---
title: "Lenny's Podcast — 2024 Q1 合集"
date: "2024-01-01"
source: "Lenny's Podcast"
url: "https://www.lennysnewsletter.com/"
---

<div v-pre>


# Lenny's Podcast - 2024 Q1 (19 episodes)

This file contains 19 articles/episodes.

---

## [1/19] The UX research reckoning is here | Judd Antin (Airbnb, Meta)

**Judd Antin** (00:00:00):
User-centered performance refers to customer obsession or user-centered practice that is symbolic rather than focused on learning. It's hugely common, I would argue. It's work we do to signal to each other how customer obsessed we are, not because we want to make a different decision. If your listeners are like, "I don't do that." I'm like, "Think about it for a second. This is extremely common." Every time a PM comes to a researcher at the end of a product process and says, "Can you just run a quick user study just to validate our assumptions," that's user-centered performance. It's too late to matter. We got to ship it. What they want is to check the box. One of my big mantras was, "We don't validate, we falsify. We are looking to be wrong." Many PMs, many designers are not in that place. They do not want to be wrong. They're looking to validate, and that's user-centered performance.

**Lenny** (00:00:54):
Today my guest is Judd Anton. Judd helped build the user research practice at Facebook. He was a longtime head of research at Airbnb, and his direct reports have gone on to lead research teams at Figma, Notion, Slack, Robinhood, Duolingo, Fair, and other amazing companies. These days, Judd spends his time consulting, helping companies with organizational challenges, product strategy, design, research, hiring, onboarding, and crisis management. In our conversation, we unpack a conclusion that Jud has come to recently about how the user research field is going through a reckoning and what needs to change both within the user research field and how companies leverage user research going forward. 

**Judd Antin** (00:04:22):
Lenny, thanks for having me.

**Lenny** (00:04:24):
It's my pleasure. So we actually worked together at Airbnb for many years. And as I was preparing for this, I realized how many of the people that you managed went on to do amazing things. So I'm just going to read a list of people that worked for you and what they do now. We had Matt Gallivan, who now leads research at Slack. We have Janna Bray, who leads research at Notion, Celeste Ridlen, who leads research at Robinhood. Rebecca Grey, who leads research at Fair, Hannah Pileggi, who I think was leading research at Duolingo, Louise Beryl, who leads research at Figma, and then Noam, who was leading research at Wealthfront. I think he moved on to something else. What a fricking crazy alumni community and group from this one team that you hired and incubated.

**Judd Antin** (00:05:11):
No, I've never looked at that list, but I'll tell you, I have been so privileged to work with all these amazing humans. I can't take credit for it. They're just outstanding people. And I'm glad the diaspora is out there, because these people, rock stars.

**Lenny** (00:05:23):
Okay. The main reason that I wanted to do a podcast episode with you is that you wrote this piece that was titled The User Research Reckoning is Here, which I understand caused quite a stir in the research community and I think adjacent communities. And let me just read one of your takeaways at the top of your post to give people a sense of what it was about. You wrote, "The user research discipline over the last 15 years is dying. The reckoning is here. The discipline can still survive and thrive, but we'd better adapt, and quick." Before we get into the meat of the piece, could you share a bit about just the reaction to this piece and maybe if it was a surprise and what you expected would happen when you put this out?

**Judd Antin** (00:06:06):
Yeah, I was definitely surprised. I wrote it because I wanted to start a conversation about something I was thinking about. I didn't really know who would read it. And in the end it turned out a lot of people read it. I learned that using the word reckoning may have been a mistake because it inspires a lot of drama in a conversation that I wanted to be really productive and positive. Overall, I would say, though, that the response was very positive. It seemed to resonate with a lot of people who reached out to me. I spent a lot of time talking to teams, to designers, to researchers, but there were also a ton of critiques. 

**Judd Antin** (00:06:43):
I would say some of it was like people thought I was throwing research or researchers under the bus, like, "It's researchers' fault. We're doing it wrong." Which I don't believe at all. And that I wasn't taking responsibility as a research leader or a design leader myself. And the most interesting one I would say was the anti-capitalist crew, because one of my points that we'll talk about is that I think researchers need to be more profit focused. And there are a lot of people out there who, I think they think that's not cool or not research's job, and I'm like, "Well, what are we doing then, if we're not helping businesses succeed?" But that was the most surprising critique, for sure.

**Lenny** (00:07:23):
I've worked with some of those people who are just like, "Why are we growing? Why do we focus so much on growth? Why do we need to grow this business?"

**Judd Antin** (00:07:29):
Yeah. 

**Lenny** (00:07:29):
So I get that. 

**Judd Antin** (00:07:30):
Maybe it's the wrong industry for them.

**Lenny** (00:07:32):
Yeah. I'm not a fan of that. Okay. Let's actually dig into the meat of your message, and the big takeaway, and the conclusion of what you're finding is happening in user research. And I know a lot of this comes from a lot of user researchers have been laid off at a lot of companies. It was one of the hardest hit teams. And so I think a lot of this comes from that. So yeah, so let's just start big and then see where it goes.

**Judd Antin** (00:07:53):
So yeah, everybody who's paying attention has noticed that there have been a bunch of layoffs. And I think back in the summer I was thinking, "Listen, this seems to be hitting UX and UX research particularly hard. Is there something going on? Is there a bigger picture?" The reason I use the word reckoning is because to me that's like, "Hey, a moment to take stock." And triggered by the fact that a lot of wonderful humans may have lost their jobs, and many more are afraid of losing their jobs. And so if it's a sign, the fact that research has been hit so hard, it's a sign of what? And so the thesis of my article is really, it's a sign that maybe the system is a little more broken than we think and that research is not driving the value or impact that it should or could. And that's for a bunch of reasons, I think. Some of it is stuff that research can do better, and a lot of it is how research is integrated and positioned in companies. 

**Judd Antin** (00:08:46):
And at the root of all that, I think, is that we're just doing too much of what I would consider the wrong type of research. And what I mean by the wrong type of research is I have this framework, and it's in the article, macro, middle range, and micro research, at least three ways to talk about it. And it's pretty simple, the intuition of what those are. So macro research is big picture, strategic, business focused, forward-looking innovation, look at the market, look at competitors, long-term research to understand where the product should go next, stuff like that. 

**Judd Antin** (00:09:20):
And then you have micro research, which a lot of really technical usability falls into this, all the beautiful stuff that researchers do to enable a really high quality, excellent, pixel perfect thing to go out the door, laser-focused research to understand AB test results, stuff like that. And then you have this middle range, which is this blobular place where the research questions are middle altitude and a lot of the core, let's say user understanding questions fall here. And a lot of what research is doing is research in that space. It's, "Let's take a group of people and ask some questions about how they think, feel, behave, how they're using a product or not using a product." And it's just this devastating mix of really interesting to many, including researchers, and not impactful enough for the business. That's the core thesis. Researchers do it because it's interesting, but honestly, and a thing we should talk about, Lenny, is researchers also do it because it's the kind of work we most often get asked to do. 

**Lenny** (00:10:22):
Yeah. That's exactly what I was thinking. As a PM, that's what I want to get answers to, is like, "How should we think about this one product?" And I totally get this.

**Judd Antin** (00:10:31):
Yeah. The questions turn out to be really interesting and there are many cases at many companies where it's super impactful. But the problem with those types of questions is they tend to, they trigger all the worst stuff that researchers experience. So they yield results which are interesting, but sometimes hard to operationalize. They trigger the post hoc bias, really, really, really well where a lot of people can say confidently like, "Oh, that was obvious. We knew that already." And they fulfill this need for us to feel and be customer obsessed, user-centered, without changing anything. So doing too much of that research to me is a symptom of a broken system, and where companies are really different from each other. I heard from so many after this article and they're like, "Well, my company and my industry is like this or not like this." 

**Judd Antin** (00:11:24):
But in tech, we spent the last many years hiring, hiring, hiring researchers, but maybe, I'm sure most of your listeners are familiar with the idea of a ZIRP. Maybe it was a zero interest base phenomenon, where it was okay when the money was easy, to hire researchers, even though we were not setting them up properly. We're were going to set them up to fail. We set them up as a service function. We didn't know what research was for. We didn't know how to really drive impact with it. And that's where the reckoning comes from. It's like that era is over. Research, I think, is more crucial than ever. Good, great researchers are more impactful than ever. But it's in a new space. We're in a new space now.

**Lenny** (00:12:05):
I want to make sure people understand this framework. And specifically, how would you best describe the difference between this middle range research and macro research?

**Judd Antin** (00:12:16):
Middle range research is usually focused on a more specific set of research questions or a constituency. So if macro is like, "Let's understand the overall competitive landscape. Let's do a concept car type project where we really look ahead. Let's get involved with strategic planning," which is a wonderful thing for researchers to do, do TAM studies, other things like that, that stuff lives in the macro space. 

**Judd Antin** (00:12:42):
The middle range space is like, what's a good example? "We want to know how Airbnb hosts feel about their payment options." That's a really interesting, reasonable question. And we can go out and do research on that, but it's not that specific. It's not really targeted at a business problem yet. It could be. Maybe that's a result of the research, but it yields these middle range insights in which we've learned things like, "Well, hosts want flexibility about their payment options." I'm making this up. And that's a good example where it's like, "It's not that that's not an interesting set of questions, it's just not quite pointed enough." And it's not framed in the language of the funnel, or the business strategy, or the OKRs. It's not quite enough aligned enough to that. It's too blobular in that middle level and it ends up not driving impact.

**Lenny** (00:13:38):
I think it also leads to a lot of the things as you described, people don't like about research. It delays everything. You have to wait for the research to be done to have an answer, to make a clear decision. It also creates this issue that people complain about, that PMs and product teams don't want to just make a decision on their own. They're like, "I will get this additional data point and make sure research tells us this is the right answer instead of just trusting there." God, I guess maybe along those lines, this might be going off a little track, but what's your advice there for, say, product managers or PMs or product teams to not necessarily rely on research for that middle research?

**Judd Antin** (00:14:14):
I think the reason why so many PMs ask for those middle range questions is because they haven't really gotten deep with their researcher in a way which can leverage it for maximum impact. So if the question is like, "Hey, Judd, you just pointed out a bunch of problems, can you be more solutions oriented?" Well, the solution is simple but not easy to me. It's that we need to restructure the way we make products in a way which integrates research much more fully. It looks like consistent relationships in which researchers, and the work, and the insights they provide are a part of the process from beginning to end.

**Judd Antin** (00:14:51):
And I think, Lenny, you as a PM, that's how you worked. I remember you, I know who you worked with. You worked with great researchers. But honestly, most product processes are not that way. And so that's when research is a service function. It gets called in right at the end. It's reactive in the sense that a researcher in the room listening and participating in the conversation could have a ton of impact on framing exactly the right question that will drive maximum business impact, maximum product improvement at that moment, and then go do it quick, and get back, and we're onto the next. But they weren't there, the relationship wasn't there. They're not engaged in the project from the beginning. And that's the number one root of the problem. As long as research is a service discipline, I think we're going to be stuck in this spot.

**Lenny** (00:15:37):
When people might be hearing this, on the one hand, it's research has been not as helpful to teams as they thought, and researchers have been spending time on the wrong thing. On the other hand, your advice is integrate research from the beginning, make them more involved throughout. And I think that might confuse people. How should people think about, like, "Research is actually more important? You should integrate them more deeply."

**Judd Antin** (00:15:59):
There's a vicious cycle that's been happening, is from where I sit, and this is what I hear from many, many researchers and research leaders, which is a lot of companies hired a lot of researchers with great intentions, didn't quite know how to integrate them. And UX research is a newer discipline, so maybe that's not surprising. We're still learning how to use it. "Cool, let's evolve." But a lot of companies hired these people, but they hired them into kind of like a service discipline, very reactive, not in the room, not integrated in the way I said. 

**Judd Antin** (00:16:30):
And so they had less input on the questions to ask, or they're included, but only at the end. And then they're unable to build those direct relationships, to be there in the room to actually drive the questions and insert insights. Because a good researcher is like the repository of insights you need for growth, but they're not there. They don't participate in the decision. So they end up doing research. They have jobs to do, so they do research that is too reactive, it doesn't matter, and then it's less impactful. Executives conclude that therefore researchers are not as impactful and then they get sidelined or laid off and the cycle continues. 

**Judd Antin** (00:17:07):
So I think the short circuit is the constant engagement. If you take a great researcher and you insert them consistently in a product process, I feel confident that researcher will drive a product improvement, metrics impact, growth, all the things that you want to see as a PM and a product leader. It's just that's the exception, not the norm these days.

**Lenny** (00:17:31):
This may be a hard question to answer, but when people hear, "If you have a great researcher, here's how you approach it." What are signals that your researchers is great versus not great? What are some things people could look for to tell them, like, "Oh, maybe I have the wrong researcher on my team."

**Judd Antin** (00:17:44):
The best researchers I think are first of all, multi method. The first iteration of user research was primarily a qualitative discipline. But a strong opinion that I have is that is largely one of those models that needs to evolve. It's not that qualitative user research is no longer important. It's that the best researchers have five tools. I think they have five tools. And those five tools are number one, what we would call formative or generative user experience research. So looking ahead, innovation focused, really open-ended, maybe more ethnographic, "Let's go out into the field and talk to host and guests on Airbnb. Let's see people using our product in the field," stuff like that. So that's formative. 

**Judd Antin** (00:18:27):
The second type is evaluative, so more like usability testing. The third tool is a basic rigorous survey design. It's the best scaled way to get responses from communities small and large. You can get a lot out of really well crafted surveys. But to do that, you have to have the fourth tool, which is applied statistics, the best research, know a little bit of stats. You can't interact in a world of AB testing without knowing basic statistics. 

**Judd Antin** (00:18:56):
And then in the old version of this, the fifth tool was SQL, because I think good researchers need to be able to run their own queries. These days, so much of that is dashboarded, that the fifth tool may now be prompt engineering, which is a thing we could talk about, but I think maybe that's the fifth tool is somewhere, is it technical skills that fall in between querying your own data, understanding it very well in companies that are awash with data and then interacting with generative AI.

**Lenny** (00:19:24):
Amazing. That's such a cool list. Okay, so just to playback, formative, generative, innovative skills to think bigger and come up with new ideas, usability.

**Judd Antin** (00:19:35):
Yep.

**Lenny** (00:19:35):
Yeah, usability. How did you describe it? I have a different word, here. Evaluate? Evaluative?

**Judd Antin** (00:19:41):
Evaluative, right.

**Lenny** (00:19:41):
Okay.

**Judd Antin** (00:19:41):
So we're evaluating products and doing more. Really that's the micro level of research. 

**Lenny** (00:19:47):
Survey design, being really rigorous about it, applied statistics, and then SQL/dashboard/prompt engineering. 

**Judd Antin** (00:19:53):
Right. 

**Lenny** (00:19:54):
Maybe just one last question along this thread, also a big question, but any advice for how to evaluate these skills/interview for them? I know this is its own deep topic, but any advice for someone trying to find this person?

**Judd Antin** (00:20:05):
I've interviewed hundreds or thousands of researchers, and the way I usually approach that is you want a researcher who's got a Swiss army knife, because if all you have is a hammer, then everything looks like a nail. And so if you give in the context of an interview, let's say, a researcher, a pretty juicy, open-ended research question, and you want to see how they handle it, and a good answer is usually multi-method. We're not going to handle it in any one way. We're going to say, "Well, here's a couple of ways we could deal with this. Here's how we could do this in a day, or a week, or a month." We usually don't have a month, but sometimes big research projects go on for that long. "And here are the different sets of methods that we can use." 

**Judd Antin** (00:20:44):
So see where they go. It's actually pretty simple. Most researchers are deeper in one than the other, and sometimes you can make up for those five tools with the team. So you have experts who are t-shaped, but maybe deeper in one or several of those ways. But when I built a team at Meta and at Airbnb, that was my goal, is individually as researchers build up those tools and then as a team build deep expertise that would fill all the gaps.

**Lenny** (00:21:10):
Coming back to the main premise of your post, one of your big takeaways is, "Researchers need to be much more business oriented, thinking about what helps the business versus the user." Which I think to a lot of researchers will feel really weird. Can you just talk about your takeaways there?

**Judd Antin** (00:21:25):
So much of user experience practice, not just research, but design too, is focused on empathy and very user-centered. This is beautiful. I'm not saying that we should abandon that. I think what I'm saying is there's an overlapping event, where you have the user and profit or the business. And what researchers need to do is be way more explicit about finding that overlap. So one thing, when researchers ask for advice, they're like, "Well, what should I do to be more business or profit focused?" I say something like, "Did you read the last quarterly report, If it's a public company? Did you listen to the shareholder call?" And they're probably like, "No, it's full of a bunch of language I didn't quite get." 

**Judd Antin** (00:22:12):
And I'm like, "Yep." So there you go. That's the language you need to learn. Scour your Google Drive folder, your internal folder and look for all of the documents that are about this quarter, or this halves, or next half strategy. What are the OKRs? Understand the metrics and the conversion funnel, know it back and forward, because then what you're doing is you're proposing, if you're in the active conversation, you're saying, 'Cool, I hear you asking that research question. I've identified this is exactly the spot in the funnel where I think we need to do work. There's an opportunity here. Or that competitor is eating our lunch with this group of users. I know that because I read the competitive report and I understand it deeply.'" So those are skills that some researchers have and a lot are building these days, but historically, last 15 years, it hasn't been a thing we've been as focused on, and I think that's an evolution that needs to happen.

**Lenny** (00:23:06):
I think a lot of PMs listening to this are going to be like, "Hallelujah." This is exactly what I've been trying to convince people of. It's what I've been trying to convince my researchers of, and design often falls into this.

**Judd Antin** (00:23:17):
But Lenny, the opposite is true, too, because you got to take the average PM who lives in that land, all day, every day, and what they do is not in the Venn. I think those are people who are also performing customer centricity and performing user-centeredness a lot, when they're really not interested. And so this is not about researcher. This takes two sides. Fixing this broken system takes everyone, researchers, PMs, designers, everyone at a company, but also the way that organization is structured, and integrating itself in a different way. Everybody's got to come to the table.

**Lenny** (00:23:55):
Such a good point. And you have this actual term that you call user-centered performance, where it's the performance of being user-centered. Can you talk about that and then just what advice you'd give to PMs that, hearing this, are like, "Yes, I love everything you're saying," and then not realizing maybe they're too far in that extreme?

**Judd Antin** (00:24:11):
User-centered performance is a term I made up, because it's fun to make up terms. And it refers to customer obsession or a user-centered practice that is symbolic rather than focused on learning. So it's hugely common, I would argue. It's work we do to signal to each other how customer obsessed we are, not because we want to make a different decision. And if your listeners are like, "I don't do that." I'm like, "Think about it for a second." Because this is extremely common. It shows up in explicit ways and implicit ways. 

**Judd Antin** (00:24:52):
So explicitly, I would say every time a PM comes to a researcher at the end of a product process and says, "Can you just run a quick user study just to validate our assumptions?" That's user-centered performance. It's too late to matter. That PM is not interested in being wrong at all. It's too late in the game for that. We got to ship it. What they want is to check the box. So any check the box style research is a wild example of user-centered performance. 

**Judd Antin** (00:25:22):
I would argue every researcher has probably had to do executive listening sessions because a lot of PMs, founders, product people, but designers, too, they want to get close to the customer. And so, like, "Can I do some focus groups? I want to be there. I want to ask them questions." This is 97% performance. It's well-intentioned, but it isn't focused on learning. It isn't going to drive better outcomes or more impact. 

**Judd Antin** (00:25:49):
And then there's all these implicit ways that people engage in that kind of user performance, too. A lot of it comes down to cognitive biases, confirmation bias, ego. One of my big mantras was, "We don't validate, we falsify. We are looking to be wrong." That is the mindset you should use when you're approaching insights and research. "I want to be wrong. I want you to do research that shows we were off base in the following ways. Tell me exactly how and why in a way that allows me to fix it quickly." But many PMs, many designers are not in that place. They do not want to be wrong. They're looking to validate. And that's user-centered performance.

**Lenny** (00:26:29):
Oh, man. I think a lot of people are hearing this and feeling exposed.

**Judd Antin** (00:26:33):
Exposed.

**Lenny** (00:26:35):
I feel like you're like this Deep Throat person coming from sharing these things people don't want to talk about at the office.

**Judd Antin** (00:26:35):
I know.

**Lenny** (00:26:42):
There's this quote in your post I'm going to read. "Product managers love to ask for middle range research that they can use to justify decisions they're reluctant to make on their own. User designers love to ask for middle range research because it fits their model of what proper design process should look like. Executives love to ask for middle range because they don't really understand what research is for, and helps them do performative user-centeredness. In the end, they will decide based on their own opinions."

**Judd Antin** (00:27:07):
There is an important place for intuition in product development, of course. The best designers, researchers, product people develop strong intuition for the product. But you got to understand, intuition is where all of those biases lie. It's where all your blind spots are. And what great insights people do, what great researchers do when you're next to them all the time, is they'll expose you. I don't have to be the Deep Throat, because you have somebody who's professional job is ... Keeping you honest is probably the wrong way to put it, but as somebody whose capabilities are about expanding your horizons, making it so that your intuition is constantly improving, you don't have to rely on it when your intuition and the evidence sort of collide in a way that either affirms or falsifies the product decision you made. Now something really good is happening. 

**Judd Antin** (00:28:00):
And the other thing that is inherent in that quote is I, at Airbnb, wore many hats over the years. I was head of research two different times. I was head of design for guest products. And my last job was I was head of the design studio, so UX research, UX design, writing, localization, they all reported up to me. So I've seen this from many disciplinary angles in the UX field. And researchers aren't the only ones who are guilty of this. I would say design has a ton of performance. And it comes from the fact that we have figured out user-centered design, this process, or design thinking, which IDEO popularized. Like, "That's what we're supposed to do, right? Bezos told us that we, as PMs, had to be customer obsessed. So that's what we're supposed to do."

**Judd Antin** (00:28:48):
It's a really common and damaging thing when we don't genuinely have that growth learning mindset, and it's easy to sideline researchers. We don't need them in that situation. We've got our guts. Isn't the gut where a great PM, a great founder needs to have that gut? And they do, but they need to be open to the fact that your gut, is limited, and biased, and narrow, and wrong sometimes.

**Lenny** (00:29:13):
The two sides of this is trust your gut opinion, "I don't need research, I don't need data. I have opinions, and my own experience, and I'm going to use the product, and let's just go with what feels right to me." Versus pure data-driven research driven for designers that are maybe listening for product managers. Do you have any advice for just where to fall on that spectrum and just how to best leverage research to inform that opinion?

**Judd Antin** (00:29:36):
Yeah, I taught a class at UC Berkeley this semester on leadership, and we talk about that a lot, because great leaders develop intuition. It's the pattern matching part of experience, where you develop heuristics which allow you to make good judgments even if you can't quite explain where that judgment came from. That's what the gut is. But it's also, like I said, where bias comes from, where all the cognitive biases, there's a list of 151 of them on Wikipedia, I won't name them, but all those thorny things that lead us astray, the behavioral economists and social psychologists study, those live in the gut. And so the advice is when you are looking to check your gut, you have to do that thing. A lot of your listeners have probably read Thinking Fast and Slow, System 1, System 2. Right? 

**Lenny** (00:30:29):
I have it here, right under my laptop, actually, holding up my laptop screen. 

**Judd Antin** (00:30:32):
That's so appropriate, Lenny. So the secret is not that sexy. It's System 2. So you engage that slow, methodical process in which you do analytic thinking as a means of checking your gut. Slow in the grand scheme of things. Slow meaning not a split second decision, not like months of analysis. That's not what I mean. 

**Judd Antin** (00:30:54):
The other thing you can do, and there's really great research on this, is you bring in the wisdom of the crowd. So the wisdom of the crowd is a phrase a lot of people are familiar with, and it works in a specific situation. The wisdom of the crowd works when the people involved with the decision are bringing diverse sources of information and judgment to the table. Obviously, if everybody has the same sources of information, then it doesn't matter how many people are out there. So if you want to check your gut, get a bunch of different guts together, get a bunch of different people in the room who can bring evidence and intuition to bear, and have an open, direct end kind conversation in which we might disagree. You know who's great at that? Researchers

**Lenny** (00:31:38):
Leading those discussions essentially, and getting a bunch of people's opinions.

**Judd Antin** (00:31:41):
Yeah, this is the structural solution I'm talking about, Lenny, is like, "I never asked for research teams to have their own separate OKRs." I said two things, "Number one, what's the teams? Shouldn't the PMs, the engineers, the designers and the research, everybody should have the same set of metrics for success because either we're doing it together or we're not." And then I said, "My metric for success is when they won't have that meeting without you." That's my metric for success. If they cannot have that decision making meeting without the researcher there, that means you've developed influence, strong, trusting relationships, you're an active participant in the process, not just somebody who provides input into someone else's process. And that is when researchers can have huge impact.

**Lenny** (00:32:29):
I think of the PM role in a similar way, even though people won't have these meetings with PMs, because they're often at the center of lot of the stuff, but you want to be a PM that people want on their team. There's a lot of teams that are like, "We don't want and PMs, we don't need product managers. They just get in the way." And I find that that's only the case when the product manager's not great, and not really good at their job, because most great PMs just make everyone's life easier.

**Judd Antin** (00:32:50):
They do. The grease, I-

**Lenny** (00:32:51):
The grease.

**Judd Antin** (00:32:53):
... love it.

**Lenny** (00:32:54):
You mentioned also, before we started recording, that the biggest challenge for user researchers is in their relationship with their product manager. Can you speak to that and what you've seen there?

**Judd Antin** (00:33:04):
I'm wary of overgeneralizing, but I can tell you that from my experience and from what I hear, the product research or product insights relationship is one of the most challenged. And I think it comes from the fact that fundamentally, many researchers are just not included in the process that PMs are running. And then, actually, I did some asking around before this podcast, and so I thought, "There are some tropes that researchers have about PMs that are worth PMs knowing, just like four or five of them, the things that researchers know PMs say, which drive us nuts because they're not true." 

**Judd Antin** (00:33:51):
So the first one is that research just slows us down. Research is too slow. This is bullshit. A great research team can do research in a day, a week, or a month. It just depends on what you want to get out of it, like, "How much detail do you need? How many people do we need to talk to? What is the depth or breadth? Do we need to go to seven different countries to talk about our constituencies in Latin America?" Well, that's not going to happen overnight, but we don't often need that. The other way to look at that is that is it slower to get it wrong and fix it than to take a hot second to do the work to get it right the first time? So that's BS. Good research doesn't slow us down, it speeds us up.

**Lenny** (00:34:36):
And also just along those lines, a big part of your premise is you don't need to do as much research as people are doing, like this middle research that a lot of the time is put into. 

**Judd Antin** (00:34:45):
Yeah. Research can go super fast. I think especially, so the macro level research, I hope what it is tied to things like annual planning processes. We did a thing at Airbnb several years that we called, it was like Insights 2019, Insights 2020. They were concept car projects. And we spent quite a long time synthesizing the entire year's worth of insights from every place we could get them and then developing with designers and engineers like a concept car for five years in the future. So that's a long process. 

**Judd Antin** (00:35:16):
But the micro level, there's so much business value to be derived there, so much business value, and it can go so fast, Lenny, it can go so fast. You can have results in 48 hours on these things. We did a thing at Airbnb. There's a famous story which I'll only tell in the abstract, because I don't want to out anything, but we call it the multimillion dollar button. And basically we did research which revealed that people weren't going down the purchase funnel because they were afraid. The calls to actions on the button was making them afraid that it would initiate a purchase when really it was just taking the next step. 

**Judd Antin** (00:35:58):
We changed the text on the button with help from our amazing content design, our UX writing team. We basically changed seven characters and made Airbnb millions of dollars, because what we found out was really simple. It was just like, "Hey, this button feels scary. The CTA on the button feels scary." So that's a great example of how micro ... And that happened in like 48 hours, we would discover that insight, or overnight, basically. And we were like, "Hm, maybe we should test some other CTAs." We did the conversion, we added like 1%, which is really, really hard to do. So that's a quick example of how that type of quick research can drive a huge amount of business value.

**Lenny** (00:36:39):
**Judd Antin** (00:37:55):
Exactly. The micro research should be much more common. A lot of researchers think that that's scut work, that usability is something junior researchers do. I completely disagree. I think we need to get back there as an industry and be like, "When you make a product easier to use, when you discover problems with functionality, business metrics we care about will go up." I've seen it happen. But that's not just work for interns and new grads, that's for sure. 

**Judd Antin** (00:38:24):
And then the planning process, absolutely. If we're integrated from beginning to end, we can help. And the thing about that middle range, I think you're right. That's the stuff that makes the stereotype that research is slow, and a lot of times it's also because it's just not pointed enough. The researcher can also say in that moment, "I have studied the business plan. I know exactly where, I've seen the metrics trend, I have an idea about exactly where that's going to go." We still need to do that middle range research. The question is valuable, but it's now very pointed and the time is worth it.

**Lenny** (00:38:58):
Amazing. Okay, I want to cure the rest of these tropes.

**Judd Antin** (00:39:01):
Okay, research is too slow is the first one. The second one, I can do my own research. Why do I need researchers? And that's true, as product people, I hope you are engaging with customers and listening well. But no offense, garbage in, garbage out. The thing is, anyone can talk to a user. That does not constitute research or insights work because one user can be powerful, but one user can be idiosyncratic. And a researcher knows how to get to the heart of that really quick. They know how to take that conversation, and understand, and situate it in a way which means like, "Sure, democratize research. That's happening. There are tools out there that will let anybody get customer feedback, voice a customer type stuff." But a researcher is there to help you turn garbage into something that's not garbage and avoid the bias that can come from you just reaching out to your cousin's family and then doing whatever they thought you should do to the product. So that's the second trope. 

**Judd Antin** (00:40:08):
The third one is AB test everything. And AB tests are great, but one of my most painful things to do is to sit in a room full of PMs and data scientists who have just seen the results of an experiment that flipped a stat sig, and then they're like, "Cool, I was significantly down over this course of time for these users." And then they just start speculating about why that is, because the AB test rarely tells you why it changed in the way it did. And then this endless flywheel of AB testing goes and I'm like, "Hey, you don't have to guess. I know somebody who can get you an answer or at least evidence that addresses the question of why did we see the test result we did in a very short amount of time? Or you could use your customers as Guinea pigs, and throw more experiments at them over and over, and spend a long time on it, and come to the same place in the end."

**Lenny** (00:41:03):
I think a similar critique that PMs often have is AB testing is conclusive scientifically, statistically, user research is just talking to a bunch of people. Why would I trust that? What is your best way to help PMs realize that this is actually very valuable data and you should listen to it? It's not just, you know, a story here and there. 

**Judd Antin** (00:41:26):
Yeah. No, I think they're both right. AB testing is as close as we can get to making causal claims about products. Research is usually not oriented towards making causal claims or it should not be, but those causal claims rarely tell you how and why things happen. And if you want to not make that mistake again in the future, you need to know how and why. If you want to build a better product in a way that doesn't just answer this narrow question that an AB test answered, you need to know how and why. And so you need both. Beautiful partnerships between data scientists and research and insights people are, I think what we're going to see in that next evolution. And if you set that virtuous cycle up, if you set up the engagement where those people are involved from the beginning, you don't make those mistakes. You get the causal relationship, which is valuable for one reason and the hows and whys, which are valuable for other reasons. 

**Lenny** (00:42:19):
Awesome. Okay. I think there's two more tropes you had. 

**Judd Antin** (00:42:23):
One of them is a simple one, which is like everyone loves to quote that it turns out a totally apocryphal Henry Ford quote about, "If I'd asked my users." It turns out to the best of our knowledge, he did not say that. And-

**Lenny** (00:42:35):
Really? What?

**Judd Antin** (00:42:36):
Yeah, I know. Isn't that sad? 

**Lenny** (00:42:36):
I didn't know that.

**Judd Antin** (00:42:38):
I know. Sorry to burst your bubble, Lenny. 

**Lenny** (00:42:40):
Oh, wow. 

**Judd Antin** (00:42:41):
Who was-

**Lenny** (00:42:41):
Does anyone say anything? I feel like every quote is-

**Judd Antin** (00:42:44):
Is apocryphal, now? I know. 

**Lenny** (00:42:46):
Yeah. What is reality? Geez, can we? Well, let's just- 

**Judd Antin** (00:42:49):
Okay, maybe he said that. He certainly believed that. That's what the historians say. But the reason that makes researchers so angry is because that's not research. That's not what researchers do. A researcher who's going to ask customers what they want is a bad researcher. You need a different researcher. I've never done that in my career. No one on my team has ever run a study that's like that. So that just makes researchers mad.

**Judd Antin** (00:43:16):
And then the last one is about post-hoc bias. It's, "We knew this already. That was obvious." And I think a lot about this book, which I would recommend to your listeners. The author is a sociologist at UPenn named Duncan Watts, and the title is Everything is Obvious If You Already Know the Answer. And it's about hindsight bias. He makes the argument that we rely too much on intuition, heuristics, and pattern matching in a way that is inappropriate to our experience. And it's like it leads us astray. It's like a form of self gaslighting. And it happens because we end up selectively remembering things and then constructing narratives around them in a way which makes us feel like we already knew that, when we in fact did not.

**Judd Antin** (00:44:49):
That's beautiful.

**Lenny** (00:44:50):
Thank you for these tropes, by the way. This was fun. I didn't know you were going to do that. So that's a fun, little collection we've got, here. 

**Judd Antin** (00:44:54):
Thanks.

**Lenny** (00:44:56):
I wanted to ask about, there's this tweet by Patrick Collison that I've brought up a couple of times on this podcast, that I think is really interesting. And his tweet is this, "In my opinion, the best product will stem from a very strong mental model of the domain and user. User research can help you get such a model and validate it along the way. But it's important to view the syllogism of UXR as model of user research, to improving your mental model of the user, to what product you should build versus user research tells you what product to build." Does that resonate in any way thoughts on that way of thinking about user research?

**Judd Antin** (00:45:34):
Yeah, there's a double-edged sword we talk about a lot in the research community, which is about making recommendations for design. So the best research doesn't leave it at that. It tells you, and it's like the what, the so what, and then the then what. But the problem with that is some researchers go too far in the other direction, where they're like, "We ran this study, it yielded these insights, and therefore this is what we should build." And everyone else on the team is like, "Whoa, whoa, whoa. Glad to hear your thoughts on the matter, but there's a lot going on here. Maybe we should talk about it." And that makes perfect sense. That's a failure of communication. 

**Judd Antin** (00:46:19):
And I think that speaks to the thing that Patrick is saying, is like, "Good research can sometimes tell us exactly what the problem is and exactly how to fix it." An example of that is the multimillion dollar button I told you about. But in a lot of the bigger picture questions, especially the macro ones and maybe also the really pointed middle range ones, the point isn't really, "This is exactly what we should do and this is exactly what we should build." It is, "Let us develop a framework which is based on actual evidence, and then together as a team figure out how we want to experiment our way to a successful product."

**Lenny** (00:46:53):
To close the loop on this specific thread, what is your advice to teams, researchers to help move out of this reckoning, and to move forward, and help the field, both from a user researcher perspective and also from just a company that maybe laid off a bunch of user researchers or is trying to decide what to do with their researchers?

**Judd Antin** (00:47:14):
Thank you for asking. I think I said to you earlier, and I feel some pressure as maybe the first conversation that you've had specifically about research on this podcast.

**Lenny** (00:47:23):
Yeah, I think so. 

**Judd Antin** (00:47:25):
And I want to help. I believe so much in this discipline of research and insights, and I think when I said, "The UX research discipline of the last 15 years is dying," I didn't mean that I think research is dying, far from it. I think that there's a version of it, which we're now moving past and into a new version. We're going through an evolution, as many do. And so the question for me is like, "How can researchers, and the companies, and the other people with whom they work create a new version, a different version, an evolution, which is hugely impactful for the business?" 

**Judd Antin** (00:47:57):
And so the advice I'd give to researchers about that is develop diverse research skills. Remembering the five or five and a half tool list that I mentioned earlier, really go deep on that business knowledge, so speaking the language of product, and business, and metrics, and understanding exactly how to use your insights like a scalpel, building those strong relationships, which is not a thing that researchers can do by themselves. It requires two-way engagements, and also in a way which allows researchers to do fewer things better. 

**Judd Antin** (00:48:30):
So most researchers that I know are working on teams where they're like, "I'm the only researcher, and I have seven PMs and 20 designers, and I'm trying to do 10 projects." And no one's going to do a good job that way. So researchers have to learn with their partners about how to say no and focus on the most important things. But that's only half of it, right? That's the research side. 

**Judd Antin** (00:48:51):
I have two thoughts about what companies should be doing. The first one, it's a little bit of an aside, but not really. One thing I learned by through the responses to the article was everybody came out of the woodworks from the variety of insights disciplines that are out there. Because I come from a tradition of user experience research or user research, but there are many insights disciplines in many industries, and they all wanted to claim one type of research or another, and say, "Oh, well, we overhear in consumer insights or market research have been doing that well for years." And there are many insights disciplines. And generally I think creating silos is stupid. 

**Judd Antin** (00:49:33):
Actually, I'm curious what you think, because here's the number one thing I heard when I joined Airbnb and you were there, is I did it a quick listening tour where I talked to a bunch of product people. And they all said the same thing. They were like, "Listen, we have all these different people throwing insights over the transom. And it's great. We want to hear from the data scientists, from the product specialists, from the customer service people, and the voice of the customer, whatever, all that stuff. But they're all coming over the side and we don't know what to make of it. It's too much."

**Judd Antin** (00:50:03):
And that, as much as anything, is an argument for companies to stop siloing research disciplines. So when I joined Airbnb, I set out to create an integrated insights function where it's like, "Let's do UX research, let's talk about the market and competitors when we have to. Let's integrate smartly with data science functions. Let's integrate all the stuff we're getting from customer service feedback." We brought over what was then the NPS program and said, "Hey, if we're getting customer feedback there, let's all just use it all to fuel this one insights machine." So that's the first piece of advice I'd give companies.

**Judd Antin** (00:50:38):
And the second one, without being a broken record, is to think differently about the broken cycle. So integrate researchers into a unified, lean process. So if the researcher is not there from beginning to end, if there are not strong relationships between product people and design people at every level, engineering people at every level, and somebody who's their insights partner, we're going to fall back into this problem where we're just a service discipline, we're not extracting the maximum value, it comes too late, we don't know what questions to ask, we're ignorant about what research can do. And so creating that integrated, lean process where a researcher is arm in arm from the beginning, is the most important advice I'd give.

**Lenny** (00:51:19):
That last piece may be the answer to this next question, but the question is how can product managers be better partners to user researchers/get more leverage out of user researchers?

**Judd Antin** (00:51:31):
I think that is in many ways the answer, making sure that they are creating a process for the product, for their products, that it integrates user researchers and insights from beginning to end. Also, being willing to partner with the research on the roofless prioritization. I used to say that, "A full plate for a researcher was probably three things, two big projects and a small project, like a side project. More than that, your researcher is probably not doing a very good job. And a project may take 48 hours. That's okay. But so they need your help to prioritize, they need you to participate. Great PMs will take the time to be with researchers to go into the field, even to travel." Did you ever do that, Lenny?

**Lenny** (00:52:15):
I did. I went with Louise, who introduced, we came up with this, basically told me to chat with you about this topic. 

**Judd Antin** (00:52:23):
Thanks, Louise.

**Lenny** (00:52:24):
Thanks, Louise. We did a whole tour to Paris, our whole team, or the leads of our team went to Paris to do a bunch of focus groups and a bunch of user research behind actual mirrors. I've never done that before that trip, and it was amazing. We learned a ton.

**Judd Antin** (00:52:38):
Can I tell you a quick story about behind the mirror? 

**Lenny** (00:52:40):
Please.

**Judd Antin** (00:52:41):
This is back from when I was at Facebook. And there was the high times there, it was like 2012, '13, and newsfeed is really taking off, ads are going into newsfeed. And I was a leader of a team that was working among other things on how to address post quality. Like, "How do we think about what's a good post and how do we get feedback about it?" And so there was a team of engineers that thought, "One thing that you can do on Facebook is hide a post." So they were like, "This is easy. Let's look at the posts that are hidden the most and use that as the signal of what's a good post on Facebook?" Seems reasonable. And something tripped me on this one. And so I did two things.

**Judd Antin** (00:53:26):
So the first thing I did is I looked at the distribution of hiding by user, and found out that it's power law distributed, like everything on the internet. There are a few people on Facebook who hide a ton, and then most people don't hide at all. And so then what we did was, we call these super hiders, we called them super hiders. And so we said, "Let's find super hiders around the office, and we'll get a super hider in, and we'll do a really traditional user interview." We just wanted to see. So literally the first person who walked in, I remember, because this was a person who had those fingernails that are so long, you don't know how they can do touchscreens, but they did. They were amazing at it. And it was one of those rooms with the glass. And I insisted that the ENG directors, the product people, and they were willing, whatever.

**Judd Antin** (00:54:20):
So everybody's behind the glass, and I'm there with them, and the excellent researcher is in the room, and they come in, and we're just doing a traditional think aloud study. And so they go, "Hey, can you open up your Facebook app? We would just love to see what your experience is like." So they open up Facebook, and were looking, and they look at the first story, and they hide it. They go to the second story and they hide it. And this went on for a while. 

**Judd Antin** (00:54:43):
And she's definitely using Facebook, but every time she'd finish with a story, she'd hide it. And the people in the back room were starting to chatter. And they're like, "Wait, what? What is happening right now?" And like the good researcher that this person was, they let it continue, and they're like, "Whoa, can you tell me what you're thinking right now?" Come to find out that she was like, "Well, I hid that story because I'd seen it already." The model she was going for was inbox zero, which was sad, because it was infinitely scrolling. She would never get there. 

**Judd Antin** (00:55:16):
And the reason I liked that story is because the people in the back room had their minds blown. It was not that we assumed that was common behavior, like this person could have been unique, but it was enough, because those people were there, experiencing the research, that N of one allowed them to burst their own bubble and realize, "Okay, we can't think so naïvely about hides as a signal anymore." And we came up with a better solution.

**Lenny** (00:55:47):
That is an awesome story and such a good example of you don't need statistical significance to get massive insights. One example just gives you a, "Wow, this might be exactly what's happening. Let's go validate that." Versus, like, "We are confident, 100%, this is what happened." I love that. It reminds me actually in the mirror study that I was talking about in Paris, there's a Facebook element to it, too. We were trying to convince hosts how to feel more comfortable accepting guests who are booking instantly. And one of our theories was if they were connected on Facebook, they would be more comfortable letting someone book instantly. 

**Judd Antin** (00:55:47):
Yeah.

**Lenny** (00:56:21):
And we're just like, "Hey, what if you were to connect Facebook and see if they're friends?" And everybody in Paris was very afraid of connecting and giving Facebook any data, way ahead of what the US hosts were feeling. 

**Judd Antin** (00:56:34):
Yeah.

**Lenny** (00:56:34):
So it just made it very clear nobody wants to actually give Facebook any data. So it was very anti-Facebook at that point.

**Judd Antin** (00:56:40):
Yeah, that's so interesting. Germany and France were always our bellwethers for what the rest of the world would be thinking with data privacy concerns.

**Lenny** (00:56:49):
Oh, man. Okay, a couple more things. A lot of this started with a lot of layoffs within user research. And I think between the lines, there's a sense of teams don't need as many researchers as they hired during the ZIRP era. I think a question in everyone's mind is just like, "How many researchers do we need? What is a good ratio?" I imagine there's not a simple answer, here, but just what's your general advice to companies of how many researchers is it right?

**Judd Antin** (00:57:15):
This is a thing I've thought a lot about, especially in my role as the head of the design studio, that was my fundamental question. It's like, "You have all these writers, designers, researchers, how do you structure them, how many, and where, and who works on what?" And the organizing principle for me was always relationships. You know you have enough when the people who need to have a concept research partner have them. And I would much rather create pain in that situation than spread someone too thinly. So my advice was always like, "Don't try to create a researcher to cover this entire product space. Pair a researcher up with somebody who's going to involve them in a consistent, engaged process, and let them go to work, and see the impact they're going to have, but protect their time. And then other people are like, "Wait a second, that person's doing great work. I want some of that."

**Judd Antin** (00:58:02):
And creating that pain for them, because it's a pain of loss, is the number one way to grow headcount. That's how I always approached getting more headcount, was not arguing abstractly for why research is important, but by asking partners who wish they had it, to do the arguing for me. And so you're right, there isn't a clean answer for like, "Hey, this is the right ratio," because it really depends on the nature of the product. Like, "Is it a early stage product? Is it a late stage product? Are we talking about a startup or a late stage company?" But I would argue there's always room for a researcher. Lenny, I'll tell you, and I used this in a keynote talk I gave lately. You published recently a list of, I think it was about 20 B2B companies and their first 10 employees. Do you remember doing that?

**Lenny** (00:58:51):
Absolutely.

**Judd Antin** (00:58:52):
Do you remember how many researchers are anywhere on that list? I'll give you a hint.

**Lenny** (00:58:57):
Not too many.

**Judd Antin** (00:58:57):
It's between zero and two. It's one. There's one researcher on that list, anywhere. Anywhere. And that's messed up to me. Now, look, it's just these 20 companies, and each is in their own space, so I'm not going to overgeneralize. But a researcher can drive incredible value no matter what stage a company is at, because a good researcher makes you go faster, not slower, and they drive impact because they answer questions which are impossible to answer in any other way. That's true if you're a startup. It's true if you're a late stage company. Now, if it's your first 10 employees, one researcher is going to go a long way. As you grow, making sure that you're matching up researchers so that they have strong partners in the key parts of the business is the best way to figure out if you have enough.

**Lenny** (00:59:45):
Interesting. So your advice is, as you're starting a company, your pitch is that you'll have a lot more leverage and move faster hiring a researcher versus generally an engineers, but you'd be trading off, essentially. That's what most of the hires end up being.

**Judd Antin** (00:59:58):
I am reluctant to overgeneralize, and I would say I know many founders who are in startup mode are like, "I know what I need to build. The problem is that I need people who can help me execute." And I think that's right. And so everything's a trade off. But remember, imagine that you could have that Swiss army knife at your disposal. Maybe you've got an MVP out the door, and you're looking to make your first major iteration, or like many startups, you need to pivot. This is where it's like, "Hey, you don't have to do that alone." We deify startup founders who pivot appropriately, but I think that is what we would might call moral luck, where we deify the ones who got it right, and even though they made exactly the same decisions as the one who got them wrong. 

**Judd Antin** (01:00:46):
And the fact of the matter is, if you have an insights person with you who has that Swiss army knife of tools, you're not in it alone. You don't have to guess. Ultimately, it will still come down to a tough decision that you and founders have to make, but you can have evidence that bears on that decision, which you wouldn't be able to get any other way.

**Lenny** (01:01:05):
To close out on this, and I have just a couple more questions on this thread, I think one of your big messages to researchers is, "You can be empowered. It's up to you to do the right sort of research and to move your career in the right direction, not become a researcher people don't need." And there's this quote that you have at the top of your post, where a lot of the reaction, or I guess the way you put it is, "I know what you're thinking, they just don't get it. We're so misunderstood. Our plight is to deliver insights that users use to drive business value while we're forgotten, never driving the roadmap, no seat at the table, consistently miscast, only to be laid off in the end." And what I'm hearing from you is like, "You can change that. You can push back on doing research that isn't actually contributing." But let me ask you, what's your lasting, I don't know, advice you would leave researchers with to be successful?

**Judd Antin** (01:01:56):
Yeah, it's tough to be operating in a broken system, and so I feel that response, where you feel kind of powerless, but I think that's not likely to lead us past this moment to the next evolution of research. So that's where it's like I don't blame any researcher at all for being in the spot they're in. It's been a tough go. However, crying about our lot is not going to get us anywhere. So I think the point of the article for me, and this is advice I give companies all the time when I do consulting with them, is like, "Hey, we can set this up in a different way, which responds to the current environment in a way which will drive a huge amount of impact." Now, that takes companies making the right choices. It also takes researchers owning up and developing skills, pushing back, understanding what research can have the most value, developing the skills, and the knowledge, and language around the business, becoming more influential, being excellent communicators.

**Judd Antin** (01:02:55):
It's one of the things I would evaluate the most in hiring, especially research leaders, because I needed them to show and teach by example, is like isn't just rigorous research. It's like if a tree fell in the forest and no one was there to hear it, you need to communicate it effectively, and you need to do it in a way that's appropriate to the audience. Because If I'm talking to you, Lenny, it's different than I'm talking to Brian Chesky at Airbnb. And so I got to be able to give that presentation effectively, and get right to the heart of it, and speak the right language. And so if you're a researcher, it's not hopeless. Actually the discipline, the future is so bright, and we can help it along by continuing to develop these different skills as companies build a model that's more inclusive.

**Lenny** (01:03:38):
Awesome. Okay. I have one just random, tangential question about NPS. You have strong opinions about NPS, and I just wanted to hear your perspective on the value of NPS, your experience with NPS. 

**Judd Antin** (01:03:50):
Yeah. I do have a strong opinion about NPS. I like to say, "NPS is the best example of the marketing industry marketing itself." And the problem is this threatens many people's livelihoods, because there's an entire industry of consultants and software providers that want you to believe NPS is a useful and accurate metric. The problem is, the consensus in the survey science community is that NPS makes all the mistakes. So it's a garbage in, garbage out problem. So the likelihood to recommend question is bad for a whole variety of reasons. So it's bad because it's a zero to 11 scale. It's bad because it's usually unlabeled. So we label the polls, but that's not the gold standard for research. It's bad because it's 11 items. 

**Judd Antin** (01:04:37):
And there's a couple of problems with that. Number one, we find that precision goes down after five items on average, maybe seven. Number two, especially on mobile, if you're taking this survey, what percentage of those options are below the fold? We are not going to get accurate survey data. And so from a survey perspective, it's really bad. There's also this intuition, which is like, "How likely are you to recommend Windows 11 to your friends and family?" I am not a person who goes around recommending operating systems. The question is fundamentally flawed. 

**Judd Antin** (01:05:11):
The argument is that that question is a good indicator of loyalty, but there's a really simple solution, Lenny. Customer satisfaction, a simple CSAT metric, is better. It has better data properties, it is more precise, it is more correlated to business outcomes. I wanted to prove this. This is something that survey scientists know and marketers don't want you to know. And so we did the work with Mike Murakami, who led survey science at Airbnb, and he's still there, great researcher. And we basically redid all that work to find out if all that stuff was true just for Airbnb. And it is. It's simple. Don't ask NPS, ask customer satisfaction

**Lenny** (01:05:50):
And the customer satisfaction question, what's the actual question for people to make sure?

**Judd Antin** (01:05:54):
Overall, how satisfied are you with your experience with Airbnb? Or it could be some version of that, which is like, "Overall, how satisfied are you with your experience with customer service when you had a problem?" So there could be a more specific version of that question, but those questions have better properties. And a lot of people say, "Well, hey, everybody's using NPS. So at least it gives me a benchmark because I can compare my NPS to industry NPS." The problem with that is the research shows that NPS is idiosyncratic, so it goes up and downs in ways that we don't understand, and there's a lot of inconsistency in how it's asked, that creates variations in the data, which means it's not apples to apples, so you can't even compare your NPS meaningfully to somebody else's.

**Lenny** (01:06:37):
I love these hot takes. I'm curious to see who comes out of the woodwork, too, when-

**Judd Antin** (01:06:41):
People are going to be so mad, Lenny.

**Lenny** (01:06:42):
I love that. I think, yeah, I've heard this many times and people don't talk about it. Okay. Is there anything else you want to share or leave people with before we get to our very exciting lightning round?

**Judd Antin** (01:06:54):
Can I? Yeah, I want to add one thing if I could, because this has come up on your podcast a few times recently, which is about the idea of people doing their own product walkthroughs. So should a PM just rely on their own dog fooding of the product and their own walkthrough to figure out how to fix it? And a couple of times recently this has come up, and I think the consensus seems to be, "Yes, this is a good thing." And I have a contrarian opinion there, too, which is that I think it is really important for everyone to dog food their own products. The problem is related to relying on your intuition about those products, which is the thing most PMs have trouble with is realizing, "You are nothing like the user. You are nothing like them in ways that will bias the way you think about what's good and bad in your product in ways that you can't necessarily recognize. Some things with a product, some problems with a product, you need a pulse to recognize."

**Judd Antin** (01:07:57):
And most good PMs that I know have a pulse and so cool. But a lot of them require context of use, priorities, constraints that you just don't have and you can't imagine purely on the basis of your own usage. So what I think that means is that you should definitely dog food your own product. Doing product walkthroughs to identify lists of potential issues is a great thing to do. Prioritizing that list, figuring out which ones are more or less a problem, and for whom is an area where you should be extremely wary of relying on your own opinion, expertise, or intuition when you are dog fooding your own product.

**Lenny** (01:08:39):
Thank you for sharing that. It's definitely come up a bunch on this podcast, so I think that's an important lesson for people to take away. Anything else before we get to our very exciting lightning round?

**Judd Antin** (01:08:49):
I appreciate you, Lenny. Thanks for having me on. 

**Lenny** (01:08:51):
I appreciate you, Judd. Well, with that, we've reached our very exciting lightning round. Are you ready?

**Judd Antin** (01:08:56):
I am ready.

**Lenny** (01:08:57):
What are two or three books that you've recommended most to other people?

**Judd Antin** (01:09:02):
I recently read a business book by Barbara Kellerman called Bad Leadership. And what I love about it is that we spend a lot of time talking about good leaders, and she really dives into the worst leaders and what makes them bad leaders in a way that I think is really valuable for everybody. 

**Judd Antin** (01:09:19):
I'd also recommend, I read a lot of fiction, so two recommendations, there. One, a recent Pulitzer Prize winner, Demon Copperhead by Barbara Kingsolver. It's an outstanding read that also is really sad, and moving, and illustrative, especially if you want to understand rural poverty. And then completely other side of the fiction spectrum, if you're interested in science fiction, which I am, read the Murderbot Diaries, it's about a sarcastic killer robot. And who doesn't love them?

**Lenny** (01:09:48):
I love these fiction recommendations. I feel like we need more of these on the podcast, so thank you. 

**Judd Antin** (01:09:52):
Yeah. Everybody goes to business books.

**Lenny** (01:09:53):
Yeah, absolutely. What is a favorite recent movie or TV show that you really enjoyed?

**Judd Antin** (01:09:59):
We recently watched The Last of Us and it blew our mind. I watched it after I played the video game after long last, if you are a person who plays video games and you haven't played The Last of Us, play it. If you don't know, the show is based on the video game, not the other way around.

**Lenny** (01:10:14):
Do you have a favorite interview question you like to ask candidates that you're interviewing?

**Judd Antin** (01:10:19):
Think of a topic that you had to explain lately that was the most complex, and then explain it to me like I'm five. And there are a lot of ways to vary that question, but the reason I like it is because I think, and I've asked this question to VP and C-suite candidates in multiple disciplines, and sometimes it's related to a conversation, like I might ask them to explain something complicated about quantum computing, or music theory, or it could be a complex business decision, but I want to see if somebody can break a complex problem down in a really simple way, and give me an intuition for it in a short amount of time. I think that is a differentiator between good and great for many people.

**Lenny** (01:11:02):
Do you have a favorite product you recently discovered that you really like?

**Judd Antin** (01:11:06):
Yeah, this is a really weird one, but my whole family started indoor rock climbing recently, and there's a challenge you have when you top rope, which is that you're looking up all the time. So they make these glasses, which are called belay glasses, and they have an angled mirror embedded in the lens, so that you can look straight ahead, and the view you see is up towards the person who you're belaying. And I just thought that product is so perfect for that. That's a niche problem and there isn't a better way to solve it.

**Lenny** (01:11:37):
Do you have a favorite motto that you often come back to, that you share with friends either in work or in life that you find useful?

**Judd Antin** (01:11:44):
Yeah. This is going to seem like pandering, Lenny, but I don't know if you remember a conversation that you and I had, it must've been eight years ago. I remember where we were sitting. And it was about stoicism. Do you remember this? Anyway, we had this conversation.

**Lenny** (01:11:59):
I don't, but I was into stoicism for a while.

**Judd Antin** (01:12:01):
I know you were, because we talked about it. And so the motto comes from stoicism, which is basically, "Focus on the things you can control and ignore the rest." And a lot of people think of this as the serenity prayer or the serenity saying, that was a 20th century invention, but Epictetus was writing about this BC, and I think about it all the time. So much of the stress, and pain, and worry that we have in life comes from things we can't control. So I try to let those things go.

**Lenny** (01:12:34):
Amazing. I learned that lesson from 7 Habits of Highly Effective People, and just the importance of thinking about these circles of you can control, you can influence, and you have no control over, and there's no reason to think about those other things.

**Judd Antin** (01:12:46):
Absolutely.

**Lenny** (01:12:47):
Judd, this was everything I hoped it would be. We got into some really good stuff. I'm excited to hear how people react. Two final questions, where can folks find you if they want to learn about what you're up to, actually share what you're up to these days, and how people can find you, and then also how can listeners be useful to you? 

**Judd Antin** (01:13:01):
Yeah. Thanks for asking those questions. People can find me at juddantin.com. That's the best way to find out what I'm up to. These days, I'm a consultant. I help people with UX strategy, org design, and crisis management. Somehow I love dealing with other people's dumpster fires, and I've found that I'm constitutionally good at it somehow. So juddantin.com is the place to find out. I also write. I write a medium post that you can find at onebigthought.com. And you'll find a lot of the topics we talked about today, including the original post that started this at onebigthought.com. If there's one thing I could ask your listeners to do is to get next to your researcher. I just think if you build those relationships and involve a researcher and insights person early and often, beautiful things will happen for you and for the business. So that's the thing everyone can do for me.

**Lenny** (01:13:56):
I love that. I've always done that. I loved my researchers that I've worked with, many of them reporting to you, and so beautiful takeaway. Judd, thank you so much for being here.

**Judd Antin** (01:14:07):
Lenny, thank you. It's been a pleasure.

**Lenny** (01:14:09):
Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [2/19] The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)

**Will Larson** (00:00:00):
I think that we often treat engineers a little bit like children instead of giving them the responsibilities and ability to actually thrive as adults. And so like, "Oh, the engineers won't want to do that work." Well, that's actually not good for the engineers to be sheltered from what is important. And so actually one of the, I think, highlights is that I think we're coming back this moment where we can actually treat engineers like our peers and put them into really senior leadership roles and not have this kind of baseline assumption of like, "Oh, we have to coddle them or hide them from the real problems." And this is how they're going to get the opportunity to grow as well.

**Lenny** (00:00:35):
Today, my guest is Will Larson, one of the most requested guests I've had on this podcast. Will is currently CTO at Carta. He's been a software engineering leader at Stripe, Uber, and Calm. He's the author of two essential books for all engineers, An Elegant Puzzle and Staff Engineer, and he's releasing his newest book The Engineering Executive's Primer in February of next year. He also publishes regularly on his blog at lethain.com, which is a must read for every engineer and eng leader.

**Will Larson** (00:03:40):
Thank you so much. Super, super excited to be here.

**Lenny** (00:03:42):
So many people have suggested that I bring you on this podcast. You have a lot of fans out there and I am excited to be digging into engineering topics, which we don't do enough of on this podcast. So thank you for making time for this.

**Will Larson** (00:03:54):
No, thanks. I hope to be a good early engineering guest before you pivot entirely to engineering at some point in the future.

**Lenny** (00:04:04):
Wow, I love that. How cool would that be? I was an engineer actually when I started my career. How interesting would that be if we come full circle? Anyway, I thought it'd be fun to start with just what is changing in engineering? It feels like there's been a lot that has changed over the past few years, especially from kind of the ZIRP zero interest rate era to today's market, which is very different. What have you seen most change from an engineer's perspective and then just also what are you telling eng leaders about how to handle all this change?

**Will Larson** (00:04:32):
I think it's a pretty strange time in the market. So I think that I started working and right before the 2008 kind of crash. And so the first two years there were not so good. When I joined Yahoo, there was a layoff basically every four months. There was a layoff of some sort. It's pretty chaotic. But then we got into the last decade and it was just smooth. So numbers went up, revenue went up, headcount went up and people started learning how to build really large teams.

**Will Larson** (00:05:02):
People started learning how to hire a lot. When I was at Uber, some days I would do six interviews back to back. I would just be in a conference room and at some point you can't even remember who you're talking to because you talk to so many people, one after another after another. You just have some scrambled notes you're trying to decode afterwards.

**Will Larson** (00:05:20):
Pretty different now. A lot of engineering managers are spending half their time or more hiring 18 months ago and now they're doing two interviews a month or less. Maybe zero interviews a month. So there's a real shift in just the amount of time people are putting into hiring. Instead, all these different competencies that have become more critical or a really great engineering director might've just been spending their time hiring really well and that could be a top performer and now that person can't actually demonstrate what they're great at.

**Will Larson** (00:05:51):
So that person might be perceived as a low performer if they're not also figuring out how to lead the team, getting deeper into the details and also sometimes getting into the figuring out what is the right allocation, what is the right sizing of the engineering teams, this is stuff that we weren't talking about much or maybe if you really pissed off the CEO, maybe an infrastructure you just grew a little bit slower next year, but different ballgame at this point where teams are actually disappearing, teams are getting cut down, teams are getting consolidated. And that's just something that we've avoided for that ZIRP era that now we become a core part of a lot of the job.

**Lenny** (00:06:27):
It feels like also engineers... They used to have a lot of leverage over companies, inside companies. I imagine that's also changing in a big way.

**Will Larson** (00:06:37):
I think that's true. I think this actually has been bad for engineers in some way. One of my hobby horses is that I think that we often treat engineers a little bit like children instead of giving them the responsibilities and ability to actually thrive as adults. And so like, "Oh, the engineers won't want to do that work."

**Will Larson** (00:06:53):
Well, that's actually not good for the engineers to be sheltered from what is important. Actually one of the, I think ,highlights is that I think we're coming back this moment where we can actually treat engineers like our peers and put them into really senior leadership roles and not have this baseline assumption of like, "Oh, we have to coddle them or hide them from the real problems." And this is how they're going to get the opportunity to grow as well. That's a highlight for me and the shift recently.

**Lenny** (00:07:18):
I have definitely worked with that and experienced that where you don't want to piss off engineers. And so are you saying that because that's changing, leaders maybe don't have to worry as much about upsetting engineers plus you just generally think we shouldn't treat engineers that way?

**Will Larson** (00:07:33):
Yeah, I think a little bit of both, but I think there's been, in this previous era, where hiring and retention were one of the biggest ways you evaluated middle management. Losing team members was huge, huge issue. And so you started to coddle a little bit, which is actually bad, again, bad for the engineers, bad for the teams, bad for everyone, bad for efficiency of the organization. But now something that I love is we get to give engineers real hard problems and we get to actually hold them accountable. And that means we can put them in senior roles.

**Will Larson** (00:08:07):
One of the things that I've been pushing on, I wrote my last book, Staff Engineer about what is the career path for senior engineers. One of the challenges is if we aren't comfortable holding engineers accountable because we just want to retain all the engineers, then we can't put them in senior roles. And so I think we're actually seeing a bit of a shift where we can actually hold them accountable, which means we can put them in senior roles, which means the engineers can actually get what they've been trying to get the entire time, but we haven't been able to because we've been coddling them a little bit too much.

**Lenny** (00:08:33):
Okay. So there's a few directions I want to go and I'm just going to poke around and see where we go. The first is you're a big advocate of systems thinking. We were chatting about this before. I think a lot of people have heard this term systems thinking and there's books about it. It's sounds great. I want to be a systems thinker. What does that actually mean? How do you find you apply it in your work? How do people get better at this way of thinking?

**Will Larson** (00:08:57):
A lot of the least successful but smartest people I've worked with were really strong systems thinking advocates. And so I do want to say every kind of framework has a lot of downsides. There's no framework that people can apply consistently, universally, and get good results. And so briefly on this one, what I see is often people will find a spot where their system and reality are in conflict and they'll be like, "Reality is wrong." And so what's a concrete example?

**Will Larson** (00:09:28):
At Stripe, we worked on incident management. And so Stripe pretty important company where our API is available. If the API is down, you lose money and if you lose a lot of money, you leave Stripe because you're pretty upset about that. The number one thing businesses need to do is to collect money successfully for the service that they're selling, right? Stripe is super important.

**Will Larson** (00:09:49):
And so we did a lot of analysis on incidents trying to understand why things weren't working, what we could do better, but we got so caught up in the analysis that we lost track of whether we're actually improving things. And it took us a while to figure that out because we were so stuck in the systems thinking model and it's not like, "Oh, the team was wrong." It's like, "I was wrong." I was caught up in that model myself, to realize like, "Hey, we weren't actually prioritizing improvements, we were just prioritizing measurement." And you can't keep measuring. There's measure twice, cut once. Sure, but you don't measure infinite times and never get to cut.

**Will Larson** (00:10:25):
And you do have to cut at some point to actually make impact. But we just got caught a little bit there. I think a lot of people who get too far in systems thinking make the same mistake where they think reality is wrong and reality is never wrong. Reality is always right. Your model is always wrong if it's in conflict with reality. But that conflict, that gap is really interesting and that's where you can learn.

**Will Larson** (00:10:49):
And so I had this model. It's really clean. It represents your hiring pipeline that moving through different steps. It represents your incidents and how you remediate incidents. It can model almost anything pretty quickly when you get good at it. And then understanding how reality is in conflict with that, you start to understand where your mental model is wrong and then you can go educate yourself and improve the model and just keep doing that.

**Will Larson** (00:11:12):
At some point the model is close enough and you can stop doing that and go actually do the work. So that the biggest thing I tell people is this is a great way to learn, but you also have to do things. You can't just learn. That's not our entire job.

**Lenny** (00:11:25):
To make it a little more concrete, how would you best describe this idea of systems thinking? What's a good way to just like, "Okay. I get what you're talking about?"

**Will Larson** (00:11:32):
This is probably a better place to start versus a rambling anecdote about using it.

**Lenny** (00:11:38):
We can go backwards. It'll be great.

**Will Larson** (00:11:41):
Systems thinking is basically you try to think about stocks and flows. So stocks are things that accumulate and flows are kind of the movement from a stock to another thing. So what's a simple example of a stock? A stock could be the number of fish in a lake. A stock could be the number of people fishing in a lake. And so a flow between those two could be the number of fish in a lake will decrease at some rate based on the number of people fishing in that lake.

**Will Larson** (00:12:08):
So if there's a ton of fishers, the stock of fish will go down faster. There's only a couple of fish, IT will go down slower. But also then there's these flows which kind of dictate that where if we've got much more efficient fishermen, the flow of fish out might go down, but also the fish do reproduce. So then there's another flow going back. So based on the current number of fish and the reproduction rate, the current number of fishers and their fishing rate, you start to see how these can evolve over time. And a lot of this.

**Will Larson** (00:12:38):
So first always recommend Thinking In Systems by Donella Meadows. Really phenomenal book. And a lot of her work is also kind of referencing the work in Silent Spring by Rachel Carson, which talks about how small amount of carcinogens or something low in the ecosystem or the food chain rather as they get consumed by predators further and further up get concentrated. And that's a kind of a classic systems thinking problem to think about where you wouldn't think a small amount of carcinogens and a small fish actually matter. But as they go up the food chain, they start to concentrate it and an unexpected change can happen.

**Lenny** (00:13:14):
So then going back to your example of the hiring pipeline, let's come back to that to help connect this definition, which I've never heard, which is awesome, very clear to how you actually implemented say in hiring.

**Will Larson** (00:13:23):
The first thing to do is to get a model out there of any sort. And so you think about your stocks. And so in a hiring pipeline you might have potential candidates and this could be basically infinite, and then you have a couple of inflows. So you could have sourced, you could have outreach, you could have referrals, and then you have the candidates and those... How many people get sourced. There's probably a function of number of sources you have dedicated to a role. So you'd have another stock of how many sources you have and then that would impact the rate going from potential candidates to actual candidates you've sourced.

**Will Larson** (00:13:59):
And then from candidates that you have in that box, you'd have a conversion rate for people who pass the first recruiter screen and that would move into step two of your process. And then from step two you have maybe a hiring manager screen and that would be another conversion rate. So you can see over time how the candidates of the infinite potential candidates like wandering around LinkedIn, posting about their deep thoughts, convert into actual people, your first, your second, your third.

**Will Larson** (00:14:26):
But then as you get deeper into it, you start to actually see interesting things. And so for a lot of candidate or a lot of pipelines, the biggest issue is hiring managers don't want to extend any offers because the hiring managers can't get to confidence on any candidate. And you'll see in this pipeline, you'll see a ton of candidates getting to offer stage, but almost none of them converting from a potential offer to actually offer. And then you can say, "Hey, here's the problem. You need to go work with the recruiter and the hiring managers on getting conviction about who they should hire.

**Will Larson** (00:14:56):
Classic problem with early managers, right? Here's a second problem. Manager wants to extend a ton of offers. They do extend them and none of them actually accept. And so that focuses you on the second problem. But there's a third potential world where actually you're just not getting enough candidates in. You're actually doing a great job of making decisions, great job of closing candidates. There's just not enough candidates coming in. And so by looking at this and you can build this model, then you can go to your applicant tracking system, a greenhouse or whatever and pull the historicals and you can just see how the historicals work versus how you'd expect it to work.

**Will Larson** (00:15:32):
You can see the drop-offs and this helps you figure out where should you go try to fix things first. I think we've all worked in companies where you roll out big changes with no data behind them because like, "Oh, it feels like we're not hard enough in how we evaluate candidates or something." You go change a bunch of stuff. But often the real problem might be that the hiring managers making offer extensions to people who never passed the loop anyway. It's just the managers are issuing too many offers because they're panicking. And man, less true now, but a decade... Or not a decade, two years ago, hiring managers panicking to get offers out, that was a real thing that happened a lot. And this just helps you take a complex kind of abstract problem and turn it into something you can actually work in a systematic way.

**Lenny** (00:16:17):
I feel like product managers will either naturally do it things this way already because a lot of them think in funnels. And it's interesting to hear this version of it of this idea of just following the stock through the flow of the different steps. Awesome. Another thing that I know that you are very passionate about and spend a lot of time thinking about is engineering strategy. I think you have this kind of feeling like engineers don't think enough about the end strategy. Every other function has a strategy and engineers often don't. Talk about what you find there and what your advice is around that.

**Will Larson** (00:16:52):
First, I start to question whether any function has a strategy at most companies. My general experience is that there's very rarely a written strategy for any company. Sometimes it's a value statement. It's like we build the highest quality products and you're like, "Good. Okay. What do I do with that?" You're like, "Build a high quality product." You're like, "Okay. I don't don't know what that means."

**Will Larson** (00:17:15):
Engineering often has this problem where I think people will make comments in their culture amp or their quarterly surveys or whatever. It's like, "Hey, the strategy is not clear or where's the engineering strategy?" And the biggest thing I tell people when they complain and then engineers complain about the product strategy. The PMs don't have any strategy or the business has no strategy. And the reality is product eng and business always have a strategy. It's just often not written down.

**Will Larson** (00:17:45):
And so the first thing I want to do is I push people not to get caught up on the fact that there's no template out there, which is product strategy that someone has forked and filled in. It doesn't mean you don't have a strategy. You do have a strategy. It's maybe a little bit hard to articulate and maybe it's applied inconsistently across different layers of the product reporting chain because it's not written down. But it's never true that there's no product strategy. There's always a product strategy. Sometimes it's bad, but there's always one. And true for engineering as well. There's always an engineering strategy. Just sometimes it's bad.

**Will Larson** (00:18:21):
The first rule of strategy is that if you write it down, then you can improve it. If it's not written down, it's hard to say if this PM is just not a good PM or if they're trying to apply the strategy that they've misunderstood or if they actually are correctly applying the strategy from the head of product that's just not appropriate to the problems they're working on, how do you debug any of that?

**Will Larson** (00:18:43):
If you have a written document, even if it's not a super compelling strategy, at least you can start debugging. It's like, "Hey, the head of product should improve the clarity of this document. Hey, this DM actually isn't applying it correctly. Hey, the strategy actually isn't appropriate for this one business unit where it makes sense for the others."

**Will Larson** (00:19:02):
So that's the first thing I think about. But the second big theme on strategy I think about is that often good strategy is so boring. It's hard to talk about. For example, on the engineering side of thing, a common strategy that's really good but very boring is we only use the tools we have today. So a lot of times you'll get engineers that want to introduce new programming languages, new databases, new cloud providers. And a really good strategy for almost all companies is like we just use the standard kit we already have today.

**Will Larson** (00:19:39):
And at Carta, when I joined one of the engineers, Eric Vogel wrote the standard kit and that is our strategy of the tools we use. And you know what? Some people are really frustrated by that and I feel for them. It feels like they're losing control, but the power of these boring strategies is that it focuses people's energy on the problems that we value as a company. And so it is painful coming into alignment if you're kind of slightly misaligned over time, but boring strategies that tell you what actually matters and aligns you with what the company actually caress about are really good for you even if they're a little bit annoying at a time. And I can expand on this idea a lot, but I won't ramble indefinitely on it.

**Lenny** (00:20:21):
Well, maybe what might be helpful is what are some other examples of engineering strategies that you've seen just to give people even more just like, "Oh yeah, maybe this should be part of our strategy."

**Will Larson** (00:20:31):
So first, what is a definition of strategy? And the best one I've ever seen is from Richard Rumelt. He wrote Good Strategy, Bad Strategy.

**Lenny** (00:20:40):
He's coming on the podcast.

**Will Larson** (00:20:42):
Amazing. He also wrote, The Crux I think came out this year sometime, which I also read. I think both great and just a phenomenal thinker who has so much depth. I think one of the challenges of writing about strategy is you're like, I've seen two things and I write the book, but I think the thing that's impressive about Richard Rumelt is he's seen so many different scenarios that he's able to really operate from both the particular but also the general and dataset in a really interesting way. Another book with similar characteristics is How Big Things Get Done by... I forget the authors, but really amazing dataset of how mega projects kind of succeed and fail.

**Will Larson** (00:21:21):
But anyway, Richard Rumelt, definition of strategy is basically three components. There's a diagnosis. What is the current status quo? What are the things that are real today? There are guiding policies which are basically based on the diagnoses, how do you want to address them? And there's actions. And actions are how are we going to implement these guiding policies. He talks a lot about actions because concerned about this idea of inert strategy where you have like, "We're going to deprecate our old product features we don't use, but no one deprecates any of them."

**Will Larson** (00:21:52):
So he's really concerned about this non implementation kind of useless strategy that doesn't do anything. On engineering, I'm a little bit less worried about that. I think strategy is more interesting on engineering in terms of clarifying how we make future decisions. And so what are a few examples of that? At Uber, we only used our own data centers. We didn't use the cloud. And this has changed since the era I was there, but in the 2014 era, no cloud, and we had a strict no cloud policy. And this was annoying because we had to indent everything ourselves or run copies of everything ourselves.

**Will Larson** (00:22:28):
But it also meant that we were able to spin up in China in literally three months and some surreal stories from that. We couldn't fit our racks into the data centers, so they had to take the roof off the data center and lift the racks in with the crane.

**Lenny** (00:22:43):
Holy shit.

**Will Larson** (00:22:43):
Just tons of stories and all this had done in three months and truly phenomenal. And Uber wasn't in China for very long, so in some ways you're like, we did all that just a leave? But they left with a nice stake of Didi Kuaidi and not a bad outcome overall. But I think that strategy, we run everything in data centers. We don't use the cloud, meant we were able to move in and out of different geopolitical constraints and companies that relied on cloud presence simply can't. There are fully constrained by where AWS or Google Cloud or Azure have built out. So that's one good example.

**Will Larson** (00:23:21):
Another good example at Stripe was this idea of we run a Ruby monolith and that's what we did and that's evolved a bit since then. There's more Java and the Stripe of 2023 than there was in the stripe of 2016 or the 2012 or whatnot. But that policy really focused the engineers on building innovative features for our users rather than building different tooling to support different programming languages. And so in both cases, both the Uber policy around running our own data centers and the Stripe policy around Ruby monoliths, a lot of engineers hated these.

**Will Larson** (00:24:02):
But the goal of good strategy is not to appease everyone. The goal of good strategy is to dictate how we invest the limited capacities we have or the limited capabilities we have into the problems we care about. And I think both of them were really effective towards that end.

**Lenny** (00:24:17):
A common theme across all these examples is essentially constraint, deciding we will constrain our options to move faster and focus on the things that really matter.

**Will Larson** (00:24:28):
In solving the constraints is to me, I think the most interesting thing that strategy really does, and I think when we talk about bad strategy usually is because the diagnosis is bad and it's usually because people are exerting what they want to be true on constraints where it's like, "Hey, we can do all of these projects at once." And often that's just not true, but it's hard to convince people that when they're the CEO or they are really committed to believing it, but almost all bad strategies basically come down from a willful disbelief of what an accurate diagnosis is, which means then your guiding policies are kind of incoherent to begin with.

**Lenny** (00:25:08):
Awesome. I'm excited for that episode of Richard where we're going to go real deep into strategy, but maybe just as a lasting topic around there, if someone listening wanted to get better at say end strategy specifically or a strategy in general, is there anything you recommend they do? Is it read these books? Is there anything else?

**Will Larson** (00:25:26):
If people want to get good at strategy, there's a lot of different types of strategy, but here are some things I'd really recommend. First, I think the Richard Rumelt book, I think Good Strategy, Bad Strategy is probably the right starting point. I think The Crux also quite good, but maybe I would read that one second. Great overview of how to think about strategy. Also Thinking in Systems, I mentioned that before related to systems thinking, a big part of strategy is being able to model the reality so we can improve your diagnosis.

**Will Larson** (00:25:56):
So I think that one is really quite good as well. If you get into the engineering side of things, there's a lot of interesting books here. There's Technology Strategy Patterns by Evan Hewitt. There's The Value Flywheel effect by Anderson, McCann and O'Reilly. The Phoenix Project by Kim, Behr, Spafford, which is a modern rewrite of The Goal by Goldratt. But I think there's still the missing canonical book is kind of missing on this one. So I took a stab at strategy and my upcoming book, which is coming out the Engineering Executives Primer coming out early next year.

**Will Larson** (00:26:33):
Also, took a stab at it. In staff engineer my previous book, but I still think there's a missing book here. So I am dreaming of writing an engineering strategy book for my next project, although we'll see if that actually comes together.

**Lenny** (00:26:48):
Well, let's actually follow that thread of writing something I was definitely hoping to chat about. You write a lot. You've written two, three, four-ish. You're writing a new book. How many books you've published? Two books and there's a third one coming up.

