture funded startup to starting to write full time.

**Lenny** (00:23:05):
Awesome. And we're going to talk about what advice you have for folks that are thinking about starting something like this at the end. What was the period between leaving Uber and starting the newsletter?

**Gergely Orosz** (00:23:14):
It was pretty much a year, a little bit less than a year. Might have been like ten months or so, but it was a year from when I decided to leave Uber. So Uber did layoffs in April, and it was really stressful. It was the first time I... I didn't lay anyone off, but people on my team were laid off. I wasn't told who's going to be laid off. It was just really stressful. It's weird, in the sense that the people who were let go, obviously worse for them, but I still felt terrible, and I just didn't feel very good about it. I think this was the breaking point. This was the point where I realized that it's not a family, which is weird because it never was, but it kind of felt family-like, but it's just a corporate, and I'm just a number, and this could happen to me, I guess. So I think I lost my sense of the trust in the system, that it'll take care of me, because I saw some of my colleagues who were really good professionals, I'd argue they were better software engineers and managers than me, they got let go because they were in the wrong team.

**Gergely Orosz** (00:24:08):
So this was April, and in July I went to a holiday, and two weeks in, I just realized I need to leave. And I really had the urge to do somewhere where I'm in charge. And if you're a manager listening to this, you might relate to this. If you're an engineer listening to this, maybe just shut your ears or you'll figure it out eventually. But when I was promoted into management... It wasn't promoting into it, because it was a side step, I didn't get [inaudible 00:24:34] or anything, but it still feels a promotion. They only promote the people who are... Only let people transition who are considered pretty good. I felt this would be a big deal. I'm now a manager. What no one told me is, yes I was a manager, but I was a middle manager. I didn't have too much authority. I didn't even have budget for my team. Someone was underpaid and I couldn't do anything except complain for HR for six months and hope that they'd do something.

**Gergely Orosz** (00:24:58):
So it was pretty frustrating, because I didn't feel in charge in the sense that I didn't have decision making [inaudible 00:25:02]. And the reason I wanted to do a startup is, I decided I liked being a manager, but I did not how I was not in charge and I couldn't take corporate [inaudible 00:25:12] telling us to do stuff, and then we were telling them no [inaudible 00:25:16] I don't want to do that with my people. So I decided for next job, I could be doing this, but instead I'd like to be in charge. So I'd like to be a founder or someone who's high up, so that I can actually take full responsibility for the things that I want to do or I don't want to do. The short of it is, I decided to leave in July. We have longer notice periods in Europe, so I served a longer notice period, and then left. But it was a year after the decision.

**Lenny** (00:25:41):
Let's talk about what your life is like these days, writing a newsletter full time. People might be listening and be like, "Man, $300,000 for writing an email a couple times a week, that's pretty sweet." So I want to talk about the good and the bad of this life. So maybe to start, how many posts are you putting out a week?

**Gergely Orosz** (00:25:59):
I started the newsletter saying I'm going to post once a week. You'll have one pinned up post. And I started to do that, but interesting enough, eventually I upped it to two, so I now promise people two posts a week. There's more in depth and more timeless posts about some software engineering topic on Tuesdays, and there's something that's called the scoop, something a bit more timely, where I reflect or analyze what's going on in the market, interesting stuff I'm hearing. And every now and then there's a bonus post. So I'll say two on average, but the second one came a lot later. But initially in the first few months I was like, I have this one post per week, and it needs to be good.

**Gergely Orosz** (00:26:37):
And it was interesting, because you would think writing a post a week is not a big deal. It's easy. As you said, let's say you're making 300K just writing one post a week. But it actually was pretty stressful in the beginning, because it turns out to write that post, it takes at least a few days or sometimes even longer. Sometimes it takes a week or two for me to research in terms of talking with people. I chose topics that are not covered, because why would people pay for something that is out there already or well known? Then I need to write [inaudible 00:27:10] a first draft. I get some feedback from people who I trust often, not always, but I often do. And then there's an editing phase where I work with an editor who helps make sure that it's just correct. And all these things add up. Even if I only spend a day researching the stuff, it's a day researching, then I have a draft on day two. Day three I get feedback, on day four it's editing, it's almost a whole week.

**Gergely Orosz** (00:27:32):
So I was working on parallel things at the same time, and I was often running against the deadline, I was barely finishing it, which is not what I was expecting initially. The first few months I feel was a bit more stressed, but again, the good thing is I cleared my calendar, so I said I'm not talking with anyone, I'm just doing this. So in that sense it was good. But the one thing I realized, if you look at any journalists who's doing stuff full time, and they're writing, not these clickbait articles, but actually in depth. You look at the Washington Post or New York Times, search for their name, and look up the articles that they write, and they're going to be longer articles. They have like one a month. Seriously. You look at the investigative journalist, they might even have less. And they have a bit of a different level, they have to check with legal and all those things, but my editor is a journalist, so he was actually telling me, even back then, "You actually write a lot of original stuff," because a lot of my emails are about five, 6,000 words, which is considered very long.

**Lenny** (00:28:32):
Yeah. When you said that people listening might be like, one post a week is easy, I think most people are the opposite. They're just like, I can't write anything. I don't have time for any writing. How can you ever write one good thing a week? So I think there's both sides to it. And it's cool that you shared the process. Do you have a specific cadence per post? It's like Monday draft, Tuesday review, Wednesday editor. Is that how you work?

**Gergely Orosz** (00:28:58):
I write every post over multiple weeks, most of them. Some of them I might be able to write faster, but what I now have is, nowadays I actually write two articles. So I have the Thursday that is the scoop, which actually is a lot easier for me to write, interestingly enough. And my cadence is, on Monday I finish up the last of the post that goes out on Tuesday. It's just small edits, but it's already done pretty much, so it's just a few small tweaks, and maybe I have some feedback coming in. On Tuesday, I publish this post, and I do some free writing. I write about some other ideas that I have that's going to be future posts. On Wednesday, it's my free day in between, where I... It's interesting, because what I feel is, when I don't have pressure, I tend to not do much stuff, which might just... My mind's saying, "You just need to chill." Maybe that's it.

**Gergely Orosz** (00:29:49):
But one thing I miss from the corporate world... And if you're listening and you're in a job and you're thinking, "Gergely's job is so amazing," one thing that I liked and I really miss about working at Uber is, I actually had a schedule. This is weird, I hated it back then, but I needed to do these things, and whenever you have a pressure, you do it. And this works with my newsletter. I put in the second newsletter I think to have a bit more pressure. Because the second part of Wednesday, I'm already starting to write my Thursday newsletter. On Thursday, I write that Thursday newsletter, and on Friday I'm now writing the next newsletter for Tuesday. So almost every day except for Wednesday, I have a strong pressure to write. Which when people ask, "Gergely, how do you write so much?" Because I did the maths, and I wrote four or five books' worth of content just last year. It's because I have these deadlines, and as you said, I also know that thousands of people are paying me, they have expectations of me.

**Gergely Orosz** (00:30:46):
And so this is how it's done. If you want to write a book, the easiest way is go to a publisher and sign a contract, not because of the money. In software engineering, you're not going to get much [inaudible 00:30:57] $5,000 or something like that. That's what I was offered initially. But it's the pressure. You absolutely should go to a publisher or have some external... Someone to hold you accountable, and then you'll get it done. And I'll let you in on another secret, or not so secret.

**Lenny** (00:31:16):
Do tell.

**Gergely Orosz** (00:31:16):
In my mind, when I started newsletter a year ago in this crossroads, I want to write this book, which I think will be a great book, the Software Engineer's Guidebook, I feel it'll be my summary of my last ten years of what I have to share as advice, but I was worried that it's just a big project that's just going to take months, and I'll lose motivation midway.

**Gergely Orosz** (00:31:37):
And partially, I went down the newsletter route because I liked how every week I would have to write something, and I had this sneaky idea of, what if I wrote this book where I write some posts that will be part of the book, and then the book will just come together partially. And I've kind of been doing that. I haven't been telling people, but some of the posts are going to be... Not exactly, but the idea is that I have this chapter, and I have this list, have I written about this topic in the newsletter? And you know where I got this idea from? There's the book The Three Musketeers, from Alexander Dumas [inaudible 00:32:12]. And do you know how it was written?

**Lenny** (00:32:15):
I don't.

**Gergely Orosz** (00:32:16):
So he wrote the book for a magazine. He was apparently just low on money, and he started to write for this magazine who told them, "All right, we need you to write something that our readers will want, so that they will buy the magazine." I think he was getting a cut of some sales or something. So he needs to write in a way that was interesting, and then cut it off in a way that people would come back and buy the next one. And he wrote a whole book, and that book, when I read it, it's really long, and I was like, hold on, if he could do this, then this is a good strategy. He was writing it because he just needed the money. That's all. And then he wrote a really good book on the way.

**Gergely Orosz** (00:32:52):
So one big learning for me from newsletters then... I would argue that you can use this not just for newsletters, but any business that you do. If you're going to go out and start a new business, you'll probably have some ideas. And it's not just going to be a newsletter, it's going to be a bunch of other things. If you put in ways that you have to do certain things, put in constraints for the things that you need to do, and then you're going to do that.

**Gergely Orosz** (00:33:16):
Without that, when you're on your own, when you're entrepreneur, I was a great... I think I was a really diligent employee. I always tried to get my work done, show up on time, I tried to meet all expectations. But what I noticed is, when I started to work for myself, it just went out the window. Almost 15 years of being this star employee who really wants to do well, I found myself upset at myself for not... Just wasting my day. But I fixed it by telling people, "You're going to get this every week," and now I have to do it. I just have no choice.

**Lenny** (00:33:51):
**Gergely Orosz** (00:35:49):
So a problem that I have, and this might be unique to newsletters, I'm not sure. I use Twitter for a lot of research. And unfortunately what that means is when I start to write something, it can really pull my attention, because I have Twitter open and then I get a message from someone. It's a little bit like Slack, but I'd argue it can be worse, because also Twitter for me is also something that is very useful in generating people [inaudible 00:36:16] raising awareness. So whenever I tweet, it helps my business. So that's a good thing. But it also justifies for me spending more time on, for example, Twitter than I would want to. So I find that I come up with a method, and it works for a few months, and then I need to change it because my brain just learns to work around it. So I'll tell you a few things that I did, and I'll tell you where I'm at right now, but I use for example apps. I use this app Centered, but I know you're also there.

**Lenny** (00:36:45):
Yeah. I love that app. Also an investor [inaudible 00:36:49] disclaimer, but I love it.

**Gergely Orosz** (00:36:51):
Yeah. And I found that helpful, the idea of focused time and [inaudible 00:36:56] turned on, but it might just be me, but after a while I get used to these things, and I find it not as efficient. I found the Pomodoro method for a few months useful, when you have the 25 minute intervals. And the one thing that has never failed me, but I just find it hard to do, is I find it hard to start. I have this benefit that I have all this time... Sorry, there's two things that always work. One is, it's almost time for me to go home, and then I'm super focused. So when I have this external thing, and I know that there's no way [inaudible 00:37:30] I need to focus on basically the deadline. So if you have deadlines, that works.

**Gergely Orosz** (00:37:36):
The other thing is, if I start to spend three or four minutes doing something focused, and I get the flow of it. So a trick I sometimes do when I'm just, I just don't feel doing anything, is I set a timer of 20 minutes, and then I say, "All right, no distractions." I have a script where I just kill... I use a [inaudible 00:37:57] host file, I just kill all LinkedIn, Twitter, Facebook, whatever sites. So I just cannot reach it. It's just a very simple Python script that I wrote for myself. And then in the first few minutes I'm grumbling, I'm like, "I wish I could do this, I wish I could just look at Twitter to research," but about five minutes in, there's a switch, and I'm now actually heads down and doing it. And this has been the thing that has consistently worked.

**Gergely Orosz** (00:38:21):
The interesting thing is that I feel guilty a lot of times that I'm not working as hard as I could. And I do wonder if it's guilt, or if it's my mind or body telling me that it just wants a break or it wants to do something else. I still haven't figured it out, but I'm on the way there.

**Lenny** (00:38:39):
Awesome. That's a really cool trick, the host file trick. So that's [inaudible 00:38:43] something that you have to be technical to do. I imagine there's some chrome extensions that could do that to some extent for folks. But the whole idea there is, force your brain not to have any way to look at something that'll be distracting, by blocking your computer from even being able to go to the site. That's awesome.

**Gergely Orosz** (00:38:59):
Yeah. So there is definitely going to be extensions that you can use, and on this podcast we'll have a variety of people. If you're a software engineer, it's pretty simple, and even if you're not, you can look it up [inaudible 00:39:10] when you override your host file, you can actually block [inaudible 00:39:13] what you do. And I did this because I wrote a script where I need to run the script, and I need to run the script again to unblock it. And it's kind of cool, because I put it together for myself. So I usually find that the tools that other people use, maybe this is just me or maybe this is software engineers, I don't like them because I feel they're either too opinionated or they're not opinionated enough. So I don't know if this is just the fact that I used to like to build my own tools and my own scripts, because I can, so I found that my scripts worked the best for me.

**Gergely Orosz** (00:39:44):
But as you said, there's a bunch of really good tools. So my advice to people would be, look up all [inaudible 00:39:50] let's try them out. You won't know until you try them. And again, I had stuff that worked really well for a certain amount of time. I don't know why, maybe I just get bored easily or something, that I just need to rotate. But for example, when I went back to Centered... I have no affiliation by the way, so I'm just telling this. But I really liked how they keep evolving as well to do cooler things. They have a community element where you're competing with people on uninterrupted time and closing stuff. So that to me is a... I'll do one last [inaudible 00:40:23] Centered again. I have no affiliation. What I really liked about Centered is, it allows you to turn on your video camera, and I felt really forced to do work, because I knew that people on the other side of the world might be watching me, even if it was not true.

**Lenny** (00:40:37):
Yeah. I love that feature. It's centered.app, by the way, if folks want to check it out. So to summarize some of your tips, which I love, Centered, deadlines, totally work for me too. Blocking sites so that you can't get distracted by Twitter and LinkedIn and TikTok and all the things. And I guess that's the three that work best for you.

**Gergely Orosz** (00:40:55):
Yeah. And the simple thing, start a 20 minute timer, and you say, "For 20 minutes, I need to focus on this thing," on your iPhone or somewhere else. It's just 20 minutes, but during that time you cannot do anything else. And just try it. It works for me, like a charm, once I decide to actually do it.

**Lenny** (00:41:13):
It's cool Centered does that for you, and it has music and all the things. So I that a lot. Awesome. What do you love most about this life that you lead now, versus what you used to do? And then I'm going to ask you the opposite, but let's start there.

**Gergely Orosz** (00:41:27):
I really like that it forces me to have my calendar empty, because for so many years my calendar was this giant mess of meetings on top of meetings, and I would barely have any time to actually have focus time. Now I actually have the opposite. I usually have a lot of focus time, and I have very, very few meetings or things. And even now I get a little bit cagey [inaudible 00:41:51] I have this one meeting in the whole day. So I like how it's [inaudible 00:41:55] manage your time [inaudible 00:41:58] so that's the best part.

**Gergely Orosz** (00:41:59):
And I also like how much in charge I am. Initially it freaked me out, in the sense of how much creative freedom I have. I can write about whatever. I can change a format, I can do this, I can do that. It can be a little bit overwhelming, because I also know that people are going to be reading this, and what are they going to think about it? But I do like that it's very entrepreneurial, so I get to experiment a lot as well, which reminds me a little bit of my old job, because at Uber we also experimented a lot, and obviously more in a corporate setting. But I guess that's just gotten extended. So these are the two favorite things, is the open calendar or very few meetings, and experimenting, trying out stuff and being able to decide what I want to try out.

**Lenny** (00:42:46):
Plus one on both those. I have a rule of no meetings before 3:00 PM, and it generally works 99% of the time. And the reason I do that is, to your point, if there's a meeting at 11:00, I just can't do anything really deep until that point, and then afterwards I have to get back on track. And having that deep focus time is so important for this work, even though half the time I'm on Twitter and distracted, as long as I get enough time to focus, good things happen. Okay. Opposite. What are some of the most surprising downsides and sucky parts of this path that you've taken?

**Gergely Orosz** (00:43:24):
One is obviously it's lonely. I do miss... I had a really good team at Uber, and it wasn't just a team, it was the people. I liked... Everyone has different views on remote work. I actually didn't enjoy remote work as much, because I just liked hanging out with people. I guess I'm that more outgoing type, and I really like walking up to the coffee station and having a chat with people, or at lunch sitting next to someone and talking about it. And obviously in some sense it was annoying, because I wanted to get work done, but for the most part I miss it more than I have. And so I miss not having that. I compensate for that by working in a shared workspace, a shared office, which is a techy workspace. So everyone needs to work in tech. So I actually get to say hi to people and have a little small talk.

**Gergely Orosz** (00:44:08):
The structure is weird, because I felt really guilty for the first few months, because I felt that at Uber I was more productive, because I had to be. I was doing so many things. In a day, I would start my day let's say at 9:00 or at 8:30, and I'd finish it up at, I don't know, 6:00 or 5:30, it depends. I would probably have, on an average day, I would have a good eight meetings, I would finish two or three documents, I would send over this, send over that. I actually have... Looking at my output, now I write a lot, but I wrote a lot. I think I wrote almost as much in terms of emails, chat messages, et cetera. So the downside is, I felt very guilty and a little bit frustrated for myself, for feeling that I'm slacking off. That's one.

**Gergely Orosz** (00:44:55):
And the other thing, it is surprisingly stressful. So when you start off, it's kind of lonely. Not many people do this, what we do. That's also one of the reasons that we connected, because it's a very small community. And even within the community, I feel, in the newsletter community, it's different. You're all running your own business, and there is some level of competition. So you might not... Because it's a little bit of attention economy as well. People are not going to subscribe or pay for ten newsletters on the same topic, so that makes it a little bit more... It's not the same as when you work in tech, and you just share exactly everything that you do, because you can only win.

**Gergely Orosz** (00:45:35):
So there's that part, but there's a lot of external validation, so whenever looking at your subscriber numbers, which brings a bunch of stress that I didn't expect. And I'm a successful newsletter [inaudible 00:45:47] I think my success is quite rare. There will be one or two or a handful of people who have similar success, but I'm an outlier. So that's another thing that I think is just good [inaudible 00:45:58] putting out there. And the downside is, you don't really know how well you're doing. External goals are kind of meaningless. Internal goals, either you smash them or you don't reach them. So there's this constant sense of, where am I? How am I, and how do I judge myself? Did I make a mistake for leaving my job? I actually asked myself for several months actually, after I started. Or did I make a good one? And I think for a lot of these questions and doubts, having past professional experience working at a company is really useful to set yourself grounded.

**Lenny** (00:46:33):
I actually want to ask you about that, but I'll add a couple things that I also find are major downsides of this life, because it's not all rainbows and butterflies. One is, with a paid newsletter especially, but even with a sponsored newsletter, you basically have to get something awesome out every week, in theory for the rest of your life. People are buying an annual plan every day, so that means at least a year you have to write something awesome, if you want to stop. But it's hard to stop, because as you pointed out, the income is very meaningful, and that's a hard thing to give up. And so I'm not sure exactly the exit path that exists for us, where we might have to keep writing something awesome for the rest of our life, but I imagine something will emerge and we'll think of something else that we could do.

**Gergely Orosz** (00:47:19):
Yeah. And it's a really good example, because for a lot of companies, and I assume a lot of listeners are working in tech, typical thing is you work hard, you build equity at a company or you build the value of the company, and then you can sell that company, and then you can have an exit and you can do whatever. For what we're doing, it's really tied to us. So however much or little my newsletter will make, it'll have a value let's say four or five times the annual revenue as a business, but you cannot really sell it like that and you cannot really walk away.

**Gergely Orosz** (00:47:49):
So that makes it unique, it makes it harder to compete with, which is cool, but it does not create that much of an exit path unless you start to build a company around it, build an organization that can run without you, for example. This is what a lot of book publishing companies... So basically you build a publishing company where you start to hire people, who start to write some of the articles initially, and then later more of them, but it's not a one-person newsletter any more. Or you keep doing this, until you either stop and then the revenue stops, or you might be able to sell it, but at really under value.

**Lenny** (00:48:24):
Yeah. I really don't want to manage people. I don't want to have employees. And so building a media company with writers, that doesn't sound too fun, but maybe that's where this goes. That is one route, for sure. The other downside I'll just add is the fact that you have to write something awesome every week, it's hard to take meaningful time off, because if you stop producing great stuff, people leave. And I invented this PTO policy for myself where I take four weeks a year off, where I don't do a newsletter, but that means I can't take more than a week off usually [inaudible 00:48:58] weeks in a row, I don't know, people probably won't care, but it feels like things start to not go great if I just don't keep producing great stuff. So that's another downside, just [inaudible 00:49:08] topic.

**Gergely Orosz** (00:49:09):
Yeah. But a lot [inaudible 00:49:11] very early. So I think the whole concept of paying users is new, so I think we're going to do a lot of experimentation. And also a lot of it, I think you need to figure out what your needs are. So in the first year, I did not take a holiday in terms of... Or even when I [inaudible 00:49:25] I was writing, and it caused a bit of friction with my family. And now I'm solving it in a different way, so I am planning to take more time off now, and I'm doing it by working ahead with some of the less time sensitive things. But it is tough.

**Gergely Orosz** (00:49:43):
So a downside we haven't mentioned, but I'm just going to call it out, is holiday. The great thing at... I never felt... Well, I felt a little guilty sometimes taking holiday, but when I want a holiday, I took it off. When I had my son born, at Uber, they gave me a four month paid holiday. I took the whole four months, I just logged off. It was great. It wasn't my company. I was still getting stock. The stock price was independent of mostly what I was doing, just being honest. And that was really, really good. So this might be true, by the way, if you start any business, especially while it's just yourself, it's hard to turn off. And I think most people don't mind, I don't mind, but it gets to you. We should be conscious about burnout as a whole. So you need to solve for that, and I'm starting to solve for that as well.

**Lenny** (00:50:30):
Yeah. Okay. Enough about the downsides. Overall, it's pretty amazing making hundreds of thousands of dollars writing an email once a week/twice a week. So just to wrap up on that, I'm curious, where do you think this goes long term for you? And then I want to talk about just what it takes to be successful, but before there, do you think this goes long term?

**Gergely Orosz** (00:50:50):
I stopped making long term plans, because three years ago you would've asked me what I wanted to do, and I was like, "I want to be, I don't know, a manager of managers." And then I became one. And then [inaudible 00:51:01] what is my dream? I would've been like, "It's a stretch, but maybe I want to be a site lead." And I didn't become one per se, but I never thought of writing a newsletter, or now writing a successful newsletter. So I'm going with the flow. I'm seeing this less, by the way, as a newsletter or creator, or creator economy as people like to see it. I see this as a business, and I'm trying to put on that business hat. I'm building a one-person business. I want to make it sustainable, I want to make it successful, and I find that this thinking really helps me detach as well. I can actually enjoy my weekends as opposed to thinking, "I need to write this, or I need to write that." So I also want to make it work for me.

**Gergely Orosz** (00:51:40):
And I'm not married to the idea of, it always needs to be a newsletter, et cetera. Right now it is, but where I see us going is, I'll keep building the business, I'll keep playing to my strength, which is I love talking with people, I love writing [inaudible 00:51:56] I love software engineering. So this is a great format, but over time it might shift. So I'm keeping my options open. And what I've learned from this journey is, you need to create time for that spark to come. So one of my goals for next few years is to not spend 50 hours a week on a newsletter, which I'm doing right now, but spend 20, and then maybe take a few weeks off and have that spark come. Because the reality is, this newsletter only came because I gave myself six months of unpaid... I'm not going for work, I didn't ask for any LinkedIn emails. And the idea came and the inspiration came and the motivation came.

**Lenny** (00:52:36):
There's a lot of similarities with my approach. I don't think too far long term. I have no idea what's going to happen. I just take it to... I see where pull is coming from, and if it feels like an interesting opportunity and something that I'd be excited to work on, I explore it, like the podcast for example. And on that point, I will say, once you find that you can spend maybe 20 hours on a newsletter, I guarantee you'll find more work to fill that gap, because that's what I've been doing.

**Gergely Orosz** (00:53:00):
Yeah. And one last thing to touch on, you said something really important [inaudible 00:53:06] pull, and I want to double down on that. One of the biggest, best things about doing what we do when you're in charge of your time is, you can double down on pulls. So [inaudible 00:53:18] Uber, like I said, my plan was, I'll write this book for six months. Two months in, I just put a draft [inaudible 00:53:24] a really long blog post about mobile engineering, and I got a ton of messages, a lot. I usually used to get like three or four messages on Twitter per day. I got 20 in an hour, people saying, "Can I read the draft?" And I was like, that's interesting. I just felt this pull, of this huge interest of people caring about this. It was this really long blog post about mobile engineering at scale, and someone suggested on a private message, "You could probably turn this into a ebook." And I was like, that's a good idea, because it's a really long blog post. So I said, "It's going to be an ebook, and it'll be pay what you want." And then people started to buy it. And I was like, that's interesting.

**Gergely Orosz** (00:53:57):
So I didn't have much else to do, so I was able to double down. I said, for the next two months, I'm going to write this book, because it seems there's an interest in it. And [inaudible 00:54:07] I turned it into a book that was free for two months, but I got sponsorship. The point was, I was able to double down on this pull. And same thing with the newsletter. So we're going to talk about how I got the first few thousand subscribers, but the point was, I was able to double down on something that I felt like, this is super interesting, I never expected that people would care about building a large mobile app, more than a few hundred people. Turns out they do. Thousands do.

**Lenny** (00:54:30):
Let's actually jump to that. Let's talk about just how to get started, for folks that are like, "This is cool. I want to do a newsletter." Let's talk about just how you got started briefly, and then what you think it takes to be successful in the life of a newsletter person. So how'd you actually get your first thousand subscribers?

**Gergely Orosz** (00:54:51):
I'll tell the story that is kind of true, and people will think it's amazing, and also the real deal behind it.

**Lenny** (00:54:57):
Okay, great.

**Gergely Orosz** (00:54:58):
I announced my newsletter, I told people, "I'm going to go full time on this." I had maybe 10,000 Twitter followers and, I don't know, maybe 1,000 on LinkedIn or something that. And people started signing up the next day. I had 100 subscribers in the first day before I published anything. And within six weeks, when I published my [inaudible 00:55:15] I had 1,000 paid subscribers. And this sounds like a fairytale. And if you do this, I guarantee you're not going to get the same results. In fact, you'll probably see way smaller numbers.

**Gergely Orosz** (00:55:25):
What I didn't tell is that there was at least six years of accidental work behind this. I started a blog six years before... Actually, I've always been blogging since I graduated. I had this personal blog where I just published all sorts of random things about software engineering, but it was really... Sometimes it was about an app that I published, sometimes it was a problem that I came across. It was is all over the place. And I got fed up with this, the blog wasn't going anywhere, and I was just writing for myself, by the way, but I didn't how it was just all over the place.

**Gergely Orosz** (00:55:56):
And I said, "I'm going to start a blog, it'll be about software engineering and I'll call it The Pragmatic Engineer." I bought the domain, and I read this blog post from Jeff Atwood, who's the founder of Stack Overflow, and back in 2010, or I think in 2007 when I was still in college, he had the most popular blog on the internet for software engineers. It was called Coding Horror, and all the software engineers I knew read it and were drinking it. It was next level wisdom every single week, twice [inaudible 00:56:26] a week. You read it as well?

**Lenny** (00:56:29):
[inaudible 00:56:29] Yeah. I used to be an engineer, and I was all up in that. And I think Coding Horror came from a... I forget the book, but there's a book with that graphic.

**Gergely Orosz** (00:56:36):
There's a book, and there's a graphic. Yeah. And he wrote a post which really stuck with me for years. He said, how to be famous on the internet. He said, there's three simple steps. One, write a blog post. Two, do this three times a week. Three, do it for two years. And I guarantee, if you do this, you're going to be famous. And I always thought it's kind of ironic, but the more I read it, the more I thought he actually means something with it. And when I started this blog, The Pragmatic Engineer, I said, "I'm tired of my old blog being all over the place, and there's no focus, and no-one really cares about it. I'm going to do what Jeff Atwood said. I'm going to publish... Okay, it's not going to be twice a week, but every two weeks I'm going to publish an article, and I'll do it for a year." So I started to do this. I published six blog posts about software engineering, going into topics that I [inaudible 00:57:25] research and all that, and then I gave up.

**Gergely Orosz** (00:57:27):
And I'm saying this because I kind of gave up, and I left it for a few months, but then something interesting happened. I had a huge traffic spike, and it crashed my shared hosting at the time. And it came from a site called Hacker News that I [inaudible 00:57:41] heard about, and people were discussing my posts, and they were adding a lot of things. And I was like, that's interesting. People care about what I wrote six months ago.

**Lenny** (00:57:49):
What was that post, by the way?

**Gergely Orosz** (00:57:50):
It was called, "A comment is an invitation for refactoring." I wrote my view that if there's a comment in a code, that means that comment should be deleted and you should just refactor the whole thing. And it exploded on Hacker News. Some people called me an idiot, some people called me absolute wisdom, and it was these two crowds battling it out. And I was like, wow, I actually made software engineers in Silicon Valley argue about my stuff. I saw some of the [inaudible 00:58:17] people, some really high [inaudible 00:58:18] people were really going for [inaudible 00:58:21]. So that's when I thought [inaudible 00:58:23] my writings, some people might read it, it's not guaranteed.

**Gergely Orosz** (00:58:26):
And I started to write on that blog once every few months, depending on my mood, but I never stopped doing it. And I partially did it [inaudible 00:58:35] always hoped that it would get onto this site called Hacker News. But by the way, for a while, I didn't even know you could submit it, so I never submitted my own things. But the other thing was, I just kind of liked it, and I had this habit, and over years... I had this blog from 2015. For six years I was writing that blog, and in the last year... When I worked at Uber, on the side I wrote about my work, in terms of the things that I could write about, not about the details that we did, but some of the learnings [inaudible 00:59:02] for example, distributed systems. And more and more of these posts just started to just pop up on Hacker News. People would either submit it, or sometimes when I submitted it, it would just do well. And I was thinking, so people... I started to get this validation, people care about what I write.

**Gergely Orosz** (00:59:16):
And to question of the success of the newsletter, by the time I launched a newsletter, I had a lot of posts that a lot of software engineers read, and there was a very famous post about performance management, how to do performance reviews. I wrote one about the tri-modal nature of software engineering salaries, where I observed that there's three different tiers that are... There's big tech and there's local companies. And I think what happened is, when I announced that I'm going to write this newsletter, I also put it on the blog. A lot of people realize that they... "I've been reading this Pragmatic Engineer, I don't know who is behind it, but I like it. Let me sign up. I do want to get an email every week, instead of the things that were every now and then."

**Gergely Orosz** (00:59:56):
So there was years of work, and I wish I could tell you how to build a successful newsletter, but the best advice I have is still what Jeff Atwood does, except I have less conviction. But if you start writing, and you do it regularly, two things will happen. First of all, you're going to [inaudible 01:00:11] you write for yourself and you keep improving, you'll be a better writer. That's for sure. If you're lucky or if you're right about stuff, you might start to attract people who think similarly. So step one is get started. Step two is keep it up. And my suggestion is [inaudible 01:00:26] for yourself. The weird thing is, until I started my newsletter, I never thought I would turn this ever into a business, but it always felt rewarding. So I never... If you're starting out writing a newsletter to do what I'm doing one day, it might work out. But interesting enough, I never even thought that this was an opportunity.

**Lenny** (01:00:48):
So people listening to this that are thinking about, should I explore this life? If you think about your story, you wrote a book, you blogged for a while before this, you worked at Uber for a number of years. In a sense, it comes across a little bit like, there's no way I can be successful if that's the background I need to have. I have to have written things and worked at an awesome tech company. What advice do you give folks that are coming to you being like, "Gergely, should I start a newsletter? Does it make sense for me?" Do you need the background that you have, do you think?

**Gergely Orosz** (01:01:21):
Don't forget that when I started my blog, I didn't have any of this.

**Lenny** (01:01:24):
And this is while you were at Uber. This is before you started the newsletter.

**Gergely Orosz** (01:01:28):
It was before I was at Uber. So I was maybe at Skyscanner, or maybe at Skype, but I was even blogging before. I was talking to conferences before. So my advice really would be, if you're thinking of a newsletter or something similar, start teaching and sharing what you know and what you're observing. This could be a newsletter, this could be a YouTube video, this could be going to meetup. Actually, ten years ago I went to a lot of meetups where I presented all sorts [inaudible 01:01:54] I met a lot of cool people. I would say, share your knowledge one way or the other. And as you're doing it, you're going to learn a lot more.

**Gergely Orosz** (01:02:01):
So what I find... This is true, when I was a manager, we had to set goals, and I told people there's two types of goals you can set. One is [inaudible 01:02:12] people set this goal, I want to be promoted the next thing, or I want to lead this big project. And those are bad goals, because it's not in your control. So setting a goal that I want to have a successful newsletter with, I don't know, 20,000 subscribers, that's a goal where you're not in charge. A good goal is what you can do. So a good goal for example is, I want to learn this new language in the next year, which I'm going to spend time on, or I want to leave work at 5:00 PM on Fridays to be home with family. So set those goals that you can control.

**Gergely Orosz** (01:02:41):
And this is how actually my blog started initially. My goal was, I want to write once a month. And I did that for a while, and I was proud about that. Or whenever I learn something, I actually want to share it every now and then. So I would say set those goals, and the rest will come, probably. Again, don't get me wrong, I'm not trying to talk people out of doing it. But for me, a lot of this was luck. And the other thing that I would suggest is be curious, and look at your professional career as well. One thing that definitely helped me is getting pedigree. I come from a small country, from a really good university which no-one knows about, but I didn't grow up in let's say Silicon Valley, so I actually made a subconscious point to try to work my way up. And after I got to let's say JPMorgan in London, I was pretty picky of where I would go next. So that's why, when Skype came along [inaudible 01:03:36] this is great. Everyone knows Skype, I love Skype. And it was same thing with Uber.

**Gergely Orosz** (01:03:40):
So especially these days, people would not pay nearly as much attention to me if I worked at Small Parts Limited. So there's that part as well. So you need to manage some of these things, figure out what you want to do. For a long time, I pretty much thought that I just want to climb the corporate ladder and prove that I'm good enough at all these companies. I was just doing all this stuff on the side. It's interesting how it's now flipped, and now doing these things, this is my main thing, which used to be my side project.

**Gergely Orosz** (01:04:07):
And I guess one last advice is, do some side projects. All of this starts as a side project. At work, no-one's really going to appreciate that you're doing a newsletter or this or that. Try stuff on the side, assuming that you have time. Or if you don't have time, try to make time. Because I feel a lot of what we're doing is pretty entrepreneurial, and the only way you're going to get these muscles, if you start some small things.

**Lenny** (01:04:31):
You talk about the pedigree being important. I think there's also an even deeper point, that you actually need real experience doing real things that scaled and worked and mattered and worked with amazing people, to actually build a foundation to write about, share wisdom from. And that's really important. There's a lot of people starting newsletters and tweeting who haven't done much and don't have a lot of real life experience to share. And I think that's the core of a lot of what we do, is it needs to be based on real things that worked and that you've learned, or that you have access to other people who have learned these things.

**Gergely Orosz** (01:05:06):
I would say that, but one thing that I'll double down [inaudible 01:05:09] that's a really good observation is, if you're serious, like one day I will want to write a book or a newsletter, it's kind of the same thing, or teach people about stuff, look at the people that you look up to that you actually trust. Maybe it's me a bit or maybe it's you, but it's more likely people like Kent Beck, for example. He's the creator of TDD, and he's written a lot of books. He's one of my favorite people, I think he's coming up 50 or 60 [inaudible 01:05:36] if he listens to this, sorry if... I don't want [inaudible 01:05:38] seem old, but what I love about Kent Beck, is he's been in the middle of it. He has always worked in the industry, and that he wrote about it. But for example, I think he invented or he was a co-inventor of... Was it TDD or extreme program... Anyway, one of these methodologies.

**Gergely Orosz** (01:05:58):
And then [inaudible 01:05:58] went to work at Facebook. He took a title cut to be a software engineer, and then he hosts the TDD workshop, the test driven development workshop, and no-one showed up at Facebook. And Facebook did no testing, which went against all commercial wisdom. And he took that risk joining this company where he could have been... People would've knelt down to him anywhere else, but he went to this company where he just wanted to learn. He's this lifelong learner. He's right now writing a book. But what I think [inaudible 01:06:26] if you want to be someone who people listen to, yes, do cool and interesting stuff, push yourself to get into places that do these interesting things.

**Gergely Orosz** (01:06:33):
That's how, when I went to Uber in 2016, it was one of the highest regarded places back in 2016, and in 2017 it was the other way around. But back in 2016, people were turning down Facebook and Google offers to go at Uber, which we all thought would change the world. So you do need to get into those teams that are doing interesting stuff, prove that you can do that, and you'll have a lot more interesting stories to share, that's for sure.

**Lenny** (01:06:59):
If you had to boil down advice for how to be successful in this life of a newsletter, you had to boil it down to just one or two key pieces of advice, what would you say?

**Gergely Orosz** (01:07:10):
One is habit of depth in the field, whatever field you do. So this might mean that I think... I don't want to say that if you don't have experience, don't start one, but it's kind of true. So become an expert somewhere, somehow, before you start, because you'll be a lot more credible. I think there's no shortage of reporters and journalists who don't know about stuff, but they can interview people, but that doesn't give anything extra, and I think people feel that.

**Gergely Orosz** (01:07:38):
**Gergely Orosz** (01:08:19):
He used to work at Amazon, and then at Google he wrote this internal email about platforms, about how Amazon is great at platforms and Google is terrible. And he was really well known at Google, because he wrote stuff inside Google. So he's experienced, knows a lot of stuff, and then he quit Google and he started to do a podcast that's on YouTube. You could check it out, it's called Stevey's Podcast. And what he did is, every week he recorded an episode and he talked about a bunch of his learnings, a lot of stuff, and he was pretty clear up front when he started the first one, he said, "What I'm doing is, I'm going to do this for six months and I'll see if it sticks, see if people care about it or people watch it."

**Gergely Orosz** (01:08:55):
Now, this guy had a lot of experience, really fun [inaudible 01:08:59] I think it's really fun to listen to. And in the end, it was I think successful. It got a couple thousand or maybe even 10,000 subscribers, but it wasn't this rocket ship. And I think what he did, he just stopped after six months, and he actually started head of engineering at Sourcegraph, he actually went back [inaudible 01:09:15] industry. But what I love about this, it shows that you cannot guarantee having success, but you can do what he did, which is start something, do a cadence, see if it sticks. If not, either pivot or do something else. I feel the world is kind of about that as well.

**Gergely Orosz** (01:09:30):
If you think about... Take a step back of, what is a successful newsletter? What is a successful podcast? What is a successful YouTube channel? And it's stuff that's interesting. It's either entertaining or educational. But all of these things, you can't really put a finger on. If you watch YouTube, Mr. Beast is someone who you probably came across, I actually like watching his videos and [inaudible 01:09:56] how good he does it, but it's not something you can [inaudible 01:09:59] anyone would have written in a book. So there is a sense of trying to understand what people care about, and a good way to understand is either experiment or observe or just try out stuff.

**Lenny** (01:10:12):
This is great. I feel like I can boil this down even further from everything you just said, which is, build depth in an area, then write a blog post twice a week for two years, and good things will happen.

**Gergely Orosz** (01:10:25):
I'm pretty sure. And here's an interesting thought as well, just for closure. I was talking with someone on why my newsletter is so successful. It's really successful, and I honestly don't know why. And this person told me something interesting. This is a person who had a really successful YouTube channel with about 200,000 subscribers, so more than my newsletter. And he said this. He's like, "What I noticed is, you started your blog in 2015, 2016, and I started my YouTube channel in 2019 or something like that. And on YouTube, there's so much quality, there's super high great productions, everyone is doing YouTube." And he said, "You know what I don't see? I don't see many blogs that are writing in depth stuff regularly. I feel everyone went over to YouTube or TikTok. So there is the other angle of the medium." And I'm saying this, not [inaudible 01:11:16] but it might be an advantage. These days, fewer people write, because I think a lot of people find it hard and more people will do videos. And you can take advantage of some of these shifts, which might be good or bad.

**Gergely Orosz** (01:11:27):
So if you're going to be a really well known person on YouTube, you might get more people watching you, but you'll have a lot more competition. And the last thing is that for me, writing, especially with software engineers, it's really efficient, because I can scan through it. I don't like YouTube videos, especially for learning about stuff, because I can't even scan through the whole thing. It's just really time consuming.

**Gergely Orosz** (01:11:47):
So I think, decide if you want to do entertainment, which for these podcast listeners, I don't think that's in the question, you're competing with the likes of Spotify and Netflix. Education, which is a little bit more dry, but it's really useful. Or edutainment, which is entertaining education. And once you figure that out, either if it's education or edutainment, you can figure out what format might work both for the medium and for you. And at end of the day, you need to enjoy it. I personally have learned over time to love writing. I love being in the zone. So for me it's not really work, but it's fun. And once you find that thing, whatever that might be, it just makes it easier.

**Lenny** (01:12:27):
Gergely, it's always so fun talking about newsletter stuff. I don't have many people to talk about this life with. I hope this was useful to people who are exploring this path, thinking about it, or even the different creator path. Just 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?

**Gergely Orosz** (01:12:45):
You can find me at pragmaticengineer.com. There is a bunch of stuff listed there from the Twitter, LinkedIn, my talent collective, some of the companies that I invest in, et cetera. Everything's there. And you can also sign up to my newsletter. Listeners being useful to me... If you work in tech, consider signing up to my newsletter. I always tell people we're a complimentary newsletter. If you work in product or have an interest in product [inaudible 01:13:11] newsletter is an awesome choice. With software engineering management, it goes the other way. And it's not just... People are telling me when they're data scientists or even product folks, sometimes they get some value out of it.

**Gergely Orosz** (01:13:23):
I write this column called the scoop every Thursday. If you hear of any interesting scoop happening, especially relevant for techies, this might be some change in the workplace, like your company is just rolling out agile [inaudible 01:13:36] team at Twitter did, feel free to ping me, just a short search for sending scoop to the Pragmatic Engineer. I treat everything as anonymous, so you can tell me interesting stuff. I'm typically interested in the stuff that you might not read about in the traditional media, but us techies really care about.

**Gergely Orosz** (01:13:51):
And finally, if you work at Google and you want anonymity to talk to me, just ping me, because one of my next articles will be Google's engineering culture. I wrote one about Facebook, one about Amazon, and I tried to talk with mostly software engineers to get a sense of how these companies work from a software engineer and engineer manager perspective.

**Lenny** (01:14:11):
Awesome. I hope this comes out before that post comes out, but if not, then enjoy that post. Gergely, thank you so much for being here. This was awesome. And maybe we'll do a V2 as things continue to grow.

**Gergely Orosz** (01:14:23):
Awesome. It was great being here, Lenny.

**Lenny** (01:14:27):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or 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] What it takes to become a top 1% PM | Ian McAllister (Uber, Amazon, Airbnb)

**Ian McAllister** (00:00:00):
If you forget about everything else, forget about politics, forget about promotion, or having a bigger org or whatever, if you simply wake up every day trying to have the biggest impact you can, or if you're a leader trying to use your team to have the biggest impact you can in the company, how you do every part of your day, that's a really good guiding light.

**Lenny** (00:00:22):
**Ian McAllister** (00:03:57):
Thanks for having me, Lenny. I've been looking forward to this.

**Lenny** (00:03:59):
Me too. I'm sure you hear this a lot, but when I was a new product manager, a very new PM, the post that you wrote on what makes a top 1% product manager was really influential and really helped me figure out what to focus on and what skills are really important. And I find that it continues to live on as this very legendary post for product managers who are trying to figure out what to do. And I just reread it in prep for this post and I was just like, wow, this is ... Now that I'm on the other side, I'm like, this is so right. And so I'm really excited to dig into a lot of these things in person, virtually in person, and with you. So thank you again for doing this.

**Ian McAllister** (00:04:35):
Yeah. Man, it's awesome. I'm excited just to spend some time talking with you about product and we'll see what happens.

**Lenny** (00:04:42):
Did you expect the impact that this post had when you were writing it, when you were just putting this together, the impact that the post had in your career or just the PM industry?

**Ian McAllister** (00:04:51):
Definitely not. I used to lurk on Quora at the time and then I was just having fun reading things and answering some questions and I used to look for questions in the Goldilocks zone. They weren't too high level of abstract like how do you be a good problem, but they weren't too super specific and this one was kind of right in the middle. And so I'd pluck off a couple of those and I think more as a way to structure my own thoughts, that was what was interesting and fun for me to do that. Not because I thought it'd have any kind of real reach. But obviously it's been cool to see that people reference it pretty often and that's been pretty fun.

**Lenny** (00:05:23):
We'll link to this in the show notes. If folks that are listening don't know what we're talking about, we'll link to it and you can check it all out. And we're going to be talking about a lot of this stuff in the actual chat, but there's a couple things there that are worth maybe drilling in on a little bit. One is just the impact that writing on the internet can have on someone's career. This one post I imagine had a lot of impact on the trajectory of your career. Is there something you could share there? Is that true?

**Ian McAllister** (00:05:45):
Yeah, it did. And there's another post, I think it was before this one, someone just asked about Amazon's product development process and so I wrote about the working backwards process. Which isn't my process. I just used it and just described it and just kind of caught on a little bit there as well. I think those two, and then I started to write more about people management and product management. And I think the value for me was so awesome just to make connections with people in the industry and it felt like this is, I guess, the 2010 or something like this where a lot of Amazon people I of thought were just so 100% heads down. It was a little bit of a secretive culture, not maybe like Apple, but it was pretty private. But I was interested in the startup community and product in general and so I think I spent a little time trying to engage with folks and I just made so many great connections and relationships from this.

**Ian McAllister** (00:06:39):
I remember interacting with you and getting to know Joebot and other folks at Airbnb early on even before I joined. But obviously I'd credit this work and those relationships for me ultimately going there and so many great relationships and people I've met because of it. And aside from just the little positive feedback, I mean people tweet at me periodically, be like, "Hey, by the way, just love this post," and whatever. And so it's super gratifying.

**Lenny** (00:07:03):
You mentioned a little bit about your background and we're about to get into that and I want you to share all the things you've done. But the other piece there that I think is interesting that comes up again and again in the power of writing is it often just starts with you trying to collect your thoughts and putting it out there and ends up, wow, so many people find that valuable and it spreads. And so that's just a really simple way of thinking about if you're starting to write online, just summarize something that you've been thinking about that you want to just crystallize in your own head. There's this quote that's probably falsely attributed to Mark Twain and Hemingway often of just like, I don't know what I've thought until I've written it down. And that's super true with these things and so that's a good example of this.

**Ian McAllister** (00:07:42):
And I think with any kind of writing, it was probably less structured initially, but I would, partially because I was trying to share something for an external audience, try to just organize it and make it compact and not too wordy or rambling. And I think business writing, I spent a lot of that time doing that at Amazon, is so valuable because you've got to be a clear thinker to be a clear communicator. And so there's two tests in writing well or communicating well. It's both those things. So I found it's pretty valuable in kind of sharpening your ax.

**Lenny** (00:08:15):
So these are the two things we're going to focus our chat on is what makes a top 1% product manager and then the Amazon way of working and especially working backwards. So these are all good cues for where we're going. But before we get there, can you just spend just a minute giving us a sense of some of the wonderful things you've done in your career and what you're up to now?

**Ian McAllister** (00:08:31):
Well, I can tell you what I have done. I'll let others decide what's wonderful or not. So after doing finance and economics in school, I made the logical choice and I got a job doing marketing in the beer industry and then the next logical choice, I moved to Tokyo and I bootstrapped my way into software development without knowing Japanese or software development. Did that for a few years, came back to the states working as a developer at a startup and then kind of a midsize company and then moved to Microsoft as a program manager, pretty much a product manager. The same thing there in that role. Learned some good stuff and then made a connection with Amazon and moved there 2006. And that was really the start of when I think about building my product toolbox and leadership toolbox. So few different things I did over 12 years, a few years in retail and conversion.

**Ian McAllister** (00:09:22):
I then moved in traffic and direct traffic loyalty when I created Amazon Smile. The role in Alexa. I led Alexa International, so scaling Alexa and Echo to six more countries. And the last role in delivery experience and operations. So I led a number of different programs there and then recently joined Uber where I'm a senior director of product and tech for vehicles. So that means everything, all the tools that help fleets and rental companies make their vehicles accessible to Uber drivers so they can earn. Sustainability tech and electrification, our vehicle platform, and then creating a path for autonomous vehicles to come onto the platform. And that's it.

**Lenny** (00:10:03):
Amazing. I just realized this one thread through your career is autonomy and AI a little bit, right? With Alexa and then with Uber, with these autonomous cars stuff you're working on now. Is that something realized or is that an accident?

**Ian McAllister** (00:10:18):
Well, I mean I guess you could connect those things. Obviously both are machine learning, AI. The way I think about it is that I've done a whole bunch of different lifetimes, especially around eCommerce, and so it allows me to cover the gamut. Plus, I guess I forgot to mention the time at Airbnb working with Joebot and you and Vlad and Dan and Shirley and there was focused on building out the customer support technology platform. So that's another part of the eCommerce platform. Covers the gamut.

**Lenny** (00:10:45):
I forgot to bring that up too. I'm glad you touched on that.

**Ian McAllister** (00:10:48):
I don't know how I missed that. I guess I skipped past that with the Amazon stuff.

**Lenny** (00:10:50):
The most transformative time getting to work together.

**Ian McAllister** (00:10:53):
That was awesome. That was awesome. I learned a lot from you too during that time.

**Lenny** (00:10:56):
What a time. This is a good time to chat about, speaking of Airbnb and all that, to chat about what makes a top 1% product manager. So I know your post was really titled what separates a 1% PM from a 10% PM, but it feels like it's even broader, just like how do you become a top 1% product manager. And I thought maybe a good way to start here is maybe just run through the attributes that you've found over the years or here's the things that a top 1% PM needs to get great at. Maybe just run through them and then we'll talk through them in a little more detail.

**Ian McAllister** (00:11:28):
Yeah, I was going to pull up my post here so I could actually refer to it. Do you want me to go through all of them or just pick out a couple to touch on?

**Lenny** (00:11:33):
Let's maybe just go through them quickly just to put them out there and then I'll have some follow up questions to dig into a few of them.

**Ian McAllister** (00:11:40):
All right, sounds good. Well, the way I listed it at the time, think big. Always want to hunt for bigger impact. Communicate, I think we'll probably touch on that a little bit. It's super important for PMs as a test of their thinking and their communication. Simplify. How you can do more with less and have more impact. Simplifying is a great way to do that. Prioritize. That's I think the core skill after communication of a PM and there's so many different lenses to view that. Let's see here. Forecasting and measuring. I think that it's really important. What separates product managers from consultants sometimes is you forecast and then you execute and then you measure and validate and that helps you build your instincts. Just obviously the core execution of just shipping and doing what you said you do. Understanding technical trade offs is that you don't have to be a software engineer to be a great PM, but the more you learn about technical trade offs, not just product and customer trade offs, that will help you simplify and get more yield out of your resources.

**Ian McAllister** (00:12:40):
Understanding good design. If you're working on anything customer focused, that's always going to help you think in the mind of a customer or user. You don't need to design, but the more you understand helps. Writing effective copy. This goes a long way not to get close and not to sub out the copy to somebody else, but to get good at communicating with a couple words to your customers. That's a great skill. Those were the ones that I wrote at the time, I guess 10 years ago, and then I refreshed the post recently in my newsletter. And I added a couple new ones honestly, because as I reflected back, there was a few that I think a lot about these days that I missed the first time around. Earn trust with others. That's so important as a PM, but especially if you're going to grow as a product leader becomes even more important.

**Ian McAllister** (00:13:29):
And I think trust is the currency of a product manager and a product leader, especially if you're going to grow in your career. Digging for data. It's out there and you got to develop the tools to go find it. Not to depend on your analyst or what's in the reports today. So that's a really important skill for anyone in product. And probably the more junior you are, the more important it is as you're really in the weeds there building product. Pushing back effectively. This is an art and a skill, but I think your ability to do this is pretty correlated with your ability to grow and succeed as a leader. Because if you say yes to everything, you're going to go nowhere. Adapting to change. How you react to change will obviously impact one, your mood and your morale, as well as how effectively you can rally yourself, your team. And then driven by impact, not promotion. Ultimately that's what you want to wake up every day thinking about how to have an impact for your business and that will be an indicator on your likelihood of promotion. So do that instead of just focusing on how to get promoted and having that guide your day.

**Lenny** (00:14:33):
Awesome. So it's a long list. There's a lot that a PM needs to be good at, which I think if you're a PM you already know. It's a wild, crazy, impossible job to have everything nailed down. And at the end of this post even mention you've never met a 1% PM that does all these things. And I think that's important. No one's going to be the best at all these things. And so just to drill down a little bit and get a little more focused. Say you're a new product manager. Of these, I forget how many there, maybe 10, 12, what are the top three that you think new PMs should get most good at and focus on?