**Will Larson** (00:27:00):
So I have two books. First one with Stripe Press, the second one, self-published and the third one with the Riley coming out in two months effectively.

**Lenny** (00:27:08):
Okay. And then also many, many blog posts for many, many years. I asked a few people what to ask you, and this came up a lot, Gergely Orosz and Alex Xu from ‎ByteByteGo both asked just this question of just, "How do you make time to write as much as you do?" And then I also, I'll ask this too and just answer it either first or second, just what impact has writing had on your career? Why do you keep doing it?

**Will Larson** (00:27:37):
I feel really strongly that you can write a lot more if you write what you want to write. And so this is one of the reasons I don't write for financial gain and I don't write very much on a schedule, so I've done a few pieces for magazines, et cetera, but I find that actually really draining to be you have a topic, you have to agree on the topic. If a topic starts missing what you want to write about, you can't fix it a lot of the time and you're also on this deadline. You're like, "Ah, I'm screwing up. I need to ship this. It needs to be done tomorrow."

**Will Larson** (00:28:12):
I just find that really draining. Conversely, when I own the schedule, when I get to write about, "Hey, I'm writing out something." So I started writing this infrastructure engineering book a couple of years ago. It just wasn't there. I just couldn't get it to come together and so I just stopped. I'm not writing it anymore. Maybe I'll come back to it at some point, but probably not.

**Will Larson** (00:28:34):
To me, the biggest strength of writing what you want is you get to write where there's energy and you don't have to write where there's no energy, which takes you really, really negative. And this also ties into how I write books, which is that I basically write the entire thing before I start working with a publisher. And if you are, I think diligent and good at anticipating what their concerns are going to be, you can mostly reuse the content that you're trying to write. This is also easier in the sorts of books I write.

**Will Larson** (00:29:05):
I think harder to do in a really technical introduction to MySQL or something, you can't just resequence those chapters and pretend it's going to work. Those chapters build in a different way than the sort of business book that I write does. Writing the stuff that's energizing and just giving up on the stuff that's not energizing, that's how I write a lot and how I've been writing for 16 some years. And the way I keep doing it is just by writing what's energizing and what I'm thinking about now.

**Will Larson** (00:29:38):
I don't write what I'm not thinking about and I don't write for any audience, I just write what is interesting to me. And that means some people don't like it and that's great. That's totally fine. It's not really for them, it's for people who want to follow the ride and that's where I focus.

**Lenny** (00:29:57):
**Will Larson** (00:31:00):
I would guess about a thousand. That would roughly be my assumption. I think there are a few years where I wrote hundreds of posts, and so if you do that like three years, it's not that hard to get to a thousand from there.

**Lenny** (00:31:16):
That's incredible, especially because you've had intense jobs for all of those years or most of those years. Very high pressure, fast growing hypergrowth companies. Somehow you find time to work. So first, let me just double click slash co-sign your advice here around paying attention to what gives you energy and working on things that you're actually curious about. This is exactly the advice I give to people. A lot of people start this full-time writer, creator life, and they're like, "What do people want? What do people want me to write about? What's popular? What's going to inspire go viral?"

**Lenny** (00:31:48):
And that's easy to do a couple times, but then you end up creating this job for yourself that you don't want. You don't want to be spending all your days writing about AI if you're not that excited by AI or whatever's hot these days. What I find is important is almost like 80, 90% of what you write has to be stuff you're excited about. And then maybe there's a bit of, "Here's what I know people really want. Here's what I know is going to do really well." Because otherwise you just burn out. You create a job for yourself that you don't want. Why would you do that?

**Will Larson** (00:32:13):
Yeah. I just a hundred percent agree with that. I think the other thing is that everyone converges on the same thing that they think people want. So it's crypto two years ago. It's like AI right now or it's counter AI. AI is going to ruin the world. It's hard to say something very novel because, one, everyone is trying to say something about it. Two, it's almost certainly not what you're that knowledgeable about where if you just stick in your lane, I think the biggest risk to writers is quitting.

**Will Larson** (00:32:43):
A little bit like the 40-year career idea. The biggest risk to content creation of any sort is quitting soon because you get burned out. The biggest risk is not that you grow too slow initially. There's always this sense that you've missed the wave. It's too late to join Substack. The top writers are already there. You'll never be a top writer. It's too late to podcast. There's too many podcasts. You'll never make it. It's too late to join Medium. You'll never make it. There's too many Medium writers.

**Will Larson** (00:33:11):
But it is just not true. If you just keep writing good stuff, you'll build an audience over time and you can take that audience from platform to platform. What really matters is finding something you can actually keep doing for the next decade. That's way harder than doing it for one year.

**Lenny** (00:33:25):
We have the same exact advice on this. This is exactly the things I tell everyone. When I joined Substack, I thought it was too late. I was like, "Man, it's over." And when I started this podcast like, "Oh man, there's a billion podcasts. How is it ever going to work?" So I so agree, and I also so agree on the fact that this whole thing is such a... It's a long game. There's a lot of people. I always say it's easy to start a newsletter, hard to keep it up. Nobody actually keeps it up because people are going to come and go. The thing that really separates success from failure is just people that can keep at it. There's not an end game to this. It's an infinite game and it's about being able to sustain that over the long term.

**Will Larson** (00:34:04):
You're not competing with other content creators. If you think of it as an infinite game, you're all working together. You can all help each other grow. There's no maximum number of product writers or thinkers who can be doing something. You're not less successful because [inaudible 00:34:22] exists or something like that. There's no competition there. It's like a false, false dichotomy.

**Lenny** (00:34:27):
Yeah. I totally agree with that. Unless there's so many and then all of a sudden what happens is the bar just gets higher, which is good because then people get better stuff and that's fine. That's happening anyway. Just the bar continues to increase because there's more and more content out there. And to me that's the ultimate thing you got to get right is just the bar. You just got to be at a high bar for anyone to care about anything you're writing about. And to your point, to do that well, you have to actually be excited about writing about it and have background and have something to contribute.

**Lenny** (00:34:59):
I'm just ranting here, but the way I think about this is you need to add something new to the conversation for anyone to pay attention because there's so much fluffy, superficial stuff. And to get anyone to care is you need to say something new that no one's heard before or share new information they haven't seen anywhere else.

**Will Larson** (00:35:15):
I totally agree. I could keep ranting about this for the entire time. I don't want to derail on this, but I totally agree.

**Lenny** (00:35:23):
We'll control ourselves. So then getting very tactical, I think this is what a lot of people are always wondering, how do you make time? What's your workflow? How do you make time for writing so that you keep at it with knowing you have an intense full-time job?

**Will Larson** (00:35:34):
I used to do things differently before I had a kid, so I have a three and a half year old and just timing your life just really shifts a lot once you have kids. But the biggest thing that I found is finding things to write about that also directly relate to what I'm working on. And this is where I can do something that helps me at work and helps me write at the same time because I think it's incredibly hard to find time to write about stuff that has nothing to do with your work.

**Will Larson** (00:36:05):
And this distracts you from your work because these... Particularly if you're in a senior role, these can be pretty demanding jobs, but they're not demanding because you're responding to an urgent DM on Slack every five or six minutes. They're demanding because you need to make some really difficult decisions really well. And I think writing about related topics is a great way to refine your thinking and improve your performance. It's not like a conflict or you do one.

**Will Larson** (00:36:34):
You either write or you do your job well. I think you can find a way to align. And so a lot of podcast folks do interviews with folks who are related to what they're thinking about at work, and that's a great way for them to learn, build their network, to refine their thinking, to test their thinking against experts in the field. It's not like in conflict with the work, it's in alignment. So that's one piece. But yeah, I've played around with my schedule a lot.

Before I had a kid, often Saturdays would be the writing day and so morning and early afternoon would just be writing. I can't do that anymore, so now I mostly write at night, which is tricky from an energy management perspective. But the biggest thing I would say is just if you're actually excited about something, you will find time and energy for it. If you're not excited about it and it's 9:00 PM, you're just going to get asleep. And so I really think that this is where you have to schedule a little bit deliberately, but the first thing we talked about around energy management, they really come together. When your schedule gets tight, if you're not energized, you just won't get it done. And why would you? It just doesn't make sense.

**Lenny** (00:37:41):
Just to close out this thread for someone that wants to do more writing knows that it's going to be valuable, but just hasn't any one tip that you would leave them with to get on this train?

**Will Larson** (00:37:51):
It depends why people want to write. I tell people, if you just want to write something that is going to help advance your career, you should really focus on writing two or three really good things and spend a ton of time drafting, revising, getting feedback. You just focus on making one great artifact or two or three great artifacts. You don't need to create a long-running blog where you publish every week. There's really no need to do that if your goal is just to create some artifacts that show you're a deep thinker, that help position you in the industry.

**Will Larson** (00:38:21):
Don't start a newsletter if you just want to advance yourself in the industry a little bit. Just write two or three really good things. So that's the first thing I'd say. But if your goal is to write a lot consistently over time, my biggest advice would be just publish. And so there's a lot of people out there with stuff that hundreds of drafts and they've not published anything. And my thing is I publish almost everything I write. If there's something that I'm not going to publish, I don't start writing it because I have a quick check in my head like is this something I can write and publish?

**Will Larson** (00:38:56):
And if my answer was like, "No, I just don't even start." And my accuracy has gotten higher over time as I've written more, but I published pretty much everything I write. That's why some of it is not that good. And that's okay. Again, I want to write. I want to get these ideas out. I want to show what I'm focused on and my evolution as a thinker trying to learn how to operate in these different roles in these different companies. I'm not writing trying to create a polished perfect thing, and also I'm not writing to maximize a reader's experience of reading it.

**Will Larson** (00:39:27):
Some people don't like that, and I think that's a totally reasonable thing not to, but I think what I can bring you is my experience as an operator who's actively learning and thinking through. I think that's really valuable to other operators in the industry. In terms of giving you the perfect writing, I try to do that, closer to that. I don't know if I ever hit perfect writing, but that's where my books are. The books are taking a collection of thoughts over a couple of years, cleaning them up a little bit, packaging them. They're way higher quality than my typical writing.

**Will Larson** (00:39:56):
But yeah, I would just publish a lot. Don't worry about the quality. Sometimes people will send you silly feedback and I just don't respond to that stuff anymore. You never know why people send you something like that. I think trying to debug people you don't know is a bad use of time. It's just kind of like, "Thank you. Move on to the next. Don't even spend time worrying about it."

**Lenny** (00:40:19):
I like that term debug people. I think people way overestimate how much anyone cares about what you put out. Most people are going to look at it for three seconds and be like, "Eh." That's the worst case scenario basically is just like, "I don't care about this." Not like, "Oh, Will is such a fool." What a dumb thing to say. Right? No one has time for that.

**Will Larson** (00:40:38):
And if they do, that's a them problem, right? The internet is a big place with a lot of people and there are people who are going to be having a really bad day when they encounter something you do and they're going to channel that anger at you or that frustration at you, but that's not about you. That's just like you happen to be there when they engage with it. You don't have to take that on. That's not your situation. It's okay.

**Lenny** (00:41:03):
Also, when you're just starting out, that's going to be the least stressful time to write because nobody knows it or sees it, so that's when it's like "Take all the crazy... Just do stuff." It only gets more stressful as you build an audience over time.

**Will Larson** (00:41:15):
Yeah, absolutely. Absolutely true.

**Lenny** (00:41:18):
Okay. Shifting topics. There's a lot of product managers that listen to this. Something PMs often wonder is how to have better relationships with their engineers, their eng managers. What advice could you give to product managers to build more productive happy relationships with their engineers and eng managers?

**Will Larson** (00:41:37):
So the core problem, and most of the EM PM peers that I've worked on... There's two core problems. So one, sometimes the incentives are misaligned and that's hard to navigate, but if you can just be honest with each other and understand the incentives, sometimes you can find a compromise, but sometimes the EMs and PMs will be misaligned because just their incentives are so far apart that there's no way to get to the bottom of it. And so this might be timeline related or saying yes to sales related. Or the engineer is like, "Hey, we definitely can't say yes to that." And the PMs are like, "Actually, we're going to say yes to it because really important for me getting promoted," or something like that.

**Will Larson** (00:42:19):
Is it ever this simple? It's really never that simple. People create simplistic narratives to find villains that they work with. There are no villains in the workplace. They're just people with complex incentives that are doing complex things. But sometimes I talk to EMs who think, "Oh, the product manager is just saying yes because they want to get promoted because the salesperson will review their promotion or something."

**Will Larson** (00:42:40):
The reality is never as simple. The reality is the business needs to sell stuff to remain functioning. You can't just say no and have the business succeed. That doesn't work either. So one, understanding the incentives. The other piece though, and I think this is the more common case or just that the EM or the PM just don't understand the other person's needs and they start arguing before understanding. So my biggest advice to both the EMs and the PMs, is before you try to solve the conflict, it's like pushing to ship this feature, pushing to change the approach. Just make sure you actually understand what they care about.

**Will Larson** (00:43:17):
There is this idea that you have to make trade-offs and that there are tons of hard trade-offs to be made in the field, but my experience is if you really deeply understand what everyone wants, there's usually a compromised solution that gives everyone exactly what they want. That doesn't take more time. You just have to be willing to dig deeper into it and understand the true needs for each party, which is often not what they're saying by the way, which is part of the confusion.

**Lenny** (00:43:45):
On the incentives piece, is there anything you've seen work to fix that problem? Because if PM performance reviews are based on impact engineering, performance reviews are based on interesting projects or uptime, do you just work to change those ladder definitions? What actually can help that situation?

**Will Larson** (00:44:05):
So my biggest thing has been trying to force this idea that EM/PM pairs are peers and they generally have the same performance rating. And there's exceptions here. It could be the EM is clearly not performing and then it's not the PM's fault if the EM is can't show up to work. The team doesn't respect them. Sometimes there's clear non-performance, but generally hard situations are not situations where one person is obviously terrible. Those are easy to diagnose, those are the easy ones. But in cases where there's two folks who seem to be pretty good, but just the overall execution is not working out, I think this idea that same perf rating for both drives a level of one pain, but the right perspective.

**Will Larson** (00:44:56):
Also, something that I think Carta has experimented a little bit with over time. Henry, our CEO has a blog post about trifectas in doing that, but not just for EM and for PM, but also for that business leadership as well where you all get graded the same score based on your ability to evaluate and solve for the entire set of constraints, not just your functional constraints.

**Lenny** (00:45:20):
Wow. That's so interesting. So your recommendation, something you're doing, it sounds like is the engineer manager and the PM get the same performance review rating? And so they're discussed in the same meeting.

**Will Larson** (00:45:33):
Our chief product officer, Vrushali and I spend a fair amount of time calibrating together and making sure... Again, there's cases where there's an exception because there's clear issues happening for someone. But on average that is what's happening. And I think people know that's what's happening because we told them that. And I think that's pretty powerful.

**Lenny** (00:45:55):
That is so interesting. I've never heard of that approach. That is definitely solving that problem of EM/PM or...

**Will Larson** (00:46:01):
Yeah, the incentives are shared now, which isn't perfect. It's still hard to balance them. They can still make the wrong trade-offs, but at least they understand the incentives are shared, which I think is a pretty powerful idea.

**Lenny** (00:46:15):
That is really interesting. I imagine some companies might even want to include design managers in that, take another step.

**Will Larson** (00:46:23):
The role and the primacy of different functions in different companies varies so much that it's hard to have a one size. You could also imagine where you want a staff engineer in that or not. And so I think very company specific. But yeah, I think design could absolutely be involved particularly for a design led company like an Airbnb or something like that.

**Lenny** (00:46:43):
Wow. So interesting. Maybe just as a final thought there, if a PM is having challenges with their EM, what do you think PMs maybe don't realize their engineering managers are finding important or maybe are stressed about that they're just like, "Oh wow, I never thought about that."

**Will Larson** (00:47:00):
I think one of the biggest challenges I've historically seen, particularly in the last decade is this idea that engineering managers have the job of giving their team interesting work. I think that that can put... You often see this in growth teams where the growth team is like, "Hey, we just need to do a ton of experiments." An engineer is like, "I want to build something brand new." And the eng managers in between those try to figure out, "Need to ship 50 experiments that are pretty boring and they want to do something brand new. I don't know how to do solve this."

**Will Larson** (00:47:30):
So it's a tricky moment. And good EMs find the way to balance, but that's the biggest source of ongoing friction where the EMs have been told by their teams they need to do something that the PMs just have no visibility into. And it makes the EM seem totally unreliable partners because they're trying to solve these little bit of these invisible constraints. And that's where I think pushing further to understand, "Hey, you keep prioritizing this rewrite into a new programming language."

**Will Larson** (00:48:00):
To me that seems like completely idiotic thing to be doing. What's going on? And then once you understand, you might not agree with them, but at least you can have an honest conversation about how to navigate those constraints versus just like, "Man, you won't believe what my EM partner did today. This bozo did blah, blah, blah." And having this victim villain mindset about your peers.

**Lenny** (00:48:24):
An adjacent topic that I wanted to spend some time on is measuring engineering velocity productivity. I think it's probably one of the most common and also maybe the most annoying questions eng leaders get is just how do I know if my engineers are moving as quickly as they can? How do we help them move faster? What advice do you give to eng leaders for eng teams just for how to measure productivity well?

**Will Larson** (00:48:44):
This is a question that's coming up even more in a moment when we're reducing a lot of the size of teams from the industry when the venture capitalists that are on the board for these venture-backed companies are pushing on the efficiency of engineering. Engineers are trying to figure out how do we represent this? How do we prove that we're appropriately productive for the amount of headcount and funding that we have as an organization?

**Will Larson** (00:49:09):
And man, that's hard. So the first way that people focus on trying to answer these questions is just benchmarking by the amount of funding that you have. And that's pretty straightforward to do is a mechanical exercise. You get a data set from your venture capital funds or whatnot, and you figure out, "Okay. How much should we be spending in R&D? How much should we be spending in engineering? How much should we be sending on infrastructure engineering in R&D?" And you can benchmark this all out and figure out what the correct numbers are there.

**Will Larson** (00:49:40):
The problem is this is a very mechanical and not very insightful, driven way. It'll get you a defensible answer. It's like the old, no one gets fired for buying IBM, which definitely hasn't been true in my career ever. But this idea that if you just have the right benchmarks, DCs won't judge you for spending too much in engineering, but this doesn't actually help you get to the right place. It just helps you get your board to be less angry at you, which is useful because it's hard to do good work when your board is angry at you.

**Will Larson** (00:50:13):
But it's not useful in the sense that it doesn't actually help you run your organization effectively. So then there's the much harder mediator problem of how do you actually know if your R&D team or engineering team is effective? What I find is a couple of things. First, if you're a good leader and you talk to engineers, they will tell you... The engineers know if their teams are effective or not. And if they're not, they'll also tell you why not. And their diagnosis can be wrong, but there's a crumb you can start picking up and you can trace the crumbs to figure out what's wrong.

**Will Larson** (00:50:49):
Often you'll have more experience to analyze the complaints to figure out what kind of the contributing causes are to them. But yeah, if you just go talk to the team on an ongoing basis, you'll know if they're effective or not and you can go work to solve those specific problems. But again, you can't tell your board, "Oh, it's fine. I talked to the teams that they're good." My intuition's spot on because how do they know if your intuition is good or not?

**Will Larson** (00:51:17):
They're dealing with a huge portfolio and some of their leaders are talking to are good, and some of them have terrible intuition. How do they actually assess? I think it's tricky. What I've tried to do is basically two things. One, aligning engineering evaluation to the business and product goals. So I want us to be wholly accountable with the product goals. Well, we did a good job products like screwing up over there. Obviously, a lot of companies find comfort in doing that, but really we're here to support the product, to support our customers in doing something interesting. We're not here to build novel systems unless it supports the customer and the product.

**Will Larson** (00:51:59):
So first try to align heavily there. Second, I think just showing the roadmap of the valuable things we've done in the last six months is really powerful. I think sometimes people are like, "I don't have anything to put there." And you're like, "Yeah, that's a real issue." Or if you have the ton of stuff to put there, that's great. I really find that if you just commit, show the number of meaningful, meaty things that have impact that you're doing and you can explain the impact, people will step back and give you space. If you can't populate that list, people will have concerns and rightly so, they should be concerned about that.

**Lenny** (00:52:36):
Is there any metrics or tools or anything like that that you find useful too? Because these are all awesome piece of advice, but I imagine everyone is always just like, "Give us this number we're tracking, give us this dashboard, see what engineers doing."

**Will Larson** (00:52:49):
So one of the most influential books in the last decade in software engineering leadership and infrastructure is Accelerate by Nicole Forsgren, Gene Kim, and I believe there's a third author on that one, but I'm forgetting right now. Really phenomenal book and it comes up with these four metrics. It comes up with lead time. It comes up with incident remediation time. It comes up with failure rate. And the fourth one of some sort. There's at least 50 different startups out there that are selling you dashboards that instrument these pieces of data and they want you to just evaluate your team on them.

**Will Larson** (00:53:30):
The challenge is these are really good diagnosis metrics. And so hey, our deployments are slow. Why is that? How do we speed them up? But your deployments being slow doesn't make you a good company or a bad company, it just tells you where you should focus on improving. It doesn't actually change how you are. And similarly, if your lead time is quick or slow, it tells you where you should invest or it doesn't actually tell you if you should fire your engineers or something like that. That's way, way more details specific.

**Will Larson** (00:54:00):
So people do like to see these metrics just like they see uptime metrics. A lot of engineers report on sprint points or stuff like that to their board, which are just totally, totally fake thing to be reporting on. But people get some comfort on it. So my biggest thing here is when people measure things, this isn't an engineering only problem, but when people measure, they take on the perspective of an expert and they can tell you why not to measure everything. They can tell you why every measure is wrong or inaccurate and they rule everything out and so they measure nothing and they go to someone who's not an expert and well actually there's no accurate measure to give.

**Will Larson** (00:54:37):
They're not an expert is like you don't know what you're doing. And so you just have to get comfortable measuring something that's not perfect, but you can actually measure and reporting on it and then the measure that's imperfect as people ask questions, that's an opportunity to educate people on why the measure is imperfect. What are some things that misses or kind of the lies from the conversation.

**Will Larson** (00:54:59):
Metrics are about educating the people consuming the metrics about the reality of the rich data underneath. They're not about this perfect data set that shows everything starting with something mediocre and the Dora metrics are really helpful for diagnosis, but if you have to, they can also be a good enough starting place to start reporting to your board or your CEO or to the other executives and then you're like, "Oh, there's all these problems with them."

**Will Larson** (00:55:22):
Yes. There are all those problems with them, but that's this place you start and you educate people up from there to help them understand the nuances and that's how they become more sophisticated, understanding engineering, not by refusing to give them anything they can possibly measure.

**Lenny** (00:55:36):
Awesome. I'm glad that was your answer because we had Nicole on the podcast and she talked through Dora and all the frameworks that she recommends. And she even actually shared some benchmarks that she points people to that give you some sense of just like, "Are you in a good place roughly or not?" So we'll point people to that episode to dig deeper. Awesome. I'm glad that you're a fan.

**Lenny** (00:55:55):
Okay. Just a couple more questions before we get to our very exciting lightning round. One is around values, company values, org values. Do you have some really good advice for people for how to think about coming up with values? What do you share? What do you recommend to people that are trying to figure out what values they should define for their org and their company?

**Will Larson** (00:56:14):
I mean, values are really interesting, right? And different companies talk about values in different ways. I once worked at a company where the execs went to visit the Facebook campus. They saw the values written up on the wall and they took the Facebook values and wrote them up in our walls and that didn't do a whole lot. It maybe undermined people's confidence in the critical thinking of the executive team that just took these written up on Facebook walls and replicated it.

**Will Larson** (00:56:39):
But I think those values did work well for Facebook and those values were meaningful for Facebook. And so first you can't do is just steal values. Value cargo culting. Users first. Great Amazon value. A lot of companies aren't users first and that's okay, but what's not okay is when you put, "Hey, we're users first," and then you actually show the decisions you're making and you clearly aren't users first.

**Will Larson** (00:57:06):
So one of the things I think about is just honesty. And so good values have to be honest and so any value can be honest or there's no universally honest values. You can say something like, "We're thrifty." Or we can say something like we spend as much as we need to get the best value. Those are totally different and good companies are run both ways. So the first rule I think about a lot is honesty. You actually do what you claim you do and the value. The second one is applicability. You have to have value that you can actually figure out how to apply to your work.

**Will Larson** (00:57:39):
And so one of Stripe's values was no longer a value I believe, but it's optimized globally. And so optimized globally is a really interesting problem because sometimes you'll have something you wanted for interesting value. Sometimes you want to do something and you're like, "Hey, I want to introduce a new programming language that's better for my team." For the organization overall, this is actually much worse for the organization so I'm not going to do it.

**Will Larson** (00:58:03):
Uber didn't have this as a written value, but implicitly Uber's value was do what's good for your team and ignore everyone else because that will slow us down. So the two different companies had opposite values, but they're both very applicable. It's like how should we navigate decisions? Should I optimize for my team or for the organization? So those are applicable to real problems and they were honest where Uber was just like, "Don't worry about other people." Make it work for your team. And that's how they moved so fast because they just didn't worry.

**Lenny** (00:58:32):
Wasn't their value of toe-stepping, encouraging toe-stepping, something like that?

**Will Larson** (00:58:36):
Let builders build toe stepping. There were a number of values that could be interpreted in different ways and sometimes they got weaponized in various ways as all values do. But these are both interesting in different ways. And so number one is honest and two is applicable. Three is I think the last thing for a good value is this idea of reversibility. So there's some values that aren't actually usable. And so here's a good example. We build good software. Okay. But why would you ever not build good software? That doesn't make sense or we solve customer problems that matter. Good.

**Will Larson** (00:59:22):
What company doesn't think they're solving customer problems that matter? And so there's certain values that just you can't apply. And so I think of these as identity values. These are really just you describing who you want to be or we care about our customers. Great. But who would say they don't care about that? There's certain values that I think of as just identity values and they're not wrong to have identity values, they just aren't very useful.

**Will Larson** (00:59:51):
You can't actually use them for anything. And so I just always push people not to spend too much time on these because they feel good when you're an executive team debating what are these identity values? It's like we're kind to other people or sure that sounds good. We're a family. Sure, that sounds good. That one I guess is a little bit reversible. There's Netflix, which is like, "We're a team like a sports team. We're not a family." And so a little bit reversible, but not perfectly.

**Will Larson** (01:00:20):
But yeah, these are the three that I found really useful for any value. Is it honest? Is it applicable? And can you reverse it? And if not, it's probably actually not helping the team make decisions.

**Lenny** (01:00:30):
These are great. It reminds me a lot of... I was there during Airbnb's period of coming up with values. Something that I would maybe add and maybe fits into one of these buckets is it needs to be clear who doesn't? There needs to be a group that doesn't quite fit because if everyone fits, you're not doing anything useful. What's the point? Which feels weird to say, why would not everyone fit in our big group of awesome company? But it's clear who is not a good fit, who doesn't belong basically. It's kind of like a cult a little bit like, "Who's not in our cult? Who doesn't belong?"

**Will Larson** (01:00:59):
But I agree. If it doesn't apply to anyone, then why bother saying it? It doesn't mean anything. And you could say it's actually the hiring filter where there are people who you've explicitly chosen not to hire because this wouldn't apply to them. Then I think it's useful because it helps you actually figure out who to bring in. But if it doesn't apply to anyone you're hiring or anyone that you have in the company, then it's just isn't worth having because you already have too many values. You are already trying to get rid of values because you have 17 and you need to get down to four where people can remember them. So if it doesn't apply to anyone, why bother having it at all?

**Lenny** (01:01:32):
Yeah. Integrity is a common one. Integrity. Everyone has that. Nobody wouldn't want integrity. What is unique?

**Will Larson** (01:01:38):
We're a non-integrity company. We're the company that thinks integrity is bad. That's not a real thing.

**Lenny** (01:01:45):
The other one I'll add to is honest. So Airbnb, we had six values initially. One of them was simplify and a year or two later everyone just realized we're not actually good at this. We want to simplify, but we're not great at this skill and values should describe who you are not who you want to be and aspire to be. So they cut two values including that one, and they're just like, "Let's just do these four because this is actually who we are. Let's be honest with ourselves."

**Lenny** (01:02:11):
Okay, final question. I wanted to visit Failure Corner, something that I've added recently to this podcast where people share a story of failure. And you have this amazing post about your experience with Digg and the rewrite that you all went through. I think it was the version four of Digg. Can you just tell that story and what happened? How much of a mess it ended up being?

**Will Larson** (01:02:33):
Yeah, Dig V4 is... I mean, it's still something I have a lot of fond memories for. There's one picture that I've kept and there's a picture of a lot of the engineers around this table in the middle of this giant office and they're serving sushi. We had waiters, caterers come in that day. They're serving sushi. They have plates with champagne flutes on it. There was a full bar and we're all around this table because the site is not up.

**Will Larson** (01:03:03):
And so Digg before essentially what Kevin Rose or the board or some combination there realized is that Digg was losing to the social networks and that this idea of aggregated news was going to be outcompeted by the Twitters, the Facebooks, et cetera, if we didn't find a way to move to have a social component for it. It even outcompeted by Reddit longterm was kind of the fear. Although at the time that that was far from obvious. And so we needed to move to support social functionality and the previous version we simply couldn't get it to work.

**Will Larson** (01:03:39):
So the decision that was done, I think two and a half years before I joined, and the shift about six months after I joined was they needed to do a complete rewrite in order to get there. This is a decision that never works out for anyone. So I think as someone with more experience, I could have predicted this wasn't going to work out. But I was earlier in my career. My PM counterpart at Yahoo, Das Kofinovsky. He went to Yahoo and he's like, "Come to Digg."

**Will Larson** (01:04:10):
Worst case you'll make a couple hundred thousand in a year. Worst case. Probably really great outcome. Anyway, that's not what happened. The worst case was a little bit optimistic. So we go and the CEO got fired two days before I joined. So the current CEO left and then Kevin Rose came back for about six months, something like that. And we're just on the death march trying to get this thing out.

**Will Larson** (01:04:37):
So we pushed really hard. This was before the cloud for the most part. So we wiped pretty much all of our existing servers to re-image them to the new software. We try to bring the site up and just keeps crashing. And so it basically takes us a month to get it fully functional again. And so that day sitting around that table with champagne and sushi, that's just like day one. And by 30 days in, most people aren't even trying to get the site back up anymore.

**Will Larson** (01:05:08):
There's maybe five of us who are still trying. And we did. I think that was a really powerful moment for me. I think in the first two days myself and Rich Schumacher, one of the other engineers, we had to write a caching system from scratch, which got us half the way up. Really a terrible way to do software on a side note. I'm not recommending this to anyone. This was a series of anti-patterns kludged into a launch. But we got it partially up, but we had to restart it every 12 months.

**Will Larson** (01:05:41):
Every 12 hours, every server had to be restarted even with the caching mechanism. And then about three weeks after that, I finally figured out what the core bug was, that was bringing us down every 12 hours. It was this incredibly simple issue that had just been hard to debug, basically related to the way that Python initiates variables used as default parameters. It's something super silly and we just had someone who hadn't written Python before who was working on the API code, so they didn't realize it's gotcha.

**Will Larson** (01:06:15):
Then no one else caught it when it was reviewed and it just took a long time to debug. It was such a non-obvious. It didn't break anything, it was just doing a lot of extra load on the servers. We finally figured it out and it was just really remarkable experience pulling through. And you know what? The company still went to zero. So we had this at launch. I think we did this heroic, heroic stretch to get it working.

**Will Larson** (01:06:43):
A couple weeks after that, a new CEO came in, did a round of layoffs. This is back I think 2012. The team nine months after I started was down to 30 people from about a hundred and it went downhill from there, from a business perspective. But we launched a lot of functionality, has really learned just a tremendous amount. And it kind of shaped what I think about in terms of early in your career, getting learning and going into a company that is maybe having a rough time.

**Will Larson** (01:07:15):
I became a manager two and a half years into my career. Basically running the entire engineering team there because everyone who had a lick of sense quit or got laid off, and it was just complete idiot me trying to be the manager for the engineering org, wasn't qualified and no one would've given me that job, but I was the only one dumb enough to take it at that point. I learned so much and I really the kernel that turned into my entire career where it was that opportunity, even though at the time it was pretty grim.

**Lenny** (01:07:49):
That's an amazing story. I feel like a lot of these experiences were in the moment, it's just like, "What is going on? This is so bad and hard," end up being the most interesting and looking back end up being the most biggest teaching experiences. The ones you like bond over with people you work with like Apple. It always comes to mind where it's just like Steve Jobs's joke, people like crazy and then they look back and that was the best moment in my career.

**Will Larson** (01:08:12):
You would never voluntarily take on a lot of these really challenging things, but sometimes when they show up, you're with a group of people you really respect, you love working with and you want to overcome together. And that's really powerful experience. Even if Uber China was similar where if someone had been like, "Hey, do you want to go work on this Uber China migration?" I would've been like, "Absolutely not." But no one asked. They're just like, "Get this done," and so we did. I think these things are pretty remarkable.

**Lenny** (01:08:39):
And just to be clear, so Digg was down for a month basically during this period? Is that...

**Will Larson** (01:08:43):
So it basically didn't work properly for much of the month. It was like read only was back up in about three days, but the vast majority of the actual user functionality just wasn't working properly for pretty much an entire month and it was not that good. I mean not great, but that wasn't the biggest problem Digg had at that point. But it was one of the biggest problems that had at that point and it wasn't a real sign of things likely to go well for us. But like I said, you learn from those and I'm really proud that we and the team got it working, got it running even if ultimately we still went to zero and ran out of money and kind of sold for parts.

**Lenny** (01:09:32):
Do you think Digg could have made it? There was a world where Digg would've been a hugely successful business or do you think it was just way too late and it's the wrong product?

**Will Larson** (01:09:39):
The thing that really killed Digg is the change. It wasn't SEO driven. So monetization was from ads. Well, many companies including Digg claimed that it was the first in kind of stream, in feed like advertising company where Twitter has ads within the tweets or Facebook does. But Digg did that before Facebook or Twitter really innovated the ad format. But the vast majority of monetization was on these... We call them permalink pages, which is page 40. Then article we crawled and the vast majority of traffic for that was driven by Google search. And so there was an SEO change, which really is the thing that started creating the urgency for us to launch this migration.

**Will Larson** (01:10:20):
SEO changed, traffic started going down, monetization was driven by that. And so we were already on fire by the time we tried to launch this. But I do think that I still want something like what Digg was trying to become today. Social news based on like what my friends are actually reading and liking merged with a global index of similar users who are interested in similar topics. It's still a product that I think Google Reader has some kind of similar components to it.

**Will Larson** (01:10:49):
These are both interesting products solving interesting problems that have not for whatever reason been successful as businesses. And I do think there's a gap there still, but there's a lot of people trying unsuccessfully to fill it and there must be a reason why people struggle to fill it despite so many people trying.

**Lenny** (01:11:06):
Awesome. Will, is there anything else you want to share or leave people with before we get to our very fast lightning round because I know you have to run in about five minutes?

**Will Larson** (01:11:16):
I think we've covered a lot of it. New book coming out. New book coming out in February, Engineering Executive's Primer, O'Reilly. But that's probably it.

**Lenny** (01:11:25):
Awesome. Where do people find that? I know it's on O'Reilly. You can look at a preview of it even today, right?

**Will Larson** (01:11:29):
Yeah. O'Reilly, you can see the early copy. You can order it on Amazon as well, but it won't be shipping until February.

**Lenny** (01:11:37):
Okay. And then just to be clear, who's this for? It's for engineering executives by the sound of it.

**Will Larson** (01:11:42):
It's for engineering executives, but more so like anyone who wants to be one, anyone who's trying to figure out how to work with an engineering executive. So I think if you are struggling to understand why your CTO keeps doing boneheaded things, or if you want to side manage them, you're the head of product and you can't get the CTO to stop complaining about the engineers need more interesting projects to work on, this might be useful for you too.

**Lenny** (01:12:04):
Amazing. Okay. Ready for the lightning round?

**Will Larson** (01:12:07):
Let's do it.

**Lenny** (01:12:08):
What are two or three books you've recommended most to other people?

**Will Larson** (01:12:11):
So I talked about Thinking in Systems and Primer. I talked about Good Strategy, Bad Strategy, but I'll give you a third one, which is Don't Think of an Elephant by George Lakoff. It's a really interesting book about framing things in conversations that has really changed how I communicate.

**Lenny** (01:12:24):
Amazing. Favorite recent movie or TV show you've really enjoyed?

**Will Larson** (01:12:28):
I don't watch much TV or many movies anymore, but something I do still watch is Top Chef with my wife. She's a Top Chef, super fan. And there's something just very relaxing from these formulaic structured shows where you kind of know what's going to happen. There's no real consequences that matter too much and just escaping from real life to these formulas can be pretty peaceful.

**Lenny** (01:12:50):
No one has ever mentioned Top Chef before, so that's fun. Do you have a favorite interview question that you like to ask candidates that you're interviewing for a job?

**Will Larson** (01:12:58):
A lot of my interviews now are trying to help people decide if they actually want to join a company. And so my favorite question I ask now is like, "Hey, we've really loved you. You're going to come through. I think you're going to get a lot of offers from other companies too. I bet you'll have three or four really compelling offers because you're a fantastic candidate. How are you going to figure out really specifically which of those options are right for you?"

**Will Larson** (01:13:22):
I think it forces people to tell you what they want and then you tell them why you have that more than anyone else, and then you can actually pitch them on what matters versus pitching on things that don't.

**Lenny** (01:13:31):
Love that. Do you have a favorite life motto that you often come back to share with friends, find useful either in work or in life?

**Will Larson** (01:13:40):
No mottos, but I can think of two things I thought about a lot. At Uber is something I talk to people a lot because it was a challenging time for much of it. It was there's no way around, just through.And that was like, "Hey, we're not going to dodge around this. We're going to gut through it and we're going to get to the other side and then we're going to be there." What I think about a lot more now is, will anyone remember what we decided in six months? Because I think people stress out about a lot of decisions, but I increasingly believe most decisions people stress out about just aren't that important.

**Will Larson** (01:14:11):
So I'm like, "Will anyone care in six months what we did here?" And the answer is no. Just do something reasonable and let's move on to the next more important thing.

**Lenny** (01:14:17):
I love that. You've done a lot of writing. Is there a piece that you've written that you feel like is underappreciated that no one really totally got and hasn't spread and you're like, "Ah, I'm so proud of that one"?

**Will Larson** (01:14:30):
Maybe the piece I'm most proud of from last year was Hard To Work With. So Hard To Work With is basically I see a lot of people who are incredibly talented, but they try to hold their peers to a high standard and then they're viewed as combative or difficult to work with. And this one comes from a core struggle of my early career where I kept trying. I thought I was holding people accountable and people were just like, "You suck to work with."

**Will Larson** (01:14:58):
And I was like, "But I'm just trying to have a high standard. Isn't that what we want?" And talk about honest values. Every company is like, "We have high standards," and you're like, "Well, let's do it." And then they're like, "We don't have high standards here. You suck." So that one is one that really is so transformational to me, and I think it really hits some people hard because I think a lot of people really go their entire career without figuring this one out.

**Will Larson** (01:15:20):
And they're some of the most talented, hardest working people you'll ever work with and can't quite land this one idea that's holding them back. And they care so much and they are often despised because they care so much. I think this is one that I hope more people will read over times and there's a really important lesson for me in there.

**Lenny** (01:15:42):
Well, we will link to it in the show notes and help more people discover it. Two last questions. Where can folks find you online if they want to reach out and maybe follow up on questions? And how can listeners be useful to you?

**Will Larson** (01:15:51):
So find me online, lethain.com, lethain.com. All my writing, my books, everything links linked there. And the biggest thing that I'm thinking about right now is just strategy. So really curious for folks who are thinking about strategy, who think they've done product, business, or engineering strategy well. Would love to hear from folks what they're thinking about, what's actually worked and maybe what are the lies that have not turned out to work that they thought might work earlier in their journey.

**Lenny** (01:16:19):
Amazing. Will, thank you so much for being here.

**Will Larson** (01:16:23):
Thank you so much. This is really fantastic.

**Lenny** (01:16:25):
Same for me. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [3/19] How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)

**Sam Schillace** (00:00:00):
We tend to undervalue the things we're good at. We tend to think work has to be unpleasant. And so if something is easy and fun, we don't tend to think it's valuable. So I think lots of people gravitate in this direction of like, let's go do unpleasant things and grind our way through the career because that's the way to make it. But the reality is you should go do the thing that you feel guilty to get paid for, if there's a thing like that, and do the hell out of it, right? Do it as hard as you can. If you get pleasure from doing something that people want to pay you for, do it the best you can do it, as hard as you can do it. And if that's messing around and playing around with cool ideas, do the hell out of that. Work doesn't necessarily have to be hard.

**Lenny** (00:00:37):
Today my guest is Sam Schillace. Sam has an incredible resume that is very hard to summarize succinctly. I'll give it a shot. Currently, he is corporate vice president and deputy chief technology officer at Microsoft, where he leads efforts in the consumer product space, infrastructure, and AI. Sam is most known for basically inventing Google Docs with his company Writely, which was acquired by Google, and became the foundation for what is now Google Workspace, which currently has over one billion active users a month. 

**Sam Schillace** (00:03:51):
Thank you. Happy to be here.

**Lenny** (00:03:53):
A really fun fact about you is that apparently you have the very first Google Doc file. I don't know what you call it. The very first Google Doc document saved somewhere from before even Google Docs was a thing. And does it still work in today's Google Docs? And what is in this document?

**Sam Schillace** (00:04:08):
Yeah, it does actually still work. It's pretty funny. Actually, if I move my camera for a second you might, if you're on YouTube, you can see the Writely thing in the background. Writely was the company that did Google Docs. Yeah, it still works. And it's funny though because it's like the document of DCS, right? So we started off 2005, wrote this thing in C#, which is a little known, in our own... It was pre-cloud, so we had three file servers that we rented that were Windows machines in a data center in Texas with a sysadmin in the Philippines running them. So it started there.

**Sam Schillace** (00:04:43):
And then when we moved to Google, we ported everything to Java, we moved all the data over into Bigtable. And we didn't lose anything. We never lost anybody's stuff. So it's still there and moved across. And then so that's one backend migration, and there's another one with Spanner. And then the front end has been rewritten twice as well. So it's like, is it really the same document? I don't know. The front end, back end have been rewritten. It's not much. It's just me saying something to Steve about, is collaboration working? Are we colliding on each other? Because we were trying to figure out typing on one line, if that algorithm was working.

**Sam Schillace** (00:05:14):
And then there's a picture of Edna from The Incredibles pasted into it. I don't know why. I think that came after, so I might've gone back and pasted that in. I'm not sure when. We must've been testing pictures or something. Unfortunately, we don't have the version history anymore, so I don't know what was original, original. But it is the oldest Google Doc from October 2005 or something like that.

**Lenny** (00:05:34):
I love that this philosophical answer of, is it still the same Google Doc, considering all the code has been redone.

**Sam Schillace** (00:05:42):
Well, the Computer History Museum wants to curate it. I talked to these guys and they were like, "Oh, that's so cool. We'll take that." I'm like, "How?" I can make you a PDF. Now it's not the document. I can share you into it, but please don't edit it. How do you curate this? So that's funny.

**Lenny** (00:05:58):
Yeah. It needs to be on the blockchain.

**Sam Schillace** (00:06:00):
Yeah. Yeah. If you made the NFT of it, that would be more authentic, I think, than the document almost. It's kind of funny.

**Lenny** (00:06:07):
That's amazing. And it's amazing that it still works. That's a testament to, I don't know, you/Google.

**Sam Schillace** (00:06:12):
Well, I'll tell you a quick Google story. When we migrated in to Google, we were very sneaky about it, and we put the site into "maintenance mode" for eight hours on a Sunday, where everything was just read-only. And then we migrated all the data and moved everything and brought the new system up. And three days after that, Sergei was in a meeting with me and he's like, "So when are you guys going to move over to Google infrastructure?" And I got to tell them, "Oh yeah, we did it this weekend." No one noticed. Some blogger in Germany noticed that the IP address changed and that was it. Nobody noticed it at all, so we were really good about it.

**Lenny** (00:06:46):
Man, I love these sneaky stories. I'm hoping we hear more. There's a bunch of stuff I want to cover, the first is this broad idea of disruptive innovation. I know that you spend a lot of time thinking about this. Google Docs is a great example of this. It feels like Microsoft increasingly is getting really good at this. Just the idea of doing something completely new, oftentimes things that people didn't think were possible. So let me just ask a broad question. Why is this important to you? Why do you spend a lot of time thinking about this? And then just what are some tools you've found to help you and other people think more innovatively, more originally?

**Sam Schillace** (00:07:18):
It's an interesting question. The why it's important part, I don't know, it just is. Everything you're wearing, eating, using, listening to, sitting on, was a disruptive innovation at some point. That's how everything happens, right? I think there's this really interesting thing where everything new is threatening at some level at the beginning. I mean, probably literally the first guy who invented chairs got shit from his tribe mates for making a chair. And they're all obvious in retrospect, right? Everything is obvious in retrospect.

**Sam Schillace** (00:07:51):
But I think there's this really deep thing that people have where if something is disruptive of your worldview, it feels threatening, and you have this very stark choice to make that's either you're wrong or it's wrong. And humans are storytellers. It's very easy for us to tell stories about why something is right or wrong if we're motivated to. And so I call these why-not questions. People ask these why-not questions a lot. So a new thing pops up, and if you're not ready to receive it for some reason, you're not already half there or you don't have a problem that it solves or whatever, it's just threatening and irritating, and you come up with a why-not question.

**Sam Schillace** (00:08:29):
We heard a bunch of these with Google Docs, with Writely, in the early days about the browser wasn't ready, people wouldn't... The whole model of the cloud was like, people aren't going to trust you to store your files. That's really weird. What if there's no connectivity? I heard the no connectivity on an airplane story 100 times from journalists. Like, "What if I'm on an airplane and I write stuff?" I'm like, "I don't know. There'll be connectivity on airplanes soon." Which there is. And those are all just why-not questions.

**Sam Schillace** (00:08:55):
I think the more interesting ones are the what-if questions, like, what if this does work? Just use your imagination. Think about, how far can I extend the curve? What are the implications of that? I'm an engineer, and engineers are fundamentally pessimistic people. Somebody once told me engineers come into the world broken. They just look at everything as a problem to be solved. And I think there's something to that. But I feel like I've missed out more by being pessimistic than I have by being too optimistic too early.

**Sam Schillace** (00:09:26):
So I have this kind of mantra now that there's just not that much of a prize for being pessimistic and right, particularly in a moment like this. It's much better to be optimistic and wrong than pessimistic and right, I think. So I don't know. And I'm an impatient person. I'm a creative person. I'm a messy person. I just like to create and explore and find stuff. So disruptive innovation just seems natural to me. But I think it's not an exaggeration to say, literally, that wheat you had in your bread this morning, if you eat bread, some weirdo was messing around with plants 1,000 years ago and everybody thought he was a nut, or she was a nut, and then we had wheat because somebody... Just everything, right? Everything is like that.

**Lenny** (00:10:12):
Along the same lines, I was actually just working on a post around first-principles thinking. And I found this quote from Steve Jobs just reminding us that everything around us was designed by some person that wasn't necessarily that much smarter than you. And there's no reason there isn't a better way. It just happens to be the way it is today.

**Sam Schillace** (00:10:26):
Yeah. One of the other ones that I like to keep in mind is every new idea looks dumb at first. Unfortunately, the dumb ideas also look dumb at first. It's not a perfect [inaudible 00:10:35]. But the more disruptive they are, the more dumb you're going to feel they are. You always listen for stuff like if they say it's a toy or if it's practical or it's stupid or I don't get it or whatever, those are often... Toy is a good keyword. If you hear people saying something's a toy, that's often a really good signifier that it's actually something real and threatening, and they can't think of a better criticism for it than it's just a toy right now.

**Lenny** (00:11:01):
Yeah, I imagine people thought about Google Docs that way initially. It was like, "Oh, this little toy in the browser."

**Sam Schillace** (00:11:06):
Yeah, we got all this stuff. I mean, the real interesting thing, like I said at the beginning, you have this very binary reaction that's possible, right? You either understand it, in which case, you're super excited about it like, "Cool, the world's going to change in this exciting way." Or you don't and you reject it. And to the degree that something is really disruptive, that reaction, that binary reaction gets really strong. And so with something like G Docs, we got this thing with G Docs that was really confusing in the early days to me, where there was a small group of people that really liked it. Some of them liked it more than we liked it. Nate Torkington over at Writely was this super huge early booster for it. And I did not understand what he saw in it at first. But then we had people that just wanted it to die in a fire. 

**Sam Schillace** (00:11:52):
And that bifurcation of love it, hate it, is really how you have an idea of whether you have impact in what you're building. If you get more of the bell curve of modern indifference and maybe mild like and mild dislike, that's an's an incremental product. That's not really disrupting anything. But if you look at something like ChatGPT where the entire world is like, "This is amazing." Or, "This is terrible." And there's not a whole lot in between, that's a very good signifier of it being truly impactful and disruptive. Whether it's actually good or bad is a separate question. But there's no denying that that's a disruptive technology.

**Lenny** (00:12:33):
That's an awesome framework. Basically, if it feels like people sort of like it, mostly people don't care, very few people love it or hate it, probably not disruptive. If some people absolutely love it and a lot of people really hate it, good sign.

**Sam Schillace** (00:12:45):
Right. Yeah. Actually, weirdly enough. It's not voting, right? In the early days, we had, I don't know, a couple of million users, five million users, and there were still executives at Google telling me that it was a stupid idea and that it should stop and we shouldn't be doing it. So, for a long time, the haters outnumbered the people who were fans. And who cares? Whatever. It's fine. As long as you don't run out of the people who love it, that's fine.

**Lenny** (00:13:18):
Is there another example of you using this what-if approach either on a product you worked on or something you've seen and it working out?

**Sam Schillace** (00:13:25):
I'm doing a lot of it right now, honestly. I mean, that's probably the most immediate example. But I could almost point at any product and there's moments like that in there. But right now there's a lot of why-not stories, right, around generative AI. So it's expensive, it hallucinates, you can't necessarily... It's sarcastic, it's random, it doesn't do the same thing twice. Yeah, they're real, they're actual issues to solve, but I look at it and think, "Well, what if? What if we can build software around it? What if we can build more complicated programs than what we've been able to build? What if we actually have a reasoning engine that we can use to do meaningful things? What if this is really the second Industrial Revolution where, in the first one, we had a surplus of physical energy beyond just our bodies and things like water reels, and now we have a surplus of cognitive energy beyond just our brains, right?"

**Sam Schillace** (00:14:17):
And that's a really transformational idea. So I'm completely in that mode right now, honestly. I think that's just the right mindset for something that's obviously this disruptive, right or wrong. Tesla is a great example. SpaceX is a great example where people are like, "That doesn't make any sense." And Elon's like, "Well, what if you could land rockets and reuse them and they get really cheap? That's pretty amazing. What if I can fix the battery problems and a car is basically a software product, right?" Those are pretty amazing what-if questions, right, of those products.

**Lenny** (00:14:49):
Yeah. So in this work on understanding what first principles actually looks like when you're thinking from first principles, the steps are essentially, figure out what you want to do, figure out the levers that keep you from achieving that thing, and then basically question every assumption that stands in the way of making this possible. So I think Elon's a great... The classic example. You can't talk about first-principles thinking without quoting Elon, telling stories of Elon. But essentially, it's just, okay, how much would it cost to make this if we were to start over and not...

**Sam Schillace** (00:15:16):
I mean, the why-nots, there are actually problems you need to pay attention to eventually to build stuff. But once you have the what-if, right, just to pick on SpaceX for a second, right? If you have what-if of like, "If I could make payload to space cost a lot less, what if?" Okay, that's amazing. That's an amazing world. Let's see if we can work on that problem. And then now you have all the why-nots? Why not? Why isn't it as cheap as it could be? And you can start to break the problem down and think about it that way. It's a good model.

**Lenny** (00:15:46):
This connects to something else that I know you're big on, which is optimism, being optimistic. There's this feeling that pessimism, you're often right. There's growing pessimism in the world in a lot of ways, especially in technology. I know you're a big proponent of staying optimistic. Can you just talk about why you think that's important and how you approach that?

**Sam Schillace** (00:16:06):
It's funny, it's a choice. I'm not an optimistic person by nature. I'm just not. All the people in my life, if any of them listen to this, they'll just laugh at the idea that I'm a proponent for optimism per se. It's just a conscious choice. I don't think you get very much for being pessimistic necessarily. You definitely don't get a lot for being careless. You can be optimistic to the point of being careless and causing harm, for sure.

**Sam Schillace** (00:16:33):
Maybe a better way to say it is growth mindset, right? You want to look at the possibilities rather than the limitations, and suspend some disbelief and just work on these problems. I just personally feel like I've missed out on more than I've protected myself from. If I sum up both sides of that equation over my career, I wish I had been more open-minded and more optimistic, and more willing to try things, and more focused on possibilities rather than problems.

**Sam Schillace** (00:17:00):
And so I'm just personally choosing to do that, try to do that as a habit. Nothing deeper than that. I just think it's a better place to be, particularly... It's kind of funny. When I came out here, I was pre-med. I dropped out of school. I came out to be a computer scientist with my friend. I didn't think of it that way. I came out to have a job at Ashton-Tate with a friend of mine, and spent 10 years not understanding that I was actually in a career and thinking that it was a temporary thing where I had to go back to med school and get my degree and be a doctor or something boring like that. And so for 35 years of doing this, it hasn't occurred to me that, oh, actually, I'm in this computer industry that's this technical industry that's constantly growing and constantly inventing things and constantly coming up with these new ideas. And actually, the best posture in that world is to be creative and curious and open and optimistic and try things and stuff like that.

**Sam Schillace** (00:17:54):
The other thing I'll say about optimism too is related to doing these disruptive things like G Docs. Going back to this idea of all the good ideas look bad at first. Okay, so that's a first principle. That's a sort of fundamental thing of you're going to constantly be challenged by the really good ideas. So how do you overcome it? Well, one way you can overcome it is you want to be able to try things more easily. So part of that is being more optimistic, so being more willing to try stuff, and part of it is also just making it cheaper to try things.

**Sam Schillace** (00:18:26):
Very early story of G Docs, when I had the idea for Writely, my two co-founders who were both deep domain experts in both app building and word processors were like, "The browser is never going to support this. It's a bad idea. Let's not do this." And they were right and wrong at the same time. They were right that it didn't support even what we have today and wouldn't have supported a full experience, but wrong in that the world was going to change and evolve. And we would never have done the first experiment if it had been a long and costly thing to do, right?

**Sam Schillace** (00:18:58):
So the fact that our tools were sharp and I could say, "Let's do this thing." And it only takes a couple of days to get it on its feet and see how it feels, it's kind of a form of optimism, right? If you're super pessimistic, you can be like, "Even that's not worth it. Two days is a waste of time." So there's always a little bit of a leap of faith. And then you want to make those as consumable as possible. You want to be able to try things out quickly and learn things and do these experiments. 

**Sam Schillace** (00:19:23):
Now, lots of people have said that before, but I think all those pieces connect for me in this idea of being optimistic and open to trying stuff. Because stuff always is different. You're always wrong about products. That's one of my other rules is you're just always wrong. And so you have to try it. You have to put it in front of people. You have to try it yourself before you'll understand it. No one can really design products in their head completely as far as I can tell.

**Lenny** (00:19:47):
Awesome. There's a few threads I want to follow there. But this is also a tool that I found came up again and again in first-principles thinking, people that are really good at this, is just trying it. There's a lot of just, "Nah, it's not going to work." And exactly as you just described, you often find out you're completely wrong when you actually try it out. And you have this quote, I think in one of your newsletter posts, talking about building Google Docs. You describe it as just fuck around.

**Sam Schillace** (00:20:12):
Yeah. Kind of.

**Lenny** (00:20:13):
Get to the edge of something and fuck around. That's the strategy.

**Sam Schillace** (00:20:15):
Yeah. Yeah. Get to the edge is only... Get your tools as sharp as you can get them to be. Make it so that you can try lots of cheap experiments, right? And just mess around and see what happens, see what pops out. And just try to be observant. I think the other part of optimism too is there's a receptiveness to it, right? If you're very pessimistic, you might miss the surprising result that pops out of an experiment. You might force yourself to do a bunch of experiments grudgingly, but you're like, "You know what? I hate this. I'm doing four experiments today because I have to do it because I want to be an entrepreneur, but it sucks and everything's miserable and black." And then you won't notice that, oh, this thing didn't work, but it didn't work in an interesting way. And you're more receptive to that kind of surprising thing, I think, when you're in an optimistic frame of mind. Like, "Oh, let's see how far I can get with this. Oh, it's not working, but why isn't it working? Well, that's kind of interesting. It broke here."

**Sam Schillace** (00:21:04):
And we've done stuff like that in some of the things, the projects I've got going in Microsoft right now, we've got a chatbot thing we've been working on for a while and with memory, long-running memory so that you can have long conversations with it. And they work okay, but they don't work great in some ways. And we were trying to get multiple versions of them working together, like multi-agents working together. And we gave them whiteboard working memory as a shared working memory thing to fix this problem. And that turns out to make them much smarter. Don't know why. It just makes them smarter. So that was one of these nice little bits of discovery where if you're in a pessimistic frame of mind, you might've said, "Well, these don't work that well, let's give up on it." More optimistic frame of mind was like, "Well, let's try to give them a whiteboard just like a person and see if they cooperate better." And it turns out they really do. So another example of that mindset.

**Lenny** (00:21:54):
Along this thread, I was going to ask about this earlier, but there's a lot of technologies people get optimistic about. Crypto comes to mind, not that there's nothing there, but a lot of people got really optimistic and then it turned out there wasn't really a lot of business to be built and then things entered wintertime. Is there anything you've learned that gives you a signal that, "Lets keep working, I'm going to stay optimistic about this thing?"

**Sam Schillace** (00:22:15):
I spent a lot of time really thinking hard about crypto and whether I was just reacting to it because it threatens some part of my identity or whatever. And I never came down to anything that seemed valuable. I mean, that was always the thing for me is just there has to be a what if that I can say, "Well what if this works? How valuable is it?" And for crypto I was always like, "Well what if it works? Then I have to run up sec on my personal finances. That sounds dystopian. I don't want that." I can't think of anything as a user that I think actually is valuable here, even in the best case. So I feel like the pessimism is justified. 

**Sam Schillace** (00:22:53):
So that's one of my other root principles is just like it's all about user value. Users are lazy, right? We're all lazy. We don't really care that much at the end of the day. No one's going to do something really in their life for any other reason other than it makes their life better. Nobody cares that you're friendly or nice or the logo is pretty or whatever. They care about making their life easier. We're all cynical at heart at some level, so if you can't point at user value, significant user value, it's not going to work. It doesn't matter. Shove all the marketing dollars into it you want, you can write all the articles you want, but it's got to actually solve a problem, a real problem, at the end of the day. I just never saw that with crypto.

**Lenny** (00:23:34):
Yeah. So I think the lesson there is truly understand if the value is real, versus, this sounds really cool, you think a lot of... Would you want it? I think is a nice exercise there.

**Sam Schillace** (00:23:43):
We pick on poor Elon, but I feel like with a lot of his products, at least he... He's got lots of other issues, but he articulates clear user value even in the beginning when he's hyping things up. Like Teslas, right? Okay, so electric cars weren't ready, he did the Roadsters, whatever. But he at least articulated this idea that we're going to put a lot of batteries in these things. They're going to really be real cars. They're going to have a real range. We're going to figure out the charging problems. As an end user I'm like, "Okay, that's great. Now I have a car that works like a car that solves some problems that's way cheaper to operate, because the fuel is cheaper. He's solving all the end user problems for me." That at least makes sense. Even if you don't believe that he's going to do it or believe in the way he did it, at least the end user value proposition makes sense, right?

**Lenny** (00:24:32):
You have this other great quote in your newsletter, "People are lazy. Look beyond cool too, on how much easier new tool or tech makes someone's life. Convenience always wins." Can you talk about that, just this realization people are just lazy and that's the key?

**Sam Schillace** (00:24:44):
Yeah, well I mean that is the thing. I think as product builders, it's hard to not love what you're doing. You build a product because you love it, you build it because you understand some problem, you build it because you want a paycheck maybe sometimes. But we build it for all these reasons that just do not matter to the end user at all. And if there's one thing I've learned about product, particularly in the consumer space, just kind of in general, is people are just lazy about stuff and don't care about anything other than it making their life better. The thing that's complicated with that is there's two things about it that I think are interesting that follow from that principle. One is, I think products almost follow these thermodynamic rules where if you add a little bit of value, your adoption goes slowly and if you add a lot of value, your adoption goes really quickly, right? 

**Sam Schillace** (00:25:32):
I think ChatGPT is a great recent example of something that was just added a ton of new value to the world and got this explosive growth, and then you see lots of other AI stuff that people are doing that's just not bad, but not great, and it's sort of kind of adding a little bit of value and slowly lumbering along, or maybe it's going to collapse under its weight. That's one thing about the users are lazy part of this. And then the other one I think is, again, it's almost like physics. I think of this as entropy, or people who are confused about entropy or will be like, "Entropy is not real. Look, it runs backwards all the time on earth. Life gets more complicated. What is the deal with entropy?" And like, "Well no, you have to consider the whole system, right? The entire system of the solar system, including the sun is increasing in entropy all the time. We're just making use of some of it."

**Sam Schillace** (00:26:24):
And I think the same thing is kind of true about user laziness, where people are like, "This tiny thing that I'm focusing on, this feature that I added is better. Therefore, users should adopt it." But you forget all the stuff around it. The user has to hear about it, the user has to remember it in the moment. The user has to learn how to use it, they have to build the habit. That's all effort, right? Not to mention the fact that the actual use of your feature might have friction on the way in, right? It might be hard to sign up for it. 

**Sam Schillace** (00:26:50):
When we did Writely at the beginning, we didn't even ask for an email address, because it was such a novel thing. We didn't want any friction at all in the onboarding process. So you could just come in and make a document and start using it without telling us anything at all about yourself. And after about two minutes of typing, if you're still there, we'd very gently just say, "Please give us your email address, no password, no anything. Just give us your email address so we can send you a URL of this document in case you care about it later. Because if you leave, we'll never know where... We'll never be able to find it again." 

**Sam Schillace** (00:27:21):
But we were super focused on that, as little friction as possible. And I think it's well known in the consumer space, you don't have... The number of seconds you have is not many. 15 seconds, 30 seconds, right, to convince somebody that there's some value there. They're not going to hang out and grind their way through a bunch of high-friction stuff to sign up for your thing. That's the other part of it is just, users will only adopt what you're doing if that sum total of energy that they have to expend is less than the resulting ease in their life that they get, usually by a factor of at least a couple, right? So it has to make your life a lot better, hopefully a really a lot better, like 10X better than what you spend to use it.

**Lenny** (00:28:10):
What I think of as you're describing this is, Microsoft Excel had a billion toolbars and buttons and options, which allowed Google Docs essentially to come in with a much simpler experience. Now you're on the other side of that, which is I didn't think about.

**Sam Schillace** (00:28:25):
Yeah, it's a really funny place to be. And it's funny to be at Microsoft, because I'm kind of the enemy, right? Because I'm the guy who messed them up a little bit. So there's some friction around that. Yeah, I mean I think there are similar trade-offs to be made right now, by the way, with AI. I think there's similar opportunities. But we made this choice with... So it's a little hard to remember, right? Because it's like 18 years, 17 years ago now, 18 years ago almost. In that era, Office was impregnable, right? So software had to be distributed physically, right, it had to be shipped around, it had to be bought and installed. It was harder to use.

**Sam Schillace** (00:29:01):
And so there's a very high transactional cost. Because there's a very high transactional cost, the buyers would always make this decision like, "Do I want the thing with 1,000 features or the thing with 995 features? I don't know what those last five are, but I might as well have all of them." And so that was just the lock-in for Microsoft, right? So we made this trade-off, we're like, "Look, we're easy to use, we're zero install, you don't have to ever deal with it, it's super convenient. Plus you get this one new feature that's really, really useful, which is collaborating with each other and not having to send attachments around the old file servers, but we're going to take away most of the features, because we don't care about them that much." 

**Sam Schillace** (00:29:39):
And we took away a little bit more than we should have. In the early days, we'd get all these complaints about people who wanted word count, which I thought was a really weird... I thought that was going to be way at the end of the list. We didn't have rulers, we didn't have any kind of formatting at that point, any real pagination. We just had these basic documents. But page word count came in, of course it was students, was one of our early adopters. So they really wanted to know if they were at the word count for the essay that they had just had assigned to them.

**Sam Schillace** (00:30:06):
So there was this dance with Microsoft that we deliberately made this trade-off. And I think it's almost like a classic innovator's dilemma model, right? We had this incumbent that was asymptotically approaching usefulness, they're adding stuff. Whenever they added stuff, it wasn't really that much more valuable. And then we were this small thing that came in into a market that they didn't care that much about, that they didn't understand that well, which is the internet stuff, this disruptive new thing. We just chipped away from the bottom, like the innovator's dilemma. And I think it was hard for Microsoft to respond to it. I think it took them a while to even have a clear idea of how they were going to respond to it. In retrospect, they did fine. We took a bunch of market share, but they kept all the money basically. So we being Google. So they survived it. They did a good job surviving the challenge. We have all the users now, but they have all the money. We have all the money, I guess now.

**Lenny** (00:31:07):
I want to spend more time on Google Docs and the story there. A couple questions. How long did it take from starting on it to feeling like it's working? Whatever you consider product market fit.

**Sam Schillace** (00:31:17):
Almost immediately, honestly. It was weird, the process of it was, I had this idea, we set this thing up, we started working together. We're like, "Ah, that's actually pretty..." So basically history is like I noticed contents editable, so the browser would do some editing for you. And then I noticed JavaScript, I never realized that JavaScript is out there. And we had done word processors in the past, this team, and for a long time. In fact, my co-founder, Steve, the other person on that document, wrote this thing called Full Write way back in 1987 or something like that, that was a direct competitor. '85 I think even, that was a direct competitor to Word one. 

**Sam Schillace** (00:31:57):
So we knew word processors, and so we decided to just try it. What's it like to build a word processor? And the fact that you could collaborate on them was kind of an accident. They're just these things on the server. We hadn't built the thing that would lock somebody out yet. So there was just like, "Here's a document, you can edit these two things." Which we, A, immediately realized was really cool. We could both work in the same document at the same time. And then, B, realized, "Oh, crap, we're colliding with each other, because there's no presence or anything like that. And there's no collision detection or anything like that."

**Sam Schillace** (00:32:26):
So pretty quickly we're like, "Oh, that's kind of cool. That feels good as a development team to have these shared documents, not to send stuff around and not... So that's cool. So let's build that out." But like, "Oh, bummer, collaboration's a problem. We'll have to go fix that." And naively figured out that that's a problem. And it took forever to get that working. It was really, really hard in the time, because we didn't do operational transform. I don't think that technique had been quite invented yet. And so we did three-way merge, which doesn't work that well, because the browsers... The logical document, a document can be rendered differently in HTML. There's not a canonical representation. 

**Sam Schillace** (00:33:04):
And so you're doing merges where alphabetization can change, the order of attributes can change, the tree structure can change. Firefox would do a blank paragraph with a singleton BR tag, and IE would do it with an open closed paragraph tag. And so even the tree doesn't match. So it's a really hard merge problem. So that turned out to be a gnarly hard problem to solve. But once we had seen the value of working together, we were motivated to do that.

**Sam Schillace** (00:33:32):
The interesting thing too with that is, I think if we'd gotten it in the other order, we might not have done it. It's another good example of why not and what if, right? Where we got really lucky that we saw the what if part, that we saw how cool a document in a browser that you could collaborate on would be, because if we understood how hard the collaboration piece would've been first without understanding that value, we might've been like, "Eh, it's not worth it. It's going to be so hard to solve that problem. It's probably not a useful app." So I think it's a good little counter example of that optimistic, pessimistic perspective we were talking about. We could easily have missed that idea, easily have missed that idea. And we just got lucky I think in the order it got presented to us.

**Lenny** (00:34:16):
That is really interesting actually, that you need to be pulled to the what if getting you so excited that you're going to spend however many years it took you to solve that problem, because you are so excited about this what if. I think that's a really good-

**Sam Schillace** (00:34:31):
Yeah, yeah, I mean I've spent a lot of time. It's kind of funny, I keep expecting people to just be like, "All right, grandpa, stop talking about G Docs. It's been a long time." Right? So it has been a long time. It's been 17 years, but it's still very relevant. It's got a couple billion users now I think, it's a big thing. But I've spent a lot of the last 10 or 15 years just thinking about, why did that work? What worked about that? What lessons can I draw from it? There was a lot of energy around it, positive and negative. The first week I was at Google, an executive there refused to give me hardware, because he thought that Google was an app company not a... It was a search company, not an app company. And literally the guy in charge of hardware at the time refused to give me hardware for this service. And I had to threaten to either sue him or haul him in front of Eric Schmidt, because I had a contract and I had contracted earnouts.

**Sam Schillace** (00:35:20):
So that was another one of these interesting lessons of sometimes the opposition is enormous. And if I had just been a random Google employee with this idea and no legal protection, and the CEO wasn't a fan of the project, it would've died. There's no way it would've made it through that negativity and that pessimism and that person being either challenged or afraid of the idea, or just not able to imagine it, or what. I'm not sure what. But we'll keep coming back to this idea of optimism, but I have this very strong feeling about that most of the reason people don't do really innovative good products is this kind of mindset. You're just not seeing the opportunities.

**Sam Schillace** (00:36:02):
There's a lot of hard work for sure. There's a lot of stuff that you can read about and best practices of doing iteration and user testing and user interviews and really listening and all the engineering best practices. That stuff is pretty mechanical. Once you know where you're going, you can do that. It's not that hard to learn and to master it. I think the hard stuff is this mindset of being open in the right ways and understanding that some kinds of pushback are good pushback. Some are bad. 

**Sam Schillace** (00:36:32):
I always think that product builders and entrepreneurs, you have this really hard problem of you have to be very rigid about your mission. I know where I'm going. I know what my mission is, and I'm going to go there because the world doesn't care, it's going to push back. But you also have to be really flexible about feedback. You're probably aren't going to be right about a bunch of it. And so you have to blend these two things together somehow. It's like a samurai sword that's hard on the back, but softer on the edge so it doesn't break. Or the other way around I think. But there's this hard thing you have to do as an entrepreneur, and I think it's the real core of building really great products is finding that balance and really listening to those signals, being open to it.

**Lenny** (00:37:16):
And also knowing how long to commit to it versus time to move on to something else. So along those lines, what was the moment where you finally felt product market fit for what became Google Docs, and how long was that from the beginning of starting to work on it?

**Sam Schillace** (00:37:30):
It depends on what market we're talking about. I've been continually surprised at the adoption of G Docs. I think we knew there was something there pretty quickly, probably in the first couple months. There was a lot of energy around it. It was a weird ride, because we built this thing on a whim, and as an experiment. We liked it. We decided to go just advertise on Google. At the time, 37signals was the cool company. And we're like, "That looks cool. We'll just be some engineers and we'll have a little subscription SaaS business thing and chill out. So let's see what it costs to acquire customers. So let's go advertise on Google and see how much it costs to get people to sort of show up, and then we'll figure out if we have a subscription business or not."

**Sam Schillace** (00:38:12):
And that just got us noticed. That got us noticed by Google. It got us noticed. We were I think one of the first 10 articles at TechCrunch, like Michael Arrington. Another funny story is that I had a breakfast with Michael Arrington at Bucks, in that era where he was trying to decide, he had this spreadsheet idea he wanted to work on and he was trying to decide he should go do that and maybe join forces with us, because we were cool, or if he should continue to work on this blog thing he had gone called TechCrunch. So I might be partially responsible for TechCrunch, because we turned him down and said, "You should go do TechCrunch instead." Every time I would bump into him, I would laugh about that one. 

**Sam Schillace** (00:38:50):
But when we got noticed, we really got noticed. There was just this period where we were the hot thing for a couple months, where every VC wanted to talk to us and everyone's trying to figure it out. Because I think we're like... When you see one point on the line, like Gmail, which came before us, you're like, "Oh, that's kind of cool. That's an interesting quasi-app." But it's like a weird kind of app. It's serialized. You can't really interact with it that much. And then you see this as another point on the curve and you're like, "Oh, that's a real app. Oh, crap. I wonder, is there anything stopping us from doing the rest of Office? Oh, probably not. How far is this going to go?"

**Sam Schillace** (00:39:27):
And so I think we were that second point that showed that there was actually this totally different paradigm. And so we just got this enormous amount of tension pretty quickly. And then the rest of it was feeling our way through what does it actually mean? How much of the functionality do we need to build? What's the really important part about it? How much of its collaboration? We spent a bunch of energy on offline, which was miserable, which never turned out to matter that much. 

**Sam Schillace** (00:39:51):
Now that team has spent a long time replicating all these features that we abandoned by the wayside, which I think I'm not that interested in. I think the future of documents looks very different than what we have now. I think it's kind of funny now that we're spending billions of dollars on GPUs to emulate wind pulp and ink pressed by metal type. We're building linear documents that are fixed, that are static. So one of the things we've been doing with these chatbot things is they also serve as documents. I say bots or docs all the time. And so you'll do these things where you... I do this all the time, where we'll interview... We'll create a new one. It has a separate identity, as a separate document, and then you tell it like, "I'm going to write a technical document. Here's roughly what it's about. Why don't you interview me?"

**Sam Schillace** (00:40:35):
So it interviews you for an hour, and now you've got this nice linear artifact which you can read. It's very readable because it's conversational. But at the same time, you've been building all these semantically encoded virtual synthetic memories in the Spectre database. So you can come in and say, "Show me a diagram of this. Draw this diagram for me, change it in the following way. What is this? If I change this, what if I change that? Summarize this part of it." So you can start to interact with it. That's still creating stuff at the bottom of this linear artifact. But the next step that we're working on now is just making that dynamic where you just come to something and you talk to it and interact with it. 

**Sam Schillace** (00:41:12):
I think one of the things that's going to happen is, just like it seems... Well, in the early days of G Docs, people would say, "Well, what if I'm not connected?" And one of the things I would say is, "In three or five years, if you get handed a device that's not connected to the internet, your word for it is going to be broken." Which is true, right? It's anachronistic and weird if something's not connected. I think we're going to feel the same way about intention and interactivity in our products very soon. If I can't tell something what my intent is and have it configure itself in an intelligent way, have it converse with me, whether that's a device or a piece of GUI UX somewhere, I think it's going to feel anachronistic. It's going to feel really weird. 

**Sam Schillace** (00:41:55):
There's that scene in one of the early Star Trek movies where Scotty tries to talk to the mouse, right? He's like, "Computer make the..." He's pissed off because he can't talk to the computer. We're all going to be like that in five years I think, about it. And it's going to seem really weird that we have these applications that I can't collaborate with the application. Why can't I collaborate with the applications? It's like the application's locked on a file server just like the pre G Docs days. Why can't I just interact with it and have it configure itself the way I want it to configure itself, and show me the data the way I want to see this, and let me build the workflow the way I want it, and remember it for me and bring it back later, and all that stuff? So that was a long digression, but I would just like... You're asking about features and functionality, and I feel like where we are now with these feature wars, it's just silly. It's not the point at all. I think documents are going to change radically in the next few years.

**Lenny** (00:42:46):
I want to follow that thread. Before I do, I found the first TechCrunch post about you guys. Starts with, "Imagine Word, but as an Ajax browser application."

**Sam Schillace** (00:42:54):
Oh, yeah, there you go. Yeah. It wasn't even JavaScript. It was Ajax.

**Lenny** (00:42:58):
Ajax, so hot back then.

**Sam Schillace** (00:42:59):
It's also funny too, because I'll talk to young front end developers these days. I'm like, "I don't want to scare you too much, but jQuery didn't even exist when I wrote this thing. This is like bare metal in the DOM, and there were bugs." When I went to Google, I had to write this little network stack at the bottom of the JavaScript that in theory [inaudible 00:43:21] you could interrupt, you could have multiple requests inflate and you can interrupt them and discard them and stuff. 

**Sam Schillace** (00:43:25):
But the stack at the time was really buggy, and I think it was IEE. And so I wrote this little network queue that would keep track of whether there were requests in flight, and kill them in a way that didn't break everything. And it was hard to do, because it's this weird asynchronous programming. And that piece of code, when I went to Google, they made me reformat it for the JavaScript readability standards, and I could not get it to work with their formatting. There was some bug in the JavaScript compiler of the time that whitespace mattered. And so I wound up checking it in broken, got the readability badge and immediately fixed it. It's like that was another one of our little hacks to get this working.

**Lenny** (00:44:06):
**Sam Schillace** (00:45:22):
I'm guilty of that. I mean, I like to play with stuff. I tend to think with my fingers as much as anything else. So I actually think there's a good place for just play with the tech a lot and figure out what it's good for. What I've evolved to doing these days with my teams is I pick what I call north stars that I think are interesting, useful things to get to rather than just messing around. What's a cool thing that I think might be buildable with this? 

**Sam Schillace** (00:45:49):
So right now we're doing these multi-agent systems. We're trying to figure out how much independent work they can do without a person holding their hand. And so a nice domain to test that out in is programming, because you don't have a whole lot of... You just give something a Python environment and a file system and that's it and that's all it needs. And so you're not distracted by connectivity issues or whatever.

**Sam Schillace** (00:46:11):
So one of the problems right now is go write the eye in Python. That's a problem I could give to an intern and it would take them a summer to do some halfway decent job of it. It's a thing you could expect a reasonably competent programmer to do, mostly independently. And so it should be possible for the system, if it's independent at all, to go do that. So is that useful by itself? No, because we already have the eye, it doesn't matter. But if we build a system of programming agents that can self-monitor and self-correct and bug themselves, that can build things that are roughly that scale of complexity, that's valuable. That would be a valuable thing to have. 

It's kind of interesting too, because that system already, it's produced a bunch of good insights. One of them is its kind of complicated and then hard to debug it. It's this asynchronous system of stochastic agents. That's a lot of stuff to deal with. So we wrote a debugger agent. And debugger agent watches stuff, and when there's a problem somewhere, it goes and figures out what the problem is and then gives you a nice explanation of what you broke and what needs to be fixed. And we haven't turned it loose on actually fixing things yet because we don't trust it, but it's very helpful as an assistant [inaudible 00:47:15]. We had one that documented itself too. That's the other one we did recently. Just turned it loose on documenting the code base and did a pretty good job of it.