**Ian McAllister** (00:15:06):
Probably communicate, prioritize, and execute. I think those are just the core building blocks. Other ones will be more important as you grow and become more senior, but those ones, no matter where you are in your product career I think are super important. Being a better communicator is something I've been working on my entire product career and I'll be working on until the day I stop. And I remember years ago I was at Microsoft, my first effectively product manager role and my product unit manager, Thomas, came by the office and I think he asked me, "When is this going to ship?" And I was like, "Well, this thing is taking a little bit longer here and this other thing and yada yada." And I gave a bunch of background, but I didn't really answer the question. And I got a little feedback from him like, that's not really the ... Ultimately he's waiting for a date.

**Ian McAllister** (00:15:53):
And so I just reflected on that and that was, as I remember, my journey to try to be a better communicator over time and I'm still on it. When I went to Amazon, I worked for Kim Rackmiller who was our, I think at the time, SVP for Worldwide Discovery. And I think she was Amazon's first TPM. And she was tough but super smart. And so that was also an early experience to learn from her. And sometimes you get some feedback when you didn't really answer the question. And my first boss, Russell and I organized and started to gather this thing called the Book of Kim. And so we would gather these best practices that we learned from her elsewhere. Avoid weasel words, answer first and then explain, own your problems. And started building this.

**Ian McAllister** (00:16:36):
And then I extended that over time and added a bunch more and wrote a post called the Operators Manual. I tried to gather all these things together. But it's such an important thing and the stakes get higher as you work with more and more senior people. But if you can get in the habit early of answering a when question with a date, knowing how to use numbers to answer questions and honestly just learning from feedback and grade yourself after you get feedback on a doc or after a meeting or after answering a question in an elevator. And if you try to say, "Gosh, how could I have done that better?," and then try to get better, you can. And you can go far if you just focus on that and all the other 150 skills of a product manager, but if you don't have that, it's unlikely that you're going to really go too far in your product career.

**Ian McAllister** (00:17:24):
So that was communicate. I guess prioritize as the next one. And so I think this is the number one key tool of a product manager is prioritization. Because so many things come from being good at prioritizing. And it's not just what project do you do next or do you do this project or that project. There's so many different dimensions to prioritization. There's which themes are you going to prioritize in a roadmap and which projects within a theme and how are you going to sequence those projects, how much of a project you're going to build. And also just time management is also a prioritization function. Like what are you going to choose to spend your time on? Which things are you going to really go all out to make great and which things are you going to starve for attention or just not do? Given the same amount of skill intelligence and resources, a product manager with a great innate ability to prioritize is going to generate 5X the impact of someone without that skill.

**Ian McAllister** (00:18:18):
My early, if you could call it success at Amazon, I think was completely dependent. It wasn't because I worked smarter or I was smarter, I worked longer hours or I was more technical than other people. I think it was just because I was one, super hungry for impact. And if there was a number or a metric that measured success at the business I was running, I wanted that to go up and to the right. Not to hit a goal, but just to go as far and as fast up to the right as possible. And if anything, it was just working with a team to hone in on the projects that would do that with the greatest leverage and just marshaling all the team's resources. So that was a good start. That was a fit with Amazon in terms of working backwards from a fitness function or a metric.

**Ian McAllister** (00:19:01):
And so did that with the first team I was there and then again later managed the gifting business. And so it just was one skill that I think helped me as well as make up for maybe some deficiencies I'd had. I don't have the biggest brain in the world and I don't have the biggest working memory and I wasn't the most technical, but by trying to really get good at that prioritization, I think that's helped me and it still does.

**Ian McAllister** (00:19:23):
I think execute is the third one, which is no surprise that every PM has to execute. And I think assuming you prioritize well then execution means sort of molding what you want to build into a simple compact package that has the highest impact possible. And then also execution's a big function of the team you're working with. So it's your designers and your data science folks, and especially your engineers.

**Ian McAllister** (00:19:47):
So anything to do with how well they're doing their jobs or how well they're resourced or whether they're getting better and better at every sprint, you have some amount of ownership in helping make that happen because that directly impacts your team's ability to execute and ultimately your reputation as well for being able to execute. The drive that goes into execution, product managers are the mode of power behind execution and impact. And if you stall out or you don't do your job, the project's probably going to stall out as well. And so you're the ones, especially with a TPM, if you're lucky enough to have one in the back of the ship, kind of beating the drum and driving everyone forward. But again, lots of people have written a lot of stuff about execution and there's a lot to it, but I think those are probably the three I'd focus on.

**Lenny** (00:20:32):
Awesome. And what's interesting about these three is if you look at the rest of the list, think big, understand technical trade offs, understand good design, I think what I would take away from this is those are the things you don't need to focus on that much when you're a new PM. Focus on, as you said, communication, prioritizing, executing. Focus less on these other things because later they'll become more and more important and obviously learn as much as you can, but it's almost bit easier to think about the things you don't need to stress about when you're starting out.

**Ian McAllister** (00:21:02):
Yeah, I think that makes sense. If there's a core or think about in year one as a PM, focusing on those things. And you can develop other skills over time. But yeah, I think you're spot on there.

**Lenny** (00:21:14):
If we were to go back through these three, just maybe as a last question, and you may not have an answer to this, but if you think about communicating, prioritizing, and executing, is there one tactical thing you could suggest that a PM listening to this can do to get better at one of these things? Is there a trick you've learned of, wow, this is one way you could level up communicating, executing, prioritizing or not?

**Ian McAllister** (00:21:37):
The closest thing to a checklist, the post I mentioned, the Operator's Manual, that was the closest thing to, if you do these things, these specific actions, I think it'll go a long way. Because a lot of them are guided around not doing the easy pitfalls and communication mistakes like rambling. If you're asked a question and you explain and then maybe you get to the answer, if you just think, answer and then explain or sometimes answer and then shut up, that actually is a tactical thing you can do to get better at communicating. And there's some other tips in there as well. So that was my attempt to try to encode, to take some of the ones that we gathered early at Amazon, add some more. The others are ... Yeah. There's no just simple trick unfortunately to prioritize other than ... I mean I think working backwards is a good technique to have impact to guide your prioritization. And that is something where it's not a simple tip, but there's a set of practices and behaviors that you can do that will ultimately lead you to prioritize better.

**Lenny** (00:22:39):
Awesome. We'll talk about all that.

**Ian McAllister** (00:22:40):
And then I think communication, the simple tip was just grade yourself after you communicate and try to just take a moment and after a while you'll just do it naturally to think about, "Gosh, how would I have answered that question better?" And so the next time you could try to answer that question better and it's just a continuous improvement process.

**Lenny** (00:22:58):
Or maybe even ask your manager, "Hey, what could I have done better in terms of how I communicated in that last meeting or that last email?"

**Ian McAllister** (00:23:04):
Yeah, absolutely. Absolutely.

**Lenny** (00:23:06):
Okay, so then coming at it from the other direction, say you're a senior PM, what are three of these attributes that you would suggest folks focus on to get better and level up in their career?

**Ian McAllister** (00:23:17):
Gosh, it's still communicate, to be honest. I think that's the one at every level of product, just the stakes are higher. I think think big is one for sure. There was a phrase I think Warren Buffett in the Berkshire Hathaway letter used at some point. Was at our scale we got to hunt for bigger elephants. And so I think at any scale as a PM, whatever your idea is or whatever your solution or the problem you're solving, take a minute at the beginning to say, could this be bigger? Could this be a bigger thing and more impactful than the initial idea, even if the initial idea sounds big? So that's a tool and that's often where I'd start when my PMs were sharing an idea is I'd try to expand it to the degree it might be expanded, think about it from that perspective and then maybe you want to still start small, but with a bigger vision in mind.

**Ian McAllister** (00:24:04):
Earn trust is a huge one and that's kind of why I added it more recently. And it becomes even more important as you get into senior roles because I think it's truly the currency of a product leader or probably any leader in any function. Because if you want to ask for more resources to do something bigger, if your leadership doesn't trust you to use those resources well or do what you said you're going to do, you're probably not going to get them. But if you've built trust that you're a good steward of resources and you make a lot of impact with a given team, that's directly going to correlate with your ability to gain more resources. Trust is just built by repeatedly setting and meeting expectations. And I think that's a good mantra to think about as a FM. Am I meeting the expectations that I set? And not just doing good things, but calling your shots, forecasting, setting a goal, and then hitting it.

**Ian McAllister** (00:24:54):
And if you do that repeatedly, you're going to be in pretty good shape. And there's so many practices as a product manager or product leader that build trust. You tell the truth without fail. And you launch when you say you'd launch and you launch what you said you'd launch and you own your mistakes. And then the other practices just lose trust. If you lie or if you're evasive, if you don't ship what you said you're going to do, if you ignore your mistakes or you repeat them. And so I think just simply having high standards for yourself and think of trust as that currency, that's going to correlate well as a PM, as a GPM or director of product in any level, that's the thing that you want to build.

**Lenny** (00:25:34):
So thinking big, building trust. Was there a third?

**Ian McAllister** (00:25:37):
I think maybe the last one, which is certainly relevant for a PM but is really true as well, is driven by impact. And if you forget about everything else, forget about politics, forget about promotion or having a bigger org or whatever, if you simply wake up every day trying to have the biggest impact you can, or if you're a leader trying to use your team to have the biggest impact you can in the company, which will influence how you build your roadmap and how you do every part of your day, that's a really good guiding light. And I remember in my first 10 years at Amazon, just naturally not because I thought about it, I was just hungry to have an impact. Take my business, grow it as fast as possible. I wasn't maybe loosely thinking about promotion, but I wasn't thinking about it. I never talked to my manager about it and I wasn't bringing it up. I was just focused on taking my book of business and making it bigger. And then the net result was I was promoted several times and I did grow in my role, but that wasn't what drove me. It was just the impact.

**Lenny** (00:26:38):
Would you say that driving impact is more important for a new PM or senior PM? It feels like impact is the soup within which all PMs swim and that's constantly important, but it's interesting that you mostly put that into the latter part of a career. Do you feel like with new PMs on your team you're less expecting them to think about impact and focus on impact?

**Ian McAllister** (00:27:01):
Well, I mean I think for junior PMs, if you're a brand new PM, then yeah, you want to have an impact, but you're really just ... You have a project or a feature to ship or something like that and you're often not necessarily given a lot of latitude to build your own roadmap. But you're asked to ship this. So you want to spec it, you want to execute and do it. But increasingly as you grow, there are opportunities to sense out and try to have a bigger impact maybe and then start to influence prioritization or roadmaps. It's just that the expectations, it goes from being a nice to have as a junior or first time PM to as you get a little more senior, hopefully if things work the way they should work, that's really how you're evaluated. Yes, you want to treat your team well and you want to do a whole bunch of other things, but take two people, one has a massive impact on the business and one who doesn't, then the right way to work should be that first person should be the one that grows and develops and is tasked and with bigger challenges just because if you're impactful at a bigger challenge, that's even more important for the business. So I think that's a good way to think about the flywheel of product leadership.

**Lenny** (00:28:11):
It feels like a lot of times you get lucky as a new PM. You work on a project that ends up having a lot of impact that you didn't necessarily drive. You just happen to work on something that, wow, this was a huge deal and that feels like an important thing to optimize for a little in your early career is work on something that's likely to have a lot of impact even if you're not responsible for setting the strategy and prioritizing.

**Ian McAllister** (00:28:29):
Well, I think that's true if you have a choice in where you work in product. If you have a choice to work on something that's part of offense, something that drives the business. And it's true that executives wake up if something drives dollars or customers or offense things and it just maybe shouldn't be this way, but a little less interested in things that maybe less than a risk that just the risk never happens, it comes to pass or a cost center that operates a little more efficiently. So that it's one lens where that might relate to your success. I think also who you work for. And I think most of us don't get to choose that especially early in our career. It either works out in your favor and which is great and that was the case for me, especially at Amazon, some of the leaders I worked with. But sometimes it doesn't. But I think the more that you can suss out who you work for because then the better they are at these skills and prioritizing, one, they're just going to be a better teacher and a better role model to learn from. So I think that's an important thing to think about in any kind of job change.

**Lenny** (00:29:30):
To close the loop on this piece for more senior PMs, the skills to focus on, you said, thinking big, building trust and driving impact. I'll put you on the spot. I'll give you two options, two directions to go with this. One is if you want to get better at each of these three things, do you have any one thing someone could do or what does great look like for thinking big or building trust or driving impact? Those are two options.

**Ian McAllister** (00:29:58):
That was six questions there Lenny. Let me see here what I'm answering. Well, I think the think big one is interesting and one way to think about thinking big, especially as you grow in your career is most people operate within a box. There's a box of there's product management and these are the things that product managers do. And you basically build a roadmap and you prioritize features and you work with eng. And so that might be the typical kind of product scope and tech. Most of my roles were ones where I was kind of a GM but a really product focused GM and so I naturally found myself taking a much wider view of what product is across disciplines. And I was lucky enough that I had engineering teams and marketers and analysts and other folks and so that helped me. But I think as a PM you can still do that, even if those functions don't report to you, is take that really wide view of what success for your product is and not have the blinders on its product or tech.

**Ian McAllister** (00:30:58):
It's anything. It's anything that influences the success and your customers' success or anything else. And it just means, you don't own marketing or you don't own this other function, but you own it until you find somebody else to own it. And so that's not necessarily thinking big in terms of scale or whatever, but in terms of how you think about your role as a PM and what your ownership responsibility is. And so I think just the more that you ... You don't want to get over your skis as a PM and then you're trying to change your CFO's mind about something necessarily. But the more you grow, that you have to increasingly do that and find the constraints or barriers to your success or your product success and knock them down no matter what they are.

**Lenny** (00:31:43):
Yeah. It makes me think about just the advice of think like an owner, think beyond just your one little bubble, think about the broader business outside of the one little product you might be working on. So that's great advice.

**Lenny** (00:31:55):
**Ian McAllister** (00:33:15):
I might just talk about earn trust because this is one that I didn't put in there initially and I honestly don't think that I recognized the importance of it early on in my career or even in the middle of my career and it's been in the last couple years that I really understood the importance of it. My wife Sarah is a product manager in AWS and so as I've mentored her a little bit in her career and I've seen how this is really a superpower for her, it really made me reflect like, what are the things I could have done better in different roles to earn trust more? And it's not just the basic things like to be honest and tell two different people the same thing versus different things. I think it's trying to really understand, work backwards from that person and what are their goals and what are their organization's goals and honestly spend the time and the energy to try to get to alignment in the same place.

**Ian McAllister** (00:34:09):
And be willing, not just bullheaded, which I might have been earlier in my career, maybe still to many people, but charging forth what do I think's right but taking some more time to try to forge an alliance with someone because if you do that you're ultimately going to be more successful. So that was just one that I was probably slow to recognize the importance of and I'm trying to catch up now.

**Lenny** (00:34:30):
Is there a story that comes to mind where you look back and I should have earned trust there or I broke some trust here that you'd be willing to share?

**Ian McAllister** (00:34:39):
When I was working with you and the team at Airbnb, I think this is one where Joebot brought me on to help build out the customer support technology platform maybe more how Amazon would do it. To maintain a high level of quality but to become more efficient as well and to reduce the cost so that Airbnb wouldn't have to scale customer support this to the same degree the business was scaling. And so trying to build a new team and develop and I was pretty heads down doing it the way I thought it should be done and working with the team there in terms of let's get a strong analytics framework. Let's measure all these things and really understand what's going on at the data level and then let's use the same prioritization muscles that had made me successful at Amazon to prioritize things that were best worked backwards.

**Ian McAllister** (00:35:26):
And I think that what I didn't do as much as I should have is obviously really partnering with the customer support leadership team as well. That was something where I think in some ways it felt like we were in alignment and getting on stage together and stuff, but it turned out I maybe hadn't spent as much time and effort on that as I thought to build that true support there such that that leader would rally the organization around it as well and we'd be marching in the same beat. And so that was something that I would reflect. Now, I think the team did amazing things and Shirley really carrying the torch there in the entire team and so accomplished a lot. But that was a learning about ... Going back, I probably would've spent more time and really tried to do even more on that.

**Lenny** (00:36:12):
Thanks for sharing that. I never knew that story. And it sounds like the takeaway there is maybe don't take for granted the leadership team, the team that'll actually be using the product. Is that a roughly way to think about it?

**Ian McAllister** (00:36:23):
Well I would say that if you have a certain approach you may be believe it's the right one and it may be the right one, but if you don't build the support and the relationships that they're going to help carry that out and execute on that strategy, it may not get executed as well as you think it should be. And so that's an important part of success. It's a risk that you have to mitigate. And trying to earn trust and to do it that way is a way to mitigate that risk that the right product and the right direction and the right strategy, it may not land if you don't have that support that you need. And so that I think was my learning.

**Lenny** (00:37:00):
What better way to learn a lesson than get some wrong and then you never forget it again.

**Ian McAllister** (00:37:06):
You could call it getting wrong. Just think of something I could have done better. And just that same continuous improvement mindset. It's to everything, every role, every experience, every project, every communication. And if you build that muscle to try to do it better the next time and also just the try to be a little self aware about what could have gone better, then I think it's a really good muscle to build.

**Lenny** (00:37:27):
This is a good segue to the second area of where our chat is going to go, which is Amazon and things you've learned about just the working backwards process. How many years did you say you worked at Amazon total?

**Ian McAllister** (00:37:38):
12 years.

**Lenny** (00:37:39):
12 years. It feels like everyone that worked at Amazon is 10 years or more. It's these large numbers. So they must be doing something right and I don't know. What do you think that is actually? Why do people stay there so long? It's amazing.

**Ian McAllister** (00:37:52):
What's interesting about Amazon, and it's changed over time, is that I think pretty quickly whether you're a fit for it or not. And it can be kind of a crucible and a little spartan. And it just clicked with me though because I'm kind of a structured thinker and right brain. And so this idea that hey, I could have this business and then figure out one metric or fitness function that determines success and then my job is to make that number go up and to the right. That kind of fit with me. And then I rewired my brain probably over the first 10 years around this concept and I just felt like I was learning, I was not only working with smart people that were driven, which was true at Microsoft as well, but there was kind of this DNA in the organization and this wiring that I thought was really effective and it just kind of clicked with me.

**Ian McAllister** (00:38:44):
And so I molded myself to the environment and at every step of the way I felt like I was learning and growing and one of the benefits for me is you get a chance to learn from so many other people in these different settings. You get the chance to read documents that make you learn more so than probably a slide deck. You get a chance to be in weekly business reviews with really smart people and learn from that. Not just learn from your own experience but from everyone else in that room. So I was just a sponge and so much learning happening that I think propelled my career. And so that was why, especially the first 10 years, that it was so fantastic of just growing and feeling yourself build these new muscles and develop these new tools and I loved it. So that was why I stayed so long and obviously Airbnb then, it was the time to try something new, which was a great experience and kind of a test. I was in Seattle and the company was in San Francisco and spending three days on a road each week was a good learning and ultimately a reason to come back and be Seattle based. But then I chose Amazon again because it was still a great place and I thought I could continue to learn.

**Lenny** (00:39:52):
Awesome. I was going to mention they drew you back in. So yeah, that's pretty rare. What did you learn from folks like Jeff Bezos and Jeff Wilke about building product leadership, company building? What's stuck with you working with folks like?

**Ian McAllister** (00:40:04):
I would say two very different people but complimented themselves so well. I didn't have hundreds of meetings with Jeff Bezos while I was there, but I did have a chance, especially in the development of Amazon Smile and then early when I started the social team to have some of those meetings where I wrote the doc and it was Jeff and 10 other people reviewing. The process of doing, even before hitting on Amazon Smile, it was really kind of a innovation process I guess you could call it, where we had a goal in mind to increase customers' loyalty to Amazon, their direct traffic loyalty, not in the way Prime did, which is a paid program, but to try to come up with another program or way in which customers might start their shopping on Amazon instead of elsewhere. And so I was running the gifting business. I moved over to the traffic org to try to come up with a new program with no team or anything.

**Ian McAllister** (00:40:58):
And then I would meet with Jeff Bezos and Wilke and others every couple months and I would profile a couple different options and use the working backwards process and we'd review some facts. And so there was a bunch of learnings throughout that process. One, I found Jeff to be super encouraging. And each time we'd leave one of those meetings, we maybe didn't find the thing in that meeting. We'd talk about it and brainstorm a little bit, but he would always leave and be encouraging and with a quote. One time he was like, "Remember, this process doesn't have to be efficient because the prerequisite for efficiency is knowing where you're going." And then he'd leave the room and whatever. So I found the rhetoric around Jeff or blowing up or whatever, I didn't find any of that and I found him to be super encouraging and he found all these times to help train me in the working backwards process.

**Ian McAllister** (00:41:52):
There was a time when I came with a press release for a concept and it didn't have a problem paragraph. I'd skipped that. And he reviewed it and so forth and he was like, "You know what, maybe if you don't have a problem paragraph, there's not really a problem." And so it was kind of a little lesson to me like, "Yeah, maybe that is why I did it. I wasn't really working backwards, I kind of had the solution in mind and so I'd skipped over that part." So that was one just very specific learning about the process from Jeff. So Jeff Wilke, I probably learned more from Wilke just because I had more exposure over my time there. At one point he was my skip level. And I have such tremendous respect for Wilke or Jaw as he was called internally because he was sort of the consummate operator.

**Ian McAllister** (00:42:34):
This muscle that I think you learn working at Amazon about being an operator, whether you're ... You're not in operations, but any part of the business that I think came from him. And I think it was due to him that Amazon developed that muscle. And I think it's one way that separates some Amazon PMs from people who haven't worked there in that environment and that continuous improvement mindset. That's so important. And one of the forums that was a great learning was the WBR or Weekly Business Review. Or later called Consumer Business Review. So this was a forum where Jeff would lead the meeting. It would be a series of metrics for different parts of the business. Everywhere from fulfillment to customer support, to traffic to category teams to programs. And I would present on Amazon Smile there. And the way he would run that meeting and enable you to get through a metrics meeting for the entire North American retail business in one hour.

**Ian McAllister** (00:43:27):
And the way he ran that meeting would lead all those leaders to build these muscles because you wanted to be prepared to speak to the variances or trends in your business in a key metric and know your business and know what you were doing based on that thing. And so just this hour a week of probing and asking questions and everyone ... There might be a hundred people in that room prepared to answer questions about your business. And it had this cascading effect that not only was I or the leaders there on the spot having to answer a question and being prepared, but then I would do the same thing with my team, et cetera. And so I was trying to build those muscles in my team such that they could bring their insights and understanding and actions on things in this cascading effect. So that was a mechanism, which is another really big thing at Amazon that led to all these amazing behaviors.

**Ian McAllister** (00:44:17):
And I think a lot of those mechanisms came from Jeff Wilke or he created an environment where they would be developed throughout the organization and then propagated. And so that was one thing, just that operational mindset and rigor that being a product leader is not just about building new things, it's about how well you run what you've already built. And if you're really paying attention to the product that you operate, it will give you ideas for things you could do to double down on something that's happening well or to prevent something bad happening. And I think that's been a very key reason for Amazon's scale. Another thing I really respect about Jeff Wilke, and I think Doug Harrington has some of this as well, is the notion of a little bit of tough love. And I think that's important and that neither were assholes, but sometimes, and especially Wilke, you need to get that look kind of like your dad might look over his glasses at you and be like, "Hey."

**Ian McAllister** (00:45:15):
And so I think that was kind of the vibe that you would get. It was professional, it was respectful, but sometimes everyone needs a little kick in the ass and I think that was something, but it almost builds more respect from him and just incredible leaderly behavior, which I really respect and I try to model and I try to do the same because I respected it so much. And then I guess the last attribute of Wilke, which I really saw was teaching. And it wasn't just saying this is the right thing or this is what my decision is in a meeting, but teaching the why and the pattern, the mental model that informs him to think this is the right thing. And so I think he was just great at teaching, taking a moment. It might just take 10 seconds in a meeting to teach.

**Ian McAllister** (00:46:01):
And that's something that I've forgotten at different parts of my career, especially as you get more experienced and you know the right decision to do and you know what you want, whatever, that may be the right thing, but I think you'll have a lot more lasting effect if you could abstract it to a degree and teach the lesson. Because then that person will hopefully learn the lesson and can apply it to a bunch of future situations and also understand the why more. And it helps them sometimes disagree and commit more so than just being given prescriptive advice.

**Lenny** (00:46:33):
Sounds like it must have been an incredible experience learning from these two. Thanks for sharing all that. I want to get to the working backwards stuff. I feel like we've talked about this a lot. We've talked about this on other podcasts with other guests. I feel like people understand the general idea. Yeah, Amazon works backwards. They write a PR. Maybe there's a six pager thing they do. But I feel like there's not a lot of, here's how actually do this thing. And so just to spend a little time on this, when you see teams trying to work backwards and be like, "Let's work backwards. We're going to be like Amazon.", what do you find they do wrong when they're actually trying to implement this idea of working backwards? What's the most common mistake do you find?

**Ian McAllister** (00:47:11):
Well, working backwards is all about the problem and starting there and obsessing about the problem and being guided by it to then go into the solution. So when teams that do it wrong is they don't do that. They don't work backwards. They have something they want to build. These things look similar. These two technologies or whatever. We could combine them and then do this. And if you say we could and it's not grounded in a customer or customer's problem, you're not working backwards. And then you may use "the working backwards process", but you already have the solution. And so you're adding the problem after the solution. You're retrofitting the problem, retrofitting the customer. And so that I think is the number one thing is that they don't get the importance of truly starting with the problem that you're trying to solve and being faithful to that working backwards from the problem.

**Ian McAllister** (00:48:03):
When I first started at Amazon and community, we had this business of automated merchandising using community content, and that was the core thing we were doing is to grow that. But there was this Jeff idea that a team was super excited about. Because I think in some meeting he'd kind of sketched it out or whatever. And so that there was already all this momentum to build this thing that was actually a Jeff project, but I should have known at the time, in hindsight I do, because the name they had for this project was ASIN to ASIN linking. And ASIN was the identifier for a product on Amazon. And so it was kind of this not working backwards idea ultimately of if you could link to products by a subjected attributes and then you could build a feature around it that allowed customers to vote on these things and then it would be kind of ...

**Ian McAllister** (00:48:50):
So in spirit, it really wasn't working backwards. But the team was all excited and so we eventually wrote the press release and we did it. And it turned out, it wasn't successful. We ended up shutting it down later. And so I learned a lot, this was the first year or two at Amazon, about using the working backwards process but not really working backwards. And so that's literally, if I'm reviewing a working backwards press release or fact, or even talking with someone about a new initiative, my brain is wired now to not be able to process any information until I focus on the problem and the customer. And then once we start talking about that, then I can engage and literally work backwards to say, okay, how do we solve that problem? And what's the most elegant way to solve it? Or if there's three problems, what's number one or two or three? So it's probably a gap in me that I can't process information without working backwards from the problem, but I find it to be helpful when people do that.

**Lenny** (00:49:47):
So when people talk about working backwards, the way you're describing it is interesting where it's focused on start with the problem, which I think generally product teams try to do. Their one pagers their PRDs often have, here's the problem we're solving, here's why it's a problem, here's how we think about ... Is that the core of working backwards? I always imagined it was the launch release and the PR thing and maybe the FAQ. Working backwards at Uber and other and Airbnb, do you actually do that for every project yourself at this point?

**Ian McAllister** (00:50:17):
There's two parts of it. One, there's the concept of working backwards from what you're trying to accomplish. And I still absolutely do that with my teams as well. What are we trying to accomplish for the business or accomplish for a customer and let's start there. And if they have a problem that is interfering with their ability to be profitable for their ability, if it's a business customer or it's a customer trying to accomplish a goal, starting with that problem. That's different from the working backwards mechanism, which is the press release and the FAQ, which was the mechanism that Amazon used to enforce working backwards, which I think is effective. And I've tried to teach that and write some posts about with templates and things like that because it's a great way to start of the press release has a paragraph about the problem. That's what you write.

**Ian McAllister** (00:51:00):
And then you write the solution paragraph and then the customer quote. And then the fact which is is there a legitimate plan to succeed? So if you don't have that muscle to work backwards already and your team, it's a great thing to try, but that's not the only mechanism that can do it. And eventually if you do it enough and you build that muscle to work backwards, you can do it in any number of formats, whether it's something in a PRD or some other way. But the key is that you don't think what we could build, you think about the problem and then the solution that solves that problem.

**Lenny** (00:51:35):
Got it. Okay. So the press release is not core to it. It's like a trick to get you to think about the problem you're solving. It's not how you plant announce it.

**Ian McAllister** (00:51:42):
Yeah.

**Lenny** (00:51:43):
Interesting. I never thought about it that way. So when you're doing this process at other places outside Amazon, say you're a product leader that's trying to ... I want to improve the way we think about product. What is it that you suggest they do specifically? Is it write out, here's the problem we're solving? Is there more to it? What would you suggest there?

**Ian McAllister** (00:52:02):
If it's a blank slate, truly, you could certainly use the working backwards process like Amazon does with the internal press release and then the fact and so forth. So that's fine. But a lot of companies have a different way they go about it. Some companies are very much, it's slide culture and presentations and so forth. And so as a product leader you could think about what you do with your team and what you do upwards or across. And so you may have the latitude to use any process with your team. And I've done that at some companies where using documents and if they're supportive of the team and they recognize the value of that, like, oh actually this is good and this is a great way to write things down on paper and to have better information content and richer discussion that oftentimes I think people will find that versus a slide with a couple bullets is not great. Then you can build that muscle.

**Ian McAllister** (00:52:54):
And I've found it's a great way to teach and use those to dive deeper into product. But depending on the organization you're at, that may not wash to train your senior leadership to use the process you want to use. And so then it might be a matter of finding the opportunities to try something and saying, "Are you open to doing something this way?" A review of a doc instead of a review of a whatever. So that's a little separate than just working backwards, but I think you just have to acknowledge the environment you're in. And also, unless the organization has a specific format to do this. If it does, you probably just need to use it. Different leaders process information, different ways. You may find one format's effective with your leader, but another one to educate a broader organization. But it's very company specific. So despite what I might want to do, I've just got to recognize that I have more leverage down with my team versus up or across.

**Lenny** (00:53:51):
Is there a template that you use consistently? Is that something that you've published of how to frame the problem, how to frame all these other elements?

**Ian McAllister** (00:54:00):
I have shared posts on, I know for sure LinkedIn and I probably should put it on the newsletter, on my newsletter, that's a working backwards template and some posts about how to do the process or tips on how Amazon does the process. And so I'll make sure to put those up on my newsletter as well. And the template's free. Obviously anyone could just copy it and grab it.

**Lenny** (00:54:19):
Awesome. We'll link to that in show notes. Definitely send that to me after we wrap this thing. And I was going to ask, does Amazon work backwards on every product they work on/do you suggest working backwards in every feature and product?

**Ian McAllister** (00:54:33):
I think there's some scale below which it doesn't probably make sense to do this process because there's a little bit of overhead to it. But I think if it's a new product, absolutely. And I'm sure there's some at Amazon that don't use the process, but in general that was the way and often enforced that you need a working backwards review. Ideally that would happen at the outset, but sometimes it would be added later. And yeah, I think it's a great thing whether you use the mechanism. Again, it's a great template to start with and use if you have the flexibility to, but I think it's also possible just to have the spirit and to try to be true to the spirit of working backwards from what you're trying to do for customers and what problem. That's the most important thing. The template is just a mechanism to help ensure that happens.

**Lenny** (00:55:18):
Got it. You mentioned a review. What is that? Working backwards review?

**Ian McAllister** (00:55:22):
Well that would just be a meeting with leadership or other folks to review the concept, review the press release, review the FAQ and ask questions. And in some cases that would be the gate to approving it. That was the case with me and Bezos before we went off and built the team and launched Amazon Smile is I would do these reviews about different concepts and that was the one that we green lit. I mean that's often the case. It's also just a great way to educate other people about what you're trying to accomplish. Ground them in the customer problem and solution. And the FAQ is a whole nother concept. It's about the legitimate plan to succeed. One other thing that I use, I got a chance to have lunch with Jeff Bezos. It was probably back in 2008 or something like this. And I asked him, "What's your criteria for investing in something new?"

**Ian McAllister** (00:56:09):
And he said, "Well it's three things. One, is it a big idea? And then second, is it something we should be doing?" So if maybe you have an idea, if you have this new way to extract oil from shale, is it a big idea? Yeah, probably could be a big idea. Is it something Amazon should be doing? Probably not. And the third test, is there a legitimate plan to succeed? And you got to have all three of those things. And I think the FAQ part of the working backwards process is that early stage legitimate test of whether this thing has a plan. Because you could have this internal press release or big idea or big idea for a solution, but the FAQ basically says, okay, I've thought through the internal components or the finances or the key technical hurdles or whatever. And so that's one that's not written about as much, how to do the FAQ, but I think it's another way to build trust that you've been thoughtful enough given the stage of the product to deserve the resources or deserve to move forward with it.

**Lenny** (00:57:03):
That's awesome. I feel like most PMs listening to this are going to be like, "I always start with a problem. I'm always problem focused so I'm working backwards. So I'm good." Other signs of just like, no, you're not. You think you are but you're probably not doing this well. Is there a symptom of you're not actually doing this correctly?

**Ian McAllister** (00:57:23):
The most common thing that I see that tips me off is when they talk about something, there's different pieces in the pantry and we have these ingredients, we could put them together, we could add these two things together and make a meal out of it. And so it might be a technology, it might be a service, it might be two different things or the building blocks are there and what's enabled if you add these two building blocks together is something. But that's not really working backwards. It may be true that there's some leverage or some benefit from the company having these technologies or assets, but that to me is often the first step that these two things look similar. We combine them and it's all goodness in this new thing.

**Ian McAllister** (00:58:09):
So if you start talking about those things or the technology, I think that's a likely case that you're not really working backwards as opposed to the opposite is if there's a customer problem that feels compelling even before the solution, yeah, that does feel compelling. And just like with every startup out there, probably a lot of the pitches are there's a big audience and a painful problem and it's the painkiller versus the vitamin thing. And then we have a novel way to solve that. That's kind of working backwards. But more often, especially in a big company, you'll have all these ideas because you have more ingredients in the pantry of ways you could combine them and try to feed it to someone but may not be working backwards.

**Lenny** (00:58:56):
Awesome. We're reaching about an hour chatting and so I want to let you go. Before we get to our very exciting lightning round, is there anything else you want to share on anything we've chatted about?

**Ian McAllister** (00:59:06):
Let's see. No. I mean I think we covered a bunch of good ground. It's been fun, but nothing particular.

**Lenny** (00:59:11):
Okay, great. Well then we've reached our very exciting lightning round. We've got six questions here. They'll be pretty quick and easy. Whatever comes to mind, share and we'll go through them relatively quickly. Sound good?

**Ian McAllister** (00:59:22):
All right. Let's do it.

**Lenny** (00:59:23):
Let's do it. What are two or three books that you've most recommended to other people?

**Ian McAllister** (00:59:28):
I say Getting Real by 37 Signals and it's specifically the chapter on epicenter design. I've shared that many, many times. You can link to it. That's definitely the most thing I've shared. For fun, The Wool Trilogy by Hugh Howey, he's probably my favorite author and a great series. And then for learning, just a recent one that I thought would be super fascinating was Energy and Civilization by Vaclav Smil. So it might not be on the best seller list, but I thought it was interesting.

**Lenny** (00:59:55):
What's another favorite podcast of yours other than this one possibly?

**Ian McAllister** (00:59:59):
I think How I Built This is really interesting just to decompose how interesting businesses and products came about. And then just because of my work, EV News Daily is a daily digest of what's going on in the electric vehicle space. So that's a very good use of my time, five minutes a day to get up to speed.

**Lenny** (01:00:18):
Very niche. I love it. What's a favorite movie or a TV show you've recently seen?

**Ian McAllister** (01:00:24):
Yellowstone. That's definitely my favorite. Can't wait for the next season. Montana's my happy place, although I'm probably the kind of person that they rail about in the show, so it's kind of ironic. And I think the movie was Everything Everywhere All At Once. I love movies that are not predictable and I thought that was just very creative.

**Lenny** (01:00:40):
I'm shocked by how many people on Yellowstone die. That show is just murder left and right. I was not expecting that on a ranch oriented show.

**Ian McAllister** (01:00:50):
It's a harsh environment.

**Lenny** (01:00:51):
Quite harsh, turns out. Especially if you mess with the Duttons. Next question. Favorite interview question that you like to ask.

**Ian McAllister** (01:00:58):
When I'm coming out of left field, I ask people at this stage in your career, what have you learned about yourself? How are you different from other people? No one's prepared for that.

**Lenny** (01:01:06):
What do you look for in their answers?

**Ian McAllister** (01:01:08):
I don't know. There's not one specific thing and there's no right answer, which maybe makes it unfair, but just maybe a little self-reflection and maybe they will have understanding their strengths and that might be a good bit of self-awareness about what makes them different, where they can harness that and that makes them a better PM or engineer or something. And so that's kind of what I'm looking for, but there's no set answer. It's more just to throw them off balance.

**Lenny** (01:01:32):
Interesting. Favorite app right now.

**Ian McAllister** (01:01:35):
It's probably not too interesting, but to be honest, YouTube. It's like the eighth wander of the world and just every day I'm amazed if I want to learn about something new. A couple summers ago I had some time off and so I basically taught myself how to do woodworking and built a kitchen and other stuff. And so it's just like it continues to be this resource and this jewel that helps me grow and learn about anything.

**Lenny** (01:01:58):
I imagine some people are watching this on YouTube right now.

**Ian McAllister** (01:02:01):
All right.

**Lenny** (01:02:02):
I just read a story about an Olympic javelin thrower who learned how to do this watching YouTube. He was somewhere in, I think maybe Africa. He had no coaches around and he just watched this one other javelin guy that just shared lessons on how to do this and became incredibly good. It's insane.

**Ian McAllister** (01:02:18):
And I mean, I'm old, so I didn't have this when I was growing up. I remember going to the library and sending away for a brochure in the back of a magazine and things. Learning was not so easy back then. The internet obviously was a huge resource and is, but then YouTube as well to see somebody do it. It's also interesting to see somebody live. So anyway, I'm a fan.

**Lenny** (01:02:40):
Final question. Who else in the industry do you most respect as a thought leader, someone you look up to?

**Ian McAllister** (01:02:46):
I say Gibson Biddle. I think that he is one, just tremendous amount of product experience that I think is valuable. I respect the fact that he takes the time to share it. He doesn't have to, but he does. And he's also a great communicator and he invests in being ... You can tell he measures [inaudible 01:03:02] of his talks and things like this. He's invested over his career to be a great communicator. So I think he's a good role model for me and I think for others out there.

**Lenny** (01:03:11):
That guy's a force. I'm happy that we've had him on this podcast. I'm hoping that everyone eventually, that people mention in this question we end up having on this podcast. So that's great to check. I also love Gibson. He's got a great newsletter. Askgibbs.substack.com I think. Ian, thank you so much for being here. This was amazing. I really appreciate you sharing all this wisdom with us. 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?

**Ian McAllister** (01:03:38):
Yeah, I guess Twitter's a great place. So IanMcAll, I-A-N-M-C-A-L-L, is my handle. And then I've started a newsletter. I'm not that frequent to be honest. I have a lot of good intentions and a bunch of ideas. Ianmcallister.substack.com. And that's something to connect and feel free to subscribe and hit me up on Twitter if you have ideas for posts or questions. And if I can answer in a tweet, I will. If not, I might put it on the queue of things to write about. And yeah, thanks for having me on Lenny. We were talking earlier about writing or doing other things and the value of that is just making connections with people. And so that was what I was one, just to reconnect with you is awesome. And to whatever extent I get a chance to make new connections in the world, that's a good thing.

**Lenny** (01:04:25):
Amazing. And we originally connected over that piece that you wrote, so it all circles back 10 years later maybe. Thanks, Ian.

**Ian McAllister** (01:04:32):
All right. Thanks Lenny.

**Lenny** (01:04:34):
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] How to be the best coach to product people | Petra Wille (Strong Product People)

**Petra Wille** (00:00:00):
Getting promoted is way harder if you're not good in telling stories and rallying the team behind the shared goal and all these kind of things, and you usually achieve this through good storytelling techniques. And in some teams, I've seen the product person not being really, really good at it, but then the whole team helped creating these stories and stuff like this. So you definitely could compensate to some extent, but I would consider it a bit of a career staller if you don't get to a decent level of storytelling and to a decent level of public speaking.

**Lenny** (00:00:35):
Welcome to Lenny's Podcast. I'm Lenny, and my aim here is to help you get better at the craft of building and growing products. Today, my guest is Petra Wille. Petra is an independent product leadership coach and author of Strong Product People. And for the past 10 years, she's been helping product teams boost their skill sets and up their game. Alongside her freelance work, Petra organizes events in Hamburg, Germany, where she's based, and does a ton of one-on-one coaching, and speaking, and writing.

**Lenny** (00:01:03):
**Ashley** (00:01:40):
At least 40%.

**Lenny** (00:01:42):
And how many of them screw that up, and what happens when they do?

**Ashley** (00:01:44):
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** (00:02:04):
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** (00:02:19):
Totally. It's incredible to see how our customers like Square, Spotify, and Zuora are able to grow their businesses on top of Flatfile. That's because flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:02:36):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny.

**Lenny** (00:02:43):
**Petra Wille** (00:03:39):
Hi, Lenny. Such an honor to be here on a Friday night.

**Lenny** (00:03:43):
Friday night your time, Friday morning my time. Thank you for making the time.

**Petra Wille** (00:03:47):
Of course.

**Lenny** (00:03:48):
You're a product leadership coach. Can you just talk about what you do as a product leadership coach and then also just a bit about the numbers of PMs you work with, the number of companies you work with, the impact you had, just to set a little bit of context in your background?

**Petra Wille** (00:04:01):
How I usually describe it is that I work with people leading product people, so that's the product leadership level that I'm looking at. So that might be a CPO in a smaller startup or a product director, a product team lead, these are the folks that I'm usually working with for the last four years, I'd say. And before that, I coached product managers, so IC level product folks. And before that, I did a lot of product discovery coaching for teams and whole product organizations. And you asked about how many people I may have influenced. That's a real hard question so to say. So in one-on-one coachings, that's what I know. I coached around 130 people so far over the last few years, which is already a lot. Most of them have, yeah, 10 to 20 sessions with me. Some really stick with me over the years so they have more sessions.

**Petra Wille** (00:04:55):
So that's that. And then I have group coaching sessions and corporate and then public setups. And that's, I would say, another 150. And it's all product leads. So usually, those people are working with a team of 10 product people and there are some ripple effects. So I think I have an impact on their lives as well if I'm coaching their boss or the line manager so to say. Plus, the teams that I work with as a discovery coach, plus the people that read my book and hopefully are using some of the techniques. And in the end, yeah, I did a bit of the math and I think it might be around 50,000, 60,000 people. If we look at it from the product leadership to IC level structure, yeah, that might be the impact. So that's a pretty impressive number.

**Lenny** (00:05:35):
Wow. That is an impressive number. And I always love chatting with folks that do the work you do because there's such a unique insight into working one on one with PMs that are trying to get better and understanding what trends are happening across PMs at different companies and different countries and things like that. So I'm excited to dig into a bunch of stuff.

**Lenny** (00:05:53):
The other thing that I love about where you're focused, there's a lot of people that focus on ICEPMs and there's a lot of people that focus on senior leaders, VPs, CPOs. And I love that it feels ... And correct me if I'm wrong, but you are focused on this middle layer of first line managers, directors.

**Petra Wille** (00:06:08):
Exactly, yes.

**Lenny** (00:06:08):
Which I feel like is often the most important and influential layer of a company because they're the ones doing a lot of the work at making a lot of the decisions day to day.

**Petra Wille** (00:06:16):
That is the case. Plus, at least with a lot of clients that I'm working with, they are not trained product people. So they often come from a marketing background, or a business background, or from the data background, so to say, or the engineering background, but they often never have worked in a product management role. So they're missing a lot of basic product management practice and a lot of empathy for the struggle of the product people to some extent. Plus, how should you help people grow if you have no clue what their role actually is all about? So that's what I actually like to help them with, to get this clarity on a strong compass how the best product organizations and product managers should be working.

**Lenny** (00:07:02):
Just to go a little bit on that tangent because that's an interesting point you just raised. When you work with folks that are not product people and that end up leading product people and trying to better product, what's the thing they lack most, the skill or the understanding of product? If you had to think of one or two things that these people are like, "Okay, they totally missed this part about product management, about building product."

**Petra Wille** (00:07:23):
One thing that has made me sense out the most is I see product people on the IC level have to go through some of the struggles on their own, even if our product community has some best practices to it. Because as the line manager has no clue about the product community out there and the craftless product management, they often struggle to point them in the right direction to say, "Hey, I think that's a problem somebody else already had. So maybe you could watch a talk or read this blog post or there's a book about this particular thing and then go try it." So that's the first thing. So product people IC level often have done to learn a lot of things on their own, so to say, because nobody's curating their progression for them to some extent. So that is one thing.

**Petra Wille** (00:08:13):
And then I use this metaphor of the eight-legged creature because people tend to talk about T-shaped employee profiles, but T-shaped is so not enough for a product person, right? We want them to understand underlying problems of the business and the users finding solution for those, getting things out of the door with the team, doing a lot of product discovery, looking at the data, how people are using it, iterating on the products. So there's so many things that we want them to be good at and to understand that and the complexity that the role actually brings with it. That's sometimes hard for people that have never worked as a product person to really understand. So, yeah, if I would need to pick two things, then that's maybe the two biggest differences.

**Lenny** (00:08:56):
The first one is such a great one. It comes up a lot on these chats of just how much of getting better product is just doing it. You can read all the books, you can take all the courses, you can read my newsletter, you can read your book, which we'll talk about, but there's only so far you'll get without actually just doing it and just failing, doing great things that succeed. And it takes years, right? It's not like something you'll do six months, "All right, I'm feeling really good about being a product manager."

**Petra Wille** (00:09:20):
Yeah, I totally agree. I so often have said the sentence of, it's not a role, it's a career being in product and, really, there's so many things to learn and so many things to get good at. Yeah, I totally agree.

**Lenny** (00:09:32):
Yeah, crazy ass role. Speaking of your book, you wrote a book, it's about product leadership and coaching, and we're going to touch on some of the things you wrote in the book, but can you just briefly describe the book that you wrote, who it's for, what it's about?

**Petra Wille** (00:09:42):
It's quite a niche book, right? So it's focusing on people managing product people, so product leads and then the people development part of their job. So it's not another book talking about how to come up with a great product strategy. There definitely is a chapter on that to some extent, but it's more how you coach those things. So it's not so much about how you do these things on your own, it's more how you could help product people to understand hypothesis-driven product discovery a bit more, or how could you help them think about team motivation, or how could you help them get better and giving feedback, all these kind of things.

**Petra Wille** (00:10:20):
So this book has this meta level of helping product leads to develop their product folks. And that is actually what the book talks about in five different parts. And I think 28 chapters if I get it right.

**Lenny** (00:10:35):
Wow, it's a lot of chapters. What is it called? Where can people find it? Just while we're on this topic and then we'll get into some of this.

**Petra Wille** (00:10:41):
It should be available on Amazon and it's Strong Product People: A Complete Guide to Developing Great Product Managers. That's actually the title and the subtitle, so to say.

**Lenny** (00:10:52):
Awesome. Strong Product People. Okay. I read parts of the book, I looked at a lot of the stuff that you write online and some of your videos, and there's three things that I want to spend our time together on to dig into. One is what you just talked about, how to become a better coach to product managers for PMs. Two is storytelling skills. You have a lot of great stuff on just becoming a better storyteller. And then three is how to find great community to become a better PM. Does that sound good?

**Petra Wille** (00:11:18):
Yeah, that sounds amazing. That stood up.

**Lenny** (00:11:21):
Okay, great. Awesome. So the first topic, basically, the premise of your book is just how to become a better coach to product managers. And for me, actually personally, the biggest inflection in my career was having an awesome manager who helped me become a better PM, and that was the point in my career where I really accelerated. And so I fully buy into the power of having a great manager and a coach, and oftentimes those aren't the same people. And you have these five ingredients that you have to be the best coach to product managers.

**Lenny** (00:11:52):
And so just to start, what are these five ingredients? What do you have to get right to be a great coach to PMs?

**Petra Wille** (00:11:57):
Yeah, I'm glad you're asking. So I was already referencing to number one. And number one is really having a solid definition of what a good product person looks like in your context. So what is your definition of good, so to say? And a lot of the product leads that I'm working with have this as an implicit feeling based, experience-based thing. They can talk about some of the aspects, but it's often the case that they not have fully reflected on what a personality traits that I want to see in product people that are hard to develop while I'm coaching them, and what are skills, and know-how, and capabilities that I want to see in the product people that I'm working with. And some are super good and have it all written down, but most of the product folks that I'm working with haven't. So that is step number one is doing this reflection.

**Petra Wille** (00:12:54):
Then step number two is having a clear idea where every PM currently is in their current career, in their situation, life in general, all these kind of things. So put the pin on the map, so to say, and then think about what is your vision for them in the future, so how good could it get? And I usually encourage product leads to think bigger than their current role at the current company because that's the longer term thing. And then even more important is what I call the next bigger challenge.

**Petra Wille** (00:13:27):
So what is the next bigger challenge I would love to assign this product person to if I could because I know that would help them to learn a new skill or to, yeah, again, you know how, whatever it is, right? And creating such a list once a quarter, for example, you block yourself an hour in your calendar, you write down the names of your direct reports, and then you just think about, "Okay, what would be this next bigger challenge for them?"

**Petra Wille** (00:13:53):
It's not always the case that this comes around the corner the next day. Sometimes it takes a quarter or two or three, but if you wrote it down, you will see this opportunity and then you could assign this person to the opportunity and really help them grow substantially over time. So that's number two. Then, hopefully, you share this vision you're having for them with them and do a bit of an alignment session because it's not always that they have the same things in mind. Maybe your vision for them opens up their thinking and reflection a little bit more, but you have to have this conversation where you actually see them, and that's a lot of encouragement and bringing out the best in them and these kind of things. Then it's definitely a development plan, but I think that's more on them than it is on you because you don't get the apps from other people's branches.

**Petra Wille** (00:14:45):
So you cannot really help them develop, but you could remind them of going to the gym, for example, which would be step number five, by the way, that's the follow-up. But the development plan is something where a lot of product managers need help with because that's the inspirational part, that's situational part. That's where you could help them to really see some of the differences between your definition of good and their current profile, and maybe they need to get better in prioritization, maybe user interviewing is something they want to get better at. And then you could help them defining steps that they could take small things that they could learn. Maybe it's a book, maybe it's giving a presentation at a conference, maybe it's reflecting on your way of prioritizing, and then look at what others are doing. So whatever it is, that is something you could help them with.

**Petra Wille** (00:15:30):
And then finally, it's the follow-up. That's sometimes just a nudge every once in a while at the water cooler to say, "Hey, how is it going with your personal development plan?" And some really need the weekly reminder and some maybe need even a daily email, whatever it is, ask them how they want to be reminded of the personal development and how you could help them and the system while doing that because they still have a day job, right? So the development will never be the number one priority, and it shouldn't.

**Lenny** (00:15:58):
Awesome. So just to summarize really quick, I have the list here in front of me. One is have a clear sense of just what it takes to be a competent PM in your role. Two is an idea of where that PM is today and one thing they could do to improve. Three is a shared vision of how they'll take that next step. Four is having a development plan of how they can move towards this vision. And then the last piece is a commitment, just following up with them and making sure they're staying on top of this.

**Petra Wille** (00:16:23):
Exactly.

**Lenny** (00:16:23):
What's interesting about this, just looking at this, it feels a lot like a roadmap and a strategy and a vision for a product. The definition where you're today is the problem, idea of where you're going to go next is like a strategy, and then there's a vision of where you're going to go together and then you check in. So it's these standups. Do you think of it that way at all or is that just something I'm noticing?

**Petra Wille** (00:16:42):
I think about it that way as well, even to an extent because so many companies are lacking the real strategy bit, right, and it's similar with the people development strategy. That is something that I see not being present in so many environments as well. So even that similarity is a given, I'd say. Yeah.

**Lenny** (00:17:00):
Which of these do you find is the most lacking usually or slash where do you think the biggest ... If someone were to just like, "I want to be a better manager," where would you suggest they start? Is it right at the top, figure out what a great PM at this company is?I'mq

**Petra Wille** (00:17:14):
That is a great question. No, I usually advise people to start with the development plan because even if you have never done the assessment and even if you don't have your compass, your definition of what makes a good product manager, you usually have an idea or they have an idea of what they want to learn next or where they want to get better at. So I said they say something like my storytelling capabilities are maybe not as good as they could be or prioritization is people are constantly complaining behind my back that they don't get the order of the things in my backlog or whatever it is, or they think my opportunity solution freeze, and suck, or whatever it is.

**Petra Wille** (00:17:55):
And you could use that and start helping them creating this development plan. That's not a structured assessment, but that's a perfect start. And then it's obviously the follow-up that makes a big difference and that just takes so little time from the product lead, the small notches, that's super easy. And these development plans, I usually tell people to create a new one with a new headline or topic once a quarter or every four months. So that is not a massive time invest as well. So that would be my suggestion for where to start, if that helps.

**Lenny** (00:18:29):
Yeah, I love that advice because I can imagine a lot of people get stuck in that first one of, "I don't know all of the things that I need to know about what a great PM right now is." So that's a nice simple way to start.

**Petra Wille** (00:18:38):
And there is another aspect to it. A lot of product leads try to create their compass. And while they do so, they think about, "Maybe I should have an aligned version with my peers." So the other product leads in the company. And then we're talking about the career levels and all these things and often takes ages until something is coming back from HR or you have a unified version. So that is something where I usually say, "No, start with your own personal team because the folks in your team usually just have you as a line manager. So grade your compass and encourage your peers to grade their compass and, a bit down the line, it might make sense to harmonize some of that, but it's better to start helping your product folks and giving them some orientation than being totally paralyzed by the fact that it's not a compass that is used in the whole company."

**Lenny** (00:19:31):
I want to talk about this compass and how to figure out what a competent PM is. And I know you have a framework around this and I have some stuff I'll actually share, too. But on this latter piece of checking in the development plan, I wrote about this once, but I'll share it here briefly. Something that I did with my PMs that was so effective was every time we did a performance review, every six months, we had a performance review, we put together a Google Doc with all of the things that we agree they should be working on and we pick, say, five themes or three themes, and then we pick very concrete things they should do over the next six months that will help them develop these things.

**Lenny** (00:20:06):
And then more importantly to your last point is we did a monthly coaching session where we looked at the status of each of these things. So there's a color code for each of these 10 things that we all agreed you should be doing these things over the next six months and we checked in how they're going, so that the next performance review, it's not like, "Oh, I forgot all these things."

**Petra Wille** (00:20:24):
Yeah.

**Lenny** (00:20:24):
It's all like, "Oh, yeah [inaudible 00:20:25].

**Petra Wille** (00:20:26):
Yeah. Yeah, exactly. And really, all of us know consistency beats intensity. So, really, the smaller time investments on a weekly basis and that applies for the PM's time investment in learning new things and it applies to the product leads investment and helping their people to grow. I think for both parties, it's more likely and more pleasant if you have small chunks of people development in your calendar. And that's why I like your story, right, because you were focusing on regular check-ins more than into the big bang 360-degree reviews.

**Lenny** (00:21:00):
And it builds on what your point of the development plan is something the person develops like, "Here's what I believe I should be working on." And it's not like you inform it a bit and give them feedback and maybe this isn't or maybe [inaudible 00:21:12] this other thing. But, yeah, the fact that they own it, I think, is really powerful.

**Petra Wille** (00:21:16):
Yeah, yeah.

**Lenny** (00:21:16):
Going back to knowing what is a competent PM at a company. Something I want to ... I'll make sure to include in the show notes for this is I actually did all this research on the career ladders at all of the biggest tech companies. So I have the spreadsheet that it's public of just the skills that every company evaluates your PMs by, but most companies don't have. They're not great. So say your company doesn't have a career ladder competency framework leveling thing, what do you suggest folks do to help figure out what is a competent PM here at our company?

**Petra Wille** (00:21:50):
I'd say use one of the assessments that are already out there. Maybe we can include this as well. I wrote a blog post where I put all the ones that I'm aware of into, so there's the PM Daisy and, obviously, Marty Cagan has an assessment, and I created a framework called the PMwheel and there are a few others in there. Go find one that is close to what you actually think a good PM should look like and then customize it. Don't use it just by copy paste because sometimes you have just rather technical PMs in your organization and then all these assessment points about user interviews and discovery are maybe not that applicable in your situation, right?

**Petra Wille** (00:22:33):
So use one template that is close what you want to achieve, heavy customize it because it is really a great inspiration to see, "Oh, these are all the things that other people think a PM should be doing." Or maybe you could merge one or two of those and tailor it to your needs. So that will be my first suggestion. Plus, reflecting on the personality traits because I think there are some things that you better hire for and that are super hard to develop in a corporate environment. So for me, that, for example, is curiosity. I think product people need to be curious about the world, how it works, about things, no matter the topic.

**Petra Wille** (00:23:14):
The best product people that I know, whatever the topic is, they're interested and tell me more about it. So that is, for example, there's something I would always check when hiring product people because I know it's hard to build that muscle or empathy, definitely something that I want to hire for. I know that I can help them develop this muscle a bit more and stepping into shoes of users, and stakeholders, and colleagues easier. But still, if there is, yeah, not a decent level of empathy built into this person, then it's nearly impossible for me as a product lead to help them get towards a seasoned level. So that's another important thing. Think about personality traits and think about skills and know-how and to think about skills and know-how. Use some of the already established assessments.

**Lenny** (00:24:03):
So we will try to link to as many of those that you mentioned in the show notes. Maybe talk about the PMwheel, which is the framework that you suggest for folks to understand, just like what are all the skills that a PM needs to have.

**Petra Wille** (00:24:14):
It's hard to talk about that really briefly. So I split all the things that PMs usually do in eight buckets, so to say. And it starts with our day able to understand the underlying problems that users and the company actually is having. Are they good in finding solutions to those problems? Then they do some planning parts. Are they able to maybe come up with a roadmap or with good goals that are aligning the team, these kind of things. And it's get it done that's already able to actually deliver the thing to work with the team that's maybe writing backlog items and all these kind of things.

**Petra Wille** (00:24:51):
Then it's listen and learn. So are they able to really gather a lot of data these days and then look into what customers are actually saying. So the qualitative and quantitative aftermath of stuff going live. And are they able to iterate on the solutions that they shipped?

**Petra Wille** (00:25:07):
And then it's another three buckets that are a bit out of the PM process, which is team. So do they know about how teams actually are different from working with individuals? Do they think they have to motivate a team? Can you motivate a team? So this whole teamwork part. Then it's personal growth. I put it on my PMwheel because I want that to be part of every conversation that I have with my PM. So that's why it's on the wheel. And then last, but not least, it's agile because when I was still coaching PMs, I often found that they never reflected on the underlying basics of agile ways of working. So they often never heard about the agile manifesto, or agile values, or agile principles, no matter what framework they're using. But I think that is key. So that's bucket number eight.

**Petra Wille** (00:25:57):
And every of those buckets comes with at least 15 framing questions. So is this person good at doing this? Is this person good in doing that? And it hopefully gives you a really nice and well-rounded picture of where this person currently is. And I usually advise people to do a self-assessment, then ask their line management for an assessment, and ideally some of your team members because they have a different perspective on you as a product management personality as well.

**Lenny** (00:26:27):
So folks who want to see that, maybe they Google PMwheel, Petra, and also link to it. How did you develop this? I managed it and came from talking to a lot of PMs and just like, "Here's the things that I see again and again PMs need to be good at to be successful."

**Petra Wille** (00:26:42):
Yeah, it was actually ... That would have been pretty cool. It was more the personal need of me starting off as a product coach. And you had this sense of, "I need this compass," because how should you start a coaching conversation. I first have to learn about what is their perception about them and their capabilities in there and the help. And then I can help them work on some of the things they want to work on. But it is often that coaches come totally unprepared to the coaching, especially when the companies actually are paying it for them and to some extent forcing them into the coaching. And then they're just like, "Okay, they told me to show up. Petra, what should we do in these sessions?" And then that's why I created the PMwheel to have these first conversations about where they think we should invest more time in our coaching sessions. So that's how I created it.

**Lenny** (00:27:35):
Cool. Coming back to just the bigger question, we've been talking about just how to become a better manager lead, a coach to your product managers. It's interesting how simple it is. The way you frame this in your writing is it's like five ingredients to be the best coach your PMs have ever had. And if you look at this list of things to do, it's very straightforward and not a lot of work. Figure out what they need to do to be successful, where are they now, align on that with them, and then just give them some things to focus on to move closer to where they need to be. That doesn't take a lot of time.

**Petra Wille** (00:28:11):
Yeah, I totally agree. The book talks about some more aspects, actually. So that's more or less the first two parts of the book. And then there is more on onboarding and hiring, create product people. There is a lot more. So that's actually the biggest part about how to coach certain concepts of today's product management industry, so to say. Hypothesis-driven product development, for example.

**Petra Wille** (00:28:38):
How do you explain these concepts to people that are not yet familiar with these things? And really, it helps product leads to reflect, "Okay, what are the small things that I could help them to get better at certain things?" Because that's actually where a lot of the magic happens. We tend to read all the books and we tend to know all our thought leaders and all these kind of things, but our product people often need super practical advice. So maybe it's really something like explaining them the Eisenhower matrix for getting better time management because they never heard about anything that could help them prioritize their tasks because that's the reality that we find in a lot of the companies, right? So that big part of the book is really this, how do you really help them understand the small tasks and things that the daily work requests them to do.

**Lenny** (00:29:31):
I think a lot of that I find is when you need something, that's the time to find it, and introduce it, and read about it. There's so much content.

**Petra Wille** (00:29:40):
Yeah.

**Lenny** (00:29:41):
I'm guilty of this. Just there's a lot of stuff to read and listen to as a PM. And I find you don't need to be listening to and reading everything all the time. It's just like, I need to figure out how to prioritize. Let's see what's out there that's awesome. And maybe save it for the future, but there's so much stress, I think, that goes into like, "Oh my God, I got to read everything all the time."

**Petra Wille** (00:30:00):
Yeah, I totally agree. I think two weeks ago, one of my coaches told me that he stopped reading a lot of books and consuming a lot of content and he instead dedicates the whole year to using one methodology or book. So in that case, pick Teresa's Continuous Discovery Habits and that's what they read over and over again for the whole year. And I think it's an interesting way of looking at things.

**Lenny** (00:30:30):
That is interesting. That's a very committed, better pick the right book that are or whatever [inaudible 00:30:35].

**Petra Wille** (00:30:35):
Yeah, that she has said is true. Yeah. But maybe some of your colleagues pick another book and then you can just share what you learned, and what works better, and a bit of a community thing.

**Lenny** (00:30:44):
Oh, we're going to get to that. I like that. Before we get to retelling topic, is there anything else you want to share along the lines of the folks are just like, "I want to become a better coach to my PMs?" Any other thoughts you want to close with?

**Petra Wille** (00:30:57):
Yeah. One easy tip is get yourself a list of great questions that you could ask in one on ones if you don't have the time to prepare. That will be one of my tips as well. There's several great coaching books out there. Some of questions are in my book as well. Yeah, just find some coaching questions, make your small compilation, and then really see what resonates with your team, and that often is a bit of a health check. So how are you doing? What would make you more successful in the role that you're currently having? All these kind of things could be helpful.

**Lenny** (00:31:38):
Do you have any other examples of those? That's actually useful and just a few more examples of coaching questions.

**Petra Wille** (00:31:44):
Yeah, it really depends. So what I find super helpful is a list of emotions because people tend to find it really hard to talk about how they currently really are. And I don't know why this is the case, maybe it's stress, maybe it's not feeling comfortable to talk about this with your line manager, which is another topic, and bringing us back to the topic of company culture. But that, for example, is something that I always have handy. And if I have this notion of, "Okay, this person maybe really needs a hack to some extent," then this conversation about, "Hey, look, there is this list of 30 emotions, where do you think you currently add and why and could I help you with that?" So that could be something. And then there are ... I think you talked about Mochary the other day, right?

**Lenny** (00:32:31):
Yeah. That episode just came out.

**Petra Wille** (00:32:33):
Yeah, exactly. And he has a great framework as well. I would need to look the questions up, but maybe we put them in the show notes as well. That's a bit of in-house check as well and huge. First of all, it's five easy assessment questions for your folks. And then it's more of, "Okay, if you're ranking yourself a six, how could I help you to make it a seven?" So it really focuses on incremental improvements, not crazy stressing everybody out improvements, not, "What could I do to make it a 10?" It's more really, "How could I improve your situation? Really build rapport, really be there for your product folks.

**Petra Wille** (00:33:11):
And I think creating this list of coaching questions as a go-to list could improve the quality of your one on ones because, let's face it, we often run into those ones. Either we ditch them or we run into those ones completely unprepared. And a development plan could help and a prepared list of coaching questions could help to make it way easier. And for your PMs to feel more valued.

**Lenny** (00:33:37):
That's a great callback to the Matt. And by the way, his name's France, Matt Moshary, instead of Mochary. The C-H was like a sh.

**Petra Wille** (00:33:44):
I see.

**Lenny** (00:33:44):
Yeah. Now, we know.

**Petra Wille** (00:33:46):
[inaudible 00:33:46] learn something. Now, we know. That's good.

**Lenny** (00:33:49):
Yeah. And you pointed out in his curriculum, he has a bunch of questions that you mentioned about where are you at one to 10 on this thing and then how do we get you to ...

**Petra Wille** (00:33:56):
Yes.

**Lenny** (00:33:57):
... eight or nine. So we'll link to that in the show notes also. So many more things to read from this podcast.

**Petra Wille** (00:34:02):
So many things to link. Sorry.

**Lenny** (00:34:06):
Good God, poor listeners.

**Lenny** (00:34:06):
**Petra Wille** (00:36:18):
Yes, I think I would love to mention two things. So first of all, people that's starting, often they are getting a better storytelling journey. Often totally underestimate how many time actually great storytellers are investing in creating the stories and making sure they can share the story in nice ways and formats. So that's maybe the first tip, you have to plan to put in a lot of work to create your story.

**Lenny** (00:36:46):
And when you say a lot of work, what are you thinking? What's an order of magnitude of time depending on the scale of the story or a deck, or?

**Petra Wille** (00:36:55):
Rule of thumb. So I think if you ... Let's say you want to explain the rest of the company what you and the team are up for the next three to four months, so to say. Then I think that's two weeks of work, not eight hours a day, obviously, but two weeks of work, maybe one or two hours a day to really carve that story and think about different audiences and different framings of, when am I able to tell the story? And that is actually, I think, a rule of thumb of time investment. So it takes time because people often think, "I don't know, you just get better overnight in telling great stories." It's just not how it works. So you have to practice and you have to put in a lot of work and time to come up with a logical, compelling, motivating story that then lasts for longer than a week or two. So that's a lot of work.

**Petra Wille** (00:37:48):
And then the other tip would be really make sure that you're using language that speaks to the heart and the minds of the people because we constantly tend to use too much of our business lingo and it's banner blindness. Some of the words that we're using people totally overhearing them because we're using them so often. And it could be even things like product discovery. So maybe your company is already so fed up with all your product discovery stuff that you should start using different terms. Even if then, say, hypothesis-driven product management, it's more or less the same thing, and maybe it's even too complex. Maybe you can find something simpler and say, "We need to learn something about this particular thing," because studies show that's a scientific background. Stories really have an impact on our brain.

**Petra Wille** (00:38:45):
So hormones get released depending on how the story is actually formed, if they have cliffhangers or if it's really like, whoa, with the hero and think, "Where is it going to take him", or something like that. And that releases, yeah, hormones in your brain and that only happens if you're using natural world, so to say. So you could talk about smell, and sense, and how people feel, and how their life would be better if this product would be out, all these kind of things. So really make sure that you think about that really speak to their minds and to their hearts and remove all your three-letter abbreviations and all these kind of things, which is something that everybody says as well. But it is way harder to do it when you really start to create your story to remove all these terms. And that takes a lot of time, yeah, as well. So you have to really put an effort into the don't use too much [inaudible 00:39:46].

**Lenny** (00:39:47):
So the first point, which I love, is you think people are just good at this and naturally great at telling a great story. But a lot of it is ... Right. Some people are ... You do it enough and you're like, "It'll be quicker probably." But for most people, it's going to be just put in the time and it gets better and better and your story merges, you practice.

**Petra Wille** (00:40:04):
Yeah. And it's a cultural thing. So I really find in average Americans, for example, being better at it than most of us Europeans. And I think that's because even in your school system, it seems to me, I don't know, you tell me if that is the case, but storytelling and being in front of a class or something like this is something that is encouraged and valued already, where at least when I was at school, this was not part of the whole system at all. So really late it was part of what we did, but not from an early age. So it's just not something, yeah, that we trained in or that we used to. So sometimes even speaking in front of 30 people, people are freaking out because they never did that. So that's their cultural differences to that definitely as well.

**Lenny** (00:40:57):
Speaking of the idea of speaking in public and being nervous and that kind of thing, which I always get really nervous speaking in public and people don't think that when they hear me and other folks that are publicly speaking, but it's like freaks me out every time. Do you have any advice for people that want to become better public speakers/be less nervous speaking publicly?

**Petra Wille** (00:41:20):
I was really bad in [inaudible 00:41:21] as well, I have to tell you. And it's still not something that I love, but I know it's part of the work that we do.

**Lenny** (00:41:30):
Yeah.

**Petra Wille** (00:41:31):
And so the easiest way is to get in front of really small and super friendly audiences. So that is, I think, the first starting point. And I don't know where that is. That could be your team, that's a super small audience, usually five to 10 people, or maybe you pine with your company of 80 people or 120 people, maybe the company all-hands is already something where you could actually speak. That was my first time and I had to speak in front of the whole company at a company all-hands around 90 people back at the time. And I only had to give a brief update on what we did the last two weeks and it was like five minutes on stage, but it freaked me out.

**Petra Wille** (00:42:14):
So that's where I'm coming from and it really helped me to start small. Then product tanks, for example, this local product community meetups totally helped me because friendly human beings and not too many of them. So sometimes they're just 30 people attending and then you in the summer, not so many people are coming, so why not giving a talk there? So really start small and then grow the audience over time and always make sure, because that helped me a lot, to get feedback from strangers and peers if possible. Because the peers tend to give you the harsher critique, so to say, where the strangers are more polite, but they're not so familiar with the work you do or with the story that you want to tell so they can spot some gaps in your storytelling technique or something like that.

**Petra Wille** (00:43:07):
So that is something that helped me a lot to always have this friendly soul in the front row, where I know I get some feedback from later on. Plus, then having complete strangers and there's always somebody coming up after the talk, right, so they could be your first person giving you some stranger feedback, so to say.

**Lenny** (00:43:25):
What about if you're just about to give a talk and you're like, "Oh my god, I'm so nervous," do you find anything that helps you get over that?

**Petra Wille** (00:43:33):
I think the two things that work well, it's either the Superman pose, so that is one thing. If you're standing like this looking straightly up, that is one thing that helps many people. It's not my preferred one. And then the other one is a bit of the gorilla thing, just like tapping here. There is ... I don't know what's the English-

**Lenny** (00:43:56):
Vagus, the vagus nerve.

**Petra Wille** (00:43:57):
No, it's not the vagus nerve.

**Lenny** (00:43:57):
Oh, a different.

**Petra Wille** (00:43:58):
I think it's thymus.

**Lenny** (00:43:58):
Okay.

**Petra Wille** (00:43:59):
I need to look it up. And if you just, yeah, hit that softly for some time ...

**Lenny** (00:44:07):
Yeah, I can hear it.

**Petra Wille** (00:44:07):
... then, yeah, that bumps your energy level, so to say. So that helps me. And again, friendly faces front row. So find people that you like and respect and that you know have the spark in their eyes when you start talking. That definitely helps as well.

**Lenny** (00:44:24):
Do you suggest doing these moves in the bathroom where no one can see you, or?

**Petra Wille** (00:44:29):
Yes, backstage. You're doing those ones backstage. And think about what you're wearing because if you're wearing something like that and do this before you enter the stage, people might see that.

**Lenny** (00:44:38):
They might love that.

**Petra Wille** (00:44:38):
Yeah.

**Lenny** (00:44:38):
Just come out beating your chest. It's a power move.

**Petra Wille** (00:44:38):
Yeah.

**Lenny** (00:44:39):
Do you think it's important for PMs and leaders in general to get great at public speaking or do you think it's okay if they are just okay?

**Petra Wille** (00:44:53):
It really depends. So I think not being able to speak publicly and to bring your point across ... Because a lot of people do public speaking, but they never bring their point across. So if you want to achieve both things, I think it is a career solo if you can for a product person. Can do the IC level product management job, but getting promoted is way harder if you're not good in telling stories and rallying the team behind the shared goal and all these kind of things. And you usually achieve this through good storytelling techniques.

**Petra Wille** (00:45:33):
And in some teams, I've seen the product person not being really, really good at it, but then the whole team helped creating the stories and stuff like this. So you definitely could compensate to some extent, but I would consider it a bit of a career solo if you don't get to decent level of storytelling and to a decent level of public speaking. So, yeah, I think it's important.

**Lenny** (00:45:54):
Who's the best storyteller PM that you've met and what made them great?

**Petra Wille** (00:45:59):
That's another hard question. So who had the biggest influence on me was definitely Jason Goldberg. He was my former boss and he was the first person that came into the startup that I was working for back at the time. And he was really the first person who entered every stage that he could find to talk about the things that he wants to achieve with us as a product team and as a product organization. In a way, it was really motivational, so it really helped me to experience that and how he was using this product, evangelizing techniques, yeah, to actually really tell the whole company what we're up for currently and what the problems out there he thinks are worth solving. So that was definitely an inspiration.

**Petra Wille** (00:46:47):
And then I think another great speaker is definitely Hans Rosling. He's no longer with us. That's sad. But he gave great TED Talks, really data-heavy TED Talks because they often hear from product people, yeah, but the work we do that's so boring, how could we make a great story out of that? And I think Hans Rosling showed over and over again that you can. So that definitely is an inspiration.

**Petra Wille** (00:47:14):
And then on a totally different note, I love spoken word poetry because it really talks to the heart and minds of people. And in my coaching, I usually send people off to the TED Talk from Sarah Kay, which has the nice title, If I Should Have a Daughter. And that really helps people to understand, "Ah, okay, that's how you could be playful with words." And that's what happens to me personally and to my body and to my emotions if I listen to something like that. So that's maybe three things I could be mentioning.

**Lenny** (00:47:49):
Hans Rosling's the guy with the world poverty charts and ...

**Petra Wille** (00:47:54):
Exactly.

**Lenny** (00:47:54):
Yeah, yeah.

**Petra Wille** (00:47:57):
On world and data.

**Lenny** (00:47:57):
Right.

**Petra Wille** (00:47:57):
Now, his son is, I think, in charge, but, yeah.

**Lenny** (00:48:00):
Cool. I'm excited. I'm going to watch that one again. That's a good reminder. Maybe just another question around storytelling. Say you're a PM and you're about to start a document or a deck and you just want it to be a good story, what are two or three things you should just do to set yourself up for success?

**Petra Wille** (00:48:17):
Yeah. First of all, don't sit in front of the blank page for too long, just start drafting something. I think there's a lot of beauty in story as a design tool, so to say, because it's even easier to change a story than it is to change a prototype, right? So even before you put something in writing, you could start talking about it and see how it lands and then tweak it. And I think that's the first thing, get going.

**Petra Wille** (00:48:43):
And then the other thing is go start talking about your story, go test it, see how it resonates, and then tweak it. And maybe you could use one of the proven story structures, find the one that helps you most. Really, even if it's super boring, but I'll use this hero's journey a lot where I think about, should I put the team in the heart of the story? Because if it's a story that should help me to motivate the team or to inspire the team to actions or something like that, then maybe it's nice if I put them in the center of the story and make them the heroes and talk about the demons and monsters they have to fight to once arrived at this brighter future.

**Petra Wille** (00:49:25):
And maybe some other times, it makes sense to put the user there and really talk about how their world and lives would have improved once this product is out and available. Or maybe it's even a feature that we're talking about or a bigger redesign or whatever you're currently working on, right? But you could use this proven story structure and see what are the things in there. So the call to adventure, what is the call to adventure? What is this bright future? And it helps you to start and to get going.

**Petra Wille** (00:49:55):
And then I usually advise people to have the story handy in various formats. So spoken that you could actually talk about it. Written, because we all tend to work in remote or asynchronous environment. So just a recorded video maybe. Yeah, it's good, but maybe a written version of it is nice as well. And the next one is an illustration that helps you making some of the core points of your story visible to the audience. And that could be a whiteboard drawing, a flipchart drawing. It could be a bigger, maybe it's five slides with emotional pictures on it or whatever it is, but be visual with your story as well.

**Petra Wille** (00:50:37):
And then you should have it ready in three different formats in a super short 75-second elevator pitch version. In the six minutes, I can do this before we actually start planning version. And ideally, I have to go to the company all-hands and have to talk about what we will look into for the next four months. And that's maybe an 80 minutes version. And 80 minutes is the length of an average TED Talk, and there is a reason for that. It has to do with attention spans and all these kind of things. So that's why I advise people to use this three length.

**Lenny** (00:51:14):
An example you're using there is a PM designing the vision for their team potentially or their strategy for the next, say, six months, right?

**Petra Wille** (00:51:21):
Yeah, exactly. So we don't need to create this complicated story for the next sprint, I'd say. That's too much of an effort, maybe waste of time. You need to look a bit further out to make it worth spending a lot of time on creating your story.

**Lenny** (00:51:38):
If you had to pick one book or resource that helped you become a better storyteller or that you found other people coming back to that helps them level up their storytelling skills, what comes to mind? I'll share one first as you think about that. There's a recent book that you wouldn't think would be good at this, but it is really good at helping understand how to tell a story. And it's called Nobody Wants to Read Your Shit. And it's by ... Yeah. And the title alone is a great lesson, which is, nobody wants to read your stuff. Yeah. But the premise of the book is how to make it so that people find it interesting and useful. It's by Steven Pressfield who wrote The War of Art and Bagger Vance and all these things. So it's one of his new books, I think. So that's what comes to mind.

**Petra Wille** (00:52:22):
That's pretty cool.

**Lenny** (00:52:22):
What comes to mind.

**Petra Wille** (00:52:23):
Back in the day when Marty Cagan was my product coach, he made me read Selling the Dream, which is the Macintosh story on product evangelizing by Guy Kawasaki. And it didn't help me to become a better storytelling, but it helped me realize that it's really important that I work on that skill. So that is actually the trigger and material that helped me is basically everything from Nancy Duarte and Duarte Inc. So there are even leadership books about rituals and how to ignite the spark in all the people you're having. So they're talking a lot about the leadership aspect of storytelling, but they have something for the IC level as well, 72 rules on storytelling and all these kind of things. And I have a lot of free material. I know it's not a book, but they have several books and that was great material that helped me to become better.

**Lenny** (00:53:16):
Man, the show notes on this episode are going to be out of control. It's going to hit some limit for [inaudible 00:53:20].

**Petra Wille** (00:53:20):
Yeah, maybe we're ... Yeah, the longest show notes ever. Sorry.

**Lenny** (00:53:24):
Oh my God. Yeah, it's going to be rough. I'm actually going to try to get Nancy Duarte in this podcast.

**Petra Wille** (00:53:29):
Ooh, yeah.

**Lenny** (00:53:30):
So that's a good ... That's-

**Petra Wille** (00:53:31):
Say hi if you do. Yeah, I'm a fan.

**Lenny** (00:53:34):
Okay, I'll do that. I'll do that. Okay. So getting to our final topic, which is around community. You're a big fan of finding community and just the power of being in a community, and I know you've done a bunch of research there, you're just like pumping your fist as we talk about this. I love it. So tell us why you're such a big fan of the power of community for product managers in general.

**Petra Wille** (00:53:54):
Again, the starting point was a rather egocentric starting point because I'm constantly thinking about, how could I scale the work that I do because I still see so many companies not getting a product coach or I still see so many companies where people development is not a priority, all these kind of things. And at some point, I thought, if the line manager is not taking care of the personal development, who could? And I talked to several of my colleagues about the question and, at some point, somebody said, "Yeah, that's what community of practices are often used for." So that's where a lot of people get their inspiration. And basically, I reflected on my career. And early on, I was in a super engaging product organization where, really, we tried a lot, we shared a lot. A lot of the things that we tried didn't work at all, but others really fell on fertile grounds and we could learn from each other.

**Petra Wille** (00:54:55):
And we invested quite some time in this sharing, but everyone got better over time because of this community being present. And so I decided to make this my topic for this year's research, so to say. And I was talking to a lot of my clients and former clients, "Hey, are you running a community of practice? If you don't run a community of practice, why is that?" Often, they have never considered running one, they don't know where to start. So that's another problem, obviously. And at some point, I decided to conduct a survey to see if random strangers can tell me about their companies and their community of practice. And it was super interesting as well.

**Petra Wille** (00:55:34):
For example, I found that oftentimes there is a bit of a community of practice internally, but they never heard about external product community. So they never heard of your community or to raise this community or mind the product or any of those external communities. And that is shocking to an extent as well because we're all so friendly human beings, happy to share what we learn, and they don't have to go through the same things over and over again. So that's why I think it's a super important question and I would love to help a bit more companies to start a community of practice or to mature the community of practice that they're already having.

**Lenny** (00:56:14):
What impact have you seen folks get when they join or find a great community? And then what are communities that you find are most useful? You mentioned ... And I want to get your advice on what I could do to make it even better, but maybe those two questions. What impact do you find when you find a great community and then what are some that you [inaudible 00:56:31]?

**Petra Wille** (00:56:31):
One impact, definitely, is stickiness. So people tend to stay with companies where they're learning and growing and can, yeah, get to mastery, so to say. Hello, Daniel Pink. So that is really something that people are thriving for, and if they find this in a company and a product community of practice could be a big part of that. So that is one impact.

**Petra Wille** (00:56:59):
Then the other impact, there's less people development on the desk of the product lead if there is a good product community of practice. So product leads, your life will get so much easier if there is a product community of practice. And it's actually a pretty cheap way of doing people development because trainings are expensive, conference tickets are expensive, getting external product coach, expensive. But helping people to learn from each other by making room for that and giving them a bit of time to reflect and to share what they're learning, that's rather cheap. So I think that is the benefits that I see.

**Petra Wille** (00:57:40):
Training budget impact. People tend to stay with the company a bit longer. Leadership wise, it's less a time that you have to invest in people development. And then it's just fun for a lot of people. That's another uptake, I'd say.

**Lenny** (00:57:54):
What are signs that the community that you're in, say, you found?You mentioned a bunch that I think are awesome. Teresa's community, we'll talk about my Slack a little bit. Mind the Product.

**Petra Wille** (00:58:02):
Yes.

**Lenny** (00:58:03):
What are signs that the community you're in is good with your time? Something you should stick with versus like, "Nah, get out of there."

**Petra Wille** (00:58:10):
That is actually a good question. So I would say, if it helps you with networking, that is really something good if you meet nice, interesting people. So that is one thing I would love to mention. And then if you're learning something new every now and then, maybe not every day, maybe not every week, but every now and then, there should be some real nuggets where you think, "Oh, this is making my life easier," or "This is super interesting. I would never ever have stumbled upon this thing without the community." So learning something new and then reflecting on how much you already learned about a certain topic or know about a certain topic, which is contributing to the community.

**Petra Wille** (00:58:55):
You could be a community moderator, you could be somebody organizing some of the rituals, you could be somebody just sharing what you learned. So I think that is something that could be in a good community that is possible at least to share that everybody's sharing and that there's mutual trust and then it's often just, if you enjoy being part of this community. That's, I think, another super important thing to look into. Do you like the people there? Do you like to hang out with them? Do you think they're kind, lovely human beings? And is there some level of activity in the community because there's too many dead ones out there, more or less? And I think these are the things that I, yeah, would use as a benchmark.

**Lenny** (00:59:37):
When you're talking about this, initially, I was just imagining online communities, but there's also, obviously, offline communities probably somewhere in your local city.

**Petra Wille** (00:59:44):
Yeah, product things.

**Lenny** (00:59:44):
Right. Just like ... Yeah.

**Petra Wille** (00:59:46):
Yeah.

**Lenny** (00:59:46):
Yeah. So I think ... I don't know if people thought that when I was talking, but, yeah, there's probably meetups happening in your city with product managers that are meeting each other every week, every month maybe.

**Petra Wille** (00:59:55):
Yeah.

**Lenny** (00:59:56):
That sounds awesome. And I love your point about the why of the community versus a course versus reading lots of books. It's really affordable to join some product community, especially if it's online.

**Petra Wille** (01:00:09):
Yes.

**Lenny** (01:00:10):
And the ROI could be really high.

**Petra Wille** (01:00:11):
Yeah. And it brings so much clarity in your thinking if you're sharing some things you learned with the community that this is a massive uptake as well, so give back. That really makes sense for you personally as well.

**Lenny** (01:00:27):
So you mentioned my Slack community. So if folks don't know this and they're listening, basically, if you're a paid subscriber committees letter, you get access to the Slack and there's about 10,000 people in there, mostly PMs and founders and growth leaders, and it's pretty damn incredible. It's probably the thing I'm most proud of of all the things I've done over the last few years around this newsletter and podcast.

**Lenny** (01:00:48):
And so if you're not in there, you should definitely check it out. It's thriving. There's meetups happening all over the world every month. There's a mentorship program, there's mastermind groups, all kinds of stuff. And you're familiar with it. And so I just wanted to ask you while I have you here, do you have any advice for how to make this community even more great?

**Petra Wille** (01:01:06):
That is not an easy question. First of all, congratulations. I really think it's a massive achievement to start such a community and to really have such a vibrant community because I know it takes a lot of energy investment at first to get it going and then a lot of energy to keep it on a certain level, so to say.

**Petra Wille** (01:01:29):
Yeah. What I found helpful is I have this community canvas that I use when I'm working with clients and some of these things require workshops to some extent. So it helps to reflect on what is the purpose of the community and that changes over time with the community members that are currently part of this community, right? So that is not a stable thing. So sometimes everybody has to pause for a second and then think about what is the purpose of this community, what are our values, and how will we define success?

**Petra Wille** (01:02:05):
It's pretty boring, I know, because it sounds so, so familiar with what we do in product management, but I think it applies for product communities as well. And then you need to find good rituals and rhythm, and you, Lenny, were already talking about some of the ones you are using. I know, for example, what Teresa is doing in her community. I interviewed her this year, so there is a blog post on that online as well where she talks about what she tried, and what did work, and what did not work. So I think that is important.

**Petra Wille** (01:02:36):
Then maybe not so important for your community. Well, let's see. Let's discuss, let me hear what you think, which is incentives and sponsoring. So how do you, yeah, value contribution? Are you giving back? Is it a kudos mechanism or is it something where people really earn badges of honor or earn time, earn more training budget. That's what a lot of companies do, right? If you're playing an active role in the community, then you get more training budget to spend or something like that, or they grant you time to do so. So if you say like, "Hey, I want to be part of this product community, could I travel a quarter or something like that because I want to go and see those people?" That is something that people do. So incentives and sponsoring, then it's roles. And that will be interesting in your case as well. Is Lenny the center of the community?

**Lenny** (01:03:34):
Yeah, I try really hard not to do that, actually.

**Petra Wille** (01:03:36):
Yeah, right. Yeah.

**Lenny** (01:03:36):
That's a [inaudible 01:03:36] try to not be the beacon of all answers. The actual goal of the community was I will not have all the answers. Let's just bring a bunch of smart people together that are already there's this interesting filter of who pays for content about product and growth and stuff.

**Petra Wille** (01:03:52):
Yeah.

**Lenny** (01:03:53):
Filter's really interesting. So the whole idea was get out of the middle of this thing and let people help each other and it's worked out really well.

**Petra Wille** (01:03:59):
Yeah, because that's what I would say after doing all this research, it's not sustainable if the whole community is on the shoulders of one, two, three people. So you need to distribute the workload and you need to distribute this responsibility because sometimes even things like, yeah, policing the community is not a pleasant job. And if there's only one person dealing with all of these things, then it's not really community because then it's a bit organized like a company in this pyramid scheme.

**Petra Wille** (01:04:30):
So I think more of it as circles, different circles of interest, and then building bridges between them because maybe not everybody in your community is interested in the same topics, but maybe they are the smaller circles of 10, 15 people interested in this one topic, 10, 15 people interested in this other topic. You may be connecting the dots, you may be giving a bit of impulse and inspiration, but maybe other people are doing the exact same thing, sharing their best reads and their worthy to watch videos, and all these kind of things. So content and curation, definitely, is another thing that you should think about and reflect on once in a while.

**Lenny** (01:05:08):
Cool. Thanks for the advice. Curious is so important. Especially early on, I found keeping the signal to noise high always. And especially early on, it was a really prayerful. So there's a lot of focus [inaudible 01:05:19] detail oriented about it all.

**Petra Wille** (01:05:21):
Yeah. Plus, a lot of communities that I see use engagement as a success metric, and I'm actually not sure if this is a good success metric. So as you say, signal versus noise is maybe the better success metric, which leads us the down the rabbit hole of how to [inaudible 01:05:38]. But, yeah, engagement is maybe not the predominant success factor for a community.

**Lenny** (01:05:44):
Yeah, that's interesting. You also said it's a lot of work. And just to give some shout-outs to folks that help me run this community that we have, I couldn't do this without them. Trey, who leads the community. Keani who-

**Petra Wille** (01:05:54):
Hello, Trey.

**Lenny** (01:05:55):
Hello, Trey.

**Petra Wille** (01:05:56):
I know Keani.

**Lenny** (01:05:58):
Keani curates the best conversations in the Slack every week and then shares them in this bonus email, Community Wisdom.

**Petra Wille** (01:06:04):
Nice.

**Lenny** (01:06:04):
And then Ria, who's been helping out run the meetup program. And then Jess who's helping with our mentorship program and a few other things. So that's the core team that helps this whole thing run. Thank you to them all.

**Petra Wille** (01:06:15):
Thank you. And it's super interesting that you're sharing that because companies often don't want to invest in, yeah, full-time community manager is maybe the wrong word because that not necessarily has to be a full-time role, but there need to be some people that really have a decent amount of time to invest in running this community because otherwise it's not working. And I still think it is still cheaper than sending everybody to trainings and conferences all the time, and it has a lot of, yeah, ripple effects and network effects.

**Lenny** (01:06:48):
Well, guess what, we've reached our very exciting lightning round.

**Petra Wille** (01:06:51):
[inaudible 01:06:52].

**Lenny** (01:06:52):
So I'm going to ask you a few questions. Whatever comes to mind, let me know. We'll go through it pretty fast.

**Petra Wille** (01:06:57):
Yes.

**Lenny** (01:06:57):
And are you ready?

**Petra Wille** (01:06:58):
I'm so ready.

**Lenny** (01:06:59):
So ready. What are two or three books that you recommend most to other people?

**Petra Wille** (01:07:05):
The Art of Thinking Clearly by Dobelli. It talks about human biases in a really nice and illustrated way. Then what I use a lot in my coaching practice, especially with senior executive, is Outcomes Over Output because it's a super strong concept, I'd say. And then maybe I want to mention two books that are not yet written, but two concepts that I hope will make it into books, and one is Martin Eriksson's Decision Stack. And then there is another book about public speaking that hopefully might come out if some people are supporting it on Kickstarter. And that is called Present Yourself, a public speaking book.

**Lenny** (01:07:42):
Awesome. If you can sign a link to that, we'll include it also in the show notes.

**Petra Wille** (01:07:45):
Of course.

**Lenny** (01:07:46):
The record ...

**Petra Wille** (01:07:47):
Show notes, hello.

**Lenny** (01:07:48):
... longest-ever show notes. Speaking of that, what's another podcast that you love?

**Petra Wille** (01:07:52):
I love the Product Experience podcast. And if you're able to speak German, then there is one that is called [foreign language 01:07:58]. That's a nice interview series.

**Lenny** (01:08:02):
[foreign language 01:08:02], I like that. I do not speak German, but I thought it'd be fun to listen to, anyway. What's a favorite recent movie or TV show that you've enjoyed?

**Petra Wille** (01:08:11):
Maybe New Amsterdam. I loved it. That's actually a medical director, Matt, and he's finding very unconventional ways to solve problems and I think he's a great leader, so maybe that's a nice framing for watching the show.

**Lenny** (01:08:26):
What was it called? New Amsterdam?

**Petra Wille** (01:08:27):
New Amsterdam.

**Lenny** (01:08:28):
Sweet. What's a favorite interview question that you'd like to ask when you're interviewing folks?

**Petra Wille** (01:08:32):
Definitely the tell me about the last time. So tell me about a time when you did your last round of user interviews. Tell me about your last time when you onboarded a new colleague because I think as a user interviewing this, tell me about the last time you really, yeah, sparks nice conversations and interviews.

**Lenny** (01:08:54):
What are five SaaS tools or products that help you do the work that you do now? And if there aren't enough of those, just great apps that you love right now.

**Petra Wille** (01:09:04):
I'm totally not into product management SaaS tool these days because as I'm just coaching people on hourly basis, I'm no longer the one looking into the SaaS tools they're using. So that's quite a tough question. Things that I use a lot in my personal work is rather boring stuff like bookkeeping software and time tracking [inaudible 01:09:25]-

**Lenny** (01:09:24):
Which ones? That's interesting.

**Petra Wille** (01:09:27):
Harvest is what I use for time tracking and bookkeeping, and I love that. It makes my life easier since a few years already. And then, yeah, new banking apps that are coming up that I'm using for my accounts. One is Qonto, I think it's a German bank, but they really did a great job in the user experience, super seamless in the apps and all these kind of things. Yeah. So that's two cool products that I love to use.

**Lenny** (01:09:54):
Great. Who else in the industry do you most respect as a thought leader, influencer-type person?

**Petra Wille** (01:10:01):
As I'm a conference organizer as well for a conference that was called the Product Engage here in Hamburg, that is the super hard question for me to ask because so many people have been on that stage, that I would consider being a thought leader, they would maybe not consider them being a thought leader. I think the thought leader thing is pretty hard anyway, so there's so many different voices in our industry. And I think looking at the guest list of your podcast actually is a very good start when you think about thought leaders and getting more inspirations because they are ones that we know and some hidden gems on there.

**Lenny** (01:10:37):
Great answer. Great answer. Petra, thank you so much for doing this. We've hit the record on show note length, I guess, so that's a milestone. Congrats.

**Petra Wille** (01:10:48):
Yes, thank you. Was a pleasure.

**Lenny** (01:10:51):
Two final questions. Where can folks finding online if they want to learn more, reach out, maybe work with you and how can listeners be useful to you?

**Petra Wille** (01:10:58):
Ooh, interesting. Yeah, the first one is easy, LinkedIn, Petra Wille, you can find me there. And then there is my website, Petra-W-I-L-L-E.com. That's my website. And how can listeners be helpful to me? Whew, that's a tough one. I think it could be mutual beneficial if you are a product manager IC level and you would love to get better supported in your personal development and go by my book and just hand it to your manager, if that's appropriate. Or just put it on their desk and just forget that it's there and hopefully they read it or something like that. I think that is how I would love to answer the last question.

**Lenny** (01:11:40):
Remind folks what the book is called and they can find on Amazon [inaudible 01:11:43].

**Petra Wille** (01:11:42):
Strong Product People.

**Lenny** (01:11:46):
Strong Product People. Go check it out on Amazon.

**Petra Wille** (01:11:48):
Exactly.

**Lenny** (01:11:48):
Petra, thank you so much for doing this.

**Petra Wille** (01:11:50):
Lenny, was a pleasure.

**Lenny** (01:11:52):
It's my pleasure.

**Lenny** (01:11:54):
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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## [16/20] How to hit revenue targets in a recession | Sahil Mansuri (Bravado)

**Sahil Mansuri** (00:00:00):
It's hard to plan what you should do for all of 2023. I think the advice that most founders are getting from their boards is when you have limited visibility, you have to plan in the most conservative way. On the one hand, of course that's true, you have to be conservative. But on the other hand, you don't want to be unreasonably conservative because you don't want to be floundering from like, oh, we're screwed to everything's better, to we're screwed, everything's better. 

**Sahil Mansuri** (00:00:29):
So the way I think about setting up a plan when you have limited visibility and some major headwinds is setting up a really conservative plan and then having milestones, short term milestones that unlock the ability to lean into growth and spend based on hitting those targets.

**Lenny** (00:00:49):
Welcome to Lenny's Podcast. I'm Lenny, and my aim here is to help you get better at the craft of building and growing products. Today my guest is Sahil Mansuri. Sahil is the CEO and founder of Bravado, which has built the world's largest online sales community of over 300,000 salespeople, and they're now building SaaS products for salespeople. Sahil has one of the most unique perspectives on the art and skill of sales, partly because of the community and the company that he runs, and partly because he was a longtime salesperson himself. 

**Lenny** (00:01:21):
As you'll hear in this episode, he has closed some incredible deals, including a wild story about cold emailing Sheryl Sandberg at Facebook and what that led to. In this episode, we focus on what founders should change and how they do sales during this market downturn, including how you should approach sales quotas, how you should rethink the way you do comp plans for salespeople, how you do forecasting, also why you should refocus on retention and your existing customers, how to improve your sales technique in general no matter what role you're in. 

**Ashley** (00:02:13):
At least 40%.

**Lenny** (00:02:15):
How many of them screw that up? What happens when they do?

**Ashley** (00:02:18):
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** (00:02:38):
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 longterm retention. Getting people to your aha moment more quickly and reliably is so incredibly important.

**Ashley** (00:02:52):
Totally. It's incredible to see how our customers like Square, Spotify and Zora are able to grow their businesses on top of Flatfile, this because flawless data onboarding acts like a catalyst to get them and their customers where they need to go faster.

**Lenny** (00:03:09):
**Sahil Mansuri** (00:04:21):
Thanks Lenny. Thanks for having me.

**Lenny** (00:04:23):
So we're going to be talking about sales and in particular what you should be adjusting in your company during these very turbulent market conditions. But I thought first it'd be helpful if you just gave a little background on yourself to kind of give folks a sense of why you have such unique insights into the sales world. So maybe just talk about a little bit of your background and then what you do now, the company that you run now. 

**Sahil Mansuri** (00:04:46):
I've spent my whole career in sales. I started out in sales when I was in college. I worked on the Obama campaign. We didn't call it sales, right? We called it turning out the votes or street teamwork or field ops or phone banking, but it was sales. We were just selling the dream, literally the American dream as it were. So I've been in some sort of a role where my primary responsibility was to cold call, send emails, have conversations, objection handle, and try to get someone to sign a contract for my entire career.

**Sahil Mansuri** (00:05:22):
I started selling in September of 2008 was my first month with a quota. So I started selling in the middle of the last financial crisis. In 2009, the company that I used to do sales for, which is called Meltwater, this company, it's a pretty crazy story. It's one of the few companies that has made it to $100 million in recurring revenue without a drop of venture funding. It's a Norwegian company actually. 

**Sahil Mansuri** (00:05:52):
If I remember correctly, don't quote me on the exact numbers here, but the company had basically gone 10 million to 30 million to 50 million to 70 million, and then in 2009, they went from 70 million to 69 million. It was the first year that they hadn't not only increased revenue, but revenue had gone down. In that year, in 2009, I broke the company record for the most sales by any individual person in one year in the history of the company. I say that not out of hubris or out of pride, I say that because I've literally sold in a downturn. In the middle of a recession, I have been an account executive selling, carrying a quota and have been successful in doing it.

**Sahil Mansuri** (00:06:37):
Then went on to be a sales leader at a bunch of different places, probably most notably at Glassdoor, where I joined as one of the first 20, 25 employees. Was responsible for enterprise sales there. Personally closed Facebook, Google, Amazon, Microsoft, Ford, Visa, Bank of America, JP Morgan, Walmart. At its peak, at one point I think Glassdoor had about 100 of the Fortune 500 customers and I'd sold about 60 of them myself. I've done a lot of selling in my career, also a decent amount of sales management and sales leadership. 

**Sahil Mansuri** (00:07:14):
But really my forte is selling. I love to sell. I love to talk to customers. I love to train salespeople. I've been a VP of sales and CRO in a couple different places. Then for the last five years I've been building a community for salespeople that's called Bravado. Bravado is a network of about 300,000 B2B tech sales. That's about 50,000 VPs of sales and CROs, about 150,000 account executives, another like 40 to 50,000 SDRs. Then the rest of it are kind of customer success, sales engineers, sales ops, sales enablement, et cetera. 

**Sahil Mansuri** (00:07:59):
So it's a network that purely focuses on sales, and much akin to your business, I suppose, marries community learning, upskilling, recruiting as this one place that a salesperson can go in order to beat the odds, be successful in their career, find a great job, or hit and crush quota in their role.

**Lenny** (00:08:22):
Awesome. I think that gives a clear picture of why you have such unique insights. I don't know if there's anyone that has such a broad access to so many salespeople and what they're doing, what they're thinking about. The core part of the Bravado product, just to make it even clear, is a community or people ask questions, help each other through sales issues, things like that, right?

**Sahil Mansuri** (00:08:41):
Yeah. So if you're familiar with Stack Overflow and what that network and community means to engineering, Bravado has a product that's affectionately known as the War Room, which does the same thing. So you have 50,000 companies, sales teams that are on Bravado. We get a realtime pulse of which companies are hitting quota, which ones are missing quota, which sales reps are closing deals with which organizations, which industries are doing better or worse. 

**Sahil Mansuri** (00:09:12):
So we do get a really interesting perspective within the world of B2B tech sales, to be clear, a really interesting perspective on what's happening in terms of companies and revenue and forecast and quota, which gives us hopefully an opportunity to serve those members and the general tech community at large in terms of how they can beat the odds, especially as we're back to that 2008 crunch that we saw then as well.

**Lenny** (00:09:39):
Awesome. Just to put this out there, I'm a very small investor in Bravado. I'm just a fan of these kinds of companies, community led SaaS tooling. I was really impressed with the way you're building and the way you're approaching it. Also, I don't have a lot of depth in sales, and so I loved this opportunity to learn about how sales works by participating. So thank you for letting me join the journey of Bravado. It's a really unique company and I'm excited to see where it all goes. 

**Lenny** (00:10:05):
So with this podcast, we were planning to talk about sales. Initially, it was going to be how to get better at sales, how to be a better salesperson. But you had this great suggestion that we instead focus more specifically on what founders should change in the coming year knowing the conditions of the market and how things are turbulent and how people are spending less and things like that. So we're going to talk about five things that you can do right now to change the way your sales process works starting now for the next year. The idea is once you listen to this conversation, you can go and do these things immediately with your team. So that sound good?

**Sahil Mansuri** (00:10:41):
Yeah, it sounds great. I mean, I think, inherent in this conversation will be things that you can do to be better at sales, but I think the way in which you sell has to be different based on market condition. So if we had done this podcast eight months ago or 18 months ago or 28 months ago or 38 months ago, I think we would've had one set of conversation. We would've talked about growing top line revenue. We would've talked about how to get your first 20 customers. We would've talked about how to build and scale a sales team. We would've talked about setting quotas and whatnot. 

**Sahil Mansuri** (00:11:18):
I think that today, the market has shifted because we know that the cost of capital has gone up. We know that funding has dried up. We know that investors today are only interested in companies that have strong unit economics and have high retention rates. Cold prospecting goes down in favor of cross-selling and upselling your existing customer base because it's hard to break into new accounts when companies have budget freezes and hiring freezes and layoffs, and everyone is watching really closely the capital outflow of their business. So your sale strategy has to fundamentally change in order to meet the moment and meet the market to where it is.

**Lenny** (00:12:00):
Great context setting. You touched on a few of the things we're going to talk about, so I'm excited to get into it. The first topic I wanted to chat about is forecasting and quotas. You have some advice on how founders should be thinking about adjusting their forecast plans and their quotas for next year. Can you talk about that? 

**Sahil Mansuri** (00:12:18):
Yeah, so let's start with some data and then we'll talk about why this matters. So on Bravado, as I mentioned, we have 300,000 members, but only about 200,000 of them. So about 65% of the network uses a product called the Seller Portfolio. The Seller Portfolio is a realtime tracker of how you and your sales team are performing relative to quota. You can kind of think of it like mint.com, but instead of being for personal finance, it's for sales. Based on that, we're able to get a realtime perspective on which companies in specific, and then overall which industries and in which sectors are at or above or below quota. 

**Sahil Mansuri** (00:12:57):
So I'll share some stats with you. So in Q3 of this year, so I guess as of last month, in Q3 of this year, 63% of sales reps missed quota, 63%. That's up from 54% in Q2 and 46% in Q1. So you've basically got 30% more of the sales team missing quota today than you did literally just six months ago. If you broaden that out to a team wide structure, 76% of companies missed their Q3 target. 76% of companies missed their Q3 target. That's up from 59% in Q2 and 51% in Q1. So you actually have 33% more companies that are missing target. 

**Sahil Mansuri** (00:13:46):
Then at this point, it's gone from being like the occasional company is struggling to pretty much every tech company is struggling. We would predict, based on the data that we're seeing, that over 80% of companies will miss their Q4 goals. So in a world in which the vast majority of sales reps are missing quota and the even larger vast majority of companies are missing quota and their forecast, that on the one hand explains why you're seeing this bunch of layoffs.

**Sahil Mansuri** (00:14:15):
On the other hand though, it raises the question of what do I do for next year? On the one hand, you don't want to bring down targets too significantly because it's going to raise a lot of red flags in terms of spend and burn and probably meet a lot of really painful decision. On the other hand, it's really hard to have visibility into what the market's going to look like six months, I mean, heck, even like six weeks from now. Things are changing on a realtime basis. 

**Sahil Mansuri** (00:14:44):
Something interesting that we saw is that we have quarterly tracking, but we also have monthly tracking. So something interesting we saw is that from November until March of last year, companies were basically blowing out their quota, sales reps were blowing out their quota. All of a sudden everything came to a screeching halt in April, and April, May and June were really tough times. You saw that outwardly in the market in terms of layoffs and hiring freezes and such. But we saw it on a realtime basis in terms of percentage to quota and companies missing their target.