**Sam Schillace** (00:47:21):
So it's starting to produce interesting stuff, right? Because we have these north stars that we aim things at. And I think that's maybe a good antidote to this. Just playing with tech without being focused doesn't tend to produce anything that's super valuable. But picking these, even if they're arbitrary goals, as long as they're real goals that you're trying to get to, that's useful, right? Where you're like, "I wonder if I can get this to work. I wonder if I can build this thing." Then grind away at that for a week and see how close I can get. See what I learned about why it's hard. That's probably better than just like, "Let me poke at JavaScript for a while."

**Lenny** (00:47:59):
It's also different, I think, at a bigger company where you need to achieve something, versus I think as just an engineer out of college just playing around, like, go for it, right? It's just like, what's the worst that could happen?

**Sam Schillace** (00:48:09):
Even the early days of Writely, the very... I mean, we had a goal from the beginning. The beginning was like, "Can I write a word processor in a browser?" That was literally the problem statement, right? It was like, "I have content edible, I have Ajax or JavaScript. Can I put these together and something that feels like a word processor? Let's go do that." It's kind of half messing around with tech, but it's also half an actual goal. So I don't know. 

**Sam Schillace** (00:48:35):
I like playing around with... I think a lot of the good product ideas, most of the good product ideas actually come up from engineering. So I think there's a lot to be said for, get familiar with tools, particularly weird esoteric combinations of tools can often be useful. If you understand or three things... At Google, I was one of only two people in the company who had the code readability, which is the right to check in code in this language, and both a backend language, which is the monitoring language, Org Mode, a middle tier language, which is Java, and a front language, which is JavaScript. No one else would do that full stack. I think it's useful to have that broad perspective sometimes.

**Lenny** (00:49:15):
Sam, the Renaissance man of all languages.

**Sam Schillace** (00:49:19):
Yeah, ADD more like it, but yeah, I pay attention to things.

**Lenny** (00:49:22):
I wanted to follow this thread a little further around being good at these what if questions. It feels like you've built this, or maybe you were born with this skill of thinking in the future, thinking about what's possible, thinking about where things are going. Is there anything that you could recommend to people listening to get better at the skill? Because for a lot of product people, this is really important to figure out, where could we be going and let's work back. 

**Sam Schillace** (00:49:45):
This is a really interesting question. And I may actually write, I've been thinking about writing a book from some of my Sunday letters, and this is maybe the frame of it. So I'm curious to see how flamed I get from saying this, it'll be interesting to see. I think there's this weird thing that I've noticed. I go talk to university kids and stuff like that, and there's this weird thing I noticed where when I was in university and I would talk to old guys like me, they would all say the PC is this stupid toy, whatever, it's not real computing, go on a mainframe or whatever. And my attitude was like, "Out of the way, old man, just like, you're irrelevant. I'm going to go do this thing. It's awesome." And go, go, go. 

**Sam Schillace** (00:50:21):
And now when I talk to kids, I actually had a slide up at Michigan when I was talking recently that was titled, okay humor, and the professor actually put it up there. Because this generation is very pessimistic and doesn't seem to be quite as engaged and energetic about solving problems. And I've been puzzling through it. And I think maybe there's a bunch of different things that intersect.

**Sam Schillace** (00:50:41):
I think one of them is, I think they all have to do with the willingness to take risk and to fail, honestly. I think that's really where it comes from. So I think you see a lot of filtered content. And that filtered content presents low probability events like five and six-sigma events as though they were normal. So you see everybody makes $100 million in their startup in the first three months. So if your startup isn't making $100 million, you're an idiot. There's that stuff. There's also, you're living out loud, so when you fail in that context it feels very painful. 

**Sam Schillace** (00:51:12):
But I think there's also for elite students, like people at these elite schools, they're hard to get into. I went to Michigan, "You're kind of smart. Michigan's a good school. You live nearby, go apply to that one." Nothing serious about it, but kids in the elite schools, their lives are highly curated going up to getting into a school like that now, right? Those students like, "I didn't do sports, I didn't do extracurricular. I was just a weird nerd having to be good at math." And so I think there's that as well. If you're highly curated where you've spent a lot of your life thinking, "Everything I do has to have a reason and an output." It's very hard to just mess around and do something that might lead down a surprising path, right? So that's the curation is part of it. 

**Sam Schillace** (00:51:55):
And then I think just in about the mid '80s when I graduated from high school, we stopped letting kids just play on their own, unsupervised outside with other kids. I grew up in this neighborhood full of, it was like the faculty ghetto for this small university my dad taught at, and we just ran wild. It was on the estate of widow of Dodge Motor, founder of Dodge Motor, so we had a couple hundred acres of swamp and fields to go run around in. We did hair-raisingly, dangerous things that my parents never knew about, and really explored and had fun. 

**Sam Schillace** (00:52:27):
I think if you put all those pieces together, I think there's much less of an ability and willingness and skillset around experimenting to the point of failure, making a fool of yourself, having bad ideas. I send stupid emails to Satya at Microsoft all the time where I'm just like, "I don't know what the hell he thinks of me at this point." Because I send him all these goofy ideas. I think he actually gets it and he's like, he likes it, because I don't think people usually do that for him. But I'm just like, "Man, this is..." Then I'll send him an email a week later. I'm like, "Yeah, that was a dumb idea. Sorry about that. I've decided that wasn't a very good one."

**Sam Schillace** (00:53:01):
But I think you cannot dance if you can't... If you're afraid to embarrass yourself. You cannot succeed if you're afraid to fail. That's just how it is. You have to have that sense of play. You have to have that sense of, it's okay if this doesn't work, I'll iterate on it. I have this personal motto, which is, from error comes virtue. Because I'm a maker, I make stuff. And I fuck it up all the time. I have poor motor skills, so I make mistakes constantly, and then I just figure out how to make the mistake into a virtue somehow. So I think it's a really good skill to have. The saying I took on this year and I really, really like it as my... I never had a personal motto before. I think it might be my personal motto, it's like, virtue from error.

**Lenny** (00:53:49):
Amazing. On this topic of failing. I think a lot of people hear this advice and they're like, "Yeah, okay, I need to fail more." It's hard to do. And oftentimes your performance at a company is negatively impacted. And it feels like for you it was just, you've done it enough times where fine, okay, it's going to be fine. I launch this thing, no one cares. I email Satya this thing, he ignores it or he doesn't. It's going to be okay. Is that maybe the key to this or is there anything else that you've done to allow you to be okay with failure?

**Sam Schillace** (00:54:19):
I feel like you can have a linear return on your effort if you manage things in a linear way, which is I think that tightly managing, okay, nothing's going to be surprising, I'm going to be within this boundary, I'm going to slowly accrete value, I'm going to play this game, whatever. I think you can have a nice linear, boring return to your career and you'll climb the ladder, it takes 30 years or whatever. I don't have the patience for that. And I think the way you get extraordinary returns is you do extraordinary things, right? You have to take bigger risks, and have more interesting shots to have this kind of extraordinary result in your career. 

**Sam Schillace** (00:54:56):
I feel like I always tell people, I think... I mean, I pitch this because I've observed myself and thought about what has been successful in my career. It's not a thing everybody can do. I'm just kind of like this. I never really fully grew up. I'm kind of this weirdo. I still feel... I'm 57 now, and I feel like I'm about 17. I'm still very immature and like to mess around with stuff and play with things. So not everybody can do it. But I think there's, at the end of the day, the reason you get ahead in your career is you had a lot of impact. And the reason you had a lot of impact was because you picked something that you're good at that you did with a lot of intensity that wound up having impact, right? And so I think the good at part of it is hard too. We tend to undervalue the things we're good at. We tend to think work has to be unpleasant. And so if something is easy and fun, we don't tend to think it's very valuable.

**Sam Schillace** (00:55:51):
So I think lots of people gravitate in this direction of, let's go do unpleasant things and grind our way through the career, because that's the way to make it. But the reality is, you should go do the thing that you feel guilty to get paid for, if there's a thing like that, and do the hell out of it, right? Do it as hard as you can. If you get pleasure from doing something that people want to pay you for, do it the best you can do it, as hard as you can do it. And if that's messing around and playing around with cool ideas, do the hell out of that. 

**Sam Schillace** (00:56:19):
Work doesn't necessarily have to be hard. It often is, but it doesn't have to be. And the best case is that it isn't. The most impact you'll ever have is where you're in that mode where you're just in the flow and doing your thing and you're happy to do it and you can't quite believe they pay you and you don't understand how you're getting away with this, but it's super cool anyways, right? I think that's the career thing that makes sense to me. At least that's what I've done. Who knows? It's all luck sometimes, so it's hard to replicate these. Everybody has a different path.

**Lenny** (00:56:50):
Amazing. I love that advice. It's exactly where I was going to take our conversation, so I love that you took us there. It makes me think of, I'm reading Charlie Munger's Almanac, which just came out through Stripe Press. And Warren Buffett and Charlie Munger's whole philosophy is, when you find an advantage, just go huge. Just go big, right? Make one bet a year. But when you find that, go for it. Don't buy a little bit at a time. And I love that. That's exactly what you're saying.

**Sam Schillace** (00:57:18):
Sometimes things don't make sense either. So I'll lean over and show you, for people with the video. That's an instrument I made. It's an instrument. So the top of that's a piece of redwood, this one right behind me with the cat eyes, the reason it's got these weird cat eyes, by the way, this is virtue from error right there, I dug this piece of wood out of the forest. It'd been sitting on the forest floor for 80 years trying to not rot and doing a pretty good job of it, because it's Redwood.

**Sam Schillace** (00:57:43):
And there were knots in it. So those two cat eyes are where the knots were. There's another knot right here that I couldn't get out. But there's two knots in there that I had to carve out of there. That's a very weird design that I did by hand. It doesn't quite work. It's kind of a failure. The arch of it's a little bit too high, so it's a little hard to play, because the pick hits the top because the strings get a little bit close to the top. So like that... 

**Sam Schillace** (00:58:02):
But that's an experiment. I was playing around. I wanted to do this thing. It was fun to do. It was a passion project. Now it's just hanging on the wall. Not everything works. Clearly I don't have a career as a luthier either. So it's more just a fun thing to do. But that's just a good example of the... I don't know. Sometimes I don't even understand why I do stuff. You just do it because you do it. Because it makes some sense to you.

**Lenny** (00:58:25):
Many people are in the opposite boat where they don't like what they're doing, they're miserable, but they have to have a job. They need income, they need to pay their rent, feed their family.

**Sam Schillace** (00:58:33):
I know, I realize what I'm saying is very privileged, and I am sorry about that. But from some perspective.

**Lenny** (00:58:38):
But I imagine you were also in those situations occasionally. Is there anything you recommend to folks that aren't in that, I would do this for free, I'm so excited about this work? Do you recommend try to get out that as soon as you can? Is it enjoy it as much as you can, get the most out of it?

**Sam Schillace** (00:58:53):
I mean, I've done plenty of things for money. I've done plenty of jobs to make money for my family, things I did not enjoy doing. All I can say is really, I stopped doing those things as soon as I could stop doing them. Not only as fast as I physically could, because I definitely had that Calvinist, oldest boy thing of, must provide, must suffer kind of thing. So it took me a long time to realize, no, actually I'm really creative. I don't have to be like everybody else. I can have my own path, and I can be this weird engineer. I always joke that I'm an engineer. Two is a prime number. It's just like I'm kind of a programmer, but not real... I'm this weird non-linear person that only barely fits into the programming world. But it's okay. It took me a long time to figure out that I could do that, that I could be comfortable with that part of myself. 

**Sam Schillace** (00:59:40):
And I'm fortunate enough now that I've done enough things and have enough of a connection and network that people understand who I am and the value I can bring. And so I get away with doing that stuff that I like doing. So it is kind of privileged advice, and it's not something everybody can do at every stage in their career. Certainly earlier stages you often have to make compromises, but I still think it's worth paying attention to, right? When you're working, what makes you happy? What is the stuff that you feel guilty for getting away with? When I started managing people, I couldn't understand why people were paying me and I wasn't writing code, because all of my energy was attached to, "I can produce a lot of lines of code every day." And I asked my boss at the time, "Why are you so happy with this? I'm not writing anything." He's like, "I don't know what you're doing. Everywhere you go, it gets better. So just keep doing whatever it is you're doing."

**Sam Schillace** (01:00:29):
And that was one of these moments where I was just like, "Oh, I could do something else and it's kind of fun. I like talking to people all day. That's great. They're going to pay me for talking to people all day. If they seem happy, I'm happy. Let me just lean into this for a while and see where it goes." So I think you just look for those moments when somebody is willing to let you do something that you feel happy to do, surprisingly happy to do, or doesn't feel like it's the thing you "should be doing". If you get those surprises like this, I think this goes back to this openness, the optimism that we were talking about. You have to be receptive and attentive to those moments when they show up. So I think they are in every career. If you listen for them, you'll see stuff show up where you don't think of it as who you are, but somebody else sees it in you and if you can be open to it, you can do these pivots.

**Lenny** (01:01:21):
When you talk about that, that makes me think of Seth Godin has this really important advice that's always stuck with me, that no matter what job you're in, just try to enjoy it and do the best version of that job you can, because you'll enjoy it more, that you'll end up being more successful, and it's just a good habit to just like, "I'm just going to do the best I can at being a waitress at this place. I'm just going to do the best at greeting people entering the Apple Store."

**Sam Schillace** (01:01:45):
Absolutely. Yeah, I think that's absolutely right. And even more than that, just find a way to bring yourself to it, right? What is the thing that you can do in this role that is unique to you that you're the most comfortable with, right, where you really have high impact. I don't know. I tend to be very, it's kind of a joke because I'm a programmer, I tend to be a very binary person, right? I'm either all in or all out on something. So whenever I do something, I do it with just a ridiculous amount of intensity, for better or for worse. So I find the ways to do stuff. I tend to be very unhappy if I can't be intense in something successfully, and then if I can be intense in it successfully, I'm happier and the people around me are probably less happy, but stuff happens. Anyways, I get things done.

**Lenny** (01:02:35):
Speaking of getting things done and being intense and working things that are really interesting, you're responsible for some of the cutting-edge work happening at Microsoft in AI. You're spending a lot of time in AI. I'm curious to get your take on just what you find interesting, where you think things are going, what people should know about AI. I'll share a couple of quotes that you put out somewhere that I have here that I think are cool. One is, "AI isn't a feature of your product. Your product is a feature of AI."

**Sam Schillace** (01:03:01):
I love that one. Yeah.

**Lenny** (01:03:03):
Another is, "It'll be possible to add some value by building AI into your product, but really transformative massive value will come from building apps and solutions that won't work at all without it, that treat it as a true platform."

**Sam Schillace** (01:03:14):
Yeah, I think both of those are really true. So what I'm working on is, most of the industry right now is focused on, when you talk about somebody who's working in AI, it's somebody who's creating models, right? It's somebody who's figuring out how to do some new open source model or somebody who's doing some new training or make some model bigger. And I think that's very, it's valid, useful work. It's just not the kind of work I like to do very much. And a lot of people are doing it. 

**Sam Schillace** (01:03:38):
And so I'm an app builder, I'm a tool builder, and so I don't create models, I consume them, right? I want to build things around them. And so when I started with Microsoft, started working on GPT-4 with Microsoft in September of last year, my immediate reaction to it after picking my jaw up off the floor, which we were all doing in the early days, was, "Okay, this is cool, but in some computer science sense, it's just this function, this stochastic pure function that just takes a character array and rearranges it and hands it back to you. That's not much of a building block for building programs. We need state and we need control flow, and orchestration, and call-outs." 

**Sam Schillace** (01:04:19):
So that just started me down this rabbit hole of thinking about building the Semantic Kernel, which we built, and then building Infinite Chatbot, which was next, and these other projects we've been working on. And the more I think about this stuff, the more I do think those two quotes are good quotes. I think what's going to happen over time... I actually think we're at the beginning of this just gigantic disruption in the software industry. I think the way that the internet made distribution of information free, I think AI is going to make pixels free. 

**Sam Schillace** (01:04:49):
So pixels are expensive to produce now, they take programmers and they take lots of infrastructure, and putting a pixel in front of the user is a hard thing to do and lots of software is predicated on that. Lots of business is. The way lots of businesses were predicated on it being hard to distribute information 25 years ago. But you can see this already with things like just images, right? Two years ago, if you wanted a piece of digital art, you had to go invent Photoshop, learn to use Photoshop, use Photoshop to do the drawing, build the skills up. That's a lot of work to produce those pixels. Now it's like, I want a picture of a cat riding a bike eating a banana, done, right? So those pixels got really free. 

**Sam Schillace** (01:05:28):
And the similar things are happening in the business world as well, and I think it's just going to start to happen everywhere. So you can draw... This is what if, let's go ask some what ifs. So what if the models get really good at planning, so they get more independent, they can do longer and complicated things? What if the multimodal stuff gets really good so that they can both consume and produce dynamic UI like I was talking about? What if we figure out a good way to store state, this is my bots or docs thing. So what if do we figure out a good way for you to really highly personalize something so it knows you really well and you trust it with confidential information? 

**Sam Schillace** (01:05:59):
If you have all of those things, you're just going to spend a lot of time talking to that agent. It's like, what would you do... If you imagine you're the richest person in the world, you've got 100 of the best people working for you, and a chief of staff, and they're tireless, and they never fight with each other, they do everything you want. With that staff supporting you, what are you doing with software? What are you doing when you're sitting in front of a screen? Well, you're probably communicating intention and you're probably consuming some either entertainment or some of the products of that intent. And that's about it. You're not messing around with pokey static apps and stuff. That doesn't work, right? You're just telling your staff to deal with stuff for you. 

**Sam Schillace** (01:06:36):
So I think that's where we're headed, I think, in the world of software at least. Things are going to get more dynamic, more intentional, more semantic, more fluid, then more personalized. I think there's a ton of problems to be solved to make that vision real. But I think this feels to me a little bit like seeing the Palm maybe, or the early iPhone, where you're just like, "Okay, I get it. Phones are going to get interesting. That's a new device. Now we got to go do a whole bunch of engineering before they actually are as useful as they're today." Right?

**Sam Schillace** (01:07:09):
So I get it. I think software is going to change radically now. I had the same feeling when we started doing... This is going back to G Docs again. It's another lesson. It's another one of these category shifts. The second we got Writely up on its feet and I was like, "Ah, the browser is actually a platform that you can actually build real apps in. I get it, the world's going to change." And we had a ton of stuff to do, right? Nobody really understood distributed systems. Nobody understood how to build stuff in multiple places at once or how you deal with replication, how you deal with security, all kinds of hard... All the development patterns had to shift from Waterfall, to Agile, to CI-CD, all this stuff had to change to fully realize that world.

**Sam Schillace** (01:07:51):
But I remember back in 2005, this very quick... And the people who were the strong proponents, I think all saw this, instantly saw that the world had changed and there was this new category. And I have exactly the same feeling about generative AI. Like, yep, software's going to totally change. These businesses are going to totally change. It might take 10 years to really work through all of it, but yep, door open, new room, new game, start coloring in the blanks, right? Let's go.

**Sam Schillace** (01:08:19):
So that's where I think we're going. And that sounded really certain, it probably sounded more certain than I should sound. I think there's a lot of, probably a quarter at least, if not a half of what I just said is wrong in some way. So we're going to learn a bunch of stuff along the way. And there's a lot of work to do, a whole lot of work to do and a whole lot of unanticipated side effects are going to pop out, and there's just a whole lot of stuff to get that to be real the way there was with all of the last transformations. But I think this is just a giant category shift. I think it's just incontrovertible that it is. 

**Sam Schillace** (01:08:55):
It's kind of funny when Gemini came out, all the press take was like, "Oh, it's not that different from GPT-4. I guess we're done with AI now, we can go back to bed." I'm like, "That is the dumbest possible interpretation of that story that you could come up with I think." Of all the takes you could have had on that, I think that was the dumbest one honestly. It could say many things about either company. It could say many things about the science. But, "Guess there's nothing here to see." Is not one of them.

**Lenny** (01:09:28):
For somebody listening that wants to not fall behind on this and or find opportunity for their product, other than just playing with it, which is what everyone is always saying, just like, "Play with it. Use ChatGPT, use Bard, and all these things." Is there any advice you'd give listeners for how to approach thinking about AI, how it integrates into the stuff they're doing?

**Sam Schillace** (01:09:48):
Yeah, I agree with you. Just play with it, is not really great advice. I think the best technique I've really seen for learning things is to pick a thing to do with the thing you're trying to learn, right? Even if it's an unreasonable... Even if it's a goofy, weird thing, right? Like I'm going to figure out how to draw funny pictures with this programming language or whatever. Even if it's a dumb thing like that, picking some arbitrary goal and being a little bit stubborn about trying to get yourself to it is a good way to learn stuff.

**Sam Schillace** (01:10:17):
And then the question is, "What goals are you picking?" So try to pick goals that lead somewhere maybe at least a little bit interesting. So if your goal is just like, "I'm going to mess around with ChatGP for an hour." That's not really much of a goal. If it's like, "I'm going to go try to GPT that can do this part of my job, let's see how close I can get." That's more interesting, right?

**Sam Schillace** (01:10:41):
And I do think unfortunately, one of the other ways in which this is very reminiscent of the early dot com era, and I think plenty of people have said this, is this sense of exhaustion in keeping up. There's so much stuff going on right now. And that's I think another good strong indicator that something really big is going on, where it's just very, very difficult to keep track of all the stuff that's happening. It's kind of interesting, because I remember, just to kick crypto's corpse one last time, there was a tweet at the beginning of the year that I saw that somebody was like, "Yeah, it took the AI bros a week to come up with as many use cases as crypto came up with in a decade." Which definitely feels true, right? It's just so much stuff going on. And I think you just have to try to keep track of it. 

**Sam Schillace** (01:11:29):
One of the other things I think is going on in the moment, which feels a lot like the cloud moment to me, is it's hard to get the first idea. The zero to one is hard. Understanding that there's something there at all is the really hard part, because you have to be lucky and you have to be talented and you have to look in the right place and do some very hard work. But once you understand that there's something there, like the cloud model works, or their generative AI matters and scale works and stuff like that. Once you're there, the one to many, all the optimization stuff, that happens in parallel, it happens really quickly. Many, many, many people can do it. There's a lot of energy. It'll just go really fast. 

**Sam Schillace** (01:12:05):
So I think we're in that phase where just like we're in the elaboration phase where we understand this step and people are just filling in all the white space as fast as they can. So that'll slow down eventually, hopefully. We'll see what the next year brings. But yeah, it's a hard time. It's hard for professionals even. I think you just have to read a lot. You have to think a lot. You have to play with stuff. You have to choose your battles. You have to pick good targets. Pick a goal in your domain that would matter to you if you can get to it, and then go try to solve that problem with some specific technology and get to know that technology.

Maybe pick the technology based on how popular it seems, if you want to learn something lots of people [inaudible 01:12:44]. Those are all good. I think you just have these kind of mundane... I don't think it's really a secret, I don't think. They're kind of mundane strategies, but you just have to pick some stuff and do some homework. And there's no magic single bullet to learning this stuff. You just have to run. It's like, "How do I run this sprint without getting out of breath?" You don't. You're going to be out of breath, run hard. It's just what it is.

**Lenny** (01:13:09):
I love that advice. And I love it connects to everything else that you've been talking about is, find some problem someone has, find some value you could provide, and then think about, how can AI potentially provide that? I think that's really practical. Great advice. Maybe a last question just around Microsoft. It feels like Microsoft is firing on all cylinders. It feels like it's become one of the most innovative companies out there. It feels like Satya is known now as the most innovative, best executing CEO out there potentially. That's just what it feels like. Being on the inside, I'm just curious, what is it that you think Microsoft is doing so right or how they think that enables them to be so innovative and continue to be such a behemoth as so much has changed in tech?

**Sam Schillace** (01:13:52):
There's a couple of things. First of all, I think very, very highly of Satya, or I wouldn't be there. I really, really like Satya. He is very much what he appears to be from the outside. I've had plenty of candid private conversations with him and watched him in meetings and stuff like that. He's a very decent, genuine, honest, high energy, caring individual with a ton of empathy. He's really motivational in a way that is not destructive. He believes very strongly that a leader's job is to raise the energy of the organization and he really lives that. And I watch him in meetings where I'm a domain expert and I cannot believe how engaged he is in stuff and how much he understands about something that I know he's not as deep an expert as some of the people in the room are and he's fully in there. So he is a really incredible leader in many ways. That's one thing. 

**Sam Schillace** (01:14:44):
I think another is that culture is very humble, honestly. I mean, it's interesting going from Google to Microsoft. And I don't want to draw comparisons or anything like that, but I think there are definitely similarities and differences between the companies. And I think one thing that stands out with Microsoft is it's a humble culture. It does unglamorous work all the time to make businesses be successful. So it's got that sort of mindset of just hard work and humility, which I value a lot. And then I think there's just, I mean honestly, there's just a fantastic number of really talented people working there. 

**Sam Schillace** (01:15:18):
It's kind of funny, this year I've been writing a lot of patents, because there's just a lot of stuff going on in the world. And I've written more patents this year by a lot than the rest of my career combined. And I commented on the number. I'm like, "I've written 15 patents this year." I commented to the patent attorney that I work with. He's like, "Ah, that's nothing. The chief science officer wrote 700 of them one year during the mobile boom." It's like, whatever you feel about patents, and I don't necessarily love patents, although it's part of my job to write them, but that's the kind of people that are there, these just fantastically talented people with just really deep experience at a lot of different levels. 

**Sam Schillace** (01:15:58):
I think that's part of it too. There's just a lot of really good folks there. Kevin Scott, who I work for, is one of the smartest... He's probably the smartest person I've ever been fortunate to work directly with. He's definitely one of the smartest I've ever met. He's pretty fantastic. And the group around him is pretty fantastic, and the leadership in Windows and Office is pretty fantastic. So it's just a lot of good people and a lot of good attitude, and a good leader I think is the answer. And luck. It's always luck too, right? Kevin and Satya made a bet on OpenAI a few years back, and they're doing some extraordinary things with capital raise and the support of that technology and stuff like that. That doesn't happen by accident either.

**Lenny** (01:16:39):
No drama there, by the way.

**Sam Schillace** (01:16:41):
I wouldn't know anything [inaudible 01:16:42] there. I hear it's calm. I stay far away from it as possible, honestly. 

**Lenny** (01:16:47):
Most under-the-radar startup out there. Amazing. Sam, is there anything else you want to share before we get to our very exciting lightning round? Is there anything you want to leave listeners with?

**Sam Schillace** (01:16:58):
Mostly I think probably take all of this as more my personal opinions and not Microsoft's official stands. This is just me being an engineer. I'm not here as a Microsoft representative necessarily. But yeah, I don't know. Build stuff, solve problems, build stuff. That's what it is, right? That Jobs quote-

**Lenny** (01:17:21):
Fuck around. 

**Sam Schillace** (01:17:21):
Fuck around. Well, that Jobs quote is right. The world was built by people just like you. That's that's the thing. It's really true. You don't have to have permission, you just have to have energy.

**Lenny** (01:17:33):
With that, we've reached our very exciting lightning round. Are you ready?

**Sam Schillace** (01:17:36):
Probably not.

**Lenny** (01:17:38):
Great answer. Sam. What are two or three books that you've recommended most to other people?

**Sam Schillace** (01:17:44):
I like weird book. There's this book called Invisible Cities by Italo Calvino, which is this very beautiful meditation on the nature of cities and the nature of Venice. And I read it the first time I was in Italy right after college, and it just blew all the circuits in my brain when I went to Venice, and so that was pretty cool. The other one I recommend to people with some caution is this very intense and disturbing book called The Wasp Factory by Ian Banks, which is probably the creepiest and hardest book I've ever read, but it's a very interesting psychological deep dive. So those are both fiction. If you're looking for business advice, I think the business advice one is probably, Where Good Ideas Come From, Steven Johnson. I really like that book. I think some of the stuff about the adjacent possible. I think it's an old book now, but I think it's pretty timely still. I think he had some good stuff in there.

**Lenny** (01:18:36):
What is a favorite recent movie or TV show that you really enjoyed?

**Sam Schillace** (01:18:40):
My favorite one right now, my guilty pleasure is watching Gary Oldman be a completely disgusting over-the-hill British spy in Slow Horses, which is pretty fun. And I'm actually having a little fun with the retro monster stuff like Monarch and stuff like that. It's kind of fun to watch. I don't know. I have absolute junk food taste when it comes to media.

**Lenny** (01:19:04):
Love creepy monsters and bugs.

**Sam Schillace** (01:19:06):
Yeah.

**Lenny** (01:19:07):
I love it. 

**Sam Schillace** (01:19:07):
Shooty science things that blow up a lot. I'm not very deep.

**Lenny** (01:19:13):
By the way, have you seen Scavengers Reign, Scavenger Reigns, Scavenger Reign? Okay. You'd love it. It's on HBO. It's incredible. It's an animated sci-fi thing, and it's very creepy, slimy, kind of alieny things, and it's so beautiful. Do you have a favorite interview question that you like to ask candidates when you're interviewing them?

**Sam Schillace** (01:19:32):
I have one that got banned at Google, and I liked it. I still think it's a fun question. It's, how many zeros are at the end of 100 factorial? And the reason I like it... Yeah, it's like, you made the face, right?

**Lenny** (01:19:43):
Going to ask ChatGPT for this answer.

**Sam Schillace** (01:19:45):
Well, here's the thing. Well, don't though, because the reason I ask it is, it seems like an unreasonable and impossible answer. And if you sit down and think about it a little bit, I'm not going to tell you how to reason through it, but you can figure out the answer to it in a few minutes. And so the reason I ask is not to get to the answer. It's because I just want to see how people react when I give them something that seems impossible and unreasonable. 

**Sam Schillace** (01:20:07):
And some people just back off and refuse to engage with it. And some people are just like, "I don't know, let me roll my sleeves up and see how far I can get in this thing." And if you do that, you can actually get through it. And I just think it's interesting, because that's building stuff, right? That's a good signal of when somebody tells you you can't write a word processor in the browser and you can't do collaboration. Do you roll your sleeves up and deal with it or do you fall over?

**Lenny** (01:20:32):
And what was the question again? Just to [inaudible 01:20:34]. 

**Sam Schillace** (01:20:33):
How many zeros are at the end of 100 factorial in decimal?

**Lenny** (01:20:39):
And then why did it get banned?

**Sam Schillace** (01:20:41):
I think it got known, and somewhere... Actually, the funny thing is, one of their more senior directors, actually he's a SVP now I think, Dave [Bezeras 01:20:51], I interviewed him when he came in, and I asked him that question. And his response was, "I don't do math. Next question." And so I failed him. I was the veto. And they have this policy where... We're friends now. They have this policy where one veto is actually a good signal. If you're controversial as a candidate, they would take a hard look at you. And so my veto may have gotten him higher, because I was like, "I don't know, he wouldn't answer this question. That's a red flag for me, so don't hire him." And he turned out to be a great person. So it's maybe not a good question anyways. 

**Lenny** (01:21:20):
That comes back to one of your other lessons of the best ideas have some people that are just very anti that idea. 

**Sam Schillace** (01:21:26):
Yeah. Yeah. Yeah. 

**Lenny** (01:21:27):
It all circles back. Next question, what is a favorite product you've recently discovered that you really love?

**Sam Schillace** (01:21:34):
My father-in-law and my brother-in-law worked for the American car companies. And I've never had American cars. I just drive Japanese cars, because I grew up in Detroit and just hated that culture. And so recently we bought a Ford Mustang Mach-E, the electric Ford Mustang, and I just love the shit out of that car. I don't know why. It's just a really fun car to drive. It's very surprising to have this American muscle car that I'm just really... An electric American muscle car that I really like. So that's probably the current product I really am enjoying the most right now.

**Lenny** (01:22:03):
Next question, do you have a favorite life motto that you often repeat to yourself, find useful share with friends or family, either in work or in life?

**Sam Schillace** (01:22:11):
Virtue from error. Yeah, I think that's... It's become one for me, and the more I say it, the more I like it. But I just like this idea of, you're going to fuck up, make something from it and be creative with your mistakes. I like that a lot. So I think that's at least my current one.

**Lenny** (01:22:33):
And say it again, just so people get it.

**Sam Schillace** (01:22:35):
There's lots of different ways to say it, but I just like, virtue from error, is probably the cleanest way to say it, or from error, virtue.

**Lenny** (01:22:42):
Final question. Apparently you're the only person who has sold both a company to Google... I like that you already know where I'm going. Both a company and also 200 pounds of blood sauce.

**Sam Schillace** (01:22:53):
Yes.

**Lenny** (01:22:54):
Both to Google. Tell us the story.

**Sam Schillace** (01:22:56):
The story? So I have a friend who dropped out of the tech industry to start a company up in San Francisco called Boccalone, which was an artisan salumi thing in the Ferry Building. And so he'd make blood sausage and stuff. So there was this wonderful insane chef back in the day when Google had really high-end cuisine in the campuses, probably like 2005 or something, or no, sorry, probably 2008, something like that. And so my friend Mark shows up. This Chef JC had the word foie gras tattooed onto his knuckles. So that's the kind of guy he was, he was just super awesome. 

**Sam Schillace** (01:23:30):
And so I had Mark show up to talk to JC about buying some of those products, because I was an investor in that company. And he showed up with a bag of blood sausage that was, he's like, "Here, you should take this one and put it in the refrigerator." And like, "Why?" He's like, "It's dripping." I'm like, "It's all right. It's fine." He's like, "It's dripping blood." Because they hadn't got the packaging right. So we showed the blood sausage to JC. He cooked some of it up. It was really good, and he was like, "Yeah, that's awesome. I'll buy a couple hundred pounds of it." And so technically, because I was an investor in that company, I sold both the company Writely and 200 pounds of blood sausage to Google, which I think is a unique accomplishment. And I would just absolutely love to meet anybody who has also done that. We'll have a party.

**Lenny** (01:24:13):
Did you get stock though, for that blood sausage?

**Sam Schillace** (01:24:16):
No, I did not get stock or anything. That guy was crazy, at one point... Just a quick JC story. At one point Google rented some goats to graze the hillside across the way. And JC was a very non-politically correct, non-woke kind of guy, and he did not like all the sort of attitude at Google. So when these goats were across the hill, he bought a goat carcass from somewhere else and roasted it over a spit and carried it whole through the line for lunch one day to serve up, just to completely tweak people. So that was a different time at Google.

**Lenny** (01:24:51):
The good old days. 

**Sam Schillace** (01:24:52):
Yeah. 

**Lenny** (01:24:53):
Amazing. Sam, that's it. We did it. Two final questions. Where can folks find you if they want to potentially follow up on any of this? And then how can listeners be useful to you?

**Sam Schillace** (01:25:02):
Well, I have a Substack, which is Sunday Letters From Sam, that I write a letter roughly every Sunday, that I've been doing for about 10 years. Not that particular... Well, I've been writing letters to my engineering team on Sunday since I was the head of engineering at Box, and I think that's 12 years now or something. I just started doing it to keep myself accountable, and people liked it, so I just kept doing it. So now I do it in public. I repost them on LinkedIn. You can find me there. You can message me on LinkedIn if you want to. I'm hesitant to give out my personal email address, because this is probably going out to a lot of people and I don't want to get spammed. 

**Lenny** (01:25:37):
Smart, smart man. 

**Sam Schillace** (01:25:38):
Last funny story. At Google, my email address at Google got leaked somehow and a spammer... I was a little but notorious during the early days of Writely, and so a spammer used it for what's known as a Joe job, where you send something out, fake emails out, with somebody else's email address as the reply to. So several hundred million emails went out, and all bounced. And so for a while I had my own Gmail front end server that would filter them out for a couple of weeks until that died down.

**Lenny** (01:26:08):
Let's make sure no one does that to you right now.

**Sam Schillace** (01:26:10):
Oh, yeah.

**Lenny** (01:26:12):
You didn't answer the final question. How can listeners be useful to you other than not doing that, spamming things to you? 

**Sam Schillace** (01:26:17):
Oh, I guess, the thing I guess I'm interested in is people making interesting progress in the direction of that product vision that I talked about. Independent action, the UI part of this stuff, generating UI, consuming UI, all that stuff, I think I'm curious about that. I mean, and interesting ideas. Anything surprising that seems that you'd like to have somebody pay attention to. I entertain weird ideas all the time. I do my best to entertain weird ideas and live what I preach. So if you think you have something that's really resonating that you think you want to have somebody pay attention to, you can connect me. I'll take a look at it, I'll do my best. I won't look at stuff that's incremental and boring. It has to be actually interesting and disruptive. So I don't care. I'm not going to review the 27th memo writing AI chatbot thing that plugs into Outlook or whatever. I don't care.

**Lenny** (01:27:11):
I think that's a final good takeaway, is that's a litmus test for, are you working in something innovative? Which I think has been a great theme of this conversation. 

**Sam Schillace** (01:27:18):
Yes. Tell me something that'll piss me off. That'd be more...

**Lenny** (01:27:21):
Sam, thank you so much for being here. 

**Sam Schillace** (01:27:23):
My pleasure.

**Lenny** (01:27:24):
Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [4/19] Taking control of your career | Ethan Evans (Amazon)

**Ethan Evans** (00:00:00):
People think invention takes all this time, but you only need two hours once a month. The thing is, once you have one good idea, it often takes years to express that.

**Ethan Evans** (00:00:09):
So you had the idea to have a newsletter. I know some of the history of your newsletter. You've been working on the expression of that idea for years now. Jeff and Amazon had ideas like, "Let's have Prime shipping." Prime is still getting better and still being worked on. It's a 20 some year old idea. The Kindle, a decades old idea now still getting better. The point here is you don't need very many good ideas to be seen as tremendously inventive.

**Lenny** (00:00:38):
Today my guest is Ethan Evans. Ethan is a former vice president at Amazon, executive coach, and course creator focused on helping leaders grow into executives. Ethan spent 15 years at Amazon, helped invent and run Prime Video, the Amazon Appstore, Prime Gaming, and Twitch Commerce, which alone is a billion-dollar business for Amazon. He led global teams of over 800, helped draft one of Amazon's 14 core leadership principles, holds over 70 patents, and currently spends his time executive coaching and running courses to help people advance in their career, build leadership skills, and succeed in senior roles.

**Ethan Evans** (00:04:30):
Lenny, thank you a ton for having me. I'm super excited to talk about some of the things we have teed up today and to help people.

**Lenny** (00:04:37):
The first thing I thought we could chat about is The Magic Loop. So you wrote this guest post from my newsletter sometime earlier this year. It is, I don't know if you know this, but it's currently the sixth most popular post of all time on my newsletter across 300 plus posts. Did you expect this advice to resonate the way that it did, and why do you think it resonated as much as it did?

**Ethan Evans** (00:04:59):
So the competitive part of me really wants to analyze spots one to five and figure out, do they have an unfair advantage that they had more time? But I was very hopeful that the advice would resonate that way, because I put a lot of work into simplifying it and making it really easy to understand and follow. So I'm very pleased it has, but I was hopeful it would do so well.

**Lenny** (00:05:24):
Well, I will say sometimes they keep growing, so this isn't necessarily the terminal point for the post.

**Ethan Evans** (00:05:28):
The final position. Yeah.

**Lenny** (00:05:30):
Okay. So for people that haven't read this post, or maybe for folks that have and maybe could use a refresher, let's spend a little time here. Could you just briefly describe this idea of The Magic Loop that you wrote about?

**Ethan Evans** (00:05:40):
Yeah, absolutely. So The Magic Loop is how to grow your career in almost any circumstance, even with a somewhat difficult manager. It does assume that you're working in some environment, normally as an entrepreneur or with a boss. But the basic idea of The Magic Loop is five steps and they're very easy.

**Ethan Evans** (00:06:01):
The first one is you have to be doing your current job well. It's not possible to really grow your career if you're not considered at least performing at a solid level. Now, it doesn't mean you have to be the star on the team at this point, but what you can't have is your boss wishing that you were different. Like, "Ethan's not very good." So you have to talk to your manager and find out how you're doing and address any problems. So step one is do your job well.

**Ethan Evans** (00:06:31):
Then step two is ask your boss how you can help. Speaking as a manager, and I've talked to hundreds of managers, very few people go and ask their manager, "What can I do to help you? What do you need?" And so just asking sets you apart, and it begins to build a relationship that we're on the same team, that I'm here as a part of your organization to make you successful, not just myself. 

**Ethan Evans** (00:06:53):
Step three is whatever they say, do it. So you dig a big hole. If you say, "What could I do to help you?" And they say, "Well, we really need someone to take out the tray sheets day," and you're like, "Oh, I didn't mean that. I wanted exciting work. I don't want to do sort of this maintenance work or whatever." So do what they ask, help out even if it's not your favorite work. 

**Ethan Evans** (00:07:14):
Once you've done that though, and maybe you do that a couple times, the fourth step is where the magic comes in. You go back to your manager and say, "Hey, I'm really enjoying working with you. I'm wondering is there some way I could help you that would also help me reach my goal?" And whether that goal is to change roles or get a raise or get a promotion, you say, "My goal is I'd really like to learn this new skill. Is there something you need that would also help me learn this new skill?" And the reason this works is managers help those who help them. It's just human nature. We all do that.

**Ethan Evans** (00:07:52):
Generally, they're very open to meeting you halfway and saying, "Sure, I need this. We can rearrange it. We can find a way to meet your goals over time." Now for step four to work, you do have to know what is your goal, so you have to be clear on what it is you want. Well, that part's up to you. 

**Ethan Evans** (00:08:15):
And then step five is the easiest step of all. It's just repeat. So like lather, rinse, repeat with your shampoo. Step five is once you're working with your manager towards your goal and discussing where you're going, and you're helping each other, the magic of the loop is just go around and around.

**Lenny** (00:08:31):
I was going to ask you, why is it that you call it The Magic Loop? Also, we kind of dived right in, but what is the goal of this? I guess it's pretty clear maybe at this point of this helps you advance in your career, but whatever you want to share along those lines.

**Ethan Evans** (00:08:43):
Yeah, okay. Very fair. So I called it The Magic Loop because I pioneered it with my audience a few years ago. And it works so well, that people were writing back in and saying, "How do I turn this off? I'm in over my head now. My boss has asked me to do all these cool things, and I feel like I can't catch up, and I've already been promoted once and I need time to digest it." And it just seemed like it worked like magic. It worked in almost every circumstance. 

**Ethan Evans** (00:09:15):
There are of course exceptions where you have very exploitative managers who are like, "Oh, it's great. You're working harder, keep doing that, and they won't do anything for you." But those are rare. And then the purpose, yeah, to help you get satisfaction in your career. A lot of people are unhappy with their jobs. Many people want to move up a level or get paid more. Not everyone. Some people want to change what they're doing, they're bored. This is a path to all of that, because it's forming a partnership with your leadership to say, "Look, I'll help you, but I need you also to help me." And most good managers are very open to that.

**Lenny** (00:09:52):
When we were working on this, one of the pieces of feedback I had was I feel like I could just tell my manager, "Hey, I want to grow my career. What can we work on to help me get there?" And your feedback was like, most managers are not that good and not that thoughtful about their employee's careers. Can you just talk a little bit about that? People may be hearing this and be like, "Why do I need to do this? This seems like a lot of work."

**Ethan Evans** (00:10:15):
If you have a great manager, you may not need to do nearly as much formality. They may have given you good feedback, so you don't need to ask for feedback. They may have offered you opportunities to step up, and you've said yes to some and maybe no to others. That's fantastic. I designed The Magic Loop for the people who either don't know what to do or their manager is either not that good or just very busy.

**Ethan Evans** (00:10:37):
Remember, lots of managers have great intentions to help their employees, but they get busy with their own lives, their own work, all the things they're focused on, even also their own career. The manager is often busy thinking about their own needs, and so they mean to get to you next week, and next week drifts on for a year.

**Lenny** (00:11:00):
What has come up since this has come out that you would want to either add to, or tweak, or help people better understand? I imagine there's some criticism. I imagine there's a lot of, "Yes, yes, yes. This really works."

**Ethan Evans** (00:11:12):
Two things I'd love to clarify. The first is many people ask me, "Why do I have to do this? Shouldn't my manager notice what I'm doing? Shouldn't my manager help with my career? Shouldn't my manager be planning for me?" And what I say about that is what your manager should do and $4 will get you a cup of coffee at Starbucks. 

**Ethan Evans** (00:11:36):
The point of this loop is it's in your control. It is true that a good manager would do all those things I just mentioned, but not all managers are good and some of them need some help. And the thing I would just say about The Magic Loop is it's in your control.

**Ethan Evans** (00:11:52):
And so you can be upset that your manager isn't perfect, but move on from that and take control of your own situation. That's the first thing I'd say. The other big extension I would make is look, if you are a manager or a leader of any type, you can initiate The Magic Loop from your side, so you can talk to your employees and say, "Hey, what are your career goals? Would you like to form a partnership where you step up to new challenges and I help you get to your goals?"

**Ethan Evans** (00:12:26):
I had a lot of success forming this kind of partnership with my employees, where as they saw growth and success, they really leaned in and like, "This system works. You're actually investing in me now. I'll work extra hard." And I'm like, "Yes, and we can grow your team or grow your opportunity," and it was very win-win.

**Lenny** (00:12:46):
To give people a little bit of social proof, you mentioned some of the folks you've worked with on this. Can you share some stories, or stats, or anything to help people understand how helpful this ended up being to folks you've worked with?

**Ethan Evans** (00:12:58):
Yeah, absolutely. I'll tell one story from each end of the spectrum. And what I mean there is entry-level people and then high level executive leaders. I had an entry-level person write me back and say, "Look, when I learned about The Magic Loop, I was at a company and not doing very well. I started applying it. They offered me a $30,000 raise and a bigger job. And I turned it down because I got hired at this other company that was offering me even more, and I went there. And they've promoted me also," and he was one of the people who wrote in and said, his exact words were, "A year ago I was made redundant." So he is in the UK, redundant is their word for laid off. "A year ago I was made redundant. I got this first job and I got an offer for an increased salary, and then I got the second job and I got an increase when I joined that was even bigger." And he was in that situation of, "Mow I need to sort of slow down and digest all of that."

**Ethan Evans** (00:14:05):
On the complete other end, one of my best people I ever worked with joined my team at Amazon as what we would call an SDE II, which in Amazon is a level five employee. He grew with me kind of following this process to a senior engineer. Then he switched to management and ran a small team. Then he became a senior manager and he relocated with my organization. He opened a new office in another city, was eventually promoted to director running his own office of a couple hundred people. And this was over the course of about eight years. He went from a mid-level engineer to an executive with a team of 800 people. Now he was a very hard worker, but over this eight years we just saw all this progress.

**Ethan Evans** (00:14:56):
And then eventually he moved on. He founded his own startup, sold that, and now works as an executive vice president at one of the major online banks. And so his career in some sense has exceeded mine, but during that eight year span, he just grew so much. And this is the process we followed.

**Lenny** (00:15:19):
Wow, those are excellent examples. What levels does this help you with? At what level is this most useful, and then does it kind of taper out it? I don't know if you get to VP level, do you still try using Magic Loop?

**Ethan Evans** (00:15:33):
So I think it works anywhere from the start of your career to pretty far into it. I think at my level, I finished my career as a vice president at Amazon. It does peter out in the sense of the active. And what I mean by that is you're still doing the same thing, but you don't have to talk about it. Your managers are expecting you to step up and recognize challenges. They're expecting you to ask for resources when you need them, and you don't sort of have this level of explicit conversation around, what can I help you with? They're expecting you to anticipate what's needed.

**Ethan Evans** (00:16:09):
So in the newsletter we did together, I wrote about how over time, you go from asking your manager, "How can I help?" To suggesting to your manager, "These are some things I see that seem like they need to be done. Would you like me to do them?" To just seeing what needs to be done and sort of keeping your leader in the loop and saying, "Hey, I noticed that we have this problem. I fixed it. I noticed we have this opportunity. I've started program against it." I think at the executive level, it's much more you being proactive and just keeping your leader in the loop.

**Lenny** (00:16:44):
I think in the post, the way you described this step is this is advanced mode. Don't jump straight to this. Don't just start suggesting things, because you may get it wrong.

**Ethan Evans** (00:16:53):
Yeah, well, it's all a matter of rapport and trust. A huge part of career success is how much trust you have, mutual respect with your leadership. When they're confident that you're going to make the right decisions, they're confident to let you go. But yeah, when you're brand new or you're new to a manager, if you just jump in, you may either not work on the things they value or even find yourself working across purposes, and that isn't the right place to start.

**Lenny** (00:17:19):
Awesome. Okay. Just to close out this conversation. You touched on this, but why is it that you think this is so important and effective? Why do you think this works so well? People may not recognize, "I see this is the key to this."

**Ethan Evans** (00:17:31):
Well, I think it's two things. First, I mentioned how rare it is for managers to be offered help. If you're a manager, you'll recognize this. If not, feel free to talk to any manager, whether your own or somebody else. Ask them how much they worry and how much they feel overwhelmed and wish someone would give them a hand. Management can be a lonely job, because you feel like you're responsible for everything. So having an ally, it's just a huge weight off people's shoulders.

**Ethan Evans** (00:18:01):
And then I think a lot about social engineering. The social engineering's here is just the simple, "You help me, I'll help you." It doesn't have to be exploitative, it's just we help those people who help us, and that's built into human survival. 

**Ethan Evans** (00:18:18):
And I think this loop works so well because it's just leaning a little bit into that behavior. So many relationships with managers are oppositional. You tell me what to do, and I'm kind of like a kid in high school who's trying to figure out how do I skip as many classes as possible and turn in as little homework and still get by with a D? That relationship won't build your career.

**Ethan Evans** (00:18:45):
Some people approach their jobs as my goal is to do the least I can and still collect my paycheck. That's an approach if you're okay with where you are. It's not what I coach though. I assume people want to grow.

**Lenny** (00:19:02):
Okay, so maybe it's just as a closing question, for people that are listening and want to start putting this into practice slash are stuck in their career and are just like, "Okay, I see. Here's something I can do." Could you just again summarize the loop briefly?

**Ethan Evans** (00:19:15):
Sure. Step one, make sure you're doing your current job well. The way I explain this is when you go to your manager and ask, "What could I do to help?" You don't want their answer, even if they don't say it quite so bluntly to be, "Do your F-ing job." You need to be doing that already. So be doing a good job.

**Ethan Evans** (00:19:34):
And unfortunately, a good job is in the eyes of your manager in this case. You may think I'm doing great work, but if your manager doesn't, they're the ones you need to build as an ally here. 

**Ethan Evans** (00:19:46):
Once you have that, go ask how you can help, do whatever you're asked, and then go back to your manager and suggest or ask, "I would like to meet this goal. Can I keep helping you? What could I take on that you need that would also help me meet this goal?" And that's where you start to try to bring your two sets of aims together. What do you need done, how can I get to my goal? And let's do those things together.

**Ethan Evans** (00:20:11):
And then you just repeat this loop. You build trust, you build the relationship. And with all good managers, and even a lot of moderate managers, they appreciate the help so much, they really lean into that.

**Lenny** (00:20:23):
I think there's two really important elements of this that you haven't even mentioned necessarily, that I think are part of the reason this works so well. One is this forces you and your manager to identify the gaps that are keeping you from the next level, which it's often vague, and then you get to a performance review, and then your manager's like, "Ethan, you're still not good on this and this and that," and you're like, "You never told me that that's the things you're looking for for me to get promoted." So I think there's this implicit, here's what you need to work on to get to the next level, which I think is part of step four. 

**Lenny** (00:20:53):
And then you actually did touch on this that it's important to share your goal to your manager. Here's what I want. I want to get promoted. A lot of times they don't know that and you helping them understand, "Here's what I want, help me get there." It goes a long way. So there's a lot-

**Ethan Evans** (00:21:06):
Managers often fall into the trap. They chose to become managers, so they assume one of two things about you. They either assume that you want to keep doing exactly what you're doing forever, just maybe make a little more money.

**Ethan Evans** (00:21:16):
So you're an artist, you want to keep drawing forever. You're a lawyer, you want to keep writing contracts forever. Or they assume that, "Hey, I became a manager. I'm very proud of my career. That must be what you want."

**Ethan Evans** (00:21:29):
And these assumptions are natural, right? We tend to view by default that our path is great and everyone would want to be us. Now of course, some good managers don't do that. But if you clarify and express your goals, you remove that ambiguity.

**Lenny** (00:21:45):
I actually had a period in my career where I specifically did not want to get promoted. I was very happy where I was, and I just wanted to keep doing this awesome IC role. Is that something at all you see where people are just like, "I'm good. I don't need to get promoted," and then is this helpful in that in any way or is it not as big a deal?

**Ethan Evans** (00:22:02):
So first, I reached a point in my career where I was no longer pursuing promotion either, and I wanted to do other things. So I've lived that myself and I've used the same loop, but I used it to go do what I wanted to say, "This is now what I want, and how do we get there? How do we create a role where I'm adding value appropriate to my level, but I'm doing this other work that's fun?" I moved into gaming and I really wanted to do that.

**Ethan Evans** (00:22:25):
Second, I think it is still helpful because there's something you want probably. Maybe you want to work on different kinds of projects or maybe you want to work with a different higher performance team. Or maybe you want to rebalance your life and say, "Hey, I love what I'm doing, but how can I be a star performer for you but within these boundaries?"

**Ethan Evans** (00:22:47):
So if you truly have the perfect job just as it is, you may not need The Magic Loop. But I know so few people if you're like, "Nope, there's absolutely nothing I could improve about my role."

**Lenny** (00:23:00):
Yeah, I think that your point about your goal doesn't have to be promotion. It could be work on a different part of the org, try something totally... Maybe transition to a new function that could be part of your goal. Awesome. 

**Lenny** (00:23:09):
Okay, so along the same lines of career progression, you work with a lot of senior manager types, kind of the level of L7 and one M2-ish, and you share with me that one of the most frustrating parts of their job in that specific portion of their career is they get stuck at that level and they don't move up, and it becomes really annoying, and they're not sure how to break out of that. What advice you share with folks like that, that may be listening?

**Ethan Evans** (00:23:36):
Yeah, so it's common to get stuck there, and there are a few reasons for it. First, there are a lot of senior managers. If you think of your average director, they may have six to eight reports. How many more directors are needed? So there's a choke point.

**Ethan Evans** (00:23:52):
Second, that choke point is worse in the current economy, and in the past maybe a lot of companies, Amazon, Google, apple, etc., were growing very rapidly. And so it wasn't just you were waiting for some other director to leave. The teams were getting bigger.

**Ethan Evans** (00:24:07):
I experienced this at Amazon, where over a nine-year period I went from managing six people to 800. And so I went from a senior manager all the way to a vice president, and I described I was, in some sense just riding the elevator. The elevator was going up, and as long as I managed to stay on it, I was going to arrive at vice president.

**Ethan Evans** (00:24:29):
But the other thing that causes people to get stuck is the difference between a senior manager and a director is how you lead and the work you're doing. And you can get as far as senior manager by being really strong in your function and being really good at getting things done. As a director, and as a VP beyond that, it becomes much more about influence, coordination with others, and letting go of being in all the details yourself. And so senior managers really have to change some behavior.

**Ethan Evans** (00:25:03):
I often reference the book by Marshall Goldsmith, What Got You Here Won't Get You There. Not only because it's a great book classically on this problem, but because the title tells the story. All the great traits that got you to this one level won't get you to the next level where you're more expected to be thinking in strategic terms, thinking longer term.

**Lenny** (00:25:26):
So to someone that may be in that role today and they're not moving up, is there anything they can do? This point about just there's no roles for you, there's only so much you can do there, is the advice just wait until an opportunity arrives? Is it run this Magic Loop until something happens? Is there anything you can do?

**Ethan Evans** (00:25:42):
I would be honest with people and say some patience is required. At this level, there is some notion of, do we need a director? Do we need a vice president? Do we have a challenge at that level that needs that person? And so promotions at this level, I often teach have two components. The first component is can I eat and do that job? Am I qualified? Do I have the skills? But the second piece is, do we have such a job that needs that?

**Ethan Evans** (00:26:09):
However, there is a lot you can do. A lot is in your control. And what is in your control is to start practicing those next level skills. Start working with your leadership on, where can I take on a strategic project? How can I become more of an inventor? I teach some about how to sort of systematically be inventive. It's not pure magic. Edison said it's 1% inspiration and 99% perspiration. You can learn the 99%, and the 1% isn't as hard then. So you start showing those next level traits. And as I describe it most succinctly, how do you make yourself the person who will be chosen out of the eight?

**Ethan Evans** (00:26:51):
And you can be chosen, there are several ways to move up. Your boss can leave or be let go. They can be promoted to another role. But another way is I coach now, and I have several clients recently. I was just talking to a client yesterday, her two peers were let go. They were all the same level. Her two peers were let go and she was given their teams. And she expressed that her boss had been told, "You have too many senior managers for the size of your organization. We need to do some change in the organization, clean house, and put all your people under the folks who have potential."

**Ethan Evans** (00:27:32):
Well, obviously she must be one of those people, because she still has her job and has more people and more to do. And unfortunately, her peers are shopping for new employment. So be that person, and that's where The Magic Loop comes in. Be that person.

**Lenny** (00:27:48):
I was just talking actually to a senior PM leader who pointed out that with this kind of lean environment of a lot of flattening of orgs and a lot of layoffs, that this is becoming increasingly hard. Exactly what you're describing. There's just less spots, because companies are running more lean, and so you just kind of have to wait. 

**Lenny** (00:28:06):
I think part of this advice you just shared, which is classic do the job before you have the job makes all the sense in the world. Because once people see that you can do it, obviously they'll feel a lot more comfortable putting you in that position.

**Ethan Evans** (00:28:18):
And they'll be looking. I always remind people, as a leader, I want the best people under me I can have. It's not that I don't wish to promote you. If you think about my job, this helps people, right? I have selfish motivation to promote you. A lot of people think, "The bosses there holding me down." Well, maybe some bosses are, but why wouldn't I want stronger, more capable direct reports? Why wouldn't I want people under me who can do more of my job? Frankly, that's the only way I can do less of my job.

**Lenny** (00:28:47):
Plus this pressure you're always getting from your reports. So like, "Hey, I'm ready to get promoted, because this time"... You mentioned this word inventiveness, and I was just listening to Jeff Bezos on Lex Fridman, and I don't know if you heard this, but Jeff Bezos described himself most as an inventor more than anything else that he does. Is that something that you think about? Is that influenced by Jeff Bezos any way, that idea of being an inventor as a leader?

**Ethan Evans** (00:29:13):
I'll say a couple things about that. First, I know you talked to my old boss, Bill Carr, who wrote Working Backwards. What I don't know is if he shared with you that after he published it, he actually realized there was a better title. He wishes that he had called the book The Invention Machine, because what Jeff was trying to do with Amazon was create the most inventive company, the company that would systematically out-invent others. And so while Working Backwards is a great title, Bill and Jeff think they should have called it the Invention Machine.

**Ethan Evans** (00:29:47):
When I joined Amazon, I did not think of myself as an inventor, but I saw that we had these leadership principles think big and invent and simplify that pushed on that. And I said, "I'm in trouble. I don't know how to do this." And I sat down and thought about that. What am I going to do? It seems like that's required. And I figured out how to become systematically inventive. So I now hold over 70 patents as one benchmark of inventiveness, and they were all created during my 15 years at Amazon. 

**Ethan Evans** (00:30:22):
And the way I did that, inventiveness actually isn't that hard. I teach about this. And to invent systematically, first you do need to be somewhat of an expert in whatever area you want to invent. So Lenny, if you and I say let's get together and we're going to invent cancer drugs, we have the problem that neither of us, as far as I know is a biologist, a doctor. We don't have the right background, we don't know what we're doing. So we would just be fumbling around I guess with a bathtub full of chemicals hoping. It's probably not going to work out that well. So you have to be something of a knowledgeable expert.

**Ethan Evans** (00:30:56):
But then the second thing people don't do is they don't spend dedicated time actually thinking. They feel like, "Invention is just going to come to me." When I want to invent, I get away from all my devices. I go in a room with the problem I have, and I force myself to actually concentrate on what do I know and how can I invent? And the most straightforward way to invent is not to somehow come up with something completely new, but instead to put together two things that exist. 

**Ethan Evans** (00:31:28):
And so my example of this, I have a patent I talk about a lot for a drone delivery for Amazon, but the drone doesn't fly from the warehouse. Instead, a truck with no top drives slowly around the neighborhood, and the drones go back and forth from the truck. As opposed to the driver stopping at every house, you can have four or six drones hitting everything in the neighborhood. 

**Ethan Evans** (00:31:55):
And the way I came up with this idea is one day I was thinking about drones and delivery, but I loved military history. And so I was thinking also about an aircraft carrier and I was thinking, is there a way to have an aircraft carrier for drones? And from that, it was very quick for the light bulb to go on and say, well, what about a truck? 

**Ethan Evans** (00:32:17):
And so I have this patent, and we haven't seen this become reality yet. I'm waiting for my idea to become part of Amazon's drone delivery system, but I think ultimately it will.

**Lenny** (00:32:32):
That is badass. I'm imagining returns come back to the truck. We're using that rope thing that just captures them with that little hook.

**Ethan Evans** (00:32:42):
Yeah. Well, there's no reason... Same thing. When you want to return something as opposed to taking it to the UPS Store or whatever, you just put it on your porch, and then on your phone, on your app, maybe you take a picture of it so that the drone can recognize the box or you put it in a designated spot, and you push a button and the drone takes your return away. Yes, there's no reason.

**Lenny** (00:33:03):
Can't wait for that. And it takes your dog backs in it sometimes, part of it.

**Ethan Evans** (00:33:09):
My dog's too heavy, thank you.

**Lenny** (00:33:11):
My dog's not. There's an owl in our backyard that we sometimes worry he is going to come grab our dog on. This idea of invention, this is really interesting. I didn't plan to talk about this, but for someone like say a PM on a team that wants to get better at invention, innovation, big thinking, is there a practice you find helpful here? Is it block off two hours, get a pen and paper, and just think about the specific two adjacent things working together?

**Ethan Evans** (00:33:34):
So that's part of the process, is put in dedicated time. The interesting thing I would say is you don't need that much time. Two hours is great, but you only need two hours once a month. People think invention takes all this time. The thing is once you have one good idea, it often takes years to express that.

**Ethan Evans** (00:33:52):
So you had the idea to have a newsletter. I know some of the history of your newsletter. You've been working on the expression of that idea for years now. Jeff and Amazon had ideas like, "Let's have Prime shipping." Well, Prime is still getting better and still being worked on. It's a 20 some year old idea. The Kindle a decade's old idea now still getting better. 

**Ethan Evans** (00:34:16):
So the point here is you don't need very many good ideas to be seen as tremendously inventive. Like Elon Musk, Tesla, he can kind of dust off his hands and be like, "I am now an Edison-like inventor." So he keeps doing it, but you don't need that many inventions.

**Lenny** (00:34:36):
This touches on something else Jeff Bezos shared on the podcast that most of his innovation and work is in the optimizing phase. It's not the here's the idea, it's the making it cheaper, and better, and faster. And that's where most of the good stuff comes from. In this point of Tesla, Elon had this idea, and now the hard work is actually making it scalable and cheap enough for people to use, not just an electric car.

**Ethan Evans** (00:34:59):
With the idea of Jeff saying that invention is really a lot of the incremental and optimization, I completely agree with that. To invent well, you need a base idea, but then there's so much of the work is making that idea real.

**Ethan Evans** (00:35:15):
And again, Prime is a great example of this. The Amazon Prime program was a great example of, okay, we want fast free shipping. We want this program. That was a one-time idea that they did build, but now Prime has expanded. First it was two-day in the US, then one-day in the US, now it's same day in the US. But also they added Prime Video, Prime Music, Prime Gaming. There's actually something like 25 things you get free with Prime. Most people have no idea, because you get free photo storage and this ongoing list. And all of that is that incremental optimization to make it better, better, better, better. And of course Jeff's goal, which you probably heard him say, was to make Prime a no-brainer, to where you would be irresponsible really not to be a member.

**Lenny** (00:36:06):
I know you have an awesome Jeff Bezos story that I want to get to, but before we do that, one more question along this line of career advice and progression. So I read somewhere that you've interviewed over 2,500 people over the course of your career. And so kind of going back to the beginning of a career, or at least getting a job, what have you found is most helpful in standing out as a candidate when you're interviewing, and essentially getting hired? What advice do you have for people that may be going through an interview process right now?

**Ethan Evans** (00:36:33):
There's a lot of evidence that suggests that the number one and two factors in any interview are appearance and enthusiasm. And it doesn't mean you have to be beautiful, but show up somewhere looking like you're interested in the job, not in your pajamas. And most importantly, be enthusiastic. People want to work with people that want to work with them. So if you seem very judgmental of the company and like you have to sell me on it, you're going to turn them off. I look at every interview of whether or not I really want this job, I might've decided I don't want the job. I still want the offer.

**Ethan Evans** (00:37:10):
And so I come to any interview I do leaned in and talking about how excited I am to be a part of this opportunity and what I know about the company. Beyond those cosmetics, the biggest thing I see particularly at higher levels is people talk about what they have done but not why it mattered. They don't talk about the impact.

**Ethan Evans** (00:37:32):
See, a leader is not hiring someone to just do work. They're hiring someone because they have a problem or a need. And so if you can show them, "Look, here's the things I've done that have made a difference. Here's the things I've done that have helped my past employers where I've had an impact." So I didn't just do work. That makes you a worker. Someone who has an impact is more of a leader.

**Ethan Evans** (00:37:57):
And leader doesn't need to mean people manager, just a higher level, that I have done something that solve the big problem, and here's how it changed the company or customer outlook. That's what I'm looking for in an interview, is are you bringing me an understanding of the business that shows you contributed to the business, or are you just telling me how hard you worked?

**Lenny** (00:38:19):
Awesome. On that first piece, now that most interviews I imagine over Zoom, in terms of enthusiasm and looking professional, is there anything you've found that people may not be thinking about in those two buckets?

**Ethan Evans** (00:38:33):
Yeah. Show the person full-time dedication. So unless you really don't have any choice, don't take an interview from a car, don't have your camera off. Eye contact is still a real thing. Body language is still a real thing. Gestures like I'm making now with my hands, they're part of your presentation.

**Ethan Evans** (00:38:53):
So be fully present and try to project through the camera a little bit of I'm excited to be a part of this and I appreciate the opportunity. I often tell people the best way to prep for an interview might be a good night's sleep and a pot of coffee, that being fully engaged and energetic is a huge lever.

**Lenny** (00:39:18):
Awesome. And I think basically, the feedback there is don't over obsess with the content. There's a lot of value in just how you come across.

**Ethan Evans** (00:39:27):
Yeah, 100%.

**Lenny** (00:39:29):
**Ethan Evans** (00:41:00):
I do. It's both a highlight and a low light. So I had been at Amazon about six years. I had become a director, and I was responsible for launching Amazon's app store.

**Ethan Evans** (00:41:14):
And so we were building an Android-based app store to go on Google phones and eventually on the Kindle tablets. And we got to launch day. And at that time, Jeff used to write a letter introducing new products. He would write a letter that said, "Dear customers, today Amazon's proud to launch blah blah, blah, and it's got these great features and I hope you really enjoy it. Thanks Jeff." And we would take down all the sales stuff on www.amazon.com and that letter would fill the whole screen. 

**Ethan Evans** (00:41:48):
And so he had written a Jeff letter, and this Jeff letter emphasized a particular feature of our product that he really liked. So that something that made it a little different.

**Ethan Evans** (00:42:00):
And that specific thing was we had a button called test drive that you could click on and it would open the app in a simulator in your web browser, so you could check out the app and interact with it before putting it on your phone. So he thought this was really cool and he was all about it. 

Well, my team had built all this technology. We had test drive working. It was kind of a hard piece of technology if you think about simulating any of thousands of arbitrary apps. And we worked all night to launch it, and it wasn't quite working at 6:00 AM. We were still debugging.

**Ethan Evans** (00:42:38):
Now you know engineers very well. And I'm sure most of your listeners know about engineers, even if that's not their discipline. We always think we're this close to finding the last bug. 

So about 6:15 AM, I get a message from Jeff that says, "Hey, I woke up, where's the letter?" Because it was supposed to go live at 6:00 AM, right after the markets in New York would've opened at 9:00 AM Eastern. And he says, "Where's the letter?" And I write him back and I say, "Well, we're working on a few problems." And what I'm thinking in my head is, "Get in the shower, get in the shower. I just need 20 minutes, get in the shower."

**Lenny** (00:43:18):
For Jeff to get in the shower.

**Ethan Evans** (00:43:20):
Yeah. And 30 seconds later, I have an email back that says, "What problems?" And at this point I have to start explaining, and I end up explaining that we're having a problem with a database, and we're debugging this database problem. And he's like, "Wait, there's a database in your design? We're trying to eliminate all Oracle databases and move to AWS. Why do you even have this?" And he is just getting more and more frustrated and angry.

And he starts copying in my boss, and my boss's boss who's with Jeff Wilke, the CEO of retail. And they start asking me questions. And it's just this snowballing, but 7:30 in the morning, Jeff is clearly angry. And there's this list of other people waking up and feeling like, "Well Jeff is angry, so my job is to be even more angry," and it's just raining in on me.

**Lenny** (00:44:14):
Oh man. 

**Ethan Evans** (00:44:15):
So what did I do? The interesting thing is what do you do when the future richest man in the world is mad at you? He wasn't quite richest man in the world yet, but he was headed there.

So the first thing I did was I owned it. I said, "Yes, it's not working. It's my fault. I will deal with it." I took ownership. And the second thing I did was start updating him very proactively and saying, "Here's where we are." 8:00 AM, "This is exactly where we are. This is what we're going to do and the next hour, and this is when you'll get your next update. I will update you again at 9:00 AM, so here's our plan."

And even though Jeff had sort of lost trust in me, like it's down, and it's not right, and I'm mad, given that he agreed with the plan, he was willing to give me 60 minutes. And then I would update him again and say, "Okay, this is what we've done and this is what we're going to do, and we'll update you again at 10:00 AM." So I was buying life one hour at a time.

**Ethan Evans** (00:45:17):
Now the other thing I did, and this is a good thing about Amazon, as more and more leaders got copied into this angry thread, they started reaching out in back channel and saying, "We've all been under Jeff's Eye of Sauron, we know it's miserable. What can we do to help?" And essentially Andy Jassy's organization, which was AWS at that time, and his CTO, a guy named Werner Vogels said, "You're having a database problem, let's get you some principal engineers from the AWS database team." 

And these principal engineers showed up at 9:00 AM roughly, and they looked at our design. We had made some fundamental mistakes in our database usage and they said, "It's too complicated to fix this. We're just going to give you 500 AWS machines so that your crappy design will run anyway. That's the immediate fix." And I'm like, "Okay, well I guess if you have 500 databases lying around because you're AWS, it's a great solution," and that's what they did.

**Ethan Evans** (00:46:27):
So the next step is we fixed the problem. A bunch of us worked together very hard to get the problem all fixed. Now it took all day, and Jeff was still frustrated because the opportunity to sort of control the messaging and the media by having his letter up had passed. People had noticed our launch and the articles had been written, and so Jeff was still very mad.

**Ethan Evans** (00:46:52):
So we fixed the problem, but Jeff now had no trust in us. The weekend went by. He was using the system looking for bugs because he is like, "This team's not reliable now. Ethan's not reliable. I better check it myself." So you have the CEO checking on you.

And he found a problem and emailed me like Saturday night at 9:00 like, "I was doing this and it broke." And luckily I was able to tell him exactly what happened by 9:30. Anyway, the next part of the story is that following week, I had a meeting with him on another topic.

**Ethan Evans** (00:47:32):
So I was part of this small group that was trying to figure out how to build a competing browser. You may not remember, but Amazon had a browser called Silk for a while. And I was invited to this meeting, but I wasn't a critical participant. So you may know this idea from Scrum where they say some people are pigs and some are chickens, and the chickens are sort of observers. I was a chicken in this meeting, and that turns out to be a great analogy because I was thinking, should I chicken out and not go? I could skip this meeting with the CEO who's angry at me. But when I had that thought, I realized if I can't face the CEO, I'd better pack my desk. That's the end. 

**Ethan Evans** (00:48:13):
So I went to this meeting early, and Jeff always sat in the same chair, so I knew where he would sit when he came in. So I sat down right next to his chair and I thought, "I don't know, let's find out."

**Ethan Evans** (00:48:24):
And so the meeting goes by, and of course in my mind Jeff is totally ignoring me, not even looking at me. But I think that's just me projecting, because remember I wasn't central to the meeting.

**Ethan Evans** (00:48:35):
So at the end of the meeting, everybody gets up to leave. He turns and looks at me and says, "So how are you doing? I bet it's been a hard week." And I thought, "Oh, okay, we're going to talk." And I said, "Yeah," I just sort of answered him with, "Of course it's been hard, but here's what we're doing and here's what we're going to do in the future." And we had a very human conversation. And I didn't believe Jeff would've forgotten that I let him down, but it was clear he had forgiven it. 

**Ethan Evans** (00:49:05):
So I was still going to have to, as it turns out, re-earn his trust. But the thing I did that's key for people to learn from is it's really easy to flame. He had been flaming me, writing angry emails. Angry emails are easy. Sitting three feet from someone and being angry with them face-to-face is hard. And when faced with, I can either start ranting at this person who reports to me, or I can say something nice, he chose to say something nice, and that rebuilt our relationship.

**Ethan Evans** (00:49:42):
So the end of the story is two years later, I was promoted to vice president. So even though I had failed the CEO on this very public launch where he was very definitely mad at me, I re-earned the trust, I showed I had learned the lessons of how to launch more reliably without outages, and I was promoted.

**Ethan Evans** (00:50:07):
And so I share that story because I think what I want people to understand is if I can get away with publicly failing one of the richest and most famous inventors on earth, and then get promoted and finish my career at Amazon very successfully, you can dig out of any hole. You just have to manage it right.

**Lenny** (00:50:30):
That is an amazing story. So there's a lot of lessons that I want to pull on here. One is just if you get caught in a situation like this where something completely fails, what I took down as you were talking, one is admit, yes, this is a huge problem, own it. This is like, don't try to deflect.

**Lenny** (00:50:47):
Two is the way I describe what you did here, is something I call prioritizing and communicating, where you prioritize, "Here's what we need to do," and then communicate. "Here's our priorities." And I love that you have this every hour, "Here's the latest, here's the latest." So make people understand you are on it and you'll continue to keep them updated. I imagine one of the worst fears is I have no idea what's happening here. I'm going to go in and start micromanaging.

**Ethan Evans** (00:51:11):
You're exactly right. I'm trying to hold off micromanagement. I'm trying to give them, "Okay, I believe with this and I can wait an hour," and then I can wait an another hour because that team seems to be on it. So I'm trying to rebuild trust one hour at a time, and avoid having three or four levels of management all come in and start helping.

**Lenny** (00:51:31):
Then I love this other piece of advice of meet them in person, try to take it offline essentially, which I know you did later. But that's such a good point that it's hard to be as mad, and angry, and flamey in person. People are just going to be like, "Okay, I get it. Let's try to figure this out." Amazing. Is there anything else? Those are the three that I took away. Just like if you're caught in that situation in the moment, is there anything else that you found to be really helpful?

**Ethan Evans** (00:51:55):
I mean, work hard and fast, right? You do have to fix the problem. My team had been up all night. I had to start sending people home to sleep in shifts. We had to pull in all this help. And so it was a very hard weekend.

**Ethan Evans** (00:52:10):
When you have a mistake, it's on you to pull out the stops, even if it's uncomfortable to recover from it. And again, this is not the time to be like, "Well, it's the weekend now, and my team, we'll hit it Monday." I'd have been out the door so fast, I would've had the comic Wile E. Coyote skid marks as I bumped down the street. So I would say that's important. It's part of showing ownership.

**Lenny** (00:52:39):
The other part of this is something I went through for a while when I was starting to become a more senior leader is I had a lot of imposter syndrome, and this fear that if I messed up, everything would crumble. People would see that I don't actually know what I'm doing, and I'm not really ready for this level of seniority. And so there's this fear of one big mistake, it's over. Clearly this was an example of a huge mistake and it was not over for you. Is there any lessons there that you take away of you can mess up and still do well, even if it's this level of mistake?

**Ethan Evans** (00:53:11):
I think a lot of people in my position would've quit. They would've let the shame... I was just a little bit bullheaded where I'm like, "Yeah, I messed up. But I know I'm still a good person and a good worker. Yes, I made a mistake, but I'm going to move on." Part of the story I haven't told that you might enjoy is I mentioned that Jeff Wilke was Jeff's number two at that point. Jeff Bezos, number two person, and he was my skip level. 

**Ethan Evans** (00:53:38):
Well, during this process, he came physically into our offices and he wanted to talk to me, and my manager who was vice president said, "Hey Jeff, this is my team. I own it. If you have any criticism, say it to me. You don't mean to talk to my team." And Jeff Wilke said to my boss, whose name was Paul, "Paul, that's excellent leadership. I really appreciate what you're doing. Please step out of the way. I want to talk to Ethan. You're doing a great job, Paul. Now step aside." And then he kind of read me the riot act.

**Ethan Evans** (00:54:15):
And the rest of that funny story is I was so happy with how well my meeting with Jeff Bezos went, I patted myself on the back and like, "I'm going to go face Jeff Wilke now. I'm going to schedule a meeting with him and do the same thing. I've got this down."

**Ethan Evans** (00:54:31):
So I go to meet with Jeff Wilke, figuring I'm going to run the same playbook. I'm going to look him in the eye and all will be forgiven. And Jeff Wilke looks at me and says, "Ethan, when you launched this, did you know you were gambling with the result? Did you know it might not work?" And I said, "Yes. We had a media commitment to launch on that day, and I thought shooting for the date was more important than perfect certainty."

**Ethan Evans** (00:54:55):
And he said, "Well, two things. First, you were wrong. You were wrong to prioritize date over our reputation. You let Amazon down in public and that was a mistake." He said, "Second though, at least you knew you were gambling. If you hadn't known you were gambling, we'd be discussing your departure." And I'm like, "Okay." Here I thought I was rolling in this meeting like I'm going to run my relationship playbook. And he's evaluating whether or not to keep me.

**Ethan Evans** (00:55:25):
The bullheadedness is even after he had told me he had been considering firing me, I'm like, "Well he isn't. So I'm just going to go forward." And a lot of that stubbornness of sure I made a mistake, but I'm not going to live in shame about it, I think is what people can take away. I think a lot of people feel they're more dead in the water than they are. 