**Sahil Mansuri** (00:15:15):
What was interesting is that a bunch of companies then revised down their forecast for the rest of the year, but then companies started beating those forecasts in July, August, September. So for a moment there, it actually looked like we might be out of the worst of it, and then came obviously a much maligned double dip recession, which then in October, November, all of a sudden everyone just started missing. Many of your listeners, I would imagine, work at VC backed SaaS companies, so they can, in the comments or whatnot, speak about whether this is also true for them. 

**Sahil Mansuri** (00:15:48):
But I would imagine that for most of companies going into the middle to end of September, they probably felt pretty good. They actually thought like, "Oh, maybe we can actually squeak by in Q3. Maybe we can revise up forecast in Q4. Maybe we can hire into next year and we can go back to growing the way we were for the previous 10 years." Then October was just a bloodbath. On companies that do monthly quotas, 85% of sales reps missed quota in October for their monthly number. I think it's going to be even higher in November based on what we're seeing. 

**Sahil Mansuri** (00:16:26):
So again, I share all this information with you to just kind of set the stage on what's happening realtime in the market. So given that September felt good, but today we're totally screwed, it's hard to plan what you should do for all of 2023. I think the advice that most founders are getting from their boards is when you have limited visibility, you have to plan in the most conservative way. On the one hand, of course that's true. You have to be conservative. But on the other hand, you don't want to be unreasonably conservative because you don't want to be floundering from like, oh, we're screwed to everything's better, to we're screwed, everything's better. 

**Sahil Mansuri** (00:17:06):
So the way I think about setting up a plan when you have limited visibility and some major headwinds is setting up a really conservative plan and then having milestones, short term  milestones that unlock the ability to lean into growth and spend based on hitting those targets. So here's an example. Let's say that you did $10 million in revenue this year and next year you have no idea what that's going to look like. Maybe you say, "Okay, let's plan like we're going to be down to 9 million. We're going to lose 10% of revenue next year despite our best efforts because the market's going to be really tough."

**Sahil Mansuri** (00:17:45):
So that would mean that in Q1 you need to hit 2.5 million in revenue. Let's say in Q1, if we hit 2.5, then we should revise up our targets for the rest of the year and we can unlock this additional budget to kind of spend off of. If we hit below 2, we should revise down our number. So kind of being comfortable with regularly reforecasting. Forecasting, you can't just forecast a quarter out every time. Obviously that's a tough way to run a business. So you got to forecast a year, but then set milestones, checkpoints and kind of make predetermined decisions that allow you to avoid the bias of then walking into Q1 and being like, "Oh, we missed in Q1, but no, no, we're really going to hit it in Q2."

**Sahil Mansuri** (00:18:29):
You got to set the targets upfront because as founders, we tend to have a bias towards optimism. That's generally how founders operate. In today's market, that's more of a disadvantage than an advantage. So my suggestion is to really think about forecasting conservatively, setting up checkpoints and milestones around what future success may or may not look like. If you hit those goals, then decelerating or accelerating into it depending upon what you get there, and coming to an agreement with your board, with your sales team, with your sales leadership in advance so that there's no debate about what to do when you actually get there.

**Lenny** (00:19:06):
That is awesome advice. As a PM, it makes me think a little bit about moving to an agile sprint sort of system versus this long term waterfall oriented planning process. Have you seen this need happen in the past? Is this the first time we need to plan to reforecast throughout the year? Or have you been through periods where this is just the way people operate when times are super uncertain?

**Sahil Mansuri** (00:19:28):
First of all, I think the vast majority of CEOs and sales leaders haven't been through a period of dramatic uncertainty in their careers. I mean, there are obviously people who have been in business for more than 15 years and who have been through other downturns. But unless you were a sales leader, a CEO, an executive in 2008, which I would imagine that not very many people were or certainly not everyone was, then you haven't seen anything like this. People try to analogize it to COVID, but I think that that's actually not a good analog for this. 

**Sahil Mansuri** (00:19:59):
The reason why is because COVID was an external factor versus this is actually an internal issue, which is to say that there are actually industries that are doing much better these days except for tech. Tech is getting crushed, right? In COVID, everyone's getting crushed. So it didn't matter if you owned a yoga studio or gas pump or whatever, a hotel. There was nothing that was working well unless I guess you owned Amazon Fresh or something. There were very few businesses that were doing better as a result of COVID. But there's a bunch of companies that aren't doing that bad. I mean, if you listen to other podcasts, you've probably seen that tech is the one that is getting the most hammered in this, although I think in the last two weeks, crypto has caught up pretty quickly.

**Sahil Mansuri** (00:20:47):
But it's really kind of tech, right? So when you see a slowdown in tech that is disproportionate, you have to assume that it may last for a much longer period of time than you imagine. I think that given the lack of visibility and the amount of volatility, I think it is a unique situation for most companies, for most leaders. I think that the only response to which is to try to get really comfortable with being wrong and adding new data in in order to make decisions regularly without the fear of coming across as not knowing what you're doing.

**Lenny** (00:21:27):
Things seem to have been crazy for a long time. It's interesting that this is the first year where you're finding that companies have to do this. Before we get to the next topic, I wanted to come back to the stats that you had real quick. Can you talk again about how you get those stats? Is this like a salesperson plugs into their system somehow in exchange for getting access to the benchmarking? How does that work because that's very cool?

**Sahil Mansuri** (00:21:49):
Yeah, exactly. That's right. It's a gift to get model. So the way it works is that you enter your stats, and in doing so, you get global benchmarks of how you're doing versus other reps or other companies. So there's a premium for being accurate here because otherwise you don't actually get a real sense of how you're doing versus others. So there's an incentive structure that's built in to be really precise. Then that information feeds into our kind of global leaderboard where we are able to slice and dice and say, "Okay, of companies that are headquartered in San Francisco, here's how your company's doing. Of sales reps that sell to CMOs, here's how you're doing. Of reps who carried a quota of between 500, 700K this quarter, here's how you rank." So we do global benchmarking for sales reps and sales teams and we share that information for free to anyone who is willing to participate in the ecosystem.

**Lenny** (00:22:43):
That is very cool. I had no idea that was something you did. How do folks join that if they want to join up?

**Sahil Mansuri** (00:22:49):
Simple, everything's available for free. Just come to bravado.co and we have something called a Seller Portfolio. Go ahead and build one of those and then enter the information and then you'll start to receive the stats as they come out each quarter.

**Lenny** (00:23:00):
Sweet. Okay, second topic, comp plans. You have some advice for how teams should think about comp plans for their sales people? What's your advice?

**Sahil Mansuri** (00:23:09):
So comp plans are, or compensation plans for sales, are very different than they are for most other profession. So in most professions, yours and product management, you have a base salary that encompasses the vast majority of your cash compensation. You then often have bonuses that are either based on company or sometimes personal milestone, which are often paid out end of quarter, end of year. Then you'll have an equity grant that you vest over the course of time. That's not how it works in sales. 

**Sahil Mansuri** (00:23:39):
So the way it works in sales is that you have what's known as a base and then what's known as an OET. An OTE or on target earnings is how much you make if you hit quota. The most common ratio that you see in SaaS is what's known as a 50-50 split. So let's just use some round numbers. Let's say that your OTE is $200,000. What that means is that your base salary is actually only $100,000. So unlike in most other professions, sales reps make very little base salary, but their OTEs are often higher than in most other professions because they're variable, so the second $100,000 you unlock through your performance on the sales team. 

**Sahil Mansuri** (00:24:25):
Again, I'm going to use the most common examples for this, and every combines different, et cetera, but what's really common is if you have a 200K OTE, 100K base, 100K commission, then your quota will be $1 million. So the ratio between your OTE and your quota is typically five to one. So your quota is usually 5X. This comes from this idea that your cost for a sales rep fully loaded should be about 20% so you can afford to pay 20% of your salary to a sales rep. So let's talk about what that all means. 

**Sahil Mansuri** (00:24:59):
So what that means is that you as a salesperson have to sell $1 million of software in order to make $200,000 of money. But that $1 million of software is only around new business. The vast majority of account executives are only responsible for new business, which means top line revenue growth. So let's pick two theoretical examples. Okay, let's say they're sales rep A and sales rep B, and they both have the same quota, same OTE, okay? We're selling for the same product, same sales team. Sales rep A closes $1.5 million in 2022. Just for easy math, let's say that's 15 100K deals. So product is 100K. They sold us 15 deals a year. They would close $1.5 million. 

**Sahil Mansuri** (00:25:46):
That means that they would hit 150% of quota. When that happens, when you exceed your quota, you hit in sales what are known as accelerators. So it's not like if you hit 1 million, you make 200, but if you hit 1.2 million, you just make an extra on that 200K. You actually often make extra money for exceeding your quota. The more you exceed your quota, the more money you make. So you would imagine that if someone sold 1.5 million, they wouldn't make 300K, which would be 20% cost to sale. They might make 400K. That's pretty common in sales. 

**Sahil Mansuri** (00:26:21):
So this person who closed $1.5 million in business from 15 deals ends up making $400,000 and they get taken on a free trip to Cabo because they made President's Club and they're put on the leader board and the CEO of the company gives them an award at the end of the year and they are heralded as the pinnacle of all things that are sales. The VP of sales says, "Wow, I can't wait to clone 10 of you." That's how sales teams are set up, right? 

**Sahil Mansuri** (00:26:47):
Then you have sales rep B. Sales rep B only closes 12 deals for 1.2 million. So they still exceed quota, but they only exceed quota by 20%, not 50%. That sales rep ends up making let's say 250K. So they make $150,000 less money. They don't get to go on the trip to Cabo. They don't get the award at the end of the year. They're not the ones that are celebrated or championed and they're seen as a good performer but not as good as team player A. That all makes a lot of sense in a world in which companies are really focused on top line growth.

**Sahil Mansuri** (00:27:25):
Nothing is more important than the amount of ARR you're making and how fast you're growing and investors are basically demanding that you go 3, 2, 2, 2, which is common parlance for if you make 5 million this year, you should make 15 million next year, you should make 45 million the year after, and then you can slow down to going 90 then 180. This is how VCs often think about funding SaaS companies. They look for this 3, 3, 2, 2 sort of multiple growth on ARR, new business ARR. That's how the world used to function until six months ago. 

**Sahil Mansuri** (00:27:58):
Then six months ago, all of a sudden the music stopped and capital got expensive and everybody started being like, "Whoa, wait a minute. We should think about things like net dollar retention and we should think about what renewal rates look like and we should think about how efficient you are at acquiring customers." All of a sudden, profitability, efficiency, retention came into focus as everybody realized that unprofitable growth was no longer going to be rewarded because you couldn't just keep spending in order to acquire customers. Acquiring new customers was going to get harder so retaining the ones you had and making sure they were happy was actually far more important.

**Sahil Mansuri** (00:28:35):
So let's go back to our example. So team player player A who closed 15 deals for 1.5 million, poster child for the company, got $400,000. Let's say out of their 15 customers, 10 of them churn next year and only five of them actually end up renewing. How much does that affect player A's compensation, their performance, their celebration, et cetera? Doesn't affect them at all. Make no difference. 99% of SaaS companies are set up this way, right? Every SaaS company of, with very small exceptions, HubSpot, monday.com, there's a handful of them, except for very few SaaS companies, no difference to the salesperson's performance. It's seen as a failure of customer success. Other people get blamed for it. Sales rep, no change in their comp work or their success.

**Sahil Mansuri** (00:29:32):
Meanwhile, sales rep B who closed fewer deals, 12 of them. Let's say all 12 renew, and not only do all 12 renew, but let's say that three of them actually are so happy with the product and service that they're willing to be featured on your website as the folks that you advertise. Let's say six of them are actually willing to be references. So they help you close even more business by getting on the phone with prospective customers and are willing to actually advocate for your product. Let's say that not only do they renew, but four of them actually upsell because they're so happy they end up spending more and they sign multi-year contracts and whatnot. 

How much did that affect sales rep B's performance? Do we go back and revise and say, "Well, wait a minute. Actually sales rep B's customers were way better and actually we should probably have rewarded sales rep B because they actually had done the homework of finding the right clients instead of just shoving product down people's throats." No, none of that happens. Again, that kind of made sense up until six months ago, but it makes no sense today. So sales comp plans are stuck in the stone ages. They're stuck in the world of Glengarry Glen Ross, Boiler Room, Wolf of Wall Street, get the dollar in through the door, Matthew McConaughey [inaudible 00:30:45]. That's where sales comp plans are. 

**Sahil Mansuri** (00:30:49):
What we haven't done is built a modern technical sales compensation plan that actually aligns the needs and incentives of the business, the customer and the rep. So I think that for a while there, I mean, I've been writing and talking about this for years, for a while there it fell on a lot of deaf ears because no one cared. People care now because all of a sudden for the first time, all of the things that we're talking about around retention and renewal rates and stuff are coming up. So I would say that my general advice to companies is to say what are the metrics that matter and ensuring that those metrics are the ones that your sales team is rewarded for. 

**Sahil Mansuri** (00:31:31):
I also call into question the notion that your sales team should have a 50-50 split on compensation. By the way, that doesn't just extend to the sales team. That's often how the VP of sales is compensated. So your executive, your chief revenue officer, your VP of sales who sits at the same table as your CMO and your CFO and your COO, that person also has a 50-50 split in most cases. Sometimes it's 60-40, but it's very rarely 90-10, which is what it is for almost every other executive on your team.

**Sahil Mansuri** (00:32:00):
So salespeople get labeled as coin operated and mercenaries and all these other adages because the way we compensate them, the way we treat them, the way we measure them is in a mercenary sort of way. Again, I would call on founders and VCs and executives to rethink that and to instead come up with compensation that aligns the incentives, again, of the customer, the business and the rep and the leader. So I think that setting up a longer horizon where if the customer you sign up today ends up renewing tomorrow, the rep should get a kicker on it. 

**Sahil Mansuri** (00:32:40):
We should look at what the overall renewal rate is of the sales rep comparing it of course to the renewal of the rest of the business. If one rep is doing a better job of qualifying the right customers upfront, they should be rewarded for that. So things like that I think are missing from sales compensation and I'm excited to see them come to the front this year.

**Lenny** (00:33:00):
As an outsider, this all sounds very obvious like this is how it should work. I imagine a reason it doesn't is it adds complexity and then there's this feedback loop that's a lot longer because you have to wait to see if they renew. So two questions that I guess. One is you're saying that it works companies are doing it this way. You mentioned a few, HubSpot, monday.com. Are there others that folks can look at to model how they could approach it this way? Then is there any other reason that folks haven't rethought the way comp plans work? Is it just like, "Nah, it's working, we don't have to break it"?

**Sahil Mansuri** (00:33:36):
I'll answer the second question first because the answer to the first question is really simple. I think that there is a lack of transparency around how a lot of sales compensation plans work and companies tend to make it up as they go along. Oftentimes companies change their comp plans like each month, each quarter based on whatever is the business unit or the goal of the business. So I've seen things like, oh, company release product B after only selling product A. So we'll double the commission on product B because we want to get it in people's hands. Or we really want to target CPG customers so CPG customers are worth extra commission. 

**Sahil Mansuri** (00:34:12):
So companies tend to weigh down comp plans with basically a bunch of bullshit that doesn't have anything to do with how the compensation plan should be structured, but just has to do with the whims of the executives and the board that month or that quarter. So I don't know of any organizations I think do this excellently. I just know a lot of companies that do it better than most. I think it depends on your company or business and your incentive. But I would say that in today's economy, taking a longer term view to a sales compensation, instead the short term, like you're a hunter, your job is just to close deals and doesn't really matter, a dollar is a dollar no matter where it comes from is not true anymore. 

**Sahil Mansuri** (00:34:55):
So I guess that's the answer to that. Coming back to the other question though, which is why are sales comp plans not innovated off of because this seems obvious? First of all, it's obvious because of how I explained it. I'm not taking credit for it. It's just that I'm giving you a lot of context that you would not get otherwise, right? The context you would get otherwise if you just walked in and you got your traditional old school VC and CEO doesn't really know what they're doing and just listening to their board is like, here's how sales comp plans work, right?

**Sahil Mansuri** (00:35:25):
You want to grow revenue, you want to get customers, you got to pay top dollar and you got to fire them up and set aggressive quotas and you got to push them and you want to put these big spiffs out there because that's how salespeople work. A founder doesn't know. This is the problem is that people don't know because nobody really understands sales and salespeople. They just kind of are like, "Well, I can't sell and I don't really want to do that. So I'm just going to hire this 50 year old white guy who's done this at a bunch of different companies and then have him bring in because it's always a 50 year old, it's always a white person and it's always a guy, right?"

**Sahil Mansuri** (00:36:01):
Sales is one of the least diverse professions when it comes to leadership and it's one of the things that we really champion here at Bravado is this idea that 92% of sales leaders or VPs of sales are white. Over 85% of sales leaders are white. So is that representative of the total population of who should be a sales leader? No, of course not. It's just representative of the fact that like, oh, you don't want to innovate here. Just hire someone who's been there, done that before. 

**Sahil Mansuri** (00:36:31):
So you get a lot of sludge in the system. You get a lot of people doing the same shit over and over again even though it doesn't work, which is kind of the opposite of that Einstein quote, right? So founders don't know how to set comp plans. They are just listening to what other people tell them should be the way they do it. There's a way it's done and it's really hard to break that. It's kind of like when you talked about waterfall versus agile. Once you do agile you're like, "Wait, why would we have ever done it the other way?" Well, it's because everyone was always doing it that way, et cetera, et cetera. No one ever got fired for buying IBM, et cetera. You get where I'm going. 

**Sahil Mansuri** (00:37:06):
But the other thing Lenny that I think is problematic is everyone loves to optimize in the short run when it comes to revenue in sales. That's really I think the other big driver. If I offered you a plan that said, hey, you can grow by 20% revenue quarter over quarter or we can spike revenue by 75% this quarter though I don't know what that's going to do to the business in the future. Which of these do you want? Tell me how many founders really are willing to take option A? What do you think? 

**Sahil Mansuri** (00:37:37):
Let's say I just told you those were your options. I can figure out a way to increase revenue by 75% this quarter though I can give you no promise as to what that means for the future. Or I can make you a plan where we increase revenue 20% quarter over quarter for the next six quarters. Which of those two plans would you sign up for? What do you think is a percentage of startup founder six months ago, eight months ago, 10 months ago to indefinitely that would've signed up for plans?

**Lenny** (00:38:01):
Yeah, it's interesting. Hearing you describe the way it should be structured and then hearing you pitch this. I would definitely pick goal one. Let's grow. Let's get this. It'll work out, it'll work its way out. We'll figure it out later. Let's just keep new customers coming in. So I don't know. I guess like 99% probably choose that first one.

**Sahil Mansuri** (00:38:25):
Yeah, I think that's right. Well, I mean that is right because that's what everyone signed up for. But then all of a sudden, and again, that was okay because even if all your customers churned, it didn't matter because you could just go raise more money based on the growth and then just keep pouring more money on it, more money on it. No one gave a shit about the leaky bucket, right? Because you could just keep adding more water at the top. Now all of a sudden the faucet's off. 

**Sahil Mansuri** (00:38:42):
So given this seismic change in the market, how is it that we can reverse the short term thinking and start to actually build good businesses? Because I think that's the real problem, right? The real problem isn't sales compensation plans and quotas. That's a symptom. A real problem is we all just wanted to have hyper growth instead of thinking are we actually building good businesses. I wouldn't say that we at Bravado were immune from this by the way. It's not like I'm sitting here on my golden throne pontificating to the masses. 

**Sahil Mansuri** (00:39:23):
We made a bunch of decisions over the course of growing this business that were incentivized for the short term. Every single time we did that, it ended up being really expensive. Now, sometimes we caught that before money ran out and before we saw the problem. Sometimes we didn't and then we were like, "Oh, shit. It's a fire drill." But at the end of the day, there is no replacement for building a product that customers love and having a great go to market motion that brings that product and that value to your clients and ensuring that they actually are thrilled that they bought your product and are getting a lot of value from it.

**Sahil Mansuri** (00:40:00):
Yeah, it sounds so simple, but the amount of companies that actually don't really care if their customers get value from their product versus just measuring top line revenue growth numbers and logos and whatever is I think more meaningful than people are willing to admit.

**Lenny** (00:40:16):
**Sahil Mansuri** (00:41:42):
Let's start here, which is cold call, cold email response rates have never been lower. Never been lower. I think you're seeing this across every sales team. Again, if you're listening to this and you have a sales team, you know what I'm saying is true. Top of funnel pipeline is drying fast faster than our planet's drying up in fact. Enterprise sales cycles are just getting longer and longer. We are lucky to have a couple of investors who have really, really broad exposure to the tech market. Everything from really large public IPOs all down to small startups. 

**Sahil Mansuri** (00:42:21):
In conversations with them, they've been really clear that they're seeing this incredible, the average enterprise sales cycle is 62 days, it's now like 115 days or something. So customers are dragging their feet, everything's going to no decision, no decision typically means I'm not going to say yes now because I don't want to spend the money. I actually like the thing but I'm not going to buy it. Which means the same thing for you as a business, which is that you're not making any money. 

**Sahil Mansuri** (00:42:45):
So in a world in which you can't sell to new customers, your only hope is to keep the ones you got for long enough to survive and then hopefully even maybe be able to upsell and cross-sell those customers into new products, as well as potentially leverage those customers to get warm intros into a potential new business. Psychologically, when times are tough people hoard, people keep their things close and people trust the safety of those they know versus those they don't. This is basic human psychology, right? 

**Sahil Mansuri** (00:43:18):
So given that that's the case, if you're a company that doesn't have a lot of customers and you're trying to go out to market and sell your product, you're in a lot of trouble. If you are a company that has a large customer base and you've done a shitty job of engaging, retaining, maintaining relationships with them and prioritized top of line growth, this is your alert. This section is for you. Because what you should be doing, I will tell you the most dramatic thing you could do and then we can kind of work backwards. Take your best sales people and make them CSMs. There's no point. There's no point in having your best salespeople sell.

**Sahil Mansuri** (00:43:59):
Well, what's the point if people aren't going to buy anyway? If they do, they're going to buy in onesie, twosies, not these big enterprise deals. No one's going to sign these big accounts right now. Who in tech today is like, "Wow, I can't wait to sign a multi-year contract with a new vendor we've never tried." Right? Nobody's doing that. If people are signing things, they're signing for three month pilots or kind of like all sort... I mean, the deal sizes are coming down, et cetera. I mean, this is all very common. Make your best sales people CSMs and be like, "Your job is to make sure that all these great customers we have never, ever, ever leave."

**Lenny** (00:44:33):
CSM is a customer success manager?

**Sahil Mansuri** (00:44:35):
Thank you. Sorry, sorry. I'm too jargony. Thank you. So typically most sales orgs are divided into pre-sales and post-sales. Pre-sales worked with companies that are not yet customers to get them to sign up. Post-sales works with companies that have already signed up to help them either find value or retain or renew or upsell. That's how most sales orgs are divided. Typically, you put your best people in pre-sales because it's harder. It's harder to sell a new customer than retain the one you have. That's always the case because you got to actually be able to build trust, build the relationship, evangelize something that they haven't bought before. 

**Sahil Mansuri** (00:45:08):
So you typically take your best talent and put it in pre-sales, and then you take the people who are really good relationship builders and really caring and nurturing and not necessarily the people who are the most gifted at creating value or whatnot and you put them in CSM. That's obviously a huge generalization because I know many CSMs who are much better at sales and new business. In many businesses, it's actually harder to be a CSM because the product isn't very good. So you actually have to do a lot of selling even after the product is sold. So that was a big generalization. But it is, in broad strokes, true.

**Sahil Mansuri** (00:45:44):
I would take your best account executives, pre-sales reps and I'd put them into CSM. I'd say it doesn't matter how much new business we work on in the next six to nine months because it's going to be hard anyway. But what we cannot under any circumstances do is lose our existing customers because replacing them is going to be impossible. So it's kind of like you got your leaky bucket, you got to patch that leak really, really fast and really hard. I think putting your best people on it is one good way to start.

**Sahil Mansuri** (00:46:09):
Now, there's a lot of people who are going to listen to this and think that's crazy. Why would I take my best performer in a tough market and move them to post-sale? This is bad advice. Maybe. Maybe it's bad advice. I can't predict the future anymore than anyone else can. But I can tell you it's what we're doing. I can tell you I'm actually doing it. We're taking our best people and are moving them into CSM at Bravado. We're trying to maintain every customer we have because I believe that doing so sets us up for the best chance of success in the business. Maybe you disagree with that and you think that that's not right for you. You should do what's right for your business. 

**Sahil Mansuri** (00:46:45):
But I would say that it's not just talk, it's action. I'm doing it. I'm also telling every one of my portfolio, I do a decent amount of angel investing, I'm telling everyone of my portfolio companies to do the same thing. Discussing the same thing with our investors, with our board as well. 

**Sahil Mansuri** (00:46:58):
Okay so you put your best people on it. What else should you? So I think that what often goes underserved is the opportunity to help your customers themselves survive. I don't know. What's a good product example? Let's take something like a analytics product. Let's pick on Amplitude or Mixpanel or pick your favorite. If I was a company like that and I was like, "Okay, don't know how many new customers I may be able to sell, but I've got a lot of really good customers I want to keep." I would invest a tremendous amount of energy into helping product managers and product leaders get benchmarks and stats on how other product teams, what changes they're making. 

**Sahil Mansuri** (00:47:46):
Because the advantage you have as a vendor, this is advantage we have in sales as Bravado, but it's the advantage that every vendor has is you get a cross=section of what everyone who fits a certain ICP is doing at the same time. How good are you at extracting value out of that and finding ways of becoming less of a tool as part of the SaaS stack and more of a value added advisor that can help you actually plan and prepare for what to do next. I think most companies are not good at it. They put out a white paper for lead gen. I want to put out a white paper for customer retention. 

**Sahil Mansuri** (00:48:26):
One thing that we're actually doing is we're basically saying to all of our clients, "Hey, we'll tell you what percentage of companies that look like you are hiring or not hiring. I'll tell you how they're adjusting quotas. I'll tell you how they are changing their comp plans. I'll tell you how much they're paying. I'll tell you what percentage of their sales teams' hitting quota, et cetera, if you stick around with us as a client." I'm not just placing sales reps and say we make our business as a recruiting marketplace. So we help companies hire salespeople. Obviously that's slowed down tremendously because people are scared to hire and spend money right now. 

But if they're getting insights on what's happening in the market, that's still valuable. That's still something that they can't get elsewhere that I am uniquely positioned to offer to my customer base. What are you uniquely positioned to offer to your customer base? Let's pick another example that I think is really easy which is Greenhouse or Lever or another app and tracking system. If you're an ATS and all of a sudden every recruiting budget's getting slashed and recruiters are getting laid off faster than any other department because no one's hiring, et cetera, you're probably at the most risk of being ripped out or being downsized or getting downward pressure to your [inaudible 00:49:37].

**Sahil Mansuri** (00:49:39):
Can you do that nobody else can do in order to give your customers a really good insight into how they should navigate thinking about hiring versus layoffs versus headcount versus burn per department, et cetera? You've got some really interesting data, don't you? You know exactly how many customers have paused, how many roles and whatnot. If I was Greenhouse, I would be putting out all kinds of reports that tell me, let's use me as a customer here, "Hey, of series B companies that have roughly 50 employees, they used to have eight open head count, but now they're down to four. The main area that they're investing are X, Y, and Z. Salaries are moving up and down."

**Sahil Mansuri** (00:50:21):
You could get a lot of insight from a company like Greenhouse. Then I'd be like, "Whoa, this is so valuable. I can't live without this data because this is actually helping guide my business decisioning." I think moving from a world where you're just focused on how can I jam product down your throat to how do I use my unique perspective in the customer segment we serve in order to create broader insights for the industry is something I would heavily prioritize. I'd take my product marketing team and I'd kind of shift them to be my research team. I'd take a data analyst or two and stick them on the project and start to create content that is exclusive for my customers and have them see that as another point of value that they can get that would maybe help stay off chart.

**Lenny** (00:51:07):
I love that advice. Be helpful. Find ways to be helpful even if your core product isn't... Basically go above and beyond what you're already doing as a software product and find ways to help your companies be more successful. Feels like there's just a ton of nuggets you just shared. I want to make sure we also get to this other topic that I think is also going to have a lot of great nuggets, which is around just advice for closing deals in this time. You touched on a couple of these, warm intros, a couple things. Anything else you could share of just ways to increase the rate at which you close deals during this wild time in the market?

**Sahil Mansuri** (00:51:40):
This is a good segue because it'll bridge us back to where you just came from and hopefully move us forward, which is warm intros. So if cold outreach is going to be less effective, then what increases in efficacy in this time is, again, warm intros. So one thing you got to remember as a more general statement is that companies either grow or they die. There are no middle. There's no, "Oh, we're going to cut burn and just try to survive the winter long enough so that..." That doesn't work, right? Because employees get demoralized, investors lose faith, the days become long and the nights become longer and eventually you just run out of energy as a business. 

**Sahil Mansuri** (00:52:20):
I think startups in particular are effectively energy driven. The more energy, the more belief, the more momentum that you have, the more tailwinds you have, the more things grow and feel possible. But of course if you look at the odds empirically, no startup should never begin because the odds are you're going to fail. That failure meets you in the eye over and over again as you're shrinking the size of your team, as you're shrinking the size of your budget, as you're doing fewer things and you're taking things away. 

**Sahil Mansuri** (00:52:50):
So I don't really believe in this like, oh, we are just going to survive mentality. I think you have to adjust, of course. I think you have to be a realist. I'm not suggesting that you be blind to reality. I'm just suggesting you also have to keep the energy going. So what I mean by keeping the energy going is to say, "Okay, let's get..." So here's a couple ideas. First is let's cut a bunch of stuff but keep some money that we're going to invest in doing an in-person customer event. Okay, why do I think that's a good idea? 

**Sahil Mansuri** (00:53:21):
I think it's a good idea because, first of all, we've all been stuck in our houses for a couple years and so when we get a chance to go on a trip for free somewhere, we tend to say yes. That's nice. Secondly, I think that you could be strategic and maybe have the trip be for customers only and in February or something. So maybe you survive the budget cuts this year because people are like, "Well, I got this great trip and I really don't want to miss it. Is there a way we can just keep this tool on?" You might think, "Oh, well, are you bribing customers or whatever?" 

**Sahil Mansuri** (00:53:52):
I mean, it's just psychology. I think you have to use psychology to your advantage. I would do a big customer event in February, invite all my current customers and say, "Hey, as long as you're still a customer as of Feb 10, 2023, you're invited to this all paid trip to Napa to go drink a bunch of wine for a week." I bet that would probably meaningfully change your churn rate. Yeah, it's not going to change everything but it'll change something. I bet it would. Because at the end of the day, people are people. Sales is done by people. It's a belly to belly human sport. It's not just lines of code on a piece of paper.

**Sahil Mansuri** (00:54:26):
You got to talk to another human, which is what makes it hard and unscalable and more of an art than a science. But also makes it really fun because it just plays by different rules, a different set of rules than many other things do. Recruiting being the other thing that is this. So in-person customer event. The other reason why I like in-person customer events is because they're a perfect opportunity for you to get new deals done. So how does that work? Does that mean I also invite prospects to the event?

**Sahil Mansuri** (00:54:53):
No, actually I wouldn't do that. So I think a lot of companies do this where they'll invite customers and prospects to the same event. They're like, "Oh, commingle and sell each other." Not the smartest way to do it. You want only customers in the event and you want to use that again to share thought leadership and such. But then, during all the happy hours and the lunches and the late evenings and whatnot where you start to say, "Hey look, in this market you're finding value in our product. Who are one or two other folks that you know in the same position as yourself that might also find value? Who do you know that has the same problem? Who do you know that's going through this? Who do you know that might benefit from this research paper, et cetera?"

**Sahil Mansuri** (00:55:30):
You just start collecting a bunch of warm interest. But then you don't just stop at getting the name because a lot of teams stop here. They'll basically get the name and then they'll be like, "Okay, got the name. Now I'm done." Actually not the right way to do it. You get the name and you say, "Great, can you make me an e-intro? Actually even better. Can you connect me over text?" So one tip that I have for all founders, all sales leaders, everyone out there, stop using email. Email is where deals go to die. Text message is where deals get done. 

**Sahil Mansuri** (00:56:03):
So this notion that I'm going to e-intro you over email and that's how we connect is just far worse than the thing that I would really recommend, which I do all the time. We have a Webflow as a customer. I love Webflow. I know their sales leadership. We try to do a really good job for them. Anytime that their sales leader mentions a company that might be needing to hire or whatnot, my only response is, "Great, connect me over text." Then I get the text intro with the person. 

**Sahil Mansuri** (00:56:31):
Here's the other fun part. I don't take the introer off the thread. So the other thing we tend to do is we CC the person who responded, but in text you don't need to do that. You can keep the person on a little bit and it holds the person's feet to the fire to actually show up for the meeting. Again, it's these little things, right? 2% here, 3% here. This is how you win in this economy. You got to do all the things right. So you keep the person on the thread long enough so that you've actually built that relationship for the first call, obviously not forever. But in the first 10, 20 messages, I'd keep the person on.

**Sahil Mansuri** (00:57:06):
That allows you to ensure that the person goes to you, which happens a lot, I'm sure you know. You get an intro and the person never responds or they cancel on you. You can't get back on their calendar. You stay with them. This happened recently where I got introed from one sales leader to another and that sales leader basically then had a family or legit situation but then got busy and was like, "I'm not taking this thing." But I just kept pinging into that group every week or two for actually nine weeks. Then by two and a half months later, the person finally is like, "I'm so sorry, et cetera." Only after my original contact was like, "Yo, you're making me look bad here."

**Sahil Mansuri** (00:57:45):
So that pressure is what forced... Then we got them as a customer and now things are good. So it just takes all that. It takes those little things. You got to build a bridge from your current customer base to future customers and parlay the goodwill, relationship, et cetera that you've earned in serving your current customers to get new ones. Because otherwise, I don't think it's just relying on a bunch of SDRs and cold emails and stuff is going to get you through the next six to 12 months.

**Lenny** (00:58:14):
I love that tip. Feel like there's probably more nuggets. I'm going to keep fishing in this well of tactical advice for closing deals. Is there anything else that you've found? I love that texting tip. I feel like I've been on the end of that one. It works great. So yeah.

**Sahil Mansuri** (00:58:30):
From me. Yeah, that's right. That's right. For example, I didn't have your phone number and I told my wife, "Make sure you take a selfie with Lenny and then send a text message to the three of us on one grad so that I know how to get a hold of Lenny in case he calls.".

**Lenny** (00:58:44):
Here we are now.

**Sahil Mansuri** (00:58:45):
Here we are now. That's right. But the point is sales when done well doesn't feel weird, okay? If it ever feels weird, you're a bad salesperson, right? I've been selling now for 14 years. I've sold literally hundreds, millions of dollars worth of deals. I could pretty much call any customer I've ever sold to and have a conversation with them and it would say, "How's it going?" Whatever. That's because I put a tremendous amount of energy into investing and building a real friendship, not relationship, not business, friendship with the people that I sell to.

**Sahil Mansuri** (00:59:22):
So I'll tell you a couple of sales stories and maybe from that we can mine the nuggets that you're fishing for. I will tell you about how I sold to Facebook when I was at Glassdoor. This is a fun story. So Facebook was the Moby Dick of Glassdoor. I think the first time they tried to sell to them was end of 2008 or something like that. Facebook was one of those accounts that obviously should be on Glassdoor because the way Glassdoor's product worked is that the more people that came to your company page on Glassdoor, the more value there was for you as a recruiting firm to put branding and to put jobs and whatnot. 

**Sahil Mansuri** (01:00:01):
Facebook was the most visited page on Glassdoor. So by virtue of that, it was the best account to sell to. It had gone from CEO to VP of sales to new VP of sales to rep to rep, et cetera. I finally got my hands on it Feb of 2011. The only reason I got my hands on it is because I closed Microsoft. I think I closed both Microsoft and Google at that point. But certainly at least Microsoft. Certainly at least Microsoft. Well, it's important to the story, not to brag. 

**Sahil Mansuri** (01:00:32):
So I looked at it and I looked at who we are talking to, Lori Goler, who's the chief talent. I think she's still the head of talent there, but was the head of talent who we had pitched and every time we got the same response, "No, we are not interested in outside partnership at the time. No, we are not interested." I think she had a canned response for all vendors and it was just the same response in the CRM over and over again. So again, Einstein, right? Same thing over and over again, different result.

**Sahil Mansuri** (01:00:58):
So I tried something different and I sat there and I went through every single review that had been written about Facebook on Glassdoor. First I had it pulled by a data scientist and did a word cloud and did a bunch of analytics on what was being discussed there. Pulled salary ranges, pulled salary ranges for Google and Amazon and Microsoft. So Glassdoor had three types of information. They had the review of the company, they had the outlook of the company and then they had the review of the CEO. 

**Sahil Mansuri** (01:01:28):
So it was like, "Do you approve of Mark's handling the company? Yes or no?" Mark had I think 96% approval rate. He was one of the highest rated CEOs on Glassdoor at the time. I have no idea what it is today, but that's what it was then. So I basically called every review, all the salaries and then Mark's approval rating, and turned it into a nine page report that broke down how Facebook employees, specifically software engineers because that's what we're specialists at recruiting for, how software engineers at Facebook talked about working at Facebook and how it compared to how Google engineers talked about working at Google and whatnot, salary band comparisons and even reviews of Mark specifically versus the other CEOs of the other big tech companies.

**Sahil Mansuri** (01:02:16):
Then sent an email to Sheryl Sandberg, a cold email to Sheryl Sandberg whose email address I did not have, but that I assumed had to be one of 15 things. So I think I put ssandberg@facebook.com in the two line and then in the BCC line put every variant I could think of, everything. I mean everything I could think of I put, underscores and dots and first name and last name and abbreviations and et cetera. The title of the email was Mark's approval rating on Glassdoor. 

**Sahil Mansuri** (01:02:54):
I was like, "Hey Sheryl. I'm from Glassdoor. I was doing research on Facebook and comparing it to all the other big tech companies. I personally work with Microsoft. So I have a little bit of insight in this. Here's what your employees think about you. Here's what Mark's approval rating looks like versus others, et cetera, et cetera." This whole research report, I kind of broke out some highlights, a couple screenshots, attached the report and said, "Hey, I'd love to discuss this with you sometime."

**Sahil Mansuri** (01:03:18):
I think I sent the email around 3 or 4PM on a Sunday. By 6PM I got a response back from Sheryl Sandberg CC'ing elt@fb.com or something like that, which I later found was executiveleadershipteam@facebook.com saying, "Hi Sahil, this is super interesting. We'd love to meet with you tomorrow. Are you available to come to Facebook HQ at 10AM.' So at the time I was 22, 23 years old or something like that. It was pretty new to Glassdoor anyway. So then of course I said yes. I sent the email to the CEO. He was like, "Do you want me to come and whatever?" I just said, "No, I'll handle it." I brought a customer success person and the two of us went.

We actually got to meet first with Sheryl and then I got to go to the fishbowl. I don't know if you know this story, but Mark had a famous office that was all glass in the middle so that he really played [inaudible 01:04:15] or whatever so his known as the fishbowl. So I got to go to the fishbowl. I met Mark Zuckerberg himself. As it turns out that report and that rating got added to their weekly packet because Mark wanted to know on a weekly basis how his rating and how the employees view of Facebook was, how it was changing week over week and what people were writing, et cetera, and it became a thing. 

**Sahil Mansuri** (01:04:43):
I don't know if it's still a thing today, I have no idea. But I got to have this in depth strategic conversation with the executive leaders of Facebook around their reputation, what their employees thought, their pay bands, their interview questions, leadership, guidings, shared the word cloud, sentiment analysis, et cetera. Needless to say, of course, we closed a massive deal with them and whatnot. But that's the kind of shit it takes in order to close deals, right?

**Sahil Mansuri** (01:05:12):
So this idea that I'm going to go onto my CRM system and fire up a hundred cold emails and I'm going to close business, that works when capital is cheap and everyone's buying everything and every rep hits quota and every company's growing, et cetera. That shit does not work when you are in tough times and desperate measures, you got to figure out a way to build your business. So what I would say is you got to really over, over, over index in the whole I'm going to teach you something, right? 

**Sahil Mansuri** (01:05:41):
It's not that I'm going to give you value because that's a really weird thing to say and it's not like my product's going to solve a problem for you because, frankly, I don't know if you know what my problems are. But I think that one thing I would advise is how can I do something that will make this worth your time in a way that it isn't about buying my software or putting job ads on my site. So that's how Facebook became a customer of Glassdoor.

**Lenny** (01:06:06):
That is an insane story. I feel like those are moments that salespeople live for. How did you feel once you got that email that day? Were you just freaking nervous? Were you jumping up and down [inaudible 01:06:15] might work?

**Sahil Mansuri** (01:06:16):
I love to play chess. It's my favorite game. The reason I love chess is because I love to think a few moves ahead. I expected to get that email back. I knew when I sent the email that this was going to work. I was like, "There's no way this won't work." The only way it wouldn't have worked is if she never saw it. So if she sees this, she's going to respond because it would be crazy for her not to. The information on here was so good. So I felt a sense of satisfaction that I had played the game right in a way that no one else that my company had. No one else understood the psyche of the buyer. 

**Sahil Mansuri** (01:06:49):
So to me, sales is I don't care about the commission. I've never cared about the money. I think this is true for most great salespeople. I think this is actually true for most people who are great at something is that they don't do it for the money. They don't do it for even necessarily the trophies or whatever. They do it because they love it. Winning, it's contagious, it's addictive and it's rewarding. Closing Facebook was a blast because I really got a chance to flex into something that I take a lot of pride in, which is being able to deeply understand my customers where they sit and how I can be not a sales rep, but someone who actually changes your perspective and how to do your job. That's what I live for.

**Sahil Mansuri** (01:07:36):
So I think that's what you have to do in order to be a great salesperson is I think you have to be willing to go beyond just the, oh, I want to hit my quota or whatever. If you're a founder and you're trying to sell in this market, it's like how do I get my product in the hands of customers? You got to go beyond. How do I change the way you operate as a business? How do I do something that is transformative? That Glassdoor rating literally got added to the ELT report that went out every single week. That's the part of the story I'm proud of. 

**Lenny** (01:08:09):
You just mentioned that you don't do sales, that you're not a salesperson technically anymore. You run this company. Do you miss that job being a full-time salesperson?

**Sahil Mansuri** (01:08:19):
I think CEOs are full-time salespeople. I mean, think about the job of a CEO, right? Let's start from the infancy, right? Let's start from starting a company from scratch. First thing you got to do if you want to start a company is you have to convince yourself to do it. You got to sell yourself on the fact that you want to do this. This is where most people fail actually. They can't sell themselves. They're not able to convince themselves that they should take this leap. They don't believe in themselves enough to do it. 

**Sahil Mansuri** (01:08:45):
So first you got to be good enough to sell yourself. Maybe that's delusional. I don't really know how to coin that, but let's just say sell yourself. You got to then sell other more talented people than yourself to join you at a time at which you have no money, often no idea, no traction, nothing. They're typically making a lot of money at a well paid... If you hire great founders, they have a choice somewhere to work and  you got to convince them to believe in you, believe in your idea, believe in the future that can be. This is the second place where most people fail. 

**Sahil Mansuri** (01:09:15):
Assuming you do those two things, you still got to do one more thing, which is you got to actually sell an investor to give you capital based on typically virtually nothing or maybe very little attraction. Then you have to go and convince your initial customers to believe in you. Because sure as heck no startups product is great. Everyone wants to be like, "Oh we're going to go change the world." But you're not changing the world today, right? You've got 1/100th of the feature set of any of your competitors and all you have is this dream and this energy and this belief and somebody who's willing to take a bet on you. You got to get someone to be willing to bet on you. That's sales. 

**Sahil Mansuri** (01:09:51):
Then if you do all that, then maybe you need to get some press. So now you got to convince a reporter to write about you and you got to be able to do that. Then maybe you need to hire some more people. So you got to convince some candidates to come work for you. I mean, spend my whole day selling. All I do is sales. All any founder does is sales. It's kind of like venture. People misunderstand this. VCs are salespeople. 100% of VC is a salesperson because they're selling LPs to give them money and they're selling CEOs to take their money in exchange for equity. That's the job of a VC. 

**Sahil Mansuri** (01:10:27):
All the analytics, all the data and the this and the that, those are just updating their CRM. The core function of a VC is to sell. The core function of a CEO is to be a great salesperson. Like any great salesperson, you have to balance cynicism with optimism. Great salespeople don't have what I call happy ears. This is a problem that people misunderstand. People think that being a great salesperson is being ever the optimist. That's actually not the case because then you'll waste your time on a bunch of deals that'll never close. Great salespeople are extremely pessimistic internally and are great at being able to then still be optimistic externally.

**Sahil Mansuri** (01:11:09):
Where they're actually trying to disqualify you. They're looking for signals that you're not going to buy and weeding those out, while still at the same time positively spinning you and selling you. That ability to juxtapose is what diverges good from great. Because good salespeople will get misled by customers who tell them they want to buy, but if you would really press harder, you'd understand that they can't or won't or whatever. So you waste your time on a bunch of companies that never buy versus great salespeople know how to prioritize and spend their time properly.

**Sahil Mansuri** (01:11:39):
The same applies in venture. If you are a CEO who's fundraising, I cannot tell you, honestly Lenny, I can't tell you how many other CEOs I know get constantly misled by VCs where the VC says one or two good things and they're like, "Oh, they're definitely going to invest." As opposed to giving that VC every out to not continue the conversation. If they still are willing to talk to you after that, then that they're for real. I think that being a CEO and being a salesperson are the same job. Different forms of it, of course, different audiences, different products, et cetera. But ultimately they're the same thing. So no, I don't miss it. I do it every single day and I love doing it. I'm learning more and more every day from the failures and shortcomings I have.

**Lenny** (01:12:36):
It's very clear that you love doing it. It's so interesting just to watch the energy when you talk about sales. I rarely meet folks that do sales. So it's really fun to dive into all this stuff. We promised folks five topics, you've gone through four. The last one I wanted to touch on, and you've already talked a bit about this and maybe there's just a quick tidbit to add here is around just how important growth continues to be for companies at this stage. It's easy to be like, "No, the markets are tough. People are going to give us a little bit of a leeway because no one's going to be able to grow." Your point is it's still incredibly important. Is there something you want to add there before we get to our very exciting lightning round?

**Sahil Mansuri** (01:13:13):
I guess there's just one last thing, which is innovation is often put to the side. People just try to do the things that everyone else is doing. So I'll tell you something that we did at Bravado as an example of this. So we run a recruiting marketplace and competing with LinkedIn and AngelList and hired and all the rest of it. Like all those companies, we have seen a massive slowdown in our business. Unlike those companies, we didn't take that as kind of the end of the road for growth for now. But instead said, "Okay, so let me put myself back in the perspective of my buyer, my customer who are often founders and CROs and CFOs."

**Sahil Mansuri** (01:13:53):
Those are the people that tend to buy from Bravado because they're the people who care the most about growing revenue. I can't hire anymore full-time salespeople because the market is tough right now and I can't increase my burn or what, but I still want to get new customers. It's just I can't afford to hire full-time people. In fact, I might be forced to lay off my team. What do I do? We kind of just sat there with a think whiteboard and just said, "All right, let's put ourselves in this situation. What would you do?"

**Sahil Mansuri** (01:14:22):
One of the things that I think would be really interesting is I'm actually willing to pay money to acquire customers. I just can't take the risk that I hire someone and they won't bring me customer. What if we created a 100% commission only sales role? It doesn't exist today in SaaS. It does exist in other places, it just doesn't exist in SaaS really. But what if we created a way for sales reps who can't find a full-time job because the market is slow and companies who can't hire a full-time sales rep but still want customers to work together on a commission only basis.

**Sahil Mansuri** (01:14:57):
Now a year ago, this product would not have worked, right? Because the supply-demand equilibrium was so tilted where every company needed great sales talent and every sales rep was getting multiple offers. So in that world, this product makes no sense. But in a world in which you have far more sales reps who are looking for work and far fewer companies who are hiring, maybe we can create a new model of sales. 

**Sahil Mansuri** (01:15:22):
If Airbnb and Uber grew dramatically during the pandemic and actually are somewhat counter cyclical businesses, because if you can't find a full-time job then you find gig work, what would we be able to do for our community that instead of putting them in a different field, lets them use the skills, the network and the expertise they already have in order to do the thing they want to do, but be able to do it in a down market as well. So we launched something called Bravado Flex, which is a way for companies and candidates to work together in a non full-time employment way. 

**Sahil Mansuri** (01:15:57):
That can mean contract hire, it can mean a hundred percent commission, it can mean fractional work, it can mean small stipend plus milestone base. There's a bunch of different ways at work. Overnight, we went from having a massive slowdown to our business to one of the best months that we've ever had in company history, which was last month, and this month will be even better than that. So while our full-time recruiting business slows, our fractional business grows.

**Sahil Mansuri** (01:16:25):
So I use that as an example of the type of innovation that companies should be thinking of. As well as if you are a company that is thinking of increasing revenue but doesn't have enough levers to pull, maybe this is one that you might want to explore. But I think it comes back down to that fundamental staring at the whiteboard being like, "If I'm a customer and I'm in this world, what can we do today to change the rules of the game?" Because sometimes the rules of the game are stacked against you. As a recruiting business, the rules to the game were now stacked against us. 

**Sahil Mansuri** (01:17:00):
No one's got money. People don't want to hire. There's hiring freezes, et cetera. There's more candidates in the market than ever before. Companies are going to be less and less likely to want to pay us to recruit for them. There's nothing I can do about that. I mean, I can stick my head out the window and scream and cry and complain, but that ain't going to get me anywhere either. So what I need to do is change the rules of the game and start to think about the problem differently.

**Sahil Mansuri** (01:17:23):
I think that not enough founders do that. They just kind of bash their heads against the wall with the same kind of preconceived notions of what success may or may not look like. So I would really advise, and I'll give you some examples of where this goes beyond Bravado Flex, but change your pricing strategy. Now, let's say that you sell a product and it's $12,000 per year. Try charging a thousand dollars a month and going month to month. Try charging 20 bucks a day and going day by day. Then you might be like, "Well, wait a minute. That just changes to every..." But you have to adapt, right? 

**Sahil Mansuri** (01:17:51):
If your old model is not going to work, it's asinine to just sit there and then try to make minor changes like, "Oh, instead of 12 we'll reduce price to 10 or something." People try to optimize their way out of problems. You can't optimize your way out of a problem. You got to completely change the rules of the game. In doing so, you suddenly will learn something new. Bravado Flex may not work forever. Who knows? But maybe, just maybe, as we've been doing this, we've realized that there's actually a lot of sales reps that prefer this because they can do flex for multiple companies. 

**Sahil Mansuri** (01:18:26):
So all of a sudden we learn something really new, which is that our audience are the same candidates that we're replacing to full-time jobs, are actually in some cases preferring doing this fractional work. Because now they don't need to go to all the meetings and they don't need to update Salesforce. They don't need to do all the boring shit that sales reps don't like to do. Instead, they can just work for three companies, use the existing network they have, get meetings set up for all of them, pitch the best product to the right customer, and all of a sudden they feel like instead of having to pitch the one hammer that you need to use for every... They have a wide tool set that they can bring to their customers.

**Sahil Mansuri** (01:19:01):
All of a sudden companies are like, "Well, wait a minute, this is actually pretty cool because now instead of just hiring one person at a time and training them, I can hire 10 people at a time and I can have multiple kind of fish in..." So we just changed the rules of the game around sales hiring as a market. I think that's the sort of innovation that you have to bring to the market if you want to survive in the downturn, which you can't just sit there and just try to do the same stuff over and over and over again. You got to really be willing to break all preconceived notions of what success looks like, innovate something new and then take bigger swings I guess is the thing I would say.

**Lenny** (01:19:38):
That's a very empowering way to close out our chat. But first, we reached the very exciting lightning round. I'm going to ask you five questions. I'll go through them pretty fast. Whatever comes to mind, fire it away. Does that sound good?

**Sahil Mansuri** (01:19:53):
That sounds great.

**Lenny** (01:19:54):
What are some books that you recommend to other people, like two or three, maybe even one book that you most recommend to other people?

**Sahil Mansuri** (01:20:01):
There's one book that I think every person should read. It's called Stumbling Upon Happiness.

**Lenny** (01:20:05):
Yeah, Dan Gilbert I think is the author.

**Sahil Mansuri** (01:20:07):
Yeah, that's right. That's right. It's a really fun book. A lot of interesting studies and readings. I think especially if you're a founder or an executive who wants to learn how to sell and wants to understand how your buyers make decisions, I think it's really impactful and teaches you a new way to think about sales using psychology.

**Lenny** (01:20:24):
Great pick. Second question. Favorite other podcast that you like to listen to?

**Sahil Mansuri** (01:20:29):
There's actually only two other podcasts I listen to, so it's a small choice. I listen to the All In podcast because I love the fact that they have really good show notes so I can just jump to the section that I want to hear them talk about instead of listening to like-

**Lenny** (01:20:42):
We got those show notes here too.

**Sahil Mansuri** (01:20:43):
That's right. I'm excited for that as well. Of course, I listen to yours, but I figured that was too on the nose.

**Lenny** (01:20:48):
It's off limits.

**Sahil Mansuri** (01:20:50):
On the nose, yeah. Then the other one is the How I Built This.

**Lenny** (01:20:54):
Great choices. What's a recent favorite movie or a TV show that you've really enjoyed?

**Sahil Mansuri** (01:20:59):
I don't watch a lot of TV or movies. but I would say that a strong exception to that is I really like The Blacklist, if you've seen that show. But it's a pretty good one. James Spader. Yeah, I really love James Spader. I find him to be someone I really, really like. I'm also a big fan of Aaron Sorkin so I liked The newsroom a lot and then West Wing and whatnot. I think the thing is I really nerdy stuff like Jeopardy and Frasier. I never liked Friends. I think it's just the dork in me that I like to watch nerdy stuff.

**Lenny** (01:21:34):
Final question, what are five SaaS products that you find incredibly useful at your company, especially new ones? But if not, anything that are just I love these products.

**Sahil Mansuri** (01:21:45):
I'm a huge Luddite because my favorite tools to use are pen and paper. I like to write by hand. I like to write on a whiteboard. I enjoy the tactical part of that. I've tried to use the reMarkable tablet and other stuff like that, but I don't get the same pleasure of writing on actual pen and paper. That's my favorite. I mean, in terms of tools that we use it at Bravado that are hugely impactful, I mean, Slack is the central OS of our business as I'm sure it's for many others. Obviously we use Zoom a lot to meet and that's a core one. 

**Sahil Mansuri** (01:22:17):
Noshell operates everything for us as well. So I don't think I'm saying anything that that's exciting here. There's a product called Grain that I really like that I think is really cool. Grain allows you to make clips of Zoom meetings and send them out. The reason I really like that is because if I have a customer call, if I have a user interview or a VC call or whatnot, I can take a snippet of something that someone said and let other people hear it from their words. I think that's really powerful and something that I really enjoy.

**Lenny** (01:22:47):
Great.

**Sahil Mansuri** (01:22:47):
Maybe that one.

**Lenny** (01:22:48):
Great. Love it. Sahil, this was amazing. I feel like I want to be a salesperson now. You infected me, but I still would be really bad at it. But there's a lot of nuggets in this episode that would make me less bad. So thank you for that. 

**Sahil Mansuri** (01:23:02):
I'm going to jump in. You've said that once. you've said that once to me before and I can't let you end on that note because it's not fair because Lenny, you are a salesperson and you are one of the best that I have met. The reason why that's true is because you have built a business from the ground up. I didn't know who the heck you were a couple years ago now. Maybe you had a big brand more than a couple years ago too, and I was just the idiot. But everybody I know now knows and respects you. The reason for that is because, I mean, I think you have really deep knowledge on product. I think there's probably other people that have really deep knowledge on product too.

**Lenny** (01:23:02):
Many, many more.

**Sahil Mansuri** (01:23:41):
But you are the best at marketing that and turning that into... You got distribution around it. You've given so much to the world of product and been kind of a bright light that so many people have gravitated around and such so that when you launch Lenny's Talent Collective or Lenny's whatever podcast or whatever's the latest Lenny thing, in fact I remember you did a poll to try to figure out what should be the name of this podcast and ultimately the thing that one was Lenny podcast I think. So I think that is the core of sales. 

**Sahil Mansuri** (01:24:15):
I want to go back to the first principle, which is that sales when done well does not feel salesy. Sales when done well is a delightful experience. People love paying you money. People love consuming your content because it's good. That's what makes a great salesperson. Facebook didn't regret taking that meeting with me. Facebook didn't regret signing that contract. They enjoyed it, they liked it, they were happy for it and it felt delightful to them and that's how sales should feel. 

**Sahil Mansuri** (01:24:47):
So this notion that the way you're good at sales is because you're super extroverted and pushy and willing to put yourself out there and whatever is a misguided notion. You are the future of sales. If every salesperson gave a ton of value, played the long game, nurtured their community and created products and services based on the feedback from their customers, the world would be such a better place. So don't sell yourself short, my friend. I think you are a phenomenal salesperson.

**Lenny** (01:25:16):
Damn. What a way to end it. I so appreciate that. I'm going to deflect from this epic compliment and move on to closing this out, but I really appreciate that. Where can folks find you online if they want to learn more about you, Bravado and how can folks be useful to you?

**Sahil Mansuri** (01:25:32):
First of all, you can just email me. I'm just sahil@bravado.co. I love responding to emails and meeting people, so I'm always down for that. Secondly, you can find me on LinkedIn where I regularly post content around sales and revenue and hitting targets and all that. Then lastly, if you want to learn more about Bravado, it's just bravado.co. Sign up and check it out. If you like something, let me know. If you don't like it, then please let me know so we can make it better.

**Lenny** (01:25:59):
Amazing. Sahil, thank you again for being here, for sharing all your wisdom with us.

**Sahil Mansuri** (01:26:04):
Thank you. Thanks for having me.

**Lenny** (01:26:06):
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.

---

## [17/20] How Notion leveraged community to build a $10B business | Camille Ricketts (Notion, First Round Capital)

**Camille Ricketts** (00:00:00):
The way that you think about product market fit, you have to think about content market fit. So even though content feels like it's running adjacent to the actual product that you're putting out there, you still have to think about who is my audience? Who is the audience that I really want to have? Who is the audience that is going to be drawn to this most? Who are they? What is it that they really need in their lives? Even abstracting content from it at all. What is it that they need to get promoted? What is it that they need to avoid failure? What is it that causes them a great deal of anxiety in the day-to-day of their lives or their work? And can you create some type of content product that is going to address this for them?

**Lenny** (00:00:38):
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 growing today's most successful companies. Today my guest is Camille Ricketts. Camille was the first marketing hire at Notion and longtime head of marketing at Notion. Prior to that, she was head of content and marketing at First Round Capital, where amongst many other things, she launched the First Round Review, which holds a very special place in my heart because a guest post in the First Round Review essentially helped me launch my now career of newsletter and now podcast. Camille also did content marketing at Kiva and also comms and PR at early Tesla where she sat right next to Elon Musk for about a year and she shares some really fun stories about that.

**Ashley** (00:03:21):
At least 40%.

**Lenny** (00:03:23):
And how many of them screw that up and what happens when they do?

**Ashley** (00:03:26):
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 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** (00:03:45):
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** (00:04:00):
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** (00:04:17):
If you'd like to learn more or get started, check out Flatfile and flatfile.com/lenny.

**Lenny** (00:04:27):
Camille, welcome to the podcast.

**Camille Ricketts** (00:04:29):
Hello there. Thank you so much for having me.

**Lenny** (00:04:32):
Absolutely, my pleasure. You have such a fascinating background working at so many world-class companies with so many fascinating people. Could you just take a minute to talk about some of the wonderful things you've done in your career just to set a little context for folks?

**Camille Ricketts** (00:04:47):
Yeah. Well thank you for characterizing them as wonderful.

**Lenny** (00:04:50):
It's true.

**Camille Ricketts** (00:04:51):
I feel like it's been a quite circuitous path, but definitely has taken me to some interesting places. I started off as a journalist at the Wall Street Journal and then found my way into communications and marketing at Tesla Motors where part of my responsibility there was to sit to Elon's right and make sure he had all the data he needed at his fingertips when talking to the press, which was deep end of the pool on the PR learning. And then after that, found my way to First Round Capital where I was really fortunate to be at the ground floor of First Round Review, if anyone out there watching this is familiar with those pieces. Was there for about five years. Loved that team. Really incredible folks. And then they had invested in Notion really early on, and so I was able to meet Ivan Zhao as a result of that and him and Simon, and they gave me the opportunity to join as the first marketing hire at Notion. And that's what I was doing up until recently.

**Lenny** (00:05:44):
I love that Elon tidbit. I like that it was on his right. His right hand person. What was that like? And is there something that you learned working alongside Elon, sitting next to Elon, about operating, working that maybe you've taken to other places you worked at?

**Camille Ricketts** (00:05:59):
I mean, it was a long time ago, so I'll caveat that. This was before Model S came out even. So a lot of my work was, and this was a great opportunity, but driving around in the Roadster and talking to journalists and letting reporters ride in the car, which was very seductive and I think maybe just a little unfair from a PR standpoint. But in terms of what I learned, that was really the first job that I had that was necessitating just being incredibly on point with all the information. So making sure that I knew everything that could possibly come up in a conversation, being incredibly well-versed in just the topics at hand, I think that served me really well. I just have to be really, really, really quick and on it. And then the other thing that Elon I think is very talented at or definitely at the time really made an impression on me was painting an emotional picture of the vision that he was really going after and being able to convey the emotional quality of the mission to the people he talked to. So definitely at the time about the electric vehicle revolution and then space travel, I think he just knew how to make people feel about it that really enlisted a lot of hearts and minds and that is something that I've taken with me for sure.

**Lenny** (00:07:09):
Would you say that was the most stressful place you've worked or have you found more stress post Elon?

**Camille Ricketts** (00:07:15):
I think that that was the place where you just needed to be so on your game. Game face every single day. Which is a wonderful skill to learn. And then I think there were other moments in my career where just the stakes might have been a little bit higher. Certainly at Notion every day felt like we're building this thing together and we're in this very special moment. So yeah, I think there was a mix there.

**Lenny** (00:07:39):
Speaking of Notion, I think you mentioned this and if not, you were the first marketing hire at Notion. Is that right?

**Camille Ricketts** (00:07:44):
Yes.

**Lenny** (00:07:45):
What employee number was that?

**Camille Ricketts** (00:07:47):
I was number 11.

**Lenny** (00:07:48):
Wow.

**Camille Ricketts** (00:07:49):
Yeah. So it was really a small squad of folks at the time.

**Lenny** (00:07:53):
And how big are they now, roughly would you say?

**Camille Ricketts** (00:07:55):
The last I heard, I think that they were around 400. Maybe a little over 400.

**Lenny** (00:07:59):
Amazing. And I think they're worth ... I don't know. Last valuation was like $10 billion. So there's been quite the journey. Must have been quite the adventure being at Notion during this time. What's maybe the most tangible memory of working at Notion in the early days? What was it like early day Notion?

**Camille Ricketts** (00:08:15):
I think a lot about just what the environment felt like. This was the first very small startup that I had worked for. When I left First Round, I really wanted that experience. And the first office that I worked in was really just like a home. It literally had an apartment on top of this loft space and it just felt like we were a group of people who lived there together during the day, but it had that kind of home spun really warm quality. So we all took our shoes off. There was beautiful furnishings and rugs and we would all just sit around and drink tea and work together on these couches. So it really had that feeling to it. And then there were little quirks. I like to reminisce with my colleagues who were there at the time that we didn't have a great HVAC system.

**Camille Ricketts** (00:08:58):
So during the summer it was really hot and then in the winter it was really cold and we would have these big industrial fans and at the time we were like, "Oh, this is really bizarre." But now it's one of our favorite memories to talk about. Or for a while we didn't have overhead lighting, so me and my colleagues who were there working really late at night, it would just get darker and darker and darker. And one of my favorite folks there actually had a headlamp that she would switch on at a certain point in the evening. So that's the stuff that really comes up for me. We were all working really hard and in this thing together, but it's that team familial quality that stands out to me.

**Lenny** (00:09:35):
I love how some of these early moments where it feels like, what the hell are we doing? We have to wear headlamps? It's super hot. When you're in it, you're like, this isn't maybe how our startup should be going. And it feels really painful and hard. But looking back, it's always the best memories, those hardships.

**Camille Ricketts** (00:09:52):
It truly is. And the moments that we were there late at night really trying to get something done before a big launch the next day, that's where our hearts lie, I think, to a large extent. That crew that was there.

**Lenny** (00:10:04):
On that note, and when you're talking about stress working with Elon, you talked about Notion had a different kind of stress. What's maybe the most stressful memory you have of working at Notion? Whatever you can share.

**Camille Ricketts** (00:10:14):
This is something that has long since been rectified, but the first day that we came back from break in 2021 ... We had all been sort of away for the holidays. We reassemble. I think it's January 3rd, 2021 perhaps. Had a massive outage that day that took down, not just us but also a lot of our peer companies. And so it was literally all hands on deck. We're suddenly seeing all of these people on Twitter pop up, on the Reddit pop up being like, "Oh my gosh. What am I going to do?" And it really reinforced for us how central Notion had become to so many people. So on one hand it was kind of this amazing moment of realization of how vital this thing we were building was all the time, which adds to the stress in the moment, but also your motivation overall.

**Camille Ricketts** (00:11:01):
And then we also saw on Twitter, and this is part of why community is such a core focus of mine, but people being like, "They're trying really hard to get it back up. Give them a break." Or like, "Sending hugs to the Notion team. We know you've got this." And we really appreciated that and that was just a very heartwarming aspect of it. But that day was definitely a scramble and we wanted to be as communicative as possible. So my team was really central to making sure that everybody knew what was going on, what the efforts were being made to fix it, time horizon, all of that. So they've long since hired the best infrastructure people I think in the industry and refactored the database and everything. So it's not an issue anymore, but certainly that was a moment of stress at the time.

**Lenny** (00:11:50):
It's interesting looking at those times. When you're in it, you're like, "We are going to die. We're down. People will stop using Notion. We're in big trouble." When really people always come back if it's an awesome product. I think of last things down for a week, JIRA or Confluent, and people come back if it's an awesome product.

**Camille Ricketts** (00:12:07):
I think that's a good tactical learning and hopefully a takeaway for folks who maybe will experience that moment is that truly there's more resilience built into the system than you might think.

**Lenny** (00:12:16):
So speaking of community, you talked about just how important that was during this time and then just in general. I was doing research on you and things that you've done over your career to prep for this podcast and I found there's two areas that you've led the charge on and we're ahead of the curve on and in part help innovate. One is community led growth and two is content marketing in a big way. And so I wanted to focus a lot of our chat on these two areas. Community led growth, it feels like a very buzzy topic on Twitter. Everyone's always talking about how the future of growth is community. You've got to build a community. You got to be community led and all these things. And so I want to try to make this concept concrete and help people understand should they invest in community. How can community help you? When does it make sense to you? When does it not make sense to invest? And so maybe just as a first question, just what is community led growth? What does that actually mean as a concept?

**Camille Ricketts** (00:13:09):
Yeah. I think it has become quite buzzy and it's certainly aspirational for a lot of product led growth companies and even those that are maybe a little bit outside of the product led growth orbit. And we're seeing all of these startups I think also come out that are about community and how to enhance the effects. In terms of how I think about what it actually is, it's when your community helps you achieve such ubiquity and such name recognition that it actually allows you to start moving upmarket into the enterprise. And I know that might be very specific to enterprise oriented companies, but that's how we defined it at Notion was the fact that so many people were talking about this, sharing what they had built about it, honestly starting businesses of their own around it to formalize the relationship with teams that I think it de-risked Notion as a choice for a lot of companies just because they had heard about it through so many channels. They had seen it on social media, they've heard about it on a podcast, their friend told them about it, they saw a billboard. All of that lended itself to larger and larger companies and teams buying more and more seats. So I think that's the power that the community had for us. And I see that also being analogous to what companies like Figma have been able to achieve.

**Lenny** (00:14:21):
It sounds like a lot of the way you're describing it is basically awareness. Brand awareness is what you found to be maybe the most useful element of this community that you built around Notion.

**Camille Ricketts** (00:14:31):
I love using the word discovery because I think that that is even a little bit like a step further than awareness where true discovery is when you have intent to find out more. You've heard about it so many times or you've been intrigued by something that someone has told you to the extent that you're actually going to take the step of now learning about it. And that's where we really wanted to play and to emphasize our work.

**Lenny** (00:14:59):
Got it. So it sounded like the KPI/OKR of your team was get more people aware and excited to explore Notion.

**Camille Ricketts** (00:15:08):
Yeah. And maybe this is a helpful tactical point. I think when people think about acquisition or discovery or brand awareness or brand in general, they're like what collection of metrics are actually going to give us insight into this? And the one that I found to be the most instructive was net new visitors to the Notion website. So month over month, how many new people who had never been there before were motivated enough to come and actually learn about the product. And that was really the responsibility of the brand team and the folks that worked with me on community and content and all of the awareness campaigns that we were putting out into the field was about getting more new people interested.

**Lenny** (00:15:49):
So that begs to the question, did you have any clever ways of attributing that new traffic to stuff your team did versus the SEO team or other teams?

**Camille Ricketts** (00:15:58):
In particular I'll call out the influencer marketing efforts that were really being run by this incredible woman, Lexi Barnhorn, where they were incredibly measurable. Where we were like, okay, well we're sponsoring people for this amount, these creators across these platforms and we know that people came from that content directly to the Notion website. So we were able to draw really tight connections. So I think that some types of content lend themselves to that. And then also with community, there's certain things you can do around helping your community members report on how many people are attending, et cetera, to give you that sense.

**Lenny** (00:16:36):
So you may be already answering this question, but I'm curious what efforts had the most impact to achieve these goals that you had of creating more awareness and discovery motivation and things like that. What actually worked?

**Camille Ricketts** (00:16:48):
So I'd say that the community efforts that were very big for us we're the ambassadors. Also making sure that people were hosting in-person events. This really took off in 2019. Obviously we paused for 2020, 2021, but now I just spent time with Notion's head of community, Ben Lang, who truly is the mastermind and genius behind so much of this and he says that they're back up to 30 in-person events a month around the world. So that really helped on the international scale of spreading ubiquity and ended up lending itself to relationships with Station F in France, which is the biggest startup campus in Paris. So really helping us work our way into those types of networks and then supporting those people to also start their own businesses and derive whatever reward they were looking for themselves. So we really wanted to align our goals with theirs.

**Camille Ricketts** (00:17:38):
A lot of those folks actually started revenue generating businesses as consultants or course makers or influencers. Some of them just wanted to build their own platforms online. So all of our efforts there are around building guides or counseling people one-on-one or making it easier for them to actually achieve those goals for themselves was also a big part of this growth. And then like I said, influencers. This was something that Ben started exploring in 2019 and we were so pleasantly overwhelmed with the amount of traction and traffic that was driven by working with some of these influencers. And now that program has exploded into a multi-channel effort that's huge for Notion.

**Lenny** (00:18:24):
Awesome. The influencers makes a lot of sense. I want to learn more about this ambassador program and what that was about with events and maybe just broadly, I imagine a lot of founders might be listening and they're like, "Yeah, this all sounds awesome, but how do you know if it's doing anything?" Events. That would be great, but how much is it worth investing? How much time and attention does it take? How do we know if this is actually ROI positive? Is there anything you learn there about just ... Is it a founder must believe in this as a thing that is probably going to work sort of thing? Or is there something you found to convince people like, yes, this is how you can know it's working?

**Camille Ricketts** (00:18:58):
That's a great question. I think that we were really fortunate that Ivan saw the inherent value in community from the very beginning and was deeply supportive. And actually one of my number one recommendations for anybody who suspects the community could be a big growth driver is to not make metrics the be all end all at the very beginning. So we didn't necessarily start measuring things very concretely until last year with community. Mostly because we had already seen so much organic scale that we saw being tied to our community efforts in some way in terms of where we were geographically expanding, how people were reporting that they had discovered us whenever we surveyed them. So that type of motion. And I think for any company that is seeing this type of just organic fervor, one of the worst things you can do is say, let's cut this off at the knees if it's not generating ROI.

**Lenny** (00:19:52):
I imagine internally there's just like obviously this is good. We may not be able to measure it, but it feels like this is very good for Notion. It feels like especially for a prosumer product like Notion, it makes a lot of sense because it's driven by people using it and then they bring it into the company, like you said. Maybe it's less ROI positive or just one enterprise product. Do you have any thoughts there? Is this a great strategy for prosumer enterprise products more so than more enterprise-y?

**Camille Ricketts** (00:20:19):
Definitely I think if you have a long sales cycle or a high price point where there has to be many, many, many touchpoints in order to get somebody to decide to buy, I'm not sure that community should be the number one thing that you invest in. Certainly for freemium products, I think for a lot of them, especially if they have what I'm going to call the atomic unit of sharing, which I will define out, it becomes a no-brainer. I think that community lends itself particularly well if you have something that your product creates that people want to share because it exhibits something about themselves. So at Notion it was templates or even people just creating their own workspaces and being really excited to show them off. So Notion really benefited from being a creative product, but the same is true of Figma or Canva or any of these where showing people what it is that you've created is an aspirational thing to do. Because you are showing that you are really well versed in how to use the products, extremely organized. You're self expressing in some way. So if your product does have that element to it, I think that community is a great investment.

**Lenny** (00:21:34):
You touched on this point, and I don't think people realize this, but you can make a lot of money creating templates on Notion, right? That's a whole ecosystem. Can you talk about that? Because I don't think a lot of people know this.

**Camille Ricketts** (00:21:45):
Yeah. This is one of the reasons that I would advise any of the companies that feel like they fall into this category start early. Because you need to nurture all of these different routes that people in your community can take. Certainly early on I think that the people that we initially recruited in the ambassadors didn't see themselves doing maybe even close to a million dollars in business around helping other teams succeed with the product or selling templates. I remember really early on, probably mid 2021 we heard of one creator who had made $35,000 in four months selling one template and that was a very common story then from that point forward. And helping them do that, actually creating the guide material and the networks and also the connections between the people who are running similar businesses who could help each other, that all became really fundamental. But to your point about, oh is this actually related to the enterprise motion for Notion? So many companies now of many sizes are relying on the consultants that first came up through our community and some of those consultants are now employing dozens of other people.

**Lenny** (00:22:53):
That's incredible. There's no better way to motivate someone to evangelize Notion than have their income rely on Notion.

**Camille Ricketts** (00:23:00):
And it's also just inspiring for us, honestly. There's so many people who started off with not very many followers and now they are celebrities within this ecosystem.

**Lenny** (00:23:12):
So maybe coming back to the ambassador program, that's separate from this selling Notion templates ecosystem. What is the ambassador program?

**Camille Ricketts** (00:23:19):
They're actually quite blended because the folks who are excited about Notion, it takes a lot of forms. Sometimes they want to host events, sometimes they want to build templates. So we would actually have channels inside of our Slack instance for the ambassadors that had these areas of focus based on what people really were passionate about or wanted to do and they were like a force multiplying flywheel for each other. Because a lot of folks would enter the ambassadors program and then I'm happy to talk about champions as well, which is a little bit different, and then discover what it would mean for them to build templates and it became motivating for that reason. So on the champions side of things, and this is maybe speaking a little bit more to the enterprise as well, we wondered if the same DNA that existed among consumers for the most part in the ambassadors could work for folks who were inside of our customer companies. And so we launched another community, another Slack instance for folks who were the most passionate or the most avid users of Notion inside of our customer companies, which has become just a wonderful channel for customer success to be more communicative with those companies, make sure that things are sticking or obstacles are being overcome. And that's been designed very specifically that way and it has been really, really valuable over time.

**Lenny** (00:24:35):
Okay. So let me try to understand this. Champions are basically the most active users of Notion. You put them in a Slack and help them become even more excited and make sure they're happy. Ambassador. I still don't totally understand what is an ambassador? Is that someone you're paying to help promote Notion? What does that actually mean when you're an ambassador?

**Camille Ricketts** (00:24:52):
They're people who are really just passionate about the product. So it's not transactional. They're people who love building with Notion. They love sharing what they've built in order to help others. And they really just want it to be a bigger part of their lives. And I think that one of the points about community is that it's not just a one-to-one conversation with us. The big draw over time, maybe people joined because they would get early access to features. We would get their feedback. That became really important for our product team or because we would offer AMAs with some of our folks internally. But over time it was really because they were forming these bonds with each other and learning so much from each other that most of the time someone would come in and say, I'm struggling with this or I don't quite know how to use this and it would be another member of the community that would help them more immediately. So it really allowed them to form these dense networks of friendships that I think became just a positive part of people's lives.

**Lenny** (00:25:51):
What I'm taking away from this partly is you identify a group of people that are interested in Notion, excited about Notion and then just lean in to support them. There's people that are buying Notion and that are power users, help them be better power users. Influencers that are kind of excited about Notion, pay them to promote Notion. Then the ambassadors that are people just passionate about Notion, help them be more passionate. And then the people making templates, help them be successful. Is that roughly how you think about it? Just identify something that's working and make it more effective?

**Camille Ricketts** (00:26:21):
I think if it doesn't sound too reductive, yes. I would also say that one of the things that I think Ben was best at is not putting a one size fits all experience on any of this. I think that some communities get built where people are like, okay, well we have this community and it's going to be this and this and this, or these are the types of programs we're going to offer or these are the types of interactions we're going to have. As opposed to I think a lot of listening of the people who are actually participating. Really early on one of the things that Ben did that I thought was really amazing was he'd spend a ton of time just on Zoom having conversations, one-on-one conversations, semi small group conversations just saying, "Why are you here? Why do you like participating in this? What is it that would make it better?" And really helping our entire team follow their lead. I would recommend highly not necessarily coming in with preconceived notions about what a community needs to look like.

**Lenny** (00:27:21):
You touched on this, that if the founder believes in the power of community, this becomes so much easier. A lot of founders are like, "Nah. That's a waste of time." Do you think founders are convincible that building community and investing in community is worth it? Have you seen that effective where a founder just comes into it being like, "Nah, I don't think this is worth our time," and then they get convinced later? Or is it just like, "Nah, forget it. Don't even try."?

**Camille Ricketts** (00:27:45):
I mean I've talked to a lot of different people who come at this with different impressions and everybody knows more about their company than I do, but I do think that if ubiquity or just the sheer word of mouth engine is something that is going to be valuable for your company over time, I would really urge people to sit down and really think carefully what is going to be more conducive to our long-term success? Is it going to be that ubiquity or is it going to be revenue now? And I think if we look at a lot of the companies that have been just wildly successful from the start, they're people who have pushed off maybe monetizing every little thing if it's going to really put a damper on that type of enthusiasm and momentum that people have to share it at what it is they're doing. Because there's always opportunity I think later once you have that big tide of people who are not just excited but also legitimizing what it is that you do every single day, that gets mobilized in a lot of different directions and you have a lot more options then.

**Lenny** (00:28:47):
What's interesting about Notion is you have high LTVs when you sell to larger companies, but the initial users are often just regular folks. And so I think it's a unique place where you have cash to spend on making it ubiquitous and getting the word out through all these community efforts because it'll pay off. And a lot of companies probably don't have that advantage. So would it feel right to say that this is really effective for product led, growthy, freemium products most? Is that a good way to think about it?

**Camille Ricketts** (00:29:20):
Yeah. Or I think if organic growth is something that you see being really beneficial or if organic growth happens to be something you really have to crack because you don't always have everything you need for paid growth from either a resourcing standpoint, team standpoint, really figuring out how to get that organic flywheel going can serve you well. It becomes this buttress for any paid growth you explore in the future.

**Lenny** (00:29:47):
**Camille Ricketts** (00:31:14):
I've mentioned Figma a couple times here so I don't want to beleaguer the point, but they're certainly a team that I've looked up to through my entire experience at Notion. We were kind of sibling companies in a way. Huge kudos to Claire Butler over there who I knew led all of those efforts and we would trade a lot of knowledge back and forth, which was so lovely to have that relationship. But they did an amazing job I think in a similar vein to Notion of saying, okay, people are really excited to create these things and then put them out there on the internet. So how can we just fuel that particular motion out there? The other example I'll give, which is a little bit of a different tack is Stripe. And when Stripe launched Stripe Atlas, not necessarily core to the initial product line that Stripe was known for and what had been foundational for them, but allowed them to build this community among probably their core demographic at the time, which was founders and startups that were growing through the stages to mid-market, they were able to cultivate this huge audience of founders around giving advice and providing them with resources to actually get started and do that zero to one journey.

**Camille Ricketts** (00:32:22):
So while it was adjacent to maybe what the company's core mission was, it allowed them to actually create community among their customer base because they were like, "We're knowledgeable. We can share these things with you that we know are core to your journey." So I would encourage anyone who's thinking about community that way to be like, "Oh, maybe it doesn't have to be around our product. So specifically. What other knowledge or resourcing can we offer to the people who we do want using our product that's going to be really instrumental for them and can we convene them around that idea?"

**Lenny** (00:32:54):
I'm noticing a strong correlation between legendary generational companies, Figma, Stripe, Notion and community efforts and building community. That's interesting.

**Camille Ricketts** (00:33:05):
Yes. I'm a big proponent. At the same time I don't think that community is right for every company. I think that there is definitely an analysis to run on that. But hopefully this is helpful for those who can identify that those are attributes they have.

**Lenny** (00:33:19):
To pull on a thread there, what are maybe thoughts for when it probably doesn't make sense to invest a lot of efforts into building a community around your product? We talked a little bit about high-end enterprise products. Is there anything else that just like, man, it's probably not worth your time?

**Camille Ricketts** (00:33:34):
Like I said, if it's more of a sales led culture that you have, which is definitely true of products that are a little bit pricier or that require longer contracts, so understanding that. But I do think the community takes on different forms and I think when you hear the word community, you think of a big forum of some type, whether it's a Slack instance or something else where people are chatting away all day long. And I don't think it has to be that. That's not the only representation of it. So if you think about what is going to be right for you at any given time, I actually created this two by two matrix, which maybe I'll share with you after this. And on the axis you have, whether you have hit product market fit or if you're still exploring product market set and then whether you're strongly enterprise or strongly consumer. And based on where you land in that two by two matrix, there's a form of community or a community related initiative that could be right for you.

**Camille Ricketts** (00:34:31):
So just to give you an example of maybe an extremely different form factor from Notion, let's say that you're still on your way to product market fit and you're a strongly enterprise oriented product. I think that you have the opportunity to do customer advisory boards, which is really convening even smaller circles of ideal fit users and making sure that they are connected to each other as well as you, and then incentivize to provide you with feedback. Understanding that they're really on the ground floor of this journey with you and that they're going to be able to have influence over whatever you do in the future. Those folks can end up growing into your biggest evangelists and I've seen that happen a number of times and I would still consider that community even though maybe that is not what comes to mind for folks.

**Lenny** (00:35:20):
Well I imagine that becomes the seed of a community that you eventually build. Let's definitely link to this in the show notes. Can you give maybe a couple more examples of this grid? So that was pre-product market fit and then what was the other?

**Camille Ricketts** (00:35:32):
Strongly enterprise.

**Lenny** (00:35:33):
Enterprise. Okay, cool. Yeah, what are a couple other of the elements of this grid?

**Camille Ricketts** (00:35:37):
So if you're strongly enterprise and you have product market fit, let's say, this is something that Notion has really benefited from, but really emphasizing the champions in the consultants communities. So the folks who, like I said, may be inside of your customers who really get it, really get your value, really are excited to help you land and expand perhaps inside of their companies, making sure that they have a place to gather and a place to feel like they are more connected with your team than the average person gets to be. That they are special and that they have access. And then on the consultant side, like I said, just making it really easy, removing friction, helping promote the folks who want to be out there, helping you succeed with more customers. Like Salesforce. I know that this is a golden oldie of an example, but if you talk to anybody who was really early at Salesforce, they really went into this where they saw people emerging who wanted to help other companies. This layer of people who didn't work at Salesforce but saw the opportunity to help other companies actually succeed with it, implement it, grow with it, and that's become a massive part of Salesforce's model. And so if you're in that quadrant, figuring out how to start moving people in your customer base into those categories.

**Lenny** (00:37:00):
This is awesome. Maybe let's do one more of this grid and then we'll leave one for people to click into and check it out.

**Camille Ricketts** (00:37:04):
I'll talk about Notion's quadrant, which is the one that I would put up and to the right, which is you have product market fit and you're maybe a little bit closer to the consumer side of the spectrum. Obviously Notion runs the full gamut, but I would say especially early on I think that that's where we saw things take root and that's where I think ambassadors and influencers really take off. Individuals who are going to be extremely vocal, extremely excited, and where you're going to see more of this wildfire spread, at least trying the product, using the product, understanding what the product is. So if you can try to fuel that type of motion if you're in that quadrant, that's helpful.

**Lenny** (00:37:43):
I want to come back to this ambassador program real quick because it feels like something that a lot of people talk about and can do and especially in this quadrant of product market fit and consumer. How does this work? Is it you select, here's 100 ambassadors we're going to pick because we think they're awesome and they're great examples of people using, say, Notion and then we're just going to provide them with all the help they need to be successful with Notion. How do you think about creating an ambassador program?

**Camille Ricketts** (00:38:10):
I actually think it's pretty analogous to when you're thinking about positioning your company because I think the best first step for any positioning exercise is to think who are our best fit customers? And it's not necessarily who we wish they would be, but it's actually the hard cold reality of who they actually are. Where it's like these are the people that seem to be really getting it. They're paying us more, they're talking about it just organically. So really figuring out everything about who they are and making sure that those are the people that you're actually inviting in early. So the initial base of the ambassadors program which started back in 2019 was just 20 people and they were the 20 people who we happened to see be the most vocal already across Twitter and a couple of other social media platforms because they had that shared quality of wanting to be really vocal and expressive about their experience with the product. So that would be my advice for how to get one of these rolling.

**Lenny** (00:39:13):
And then what do you do for them?

**Camille Ricketts** (00:39:13):
Definitely making sure that there's enough incentive built in, right? Because like we said, it's not meant to be a transactional relationship, but we want them to feel like they are having a special experience, that they are connected with the company in a unique way. And it was so interesting to us how giving them the preview of features was so motivating to them and being able to use them and then give us feedback and feel really heard by the product team. So that was a big area of focus and I know that that still is and it's become even more of a robust conversation between the community and the team at Notion itself.

**Camille Ricketts** (00:39:52):
And then also we would do these very special experiences where Ivan or Akshay or Simon or MLM who's the head of engineering there would be available for these conversations where they would answer questions and it would feel like a very proprietary space. I think that that was really interesting to people. And then of course the things that you would suspect around subsidizing events. Making sure that people felt that they were actually supported by us to throw these events. And then also promoting their work. So if you look back at the social media channels, so much of the focus is on putting the creations of the people we were working with front and center as opposed to talking about just what the company was up to.

**Lenny** (00:40:36):
Have you ever written about just how to design an ambassador program or has anyone written about how Notion did this? Because this is really interesting.

**Camille Ricketts** (00:40:42):
I don't know if anything has been written or went into all of this detail, but it was truly one of the more magical and I think still is one of the more magical parts of this entire endeavor. And now that team is three people. So Ben who's still there doing amazing things, Francisco who joined us in 2021. Or sorry at the end of 2020. And then Emma. And they are just all day every day talking to people around the whole world. The international component of this is also just completely wild to see.

**Lenny** (00:41:18):
This could be a future First Round Review post, which we'll talk a bit about.

**Camille Ricketts** (00:41:21):
Yes. Perhaps.

**Lenny** (00:41:24):
Last question about this segment. Say someone is convinced they want to start investing in community and we talked about this two by two, but maybe just broadly if you had to boil it down to two or three pieces of advice for founders, for teams thinking about investing in community led growth and community in general, what would be some of those pieces of advice?

**Camille Ricketts** (00:41:44):
I don't know if you want to link to this in the show notes as well, but I actually put together some commandments for community builders.

**Lenny** (00:41:50):
Ooh. Absolutely.

**Camille Ricketts** (00:41:51):
Some alliteration. So the thing that I think were very defining for us early on, I already mentioned something about this, but not trying to hit a number early on. So don't dilute the impact of what it is that you're trying to do in order to show growth. I think that that's very important to protect yourself early on. So making sure that you are learning what individuals really want out of this and making them feel like they're very seen and very heard. That was a big area of focus and I think it's what kept people really engaged and coming back and feeling like this was a secondary family for them. And then one of the things that was most interesting to us that once we started sharing what was going on in the community with folks at Notion. So we would do this during all Hands meetings or on Slack, Ben would post these really incredible updates of just all of the activities of people in the community and what they were up to every month.

**Camille Ricketts** (00:42:46):
And it was just so inspiring for everybody inside the company that I think it all rallied us to do even more, I guess, day to day and really understand who it was we were building for.

**Lenny** (00:43:00):
Is there any other commandments you would add for if you already have a community going? If you have something bubbling for things you should do to keep it healthy and consistently good and growing?

**Camille Ricketts** (00:43:12):
Yeah. I mean this is going to be a little contrarian perhaps, and I mean this is just one data point for me, but not growing it so big so fast. One thing that we actually thought about pretty carefully was what a rate of healthy growth would be. So there actually is an application process for joining the ambassadors. It's a very light application process and it really is just so that we know how many people are interested in this. And then they're inducted around ... I think at the time it was 20 people at a time every month. So that it wouldn't feel like all of a sudden this had changed in terms of how the interactions were feeling, but rather gave everybody time to welcome the new people in and get to know them. And one of Ben and I's favorite things ever about working at Notion I think was when we would induct new people into the ambassadors and they would introduce themselves and say, "Hey, I am from Venezuela and here's the ways in which notion has changed my life."

**Lenny** (00:43:12):
That's awesome.

**Camille Ricketts** (00:44:11):
"I'm from Hong Kong and here's how it's changed my life." And all of that was just so fulfilling. That would be the number one thing I would say is give your community time to actually grow in what feels like an organic fashion as well. Because I think ironically, and then I'll stop rambling about this, but if you grow to something like, oh we have 5,000 ambassadors, which feels really good to say on a website, the conversation is actually very muted. I think because people feel like they're speaking to an auditorium whenever they say anything. I think it's because you don't really have a sense of who else is there with you. So helping to defray those concerns I think is a good course of action.

**Lenny** (00:44:57):
I've seen the same thing with the growth rate being really important with my newsletter Slack community. I think most listeners probably know this, but if you're a paid newsletter subscriber, you get access to the Slack community. There's about 10,000 people in there. And I find the filter of people that are willing to pay for content like a newsletter is a really good filter for awesome people. And so it ends up slowing growth in a really healthy way and then just creating this filter of the people that really want to self-improve and value the sort of thing join, and it becomes a really amazing group of people.

**Camille Ricketts** (00:45:31):
Yeah. It feels like such a ... I don't know. There's an emotional quality to it I think when that's the case. And all of those people end up being so incredibly impactful. The last point I'll make about community at Notion is that a lot of those people, and we actually ended up launching I think a channel for folks who wanted to do this in particular, but run communities external to Notion's actual owned communities. So you end up with Facebook groups that have ... I think Notion in Vietnam has like 250,000 members. Or the subreddit, which I now know has 210,000 people in the Notion subreddit. And those are all run and moderated by community members who just love running their own communities.

**Lenny** (00:46:14):
I feel like you've achieved your OKRs of ubiquity of Notion.

**Camille Ricketts** (00:46:19):
Yes. It was always a value at Notion to make sure that we were reaching as many people as possible.

**Lenny** (00:46:26):
It's working. One tactical question. Where does the own community of Notion live? Is it a Slack? Is it an online thing you've built yourself?

**Camille Ricketts** (00:46:34):
It is in Slack. And the thinking there, and it still is, was that we really just wanted to be in the course of people's everyday lives. We didn't want to be this other destination that you would have to make a point to going to every day.

**Lenny** (00:46:45):
That's exactly how I thought about it with my newsletter Slack community. PMs and founders, they're already in Slack all day. And just that badge, being on the app telling them there's something to check is such a powerful feature versus download a whole new app or go to a whole new website, you're never going to go there. It has to be 10 times better to pull you to a whole new site and change your habits.

**Camille Ricketts** (00:47:05):
I absolutely agree.

**Lenny** (00:47:07):
I'm glad we're all on Slack. Slack's so underrated. I feel like people hate on Slack all the time, but it's such a good product.

**Camille Ricketts** (00:47:14):
We all love it. It's just becomes something we take for granted in the background there.

**Lenny** (00:47:17):
Yeah, exactly. Okay. This is a good time to shift to our second topic, which is around content and content marketing. So you started the First Round Review at First Round?

**Camille Ricketts** (00:47:26):
Yes.

**Lenny** (00:47:27):
I don't know if you know this, but First Round Review was a big part of my early trajectory with this newsletter life. I did a guest post in the First Round Review and that was-

**Camille Ricketts** (00:47:37):
I remember this.

**Lenny** (00:47:38):
That was a huge deal for me. That was my first 500 subscribers to my newsletter.

**Camille Ricketts** (00:47:42):
Wow.

**Lenny** (00:47:44):
Then I did another guest post down the road, but that was not as important. It was a big part of my early path down this life. And so thank you for creating that platform. I was very honored to be involved.

**Camille Ricketts** (00:47:57):
That's fantastic to hear and exactly what we wanted to have happen. Just extraordinary operators being given a platform and then using it to do whatever it is that they wanted to do. That was part of the dream always.

**Lenny** (00:48:10):
It's working.

**Camille Ricketts** (00:48:11):
Yeah. I'm thrilled because now people are learning so much from you.

**Lenny** (00:48:14):
Yeah. It's an inspiration for where when I started too, just I wish I could be as good as the First Round Review and the stuff just keeps coming and coming. It's amazing. And I know other folks run it now. I don't know if they want to be named. They like to be behind the scenes.

**Camille Ricketts** (00:48:27):
They do, but I'm going to shout them out anyway because they do such an extraordinary job. I mean, Jessi Craige Shikman over there has been doing this now for longer than I did and she is absolutely incredible and her team is extraordinary and I don't miss it every single time it comes out.

**Lenny** (00:48:44):
Yeah. I tried to thank her my post. She's like, "Don't mention that. I'm behind the scenes."

**Camille Ricketts** (00:48:44):
Maybe I'll ask her.

**Lenny** (00:48:53):
We have to give her some cred somehow.

**Camille Ricketts** (00:48:56):
Yeah, absolutely. She deserves it.

**Lenny** (00:48:58):
So kind of zooming out, content marketing, maybe just to give some examples of just what are some of the most impactful things you've been a part of that come from creating content? Whether it's Notion, First Round, anywhere else, what are some examples?

**Camille Ricketts** (00:49:11):
Yeah, I'll give a few examples. Obviously First Round is a huge example and so I'd be remiss in not going into some detail there. And truly that was a team effort from the very beginning. I joined in 2013 and again, I was just so fortunate to work with a leader who believed in it from the very beginning. Josh Kopelman, who's the partner there who was just a massive supporter of mine. Phin Barnes on the partnership team. But then particularly Brett Burson who was running the platform team, which is where all of these value added services lived.

**Camille Ricketts** (00:49:40):
So it was me and an events person and the talent person and Brett just gave us all of the runway and all of the belief and support that we needed. And he was really bullish on content and really helped from the beginning, connecting me with incredible interview subjects. Because this whole thing, the only reason I think it survived and did as well as it did is that we were able to land a few really big names at the very beginning. And then of course that helps you down the road whenever you're trying to convince anyone else to do it because you say so and so and so and so have already been featured. So that was I think just a big point of confidence and also tactically, for anyone out there thinking about it, if they can leverage whatever connections they have in that vein.

**Lenny** (00:50:27):
I was at dinner with Brett yesterday.

**Camille Ricketts** (00:50:29):
Oh my god. What a guy, right?

**Lenny** (00:50:31):
First Round event. What a guy. That guy's amazing. I'm a huge fan. He's built an incredible platform and program at First Round.

**Camille Ricketts** (00:50:39):
And he's one of the people that I've learned the most from, certainly. But more specific to your question around what the content program was able to do there, certainly discovery of First Round. I think prior to that it was a very successful VC fund, but I think we got in front of all kinds of people, particularly in non-traditional geographies or non-traditional founder types or all of that. People who are inside large companies like Google, Apple, Amazon, whenever we would look at our list of subscribers, we had an disproportionate number of email addresses within those companies that were clearly curious about the startup experience. And I think First Round Review was helpful in moving them more toward that mindset and then them obviously understanding that First Round would be a great first stop for them.

**Lenny** (00:51:23):
What would you say is key to content being valuable? So you're talking about the First Round Review became really effective for people learning about First Round, working with First Round, discovery of First Round, but it's not just with content you just write some stuff and it works. It doesn't work that way. What have you learned about just what do you have to get right? You mentioned have names people recognize. Is there anything else you've learned over the years of just like, here's what we need to get right if you're trying to use content as a way to create discovery and awareness of your stuff?

**Camille Ricketts** (00:51:54):
This is something that I think we chatted about briefly, but the way that you think about product market fit, you have to think about content market fit. So even though content feels like it's running adjacent to the actual product that you're putting out there, you still have to think about who is my audience? Who is the audience that I really want to have? Who is the audience that is going to be drawn to this most? Who are they? What is it that they really need in their lives? Even abstracting content from it at all. What is it that they need to get promoted? What is it that they need to avoid failure? What is it that causes them a great deal of anxiety in the day-to-day of their lives or their work? And can you create some type of content product that is going to address this for them and is actually going to have that value?

**Camille Ricketts** (00:52:36):
So I think approaching content the way that you would a product in a lot of ways is very instructive way to sort of start hashing out your strategy. Starting with your audience, understanding their big needs. You've heard this, I'm sure, and most of your audience has, but there's the vitamin versus painkiller dichotomy. And painkillers always win. So can your content be a painkiller? Can it help people out of situations that are causing them a lot of pain? Can it help people stop being so confused or can it make them even feel less alone in their experience? That was a big one for First Round Review is helping operators share failures or suboptimal situations in the spirit of helping many other people feel like that was normalized and that the experiences they were having weren't as dire as maybe they had thought.

**Lenny** (00:53:27):
I love that. It connects so much with the way I think about writing. I use the jobs to be done framework a little bit here where I'm just like, what job am I doing when I'm writing a post? And you tell me if this makes sense to you, but I feel like there's four jobs to be done of a newsletter. Either how people make money. There's newsletters, here's how to invest, here's how to buy Bitcoin and win. How people make money. Entertain people. There's a lot of funny things, memes and cartoons and things like that. How people get better at their work or life, which is the category we're in. And then inform people. Like news.

**Camille Ricketts** (00:54:02):
Yes. What they didn't know before. Yeah.

**Lenny** (00:54:05):
And it feels like you got to do really well. You got to pick which bucket you're in. And let me know if you can think of any others because these are the four that I always come back to. And then pick your bucket and then it's be the best at that thing in your category. The way I think about it.

**Camille Ricketts** (00:54:18):
I love that listing out of those and also the acknowledgement that there are emotional jobs to be done. That there are not just utilitarian jobs to be done. It's not just, you didn't know this before and now you do, but it's like you felt this way before and now you don't or you do. And I think that that's underestimated. So I love that you called out entertaining people because we're all working in an industry where it's wonderful to interact with some of that sparkle and levity. So I love that approach.

**Lenny** (00:54:45):
And something else that goes unsaid I think in the way you talked about this is just putting in the time to make it really high quality. If you look at a First Round post, how much time would you say goes into in the typical First Round Review post?

**Camille Ricketts** (00:54:58):
Oh gosh. Here's where I'm going to shout out my writing partner at First Round, Sean Young, who was there with me for most of my time there and he and I would always, always talk about this. But it would take eight hours to just write the thing. And that's after you had done all of the prep work of making sure that your interviewee was feeling really anchored and understanding a topic that you were both really excited about and making sure you were mining all of the tactical gems from that conversation. And then you would start writing and that would be another eight hours. I don't know if that's your experience, but certainly was ours.

**Lenny** (00:55:31):
Yeah, very similar. I don't tie myself, but I feel like the median time to write a post for me is about 10 hours.

**Camille Ricketts** (00:55:37):
Yeah.

**Lenny** (00:55:37):
And that's I think the key that a lot of people don't think about. One is they don't have the time, and two, they don't realize they should spend this much time because the bar's so high for content on the internet as we all know. There's so much stuff out there. And so to get above that noise you have to really make it really good and that just takes time. And I find this really strong correlation between the time it takes me to write a post and how well it does. It's very highly correlated. And the advantage folks like say the First Round Review have and I have is I do this and there's a team doing this. And so people that are doing this on the side, it's much harder because they don't have that time.

**Camille Ricketts** (00:56:14):
It is. I end up admiring those people a lot where I'm like, how are you doing this?

**Lenny** (00:56:18):
Yeah. They're sacrificing something.

**Camille Ricketts** (00:56:19):
Yeah. But truly, it's a very shared experience with you. And I think that a lot of that was making connections between the information that you had available from these interviews. So not just straight here's what this person said, but how can you draw connections between those things, connect the dots, pull out bigger themes. All of that is really where I think a lot of the time went.

**Lenny** (00:56:43):
So you said you had this content market fit questionnaire that you talked through. You're going to send me a link that we can point people to check it out, right?

**Camille Ricketts** (00:56:51):
Yes.

**Lenny** (00:56:51):
Okay, awesome.

**Camille Ricketts** (00:56:52):
Absolutely. A lot of it is about getting to know your audience to an almost beleaguered degree.

**Lenny** (00:56:57):
Which is basically what job will you do for them, like you said. And so that makes sense. Maybe a couple more questions. Something that I've noticed a lot, and this is related to content and just PR and stuff like that. I've noticed a lot of people on Twitter and founders are trying to pitch this idea that you don't need to think about comms and press and PR as much because now you can go direct. You can have a newsletter, you can write, you can tweet, you can LinkedIn. Do you feel like that is where the future is going for founder press and comms and things like that or do you think you still need to have a really strong comms, press, PR org within your company?

**Camille Ricketts** (00:57:36):
That's a great question because I think that there's been just a lot of change in this space over the last five years and certainly very strong opinions from all over the ecosystem. I'm a big believer in comms. And I don't just say that because I used to be a journalist or I used to work in comms. But I think that there are very few and far between incredible megaphones for what it is that you or your company is doing where you get to reach such a breadth of people with that stamp of credibility and notice. How do you get somebody to say, "Hey, this is really something you should pay attention to."? Obviously I support all of the owned media efforts that are really working and bubbling up. And like I said, influencer I think is going to be a massive shift in how we discover things, but maintaining a wonderful relationship with the press, being straightforward, being that brand that is going to be accessible, I really think that that pays off.

**Camille Ricketts** (00:58:37):
And just to give you one example, David Pierce, who I think is one of the best working journalists in tech today, he's at The Verge now. He was covering personal tech for the Wall Street Journal early on at Notion and published a story that said this is the one work-life productivity app that you'll ever need. And that was Notion's big break. Truly, if you look back at the graphs, that made a demonstrable difference. And I've seen that happen time and time again. And one of my other efforts at First Round was helping companies in the portfolio figure out how to DIY comm strategies. And I saw this again and again that the companies that did get stories that really told their mission, it made a big difference for just discovery awareness. The number of people who wanted to be involved with them as candidates, as investors, as customers.

**Lenny** (00:59:29):
This gives me a new post idea of just what are the big breaks of companies? What was the moment where they started taking off? Note to self?

**Camille Ricketts** (00:59:36):
Yes. The other big thing for the Notion was product hunts. I want to give them-

**Lenny** (00:59:40):
Oh, okay. So posting on Product Hunt, that was a big deal for Notion.

**Camille Ricketts** (00:59:44):
It was. And it remains a big deal. If you go on Product Hunt and you type in Notion, you'll see just how many templates have been able to get noted because of Product Hunt.

**Lenny** (00:59:54):
So it's the templates being posted, but then also the launch of Notion on Product Hunt?

**Camille Ricketts** (00:59:58):
Yes. And Notion 2.0. And then whenever we would have a major productized launch.

**Lenny** (01:00:05):
Wow, that's awesome. Man, Product Hunt just keeps kicking.

**Camille Ricketts** (01:00:07):
Notion AI very recently for them, which couldn't be more exciting.

**Lenny** (01:00:11):
I have access to that. I've been playing around. It's awesome. Maybe a last question along these lines is thinking about the founders that you've worked with. So on the one hand you have Elon who is very direct on Twitter to his audience, and then Ivan feels much less so and more under the radar and doesn't love tweeting a lot. And then First Round Review somewhere in the middle. Do you have any thoughts on how much a founder should invest in, say, tweeting and going and communicating direct to folk? Or is it more just whatever the founder is, their personality, just go with that?

**Camille Ricketts** (01:00:41):
I really do think it's about personality and what feels authentic. I think that so much of a founder's strength comes from leaning into where they know that they love to work, what they know about themselves. And I think that one of the biggest mistakes you can make on social media is giving yourself a quota that you have to hit and say, I have to say X number of scintillating things every week on these platforms. We've just seen so much more traction, even from the main Notion accounts when we're a little bit more reserved and we wait until we have something to say that has value.

**Lenny** (01:01:12):
Awesome. Any last closing thoughts before we get to our very exciting lightning round?

**Camille Ricketts** (01:01:19):
Closing thoughts. No, this was a wonderful conversation. Thank you so much for letting me share. Truly, I also want to make sure I'm giving a lot of credit away from all the people that I mentioned throughout. It was all just a major team effort and I've gotten very, very lucky to work with the best people.

**Lenny** (01:01:32):
Awesome. We'll try to link to all of the people you mentioned in our show notes. We try to do that every time. So it'll be a long show notes. And we're not done yet. We've reached our very exciting lightning round. I am going to ask you six questions real quick. Whatever comes to mind, we'll go through it pretty fast. That sound good?

**Camille Ricketts** (01:01:48):
Yeah. We'll see how it goes.

**Lenny** (01:01:50):
Let's go. No pressure. What are two to three books that you recommend most, that you've recommended most to other people?

**Camille Ricketts** (01:01:57):
Obviously Awesome by April Dunford. If you're looking to position your company, I don't know if you've read it, but it is a step-by-step guide. It's like 100 pages long.