**Ethan Evans** (00:55:53):
Because everybody makes mistakes, right? I mean Jeff and Fire Phone, that'll be an albatross around his neck. Jeff and Fire Phone will be a phrase of anybody who knows Amazon for the rest of his life.

**Lenny** (00:56:08):
Yeah, we talked about it on the Working Backwards podcast, and why didn't Working Backwards work for the Fire Phone, we talked about it. I love that these quotes and lines are so seared in your brain. You can remember it like word for word exactly what-

**Ethan Evans** (00:56:20):
Well, I've relived that moment many times.

**Lenny** (00:56:26):
And then just along the lines of working your way out of the hole, is essentially what you did just succeed for two years and do great, and that was the key there?

**Ethan Evans** (00:56:34):
No, I think I did have to learn. I've always been sort of an operational cowboy, meaning I like to go fast and loose. I prioritize speed, and I really had to step back and say, "Okay, Amazon at this level and scale doesn't like that." So I've taught myself a new phrase which was fear the New York Times headline. Be aware that if Amazon is down, it goes up on every news website immediately. And so if Amazon has some kind of mistake, it's on Wall Street Journal and CNN.

**Ethan Evans** (00:57:07):
And so as a leader, I had to think, is what I'm doing going to generate a New York Times headline? Because if it is, I'd better be really careful. And that's what I taught myself is you can't be paralyzed, but I taught my whole team, we don't want to be in the New York Times for the wrong thing. And that was the lesson

**Lenny** (00:57:32):
Along the lines of lessons, last question here, what's something that you took away from the way you approached it that you should have changed or should have done differently, that you've done differently since? Obviously don't... You mentioned this idea of don't promise a date that you're not that certain you're going to hit. I guess is there anything along those lines?

**Ethan Evans** (00:57:52):
I have two things here. First, Amazon loved in the past, they loved surprise launches. They love the idea of we're going to be quiet, quiet, quiet. Because basically it was a reaction I think to Microsoft where they felt Microsoft always talked about what was coming and then pushed the dates back. And so there was this whole thing about vaporware. And Amazon wanted to be the other way, which is we won't say anything and then it will just be there. The problem I came to say is the biggest thing I learned with surprise launches is that you're surprised by what doesn't work. 

**Ethan Evans** (00:58:23):
And so I shifted the approach to let's do a lot of beta testing. We always, even if others don't agree quite and say, "You're right, we're not going to have a surprise launch." Some of our beta testers, even if they sign NDAs are going to leak. And that's a better outcome than launching something that doesn't work. That's one lesson.

**Ethan Evans** (00:58:46):
The other lesson is this thing that broke in front of Jeff Bezos, ultimately it was a new college graduate engineer who wrote that code. And he had been left alone to write part of our user interface, but he had written it in such a way that it didn't scale. Now we didn't give him any help or oversight. We left him on his own, because we were busy focusing on other pieces of the problem.

**Ethan Evans** (00:59:20):
And shortly after the disaster, he left the company. And the mistake I made was not reaching out to him and really reassuring him of, "Yes, you wrote the bug, but that's not on you. The system failed you and we don't see you. Bugs happen."

**Ethan Evans** (00:59:38):
So the thing I regret in this whole thing is not realizing that even though no one in the team ever yelled at him or whatever, he knew it was his bug, and he obviously saw me and others sort of taking a beating. And so he left, and I wish he hadn't done that. And I wish more than that I had stepped in. I didn't realize what he was feeling.

**Lenny** (01:00:05):
It's interesting, the lesson there isn't catch that person sooner, and notice these links in the chain that may break. But it's more just be there for that human that have this challenge, that people may not be focusing on.

**Ethan Evans** (01:00:19):
Because we lost a good person, and he probably felt very bad about it. And we all feel bad when we make mistakes. That can't be prevented. But he felt undue responsibility I think, and that I really regret.

**Lenny** (01:00:35):
This is actually a really good example of ownership. You mentioned this term ownership and that connects to... Amazon has these leadership principles. I think there's 14 of them. One of them is around ownership. And apparently you helped craft the actual language for that principle, which I think is a huge deal with Amazon. I imagine very few people have a say over how to define, and describe, and say these principles. Could you just talk about this principle that you contributed to, how it came to be that you helped actually write it?

**Ethan Evans** (01:01:08):
Amazon is now kind of on its fourth version in my mind, maybe there's more. But its fourth major revision of its leadership principles over its 25 plus year history.

**Ethan Evans** (01:01:18):
And when it was going from version one to version two, Jeff and his leadership team sat down together. And actually in version one, there were three different lists. They were leadership principles and core values, and something else I don't remember. And they were like, "Three lists is stupid. Let's make one list."

**Ethan Evans** (01:01:36):
Well ownership, the term had been a part of one of those lists, but when they merged everything, they took it out. And this guy Jeff Wilke I mentioned, the number two and the leader of retail, he brought a bunch of us a bunch of his directors. He brought the proposed list to us in a meeting and said, "Hey, this is the proposed new version, do you have any comment?" And we all sat around and talked and said, "Where's ownership? Ownership is missing." So we told him, he said, "Look, ownership is missing. We think it should be there." And he said, "Well, why don't you propose a draft?"

**Ethan Evans** (01:02:15):
And so about a half dozen of us sat around and roughed out a draft of how we felt ownership should be written. And I proposed these six words, which are, "An owner never says that's not my job." Maybe that's seven words.

**Ethan Evans** (01:02:36):
So I propose this specific language as a part of it and we sent off this draft. And months go by, we hear nothing. And then one day the leadership principles are announced and ownership is back in. It's been modified, but that, "An owner never says that's not my job," is a part of the leadership principle, and it's remained to this debt. 

**Ethan Evans** (01:02:58):
And what I love about that is because Amazon has one and a half million employees who live by these leadership principles, it's probably the most impactful thing I've ever written.

**Lenny** (01:03:11):
Wow. So those seven words are the most impactful thing you've ever written. I love that and I totally get that. I'm looking at the principles right now and it comes right at the end of that principle. We'll link to the 14 leadership principles. Is there another principle that you really love or one or two? I don't know. It's probably hard to pick your favorites.

**Ethan Evans** (01:03:28):
I'm a huge proponent of bias for action. Bias for action says speed matters in business and many decisions are reversible. And so it's important to go faster. 

**Ethan Evans** (01:03:41):
And I think people don't understand that in a competitive environment, being right is good, but being quick is necessary. Because if there are 10 startups working on an idea, some of them will gamble, and they'll make bad gambles, and they'll go out of business. But some of them will gamble and make an early bet and be right. And if you are not moving quickly, you'll be beaten by the people who maybe got lucky. 

**Ethan Evans** (01:04:05):
And so you've got to have a process that values speed, values, what can we do today? What can we commit to today? So I really like bias for action. Now that is what got me in trouble with Jeff, right? I was willing to gamble. So it has to be in balance, but that's my other favorite.

**Lenny** (01:04:25):
Again, the Jeff Bezos interview with Lex Fridman, he was talking about how with Blue Origin, with the way Amazon, he thought about Amazon is customer obsession. That was the core goal and differentiator of Amazon. With Blue Origin, he wants it to be decisiveness. It's basically leaning into this bias for action fully, which is really interesting.

**Ethan Evans** (01:04:44):
I saw that part of the interview and I thought, "Wow, that's exactly right." Because again, rockets blow up and they have people on them. You've got to get it right, but you also have to keep moving, because there's always one more thing you can safety test. So how do you balance it?

**Lenny** (01:05:04):
Yeah, it's interesting. With rockets, that's the one that you pick. It's pretty bold to be all move forward kind of thing. So this principle, again, going back to ownership, so you basically suggested this phrase, "You didn't hear anything," and all of a sudden it becomes part of the whole thing. Did that feel weird that they never told you, or I don't know if they gave you credit for that, or it's like, no, it's great?

**Ethan Evans** (01:05:24):
Yeah, I wouldn't even claim credit for it, except I kept a copy of the email that says, "Ethan thinks it should say blah." I have the written proof. Because it's not about the credit. I'm very happy and proud that those words were kept. But in Amazon, I doubt if Jeff knows I wrote those words. It's not like I've ever told him, "Hey, do you know you kept my words?" That's not appropriate. It's just a fun anecdote.

**Ethan Evans** (01:05:55):
And it does show, I guess something people can learn from that though, you can influence way up in a company if your ideas are good. And also, when we challenged, Jeff Wilke was a strong opinionated leader who didn't necessarily always love being challenged.

**Ethan Evans** (01:06:15):
And so when we first told him, "Well, we think you're missing ownership," he was like, "You're staying that the whole S team can't get its leadership principles right?" I mean it wasn't exactly that way, but he was very much like, "Well, is this really necessary? Why do you think it's necessary?" And his challenge to us to write it was kind of framed as, "Well if you're so sure it's good, show us." But again, I'm stubborn and I'm like, "All right, let's write it." And we did.

**Lenny** (01:06:47):
That's funny. That's not a great example of leadership where he is like, "Hey guys, I need your feedback on this thing. But no, don't actually tell me anything's wrong."

**Ethan Evans** (01:06:57):
Well, yeah. I mean for a bunch of directors to kind of critique the work of people two levels higher, he wanted it, but then he's sort of naturally resistant to it if we're kind of poking at his baby.

**Lenny** (01:07:14):
It's unlikely that there's something huge missing and it turns out there was.

**Ethan Evans** (01:07:18):
Yeah.

**Lenny** (01:07:19):
And I guess just on these principles, people may not know this, but this is where disagree and commit comes from. It's actually have backbone, disagree, and commit. We talked about this on the podcast about working backwards. I also love leaders are right a lot. That comes up a lot and I love that, to be successful, you need to be right. You can't just project confidence. You can't just be in a bunch of meetings and ship things. You need to be right to be successful.

**Ethan Evans** (01:07:42):
And that one's been rewritten to carefully say, it's always interesting what is the history of the edits, which you wish you could see the edit history on these. That one got modified to say something about leaders actively work to disconfirm their beliefs.

**Ethan Evans** (01:07:58):
And the key there is it was trying to get at the idea that you've got to be very open and always be questioning, "Yes, I think I'm right, but what's the new evidence? What am I learning? What's changing?" And in fact, it also says they seek diverse perspectives.

**Ethan Evans** (01:08:20):
And that was a way of getting at what's called DEI, diversity, equity, and inclusion. That's a subtle nod towards if everyone in the room is a 50-year-old white man, you may not really be making the right overall decision for Amazon's customer base. You may be making the one for 50-year-old white suburban Seattleites. And so it's just some of these, every word in those has been studied as an individual word inside the company.

**Lenny** (01:08:52):
Amazing. Okay. Let's move on to the final area I wanted to spend a little time on, and this is called contrarian corner. I'm curious if you have any contrarian opinions about things basically that other people believe that you don't believe, something you see that many people don't see. Is there anything that comes to mind?

**Ethan Evans** (01:09:11):
Yeah, I think a place where I'm currently very contrarian is the return to office movement. Many leaders at my level appear or publicly favor the need to get back into the office potentially full-time. 

**Ethan Evans** (01:09:27):
And I'm contrarian on this because of innovation. Specifically, I looked it up, you can check my facts on Wikipedia. The first purpose-built office, the first building ever built to be an office was built in 1726 in London. And so we're about 300 years into learning how to use offices well.

**Ethan Evans** (01:09:51):
And what that means is offices aren't going to get much better. What's the last major thing you can think of that got better in offices? You might say well open offices, but a lot of people would say that's not even a good idea. These big rows of desks and loud pits.

**Ethan Evans** (01:10:06):
With working from home, we've only been doing that for a few years since the pandemic began and at all since the internet started 20 years ago. Which one is likely to have more opportunity for improvement? There's so many things we haven't explored with remote work. And I think the people who say, "Back to the office, it's because we know it works," well we know what it is, but I have so much more faith in the opportunity to improve the remote experience. And so I think long-term, it's going to triumph.

**Ethan Evans** (01:10:40):
The one other place where I'm a huge contrarian is doing business on a handshake. I understand companies need lawyers, and I have an attorney for certain things. But I coach people. Most of the people I coach, there's no NDA in place. There's no contract in place. They pay me through PayPal and I do good coaching for them.

**Ethan Evans** (01:11:01):
I think too much of the world is contract driven, and we've lost the idea of your word being your bond, and you can actually trust me to follow through on my commitments. And I'm a contrarian there.

**Ethan Evans** (01:11:14):
I realize I will occasionally get burnt. Someone will behave in a way, they'll let me down. But I think when we're always suspicious of people, that's a high cost. And the other place I'm contrarian is just doing business on faith.

**Lenny** (01:11:32):
That reminds me, Sam Altman has a similar philosophy of just trust people and assume it'll all be okay. Sometimes you'll get burned, but on balance, it'll end up being much better for you and for everyone around you. 

**Ethan Evans** (01:11:42):
I didn't know that Sam had said that, but I strongly agree with it.

**Lenny** (01:11:45):
Yeah, although he had some challenges recently. I don't know if it's working great, but it ended upgrade for him. So anyway, okay. We've actually reached our very exciting lightning round. Before we get there, is there anything else you wanted to touch on, or share, or leave listeners with?

**Ethan Evans** (01:12:01):
No, I've really enjoyed this conversation. I could talk about careers forever and I love doing that, but I think we've covered a ton today that will really help people. So I'm good. Let's hit the lightning round.

**Lenny** (01:12:14):
All right. With that, we reached our very exciting lightning round. Are you ready?

**Ethan Evans** (01:12:19):
I'm ready.

**Lenny** (01:12:20):
Ethan, what are two or three books that you've recommended most to other people?

**Ethan Evans** (01:12:25):
Two or three books. My number one recommendation is a book called Decisive. It's by Chip and Dan Heath, and it's about the science of making better decisions. The reason I recommend it so much is it will make your career better because leaders are decision makers, but also your personal life. So I apply it at least as much in my personal life as I do in my professional life. 

**Ethan Evans** (01:12:47):
My second most recommended book is Leadership and Self Deception, much less known than Decisive, a little bit harder to approach. It's by a group, a research group called the Arbinger Institute, and it's about, the self-deception is we cause a lot of our interpersonal problems while blaming them on others. And it walks through how are you part of the problem you're having with somebody else and what can you do about it?

The third and final book was recently brought to me by someone I work with that you know, Jason [inaudible 01:13:21]. That book is The Almanack Of Naval Ravikant. And Naval Ravikant is an angel investor responsible for AngelList. 

**Ethan Evans** (01:13:30):
But what I love about that book is he has a recipe. He really boils down how to be successful while loving what you do. And he says, "No one can be a better version of you." Don't try to copy me and be, "I'm going to be like Ethan, or I'm going to be like Lenny." Instead, figure out what you uniquely do best that you love, because no one can copy you being you. And that's your defensible sort of career value. And I really like that mental model.

**Lenny** (01:14:03):
Yeah, Naval has so many insightful messages, and you can read all these on his Twitter. We'll link to his Twitter, and someone just made a book out of his tweets basically. He's such an interesting dude.

**Ethan Evans** (01:14:13):
Yes, that's right.

**Lenny** (01:14:14):
Awesome. What is a favorite recent movie or TV show you've really enjoyed?

**Ethan Evans** (01:14:19):
So I grew up on a farm, and so all the Taylor Sheridan, 1923, and Yellowstone, and all of those series, we've watched everything he's put out. We do kind of laugh like, wow. Are you familiar with Yellowstone at all?

**Lenny** (01:14:37):
Absolutely. A lot of death.

**Ethan Evans** (01:14:39):
Yeah. At one point my wife and I were watching it, we would start betting. So the episode is starting, how many people will die in this episode? This ranch in Montana, but yet somehow they're always killing people. How does this work?

**Lenny** (01:14:55):
That's what your life was like, is what I'm hearing. Favorite interview question that you like to ask candidates?

**Ethan Evans** (01:15:03):
I think my favorite interview question is, "Tell me about a time where you needed to disagree with your management, where you needed to stand up or fight for a position against higher leadership or people in power." Because I think that's really hard to do. I'm normally interviewing leaders, and I think having a bunch of people who just say yes isn't helpful. You need people to have, as you said, have backbone, disagree and commit. So that's what I'm normally looking for.

**Lenny** (01:15:33):
Awesome. Is there favorite product you've recently discovered that you really love?

**Ethan Evans** (01:15:38):
It's silly, but my favorite product that I've discovered recently is the Chuckit!, which you use to whip a ball for your dog a quarter mile. It basically extends your arm. And it's just fun to send a ball soaring way further than you could ever throw it. And you feel like, "Wow, look at me. I'm a major league pitcher." Because I have this three foot lever arm and I understand physics. If we look at tech products, there's so many I love. It's too easy to say ChatGPT and stuff, so I won't go there.

**Lenny** (01:16:16):
Awesome. My dog does not love chasing balls, so I haven't had a reason to buy that, but I've never thought about just the joy of flicking a ball really far. Do you have a favorite life motto that you often come back to, share with folks, find useful in work or in life?

**Ethan Evans** (01:16:31):
I happen to be a Christian, and the motto that I think about the most is, "To whom much has been given, from him much will be required." And so I think a lot about what is my social responsibility. 

**Ethan Evans** (01:16:44):
I've been very lucky. I grew up on a farm in Ohio now. I wasn't a farm boy, my father was a chemist. But I grew up in upper middle class settings, and I've ended up being extremely successful, able to retire from my job at 50 to kind of coach and teach. What do I owe to pay forward? So those words are obviously ancient spiritual texts, but they're the ones I take away and think the most about. What's my responsibility?

**Lenny** (01:17:11):
As an example of someone that to whom much has been given, but because he's worked so hard, Jeff Bezos is starting a space business as you know. If you had the chance to go to space, would you go?

**Ethan Evans** (01:17:22):
Well, I of course saw his interview where he talked about how he thought about the safety and the conversation he had to have with his mother. I would like to go to space. I'm not willing to pay what I think the current tickets are, but I would take the risk. So what's the risk of that ride? One in a hundred, one in 50, even more that you won't come back. I would probably take the gamble.

**Lenny** (01:17:46):
So you'd be an early adopter? Where along that curve would you be, an early adopter, laggard?

**Ethan Evans** (01:17:50):
Well, I'm old enough that I remember when the Challenger space shuttle exploded, and I said I would get on the next one and I said, "They're never going to be more careful than the next one, so I'll get on the next one."

**Ethan Evans** (01:18:04):
So I think I would get on any one I was offered because of the chance. Unlike Jeff who claims he wasn't scared, I would probably be really terrified, at least at liftoff. While you're up there, it's great. Everything either goes wrong going up or coming down. It's not the middle.

**Lenny** (01:18:25):
Ethan, I think we're going to help a lot of people with their career. I think we're going to help them work through failure, become better owners. Thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out? Also, just share what you do now in case people could use that help. And then how can listeners useful to you?

**Ethan Evans** (01:18:42):
So the best place to find me online, I do all my writing on LinkedIn. It's where the professional community is. So Ethan Evans on LinkedIn. My actual handle there is Ethan Evans VP for my history as a vice president. That's the best place to find me. I do have a Substack newsletter. I do teach through the Maven platform, but all of those are linked off LinkedIn.

**Ethan Evans** (01:19:02):
And really, how readers help me, they comment on what I write, because I miss things. I am one person's perspective. And so I actually have a process where I take in all the comments people write, all the different perspectives, all the different exceptions, or special cases, or examples, and that's how I improve my own thinking is I read every comment and think, "Okay, what did I miss? What could I have said better? How can I incorporate this if I ever talk about this again?"

**Lenny** (01:19:31):
Just to give you another opportunity to plug the stuff you do now, what do you help people with in case people could value could you use the stuff that you offer? You said you coach, you have a course. What sort of stuff?

**Ethan Evans** (01:19:40):
I focus on two topics, career development. So how do you row in your career, the whole Magic Loop, and how do you attain promotion or attain a new role raise if that's your goal? And then leadership specifically. I teach a course that's been very popular called Stuck at Senior Manager - Breaking Through To Executive, which is how to get out of that sort of stuck, "I'm working really hard, I'm pretty good. I'm managing 25 or 50 people, but how do I get to the big chair? How do I get to the division level leadership and what do I need to change?" It's that whole what got you here won't get you there. And I love to see people succeed at that. People write me back and say, "I did get a job. I did get promoted, I did get a raise," and that's my fulfillment.

**Lenny** (01:20:25):
Amazing. Ethan, thank you so much for being here.

**Ethan Evans** (01:20:29):
Thank you, Lenny. And I got to say, you are very good at this. You're so smooth and you just do a great job interviewing. It's been really been a pleasure.

**Lenny** (01:20:37):
I really appreciate that, and so are you. Thank you. Bye everyone.

**Ethan Evans** (01:20:42):
Bye everyone.

**Lenny** (01:20:44):
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.

---

## [5/19] The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming)

**Heidi Helfand** (00:00:00):
Reteaming is hard. Reorgs are hard. You can't lump them all into one thing with oh, it's all great all the time. No, it's not. If we could just build the software, deliver to the customer, get the product market fit, hey, have we delighted them or not? If only it could be that easy. No, we have the people layer, so let's focus there too.

**Lenny** (00:00:25):
**Heidi Helfand** (00:03:45):
Thanks, Lenny. Great to be here.

**Lenny** (00:03:47):
It's great to have you here. So I had this colleague at Airbnb, her name was Jana, and she always had this joke that she shared that if it's been six months and she hasn't switched teams or hasn't moved desks, she knew there was this reorg coming, there's something happening, something was coming to change everything. And you wrote a whole book about this general idea of teams changing, reorgs, you call reteaming. I have the book right here. It's called Dynamic Reteaming: The Art and Wisdom of Changing Teams. I feel like just people underestimate the opportunities and benefits of change, and I think that we see it as a scary thing. So I'm really excited to spend time with you and chat about this topic. Before we get into the meat of it, I'm just curious why you decided to spend so much of your time researching this area of team change, reorgs, reteaming.

**Heidi Helfand** (00:04:35):
Yeah, that's a good question. It wasn't necessarily planned. I had been working in a variety of different fast-growing startups for most of my career in 20 years in software-as-a-service companies in particular. And I read a lot of books to try to get better at my work and what we're doing in our teams. I have a lot right over there as you can see, and a lot of the books I would read on teams and the advice that I would get from people would be, you really want to keep your teams the same. You want to go for that forming, storming, norming, performing kind of thing. And I had thought about that and I was like, wait, well it wasn't really possible for us when I was at a startup and I was the 10th employee and we grew to 900 people and now thousands of people, our team's kind of morphed and changed.

**Heidi Helfand** (00:05:28):
So I feel like if you're in a fast-growing company or a shrinking company, look there, don't look at trying to fight the natural evolution. I was just trying to prove a point and to illustrate that teams change. And I was also curious to see, well, was that just my experience and the experience of my colleagues in Southern California? What is it like for other people? So I was just curious.

**Lenny** (00:05:56):
You have this code in your book where you say something like, sure, we deliver software on time, we make products people love and want to buy, but there's this people layer that happens that people may not be thinking enough about. Is there anything more you can say to that?

**Heidi Helfand** (00:06:11):
Yeah, I think a lot of the things that I would read about teams just are naturally focused on, well, you want to build things that customers love. You want it to be an enjoyable experience, you want to deliver on time. There's a reason we're there as a business, but there's also a lot of company building that happens in building the people structures and just when you go from one to many to a multitude, there's a lot of work that goes into it. This is enablement type work and it's where I focused a lot of my time and my career helping make teams and organizations successful. So there is this people layer, however, I've thought about this a lot over the years and I think it would be highly convenient if we could just focus on building products that people love and getting product market fit, talking to customers.

**Heidi Helfand** (00:07:06):
It would be great if it could only be that, but the reality is we're humans together and there's a lot of opportunity to build companies that delight people where they're excited to be included in decision-making about how the organization grows and changes or shrinks. So yeah, there's this whole kind of other area of work that I think just doesn't get enough attention and I guess that's where I live and breathe.

**Lenny** (00:07:38):
Awesome. Okay, so I definitely want to get into the five types of reteaming as you described, but before we get there, what I find with reorgs and change is that it often leads to the biggest career opportunities because there's new roles to be filled. If things aren't changing, there's not going to be all of a sudden, "Hey, we have this new role that we want for you." I don't know. A lot of the leaders that move up quickly are the ones that seem to take advantage of change and think ahead and get involved and position themselves in a way where like, "Okay, cool, there's a new position. Oh, clearly it's going to be Heidi." Is there anything you can share there? Any advice for people that maybe see reorgs coming and what they can do to help themselves in that pending change?

**Heidi Helfand** (00:08:21):
I really like it when there's transparency in reorgs. There's a story in my book from Christian Lima at Spotify about how they reorged a large infrastructure team. They visualized it on whiteboards and brought people over to the whiteboards to see the future team structure that the leaders wanted and they got input into the design. We did this at Procore as well inspired by Christian and his story and we had... I think there were 80 people involved in this platform organization that was splitting from two large clusters of teams into three. And I remember when we rolled out the whiteboards from a back office where we were talking about this change for a few weeks and it was scary to roll these whiteboards out because it impacts people's day to day. It's like when somebody is suggesting that maybe you do something different or that something different happens, sometimes it can be kind of triggering. You want to know what's going on. So anyway, but we had courage together.

**Heidi Helfand** (00:09:31):
So we rolled these whiteboards out and it had the team structure with everyone's names on it. It had the name of the team, the mission of the team, how many open slots for hiring across all of these different teams, and then people's names in their existing team positions. And people were invited to look, give feedback. They identified mistakes that we had in the design, "Oh, this team might be better over here and here's why." And people had the opportunity to see opportunities within their own company that they might say, "Hey, I'm interested in this, might I be considered for this?" And then they could have their discussion. So I really liked that the opportunities were shared and presented, so it wasn't some sort of thing that happened in some kind of back room for the whole time. We unearthed the beginning of a plan.

**Heidi Helfand** (00:10:31):
I think sometimes when you convene people for a meeting to talk about anything, it's good to have a starting point. So we had this starting point, we had a variety of different things and I call it whiteboard reteaming in my book and I write about that. And there's even structures that are more open than that. Redgate Software in Cambridge UK. Chris Smith is a colleague of mine and they do regular open self-selection reteaming activities when they're changing their strategic priorities. He talks about this globally very interesting space and it's even more open than putting the names on the whiteboards. They have teams give pitches and this is what they're looking for and they have a whole method for enabling people to say, "Hey, I'm interested in this." I think that really helps because sometimes you might think, "Oh, no one's going to want to work on this." But people can be delighted by working on things that another person doesn't think are particularly interesting.

**Heidi Helfand** (00:11:38):
So giving choice is important. And again, there are different grades of transparency. We weren't up for doing this kind of open reteaming self-selection event, but we were open to the whiteboard variant.

**Lenny** (00:11:56):
I imagine individual employees hearing this of just being involved in the reorg strategy sounds amazing. Executives and leaders hearing this are probably really afraid and feel like there's no way this can work well. And so what I want to understand is how do you actually set this up for success? What I'm imagining when you do this is many people disagree. There's teams people want to join, there's teams people don't want to join. It seems like there's a consensus challenge where do you wait for everyone to agree? Does someone end up making a decision? Does it distract everyone from the work they're doing when you're kind of involving everyone in the reorg? Versus what typically happens, it secretly is planned amongst executives. No one knows it's coming. And I think the reason they do that is because they don't want to distract anyone and they don't want anyone to start freaking out until it's like, "Here's the final plan. Here's what we're doing." So what other advice do you have for people that want to practice this way of reteaming and reorging where they involve the actual team in the plan?

**Heidi Helfand** (00:12:58):
There's a book by William Bridges called Transitions: Managing Life's Changes. I have it right here. Making Sense of Life's Changes. He talks about endings, neutral zone, and new beginning. Ending: you're going through a change, your team is changing. Neutral zone: the period of kind of liminality where you're like, "Gosh, I don't know how this is going to go." You're not quite comfortable. You're not quite in that new reality yet. You're still thinking about what it was like before. And once you're in that new reality and leaders can paint the vision and picture about the benefits of the new reality and the purpose and why we're here and anchor to that to try to raise positivity. But once I learned about that transition framework, going through any subsequent changes myself became a lot easier to grasp and it really kind of makes changes in any part of your life. I mean, his book is not written about software development or product development.

**Heidi Helfand** (00:14:00):
Sometimes we're going to have a say, we're going to be able to participate, sometimes we're not. And being clear on who the decision maker is in a change is really important.

**Heidi Helfand** (00:14:11):
There's another framework that I really like. I don't think it's in my book, but I've written about it in my new book, but it's called RIDE. And we had a chief people officer at Procore and she's now at UKG, Pat Wadors. She taught us the RIDE framework for decision making clarity and it's who's requesting the change, who can give input to the change, who's the decider on the change, and who's going to execute on the change? So it's like R-I-D-E. And I googled this for a while; I couldn't find anything on it. I encouraged her to write about it and I credit her to that, Pat Wadors. She's awesome.

**Heidi Helfand** (00:14:53):
So a lot of the times it's like, what's the problem you're going to solve? You have a current state and a future state and that future state might be up to discussion, but maybe it's not depending on what it is. You're getting acquired, you're probably not going to have a standup meeting and talk about should we get acquired or not? No, you're not part of that decision. And then how's the change going to get rolled out or how are we going to do it?

**Heidi Helfand** (00:15:22):
In other cases at the team level, maybe you have a retrospective and you determine, "Hey, I think we'd be a bit more effective and we'd be able to deliver at a better cadence if we were two teams instead of one team." And if teams have the ability to talk about that and impact and have some agency into how their part of the org evolves and change, I think that could be really cool. I think that could be really empowering. I think that could help us feel more ownership in that company that we're in. It doesn't always have to be like decision making equals hierarchy or the person at the top. It doesn't have to be like that.

**Heidi Helfand** (00:16:01):
But again, reteaming is hard. Reorgs are hard. You can't lump them all into one thing with, oh, it's all great all the time. No, it's not. It's not. But anyway, we need to focus there. We got to focus on this people layer because reteaming is inevitable. We might as well get better at it because we're going to have to deal with it. If we could just build the software, deliver to the customer, get the product market fit, hey, have we delighted them or not? If only it could be that easy. No, we have the people layer. So let's focus there too.

**Lenny** (00:16:37):
On this transparent collaborative reteaming, final question here is just would you recommend time boxing this so that it doesn't suck up everyone's brain power for weeks and weeks and weeks? Or is it very dependent?

**Heidi Helfand** (00:16:48):
Yeah, you got to time box it.

**Lenny** (00:16:52):
Okay. Is there advice you have on how long?

**Heidi Helfand** (00:16:53):
Make a schedule biased towards shorter as opposed to longer. You don't want to deliberate on this forever, because especially as you include more people, it can be distracting. So you want to proceed as expediently as you can.

**Lenny** (00:17:10):
Okay, let's talk about the types of reteaming. This is kind of the core of your book and we haven't even gotten there yet. So you've identified there's five ways teams change. Can you just walk through them, help people understand what they are. And then also, we use this term reorg a lot in this conversation. I think that's the way most people think about change. After we go through this list, what does reorg refer to when it's maybe from the perspective of these five ways of teams changing?

**Heidi Helfand** (00:17:32):
Sure. Okay, so the five patterns of reteaming. One by one, someone joins your company or someone leaves your company, grow and split. It's a growth pattern. Teams grow bigger and then they split into two or more teams. Opposite of grow and split is merging. Sometimes two or more teams merge together. It's more of a shrinking pattern. We might be seeing more of this these days as companies downsize. Things merge together and consolidate. Isolation is, or innovation by isolation. Start a new team off to the side, a beneficial silo, give that team process freedom, great for catalyzing new product lines within your existing company. Also great for emergencies and they just happen anyway if we have incidents and people have to come together, solve an incident and then go back to their teams. And switching. So switching is moving from one team to another team. You can do this at a variety of cadences, short term, long term.

**Heidi Helfand** (00:18:36):
And then difference between a reteaming and a reorg. I think reorg is a word that has very traditional baggage and connotations. And when I was writing Dynamic Reteaming, it just didn't feel like an appropriate word to use for, well, Sue is looking to learn a little bit about how our web operations work, she's going to move to that team. It didn't feel appropriate to call that a reorg because Sue's moving and switching from one team to the next. I think reorg again... Reorganization is a traditional word. It implies on the large, it implies top-down changes that you have say no. It's something different than what I consider reteaming, which is these five patterns that happen at different levels.

**Lenny** (00:19:30):
Awesome. So let me just repeat back these five. So one by one, basically people joining your team, leaving your team, something very natural. People do all the time.

**Heidi Helfand** (00:19:37):
Your company.

**Lenny** (00:19:39):
Or your company, yeah. Growing, splitting a team gets really large and then it's like, okay, let's just split this into two, focus them on specific things instead of this one team trying to cover too much. Merging teams, the opposite of that. Isolation. I want to chat about that one a little more where you just have a team off to the side and they're just dedicated to something that you find really important. So with isolation, you have this awesome story of your time at a company called Expertcity, which turned into something people know most likely and ended up being a great outcome because of this reteaming into an isolation team. Could you talk about that?

**Heidi Helfand** (00:20:14):
Yeah, so I've been at different startups that have grown bigger and one of them, I was the 15th employee. I started as a web editor and became an interaction designer. And we were going to change the world and it was very exciting. We were in Santa Barbara, California. So the company's called Expertcity. And we were working on our first product, which was a marketplace for tech support. So imagine you have a problem on your computer, you can go to our website and then you can select an expert to see and control your screen to help you solve your tech support challenge. And so we had the screen sharing technology that we were inventing in the company. We had the web-based software to manage the interaction between the customer and the expert. We had the experts. We had in-house experts and then the vision was global worldwide experts. You were going to be like this marketplace, this eBay of services is what we talked about in the early days. I was really into this.

**Heidi Helfand** (00:21:17):
This was my first job in tech and I became an interaction designer working on kind of front-end UI flows with engineers. It's actually before the word interaction designer, my title was navigation designer. We made this up. So I was very into... It was before the words like UX and other things. People were talking about information architecture and other sub-genres of design. And we had individual offices. I had all the interaction flows on my walls. I was really into the words and one day I was in there and we were working on a new flow. We had all these hopes and dreams for this product and the CEO came into my office and he said, "Heidi, stop working on the marketplace. We're not going to do that product anymore. We're killing it because nobody's buying it and made six bucks or something last month." And he said, "Go to the beach." We were by Santa Barbara. I'm like, "What do you mean go to the beach?" He's like, "Well, I don't want you to start any work that you're going to have to maintain later as we figure out our next step." And I was like, "Okay."

I remember that day and I'm looking around my office and all these flows on the walls. So really these were domains like domain-driven design. It was all these web domains and which user interactions were going to happen and all these hopes and dreams and it was the first time in my career where we were told not to work on something. It wasn't paused. Some people say, "Oh, we're going to pause this," and then they never get back to it. This thing was like [inaudible 00:22:59]. And I didn't get it. I just didn't get it. I cried, I acted out, I sent this email like, "How can we kill the marketplace? It must live." It was quite an experience.

**Heidi Helfand** (00:23:14):
But then, and I don't know what the timing was, I was invited to be on this team off to the side and there was market validation going on. Our founders and product and others became students of market validation, Four Steps to the Epiphany. So we had built this thing, we spent all this time on this marketplace, but nobody would buy it. And so it was like do or die. We had to shift. This was before lean startup. So Four Steps to the Epiphany was the book, it was the manual, it was guiding the way. And so there were people that had a ton of conversations with potential customers about this new thing that we were going to build.

**Heidi Helfand** (00:23:58):
And so I was invited to be at this team off to the side and there was a small team and we didn't have to do waterfall software development. We were freed from that. We were liberated from that. We got to work in other ways. And I remember working with an engineer and we were figuring out how to create a forgot password flow because none of these patterns existed back then and we got to do this stuff. We got to deploy more frequently and the product was called GoToMyPC where you could see and operate someone's computer from a distance. And that was essentially the pivot that I feel like saved the company. Later we went on, we got folded back into the teams and we built GoToMeeting and GoToWebinar as a technical project manager at that time. So taking a team off to the side, giving that team process freedom. They didn't want us distracted from the drag.

**Heidi Helfand** (00:24:58):
When you're working on an existing product line, you get this cadence and it can become a mature cadence. Maybe people work in two weeks or one week now, but when you're working on something new, you need faster iteration loops. And our founders knew that need. So it was a privilege and I was delighted to be part of this other team and it was really, really exciting. So then looking back over the years, I was like, yeah, isolated teams, beneficial silos. Again, it's going against green of what some of these books say, oh, you want to desilo everything? No, sometimes there's a reason why you have a problem. You want to solve the problem. This was like, I mean, was this company going to go under? I didn't think of those kind of things at the time because I was just super into the work and very passionate and motivated about what we were building. But yeah, isolation pattern came up and we used it at another startup as well ever since.

**Heidi Helfand** (00:25:59):
So yeah, that's the story of Expertcity and from my perspective. Ask different people at different vantage points, but that... If we would've stayed within our teams and we would've had to develop with pixel-perfect mockups done in Photoshop like, "Here you go," I don't think we would've been fast enough. That was not good for the innovation that we needed. So it's also like innovation by isolation. It's good for emergencies. I was at another startup, we had performance issues with our first product. People left teams, brought a consultant in, went into a conference room for a couple of weeks, figured out some major changes that needed to happen, solve them, went back to the teams. This is not a new concept. The Chicken McNugget was saved by an isolated team, SWAT team.

**Heidi Helfand** (00:26:57):
There's a book called Teamwork. It's an old book from, I think the '70s, I have in my bookshelf here, and there's a story of the Chicken McNugget that you can read about where they brought in a consultant and had a very small team who worked in a different... They didn't work in their same plant where they were developing the product. They worked in a different plant. They reported straight up to one of the executives at McDonald's. And yeah, the Chicken McNugget lived on because it was like having challenges in the test marketplace in Indianapolis. So we didn't make this up. It's just like some of these things are kind of like, "Oh, it's like a noticing," and then you're like, "Oh, that's pattern." So it's collection.

**Lenny** (00:27:39):
There's this idea of a startup within a big company. Everyone's like, "Oh, it's just like the startup within a big company. We have all the resources that we need. There's no less risk, but we can innovate and try new things." Rarely does it feel like it work out. You're sharing stories where it does. Is there anything you found or any advice for how to actually be successful in this idea of having a team off to the side doing something innovative and different?

**Heidi Helfand** (00:28:00):
At AppFolio we did this. So there's a company called SecureDocs; it branched off into its own company and it was just acquired, I believe in 2022. When SecureDocs was happening, I was not on that team. I was on the other teams and I was watching, and again, same pattern. A team was created off to the side and they were given process freedom. They worked in more of a daily sprint style as opposed to the two-week sprint style that our other teams were doing at the time at early AppFolio. And so, one, isolate the team or put them in a different area. We could still see them. We were in this big open room, but it was their team area. I mean we had these impermanent walls between some of the teams. It was their region and they claimed it and they named themselves.

**Heidi Helfand** (00:28:58):
And so, one, separate location. There's another story in the book about a team that incubated a product idea within Citrix and they were in a garage of all places, so they were really isolated. But just put the team in a different region, make it that area. That's number one.

**Heidi Helfand** (00:29:17):
Number two, tell other people not to disturb this team. That's key. And hearing it from a leader is really, really important. No, you're not going to pull them into something else. They're working on this other thing. So people need to shed their skin of the other things that they're working on. If you take a bigger picture, kind of forest through the trees picture, you want people pairing and switching pairs so they're not single owners of the system. So when they have an opportunity to do something that could be really important to the company beyond one of these isolated teams, they can fade out and not be the only owner that has to transfer knowledge and then field questions for two years on how that system works. You want to build this redundancy in your teams. So that's like if you really want to plan ahead, do that first. Have that as part of how you operate, building this team redundancy and switching, because then it frees people to not be the only owner of a system and chained to a system.

And so isolate them. Tell people not to bother them. Do pairing and have shared ownership so it's easier for somebody to switch into something like this. Process freedom. Again, they can do things differently. Ideally they report up to someone that really has decision-making authority and decisions won't get reversed. Or they have to go through some complex web of like, "Is it okay if we do this?" No, you need a clear decision-making structure. They saw that at the McDonald's case study as well, which is not in my book, but it's in [inaudible 00:30:52] book called Teamwork.

**Heidi Helfand** (00:30:53):
And then that group, having that senior leader that they report into, getting the clear lines of communication there is also really important. So not having this heavyweight bureaucracy of, I don't know, quarterly business updates where everybody's making a slide deck for two years before they go to that meeting, trying to relieve the team of things like that and make it lighter.

**Heidi Helfand** (00:31:25):
And some of these teams, like SecureDocs became another product at AppFolio that was very, very successful. At one point, I think it was before we went public, it branched off into its own separate entity. I think maybe they shared a board member or something. I don't know how that worked, but it became its own entity. SecureDocs became separate and then it grew from there. And then it became this wonderful successful product that was recently acquired. People come and go at companies and companies grow and change and morph, and that was one case of departures that it's like bitter, sweet. You're happy for your friends and colleagues say, "Oh, he's going to be a CTO. He's going to be the CTO."

**Heidi Helfand** (00:32:14):
There's this entity. I remember visiting their office in Santa Barbara. It's great to see your friends succeed and thrive. And we developed other companies in that way.

**Lenny** (00:32:28):
Awesome. I think it's really nice to hear there's many success stories of this idea of a mini little startup within a company, and these are really good tips.

**Heidi Helfand** (00:33:43):
Yeah, I think that's really, really important. I'll also say that things don't always succeed a hundred percent. I've seen isolated teams within companies where someone has the opportunity to sell something, they talk to their friends who are the engineers who build the feature for them, but then it leaves something for other people to maintain later and they weren't involved in the decisions. And it can be a big mess for all of these patterns there. It's like kind of like balconies and basements. You can screw it up too. It's not all stuff is hard. That's why I like to lean into it and I've written about it. Things take effort. The tree is going to drop the leaves and you got to sweep them up. Everything takes work and effort.

**Lenny** (00:34:33):
We've talked about the isolation pattern. I thought it'd be good to talk through the rest of the patterns real quick and share maybe one or two tips for how to be successful or make it work well or better.

**Heidi Helfand** (00:34:45):
Sure.

**Lenny** (00:34:46):
Before you start, actually, I think I missed a nuance and you corrected me, but I think I missed it, which is for the one-on-one pattern, it's actually describing joining the company specifically not joining a team. Is that right?

**Heidi Helfand** (00:34:56):
Yeah. And in the book it might be a little blurred because this is like some of the... Switching and one by one sound very similar, and they do have some Venn diagram overlaps, but I'll distinguish them as I talk about them.

**Lenny** (00:35:11):
Cool.

**Heidi Helfand** (00:35:12):
So one by one, someone joins your company or they leave your company. So the tip with one by one is when someone joins, help them feel a sense of belonging, and you can do that through not having their first day be them sitting over there alone. You could have someone have a first pair. There's a chapter in my book about onboarding. This is in the space of onboarding. Also with one by one, when people join, you also need to pay attention to the people who are already there and it's good for them to know when someone is joining the company; that it shouldn't be a surprise. So visualizing the hiring and the opportunities is something that I think is a really good idea. It could be challenging for someone if somebody joins and they become their manager, but what if that person wanted to be the manager and then they brought in someone from the outside to become the manager?

**Heidi Helfand** (00:36:08):
So you need to pay attention to the new hires that are joining, help them feel a sense of belonging, get them to talk about themselves, which is said to increase their sense of connection and retention. There's some research in the book The Culture Code by Daniel Coyle, which talks about that. But then it's also important to coach the people through change that are already at the company, especially if they weren't involved in the particular decision, bringing on this new leader that comes in and brings in all their people. So you got to pay attention to different people.

**Heidi Helfand** (00:36:45):
Grow and split is a natural thing that happens when you're like startup scale up and growing bigger and bigger. The first team probably grows bigger and then splits into two or three. So when the team gets bigger, facilitation and communication tends to break down. So some signals that teams might bring up when they feel like a change might be helpful is the meetings are taking longer. You're in that case where it's harder to make decisions. It was easier when there were like five of us, but now they're 13. The work becomes divergent. They're working on this one thing, they're working on something else. No one's paying attention in the standup so much anymore because this work has diverged. And those are a few of the signals. And then someone typically brings it up. If you normalize the idea that it's okay for teams to have input into their future structures, maybe they'll bring it up and decide that, "Hey, it might be better if we split."

**Heidi Helfand** (00:37:52):
Sometimes splitting though can create dependencies that weren't there when you were together as one team. So you inherit other problems or you might inherit challenges like, all right, the team decides it's far effective if they split into two or three, but we just have one product manager, we just have one designer. We just have one person who helps us anticipate quality challenges. So it's a lot of problem trading when you do a lot of this stuff. Like anything, you have a challenge, how might we solve it? Well, there's option A, option B and option C. So that's grow and split and it's very common I think when your company is growing and changing, kind of like that.

**Heidi Helfand** (00:38:37):
Merging is the opposite of grow and split. Two or more teams combine together. Or at a higher level, a company acquires another company and then there's a merging that happens. So merging I think is related to when companies downsize or shrink, things consolidate, come together, or again, when at the company level companies combine, one acquires another, gets acquired. How that goes down varies, but there's this concept called panarchy that I write about in my book that a lot of these changes is changes at the individual level, the team level, the team of teams level, department level, the company level. So yeah, merging. So there's a business decision that the companies merge together and then changes might ensue.

**Heidi Helfand** (00:39:28):
So maybe the company wants to get ahead on building and having another vertical in their SaaS company. We acquired a company at AppFolio to bring us faster into workflow software for law firms. So we acquired a company based in San Diego, and that got us a couple of years ahead. I remember one of the leaders saying that. So again, we weren't involved... I wasn't involved in this decision as an IC at the time. So it could be a business decision for merging at that level. It could be that people leave, there are departures and teams and responsibilities consolidate together. That's merging. So it could be that kind of shrinking that we're seeing. It could be that the company is having one leader instead of three and there's a consolidation and the teams kind of merge together. So it's the opposite of grow and split.

**Heidi Helfand** (00:40:23):
One activity I do like to do with teams that merge is called story of our team. That's in chapter 13 of the second edition. So with story of our team, each team makes a timeline of... They stand in order of when they joined their team and they make a timeline with milestones of when they joined their team, when people left, and significant events and things they created that they're excited about and that they're proud of. And that they branch together with their newly merged team, and then it's good to get a shared sense of history. So you have these teams or companies that come together, they make shared timelines, they share their milestones and things that they built that they're proud of. They tell each other about it and then they have a sense of like, "Wow, we didn't know that. Oh, I didn't know that you had built a system like that. We did too." Or, "We've never built anything like that. That is so cool. What did you learn from that?" We get to learn about each other and then we're together. We're like, "All right, we're this merged entity now. What's next?" Looking out to the future so we have the same shared vision. So I love doing that. There's different tactics you can do before, during, and after each of these patterns. Yeah, that's merging.

**Heidi Helfand** (00:41:46):
Isolation we talked about before. Put the team up to the side, give them process freedom, have them report up to a decision maker, tell the other teams not to bother them. Let them work at the cadence that they want to work at. That makes it easier. If you are doing a short-term thing, you got to work it out with the larger entity so you don't create something in isolation that other people have to maintain. There's ways that this can be messed up.

**Heidi Helfand** (00:42:15):
And then switching. Switching pattern is really tied to learning and development and fulfillment. It could be that you want to work with other people. Like forming, storming, norming, performing, Tuckman's model, he forgot the phase called stagnating. Sometimes it feels like we're in a team for too long. We're tired of working with these people. We want a little variety. We want to work with that person over there. Or maybe we want to work on a new system. We don't have the opportunity to do that in our current team, but what if we could work on that system over there with those people? It could totally refresh us. It could be like having a new job within our same company. It could extend the lifespan of the amazing employee in your company. So switching is tied to that kind of fulfillment, which is one of the reasons why I made it separate from one by one and tied that to the company.

**Heidi Helfand** (00:43:11):
The other thing with switching is that you could create safety nets in your company through switching. I just wrote a newsletter post about this yesterday because maybe we're going to have some more changes this year. Maybe companies are going to be hiring less. I don't like the thought of companies downsizing or having layoffs or anything like that, but I think to myself, well, have multiple owners of a system. So not only one person is that tower of knowledge that owns that one system. There's some stories in my book where I interviewed Richard Sheridan, who is the chief storyteller and co-founder of a wonderful company called Menlo Innovations in Ann Arbor, Michigan. They built their company Menlo to have people work in pairs. Not just the software engineers; team members work in pairs and they switch pairs at a regular cadence. And you know that when you're joining the company because you're involved in some kind of pairing. So there's parity from when you're interviewing to when you're at the company.

**Heidi Helfand** (00:44:14):
But switching also helps build that knowledge redundancy in your company. A little more about tolerance. So if someone leaves, they don't leave with all the information in their head. We had that. At that first startup Expertcity, we had some single owners of systems and when they left, it just becomes a challenge and a setback. And at AppFolio we shared a founder between the first startup and the second startup. Many of their early engineers from that first startup went to the second startup.

**Heidi Helfand** (00:44:50):
I was 10th at AppFolio. I was 15th at Expertcity. So we wanted to work together. So it was that global idea of switching one by one or similar. But anyway, at the second startup we had the chance to do things differently. So we had pairing and switching pairs and test-driven development. We had help to do that, but this kind of redundancy built safety into our systems, especially when AppFolio is processing a lot of rent payments. There's a lot of money. There's ACH going through. Those are critical systems and it's very important that things are safe and secure. You don't want to haphazardly switch people around. You can screw this up, again, that balconies and basements concept. You don't want somebody over here, they will switch every two weeks and have no say in their team. There's ways to screw all of this up, but there's other ways to do it well.

**Heidi Helfand** (00:45:48):
I remember when we were at our first team at AppFolio and we did a grow and split. It grew and it split into two or three teams. I remember there was a loss for some of the engineers who wanted to pair program with some of the other engineers, and they started a regular rotation themselves from one team to the next, and that brought fulfillment. It brought joy. I mean they would see each other in the workspace every day, but they wanted to work together. It brought them learning joy and fulfillment, and I love that. For those who are like keep the team stable and the same forever, I'm like, "Well, what about that?" It brings me satisfaction and joy when I see my colleagues. It's like autonomy, mastery, purpose, like Dan Pink's book Drive, when people are really given some agency and the opportunity to work a little bit differently than maybe that traditional boxed version you might see on my bookshelf. You can really create not only products that people love, but companies that people love and want to be at.

**Lenny** (00:47:03):
All these stories of team changes and reorg, it made me think about a quote that one of my managers always used to say about reorging and changing teams is that there's no perfect org structure. There's only the best idea you have at the time for what the org could be. And then there's the issues with that org that you identify as you're putting in place and then set up processes and systems around to try to catch that dependencies, as you said, or overlap of ownership. Is there anything along those lines that comes up of just things you found of just like, there's never going to be the perfect way to do it. This is just our best idea at the time and here's how we deal with the downsides of this approach?

**Heidi Helfand** (00:47:41):
Yeah, I think there's a lot of wisdom to what your manager said and your colleague there because yeah, I mean as time goes on, conditions change. We evolve and change. We're subject to different influences. COVID happens. We weren't dealing with that 10 years ago. We grow and adapt and morph. We try to get together and make the best decisions that we can when we're faced with challenges, and a lot of it is problem trading. We have this challenge today. We decide, oh, there's a few ways we could handle this. Pros and cons of each solution. It's like the Toyota Kata, like grasp the current condition. You'll experience you have challenges. What's the next evolution or the next target condition? How might you get there? And then you're there and you're like, okay, grasp the current target condition. What's it like? What are you experiencing? Oh, we might try this. We're always transforming from the current state to the future state.

**Heidi Helfand** (00:48:54):
So to that, I would ask people, well, how do you want that to be? And how do you want to show up and be as a leader? You want to just be like, "All right, I've got to get this done. The reorg is done by an email and we're just sending it out, or this small team change. And here it is; it's done. Goodbye." Or is it a little bit where you get people's input? And that in itself, you got to weigh what you're dealing with, again. But I like to think about that. What kind of leader do you want to be? Leaders need patience. It's hard to be a leader. It's challenging, but what kind of an environment or vibe do you want to cultivate in your teams and what do you want the people to be like?

**Heidi Helfand** (00:49:42):
I have a degree in teaching English and applied linguistics, and I remember studying Paulo Freire and other educational problem-posing methods of education. We have these teams that solve these complex problems and challenges and build these really cool things for customers. Let's involve them in some of the org decisions that are going to be part of their daily life. Really, you like that idea. Again, it's not perfect. You can't involve people on everything, especially if they're wide-scale changes that you just can't.

**Lenny** (00:50:19):
Along these lines of doing things badly sometimes, you have this whole section on anti-patterns of reteaming. I think there's about five of them. I don't know if you have these all top of mind, but if you do, I'd love to hear some anti-patterns.

**Heidi Helfand** (00:50:34):
Yeah. Well, one of them is people always think that reteaming is, you have a pool of people and you're assigning them to a bunch of different projects like, "Okay, you'll work 10% on this one, 5% on this one, 20% on this one. We are going to allocate the resources from our component-based teams into these different projects." We did that in Waterfall like many years ago, but that doesn't really work. A lot of the times the percentages don't add up. It's very hard for people to multitask and be involved in multiple efforts at once. It's hard for the brain with all the context switching that needs to happen in that case. So I call that the percentage anti-pattern.

**Heidi Helfand** (00:51:15):
There's also, I probably wrote about it like, poof, they're gone or suddenly they're here. Reteaming or having people suddenly show up and you weren't expecting them or suddenly they're gone and there's no communication around it whatsoever, that's another anti-pattern.

**Lenny** (00:51:32):
One of the ones I love is this idea of spreading high performers. This idea of we're going to spread the high performers across other teams.

**Heidi Helfand** (00:51:38):
That's an AppFolio story. Jon Walker was telling me back in the day that... I mean, he did this experiment. He had this thought that many of... There's one team that was like, I guess they were delivering at this cadence that they loved and they were building this stuff and there's this energy and you can almost feel it. Like let's just spread the people from that team across the other ones and then we'll have that. And it didn't work. He didn't have that. It didn't happen. And that was a visceral learning for him that it doesn't essentially work. And people are like, what does it take to be a high performing team? What does it take to have that magical team experience where there's that chemistry and the people are together? And there's stories in the book. Damon Valenzona was telling me one about how it's like's a band and we're with off each other. We're creating this music together. So John felt like he essentially destroyed that when he split up that team. So that's the story that inspired that anti-pattern.

**Lenny** (00:52:49):
The reason people are worried about reteams and reorgs is this... A lot of times it's exact reason that you just shared, which is our team is amazing. I don't want it to change. I don't want to split. I don't want to add anyone. I don't want to remove anyone. I guess is there anything else along those lines to help people feel better about, no, this is actually going to be okay and/or it's inevitable. It's not going to last.

**Heidi Helfand** (00:53:13):
I think sometimes you have that awesome team situation. It's an enjoyable experience. People are learning. You're looking forward to it every day. You're delivering the stuff that people love. You're telling people what's going on. You have that matched expectation where people aren't breathing down your neck because it's late or something. Sometimes you want to keep that team together. You don't want to destroy that dynamic. But the thing is, maybe that's a small startup that grows and you need to grow because you have a bigger vision and it needs to be more than these 10 people. And so there is sometimes this feeling of loss, like, "This is our company. This is my experience at this company of 10 people, but suddenly we're 20 people. It doesn't feel the same like it did anymore and it feels different."

**Heidi Helfand** (00:54:05):
And people, they always ask the question, "How do we maintain our culture? It feels different than it was before." The thing is, it is different, and our companies go through stages. The company of today is not the company it was a year ago. The people turn over and change, what we work on turns over and change. The whole world and industry and global events change and put different pressures on us, and we got to live in this global context. So nothing lasts. Sometimes I have a picture of myself holding an ice cream cone that's melting. Not to be a total downer, but appreciate it when you're on a team and you love it and it's amazing because these are our lives and we have to have gratitude and appreciate what we have because naturally things evolve and change. It's just inevitable. So we appreciate what we have.

**Heidi Helfand** (00:55:07):
A lot of us can look back on our careers and remember those times when we were, in my case, skipping through the halls because I was so happy. And I was like I couldn't even tell you. Well, why was I skipping through the halls at that moment? What was it? Well, it was the people and the conditions and what we were doing and the time, the era almost because yeah, it does change.

**Heidi Helfand** (00:55:30):
There's a book by Ichak Adizes called Managing Corporate Lifecycles. It's one that many of us read for years at AppFolio, maybe the previous company as well. The Adizes Institute influenced some of our leaders and they influenced us with this. And it talks about the different stages of companies from birth. There's go-go stage, maturity, death of companies. These are like lifecycles. The company grows and changes and morphs and changes. The people in the teams do that as well. I have an ecocycle in my book where I talk about that kind of aging and changing. Then there's a disruption and you have a new beginning. We're part of these stories that are in progress. This is not an unchanging, unmoving entity that we work in. So just be kind to each other, enjoy your experiences and learn as much as you can.

**Lenny** (00:56:30):
It reminds me of advice Sheryl Sandberg shared when she came to the Airbnb offices. Someone asked her: "What advice do you have to deal with all this constant change?" Like the quote I shared at the top of the episode of every six months, there's a massive reorg. Our culture's changing. Teams keep changing. It's constant flux. What is your advice to deal with that? And her advice was: That is good. The fact that you're growing so fast and having to change is the best case scenario because the alternative is you are not growing and it's much harder and much more painful because the changes are much harder. People get let go. Your business may go away. So her advice is just, this is good. Change means things are... And growth leads to change, especially hypergrowth, and that you should appreciate this time versus be afraid of it and think that it's a negative.

**Heidi Helfand** (00:57:23):
And it seems like she had such a wide vantage point and could see the forest through the trees of the fact that, well, this company's doing well and this is why we're growing and changing. And I remember one of my leaders, CTO Jon Walker, AppFolio, he told me that once too. He was like... I'd be having a problem or something and I'd come to him and he'd always say to me, "It's always great to be at a successful company, Heidi." And it's like, well, yeah, sometimes you don't think about the finances when you're in your day to day and you have a problem with another person or they come to you and they have a problem with this other person. But in the grand scheme of it, how is the company doing? It's really a critical vantage point that we need to remind ourselves of. But yeah, I wouldn't say all change is always good. Your mileage may vary there, but the general idea that the company is doing well, you're growing and changing, you're trying to make things happen, I think is definitely the space I'd rather be in than the opposite.

**Lenny** (00:58:31):
And I think it's especially true for people that haven't worked at a company that didn't work out where they think this sucks when really this is pretty good compared to all the things that could be happening.

**Heidi Helfand** (00:58:42):
Yeah, yeah, definitely. So we coach and help each other as we go along.

**Lenny** (00:58:48):
Final question before we get to a very exciting lightning round. Used to work with John Cutler, who was a previous guest on this podcast, and he had a question that he wanted me to ask you. He said that, "Heidi is one of the best listeners I've ever worked with." And so the question is, what's your secret to being a good listener?

**Heidi Helfand** (00:59:07):
Well, listening is a muscle to build and to always work on. You got to put your attention out. Focus on the other person. Sometimes if I'm looking down, maybe I reconnect and look at them. You got to read body language and other things. I'm trained as a co-active coach, which involves different levels of listening. So you have level one, which is internal listening. Like if you and I are talking, but I'm thinking about what am I going to have for lunch? I'm in level one. I've got to redirect it out to you and focus on you. So when I focus on you is I'm in level two listening. I'm putting my attention out and I'm really anchoring towards you. It's a coaching skill.

**Heidi Helfand** (00:59:47):
And then level three is global listening, environmental listening. If a marching band suddenly walked behind you, I'm going to point that out because it's in my field. I'm not going to ignore that. I'm going to bring that up. So we pay attention to the vibe and the feel in the room and where we're at. But then also if you're talking about something and suddenly you go like this or you have this kind of sudden pain in your neck when you're talking about this one thing, I might notice that you're doing this and touching your neck because that's information. That's a kind of listening, and so I might ask you about that. Or if the face turns red or you look down or away, it's another kind of listening. So Co-Active Training Institute, coactive.com is my co-active coaching training, so I learned it from them, Henry Kimsey-House and-

**Lenny** (01:00:48):
Wow, that is an awesome answer. There's a lot of depth there. So coactive.com, I'm going to check that out. So you actually got trained in this skill. Okay, that's great. That'll make people feel better. They're like, okay, amazing. I'm going to check this out. I'm going to try to be a better listener through the rest of this podcast episode from these tips.

**Heidi Helfand** (01:01:08):
I will say that sometimes I'm not a good listener though.

**Lenny** (01:01:13):
Yeah, so it goes. Heidi, is there anything else you wanted to touch on or share before we get to our very exciting lightning round?

**Heidi Helfand** (01:01:22):
I don't think so. I really appreciate your questions and talking with you.

**Lenny** (01:01:28):
Well, we've reached our very exciting lightning round. Are you ready?

**Heidi Helfand** (01:01:33):
Yeah.

**Lenny** (01:01:34):
All right. First question, what are two or three books that you've recommended most to other people?

**Heidi Helfand** (01:01:39):
Leading Intelligent Teams is one, Liberating Structures is another one, and of course, Transitions by William Bridges. I also like the Leader's Guide to Participatory Decision-Making.

**Lenny** (01:01:53):
Is there a favorite recent movie or TV show that you really enjoyed?

**Heidi Helfand** (01:01:57):
I did like The Bear, the cooking-related show, the restaurant-related show, and gets into the hospitality industry. I really like that. Movies, there isn't really one that stands out. I always look forward to being on an airplane to see what movies are playing, but no movie for you.

**Lenny** (01:02:21):
What is a favorite interview question that you like to ask people that you are interviewing?

**Heidi Helfand** (01:02:27):
I always like to ask people, "Well, why do you want to join our company? What is it about working with us that would be exciting for you? Why our company as opposed to another one?"

**Lenny** (01:02:39):
What do you look for in their answer that is a good sign?

**Heidi Helfand** (01:02:43):
They have some knowledge about what we do, what we build. Maybe they bring up that they've noticed something on one of the websites or a product launch that we just announced, just that maybe it's part of their story in their career. They're going in this direction, and they heard about us and they thought, "Wow, I would love to work on that."

**Lenny** (01:03:08):
Is there a favorite product you've recently discovered that you really love?

**Heidi Helfand** (01:03:11):
I'm very into vintage clothing and specifically real wool cashmere, not synthetic blends. I also like vintage blazers. A lot of the times where I'm giving a talk, I'm wearing a vintage blazer. I really like the clothing and design, and I kind of really, really love unusual vintage pieces that I could find, but they do need to... A lot of the fast fashion that's out there today is a lot of these blends with these materials that you've never heard of, but there's something special about vintage cashmere, for example.

**Lenny** (01:03:56):
Do you have a source for some good stuff? Is it like eBay? Is it stores locally? Is there a site? Is there somewhere you're finding some good stuff?

**Heidi Helfand** (01:04:03):
I travel around the world and I give talks on reteaming. I do workshops. And usually I go to vintage and antique stores. I was just in Berlin. I was doing that. I was doing it in London. And yeah, I love thrifting, Salvation Army, Goodwill, any of these places that we have in many of the US cities, the Humana line of stores that I've been to in Europe and other places. I try to find the small, unusual antique places as well. My aunt's an antique dealer in Michigan, and she doesn't specialize in vintage clothing, but I just love that idea of discovering unique and unusual things that maybe they remind you of times in the past. Maybe you find that, "Oh my gosh, we had that mug back in the '80s or whatever, or in the '90s." Things can kind of remind people of other times. So I like that. I think there's information stored in unique items.

**Lenny** (01:05:12):
Beautiful. I bet Berlin has some really cool vintage stuff, really wacky stuff.

**Heidi Helfand** (01:05:16):
Yeah, there's a lot of really interesting places to explore, and I think it's just so much more interesting than some of the brand new kind of stuff.

**Lenny** (01:05:30):
Agreed. Two more questions. Do you have a favorite life motto that you often find yourself coming back to or sharing with friends or family, either in work or in life?

**Heidi Helfand** (01:05:41):
I like asking people how can you be kind to yourself?

**Lenny** (01:05:47):
Say more.

**Heidi Helfand** (01:05:48):
I ask myself that too. I used to run a lot in Santa Barbara at Ellwood, which is a beautiful trail that you can go down to the ocean, you come back up. It's like More Mesa in Santa Barbara, and I would run and then I'd be like, "God, this is so hard." And then I would walk for a little while and I'd think to myself, "Well, how can I be kind to myself? I mean, what am I doing here? Does it have to be fast? No. I am here to decompress and enjoy, so how can I be kind to myself?" I think sometimes I get hard on myself or have very high expectations kind of achiever mentality, and I've learned through the years that it's okay to slow down. It's okay to not go, go, go the whole time. So I would ask other people that as well, especially if they're going through a challenge or burning midnight oil or whatever. It's like, "What about self-care? How can you be kind to yourself?"

**Lenny** (01:06:56):
Beautiful. Final question. I was scouring your LinkedIn and I saw a quote from the CTO of AppFolio in his endorsement of you. Said that you were the unofficial director of fun at AppFolio. Is there a story that comes to mind of something that you did at AppFolio that created a lot of joy and fun for the team?

**Heidi Helfand** (01:07:15):
We had these hack days, and I think they do that to this day. So twice a year we'd bring people together and we copied and learned from Atlassian. I remember we had calls with some coaches from Atlassian for how did they do their ShipIt Day, or they originally called it FedEx Day, changed it to ShipIt Day. We followed their model and we'd had this two o'clock on Thursday at two o'clock on Friday where we'd build whatever we wanted and we'd have a theme, and then we'd have goofy prizes at the end that were like traveling trophies. One of them was like a clickety-clack keyboard that we spray-painted gold by the railroad tracks, but people could work on anything. There were teams that formed... We did it with a self-selection marketplace. People formed their topics and teams, and one team hid geocaches throughout Santa Barbara. They're there to this day because we registered them with the Geocaching website. Another team built a vintage video game machine, and it was in the dev room. Another one they catapulted. They built this... Is it a trebuchet?

**Lenny** (01:07:16):
Yeah.

**Heidi Helfand** (01:08:27):
That catapult this fruit in the parking lot. I don't know how we got away with that, but we were in the early days. We did a lot of fun stuff like that, and you could work with different people, build these larger relationships, which later makes it easier for reteaming, because then later if you reteam, you're not strangers with people, so you want to cultivate the community. So we had this department of fun. We would plan the fun in a variety of other ways as well.

**Lenny** (01:08:56):
So fun. Heidi, you're awesome. I think we've helped a lot of people feel better about the endless change that they're probably going through right now. Two final questions. Where can folks find your book, find you online if they want to reach out, and how can listeners be useful to you?

**Heidi Helfand** (01:09:10):
You can go to heidihelfand.com or Google my name and I come up. Heidi@dynamicreteaming.com, heidi.helfand@gmail.com you can find me. I'm out there. And yeah, I love to work with companies and teams going through change, and I do that in a variety of ways. Teach workshops, do talks. So if any of this is interesting, reach out.

**Lenny** (01:09:33):
And then do you also consult and work with individual companies or not?

**Heidi Helfand** (01:09:37):
I do. Yeah. I do that now. I like to work on a retainer basis or I'll even join a team, so looking for the-

**Lenny** (01:09:37):
All right.

**Heidi Helfand** (01:09:45):
... next one.

**Lenny** (01:09:47):
Amazing. And we'll link to all this stuff in the show notes. Heidi, thank you again so much for being here.

**Heidi Helfand** (01:09:53):
Thanks so much, Lenny.

**Lenny** (01:09:54):
Bye everyone.

**Lenny** (01:09:57):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [6/19] Good Strategy, Bad Strategy | Richard Rumelt

**Richard Rumelt** (00:00:00):
Don't call it strategy, call it an action agenda. It's huge numbers of people out there willing to sell you advice on mission and your vision and your values, all these things that have to be in place before you can have strategy. That's not true. Begin to try to identify the one or two key challenges that can actually be addressed and what are we going to do about it? What are the coherent actions we're going to do to take these on? Okay, we're going to go after this and here's the action steps we're going to take to do that. That's the essence of what you're doing when you're thinking strategically.

**Lenny** (00:00:42):
Today my guest is Richard Rumelt. Richard is an absolute legend in the world of strategy. It was such an honor to have him come on the podcast. He's the author of Good Strategy Bad Strategy, which I've gifted to countless people who wanted to become more strategic. He's been mentioned so many times on this podcast. He's also the author of The Crux, his most recent book, which some consider his best book, which delves even further into his advice on how to craft a winning strategy.

**Richard Rumelt** (00:04:33):
Thank you for having me, Lenny.

**Lenny** (00:04:35):
It is such an honor to have you on this podcast. So many guests on the podcast have mentioned you and mentioned the book. I probably bought your book for, I don't know, dozens of people over the years, and it is just so cool to have you on and to get to delve into the stuff that you teach. So thank you again for being here.

**Richard Rumelt** (00:04:51):
Thank you.

**Lenny** (00:04:51):
I thought we'd start at the beginning and then work our way up and kind of see where the conversation goes. What is the simplest way to understand a strategy? What is a strategy, and then what are the essential components of a good strategy?

**Richard Rumelt** (00:05:05):
Well, a strategy is a design for overcoming a high-stakes challenge. It's a mixture of policy and action designed to deal with a challenge. The challenge could have an upside. It could be, "Oh geez, we were fooling around in the back 40 and we discovered oil, what we do?" Or it could be negative, could be that new innovation is driving us out of the market. But a challenge is the hardest strategy. The work comes from Strategos, which is Greek. The Greeks elected 10 Strategoi to serve as strategic leaders at Athens. And they were elected and they dealt with issues of the day, the Persians are invading, there's a plague in town, we need money for a new temple. And that's where the word comes to us from. It isn't just military, it wasn't in Athens. So strategy is always about dealing with an issue, a challenge, a problem. What are we going to do about global warring? What are we going to do about China wants to reunify with Taiwan?

**Lenny** (00:06:24):
You obviously have these very infamous famous elements of a good strategy, something you call the colonel. Can you just talk through those pieces?

**Richard Rumelt** (00:06:33):
Right, sure. So when I used to teach strategy for many years at Harvard and then at UCLA and other places, there's lots of ways of looking at strategy. And so years and years ago, we used to look at the [inaudible 00:06:51] and the matrix and the five forces and all of those kinds of analytical tools. And it began to dawn on me at some point that this is a strategy. These are analytical tools for analyzing the problem, for thinking about things, for looking at competition. But they're not strategy. Strategy is, one, and I started to write a book and the first chapter of the book was... the first part I wrote was the David and Goliath strategy story. And my point in writing about David and Goliath was that the surprise that David is able to beat this giant warrior, and that's a strategy story. Strategy story is about discovered strength.

**Richard Rumelt** (00:07:43):
It's about, oh wow, look at how they did that. Look at how he got made in five moves. That's a strategy story. Look at how Steve Jobs changed the world when people couldn't expect it. That's emotionally what a strategy story is. So I want to write about strategy. And my wife Kate asked me, "Well, do you define strategy?" I said, "Oh, it's really hard. I can't define it." And she said, "Well, you can't write a book about it if you can't define it." Because I said I had this other conceptual scheme in my head that all teachers and writers had, which is that there's a bunch of analytical tools. And this is back in 2005, 2004.

And I gradually came to the realization all strategy is problem solving. It's a form of dealing with challenges, and that was a basic idea going in the book. So if that's the core of it, what's the basic activity? What are you doing when you create a strategy? Well, you're diagnosing the situation. You're trying to figure out what's going on here. What's the nature of reality that you're dealing with? Now, humans can't understand all of reality. No one can. So part of what a diagnosis is, is a decision about what you're going to pay attention to and the hypothesis for several hypotheses about what's going on, how do things connect together. And that's beginning of the diagnosis. And so diagnosis is an understanding of the situation that you're in. Well, that's not novel. And you can use any of those tools that are famous for that and you can try to find forces. You can do any one of a number of things to try to comprehend the situation. The world is more complicated than 2x2s, unfortunately. I was educated as an electrical engineer and my early years were spent designing spacecraft for NASA. And when I got into looking at business and business strategy stuff, I was always amazed at how unintellectual it was, that I was struggling to master Z-transforms and multiple, and yet these people are looking at 2x2s and little diagrams [inaudible 00:10:19], oh, that's what the company's about. So a rich diagnosis of the situation, but then a guiding policy.

**Richard Rumelt** (00:10:28):
The guiding policy is what are we going to do? Now, it's a simple thing to say, a guiding policy, and the guiding policy is sort of the strategy. It's the core of it. It's here's how we're dealing with the situation. And yet, when I say that, it flies in the face of, as I was writing that, I had a client who had 17 priorities. This is what we're doing. We have 17 priorities. And that's the opposite of policy. That's a laundry list of all the things we wish would happen over the next year. We're going to gain market share in China, we're going to cut our emissions, we're going to save energy, we're going to become safer, we're going to cut costs, all these different things that we're going to do. And they're all priorities. Now, lots of people need misuse the word priority when they're trying to do all that. You wouldn't want to be in a commercial airplane and hear the tower say to the pilot, "I'm giving priority to the following three planes on runway five." Right away, you know there's something wrong.

**Richard Rumelt** (00:11:50):
Well, that's the word priority, it means the first. It doesn't mean the grab back everything that you can think of that might matter. It means what's first. And so the guiding policy is sort at that level of what do we really have to do here and what are we doing and what are we not doing to deal with the diagnosis that we created?

**Richard Rumelt** (00:12:14):
And then the most important part of a strategy, the part that it's so easy to leave out because people like to think of strategy as this high level conceptual thing, is the coherent action. You have to do something. And what you do has to be coherent in several ways. The first way is it has to deal with the problem or the diagnosis and the guiding policy, it has to implement. It has to be coherent in that you shouldn't do things that fight each other.

**Richard Rumelt** (00:12:51):
You shouldn't say, "Oh, we are going to burn less oil and at the same time we're going to import more oil." It doesn't make any sense to do things that are self-contradictory. And yet, people do it. Most companies have strategic goals of increasing growth and increasing profit. Magically, that can happen in some cases. Growth and profit, they battle each other. Let's say we define profit as return on equity. If you're going to increase growth and increase return on equity, how do you do that? Because you're basically trying to invest less to get your return on equity up. Or you're going to grow and get your profit margin up. Well, how are you going to do that? You get your profit margin up and grow faster.

**Richard Rumelt** (00:13:52):
This is baby talk, but CEO after CEO will stand up and say, "Well, we're going to grow and we're going to make a profit." And so having coherent actions, actions that dump milk on one another is an important part of strategy. All three elements have to be there. There has to be an understanding of the situation. There has to be a guiding policy, how are we going to deal with it? And that could be a long-term sense of how we could change. You don't have to change your strategy every five minutes or every five years. If you're making Almond Joy candy bars or something, you don't really change your strategy constantly. If you're in the tech business, of course you have a shorter time horizon. And then the coherence and action is critical. And so these are the three, what I call basic elements, the kernel that if anyone in three is missing, something's wrong. It's not really a strategy, it's something else.

**Lenny** (00:15:04):
Awesome. Okay. Is there an example that you could give that makes these even more concrete of just, I don't know, something that comes to mind that's a quick example of a strategy that illustrates these three components?

**Richard Rumelt** (00:15:17):
If you're Microsoft right now and you're trying to adapt to AI, you have a diagnosis. Well, what's going on? You see the challenge of how do we adapt to it? You create a guiding policy that you're going to invest in one of the major leaders and that you're going to begin to incorporate that into your search engine. And then you have coherent actions. You actually do some of these things. It's not rocket science. The difficulty is that companies don't do that.

**Richard Rumelt** (00:15:55):
There are companies that say, "Well, our future is"... let's say something that's not in a software business. That's industry 4.0 for 5.0 that we're going to have... we're investing in the future of robotics and AI and even computer vision and all that. That's going to be our future. And then you see what they're doing. They've bought this company, they've bought this company, they've bought this company, and that's it. It's strategic assembly without any synthesis. So strategy's not mysterious. What's mysterious to me, what was mysterious to me and what remains mysterious to me is how so many organizational leaders don't do it. They create bad strategy. They do something that they say is strategy and then it's not.

**Lenny** (00:16:55):
You have a whole chapter on this, on what is a bad strategy. Can we just touch on a few of the things you see as signs that your strategy is bad or maybe it doesn't even exist?

**Richard Rumelt** (00:17:05):
Sure. When I wrote Good Strategy Bad Strategy, a lot of people resonated with the bad strategy. Part of the book, they wrote emails and saying, "Oh my God, thank goodness someone just finally said that these long and terminal meetings I sit through are not actually strategy." Or these documents that the company produces are not actually strategy. And they're not. Bad strategy, the standard bad strategy for a corporation is a set of profit goals or performance goals. A set of goals. Goals are the engineering of how companies work to some extent. But abstract, high-level goals, they're not strategy, they're something else. They're ambitions. And ambitions are not a strategy. A list of all the different things you wish would happen is not strategy.

**Richard Rumelt** (00:18:13):
I was asked to help part of the U.S. Department of Defense create a strategy for what's 17 different intelligence agencies.

**Lenny** (00:18:26):
Wow, how cool.

**Richard Rumelt** (00:18:29):
Yeah. There's 17 different intelligence agencies. And the strategy basically that these people had written said the 17 agencies should work together more effectively. Now, you don't have to be a Russian spy to see that what they're really saying is these guys aren't working together effectively and it's a problem. But they didn't say that. They said the strategy is they're going to work together more effectively. Just like the RV always comes out with our strategy is join us, meaning we're having trouble with coordinating.

**Richard Rumelt** (00:19:08):
But then there's nothing there about that other than this is what should happen, there should be more effective coordination. And oh, we'll have an office of coordination, put a person in charge of coordination. But there's no sensible... why is it hard to coordinate? What are the barriers to this? This has been going on for 34 years now. What's holding it back? What is a problem we have to solve? It's not there.

So I was hired to do a foundry for a company and they said, "Well, our diagnosis is not growing fast enough." Okay, let's get into that because that's not a diagnosis, that's a statement. It's a statement of value, you would like to grow faster than you are. I'd like to be taller than I am. I'd like to have more hair. You want to grow faster. Okay, so what's holding you back? And from [inaudible 00:20:19]. But saying, okay, we're going to grow, that's not a strategy.