**Lenny** (01:02:05):
I've read it. She's done a guest post on my newsletter. She's been on the podcast. So all over it.

**Camille Ricketts** (01:02:11):
Oh, fantastic. She's incredible. Yes. Oh gosh. I'm going to have a hard time coming up with two other books that have had that sizable of an impact.

**Lenny** (01:02:19):
We can keep it to one too. It's all good.

**Camille Ricketts** (01:02:21):
Can we keep it to one?

**Lenny** (01:02:22):
Yes. Just the one. All you need. What's a favorite other podcast that you listen to other than the one you're on currently?

**Camille Ricketts** (01:02:30):
I mean, I love your podcast.

**Lenny** (01:02:31):
Thank you.

**Camille Ricketts** (01:02:32):
Harry Stubbings never ceases to amaze me. We've gone on at Notion a couple times and I just really appreciate his approach to mining a lot of incredible information and unexpected stuff.

**Lenny** (01:02:46):
Harry Stubbings is the godfather of this podcast because I did his podcast and at the end of it privately he's like, "Lenny, you need to do a podcast, you idiot. Why are you not doing a podcast?" And that got me over the hump and look at us now. So yeah, huge shout out to Harry.

**Camille Ricketts** (01:03:00):
I love all of these connections that exists. That's wonderful.

**Lenny** (01:03:02):
Yeah. Next question. Favorite recent movie or TV show that you've loved?

**Camille Ricketts** (01:03:08):
Oh gosh. Recent. I went to go see Tar, which I know is going to be not everybody's cup of tea, but it was just incredible to watch this performance from Kate Blanchett. She learned German. She learned how to be a credible conductor of a major symphony orchestra. If you want to see a bravura performance, that's the one to see. And then recent television show I'm watching Fleischman is in Trouble. I love the book and I just think that the detail and texture of that show is super well done.

**Lenny** (01:03:37):
Awesome. My wife and I have been watching that and it's awesome. Last episode was less exciting, so I'm curious where it all goes, but I'm watching.

**Camille Ricketts** (01:03:44):
Agreeing. But every time Claire Danes is on screen, I'm riveted. Yeah.

**Lenny** (01:03:50):
Favorite interview question that you like to ask folks, either when you're interviewing at a place, hiring, anything that comes to mind.

**Camille Ricketts** (01:03:56):
Yeah. The one thing that was really helpful, because we used to do this thing at First Round Review where we would explore topics and be like, how do we get to a topics that's going to be unique or new knowledge or whatever it was. And it was, what is one thing that you think that led to your success that nobody else in your peer set has done? What was something that you did on a lark or that you were like, this is a big bet, or this isn't probably going to work, or it's a mistake that it even turned out this way, but it ended up being great. What is that one thing that was unusually conceived that you want to share with people?

**Lenny** (01:04:24):
I love that question. I almost want to answer it, but let's move on. What are five SaaS products that you use or have used other than notion that you found to be really good other than maybe Slack, which everyone always mentions.

**Camille Ricketts** (01:04:39):
I mean, I'm in love with Notion. The other thing, the other great love of my life right now is Arc, The Browser Company.

**Lenny** (01:04:44):
Oh my God, I love Arc. I just switched to it. I love it.

**Camille Ricketts** (01:04:47):
Yeah. It was something that I tried and within an hour I've made it my default browser and I just think it's beautiful and delightful in one of those intangible ways that a lot of these products are

**Lenny** (01:04:58):
Same. Yes. Cool. Oh, there's more. Yeah.

**Camille Ricketts** (01:05:00):
I already talked about Figma. I love Figma. I actually use it in my day to day life, which is one of the best parts of it is that folks who are not necessarily designers or highly technical can also get a lot out of it. Superhuman. Couldn't live my life without Superhuman. Whenever I have to go back into Gmail to set an autoresponder or whatever, I'm like, ugh, my eyes. So couldn't live without that. Gosh, I'm on sabbatical, so I don't know how many other SaaS products I'm actually using day to day so I'm going to keep it at three.

**Lenny** (01:05:29):
All right. Yeah. Use less SaaS products during your sabbatical. It's a good philosophy.

**Camille Ricketts** (01:05:33):
Yeah. I don't know if that was your experience, but just is. Oh, the other one I'll shout out, even though this is like a sneaky Notion plug is Kron. So if anybody isn't using the Kron calendar, which is now part of Notion as some folks might know, it is in fact the best calendar product on the market.

**Lenny** (01:05:47):
Sneaky, sneaky. Last question. What's a favorite read or course or just anything you'd recommend for people to level up their community building skills to build a community, run a community? What would you point people to?

**Camille Ricketts** (01:06:01):
I'm not aware of any courses that are necessarily offered. Ben Lang has done a number of AMAs or interviews, so if you want to just Google Ben Lang and the word community or Notion, you're going to find just a lot of incredible insight. And his experience has been, I think ... In terms of community people operating in tech, Ben is top level, so find whatever he's said.

**Lenny** (01:06:27):
Awesome. We will find it. We will link to it. Camille, I just met you an hour ago, but I feel like I've known you forever. This was amazing.

**Camille Ricketts** (01:06:34):
Likewise. Thank you.

**Lenny** (01:06:35):
Thank you so much for making time for this. Two last questions. Where can folks find you online if they want to reach out, learn more? You're on sabbatical now, and so maybe share what you're thinking about next and what you could be ... I don't know. And I guess this is the second question. How can listeners be useful to you?

**Camille Ricketts** (01:06:49):
Thank you for that. You can find me on Twitter. I'm just @CamilleRicketts. Super straightforward. Still sticking with it. And in terms of where I'm at in my life, I'm just interested in meeting as many fascinating new people and learning about things as possible. I've started going to these Founders You Should Know events for anybody who's interested about FYSK, and just meeting as many cool people who are building just incredible concepts. It's inspiring every time, and I just want my whole life to look like that. So get in touch if you're building something and think I could be helpful.

**Lenny** (01:07:21):
Amazing. Camille, thank you so much for being here.

**Camille Ricketts** (01:07:24):
Thank you so much. This was wonderful.

**Lenny** (01:07:27):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or 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] Founder-led sales | Pete Kazanjy (Founding Sales, Atrium)

**Pete Kazanjy** (00:00:00):
The thing that I just like to encourage founders and product managers and what have you is just don't be afraid of sales. There's a lot of people out there who would love to tell you a story that it's magical or like, "Oh, you've got to be a born seller," things like that and it's really not. Those people are just talking their book, if you will, and so just getting good at those behaviors, it's going to benefit you in a myriad of ways.

**Lenny** (00:00:26):
**Ashley Mulligan** (00:02:53):
At least 40%.

**Lenny** (00:02:55):
How many of them screw that up and what happens when they do?

**Ashley Mulligan** (00:02:58):
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** (00:03:17):
I am 0% surprised to hear that. I've consistently seen that improving onboarding as one of the highest leverage opportunities for both signup conversion and increasing long-term retention. Getting people to their aha moment more quickly and reliably is so incredibly important.

**Ashley Mulligan** (00:03:32):
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** (00:03:49):
If you'd like to learn more or get started, check out Flatfile at flatfile.com/lenny. Pete, welcome to the podcast.

**Pete Kazanjy** (00:04:00):
Hey, Lenny, super awesome to see you.

**Lenny** (00:04:03):
Even more awesome on my part. Ever since I launched this podcast, I have always wanted to have you on it, we're finally here. We've been online buddies for a few years now, ever since I discovered your book, Founding Sales, which we're going to talk about, and it's just been a lot of fun knowing you, so thank you again for being here.

**Pete Kazanjy** (00:04:20):
The quick story was Lenny had shipped his different genres of marketplaces and how to start the liquidity and growth and whatever and I was obsessed with it, and then somehow, I ran into you at Brianne Kimmel's SaaS School. I gave a presentation on Founder-led Selling and there was a scrum of people around me and I was talking about amazing writers and amazing content online and I referenced the series, and then you raised your hand and you were like, "That was me," and I was like, "What? You're amazing." And then we got beers and now, we're happily ever after.

**Lenny** (00:04:53):
Look at us now. And then you encouraged me to make a book out of that post, which I have not yet done, maybe one day.

**Pete Kazanjy** (00:05:00):
Eventually.

**Lenny** (00:05:00):
Eventually.

**Lenny** (00:05:01):
So, we're going to be talking a lot about sales and a lot of the stuff that you cover in your book. Before we get into it, could you just take a minute to share a little bit about your background and some of the wonderful things you've done, to give folks a sense of your experience in the sales world?

**Pete Kazanjy** (00:05:14):
I think probably the most important thing to characterize for folks is that I don't actually have a background in sales originally, which were most sales leaders and sellers come from, they graduate from school or a BDR, become an AE, AE manager, or a BDR manager, and then go on to sales leadership. My background's actually in product marketing and product management. I started my tech career at VMware back in the day, tons of amazing, fun VMware diaspora. And then I started a software company called TalentBin, it was a recruiting software company in, geez Louise, 2009. We quickly realized that, "Man, this B2B software stuff doesn't sell itself, irrespective of maybe what people say on the internet," at least back then. So, I had to be our first seller, our sales manager, our first sales leader, and that's where I learned how to do sales.

**Pete Kazanjy** (00:06:02):
Also, I just realized, "Man, this isn't rocket surgery, anyone can learn this. If I can learn this, other people can learn this, even though there's not documentation on it." So, the software company was eventually acquired by Monster Worldwide in 2014 and then I wrote a book on sales for founders and other first-time sellers, it's called Founding Sales. Mainly, it was the book that I wish I had, rather than having to learn by a narrative from the first round capital portfolio and what have you. And then subsequent to that, I started what became the nation's largest sales operations and leadership community, it's called Modern Sales Pros. It's 30,000 sales operations, sales leaders, et cetera. And then started a new software company called Atrium that makes data-driven sales management software, and then here I am. So, I think a little bit about sales, turns out modern sales, not that old sales, modern sales.

**Lenny** (00:06:59):
Ooh, I'm curious to hear what that is. But before I ask you that question, I just wanted to mention your book, Founding Sales, is the book I give every founder that is trying to figure out sales. Every time I give it to them or point them to even your site that has it all for free there, they're always just like, "Holy shit, this is exactly what I needed," so we're going to be covering a lot of that stuff in our little chat.

**Pete Kazanjy** (00:07:20):
Rad.

**Lenny** (00:07:20):
Can you actually just briefly talk about what is modern sales versus what you called traditional sales or old-school sales?

**Pete Kazanjy** (00:07:25):
Oh, I just think that there's a little bit of a mindset change. It's a little bit related to some of the reasons why founders and other folks maybe have this perception of sales be like, "Ew, sales, ugh" because people, their only experience with sales is Glengarry Glen Ross or movies with a sleazy used car salesman and stuff like that, whereas the way to think about what sellers are is they're the microeconomic agents in the market that bring supply to demand rather than waiting for demand to find supply. They have supply in their back pocket and they run around trying to find people who ought to have the demand, maybe they have the demand right now, maybe they don't realize that they have the demand, and then they elucidate to them why they ought to have the demand.

**Pete Kazanjy** (00:08:08):
So, A, that process is very important from a technology deployment standpoint and also, B, it's very measurable, especially in a modern environment with modern CRMs and also all the digital activity that we do, email, calendar, phone, Zoom, et cetera, all this information is now being recorded such that you can then measure, manage, and improve behavior. So, very similar to how back in the day, you do product analytics by licking your fingers and sticking it in the wind, and then Mixpanels showed up, then Amplitude showed up, then so on and so forth, and the same is the case in sales, as well. So, modern sales is a more thoughtful, operational, rigorous, analytical bent, it's been around for a while. It's one of those things, the future is here, it just wasn't widely distributed, but now it's being much more distributed and much more embraced. Like the pre-Moneyball moment in sports and baseball to the post-Moneyball moment, we're now just flipping over there, so that's the delta.

**Lenny** (00:09:17):
Awesome. I definitely want to talk about ways to get better at sales and things you've learned about just how to improve at sales, but to set a little bit foundation for that conversation, I want to talk about founder-led sales. You touched on this topic, your book is basically named after this concept of founder-led sales. Can you talk about what that is, why it's so important, and maybe why founders often get this wrong?

**Pete Kazanjy** (00:09:37):
The way that I think about the book, Founding Sales, I like to think of it as the sequel to Eric Eric Ries's The Lean Startup or Steve Blank's Four Steps to the Epiphany or Startup Owner's Manual or whatever, where if you think about the stages, and this is all B2B, if you think about the stages that a product goes through, it's one, you've got to know what problem you're solving and validate that, and it's got to be real. It can't be like, "Oh, well, I thought I had this problem," it's got to be validated. That's customer development, that's customer research, and that's more of a product management function. And then there's building the minimum feature set in order to prove that maybe technology can fit to this problem and solve it.

**Pete Kazanjy** (00:10:26):
That's how we create value as technologists, is piecing together technology and code or bits and atoms and what have you in order to solve a problem that people have. But then the next step is like, "Cool. Now, I've got to get someone to pay for this and I've got to do that in a reliable fashion and I've got to do it in a scalable fashion," and so there's a little bit of a loop there. It's not like, "The product's done, throw it over the wall, have fun, kids." It's a loop, where the minimum viable version of your product is probably going to suck and then in order to get to the minimum valuable step, you've got to be interfacing with a lot of customers and that's a sales behavior, getting in front of people and being like, "Hey, I think you probably have this problem if you look like these other folks right here."

**Pete Kazanjy** (00:11:11):
The point is is that you can't outsource that behavior, the founder's got to do that stuff. A lot of people ask me that question, "Well, I suck at sales," or, "I'm afraid to talk to people," or, "Interfacing with non-friendly parties makes me uncomfortable." The way to think about it is, I forget who the person was who said, "Startups versus incumbents is a race between can innovation get to distribution before distribution can get to innovation?" So, this is a related concept where as a founder, it's going to be way easier for you to get good, or minimally viable good, at selling by having interactions with non-friendly parties and having commercial conversations and asking for money in exchange for the value delivery.

**Pete Kazanjy** (00:11:58):
It's going to be easier for you to do that than it is for some third party to become as expert at the subject matter that you're tackling that you are. Because as a founder, early on, use Atrium as an example, we make data-driven sales management software, which it exists to help sales managers and teams use metrics and data to improve the performance of their reps. The way I think about it is Datadog-y Amplitude-y, but for your sales reps. I'm probably the expert in sales analytics in the world, and so back in 2016 and 2017 when we were doing this, put aside the fact that I already know how to do minimum viable selling, if I had tried to get somebody else expert at that in order for them to go out and do that in the market, that would have been not good.

**Pete Kazanjy** (00:12:46):
This is why Steve Blank always talks about startups can't get to scale without firing their first VP of sales, it's oftentimes because they skip that step, and so the founder's like, "Hey, man, I'm going to pour a little bit of sales on this, hire some sales leader or whatever, some sort of seller, and outsource this." You really just can't do that, not for the first couple dozen customers, it's just not tenable. You lose that feedback loop, you lose the learnings of whether or not your message fits the market, all that sort of stuff. You're playing a game of telephone with that with a third party seller versus even you just want to keep that in one brain to start, then package it, and then when you have a repeatable while loop, a selling while loop, then package it and hand it to someone else. So, that's my diatribe on why founders have to do this.

**Lenny** (00:13:35):
I was going to try to summarize the reasons that you should be doing this and it sounds like there's so many. One is figure out what you should actually be building, that's a reason founders should be selling, two is learn how to position and pitch and sell, three is figure out what you could teach your salesperson when you hire them. Is that a summary of why you should be selling as a founder for a while?

**Pete Kazanjy** (00:13:55):
Yeah, for sure. One, it's going to help you with your product development because you're not going to have that abstracted, for sure, two, you're going to be the person who's going to figure out how to talk about it in an effective way, and then three, it's going to make it such that you can package that up such that other human... Because that's the way that B2B startups scale, is it's not WhatsApp or Twitter or Airbnb or whatever, where you have this scalability via marketing, the way that B2B organizations scale primarily is by adding more salespeople who then have customer-facing meetings with prospects.

**Pete Kazanjy** (00:14:32):
And then you cap out with the number of hours that are in the week, there's only four or 50 hours in the week, especially as a seller because you interface with other people during business hours, and so the way that you scale up is by just adding more salespeople. So, that's why packaging that up is really important, because then you're going to shove it into the brains of two more salespeople, and then once they're successful, you're going to go to four, and then once they're successful, you're going to go to eight, and then once they're successful, you're going to go to 16.

**Lenny** (00:15:00):
You talk about this while loop concept, which I love. What are signs that it's time to hire your first salesperson? It begs the question, when do I do this?

**Pete Kazanjy** (00:15:10):
I'm not a software engineer, but I like to use technical metaphors with technical audiences because I think it's helpful, so it's like when it runs on your local, now it's time to see if it reproduces over here, so if it reliably runs on your local and it doesn't air out, so then what would the definition of not erroring out look like? So, generally speaking, it is to contingent on your sales motion, but it's going to be that you can reliably, at a pretty okay win rate, so maybe 15% or 20% or 25%, turn first meetings into eventual customers and do that in a reliable fashion. It's not like, "I engaged 10 arms-length parties and I got two customers closed." It's like, "Hey, that's great. That's a good start. 5X that, 10X that."

**Pete Kazanjy** (00:16:08):
Take 50 at-bats, take 100 at-bats, and now that you know that you reliably, for every cohort of ten first meetings, what's known in sales land as opportunities, for every cohort of 10 that you engage, are you closing 1, are you closing 1.5, are you closing 2, or are you closing 2.5, if you're in there? But if you're at like, "For every 30 I interact with, I close one," well, it seems like that's probably pretty inefficient, unless you're selling $500,000 deals or something like that. So, it's at the point where it feels like it's statistically significant, it feels like it's repeatable, because what you're going to then do is now it feels like it's a safe bet to try to abstract that out to somebody else.

**Pete Kazanjy** (00:16:54):
Because the only way we're going to get to success is we're not going to have Lenny go and sell from morning, noon to night. What we're going to do is we're going to take the information out of Lenny's brain and we're going to put it into slides and we're going to put it into scripts and we're going to put it into email templates and all that sort of stuff, and then we're going to shove that into the brain of two more reps and see if now we can get it to run in the cloud, in the sales cloud here. And then to start out, it may fail, the same way you're like, "Cool, it runs on my local. Uh-oh, it breaks over here. Why?" And then that's the next stage is now you're figuring out how to get those other folks to sell as successfully as you have, and that becomes the next job.

**Pete Kazanjy** (00:17:39):
Actually, this is the presentation I gave at Brianne's SaaS School, if you Google it's just called Founder-led Selling, it's available online. Essentially, there's a bunch of stages in the B2B maturity journey and you have to go through them in order to get to the next one, if you jump stages, you're hosed. So, in this case, if you know that you can reliably sell this yourself, that's great. Then, the next thing to do is get at least a couple people reliably selling, as well as you, not 10, because you're never going to get 2 successful if you're trying to onboard 10 concurrently. And then if you get those 2 successful, now you've earned the right to go to 4, 8, et cetera.

**Lenny** (00:18:21):
I love this heuristic that you shared that you want to get to about 15 to 25% of contacts closing to a customer. I see you shaking your thumb. I think that's really useful. So, it's a bit less than a third and doing 50 to 100 attempts is roughly where you want to be?

**Pete Kazanjy** (00:18:39):
Yeah. Importantly, what you don't want to do is, and I think probably a lot of the product managers who like to listen to Lenny's Podcast here might appreciate this, is you want to bring on cohorts of users and then see what's going on, then learn, and then bring on new co cohorts of users. So, going and doing 100 at-bats and then being like, "Did it work or did it not?" Versus, "Hey, let's have 10 for prospect and try to get 10 first meetings," have all those interactions, see how your conversations land, see how the discovery questions are evoking the right response or not the right response, see how your slides land, see how your demo lands, all that sort of stuff.

**Pete Kazanjy** (00:19:15):
If it's working well and you're getting to the next stage, "This is great, I would love to introduce you to my boss," that's a good sign. If it's like, "I'm just not getting it." Cool, back to the drawing board, versus doing 100 all at once and being like, "Now, did it work?" We want to break it up and then constantly just be iterating, iterating, iterating. Again, I think your audience might appreciate this, the way to think of a sales motion, so sales motion is a fancy-pants way of describing just all the things that you do in order to take a prospect and bring them through the sales process and then eventually close them. One helpful way to think about it is kind of like software and what you want to be doing is constantly updating it. Oh, that was a really interesting question that the prospect asked right there, I didn't have a good answer for it and moreover, I didn't have a slide for it.

**Pete Kazanjy** (00:20:04):
You know what I should do? I should make a slide that handles that objection so I can show it to them visually and also, it'll help give me guardrails and a talk track and that'll be nice. So, I'm going to do that and then I'm going to update the source code. Now, my sales motion has been updated. And then the next loop through, ideally the next time that person says, "Oh, I don't know, Lenny, it doesn't really sound like X, Y, Z," you're like, "Oh, a lot of people say that, but here, if you look over here, you can see this." "Oh yeah, that's a really good point." "Wonderful. So, as the next step, let's go ahead and talk to your boss." So, now your sales motion has been updated and the collateral's been updated and now, we're being more effective sellers. You're just going to do that dozens and dozens and dozens and dozens and dozens of time before you have a repeatable sales motion.

**Lenny** (00:20:55):
What's interesting is with this heuristic, two-thirds of the time, it's not going to work out.

**Pete Kazanjy** (00:20:59):
Nope.

**Lenny** (00:21:00):
So, a lot of times, they're going to be like, "Ah, I don't get this, leave me alone." Is there other leading indicators that tell you that you're improving, knowing that only a third or maybe a fifth of the time it'll work out? Is it talking to the boss off more often, what else do you look for?

**Pete Kazanjy** (00:21:13):
Yeah, exactly. Totally. So, what are the leading indicators of success? Because if you're only looking at lagging indicators, again, it's probably a it's a funnel on a new feature, so the opportunity is an at-bat or a potential transaction, and so usually what you do is you model out the stages in your opportunity. So, generally, there will be different stages depending on the sales motion. So, use Atrium as an example, we sell on customer data. It takes five minutes to turn on an Atrium account, it's really helpful for folks. They just sign in, they OAuth with Salesforce, great. So, a really important stage in our sales motion is, we call it data light, has data been lit up? So, that's a stage, we have a discovery stage, we have a data light stage, we have what we call a preview stage, are we previewing it with the staff? Then, we get to a commercial discussion.

**Pete Kazanjy** (00:22:08):
So, you can measure how you're getting to those stages, which is somebody lands on whatever page that Lenny was in charge of at Airbnb and did they click on the right thing and do they get to the next thing and did they get to the next thing, get to the next thing? So, in sales, it's kind of the same thing. So, the more sophisticated version of this is looking at stage conversions, what have you, the less sophisticated version of it, which early on, I think is an appropriate way of doing it, is like, "Hey, man, are we getting second dates?" So, just metaphorize it to Hinge or Coffee Meets Bagel or whatever the more recent one is, it's like, "Are we getting the second dates? Are we getting the third dates? Because if we're not getting the second dates, probably something's amiss there."

**Pete Kazanjy** (00:22:51):
So, what we want to do is we want to say, "Great, of all of our ten first meetings, how many gets to second meetings?" It would be great, the lagging indicator is 2 wins out of 10 or what have you, but I'm going to come into these conversations and out of my ten first meetings, I want seven of them to get to the second meeting. And then of those seven, maybe I want 4.5 of them to get to the third meeting, and then ultimately, I want 2 or 3 to win. That's the way to think about that, those are the leading indicators. So, as those conversions get better like, "Man, I'm not getting any second dates. Oh, okay, cool, you need a haircut or you need a shower," and the same applies to your sales motion, as well. Your message is not landing, you're targeting the wrong people, what's going on here? You need to think about it.

**Lenny** (00:23:42):
You need a better pickup line.

**Pete Kazanjy** (00:23:43):
There you go. Now, you're not even getting first dates, man, go all the way up to you need a better Hinge profile picture. You're just not getting any matches, ew.

**Lenny** (00:23:55):
As a founder, do you have to get good at sales? A lot of founders are like, "Oh my God, we're going to do PLG. We're going to be self-serve, freemium, we don't need sales. I'm just going to let people figure it out." Is it a requirement of a B2B business to get good at sales as a founder?

**Pete Kazanjy** (00:24:11):
I would say you don't have to get good at it, you just have to get non-zero at it. There's this really great article on Lenny's newsletter on adding a sales organization to a self-serve product that Lenny had me write and then he edited the heck out of it, and it's really a fantastic asset. But what I would say there is that there are a lot of PLG or self-serve motions out there that they've stagnated themselves because they didn't add the sales piece to it. I would encourage people to read that article, I forget what it's called, you added a really cool name.

**Lenny** (00:24:47):
**Oh, The Transition**:
Layering on Sales to Product-led Growth.

**Pete Kazanjy** (00:24:51):
See, you're good at naming things.

**Lenny** (00:24:54):
That's inspired by David Sack's The Cadence, which I love for how to operate.

**Pete Kazanjy** (00:24:58):
There you go. That is a great article. So, it's not that you have to be great, you just have to recognize that it's important. A good example of this would be, probably the most famous example of an organization that maybe didn't get sales religion as quickly as they should have would be Dropbox. Dropbox has phenomenal early sales leadership. One of our investors here at Atrium is a gentleman named Mike Marg, he's a partner at Craft Ventures, he was an early sales manager and leader there, Kyle Parrish was the head of sales at Figma, Marissa Fuhrer is over at Figma, as well. There's all these just absolutely fantastic Dropbox folks, but the problem was is that the organization, from a product standpoint, never put all as many calories behind product development that would support the ability to sell to across an entire organization.

**Pete Kazanjy** (00:25:48):
So, the way that I try to succinctly describe that is never mistake your lead gen for your business. I think the good news is that a lot of people took a lot of lumps there and folks have learned that, maybe Slack almost missed that, but then they brought in a bunch of Salesforce folks and other folks, actually, Mike Marg was also an early sales manager at Slack, as well, and really got a religion around that. Because it turns out that people paying 19 bucks a month or 29 bucks a month or what have you is really great, but getting to a $50,000 or a $100,000 or a $250,000 contract, that's where big ARR numbers start racking up, and organizations want to talk to a human in order to navigate that.

**Pete Kazanjy** (00:26:34):
So, PLG is great for landing and permeating an organization and there's a bunch of great... Craft invests in this like crazy, so Scratchpad is a great example of very bottoms-up. Atrium's pretty bottoms up, as well. It's like, I don't know, what is the Silicon Valley joke, middle out or whatever, because we land with sales managers and SDR managers. What you're doing is you're solving the problem that the user has, but the problem is the user doesn't necessarily have large budgetary authority, so you can get them stoked up, but then you've got to talk to the person who's got the purse strings, and so that's going to require sales. That's okay.

**Lenny** (00:27:13):
Just to punctuate that, basically 100% of B2B companies end up building a sales team?

**Pete Kazanjy** (00:27:20):
I would say that's the case. It's more of a question of when versus if, so even the really famous ones like Atlassian. Atlassian, they had a sales organization, they just didn't call it a sales organization and they went pretty far without a lot, but instead what they did was they just priced the product breathtakingly low. I think developer tools can oftentimes do this, where because developers are pretty technical, they can adopt product, they don't need handholding in order to adopt a product that is complicated enough to be valuable. Datadog's a good example or New Relic or AppD, but even those guys very early on had meaningful sales organizations. There's a lot of reasons why Datadog ended up winning that market, but their sales organization is no joke. Even developer tools, you might think, cool, well, the developers can just swipe their credit cards. Yeah, they can, but then you're going to be eventually capped there. Look at Snowflake. Snowflake has, I don't know, 500 salespeople, you're going to need a sales org.

**Lenny** (00:28:28):
Let's shift a bit to talking about just how to get better at sales, at the scale of sales. I think it's interesting because you don't have a sales background and so you've had to learn how to do this and you did a lot of research and building your business, you've had to get really good at sales. So, maybe a first question, what's the number one tip that you have for getting better at sales?

**Pete Kazanjy** (00:28:50):
The first chapter of Founding Sales talks about what I call sales mindset changes. Because I think the big thing is it's just so weird, it's just such a weird shift in behavior. Because if you think about it as a product manager or as an engineer or whatever, how many people do you interact with day-to-day? Oh, 6, 10 maybe.

**Lenny** (00:29:10):
Not too many.

**Pete Kazanjy** (00:29:11):
It's always the same people and so it's super comfortable, whereas in sales or anything customer facing, what ends up happening is you're meeting multiple new humans every day, if you're doing it right, and that just is such a mindset shift. You're not going to be able to remember everybody. You're going to have to write it all down. You're going to have to use the CRM for that. You're in the starting blocks on the track. You're in the starting blocks and you have 90 seconds or a couple minutes to form rapport, to make somebody feel like they should trust you and they want to be honest with you. You have to be very focused on activity orientation, whereas engineering and product management, there's does a lot of super deep work.

**Pete Kazanjy** (00:29:52):
It's like Paul Graham's Maker versus Manager Schedule. Salespeople have manager schedules, interestingly enough, where what you're doing is you're constantly contact switching, an ideal salesperson's calendar or a founder who's doing sales is 2, 3, 4, maybe 5 customer-facing meetings a day with different humans. And then moreover, then you're having incremental interactions with those folks later on, like later that week or the next week or what have you, so then you have to keep continuity of these multiple parallel conversations. It's a totally different set of skills and so it feels super weird to start out, but what ends up happening is it's just a skill. You just start doing it, you start doing it, you start doing it, and you just become used to it, you become calloused. You're like, "I'm incorrigible now. You put me in an elevator, I can talk to anyone."

**Pete Kazanjy** (00:30:43):
So, one, just recognizing it's going to be a pretty big mindset change, and then the second thing you can do is then once you know that there's going to be a mindset change, is you can focus in on making those behaviors be better. So, as an example, one of the things I challenge my staff to do is I call it turbo rapport, it needs a better name. But think about people that you interact with in the world who maybe are a little shields up, they're probably used to interacting with people who are not going to be super nice to them, maybe it's bartenders or a flight attendant or a barista, or fill in the blank. Think about how quickly you can become friends with them, how you can break that down, because that's going to be a really good skill for you to have when you're interacting with a prospect.

**Pete Kazanjy** (00:31:31):
And then what that's going to allow you to do is then ask them candid questions about their current situation that either, A, they may know about or, B, you ask provocative questions that make them think about the world in a way maybe that you want them to and realize that they have pain they didn't want or didn't know that they had. My friend, Brett Burson, had this great tweet one at one point where he said, "Think about the things that you do in your day-to-day that are like a pianist, like a piano player, playing scales like, 'Da, da, da, da, da, da.' What is the version of that for selling?" That's rapid rapport building, asking good questions, asking follow-up questions, being willing to ask uncomfortable questions, all those sort of things, and asking for money and then shutting up and waiting for them to answer, all these are very uncomfortable things, but the more you do them, you'll just get good at them.

**Lenny** (00:32:31):
**Pete Kazanjy** (00:33:44):
I think this is like the, remember the modern sales versus old-school sales thing?

**Lenny** (00:33:44):
Mm-hmm.

**Pete Kazanjy** (00:33:50):
The old-school sales thing is like, "I'm going to sell something to a mark," or the best example of this, "That guy's a great sales guy, he can sell ice to an Eskimo." It's like, "Man, if you're selling ice to an Eskimo, you're an asshole. What is wrong with you? They don't need ice," unless they're visiting Southern California. So, as a seller, the way that I like to frame it to people is that you're a consultant that has a particular predilection for a given solution, your solution. Use Atrium as an example. Atrium's minimum ICP is probably SDRs plus AEs in an organization should probably be at 10 all the way up to 300. So, if someone shows up and they're like, "Man, I've got to get really good at sales, I need to buy your software, Pete," and I'm like, "Cool. How many salespeople do you have?" They're like, "I have one." I'll be like, "Man, I'm not going to sell you Atrium. You're just going to be unhappy, it's going to be dumb, it's going to be a waste of our customer success resources, you're going to churn," all those sort of things.

**Pete Kazanjy** (00:34:56):
But if instead what you're doing is you're saying, "Hey, I'm going to go out in the market and I'm going to find the people that have a high proclivity that our technology solves and then I'm going to talk with them about how they're solving that problem right now, and ideally, through a series of questions, I'm going to reveal that to them that they're doing it probably not great. And then once I've revealed to them the fact, through this directed questioning, what's known as discovery, that they have this high magnitude problem, that it is causing them lots of money, that it is a pain in their ass, and then I reveal to them that there is a better way of approaching it and magically enough, I happen to be a representative of that solution," well, now that's an ideal transaction and everybody wins. And then scale that up across an entire economy and you can see why I was saying that sales is the grease that makes the economy work like that and also importantly, brings new technology to the market in a way that makes everything better.

**Lenny** (00:36:01):
If someone's listening to this and they're like, "I want to get better at sales, what's one thing I could do differently tomorrow, this week, to improve my ability to sell my product?" What would that be?

**Pete Kazanjy** (00:36:12):
There's the non-complicated version and there's the complicated version. The non-complicated version would just be just walking down the street, make eye contact with everybody, and then every person that you stop next to at Starbucks or the crosswalk or whatever, just strike up a conversation with them, figure out a mechanism by which you can start a conversation with them. Compliment their shirt or their shoes or remark on something. Don't use the weather, because that's lazy, but figure that out, so that's the first version. Probably the more sophisticated version is just be very, very tight on your ICP, just be very, very, very crisp around who has your problem and why. Being more crisp around that and then having that understood is a great way of making sure that you're not wasting time on people who don't have your problem and that you're doing more of those loops with people who are right in the white-hot center. So, one is a behavioral thing and one is a more thoughtful thing.

**Lenny** (00:37:07):
That's great. Can you actually explain ICP briefly, because a lot of people may not know that term?

**Pete Kazanjy** (00:37:11):
Thank you. So, ICP stands for Ideal Customer Profile. Actually, it's important to think about there's two things in a B2B sales motion, there's the characteristics of the account, which is the company that's going to buy, and then there's the characteristics of the human and the personas that you're going to be interacting with. Let's use Amplitude as an example. Amplitude's ICP would probably be organizations that make software products, that probably have at least a couple of product managers, because if there's a single product manager, it might be too much, they might be at the point where they don't need a full-blown enterprise analytics suite, and that's probably it. And then on the human side, who are the people who participate in that conversation? Well, the product managers are going to be the ones who are going to be the users, but engineering is probably involved in order to make sure that Amplitude can talk to the cloud data warehouse and so on and so forth, and then moreover, the person who owns the budget might be the VP of product, not the product manager, or it might be the VP of engineering or the CTO.

**Pete Kazanjy** (00:38:18):
So, those three different folks that we talked about there, it's different humans. Ideal customer profile is understanding what those parameters look like for looking at an organization in order to say, "Man, that's an awesome op, let's go get in front of them," versus, "Eh, I don't know if that's a very good opportunity, maybe let's pass on that," and then the personas are, "Great, that's an awesome op right there. I know that I'm going to have my first conversation with Lenny, but with an intention that I'm eventually going to get to the VP of product at Airbnb, and that's Suzy over here. And then once we get validation from her, then I know that the VPE over here is Frank," and knowing who the personas are. So, that's what ICP and personas are.

**Lenny** (00:39:06):
Awesome. There's a template that you've created that helps you lay out your ICP, so we'll try to link to it in the show notes. I have to find it again.

**Pete Kazanjy** (00:39:13):
Nice. Sounds good.

**Lenny** (00:39:15):
So, we've talked about founder-led sales and how founders should be starting sales, we've talked about just how to get better at sales as a founder, as anyone. I want to talk now about hiring salespeople.

**Pete Kazanjy** (00:39:27):
Sure.

**Lenny** (00:39:28):
Great mug, by the way, Coffee is for Closers. I love it. Can people buy that online or is that just a one-off?

**Pete Kazanjy** (00:39:36):
This is a Modern Sales Pros mugs. I think we have a bunch of Yetis that we give away for Atrium, as well, but we're big onto sales jokes here because you have to... We stole this from New Relic, being very user-centric in your swag, so I've got my Sales Nerds jacket on here, I've got my Let's Get It hat here, I've got my Coffee is for Closers mug. These are all inside sales jokes that maybe your audience won't necessarily get, or maybe they will, but our audience very much gets them. They're like, "Oh man, your hat's so funny. Can you send me one?" I'm like, "No problem. You should buy our software."

**Lenny** (00:40:11):
Love it. So, hiring salespeople, we've talked a bit about a lot of these things, like maybe when it's time to hire a salesperson when you're closing a fourth or fifth of your opportunities when this while loop is kicking in. So, in terms of the who to find for this first sales role, and you mentioned that VP of sales are often let go, it's a very high rate of not working out, is that true?

**Pete Kazanjy** (00:40:33):
Yeah. Again, this is mapped out in the Founder-led Selling presentation and then also in Founding Sales, the book. Generally, what you want to do is you probably don't want to start with a VP of sales to start, a sales leader, and there's a couple of reasons why there. Even if you figured it out yourself, that's required, you have to get to that minimum sufficiency of 10, 20, 30 customers yourself first. But then the reason why I advocate for folks to hire a couple of sellers or a couple of AEs to start is because, again, you have that software in your brain. Unfortunately, there is no GitHub for sales motions, and so it's in your brain, it's in your documents, et cetera, and so now, you're going to teach these other folks. So, what you want to do is you want to hire a couple early-stage pioneer sellers to take that sales motion.

**Pete Kazanjy** (00:41:30):
The downside of seeking to hire a VP of sales or a head of sales, or what have you, who actually is a head of sales is coming out of an organization where maybe he or she is a manager of managers or manages eight reps or something like that, is that person hasn't been selling for a hot second. I think actually Jason Lemkin had a pretty funny tweet about this the other day where he was like, "Hiring the VP of sales who's been there and done that before, why exactly does she want to do it again?" Like, "Oh, you scaled up a Datadog or Figma or whatever, you should come to my crappy little startup," it's like, "I'm professionally rich." So, instead, the great folks to look at are the deputies or those early-stage sellers.

**Pete Kazanjy** (00:42:18):
So, the example I always use here, my last software company was in recruiting, so if you have a new recruiting technology, my buddy, Troy, runs this recruiting software company called Guide. They make this really cool, guided, hey, hiring process for candidates, whatever, but they sell to recruiting organizations. So the early-stage sellers that he would be interested in would probably be early people at Lever or Greenhouse who sell to the same persona, probably around the same average selling price, but ideally, not an AE who joined Greenhouse last year or two years ago.

**Pete Kazanjy** (00:42:59):
Greenhouse just has a phenomenal sales organization, their sales leadership is absolutely fantastic, the gentleman who's the CRO over there is a good friend of mine, Sean Murray. But early-stage selling takes early-stage sellers or people who have been there, because you're not going to have all the collateral, slides and scripts and whatever aren't going to be all buttoned up and with a bow around them, and so looking for those early-stage, grimier, grittier sellers is a more effective way of going about that. Those are the folks that you want to look for once you've gotten to that statistical significance of your own selling capacity.

**Lenny** (00:43:37):
To make that just even clearer, the suggestion is if you're, say, a Series A founder, what's a profile of a person you look for? You said it's a deputy at a successful sales org?

**Pete Kazanjy** (00:43:48):
I'll give you a couple examples. I don't know, say you're doing some sort of design tool, I would go look at the Figma sales organization and I would look at some of the earlier sellers who were there maybe two years ago or three years ago or what have you, maybe you could consider getting a sales manager there who's not super far from selling. A great example of this is there's this woman, Marissa Fuhrer, who works at Figma, she's absolutely fantastic. She works on the enterprise team there and she was at Dropbox previously as a seller for a long time.

**Pete Kazanjy** (00:44:24):
She would be a great profile for someone who's not too far from having sold and is willing to roll up her sleeves, but ideally, that would probably be the person who you'd want to hire after you've hired those couple of sellers and gotten them to success. Because the other thing, too, with Marissa, she's probably going to look at your organization and be like, "Cool. Prove to me that your product fits the market, because I don't want to necessarily take a bet on you," and then you would say, "Well, in addition to having a 25% win rate with me, I have these two sellers right here and they both have 20% win rates and you can see that they're both closing $50,000 of bookings a month, all I need you to do is scale it up." In which case, that early stage head of sales is like, "Let's do it."

**Lenny** (00:45:10):
She's about to get a bunch of LinkedIn requests.

**Pete Kazanjy** (00:45:13):
She's great. This is one of the things that we really love at Atrium, is we have really great customers. We're creating a new category of software and so it's one of those things where more advanced, more modern sales managers and leaders really get it, that's how it always is in category creation. But when you find the people who really get it and really get it, they turn out to be awesome. That's one of the things that just makes startups fantastic.

**Lenny** (00:45:40):
What's a sign that maybe it's not working out when you hire your either first salesperson or maybe first five, what are signs? Because you said it often does not work out, what are early signals like, "We should rethink this"?

**Pete Kazanjy** (00:45:56):
This is another reason why it's really important to do it yourself to start, but presuming that you've been able to close business on a reliable basis, again, with arm's length prospects, it can't be Lenny's mother-in-law buying my software-

**Lenny** (00:46:13):
Huge fan, for real, actually, she is.

**Pete Kazanjy** (00:46:17):
God bless, but she's not ICP for Atrium. This is the danger of doing revenue trades in your accelerator or whatever, it's not real. So, if you have done that and you've sold 20 or 30 deals, you know it can be done, we have an existence proof of this. So, if someone else can't do it the way that you do it, and this is why hiring two folks to start is effective, you don't want to hire just one, maybe three, but four, it's like, "Ugh, that's a lot to manage," at least to start. So, if you have done that and the person, their win rates are poor or their activity levels are poor, things like that, those are usually indicators that it's not work out, that they're not getting those second dates, they're not getting those third dates, but importantly, they have to have the materials in question.

**Pete Kazanjy** (00:47:11):
Did you create the slide deck? Did you take people through and did you give it to them? Did you take all the discovery questions that were in your brain and write them down into a Google Doc or a Notion page or what have you? Do you have a demo script for them? If those things are not present, then probably no one's going to be successful, or at least they're going to have to rederive all that stuff that you already did. But if you have all those precursors and it's not sticking for someone, that's probably a good leading indicator that they're not going to work out

**Lenny** (00:47:38):
How much time do you give these folks before you make a decision?

**Pete Kazanjy** (00:47:42):
This is why it's so, so, so important to look at leading indicators. This is something that we just think about all the time here at Atrium, from a instrumentation and data-driven sales management, is if someone's not having customer-facing meetings, if they're low activity, you're never going to win anything. If you have a 50% win rate on two opportunities in a month, that's probably still not going to be super helpful unless you have a very, very, very high deal size. So, looking at those leading indicators like, "Are they having first meetings? Are they having second meetings? What does their email volume look like? Are they progressing things through, are they getting things to proposal, and then eventually, are things closing?"

**Pete Kazanjy** (00:48:24):
I do a bunch of masterclasses for Atrium on data-driven sales management and one of them is on ramping. It's called Ramping For Success, I forget the name of the masterclass, but looking at those leading indicators like opportunity inflow, "Is a person putting meetings on their calendar, are they progressing them? Are they being active in the meantime?" Those are all really good leading indicators. If somebody's not getting first meetings on the calendar, you know within a month, it's like, "Cool, this isn't working out."

**Pete Kazanjy** (00:48:54):
Now, if they're not getting to second or third meetings, but they are getting those first meetings, well, now you know you've got a different problem, which they're getting those first dates, but they're not getting a second date and they're not getting a second date the same way that you were, maybe that's a coaching issue or maybe it's just a behavioral problem that's that you're not going to be able to surmount. But the point is having instrumentation on the most leading indicator possible gives you eyes onto whether or not things are working or not and you can make judgements fast, because the worst possible situation is nine months in, you're like, "Man, it's not working." It's like, "Man, I bet if you looked at the leading indicators, you would have known two months in this wasn't working."

**Lenny** (00:49:33):
I like that you gave us a bottom end of the range like, "In a month, you should be able to know, a lot of times." What would be the max by which like, "If things are going okay, by six months, it's probably going to be good," or what is that timeframe?

**Pete Kazanjy** (00:49:46):
Oh, where you know you're successful?

**Lenny** (00:49:48):
Yeah. It sounds like maybe from a month to some future month, this is a period where you can get a sense of this person is going to work out. What's that range, in your mind?

**Pete Kazanjy** (00:49:58):
It's almost like you're continuously monitoring. In the first month, maybe you spend that time onboarding the rep, teaching them, going through mock discovery conversations, mock demos, et cetera, having them ride along with you. In the second month, we would expect them to have 10 first meetings or maybe 20 first meetings and we would expect 50% of those to get to the second meetings, and we would measure those things. In the third month, we would expect some subset of those first meetings and second meetings that happened in the second month to get to a proposal, to get to a commercial conversation, and then maybe we would expect some of the deals in that month to close to win, or maybe the next month.

**Pete Kazanjy** (00:50:38):
It's essentially like you're looking at the leading indicators in the appropriate timeframe, such that if someone is in month three and they're getting a bunch of their deals to proposal, you can't declare victory yet because the money is not in the bank, however things are looking good. So, if you get to month four and lots of things are getting to proposal, but nothing's closing in month four and nothing's closing in month five, you still can't say "Olly olly oxen free," you should still be very concerned. But if the leading indicator is at the right level for the right period or right interval in ramp, then you can feel confident, but not declare victory yet.

**Lenny** (00:51:20):
Got it. Something that this is reminding me of is we are chatting ahead of this call and you mentioned that working from home is really bad for salespeople, in your experience. Can you talk about that?

**Pete Kazanjy** (00:51:31):
It's primarily bad for junior salespeople. Senior salespeople have been selling out in what's known as the field for a long time, but when you think about the behavior that we're talking about, which is learning, so what needs to happen? The new sellers, they need to learn the sales motion and then they need to be audited, instrumented, so the faster the loops are on that, the better off you're going to be. If the loops are once a day of listening to their calls or maybe even a longer interval, then just the correction loops are just going to be way too slow, versus if you're sitting next to somebody or you're sitting amongst three or four people and listening to all their calls concurrently and then they get off of a call and it's like, "Hey, that was really good, correction here, correction here, correction here, correction here. Here, run it back to me."

**Pete Kazanjy** (00:52:28):
Now, the loops, the speed with which you're able to update their software and make sure that the sales motion is running appropriately on them, is quite high. In early-stage startups, that's the only thing that matters, it's a race against time to make sure that you get to success, so you can raise your next round of financing or get to profitability or what have you, and so having asynchronous distance is really problematic for that, especially for junior folks, like SDRs, junior AEs, all of that, it really is problematic. Once that sales motion is baked and can be distributed, that's potentially a different situation, but very early on, having someone being able to sit side-by-side with your sellers, t's hard to beat.

**Lenny** (00:53:17):
So, what's the solution, if you're starting, now, a B2B company, your advice is, "Don't be remote, work in an office"?

**Pete Kazanjy** (00:53:25):
My point of view on that is, especially at early stage, from a founder's standpoint, being shoulder-to-shoulder with your co-founders certainly, but even a founder who has a couple of sellers that they're working with, being side-by-side with them in order to help them learn faster, teach them more, have accountability, and then have training loops is really what you need to do. Because the alternative is there's a whole generation of SDRs who are, it's kind of like learning loss, if you will, there's a bunch of 24 year olds who have never learned the skills that are needed at the same way, at the same clip, that they would have sitting amongst 10 others with an SDR manager sitting in the middle of them, or an AE manager sitting in the middle of them.

**Lenny** (00:54:20):
Any last pieces of wisdom before we get to a very exciting lightning round?

**Pete Kazanjy** (00:54:24):
I think probably the biggest thing is, the thing that I just like to encourage founders and product managers and what have you, is just don't be afraid of sales. There's a lot of people out there who would love to tell you a story that it's magical or like, "Oh, you've got to be a born seller," or things like that and it's really not. Those people are just talking their book, if you will, and so just getting good at those behaviors, it's going to benefit you in a myriad of ways. Even if you don't want to necessarily be an early-stage founder, even as a product manager within an enterprise organization or even a consumer organization, selling behaviors and good communication and persuasion and always thinking about what's in it for them, et cetera, those are really good skills for internal selling, for external selling, if you want to interface with customers, et cetera. All these skills are very important and impactful for a myriad of personas.

**Lenny** (00:55:19):
Amazing. Well, with that, we've reached the very exciting lightning round. I've got five questions for you, we're going to go through it pretty fast. Are you ready?

**Pete Kazanjy** (00:55:27):
I am.

**Lenny** (00:55:28):
Question one, what are two or three books that you recommend most to other people?

**Pete Kazanjy** (00:55:33):
The books that I recommend the most, there would be The Goal by Eli Goldratt. There are two books that inspired Atrium, one is the Goal, which is essentially is a novelization of the Toyota lean manufacturing system, so it's a process engineering book written as a novel, it's really fantastic. Sales organizations are just revenue factories, so if you want to think about systems thinking and processes, but in a way that's not a textbook, it's absolutely fantastic.

**Pete Kazanjy** (00:56:01):
And then the other one is a book by Bill Walsh called The Score Takes Care of itself. Bill Walsh is a really famous football coach for the Stanford Cardinals and the San Francisco 49ers and he just broke down how you can't worry about the score in the football game, you can only worry about the things that are in front of you, that you can control, and that if you do a high quantity of high-quality actions, whatever your position is, as a quarterback or a linebacker running back or whatever, then the score will take care of itself. That's very applicable to sales, as well, if you focus on those leading indicators and make sure that you're doing it in a high quantity of high quality way, then the score will take care of itself. So, those are two great books I like to recommend to folks.

**Lenny** (00:56:41):
Favorite other podcasts?

**Pete Kazanjy** (00:56:42):
Oh boy, I don't listen to too many. I listen to Lenny's and I listen to the All-In Podcast, just so I can get my fill of doom and gloom.

**Lenny** (00:56:52):
And knowledge, with this one. Favorite recent movie or TV show that you've really enjoyed?

**Pete Kazanjy** (00:56:57):
I've got a five-year-old, so we're all Disney all the time, so I think probably the one that's been on repeat recently has been Encanto. There you go.

**Lenny** (00:57:07):
Love that one. Favorite interview question that you like to ask folks?

**Pete Kazanjy** (00:57:12):
So, I'm going to change this up on you, it's less about interview questions. One of the things I'm a really big fan of is job simulation, especially in sales, and so I'm a big fan of doing screens, so we actually have a written screen that we do with folks, where it's the Google Doc that has a dozen or so biographical questions that we allow people to answer. You'd be shocked at how well it screens people, 57% people won't do it. These are not complicated questions, it's like, "Lenny, tell me about something that you've built that you're proud of," it's a dozen of those questions. So, one, you can filter out people who are not serious, you can filter out people who have low levels of give a shit. You also can see whether or not people can communicate in a compelling fashion with a beginning, a middle, and an end. You can also see their attention to detail, whether or not it's ridden with typos or they forget to answer some of them or what have you. So, it's not an interview question thing, but that's a huge hiring hack, from my perspective.

**Lenny** (00:58:10):
This is a form that folks fill out when they're trying to apply to work at Atrium, is that right?

**Pete Kazanjy** (00:58:14):
Yeah. Or it's just something that for all my portfolio companies, as well, that people just use it. It's a Google Doc and you just clone it, give it to them, "You have edit rights, let me know when it's done." You'd be shocked, people are like, "Oh, I didn't forgot to do it." Great, you told me everything I need.

**Lenny** (00:58:35):
Amazing. Final question, do you have a favorite story of you or a salesperson closing an awesome deal, something that seemed impossible, something that you're proud of?

**Pete Kazanjy** (00:58:47):
There's a gentleman in our sales organization named Sean, who was an early seller here, he's now a sales manager, he is absolutely fantastic. I think one of the things that early-stage founders and also sellers have to remember is you're, generally speaking, not going to close the deal on the first time through the pipe. As we discussed earlier, if you have a 30% win rate, that's pretty great. If you have a 20% win rate, that's pretty solid, but that still means that four out of five are not going to close, but the next time around, they might, so win rate on the second time through the pipeline.

**Pete Kazanjy** (00:59:21):
So, Sean closed, one of our biggest customers is a company called GRIN, they're absolutely fantastic. They make influencer management software for brands, very cool stuff. I think Sean probably ran three or four ops with them before we were able to get a toehold in the account a couple years ago, they were much smaller, and so now, I think they have 100 SDRs and 80 AEs that are being managed using Atrium. So, I think there's a good lesson there, which is it's not necessarily going to be the first time through the pipe and it's maybe not the second time, but you just have to keep pushing that boulder up the hill and eventually, when you do, good things happen.

**Lenny** (00:59:59):
What a great lesson to leave us with, very empowering. Pete, this was everything I hoped it would be. Two final questions, where can folks find you online if they want to learn more, more about Atrium, the book, and then how can folks be useful to you?

**Pete Kazanjy** (01:00:12):
I'm pretty easy to find online, I'm the only Pete Kazanjy in the United States, as far as I can tell. Google will autocorrect my name if you Google it wrong, so that's pretty helpful. Find me on LinkedIn, find me on Twitter. You can also find Founding Sales at foundingsales.com, as Lenny notes. The whole book is available online as hypertext, you can buy a physical copy, as well, but the reason why my wife put it into a Squarespace site was because we wanted people to be able to search it and come back to it and use it as a reference and so on and so forth. And then in terms of how folks can be helpful to me, if you work for an organization that has between 10 and 300 salespeople and you're looking to manage them better via metric, make them more efficient, that's a big watch word these days, is efficient sales organizations through better management, Atrium is fantastic for that. Atriumhq.com is the domain, but you can also just Google Atrium sales and we'll be the top result, as well.

**Lenny** (01:01:13):
Amazing. Pete, thank you for being here.

**Pete Kazanjy** (01:01:16):
It was awesome. Thanks, Lenny.

**Lenny** (01:01:18):
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.

---

## [19/20] Launching and growing a podcast | Chris Hutchins (All the Hacks, Wealthfront, Google)

**Chris Hutchins** (00:00:00):
Yes, there are four million podcasts. However, there are only about 150,000 podcasts that have had 10 episodes and have published in the last 10 days. So the easiest way to be in that top 5% ish. I don't know what the math there is. About 3%, 4% is to just stick to it. Like if you just do an episode a week for 10 weeks, you're now in the top 4% of all podcasts that anyone has created.

**Lenny** (00:00:30):
Welcome to Lenny's Podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. Today my guest is Chris Hutchins. Chris is not only a former product manager, founder and investor, he just this month went full-time on his podcast and the independent creator path. When I was looking for advice on how to build a podcast, Chris shared this awesome deck with a ton of great advice that he's built throughout his journey, and so I thought it'd be fun to spend an episode talking about all the things that you should know about launching and growing a podcast. Chris's podcast is called All the Hacks, covers all the ways to financially optimize your life, and it's one of the biggest business podcasts in the world. Chris has also been on the Tim Ferris Show actually, interviewing Tim Ferris.

**Chris Hutchins** (00:03:48):
Thanks for having me. I'm excited.

**Lenny** (00:03:50):
This is going to be a pretty unique episode, I think. You're a product manager and we're going to talk about some of the things you've learned being a PM on some really killer products. But what I want to spend most of our time on is talking about how to launch a podcast. You've built one of the most popular, biggest business podcasts in just like a year and a half. You've taught me some stuff, you've helped other people with their podcast and so I just thought it'd be really helpful just to talk about just the skill of building a podcast and all the things you should know. How does that sound?

**Chris Hutchins** (00:04:21):
Sounds great. You just did a episode about growing a newsletter business, which I was like, "This is awesome because I have a newsletter and I want it to be bigger." And I think anyone that's has knowledge to share. I talked to a PM yesterday who was like, "Oh, I've got all these product ideas. Maybe I'll start a podcast." So totally, this is fun.

**Lenny** (00:04:36):
Awesome. That's exactly how I've been thinking about it. First we did the newsletter and then podcast maybe the other things, I don't know what's left.

**Chris Hutchins** (00:04:42):
YouTube channel.

**Lenny** (00:04:43):
YouTube channel?

**Chris Hutchins** (00:04:44):
[inaudible 00:04:44] I don't know if you feel this way, but YouTube. I feel like just putting a podcast on YouTube isn't enough, I need to learn the skills of YouTube.

**Lenny** (00:04:51):
Yeah. All right. I got to get MrBeast on, that's the next goal. To set a little foundation for folks, to give him a little sense of your background and some of the things you've done in your career. Can you just talk about some of the biggest things you've done in your career, which you've been up to and then what you're up to now and also about your podcast?

**Chris Hutchins** (00:05:09):
I'm kind of like a happenstance product person. I basically really liked startups, but I didn't know what job I could have as a non-technical person. And I joined my first startup probably 10 years ago and was like, "I will do anything." And they were like, "Do business development." But it turns out we didn't have anyone who also was doing products, so they were like, "What should we build that people will buy?" So I was like, "Well, I got to figure out how we turned this API we were building for location services into a product." Left that to join other startup with a few people we co-founded, did the Jack-of-all-trades role at a startup and then quickly were acquired by Google about a year in, and I went through the interview process and they were like, "You're a PM." And I was like, "Oh, great, what does a PM do?"

**Chris Hutchins** (00:05:51):
I didn't really totally know I'd never worked as a PM. Went through Google's kind of like week of training and got thrown into it and I think I've now learned with a lot of time that being a PM is awesome. Being a PM at Google when we were working on Google Plus was not awesome. Transitioned pretty quickly over to Google Ventures, did venture capital for three years, left to start another company trying to make financial advice more affordable, more accessible. Grew that for about two, three years and we ended up selling that company to Wealthfront where I ran a new product strategy. I most recently just left that role after three years and started going full-time on All the Hacks, which is my effort to help everyone upgrade their life, their money, their travel. I'm the spreadsheet for everything, optimizer and do all this research to try to help people live better, happier, wealthier, healthier lives. And I have a podcast where we share all the hacks to do all of it.

**Lenny** (00:06:43):
Amazing. While we're on the podcast, we're going to dig into this stuff more. Where can folks, find it. It's called All the Hacks.

**Chris Hutchins** (00:06:48):
Anywhere you listen to podcasts right now, search All the Hacks, you can find it at allthehacks.com. I'd be surprised if someone listening to this is more of a newsletter reader than a podcaster, but allthehacks.com/email is the newsletter too.

**Lenny** (00:07:02):
Oh, newsletter. I love it. All right, coming back to your last gig at Wealthfront, from what I understand your title was New product Strategy and Andy Rachleff, who was the CEO for a while, kind of legendary figure. He co-founded Benchmark. He's just like this brain that... I listen to him every time I hear him on a podcast. He basically pulled you into Wealthfront and specifically wanted you to focus on figuring out new business ideas, new business lines, new product lines within Wealthfront. Is that right?

**Chris Hutchins** (00:07:31):
Yeah, so we had an engineer at the time who came up with this idea called Self-Driving Money. I was like, "Gosh, what if you could automate and optimize your entire financial life and you didn't have to rely on human financial advisors?" And we heard from our customers forever that they pay us to not talk to someone, our demographic doesn't want a bunch of humans in the mix. And so we had this idea but we didn't really know what it was. So Andy was like, "Gosh, you've been spending time thinking about financial planning and software and as an entrepreneur, could you come in and help us build Self-Driving Money?"

**Chris Hutchins** (00:08:00):
And I was like, "What is it?" They're like, "Well, we got a bunch of ideas from an algorithmic standpoint about how to do it." But, "What exactly is it?" So it was thrown into, "Let's do a bunch of customer research, let's talk to a lot of people and let's try to come up with as audacious of an idea as we could for how you fulfill the promise of automating and optimizing someone's entire financial life to the point that they don't have to think about their finances on a daily basis and they know the right things are happening."

**Lenny** (00:08:28):
When I think Self-Driving Money, I'm picturing money just driving around, like a Tesla. Money meets Tesla.

**Chris Hutchins** (00:08:34):
Yeah, the vision I had was what are the core pieces of financial life that are stressful? It's like, "I got to move money, I got to contribute to these different accounts. I want to make sure I have enough to pay my bills." And so what we ended up with was a product called Autopilot that would monitor your core banking account, whether it was a checking account at Wealthfront or not at Wealthfront or whether it was an account at Wealthfront. And we would say, "Let's make sure we leave a certain amount of money." And you could tell us that much. And then we would say, "Great." Now we had basically a series of things to fulfill with any excess. It was like, "Let's make sure you keep this much as a three-month emergency fund, max out your Roth IRA. Let's make sure you max out your 529 for your kids and let's put the rest in your kind of taxable just brokerage account." And we would just periodically say, "Oh, you got extra money, let's sweep it over and do what we need to do with it so you don't have to think about it."

**Lenny** (00:09:22):
Can you talk about the impact this had on the company and also just how long of a endeavor this was within Wealthfront?

**Chris Hutchins** (00:09:29):
It was a quick endeavor to try to start talking to people. This was just throw in the mix. I have a very poor sense of time, but let's say somewhere between six and 12 months maybe before we put something really in front of someone that could execute on all the features, there was a lot of prototype UI testing. I think Andy, he's legendary. If anyone listening to this, wants to learn about product market fit, Andy is your guy. I believe he coined the term, he teaches the class at Stanford. And the lesson was really find something people are reaching over the table want, and make sure you have that validation. And so we were putting things in front of people, clickable, full prototypes, and I remember we got to one where someone was like, "Can I go get my husband? I need to show him this."

**Chris Hutchins** (00:10:12):
And then I created this thing, which I'm sure is not that new, but I would start pretending that the product existed in the interviews. Only to find out, at the end, people was like, "Oh, it's not out yet." And they're like, "What I want to use..." You could really feel the like, "No, no, no, no, this has to be out. I want to start using it." So we found this thing that a small number of people were very excited about and we knew that a product, this was going to be a high risk bet because people don't automate their financial lives today. People drive to go pick up fast food and if you could with a push of a button, bring it to their house, you're making a thing that they do much more efficient. Right now, well, technically they do this manually, but trusting software to do it is something that we knew would be a higher risk bet.

**Chris Hutchins** (00:10:59):
And I think the takeaway, I would say the impact on the company was not as high as we had wanted in that it didn't become this wild top of funnel. I think it's similar to Tesla's autopilot. It's like nobody goes and says, "I just want to buy this car because of this feature." I'm sure some people do, but once you're in the ecosystem, it had huge impact on making it easier for people to start saving more, making it easier for people to be more confident in their finances and just automate all that behavior. So I would say the letdown was, it wasn't the big, huge top of funnel thing where people are like, "Oh, this is all I've ever wanted." Even though if you interview people and you're like, "Gosh, would you like a product that could just automate all this stuff?" They're like, "Yes, I would love it."

**Chris Hutchins** (00:11:43):
And then you hand it to them and you're like, "Do you want to use this thing?" And they're like, "Well." It's very hard to test that. And so what we found was it was a win in terms of it. It moved a lot of metrics for saving more money, increasing contributions and that kind of stuff, but it didn't become this growth channel, which Andy would say product market fit is exponential organic growth. So I would say by that metric, we didn't have product market fit, but as a tool to make a system of products so much better. We have the cash account with all the checking features, we have an investing account, we have retirement accounts. So this really brought it all together and that was super valuable.

**Lenny** (00:12:18):
Awesome. So here's my big question. What have you learned? You spent a lot of time thinking about big bets, big innovations, working within a company to come up with something totally new. What have you learned about how to approach that within a larger company? How do I successfully innovate? How to think about launching big bets, how to structure teams, anything along those lines?

**Chris Hutchins** (00:12:37):
I've learned a few things and I think some of them I've learned came naturally being a founder before being a PM. But you think that customer research is all you need to build a product at a company, but figuring out how to create excitement internally and get buy-in from other teams because they're the ones that are going to build it. They're the ones that are going to help market. It's all a team effort. Sometimes you get caught up, at least I found, as a PM of like, "Oh, we got the customer insights, we did the testing. It's all positive." And then you show the ratings you got from sub survey or the engagement or some clips and that's not the end of it. The end is creating this compelling vision for what you're building. And then the thing I learned from being a founder is, gosh, you have to state your vision and your mission and why you're here, every all-hands.

**Chris Hutchins** (00:13:27):
It seems so crazy because it's core to you why we would build this, what it's purposes, why it's amazing. But as a founder, I was like every week I was like, "Hey everybody, before we get started, this is the mission we're on, this is why we're doing it. This is the thing we're doing in the world." And as a PM sometimes you're like, "Well, I told people three weeks ago and I put it in that email that I sent out to everyone and it was in the top of the PRD, so why hasn't everyone understood why this product exists?" And I realized very quickly that, that same thing is true. So if you want to make a big bet, if you want to make a big impactful product, you have to bring people along with you. And your ability to speak publicly, persuade people, build influence within the company. Those things are all as important as your ability to identify a user need and build a product that solves it.

**Lenny** (00:14:15):
Awesome. This reminds me a lot of Airbnb, where the founders, all-hands share the vision and the strategy that they came up with that year. Every single all-hands. And it's always like, "Yeah. Yeah, we know. We know." But to your point, it's so powerful and important.

**Chris Hutchins** (00:14:28):
And some people don't know. Some people we're not paying attention that one all-hands, we're kind of missed it out, skip all-hands. Often there's just, you need everyone to be able to in... And this is a little segue to podcasting and we'll come back to it, but I start my show with saying, "Hello and welcome to another episode of All the Hacks, the show about upgrading your life, money and travel." Because I just want everyone to know this is exactly what this show's about, so when their friend asks them a question, they're like, "This is exactly what it is." And the same thing is true about a company's mission, a product, vision, anything you want everyone to really understand it, be able to talk about it succinctly and just have a very cohesive narrative in their head. That's a really big one. I think the other one is just understanding the customer, not just by talking to them, but just being in the mix, playing with all the products.

**Chris Hutchins** (00:15:14):
Something I asked a few of my colleagues before this, "What are things that I've particularly done well?" And they were just like, "Gosh, I feel like you understand what's happening outside of the walls of our business better than a lot of people." And maybe that's talking to a lot of other people who are founders talking to a lot of other people, starting companies, going to read all the comments on new financial products on Product Hunt. Really just trying to understand people beyond just customer research. And so that was another thing that I think... As a founder, you're always looking for product market fits, you're always trying to learn. Sometimes at a company it's really easy to get caught up in the research you've already done and the customers you've already talked to and you forget to kind of step outside and go talk to other people and see what other people are doing. And I'd say don't get caught up in what competitors are building and try to feature parody them, but just understanding the space outside of the walls of your business.

**Lenny** (00:16:06):
One thing I'll add to your point about reminding people of the strategy and the vision is if you can also help them understand how their team and project connects up through that, create kind of a little tree of, "Here's all the teams, what they're doing. Here's all connects to the pillars of focus and themes and then here's how it connects to the North Star metric and or vision mission. "That kind of adds another wrinkle of like, "Oh, wow. I get it. I get why this team's important."

**Chris Hutchins** (00:16:30):
There's a great analogy, I'm sure if I send a link you could put in the show notes or something about a football team. And it's like the GM's goal is to sell out the tickets and win the conference championship and it actually tiers it down. It's like, "Well, there's a defensive line coordinator." I'm not even that big of a sports person, but it's like the defensive line coordinator's job is just one specific thing, but they kind of explain how it all levels up to this one North Star metric for the company or two in that case. And I think that's just so important and when you're talking to people at your company with your colleagues, it's not just what it does. It's like, "This product will automate people's money movement so they don't have to move their money and it happens automatically." And that's cool, but it's equally as important to remind everyone, "And then they don't have to worry about their money every week and then they don't have to worry that their contributions might leave them without enough money in their checking account to pay their rent."

**Chris Hutchins** (00:17:22):
There's these two components of it which are, what does it do, but what's the feeling you want someone to have? And that gets into product vision versus just the product feature set. And whenever we've written product visions statements about things we're building, it's like, "Imagine a world where someone can feel this way about their money." And it's like, "And then this thing will do that." That's the product strategy. It's how you execute on it. And so Reforge has this awesome product strategy kind of product vision roadmap that levels them all up, which I really like as a another resource.

**Lenny** (00:17:54):
The Reforge. I just recorded another podcast this morning actually, and what you just said reminded me of it, where a lot of people focus too much on features and not enough on benefits. And the stuff you're talking about is just like, "Think about what are the benefits of the person." Versus, "Here's feature one, feature two, feature three."

**Chris Hutchins** (00:18:10):
The last little skill, and I know you, you've talked about this, but I think it's something that I was fortunate enough to not care about. Which I think is, when you focus too much at a company about like, "Ooh, I want the promotion" you get caught up in this world where you're like, "If I want the promotion, I need to do what my boss wants." And I had this fortunate benefit of... Like my last job, I was the CEO. I didn't care about my title, I didn't care about leveling up. I came in and I was like, "I want to continue trying to execute on this vision of this thing that I wanted to do." What that actually meant was my only metric I cared about was impact and trying to build a product that would work. And I think in any job in any company, it turns out you think that doing what your boss wants is actually what's going to get you promoted.

**Chris Hutchins** (00:18:55):
But the people that I've had work for me or I've worked alongside that seem to always be the outperformers, are always the people that are just solely focused on having the most impact on the company. I think the thing I learned, which I thanks to Andy Rachleff for teaching me this is when you push so hard for your ideas and you have really strong beliefs, you have to also make sure you state your intent. Because sometimes people think you're acting out of self-interest. I'd be like, "Oh, we should delete this feature and build this crazy thing. It's going to be amazing." And people are like, "Oh, Chris just thinks his idea is better than everyone."

**Chris Hutchins** (00:19:27):
And so he taught me, he's like, "It would go a long way before you said that, you said, "Hey guys, I've got some crazy ideas, but before I say them, I just want you to know that all I care about is that the company is successful. And I think this idea will make the company successful. And that's why I'm so excited about it. I don't need to own it. I don't care who owns it, I'm just really excited about it."" And when you state your intent, you give people a little bit of ease in thinking you know what it might be. And even though I'm sure half the people listening work at a company where their culture is like assume best intent is one of the pillars, it's still our nature to assume that if someone's shooting down an idea we have that maybe it's out of their own self-interest.

**Chris Hutchins** (00:20:03):
And I've learned that when you have crazy ideas and when you're pushing back against a lot of people, if you can make sure you constantly remind them why you're doing it and what you care about, it goes a lot further than if you just kind of come in there with sharp elbows and try to push for crazy things.

**Lenny** (00:20:19):
Reminds me, I think Andy is the person who on a podcast once said that every year he picks like a, "We're going to bet the company on this idea." Kind of project, is that?

**Chris Hutchins** (00:20:28):
I would say we've done that a few times. I think the thing that I always told people that I wanted to work on is like, "I want to work on a project that if successful makes everything we do as a company today feel like it's not that important because we did something that was 10 times bigger than everything we're doing today. And what we're doing now is just 10% of the company." Those are the kind of crazy ideas I like to work on. They're very hard sometimes you're like, "Ooh, I've got one." And then it just doesn't work. Sometimes you do one and it takes a turn. But I think that when companies find those things, they're so powerful. But if you don't have the buy-in for management that that's your goal... Andy, he always talks about slugging average, not batting average. He's like, "I don't care if you hit the ball every time. If one in 10 times you hit a home run that's better than someone who hits it every three out of 10 times but gets out a lot."

**Chris Hutchins** (00:21:15):
He thought about that and the balance. He's written a lot internally about the balance between working on iterative improvements to current features and then taking big bets and trying to find the balance amongst it all. But I think he does believe there is always exploration necessary for taking big bets and trying to take swings that could have outsized impact. You got to balance it because you're often wrong. And I think that's something that I was like, "That's the thing I want to work on." As someone who is kind of running a company, when you get to go to a big company and you're like, "Now I can solely focus just on this big product bet. I don't have to worry about hiring and recruiting and all these other things." So that was fun.

**Lenny** (00:21:52):
Speaking of being solely focused on something, let's talk about the podcast. So this is kind of the new thing that you're going to be focused on full-time. You just left Wealthfront and you launched the podcast maybe a year and a half ago, correct me if I'm wrong, by a year and a half ago. The podcast is Top 30, top 40 business podcast. It's probably gone a lot of higher at some points. And so there's a bunch of questions I want to ask about just how you launched this thing and built this thing. But broadly, what did I miss about the [inaudible 00:22:18] framing of the podcast?

**Chris Hutchins** (00:22:18):
Oh, yeah. That's it. It's about 18 months old. Been doing, gosh, probably about almost 100 episodes, not quite there. Weekly show and I went on parental leave part of the last 18 months and I tried to balance family and just grinding on this and it's been a passion project on the side and I'm very excited to see all the different kind of legs and tentacles that the brand and the content can have.

**Lenny** (00:22:45):
What kind of benefits and good things have come out of having a podcast and launching a podcast or running a podcast?

**Chris Hutchins** (00:22:51):
I think we all run into people and you're like, "Gosh, this person's really smart. I wish that I could just pick their brain for an hour." And sometimes you could just email them, be like, "Hey, could we schedule some time in a month and we could just chat?" But that sometimes just feels like a weird thing to ask. The podcast gives you this great platform, you're like, "Well, I have a podcast. And so I would love to invite you on and help you amplify your message and spend an hour trying to understand everything about topic X, Y, Z." And sometimes it's really nerdy and nuanced and sometimes it's broad, but being able to have a reason. I think one of my first episodes was with a guy named Morgan Housel who wrote a book called Psychology of Money. I read the book, I was like, "This is a great book. I have so many questions."

**Chris Hutchins** (00:23:32):
But like what I'm I going to od? Randomly email this person I don't know and say, "Hey, I loved your book. Can I just ask you questions for 45 minutes?" I would never do that. But I randomly emailed him and said, "Hey, we've never met. But I have a podcast." I don't even think it had launched, "It's launching next week, but I'm really excited about it. Could I pick your brain?" And he was like, "Sure." So I would say the biggest thing is it just gives you a platform to explore your curiosities on things provided that you can really focus the thing that you talk about on one vertical, niche, something so that people learn what it's about. Because the hardest part about podcast growth is there's like four million podcasts and you've got to find a way to stand out in a sea of many podcasts.

**Lenny** (00:24:12):
Let's actually talk about that. I was going to ask you about that. There's like four million you said, that seems right. It's probably a four million launched to date. Also, if you're someone that's thinking about, "Should I do a podcast? Should I not do a podcast?" Do you have any advice for just signs that this might be a worthwhile endeavor with your time versus signs you probably should not do this, do not even-

**Chris Hutchins** (00:24:34):
I'll give you two perspectives. So one is, yes, there are four million podcasts. However, there are only about 150,000 podcasts that have had 10 episodes and have published in the last 10 days. So the easiest way to be in that top, I don't know, 5% ish. I don't know what the math there is, about %3, 4%, is to just stick to it. If you just do an episode a week, for 10 weeks, you're now in the top 4% of all podcasts that anyone has created. Now, that doesn't mean you're in the top 4% of the 150 active podcasts. So what I would say to that is... I mean, maybe you have a massive platform already, in which case just go start the podcast. But if you don't already have a massive platform, it is unlikely statistically, that this thing is going to work. So absolutely, do not start the podcast if you wouldn't do it for free, making no amount of money in perpetuity or as long as you want to experiment with.

**Chris Hutchins** (00:25:31):
That's one thing I'll throw out there is you are most likely going to start a podcast and it will not take off and be wildly successful. However, I've met plenty of people who have hundreds of listeners and hundreds of episodes and they stuck at it because they truly loved the thing. If you don't know if you love the thing, it's very easy, which is what I did to say, "I'm going to have one season of eight episodes." And I committed to record eight interviews and put eight interviews out in the world. That was it all I committed to myself. And I said, "If that doesn't work, then I will be fine and say, "Here is season one and there's just not a season two." And I would be okay with it." So you can commit to see if you like it before you do it, but chances are, and you might have found something similar when you started creating content, it's like for the first six, nine months, there's no revenue coming in.

**Chris Hutchins** (00:26:23):
It's a lot more work than it seems. Everyone I know that has no podcast and goes to having a podcast, they're like, "Oh my gosh, I thought this was just once, one hour a week, I just talked to somebody." It's like, "Now, I have to prepare for it. I got to write up show notes, I got to make sure it's edited properly, I got to recruit people. Turns out you reach out to 10 people, two reply, one is willing to schedule this week." There's just a lot that goes into it. So I'd say only do it if you're excited to do it, even if five people are on the other end.

**Lenny** (00:26:49):
Talking about the time investment, how long does it take you per episode, hours-wise? And then how long did it take you to kind of prep launch?

**Chris Hutchins** (00:26:59):
And this has evolved a bit as the podcast has generated enough revenue to hire other people. But in general, I would probably spend, depending on how well I knew the topic or the person, anywhere from two to 10 hours preparing for an interview. If someone wrote a book at the beginning I was like, I got to read the whole book, I got to take notes. Then I was like, "Well, if I read the whole book and take notes, then I kind of know everything. So I'm going to read a few chapters." I wanted to listen to everyone on different interviews. Some people are really hard, some people have only talked about one topic and you want to get them on another topic. I interviewed Carrie Walsh Jennings, who's a three time gold medalist at the Olympics for beach volleyball. And I listened to every interview she'd ever done because only 3% of each interview was about not volleyball stuff.

**Chris Hutchins** (00:27:45):
And I was like, "Well, I don't want to talk about volleyball, I want to talk about performance and how you can train." She won a gold medal while she was pregnant. This is a serious level of physical and mental preparedness that I wanted to dig into. So that's one big piece of it. After it's done, then it really depends on the style of show. If you have this NPR style editing where it's very narrative driven, it could take you a long time to go through the editing. For me with interview style, I think it takes me about an hour to go back and listen to it at a little, speed up pace. And then go in and be like, "Ah, this thing wasn't worth keeping in. Or I mean, we had to repeat something and let's cut that out, or this person stumbled on their words."

**Chris Hutchins** (00:28:27):
Fortunately there's some amazing software. Now I use a piece of software called Descript, which basically imports all the audio, transcribes it to, let's call it like 95% accuracy. And then you can edit the podcast like you would edit a Google Doc. It's crazy. You're just like, "Oh, let's delete all the ums, control F, um. Ignore all ums." And then you listen through it and you're like, "Oh, that um, was really necessary, let's put it back in." And little edits like that. But that tool makes the editing process really easy. From the get-go, I had an audio engineer who would actually mix and master and add in the music and that kind of stuff.

**Chris Hutchins** (00:29:02):
So I would say each guest is probably at least 10 hours plus probably two or three hours of coordination and outreach to three or four people that you reach out to in order to get the one. Now I've since, hired someone who helps do a little bit of research. So they might go listen to two or three episodes, read a couple chapters of book and put up some notes with links to those various places. So I can then take that and take my time from 10 hours to three hours.

**Lenny** (00:29:31):
I'll share my experience briefly. It's a little different, which is really interesting to hear your experience. So I launched the complete opposite of your advice, which is I just launched big with like, "I will do this forever. This is my new thing. I have 40 guests lined up, here's who they're going to be." And I think it's partly because I already went through that initial period of uncertainty, whether I can keep this up with a newsletter, which you said eight to nine months. Which is exactly how long it took me to do the newsletter every week to get to a point where I'm like, "Yes, I can keep this up for years. Let's start adding a paid plan." So I think I was just more confident that I can keep at it.

**Lenny** (00:30:06):
And then I actually planned to monetize from the beginning. I think partly again, because I had the newsletter already. And I will say, so I don't edit that myself. I have a production group that is a game changer. So you can save a lot of time and I don't know if you've gone to a producer or anything, but I feel like most people eventually do.

**Chris Hutchins** (00:30:25):
I've now switched to someone who went back, listened to the first 20 or 30 episodes and said, "Oh, I get what you like to cut out of a conversation." And I'll end and say, "Hey, take that 90-minute conversation. And I think there's probably 20 minutes to cut out." And they do a very good job of getting pretty close.

**Lenny** (00:30:42):
Awesome.

**Chris Hutchins** (00:30:42):
To the point that some episodes I'm just like, I don't even look at it.

**Lenny** (00:30:45):
Yeah.

**Chris Hutchins** (00:30:45):
It's just recorded and done.

**Lenny** (00:30:46):
Yeah.

**Chris Hutchins** (00:30:47):
When it comes to launch, I would say one of my suggestions is to get a few things in the bag. Line up... You don't want to launch and then be scrambling. So I tend to think launching with two or three episodes, either all at once or in a week is a really valuable strategy. You talked about in the intro, you're like, "Sometimes it's been a higher ranked, but top 30." I think I've been top 100 in the business category all the way to top five in the business category, maybe top 10 and just all the way in between.

**Chris Hutchins** (00:31:18):
And the reason for that is that the ranking charts are all driven by different variables than you would imagine. They're driven a lot by momentum of new subscribers, at least on the Apple charts than actual downloads. So I have a friend who launched a podcast and had a huge following on social media and so out the gate was able to garner a ridiculous number of new subscribers to the point that she was the number two podcast overall, all podcasts in the world.

**Lenny** (00:31:45):
Holy shit.

**Chris Hutchins** (00:31:45):
It is crazy for a week or two, a woman named Erika Colberg, she has a podcast called Erika Talk.

**Lenny** (00:31:51):
Oh, yeah.

**Chris Hutchins** (00:31:53):
But it's not number two anymore because it's so driven on the momentum of how often you can get new subscribers. She's still in the top 100 of business podcasts, but to get to the number two spot overall, it's all about number of new followers per hour. And if you can get a ton of traffic early on, you can drive that. And I will say the value of you doing that is now you've got this screenshot of like, "Look, I was top 10." And by the way, she did the same thing I did. The moment I was top 10, the second I was in top 10, I immediately took all those guests that were on my dream list and I was like, "Hey, I've got a top 10 podcast. Go look at it right now and see that it's in the top 10." So you can always say that forever after it happens once, you can always use those things. So capitalize on that.

**Chris Hutchins** (00:32:39):
So you had the newsletter before. I had a newsletter I'd written on casually for various things throughout my life and for my last startup. And so I kind of put it all together to try to carry a big launch so that we really spike the rankings, maybe qualify for Apple does this new and noteworthy thing. And so there's a lot of stuff you can do to build momentum at launch, but at the end of the day, all the momentum in the world doesn't matter if your content's not good. So I try to say content for me is product market fit for building software. It's like you need to have a good podcast. And so if you launch big, one of the downsides is you're like, you don't really get that moment of tweaking and testing and seeing how it is. And I will say, I did five episodes in the fifth one. I was like, "This is number one." The first one I recorded came out, I don't know, fifth. But the fifth one I recorded came out first because I just knew it was episode one.

**Chris Hutchins** (00:33:32):
And the guest that I had on, and we talked about travel hacks, a guy named Leigh Rowan, he's come on twice. It was just like this awesome energy episode about everything you want to know about travel hacks, allthehacks.com/one. So save yourself the need to scroll through the whole list. But if your content isn't a unique perspective, you don't have a unique way of saying it. It's going to be really hard to stand out in the sea of podcasts. So I always say, be you, be authentic. Try to be someone's favorite. Don't try to be everyone's okay podcast. I remember Tim Ferris was saying... I got a chance to go on Tim Ferris's show and interview him about podcasting. And he's like, "Look, I did an episode about how to..." I think it was like how to make violins or something. And he's like, "I was so fascinated about this. 80% of people were like, what is this episode? But 20% of people thought it was one of the best episodes I'd done that year."

**Chris Hutchins** (00:34:24):
And I think half of his top 10 episodes of all time are people you wouldn't recognize. So I would focus on what gets you excited, not focus on what you think will move the metrics. Because every time I have a guest where I'm like, "I really think this person's going to move the metrics." It doesn't. And then I interview someone who no one has ever heard of, and I get these emails like, "Wow, that was such a good episode. Can't be. Oh man, I'm so glad you did that one." I was like, "You don't even know this person is."

**Lenny** (00:34:50):
Very similar experience in many ways across a lot of the things that you said. Something that you did mention that you shared previously with me is, and this is advice that I've thought about a lot, is you should be somebody's favorite podcast. That's like a sign that you're doing something right. Can you expand on that?

**Chris Hutchins** (00:35:08):
There's this whole idea of your build your 1000 true fans. And I think anytime you're creating something in the world, you want people to be your advocates for it because those are the people that are going to share it. Those are the people that are going to write the reviews, those are the people that are going to send you the ideas. Those are the people that are ultimately, when you make a call-out on a podcast like, "Hey, I'm looking for someone to help build this company or this enterprise." That are going to reach out and want to work for you. I find it so valuable to build that relationship with people. And it's even more valuable with podcasting because podcasting is such an intimate medium. You're in someone's ear and they're actively listening to you while they're going about their life. They're going on a walk, they're [inaudible 00:35:52], but you're right there.

**Chris Hutchins** (00:35:53):
And I get so many emails, they're like, "Ah, I feel like I'm just sitting on the couch with you while you're talking to me." And you create this really close relationship and the more you can create for those people and be their favorite time of the day, their favorite thing. Someone once told me, "Make sure you're consistent with the time you release because you'll get people that are like, "It's Wednesday morning, where's my episode? This is how I... It's become a ritual in my life."" And so, I don't know. I just think it's so valuable to build that early kind of excited user base and those 1000 true fans that I always try to put something out that's someone's favorite.

**Chris Hutchins** (00:36:30):
And I actually surveyed the audience about 50 episodes in and ask, "Which was your favorite episode?" And every episode except one was someone's favorite. There's one episode that, no one's favorite. So I'm still waiting. Maybe next time I survey someone will be like, "No. No, that one was my favorite." But every other episode of 50 episodes was someone's favorite. And it was like the coolest feeling knowing that every episode was someone's favorite.

**Lenny** (00:36:57):
That's exactly what happens with my newsletter. I get a reply with every newsletter and someone's like, "This is my favorite one yet." Okay, somebody really likes this one. It's so interesting.

**Chris Hutchins** (00:37:06):
Yeah.

**Lenny** (00:37:09):
Are you hiring or on the flip side, are you looking for a new opportunity? Well, either way, check out lennysjob.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 a hundred other companies who are actively hiring through collective. And if you're looking around for a new 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 lennysjobs.com/talent. How did you pick your topic for your podcast? And then did you have just advice for folks for how to pick the topic for their podcast?

**Chris Hutchins** (00:38:07):
This is an interesting one. So my podcast actually started as a parenting podcast from the perspective of dads. And I was doing all this research. I built this probably 75-page Notion doc all about parenting. It was like I had a kanban board for all the things I needed to do in each trimester of the pregnancy. And then the fourth trimester after the baby was born, I had all these checklists. I had a stroller spreadsheet that had, at least, let's call it 15, 20 different features that you could filter on. Dimensions, cubic volume of when you sum up the dimension, everything. It was crazy. And I was like, "I'm so obsessed with this." And I was like, "Nobody's really taking this kind of crazy optimized approach to processing parental information except a few people." Emily Oster, by the way, if anyone out there wrote a few books, I really loved her pragmatic science approach. But I just didn't see a lot of this and I especially didn't see as much content coming from dads.

**Chris Hutchins** (00:39:07):
And I was like, "I'm so excited." And then we had our daughter and for some reason I was like, "I love her. But the topic of parenting and optimizing every aspect of it just wasn't what it was before we had the child as after." I was like, "Wow. But I bought this microphone and I figured out how to use all the editing software and I had never even recorded an episode." And it just ended up that I was like, "That topic just wasn't right for me." And I went on another friend of mine's podcast guy named Kevin Rose, who was a co-founder of a company we started, he started Digg back in the day. And in the middle of it we'd been talking about this, I've been brainstorming ideas, and in the middle of his podcast he's like, "Hey, tell us about your new podcast."

**Chris Hutchins** (00:39:50):
And then I was like, "Kevin, I haven't nailed down what it is." And he's like, "Yeah, it's fine. Why don't you just record a response to that question and email it to me before this episode goes live and then you could just tell everyone what your podcast is about." And then I was like, "Okay, I'll think about it." And the next day he was like, "Dude, I need this by Friday." I was like, "Oh, man. So I have two days to figure out what my podcast is." And I talked to a lot of people and they're like, "What do you love, what do you love talking about?" I was like, "Gosh." What question someone said is, when you're at a dinner table, what's the thing that you talk about where you notice that everyone at the table is leaning in and trying to listen and pick your brain on and maybe sends you a text after?

**Chris Hutchins** (00:40:27):
And I was like, "It's probably all the hacks I have for traveling for free, for getting upgrades, for saving money, for shopping online, for optimizing my health or anything, house hacking, saving money on my rent." And every time I bring those up, people are like, "I like saving money. I want to travel for free." And they're leaning in, they're like, "Which credit card do I get? Is this one bad? What about this one?" And I couldn't come up with a name. I had hundreds of names. It was like life upgraded, optimized your life. But every time I described what it was, I just said, "It's life upgraded. I'll teach you all the hacks to do this." And then someone, I can't even remember who was like, "What about just All the Hacks?" And then I looked and I was like, "Is allthehacks.com available?"

**Chris Hutchins** (00:41:08):
I was like, "What? It's available." It's like... Get the domain. And then I very quickly recorded a response to Kevin's question, which was like, "Yes, I'm launching a podcast called All the Hacks, here's what it is." And I had to go create a trailer and upload it all in three days. And I think I was fortunate that I just had the time pressure that I had a thing to get out. So I'd say one, what do you love talking about at the dinner table? What gets you excited? What do people reach out to you for expertise on? What do you spend your time going down deep rabbit holes on the internet on? Because all of those things are going to be part of your life as a creator. And then two, if there's any way you can force yourself to just have to make a decision because I get stuck in this analysis paralysis, that's great.

**Chris Hutchins** (00:41:51):
So find some friend of yours that's like, "I'm tweeting about your podcast on Friday, or I'm going to include you in my newsletter next month." And give yourself an artificial deadline or even a real deadline to just put a stake in the ground. And you could change the name, you could pivot the topic, you could pivot the style of content. All those things can happen after, but just get started because you'll get to learn whether you like doing it, how it feels. And you could always... This is another fun hack. You could create a podcast and make a private feed and people can add a private feed to their podcast app. So if you want to get some feedback, you can just send people a URL and say, "Hey, paste this URL and the Apple Podcast player and listen to a couple episodes and let me know what you think." Before you make that plunge to send it to the whole world.

**Lenny** (00:42:34):
Awesome. I actually heard that interview with Kevin Rose back in the day, and I checked out the podcast, I think I actually subscribed and it felt very natural. So nice job.

**Chris Hutchins** (00:42:43):
Yeah. Little did you know that it was inserted in post production, recorded on a separate system. Yeah.

**Lenny** (00:42:49):
So people listening to this made feel like, "Hey, I don't have Kevin Rose announcing my podcast. How do I get started? How do I get my initial traction in my podcast?" Do you have any advice there for people that are just launching things they could do to get their initial set of subscribers and get the word out and get some kind of traction without a friend with a huge platform?

**Chris Hutchins** (00:43:08):
Yes. I interviewed a guy named Nick Gray, and it was a fun conversation because he wrote a book called The 2-Hour Cocktail Party, and it was all about how to build relationships by throwing the best cocktail parties. And it was very tactical guide, but one of the things he does is he has a friend's newsletter. And he basically created a newsletter and every time he meets someone that is a friend of his, he sends him a note, says, "Can I add you to my friend's newsletter?" People say, yes. And he just shares, "Here's some cool articles I'm reading. Here's a cool thing I'm doing in my life. Here's a picture." It's instead of waiting till the holidays to send your holiday card to everyone that's like, "Here's what happened this year. Or maybe now we've..." That's what my grandparents did. Now it's just like, "Here's a photo of the family."

**Chris Hutchins** (00:43:45):
He just sends it out. I don't even know what the cadence is. It's just like every now and then I get an email and it's like, "Oh, this what Nick's up to, this is pretty cool." Anyone can subscribe to it. And he shares all these great things. He's like, "Ah, I was thinking about a virtual assistant. Here's 75 things that I dreamed up that I could send to a virtual assistant." I was like, "That's really cool." "Here's how I tweak my Calendly. And I sent the Calendly to you. It's like I added a few little things in it that..." He had suggestions to just make it a little more friendly, make it a little more comfortable. The one I loved was like, "If I'm not arrived within two minutes of the start time, here is my cell phone number. I just want to make sure I'm prompt. And people know that."

**Chris Hutchins** (00:44:19):
And so, one thing is, before you even get started, find a way to just build an audience of your closest friends, family, colleagues, and throw stuff out in the world. You don't have to do it weekly or monthly. You could just send it out every quarter, every six months, it doesn't matter. But start to build something. So I started with a new, I think it was on MailChimp, called Life Updates. And I think I sent five of these out 10 years ago, and I hadn't really sent one out in seven years, but I still had this email newsletter with 1100 people on it that I just collected from life. And so that was one thing. Look, you can always go out and try to find other creative ways to partner with people. So you have a newsletter, but you don't have a podcast.

**Chris Hutchins** (00:45:03):
Could you use your newsletter to promote something? Could you find someone who has a platform that you could trade your services for promotional things? Yeah, I can think of any couple examples where there's been something where I've been really excited use and I'm like, "Hey, could I talk to my audience about this thing? And then you could let me use this?" So if there's anything, whether it's consulting services or anything, you could maybe trade those services for other people with an audience to share and promote you. I think that happens more often than not. But again, it all matters if you have good content. So I'd say the first thing, the most important thing to grow a piece of content is just have it be good. And it's hard to know what's good. Put it out in the world, see if people like it. Maybe get your reps in before you even try some of these growth things.

**Chris Hutchins** (00:45:46):
I think I was fortunate to have done some public speaking before, so I felt a little more comfortable. But if you... You mentioned MrBeast earlier, he's very public about the fact, if you go back 10 years and look at his YouTube videos, they were not exciting like they are now. And it took him a long time. And I think that's the reality with content is, for almost every person that you see out there and you're like, "Wow, they have this huge audience. It's so awesome." You go back 10 years and you're like, "Oh, well their first episode wasn't that awesome. It was actually kind of crazy. Or it wasn't that interesting. And they got better over time. They learned what their audience liked, they built a following." So those things are all there. Find communities. If you're talking about a very specific thing, I never forgot Gary Vaynerchuk's lesson, gosh, he probably told me this 13 years ago.

**Chris Hutchins** (00:46:32):
He was like, "When he was starting Wine Library." Which most people don't maybe even know that that's what he was originally known for. He wanted to build this business and so he went on Twitter and he looked for every single person that asked a question about wine and he at replied them back. And so a tactic that I think could work really well is, for me, I'm like, "I love travel. I love points and miles." I can just search Twitter and find every person on Twitter, every person on Reddit, every person on a forum, whatever that's asking a question about the thing my podcast answers, and go in and try to be a value add to them. I guarantee that if you have a podcast and your favorite thing is quilting and in your bio on Twitter, maybe Twitter's not the right platform, but let's just go with the analogy, right?

**Chris Hutchins** (00:47:14):
Your bio says , "Top quilting podcast." And you go find everyone that's asking questions about quilting and answer their questions with strong, good answers. They're going to look at your bio and be like, "Oh my gosh, this person knows their stuff about this topic. Let's go see what they do." And you have these advocates they share in their communities and it grows over time. I'll come back to one more tactic, which I didn't do, but there's no built-in distribution engine in podcasting. TikTok, you make a TikTok video, TikTok sends it to like a hundred people and if no one likes it dies. But if like a few people like it, they send it to more people and more people. And YouTube does the same thing. Instagram Reels does the same thing. Podcasting doesn't have that, and so it's just a slow growth effort and you just have to be okay with that.

**Chris Hutchins** (00:47:59):
But what I didn't do early on, which you can do is you can make clips of your podcast and you could put those clips on these channels that do have that built in distribution. And if those clips do take off, they could build a massive audience. And so there's a guy, Danny Miranda, he has a podcast and he launched, didn't have a huge following, but he created clips of every single episode, lots of clips. He didn't know what was the most interesting piece of content, so he made a clip for everything. He built millions and millions of views on TikTok and Instagram, just by creating content from his podcast that drove downloads over to his podcast. Helped him build his audience, and he built an audience on social faster than I have a and bigger than I currently have out of just being all in on distributing his content on platforms that had growth engines built into it.

**Lenny** (00:48:48):
The last point is interesting because what I've been hearing, and I've actually experienced it, so I have TikTok clips, I have YouTube videos and YouTube shorts, and I find they drive followers within the platform and downloads and views, but I haven't seen any actual impact on the podcast. And maybe people can measure it or maybe they can tell something's happening, but from what I hear and what I've seen, I don't know if it actually drives a lot of downloads, but it's still really useful, still useful to have an awesome TikTok account and an awesome YouTube account.

**Chris Hutchins** (00:49:16):
He said, "Look..." I don't know if it drives downloads, but it drives brand awareness for me.

**Lenny** (00:49:20):
Yeah.

**Chris Hutchins** (00:49:20):
And he's had multiple guests be like, "Oh yeah, I'd love to go on your show." One of the clips he made, he made a clip talking about Ray Dalio. And Ray Dalio was like reposting his clip. And so he was getting a lot of engagement with people that would be very difficult to reach out to saying, "I have this many downloads." But because he was getting thousands or even millions of views across a platform, it gave him the credibility to do a lot of things that he might not have been able to do now. Then he's gone and translated that into, "Well, let's go bring some of these people with really, really wide distribution of their podcast onto my show and let's do an interview with them." Then for the most part, people are like, "Oh, let's distribute that content to my audience that you had me on."

**Chris Hutchins** (00:50:03):
One thing he did that was so good is he did all of his videos in person, so he would fly to someone record in person, and the quality of the video for an in-person video was just so much better than you get doing a remote thing. It's a lot harder. It's a lot more work and it doesn't even impact the audio, but he would make the best quality clips, and Erika Colberg does the same thing. And she would deliver them and he would deliver them to the guests, and now the guest starts using those clips because he spent so much time trying to come up with the best clips, the highest quality, best produced that made his guests look amazing. And then those guests were much more likely to share those in their audiences and all of a sudden you've got a lot of momentum.

**Chris Hutchins** (00:50:44):
Does that translate to downloads? I'll give you a little shout-out, Danny has a paid newsletter on Substack where he actually breaks down all his downloads and all his tactics on how this is all working for him. And it's fascinating, it's called In The DM, because he did a lot of his early on recruiting with guests in DMS on social media. But it's to be seen, how much of an impact it can have on your podcast, but it certainly builds other things that are, I'd say like indirect... There's no direct attribution, but that doesn't mean that things aren't overall going up. And then the last one is finding other podcasts that you can go on as an expert in some area. So hopefully, you're starting a podcast because you believe something is exciting in the world, you love it, you have a passion about it, you're an expert in it.

**Chris Hutchins** (00:51:32):
Take that thing and go present yourself to other podcasts. And they all have listeners that are listening to podcasts, so it's the best medium. Because yes, someone who likes short form, 60-second videos is maybe not the best target demo to listen to a one-hour audio only thing, those two are very different behaviors. But if you can find something you're really good at and present a value add to people to come on their show, then that could help you build your audience while adding value to their audience. And I think as someone who gets a lot of pitches from people to come on their podcast, I will only caveat it with, do the work to make sure you're really presenting a compelling pitch. You're going to get a lot of nos, that's just how it works. I've pitched myself to go on lots of shows and sometimes I get nos also.

**Chris Hutchins** (00:52:19):
Many times I get nos, but I never send an email that's like someone would read it and be like, "This person obviously, doesn't know what they're talking about." But I get so many, they're like, "Oh, I'd love to have my client come on your podcast. They love talking about building a business." And I was like, "Well, I don't really interview people about that." If someone came to me and was like, "Here is a tactic to improve your life that I think your audience would benefit from and here's why my expertise makes me the best person to talk about it." I'd be much more open to it because they actually understood what my show is about.

**Lenny** (00:52:51):
Yeah, I get it. At least, one email a day with one of these pitches and I know exactly what you mean. I generally, don't reply because it's just not even worth trying to convince them they're not a fit.

**Chris Hutchins** (00:53:00):
Yes.

**Lenny** (00:53:01):
Shifting gears a little bit, I want to talk about your stack, your podcasting stack. What do you use on the software? What do you use the hardware? Mic, headphones. What do you recommend?

**Chris Hutchins** (00:53:11):
On a mic? I started out with the ATR2100X, I think it is a great entry level mic. It's under a $100. You can use old analog XLR cables if you want, but it's also USB. That mic got me through 50 episodes. I have since upgraded to a Shure SM7B, which is the XLR compatriot to, I think you have a Shure MB7.

**Lenny** (00:53:36):
Yeah, I have the USB version if that's what-

**Chris Hutchins** (00:53:38):
Yeah, exactly. And those are two great kind of upgrade mics that I think... I like the sound quality a little better, but every time I'm traveling and I'm not sure if something's going to come up, if I can make a recording and if I have to record the intro, do a remote interview, I still carry the ATR2100X, because I just think it's an easy thing to have and it works really well. I record everything on Riverside. I put everything into Descript. I plug my XLR mic into a Focusrite Scarlett 2i2, which is like a audio interface. I would say I've gone a little bit overboard with video, so we were talking right before this started. I have a Sony a7C, which is like a mirrorless, full frame camera behind a $60 Amazon teleprompter so that I can make direct eye contact with the camera while an iPad that's... I don't know, it's like 10-year-old iPad sits under it and projects as a second screen for my computer, using this-

**Lenny** (00:54:36):
[inaudible 00:54:36] If you're not watching this YouTube, you got to check out the YouTube video at least for five seconds to see Chris just staring at you. I've never seen this on a podcast video before.

**Chris Hutchins** (00:54:43):
Yeah,

**Lenny** (00:54:44):
It's the future.

**Chris Hutchins** (00:54:45):
So I have that set up using a iPad, running an app called Duet Display. I don't do the editing. I've worked with one editor that uses Audition and one that uses Pro Tools. I don't have a strong opinion there. Oh, my favorite of all, my friend of mine, Brendan Mulligan, started this company called Podpage. And so for people who don't know a lot about how podcasting works, there's a hosting platform, I use Simple Cast. I liked that they were one of the only hosting platforms that has a really affordable self-serve option, but also has a really great pro, all the features that you would want in the future for monetization, everything so that you wouldn't have to switch. Not to say that you know couldn't switch easily, it's pretty easy to switch. How it works is you upload an MP3 file, you write out all your show notes, the title of the episode, everything, and they create an RSS feed for you.

You could literally just create an RSS feed, right? That's all it really is, and you could host everything on your own on AWS or something, but they make it really easy for not that much money. And then you go distribute that RSS feed to all of these different players, so the Apple Podcast app, Spotify, et cetera. And one of the things that's amazing is this site Podpage, you submit the RSS feed to this website and they go in and say, "Oh, here's the description of the podcast. Here's each episode. Here's the cover art you submitted for that episode. Here's the title, here's the show notes." And they just auto-generate a website for you. And then they give you the tools like a WordPress style set of tools to go and change the header, change the descriptions. They're like, "You could go in and tweak things." But every night on Wednesday, or I guess Wednesday morning at 2:00 AM my podcast goes live. And at 2:05 Podpage has already noticed, the RSS feed is up-to-date and that site is posted. I don't have to do anything.

**Chris Hutchins** (00:56:30):
They even monitor for the slug, like the URL slug I put in as a checkout. This podcast at this URL and podcast page says, "Oh, that's the URL you want them to check out. We're going to inherit that and put it in so you don't even have to give us any information. And we'll just know the URL that you want to set this episode up on." I think that is a super simple way to build a podcasting website. The only other thing, we didn't talk at all about analytics at all, but I use Chartable for analytics. And podcast analytics are a little crazy because you don't have a lot to go on. But Chartable is a really cool analytics platform that becomes really interesting when you start to cross promo with other shows or run ads for other shows or do anything like that because they basically can track IP address of downloads.

**Chris Hutchins** (00:57:22):
And I say track, I don't know who's listening to what from where in any kind of very specific way. But what I do know is if I'm doing a cross promo with another show where I'm saying, "Hey, check out a podcast I love." And they're saying, "Check out a podcast I love." It actually says, "Oh, how many of the people that downloaded this episode actually went and listened to this other episode?" So you can get direct attribution of podcast listeners going from one podcast to another. So that is a really important tool in my kind of running a podcast toolkit, but it doesn't matter as much until you start focusing on growth and doing promotions and stuff like that.

**Lenny** (00:57:58):
Awesome. I host on Substack as maybe one difference. I use Podpage for my site, my producer/editor people actually use Descript/Descript also. That's kind of what they use for editing professionally, so it's good for amateur hour and good for professionals as well. I use Chartable, something's up with my Chartable, I think I've told you, or it doesn't count my Spotify downloads. It's kind of a pain in the butt, but it's still-

**Chris Hutchins** (00:58:21):
Which is funny by the way, because for anyone listening doesn't know, Spotify actually owns Chartable. So the one platform your Chartable doesn't get good download data from, is the one that it is owned by.

**Lenny** (00:58:33):
Yep. I do not understand what is going on. I've talked to them and they don't know what the fix is. It doesn't matter anyway. I get enough analytics other places. There's one other site I'd recommend called Podstatus that just gives you quick access to where you're on the charts every day, gives you these cool line charts. Which Chartable sort of does, but it's a lot simpler on Podstatus. But otherwise-

**Chris Hutchins** (00:58:53):
Awesome.

**Lenny** (00:58:53):
All the same stuff. One other question real quick. Say someone launches their podcast, what would be a good download goal to aim for, when you're getting started that's like, "Maybe this is working." Do you have a sense of a threshold try to hit?

**Chris Hutchins** (00:59:08):
I wouldn't think of a threshold to hit because you could launch with a huge audience and have a terrible podcast and you might hit 10,000 downloads and it would be crazy, right? You would feel really good. So I would care more about the direction than about the number because even the Apple charts, they're more momentum driven. You could have one download, but the next week you have a lot more and a lot more and a lot more. You would actually rise in the charts faster than someone whose podcast is kind of stagnant doing X number of downloads. If you have 3000 downloads an episode or something like that, you're in the top 1% or something. So you know, don't have to get to crazy numbers to be in the top of the charts.

**Lenny** (00:59:08):
Yeah, I heard-

**Chris Hutchins** (00:59:08):
I would say-

**Lenny** (00:59:54):
I heard a similar number, 3000.

**Chris Hutchins** (00:59:55):
The top podcasts are doing millions in episode, but that's like top 10, top 20, top 30. The next tranche of the top 50 are doing probably hundreds of thousands of downloads. But outside of the top two, 300, it's in the 10,000s of downloads per episode. And this is a little bit variable if you have a daily show or a weekly show or something. But I would say if you cross 10,000 downloads an episode, you are now taken seriously by a lot of people. So I had conversations early on with networks like iHeartMedia and different podcast networks that wanted to bring in the show and would do all that, and that all started at 10 to 15, maybe 20,000 downloads an episode. But by no means would I expect anyone to get there right away. Even I didn't get there right away. It took time even with a few friends to make announcements and stuff, it took time.