**Richard Rumelt** (00:20:23):
Bad strategy also is fluff. People will use fancy words to describe their situation. Since I wrote that, the term word salad has become common. And there's a lot of word salad writing that people try to use to describe their situation. It sounds more abstract perhaps more abstract. Therefore, it's more strategic, incoherent stuff where we're going to do A, and we're going to B and those two things obviously fight one another. All those things are part of bad strategy. Bad strategy is a document or a set of intentions or a set of verbalizations where it's not a strategy. There's no diagnosis. Of course, I don't doubt that. Started out saying where United States is falling behind in education. And he's looking at the piece of the PISA test scores of 15 year olds around the world. And it's true, the United States is down, number of 30 countries in terms of the scores of our 15-year-old, in math and in general knowledge. Okay, correct statement, we're falling behind. A real diagnosis would say, because. We jumped immediately to therefore, we're going to have more people go to college than any other country. Well, having more people go to college doesn't solve the problem of 15 year olds not being able to do elementary math. Hopefully it doesn't screw up colleges everywhere. So that kind of gap, it's there, where you don't do the diagnosis. Why do we have this? We argue over diagnosis as part of politics and part of organizational politics. That's what we do, and that's important. To do a strategy, you have to resolve the argument. Why do we have a homeless explosion in Portland or Seattle or Los Angeles? And people argue about that. Some people say, "Oh, strokes." Some people say, "Oh no, housing is too expensive." There are different diagnosis. But to deal with the issue, you have to decide on the diagnosis. The politicians right now sort of decided for a few years that the problem is housing's too expensive, we're going to build housing at $700,000 a unit and give it to the all people. Okay. If you build it, they will come.

**Richard Rumelt** (00:23:28):
But then the next problem is, well, can't seem to build a housing. And so again, you need a new diagnosis. Why can't you build a housing? You're a rich, powerful country. Why can't you build some housing? So diagnosis is critical to understanding it. And in public policy, we argue over the diagnosis. And in organizations we argue. And unless you resolve it, you can't act. So lacking diagnosis is one of the key reasons for bad strategy. The other, the fluff and the incoherent actions are fun to describe, but they're less common. The second major source of bad strategy is mistaking goals for strategy, saying these goals are our strategy. And that leaves out so many of the important aspects.

**Lenny** (00:24:22):
Amazing. So just to summarize somewhat, if you're missing a diagnosis, trying to explain what exactly is wrong, it's a sign your strategy is incomplete or bad. If you're missing concrete actions, it's a sign that your strategy is incomplete or bad. There's also I think an element of coherence. The actions have to connect and there have to be a few, very few of them. I always like to think of three as a good number. Is that something you think about, the rule of thirds for actions you want to take or even the guiding policy, or is there a number that you think about just like no more than this?

**Richard Rumelt** (00:24:53):
A few. A few. Not too many. Not 17. It's hard. Numbers. We work best when we concentrate. We're more effective when we concentrate on a few things, a few people, a few... focus, it's the fundamental source of power and strategy. Trying to do too many different things is defocusing.

**Lenny** (00:25:18):
I think there's this quote in your book that I think is, and this may be paraphrasing, each time you say yes, you risk turning a nascent good strategy into a bad strategy.

**Richard Rumelt** (00:25:28):
Yes. Focus is... when I was nine years old, I was at summer camp and I had my parents sent me a magnifying glass and I was out there using the sun to try to cook a piece of wood. I think I had a piece of cloth that I was trying to burn, wasn't having much luck. The magnifying glass focuses the sun's rays on the spot. Counselor came over and he said, "Try this," and he pulled out a black thread from his T-shirt, put it down. And I focused the sun's rays hard, popped out. So stupid little story. But to burn that black thread, there has to be a source of power, the sun. There has to be a focus, that's the magnifying that to the power. And it has to be a target that can be affected. It has to be a black thread, not white thread. And that sequence is part of strategic action. You need a source of power. I say power, I don't say advantage or efficiency.

**Richard Rumelt** (00:26:53):
I say power because there are different ways in which power is exhibited and you have to focus the power on a target that can actually be affected or achieved. And this is real simple logic, but it's a discipline to focus power on a target that you can affect. Take American power and say we're going to change China's trajectory and Russia's trajectory and our own and to name all the 30 countries around the world that we're trying... we're diffusing our efforts because they're not the same. They're going in different directions. Obvious when you say it, not so obvious as you live it, because like any organization, like any big organization, US government has different interests. They're pursuing different interests funded for different purposes with different clientele. And so there's gradually a diffusion-

**Richard Rumelt** (00:28:00):
And so there's gradually a diffusion of effort. One of the big issues in strategy is simply the organization, complex organizations particularly. You have a hard time focusing energy because of all the different interests.

**Lenny** (00:28:21):
Yeah. Actually I want to talk about both those things, so I'm glad that you teed them up. Let's talk about power. What is this idea of power and how does that play into strategy? Why is it so important? And then what are some examples of power that people can think about when they're trying to think about implementing and adding a power to their strategy?

**Richard Rumelt** (00:28:40):
Well, in a competitive situation, the fundamental aspect of power is something that's going to give you some sort of advantage. Usually it's in asymmetry of some kind. If two fighters are equally balanced or two horses are equally fetched or two armies are equally... And they meet in competition, it's 50/50. Who knows what will happen. For a strategy you need to exploit in asymmetry of some kind. You hear a little faster. Or they're a little... Something has to be different between now and between things. So that's the beginning of power, is asymmetry. We can think of it as leverage, but sometimes think first is a source of power.

Being first to recognize something can be a source of power. Having a reputation of a certain kind gives you some power that someone doesn't have that reputation doesn't have. On the other hand, having a well-established reputation of a certain type can be the opposite of power because people don't expect you to be able to do something new. They expect you to be able to do this, but not that. Having relationships can be a source of power. When Gerstner took over IBM as it was failing in the face of the microprocessor revolution, he recognized that their primary asset, their source of power, was that they were respected and they had [inaudible 00:30:38] into every large corporation on the planet. Nobody else had that as an actual producing company. And so he said, we're going to embrace our customers. Bear hug our customers. We're going to serve our customers.

**Richard Rumelt** (00:30:58):
That's our source of our power. That's our leverage. That's the synergy. Now the world begins to change and computing begins to move to the cloud. And IBM's customers, the largest companies in the world, are the most hesitant to do that, because they've got the big IT departments that don't want move to cloud. And so small companies move to the cloud and the big companies are, well, it's insecure in the cloud. We'd have to lay off people. We have these big machines we like to run.

And so IBM then becomes disadvantaged in the new world because it inherits this big company orientation and that lagging behind. So the opposite side of power is what you inherit. From [inaudible 00:32:01] can be the wrong thing. But a source of power is that. A source of power can be an invention, a source of power can be a particular customer base that you have identified. It doesn't last forever, power, but all the different sources of advantage that are sometimes transitory and sometimes permanent are sources of power that a company has to use to compete and survive.

**Lenny** (00:32:35):
I imagine people listening are just like, oh man, I got to figure out the power, the advantage that I have with my business. Is there any advice you could share about helping people figure out where their power might lie?

**Richard Rumelt** (00:32:46):
That's a good question, Lenny. So how do you figure it out? So I start, as I said earlier, with the symmetries. In what way is my company different than other companies? In what way is my team different? What do we know that other people don't know? What do we possess that other people don't possess? So there has to be some asymmetry to create competitive power, there has to be something different.

**Richard Rumelt** (00:33:17):
Sometimes you have to redefine your space down small amount. Then you can actually see it, particularly a smaller company that doesn't have worldwide power, has power in a certain marketplace or a certain set of customers or sometimes it's not customers. Sometimes the power isn't who you can bring in and hire. So if you invented ChatGPT, you can bring in the smartest AI people for a year or two because all the smart AI people want to work at the cutting edge with the current winner.

**Richard Rumelt** (00:33:58):
Then they'll start to arguing with each other and in fight and there'll be all sorts of embarrassing personnel things going on and someone else can grab that position, if it's not well managed. Business is exciting in that sense that it's not stable. It's not just as it was when I was first studying it. It's not just IBM and Sears and AT&T forever. There's a constant changing of the guard.

**Lenny** (00:34:30):
For better or worse.

**Richard Rumelt** (00:34:32):
For better. Because if you look at government, there is no changing of the guard and they get stultified.

**Lenny** (00:34:38):
Makes sense. So in your book, you have this whole list of types of power. I'll just read them real quick. Leverage, proximate, objectives, chain link systems, design, focus, growth, advantages, dynamics, inertia, entropy. There's also the book, obviously The Seven Powers, that a lot of people are aware of. I guess how do you think about just the spectrum of types of power you can have? Is this it? Are there others?

**Richard Rumelt** (00:35:02):
I started to make a list there in the book and I wrote up a bit about chain link systems and today, I mean the power that new business models are exploiting is the power of the user base. What we called years ago, network effects, where the more users you have, the more useful a product is. So I think the idea of network effects first arose with the telehealth system, which the idea was that you don't want to be connected to a telephone system that only connects to two other people. It's not all that useful. It's got to connect to the world to be useful.

**Richard Rumelt** (00:35:43):
And my colleague Marvin Lieberman was taking the economics course at Harvard University at the same time that Bill Gates was a student in that classroom. Professor's going on about network effects and of course that's what catapulted him, had his software, MS DOS at the time. Not MS DOS, he had something called basic that... The network effect was huge. He got angry about the network effect because people wouldn't pay him. They kept stealing it and using it and pretty soon everybody in the microcomputer industry had M Basic.

**Richard Rumelt** (00:36:27):
Then we get the network effects from not just software, but user base is now with the internet and so you get network effects with big social media. No one wants to be on a social media if only three other people are on. So having a large network...

**Richard Rumelt** (00:36:50):
Amazon. Get big fast because the economics are amazing. So we used to say, well, in a department store, economics are that you're saving people the cost of going out of the store and walking down the street to another store. So now it's all in one place. Supermarkets, the same thing. But look at a thing like Amazon where there the ease of shopping on Amazon keeps people from leaving it and going to another website. Now other websites have gotten better and better and some of that is less strong than it used to be and this is a constant struggle with it. Nevertheless, the size of the user bench there is an important source of a symmetry and power for the people that have come out ahead and won that battle for this round, this five years to 10 years. How long does it last before some other thing begins to take precedent. And now we have two-sided markets, whether it's credit cards or places where both buyers and sellers get together.

**Richard Rumelt** (00:38:01):
And so here these big forces that companies are playing with right now are these network effects.

**Richard Rumelt** (00:38:10):
And when the new generative AI, we have the possibility of stronger effects than we've ever seen before, but we don't know yet. But the suspicion is that size is what matters, that the size of the data that you could put into the learning algorithm is going to make your AI better. And so again, a big... It's going to matter.

**Richard Rumelt** (00:38:43):
Just think of Google and their ability to improve search based upon all the searches that go on on their base every day. It's very hard for Bing to catch up because Bing doesn't have as much data to train on. And so unless there's some new innovation there that isn't just the amount of data, the leader again has this asymmetry working for it. Now, the way you get around all that is by being specialized, by owning a particular approach that isn't the market leader's approach. And it's always been that way in business, but our attention is often attracted by these giants.

**Richard Rumelt** (00:39:34):
So yeah, sources of power today where we look at the new business models that are part of the fabric are these network effects and things like that that are very, very strong. And people are trying to get those in startups and in small firms within a certain market space and build it as fast as possible to get ahead of others. There's been venture capital available to try those experiments and some of them work and some of them don't, but that's this new age we're in now, where the speed of building a market position with network effects is a dominant game in the tech space.

**Lenny** (00:40:25):
I feel like Twitter is the ultimate example of the power of network effects, especially recently where if you think about it, everything about Twitter has changed and it still continues to run. You laid off 80% of people at the company, they changed the name, they changed the domain basically, the algorithms changed. I don't know what is still the same.

**Richard Rumelt** (00:40:45):
How can you lay off 80% of the people and it still runs? I mean you got to wonder.

**Lenny** (00:40:49):
I love Twitter. I'm on there all the time. I feel like it's never been better, which is kind of wild.

**Richard Rumelt** (00:40:54):
Twitter's fascinating. I mean I tune into it every couple of days and see what's going on and it is just an amazing rumble of opinions and statements. It's much more interesting than it was five years ago.

**Lenny** (00:41:11):
There's a lot of diagnosing and not a lot of concrete actions. But anyway, I wanted to come back to the element about power. I think when people are thinking about power, it may not be clear where that plugs into the diagnosis, the guiding policy and the coherent actions. Where should you be thinking and implementing this idea of where my power is when you're laying out your strategy?

**Richard Rumelt** (00:41:35):
To undertake a strategy that you think will work, you've got to have a reason that it makes sense and that reason is derived from some source of power, some source of advantage. Ultimately, your power or your advantage is something based in history that has the feel of reputation, or institutional skill, or it's some kind of symmetry or knowledge that you have that others don't have. So it's a resource that you can use that your competitors or others don't have equal access to because you've either have mastered it or you own it or you inherited from the past.

**Richard Rumelt** (00:42:45):
All those things are sources of the power that you use to make it not an even bet. So when you walk into a casino, well maybe if you play poker with skill, you can expect to make some money, but the general casino games, you're going to expect to lose. And in business, statistically, if you come to me and you say, I'm going to open a new restaurant. What should my strategy be? My answer would be don't open a restaurant. Invest in the S&P 500 because the statistics are that new restaurants fail. So what makes you think that you can succeed? Oh, I really want to succeed. Not good enough. I trained under a chef who's been very successful. Oh, that's interesting. Tell me more.

**Richard Rumelt** (00:43:50):
So there, where's the asymmetry here? Where's the source of power where you go from the odds... The standard odds in this game are against people where you think the odds are in your favor.

**Richard Rumelt** (00:44:05):
That's the source of power we're looking for. We're looking for this information, this skill, this thing in the field, the way the resources are arranged, that's going to give you this edge. And some of that is sort of part of the situation and some of it's how you shape and focus your actions. Strategy tends to be surprising when we see it, when we see it work, and surprising because we don't expect it. We expect people to bumble around. We expect Arby's to bumble around. We expect nation states to bumble around. We don't expect them to execute coherent strategies.

**Richard Rumelt** (00:44:54):
The United States went to Afghanistan and it wanted to catch Osama bin Laden, but at the same time they didn't want to put an army in the shield to actually catch him because it would the embarrassing to have that many Americans in the field. That's what happened in Tora Bora. The Secretary of Defense said, no, we don't want to make it look like we're taking over the country, so they didn't try to catch him as hard as they could.

**Richard Rumelt** (00:45:22):
And we want to have the education of women and we want to have a democracy and we want to have a long list that we would have no opium production, but at the same time, our allies are the opiate producers. It was the Taliban that got rid of opiate. Americans didn't do it.

So we had all these different objectives. It doesn't work. You need to have a focus on something achievable. What's achievable? [inaudible 00:46:03] Nation-building is hard stuff. It takes a century. Afghanistan, I'm off on a tangent here with Afghanistan, but it's a really interesting subject. Afghanistan was a warlord society, a bunch of different warlords running the place. Well, what's a warlord society? Where else do we look for an analogies? Well, we look at [inaudible 00:46:32] in 1650. You look at France in 1300. You can look at Japan before the modern era. These are warlord societies. Well, how did they go from that to being a coherent government that maybe wasn't democratic at first, but still, there was a government instead of just as much war. It took some [inaudible 00:46:59] to conquer all the rest.

**Richard Rumelt** (00:47:02):
And then it took a long time for them to put in the structure itself of government and then maybe became a democracy. Maybe not, but that's the process. It's not like you just go in there and say, you're now no longer a warlord with society because we've decreed it.

**Richard Rumelt** (00:47:19):
I don't know. You're going to ask me more questions about what it is people should know and how do you get these sources of power? How do you get these insights? I'm a big fan of history. I'm a big fan of knowing things about what happened. Business history, biographies, war history.

**Richard Rumelt** (00:47:42):
If you don't have access to other times and other places and other things that have happened, it's very hard to think strategically about the situation you're in because there isn't a science of strategy. It's not like physics. It's not like engineering where we can write down the equations of stress on a beam and say, how thick does the beam have to be? It's not like that. A lot of it is based on analogy to previous human experience.

**Lenny** (00:48:16):
That is an amazing insight. Is there anything you find most rich and valuable in terms of history periods, empires, stories that you find most connects as an analogy? Is there anything you find consistently is useful or is it just read as much as you can and you'll often find something in there?

**Richard Rumelt** (00:48:36):
Yeah, the further back we go in history, the leaner. It's less rich. The best histories are written by the people at the moment it's happening or very soon after. History books and things like that are someone's opinion. But our own history here in the United States, we have pretty good documentation about what went on in the Indian War, why we had these big cycles of economic growth and then depression. We had depressions in 1840 and after the Civil War and there was another huge panic depression in the 1890s. [inaudible 00:49:26]. A lot of people don't even know that these things happen. How did they happen? And of course everybody knows about the Great Depression of 1929, 30's, but go back and how did that happen? When did that happen? And you'll hear professors opine about why it happened, but there's no agreement. The biggest economic fact of the last 150 years, you don't know why it happened.

**Richard Rumelt** (00:49:58):
Go back and you can go online and look at the Wall Street Journal of the New York Times from that era and start in September of 1928 and just look at the front page every day, which I've done, and you can see it unfold and it's a surprise to everyone. There goes, well, Ford just laid off the people, but it's temporary. They'll hire them back. This economist says, well, it's a temporary this. It'll come back. And it gradually gets worse and worse and worse and there's no understanding of it. There's not a lot of analysis. And so you got Milton Friedman saying, oh, it's monetary. They didn't loosen up the money supply. You got other people saying things. But put yourself back at that moment in time and see what people saw and realize that no one understood what was happening and to form their own opinions.

**Richard Rumelt** (00:51:10):
That's the diagnosis skill or that's the feeling. Now, let's suppose you fall off a boat. You're on a cruise ship and you fall and you're now in the ocean. It's terrifying and it's confusing and there's waves and there's water and I don't want to drown. And you look around and you see, oh, here's a floating piece of wood. Let me grab it. Wow, that feels a lot better. That's how it feels when you look at a confusing situation and the first idea of how to understand it comes to mind. Oh, yeah, I've got this piece of wood. Now I'm not drowning. But is it right?

The most important intellectual tool we have is to think again, to say, okay, I came up with this diagnosis because I thought this and I thought this. Is there another way to look at this situation? Is there a bigger piece of wood over there than I can grab onto? That's the hard thing. When I looked at the Great Depression what I saw is the [inaudible 00:52:35]. So if you look at capital goods, most capital goods that the public buys, the adoption curve goes up like this, it peaks, and it declines and then it comes back up again. Because there comes a point where everybody who can afford one has got one, and then the new sales drop off. And in my mind, that's what I saw. 1929, everybody could afford a car, had a car, and the auto industry began... First signs of the Great Depression were in the auto industry.

So that was my play that I read. Now I don't see anybody else writing about that, but that's the exercise and to exercise your mind about trying to understand complex situations. It's best to go back. You don't have to [inaudible 00:53:34] to the great Depression, but you can go and try and find situations that other people have to deal with and look at as much data as you can and to practice that. That's what education should be in a business school. It's not. They teach theories now because it's so much easier to teach a theory than intellectual structure.

**Lenny** (00:53:58):
It's also a lot more work, reading a lot of books and history and studying and thinking.

**Richard Rumelt** (00:54:04):
Oh, [inaudible 00:54:05]. I had a colleague at UCLA who assigned a book to MBA students and they went to the dean and had him kicked out of the course because of a book. He wants us to read a book.

**Lenny** (00:54:16):
Oh man. It sounds like you have another book in you writing about the Great Depression and what really happened there.

**Richard Rumelt** (00:54:22):
Maybe.

**Lenny** (00:54:23):
Oh, man. Exciting.

**Richard Rumelt** (00:55:59):
I wrote the crutch because I felt that.

**Richard Rumelt** (00:56:00):
The Crux because I felt that that kernel was not sufficiently sharp enough for peak. And even in The Crux, if I could rewrite The Crux book, I would, maybe, write it a little differently today, a whole couple of things I would change. First, it's really important to understand the challenge, the problem. Diagnosis is not merely understanding the world, it's understanding the challenge you face. What makes it hard? So the question I ask client is exactly that. What makes it hard? Client will tell me, "Oh, we want to open up business in Australia. It's a market we haven't tapped." And I'll say, "Okay, so why are you and I talking about that? You're the CEO. Just tell somebody to do it. What makes it hard?" "Oh, well, we don't know anybody in Australia and they kicked us out." If you push, he'll tell you why it's hard.

**Richard Rumelt** (00:57:18):
But that understanding hasn't been percolated into a strategy. Part of the problem is that the concept of strategy has been so beaten up by thousands, hundreds of books, and thousands of more websites that people have a hard time trying to figure out how to create a strategy, because they're drawn up, down, left, right. So my two pieces of advice, anybody that's actually trying to do this is, A, state the problem, and, B, don't call it a strategy, call it an action agenda, that you're not creating a strategy, you're creating an action agenda. What are we going to do about this problem? That's essence of what you're doing. When you're thinking strategically, you're recognizing the problem and you have an action agenda to deal with it. It's not five years out and 10 years out. It's not your general mission to build a better world, it's none of that.

All of that is a different literature form. There's huge numbers of people out there willing to sell you advice on how your mission, and your vision, and your values, and all these things that have to be in place before you can have a strategy. And that's not true. It's a different model. I start now with ambitions because people want to put ambitions in place. They get angry with me. I don't allow them to talk about their ambitions. So we start with ambitions, and okay, you have all these ambitions. I write in The Crux that when I was 25, I wanted to be a top business school professor. I wanted to be on Fortune directors. I wanted to drive a Morgan Drophead Plus 4. I wanted to climb the great mountains of the world. I wanted to learn to fly an aircraft. I wanted to marry a beautiful woman and have successful children. I wanted to have a townhouse on the [inaudible 01:00:00] of Paris. All and all, I had a lot of ambitions.

**Richard Rumelt** (01:00:05):
That's not strategy. We all have ambitions, and every company should have ambitions. If we look at all those ambitions, and let's say I'm 25 years old, well, what's keeping me from reaching them all? "Well, I'm not ready to join Fortune directors. I'm not experienced enough." Okay, so I put that over here. "I can't afford the pen." Okay, put it over here. "How about the ambitions that you have any chance of making progress?" So now, well, beautiful woman. "Yeah, I don't know any, maybe I ought to meet a few." "Well, you can do something about that."

**Richard Rumelt** (01:00:52):
So which of your ambitions can you begin to make progress towards reaching, and what's holding you back? What are the barriers? What are the problems? So I approach the question of the problem now through the filter of the ambition, that these ambitions, fine, let's accept them all, and which one can you actually make some progress on today? And what's making that hard? What are the challenges? So you're choosing a challenge. You're choosing, of the possible challenges you could face up to, you can't do them all. So there's a focus thing. You're choosing which challenge to focus on, and that challenge has to be, A, important, and, B, it has to be achievable.

It has to be something that you can address. It has to be an addressable challenge. And so the search for an action agenda, I'm not calling it a strategy, is this balance between problems that are important because they're close to your ambition and problems that you can actually address and do something about. And that overlap then becomes the choice you make. "Okay, we're going to go after this and here's the action steps we're going to take to do that." And if it's a big company, the action steps may extend over two or three years. Smaller company, took [inaudible 01:02:32] year, six months to a year. These are things we're going to do, not goals we're going to achieve. These are things we're going to do, action steps. That's sort of the way I put it together today, which is slightly different than the way it's put together in The Crux.

**Lenny** (01:02:49):
Yeah, I love this advice. That's such a simpler way of thinking about strategy. It's an action agenda. "Here's the things we're actually going to do." And then it starts with the challenge. And just to talk about The Crux briefly, The Crux is named after this concept in mountain climbing of the hardest point of the mountain climb where people, if they get past that, it's all downhill. And I think basically the point there is focus on the most challenging, like the biggest challenge that you need to overcome to achieve these ambitions you're describing. Is that roughly the way to think about it?

**Richard Rumelt** (01:03:21):
Yeah, yeah, and the idea comes from a design, and it comes from climbing, because I used to be a climber, a rock climber, and a snow climber, and a crux in a climb is the hardest part, the hardest pitch or a pitch, the hardest move is the crux of that piece. And then the basic advice to a climber is if you can't do the crux, don't do the climb, because you're going to fall off there. Now that's not exactly true, because you can try it over and over again until you get it. But in general, particularly if you're looking at an alpine climb, you better not take it on a climb where you can't handle the crux. That's why people go bouldering. The [inaudible 01:04:06] still up to him [inaudible 01:04:08] crux.

**Richard Rumelt** (01:04:11):
And so that's what the concept of the crux comes from. Now in business, the crux is the hardest part of the problem. And from the design point of view, the skilled designers, whether they're an engineer or an architect, what else? There's usually a challenge. I. M. Pei was hired to take a look at the Louvre in Paris, and they had a dusty parking lot in the center of this giant palace that had become a museum, and they wanted an entrance to Louvre there. And the problem is he didn't want it, they didn't want a new building that would obscure the Louvre itself. The building itself is part of the story, it's part of the scene. And yet at the same time, they needed to have an entrance, because the entrance at that time was off on the side wall.

And you looked at the situation, and the competing needs, and the [inaudible 01:05:31]. And he had an insight into, "Well, build a transparent building, build a building out of glass, so that you see through to the Louvre, it doesn't obscure." And of course, if you can build a rectangular building out of glass, the top will get dirty. So [inaudible 01:05:55] out of glass. Now, that design insight is something that software engineers, hardware engineers, mechanical engineers, base science engineers like I was, experienced, when we look at a dilemma and we try to focus on what makes this hard. And then by focusing on the difficulty, we see a way around it. Elon Musk focused on, "Well, why is it so hard to reuse a rocket?" And it's so hard because as it comes back into the planet at 18,000 miles an hour, it burns up in the atmosphere, or we have to spend a lot of money on heat shields. And at some instant, he said to himself, "Well, why not, like science fiction, just turn it around and have it land on its rocket?" "Well, there's not enough fuel." "Well, why aren't we carrying more fuel?" So SpaceX, when I was designing, I was a conceptual designer, but machine that became Voyager and went out past the planets into interstellar space where it's floating around right now. Well, one of the problems is how do you know where Jupiter is? " It's right there." "Okay, but how do you know where it is, plus or minus 100 miles? How do you know exactly where it is? When we set a mission to Mars, we were off by 500 miles. So Jupiter, how do we know exactly where it is?" Because we can look at it through our telescopes so we can look at it from the right side of our orbit and the left side of our orbit. But still, there was a couple thousand miles error in that. That's too much. And then studying that problem, the simple solution suddenly flashed, and I wish I could claim it was mine, and it wasn't, which is, "Oh, take a picture of it once we're halfway there. We'll send that picture back and we'll see it against the distant stars. And now we'll have a triangulation, know where it is." So designers experience this sense of focusing on the crux of the problem, the hard part, and then seeing a way through. And that's strategy. Strategy isn't picking a strategy out of a list of common strategies. It's looking at the problem, what makes that problem hard, and seeing a way to solve it.

**Richard Rumelt** (01:08:54):
Now it's called insight, and insight is scary. It's scary because it's not guaranteed to happen. We want to innovate, but we're scared of insight. We want to be the first, but we'd like to pick our strategy out of a list of common strategies for being first. We want to beat the market, but we don't want to study enough to have an insight. So insight is critical. Insight is not magical. It comes from immersing yourself in the nature of the problem. And you will have, at some point, an insight about how to deal with it. It doesn't always come when we want it to. It can come while you're driving the car, it can come the next day. It can come in the shower. Charles Darwin reports that his insight into the nature of revolution came as he stepped off a carriage into the village green somewhere. Boom, suddenly, he said, "Oh, yeah, it's obvious." It's like how we raise animals, we breed the strongest. "Sure, why was that so hard for me to see?"

**Lenny** (01:10:14):
So I think one of the big takeaways here is that if you want to get better at strategy or be more successful with how you think about strategy, spend a lot more time on diagnosing the problem and finding the biggest challenge that is keeping you from what you're trying to achieve. And your insight might come the more you immerse [inaudible 01:10:30].

**Richard Rumelt** (01:10:30):
Yeah, and call it an action agenda, "Here's what we're going to do." Not, "Here's all the things we wish would happen."

**Lenny** (01:10:39):
I love it. You mentioned this point that some of the biggest challenges to executing a strategy is organizational dynamics, and politics is a part of that. Is there anything you could share for folks to help them through that? You talked about one of the biggest challenges, people just want to keep adding more priorities. There's all these needs. Everyone wants to include their thing in the strategy. Is there anything people can do to improve how this works?

**Richard Rumelt** (01:11:04):
Typically, I'll say typically, we need hierarchy of power, because there has to be some mechanism for deciding what we're going to do. And there's people with different interests and different private interests and public interests. And somehow, there has to be a choice about putting some of these aside and doing this, that you can't say, "Our strategy is to do everything that everybody wants to do." That's what happens when you form a committee in a city and you say, "What's our city strategy?" They say, "Oh, we're going to paint the park benches. We're going to clean up the grass, we're going to build a new this, we're going to..."

They have a [inaudible 01:11:49] that stuff, everything they're going to do with that. And anybody who raised their hand and says, "Well, what about the birds? Can we..." "Oh, yeah, let's put that in, too," that doesn't go anywhere. So we, inside organizations, people have different opinions. So that's part, they have interests that they may not state clearly.

I interviewed Secretary of Defense, Donald Rumsfeld, while we were invading Iraq, second time, and I was actually interviewing about budget matters, but he asked me, "Well, what do you do, professor?" And I said, "Well, I do strategy." And he said, "Well, strategy, that's a hard subject." He said, "I've got people here in the Defense Department who have an expert on anything. You want to know the clan structure in Iraq, we've got people who know. We want to know the weather, we've got people to know. You want to know how many [inaudible 01:13:05] we can fly in 24 hours, people who know. I got anything you want to know, we've got someone who knows about it, but they all disagree. And each have their own private agenda. They have a contract they want to get, they have a company they want to support, they have a conceptual idea they want to push."

**Richard Rumelt** (01:13:25):
So every little bit of information comes with an agenda, sometimes obvious, sometimes hidden. And how do you put all this stuff together to come up with a strategy? He says, "Do you academics have a solution to this?" And I said, "No, we don't. We don't know much more than, what, 2,000, 3,000 years ago, which is you put five to eight smart people in a room and you tell them to come up with something." But his question is at the heart of what I call a foundry, which is how do you get a group of people to coalesce around an action agenda?

And what process would you use and how do you do that? It's a different question than, "What should our strategy be?" The question is, "Well, how should you go about creating a strategy? Should you ask the product manager to write an account, or should you ask the CEO to come up with it? Should you hire a consultant? How do you do this?" In my experience, working with companies, is that the senior executives have to do this. And my experience is that the senior executives know pretty much everything you need to know to do this, that you don't need consulting firms to come in and analyze everything that you do. Yes, you'll gain some insight if they come in and do a competitive analysis, and a customer analysis, and all of that. But the basic issues, the challenges you're facing, they know that. It's not mysterious. They know all that stuff, but they disagree about the importance of different things. And more importantly, they occupy positions of power that, if we go this way, this is going to be hurt. And if we go this way, they're [inaudible 01:15:34] more money for that.

**Richard Rumelt** (01:15:36):
And so their interests are not aligned, which is part of what Phil was referring to. And so the problem of strategy inside an organization is diversity of interest and fear of action. Because action, when you do something in an organization of any size, it involves people changing what they do. It involves changing power relationships among humans in some way, that someone who's been the alpha maybe is not the alpha anymore, someone else is the alpha. This is heavy stuff. And this is why we have a hierarchy, because someone in the end has to say, "It's going to be this way." And people are hesitant to do that, CEOs are hesitant to do that. More so today than when I was a young man. It's become hard for people to do this. If you go to the bookstore and look at the management section in bookstore, most of it's about leadership.

And the leadership is mostly about perfecting yourself. It's not about beating anybody, but the theory is that if you perfect yourself and somehow rays come out of your head and people will follow you, because you're so magnetic, and you're so perfect, and you're so wonderful, and you're so insightful, and that people will follow you, you won't ever have to say, "[inaudible 01:17:19], do that." It's so embarrassing to tell somebody what to do.

**Richard Rumelt** (01:17:24):
And so this is the world we live in today, where one of the problems in doing strategy is that it's somehow been displaced by this literary form about mission, and management is being displaced by leadership, which is the idea that the leader has a vision and people... It happened in the '80s. There's a whole literature there about transformational leadership that is percolated through the system, and those, I'm not against leadership, but you have to tell people at some point, "We're going to do this, and we're going to do it this way, and Bob's going to be in charge of this aspect, and Joan's going to be in charge of that aspect." And there's a hesitancy to make those choices, because that's part of the action agenda.

**Lenny** (01:18:23):
So the takeaway there is essentially have a decider. It makes me think of, actually, of George Bush. You talked about Rumsfeld, but George Bush's famous quote, " I'm the decider." I don't know if you remember that?

**Richard Rumelt** (01:18:33):
Yeah, that's true. One of the things we see in government particularly is presidents have a hard time getting advice, because they surround themselves with people who want to please them. Number one, we rarely.,, It used to be, I remember during Woodrow Wilson's administration, when he decided to take some hard action, the [inaudible 01:18:58], and he had to do something, [inaudible 01:19:00], and the Secretary of State disagreed and quit. "Right, that's it. Quit. I disagree." Wow, don't see that so much anymore. All the people, organizations get frozen because of the difficulty of changing positions of interest and power in [inaudible 01:19:29].

**Lenny** (01:19:30):
Humans are complicated.

**Richard Rumelt** (01:19:34):
Well, if you look at Nokia, one of the big examples of strategic errors, Nokia was the leading phone maker in the world world, and then somehow it lost its ability to compete. And interesting question, there's been a fair amount of research on this, is how did that happen? One way it happened was they replaced the engineers who used to run the company with lawyers and accountants. Nothing wrong with lawyers and accountants, but they didn't have a feel for this hardware, software set of issues. And another was they put in a matrix organization that so diffused power inside the organization that nobody was actually in charge of anything in particular. I'm exaggerating, but the CEO kept pounding the desk and saying, "Apple's coming out with a smartphone and you have a touchscreen, and somebody here should make one of those." So there was no one in authority to do such a thing.

**Lenny** (01:20:40):
Maybe a final question on the other end of the spectrum, from an Nokia, from a startup founder's perspective, what is a strategy and what should a strategy look like if you're just a founder, pre-product market fit, just trying to figure out where you want to go? What should a strategy look like there? Do you even need a strategy?

**Richard Rumelt** (01:20:57):
Well, you're dealing with a lot of uncertainty When you're a founder in a startup, you're making a bet. You're making a bet like an oil well [inaudible 01:21:09] say, "I bet there's oil under this ground. We're going to drill, we're going to find it." There's a certain amount of bet that's going on, and you should be clear about the nature of the bet. The reality is going to be revealed to you in bits and pieces as time passes, whether a certain approach is going to work or not. What we find doing research on startups, Silicon Valley startups, is they start out typically aiming at a particular product market solution. And the idea that you have in your head is, "There's a set of customers who want A, would like to have A, are being denied A, but we have a way of giving them A," something, a product or a service.

Now, some people, they aren't that even advanced. They basically say, "I know how to make something and I'm going to try to sell it." You know, [inaudible 01:22:10] approach. Well, if you have any chance of succeeding, you have [inaudible 01:22:17], you have target market, and you have a solution to the target market's problem in mind, and now you're going to go after it. And the research that we have done on the startups is that generally it doesn't work.

**Richard Rumelt** (01:22:33):
But the ones that survive and prosper switch. They say, "Well, it isn't that customer, it's a different customer. You should walk from that customer. Oh, and that customer wants a slightly different product," and they switch over a period of a year or two period, bang, bang, until something begins to click, and they begin to grow, and begin to add functions and assets. So there's a search, there's a search like a truffle hound searching for the truffle that's going on.

**Richard Rumelt** (01:23:05):
And you've got to be able to think, you've got to be of two minds. Like so many things in business, when you're doing this, you've got to be of two minds. You've got to be convinced of the certainty that you're going to win, and you've got to be willing to shift when things aren't working, and that's a double-jointed exercise that some people can do and some people can't. It's almost a human skill to both commit and to be willing to move. But it's a bet. You should be clear in your own mind about the nature of the situation, the technology that you're betting on. Now, sometimes it's evolving so fast, like generative AI is right now, that you can't be sure.

**Richard Rumelt** (01:24:04):
... That you're going to take a position, where do you think things are going to be in a year? And that's very, very entrepreneurial, very edgy stuff, but it's not... Go back and read about the beginnings of the electrical industry or the beginnings of aviation or the beginnings of motorize this and beginnings of cars. People had to bet about what this industry would look like. The first cars were electric cars. The first car sold in quantity in the United States were electric delivery vehicles used downtown in cities, delivery [inaudible 01:24:49] produce. They were electric, ran on batteries. That was the bet.

**Richard Rumelt** (01:24:53):
All that changed with the First World War. The United States built thousands and thousands of gasoline powered trucks to go to Europe, wrestled through the mud, and people came back knowing how to fix those engines, and those trucks got sold off as wholesale to farmers, who used them on their fields, and we had the gasoline to take off like a rocket. So, you cannot predict the future. There's an Arab saying that I like that says, "He who forecasts the future lies, even if he tells the truth." We're making bets. That's what business is, we're making a bet. And if we're a rich company, we can make a bet and afford to be wrong. But if we're a startup, we have to be fast, we have to adapt as the information comes in, and that's the nature of the story. The action agenda has to be quick adaptation to changing conditions.

**Lenny** (01:26:06):
I feel like you have another book here where you could adapt a lot of this wisdom to startups. I'm looking at my notes from what we were talking about earlier, and you have this point of when you're trying to write out a... You call it an action agenda, not a strategy, you're basically on the hunt for a big problem and an important problem and an achievable problem. And essentially you can boil that down to that is the job of a founder to find an important problem and achievable problem and then solve it for a lot of people.

**Richard Rumelt** (01:26:34):
I like that. The other exercise I used to take my students through was what I called value denial. Now, what is it that you should be able to buy but you can't? And at the time I taught this stuff, I was upset because I would lose my baggage on a nonstop flight from Los Angeles to Paris, so I'd like to buy baggage... Sure, so I'd like to buy... How do you get your baggage not to be lost? Now, with security systems in place, it's less, let's call it. Can I find someone to help me remodel my home that's going to be on time and I'll bet you not available. Can't buy it at any price. If I live in Hong Kong and I'm going to the airport, I can drop my luggage off downtown and it arrives at the airport checked in. I don't have to lug it. Why can't I do that in the US? Value denial.

**Richard Rumelt** (01:27:44):
And then engineering, thinking about how something ought to be, a channel, salesforce.com got started was, "Well, how should this be? It shouldn't be a computer, it should be a webpage. It should be like Amazon where it has books." And so, that was the beginning of salesforce.com. I asked a group of students once to think about the perfect window because it's physical, something we could think about in the classroom without doing a lot of research. Well, what's the perfect window? A perfect window should be transparent, should let the sun in. All right, so it's let in the light, but not all the time. Sometimes you want to watch the television. So, it should also darken, drapes for shades. It should let in the air, good, but not the bugs, a screen. It should let in the air, but not the noise. That's a little harder.

**Richard Rumelt** (01:28:57):
So, you go down a list of things that a window should do. It should let in light, but not light. It should let in air, but not the noise. It should not let in air when we don't want it. It should not let in the bugs. It should maybe have shutters or not shutters. And so I said, "How could you design the perfect window? What would it look like?" And there's some kids at MIT that had developed this thing that lets in air, but keeps out the noise, these little auditory filters keep out noises in certain frequencies. Well, we don't have a perfect window, but think about it, windows could be better than they are.

**Richard Rumelt** (01:29:39):
And that's a real simple device that we're all familiar with, and look around you, look at everything you've got and say, well, "How shouldn't it be?" And there's opportunities there. Now, a lot of the times, the opportunities are blocked by the lack of certain materials or regulation. Regulators have decided that you can't sell a car in the United States unless it goes through a dealer. So, that holds back innovation in that business. And so plumbing, how should plumbing actually work?

**Richard Rumelt** (01:30:20):
Well, there's a whole surge of rules about how plumbing works and electrical things work. You can't innovate there very easily because of the underwriter's labs and the unions, and a lot of the stuff that's done in home construction is there to create jobs, not to reduce costs. So, how do you get around that? So, you have to look at places where it's possible to innovate first of all, but the idea of how do you make something better? How do you make it perfect? What would the perfect light switch look like, and so on? These are real simple, silly questions, but they lead to new businesses and new firms if you pursue them.

**Lenny** (01:31:03):
I love how full of startup ideas you are. I also think we came up with at least two new books that you can write. I think you're going to have a lot of work to do after this conversation. Final question, is there anything you want to leave listeners with or take away? Is there a final nugget you just want to share for folks?

**Richard Rumelt** (01:31:19):
I want to share with you that strategy's not mysterious, that I've spent my life studying strategy, pursuing it, consulting on it, writing about it. It's not mysterious. It's about solving problems. It's about solving the most important problem you're facing that you actually do something about. You don't have to be Sun Tzu to come up with a strategy, but you need to be focused on something doable and be consistent about it. I have a long list of things not to do. There's a fourth book that I'm thinking about writing called Don't Do That.

**Lenny** (01:31:59):
I would read that. I love that title.

**Richard Rumelt** (01:32:02):
Can I tell you a story?

**Lenny** (01:32:03):
Absolutely.

**Richard Rumelt** (01:32:05):
My wife Kate took up skiing when we got married 24, 25 years ago, and she had this stance that she couldn't get rid of. When you make a turn, you don't turn like that, you put the ski out the step. I made her ski on one ski, I did all sorts of things to her back, she couldn't fix it. And finally we signed up with an illustrious ski teacher in Aspen, a three-day intense program, guaranteed that she would lose her stance, exceeded them all.

**Richard Rumelt** (01:32:45):
And so we went there... On the second day, I followed behind the instructor and her to see what was going on, and they had been through some exercises on day one, but in day two they were focusing on this and she would put out her ski like that and he'd yell at her. He'd say, "Don't do that," and after a day of being yelled at, "Don't do that," she didn't do it anymore, she was fixed. So, the secret technique that they had in this program for curing your stance was to yell at you telling you, "Don't do that." And so I'm thinking about a book called Don't Do That about business things where I'm not sure it makes sense, but you have to noodle these things for a while before they begin to gel.

**Lenny** (01:33:34):
I love this idea. It reminds me, one of my friends is a therapist, and there's this video by Bob Newhart where he's a therapist and someone comes to him and they've got all these problems like, "I get really sad when I think about my mom and I have this chronic pain," and his advice, "Just stop it, just stop."

**Richard Rumelt** (01:33:50):
Don't do that, just stop thinking about your mom.

**Lenny** (01:33:50):
"Just stop it," that's the advice. And so, I feel like there's a lot of synergy there. All right, well, with that, we've reached our very exciting lightning round. Are you ready?

**Richard Rumelt** (01:34:04):
I guess so.

**Lenny** (01:34:07):
First question, what are two or three books you've recommended most to other people? I feel like this is going to be a challenging question, but what comes to mind?

**Richard Rumelt** (01:34:15):
It sort of is. The books that I'm... Clayton Christensen's stuff about The Innovator's Dilemma is always solid. Books on strategy that I recommend to other people on... There aren't that many. So, I like Playing to Win by Roger Martin. I really recommend other kinds of books, strategy books. It's easy to get a list of strategy books, but I think you should read biographies and histories. I think the book about Steve Jobs is brilliant. I like books about business leaders. I'd recommend Andy Grove's book Only the Paranoid Survive, and a few others, but I recommend that people read more broadly about people, Rockefeller's histories, it's fantastic.

**Richard Rumelt** (01:35:22):
The stuff about Rockefeller and how he put together... Rockefeller was a robber baron and he built an empire and all that, you learn that in school, but what you don't learn in school is he dropped the cost of a gallon of kerosene from $1 to 10 cents. That's the robber baron, and he made kerosene so inexpensive that he drove all the little mom and pop proprietors out of business, which is why they hated him. So, he was a vicious competitor, but he dropped the price of something by an order of magnitude, fascinating. So, it's important to understand stories, not just theories, but stories.

**Lenny** (01:36:22):
I love how this always comes back to just being steeped in history and this specific point about biographies is really interesting, and we'll link to all these books that you're mentioning in the show notes. Is there a favorite recent movie or TV show that you've really enjoyed?

**Richard Rumelt** (01:36:36):
Oh yeah, sure. Well, I like Yellowstone, like everybody else. I'm fascinated by it. Recent movies other than Yellowstone? I'm not sure. We don't have a TV in the house right now, so I'm not connected.

**Lenny** (01:36:51):
That's amazing, that's the dream. I wish I could do that.

**Richard Rumelt** (01:36:57):
There will be a TV, but that room is being remodeled.

**Lenny** (01:37:02):
I see, just a matter of time. Is there a favorite interview question you'd like to ask people you interview, maybe specifically around helping you get a sense of are they good at strategic thinking?

**Richard Rumelt** (01:37:14):
I like to ask people about, what have you done that was hard that you're proud of? What have you done that was difficult? And what was it and why was it difficult and how did you get it done? I like to ask people about what they think was an interesting strategy from any time in the past they want to call out. Depending on the person's background, I might ask them about a particular company or situation, let's say, why do you think this worked or why didn't it work? So, I don't tend to ask questions about theory, I tend to ask questions about things that happened and part of me, I'm looking, does this person have any knowledge about the world or are they just know what the professor said last year. So, that kind of thing.

**Lenny** (01:38:28):
Is there a favorite product you've recently discovered that you really like, whether it's an app, some you bought, some in the house, some on the road?

**Richard Rumelt** (01:38:36):
Well, we've got this new memory foam bed that we like, it's a pretty amazing innovation. I didn't think we'd like that, but we do. I really am fascinated by... I'm about to pull the trigger on buying one of these new smart telescopes.

**Lenny** (01:38:53):
Smart telescopes? I haven't heard of that. What makes them so smart?

**Richard Rumelt** (01:38:56):
It's a 12-inch reflected telescope, and it's too heavy to look around, it's too difficult to set up, but there are sort of new smart telescopes that run on a battery and you can put them outside. And the way they work is, first of all, they know where everything is in the sky, which has been around for a long time, but the new thing is, it's like astrophotography. They'll look at something for a minute, two minutes, 10 minutes, an hour, and form an image. You don't look through the telescope, you look at it on your phone or your computer, but you can see now the nebula that maybe the web telescope can see and you can see it now and you can see stuff out there that you couldn't before. And these are new things for $1,000 or $2,000 set that are remarkable in what they can do.

**Lenny** (01:39:56):
Excellent choice. Next question, do you have a favorite life motto that you often find yourself coming back to, sharing with friends, either in your work or in your life?

**Richard Rumelt** (01:40:05):
I used to have a final lecture I'd give to my MBA students about little pieces of wisdom, things not to do, things that offend people in other cultures. Don't do this if you're in Turkey, it means something else there. But I'd also say at some point your spouse or your partner will ask you, "Do you still love me?" And there's only one correct answer to that question, which is more than ever. And my wedding ring says that inside it, more than ever. So, I don't know if that's what you're looking for, but that's-

**Lenny** (01:40:57):
Absolutely.

**Richard Rumelt** (01:40:57):
... Getting a [inaudible 01:40:58] sense piece of wisdom.

**Lenny** (01:40:59):
That is really good advice, gave me tingles. I'm going to use that, 100%. Thank you for some marriage advice. Final question, your daughter Cassandra is a writer as well in fiction. She writes fiction. Is there anything that she taught you about writing that's helped you become a better writer?

**Richard Rumelt** (01:41:18):
Yeah, Cassandra is the... Oh my God, she's got like 25 books on the New York Times Bestseller list for teen fiction now. She started writing when she was 12 or 13. She had a talent for it. She's told me about the tension that you have to create and she writes novels and that it's not interesting unless there's... Well, we started talking about this when she was young, she was 14, and she asked me about, what is romance? I said, "Well, romance is a barrier. Romance is where there's a difficulty back to a couple, and there's some kind of..."

**Richard Rumelt** (01:42:12):
She said, "Oh, like he's rich and she's poor?" I said, "Yeah, like that." "Or he comes from the north side of town and she comes from the south." And I said, "Like that, yes." And she said, "Oh, like he's a vampire and she's not?" Okay, so she has alerted me and taught me about ways of creating that kind of tension in writing. It doesn't work as much in business writing as I'd like, but I try to create this sense of it's good strategy, bad strategy. It's a sense of there's a tension between the right way and a wrong way, or if not a right and wrong way, at least there's a tension between, should we go left or should we go right? It makes it interesting, otherwise it doesn't catch people's emotional court.

**Lenny** (01:43:14):
Amazing. Richard, thank you so much for being here. I think we're going to help a lot more people face bigger challenges and face them head-on and put together their action agendas and overcome this crux. Thank you so much for being here. Two final questions, where can folks find you if they ever want to try to reach out or learn more about the work you're doing these days? And then how can listeners be useful to you?

**Richard Rumelt** (01:43:37):
I have a little website called thecruxbook.com that has information about me and about the books, so there. Don't write to me at UCLA. I don't pay attention to the UCLA website anymore, but if you go to thecruxbook.com, there's some email addresses where I can be reached. My little company's called General Imagination. It's like General Motors, but a lot smaller. It's just me, and you can reach me at richard@generalimagination.com. You can help me out... Oh, tell me stories. Tell me stories about your experiences, trying to create strategies, particularly inside organizations. How's it worked for you trying to get something done inside organizations? I'm happy to add more stories to my repertoire. Oh, and hire me.

**Lenny** (01:44:46):
Wait, say more on that. What is it that people would hire you for?

**Richard Rumelt** (01:44:51):
At this point in my life, I do public speaking. I speak on strategy and growth, and just got back from Korea doing it, I taught there. I do a little bit of teaching, not much. Maybe for the military people, if they want me to come in and do a day on strategy and I do foundries. A foundry is where you commit to a problem-oriented approach to strategy where the organizational leader, the CEO, usually plus another seven or eight people take two to three or four days off and we meet and we try to come up with, in the end, an action agenda and it's an interpersonal exercise.

**Richard Rumelt** (01:45:52):
I'm the facilitator. I don't tell them what to do, but I urge them to look more deeply and to understand what these problems actually are. It's interesting to do a foundry. You get quite focused on problems, as I do at the beginning. I'll often get 25, 50 problems up on the board or Post-It notes around, and when people look at that, they'll say, "I haven't ever done this before." When they see the 25 different problems or challenges, they realize you can't do them all. And so, they begin to get this sense of, "Oh geez, we better focus. We better focus on something. We better do something about some of these." And so, then we begin to go through this thing, "Well, which ones are really important and which ones are really addressable?" Well, sometimes we don't know if they're addressable or not. Oh, well, is there anybody in the organization who does know? Is there someone we could fly in here or have some perspective on this? So, we begin to try to identify the one or two key challenges that can actually be addressed and what are we going to do about it? What are the coherent actions we're going to do to take these on? That's the exercise.

**Richard Rumelt** (01:47:16):
From time to time, after the foundries, they all say to me, "Well, where's the strategy? Where's the document with the mission, vision, all that?" No, that's not what we do. We're doing an action agenda and the foundry is time-consuming and a bit expensive to some extent, and most of the times we've had foundries, they really help the company gather its wits and its resources and do something, which I'm very pleased with how the foundries work. It's not so easy to figure out how to take the foundry concept and expand it. I've talked to a couple consulting firms about, "Well, the guys like learn how to do boundaries," and they say, "How does it work? It's one guy for three days? That's not what we do. We do 10 guys for three years." It's not a business model, but that's a nice symmetry for me because they're not going to compete with me.

**Lenny** (01:48:32):
I love that. I feel like you're about to get a flood of interest and requests. For everyone else, make sure to buy Richard's books, I got them right here, The Crux, Good Strategy Bad Strategy. Richard, again, thank you so much for being here.

**Richard Rumelt** (01:48:45):
Lenny, thank you for a really pleasant time chatting.

**Lenny** (01:48:49):
It was 1000% my pleasure. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

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## [7/19] Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market

**Geoffrey Moore** (00:00:00):
The tendency when you're in the chasm is, "I just need more customers. I should take any customer I could find," because we need revenue. It's like taking a match and running it back and forth under a log. It's not going to light the log. So how do you start a fire? Well, you start it by putting a little kindling, little crumpled up paper, and you hold the match in one place until the fire starts. That's why adjacency is so important. If you light the fire, the piece of kindling is here, but the log is in the other room. That doesn't work.

**Lenny** (00:00:32):
Today, my guest is Geoffrey Moore. Geoffrey is the author of maybe the most influential and important book on go-to-market ever written, Crossing the Chasm. Even though it's sold over a million copies, it still feels like people continue to reinvent many of the lessons that Geoffrey uncovered and shared in a seminal book. In our conversation, we discuss why it's so important to get very narrow with your initial audience, how the bowling pin strategy helps you get past early adopters, what the specific go-to-market playbook is for every stage of the adoption lifecycle, why using the wrong playbook during the wrong phase will slow you down. Also, the seven deadly sins of trying to cross the chasm incorrectly. Also, how to sell your product at different personas, why you don't need to focus on the problem and the pain when you're selling to early adopters, plus some real good life advice that I didn't expect.

**Geoffrey Moore** (00:04:07):
Well, it's nice to be here, Lenny, and thank you for having me.

**Lenny** (00:04:09):
It's incredibly cool to have you on. You've been at the top of my wishlist of guests to have on this podcast ever since I launched it, so it's surreal to be chatting with you. It almost feels like maybe this podcast has crossed the chasm now that you're on.

**Geoffrey Moore** (00:04:22):
If you'd called me earlier, I probably would've been on it with you. But anyway, we're together now.

**Lenny** (00:04:27):
I thought it'd be fun to start with this question of just what frustrates you most about what people still don't get about the things that you teach, particularly Crossing the Chasm. You wrote that, I think, 33 years ago at this point. You have a lot of follow-up books around the topic. What do you think people still don't really understand or often get wrong?

**Geoffrey Moore** (00:04:45):
All the books I write are about frameworks. They're conceptual models about what patterns should you be looking for as something evolves? Because in disruptive innovation, there's no history. You're always projecting a possible history, and then seeing if you can make it come true. So that implies there's a lot of freedom to exercise the framework however you choose to. People sometimes do that in ways that are just... They actually end up being very misleading about what's possible. I can remember one person early on saying, "Yeah, we're Crossing the Chasm. Our beachhead segments the Fortune 500," and you went, "Well, I don't think maybe you're as clear on this as you could be."

**Geoffrey Moore** (00:05:32):
To be fair, that's what the function of any third party advisor is, is to say, "Look, time out. You might be looking at this through an inside-out lens. Maybe you should be looking at it from an outside-in lens." That's probably number one. Gosh, after that, I'm just empathetic with the fact that their world's more important than my world, so I try to work with their world.

**Lenny** (00:05:59):
That's exactly where I actually wanted to go next is this idea of starting very focused with your initial target audience. I think people conceptually know this. They're like, "Yeah, we should be really focused with our initial target market. We should stay very small, and expand this beachhead idea." But I think they still don't quite actually do this because it's like, "Why not go wider?" So could you just talk about why that is so important, and how to actually think about how to do that correctly?

**Geoffrey Moore** (00:06:23):
If you're essentially in a business where the category is emerging, then the most important thing for you to do is to be able to create enough power around your company that you can navigate your future on your own power. Where does power come from in an early adopting technology world? First of all, it'll come from can you get a lighthouse customer? So one of the things we try to do even before you try to cross the chasm is can you get one or more customers who put you on the map? And they go, "Whoa, did you know that the CIA used AWS?" Like, "Holy smoke." Okay, that's great. It doesn't make a company, but it makes a story, and it lets people know, "Oh, here are the guys that did the CIA project," that kind of thing.

**Geoffrey Moore** (00:07:09):
The Crossing the Chasm model is, "Can you create a viable repeatable business?" And in order to do that, you need to have an ecosystem of partners work with you in order to consolidate your position. Well, why would an ecosystem work with some startup that nobody's ever heard of? The answer would be if you had consolidated a market segment where you were number one. So one of the things we've learned about company power is that basically it's the company power plus the ecosystem together. So ecosystems form around market leaders, and they do not form around the rest of us. If you're a category leader, if you're like Oracle and Databases, you're 40 years in. You're still the leader, because the ecosystem organized around you.

**Geoffrey Moore** (00:07:51):
But when you're little, the only way you can get an ecosystem to organize around you is to go after a segment where you're a big fish in that pond. We talk a lot about fish to pond ratio. You want to be... Your first pond, your target segment should be something that in the next two years, if you hit your really high growth rates, you could be 30, 40, 50% of the market share in that segment. That would cause partners to go, "Whoa, if we're going to serve that segment, we got to work with these guys." So that's the key. The concept there is, "Well, why wouldn't you also do two or three or four segments at the same time?" It's sort of the same reason, "Why wouldn't you run in three or four primaries at the same time if you want the presidential nomination?" Although why you would want that nomination, I have no idea.

**Geoffrey Moore** (00:08:39):
But if you did, you realize if you're running in New Hampshire, votes in Vermont do not count. It's the same thing with Crossing the Chasm. You need to get three or four or five or six reputable companies in a segment to all pick you, for then the rest of the segment to go, "Well, it's pretty obvious who the standard is." I'll just close with one last comment. And the reason, the mechanism behind all that logic, is that pragmatic people buy what they see their peers are buying. So if peer one is buying product A, and peer two is B and C and D, there's no market leader, and the category goes sideways. But if A, B and C, if three out of four people are using the iPhone, it's like, "Oh, I guess I'm supposed to get an iPhone," that kind of thing.

**Lenny** (00:09:29):
Awesome. I'm glad you went there, because that's essentially the root of this Crossing the Chasm idea that people after the chasm, the pragmatists, wait for references and social proof, and they're waiting for someone to tell them, "This is worth using," versus visionaries right before the chasm. They're like, "I just want to use the future. I need to be there before anyone else."

**Geoffrey Moore** (00:09:49):
You're right. One of the ways we try to capture that in a thought bubble is before the chasm, the customers you work with are people who say, "We believe what you believe." So in other words, they're on the same side. After the chasm, they say, "I'm not sure about that, but we need what you have." So transitioning from, "We believe what you believe," which is how you sell to visionaries to, "We need what you have," which is how you sell to pragmatists. That's the shift.

**Lenny** (00:10:17):
Let's actually spend some more time there on what it is that each of these segments needs, and how you convince them to use it, because this is really useful. So in these pragmatists group, you're saying the pitch there is you have a pain. I will solve this pain, and it's important pain. I think people always assume that's the pitch. But interestingly, your point is earlier in the two segments and maybe share what those two are, they use your product for a different reason.

**Geoffrey Moore** (00:10:41):
In fact, if there's a total in the model of the technology adoption lifecycle that we organize this all around, there's actually four, I call them, inflection points. The first one we call the early market. That's the one we were talking... That's the visionaries and the technology enthusiasts. They are as excited about you as you are. I mean, they want the demo. They want to see the vision. They're exciting. And the key to that market is to have an executive sponsor who has enough clout to essentially fund this thing, because there's no budget for you. So they've got to create the funding, and then drive the organization to go all the way to bright.

**Geoffrey Moore** (00:11:21):
They're not that many visionary customers, but there's always one or two. The reason why it's so important to work with a marquee customer then is you... Look, nobody's ever heard of you, and if they've never heard of your customer, I don't care how amazing the win is. Nobody's going to hear about it. So it's really important you did it with Apple, or you did it with Verizon, or you did it with Mercedes, somebody that people have heard. So that's number one, and that's a project model. Even if what you sell is a product, those early mark... Every one of them is kind of a snowflake. It needs a ton of special services. There's no ecosystem of partners to support you, so you throw a bunch of extra labor at it. You do whatever, because you got to make them successful. So you'll do whatever it takes.

**Geoffrey Moore** (00:12:13):
Okay, very cool. Got my marquee client, not scalable business, I mean, obviously. So then the second one is the Crossing the Chasm playbook. That's the one that organizes around the problem. The good news is those customers are open to hearing from someone new, because they've already talked to everybody they already know, and the problem is still... It's not that it's unsolved. It's being solved in a crummy way and, by the way, in a deteriorating crummy way. So it's getting actually worse. So there's pressure for them to act. This is where you go from the project model to the solution model, and as a vendor, you over commit to their problem.

**Geoffrey Moore** (00:12:54):
From the very beginning, you talk to them. They don't want to talk to you about you. They want to talk to you about them, and you need to ask them probing questions about them. Just like going to a doctor, you don't want the doctor to come and say, "Hey, can I show you a movie of the operation I just did? I want to give you a demo. You mind if I give you a demo?" It's like, "No. What I would like to do is talk to you about this pain I have in my side." And then when the doctor asks you good questions about it, you go, "Ah, this is a good doctor. I'm going to trust this." So that's the whole point about that. Again, that scales a lot more than a project business, but it only scales up to the limit of the target segment.

**Geoffrey Moore** (00:13:31):
So we had this bowling alley model of extending. You could go to a second segment, a third segment if it was adjacent. Adjacent means either it's the same customer with a different use case, or it's the same use case in a different customer base, because the one case, you use your customer references. The other case, you use your partners, because the partners who built the one use case will say, "Well, we got another segment that we work with. Let's bring you into that segment too." So that can take a company from, I don't know, tens of millions of dollars to hundreds of millions of dollars in the bowling alley. And in specialized industries like computer-rated design or things like that, you can actually go to a billion dollars or higher.

**Geoffrey Moore** (00:14:13):
But with most other categories, at some point, you have this third inflection point, which is it's when people go, "Well, wait a minute, wifi isn't just for financial analysts, or isn't just for... Wifi is for everybody." So instead of saying, "We believe what you believe," which we're not there anymore. And these people aren't even really saying, "We need what you have." What they're saying is, "We want what they have. This is really cool. I want what they have," and that creates what we call the tornado. That's when people... This is when you do want sales coverage, and you do want to go broad, and you do want to have a standard product. Basically, you want to capture as much market share as you can. There's a whole playbook around doing that, which was in a book called Inside the Tornado.

**Geoffrey Moore** (00:15:02):
And then the last one, which is actually becoming much more important in this century is called Main Street, but Main Street where products have become commoditized, services become the new place of innovation. We've had taxis for 100 years, but Uber is an incredibly valuable thing. You convert the product to the service, and how do you revolutionize services? That's a situation where now people are saying, "Look, I don't want to own the product. I don't want to own it." Well, kids, "I don't want to own a car. I just want to call Uber. It's convenient." So anyway, those are the four models, and Crossing the Chasm was about that second one.

**Lenny** (00:15:45):
Amazing. You touched on so many things that I want to talk about. I definitely want to dive into the bowling alley metaphor and strategy there. But to close the loop on this target audience to start with initially. First of all, you have this awesome bonfire analogy that I think might be useful to share. Then along that, is there any example or an example or two you could share of just someone that did that really well of picking a really good initial target?

**Geoffrey Moore** (00:16:08):
Sure. Well, the bonfire analogy is just the tendency when you're in the chasm is, "I just need more customers. I should take any customer I could find." Because we need revenue, but the analogy I have is it's like taking a match, and running it back and forth under a log. It's not going to light the log. So how do you start a fire? Well, you start it by putting a little kindling, a little crumpled up paper, and you hold the match one place until the fire starts. Then you want to build... The bowling alley metaphor is a little bit about, first of all, how could you win your first segment, but then increasingly, how would you go forward to win it? That's why adjacency is so important. If you like the fire and the piece of kindling is here, but the log is in the other room, that doesn't work. So I think those are the key ideas.

**Geoffrey Moore** (00:16:59):
There's a lot of people that have made Crossing the Chasm successful. The one that we wrote about first was this company called Documentum, and it's a good example. So it was a document management database back in the day that was not... that nobody had any, "Why would you need this?" It started with the pharmaceutical industry, because pharma said, "Well, new drug approvals are 500,000 page documents, and they really, really, really are hard to manage, and we're screwing it up. And every day we screw it up, we lose a day of patent life of our drug, and the day of patent life's worth about a million or $2 million a day. This is a bad situation. We need to do something."

**Geoffrey Moore** (00:17:37):
So "Okay, pharma, you got pharma." Great. Well, then what happened was the guys in petrochemicals said, "Well, we're in the chemical industry. We're not in the pharmaceutical industry, but we have these standard operating manuals, and we have all these regulatory demands on us too. Not quite like the FDA, but this looks like this could be pretty useful to us too." And then after the petrochemicals guys got... Well, the chemical guys got it, then the petrochemical guys got it. Of course, they're oil and gas, and they say, "Well, in addition, we have all these leases. The lease holds them. It's brilliant. This property is critical to our future plan, so we need a document database for the leases."

**Geoffrey Moore** (00:18:20):
So the guys on Wall Street who are financing these guys are going, "Well, wait a minute. Hell, I mean, we're paper from wall to wall here. Why don't we..." So what happens is you have this thing of this expansion, but in each case, it was into a new segment, but the use cases were close enough.

**Lenny** (00:18:36):
So if a startup founder is listening and trying to decide is their initial target audience, their ICP too wide, do you have any advice for how to know if this is still too wide, and you should try to get more and more narrow? I know you talk about a single use case. What else should people be thinking about there?

**Geoffrey Moore** (00:18:53):
Well, so first of all, before you try to cross the chasm, do you have a marquee? Have you won a marquee customer that puts you on the map? Because if you're not... You need to make yourself visible before you can make the Crossing the Chasm play. Let's assume you've done that. So then when we first saw, "Well, why don't I just use that industry?" Turns out that the visionary person you work with... First of all, they did some very weird things because they're visionaries and second of all, they don't want to help their industry. The whole point of this was they wanted to get ahead of their competitors. They didn't want to help. So normally you can't use the visionary project as your beachhead. You'd love to from a point of view of reusing the work. You just can't. So then the question becomes, "Okay, where am I going to go?"

**Geoffrey Moore** (00:19:41):
So the key formula, and this is the formula... If there's one sort of takeaway from founders listening at this point, you want to have a target segment that is big enough to matter, small enough to lead and a good fit with your crown jewels. That's the formula. So big enough to matter means do I have enough room to double or... Often venture capitalists talk about a triple double followed by a double triple. So if you said, "Okay, let's just, I'm going to make you a million dollars." Put that visionary, but just to give you a number. Okay, so a double triple would be I went from one to four and from four to 12, and then I did a triple double. So that would be 12 to 24, 24 to 48, 48 to 90. Okay, so how would you get from one to a hundred million dollars?

**Geoffrey Moore** (00:20:31):
So you want to have a segment that says that I could get to a hundred million dollars in a five year... That was a five-year window. So you say, "Okay, but what it can't be is a billion dollar segment." Because if it's a billion dollar segment, you might be able to get there, but you would not be a big fish. So that's a fish to pond ratio thing. So you want to think about, particularly as you're starting out... This is a B2B model predominantly. If I could take the top 20 customers in this segment, meaning... What do I mean by a segment? It's in the same geography. People in Japan don't talk to people in America. People in America don't talk to people in Germany, they even speak different languages. I don't know why everybody doesn't speak English, but apparently they don't. So they have to be same geography, same industry, because dentists do not talk to software designers, who don't talk to advertising people and in the same profession.

**Geoffrey Moore** (00:21:23):
So salespeople don't talk to finance people and finance people don't talk to the guys in the warehouse. So same industry, same geography, same profession. And then the compelling use case, which is the thing... That's the thing that starts the fire. There's segments everywhere and by the way, they all have that... They all do... Every segment works the same way. If I have to make a high risk buying decision, I'm going to talk to my peers about it. And I don't want to be first. I want to be able to do whatever the herd's doing. But what a compelling reason to buy does is it goes well, but I have to act faster than I want to. And that's what you need as an entrepreneur. You need the customer to be coming toward you even though you're new and you're unproven, and frankly you scare the crap out of them, but they're even more afraid of the problem that they're saddled with. So that's why you can build a relationship with them.

**Lenny** (00:22:19):
Amazing. And this phase comes... You kind of imply it comes after, say you're at a million dollars AR, you don't do this sort of work of trying to cross the chasm at that point, until you reach something like that?

**Geoffrey Moore** (00:22:31):
I'm not sure AR is going to be the right reference. Here's what you need. You need a major account who's gone all in with you on the new technology and who is willing in some way to talk about it. The good news about visionaries is they tend to have fairly big egos and they tend to like to talk, unlike pragmatists who will not want to talk. Pragmatists, they'll have to go to legal and get permission and blah, blah, blah. But once you've got that, whatever your revenue is at that point, you should be starting to think about, "Well, what is my beachhead segment?" And the good news about Crossing the Chasm, it's not expensive.

**Geoffrey Moore** (00:23:12):
Think about it, once you've said, I'm going to stay in one geography, in one industry, one profession, think about your marketing budget. You're not buying Super Bowl ads here. There's no sock puppets. That's not what we're doing. We want to get to maybe 200 people with a message. And then do you have the domain expertise to really understand the problem? And if it's a really compelling problem, they'll take the meeting and getting that meeting is... Because if you're an entrepreneurial founder, you're probably fairly charismatic. First of all, you've convinced your spouse that you're willing to work for no money with no benefits, and maybe you pitched a venture capitalist and you fooled them, so why can't you fool these guys? Anyway, that would be the way I would go.

**Lenny** (00:24:02):
Essentially, the advice here is if you're a new early stage startup, one of the biggest milestones you want to aim for is a big marquee customer. When I think about this and look at a startup deck, if I see something like Figma is using this product or notion or Salesforce. Clearly, I'll be like, "Wow, okay, these really sophisticated people decided this was useful to them." And so I will innately trust that. There's also often advice of don't work with big companies because they'll push you around, they'll take a long time, they'll force you to build a thing just for them and it won't apply to other people. What's your advice to avoid that downside?

**Geoffrey Moore** (00:24:37):
It has to do with the persona of the executive sponsor. Nine out of 10 executive sponsors are going to be the negative because they're going to be a company person working with company processes. They're going to send you to purchasing, nobody's going to be happy. You're looking for the 10th one. The 10th one is one who says, "I'm so tired of the status quo. I'm looking for people that are visionary like me. I like talking to you better than I like talking to my peers because you're different and I want to be different. I want to leapfrog the world, and these people just want to stay on the escalator. So they're staying on the escalator. God bless them, but I want to jump over the top." So it's a persona based choice is the key thing there.

**Lenny** (00:25:20):
That is really interesting. And then say that you are an early stage startup again, how soon do you think it makes sense to invest in finding that big marquee customer versus finding some smaller... I imagine you start with some startups to see how people... You don't go straight there.

**Geoffrey Moore** (00:25:36):
Yes, and so initially, I think... And of course you and I are both playing, let's be clear, we're playing a software game. For example, I was trying to apply this framework to Intel, and Intel said to me, "Geoffrey, you do understand that a prototype product in our industry costs about $500 million." Okay, okay, okay, okay. Maybe that's not the same model. I think in our world right now with digital transformation, most entrepreneurs are doing some software led play, which means you can work with a small team. So I think what I would advise is I would do projects. Even though I have a product vision, I would start with trying to make as much projects, which would be very customer led. And frankly, initially, even if I have a roadmap, the customer's probably going to take me off my roadmap a bit.

**Geoffrey Moore** (00:26:31):
I'd have to be willing to say, "I'm going to open the aperture enough." Because I just need to get enough experience with the technology. I need to put in people's hands. If it's a freemium play, you can do it for free. But that tends to be more of a consumer play. There are exceptions. There are B2B companies like Atlassian and things that did start as a freemium play, but that's not as normal. I would think more of the consultative play to do that. But what I would try to do, so I would try to get to cashflow break even on my own money with no venture capital. The only reason you need venture capital is if... Well, two things. Either A, the technology is too expensive and you cannot self-fund it, GPUs a bunch of that, training large language modules, those kinds of things. Or this thing is going to catch fire too soon and I don't have time to dither around for two or three years. So those are two reasons to go to venture capital, but just because you want to do a startup doesn't mean you need venture capital.

**Lenny** (00:27:35):
We had Jason Fried on recently the CO of Basecamp, and he made that point in many different ways. The benefits of not raising and how most VC funded companies do not work out, and even though they do, you often don't make as much as you could if you tried it to bootstrap it. So I think there's a lot of resonance there. And you have this quote that essentially kind of what you just said, that with a single round of funding, you should be able to cross the chasm and dominate a single use case in a single market within 18 to 24 months.

**Geoffrey Moore** (00:28:03):
Yeah. This is like an English major doing math, so be careful because I am an English major. But in general, because again, I said it's not expensive, and by the way, you're not discounting. In other words, you're actually using value pricing because the problem you're solving is severe enough, the customer doesn't want a discount, the customer wants you to... It is like if you have to have heart surgery, you don't want a coupon that says, "Heart surgery 9.99 this Saturday only." You want to go to the Mayo Clinic or you want to go to wherever, so you don't have to discount.

**Geoffrey Moore** (00:28:44):
What you do have to do is you have to make almost like a guaranteed commitment to the problem to solve. We're going to take this problem off the table and we're not leaving until you're satisfied. That's the key to the game. That's a little bit weird because if you've invented ChatGPT, and now you're saying, "But I am going to solve the third grade math problem," which is a real problem. But ChatGPT can do anything. I know, but we're going to solve the third grade math problem. That's hard for a lot of entrepreneurs to get their head around.

**Lenny** (00:29:23):
It reminds me of the way Figma started, even though it took them a long time to find product market fit and started scaling, they ended up working very closely with Coda. I don't know if you know the story where they just wanted to make sure the Coda team, and it was called Krypton back then was very happy with Figma. So they went to the office, they set them all up, they started using Figma. And then on the drive home they called him like, "It doesn't work anymore. Something's broken." And they were already home. And Dylan basically, and this team drove all the way back, I think it was an hour or two, and got there and turned out the Wi-Fi was down and there was some internet issue and fixed it and just was obsessed with making sure they were using it. And they're also just fixing the most ridiculous bugs that were not important because they just wanted to make sure they were really happy with it.

**Geoffrey Moore** (00:30:11):
[inaudible 00:30:11] a larger company would say, "Look, we'll put you in our queue and you'll be on our... We'll get to you." I think this is... And by the way, this is part of the fun, frankly, of being in a startup because you're so close to the action, because there's nothing between you and the action. So why wouldn't you do that?

**Lenny** (00:30:29):
Yeah, and I think one of the takeaways I've had for my own research into this is that you need to find one company that just loves you. It's not like "[inaudible 00:30:37], this is cool." It's like, "I love this product. I would never want to give it up."

**Geoffrey Moore** (00:30:40):
That's kind of what I meant by that marquee ref... We sometimes we call it a radiating reference. It's just somebody really, we talk about you when you're not even in the room. Yeah, very cool.

**Lenny** (00:30:52):
We've talked about this idea of the chasm and Crossing the Chasm, but it might be helpful just to explain what is the idea, what is this chasm? What is it that people fall into and why is this important?

**Geoffrey Moore** (00:31:01):
And this was funny, because I was working at Regis McKenna, which was this marketing agency that was sort of the premier high-tech marketing agency in the eighties. And we had all these really successful launches, and then covers of front page articles on Fortune magazine and Wall Street Journal. And then a couple of years later it's like, "Well, what happened to these guys?" So that's where the chasm was like... That's what caused the investigation. What we learned was visionaries make their own buying decisions, and they do not consult their peers. In fact, if their peers are doing it, they're probably not going to do it because they want to be different. So basically these companies were having success capturing the imagination of the visionary, and they thought, "Well, I'll use the visionaries as a reference to get the pragmatist."

**Geoffrey Moore** (00:31:53):
The pragmatist looks at the visionary and goes, "That's not my guy. First of all, he thinks I'm dumb. He thinks he's smarter than I am. Second of all, he does stuff that I would never do, and he makes decisions in a way that I would never make them. So that's not... No. So but I am interested in talking to my peers, but the problem now is, well, which of the peers are going to go first?" And it was kind of like the junior high dance problem. How do you get the party started? So that was the chasm. That was what created the chasm. The pragmatists need references and they will not accept a visionary as a reference, and they don't have any peers that have tried it yet. So that was what was happening.

**Lenny** (00:32:35):
I think that's such an important point that I think people don't quite always get that that reference, marques customer needs to be a pragmatist. It can't be one of these early adopters that are just trying stuff. And these other pragmatists need to feel that this is my person, this is just like me. And they love it.

**Geoffrey Moore** (00:32:53):
By the way, one of the reasons that pragmatists have a certain... It's not contempt for visionaries, but it's definitely wariness, it's because often they have to clean up the messes that these guys leave behind because when you're a visionary, you leave a lot of messes in your wake. And then the pragmatist has to come in and clean it up. So they're going, "Oh, that's another mark against these people."

**Lenny** (00:33:14):
I saw a deck of yours where you actually represent each of these stages of the lifecycle and the visionary Steve Jobs is the way you represented it, and the pragmatists are just like business people in suits sitting at a conference table.

**Geoffrey Moore** (00:33:24):
Exactly. And there's six of them. And the key idea behind that is none of us... By the way, I don't think any of these people are a guru and they don't think I'm a guru. We're using the antelope strategy, it's a herd strategy. But at some point... And by the way, we do this all the time, every one of... Airbnb, I want to get an Airbnb in Portland. Have you ever stayed [inaudible 00:33:53]? Is this a good hotel? Is this a good restaurant? Is this a good dentist? Is this a good lawyer? That's how we do it.

**Lenny** (00:33:58):
I think Uber and Airbnb is the best example of this in action where I would not ride in a random car, especially I think women were most like, "I will never get into a car, into an Uber." This is insane until all of their friends are doing it. And then, "Okay, let's give it a shot."

**Geoffrey Moore** (00:34:13):
I guess it's okay, yeah.

**Lenny** (00:34:15):
Yeah. So essentially most people were pragmatists and I guess that makes sense. And pragmatists make up the biggest chunk for it.

**Geoffrey Moore** (00:34:21):
And by the way, you can be a visionary with some things, a pragmatist with other things, and a conservative with other things. So the way to really think about them is, what is my persona in relation to this decision?

**Lenny** (00:34:34):
I love this example of the junior high dance problem where nobody wants to go ask the person. It's like, "I'm going to wait for them to come to me. I want to see how this plays out." It's such a good metaphor. In terms of how much of your product needs to be built at each of these stages. What advice do you share? How much do you need for these visionaries versus the next?

**Geoffrey Moore** (00:34:52):
So with a visionary, you have to have the magic ingredient working. You don't have the whole product. And in fact, your product may be buggy, but it does something... Andy Grove used to call it the 10 x effect. You need to do something that is an order of magnitude better than anything because that's why the visionary is talking to you. They're going, "Oh my gosh, you have this fusion." "Fusion, really?" "Yeah, we got fusion energy." So that's number one. Then what would still cause you to not cross the chasm yet? If there's not enough product there, pragmatists cannot put up with a product that doesn't work. So you may need to do some additional work to say, "Look, we get some more customers. I'm still living hand to mouth. It's mostly project work, but until the product has got enough stability and can be productized, I really can't afford to cross the chasm." So once you have a product that works, then you've got to say, "Okay, now I've got to find a market where it can be the dominant solution." That's the time to cross the chasm.

**Lenny** (00:36:05):
And a big part of that is obviously they have bosses, they have checklists, they have compliance people, they have IT people, they have people that need to buy into this or this meeting room with six people. They all have to be like, "All right, this is the best choice."

**Geoffrey Moore** (00:36:18):
And by the way, normally those people are designed to keep you out, and that decision process will take forever and you'll be in the welfare lines before they make their choice. So that's why it's so important to have what we call the compelling reason to buy. You need to have a group of people in a room where the leader, the guy who's going to actually sponsor make this decision is saying, "Look, I already gave this problem to everybody in the room, and our answer sucks." He wouldn't say it that way, but that's the truth. And therefore, we're kind of at the... I mean, I'm getting the message. First of all, my boss's boss's boss knows my name. That's a very bad thing. Secondly, I'm getting the message, you're either going to fix this problem, Geoffrey, or we're going to find somebody who can. So that's what gives them the energy to go against the inertial momentum of the decision-making process in their company.

**Lenny** (00:37:15):
**Geoffrey Moore** (00:38:58):
So if you're a pragmatist, the first thing is if it ain't broke, don't fix it. Which makes you totally different than a visionary. A visionary's like, "Yeah, no, come on, break it. Come on, let's move on." It ain't broke, don't fix it. If it is broke, who has fixed it? Is there fix in production? Does the fix work? I want that. In other words, basically to April's point, it is a risk reduction buying strategy. And by the way, you go as slowly as you can normally, but when you're under duress, you have to go faster. So the compelling reason to buy is putting you under duress.

**Lenny** (00:39:41):
Are there any examples of these compelling reasons to buy that come to mind that give people a sense of here's a really good compelling reason to buy? I don't know if it's a pitch.

**Geoffrey Moore** (00:39:48):
Well, there's a ton. Well, how about ransomware? I mean, all of a sudden the cybersecurity thing is like holy smoke because it used to be, "Well, they wouldn't attack my company. Or if they did, I mean, I have no assets." Yeah, well, actually... Because it used to be what they did is they would only attack companies that had data that they could resell in the dark web. Then God bless cryptocurrency, people are saying, "Is it cross the chasm yet? Well, their first use case is criminals." It's not a very good use case, I'm sorry to say. But the point is, now ransomware with cryptocurrency can be a monetization, so that means everybody is vulnerable. So that's one kind of compelling reason to buy. But if you look around kids who are struggling with school, the parent has a compelling reason. Anything with healthcare, compelling reason to buy. Anything if you're in a legal problem, you have a compelling risk to buy.

**Geoffrey Moore** (00:40:48):
So I mean, there's always these situations where you say, "Okay, that's on a personal basis." On a company-wide basis, it may be things like, "Well, what am I supposed to do my office space? Can I get my company to come back to the office or do I have to dump the space? What am I supposed to do? And by the way, I know I'm going to have some kind of space, but do I want to design it the way we used? I'm getting into some space by the way, I got a great deal if it was a fire sale, right? Cool space, what do I put in it? Is it supposed to have offices? Do they have doors, do they not have doors do?" So in other words, there's a bunch of stuff where you get people going, "Okay, how can we help? How can we help?" "I need help. And I've gone to my standard solutions and no, I don't believe that, so I need help."

**Lenny** (00:41:37):
Okay, so it's interesting that I even misunderstood what you're saying and I think this is a really important point. The compelling reason to buy is not a compelling reason to sell, which people often think about as the pitch you're making. The buy is basically the pain point. They need a really big pain.

**Geoffrey Moore** (00:41:51):
Yeah, because that's what's going to... So therefore the key to the bowling alley that's different from the tornado, and it's also different from the early market. In the early market it's about you. You tell the story about you and the visionary wants to hear about you. In the tornado it's also about you, because we now have budget to buy this stuff, and you're a candidate. In the bowling alley, it's never about you. And that is so hard for a series of entrepreneurs because they want to give a demo, they want to tell the story, they want to share their vision. The answer is, "We don't care. We don't want to hear your story. We hate demos, and I don't know who you are and I don't care. I'm in trouble. We need to talk about me. We don't want to talk about you."

**Geoffrey Moore** (00:42:35):
So we have this saying in the Crossing the Chasm playbook. First of all, "Shut the God damn laptop. Just don't open it and start with..." And the way you start the conversation is always the same. "We're here because we've been working with some people in your industry and we understand there's this really serious problem around document management or around Wi-Fi access or whatever it is, and we believe that your company might have it, is that true?" And what's interesting about it is you'll get one of two responses either, "Oh, are you kidding me? Okay, we have that." Or often they'll say, "Well, not exactly." And you go, "Oh," but then before you can say anything else they'll say, "What our real problem is..." So people will talk about their... They want therapy, they'll talk about their problems. So if you're willing to... But as an entrepreneur, you got to realize the gold at this point is problem domain knowledge. That's the thing you really want to collect.

**Lenny** (00:43:45):
Amazing. So you've sort of answered this question, but I want to make it even more complete. You have this amazing LinkedIn post of these four go-to-market playbooks based on the stage you're in. And you've touched on this already, but it might be helpful just to go through it one by one. And even more helpful would be like, what does it look like when you're in the early market? How do you know if you're in the early market versus in the bowling alley versus in the tornado?

**Geoffrey Moore** (00:44:08):
Okay, so in the early market, you know you're there because first of all, the story is the technology, and it's specifically the disruptive technology. By the way, you could start a business with a non-disruptive thing, but then you don't need these playbooks, then you're on Main Street. So the assumption is you've got something that nobody's ever done before or seen before. So in that playbook, the first thing is just you hear the responsibilities. And a venture capitalist would say the same thing to you. "Do you have a technology expert who's a wizard? Because we're not going to fund just any two guys and a PowerPoint tech, even though we like your dog."

So that's number one. Number two, "Can you demo the technology?" You have to be able to demo thing. And then three, "Can you create a vision which says what forces are going to release?" And the concept that we use in venture, I call it trapped value. And with the idea is where's the trap value that this innovation would release? Because when you release trapped value, the world will give you a portion of the gain, typically 10%. It's easy an number to do math with. As I said, I'm an English major. So if you want a billion-dollar company, you better find $10 billion worth of trapped value that your technology could- [inaudible 00:45:30]

**Lenny** (00:45:30):
Airbnb is an amazing example of that, right? Where they unlocked people's homes, basically 10%-

**Geoffrey Moore** (00:45:36):
Yeah. Uber unlocked their backseat of the car. By the way, the free labor force, it was like, "Whoa." Okay, so really cool idea early market fund. For the bowling alley one then the playbook is, "No, where's the problem?" And then you got to take it down to in what geography, what industry, what profession, what use case. And that takes... That's not just... I mean, you want to spend some time in doing that. And then what you want to really do is just maintain intellectual curiosity about the problem as opposed to jumping to the solution. So why is this a hard problem to do? What is going on? Where is the trapped value? By the way, how expensive? What is the cost of not solving this problem?

**Geoffrey Moore** (00:46:24):
Often it's a risk exposure, or it could be just a gating item on your growth or potentially a churn problem. By the way, if you wanted to pick a compelling reason to buy, how about if you help SaaS companies deal with churn? Do you think they would care about that? I think they might. So the point being... And you're going to say, "Okay, I'm going to learn more about churn and I'm going to really understand... And by the way, I'm going to understand your churn," which is different maybe from somebody else's churn. So it's the problem domain thing. And then you build your go-to market around... The lead gen is, "Hey, do you have any of these seven symptoms of fatal churn?" And the people that respond to that ad are pre-qualified. And then the BDR, if you're at Salesforce, a BDR would call you and say, "Just confirming you have these problems." "Oh yeah, RBI." "And your role at the company is... And are you responsible for doing this?" "Well, actually no, it's Harry, not Mary." "Maybe we should talk to Harry." "Yeah, you probably should talk to Harry."

**Geoffrey Moore** (00:47:32):
Then you call Harry and you get the appointment with Harry because Harry's got the problem. And then the next thing is you do a diagnostic with them. "So we understand we're talking to your colleagues, here's the problem, here's what we think we're doing. But before we tell you about how great our solution is, let's make sure that we understand what your challenges are." And your goal in that call is to get them to talk as much as possible and for you to take notes. And by the way, this is a place where you probably still want to remember to use a pen because you actually want them to see you writing down their words, because that means, "Okay, he's listening. He's listening."

**Lenny** (00:48:14):
Oh, interesting. That's a good tip. Like on Zoom, would your advice there be just make sure the camera shows your hands?

**Geoffrey Moore** (00:48:19):
Oh, yeah, yeah.

**Lenny** (00:48:22):
Okay. Lean in. Yeah, yeah.

**Geoffrey Moore** (00:48:23):
Or sometimes... I mean, no, you couldn't do this. I was going to say we record it, but they don't want to record it because they're going to say some things during the call that they won't be necessarily complimentary to all their colleagues and they don't want you to record it.

**Lenny** (00:48:38):
Got it. So in this bowling alley phase, how do you know you... I know it's not like this binary switch, but that you're ready to move into that versus the early market playbook.

**Geoffrey Moore** (00:48:50):
Well, I think you get to a point where you realize, "I can't scale my business doing what I've been doing. I mean, I just can't." And if you've taken venture capital, the thing you want to do is, "I don't want to have to raise another..." Well, so understand how venture capital funding works for a second. This is important. A venture capitalist gives you money, and what they're buying from you with this money is, "I want you to use this money to change the state of your company such that when we raise the next round, the next investor will value your company two to three times higher than we're valuing it today."

**Geoffrey Moore** (00:49:30):
So basically the purpose of this money is to change the value state of your company. If you do anything else with that money, you could have done brilliant things, created amazing demos, hired great people, but if at the end of the day you haven't changed the value state of the company and we have to raise more money, we're going to raise it at the old valuation and I as an investor lose, or even worse, we have a down round and I lose even more.

**Geoffrey Moore** (00:49:58):
So once you start thinking about that, so we're then Crossing the Chasm. The Crossing the Chasm play is I need to change the state of my company from a cool possibility to what accountants call a going concern. So what is a going concern? A going concern is a company that two years from now you would expect still to be in existence. Why would you do that? Because they have a customer base that's loyal and they have a ecosystem of partners that bring them into new deals and they have established their CAC and LTV, and they've kind of figured out their operating model. And it's not the biggest company in the world.

**Geoffrey Moore** (00:50:38):
It's somewhere we're now probably in the 10, $20 million, but it's a real company. It's a real company. And that's who you're trying to create when you cross the chasm. And you know you've crossed the chasm when you say, "I don't have to raise any more venture capital. Now, I may want to because I have ambitions to be globally dominant." But you get to raise it on your nickel and on your timeline, not on, "Oh my God, I'm running out of money." So the sooner you can get off with the, "I'm running out..." And particularly last year was fatal to a huge number of companies because that was not how they were thinking about raising funds. They always thought, "Well, there'll be another round, another round, another round." And they were not thinking about changing their valuation state and they're not here.

**Lenny** (00:51:26):
That's a really interesting insight. This idea that you know you've crossed the chasm if you can survive without more venture funding, how do you think about that, the profit element of that? Because it feels like that's the core to being able to survive without venture funding. Is it about making enough money that you can cut and make a profit, or is there some other reason?

**Geoffrey Moore** (00:51:47):
All you really care about is cashflow positive. I just want to be able to keep doing what I'm doing. So you don't care about the actual GAAP accounting at all.

**Lenny** (00:52:01):
I see. So you could cut back and you can get to profitability if you need, but the idea is your cashflow positive?

**Geoffrey Moore** (00:52:08):
And you'd like to grow and you might want to raise money. But the point is, if you do go out to raise money, you get to raise money at a different valuation. So the way in which venture capitalists categorize you is they say, "What risk is my money going to take off the table?" So an angel investor says, "Well, my money is going to take off the table, the risk of whether you can even create anything, I'm going to give you enough money to get into trouble." That's basically it. And then the Crossing the Chasm money says, "I'm going to take company existence viability off the table. I don't know if you're going to grow, I don't know if you're going to become a venture return, but I'm going to take you going out of business off the table."

**Geoffrey Moore** (00:52:48):
And then the bowling alley stuff is, "Okay, now I'm buying probably a journey from 10 million to a hundred million dollars," something like that. "And I'm expecting a growth rate," and this is probably where the rule of 40 starts to kick in. If you're playing the rule of 40, we want to raise more money later on, you're going to have a different valuation than we had before. And then the tornado thing by that point, now you say, "You're in Gen AI? You have a large language module? Whoa, okay. You're worth a lot more than we thought," because now the category's in the tornado and that's a different game.

**Lenny** (00:53:29):
Yeah. I was going to say AI is clearly an example of being in tornado. So maybe just talk a little bit about what that is, the tornado phase and then there's the Main Street playbook.

**Geoffrey Moore** (00:53:39):
So how do you know the difference between the bowling alley and the tornado? Prior to the tornado, when your sales team calls on the customer, they do not have a budget for you. In the early market, there's no budget for anything. In the bowling alley there's budget, but it's budget for a solution that's not you. It's for the old way of trying to bandaid the problem. So we say in the early market, you have to create budget. In the bowling alley, you have to redirect budget, but that takes sales cycles. It takes time. And if it's a small market... This is why entrepreneurs can win these market segments, because if you're a big established company, this is just a pain in the ass. It's too small a market, it's too much work, it's too hard. Redirecting the... I want my salespeople to go where the budget's already established.

**Geoffrey Moore** (00:54:28):
Well, when does budget get established? When a category goes horizontal and people go, "Well, yeah, we all want Wi-Fi, we all want mobile apps, we all want cloud computing, we all want whatever it is." And now what happens is... And by the way the pragmatist heard is they went from, "You're not doing that, are you?" "No, me neither." "Okay, good." To, "You are, you are, you are. Oh, we're behind. We better do it." So these budgets come into the market and kind of all at the same time, which is what creates the tornado. Because if you give a department a budget, they will spend it and when they spend it, they're going to spend it with a vendor and whoever vendor they select they're probably going to stay with. So now the market share battle is now on, and whoever gets the most customers early on, the ecosystem starts to form around them.

So in the nineties, we saw a lot of tornado, gorilla play. Cisco, Intel, Oracle, obviously Microsoft. I mean these companies, [inaudible 00:55:36], they were all incredibly competitive companies. They were all tornado plays. Between client server and the internet, it just created this massive tornado effect. And that game plan is very competitive sales to grab market share. And then at some point, if you're not number one, then you have to kind of do a defensive maneuver and retreat into a niche and say, "Okay, if I can't be a gorilla, I at least need to be a chimp." And a chimp is like a local gorilla. "I'm not the gorilla, but..." "I'm not Cisco, I'm Juniper." But for telcos, Juniper was the Cisco of telcos at that time. So anyway, I don't know if you saw in the paper today, but at the other end of that lifecycle, HPE has bought Juniper.

**Lenny** (00:56:28):
[inaudible 00:56:28] is happening. I like that. That's good news. So one of the most interesting lessons you teach is also that these playbooks don't work together well. Basically if you use one in the wrong phase, it's the opposite. It has the opposite effect. So before we get there, let me just summarize maybe quickly the playbook in each of these four. I have some notes here and then maybe just talk about why is it that they fail if you pick the wrong one. So in the early market, you're looking for a visionary customer that just wants to use something new and cool and stay ahead of the curve. In the bowling alley phase, you want to engage with a pragmatic business person who has a huge problem and they need a fix and you're there for them. In the tornado, there's just this land grab, something is just going crazy, AI and everyone's just spend, spend, I need AI in my product. And then Main Street is just, it's kind of the sustaining tech that everyone just needs to make sure continues working and doesn't deteriorate.

**Geoffrey Moore** (00:57:23):
By the way, the way I would [inaudible 00:57:25] the last two is think of tornado as kind of the land and Main Street as the expand. I mean, that's not a bad way to think about the two as well. Yeah, you got it. You got it.

**Lenny** (00:57:35):
Okay, great. So why is it that these undercut each other if you're trying to use either the one in the wrong phase or use both?

**Geoffrey Moore** (00:57:42):
Well, so let's start with classic sales 101 from the nineties. Qualify the customer on budget before you make a sales call. That absolutely is critical on Main Street. I mean it's critical on the tornado, it's dumb on Main Street because obviously they have budget, they've got budgets that even has your name on it if you can go get it. But it's a big mistake in the early market or in the bowling alley because they don't have budget. So you're not going to get it. And the way you win in the early market is with a project model and the way you win in the bowling alley is with a solution model.

**Geoffrey Moore** (00:58:17):
And the problem is if you bring a project model to the bowling alley, the problem is you won't scale because it won't be repeatable. The ecosystem won't form around you. And if you bring a solution model to the early market, it's like you're over investing in one thing. The visionary's saying, "Well, yeah, but I have so many other things I want to do." So they're going to want to take you way off your solution roadmap. So each one of these things, the market dynamics call for a very clear response. It's not hard to see the response. What people struggle with is, I have been successful with this playbook, the market has moved to the next phase, but I'm really good at the old playbook, so I want to stay with the playbook I'm good at. So that's when they get in trouble.

**Lenny** (00:59:05):
So I think that's extra reason to pay close attention to which phase you're in and that you're practicing the correct playbook. We've talked about AI a little bit, and I don't want to get too far down this road, but I guess is there any advice you would share for an AI startup in being in this tornado or a company looking to integrate AI? Is there anything that you've seen of just make sure you're doing this right?

**Geoffrey Moore** (00:59:26):
Well, it's interesting about... And particularly right now, I mean the thing that's caught everybody's imagination is generative AI. So we should be thinking about things like open AI with Microsoft and Co-pilot and those kinds of things. Well, maybe not. It depends on what... So from a customer's point of view, there's AI in the early market, there's AI in the bowling alley, there's AI in the chasm, there's AI in the tornado, and there's AI on Main Street. So I mean, I would argue if you go to Microsoft Copilot, you're on Main Street, you're not taking any risk, you're experimenting with a new thing. It's kind of cool, makes you more productive. God bless. It's kind of like just an add-on to Teams or to your whole Office 365 suite. Stuff that's in the tornado right now, I don't know. I'm trying to think about what is the use case for Gen AI? I'm not sure there is one in the tornado, but the closest I would say is Salesforce is probably close enough.

**Geoffrey Moore** (01:00:23):
They have a sales co-pilot. They have a services copilot, right? I'm sure there marketing co-pilot. So you're going, but we're going to change our sales motion and we're going to use generative AI in line, in our performance on a very widespread, across our entire base. So all our salespeople are going to use this new tool. That would be okay. And that makes sense because the new tool... First of all, Salesforce has their own large language module. So it's not like you're going out to the open AI world and having all those issues. So you can do it and there's a very high productivity return at a modest risk, I think, and modest disruption. For the bowling alley you'd say, I don't know if this is bowling alley or early market, I'll say it's bowling alley.

**Geoffrey Moore** (01:01:18):
So if you're Sal Khan and you have the Khan Academy and you're saying, "Look, we want to provide educational resources for the world for young people." The problem with education right now is that particularly after the pandemic, you're a teacher you used to have... When you were a teacher in say K through 12, K through eight, you have a class of 30 kids and probably 10 to 15 of them are middle of the road and some number are actually significantly ahead and some number are behind. And your job as a teacher is to kind of work with that. Well, after the pandemic, you might have five different grade levels in the same classroom, not three or six even. That's an impossible problem. But if you said, "Look, we can use Gen AI tutoring and we can tune it to each one of those sixth grade levels."

**Geoffrey Moore** (01:02:09):
Now that's a teacher co-pilot, but that's a really specialized idea. So you go, "Well, that's amazing." And then if you wanted to go to the other side, "You say all these ad agencies say they do this really cool advertising, but I think I can do it myself with Gen AI and I'm going to sell it to other people." I mean, you can imagine a whole businesses that say we write legal opinions and we always start with Gen AI. We don't ship Gen AI, there's a human in the loop. We're going to do amazing or more images, maybe. We're going to design visual images with all the really cool stuff you could do. We're going to invent a new agency or a new kind of agency we're going to charge to..." I don't know what it would be, but the point is Gen AI I think can be absorbed by the marketplace at multiple places.

**Lenny** (01:03:02):
As you were talking about that lawyer example, I was thinking part of the pitch would be... And it's also a lot cheaper, but that reminds me of this other post that you wrote, The Seven Deadly Sins of Crossing the Chasm. And I wanted to chat about some of these, and one of them is discounting before you cross the chasm. Can you talk about why that's something you want to avoid?

**Geoffrey Moore** (01:03:20):
Back to that issue about, "Heart surgery 9.99, this Saturday only bring a coupon." I mean, the discounting model makes sense when something's commoditized or the let's even do the freemium model. The freemium model makes sense if there is no risk in adopting the offer. But chasms are based on risk bearing decisions. Basically that's the problem that creates the chasm. I have to make a risk bearing buying decision. So discounting does not reduce risk. In fact, it might even increase risk because this vendor might say, "Well, yeah, I'll give you a better price, but now I'm not going to give you the extra support or we'll have a change of scope." We'll say, "Yes, but now, that wasn't in the contract. So you have to add more." And all of that is fair game on Main Street, but it's not for crossing the chasm.

**Lenny** (01:04:21):
I'm going to pick on a couple of these other sims that you mentioned. One is you call the target customer mix up. Can you talk about that?

**Geoffrey Moore** (01:04:29):
The key to this whole Crossing the Chasm playbook is start with the world. Don't start with... Well, the question we're trying to answer is where is a small pool of trapped value that we can become our pool? So that's why we have geography, profession, use case. We're just trying to get big enough to matter, but small enough to lead is one. And then once you find that pool, the question you have to say is, "Who controls access to that? Who's going to sponsor my deal in order for me to solve that, to release that trapped value for that company?" That's your target customer. And you may not know them. Typically, my experience is you probably have worked with at least one company in the industry at some point along the line. It's kind of odd if you just had never heard of the industry and you picked that one.

**Geoffrey Moore** (01:05:24):
Usually that's why I said, "Well, maybe I should have added that to how do you know you're ready to cross the chasm?" You should at least have a hunch. You should at least, "We've done this work, and I think this is the one." Now, you still have to go validate it and make it happen. But basically the way you would validate it is rather than try to go to a research or do something, that won't work. You say, "Well, we're going to run a marketing campaign, a modest one. I'm going to see if I can't get two more of the same use case. I'm willing to bet the next three months of my company by saying in this three months, all we're going to do is try to get two more deals that have this pattern." And that would be kind of the way you might go after it.

**Lenny** (01:06:10):
So I think this is worth spending a little more time on this idea of how you know you're ready to cross the chasm. So one is you find one very excited marquee customer, then you're sharing, maybe find a couple more and see if it's actually starting to roll and tip.

**Geoffrey Moore** (01:06:26):
No. Well, I said it wrong. So the marquee customer is probably not in your beachhead market. The marquee customer is a famous company that you have the visionary sponsor. That's the thing, because that's the company that the business press wanted to write about, or the tech press wanted to write about. People went, "Oh, you were the guys who..." You're like Hans Solo. You did whatever that run was in 15 parsecs. I can't even remember what it was. But that's your claim to fame. It's your claim to fame. But the Crossing the Chasm one is, "Oh..." And by the way the press is not interested in the crossing chasm, but the local, if there was a local press, they'd be all over it.

**Lenny** (01:07:08):
The Kessel Run.

**Geoffrey Moore** (01:07:11):
The Kessel Run. Thank you. The Kessel Run in 15 parsecs. Thank you.

**Lenny** (01:07:13):
That's right.

**Geoffrey Moore** (01:07:14):
Exactly. That was his visionary thing.

**Lenny** (01:07:16):
So I think the important takeaway there is there's always this advice of talk to customers, make sure they're happy, build what... Not necessarily build what they want, but make sure you're understanding what they need. But I think when your most important insights here is make sure you're talking to the right people. Which are essentially people in the next stage, essentially of the adoption life cycle. The more pragmatists.

**Geoffrey Moore** (01:07:35):
Yes. And they have to be the... I think you need to talk to the economic buyer as opposed to the end user, because the end user will be saying, "Oh, yeah, you're right. Oh, it's just terrible and we're oppressed." But if their boss doesn't want to sponsor it, it doesn't work.

**Lenny** (01:07:51):
Which is hard, hard often when you're building B2B software, you just don't make it great. And then it's like, "Oh, these people don't actually care what they're buying it. They just have all these check boxes." And then another deadly sin, which you've touched on, but I think it might be worth sharing again, is just this idea, you call it the compelling reason, confusion, where instead of thinking about your compelling reason to sell, you think about what is the pain point you're solving, compelling reason to buy.

**Geoffrey Moore** (01:08:16):
Obviously as an entrepreneur, you have a compelling reason to sell. But what they tend to do is in trying to cross the chasm, if they're not using this approach, they think, "Well, I haven't made my product attractive enough." So then they'd say, "Well, I'm going to make a sexier demo, or I'm going to change my deck. I'm going to write a new..." And the sales guy comes back, says, "I had a great presentation. This is the deck that we ought to be using." And that's all about compelling ways to sell, not compelling reasons to buy. And the pragmatist, by the way... And by the way, the practice will take the meeting. One of the problems with the chasm is they don't say no. They just never say yes. And they actually encourage you... "You should come back again with this too. This is really interesting." Yeah, it is really interesting.

**Lenny** (01:09:09):
Kind of along those lines, positioning, how important is that, and any advice on figuring out your positioning when you're doing this? I know you talk a lot about making sure you focus on their pain point, but at some point you're like, "Here's what we're doing for you."

**Geoffrey Moore** (01:09:22):
One of the nice things about Crossing the Chasm is the positioning formula is absolutely the same every time. It's really cool. So basically when you're thinking about positioning, you're saying, "Look, I'm going with this use case in this particular segment." So they have an incumbent vendor. The advantage of the incumbent vendor is they understand the business, but they don't have the new technology. Conversely, you have technology competitors who have as good technology, maybe a better technology than you have, but they're not committed to this domain expertise of this thing.

**Geoffrey Moore** (01:09:56):
So your positioning is, "We are the technology leaders who have specialized and committed to solve this problem. And by the way, we have huge respect for your incumbent vendor. We're not asking you to kick them out. They just can't solve this problem. We also have respect for our peers, but frankly, they wouldn't know your problem if they wouldn't recognize it in a lineup. We are here, and by the way, if anybody comes into our quadrant, we're going to kick their ass. We are going to be beyond compare. Nobody is going to handle this problem with this kind of technology the way we will, and that's our claim of fame. That's what we're going to do, and that's our positioning."

**Lenny** (01:10:36):
I love that. Say you're building a product led growth company, a bottom up oriented B2B SaaS company. Is there anything that changes in your advice?

**Geoffrey Moore** (01:10:46):
Yeah, if you're going to use a volume ups approach like Atlassian or anything grows up from the bottom up, you're playing a different game. First of all, you're playing... Because you attract the end user before you attract the economic buyer. So you have some version of a freemium strategy, that's what you're going to do. And Yammer did this, right? And eventually got bought by Microsoft. So the way you play that game is, first of all, you probably do need some funding, not necessarily, maybe you can do this all on AWS and a credit card. But the game that is going to be, how do I create that moment of criticality? What you would do is you'd say... First of all, you need telemetry. So you need to figure out what are the people really doing with our product? And then you need to find a way to communicate with them to see if you can ferret out, is there a compelling reason to buy thing in their environment? So it'd be a different way of doing early market.

**Geoffrey Moore** (01:11:52):
You would not have a marquee client, but to cross the chasm... You cannot cross the chasm of product-led growth, you can't because it is like saying, "Well, yeah, I'm going to cure Covid by just putting vaccines out in public places." It's like, "No, people need to learn more. No." So you'd have to do that. Where product-led growth plays really interestingly, is in the land and expand phases of the market. If you can land with a hot product, but more importantly, product-led growth, which is really good at is expand because it prompts the user to get more involved. And that's classically a Main Street play. But there's got to be no risk. That product-led growth works when basically the extended the next purchase has very low risk, and therefore you're not really dealing with chasms.

**Lenny** (01:12:53):
That is incredibly interesting. Interestingly, every product led growth company ends up building a sales team, 100% of them, including Atlassian, which had product led growth for a long time. And I don't know if anyone's heard this perspective on it, that if you really want to cross the gap... I imagine it happens in some form of-

**Geoffrey Moore** (01:13:12):
Well, and here's the thing. The reason they build a sales team eventually is they need to get enterprise deals. And obviously you need a sales team to get enterprise deals. And one of the mistakes you could make is hiring an enterprise salesperson when you're trying to cross the chasm. Enterprise salespeople are not good chasm crossers because they're used to doing horizontal coverage model. This is like no, domain expert narrow model. You want somebody that looks more like a sales engineer than a salesperson. You want somebody very diagnostic, very committed to the integrity of the problem solution framework. So it's just different.

**Lenny** (01:13:54):
Okay. Just a couple more questions. You had this very public exchange with Martin Casado, he's a partner at Andreessen Horowitz. And just to summarize briefly, essentially he was arguing that I think some people believe once you've crossed the chasm, life's good. It's all downhill. People are going to start pulling your product out of you. It's going to be so easy. And his argument is he doesn't see that, it's endless pain and suffering and hardships. And I know you went back and forth trying to correct this, but what's a way to think about what happens?

**Geoffrey Moore** (01:14:25):
So actually, Martin and I had a couple of this... By the way, his biggest point... I'll come back to your point in a second, but his biggest point is, "Jeff..." The venture community at least, and certainly Andreessen Horowitz doesn't deal with the level of granularity of Crossing the Chasm anymore. There's too much money that wants to be put to work. By the way, there's so much software already out there that the notion that your software is going to be that disruptive is increasingly improbable because you're not standing on the shoulders of giants, you're standing on the shoulders of people standing on the shoulders of people standing on the shoulders of people standing on the shoulders of giants. So he was making a bunch of those points, which I thought were pretty interesting. But his other point about, does life ever become easy? No, life never becomes easy. The problems change.

**Geoffrey Moore** (01:15:17):
The challenge with software is... Well, there's a lot of challenges with it, but software that people use, the application software, we all have different minds. We all have different contexts. To make a product that would work, that would solve what I want and solve what you want and solve what the listener wants. I mean, the margin, no. We're going to have different expectations. So there's always... And then of course there's competition, and then there's funding, and then there's technological shifts, and just about the time it really works well, they say, "No, we got to put it... No, no, no. You put it in the data center. We got to put it in the cloud." "Oh, no, no, you got in the cloud, you got to put it in Kubernetes." "Oh, no, no, no. You don't understand. It's edge AI, it's not cloud." It just goes on and on and on. So I think if you're going to play this game, you got to be up for... Yeah, there's going to be a new headache every week.

**Lenny** (01:16:17):
That's exactly how I see it. I always tell founders, you shouldn't start a company unless you can't not start a company.

**Geoffrey Moore** (01:16:23):
Yes. By the way, why did I leave? [inaudible 01:16:28] County was a great place to be, but I had to do my own thing.

**Lenny** (01:16:32):
And that's a real pull. Kind of along the lines of something you just shared, maybe a final question. Is there something you've changed your mind about or something you've evolved your thinking on recently? Either from the beginning of the book or just even more recent?

**Geoffrey Moore** (01:16:47):
I think what I realized over time increasingly was this is a model that's really optimized for B2B markets, because it implies federated decision making around high risk buying decisions. I would say for the 20th century, that was 95% of tech. But what was so interesting about the change in the century... Because remember right at the change of the century, B2B tech went in the tank, the tech bubble just... Because everybody was afraid of the Y2K problem. So they did a whole bunch of buying up of software, and then there was a year where they think, "Well, we ate more than we could at Thanksgiving dinner. We're not interested in eating another burger here. "So the market went in the tank. By the way at that point, venture started saying, "Well, maybe we should be investing in biotech, or maybe we should doing clean tech." Venture stepped back from the table too.

**Geoffrey Moore** (01:17:46):
But out of this, consumer computing came out of nowhere. And for my generation, it was unimaginable. The first time I heard about Google and they said, "We're going to save every search argument." I thought, "That's the dumbest thing I've ever heard in my life. They're not going to be able to afford it." But their model was, "We are rethinking this thing from the ground up. Geoffrey, you have no idea what we're doing." And boy were they right. So the point was when that came in, then consumer computing and then the iPhone hits, and then we have mobile apps. You have a world now where the B2C play can actually be the core of innovation. It used to be B2C was an afterthought. Now it's like, "No, no, no, no, B2B might be the afterthought." So it's completely different... And the whole digital transformation of the universe, and we're still living through the digital transformation 20 years in, and I don't think Crossing the Chasm is designed for that problem. So that's a different problem.

**Lenny** (01:18:48):
So basically, if you're building a consumer app, don't spend time studying Crossing the Chasm.

**Geoffrey Moore** (01:18:53):
Yeah, if you're doing B2B, this is the most reliable playbook. It's still on... People are still into this playbook 30 years in. So it's obviously... The playbook kind of works.

**Lenny** (01:19:05):
I said this earlier, I feel like people are just reinventing many of the things you uncovered 30 years ago. Everyone's like, "Oh yeah, target audience, really important, or finding a marque customer." So I'm really happy that we spent this time digging into many of your theories.

**Geoffrey Moore** (01:19:22):
Well, Lenny, thank you for being... You've been a really great prompter and questioner, so thank you very, very much.

**Lenny** (01:19:28):
I really, really appreciate that. Is there anything you want to leave listeners with as a final thought or piece of advice or just anything?

**Geoffrey Moore** (01:19:35):
Look, I don't know if anybody's reading the paper recently, but the world's not exactly nailing it right now. There's a lot of stuff going on that we could do a lot better, and software enabled technology is almost certainly at the core of any solution that scales to any world problem that matters. I think it's more important to be an entrepreneur now than maybe ever. I wouldn't make becoming a billionaire my goal. Frankly, I don't even know what a billionaire would even do with their money. I don't even how to even imagine their money. That's a thousand million dollars. It doesn't make any sense, but what does make sense? But what does make sense is to... I'm happy to get two... Do I know what to do with 10 million? Yeah. Could I do 20? Probably. Could I use a hundred? Probably not. But at some point, I want people to make yourself a great living, make yourself... But after that, have an impact. If you're gifted enough to be able to start a software company and do something original, you're a scarce resource, so don't waste it.

**Lenny** (01:20:42):
Amazing. I'm going to sneak it one more question along these same lines actually. Your last book is very unlike all your other books. It's called The Infinite Staircase, which is essentially a guide to living a good life and a meaningful life. Is there maybe one piece of advice you could share with folks of just how to live a better life, a more meaningful life, happier life?

**Geoffrey Moore** (01:21:00):
The purpose of that book was twofold. One was... So I was looking around... And this is an American sort of experience between social media and the politicians or whatever. Our ability to defend traditional values is becoming increasingly challenging. And historically, you say, "Well, religion was sort of the place where the foundation for solidifying traditional values." But in my lifetime, the counter explanation of how we got here, other than being created by a creator, this whole the Big Bang and the Darwinian model, it's becoming increasingly credible and I'm fascinated by it. So the question I had in the back of my mind is how could you take that model and still support traditional ethics?

**Geoffrey Moore** (01:21:53):
So the first part was, well, what's the model? It turns out to explain getting from the Big Bang to Lenny and Geoffrey talking on this podcast, there's a lot of steps you've got to go through. But there's a whole thing about complexity and how complexity emerges in layers and the staircase is a series of layers, and the first two thirds of the book takes 11 stairs. That gets you from physics to theory. And it's like, really? Yeah, yeah. From a cloud of atoms to us talking about Crossing the Chasm, 11 steps, we can get you there. It's kind of fun. It's assembling the last 25 years of my reading. It's fascinating stuff. All these different topics, and I was just trying to knit it together. No original research. I was just literally just trying to get the story together.

**Geoffrey Moore** (01:22:41):
But then the last third was, okay, that's a very reasonable narrative. It's maybe even more reasonable than religious narratives, but now how do you validate ethical action and where does it come from? So the last part was about, okay, how do you do that? How does it derive from that creation story? The secular creation stories were. So that was what was important. At the end of the day, I think the message of that book is just, you really do need to do good, but it's not because you're obeying... In this framework, it's not because you're a bang a divine creator. It's because we're mammals and mammals nurture their young, and we were gifted with unconditional love when we were born because otherwise, you and I could not be here. I mean, a 1-year-old cannot... If somebody doesn't love the hell out of a 1-year-old, they're not going to be two. So we know where we started. So come on, those values were built into us. They don't have to come from above. They can come from below, and therefore, how can you integrate them into your life? And that was where the book... Anyway.

**Lenny** (01:23:53):
That is a beautiful message to end on. I promised I'd get you out of here in one minute. Just to let people know, you do speaking, you do consulting, where can people find you online if they want to reach out and- [inaudible 01:24:05]

**Geoffrey Moore** (01:24:05):
LinkedIn. Yeah, I'm on LinkedIn and I have a blog on LinkedIn. And if these topics are interesting to you, you'd probably be interested in the blog.

**Lenny** (01:24:13):
And then message you on LinkedIn would be the idea?

**Geoffrey Moore** (01:24:15):
Exactly. Absolutely.

**Lenny** (01:24:16):
Easy. Geoffrey, thank you so much for being here.

**Geoffrey Moore** (01:24:19):
Well, thank you, Lenny. It was a pleasure.

**Lenny** (01:24:22):
It was my pleasure. Bye, everyone.

**Lenny** (01:24:26):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [8/19] Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery)

**Jonny Miller** (00:00:00):
I have this idea that I call the feather brick dump truck phenomenon, and basically what that means is when we are showing early signs of burnout, our body will give us feedback usually in subtle ways in the beginning. So the feather might be waking up in the morning and feeling a little bit tired, maybe a little bit exhausted. The brick, maybe you ignore that or you don't notice it, and then three or four weeks later, you have a fight with someone or an argument, or you just feel frustrated and terrible and you lose your cool. And then maybe the dump truck is a month later, or even a year later, there's a full-blown health crisis, or you develop type two diabetes or there's a whole range of things, or maybe you get fired. Ideally, you want to notice when it's the feather and then make adjustments or shift then and not have to wait until you experience the full-blown pain of the dump truck, which unfortunately is what happens to a lot of people, especially when they experience burnout for the first time.

**Lenny** (00:01:02):
Today, my guest is Jonny Miller. Jonny teaches courses and does one-on-one coaching with tech professionals helping them with something he calls Nervous System Mastery, which is essentially a set of tools and techniques for cultivating calm, upgrading your resilience, and increasing your aliveness. If you can get better at dealing with stressful situations, avoiding burnout and being more confident in meetings and big presentations, it becomes a superpower and a huge advantage in both business and in life. I actually read a post by Jonny about a year ago, and it totally changed the way that I think about nervousness and stress, and I still apply many of his lessons today.

**Jonny Miller** (00:04:37):
It's great to be here, Lenny.

**Lenny** (00:04:38):
So I read this post that you wrote, I think it was over a year ago at this point. It was called The Operating Manual for Your Nervous System, and first of all, blew my mind when I read it. Second of all, I always think about it when I get nervous or anxious in a situation, it's really stuck with me. And I know that people in the workplace often get nervous and anxious doing all hand presentations, meetings, performance reviews, all the things. So I thought it'd be awesome just to dive into the stuff that you've uncovered about how we can become less nervous and less anxious. Before we get into the meat of it, I'd love to just spend a couple minutes just getting a sense of why you got into this stuff. What actually got you to spend so much of your energy and life force trying to understand how the nervous system works, how to get people to be less nervous and anxious.

**Jonny Miller** (00:05:27):
My story starts in I kind of have a background in tech. I had a startup, we went through Techstars back in 2012. About five and a half years into that experience, I went through burnout, which is pretty common in the startup world, but that actually wasn't the trigger for me. I find that usually people that get into this type of work, there's some kind of catalyst or some kind of challenging life event. And for me, that was October 23rd, 2017, and my fiance at the time had an anxiety attack and she took her own life. And that completely just destroyed me at the time. And I realized that I'd been so disconnected from my body and my emotions, and it sent me on this five plus year journey to discover all of this inner landscape that I'd been numb from the neck down, and I went into breathwork meditation retreats, did hundreds of breathwork journeys, researched with a breath lab over in Bali, and basically just kind of directed all of my focus and attention onto understanding this inner landscape that I'd been pretty much oblivious to. And since then, I've been working with founders, executives, running courses and teaching what I'm learning and hopefully still researching at the same time as well.

**Lenny** (00:06:52):
Wow. And I imagine the thinking was that if your wife had these skills, she would've had another path.

**Jonny Miller** (00:07:00):
Yeah, that was definitely part of it, yeah. And also just since realizing how many people are struggling with anxiety, depression, all of this kind of constellation of mental health challenges both in the workplace and at home as well. And yeah, it's been a very rewarding journey.

**Lenny** (00:07:19):
All right, this episode's already gotten very heavy and I'm sucked in. I'm excited to learn all these things that you've uncovered. So let's just get into the meat of it. Just talk about this kind of general method that you've found for how to help people become less nervous and anxious.

**Jonny Miller** (00:07:38):
So I find this top down, bottom up distinction to be incredibly helpful. Most people when they try to calm down, they use tactical reframes or maybe mindfulness or maybe reframing the situation in a positive light. There's lots of different practices that people use which do have some effect. But in my experience, working with the physiology, using what's known as a bottom up approach, primarily using the breath, although there's also other approaches that you can use, it's just such a rapidly more effective way of shifting your state.

**Jonny Miller** (00:08:11):
 And to give a little bit of context and maybe some science as well, we have what's known as afferent and efferent neurons going up and down our body, and there's four times more afferent neurons going from the body to the brain as from the brain to the body. So you can almost imagine there's a super highway of traffic of information going up to the brain and four times less going from the brain to the body. And so by learning how to pull on the levers of our physiology, we can rapidly change our state. And then from there, by changing our state, that impacts the thoughts and feelings that we have. So instead of trying to change the story or trying to fix something or trying to solve something, which is what most people do by default, myself included in the past, if you change your state first, then there's a cascading effect which changes your thoughts and your feelings.

**Lenny** (00:09:06):
Okay, amazing. Yeah, and just to share how I felt when I was reading this and try to understand this approach is whenever I get nervous, there's always this like, oh, my body's starting to feel anxious. And then I think of a reason. Oftentimes, I don't know why it gets nervous, why my body's starting to create this feeling of anxiety. And then I often realize I'm just now trying to just explain why it happened, "Oh, I have this big meeting coming up, or I have this podcast episode I'm nervous about, or I'm not going to make a deadline for my newsletter." I often experience this where it's just like, "Oh, something feels nervous." And then, "Okay, here's the explanation." So maybe just along those lines, what else is there that might be helpful for people to think about in this context?

**Jonny Miller** (00:09:47):
I mean, I think it's helpful to understand the process by which, by changing the way that we breathe, for example, it shifts our physiological state and changes our nervous system. So if you're listening to this, maybe you, Lenny, you can try this as well. If you start breathing into your upper chest and shallow fairly, fairly rapid, maybe even through the mouth, that will then there's a part of your brain called the insular cortex, which is basically constantly spying on the way that we're breathing and it will register that change, it will then send information to activate the endocrine system, which then creates shift in our blood chemistry. The sympathetic nervous system gets activated and that increase in adrenaline and cortisol starts to flood your body. Everyone's probably very familiar with that feeling. And then that will then have a cascading impact on the thoughts that you're having and the way that you feel. And so you just shared, we have a tendency to kind of confabulate or make up stories that match the state that we are in. And so that's kind of what happens when we're breathing in that way. And then you can also consciously change your breath to breathe in a different way, which has the reverse effects, which I can go into, but I'll pause there.

**Lenny** (00:11:05):
Yeah. So I think one of the big actionable takeaways here is that instead of trying to convince yourself, "No, this talk is going to go great, I don't need to worry about how I'm going to look in this meeting." Basically instead of going top down, trying to calm your body through thought, your advice is calm your body first because then your mind will notice, "Hey, I'm actually not as nervous as I thought. Maybe things are going to be okay." Is that right?

**Jonny Miller** (00:11:29):
Yeah, precisely. And I mean I've used this myself many times before presentations. I gave a TEDx talk a few years ago and I was like my entire body, I was just terrified. And I did in 15 minutes of this breathing practice before and walked on stage almost cool as a cucumber. It's very effective.

**Lenny** (00:11:47):
Sounds too good to be true. But we're going to do some of these exercises for people. Before we get into, why is it that breath specifically so powerful? It feels like such a strange thing to work so well, just this idea of breathing in a different way. You talked a bit about this, I forget what you called it, that kind of watches how you're breathing. But I guess what else can you share about just why is breath so effective in changing our state?

**Jonny Miller** (00:12:10):
Sure. Well, it's one of the few things which happens automatically, but we can also control it consciously. And so what scientists have discovered that when the exhale is twice as long as the inhale, it has a calming effect. And when the inhale is either more intense or twice as long as the exhale, it has an activating effect. So you can kind of think of this as an up or down lever on the nervous system.

**Lenny** (00:12:36):
You also have this really clever way of describing this system. You call it state over story, essentially focusing on the state of your body versus the story you're telling yourself. Is that the way to think about it? And can you just talk about that concept?

**Jonny Miller** (00:12:48):
Yeah, so it's basically a shorthand for what we've just been talking about, which is most people tend to approach the problem or try to solve things on the level of story. So there's multiple ways you can do that through the breath as we just talked about. You can also defocus your gaze and kind of relax your eyes, and that has a similar effect. It can expand your awareness and kind of bring your awareness to behind you and the sides of you and below you, or you can breathe in these ways which emphasize the exhale. And so when we breathe in a way with say the exhale twice as long as the inhale, that part of the brain, the insular cortex then sends signals to the parasympathetic nervous system, which then has the cascading effect on our endocrine system and calms us down. And what I usually find as well is that the kind of reactive thoughts and feelings that we have when we are in that kind of anxious loop, they can be self-reinforcing. And so if someone has a thought of like, "Oh no, I'm nervous before this important presentation." Then that exacerbates the breathing pattern and then the whole thing just goes into this spiral, which can end up in full-blown panic attacks if there's not an intervention of some sorts.

**Lenny** (00:13:57):
Yeah, that's what I find with my nerves. I hate talking on stage. I get nervous before every podcast. This is not my natural state.

**Jonny Miller** (00:14:04):
Interesting.

**Lenny** (00:14:05):
Yeah, and I hide it well.

**Jonny Miller** (00:14:07):
Is that still the case with podcast today?

**Lenny** (00:14:09):
Absolutely. And it's like different levels of nervousness, but it's always just like, "Oh, there we go." I'm not a performer person. Even I kind of push myself to do this podcast as a way to get better at this, to be honest. So it's still a thing that I think about. And what I find is the nervousness comes from exactly what you described is the nervousness of being nervous. I don't know, there's no reason specifically to be anxious, but I don't know how I'll be once I do the thing. So it's nervous of what it might look like or end up being like. So that's exactly what I ran into.

**Jonny Miller** (00:14:41):
Yeah. And there's obviously people say mindfulness, meditation, things like that, that can increase the psychological space between stimulus and response. And that is something that obviously does help over the long term, but it's in my opinion, nowhere near as rapid and effective and efficient as just changing the way that you're breathing.

**Lenny** (00:15:00):
Awesome. So let's get into it. I know you have a couple exercises specifically for this, and then we'll go from there.

**Jonny Miller** (00:15:06):
We can stack a few of the exercises and I'll try and keep it to a minute or so. So yeah, if you want to get comfy in your chair and sit up straight, feel your butt on the seat, and I find it helpful to kind of be aware of the space behind you and above you as well, kind of expanding your awareness so that you are aware of the space behind to the sides and above.

**Lenny** (00:15:29):
And should we close your eyes?

**Jonny Miller** (00:15:31):
Yeah, and close your eyes down. If you're listening and driving, obviously don't do that. But yeah, closing the eyes down for sure helps. And now we're just going to do simple breath. We're going to inhale in through the nose for four. We're going to hold the breath at the top for four, and we're going to exhale for eight, and then we're going to repeat. So let the breath go and inhaling through the nose. Inhale, 2, 3, 4, hold the breath, 2, 3, 4. And exhale, 8, 2, 3, 4, 5, 6, 7, 8. Inhale, 2, 3, 4, hold the breath, 2, 3, 4, and exhale, 2, 3, 4, 5, 6, 7, 8. And now you can let go of the breath completely and we'll end with one round of humming, which is surprisingly effect of it calming as well. So take a full breath in and humming through the nose all the way to the end of exhale. Let out a sigh if that feels good and open up your eyes.

**Lenny** (00:17:01):
I feel extremely calm. I should do this every podcast episode before we start.

**Jonny Miller** (00:17:08):
A note on the humming. It also releases nitric oxide, which is a vasodilator, and that helps to create that kind of calming effect and it also reduces eye tension as well. So I'll do it if I've been looking to screen for too long. It's really good for kind of reducing eye fatigue as well.

**Lenny** (00:17:24):
And there's also a vagus nerve component to it because your body's vibrating, is that true?

**Jonny Miller** (00:17:28):
Yeah, precisely. So it kind of tones or stimulates the vagus nerve, which stimulates the parasympathetic nervous system.

**Lenny** (00:17:35):
What's your advice for doing this? Is this before you go into a big meeting or a presentation? How do you apply this?

**Jonny Miller** (00:17:42):
I kind of like to share building a toolkit of different practices that are appropriate for different contexts. So something like the 4, 4, 8 breathing, you could do pretty much anywhere without anyone necessarily noticing. Humming is slightly more obvious, but if you're about to jump on a zoom or something, you can totally do it with your eyes closed. Things like expanding your awareness or bringing your awareness down to your feet and your hands, which creates a kind of grounding calming effect that also you can do if you're in a busy room. Maybe you have social anxiety, even orienting and labeling things that you are hearing and feeling, kind of bringing the awareness and attention back into the body that also has an effect. And then there's longer practices for say, non-sleep deep rests, belly breathing, things that you can do if you have 10, 20 minutes and you're at home and you want a downshift.

**Jonny Miller** (00:18:30):
So I like to kind of give people a big toolkit to see what works for them and then cherry-pick which ones are suitable to different situations. And another way that I think about this is, I call it, if this, then breathe. So it's like if I feel overwhelmed, then I do the humming. If I feel anxious, then I do 4, 4, 8 breathing or alternate nostril breathing and kind of having my own little recipe set that I have for different context is really helpful and I work with people to kind of build those toolkits themselves.

**Lenny** (00:19:03):
This sounds like it needs to be a website where people can go with these lists of if this, then that is there a place that we could send people in the show notes and if not, you should make one before we go live.

**Jonny Miller** (00:19:13):
There is not currently. It's part of the curriculum in the course that I have, but-

**Lenny** (00:19:17):
Okay, great.

**Jonny Miller** (00:19:18):
... I can maybe see if I can spin one up as well, but yeah.

**Lenny** (00:19:21):
Okay, cool. We'll link to the course if nothing else. Amazing.

**Jonny Miller** (00:19:23):
Okay.

**Lenny** (00:19:24):
Along this line of calming breath exercise, Huberman also has a different version, which I've tried and I'm going to do both now. You breathe in fully and then you breathe in a little bit more. I imagine you've seen that piece of advice?

**Jonny Miller** (00:19:37):
That's also fantastic. He calls it the physiological sigh, and it's both very effective, especially if you just have five seconds and you just take a full sigh, it's great. I'd also add that the sigh happens naturally as a result of doing these downshifting practices. So if you notice after you do let's say the 4, 4, 8 breathing, at the end, you might naturally just want to let out a sigh, and that's a signal that your body is naturally downshifting. Or if you are with a friend and you feel just comfortable and relaxed, then your body might sigh. And it's something that we do a lot and as you say, you can consciously do it and that will help as well. That's another one of the practices.

**Lenny** (00:20:18):
Awesome. So link to that. And I think throughout this episode, as you said, we're going to give people a bunch of tools that they can use, and it feels like some are in the moment, "I need to feel calmer right now. Here's a thing you could do." And then there's things you can do ongoing that build... I guess another way to think about it's just make your body more calm as a baseline of practice to work on there.

**Jonny Miller** (00:20:38):
Yeah, precisely.

**Lenny** (00:20:39):
Awesome, okay. I think the other breathing exercise we're going to do is the opposite. Gets you all excited, is that right?

**Jonny Miller** (00:20:45):
Yeah, sure. We can do that as well. I call this espresso breath. So this is the opposite. This is very activating. I would only recommend this if you're feeling lethargic or maybe instead of drinking a coffee in the afternoon, you could do this for a minute or so. In the scientific literature, it's bellows breath or breath of fire, and it basically looks like a series of rapid exhales through the nose. I like to keep it through the nose only if you do it through the mouth, it can be very too activating and it can kind of overwhelm people. Obviously, there's the Wim Hof practice that I'm sure many people are familiar with. So this is a more gentle version of... If Wim Hof is like Red Bull, this is kind of like a small coffee.

**Lenny** (00:21:30):
I like that. And you call it the espresso breath, espresso breath.

**Jonny Miller** (00:21:33):
Espresso breath, yeah.

**Lenny** (00:21:33):
So yeah, that's a good metaphor there.

**Jonny Miller** (00:21:35):
Yeah, yeah. So yeah, let's do it. So again, kind of sit up straight, and this time you want to be pumping the breath from your lower belly and you pump the breath on the exhale. So I'll demonstrate it briefly. It's like breathe in.

**Jonny Miller** (00:21:56):
Okay. So yeah, take a full breath in and begin.

**Jonny Miller** (00:21:58):
And let go. And full breath in. And sigh on the exhale. I already feel a little bit tingly.

**Lenny** (00:22:25):
I'm energized. Let's do this. Go, go, go, go. That was great. Okay, look at that. We're back to where we started with the full circle of energy. That was great.

**Jonny Miller** (00:22:34):
Up and down.

**Lenny** (00:22:35):
And then how long do you recommend doing that one for?

**Jonny Miller** (00:22:38):
So it kind of depends on how activating you find it, but I usually find 30 breaths per round and then take a breath, have a long pause on the exhale, and then if you want to do another round or two.

**Lenny** (00:22:50):
Amazing. And the cases where this might be helpful is maybe you're about to give a big talk, I guess in a talk you both want energy and want calm, so that's kind of complicated.

**Jonny Miller** (00:22:59):
Especially if you are meetings early in the morning and you haven't quite got going yet, you can do the espresso breath to begin with and that activates you. And then do some of the downshifting practices to kind of ground and stabilize that aliveness.

**Lenny** (00:23:12):
Are there any other tactical breathing exercises that are worth doing real quick? I know we'll get into some longer practices and deeper stuff, but is there anything else that would be helpful here?

**Jonny Miller** (00:23:21):
No, I think we've covered the bases. I don't want to overwhelm people too much.

**Lenny** (00:23:25):
Just as a takeaway, there's these two techniques. One to help you get more calm when you need to be calm in the moment. The other is to get energy. And then I guess are these things that you recommend doing ongoing to build this muscle in your body or are these mostly for you need this now in the moment and it's not worth just doing a few times a day even when you're fine?

**Jonny Miller** (00:23:47):
Yeah, great question. So I like to recommend both a morning practice, particularly to build the muscle of just doing it and getting used to it. So maybe five minutes in the morning before you start work, before breakfast, something like that. And then you are more likely to remember that you have access to that in the moment because usually the challenge is that when someone is in that flustered state, remembering to do the practice is often the last thing that comes to mind. So by having a deliberate practice for at least 7 to 10 days and so that you get the hang of it, then it feels much more natural to do it when you're feeling. That's kind of like playing the game on hard mode when you are really stressed and anxious, that's when you need it the most, but it's also when you're least likely to remember to do it.

**Lenny** (00:24:36):
Awesome. Okay, so the first exercise to calm you down is essentially breathe in four seconds, hold it for four seconds, breathe out slowly for eight seconds and do that for about 30 seconds, is that right? Or for a minute?

**Jonny Miller** (00:24:48):
Yeah, I'd say for at least a minute or two. We kind of did a shorter version. I'll also add that the important thing is that the exhale is twice as long as the inhale. So if exhaling for eight is too long, you could do 3, 3, 6 or even 2, 2, 4 or even 5, 5, 10 depending on your lung capacity essentially and your CO2 tolerance.

**Lenny** (00:25:08):
Okay, good to know. And then the espresso breath, when you need energy or you just kind of pump air out of your belly through your nose and you do that for how long would you recommend?

**Jonny Miller** (00:25:18):
Two to three rounds of 30 pumps, yeah.

**Lenny** (00:25:22):
And again, the reason this is effective and powerful is coming back to your original big insight that our state is driven by what our body is doing and our mind often explains what we're feeling based on what our body's doing. So that if you can change the state of your body and become less nervous in your body, your mind will be like, "All right, everything's fine."

**Jonny Miller** (00:25:45):
Yeah. And maybe something that we haven't touched on yet, but I think is important to add in is this idea of interoception or somatic awareness. And the reason I bring it in is because if you do this practice but you're not really aware of your body and how you feel, then it'll be less compelling to you. But if you're kind of tuned into like sensations in your body, what's going on, you're more likely to notice the difference in the shifts.

**Lenny** (00:26:09):
Great. So let's get into that. That was something I definitely wanted to touch on here. This awesome acronym to help you with this process of interoception. So talk about what that is and then how to actually go about becoming better at being aware of what your body's doing.

**Jonny Miller** (00:26:22):
Yeah. So it's this idea of interoception, which is known as our sixth sense, and basically it's our ability to sense, track and feel our internal landscape. And I like to use the metaphor of a chef in the same way that you train your flavor palette for kind of sweet, spicy, umami, things like that. You can also train your interoceptive palette and become more aware of the internal sensations, whether that's your breath, whether it's tension, whether it's moods and emotions, whether it's the quality of your awareness, the quality of your thoughts. And the more kind of in tune with that you are, the more likely you are to notice the kind of early warning signs of something like anxiety. Because usually, certainly a panic attack doesn't come out of nowhere. There will be a kind of cascade of subtle things that happen in your body that eventually result in anxiety. And so if you can catch those things early and kind of nip them in the bud and do one of these practices, then you can avoid the kind of 10 out of 10 worst case scenarios.

**Lenny** (00:27:25):
Okay, awesome. So I know that there's also specific things you recommend people pay attention to, to understand what their body is doing in this process of inter...

**Jonny Miller** (00:27:33):
Interoception, yeah,

**Lenny** (00:27:34):
Interra... Okay. What is it?

**Jonny Miller** (00:27:36):
Interoception.

**Lenny** (00:27:39):
Interoception.

**Jonny Miller** (00:27:39):
As opposed to exteroception, which is awareness of all the external stimuli.

**Lenny** (00:27:44):
Got it. I guess before we even get to that, so you mentioned that it's another sense we have, and I think that's a really important point that I think maybe people didn't catch. So we have these five senses, obviously taste and smell and vision and touch. But you're finding and research showed basically this is another sense people don't really know we have.

**Jonny Miller** (00:28:02):
Yeah, exactly. And it has been studies quite a lot, especially in the last decade or so. And there's a number of interesting findings from the research that I found. One being that ADHD tends to correlate with low levels of interoception, as does if people have PTSD or trauma. Again, interoception is lowered. And I'd certainly say for myself, for the first 25 years of my life, I was fairly numb from the neck down. I was not very aware to what was happening in my body in real time. I was also reading a book recently called The Hour Between Dog and Wolf, which looked at Wall Street traders and they correlated higher degrees of interception with basically making more money and making better decisions. And I think the thesis was that by tuning into what their body was doing in certain moments, they could pick up on things more intuitive decision making essentially.

**Lenny** (00:28:55):
So I think there's a specific list of things that you recommend people pay attention to, their posture, their breath, things like that. What is that list and then how do we actually do this better?

**Jonny Miller** (00:29:06):
Yeah. So I simplify this to APE, which basically is an acronym which stands for awareness, posture, and emotion. So to kind of go through each one by one. Awareness is, to give an example, I could narrow my awareness and become really focused and just you kind of tense up and it also is quite activating sometimes or you can relax and expand your awareness and be aware of the space above me, the space behind me, the space below me. And that is generally a calming thing. Posture is fairly self-explanatory. But again, our posture affects how we feel. You're shifting there now. And then emotion, which I include somatic or body-based sensations which arise. So both kind of what is the overall mood and the flavor or the texture that I'm feeling. Like right now, maybe it's excitement, maybe there's some joy. I'm noticing there's some heat in my belly probably from the breathing. Yeah, there's a little bit of tightness in my lower back from working out yesterday. So just sense kind of mapping that landscape of sensation. And for most people it's almost like it's like a [inaudible 00:30:22]. You have those maps of [inaudible 00:30:25] and for a lot of people there's just these big kind blind spots in their body.

**Lenny** (00:30:30):
And the advice here is, so there's this acronym APE and the advice is think about these three things when you're feeling something that you may not, basically something's going on slash just often come back to this. I imagine just whenever you can think of, "Oh, APE: awareness, posture, emotion." Is that how to use this?

**Jonny Miller** (00:30:51):
Yeah, exactly. So again, it can be something that you do before you start your day, maybe with a cup of tea. I like to drink tea and just do a body scan essentially and just check each of those three areas. And it's really valuable, particularly if you are having racing thoughts or something doesn't feel quite right. Instead of just tackling the problem on the level of the mind dropping down into the body and bringing that into the picture as well, I find to be really helpful.

**Lenny** (00:31:26):
Basically, as often as you can. And generally when things are feeling all off, just remember APE, where's my awareness? How's my posture? And then what am I feeling? Am I feeling sad? Am I feeling happy, excited, angry? Things like that. I think you also talk about breath, like you have a list you wrote about this of other things that you might want to pay attention to. Actually finding paying attention to what my breath is doing is really powerful too. So I'm going to try a BAPE version of this or I'm going to try to think about where's my breath coming from, what am I feeling there?

**Jonny Miller** (00:32:02):
Yeah. So the breath and sensations are two other ones that are really helpful. The breath in particular, often people will... There's an idea of email apnea when people are checking their emails, they will, without noticing it, start to hold their breath, which is generally a very activating thing to do. Or as I mentioned earlier, if your breath is through the mouth and shallow and into the upper chest, that will also be very activating versus is your breath through the nose? Is it kind of into the belly and into the sides of the rib cage and does it feel easeful? Basically, breathing without tension is ideal.

**Lenny** (00:32:39):
What I think about using this practice is if I were sitting in a meeting and just not feeling amazingly confident, I just come back to this acronym, BAPE or APE, whichever one you want to choose, just like how am I feeling right now? Oh wow, my whole stomach is clenched. I'm maybe nervous about what might happen or I'm not breathing at all, or my posture is really bad. So I think in a meeting would be really helpful Here, maybe you're about to get on a zoom or an important call or something like that. Maybe a one-on-one. Is there anything else, any other moments that kind of triggers for people of like, "Oh, I should really be aware of what's happening right now. Let me do an APE exercise."

**Jonny Miller** (00:33:16):
Yeah, well, just to kind of piggyback on what you just said, if you are about to jump on a meeting and you're noticing that your stomach is clenched, that's actually really useful data to be like, "Why is this happening?" Is it your intuition kind of saying that maybe you shouldn't do this deal with someone or maybe something is off and so it's a sign to explore that more. Or it could be that you've been triggered by something or something that someone said and you've only just realized it and then that's again, more information or something that you can reflect on or go into.

**Lenny** (00:33:51):
Is there anything in your life recently that is an example of this where you're feeling unsure and maybe you realize, "Oh, here's what my body's doing, maybe I should pay more attention to this."

**Jonny Miller** (00:34:03):
Actually, last week I did a podcast conversation, so I have a podcast myself, and I got off the call and I remember I felt or got off the podcast and I felt pretty exhausted and I felt like there was this kind of tension in my chest. And again, my breath was kind of all over the place and I realized that I had very much over committed myself for that week. I'd scheduled back to back podcast interviews. The podcast wasn't even the priority for what I'm focusing on in this quarter, so I then made the decision to just push back all my episodes until the summer basically.

**Lenny** (00:34:42):
I love that example. I know that feeling very well.

**Jonny Miller** (00:34:46):
I'm sure.

**Lenny** (00:34:48):
When you wrote about this idea of interoception, you connected it to burnout, and I think you talked about how this is one of the best tools to avoid burnout. Is that right? Am I remembering that right? And if so, how do you think about this burnout and avoiding burnout in general, something a lot of people experience?

**Jonny Miller** (00:35:08):
Yeah, so I have this idea that I call the feather brick dump truck phenomenon. And basically what that means is when we are showing early signs of burnout, our body will give us feedback usually in subtle ways in the beginning. So the feather might be waking up in the morning and feeling a little bit tired, maybe a little bit exhausted. The brick, maybe you ignore that or you don't notice it, and then three or four weeks later you have a fight with someone or an argument or you just feel frustrated and terrible and you lose your cool. And then maybe the dump truck is a month later or even a year later, there's a full-blown health crisis, or you develop type two diabetes or there's a whole range of things, or maybe you get fired. There's a bunch of different things that can happen, but normally depending on how attuned or depending on someone's interoceptive capacity, ideally, you want to notice when it's the feather and then make adjustments or shift then and not have to wait until you experience the full-blown pain of the dump truck, which unfortunately is what happens to a lot of people, especially when they experience burnout for the first time.

**Lenny** (00:36:18):
This is such an important point and such a good way of thinking about it. It reminds me of Andy Johns and the episode we had there of just how long and willing to the episode there of just how all these little things came up along the way and then eventually just became incredibly unsustainable to live the life that he was living.

**Jonny Miller** (00:37:55):
Yeah, so I'll tie this in with a concept that I call emotional debt, which is basically when our nervous system experiences stress, there's known as a mobilization cycle, and if that cycle isn't completed or we don't get to downshift or relax on the other side, that gets stored in the body as allostatic load, which I call emotional debt. And over time, that creates fragility in the nervous system. And so what that fragility can look like is anything from being impacted by small things in a kind of disproportionate way. So noticing that you are more reactive than normal, maybe you're a little bit more snappy, maybe you get frustrated by little things, maybe your sleep isn't as good, maybe you wake up not feeling fully rested. Maybe relationships are often, especially intimate relationships are usually a place that this shows up or relationships at work. So those are the classic early warning signs. And then as that emotional debt threshold increases in the same way that say with technical debt, if you're building a product in the beginning, it's fine, and in fact it's even necessary in the beginning. It's great that our body can buffer the stress response because it allows us to function. But if we don't pay off that technical debt or emotional debt, then over time it accumulates and it can also come out through health crises, health challenges. It just gets basically progressively worse until that debt is paid off.

**Lenny** (00:39:25):
I feel like a lot of people listening are like, "Yes, I know exactly what you mean." How does one notice that you're building emotional debt and then how do you start to release this debt and pay off this debt?

**Jonny Miller** (00:39:38):
What I've seen with some of my founder clients and in the research that we did where we interviewed 260 leaders, what can often happen is that emotional debt will increase and increase and increase until it gets to a point where we are well outside what's known as a window of tolerance. And at that point there's like a crash. It's almost like the fuse switch blows and there's exhaustion. Maybe there's complete inability to get up off the couch. And for some people, people with large nervous system capacity, they can keep going for five years, maybe 10 years, and they can keep building this up, and it becomes normalized to live in a way where you are always on and never really relaxing or coming down. Or one really key sign actually is if you are not able to naturally downshift or down regulate your nervous system at the end of the day without something like wine or CBD or some kind of external substance, that's a sign that you kind of reached a certain threshold of emotional debt.

**Lenny** (00:40:47):
And then how does one start to pay off this debt if you've spent years just working way too hard, you've had a relationship that just isn't working great, I don't know. I imagine most people go to therapy and just talk through all these things and try to work through the challenges. What do you recommend if you're just like, "Man, I feel like I have this, what should I do?"

**Jonny Miller** (00:41:08):
Yeah, well, I mean that's a big question. I'll probably get some pushback for this, but I'm not a big fan of talk therapy alone or at least therapy that doesn't have a somatic or body-based component. And from my understanding of the nervous system and how we store this stress, just talking about things and keeping things on the level of the intellect doesn't actually address the root of the challenge. What we need to do is create a certain sense of safety to kind of go into those buffered emotional responses and feel them all the way through and allow that mobilization reflex to complete.

**Jonny Miller** (00:41:48):
And so to kind of give a personal example, when I was living in Bali, I did several hundred breathwork journeys where you breathe in a certain way to get into an altered state, and then in that place, these memories would arise of these things that happened 5, 10 years ago. And my body, it would either move a certain way or the anger would come through. Sometimes there would be sadness or grief. Often there's a lot of stored emotion that's held in our body that just needs permission to kind of be felt through and be released. And so for me, it was a journey of coming into right relationship with my anger and my grief, and honestly my shame as well, giving myself permission to feel this gunk that had been stored in my pelvis.

**Jonny Miller** (00:42:35):
So I'm not saying you have to go to Bali and do 200 breathwork journeys. That's definitely not... I mean, that's a path. But first it begins with, as I said, cultivating interoception and even being aware that there is this tension, there are these things in your body. Secondly, having the practices of self-regulation so that if these things come up, you don't get overwhelmed. You're able to downshift and ground. And then thirdly, it's the practice of what I call emotional fluidity, which is basically creating the conditions of welcoming the full spectrum of emotions as they arise. And often it's very helpful to have a guide or a somatic practitioner, I like somatic experiencing, hakomi, the two modalities I'm a big fan of. And yeah, that's the journey and a process and it depends how many years you've been operating in a slightly numbed way, and it's different for everyone. But it begins by tuning into and listening to the body and then having honestly curiosity about what is there and just following that curiosity and the body starts to show you what is ready to be seen.

**Lenny** (00:43:49):
I love that it always comes back to the original place we started which is that the way we feel is a very bottom up body-based system, it's not we feel something and our body gets nervous. It's our body gets nervous, and they're like, "Oh, here's why I'm nervous." And your advice is just focus a lot on helping your body release the stuff that you've built up this debt. And then also just when you're nervous in the moment, focus on getting your body to a state versus trying to convince your mind now everything's going to be okay.

**Jonny Miller** (00:44:17):
Exactly.

**Lenny** (00:44:17):
And specifically on the therapy route, just to touch on that, so your advice there is if you were to work with a therapist and you feel a lot of this stuff that we're talking about is focused on a somatic oriented therapy where it's body oriented, not just thinking about it and talking through stuff, it's actually convincing your body, "Here's a way to helping your body release this debt, essentially."

**Jonny Miller** (00:44:40):
Yeah. I mean, you can understand in precise detail about whatever the challenge was from 5, 10 and 15 years ago, but if you're unable to connect it to the correlating sensations in the body... Usually if say, I don't know, if I was to imagine someone shouted at me yesterday and I think about that, there's usually a correlating kind of sematic sensation. The neuroscientist Damasio calls it a somatic marker. So by tracking the somatic markers and then either on your own just kind of following that sensation and allowing whatever emotion was present at the time to complete that is the way that we kind of slowly pay off that emotional debt by one process at a time.

**Lenny** (00:45:26):
So maybe coming back to this question of say someone is listening and wondering, am I building emotional debt? Am I ignoring things that are these feathers? What are signs and just, I don't know, examples of emotional debt being built up of this trauma, whatever you want to call it, being built up in the body? I don't know, is it just like anytime you feel really nervous, that's emotional debt? Is it anytime you push something down that you are pretty sure you should deal with in the moment, that's emotional debt? What are just some examples of what that feels like and looks like?

**Jonny Miller** (00:45:58):
Yeah, so it's typically different forms of nervous system dysregulation and that shows up as it could be someone's breathing pattern if they're constantly in this sympathetic or hypervigilant state, if they're always tracking for things, looking for the worst case scenario. Another common one, and this is particularly true in the tech sector, is being very much in the head and living in the thoughts and the mind the entire time. And there's a form of disassociation that happens as a kind of protection mechanism essentially because it's uncomfortable to be with the sensations in the body. And because our society tends to reward people for solving problems and being in their mind, that is a pattern that continues for many, many years or even decades.

**Jonny Miller** (00:46:43):
Other ones are, I think the most obvious one for people is emotional reactivity, where your response to a certain situation is disproportionate to what's happened. So for example, if you said something to me of that doesn't make any sense, and I was like, I freeze maybe... And this is another important point that most people have two versions of reactivity. Some people will freeze, withdraw, shut down and disconnect, and other people will become more aggressive, become bigger and attack and fight back. And knowing which way you tend to orient, for me, it's usually shrink and freeze and shut down, knowing what your pattern is and also knowing what the sensations are when this happens, it's really helpful for you to be like, "Oh, that thing's happening." My priority now is to downshift and kind of find a sense of safety basically in the body and then interact, then make the decision, then have the conversation. Because if you can keep going from that place of reactivity, nothing good happens from that place. No great decisions were made from that place. So again, that's a place where having the interoceptive awareness to know, "Oh, this is what's going on." Being able to then downshift your system, kind of access a sense of, "Oh, I'm okay, actually this isn't so bad." And then moving on from there is a profoundly practical and just useful skill.

**Lenny** (00:48:14):
Kind of along these same lines, you wrote somewhere this idea that you have a big competitive advantage if you feel the feels is the way you described it. Does that ring a bell? And if so, what can you share around that, just why this is so powerful, especially in the workplace?

**Jonny Miller** (00:48:28):
Yeah, so I think I wrote about this in one of the Every essays. I think the title was The Best Decision-Making Is Emotional. And I basically wanted to kind of poke at the phrase, I think I saw someone on Twitter say, "Fact over feelings, like don't let emotions ruin good decision making." And yeah, there's so much that I can say about this. But basically there was a landmark study by this guy, Damasio, this kind of famous neuroscientist, and he studied a patient called Elliot. And Elliot had a tumor in his brain that was removed and it basically meant that he was unable to feel emotions. So his entire emotional capacity was removed. And Elliot went from being a successful married businessman to divorced, broke and unable to choose what he could have for lunch. He was unable to make the most basic life decisions, and it's because he didn't have access to that emotional sense in his brain.

**Jonny Miller** (00:49:22):
And so our brain is like a prediction making machine, and as I mentioned earlier, there's this highway of sensory data that's coming up through the body. And if we don't listen to that when we are making decisions, then we're losing out on a lot of information. And what tends to happen, I see this in clients that I work with, is if they are avoiding feeling a certain way, let's say, that they don't enjoy feeling conflict or anger, then they will make decisions subconsciously to avoid feeling that way. And it becomes a huge bias and a huge problem because people make decisions because they're afraid of feeling a certain way. And if you are on the other hand able to just welcome and be with whatever emotions would arise on the other side of a decision, you're able to decide clearly instead of being skewed one way or the other.

**Lenny** (00:50:16):
Easier said than done.

**Jonny Miller** (00:50:18):
Yeah.

**Lenny** (00:50:21):
Do you find there's ever a downside to being too in touch with what you're feeling? I actually not a feeler of what I'm feeling kind of person. I'm pretty stable, partly because I'm not super in tune with what I'm feeling a lot of times, and maybe this is a huge problem that I need to deal with. But I don't know, it's worked out okay so far. I guess, do you ever find that sometimes it's okay, sometimes you don't need to know exactly every moment anything that's hurting you or causing you pain?

**Jonny Miller** (00:50:49):
Yeah, it's a good question. And some people do have a very high interoceptive capacity, and that can be overwhelming. In which case I would recommend focusing on the breathing practices to build that capacity to downshift, so you're able to just function. And there's definitely people who are overwhelmed by the stimuli of day-to-day life being out in traffic, like they're very easily overwhelmed. And for those people working on increasing nervous system capacity to kind of hold that amount of stress, maybe it's through sauna and cold plunge, maybe it's through gentle titration of stresses and then downshifting, that's actually really valuable.

**Jonny Miller** (00:51:28):
I'd also say that the ability to function well, this applies to a lot of high functioning people, which is probably honestly a lot of your audience. It's very helpful in the moment to, let's say something comes up, you want to be able to buffer intense emotions and say, get through the meeting, get through whatever it is. It's a very helpful skill. But if you don't, then give yourself spaciousness afterwards to downshift and allow yourself to feel whatever was brought up by that experience, you are going to be adding to this emotional debt over time. And as I mentioned, some people, it might be a year before there's some kind of breakdown, burnout. Other people, it might be longer. And usually it's more unfortunate in the longer case because it creates a long-term health crisis and then lower amount of money or time is able to repair the damage that's been done, which can be really tragic.

**Lenny** (00:52:24):
My chat with Andy Johns is a great example of that happening.

**Jonny Miller** (00:52:26):
Yeah. And Andy's a superb example, and I love his vulnerability and honesty in what he's been through.

**Lenny** (00:52:33):
Yeah, I think if you're interested in this topic, definitely watch that episode. Another exercise that you talk a lot about is this idea, it's called NSDR, I think. Talk about that and when that might be useful, how to go about using this tool.

**Jonny Miller** (00:52:49):
Yeah, so NSDR was a practice coined by Andrew Huberman, who you mentioned earlier. And it basically, it's a more scientific lens on the practice of yoga nidra, which is an ancient yoga practice. But I am a huge fan of it, and I do it myself most days for 15 to 20 minutes. Basically what it looks like is you lie down, put on an eye mask or a blindfold, and you listen to a guided audio. I've recorded some myself, so I can share these in the show note links.

**Lenny** (00:53:16):
Your voice would be so good for these, by the way. You found your calling.

**Jonny Miller** (00:53:22):
Nice, yeah. It's really fun for me to do. But basically what it involves is a guided body scan. So this is also a great way to practice interoception. It's something that I didn't mention earlier was that when there's cortisol present in our body, the cortisol basically acts as a numbing agent, so it's much harder to kind of tune into those sensations. But using this, I think it's a 14-minute guided NSDR practice, you're basically lying down, there's a guided body scan, there's relaxing music in the background. And by the end of it, you feel like you've had a two-hour nap. It feels incredible.

And particularly for people who myself tend to get tired in the afternoons, if you space this out, usually between 1 and 3:00 PM for me, that will give you a second wind in the afternoon and it'll mean you won't end the day collapse on the sofa. So I think it's great for improving interoception, it's good for allowing your body to downshift and relax instead of being in that kind of high tone sympathetic state all throughout the day. So it gives your body a break, and it just feels really good. Honestly, it's probably my most played practice of everything that I teach, just people listen to it every day. So I'll share that in the show notes as well.