**Chris Hutchins** (01:00:50):
So forget how many downloads you get on your first three episodes because you're probably going to tell everyone in the world and you're going to use all your social capital to boost those. And then look at how many downloads you get on your fourth and fifth and sixth and does it go up? Does it stay stagnant? Apple and Spotify actually give you really cool data about how long people are listening. Do they drop off halfway through? You could start to be like, "Oh, do people stay for the whole episode?" I will say I haven't found a good site for benchmarks, but it's like the average podcast I think probably has less than 50% of listeners by the end. So don't be turned off when you say, "Wow, only 40% of people made it to the end." That's not horrible. I think my best episode, it might be like 65 or 70% of people made it all the way to the end. It's not 99.

**Lenny** (01:01:37):
What I like about those charts is you can see what percentage of people skip the ads and then just keep continuing. It's like a bump-

**Chris Hutchins** (01:01:42):
Yeah.

**Lenny** (01:01:42):
The mid-rolls and the-

**Chris Hutchins** (01:01:44):
[inaudible 01:01:44] And it's not as high as I thought.

**Lenny** (01:01:46):
10, 20% depending on-

**Chris Hutchins** (01:01:47):
Maybe 15%. It depends.

**Lenny** (01:01:48):
Yeah. Not bad at all.

**Chris Hutchins** (01:01:51):
Yeah.

**Lenny** (01:01:51):
Any last words of wisdom on the world of podcasting? Starting a podcast? Continuing a podcast?

**Chris Hutchins** (01:01:57):
Yeah, I've got three things for you. One, this is a little bit of a financial outlay, but I think it's really interesting. There's this podcast app called Overcast, and it's not the biggest in the world, but you can run ads in it. And the thing I like is that the ads are much more reasonably priced than a lot of other places and they're very dynamic. So I would encourage anyone listening to watch it for a few weeks if you have a podcast and you want to experiment, because the same ad could be $200 one week and $700 the next week depending on how much demand there is for that category. So you can wait and hold out. But what I like is they take your art from your podcast and then you can rewrite your description and they tell you how many people saw the ad, how many people tapped on it, and how many people subscribed to the podcast after seeing the ad.

**Chris Hutchins** (01:02:43):
And technically they could also listen to the trailer, they could listen to an episode. And they even give you benchmarks of what to expect. So for a few hundred dollars, you could go in and run an ad for your podcast. Now, I would say in all of the experiments I've done with them, I've probably garnered... I'm looking at some numbers, like hundreds of subscribers, not thousands. And I've probably spent maybe a $1,000. The average cost to acquire a podcast listener, if you're doing paid marketing is about anywhere from three to $10 depending on the appeal of your show, what kind of audience? I'm sure it could go way over that for a business show. And by business I mean, B2B focused kind of show. So, let's call it $5. So it's not going to be the best way to grow your audience. At some point, if you're at enough scale that you have ads in your show and how much a customer's worth, maybe it makes sense to pay $5 because your LTV of a podcast listener is $7. But getting it started, that's not you.

**Chris Hutchins** (01:03:39):
What you can do is say, "Okay, what was my click-through rate on the ad?" Which will tell you if someone doesn't click, it's either not a good description or it's not a good set of content, or your cover art's not good. So you can think about, "Okay, I actually need to figure out the podcast before I even have content." And you could run this ad with a trailer before you even record anything. And then it's like, "Okay, well people tapped on it, how many of them subscribed?" And I like to use this as a way to say, "Okay, well the benchmark said I was going to get about 50 subscriptions for this ad that was going to get a thousand taps and I got seven." So these aren't people who weren't interested. These are people who read the description, were like, this is interesting, and they didn't subscribe.

**Chris Hutchins** (01:04:20):
That means my content probably sucks. That means someone listened to a trailer or an episode or something more than the description in the image and decided, "This is not for me." Maybe they looked at your episodes, I don't know. But if they don't tap on it, if you're supposed to get a 2% click-through rate and you get 0.5, then it's actually the topic or the way I describe it or the cover sucks. And so I like that as a way to, for a few hundred dollars, get a good test. I've even thought of running an AB test of the same podcast with two different descriptions. I wish you could do it with two different cover arts. So I don't know, that's like a cheap way to do a little bit of testing. One other thing that I'll share is I just try to share the podcast everywhere.

**Chris Hutchins** (01:05:05):
So you've probably noticed that in all of my emails at the bottom, it's like, "Oh, great, talk to you Chris." And then it says, "Hey, want to upgrade your life, money or travel? Check out my podcast and newsletter." I'm taking every opportunity I can to let anyone know about it because you never know it'll happen. And my favorite example, especially, when it's written that it doesn't come across a big bulky signature was we bought some floor mats and one of them didn't fit. And I was going back and forth with the customer service person and they actually replied and they were like, "Oh, thanks for sending me that podcast. I really appreciate it." They thought I was just randomly telling them, "Hey, if you want to upgrade your life, check this out." They didn't know it was my signature. So I got a new listener from customer service from a floor mat company. Which by the way, here's one hack that I also learned from the floor mat company.

**Chris Hutchins** (01:05:52):
Come to my show for hacks, but if you're ever trying to get a deal on something, that floor mat company, I just pulled up the live chat and just asked. And I said, "Hey, I'm looking at these floor mats, think you could give me a discount. It's a little expensive." And it was like, "Yeah, refresh your cart. It'll be 15% off." So, this episode's not about all the hacks, but there's one cool one.

**Lenny** (01:06:11):
We need more hacks. Wait, I think we'll get to that at the end. Keep going.

**Chris Hutchins** (01:06:14):
And then the last is, I think it's fun, that podcast you can experiment. I started out doing guests and then I did some Q&A episodes from questions listeners asked me, and then I recently did some solo episodes. I was really interested in the idea of all the ways you can rent and swap and exchange your home to stay in vacation homes around the world. So I just researched it for, I don't know, two or three days and just did a 45-minute episode of me talking. There was no guest, there were no questions, it was just me talking. And that works. I'm going to start another series of episodes where instead of interviewing people about an expertise topic, I'm going to interview people who are really dialed into a country. So I've got a guy who's written a handful of the Lonely Planet guidebook for Japan and is in Japan right now for three weeks getting dialed in, what are the latest, coolest stuff.

**Chris Hutchins** (01:07:03):
He's going to come back and we're just going to record an episode about everything you need to know about going to Japan. And I'm going to add on about 15 minutes I think at the end without him, where I just talk about all the tricks for using your points, your miles, deals and discounts. Like there's this new airline in LA that's super cheap to fly to Japan, but it comes with some caveats. So it'll be like two thirds guide to going to Japan, one third guide to getting there for cheap. And there aren't a lot of businesses or ideas where you could just have all of these things that you can experiment with.

**Lenny** (01:07:35):
And then you could do them so fast. Yeah,

**Chris Hutchins** (01:07:35):
Yeah.

**Lenny** (01:07:35):
I love that.

**Chris Hutchins** (01:07:37):
If I interview you, which I'm doing right after this, so anyone listening to this that wants to hear a little of Lenny's story, come check out All the Hacks. And for 20 minutes we talk about some topic that's a little off topic. I've sometimes just taken that it's submitted it as a bonus episode on Friday. 15, 20 minutes, it's not my regular show, but there's so many ways you can experiment and find out what you like. And then you might say, "Wow, you know what? I really like doing the solo things." Or maybe you have a co-host on for a week and you're like, "Ah, that's so much better."

**Chris Hutchins** (01:08:07):
So I just love that it gives you a good opportunity to experiment with stuff, find the thing you love, because I think my big takeaway is once you find the thing you really love to talk about, all of that, it just makes everything so much easier because it's natural and you would do it for free. And the harsh reality of this whole game is like there's probably going to be a number of months or years you have to do it for free before it takes off. So if you don't love it, that's going to be a painful few years.

**Lenny** (01:08:31):
To build on that, I find the same thing with a newsletter, same with a podcast. The last thing you want to do is create a job for yourself that you hate. And so picking a topic that is just not interesting to you, picking a medium that is painful to you, there's no reason to do that. You may become a TikTok star and you hit a viral video, but then you have to make viral videos for the rest of your life. That's no fun. You have to think about, "Do I want to do this for years and years and years." And you can stop, but then becomes hard if it becomes a really good source of income. So that's something to think about, just don't create a job for yourself that you just don't want.

**Chris Hutchins** (01:08:31):
Yeah.

**Lenny** (01:09:07):
With that, we've reached our very exciting lightning round. I don't know if you knew this was coming. So it'll be extra special, real quick, easy, whatever comes to mind, let me know, and then we'll see how it all goes. Does that sound good?

**Chris Hutchins** (01:09:18):
That sounds good.

**Lenny** (01:09:19):
What are two or three books that you've recommended most to other people recently or in life in general?

**Chris Hutchins** (01:09:26):
Two, I love. Actually, this could be three, Happy Money is a fantastic book. All about ways that you can spend your money to optimize for happiness. It's like a collection of a ton of research about the science of happier spending, so that's one. Vagabonding by Rolf Potts, who I had the pleasure... The last two I've had the pleasure of interviewing recently. It's like a guide to long-term travel, but it's just kind of a different perspective on travel. I would say if you're at the point in your life where you now have kids, it's probably going to be hard to live up to that. But I have gifted that book to so many people who are like, "Oh, I think I should take a trip for six months." I'm like, "Go read this book." My wife and I travel around the World for seven months, and that book was instrumental to us taking it and how we lived on that.

**Chris Hutchins** (01:10:09):
And then the last is called Die with Zero by Bill Perkins. And that book probably had the biggest impact. I haven't gifted it to anyone. I've recommended it heavily the last week because it had a huge impact on me. And the fundamental premise of the book is that, this isn't very lightning round response, but instead of optimizing for money, which is so tied up in American culture of how do I make more, how do I get promoted? How do I earn more money, how do I save more money? We should really be optimizing for the net fulfillment in life, and we shouldn't be trying to save all of this money. We should actually be trying to allocate it over our lives in the most optimal way to increase experiences, increase fulfillment, increase happiness. And sometimes that means saving less when you're younger and you're more able to do things like backpack around the world for seven months or go bungee jumping. And when you build those experiences early on, the memories of those experience pay dividends, the rest of your life.

**Lenny** (01:11:04):
Good choices. What's a favorite other podcast, other than your podcast and my podcast?

**Chris Hutchins** (01:11:10):
I love Animal Spirits. If you're into markets, life and investing. And they always have good recommendations at the end also on podcasts, TV shows, books, movies, that kind of stuff. So that's one I really like.

**Lenny** (01:11:23):
What's a favorite recent movie or TV show that you've really enjoyed?

**Chris Hutchins** (01:11:28):
A show that I love, which I think is kind of like a version of a show called Silicon Valley, but not, it's called Mythic Quests on Apple TV. And I haven't heard enough people talking about this that I felt like maybe it's a hidden gem. Maybe I'm amongst company of watching this show, but I think it's a funny show. It's lighthearted, it makes me happy, and hopefully at least a few people haven't checked it out. But it's like a startup life show, but just dragged out to the extreme like Silicon Valley was.

**Lenny** (01:11:55):
What's a favorite interview question that you like to ask on your podcast?

**Chris Hutchins** (01:12:00):
I like to try to ask people about their favorite misconceptions in a space. Yeah, I like to kick things off usually with, "What's a thing that you kind of have a contrarian take on or you think most people get wrong about the thing that best?"

**Lenny** (01:12:13):
Awesome. Final question. What are your three favorite money hacks that listeners can take action on soon?

**Chris Hutchins** (01:12:23):
Okay. One that has paid dividends and literally, I've had people on a podcast telling them, write back to me, guests that are like, "I just saved money." So go to your state's unclaimed money website. Every state has one, and you can go put in your name, state or city, you don't even have to give your address. And you can find whether there are people that owe you money. And oftentimes they're businesses like you moved and Comcast couldn't figure out how to get you the final part of your prepaid month. And I had someone message me the other day and they're like, "I just listened to you talk about unclaimed money on a podcast, and I just found $136. I've never gotten paid to listen to a podcast." People have saved hundreds, some people, thousands. I always say, if you're going to dinner party, you now know someone's address.

**Chris Hutchins** (01:13:07):
You probably know their name instead of bringing a bottle of wine or in addition, just check if they have unclaimed money. I brought over to a bottle of wine to someone's house and said, "Also, by the way, did you know that this pharmaceutical company owes you $200?" And I showed him how to go claim it and boom, free money. What a great conversation for the dinner table. So that's one great one I love. Another great one, you can't use it right now unless you have a trip planned. But anytime you're booking a hotel book directly with the hotel and email the hotel in advance that, "Hey, we booked. We're really excited to stay with you." If you're celebrating something, let them know. And if you can't get the email address, just call the front desk, ask for an email address, follow up a couple days before you get there, let them know you're coming.

**Chris Hutchins** (01:13:51):
And I would say, you've got a 50% chance of getting an upgrade, getting a bottle of wine, getting some comped something, getting a better view. One person wrote into me letting me know that the hotel had their initials embroidered on their pillow, which I thought was kind of a crazy thing to have happen. It's never happened to me. Personally, I'd rather have the bottle of wine, but I'll take that for what it is. And for people who like the points game, I'll share something. Just give you a little tease of how I love finding all the points and miles optimizations. If you have a credit card that pays multiple points, three, four, or five x points on things like a grocery store or an office supply store, anything like that, drug stores, that's great. You probably don't have a card that pays any multiple of points on home improvements or Home Depot, Lowes.

**Chris Hutchins** (01:14:41):
So what I like to do to make sure I get the most points I can, instead of going to Home Depot and paying with a card that's going to give me one point per dollar at Home Depot. I have a four x grocery card. I like to go to Safeway and I just buy Home Depot gift cards. I get my four x points on the gift cards, then I go buy stuff at Home Depot knowing that I got four x points. But you also have some cards that give you three or four x points, if you go to CVS or other pharmacies or drug stores, you can do it there. You can do it at Office Supply stores if you want to take it to the next extreme. If you have an Amazon card, you could buy Amazon gift cards and get your five x or 5% back on the Amazon Prime card.

**Chris Hutchins** (01:15:20):
So I'm a little crazy like that. My favorite is if you're trying to buy something at a store, always shop online for coupons. If you Google like Lowes, Home Depot, Crate & Barrel coupons, there's all these websites. My favorite one is Save n, the letter, deals.com. You could buy Home Depot and Crate & Barrel coupons online for a couple bucks, save 15%. So stack up and then the cashback portals. I'm going to buy something, I'm like, "How do I get the cashback portal? How do I get the most points per dollar on my card? And how do I get a discount maybe from asking in the live chat or going in and buying a coupon." So I go a little crazy on that stuff, but I love saving money and just feeling like I got a good deal.

**Lenny** (01:16:03):
Amazing. What an action packed episode we had. We got money hacks, we got big bets, we got podcasting, we got Self-Driving Money. What a conversation. Chris, this was amazing. Two last questions. How do folks find you online, where do they find your podcast? And then how can folks be useful to you?

**Chris Hutchins** (01:16:24):
All the Hacks wherever fine podcasts are produced for your ears search or go to allthehacks.com or check out the newsletter, just allthehacks.com/email, or you can find it on the website. That's it. How can you be helpful to me? Check out the show. Let me know what you think. Let me know what you like. Let me know what topics you want me to focus on optimizing in the future. I've mentioned I'm always trying to make stuff that someone's favorite, so if there are things you want to hear me go deep on, let me know. I'm just chris@allthehacks.com and I try to respond to everyone in some reasonable amount of time. And if I haven't responded in a couple weeks, nudge me and remind me. But I'd love to hear from you. I'd love to produce more content for you, and I'm excited that we have this conversation, and I'm excited to record one with you right after this.

**Lenny** (01:17:06):
Oh my God, here we go. Chris, thank you for being here.

**Chris Hutchins** (01:17:10):
Yeah, thanks for having me.

**Lenny** (01:17:12):
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.

---

## [20/20] EOY Review

**Lenny** (00:00:03):
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. Normally, I interview world class product leaders and growth experts to learn from their hard won experiences building and growing today's most successful companies. But today is going to be a very different and unique episode. I launched this podcast about six months ago. We've done exactly 50 episodes at this point. We've also done over 2 million downloads since we launched. The podcast is a top 10 technology podcast across Apple and Spotify globally. And I believe there's about 40 to 50,000 subscribers or followers of the podcast across Apple and Spotify, which is all very exciting and kind of blows my mind.

**Lenny** (00:00:47):
**Adam Grant** (00:01:19):
Have you ever wondered what makes great minds tick? I'm Adam Grant and on my new podcast, Rethinking, I'm trying to find the answers. Every week I interview some of my favorite thinkers to learn how we can bring out the best in ourselves and others. I talk to defying rock climbers, Oscar-winning filmmakers, creators like Lin-Manuel Miranda, entrepreneurs like Mark Cuban and thought leaders like Brene Brown. Find Rethinking on Apple Podcasts, Spotify, Amazon Music, or wherever you listen.

**Lenny** (00:01:51):
**April Dunford** (00:03:15):
I actually think the first step in a good positioning exercise is to really understand what do we have to position against? So put another way, it's like saying, what do I have to beat in order to win a deal? So in positioning work we call this competitive alternatives. Now, how people mess up this first step is, I say competitive alternatives and they think competition. So things that look exactly like me. But in B2B we kind of have two sets of competitors. We have status quo, which is whatever the company is doing to attempt to solve the problem right now, even if it's crappy and not great. And then there's, if the company does decide they're going to buy something different, they usually make a short list. So, it's whoever else lands on the short list. I need to be able to put a stake in the ground and say, I got to beat all that in order to win a deal.

**April Dunford** (00:04:10):
Now most folks will discount the status quo, but they shouldn't because in B2B we lose about 40% of our deals to, "No decision," which actually means we lost to the spreadsheet, we lost to pen and paper, we lost to interns. And if we're not positioning well against that, we're never going to get the customer to come off of that. So I got to win against status quo, but I also have to win, most of the time, if it's B2B, you don't just buy the first thing you come across, you make a short list of alternatives and I got to win against those as well.

**April Dunford** (00:04:44):
So step number one, what am I positioning against? Once I have that stake in the ground, then I can start thinking about what makes us different. So the easiest way to do this is, okay, this is what I have to position against, what have I got capabilities wise that the alternatives don't have? So feature function or even capabilities of the company, which could be pricing or professional services around other things that you've got, but also capabilities of the product. What have I got that the alternatives don't have? And I can make a giant list of these things. And then I can translate that stuff into value by going down the list and saying, okay, we have this great feature, so what? Why does a customer care about it? What is the value that feature enables?

**April Dunford** (00:05:31):
When I do that mapping over to value, what generally happens is I end up with two or three value buckets or value themes. And quite often those value buckets or value themes are different than what I would've gotten if I got all the smart people in my company together and said, hey, why does everybody love our stuff? When I do it this way I'm ensured that those value themes are differentiated and not just things that are generally valuable, but any alternative could get it done so why are we even talking about it? So in my mind, that's kind of how we do it.

**April Dunford** (00:06:07):
Once I've got differentiated value, then I can start thinking about, well look, I could sell this product to any company that has this problem, but not everybody cares about this value the same way. And so what are the characteristics of a target account that make them really, really care a lot about that value? If I do some deep thinking about that, that's going to be my definition of a really best fit customer.

**April Dunford** (00:06:31):
And then the last piece of positioning of course is market category. And so again, a lot of people will just start with market category and then try to back up, which I think is crazy 'cause then we don't have any way to judge the goodness of a market category. But if I've got, look, this is the value only I can deliver, these are the kind of people that really care a lot about that value. If I start thinking about positioning is like the context I position my product in, then the best market category is the context I position my product in such that this value is kind of obvious to these people. This is my long-winded way of doing it, but this is the only way I know how to get positioning done.

**Lenny** (00:07:17):
Next up is Crystal Widjaja, who is a longtime chief product officer at Gojek. She's currently chief product officer at Kumu, and she's one of the smartest growth minds that you probably have not heard of. Here is Crystal talking about why most analytics efforts fail at companies.

**Lenny** (00:07:32):
I want to shift a little bit to post that you wrote that maybe he's winning more popular posts, you wrote on the Reforge blog called, Why Most Analytics Efforts Fail. 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** (00:07:51):
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 Foltz 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.

**Crystal Widjaja** (00:08:27):
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. 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 a premise.

**Crystal Widjaja** (00:09:13):
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 observed fact because your transactional database obviously says that that is the case. But it's not 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** (00:09:45):
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. You're a 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.

**Crystal Widjaja** (00:10:25):
So for our purposes, if we look at a Goodfood 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 Goodfood users who are power users are more likely to use a free shipping discount on a high GMV basket versus non-power users. 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** (00:11:43):
The eighth most popular episode of the year is our very first episode with Julie Zhou. Julie was a longtime design leader at Facebook. She's now the founder of a company called Sundial. She also wrote the bestseller, the Making of a Manager and her newsletter, The Looking Glass, was a huge inspiration to me that helped me start my newsletter. Here is Julie sharing her advice on getting over imposter syndrome.

**Lenny** (00:12:06):
Going back to your time at Facebook, you've made it sound like you just kind of like, ah, I joined as a designer, figured out design became a manager, and then somehow you became VP of design and it sounded too easy. That's an insane trajectory for someone to follow. Do you have any thoughts or advice on what contributed to your success rising through the ranks that quickly for folks that are just early in their career maybe?

**Julie Zhou** (00:12:30):
Absolutely. And I want to make it really clear, I would say that the first seven or eight years that I was at Facebook every single week I felt like an imposter. I had no idea really what I was doing. The constant refrain in my head is like, well, do you really deserve to be here? Do you really know what's happening? You're not really prepared for this job. You've never done this before. What do you have to be put in this situation and get to do what you do? And that was really a constant refrain in my head.

**Julie Zhou** (00:13:02):
But looking back, I think it probably took me about seven or eight years until I became a little bit more comfortable with that. After seven or eight years I could look back, I could see all of the things that I got to work on, I could see all the ways that I had grown and learned in that experience. And something clicked for me where I realized it's kind of two sides of the same coin. Being in an uncomfortable situation, being in a position where you feel like, hey, do I really know how to do this, I'm not prepared for it, kind of coincides with the fastest and most intense periods of growth in one's career. I started to realize, well maybe it's not so much of a bad thing. Maybe if I constantly putting myself in this situation where I haven't seen this problem before, that's also what's going to push me to grow and learn.

**Julie Zhou** (00:13:53):
So yes, you asked for specific advice, I think there's two things. The first is, well, I was lucky I was in the right place at the right time. I was at a company that was scaling. And when you're at a company that grows, there's always a lot more opportunity to then be able to try something new, to raise their hand, to volunteer for things to be just thrown into because somebody has to do it because it's a growing company and there aren't a lot of other people. So the first piece of advice I would have would be like if you want those types of opportunities, sometimes you just have to be at a smaller place and you have to be at a place that is going through that rate of growth.

**Julie Zhou** (00:14:30):
The second thing is embrace the fact that it's okay to be in a position where maybe you don't know what to do, you haven't been trained for. It does coincide with that intense learning. Maybe approach it with that sense of curiosity and that sense of, yes, it's hard, yes, I might be an imposter and I might feel that way for a while, but this is also what's going to help me get there. It's going to be what forces me to do the work and in that process learn and become better.

**Lenny** (00:15:02):
It's amazing to hear that you had imposter syndrome for such a long period of time and you basically ran design for the Facebook app, right?

**Julie Zhou** (00:15:11):
Yeah.

**Lenny** (00:15:11):
It's kind of an empowering, inspiring insight that someone that at your level went through that for so long and made it through that. Do you have any other advice or thoughts on just for folks that are going through that? Because I have that to you for a number of years, just like, what the hell am I doing here? People are going to see I don't really know what I'm doing and it's all going to crumble as soon as I make my next mistake. Do you have any other advice there for folks going through that themselves?

**Julie Zhou** (00:15:34):
I think that so much of just exactly what you said, Lenny, I think so much of it that helped me was realizing that everyone feels this way to some extent. And that's also why I always want to talk about that. Because I feel like sometimes you can see from the outside you're like, oh, this person has this title, they have this position, they have these responsibilities. Clearly they've made it, they know what they're doing. But that's never the case.

**Julie Zhou** (00:15:58):
I mean, logically, let's think about it. If you're going to do anything new for the first time, how are you ever going to feel totally comfortable, totally prepared? Every time there's something new that you hadn't encountered before it's always going to be a little bit rough, you're never going to feel like perfectly at ease. It's only upon doing something multiple times that you start to see the patterns, you start to realize, okay, it's going to be all right. Even now, the people that I talk to, the people I really look up to, the people who I think are role models and mentors for me, I mean they regularly also share with me that it's the same. They still encounter things that are unprecedented. If we work in tech, I mean the rate of change, the rate of the industry and companies and these new experiences that we have, that never goes away. That's just par for the course. So I think that feeling always exists.

**Julie Zhou** (00:16:55):
What I have learned is that there are better tools in your toolkit for dealing with it. One of them is of course me just reminding myself that if I feel uncomfortable, okay, other people feel that way too. Everyone does. It's totally natural. But then to also find other pieces in that toolkit. One is I am much better at asking for help now than I was earlier in my career. I used to actually just try and hold it all in. I was like, hey, I better fake it till I make it. If everyone thinks that maybe I'm coming to the table like I know it then I can fool them.

**Julie Zhou** (00:17:30):
Now I realize I was preventing myself from being able to get that support and that empathy and that camaraderie and that advice that would've helped me actually grow faster and maybe with a little bit less pain in the process. So one of the things I've learned is it's okay to ask for help. It's okay to reach out to people who both may be going through the same things you're going or maybe are a step or two ahead of you in the journey, who have actually gone through that and have lived to tell the tale and can tell you it's going to be okay. Because often that's just what you need, you just need people to tell you it's going to be fine. You're fine. You're good. You've got this. That's so meaningful whenever we sometimes feel down about ourselves. So that's another, I would say tool in the toolkit, asking for help, finding groups of support.

**Julie Zhou** (00:18:19):
And then I think the third is it's also okay to just be vulnerable and just talk to people about. I found that some of the most meaningful conversations I had, whether with people at managers or whether with my own reports is when we can be much more open about what it is that we find hard, what are we struggling with? And in that way you actually form deeper connections and people are more able to help out. We can spread the load a little bit. We can put our heads together and brainstorm a better way to solve the problem. And I find that too, even as the head of a department or a founder, it's not going to solve everything myself. I'm never going to have all the answers. Sometimes by just sharing what the problem is by sharing the load, we're all going to collectively come up with a better solution.

**Lenny** (00:19:14):
Next up is Shishir Mehrotra, CEO of Coda, former VP of product and engineering at YouTube, PM at Microsoft. And here are two my favorite clips from Shishir. One where he shares his favorite interview question using a technique called Eigenquestions and his PHSE career growth framework.

**Shishir Mehrotra** (00:19:32):
I have an interview question I ask, it's a very simple question and it's a coded Eigenquestions test. And the question is, a group of scientists have invented a teleportation device. They've hired you, Lenny, to be they're sort of business counterpart, bring this to market, product [inaudible 00:19:50] this question actually worked well for [inaudible 00:19:52]. But say, you could be the product manager for this thing, bring it to market. What do you do? That's the whole question. 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 fast? Does it disintegrate things or not? Does it need a receiver and a sender? Is it safe?

**Shishir Mehrotra** (00:20:17):
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? And interestingly, all of a sudden, like the sharp product managers, engineers, basically every role, they very quickly find what are the two, one or two eigenquestions on this topic.

**Shishir Mehrotra** (00:20:48):
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 questions I would ask, one is it safe enough for humans or not? And that was a very crisp way to get to just safety. How reliable is it? Didn't ask how reliable it is, how many bits in the middle of this... He's like, just tell me it's safe enough for humans or not. And the second one is it more expensive CapEx or OpEx? Is it more expensive to buy them or to run them?

**Shishir Mehrotra** (00:21:15):
And then he took those two questions and he said, get 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 all have the ability to teleport anywhere you want and this is how we're going to run it. But 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 probably do is replace airports. 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? Is hell supporting people's replacement hearts, is that a really demanding thing? But these two questions kind of get to the heart of it.

**Shishir Mehrotra** (00:22:15):
The question's totally made up, no teleportation device exists, at least not yet. I find that people's ability to learn the method is significantly higher if it's low stakes. That question by the way, if you ask a kid that question, hey, teleportation device, you get to ask two questions, almost every kid will quickly get to two pretty good eigenquestions. Kids are incredibly good at simplifying these things down, it's actually a skill we remove from ourself. I'll hear candidates tell me things, I guess I would ask them what size it is and why would you ask them what size? What decision is that going to allow you to make, to know what size? And sometimes they can explain it, sometimes not and don't get hired. But then actually the thing I'd say about it is there are eigenquestions everywhere. I mean 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 you can almost take anything and say, what is the question that really drives this answer.

**Shishir Mehrotra** (00:23:27):
It stands for problem, solution, how, execution, PSHE. So here's how it works. So if you're sort of 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 we're going to organize this? What are the milestones? How we're going to get it to market? How we're going to the meetings? What are the rituals? All those things show up in the H.

**Shishir Mehrotra** (00:24:05):
At some point you become a little more senior, we hand you a problem and you come back with the solutions 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 sort of the pinnacle of this way of thinking about it.

**Shishir Mehrotra** (00:24:30):
Now just back to this picture for a moment, one of the interesting things that happened was the teams went and they evaluated their teams on these two ax axis and they end up with this sort of 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 skill. Later in people's careers, similarly, you're at that P level, just do bigger and bigger products. And it's like the job of being an entrepreneur or CEO or an owner or so on is just kind of do bigger and bigger projects.

**Shishir Mehrotra** (00:25:06):
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 drawn here for what I like to call the trough of dissolution. What happens in that phase, I was talking to the calibration companies about this, the reason we call the trough of dissolution [inaudible 00:25:22] 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.

**Shishir Mehrotra** (00:25:39):
To the calibrator, to the manager, it's also very confusing because all of a sudden the way I put it is the difference between a level three and a level seven may not be scoped. 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. 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 like the easiest thing to do is take the salespeople and rank them by who hit their quota and who didn't.

**Shishir Mehrotra** (00:26:21):
You go ask the sales team, who's the best salesperson and what you'll realize, and they'll say, quota statement is just a signal for how good you negotiate your quota and pick the right territory. And they say, 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. 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 sort of all sorts of ways. You might recognize a pattern of being a great P thinker, it's very correlated with being good with eigenquestions. Can you spot the right problems is very similar to can you spot the right questions? Can you decide what's important?

**Lenny** (00:27:10):
Our sixth most popular episode is with Kristen Berman, founder of Irrational Labs on using behavioral science to improve your product. Here is Kristen describing the three Bs of behavioral change.

**Kristen Berman** (00:27:22):
There are so many mistakes that humans make and we can call them biases, heuristics, our team uses psychologies. What are the psychologies that drive us? And so to tackle this, our team basically has created a model of behavior change we call the three Bs. And this summarizes the most important psychologies that drive user that are important to the product managers and the marketers. We've used this at Google, Microsoft, LinkedIn, so all the companies that we work with and they now use it.

**Kristen Berman** (00:27:51):
So the first B of three Bs framework, first B is actually not a psychology, but it is the most important part of behavior change and it should kind of be obvious. If you think about behavior change, behavioral economics, it is behavior. In order to change behavior, you have to pick a behavior that you want to change. So companies are really good at outcomes, but just not as sharp at picking the behavior.

**Kristen Berman** (00:28:14):
And when I say behavior, I mean action. The thing that you want someone to do, by the way, the only wrong answer here is log in. So it's really, it's not about logging in, it's about what you do after you log in. And when we're consulting teams would be like, we need to get uncomfortably specific. We say just really specific in the behavior. So example, if I'm Peloton PM and I'm working on the app, I would say something like within 7 days of somebody starting the app they do 2, 10 minute workouts with two different instructors. Now obviously that is wildly specific and you'd probably be very happy if they did one workout with one instructor, but the reality is if you don't define that behavior, you're going to change, you can't actually define the psychologies that affects someone's decision making when doing that behavior. So that's a first B.

**Kristen Berman** (00:29:02):
Second B, again, is probably pretty obvious and is very critical, it's just barriers. So we need to reduce the barriers to doing the behavior. And there are two types of barriers we look at. One is logistical, so this is just the stuff in our way could be entering a credit card, could be any form field. And then the second is cognitive. So the cognitive barriers get in our way as well. These are things like uncertainty aversion, this is optimism bias, information aversion. Status quo, big one. It's just you do the same thing today that you did yesterday, your job-

**Lenny** (00:29:38):
Can you talk about those three you just threw out there, just briefly? I'm curious about the specific biases while were there.

**Kristen Berman** (00:29:43):
Yeah, so uncertainty aversion, when something is uncertain or we're not... So I'll give you an example. If you're Lift, there's logistical friction, which is wait time. But then there's also this uncertainty of is it going to come on time? When is it going to come? And with this uncertainty, you're probably going to look for other options. You're going to open up Uber and say like maybe it'll come faster. And so when there is uncertainty in our life, we either look for other options or we just don't make a decision at all. This is by the way, very big in healthcare where when you're very uncertain about something, you may not even go to the doctor or you may just make the wrong decision.

**Kristen Berman** (00:30:24):
Same with status quo effect. Where we kind of underlying status quo effect is this idea that we always take the path, not always but majority of... You don't really say always when you're talking about human behavior. Human behavior is very complex. But more often than not, we take the path of least resistant. So we do the thing that's easiest and typically the thing that's easiest, it's the thing that we've done yesterday and the day before. So when you're asking someone to do something different, which is what most product, especially startups, are trying to do, you actually have to increase their motivation or make it easier, reduce the barriers to get them to do that. And so status quo effect, it's a big, big one that folks are fighting.

**Lenny** (00:31:03):
Awesome, thanks for sharing this.

**Kristen Berman** (00:31:05):
The third B is benefits. So this is where you want to increase the not just benefits, but the immediate benefits of doing something. So we are all present bias, which means we prioritize our present self over our future self. So there are plenty of reasons that somebody, your customer, your user should take an action, but you actually have to give them a reason to take an action today. So as an example, if you're Asana and you're trying to get someone to log a task, the right thing for them to do is log the task because it's going to get their project done on time. You're going to have a collaborative and communicative team that you're going to want to be on. But one of the real reasons we may log a task is because of completion bias, we want to see the checkbox. We may log it because of social desirability bias, where other people see that we're getting our work done, there's a notification that goes to my teammate when I complete something. So these are the immediate benefits that we have to build into products and features to drive use.

**Lenny** (00:32:06):
Awesome. I definitely have completion bias, I left checking those freaking check boxes.

**Lenny** (00:32:12):
**Elena Verna** (00:34:00):
I think every single company has to first focus on being product led and retention, period. The only way that you will ever have any chance of acquisition being product led is if you nail your product led retention. Let me break it down. Retention falls into two main KPIs, which is activation and then engagement. If your product is not able to activate and more importantly engage via habitual loops and be in the habit forming zone, then you'll have no chance to hooking an acquisition engine into your product. Because acquisition and product led means users and buy it or users refer or users create content that attracts other users.

**Elena Verna** (00:34:41):
Well, if your users are not habitually using your product, there's less and less opportunities for you to actually create any sort of product led acquisition. So never start with product led acquisition. You first always have to start with product led retention, activation, and engagement. Then you can choose, is your product has a relationship of one to many? If it has a collaboration at its core, say Slack or Miro or even the Amplitude. Or does it have more of a single mode relationship? So let's say Snowflake, there is not one to many relationships there between users. Well, if you have one to many relationships, product led is a fantastic way for you to prototype that model. If you don't have them, then it becomes increasingly hard. Most of the B2B products don't have that one to many relationship, so it's very difficult to stand up product led acquisition. So you rely on marketing led and sales led and that's fantastic, those are fantastic growth models as well.

**Elena Verna** (00:35:39):
The only other question becomes in the self-serve monetization, that's product led. Otherwise you go in the sales led and you chase after those large contract values. And you can still be product led and monetization with sales team via product led sales or you can just be self-serve if you have a specific segment that is valuable for. But the question there is your use cases and your market matureness to handle self-serve or do you need that sales touch? Every industry and every sector is going through transformation at different velocities. So even if you don't have that product like sales or self-serve in your industry now, I guarantee you it will pop up in the next 10 years. And if you are not going to introduce it, you will get disrupted by it.

**Lenny** (00:36:31):
For a product leader or founder who's thinking about what they should make free in their freemium model, do you have kind of a mental model of how you think about here's what you should make free? Or, is that too big of a question for a quick answer?

**Elena Verna** (00:36:44):
So I mean you first have to align on what your strategic value of free is. I do have a general framework of saying freemium has to check one of these boxes. Does it help my indirect monetization? So some sort of virality or network effects. If it does, I'm probably going to make it free. Does it suffice for every single user regardless of their complexity? If it does, then it's probably commoditization of the feature anyways and I should make it free. Does it help my aha moment? If it does, then I definitely want to have a POC as part of my free and I'm going to put it in the free offering. Does it create habit loops for me? So let's say notifications or some sort of channel communication. If it does, then I'm probably going to put it for free. So anything that actually creates friction for my growth model, I'll probably gate it in the paid. Anything that promotes my growth model, I will put it into free. Now it is very heavily dependent on your actual monetization strategies. So it's a little bit of over encompassing statement, but at the end of the day, I'm thinking about it very much. How does free help me achieve my growth model outcomes without sacrificing monetization potential?

**Lenny** (00:37:57):
Our fourth most popular episode of the year. Just to put this out there, the next three have came in really close to each other so you can kind of mix and match them in order. But at this point, the fourth most popular episode of the year is with Ethan Smith, CEO of Graphite, and just general SEO guru. Here are two clips from Ethan, one on how people often under invest in SEO. And two, signs that SEO might be right for your product.

**Ethan Smith** (00:38:23):
I think people under resource SEO a lot of times and over resource ads. So if you're Zillow, you're going to spend tens of millions of dollars on ads, or if you're eBay, you're going to spend tens of millions of dollars on ads. Why would you not have a really great SEO team? Like the amount of traffic you get is probably equal to that. So if you're going to spend a hundred billion on ads, why would you spend $50,000 on SEO? That doesn't make sense.

**Lenny** (00:38:46):
What are just attributes of a product or a company that tell you that SEO could be a growth driver or a massive growth driver? Because I imagine SEO isn't useful for everybody. How do you think about that?

**Ethan Smith** (00:38:59):
There's two big things. The first thing is the addressable market large, SO'S the addressable market for SEO large? And for most categories it is. The second is, do you have authority, you have existing traction? If you start from zero and you have no traction. So we talk with seed stage companies and series A companies, typically they don't have a lot of authority and it's too soon. And Google doesn't want you to just be an SEO site and they want you to be a credible domain before they rank you. And if you're starting from zero, they don't have enough signals that you are.

**Ethan Smith** (00:39:33):
So the way that we assess that is, the first signal I'll look at is what's your traffic? What's your current traffic? And your non SEO traffic is actually an authority signal. So I'll go into SimilarWeb, I'll put the domain in, I'll look at the total traffic and I'll want to see at least I would say 1,000 visits a day roughly for non SEO at least, if you have five visits that that's very little. And then the second thing I'll look at is the number of referring domains. So I'll go into Ahrefs or Semrush and look up the total number of referring domains. I'll try to have at least 1,000 roughly referring domains. You could grow with less than that and less than 1,000 visits, but it's much harder. And the more you have, the easier it is to grow and the faster you can grow and the more you can grow.

**Ethan Smith** (00:40:19):
And then in terms of the addressable market, that's a little bit more complicated, but most markets are pretty large actually in SEO, but we want it to be large. So With Power is actually an interesting example. So they're a clinical trial lead gen site. They want acquire people to take clinical trials. How many people are typing online, I want to take a clinical trial? Not very many. But the number of people that could be taking clinical trials is very large. And so if we target the persona, what's the key demographic of who might be a candidate for taking clinical trial? It's very, very large. So we can then create content that targets that, like gig economy or college students or people like that. So if you think about targeting the persona, most sites have a very large addressable market.

**Ethan Smith** (00:41:08):
But the way that I would think about the addressable market is that which is what product am I offering? What are the use cases for that product? What is the persona? What's the size of that? And then I would assess that typically by looking at external benchmarks. So if I'm a shopping site and I haven't started yet, I can look at other shopping sites, I can see how much traffic they have. So again, I can go into SimilarWeb if I'm Wish.com and I want to see what my traffic potential is, I can put in Walmart and Wayfair, put it in SimilarWeb, look at their total traffic. SimilarWeb's free for all of this. And then I can get a sense of how big I can get.

**Ethan Smith** (00:41:47):
The one other thing I'll mention is that there are product competitors and audience competitors. So for something like, I'm at a WeWork right now. So for WeWork, I could look at the traffic for other rental office companies or I could look at companies that are ranking for the kinds of things that I would want to rank for. And they may not be direct product competitors. FinTech is interesting. So for Robinhood, Robinhood could look at other sites that allow you to sell stocks in crypto or they could look at Investipedia. Investipedia doesn't allow you to buy stocks, but they have a bunch of traffic. It's not a product competitor, but it's an audience competitor. And so these competitors basically can tell you what the size of that market is. So that's how I think about the addressable market. So ideally it's large, it typically is. And then the more authority I have, the more I can compete. If I'm starting from zero, it's probably too early. But once I have traction, SEO can then multiply that traction.

**Lenny** (00:42:41):
We are now in the top three. Who could it be? Drum roll. The third most popular episode of the year at this point, Shreyas Doshi. Shreyas was a longtime PM at Stripe, before that he was a PM at Twitter at Google and is generally just an incredibly insightful and helpful human constantly sharing his wisdom on Twitter, and now he has his own course on Maven. Here is Shreyas describing the LNO framework, which people have brought up so many times after this episode and that I've personally found incredibly useful.

**Shreyas Doshi** (00:43:14):
When I just joined Google as a relatively new PM, this is back in 2008, for the first three years I was overwhelmed and stressed. And that was because, one, I was a new PM in this really high performance environment. I was working on some important products and launches and I just had too much to do. And I look back at that time, and it was perhaps the most stressful time of my career. Where I would work long hours, et cetera, but even at the end of the day, I'd feel highly dissatisfied because my to-do list was endless and I wasn't able to make a dent on it. I was also a little bit of a perfectionist. So I was like, no, no, no, I need to do this well. And yeah, I was just constantly I would come home and talk to my wife and kind of basically just complain to her about how I'm not able to make progress or as much progress as I want. That was accompanied with not being able to sleep very well because I was concerned about how much output I was producing and whatnot. So again, very stressful time in my career.

**Shreyas Doshi** (00:44:28):
And then things changed when I discovered the ideas related to this LNO framework in a blog post. Unfortunately I can't even find that blog post somewhere, but it had some ideas that I took and then kind of created this LNO framework on myself, which is essentially that as a product manager or as anybody in a creative high impact, high leverage role, all your tasks are not created equal. There are actually three type of tasks that you end up doing in such a role.

**Shreyas Doshi** (00:45:04):
So there are L tasks, which are leverage tasks. And the L tasks are such that when you put in a certain amount of effort, you get 10X or 100X in return in terms of impact. So those are L tasks, leverage tasks. Then there are neutral tasks, so that's N. And those are tasks where you basically get what you put in or just a little more than that. So you put in 1X and you get 1.1X. Those are neutral tasks. And then there are overhead tasks where you get back, again in terms of impact, you get back a lot less than you actually put in. And it turns out that many people, people who are ambitious or are perfectionists like myself, they by default treat each of these types of tasks the same way and therein lies the problem. So this was the epiphany for me back at Google when I kind of discovered some of these ideas.

**Shreyas Doshi** (00:46:07):
What I realized that is that among the things in my to-do list, there are actually only very few L tasks. And so it made sense for me to focus a lot on those L tasks, to take on those L tasks when I was feeling most productive, most energetic during a certain time of the day. And, for the L tasks, let my inner perfectionist shine because I'm going to get so much more in return. It makes sense for me to spend that time on that PRD for instance, related to an important feature that will meaningfully impact our revenue. I'm going to spend more time on that than I ordinarily would. So now where does that more time come from? Because it cannot come from just working more hours. Well, it comes from spending less time on N tasks and O tasks. And so there are some tasks that you do, a classic example of an O task is say an expense report. It sounds silly, but I used to try to make my expense reports really good.

**Lenny** (00:47:16):
Wow. That's funny.

**Shreyas Doshi** (00:47:19):
Sometimes that made no sense. But I was like, no, no, no, I need to do that. And again, this is the silliest example, but there are many examples. And something I realized is that the same type of activity can actually be either an L task or an N task or an O task. So what's an example? So say like a classic PM activity of filing a bug report. And so many companies have these bug templates, et cetera, et cetera, like that you use to file a bug report. Well, it turns out that filing a bug report, depending on the situation, depending on what type of bug it is, can actually be an L task, high leverage task, and over there you want to file a very detailed explicit bug report. In other cases might actually be an O task, where you don't fill out the template that diligently and you don't add 15 screenshots with annotations, instead you just have one screenshot and you hit submit on the bug report. So that shift where usually for the same type of activity we provide the same type of engagement.

**Shreyas Doshi** (00:48:30):
Last example I'll use to illustrate this is taking notes. It turns out even taking notes, taking notes, synthesizing them, and then sharing them can actually be an L task, an N task or an O task depending on what type of notes they are. After I understood this, previously I would just send all notes like I tried to make them really good, which took a lot of time. But then I realized, well, this is a meeting where, yes, I need to send notes, but it's just standard stuff. I just need to quickly list out, all people need to really know is the three action items that came out of the meetings, who owns them. That's it. And it is not about something highly strategic or controversial. Well, in that case, I'm just going to send the notes out the moment the meeting is over, I'm just going to hit send because I've already taken the action items. I'm not going to try to make my notes look great so that others can appreciate, oh Shreyas always sends great notes.

**Shreyas Doshi** (00:49:29):
On the other hand, if it was a product review with the CEO about a very contentious topic that you have gone back and forth multiple times and now you made a decision about something, you want to perfect those notes before you send them out. You want to get the language right, you want to be very clear on what the decision is so there's no room for misinterpretation so you don't backtrack afterwards. Or people say, well, but I thought we said this. So that's a case where it's an L task. And yeah, I would say just spend an hour or even two hours perfecting those notes because it's an L task. So hopefully that helps illustrate some of the ideas behind the LNO framework.

**Lenny** (00:50:13):
Runner up for the most popular episode of the year is my conversation with Marty Cagan. Marty is the legend of legend of product managers. And I'm not surprised this episode was incredibly popular. Here are two my favorite clips for my chat with Marty. One talking about why big companies are just bad at product often. And two, the four steps to be a good product manager.

**Marty Cagan** (00:50:36):
Steve Jobs shared his theory from 1995 for God's sake. His argument was, as a company gets bigger, product historically became less important. The people in a company that would be celebrated were marketing people, salespeople, finance people. Because 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.

**Marty Cagan** (00:51:47):
I hate the idea 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 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.

**Marty Cagan** (00:52:14):
In general, that means four things. First of all, they have to really get to know the users and customers. 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? 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. 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 that 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. The fourth area is you have to know the competitive landscape, you have to know the industry, you have to know the trends.

**Marty Cagan** (00:53:20):
Those are the four things you bring to the team. Realize the designer doesn't have this info, 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 incompetence.

**Lenny** (00:53:49):
And finally our number one most downloaded, most popular episode of the year, which raced to number one as soon as they came out, is with the one and only Matt Mochary. Matt is a full-time CEO coach. He's worked with CEOs of companies like OpenAI, Coinbase, Notion, Rippling, Angellist, so many other amazing folks that I could just keep listing. In this episode. There are just so many nuggets of wisdom, and I could share 100 clips from just this one episode, but I'm going to choose just two. One, the power of small teams and how small teams often get more work done. And two, advice for having hard conversations with your employees and with people in general. Enjoy.

**Matt Mochary** (00:54:31):
My companies have done a lot of layoffs, and here's why, the companies that I coached. Back in March of 2020, there was a chance that the world economy was imploding. Now, of course, by April and May we realized that wasn't the case, that the tech world kept going. In fact, it was even flourishing. But in March of 2020 we didn't know that. And so if you were being fiscally responsible, you needed to prepare for that eventuality, so you needed pare costs. 80% of costs in any tech company is payroll, is humans. So if you're going to pare costs, you actually have to let go of humans. So almost every one of my companies did, some on the low side of 5%, some on the high side of one company that was is a hotel company let go of 40% because that looks like their business was about to get obliterated. The results were crazy.

**Matt Mochary** (00:55:29):
Within 60 days of each layoff, the CEO reported back to me, it's insane, I don't know how this happened, but the company's now operating better. I'm not talking on a relative scale. I'm talking on an absolute scale. We're putting out more features, more code, our NPS is up. Whatever it is, what whatever department is performing better. And the only answer for it was we've got less people. So it's this coordination, issue is reduced with fewer people in the organization things work better. That's the big realization that most people never discover. So they hit product market fit, they get tons of money for investors, nudged higher, higher, higher, higher. But every additional human you have in your organization causes extra overhead and geometrically so, because now that you have to keep all those people informed, give them all context, make them all feel heard. Because unless they feel like they're contributing and you understand what they're saying, then they feel ignored and they feel passed over and they feel disrespected and grumpy.

**Matt Mochary** (00:56:36):
So there's this morale problem that exists. So there's this friction of information flow and a morale problem that grows and grows and grows. And really the only answer is, I mean, that's why people bring me in because they're growing, growing, growing, and things are breaking. So I have a system that keeps things together. But it doesn't make it like perfect, it just makes it so that the company doesn't fall apart. But really the ideal is just to keep the team super small. And that's what WhatsApp did. That's what Instagram did. That's what Linear is doing right now. That's what Notion has been doing for a while. And those to me are the real success stories.

**Matt Mochary** (00:57:17):
Whenever I have a difficult conversation I start it off, hey, this is going to be a difficult conversation. I want you to take a few seconds and prepare yourself. You are not going to enjoy this. What I found is that the way the amygdala gets triggered is often because of surprise. So if you give someone just a few seconds to mentally prepare, then the amygdala often doesn't get triggered nearly as hard because if they're aware that they're going to go into fear, if they're going to go into anger, they're going to go into sadness, then they can see it coming and they go, oh, that's what it is. But if they don't see it coming, just surprise and all of a sudden, it grips their whole brain and now they're in it and they don't even know they're in it. So, that's the first thing I do. This is going to be a difficult conversation. Are you ready? Person says yes. Then I share the news. I'm letting you go. Here's why, da, da, da.

**Matt Mochary** (00:58:14):
Then the second, I deliver the message. The third thing is now they're feeling emotions, strong ones. Even though I warned them, they're still feeling them. Now, you want them to be able to release those emotions. And so I say to them, my guess is you're feeling a lot of anger right now, fear, sadness. Is that true? And if so, would you be willing to share with me what you're feeling and what you're thinking? And sometimes they don't answer but many times they do and they share with me and they let it out, and that's important to allow them to let it out. And then I make them feel heard and I actively listen, and that makes them realize that I'm not trying to run away from the pain that they're feeling. I'm not trying to leave them alone with it. I sit with them as they have it, and then I try to help them get through it.

**Lenny** (00:59:06):
And that's our top 10. It was actually really hard to make this list because all 50 episodes have something really fascinating and interesting to share. For example, if you need help with pricing strategy, don't miss the Modavon episode. If you want to get better at communication, don't miss the episode of West Cow. If you're building a marketplace, there's the Hockenmaier episode. If you're trying to figure out your marketing and how to build your marketing function, don't miss the episodes with Emily Kramer and Ariel Jackson. I could keep going, but I'm just going to stop here. I encourage you to check out the full list of episodes in case you're currently facing a problem that one of the episodes can solve.

**Lenny** (00:59:40):
To close, this podcasting journey has been so much more fulfilling and exciting and interesting than I ever expected, and I'm so thankful for you for listening and for supporting this podcast, telling your friends about it. I'm also really thankful to our wonderful sponsors for supporting this work. In terms of what's ahead, basically more the same. More amazing guests, more topics that maybe you haven't thought about, that you need help with, maybe more amazing topics that you know need help with that I want to help you solve. I'm still learning how to interview, how to do this podcast, how to make it more amazing, and so my goal is just to continue to refine and iterate and continue making this podcast better and better.

**Lenny** (01:00:22):
With that, I'd love to hear from you. What do you love about this podcast? What do you hate about the podcast? What annoys you? What do you find most interesting? I'd love to hear your feedback. You can either email me at podcast@lennyrichards.com. You can also go to this episode on my newsletter, if you go to lennysnewsletter.com and find this episode, you can leave a comment at the bottom of that episode. You can also DM me on Twitter if you just want to reach out directly. Seriously, I'd love to hear from you. This is how I'm going to make this podcast better. Until then, happy holidays. Happy New Year. From the bottom of my heart, thank you for listening and for supporting this podcast. I'll see you next year.

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