**Lenny** (00:54:41):
And I imagine if you feel like you've built this emotional debt, this would be a really good exercise to start to do, is that right?

**Jonny Miller** (00:54:49):
Yeah, it is fantastic. I mean, there's some people who struggle with having enough energy to kind of get out of bed and function. But again, I imagine listeners to your show, people that live in Silicon Valley, their challenge is the downshifting without external substances. And so NSDR is a really great way of strengthening that ventral vagal tone, which is our body's capacity to go from on kind of go, go, go to then relaxing. There's a quote from Kevin Kelly that I interviewed recently, and he said, "If you have a great work ethic that needs to be matched with a great rest ethic." And I think that kind of piece of actually training our capacity to downshift after stress is just completely missing from most people's playbooks.

**Lenny** (00:55:38):
I think with a lot of the sort of advice, if you listen, Tim Ferriss and Huberman and everyone's got this stuff you should be doing every day list and it ends up being so long and there's so many things to do, cold plunge, sauna. What is it that you practice or come back to slash what would you recommend people try to do daily that is most impactful of all this stuff we've talked about?

**Jonny Miller** (00:56:05):
First experiment with a bunch of different practices and see which you enjoy and notice how you feel before and then how you feel afterwards. That's kind of the key because once you know that it feels good, you're not going to have to force yourself or motivate yourself to do it. You'll just do it naturally because you know you'll feel great afterwards. I would recommend starting really simple, so starting with the 4, 4, 8 breathing or humming, doing that in the morning for just two minutes, two minutes in the beginning is enough. And I would also recommend listening to the NSDR practice at least once or twice. If you work from home, it's pretty easy after a lunch break, something like that could also be in the evening when you get home as well. Some people use it to help fall asleep.

And then the final thing that I would recommend is if you have the resources and you have access, finding a somatic practitioner or somatic therapist is so [inaudible 00:57:03]. I mean, I emerged a completely different human on the other side of the 200 breathwork journeys. I have a different experience of life basically released so much time. Even my voice sounds different. If you listen to the podcast episodes I recorded four or five years ago, my voice is higher pitched. It just sounds different. It has a different resonant quality to it.

**Lenny** (00:57:27):
Wow. Okay, awesome. So you've kind of summarized, I was going to try to summarize all the advice you've given, but if you were to do the bare minimum next steps based on this advice, try this 4, 4, 8/3, 3, 6/2, 2, 4. Does 2, 2, 4 work too if you just go real fast I guess?

**Jonny Miller** (00:57:28):
Yeah.

**Lenny** (00:57:45):
Yeah.

**Jonny Miller** (00:57:46):
Okay.

**Lenny** (00:57:46):
Okay, perfect. Okay, so do that for a couple mornings. See how that does try this NSDR practice. We'll link to a recording of how to do that and then was there something else you recommended? Oh, somatic worker, basically maybe a therapist, maybe not someone that helps you with your body.

**Jonny Miller** (00:58:06):
Yeah, and I'd add in the eight practice for even 15 seconds before the breathing in the morning and after, just so that you notice the difference. And if you do the NSDR, that is basically a 15-minute interoception practice as well. So you're kind of getting two birds with one stone with that practice.

**Lenny** (00:58:24):
What's your perspective on meditation? Does that fit into this? Do you find the NSDR replaces the need for meditation?

**Jonny Miller** (00:58:29):
That is a big topic. I am an avid meditator as what I've done many 10 day silent retreats. I was in a dark room for 10 days.

**Lenny** (00:58:40):
Wow.

**Jonny Miller** (00:58:41):
With meditation, I think it really depends on what you are training. It's like saying what's your opinion on exercise? Well, are you training mobility or stamina or strength? It's the same with meditation. You could be training loving kindness. You could be training your focus and attention. You could be training spacious awareness. So I'm a big fan of embodied meditation practices. So this is often the classic vipassana body scan is a good example. Again, I mean that's basically interoceptive practice where you are just moving your attention through different parts of your body over and over and over again for days on end.

**Jonny Miller** (00:59:17):
In the case of vipassana retreat, meditation is helpful for the specific skill of increasing the psychological space between a stimulus and your response. So if you have some degree of meditation practice instead of getting wrapped up in a certain emotion or we're even believing a certain thought pattern, there's usually an ability to kind of step back a little bit and see if what it's, so there definitely is a place for meditation. But my viewpoint is that we've kind of over-indexed for mindfulness and meditation in over the last 20 years. There's so many apps, there's so there's much talk about it and we've completely forgotten the body-based approaches. So I'm not saying don't meditate. I think meditation for sure has its place, especially if your goal is more of the traditional waking up and seeing through the nature of the self, that's a different kind of path in my opinion. But if you're looking to function more effectively and be more in tune with your body, then there's a whole different category of practices in this bottom up variety that we've touched on today.

**Lenny** (01:00:27):
On the topic of bottom up, I imagine you're a big fan of this book that everyone always talks about, The Body Keeps Score, I think it's called. Would you recommend that book? Is it connected in a large part to the stuff you talk about? What do you think of that book specifically? Because I hear about it all with him.

**Jonny Miller** (01:00:41):
Yeah, it's a good book. It's by Bessal van der Kolk and there's another writer I think Peter Levine says, "The issues are in the tissues." Is basically the concept. And this is the idea that we have these incomplete mobilization reflexes that are stored in our body and often held as tension. It's not strictly true to say that the trauma is in the body. It is actually a cortical map in the brain which kind of tracks these things. But for kind of practical purposes, it looks and feels as if there is stored grief in my right hip or anger in my solar plexus, that's the experience that we have. And the more that you become aware of these sensations and start to develop emotional fluidity essentially, the more that tension is released and the less reactive you become and the more emotional debt you pay off. So I think The Body Keeps The Score, I think a more accurate way would be the body is the scorecard in a way. I think that's kind a slight reframe. And if you're interested in this, the work of Peter Levine, Waking the Tiger is the seminal book on this mobilization reflex stuff that I'm describing.

**Lenny** (01:01:51):
I never need that part of it. And basically it's actually kept in the brain, but it comes across as somewhere in the body.

**Jonny Miller** (01:01:57):
Yeah, exactly.

**Lenny** (01:01:58):
Fascinating. I want to spend a little time on a new segment that we have in this podcast that I call Contrarian Corner. So let's visit Contrarian Corner, I feel like you'll have something interesting here. So the question is there something that you have a very contrarian opinion about, something that you believe that a lot of other people really don't believe?

**Jonny Miller** (01:02:17):
We've already touched on I'm not a big fan of talk based meditation, which will probably get me some comments I would imagine. I'd say the other one that's worth mentioning is I think that we vastly underestimate the impact of burnout, particularly from a bottom line perspective. There was a research report that I did a couple of years ago where we interviewed these leaders and they'd all experienced burnout of some degree. And we said, if you were to estimate how much this costs your startup or business, what would you say? And the median response was a hundred thousand dollars, which I imagine is more than most people would think.

**Jonny Miller** (01:02:57):
And most people aren't actively investing in burnout insurance. Like it's not something that's on many people's radar besides meditation practices and things like that. And I think part of the reason that the cost is higher is because there are these second and third order consequences of talent attrition, of opportunity costs, lost productivity, you lose great leaders, make shitty decisions in the run up to the burnout itself. There's also this idea of emotional contagion, which there's some research from Wharton I believe, and they show that the leader or the CEO has a disproportionate impact or their emotional state has a disproportionate impact on the people in their team. So something I'd like to say is the nervous system of an organization is a reflection of the nervous system of the CEO. And so I think that's just something which I would like to see talked about more.

**Lenny** (01:03:53):
Just on this idea of burnout, I don't think you're saying don't work really hard If you want to work really hard, it's that you need to maintain your body and mind and nervous system if you're working insanely hard. If you're working long hours, feel free, but just know there's debt you're building up and you need to be doing things to pay off that debt as you're doing that.

**Jonny Miller** (01:04:11):
Precisely. It is very much like building technical debt in the early days of a startup. It's worth doing, but just do it intentionally. Know that you're doing that and that. So let's say you work really hard for eight months, you give yourself a month or two off to really downshift. And it's also really worth building that nervous system capacity. It's great to be able to push it really hard and focus and then combine it with that rest ethic as well. So do NSDRs, kind of find a way to downshift so that way of working can be sustainable.

**Lenny** (01:04:44):
Jonny, we reached our very exciting lightning round. Are you ready?

**Jonny Miller** (01:04:48):
Let's do it.

**Lenny** (01:04:49):
First question, what are two or three books that you've recommended most to other people?

**Jonny Miller** (01:04:53):
I actually had a sense this question was coming and I have the books with me here. The first book is Constellations by David White. This is the book that I've gifted most to friends, I think more than any other book. And he basically has 52 definitions of words like ambition is I think the first word. And his writing, it just blows me away. I open this to a random page, read the definition, and it's probably affected me more than any other book. So that's one that I love. 15 Commitments of Conscious Leadership, which is I imagine has come up before in your podcast. This is by Jim Dethmer and Diana Chapman. They have the Conscious Leadership Group. And this is basically, in my opinion, it's the best leadership book that I've come across and it combines practicality with a lot of great theory. So this is awesome. And then finally, this is a bit out there, but Recapture the Rapture by Jamie Wheal, big fan of Jamie's work, Jamie's writing. This is kind of three books in one. The beginning is addressing the meta-crisis and a lot of the craziness that we're seeing in the world. The second chapter is very related to what we've been talking about, he calls it Hedonic Engineering and it's basically practices for shifting your state of consciousness. And the third is Ethical Cult Building, which I'll leave that there. [inaudible 01:06:22].

**Lenny** (01:06:22):
Do you have a favorite recent movie or TV show you really enjoyed?

**Jonny Miller** (01:06:28):
My wife and I love animations and we saw Kubo and the Two Strings recently, which was fantastic. Just so, so great. That and also Wolf Walkers, which was an Apple TV series. Yeah, those have been my two favorite movies I've seen recently.

**Lenny** (01:06:46):
If you like animated content, check out the Scavengers Reign on HBO. I've mentioned it on this podcast before, but it's incredible. It's a TV show on HBO. So I usually ask, do you have a favorite question you like to ask candidates you're interviewing? But I know you coach people, so to kind of turn this question a little bit around, do you have a favorite question you like to ask executive coaching clients that you work with?

**Jonny Miller** (01:07:08):
I stole this question from a guy Jerry Colonna who's here in Boulder, and the question is amazing. It is so good. It's basically, how are you complicit in creating the conditions that you say you don't want? And so the word complicit there is key because it's not saying in what ways is it your fault, but it's like in what ways were you complicit in creating the conditions for anxiety, for building up emotional debt? And just the question kind of opens up the door to ways in which you are an active participant in creating these challenges in your life. And it's a really rich journal question or a question to explore with a friend, co-founder colleague.

**Lenny** (01:07:53):
I remember him sharing that on the Tim Ferriss podcast many years ago and it stuck with me and I often think of it, but I never am complicit of anything that goes wrong. It's never my fault. He has nothing on me. Just kidding.

**Jonny Miller** (01:08:06):
Excellent.

**Lenny** (01:08:08):
Do you have a favorite product you've recently discovered that you really like?

**Jonny Miller** (01:08:11):
One is these blue blocking glasses. These are raw optics, blue blocker glasses. They block out a hundred percent of blue light and they are a lifesaver if I'm ever going out of the house basically after dark, I'll wear these to drive. I'll wear these to even dinners with friends sometimes. And it basically means that I'm able to then sleep well that evening. So that's one.

**Jonny Miller** (01:08:38):
And then the other thing I'll briefly share, this came through the other day, you mentioned the vagus nerve earlier and that device, I have three devices here that are all vagus nerve stimulation devices. This one is called Neuro Sim. This one I believe is Pulsetto, and I think this is a Apollo Strap. I haven't used them that much yet, but they basically work by sending low level electrical stimulation directly to your vagus nerve. So this clips on your ear because the vagus nerve goes through the right side of the neck. Same with Pulsetto. And I'm really curious to compare the effect of these versus say breathwork, humming, the other body-based practices. Obviously, you can do both at the same time, but I am just interested in playing. So I wouldn't recommend them yet, but I think it's interesting that they exist.

**Lenny** (01:09:29):
How cool would that be? We just put these things on, we don't have to do anything else. We just get up, slap on our device and life is amazing. Don't have to meditate, don't have to breathe in a different way. I'm going to need to do this while I'm on the podcast just wear all these devices, see how that goes. Awesome. Well, I guess somehow report back to us how these go because that feels really great. Next question, do you have a favorite life motto that you often come back to share with friends, either in work or in life?

**Jonny Miller** (01:10:00):
State over story would be one which we've touched on.

**Lenny** (01:10:02):
State over story.

**Jonny Miller** (01:10:04):
And then I think the other one, which I think about often is I like to say, "Make generous assumptions." And by that I mean in any situation, what is the most generous story that I can tell of this person, of this situation? Not kind of naively fabricating something, but usually there's a spectrum of I can assume that they're a bad person and they did this thing out of spite, or maybe they had a bad day, maybe they have a lot of emotional debt. There's there's many stories that can be told. And I usually try to have a practice of telling the most generous story that I can.

**Lenny** (01:10:47):
I like that a lot. Another way of describing that is just assume good intentions, which I often think about.

**Jonny Miller** (01:10:53):
Exactly.

**Lenny** (01:10:54):
Final question. You seem extremely calm always, and very centered and stable. What still gets you rilled up and unsettled, and what do you do when that happens?

**Jonny Miller** (01:11:07):
Well, I was nervous before this podcast, so I did some breathing practices and some stretching and some humming before jumping on here. I still at times notice ways in which I'm conflict avoidant. I've been working on it actively for a while, but there's a part of me that can sometimes avoid conflict. And so I've actually noticed how there's a relationship between that and having a healthy relationship to anger. So basically giving myself permission to express frustration, not at someone, but just allow it to be there. And then from that place set better boundaries with my time with what I'm doing, saying no to certain things. I think that's the practice that's most alive for me right now.

**Lenny** (01:11:53):
Jonny, you are awesome. Two final questions. Where can folks find you online and explore the things that you offer? I think you teach a course, whatever else you offer, talk about that and then how can listeners be useful to you?

**Jonny Miller** (01:12:06):
Yeah, well, this has been so much fun. I am very active on Twitter or X. My handle is Jonny Miller. It's J-O-N-N-Y-M-1-L-L-E-R. And yeah, if this was interesting or listeners would like to dive deeper, I teach a course. Our next cohort is running in the spring, the end of March. Applications are now open, and the website is nsmastery.com/lenny. I've created a custom page and there's a $250 juicy discount for listeners if they want to sign up.

**Lenny** (01:12:39):
I got to sign up for this myself. I didn't know you're going to do that. That's awesome. And NS Mastery stands for Nervous System Mastery.

**Jonny Miller** (01:12:47):
Exactly.

**Lenny** (01:12:48):
Amazing. Anything else? And then the second question of how listeners can be useful to you.

**Jonny Miller** (01:12:52):
Well, firstly, if any of this resonates, I'd love to hear from you on Twitter or email me as well. I can pass over my email and I would just love it if you experiment with this stuff. I love this idea of just being a scientist of life. So if anything that we've talked about resonates or any of the practices you want to try, just go out and try it and see how it feels and then tell me about it. That would be the greatest gift I think.

**Lenny** (01:13:23):
And the best way to tell you about it is tweet at you or is there something else?

**Jonny Miller** (01:13:26):
Tweet at me or my email is jonny@curioushumans.com. So feel free to email me as well.

**Lenny** (01:13:32):
All right, I'm going to use all these things. Jonny, thank you so much for being here. You're awesome. I am excited for the show notes we're going to have to give people actual tools to use to become less anxious and nervous in their work and life. Thank you again for being here.

**Jonny Miller** (01:13:46):
Amazing. Thanks so much, Lenny. This was super fun.

**Lenny** (01:13:48):
Same for me. Bye everyone.

**Lenny** (01:13:51):
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.

---

## [9/19] Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition | Megan Cook (head of product, Jira)

**Megan Cook** (00:00:00):
What we put into place is something we call Fight Club. I'll probably get in trouble for talking about Fight Club. The first rule is you don't talk about Fight Club. But it's 30 minutes every week, and it's just for myself, my engineering, and my design leader; and we get together, and we know that we're going there to have a conflict.

**Megan Cook** (00:00:18):
I think often when there's difficult conversations, or those conflicts come up, you can put them off until they become much bigger. Or if somebody is conflict adverse, they can try to avoid having it at all. But by having a specific slot of time in your week for something like that, then you're sort of in that mindset. You know you're going in there to solve a hard problem. You know that there's going to be a disagreement. And it makes it much better. I think the relationship we all have is so much better because we get on top of these things early.

**Lenny** (00:00:51):
Today, my guest is Megan Cook. Megan is head of product for Jira, which is used by 75% of Fortune 500 companies, 125,000 customers globally, and is by far the most popular project management tool in the world.

**Lenny** (00:01:06):
Megan has been at Atlassian for just under 11 years. Prior to Atlassian, Megan was an analyst, a developer, and an agile coach.

**Megan Cook** (00:03:57):
Thanks so much, Lenny. I am a big fan of your podcast, and I am excited to be here.

**Lenny** (00:04:02):
I have a lot of things I want to chat about. I've heard about many things that you're extremely good at as a leader, as a product leader, and so I'm just going to poke around a bunch of different areas. I wanted to start with something that I hear you're just a big advocate of and really good at, which is creating space for play on teams and also just creating a lot of psychological safety, something that you find really important that helps your teams be as successful as they are.

**Lenny** (00:04:29):
Can you just talk about why this is important to you, why creating play and psychological safety are so important to you, and then just how you do this, maybe an example or two of how you actually apply this on your teams?

**Megan Cook** (00:04:40):
Yeah, absolutely. I think especially recently in the tech industry, it almost feels like we're going through a bit of a wake-up call at the moment. We were in this time of plenty, and everyone was hiring like crazy, and then COVID hit and suddenly people's behaviors had to really change. People couldn't travel; they had to work from home. There's a whole bunch of industries that got highly impacted by that, and it created this time of high ambiguity.

**Megan Cook** (00:05:08):
Before that, or to the start of that, I was noticing within my team just some little indicators where people weren't all comfortable to speak up when we'd had really open discussions with the most junior person, where the most senior person were happy to talk about anything. There was more anonymity in feedback. Every time things were coming to leadership to give feedback on, it was just sort of painfully polished. And I think once it gets to that level, that's a really bad time to give feedback, because it probably means that a whole ton of work has gone into it, and you might waste a whole bunch of work if you have to correct direction or make significant changes.

**Megan Cook** (00:05:53):
And so, I was looking at my team and thinking, "Yeah, something doesn't feel quite right here." And then I went to this leadership outside, and one of the speakers there was Ben Crowe. He's an expert in having the right mindset. So he works with Olympic gold medalists, and Ash Barty is another one, who's a tennis player. She's the number one tennis player in the entire world. So these athletes who have to really perform under a lot of pressure, in front of a lot of people. And he talked about how to be in that state of flow, where everything is going really well and new ideas are coming and you're making progress, you've got great momentum. And he talked about how to be in that flow state. There needs to be this sense of play and that things are fun. Your mind's open to new ideas, you feel really present. You're not stressing out and thinking about a ton of other different things.

**Megan Cook** (00:06:52):
And it's funny because when I thought about play where my mind went to the opposite of play is work. We often hear work and play as opposites together, but his point was actually that the opposite of play is fear. And I realized I think that's what I was seeing a lot of in my team and that's why the ideas were getting more incremental. So took that decision and went, okay, we need to look at psychological safety in that team or we're never going to get to some of these bigger, bolder, more innovative ideas. And so brought my group, product managers together, and we sat around and discussed it and all together came up with some ideas that we've implemented since then, which has had a really good impact. So I'll give you a couple.

**Lenny** (00:07:40):
Yeah, please.

**Megan Cook** (00:07:40):
One of the first ones was my team of PMs is big enough now where not everyone necessarily gets to know everyone else, and when you don't have that relationship, it can feel a little scary. You don't have that trust that you understand how people are going to respond to you and you're not sure about reaching out. So we divided the team into these smaller groups for peer feedback groups and the idea is that they meet every two weeks or so, somebody brings something that's in a pretty rough draft that they want to get reviewed and then everyone's expected to give feedback. And because we've got people in there who are different leadership levels, it's a really good opportunity to model the kind of feedback that's helpful and the culture there is one of everyone lifting that person up to make their work stronger.

**Megan Cook** (00:08:28):
So people can get in there, they can show that you can show work that's really in the early stages and feel comfortable with that. They can see that getting feedback can actually be really positive and they can see how all of these people together, they can rely on them and forge those relationships so they can rely on more people to help them out.

**Lenny** (00:08:47):
This is so interesting and it's such a good idea and it's such a simple and good idea and I'm surprised I haven't heard of people doing this before. Basically you pair up PMs, IC PMs and maybe managers too, to give each other feedback. And is the feedback on one-pagers and PRDs and strategy docs and things like that? What sort of documents are they giving feedback on?

**Megan Cook** (00:09:11):
So really, it can be anything. It can be here's a new experience, [inaudible 00:09:15] launching, here's a new strategy. I've taken my own strategies in there and gotten excellent feedback, surprising feedback from the team. Can be a new experiment that people think of running and anything to do with the craft.

**Lenny** (00:09:29):
And I think as you kind of implied, one of the powers of this approach is it's a small team, so it's less stressful and there's no... You're not in the room often too. I guess you are sometimes as you just said, but usually it's like peers and they could be a little more open and less worried about looking back.

**Megan Cook** (00:09:46):
Yeah, absolutely. And I think a lot of it is just building that muscle. You might go through an experience once every quarter or once every six months and that can feel really stressful, but if you're doing it again and again, you get used to it. You get used to what to expect, you get a bit more practice, it can feel much more comfortable.

**Lenny** (00:10:04):
That's awesome. So it's just simple and powerful idea. It's kind of like everyone's always suggesting getting a mentor, getting a coach as a PM and those are hard to find. And this is just a little informal. It's almost like a little peer group board of directors for your work. We talk about that on the podcast sometimes. So anyway, that's awesome. Really good idea and something anyone can do.

**Megan Cook** (00:10:24):
Yeah, thank you.

**Lenny** (00:10:26):
Great. Okay, you have a second idea?

**Megan Cook** (00:10:29):
Yeah. One of the other things we do is we get everyone together just like every six months. So all of the product managers get together in the same place and the idea is to have a bit of an onsite. Now we start off with just doing something fun because everybody... As you might know, Atlassian is a remote organization, so everybody works remote all the time. They can work from anywhere. And so people often, they're not used to necessarily being all together in the same place. It can take a little while to warm up. And then after that we talk about strategy. We do workshops on different elements of craft boosting that craft together. And so a similar kind of thing. People get to build relationships together. They get to see all these different ideas bouncing around which can help uplift their own ideas and help them be more innovative.

**Megan Cook** (00:11:23):
In this last one, I actually had some senior leaders from all over the organization come and share their stories of failure. So just to get everyone used to that idea that it's okay to fail and actually if the learnings are really good, maybe it should even be celebrated and it's not something to be scared of. And taking the big swing isn't a bad thing. It can be a really powerful way to learn as well.

**Lenny** (00:11:50):
I love that. We've been talking about failure a lot on this podcast, so we're super aligned with the power of that. And so just to be clear, so what you do there, is it the entire product team of Atlassian or is it just your team in this every six month?

**Megan Cook** (00:12:04):
It's just my team and then we pull in other product managers that we work closely with as well.

**Lenny** (00:12:09):
And then you fly them all to Australia, I imagine?

**Megan Cook** (00:12:13):
Yeah, all to Sydney

**Lenny** (00:12:15):
To Sydney. Amazing. Okay. And I think, so the key there is it's not just like go meet each other, it's training almost on different skill sets, helping people level up in say craft or I don't know, communication or writing or something like that. And then who teaches these things? Is it like individual team members or you bring someone in?

**Megan Cook** (00:12:36):
We have a real mix actually. So yeah, we'll bring in outside experts or we'll get... There's a lot of knowledge and a lot of skill within the team itself. So you'll have different product managers who have different strengths. We have totally different teams. So someone on a growth team, for example, might want to teach everyone about how to create great hypotheses or we'll get someone external from the team, but internal to Atlassian who has those skills who can come in.

**Lenny** (00:13:04):
I love that also gives those PMs a chance to, one, learn the skill better themselves because they're teaching it, and also just teach and present in public speaking and all that stuff. There's all these other benefits to doing that sort of thing.

**Megan Cook** (00:13:16):
Yeah, absolutely. And I think as a product leader, it's really important to model the behavior you want to see from your teams, whether that's getting out there teaching, presenting, explaining different concepts, explaining the business or just being vulnerable and talking about when things haven't worked out.

**Lenny** (00:13:34):
When we started this question, you talked about how there was kind of the shift at Atlassian where things started to feel more formal and people started to feel less open to sharing, being criticized in meetings. Just in case people might feel that might be happening in their company, do you remember roughly what size that started to happen at or signs of like, "I'm noticing people are sharing less or being more worried about talking in big meetings"?

**Megan Cook** (00:14:00):
Probably when we got into really different streams of work that were happening where people didn't have as much of a reason to interact with each other. So I think that was probably around, even around 15 we started to see a little bit of that.

**Lenny** (00:14:19):
15 product managers?

**Megan Cook** (00:14:20):
Yeah.

**Lenny** (00:14:21):
Got it. Cool. That's a good stat.

**Megan Cook** (00:14:24):
Yeah, you know what, I'll give one more thing that we do. So we've just started trying something new called the $10 game for priorities. And so that's where I think people might have played the $10 game for your priorities when it comes to a strategy or something like that. We started trying it out with your individual priorities. So you and your manager might come in and you can list out all of your priorities and then show you through just dividing up $10 where you're spending all of your time. And I've done this with people and we've sort of gotten down to like, "I'm putting 10 cents here this week." And I'm like, "Oh, what is that? 20 minutes, 30 minutes spending. I didn't think that's actually moving right." And so it's been great to see where people are overloaded and alignment on do my priorities stack up, but also am I spending the time on the most important things that could be moving the business forward?

**Lenny** (00:15:24):
Awesome. Okay. So you mentioned that y'all are remote. Has it been remote from the beginning?

**Megan Cook** (00:15:31):
No, not from the beginning. Actually when COVID hit, I think that was the big one.

**Lenny** (00:15:35):
Okay, okay, got it. That makes sense. So a lot of companies are moving to remote work, trying to figure out how to work remotely. It seems like it's working really well for Atlassian, at least from what I can see. Is there any advice or any big lessons or tips or tricks you've learned that you could share for how to be effective working remotely, especially as a product manager? It feels like as a PM, the job has gotten so much harder having to be remote, and so yeah, I'm curious if you just have any advice you could share for people trying to make this work for their company or for themselves?

**Megan Cook** (00:16:04):
Yeah, absolutely. It's a really good question because it's not easy and we definitely went through a whole bunch of pitfalls at the beginning, but we're really firm believers that you don't need to be in the office to build world-class products. So we call our product team anywhere, and this means that anyone Atlassian can choose where they want to work every day. We think it's a bit more human, that flexibility shouldn't be a perk, that it fundamentally can change people's lives depending on what else they have on outside of work. And so we think less about where do you work and we think more about how to be productive and effective in your work.

**Megan Cook** (00:16:44):
To your point, we started doing this right when COVID hit, so it's been about three years and actually we just released a guide with our key learnings from that. It's all about a thousand days of remote work, which folks can go and find on our Work Life blog under research@atlassian.com if they want to dive in there more. But I can give you a couple of tips from that and what we found from some of our research.

**Lenny** (00:17:10):
Yeah. And we'll link to that doc in the show notes.

**Megan Cook** (00:17:12):
Okay, great. The first one is just making time for connection. So that human connection is definitely built in person, but what we found is that it doesn't have to be something that happens every single day. So we found the connection and productivity, they both get boosted by about 30% when you bring people together but intentionally, and it lasts them months. So we found that you can do it on average like three times a year. And so that's why my PM team are getting together every six months. But in addition to that, we get the entire team together every other six months. So we end up all getting together every four times a year.

**Megan Cook** (00:17:53):
So every other six months, what we do is we get all of the engineers, designers, everybody who's working together. We book out entire floors in the office and then for an entire week we're just there. And for some of it we're just working together as you normally would, but at desks and just having those little water cooler type conversations. It builds the relationships again. Other times we're doing workshops, an important piece of work where it's easier to do when you're all in person and sometimes we're just having fun together. We call that a bit of a festival.

**Lenny** (00:18:27):
You mentioned that you measured some kind of productivity improvement. Do you happen to know how they measure that because that is really interesting?

**Megan Cook** (00:18:35):
Oh, that's a good question. I don't, but I can get that for you.

**Lenny** (00:18:40):
That'd be cool to know. So I think we'll keep this in the podcast episode and then if there's anything in the show notes that we link to that talks about how they measure that, that'd be really interesting because that's just a cool stat to have anyway, for all kinds of other things. I'm curious how they measure that.

**Megan Cook** (00:18:54):
Yeah, absolutely.

**Lenny** (00:18:56):
Okay, cool. Any other tips?

**Megan Cook** (00:18:58):
I think the second one is to be really intentional. I mentioned that we went through a few stumbling blocks at the start. One of those was immediately, everyone sort of filled up everybody's calendar with all of these meetings straight away. It was almost as if Lenny, if you and I were working together, I used to be able to just poke my head around my monitor and ask you something. And people were afraid that now that I can't do that, how do I get those answers? So I need more time with everybody and that definitely does not help productivity at all.

**Megan Cook** (00:19:33):
And so as PMs, we need time for creative work. We need that deep work time, and that doesn't happen when you've got all of these meetings with 30 minutes in between each of them. You need three to four hours to get that going, to get into that flow state. So my leadership team and I, we actually sync up our calendars, so we end up having these long stretches twice a week all at the same time. And so we all get a chance to do this deep work. It means we get less time for meetings, but it also means that if something comes up that's unexpected that we all need to work on together, then we've got that time there so we can be a bit more relaxed about it. We know we can get to it.

**Lenny** (00:20:14):
What time of the day is that meeting?

**Megan Cook** (00:20:16):
They're both at different times. So the first one's taking up one afternoon and the second one's taking up all of the time in the morning. Depending on what kind of person you are, one is going to see you better than the others. So we just went for one each.

**Lenny** (00:20:28):
I actually had the same thing just personally where I had these deep worked blocked times on Monday, Wednesday, and Friday. The title of the invite was, "If you book time during this, I'll slap you." And it really worked well. But I think you're talking about this other missing piece of remote work for PMs where you can't just walk by and ask an engineer, "Hey, how's it going?" Or ask a designer, "Oh, where are you at? Let me just take a peek at what you're working on." That stuff I think is really hard to replicate. And if your suggestion is block out this time for your leadership team to be able to check in with each other, is the idea there it's deep work time and don't bother anyone on the team or is it you can also just ping your end manager and like, "Hey, how's it going?"

**Megan Cook** (00:21:09):
The idea is that it's deep work time and it's your time to be protected to do that work. What I found that works really well, I think in the manager and report kind of relationship, so I have these really quick punchy one-on-ones with my reports every week. And then I make sure that I've got space in my calendar because something will come up where even if we had a longer one-on-one that might not cover it. They might just need an hour to run through something, there might be a really difficult strategy problem they've run into. And so they'll know that they can ping me for more time and I'll have that flex in my calendar for that.

**Lenny** (00:21:49):
Awesome. Any other tips along those lines?

**Megan Cook** (00:21:52):
Well, you probably noticed about blocking a bunch of deep work time is that you don't have as much time for meetings. So that meeting time becomes really precious. And what we do there is... I personally hate having status updates as a meeting. So I make it really clear that if we're having a meeting, this is to solve a problem. And if it's just a status update, that's fine, then I can read that asynchronously at a time that works for me. And so can everybody else in the team if they want to do that. Actually we use our own tool for this, which makes it really easy. So it's called Atlas and it lets you or the team put in status updates for a goal or a project regularly and then it'll bundle it all up into an email so you can quickly get across everything that you're interested in, which has been really helpful.

**Megan Cook** (00:22:40):
And then that just makes the documentation rigorous as well. So you document things and we use Confluence, but all of our decisions, strategies, kickoffs for projects, that's all really well documented piny starters. Or even if you're a year down the line and you're thinking, "Why didn't we come to that decision in the first place? What were our assumptions? What were our hypotheses?" It's easy to go back and take a look at that and be able to reflect.

I think the last thing is I work with people who are in the US, they're in Europe, they're all over the world. It's really hard to find a time that works for an Aussie, an American and a European to get together. Someone's waking up at 3:00 AM or something. So what's become a big part of how we work is actually audio and video recordings. I actually had someone reporting to me for a while who was in France and what we would do was record videos back and forth and they're quick. You can just use colloquial language, they're really casual, you don't have to wonder about someone's tone that comes across. So that's becoming almost like a completely new document type for us and it's been really important in remote work. You can put at the top of a document and explain the document, which is really nice. It's a big part of why we bought Loom.

**Lenny** (00:24:06):
I was just going to say that. It all makes sense.

**Megan Cook** (00:24:09):
Yeah, because it was just becoming such a big part of our life and it's just massively helpful.

**Lenny** (00:24:16):
Kind of along the same lines, being fully remote, it is harder to get buy-in on things you're working on I imagine. And something I hear you're great at is getting buy-in, especially getting buy-in on ideas and projects from executives. So I think things that make it extra challenging at Atlassian, there's two CEOs which I didn't know until recently. You're also all very remote and so maybe those two reasons make it extra hard. Plus it's just generally hard to get buy-in on projects that you're working on. What advice do you share with product leaders, PMs that come to you asking for advice on how to get better at getting buy-in for your ideas?

**Megan Cook** (00:24:56):
Yeah, this can be really hard to get right. I watch a lot of people struggle with this, and you're right, being fully remote can make it a bit more challenging. And then I think also you've got your cross-functional partners that you're working with as this tight-knit team and how do you form that relationship? But I'll start with just general buy-in.

**Megan Cook** (00:25:17):
Most of the time when people come to me and they want to ask how to get by-in, they've got a date in mind, they've got a particular meeting and they have this idea where they're going to crop this perfect proposal, they're going to present it, everyone's going to give them thumbs up and they win. And that's the wrong attitude I think even to start with to getting buy-in. It's more of a journey.

**Megan Cook** (00:25:40):
I'll give you an example where I was looking at how do people start their day in Jira and how do people get started in Jira? And we had this idea of we could craft more templates so that we could give people a better way to start with very different use cases when they came into the product. And this could change everything from even just the front homepage where they started all the way to what's happening in product. It would create this really nice flow.

**Megan Cook** (00:26:12):
Jira is also a platform as well as just Jira software the product. There's actually four different products built on top of it. So when you want to go and change something like that, you're actually changing it for all of these different products. It's not just the one. And so what was really important there was partnering with a whole bunch of different stakeholders. So every product that this could potentially negatively or positively impact, we went to very early with the idea and the proposal and we got their feedback and then we came to them and again and again as we developed it further. So as we got designs, as we got more data, as we tested things out with users, we kept coming back and we take their feedback on board.

**Megan Cook** (00:26:54):
And so I think creating those partnerships is really important. And also the same can be true at the executive level. So often you go into these meetings where you're giving a proposal and you're trying to get that final yes on the decision. You've got a lot of people in there with a lot of different angles that they can look at that problem and so much good experience to draw on. So your CTO is going to have a totally different way of looking at something and different concerns from your chief marketing officer to your head of design. They're all going to look at things differently and be thinking about it differently. And so if you know that you're going to be having a big impact in someone's space and you want to hear from them, it's good to set that meeting up early when you've got some clarity but it's not fully fleshed out and so that you can fold in some of their concerns because they'll have this much broader view. And that also creates people who will be an advocate for you once you get into that room, that final meeting.

**Megan Cook** (00:27:50):
So I think all of those in the lead up, there's a lot of lead up work to getting buy-in that makes sure that you have a good time in that meeting.

**Lenny** (00:28:00):
Just to maybe summarize so far, which you've shared, one is just... Basically it's lieu people in early, especially the person that it's going to impact most.

**Megan Cook** (00:28:08):
I think in addition to that is having that mindset of being open to not necessarily coming up with the right solution, it's more about solving for the problem or the opportunity. So you want to be clear about your hypotheses and what are your facts and what are the principles you're using to make a decision and just be open to not necessarily ending up with the solution you thought would be best.

**Lenny** (00:28:34):
I imagine most people think they are always in that state, "I am very open to feedback. I am totally open-minded, but really they're not." Is there anything that you think would either convince someone you're actually not as open-minded as you seem or any advice for how to come across as more open-minded? Or is there anything that you see... I see this all the time. People think they're listening, but they're not. You should change.

**Megan Cook** (00:28:56):
I think one way to force yourself into that situation is to be clear about the hypotheses you have and the facts. So I think often people can present as, "This is absolutely the case. This is what I know, and this is obviously the correct response to the situation." Where most of the time you've got a good set of data, you've got a good understanding with your knowledge of the space, but what is actually going to happen is a hypothesis. There's always going to be something you don't know and oftentimes you don't know until you ship it. That is absolutely the best test of whether or not what you thought was going to happen will actually happen.

**Megan Cook** (00:29:41):
And so I think when you come to the meeting going, okay, here's the top-back so we actually know, and here's the hypotheses and here's my plan to prove or disprove them, then you're exposing your idea for people to go, oh, here's more that I know about that hypotheses, or here's some data that you don't have or here's another way to think about it. I think people can feel like they're not going to be credible. That you have to come in, you have to come in confident, you have to come in knowing exactly what that solution is going to be. But I usually find that if you come in there open and you're exposed, you're thinking and where you could use some help on perspectives, that actually that builds more credibility because everyone knows that you are not going to have all the answers and you're not going to be able to see the future. And so that can really help in building people's trust in you and that you know what you're doing.

**Lenny** (00:30:34):
Is there an example of that that comes to mind to make it even more real of either someone on your team doing that or you doing that? Because I think it's still going to be hard for people to realize, "Hey, I'm not actually paying attention to anyone and I just want to convince them this idea is right. This is what we're doing. Just come on, get out of my way. Give me the okay."

**Megan Cook** (00:30:51):
An example from my past is there was this potential acquisition that we could have made, and I was really, really keen on it because it would mean adding a whole bunch of much needed capability really quickly to the product. And I just loved that momentum and I didn't see any other way that we could do this. I'd looked at a bunch of other options about building it in-house and it just didn't seem possible. And there were a few people that I needed to convince, my boss, but also the head of engineering for the area. And when I took it to them, what I learned was the head of engineering was able to pull a bunch of people from other areas within the company to come and bolster this effort and who had all of the knowledge that we needed. So what seemed like the impossible task, he actually had this extra knowledge to make possible.

**Megan Cook** (00:31:45):
And in the end, acquisition or not, that doesn't really matter. It's more about being able to get that value back to our customers. That's what we're solving for. And so it was really about coming back, not falling in love with that solution and that other company, it was just taking a step back and going, "Okay, well, really it's just what are we here to do? What's the real goal at the end of the day?"

**Lenny** (00:32:11):
Awesome. Okay. Is there anything else you wanted to share along these lines before I move on to a different topic?

**Megan Cook** (00:32:16):
The other thing I would say is that setting up the meeting when you finally get there can be really important as well. I often see people go in there and they've got a big document or a presentation or something and they just launch into it. They're really excited. But actually you want to take a step back and you want to be really clear on what are you looking for from that group. You can ask for the decision, you can ask for feedback, you can ask for... You can expose where you're not quite sure about something and you want them to be thinking about that angle in particular and helping test that hypothesis with what they know. And so setting that early, you can put that in people's heads as they read through your document or listen to the rest of the proposal.

**Megan Cook** (00:33:02):
Then I find it's really useful to have a narrative that just encompasses everything that you're going to talk about. So just really brief, what's the current situation, what has changed and what are the implications that you now want to... We mean we have a problem to solve and an opportunity that we can go after.

**Megan Cook** (00:33:21):
And the last thing is just making sure you've got your data. There's executives, there's people in the meeting. They're usually across a whole ton of stuff just hearing about... Maybe they've got 10 proposals a day and they're across all different areas in the business, and so they're not going to have the detail that you do. So being really thoughtful about what you bring, what are the key points that are going to help them understand the situation as clearly as possible. But then really knowing your data so that you can dive in more detail where they need it. And that also helps build your credibility and builds people's confidence in the plan to go ahead.

**Lenny** (00:34:05):
Would you mind just quickly summarizing these pieces of advice and then I was going to move on to another area of strength of yours that I hear?

**Megan Cook** (00:34:13):
Yeah, sure. So the first one is to find people who are affected negatively or positively or might have a really good point of view and partner with them as you develop the solution or the response to the current situation. And the second one is to come at it with this mindset of being open, of being really key on what is the core problem or the value that you want to deliver, and just being open to how you get there and things that you don't know which might adjust along the way. And the last one is just setting up the meeting walls. So coming in, making sure that it's very clear what you need. Do you need a decision or something like that? And making sure that you've got very good supporting data to build that credibility with your audience.

**Lenny** (00:35:03):
Love it. This is where the term or the cliche of product managers asking, "But what problem are we trying to solve," comes from. But it comes from a really important place of always focusing on let's all align on here's the problem we're solving. Because oftentimes as you chatted about, the biggest disagreements come from people just thinking they're solving different problems. And on that note, I have a Swag Store now, lennyswag.com, and we have stickers on there, a bunch of cliche PM terms including, "But what problem are we trying to solve?" And so I think that's... But it's rooted in, that's actually a really important question to ask. Sometimes you get annoying.

**Megan Cook** (00:35:38):
Yeah, that's such a good sticker to have front and center.

**Lenny** (00:35:42):
Just need that as a big sign. Maybe the sticker needs to be bigger.

**Megan Cook** (00:35:44):
Exactly.

**Lenny** (00:35:48):
**Megan Cook** (00:37:24):
I think that's a really good example actually, the CSAT example, because sometimes you can get caught up in let's add value, add value, add value to the product, but if the customer aren't satisfied with what you built, or in our case we found that one of the core reasons was the usability, it wasn't where it needed to be. Then we can't access that value anyway. It doesn't matter. And sometimes it can be hard to get investment for things like that because it's not like the shiny, exciting new thing. It's no, I want to work on the features we already have and improve those. So it was about two years ago, our chief experience officer, he cared really deeply about improving our CSAT scores and asked me to look into it. And this-

**Lenny** (00:38:12):
Briefly explain CSAT real quick. Some people may not be familiar with that term.

**Megan Cook** (00:38:17):
Oh yeah, yeah, absolutely. Of course. CSAT means customer satisfaction. So for us, we actually have a survey so that we can measure CSAT and it just asks customers to rate how satisfied they are with the product and then different aspects so we can see for different tasks that they need to perform or different aspects of it, like the reliability or the speed or the usability. How do customers feel about that?

**Lenny** (00:38:48):
We actually had a podcast episode recently Judd, where we talking about NPS and how much there's data showing it's not actually a great predictor of anything, and he's a big fan of CSAT instead. So you could almost think of it as little replacement for NPS in a lot of cases. And I'm sorry, pushed you off track. Keep going.

**Megan Cook** (00:39:05):
Yeah, no worries. So he cared really deeply about this, asked me to look into it. Even though this request was coming from the top, that doesn't mean that it gets any sort of funding. So we went through a couple of different steps to see what was worth investing in here. First of all, I mentioned we had that survey and so we had really rich feedback. So it's not just a rating, what we get, we get people talking about why they gave that rating and that can really help us zero in on what are the key aspects that's bringing this down. And we also had great conversations with our customers. It was the kinds of conversations that are really rich and really helpful, but so painful to listen to and go through because you're seeing somebody really struggle with something that you thought was going to bring them so much value.

**Megan Cook** (00:39:58):
And then we had a look at, well, what is this going to impact? And so logically it's what we found was that usability was one of the key reasons, like I said. And logically, if your product is hard to use in places, if some of the core actions are hard for people to do, then a new user to that product or a new customer is going to have a longer ramp up time. You've got a harder time showing them that there's value. And even for an existing customer that's using your product really well, when they bring on a new user, that user might have a really hard time getting up to speed and using it and it just completely slows them down. So from a business point of view, it can impact your new customer acquisition as well as your ability to expand. So there was some good revenue connections in there as well.

**Megan Cook** (00:40:52):
What I also found was that we have a lot of dependencies. So we've got all of these platform teams and a lot of the improvements that would be really good to make to sort out this problem depended on many, many teams around Atlassian. And they all had different goals and other products that they had to serve too. I don't know if you've ever tried to align three or four different roadmaps so that the timing is just right to get some improvement through, but it's basically impossible. There was no way that was going to happen. But we did find that they were really passionate about this area and improving usability. So we worked together to find a low cost way for those teams to help us make the changes that we need to, but they didn't have to bear the brunt of all the development costs.

**Megan Cook** (00:41:39):
So each of those teams flipped forward, we call them a shepherd, so that as our developers came in and made changes in the code base that this shepherd would make sure that they weren't causing any issues and we're doing reviews and reviews of designs and things like that. And so getting that buy-in, finding the data to support the reason why this was important. And then we constructed the roadmap so that we found this sort of a low cost, very cheap way to have some impactful change early on. I think that was really, really important. And so we put together just some of the designs for what the experiences were going to look like.

**Megan Cook** (00:42:24):
So our head of design, Charlie Sutton at the moment has this great mantra of show don't tell. And in this case, it was just at the core of getting people excited because you could show the initial experience, you could show the pain, you could bring in a video of the customer trying to use it and what they thought of it. And that just really brought that emotional aspect to it. It helped get people on board on the issue, the new experience, which is just far and away molds better, might cut out like 20 clicks or whatever. And so all that worked together to get the investment that we needed.

**Megan Cook** (00:43:04):
I think the last thing that was useful there actually is that we started pretty small too. So I think if you have a hypothesis and you can start small, you can get that investment more easily, you can show success, you can always build on that in the future to get more and more. But in this case, we got about 40 people to come and join onto this. And then as we shipped things, we just made sure that it kept being quite small. And so we got that momentum really quickly. We kept with regular updates, we kept up the excitement about what the team was doing.

**Megan Cook** (00:43:38):
At one stage, the team picked out something that was pretty impactful throughout the whole thing. So that was dark mode. That took a lot of coordination around the whole company to make that thing happen. But it was well overdue, we loved it. And then the feedback that we got as well really helps with that. Actually just yesterday, I saw some feedback on one of the changes we'd made recently, and this customer said it was the best quality of life improvement they've seen in a long time, which just the way that's phrased even, that gets you excited about the impact that you're having on that person.

**Lenny** (00:44:20):
And this was the CSAT work or the dark mode?

**Megan Cook** (00:44:24):
This was CSAT work. This was improving one of the processes.

**Lenny** (00:44:28):
Okay, cool. That's amazing. There's a lot of stuff I love about this story. One is just the power of just empowering yourself to do things that you believe need to be done. There's a lot of PMs and just people in general that just assume they don't have any power and the square peg they're in is just all they're going to be able to do and nobody's going to allow them to do things that they believe are important and no one else agrees with. So I think there's just a lot of power in just understanding that you have more power and leverage and agency than you probably think you do, but then you also have to do it well. So I took a bunch of notes as you were talking of the things that I think are core to getting stuff like this done, just a scrappy project that you're kind of doing on your own without a lot of buy-in from the top initially.

**Lenny** (00:45:14):
So I want to stay small. Two is make it visual and visceral so you can like, "Oh wow, I could see this being amazing," and getting people excited as you go. Making it really easy for people I think is a really interesting takeaway there. Just like, "We did all the work for you already for these other teams, it's going to be so easy. It's not going to be a lot of work for you." And then showed the data like, "Here's what we've gotten from CSAT so far, here's the impact you'll probably get from it. Here's how much work it'll take." Show actual data. And then keep it scrappy. It feels like a lot of this is just like stay small, keep it scrappy, don't ask for a lot of resources initially and just kind of show momentum.

**Megan Cook** (00:45:50):
I think that's really important. When you keep it scrappy and small in the beginning, it doesn't feel like it's as big of a bet, but that gives you the opportunity to really prove that the direction that you're going in could pay off. And so it's sort of like this little inroad to getting more investment.

**Lenny** (00:46:07):
Awesome. Okay. I want to move to a different topic around Atlassian as a company, but is there anything else you wanted to share along those lines before we do that?

**Megan Cook** (00:46:15):
No, let's go for it.

**Lenny** (00:46:17):
Okay. One of the most interesting things about Atlassian to me is it's a great example of a company that's been able to launch new product lines. This is the dream of every software company business in general is you start with one product that gets to a certain point and then you hit some kind of plateau, and then you add an additional business product line, and then you add more and more. Somewhere around Atlassian's 15 products. Is that an accurate number?

**Megan Cook** (00:46:43):
Yeah, that's right. Yeah, we are up to 15. Yes.

**Lenny** (00:46:45):
Jesus Christ. Amazing. So this is very rare and the dream of many companies. And so I'm just curious what it is you think Atlassian has done so right to have so many successful individual products?

**Megan Cook** (00:46:59):
You know what, it's not like we added the first product and got it just right way off the bat. So yeah, 15, we've had a lot of shots at this, so I might talk about two examples. I think the first one, if I think about Jira software, it started just as a really humble bug tracker. That was it. There wasn't as much to it, and then it sort of weathered these massive changes in how people build software. So it launched in 2003. And if I remember correctly, just to date this, the mobile phone that was most popular at the time was the Nokia 6100. I don't know if you ever had one of those.

**Lenny** (00:47:41):
I don't remember what that specific one was, but I'm picturing a Nokia phone. It's like a little small brick.

**Megan Cook** (00:47:47):
Yeah, it was my mother-in-law's favorite phone. It took us forever to get her off that onto something better. But there's a lot that's changed since that time. There's been agile, there's been cloud. And what we saw recently was more in the expansion of software teams. So they used to be extremely developer centric. And I think most people when they think about Jira software, they think, oh, that must be, well, 80% developers that are using it. But actually it's more like 50% or maybe just shy of 50% are developers. And the rest is this huge mix of support in operations, in sales and marketing, finance, design, HR, legal, just this massive mix of everybody, all the roles you could think of in a company basically that get in there and make work happen.

**Megan Cook** (00:48:36):
And so what we saw years ago was, well, software teams aren't just developers anymore. And we saw this in our teams as well, but we saw that these other teams, the finance, the marketing teams, even design teams were sort of cobbling together their own solutions. So Jira software is incredibly flexible, which is a massive pro of it. That these teams were seeing software teams get more effective at the way they were getting work done and collaborating better. And they wanted that same benefit and they started using Jira, but we hadn't set it up well for them at all. So it was quite difficult for them to do that. But the positive was that there was this really good signal from our users that they were looking for more from us, and we knew that your marketing team is going to work differently from your developer team. That's how it should be. And so we started Jira work management to be more focused on all of these other use cases outside of the software team that our users were asking us to go ahead and solve.

**Megan Cook** (00:49:36):
So that was a really great way to discover the need for a new product. Were these really strong signals from within our customers in that same area of business that we're really well set up to help them learn.

**Lenny** (00:49:50):
What was that process like from noticing, "Hey, designers are using Jira and they're not having a good time. PMs are using Jira, researchers, and here's the issues they're running." So just that insight of like, "Oh, interesting. There might be an opportunity here to launching." I don't know the first version. I don't know if you're actually involved in this, but whatever you can share would be awesome. Where there design partners they all chose and like let's work with Salesforce and Microsoft and make sure they love it? How long was that process? Because I think that's the prop people are so curious about just how do we validate and discover and then actually launch something that's going to work.

**Megan Cook** (00:50:28):
Yeah, I was just as close to that one, but I can give you a second example.

**Lenny** (00:50:33):
Oh, great.

**Megan Cook** (00:50:35):
Yeah, for sure. The second example actually came from our product internal innovation program and that we let anyone pitch an idea for new product in the company if they want to. So we had this wonderful product manager, Tammy Carson, who saw a demand for a solution for product managers to build their roadmaps a bit better before ideas get committed. So as you know, this is fuzzy area before you actually start building something as a product manager where you're looking at lots of opportunities and ideas and you're prioritizing them. And it's not really confirmed real work yet. And nobody wanted to put that in Jira because once it was in Jira, then everyone just expected it to happen. And so this is where Jira product discovery came from.

**Megan Cook** (00:51:24):
And in the past we'd tried things like this before in new products at Atlassian and they've been successful, but it'd been really hard because large parts of the company process and those checks were optimizing for the success of the bigger products like Jira software. And so we changed that to create really small groups with stage gates that we call wonder, explore, make, impact, and then getting to scale. And that meant to assess those bets at every stage. And the idea was to iterate really quickly, either to it not working out and proving that it couldn't be a business or iterate really quickly to yes it could and we should invest more in this. And so with each stage there would be a little bit of investment.

**Megan Cook** (00:52:12):
So you say that for a stage of wonder might just be the person with the idea. And then explore, you might add on a couple more people, like three people to go and really have a look at, here's a prototype, here are some customers that'd be interested in it and could help us think about this some more and put together what the roadmap looks like. And then when you get to make that's when you get a full team, but a full team is going to be 12 people or so, it's still not huge. And I think that's really important because at each stage you're getting validation, you're getting more customers who are interested and invested in helping you develop what that solution looks like.

**Megan Cook** (00:52:56):
You asked about whether we went and partnered with a partner company like Salesforce for something like this, for a new product. In this case it was just really partnering heavily with our customers where we saw that interest coming through in our other products like Jira software and building something that really works for them before expanding it to more and more customers and finding that product market fit and then upping the investment. And so we've had a couple of new products recently that have gone through that sort of stage rollout. So there's Jira Product Discovery, there's Atlas that I mentioned before, and I think Compass is the latest one.

**Lenny** (00:53:36):
So what I'm hearing here is essentially there's this step-by-step gated process that you put new product ideas through and they make it one step at a time. And I imagine there's a leader that can decide, "No, this one's not working out. Let's end it at the explorer phase and invest in other ideas." I imagine

**Megan Cook** (00:53:56):
Yeah, that's right. It might be someone who's looking after that particular market. At each one of those stages, there's that check on whether or not we continue to go ahead.

**Lenny** (00:54:08):
And the stages are wonder. I like that a lot. That's a great name. Explore, make, and then what were the other ones?

**Megan Cook** (00:54:16):
Impact and scale.

**Lenny** (00:54:18):
Got it. So impact is like is it showing any impact? We made it, is it working? And then scale. Got it. That makes sense. Just like let's go for it.

**Megan Cook** (00:54:25):
Yeah. Impact could be I can be self-sufficient in the revenue that I'm generating, and scale is just really launching it to take off.

**Lenny** (00:54:35):
Launch it. Yeah, it goes on the website. Okay. So wonder is like a PM and an engineer maybe at Hackathon where we have an idea. Explore is they maybe get a little bit of resourcing and they start exploring the idea, build the prototype, maybe find a design partner too, to think about this. Is that roughly right?

**Megan Cook** (00:54:52):
Yeah.

**Lenny** (00:54:52):
Okay.

**Megan Cook** (00:54:52):
Make sure you've got a clear roadmap. Yeah.

**Lenny** (00:54:54):
Okay, got it. And then make, is that where they expand it to a few more customers and make it more fully featured?

**Megan Cook** (00:55:04):
Yeah. Make is where you'd actually build it. So the prototype-

**Lenny** (00:55:09):
Okay, got it.

**Megan Cook** (00:55:10):
... could be pretty simple, could be a bit cobbled together, make is actually building the product and see if you can get more and more customers.

**Lenny** (00:55:14):
Got it.

**Megan Cook** (00:55:15):
That's where you'd start to make it with those customers.

**Lenny** (00:55:19):
This is really interesting because again, I think Atlassian is one of the very few companies that has done this so well. And I don't know, this number is absurd. I've never heard of another company that's 15 successful products. I don't know how successful they're, but they're out there and people seem to be... They're being promoted. I guess is there any other advice to share along the lines of if someone is thinking about launching a second product, anything you would suggest they do or think about they may not be thinking about?

**Megan Cook** (00:55:42):
I think my advice is skied towards the Atlassian case, which is where you're in a 12,000 strong employee company and how do you seed something that you want to run as more with more of a startup kind of mindset. So when you get to this size, you've got quarterly planning and business reviews and all of these different process and you don't necessarily want to put your seed startup through that. It's not quite ready for that kind of thing. So I think the key things here that make it really successful is starting really small with the idea and the solution to be proved and don't add too many people, don't feel pressured to add too many people. I think it's easy to get really excited about the potential and just want to throw four or five teams at it, but that can... We were talking about this stat. That can make things run slower and so you want to protect them.

**Megan Cook** (00:56:39):
And the second thing is just give them freedom to move really fast and solve those problems in a different way. So there are different expectations. They don't necessarily need to be a part of that process that I was talking about before. This team should just be running hard to prove whether or not the idea's going to work and whether there's product market fit.

**Megan Cook** (00:56:59):
And for different approaches. If I want to add something to Jira software, but we're talking millions and millions of users there, that thing has to be resilient. It's got to scale. There are all these things that users inherently expect from something like that. But for something small like this, we are proving product market fit. You don't need to think about that initially. So you've got to hold this to a different standard, otherwise you're just going to slow them down way too much.

**Megan Cook** (00:57:25):
And actually we found that by letting them tackle problems a little differently, we found innovative way of looking at things that we can pull back into our other products. So for example, if you look at Jira Product Discovery, and just the way that it gives more of a spreadsheet kind of view of a list of ideas and things like that, some of the experience there is definitely something that we'll be pulling into Jira software.

**Lenny** (00:58:00):
You mentioned that over the years, Jira has weathered many storms. From my perspective, it feels like it continues to weather many storms incredibly well. One, because there's just endless startups always coming at Jira trying to become the new project management tool that everyone uses. And two, it just feels like people are always dissing on Jira like, "Jira sucks, I want to use something else." On the other hand, it continues to dominate. Many people love it. I'm curious what you believe Atlassian generally has done and your team has done to keep Jira ahead of everyone. And I know you're probably going to say, "We listen to customers better than anyone." So if that's a big part of the answer, definitely share that. But I'm curious, is there anything else people may not be recognizing of just why Jira has been so successful for so long?

**Megan Cook** (00:58:46):
Yeah. I think the number of startups that enter this space, just so it shows how important the problem is that we solve and that problem of teamwork and collaboration. We've got more than 125,000 customers around the world who start their day in Jira, millions of users and the kinds of companies that use it. I just love hearing about what they do with it. They really blow me away. Like NASA landing the Mars rover or Canva building this design platform for 40 million people, it's just massive.

**Lenny** (00:59:23):
I don't think you can beat that Mars rover story array. That's a good one. I think when you follow it up with the Canvas story, that one's less interesting now, but it's also amazing. Okay. Sorry. Keep going.

**Megan Cook** (00:59:33):
So like you said, they are integral to our success. We do obsess over them. We think if we do right by them, then we're going to be going in the right direction. I don't think we've ever had this sense of arrogance of just... No matter how big we are, we've always got this healthy dose of paranoia that we need to keep working on improving things and being better. So to your point about customer feedback, that is a big part of it. We bake in these rituals just to make it super easy for everyone to do that. So the whole company gets an email every week and it's just got a random selection of feedback from our customers. It's got how they rate us and just a quote as well. And so everyone's sort of getting this dose of feedback all the time.

**Megan Cook** (01:00:24):
We have regular share outs of all of the research that everyone gets. We get in-product feedback. We make it super easy to talk to our customers through social media or LinkedIn or X now. And then we also have a whole community space where customers can have longer conversations with us about different ideas that we're coming up with or feedback that they have for us. So I think that is all massively important for keeping Jira ahead of the pack.

**Megan Cook** (01:00:58):
I think how we stay ahead in other areas is just that the culture is super, super open to innovation, kind of invites innovation. So we have these hackathons, we call them shepherd. The whole company stops and everyone can play with new ideas or technologies. It's a competition. So the best ideas get visibility. It can get people working with other people that they wouldn't normally. And also the visibility of the ideas helps generate more ideas all over the place.

**Megan Cook** (01:01:31):
Like I said before, innovation can come from anywhere. So anyone can pitch new ideas or products. And when we see new technologies emerging that we think are going to be really foundational and interesting, we'll carve off a team to go and look at that. So I think we've had an AI team central to Atlassian for a long time, but with the advent of ChatGPT, there's sort of this huge move forward. There's this leak that's happening. And so in my team, I just carved off a small team to go and explore that and see what interesting things that we could do there.

**Megan Cook** (01:02:09):
I think we don't shy away from tackling subsets of the market that we're seeing that need a bit more love, like the Jira Product Discovery story that we were just talking about a second ago. And we also use our products a lot and that helps us find all of those little problems and makes it really real. We get really excited about the different things that the whole team is working on. We send lots of feedback to each other. I think that's also a really important part of it.

**Megan Cook** (01:02:42):
Another area is when we look at how we're investing, there's always this pressure to invest in the core business, of course, but we also make sure that we invest in seeding future businesses. And like we're talking about, they might not always work out. So we had then the Compass and the Atlas example of ones that have worked out, but we also see things through Atlassian inventions. So if there are interesting ideas or technologies, these might support the products later on, that's something that we'll go and seed out there in the market. And that's led to a few acquisitions there as well, which has been really useful.

And the last thing is I think I am just really impressed at the way that we stay agile to move towards these different shifts that come up. It always surprises me just how agile we can be. For example, in 2020 we decided to double down on our mission to deliver a world-class cloud experience. And it was like hundreds of people just moved around in Atlassian to make that happen, which was in a very short period of time, which was impressive. And we're not shy about killing things off with their [inaudible 01:03:55]. So I'll give you another example of one of those products that was going through that we ended up killing off. So we had a whiteboard product that we thought would be its own product, sort of like a Jira Product Discovery. And when we came to one of those gates with the team, we realized actually this is more a really useful document type. And so now you'll see that it's a feature in Confluence. It was very quick to make that decision.

**Lenny** (01:04:28):
I have this new segment, not that new anymore, called Failure Corner. I'm curious if you have any interesting story of a big failure in your career. And if you do, what you learned from that experience?

**Megan Cook** (01:04:41):
I think I'll give you a bit of a different one because I think this one is harder to spot and I think that's really interesting. It's something that I think about all the time though. So I missed a really big opportunity to move Atlassian forward back in the day. And I, like I said, think about it every time I review a new idea or look at an opportunity that we're thinking about.

**Megan Cook** (01:05:06):
So I was on this team and I was improving the way that our products help developers get their work done. And so typically we saw them start in Jira software. They'd pick up a piece of work and then they'd switch tools. They'd create a brand, they'd start writing code. And we noticed that they would forget to come back and update the status of their work and this could create a lot of confusion in the team. Another developer could pick up that work thinking it wasn't started and then there was a lot of wasted time. Or if you're trying to track metrics like how long does it take for a piece of work to get started through to done? That'll totally ski things. So this was causing a lot of problems.

**Megan Cook** (01:05:42):
But we didn't want to make developers come back into the tool that was obviously something that was getting in the way of their work. So we decided to build automation so they didn't have to leave their ID or the command line to do that. They can just keep working. So an example is Jira would detect that a new command had been created and then it could automatically move your piece of work to in progress because there's code being written against it. And there were a whole bunch of these examples that parties integrated into it and I made the decision to put into Jira as a user was editing their workflow and we shipped it and it performed just fine. People discovered it, they used it, and seemed to give a lot of value. People liked it, which doesn't really sound like a fail. I don't think that...

**Megan Cook** (01:06:33):
Where I dropped the ball was more about what I should have realized about that feature. So automation, it's super useful. It can be used by a whole slew of people who aren't just developers. It could be used in every single product. It's more than just moving things to a new status. And so I should have realized that we could have built this amazing service that every product could have moved themselves forward with. And years later, Atlassian actually acquired a company that did exactly that, this advanced automation. And it's in every product now. And so you can imagine how much it costs to acquire a company. That was a really extensive mistake on my part. So when I see a new idea, I'm always asking myself, "How do we push this further? Is there something there that we can 10X? Can we apply it more broadly to more types of users, more products? Is there some bigger opportunity that we can really take advantage of?"

**Lenny** (01:07:31):
That's an awesome story. So the lesson there is just think bigger with the products. You almost need to wait for it to first be successful for you just to be like, "Oh, but can we do something more with this?" Do you think you should have been thinking about that as you were building it or would that have been too early?

**Megan Cook** (01:07:47):
No, I think I should have caught that as we were building it, because even when I think about the experience, so it was a really good proving ground for it for sure. But even when I think about the experience, just where that experience was designed and product limited its functionality, which is a real shame.

**Lenny** (01:08:07):
I guess the takeaway there is just if you're committing to some idea, ask yourself what would it look like if this was 10 times bigger? If this was a bigger deal, can this apply to other things we're doing? Is that right?

**Megan Cook** (01:08:21):
Yeah. Where could this go in three years, five years? And should that change the way that you think about it now?

**Lenny** (01:08:29):
Great advice. Megan, is there anything else that you wanted to share or is there anything you wanted to leave listeners with before we get to our very exciting lightning round?

**Megan Cook** (01:08:39):
I'll leave you with something. And it's just this practice that I've found really useful for my squad that we've implemented pretty recently, and especially with remote work and all of that. So like I said, we have limited time together, but what we put into place is something we called Fight Club. I'll probably get in trouble for talking about Fight Club. The first rule is you don't talk about fight club.

**Lenny** (01:09:05):
Everyone knows that.

**Megan Cook** (01:09:08):
It's 30 minutes every week. And it's just for myself, my engineering and my design leader, and we get together and we know that we're going in there to have a conflict. I think often when there's difficult conversations or those conflicts come up, you can put them off until they become much bigger. Or if somebody is conflict adverse, they can try to avoid having it at all. But by having a specific sort of time in your week for something like that, then you're sort of in that mindset. You know you're going in there to solve a hard problem. You know that there's going to be a disagreement and it makes it much better. And I think the relationship we all have is so much better because we get on top of these things early.

**Lenny** (01:09:53):
This is super cool. It's like couples therapy or something where you're just like, "What issues do we have? Let's work through them right now." I love that. I love that. And it makes it okay to bring up things that are bothering you and things that you think need to change. And with that, we've reached our very exciting lightning round. Are you ready?

**Megan Cook** (01:10:12):
Yes, can't wait. Let's do it.

**Lenny** (01:10:14):
First question, what are two or three books that you've recommended most to other people?

**Megan Cook** (01:10:19):
Look, I have a habit of sending books to everyone who reports to me every year just on a skill they're working on. So I've got a huge list that I actually send out, but the one that I send out the most to new PMs especially is just inspired by Marty Cagan. It holds up really well. It was recommended to me by my first boss, and it's just got a bunch of great tips in there, just great foundational knowledge.

**Megan Cook** (01:10:49):
More recently, what I've been sending out for my managers is Scaling People by Claire Hughes Johnson. I think that just came out within the last year actually, but it's just got an incredible amount of really useful tactical things, templates, all sorts of things that you can put into practice.

**Lenny** (01:11:11):
Great choices. We have both in the bookshelf behind me. Both of them have been on the podcast. I wish I could see the whole list of books that you recommend to people. If you don't have this written out anywhere, you should publish some kind of blog or newsletter post of here's the skill and here's the book you recommend.

**Megan Cook** (01:11:26):
Oh, that's a great idea. Yeah, I'm going to do that. Thanks.

**Lenny** (01:11:29):
Right, you have a homework assignment. Okay, next question. What is the favorite recent movie or TV show you've really enjoyed?

**Megan Cook** (01:11:35):
I am so late to TV, but Foundation is the one that I've been binging lately, and I think it's just this huge world. And I'm not usually one that gets super into sci-fi, but the way that it brings forward some of these ideas for what new technologies could mean... If you haven't seen it, and this is really spoiling it, one of the main characters or three of the main characters are actually clones of this emperor who rules the universe and decided to clone himself at three different stages of his life so that those people could continue rolling. And I think even that idea just invites the idea of what if we stretched out human life? What are the impact? How do things advance when you've got that same mindset and same people continue on? It's super compelling.

**Lenny** (01:12:28):
Foundation, the show got ruined for me by reading the books many, many years ago, is one of my favorite sci-fi trilogy of all time. And then I was so excited for the show and has nothing to do with the books, basically. It's like the storyline is completely different, the core idea is the same as the only real. So I just got tired of it and stopped. But if you haven't read the books, I think you would love it. It's beautiful.

**Megan Cook** (01:12:50):
Are the books better?

**Lenny** (01:12:53):
Yeah, the books are better. The books are always better, I think is a good rule of thumb.

**Megan Cook** (01:13:00):
Yeah, that is a good rule. I'll probably pick that up.

**Lenny** (01:13:00):
Yeah. I was like a teenager when I read them, so I don't know. Maybe they suck, but I think people love them. Highly recommend the books if you liked the show especially. Next question, do you have a favorite interview question that you'd like to ask candidates?

**Megan Cook** (01:13:12):
I think it's an old one, but a great one on the subject of failure. I love to ask people about their biggest failure and I think it's a good way to get to know somebody because you can see how introspective they are, how much they think about what's happened and what they learned from it. It shows whether or not they can be vulnerable with you. You can see what they consider to be a big failure. Some people will list something that's not really a failure. And also you can see about whether they've got that growth mindset. So have they learned something from that? Have they applied it moving forward?

**Megan Cook** (01:13:51):
Weird rule that I've found is that a lot of the best hires that I've had has had big failure stories that they've worked through and learned from. And so I think that's great to see what they consider there, what the learnings are, but also in the solution you can also see how they tackle something like that. So are they the type of person who wants to go and forge something all by themselves? Are they the type of person who will pull together a community to figure something out? So you get that insight into their values and their approach from that question too, which is hugely useful.

**Lenny** (01:14:30):
Is there a favorite product you've recently discovered that you really love?

**Megan Cook** (01:14:34):
Yeah. You might have to stop me from going on and on about this, but I recently got a smoker, a Traeger smoker for smoking meat. And just the unboxing experience was incredible. So you get this huge box, cardboard box, you open it up. If you reverse the cardboard box, it becomes like a play saloon that your kid can jump into and just mess around in which-

**Lenny** (01:15:02):
Wow, that's cool.

**Megan Cook** (01:15:03):
... rather than just throwing it out, it becomes something really cool and useful. The set of instructions has a six-pack of beer at the top, just helps you understand how far through you should be through your six-pack as you're constructing it. You get some tools with it. And they're really good actually. They're not the usual kind of throwaway tools that you get in something to put together something like this. In addition to that sort of playful delightfulness in there, as you build it, you discover things along the way. So I opened up the hopper where you put in your wood pellets and there was a baseball cap, a tray of baseball cap in there, which was unexpected and really cool. And then the whole experience of actually using it once you've set it up is amazing. So it's all connected to my phone. I can just head to the beach and have some brisket going and come home and it's beautifully done. It just works. It's integrated. It's got integrated recipes. Yeah, I love that. I like that one.

**Lenny** (01:16:12):
And salt. That sounds so delightful. Such a great product experience. I'm going to have to get one I think. I think we're going to sell some Traeger smokers.

**Megan Cook** (01:16:17):
Sure.

**Lenny** (01:16:22):
Next question. Do you have a favorite life motto that you often come back to share with friends, either in work or in life?

**Megan Cook** (01:16:28):
It's around maximizing joy. And what I mean by that is it's about finding what's important and leaning into it or finding what's annoying and turning it into something I enjoy. To give you a super small example is I'm terrible with keys. I will leave that thing all over the place. You'll find it in my cutlery drawer or whatever, and I'll never find it again. And I think an obvious solution to that could be to put a hook on the wall or something where you can just leave them and you go back to that and it's easy to find. But what gives me joy is not actually having to have keys at all. And so now I have a fingerprint reader on my front door and I feel a little bit like James Bond every time I enter my house and I can let people in if somebody needs to leave a package or something that's easy to do. So it was turning something annoying into something more joyful.

**Megan Cook** (01:17:24):
And I think the other thing there is just I really value keeping great relationships and increasing those relationships. And so I always make time for these amazing friends that I have that live in London, and we have this pact where every time either one of us goes to the others' continent, we'll go meet them there. So every time I go to Europe, which last year I was in Berlin, at one point in Amsterdam, and on the plane, they came over and we just hung out and had a great time. And so it's making sure that you make time for those important things.

**Lenny** (01:18:00):
Along the same lines, final question related to creating more joy. I noticed a beautiful surfboard behind you. For somebody that's trying to surf and maybe not being successful, what's one tip you could share with listeners to improve their success with surfing?

**Megan Cook** (01:18:18):
Isn't surfing the most humbling sport that you've ever tried?

**Lenny** (01:18:22):
Yeah, I've tried a few times and yeah, I would say so.

**Megan Cook** (01:18:29):
I think surfing's really interesting. I've never done a sport like it in that it's something that you have to really feel. So I find every time you learn and you think about surfing, you sort of feel it before you know how to do it. So even just being able to catch a wave, a green pace wave, you're paddling, you're paddling, you don't quite know where to be, you don't quite know how much to paddle for that wave, and you just have to sort of be successful a couple times before you get the feel for it. And it's the same with trying to find the right wave. When I looked at the ocean the first time to try and pick the wave and pick where to be, I couldn't even see the shape of it to find that right place. It took me just seeing a hundred waves to be able to do that.

**Megan Cook** (01:19:15):
So my best tip for surfing is get out there, keep doing it, do it over and over and over again. You will get better. You'll start to see all of these things that you've never noticed before. And get some friends. Get some friends out there, get surfing accountability buddy to make sure that you're getting out there often.

**Lenny** (01:19:37):
He's the best buddy. Amazing. Megan, we've talked about play and safety and buy-in and fighting the good fight and adding new product lines, also surfing. Two final questions. Where can folks find you online if they want to reach out and maybe follow up on some stuff? And how can listeners be useful to you?

**Megan Cook** (01:19:55):
The best place to find me is on LinkedIn. I'm Megan Cook on LinkedIn. You can also find me if you're a customer in the Atlassian community, if you want to have a chat. And I'm also on social media, so on X, you can find me there as well. And be useful to me. Look, any feedback, absolutely any feedback on Jira software, always hungry for that. Also, really keen, if you want to just chat about how people's ways of working are evolving and shifting and changing, and how do you think that's going to turn out and how you see your goals for your team changing. I would love to talk about that. Please get in touch.

**Lenny** (01:20:37):
Awesome. Megan, thank you so much for being here.

**Megan Cook** (01:20:40):
Thank you, Lenny. It's been fun.

**Lenny** (01:20:42):
Same. Bye everyone.

**Lenny** (01:20:44):
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.

---

## [10/19] Inside OpenAI | Logan Kilpatrick (head of developer relations)

**Logan Kilpatrick** (00:00:00):
Finding people who are high agency and work with urgency, if I was hiring five people today, those are some of the top two characteristics that I would look for in people because you can take on the world if you have people who have high agency and not needing to get 50 people's different consensus. They hear something from our customers about a challenge that they're having, and they're already pushing on what the solution for them is and not waiting for all the other things to happen that... People just go and do it and solve the problem, and I love that. It's so fun to be able to be a part of those situations.

**Lenny** (00:00:36):
Today my guest is Logan Kilpatrick. Logan is head of developer relations at OpenAI, where he supports developers building on open AI's, APIs and ChatGPT. Before OpenAI, Logan was a machine learning engineer at Apple and advised NASA on their open source policy. If you can believe it, ChatGPT launched just over a year ago and transformed the way that we think about AI and what it means for our products and our lives. Logan has been at the front lines of this change, and every day is helping developers and companies figure out how to leverage these new AI superpowers.

**Lenny** (00:01:10):
In our conversation, we dig into examples of how people are using ChatGPT and the new GPTs and other open AI APIs in their work and their life. Logan shares some really interesting advice on how to get better at prompt engineering. We also get into how OpenAI operates internally, how they ship so quickly, and the two key attributes they look for in the people that they hire, plus, where Logan sees the biggest opportunities for new products and new startups building on their APIs.

**Logan Kilpatrick** (00:03:55):
Thanks for having me, Lenny. I'm super excited.

**Lenny** (00:03:57):
I want to start with the elephant in the room, which I think the elephant is actually leaving the room because I think this is months ago at this point, but I'm still just really curious. What was it like on the inside of OpenAI during the very dramatic weekend with the board and Sam and all those things? What was it like? And is there a story maybe you could share that maybe people haven't heard about what it was like on the inside, what was going on?

**Logan Kilpatrick** (00:04:20):
Yeah, it was definitely a very stressful Thanksgiving week. I think in broad context, OpenAI had been pushing for a really long time, since ChatGPT came out, and that was supposed to be one of the first weeks that the whole company had taken time away to actually reset and have a break. So very selfishly, I was super excited to spend time with my family, all that stuff. And then, yeah, Friday afternoon we got the message that all of the changes were happening, and I think it was super shocking because I think, and this is a perspective a lot of folks share, everybody had and continues to have such deep trust in Sam and Greg and our leadership team that it was just very surprising. And we're also a very, as far as company cultures go, very transparent and very open. So when there's problems or there's things going on, we tend to hear about them. And again, it was the first time that a lot of us had heard some of the things that were happening between the board and the leadership team, so very, very surprising.

**Logan Kilpatrick** (00:05:20):
I think my being someone who's not based in San Francisco, I was, again, very selfishly kind of happy that it happened over the Thanksgiving break because a lot of folks actually had gone home to different places. So it felt like I had a little bit of comfort knowing I wasn't the only one not in San Francisco, because everybody was meeting up in person to do a bunch of stuff and be together during that time. So it was nice to know that there was a few other folks who were sort of out of the loop with me.

**Logan Kilpatrick** (00:05:51):
I think the thing that surprised me the most was just how quickly everybody got back to business. I flew to San Francisco the next week after Thanksgiving, which I wasn't planning to do, to deal with the team in person and seeing, literally Monday morning, I was walking into the office being, like expecting, I don't know, something weird to be going on or happening. And really it was like people laser focused and back to work, and I think that speaks to the caliber of our team and everybody who's just so excited about building towards the mission that we're building towards. So I think that was, yeah, that was the most surprising thing of the whole incident. I think a lot of companies would've had the potential to truly be derailed for some non-trivial amount of time by this, and everybody was just right back to it, which I love.

**Lenny** (00:06:40):
I feel like it also maybe brought the team closer together. It feels like it was this kind of traumatic experience that may bring folks together because it was something they all shared. Is there anything along those lines that's like, "Wow, things are a little different now?"

**Logan Kilpatrick** (00:06:52):
One of my takeaways was I'm actually very grateful that this happened when it happened. I think today the stakes are... They're still relatively high. People have built their businesses on top of OpenAI. We have tons of customers who love ChatGPT, so if something bad happens to us, we definitely impact our customers. But on the world scale, somebody else will build a model if OpenAI disappeared and continue towards this progress of general intelligence. I think fast-forward five or 10 years, if something like this would've happened and we hadn't gone through the hopeful upcoming work transformation and all those changes that are going to happen, I think it would've been a little bit, or potentially much worse, of an outcome. So I'm glad that things happened when the stakes are a little bit lower.

**Logan Kilpatrick** (00:07:39):
And I totally agree with you. It's like the team has been growing so rapidly over the last year since I joined. It's been crazy to think about how many new folks there are, and I really think that this really brought people together because most folks, historically, many of the folks when I joined, what kind of banded us all together was the launch of ChatGPT, the launch of GPT-4, and for folks who weren't around for some of those launches, it was perhaps step day. For folks who are on for dev day, it was probably this event. So I think we've had these events that have really brought the company together cross-functionally, so hopefully all the future ones will be really exciting things like GPT five, whenever that comes, and stuff like that.

**Lenny** (00:08:20):
Awesome. We're going to talk about GPT-5. Going in a totally different direction, what is the most mind-blowing or surprising thing that you've seen AI do recently?

**Logan Kilpatrick** (00:08:31):
The things that are getting me most excited are these new interfaces around AI, like the Rabbit R-1. I don't know if you've seen that, but consumer hardware device, this company called TL Draw. I don't know if you've seen TL Draw.

**Lenny** (00:08:44):
I think. You sketch something and then it makes it as a website?

**Logan Kilpatrick** (00:08:48):
And that's only a small piece of what TL Draw is actually working on, but there's all of these new interfaces to interact with AI, and I think I was having a conversation with the TL Draw folks a couple of days ago, really blows my mind to think about how chat is the predominant way that folks are using AI today. And I actually think, and this is my bulk case for the folks at TL Draw, I'm super excited for them to build what they're building, but they're sort of building this infinite canvas experience and you can imagine how, as you're interacting with an AI on a daily basis, you might want to jump over to your infinite canvas, which the AI has filled in all the details and you might see a reference to a file and to a video and all of these different things.

**Logan Kilpatrick** (00:09:30):
And it's such a cool way. It actually makes a lot more sense for us as humans to see stuff in that type of format than, I think, just listing out a bunch of stuff in chat. So I'm really, really excited to see more people. I think 2024 is the year of multimodal AI, but it's also the year that people really push the boundaries of some of these new UX paradigms around AI.

**Lenny** (00:09:53):
It's funny. I feel like Chatbots, as a PM for many years, it feels like every brainstorming session we had about new features, it's like, "Hey, we should have built a Chatbot to solve this problem." It's like the perennial like, "Oh, Chatbot," or, "Someone's going to suggest we do a Chatbot," and now they're actually useful and working and everyone's building Chatbots, a lot of them based on OpenAI APIs.

**Lenny** (00:10:12):
There's not really a question there, but maybe the question, I was going to get to this later, is just when people are thinking about building a product like, say, TL Draw, what should they think about? Where OpenAI is not going to go versus here's what OpenAI is going to do for us. We shouldn't worry about them building a version of TL Draw in the future. What's the way to think about where you won't be disrupted essentially by OpenAI, knowing also they may change their mind?

**Logan Kilpatrick** (00:10:36):
That's a great question. I think we're deeply focused on these very, very general use cases like the general reasoning capabilities, the general coding, the general writing abilities. I think where you start to get into some of these very vertical applications... And I think a great example of this is actually Harvey. I don't know if you've seen Harvey, but it's this legal AI use case where they're building custom models and tools to help lawyers and people at legal firms and stuff like that. And that's a great example of our models are probably never going to be as capable as some of the things that Harvey's doing because our goal and our mission is really to solve this very general use case and then people can do things like fine-tuning and build all their own custom UI and product features on top of that.

**Logan Kilpatrick** (00:11:17):
I have a lot of empathy and a lot of excitement for people who are building these very general products today. I talk to a lot of developers who are building just general purpose assistants and general purpose agents and stuff like that. I think it's cool and it's a good idea. I think the challenge for them is they are going to end up directly competing against us in those spaces and I think there's enough room for a lot of people to be successful, but to me you shouldn't be surprised when we end up launching some general purpose agent product because, again, we're sort of building that with GPTs today and versus we're not going to launch some of these varied verticalized products. We're not going to launch an AI sales agent. That's just not what we're building towards. And companies who are and have some domain specific knowledge and they're really excited about that problem space, they can go into that and leverage our models and end up continuing to be on the cutting edge without having to do all that R&D effort themselves.

**Lenny** (00:12:16):
Got it. So the advice I'm hearing is get specific about use cases, and that could be either models that are tuned to be especially useful for a use case like sales or make an interface or experience solving a more specific problem.

**Logan Kilpatrick** (00:12:30):
And I think if you're going to try and solve this very general, if you're going to try to build the next general assistant to compete with something like ChatGPT, it has to be so radically different. People have to really be like, "Wow, this is solving these 10 problems that I have with ChatGPT, and therefore I'm going to go and try your new thing." Otherwise we're just putting a ton of engineering efforts and research effort into making that an incredible product, and it's just going to be the normal challenges of building companies. It's just hard to compete against something like that.

**Lenny** (00:12:59):
Awesome. Okay, that's great. I was going to get to that later, but I'm glad we touched on that. I imagine that's on the minds of many developers and founders. Kind of along the same lines, there's a lot of talk about how ChatGPT and GPTs and many of the tools you guys offer are going to make a company much more efficient. They don't need as many engineers, data scientists, PMs, things like that, but I think it's also hard for companies to think about what can we actually do to make our company more efficient. I'm curious if there's any examples that you can share of how companies have taken built a, say, a GPT internally to do something so that they don't have to spend engineering hours on it or generally just used OpenAI tooling to make their business internally more efficient?

**Logan Kilpatrick** (00:13:42):
Yeah, that's a great question. I wonder if you can put this in the show notes or something like that, but there's a really great Harvard Business School study about... And I forgot which consulting firm they did it with. Maybe it was like Boston Consulting or something like that, but it might've been one of the other ones. And they talk about the order of magnitude of efficiency gain for those folks who are using AI tools, I think it was chat GPT specifically in those use cases that they were using, comparatively against folks who aren't using AI. I'm really excited, also, just as just more time passes between the release of this technology, for us to get more empirical studies. I feel just for myself, as somebody who's an engineer today, I use ChatGPT and I can ship things way faster than I would be able to.

**Logan Kilpatrick** (00:14:26):
I don't have any good metrics for myself to put a specific number on it, but I'm guessing people are working on those studies right now. I think engineering is actually one of the highest leverage things that you could be using AI to do today and really unlocking, probably on the order of at least a 50% improvement, especially for some of the lower hanging fruit software engineering tasks. The models are just so capable at doing that work. And it's crazy to think... And I'm guessing, actually, GitHub probably has a bunch of really great studies they publish around copilots and you could use those as an analogy for what people are getting from ChatGPT as well. But those are probably the highest leverage things.

**Logan Kilpatrick** (00:15:07):
I think now with GPTs, people are able to go in and solve some of these more tactical problems. I think one of the general challenges with ChatGPT is it gives a decent answer for a lot of different use cases, but oftentimes it's not particular enough to the voice of your company or the nuance of the work that you're doing. And I think now with GPTs and people who are using the teams in ChatGPT and Enterprise in ChatGPT, they can actually build those things, incorporate the nuance of their own company, and make solving those tasks much, much more domain specific. So we literally just launched GPTs a couple of months ago, so I don't think there's been any good public success stories, but I'm guessing that success is happening right now at companies, and hopefully we'll hear more about that in the months to come as folks get super excited about sharing those case studies.

**Lenny** (00:15:58):
I'll share an example. So I have this good friend, his name's Dennis Yang, he works at Chime, and he told me about two things that they're doing at Chime that seem to be providing value. One is he built a GPT that helps write ads for Facebook and Google just gives you ideas for ads to run, and so that takes a little load off the marketing team or the growth team. And then he built another GPT that delivers experiment results, kind of like a data scientist, with here's the result of this experiment. And then you could talk to it and ask for like, "Hey, how much longer do you think we should run this for," or, "What might this imply about our product," and things like that. And I think it's really-

**Logan Kilpatrick** (00:15:58):
I love that.

**Lenny** (00:16:35):
Like you said. Is there anything else that comes to mind? Just things you've heard people do just like, "Wow, that was a really smart way of... " So I get there's engineering, co-piloting type tooling. Is there anything else that comes to mind? Just to give people a little inspiration of like, "Wow, that's an interesting way I should be thinking about using some of these tools."

**Logan Kilpatrick** (00:16:50):
I've seen some interesting GPTs around the planning use cases, like you want to do OKR planning for your team or something like that. I just actually saw somebody tweet it literally yesterday. I've seen some cool venture capital ones of doing diligence on a deal flow, which is kind of interesting, and getting some different perspectives. I think all of those horizontal use cases where you can bring in a different personality and get perspective on different things I think is really cool. I've personally used a GPT, the private GPT that I use myself that helps with some of the planning stuff for different quarters, and just making sure that I'm being consistent in how I'm framing things like driving back to individual metrics, stuff that, when people do planning, they often miss in our data, and then it's been super helpful for me to have a GPT to force me to think about some of those things.

**Lenny** (00:17:43):
Wait, can you talk more about this? What does this GPT do for you and what do you feed it?

**Logan Kilpatrick** (00:17:48):
Yeah, I forgot what article I saw online, but it was some article that was talking about what are the best ways to set yourself up for success in planning. And I took a bunch of the... I'll see if I can make it public after this and send you a link, but took a bunch of the examples from that and went in and put some of those suggestions into the GPT, and then now when I do any of my planning of I want to build this thing, I put it through and have it generate a timeline, generate all the specifics of what are the metrics and success that I'm looking for, who might be some important cross-functional stakeholders to include in the planning process, all that stuff, and it's been helpful.

**Lenny** (00:18:25):
Wow, that is very cool. That would be awesome if you made it public. And if you do, we'll link to it and we'll make it the number one most popular GPT in the store.

**Logan Kilpatrick** (00:18:35):
I love it.

**Lenny** (00:18:35):
Going in a slightly different direction, there's this whole genre of prompt engineering. It feels like it's one of these really emerging skills. I actually saw a startup hiring a prompt engineer, one of the startups I've invested in, and I think that's going to blow a lot of people's minds that there's this new job that's emerging. And I know the idea is this won't last forever, that in theory AI will be so smart you don't need to really think about how to be smart about asking it for things you need it to do. But can you just describe this idea of what is prompt engineering, this term that people might be hearing? And then even more interestingly, just what advice do you have for people to get better at writing prompts for, say, ChatGPT or through the API in general?

**Logan Kilpatrick** (00:19:13):
Yeah, this is such an interesting space, and I think it's another space where I'm excited for people to do more scientific empirical studies about, because there's so much gut feeling, best practices that maybe aren't actually true in a certain way. I think the reason that prompt engineering exists and comes up at all is because the models are so inclined, because of the way that they're trained, to give you just an answer to the question that you ask. Crap in crap out. If you ask a pretty basic question, you're going to get a pretty basic response. And actually the same thing is true for humans, and you can think of a great example of this. When I go to another human and I ask, "How's your day going," they say, "It's going pretty good."

**Logan Kilpatrick** (00:19:53):
Literally, absolutely zero detail, no nuance, not very interesting at all versus, again, if you have some context with a person, if you have a personal relationship with them and I ask you, "Hey Lenny, how's your day going? How did the last podcast go," et cetera, et cetera, you just have a little bit more context and agency to go and answer my question. I think this is prompt engineering.

**Logan Kilpatrick** (00:20:13):
My whole position on this is prompt engineering is a very human thing. When we want to get some value out of a human, we do this prompt engineering. We try to effectively communicate with that human in order to get the best output. And the same thing is true of models. And I think it's like, again, because we're using a system that appears to be really smart, we assume that it has all this context, but it's really like imagine a human level intelligence but literally no context. It has no idea what you're going to ask it. It's never met you before. It has no idea who you are, what you do, what your goals are. And it's the reason that you get super generic responses sometimes is because people forget they need to put that context in the model.

**Logan Kilpatrick** (00:20:57):
So I think the thing that is going to help solve this problem, and we already kind of do this in the context of Dali, so when you go to the image generation model that we have, Dali, and you say, "I want a picture of a turtle," what it does is it actually takes that description. It says, "I want a picture of a turtle," and it changes it into this high fidelity, like generate a picture of a turtle with a shell, with a green background and lily pads in the water and all this other. It adds all this fidelity because that's the way that the model is trained. It's trained on examples with super high fidelity. This will happen with text models.

**Logan Kilpatrick** (00:21:35):
You can imagine a world where you go into ChatGPT and you say, "Write me a blog post about AI." It automatically will go and be like, "Let me generate a much higher fidelity description of what this person really wants, which is generate me a blog post about AI that talks about the trade-offs between these different techniques and some example use cases and references some of the latest papers," and it does all that for you, and then you at the user will hopefully be able to be like, "Yep, this is kind of what I wanted. Let me edit this. Let me edit this here."

**Logan Kilpatrick** (00:22:02):
And again, the inherent problem is we're lazy as humans. We don't want to type all... We don't really want to type what we mean, and I think AI systems are actually going to help solve some of that problem.

**Lenny** (00:22:12):
So until that day, what can people do better when they're prompting, say ChatGPT? And I'll give you an example. Tim Ferris suggested this really good idea that I've been stealing, which is when you're preparing for an interview, you go to chat GPT. And so I did this for you. I was like, "Hey, I'm interviewing Logan Kilpatrick, he is head of developer relations at OpenAI, on my podcast. Give me 10 questions to ask him in the style of Tyler Cowen," who I think is the best interviewer. He is so good at just very pointed original questions. So what advice would you have for me to improve on that prompt to have better results? The questions were fine. They're great. They're interesting enough, but they weren't like, "Holy, these are incredible." So I guess what advice would you give me in that example?

**Logan Kilpatrick** (00:22:57):
Yeah, that's a great example where thinking in context of who it is that you're asking questions about. I'm probably not somebody who has enough information about me on the internet where the model actually has been trained and knows the nuances of my background. I think there's probably much more famous guests where it might be that there's enough context on the internet to answer the questions. You actually have to do some of that work. You need to, say if you're using browse with Bing, for example, you could say, "Here's a link to Logan's blog and some of the things that he's talked about. Here's a link to his Twitter. Go through some of his tweets, go through some of his blogs and see what his interesting perspectives are that we might want to surface on the blog," or something like that.

**Logan Kilpatrick** (00:23:36):
It's, again, giving the model enough context to answer the question. I think, again, that prompt actually might work really well for somebody who has it, if you were interviewing Tom Cruise or something like that, somebody who has a lot of information about them on the internet. It probably works a little bit better.

**Lenny** (00:23:52):
So the advice there is just give more context. It doesn't tell you, "Hey, I don't actually know that much about Logan, so give me some more information." It's just like, "Here you go. Here's a bunch of good questions."

**Logan Kilpatrick** (00:24:00):
Exactly. It wants to. It so deeply wants to answer your question. It doesn't care that it doesn't have enough context. It's the most eager person in the world you could imagine to answer the question, and without that context it's just hard to do, to give anything a value. If we got t-shirts printed, they should say, "Context is all you need. Context is the only thing that matters." It's such an important piece of getting a language model to do anything for you.

**Lenny** (00:24:26):
Any other tips? Just as people are sitting there, maybe they have ChatGPT open right now as they're crafting a prompt, is there anything else that you'd say would help them have better results?

**Logan Kilpatrick** (00:24:37):
We actually have a prompt engineering guide, which folks should go and check out. It has some of the examples. It depends on the order of magnitude of how much performance increase you can get. There's a lot of really small silly things, like adding a smiley face, increases the performance of the model. I'm sure folks have seen a lot of these silly examples, but telling the model to take a break and then answer the question, all these kinds of things. And again, if you think about it, it's because the corpus of information that's trained these models is the same things that humans have sent back and forth to each other. So you telling a human, "When I go take a break and then I come back to work, I'm fresher and I'm able to answer questions better and do work better," so very similar things are true for these models. And again, when I see a smiley face at the end of someone's message, I feel empowered that this is going to be a positive interaction and I should be more inclined to give them a great answer and spend more effort on the thing that they asked me for.

**Lenny** (00:25:34):
Wow, wait. So that's a real thing. If you had a smiley face, it might give you better results.

**Logan Kilpatrick** (00:25:39):
Again, it's like the challenge with all this stuff is it's very nuanced and it's also it's a small jump in performance. You could imagine on the order of one or 2%, which for a few sentence answer might not even be a discernible difference. Again, if you're generating an entire saga of texts, the smiley face could actually make a material difference for you, but for something small and textual it might not.

**Lenny** (00:26:03):
Okay, good tip. Amazing. Okay, we've talked about GPTs I think maybe might be helpful to describe what is this new thing that you guys launched, GPTs, and I'm curious just how it's going. This is a really big change and element of OpenAI now with this idea that you could build your own mini, and I'm almost explaining it, your mini open ChatGPT and then people can... I think you can pay for it. You can charge for your own GPT or is it all free right now?

**Logan Kilpatrick** (00:26:29):
It's ll free right now. It's all free.

**Lenny** (00:26:31):
Okay. In the future I imagine people will be able to charge. So there's this whole store now. Basically it's the whole app store that you guys have launched. How's it going? What's happening? What surprised you there? What should people know?

**Logan Kilpatrick** (00:26:42):
Yeah, it's going great, and again, historically the thing that you would have to do, let's say for example, you have a really cool ChatGPT use case, what you would have to do to share it with somebody else is actually go in and start the conversation with the model, prompt it to do the things that you wanted to, and then you would share that link with somebody else before the action has actually happened and be like, here now you can essentially finish this conversation with ChatGPT that I started.

**Logan Kilpatrick** (00:27:08):
So GPT kind of changes this where you take all that important context, you put it into the model to begin with, and then people can go and chat with essentially a custom version of ChatGPT. And the thing that's really interesting is you can upload files, you can give it custom instructions, you can add all these different tools. Like a code interpreter is built in, which allows you to do math. Essentially you have browsing built in, image generation built in. You can also, for more advanced use cases if you're a developer, you can connect it to external APIs so you can connect it to the Notion API or Gmail or all these different things, and have it actually take actions on your behalf.

**Logan Kilpatrick** (00:27:44):
So there's so many cool things that people are unlocking. And what's been most exciting to me, actually, is the non-developer persona is now empowered to go and solve these really, really, really more challenging problems by giving the model enough context on what that problem is to be able to solve it. Going back to context is all you need, this is very true in the context of GPTs, and if you give it enough context, you can solve much more interesting problems.

**Logan Kilpatrick** (00:28:11):
There's so many things that I'm excited about with this. I think monetization, when it comes to the store later this quarter, I think is going to be extremely exciting when people can get paid based on who's using their GPT. That's going to be a huge unlock and open a lot of people's eyes to the opportunity here. I also think continuing to push on making more capabilities accessible to GPTs for people who can't code is really exciting. Even for me as someone who is a software engineer, it's not super easy to connect the Notion API or the Gmail API to my GPT, and really I'd love to just be able to one click sign in with Gmail and then all of a sudden it's like my Gmail is accessible, or someone else can sign in with their Gmail and make it accessible. So I think over time all those types of things will come, but today it's really custom prompts is essentially one of the biggest value adds with GPTs.

**Lenny** (00:29:03):
Awesome. I have it pulled up here on different monitor and Canva has the top GPT currently, and I was trying to play with it as you're chatting just to see. I was going to make a big banner that said, "It's the context stupid," and it doesn't. I'm not doing something right, but I'm not paying that much attention to it because we're talking, but this is very cool. Just maybe a final question there. Is there a GPT that you saw someone built that was like, "Wow, that's amazing. That's so cool," something that surprised you? And I'll share one that was very cool, but is there anything that comes to mind when I ask that?

**Logan Kilpatrick** (00:29:33):
I think my instinct is the Zapier. All of the stuff that Zapier has done with GPTs is the most useful stuff that you could imagine. You can go so far with what... And I don't know how it's packaged for Zapier's GPT right now, but you can actually, as a third party developer, integrate Zapier without knowing how to code into your GPT. So they're pushing a lot of this stuff, and then basically all 5,000 connections that are possible with Zapier today, you can bring into your GPT and essentially enable it to do anything. So I'm incredibly excited for Zapier and for people who are building with them so many things that you can unlock using that platform. So I think that's probably the most exciting thing to me for people who aren't developers.

**Lenny** (00:30:20):
Awesome. Zapier's always in there, getting in there connecting things.

**Logan Kilpatrick** (00:30:23):
Yeah, they're great.

**Lenny** (00:30:25):
So the one that I had in mind, so I had a buddy of mine, [inaudible 00:30:28], who's the CEO of a company called Runway built this thing called Universal Primer which helps you learn. It's described as, "Learn everything about anything," and basically, I think, it's kind of this Socratic method of helping you learn stuff. So it's like, "Explain how transformers work in LMs," and then it just kind goes through stuff and then asks you questions, I think, and helps you learn new concepts. And I think it's the number two education GPT.

**Logan Kilpatrick** (00:30:53):
I love that. [inaudible 00:30:53] is incredible, so...

**Lenny** (00:30:54):
**Logan Kilpatrick** (00:32:48):
Yeah, there's so many interesting trade-offs and all of this tension around how quickly companies can move. I think for us, again, if you think about Apple as an example, if you think about NASA as an example, just older institutions, lots of... Over time, the tendency is things slow down. There's additional checks and balances that are put in place, which drags things down a little bit. So we're young and a new company, so we don't have a lot of that institutional legacy barriers that have been put in place.

**Logan Kilpatrick** (00:33:18):
I think the biggest thing, and there's a good Sam tweet somewhere in the ether about this from, I think, 2022 or something like that, but finding people who are high agency and work with urgency is one of the most... If I was hiring five people today, those are some of the top two characteristics that I would look for in people because you can take on the world if you have people who have high agency and not needing to either get 50 people's different consensus, because you have people who you trust with high agency and they can just go and do the thing, I think, is one of the most... It is the most important thing, I'm pretty sure, if you were to distill it down.

**Logan Kilpatrick** (00:34:04):
And I see this in folks that I work with. Folks are so high agency. They see a problem and they go and tackle it. They hear something from our customers about a challenge that they're having and they're already pushing on what the solution for them is and not waiting for all the other things to happen that I think traditional companies are stuck behind because they're like, "Oh, let's check with all these seven different departments to try to get feedback on this." People just go and do it and solve the problem. And I love that. It's so fun to be able to be a part of those situations.

**Lenny** (00:34:35):
That is so cool. I really like these two characteristics because I haven't heard this before. Those are the two, maybe the two most important things you guys look for, high agency, high urgency. To give people a clear sense of what these actually look like when you're hiring, you shared maybe this example of customer service. Someone's hearing a bug and then going to fix it. Is there anything else that can illustrate what that looks like, high agency? And then a similar question on urgency other than just move, move, move, ship, ship, ship.

**Logan Kilpatrick** (00:35:01):
I think the assistants API that we released for dev day, we continue to get this feedback from developers that people wanted these higher levels of abstraction on top of our existing APIs, and a bunch of folks on the team just came together and were like, "Hey, let's put together what the plan would look like to build something like this," And then very quickly came together and actually built the actual API that now powers so many people's assistant applications that are out there. And I think that's a great example of it wasn't this top down, oh, someone's sitting there being like, "Oh, let's do these five things," and then like, "Okay, team, go and do that." It's like people really seeing these problems that are coming up and knowing that they can come together as a team and solve these problems really quickly. And I think the assistants API, and there's like 1,001 other examples of teams taking agency and doing this, but I think that's a great one at the top of my head

**Lenny** (00:35:55):
That makes me want to ask. Just how does planning work at OpenAI? So in this example is just like, "Hey, we think we need to build this. Let's just go and build it." I imagine there's still a roadmap and priorities and goals and things that that team had. How does road mapping and prioritization and all of that generally work to allow for something like that?

**Logan Kilpatrick** (00:36:14):
I think this is one of the more challenging pieces at OpenAI. There's so many. Everyone wants everything from us, and today, especially, in the world of ChatGPT and how large and well-used our API is, people will just come to us and say, "Hey, we want all of these things." I think there's a bunch of core guiding principles that we look at. One, going back to the mission, is this actually going to help us get to AGI? So there's a huge focus on there's this potential shiny reward right in front of us, which is optimize user engagement, or whatever it is. And is that really the thing? Maybe the answer is yes. Maybe that is what is going to help us get to AGI sooner, but looking at it through that lens I think is always the first step of deciding any of these problems.

**Logan Kilpatrick** (00:37:03):
I think, on the developer side, there's also these core tenets of reliability like, "Hey, it would be awesome if we had additional APIs that did all these cool things like new endpoints, new modalities, new abstractions, but are we giving customers a robust and reliable experience on our API?" And that's often the first question. And I think there have been times where we've fallen short on that, and there was a bunch of other things that we've been thinking about doing and really bringing the focus and priority back to that reliability piece because, at the end of the day, nobody cares if you have something great if they can't use it robust and reliably.

**Logan Kilpatrick** (00:37:37):
So there's these core tenets. And I think, again, we have very, other than all the principles about how we're making the decision, I think the actual planning process is pretty standard. We come together. There's H1 Q1 goals. We all sprint on those. I think the real interesting thing is how stuff changes over time. You think we're going to do these very high level things and new models, new modalities, whatever it is. And then as time goes on, there's all of this turmoil and change, and it's interesting to have mechanisms to be like, "Hey, how do we update our understanding of the world and our goals as everything the ground changes underneath of us as is happening in the craziness of the AI space today?"

**Lenny** (00:38:22):
It's interesting that it sounds a lot like most other companies. There's H1 planning. There's Q1 planning. Are there metrics and goals like that that you guys have OKRs or anything like that? Or is it just, Here we're going to launch these products?"

**Logan Kilpatrick** (00:38:33):
I think it's much higher level. I actually don't think OpenAI is a big OKR company. I don't think teams do OKRs today and I don't have a good understanding of why that's the case, whether or not. I don't even know if OKRs are still the industry. You're probably talking to a lot more folks about who are making those decisions. So I'm curious. Is that something that you're seeing from folks? Is it still common for people to do OKRs?

**Lenny** (00:38:55):
Yeah, absolutely. Many companies use OKRs, love OKRs. Many companies hate OKRs. I'm not surprised that OpenAI is not an OKR driven company. Along those lines, I don't know how much you can share about all this stuff, but how do you measure success for things that you launch? I know there's this ultimate goal, AGI. Is there some way to track we're getting closer? What else do you guys look at when you launch, say DPT Store or assistants or anything that's like, "Cool, that was exactly what we're hoping for." Is it just adoption?

**Logan Kilpatrick** (00:39:20):
Yeah, adoption is a great one. I think there's a bunch of metrics around revenue, number of developers that are building on our platform, all those things. And a lot of these, and I don't want to dive... I'll let Sam or someone else on our leadership team go more into details, but I think a lot of these are actual abstractions towards something else. Even if revenue is a goal, it's like revenue is not actually the goal. Revenue is a proxy for getting more compute, which is then actually what helps us get towards getting more GPUs so that we can train better models and actually get to the goal. So there's all these intermediate layers where even if we say something is the goal, and you hear that in a vacuum and you're like, "Oh, well OpenAI just wants to make money," and it's like, "Well, really money is the mechanism to get better models so that we can achieve our mission." And I think there's a bunch of interesting angles like that as well.

**Lenny** (00:40:12):
I don't know if I've heard of a more ambitious vision for a company, to build artificial general intelligence. I love that. I imagine many companies are like, "What's our version of that?" Before we leave this topic, is there anything else that you've seen OpenAI do really well that allows it to move this fast and be this successful? You talked about hiring people with higher agency and high urgency. Is there anything else that's just like, "Oh wow, that's a really good way of operating?" I imagine part of it's just hiring incredibly smart people. I think that's probably an unsaid thing, but yeah, anything else?

**Logan Kilpatrick** (00:40:45):
I think there's a non-trivial benefit to using Slack, and I think maybe that's controversial and maybe some people don't like Slack, but OpenAI has such a slack heavy culture and it really... The instantaneous real time communication on Slack is so crucial. And I just love being able to tag in different people from different teams and get everybody coalesced. So everybody is always on Slack, so even if you're remote or you're on a different team or in a different office, so much of the company culture is ingrained in Slack, and it allows us to really quickly coordinate where it's actually faster to send someone a Slack message sometimes than it would be to walk over to their desk because they're on Slack and they're going to be using it.

**Logan Kilpatrick** (00:41:27):
And I saw, if you saw, the recent Sam and Bill Gates interview, but Sam was talking about how Slack is his number one most used app on his phone and, "I don't even look at the time thing on my phone anymore because I don't want to know how long I'm using Slack," but I'm sure the Salesforce people are looking at the numbers and they're like, "This is exactly what we wanted."

**Lenny** (00:41:46):
I also love Slack. I'm a big promoter Slack. I think there's a lot of Slack hate, but such a good product. I've tried so many alternatives and nothing compares. I think what's interesting about Slack for you guys is one of the... You don't know if someone in there is just an AGI, that is not actually a person that's just there working at the company.

**Logan Kilpatrick** (00:42:01):
I know there are real people. There is no AGIs yet. But I think, yeah, even Slack is building a bunch of really cool AI tools, which I'm excited to... And that's why there's so much cool AI progress. And at the end of the day, it's so exciting, from being a consumer of all these new AI products. Google's a great example. I'm so happy that Google is doing really cool AI stuff because I'm a Google Docs customer and I love using Google Docs. I like a bunch of their other products, and it's awesome that people are building such useful things around these models.

**Lenny** (00:42:33):
How big is the OpenAI team at this point, whatever you can share? Just to give people a sense of the scale.

**Logan Kilpatrick** (00:42:38):
Yeah, I think the last public number was something around like 750 near the end of last year, 780 or something like that near the end of last year. And we're still growing so quickly, so I won't be the messenger to share the specific updated numbers, but the team is growing like crazy and we're also hiring across all of our engineering teams and PM teams, so folks who are interested, would love to hear from folks who are curious about joining.

**Lenny** (00:43:03):
Maybe one last question here. So you're growing, maybe getting to 1,000 people, clearly still very innovative and moving incredibly fast. Is there anything you've seen about what OpenAI does well to enable innovation and not slow down new big ideas?

**Logan Kilpatrick** (00:43:19):
Yeah, there's a couple of things, one of which is the actual research team, who seed most of the innovation that happens at OpenAI, is intentionally small. Most of the growth that OpenAI has seen is around our customer facing roles, our engineering roles to provide the infrastructure for ChatGPT and things like that. The research team is, again, intentionally kept small and there's all of this talk. And it's really interesting. I just saw this thread from one of our research folks who was talking about how in a world where you're constrained by the amount of GPU capacity that you have as a researcher, which is the case for open AI researchers, but also researchers everywhere else, each new researcher that you add is actually a net productivity loss for the research group unless that person is up-leveling everyone else in such a profound way that it increases the efficiency.

**Logan Kilpatrick** (00:44:12):
If you just add somebody who's going to go and tackle some completely different research direction, you now have to share your GPUs with that person and everyone else is now slower on their experiments. So it's a really interesting trade-off that research folks have that I don't think product folks... If I add another engineer to our API team or to some of the ChatGPT teams, you can actually write more code and do more. And that's actually a net beneficial improvement for everybody. And that's always not the case in the case of researchers, which is interesting, in A GPU constrained world, which hopefully we won't always be in.

**Lenny** (00:44:46):
I want to zoom out a bit and then there's going to be a couple follow-up questions here. Where are things heading with OpenAI? What's in the near future of what people should expect from the tools that you guys are going to have in launch?

**Logan Kilpatrick** (00:44:58):
Yeah, new modalities. I think ChatGPT continuing to push all of the different experiences that are going to be possible. Today, ChatGPT is really just text in, text out or, I guess three months ago, it was just text in, text out. We started to change that with now you can do the voice mode and now you can generate images and now you can take pictures. So I think continuing to expand the way in which you interface with AI through ChatGPT is coming.

**Logan Kilpatrick** (00:45:24):
I think GPTs is our first step towards the agent future. Again, today when you use A GPT, it's really you send a message, you get an answer back almost right away, and that's kind of the end of your interaction. I think as GPTs continue to get more robust, you'll actually be able to say, "Hey, go and do this thing and just let me know when you're done. I don't need the answer right now. I want you to really spend time and be thoughtful about this."

**Logan Kilpatrick** (00:45:48):
And again, if you think back to all these human analogies, that's what we do as humans. I don't expect somebody, when I ask them to do something meaningful for me, to do it right away and give me the answer back right away. So I think pushing more towards those experiences is what is going to unlock so much more value for people.

**Logan Kilpatrick** (00:46:06):
And I think the last thing is GPTs as this mechanism to get the next few hundred million people into ChatGPT and into AI. So I think if you've had conversations with people who aren't close to the AI space, oftentimes you talk about, even if they've heard of ChatGPT... A lot of people haven't heard of ChatGPT, but if they have, they show up in ChatGPT and they're like, "I don't really know what I'm supposed to do with this blank slate. I can kind of do anything. It's not super clear how this solves my specific problem."

**Logan Kilpatrick** (00:46:35):
But I think the cool thing about GPTs is you can package down like, "Here's this one very specific problem that AI can solve for you and do it really well," and I can share that experience with you and now you can go and try that GPT, have it actually solve the problem and be like, "Wow, it did this thing for me. I should probably spend the time to investigate these five other problems that I have to see if AI can also be a solution to those." So I think so many more people are going to come online and start using these tools because very narrow vertical tools are what's going to be a huge unlock for them.

**Lenny** (00:47:07):
So in that last case, a classic horizontal product problem where it does so many things and people don't know what exactly it should do for them. So that makes a ton of sense. Just being a lot more template oriented, use case specific, helping people onboard makes tons of sense. A common problem for so many SaaS products out there. The other ones you mentioned, which was really interesting, basically more interfaces to more easily interact with OpenAI voice. You mentioned audio and things like that. That makes tons of sense. And then this agents piece where the idea is, instead of just it's a chat, it's like, "Hey, go do this thing for me."

**Lenny** (00:47:42):
Kind of along those lines, GPT-5, we touched on this a bit. There's a lot of speculation about the much better version. People just have these wild expectations, I think, for where GPT is going. GPT-5 is going to solve all the world's problems. I know you're not going to tell me when it's launching and what it's going to do, but I heard from a friend that there's kind of this tip that when you're building products today, you should build towards a GPT-5 future, not based on limitations of GPT-4 today. So to help people do that, what should people think about that might be better in a world of GPT-5? Is it just faster? It's just smarter? Is there anything else that might be like, "Oh wow, I should really rethink how I'm approaching my product?"

**Logan Kilpatrick** (00:48:22):
If folks have looked through the GPT-4 technical report that we released back in March when GPT-4 came out, GPT-4 was the first model that we trained where we could reliably predict the capabilities of that model beforehand based on the amount of computes that we were going to put into it. We did a scientific study to show like, "Hey, this is what we predicted and here is what the actual outcome was." So it'll be, one I think, just as somebody who's interested in technology, but interesting to see does that continue to hold for GPT-5, and hopefully we'll some of that information whenever that model comes out.

**Logan Kilpatrick** (00:48:56):
I also think you can probably draw a few observations. One of them, which is GPT-4 came out. The consensus from the world is, "Everything is different. All of a sudden everything is different. This changes the world. This changes everything." And then slowly but surely, we come back to reality of like, "This is a really effective tool and it's going to help solve my problems more effectively."

**Logan Kilpatrick** (00:49:21):
And I think that is the, undoubtedly, the lens in which people should look at all of these model advancements, like GPT-5 is surely going to be extremely useful and solve some whole new echelon of problems. Hopefully it'll be faster. Hopefully It'll be better in all these ways, but fundamentally, the same problems that exists in the world are still going to be the same problems. You now just have a better tool to solve those problems.

**Logan Kilpatrick** (00:49:44):
And I think going back to vertical use cases, I think people who are solving very specific use cases are just now going to be able to do that much more effectively. I don't think that's going to... People have these unrealistic expectations that GPT-5 is going to be doing back flips in the background in my bedroom while it also writes all my code for me and talks on the phone with my mom or something like that.

**Logan Kilpatrick** (00:50:06):
I'm like, "That's not the case." It's just going to be this very effective tool, very similar to GPT-4, and it's also going to be become very normal very quickly. And I think that is actually a really interesting piece. If you can plan for the world where people become very used to these tools very quickly, I actually think that's an edge, and assuming that this thing is going to absolutely change everything, and in many ways I think it's actually a downside, is the wrong mental framing to have of these tools as they come out.

**Lenny** (00:50:39):
Kind of along these lines, you guys are investing a lot into B2B offerings. I think half the revenue, last I heard, was B2B and then half is B2C. I don't know if that's true, but that's something I heard. What is it that you get if you work with opening AI as a company, as a business? What does it unlock? Is it just called OpenAI Enterprise? What's it called and what do you get as a part of that?

**Logan Kilpatrick** (00:51:01):
Yeah, so I think a lot of our B2B customers are using the API to build stuff. So I think that's one angle of it. I think if you're a ChatGPT B2B customer, we sell Teams, which is the ability to get multiple subscriptions of ChatGPT packaged together. We also have an enterprise version of ChatGPT. There's a bunch of enterprise-y things that enterprise companies want, around SSO and stuff like that, related to ChatGPT Enterprise.

**Logan Kilpatrick** (00:51:25):
I think the coolest thing is actually being able to share some of these prompt templates and GPTs internally. So again, you can make custom things that work really well for your company with all of the information that's relevant to solving problems at your company and share those internally. And to me, that's like you want to be able to collaborate with your teammates on the cool things you create using AI. So that's a huge unlock for companies. I think that those are the two biggest value adds. There's higher limits and stuff like that on some of those models, but I think being able to share your very domain specific applications is the most useful thing.

**Lenny** (00:52:00):
I think if you're a company listening and you think a lot of employees are using ChatGPT, basically the simplest thing you could do is just roll it up into a business account with single sign-on and that probably saves you money and makes it easier to coordinate and administer.

**Logan Kilpatrick** (00:52:14):
Yeah, there's also a bunch of security stuff too, like if you want to control. You don't want people to use certain GPTs from the GPT store because you're worried about security or privacy and stuff like that. You don't want your private data going in places. It makes a lot of sense to sign up for that so that you have a little bit more control over what's happening.

**Lenny** (00:52:29):
Okay, got it. There's a launch happening tomorrow, I think, after we're recording this. Can you talk about what is new, what's coming out? I think this is going to come out a couple weeks after recording, but just what should people know that's new that's coming out from OpenAI tomorrow in our world?

**Logan Kilpatrick** (00:52:45):
Yeah, updated, so there's a few different things. A couple of quick ones are updated GPT-4 Turbo model, updated the preview model that we released that dev day. There's an updated version of that. It fixes this, if folks have seen online people talking about this sort of laziness phenomenon in the model. We improve on that and it fixes a lot of the cases where that was the case. So hopefully the model will be a little bit less lazy. The big thing is the third generation embeddings model. So we were talking off-camera before recording about all of the cool use cases for embedding. So if folks have used embeddings before, it's essentially the technology that powers many of these question and answering with your own documentation or your own corpus of knowledge. And like you were saying, you actually have a website where people can ask questions about recordings of the podcast.

**Lenny** (00:53:34):
Lennybot.com. Check it out.

**Logan Kilpatrick** (00:53:35):
Yeah, lennybot.com. And my assumption was that lennybot.com is actually powered by embedding. So you take all of the corpus of knowledge. You take all the recordings, your blog post. You embed them, and then when people ask questions, you can actually go in and see the similarity between the question and the corpus of knowledge and then provide an answer to somebody's question and reference an empirical fact, something that's true from your knowledge base. And this is super useful and people are doing a ton of this. It's like trying to ground these models in reality, in what they know to be true. We know all the things from your podcast to be at least something that you've said before and to be true in that sense, and we can bring them into the answer that the model is actually generating in response to a question. So that'll be super cool.

**Logan Kilpatrick** (00:54:20):
And these new V3 embeddings models, again, state-of-the-art performance, the cool thing is actually the non-English performance has increased super significantly. I think historically, people really were only using embeddings for... It only worked really well for English, and I think now you can use it across so many new languages because it's just so much more performant across those languages and it's five times cheaper as well, which is wonderful. There's no better feeling than making things cheaper for people. I love it. I think now it's like you can embed, I'm pretty sure, it was like 62,000 pages of text for $1, which is very, very cheap. So lots of really cool things that you can do with embeddings and exciting to see people invent more stuff.

**Lenny** (00:55:07):
What a deal. Final question before we get to a very exciting lightning round. Say you're a product manager at a big company, or even a founder, what do you think are the biggest opportunities for them to leverage the tech that you guys are building, GPT-4, all the other APIs? How should people be thinking about, "Here's how we should really think about leveraging this power in our existing product," or new product, whichever direction you want to go.

**Logan Kilpatrick** (00:55:34):
Yeah, I think going back to this theme of new experiences is really exciting to me. I think consumers are just going to be... You are going to have an edge on other people if you're providing AI that's not accessible in a Chatbot. People are using a ton of chat and it's a really valuable service area. It's clearly valuable because people are using it. But I think products that move beyond this chat interface really are going to have such an advantage. And also, thinking about how to take your use case to the next level. I've tried a ton of chat examples that are very, very basic and providing a little bit of value to me, but I'm like, "Really this should go much further and actually build your core experience from the ground up."

**Logan Kilpatrick** (00:56:20):
I've used this product that allows you to essentially manage or view the conversations that are happening online around certain topics and stuff like that. So I can go and look online. What are people saying about GPT-4? And what I just said out loud, "What are people saying about GPT-4," is the actual question that I have. And in a normal product experience today, I have to go into a bunch of dashboards and change a bunch of filters and stuff like that. And what I really want is just ask my question. What are people doing? What are people saying about GPT-4? Get an answer to that question in a very data grounded way.

**Logan Kilpatrick** (00:56:55):
And I've seen people solve part of this problem where, oh, they'll be like, "Oh, well here's a few examples of what people are saying and, well, that's not really what I want. I want this summary of what's happening." And I think it just takes a little bit more engineering effort to make that happen. But I think it's like that is the magical unlock of like, "Wow, this is an incredible product that I'm going to continue to use," instead of like, "Yeah, this is kind of useful, but I really want more."

**Lenny** (00:57:21):
Awesome. I'll give a shout-out to a product. I'm not an investor, but I know the founder, called visualelectric.com, which I think is doing exactly this. It's basically a tool specifically built for creatives, I think specifically graphic design, to help them create imagery. So there's like Dali, obviously, but this takes it to a whole new level where it's kind of this canvas, infinite canvas, that you could just generate images, edit, tweak them, and continue to rate until you have the thing that you need. Visualelectric.com.

**Logan Kilpatrick** (00:57:48):
I'm going to try that out. Is it similar to Canva?

**Lenny** (00:57:50):
It's even more niche, I think, for more sophisticated graphic design, I think, is the use case. But I'm not a designer, so I'm not the target customer. But I will say my wife is a graphic designer. She had never used AI tools. I showed her this and she got hooked on it. She paid for it without even telling me that she was going to become a paid customer, and she created imagery of our dog and all this art. And now it's like on our TV. The art she created is now sitting... It's like we have a frame TV, and that's the image on our TV. So anyway...

**Logan Kilpatrick** (00:58:21):
I love that. What was it called again?

**Lenny** (00:58:23):
Visualelectric.com. Anyway, anything else you wanted to touch on or share before we get to a very exciting lightning round?

**Logan Kilpatrick** (00:58:31):
I've made this statement a few times online and other places, but for people who have cool ideas that they should build with AI, this is the moment. There are so many cool things that need to be built for the world using AI. And again, if I or other folks on the team at OpenAI can be helpful in getting you over the hump of starting that journey of building something really cool, please reach out. The world needs more cool solutions using these tools, and would love to hear about the awesome stuff that people are building.

**Lenny** (00:59:01):
I would've asked you this at the end, but how would people reach out? What's the best way to actually do that?

**Logan Kilpatrick** (00:59:06):
Twitter, LinkedIn. My email should be findable somewhere. I don't want to say it and then get slammed with a bunch of email. You should be able to sign my email, if you need it, online somewhere. But yeah, Twitter and LinkedIn is usually the easiest place.

**Lenny** (00:59:18):
And how do they find you on Twitter?

**Logan Kilpatrick** (00:59:21):
It's just Logan Kilpatrick, or I think my name shows up as Logan.GPT or-

**Lenny** (00:59:21):
Logan.GPT?

**Logan Kilpatrick** (00:59:26):
Or official Logan K.

**Lenny** (00:59:28):
Yeah. Awesome. Okay. And we'll link into it in the show notes. Amazing. Well Logan, with that, we've reached a very exciting lightning round. Are you ready?

**Logan Kilpatrick** (00:59:34):
I'm ready.

**Lenny** (00:59:35):
First question, what are two or three books that you've recommended most to other people?

**Logan Kilpatrick** (00:59:39):
I think the first one is one that I read a long time ago and came back to recently, is the One Room Schoolhouse by Sal Khan. Incredible. Yeah, I don't want... It's the lightning round so I won't say too much, but incredible story and AI is what is going to enable Sal Khan's vision of a teacher per student to actually happen. So I'm really excited about that. And the other one is, that I always come back to, is Why We Sleep. Sleep science are so cool. If you don't care about your sleep, it's one of the biggest up-levels that you can do for yourself.

**Lenny** (01:00:14):
What is a favorite recent movie or TV show that you really enjoyed?

**Logan Kilpatrick** (01:00:18):
I'm a sucker for a good inspirational human story. So I watched, with my family recently over the holidays, this Gran Turismo movie, and it's a story about someone who, a kid from London, who grew up doing SIM racing, which is a virtual race car, and did this competition, ended up becoming a real professional race car driver through some competition. And it's just really cool to see someone go from driving a virtual car to driving a real car and competing in the 24-hour Le Mans and all that stuff.

**Lenny** (01:00:50):
I used to play that game and it was a lot of fun, but I don't think I have any clue how to drive a real car, race car. So that's inspiring. Do you have a favorite interview question that you'd like to ask candidates that you're interviewing?

**Logan Kilpatrick** (01:01:03):
Yeah, I'm always curious to hear what people's... The thing that they so strongly believe that people disagree with them on.

**Lenny** (01:01:12):
What do you look for in an answer that seems like, Wow, that's a really good signal?"

**Logan Kilpatrick** (01:01:17):
Oftentimes, it's just an entertaining question to ask in some sense, but it's also... It's interesting to see what somebody's deeply held strong belief is, I think. And not to judge whether or not I believe in that, but just curious to see why people feel that way.

**Lenny** (01:01:35):
What is a favorite product that you've recently discovered that you really like?

**Logan Kilpatrick** (01:01:38):
On the narrative of sleep, I have this really nice sleep mask from this company called... Not being paid. I just say this, but it's called Manta Sleep or something like that. It's a weighted sleep mask and it feels incredible when I... I don't know. Maybe I just have a heavy head or something like that, but it feels good to wear a weighted sleep mask at night. I really appreciate it.

**Lenny** (01:02:01):
I have a competing sleep mask that I highly recommend. I'm trying to find it. I've emailed people about it a couple of times in my newsletter for gift guides.

**Logan Kilpatrick** (01:02:09):
Yeah.

**Lenny** (01:02:09):
Okay. My favorite is called the Waoaw Sleep Mask, W-A-O-A-

**Logan Kilpatrick** (01:02:15):
What do you like about it?

**Lenny** (01:02:16):
W-A-O-A-W. I'll link to it in the show notes. It makes a lot of room. It's very large and there's space for your eyes, so your eyelashes and whatever eyes aren't pressed on, and it just fits really nicely around the head. And my wife, we both wear eye masks at night. It just, speaking of sleep, really helps us sleep. [inaudible 01:02:37] It doesn't have the weight-ness piece, so it might be worth trying, but everyone I've recommended this to is like, "That changed my life. Thank you for helping me sleep better." And so we'll link to [inaudible 01:02:51].

**Logan Kilpatrick** (01:02:17):
Look at that.

**Lenny** (01:02:50):
Look at us. So adult. Two more questions. Do you have a favorite life motto that you often come back to share with friends or family, either in work or in life?

**Logan Kilpatrick** (01:02:58):
Yeah, I've got it. It's on a Post-It note that I... Right behind my camera and it's "Measure in hundreds." I love this idea of measuring things in hundreds, and it's for folks who are at the beginning of some journey. I talk to people all the time, they're like, "Yeah, I've tried this thing and it hasn't worked." And if your mental model is to measure in hundreds, "I measure in hundreds," the five times that you failed at something, you failed and tried zero times. And I love that. It's such a great reminder that everything in life is built on compounding and multiple attempts at stuff. And if you don't try enough times, you're never going to be successful at it.

**Lenny** (01:03:38):
I love that. I could see why you are successful at OpenAI and why you're a good fit there. Final question. So I asked ChatGPT for a very silly question. "Give me a bunch of silly questions to ask Logan Kilpatrick, head of developer relations at OpenAI," and I went through a bunch. I have three here, but I'm going to pick one. If an AI started doing standup comedy, what do you think would be its go-to joke or funny observation about humans?

**Logan Kilpatrick** (01:04:06):
I think today, I think if you were to do this, I think the go-to question would be something along the, "So an AI walks into a bar," and likely because, again, it's trained on some distribution of training data, and that's the most common joke that comes up, and that's probably... I wonder if you came up with a joke right now, whether or not that would show up in one of the examples.

**Lenny** (01:04:31):
I love it. What would be the joke though? We need the joke. We need the punchline. I'm just joking. I know you can't come up with amazing-

**Logan Kilpatrick** (01:04:37):
That's what we have ChatGPT for.

**Lenny** (01:04:41):
We're already irrelevant. Amazing. Logan, thank you so much for being here. Two final questions, even though you've already shared this information, but just for folks to remind them. Where can folks find you if they want to reach out and ask you more questions? And how can listeners be useful to you?

**Logan Kilpatrick** (01:04:55):
Yeah, Twitter and LinkedIn, Logan Kilpatrick or Logan.GPT on Twitter. Please shoot me messages. I get a ton of DMs from people and it's always really, really interesting stuff. I think the thing that I would love to have help on is if people find bugs and things that don't work well in ChatGPT, I oftentimes see people be like, "This thing didn't work really well." And the key, and I think we as OpenAI need to do a better job of messaging this to people, but having shared chats or actual, tangible, reproducible examples, are the two things that we need in order to actually fix the problems that people have. The model laziness was a good example where it was hard to figure out what was going on because people would be like, "Oh, the model's lazier," but it's hard to figure out what were the prompts they were using. What was the examples, all that stuff? So send those examples as you come up on things that don't work well and we'll make stuff better for you.

**Lenny** (01:05:49):
Amazing. And I'll also just remind people, if you're listening to this and you're like, "Oh, okay, cool. A lot of cool ideas for OpenAI and ChatGPT," what you need to do is actually just go to chat.openai.com and try this stuff out. There's a lot of just theorizing, but I think once you actually start doing it, you start to see things a little differently. And at this point, every day I'm in there doing something, like asking for ideas for questions, doing research on a newsletter post, and it's just a tab I'm always coming back to. And I know there's a lot of people just talking about this sort of thing, and I just want to remind people. Just go. Sign in. Play with it. Ask it questions on something you're working on and just see how it goes and keep coming back to it. Is there anything else you want to share along those lines to inspire people to give this a shot?

**Logan Kilpatrick** (01:06:34):
I love it. I think the phrase of people being worried about humans being replaced by AI, and I've seen this narrative online, that it's not AI that's going to replace humans. It's other humans that are being augmented and using AI tools that are going to be more competitive in a job market and stuff like that. So go and try these AI tools. This is the best time to learn. You're going to be more productive and empowered in your job and the things that you're excited about. So yeah, excited to see what people use ChatGPT for.

**Lenny** (01:07:01):
And then you can expense your account. I think it's 10 or 20 bucks a month. A lot of companies are paying for this for you, so ask your boss if you can just have it expensed and make sure you use the latest version. Anyway, Logan, thank you again so much for being here.

**Logan Kilpatrick** (01:07:16):
This is awesome, Lenny. Thanks for having me in. Thoughtful questions. Hopefully those weren't all from ChatGPT.

**Lenny** (01:07:20):
Nope, only the last one. I did have a bunch of others I had in the belt or in the pocket. I don't know what the metaphor is. In the back pocket, that's the metaphor, but I did not get to them because we had enough great stuff. So no, that was all me. Human AI.

**Logan Kilpatrick** (01:07:35):
Thank you.

**Lenny** (01:07:36):
Thanks, Logan.

**Logan Kilpatrick** (01:07:37):
Lenny.ai.

**Lenny** (01:07:39):
I love it. Lennybot.com, check it out. Okay, thanks Logan. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [11/19] Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital)

**Jake Knapp** (00:00:00):
It's not really about productivity, it's not about time management. It's really just about, look, at any given day, we're lucky if we can have one great moment where we have our peak attention and we use it well. And it's not going to happen every day, but if we have some intention around it, it can happen more often than not. The notion with the highlight is imagine it's the end of the day if someone asks you, "What was the highlight of your day," what would you say? That's the anchor of everything. That's the core, that's the foundation. Things can sometimes be a mess outside of that, and you still feel really good about your days. You still feel really good about the way you're spending your energy.

**Lenny** (00:00:37):
Today, I've got two guests, Jake Knapp and John Zeratsky. Jake and John are authors of two incredible books, Sprint and Make Time. With Sprint, they've helped more than 300 teams design new products and bring them to market, including teams at YouTube, Slack, Gusto and One Medical. Previously, John and Jake worked at Google Ventures, and before that, at Google, where John was a leader on Google Ads and YouTube. And Jake helped build Gmail and co-founded Google Meet. Today, they run a venture capital firm called Character, and they actually just opened up applications for their accelerator program called Character Labs, which you can learn more about at character.vc/labs.

**Jake Knapp** (00:04:17):
Thanks for having us. We're so stoked to be here.

**Lenny** (00:04:20):
I was just re-listening to the audiobook of Make Time to prep for this conversation. And I feel like I kind of know you guys from listening to your voice for so long in the car, and it's a little surreal to be talking to you guys.

**John Zeratsky** (00:04:31):
That was really fun to record. And while we were doing it, we kept saying to each other, it was like we were recording the world's longest podcast.

**Jake Knapp** (00:04:39):
That's what it felt like.

**Lenny** (00:04:41):
Actually, on that, how long does it take to record audiobook? I've always been curious. How much time does that-

**Jake Knapp** (00:04:45):
Well, it takes twice as long as it should have because my stomach kept growling and the microphone would pick it up. And so, John would do a perfect take and we're both sitting in the little room together and the engineer was in the other room and he'd be like, "You got to do it again. You got to do it again. The guy's stomach keeps growling."

**John Zeratsky** (00:05:07):
I think it took two days, right?

**Jake Knapp** (00:05:09):
Yeah, I think it was two days. Yeah, and I think actually they thought it would take two days, so I don't think my stomach slowed us down too much.

**Lenny** (00:05:16):
That is not as long as I thought. I thought it was a month of recording and such a painful experience. Sounds like not so bad.

**John Zeratsky** (00:05:21):
No, honestly, it was really fun. I mean it's weird, but it's just like, I don't know, you can get into this very intense zone where you're singularly focused, right? There's nothing else that you need to do or should do, so it's just like read, drink tea, read, break for lunch, read, drink tea. It's just like this really satisfying flow.

**Lenny** (00:05:45):
That sounds like a great few days.

**Jake Knapp** (00:05:47):
Yeah, I think it was really fun doing it together too. I think it would've been harder to do... I mean obviously people do it and I think they like doing it on their own, but we've been working together for so long, it's always more enjoyable when we get to do something together. So, that made it cool.

**Lenny** (00:06:02):
Amazing. I want to do an audiobook now. That sounds like a lot of fun. So, to start diving into our conversation, so you guys wrote this very seminal book called Sprint, which we're going to talk about. But you also wrote this other book that I have right here called Make Time, that to me was even more powerful and I think it might be even more powerful in people's lives than Sprint. And I think it's one of the most interesting and most fun productivity books out there. My wife actually grabbed the book from my desk the past week as I've been prepping for this, and just started highlighting it. You could see all these highlights in here. She just goes-

**John Zeratsky** (00:06:36):
Awesome.

**Jake Knapp** (00:06:37):
Oh, that's so cool.

**Lenny** (00:06:38):
[inaudible 00:06:38] I want to be more productive. Also, a guest on the podcast introduced me to the book. At the end of the podcast, I'll ask you this too, but I ask people, what book do they recommend most to other people? And he mentioned this book, and so that's how I uncovered it. So, it all comes full circle.

**Jake Knapp** (00:06:49):
That's so cool.

**Lenny** (00:06:50):
So, I thought we'd start with Make Time and then get to Sprint in the second half of the conversation. First question is just what do most people get wrong when they're trying to become more productive?

**Jake Knapp** (00:07:01):
To set the answer up, I'll give you a super brief history of Make Time. And for over a decade, John and I have been, in quotes, designing time as part of our work with startups, helping them find or expand product market fit. So, we developed a design sprint at Google Ventures, which the Sprint book is about. And now, we run this venture fund of our own called Character. And we run these highly-structured sprints with companies. And when we're doing that, we get to control how everything happens. We get to change the defaults of the way the workday happens, of what happens sort of hour-to-hour, minute-to-minute, how people are using technology, how people are interacting with each other. All those things are sort of under our control because we're trying to achieve these big goals in a really short period of time. Everybody focused.

**Jake Knapp** (00:07:53):
So, as this stuff was going on, John and I started applying some of the lessons, the things that we found were working really well in those structured sprints. We started experimenting with applying those in our own day-to-day lives, and we found that some of those things were super effective and they were a bit counter to the way we'd sort of heard or learned about productivity. And there's all kinds of habit books and productivity hacks out there. And I think John and I have probably tried most of them, if not all of them. But it seems like 99% of the people who follow those things are still feeling overwhelmed, they're still stressed out all the time anyway.

**Jake Knapp** (00:08:33):
So, even though we are not productivity gurus, this hasn't been like this thing we were doing forever, it's not our full-time job, but we thought we want to share this framework. So, Make Time, the book and the blog that proceeded it was just kind this side project to share what we learned. And yeah, it seems like it is resonated with a bunch of people. There's this kind of steady stream of interest in looking at these things a different way.

**Lenny** (00:09:00):
I love it. I love that it emerged out of the sprint concept. I know you talked about the book, but I forgot that and these are all very related. I also love that a lot of the best stuff comes from people actually doing the thing. This came from, "I just have discovered all these little things and I'm just going to share it." Not just like, "I need to write a productivity book."

**John Zeratsky** (00:09:16):
Yeah, I think, like Jake said, we both had always sort of been dissatisfied with the state of the productivity art, and we had big things we wanted to do. I mean, when you work in any kind of job, I mean we've both spent our early careers as designers and the job is really all about doing big projects. It's all about being able to focus, being able to spend time on the things that matter. And that's to say nothing of what we want outside of work, things that we want to learn how to do personally, people we want to spend time with. And it's interesting, we've found that when we talk to people about Make Time, they always know. They always know what they want to make time for. The problem is not like what should my goal be or how should I figure out what to do with my life? They usually know, but it's very hard to actually make time for those things.

**John Zeratsky** (00:10:16):
And I think the problem is that most productivity advice focuses on getting better and faster about doing the things that are already in front of you. So, the messages that are in your inbox, the meetings that are on your calendar, a lot of focus on efficiency, like crank through that stuff. Our perspective is basically that those are the defaults. Just like our software that we use, apps that we use have defaults, those are the defaults of life, of the companies that we work in, the culture that we live in. And so, the solution is actually to change those defaults and to really flip this way of thinking on its head. So, it's not about how do I go faster? How do I get more efficient? It's about how do I put the thing that is the most important first in my day or in my life, and then build everything else around that and accept that you're going to need to do a bunch of those little things. You're going to need to answer those messages and go to those meetings, but really, start with the idea of what's most important to you? What do you actually want to make time for?

**Lenny** (00:11:25):
Along these same lines, we're going to talk about this kind of four-part strategy that you recommend, but a couple of things before we get into there. One is along the lines you just talked about is this insight that you had of just like willpower is never going to be enough to get you to make time for the things you want to do. And you had these two concepts of busy bandwagon and infinity pools, so maybe just talk about those two briefly.

**Jake Knapp** (00:11:47):
The idea of the busy bandwagon is just this expectation that everybody's busy. And in the United States, there's kind of this thing that I think if you travel abroad and talk to people for a while, then you come back, you'll notice, which is like if you ask someone, "Hey, how's it going? What are you up to?" And they'll be like, "Oh man, I'm busy." It's kind of the default answer. "I'm busy. Things are busy." And it means, usually, it could mean a variety of things, but usually it's good. Like, "Oh, it's busy, so business is booming," or, "It's busy, I'm overwhelmed," or whatever. But busy, it's kind of the expectations that everybody's busy. And we are, I mean we are busy, but we call it the busy bandwagon because it feels like you should be busy. And it's this inner feeling caused by what we see or perceive other people are doing that drives a lot of the stress. And I don't mean to sound like I'm above it all and have figured it all out. It still drives my stress, this inner feeling that other people haven't figured out, other people are expecting fast reactions from me, all this. That's the busy bandwagon, this sort of feeling that I should be busy, that everyone else is busy. And what that does inside of us is really the core of what we have to change and figure out, this getting out of a reaction mode. The other thing that happens to us are the infinity pools. And John, do you want to describe what infinity pools are in our context?

**John Zeratsky** (00:13:14):
Yeah, we came up with this name because we were trying to think of endlessly replenishing fount of content. So, basically if you can pull to refresh or if it streams, it's an infinity pool. So, this is pure entertainment stuff. This is stuff that people say like, "Oh, I spend so much time on Instagram," but it's also stuff that's important and necessary and productive. Email is a huge infinity pool and it's probably the single hardest thing for the two of us to control and avoid getting sucked into. And anybody listening to this is going to, I think, understand how powerful those pools are and how effectively designed and engineered those products are to be really compelling and to be friction-free and to just make it easy for us to dive back into that pool.

**John Zeratsky** (00:14:15):
And so, when you put these two things together, the busy bandwagon and the infinity pool, you kind of have this, it's like a flywheel, but bad. You feel like you really need to be busy, you really need to be on top of everything. And then, you've got this whole collection of apps and services and products there that are ready to pounce on that, they're ready to take advantage of that set of defaults, that cultural and internal set of defaults that you have about what you should be doing. And for a lot of people, it just sort of spins out of control. So, our view is if you can name those two things, if you can understand those two things, then you can start to deliberately change some of the defaults around them, so that you can put your most important projects, people, work first, like we talked about.

**Lenny** (00:15:04):
I'm guilty of both these things. I feel like the reason I do some of these chats, this one in particular is it's like one-on-one coaching almost. This is going to help me stick to some of the things you teach. And I've already actually implemented a number of the things you recommend, but this is reinforcing it. And then, obviously, also helping all the listeners get better at these things. Before we get into it, one last question is just like real talk, how how's your guys' productivity? You wrote this book, it sounds amazing. There's 87 I think pieces of advice. How is it going for you guys? As we go through, I want to hear what you're actually using, but just broadly, how's your productivity?

**Jake Knapp** (00:15:40):
At the top of the interview, Lenny, you asked, "What do most people get wrong when they think about this productivity, time management, whatever?" And I'll frame my answer in those terms. So, most people, I think they try to get better and faster at doing what's right in front of them. We don't change the defaults in our environment, so we can focus and spend time on these different more important things. And if you think of that sort of what do I want to do? What's my goal? What do I want to spend time on that John referred to as project A, generally the things we want to do, these project A things, they're big, they're not easy to start, they're slow to create, dopamine hits, they're non-urgent. Like boss is not asking for them if you have a boss. And generally, the tasks and activities that stand in our way that keep us from doing project A, they're small, they're medium size, it's obvious how to start them, they create dopamine right away, they're supposedly urgent, email meetings, TikTok, Instagram, news, what's on your OKRs, all these things.

**Jake Knapp** (00:16:47):
And I know what's on your OKRs may not sound like it's a peer of those others, but in a way it really can be. So, these big things, they're at odds with these little things that get in the way that the busy bandwagon expects us to do, these things that have infinity pools built in. And so for me, right now, it's a constant battle between the Jake and the busy bandwagon and my inner feeling of how can I live up to people's expectations of me and respond in the way that I should and react in the way that I should? And then, how can I do the project A stuff, the big important stuff? A lot has changed in my life since we wrote the book.

**Jake Knapp** (00:17:28):
The summary is every few months I need a few new experiments. I have found in what has been some trying times that the tactics and the framework that we use... Because it's kind of simple and it sort of fits with these experiences that I've had for many years doing sprints, that it works. And that if I can go back to that, that if I can create space for it, if I can think about this as it's a series of experiments, if I can look at myself with curiosity and say, "Why are things not working out?" And then try to experiment my way out of it that I'm able to. But yeah, so at any given point in time, I probably give myself a B to B-, and sometimes it's a C and sometimes it's a D, and sometimes it's an A, and I'm really plugging away, but it's totally an ongoing challenge.

**Jake Knapp** (00:18:22):
So, I'm not going to sit here and say, yeah, just follow me with a drone for 48 hours and you'll think that's exactly how you should do things. But part of our philosophy, I think that part of the way I look at it is it can be a mess. And yet, if you can create the space for those project A moments, for your highlights, that can shape everything else, if you just have those moments. Things can sometimes be a mess outside of that and you still feel really good about your days, you still feel really good about the way you're spending your energy.

**John Zeratsky** (00:18:56):
And having a framework for it gives you a path back. If you're just stuck and you're looking... You're sort of grasping for hacks. You're sort of like, "Oh, I read this blog post about this thing, I'll try it." That might have some short-term effect, but ultimately, you're probably not going to stick to it. You're probably going to fall back into that place of overwhelm and disappointment and burnout. But we find that if you have a system, that you can use the system and you can return to it and continue to build on and experiment, that you can make more sustainable progress on these things.

**Lenny** (00:19:33):
I think a really important takeaway from these two stories you guys just shared is you don't have to do all of these things. You don't even have to do most of them. If you just do one or two, if you find one or two things that can make you a little bit more productive every day, that makes a huge dent. And so, I think it's okay to feel like, "Oh, I tried this stuff. It didn't work." I think as long as you take a couple of things away today that might be useful to you, and then just try them again in the future. If they end up not working out. Like you delete an app and then you reinstall it, I think that's okay. So, I think that's an important takeaway from this is don't feel like you're failing if you're not doing all of the things that we're talking about today.

**Lenny** (00:20:10):
But let's get into it. There's this kind of four-part framework for how to help yourself be more productive. Basically, if you could just give an overview and then we'll just talk about each of these steps one by one. So, the four parts are create a highlight, laser, energize, and reflect. So, I'll turn it over to you guys just broadly, and then let's go through each of these one by one.

**Jake Knapp** (00:20:30):
It all starts with this notion of a highlight. And highlight is, I hate to say this, it's the most powerful best part, I think of the whole process. And I hate to say that because John came up with it. It wasn't even me. But I have to admit, it's really good. And I think as folks have read the book and shared it, that's the thing we hear back from people. If you could just do one thing from this book and try this out, it's a big deal.

**Jake Knapp** (00:20:54):
The notion what the highlight is, start your day out and you imagine it's the end of the day, you're looking back on the day. If someone asked you, "What was the highlight of your day," what would you say? What do you want to say at the end of today was the highlight of today? And you start there, just like, "Okay, what would I like to say the highlight of the day was?" And you might think about what's urgent. Sometimes the highlight is this thing that really has to happen today. Today is the day there's a big meeting, or there's this thing I absolutely have to get done for work for tomorrow. That could be your highlight and getting that done well, having good attention to that will be very satisfying.

**Jake Knapp** (00:21:37):
But a lot of times the highlight comes from joy or satisfaction, projects that wouldn't otherwise get attention. And it also doesn't have to just be something at work. It could be people in your life that you want to spend time with, a hobby that you want to spend time on. If you want to get better at Mario Kart, having a good session at Mario Kart, whatever might be the highlight of your day. The notion is just in the morning to think, "What is it and what is that highlight going to be?" And then, try to find a block that's 60 to 90 minutes. That's just usually the rough time we think it takes to really get in the zone on something, do a really excellent job, be totally focused on it. So, that highlight, that's the anchor of everything. That's the core, that's the foundation. And you start that way, you're now trying to shape your time around that highlight, and making sure that you have your peak energy, your peak attention when the time for that highlight comes around.

**Jake Knapp** (00:22:37):
So, laser is about the tactics you might need to actually focus on that thing. In highlight, we have a set of tactics for how to create and think about and frame that highlight. Laser, we have a set of tactics for how do you pay attention when that time comes? Then for energize, it's about having the right amount of energy to do the thing, to pay attention. My highlight for today is trying to be coherent in this podcast, so this morning I need to think about what's the best way for me to have peak energy when a podcast starts.

**Lenny** (00:23:08):
That's my highlight too, actually. I have [inaudible 00:23:10].

**Jake Knapp** (00:23:10):
Oh, good. Right on. Okay.

**Lenny** (00:23:11):
Record a great podcast episode.

**Jake Knapp** (00:23:14):
Excellent, excellent. Okay. Yeah. And if you're not watching on video, Lenny had a sticky note and he wrote it down. So, that's actually literally the best way to do this is write it down on a sticky note, put it somewhere where you can see it. And so, you've got highlight, laser during the time of the highlight, energize, make sure you have the energy you need when the time comes. And these are just tactics around sleep and food and exercise, and just things that help with your mental energy, not crazy stuff. And then the final thing is reflect, and this is where we think about this as the scientific method. Did it work? Did what I tried today work out? And if not, just being curious about it, what didn't? And adjusting and trying to think, "Okay, maybe there's another tactic I can try."

**Jake Knapp** (00:23:54):
So, the book is like... What are there like 87 tactics in the book? There's a lot of different approaches, but the expectation is not you're going to use all of them. And the expectation is not that-

**Jake Knapp** (00:24:00):
... expectation is not you're going to use all of them. And the expectation is not that all of them will work for each person. I use different tactics than John does, and some of his don't work for me, and vice versa. But that idea of centering on a thing, focusing on it, having tactics for that, having tactics for energy, and then having some tactics to reflect and reframe and be curious. That taken together, we find, just can reframe the way it feels. It's not really about productivity. It's not about time management. It's really just about, look, in any given day, we're lucky if we can have one great moment where we have our peak attention, and we use it well. And it's not going to happen every day, but if we have some intention around it, it can happen more often than not.

**Lenny** (00:24:47):
I think that last point is so important and why the highlight works so well for me is usually there's... You don't get anything amazingly done in a day, often. And usually, you're just distracted by all these things, and you're doing all the easy stuff. You talked about this idea of Project A, like here's the thing I really want to get done, but the dopamine hit us so far in the future, and it's so hard. And so, the reason I think the highlight is so powerful is, you get one thing done you're proud of, that is a great day. And it may sound crazy that that's true, but it's so true.

**Jake Knapp** (00:25:14):
Yeah, totally.

**Lenny** (00:25:17):
So, I want to talk more in depth about each of these four things, and maybe spend the most time on the highlight and the laser because I think that's where most of the impact comes from.

**Lenny** (00:25:25):
So, with the highlight, do you have any advice? You shared a couple examples of how to come up with like, "Here's the thing to pick for the day." There's a few questions that you recommend, and I think you shared a couple of them. And then, are there any examples of highlights from your guys', I don't know, past couple of weeks that would be good for people to hear an example? And then, also, there's this calendar component, which maybe fits into the laser, but I guess that feels like a really important element of this. So, if you just talk about that?

**John Zeratsky** (00:25:51):
For me, and again, this is where the framework is intentionally flexible, different people have different highlights. But for me, I am very project oriented. I'm very work oriented. And for me, most days, a really good day comes from having made progress on something that is really important to me. So, my highlights are usually focused work, creative work related. And this has become even more important since we started our own VC firm three years ago. And before that, I was sort of, I guess, more or less a writer, full-time writing, and speaking at events, and doing some consulting. And before that, I was a partner at Google Ventures, at GV, and before that I was a product designer. So, I've been through different modes and contexts in my career. But if you know any VCs, if you're listening to this and you know any VCs, they're probably the busiest, most frazzled people that you know who are constantly on email, constantly in Zoom calls and meetings, and on airplanes all the time.

**John Zeratsky** (00:27:08):
And so, the natural environment of that work is the busy bandwagon, and it's to have a lot of infinity pools that you need to care about. And so, in that context, in order for us to make progress on projects, in order for us to move the ball on a launch related to this program, Character Labs, that we run with pre-seed founders that's coming up, or we're writing a new book, and that's a big project, or working with one of our portfolio companies and running a sprint with them, or writing a newsletter that goes out to our LPs, those things are all really important, and I feel like they give us a unique edge as a VC firm.

**John Zeratsky** (00:27:55):
If we accept the premise I said before, that most VCs are just sort of frantically running around, if we can take these bigger swings at things, then theoretically, they should really help us be successful. So, most of the time, it's all a very long way of saying that most of the time my highlights are like, "What do I want to accomplish at work? What is the thing that I want to get done today?"

**John Zeratsky** (00:28:18):
And so, what I do then is, I structure my calendar around making time for that. There's a tactic in the book called Design Your Day that is really about kind of drawing out your day, and using your calendar as a canvas where you can design how you want to spend your time rather than using your calendar as a thing that is done to you, a thing that tells you what you have to do. Reclaim control over that.

**John Zeratsky** (00:28:48):
And so, most days, the first half of the day before lunch is my focus time, and I protect that very, very intensely, and then use that time to work on whatever my highlight is.

**Lenny** (00:29:06):
We had a previous guest on, Neer Eyal, also talking about productivity, and he had actually the same advice of just using your calendar as your to-do list, basically, because that's where time's going to go, what your calendar's telling you to do. So, I think there's a pattern here that I think people need to pay attention to.

**John Zeratsky** (00:29:22):
Yeah, definitely. Yeah, and I mean, we take it even further, and we have sort of a calendar template that we use as a team. So, we have certain times of the week. And it's not exactly the same for all of us on the team, but there are certain times of the week where it's like, yeah, this is when we do these kinds of things. This is when we have these kinds of meetings.

**John Zeratsky** (00:29:43):
And not to say that those are all standing meetings, although we have some of those as well, but these are kind of the content buckets in the template that we can fill with a specific type of activity, but then other parts of the template are sort of reserved for focus work, reserved for individual, solo time to work on things that we need to get done.

**John Zeratsky** (00:30:03):
So, yeah. I think the calendar is, at an individual level and especially at a team level, is this really powerful tool that most people just kind of... Not only do they not use it as a tool, they just sort of hate it. They're sort of like, "Ugh, my calendar, it's a mess. If I could live without a calendar, that would be the dream." But I think if you can use some of these tactics or use other approaches to reclaim it, and use it proactively as a tool for yourself, it can really help you structure your time around the things that you care about.

**Lenny** (00:30:41):
Yeah. The way I've been starting to use my calendar is this way, exactly, is I try to prepare for work on next week's newsletter post for like an hour and a half, then prep for the podcast coming up in a few weeks. So, it's very specific and broken up.

**Lenny** (00:30:55):
Along those lines, I often don't do these things as I planned. And one of your principles, something around Groundhog Day, it's okay to repeat it if you didn't do it. If you highlight you didn't do, just repeat it again and again until you do it. Right?

**Jake Knapp** (00:31:09):
I think that what's so cool about this notion of Groundhog Day. And if you've seen the movie... Well, if you haven't seen the movie, see the movie. What a great movie.

**Lenny** (00:31:09):
It was a good movie.

**Jake Knapp** (00:31:15):
If you've seen the movie, you know it's like, not to give it away, but he gets better and better at doing the day, and that's kind of this core philosophy that we take on.

**Jake Knapp** (00:31:30):
I think a lot of the time, when in the past I have thought about, "How can I be effective with my time? How can I be productive?" It's beating myself up. It's not a good feeling to be in that head space of like, "I'm screwing up. What can I fix?"

**Jake Knapp** (00:31:49):
And this notion that it's like, you're going to have another chance, you're going to have another chance. "It's okay, just try again, just be curious about what happened," is a big deal. And starting with the calendar, using the calendar as a framework for saying, "Hey, here's what actually happened. Here's what I think is going to happen." That's what you're saying when you do this Design your Day tactic.

**Jake Knapp** (00:32:12):
And I did this exercise earlier this week. I was switching to a new calendar thing, and trying some new features with... We invest in this company called Reclaim, and they do this stuff-

**Lenny** (00:32:26):
I'm an investor in Reclaim also.

**Jake Knapp** (00:32:27):
Oh, well.

**Lenny** (00:32:28):
How about that? Not planned, this promotion.

**Jake Knapp** (00:32:33):
Yeah, little [inaudible 00:32:36] there.

**John Zeratsky** (00:32:37):
It sounds like we knew that, but we actually didn't know that. I didn't know that you-

**Jake Knapp** (00:32:37):
We did not know that.

**Lenny** (00:32:41):
How about that?

**Jake Knapp** (00:32:41):
That was just discovered. So anyway, I was just looking at my calendar, and I was like, you know what? I'm going to do what John does. When I wake up, I'm going to schedule when I exercise, when I eat breakfast. I'm going to schedule when I take a shower, everything, and block it all out. When I walk and feed the dogs, everything's going to be on there, so that then I can have this idea, and when the day starts, I know there's slots for all those things. And then I've found this week that what I thought happened, how long I thought those things take, was not how long they take. And so, set that thing to repeat every day and look at it, and then I'm like, "Oh, okay, interesting. That's not what happened."

**Jake Knapp** (00:33:20):
Okay, so I can adjust it. I can adjust the template and be a bit more kind to myself about this part, be a bit more kind to myself about that part. Gosh, the morning time wasn't a good focus time for me. I'll see if I can... Is there a way I can make that block happen in the afternoon? It's just a helpful way to track stuff and see it.

**Jake Knapp** (00:33:41):
Especially, I think a lot of people are visual learners. We can benefit from seeing things. It's not everybody, but a lot of us are in that camp. And when you put it on the calendar, you can see it, and that helps a lot.

**Lenny** (00:33:54):
And also keeps someone else from booking that time. Double win.

**Jake Knapp** (00:33:58):
Not to be undervalued, keeps someone else from booking that time. Right. And they look, they see, oh, okay, Lenny's already got stuff going on. I figured out, okay, I better be cautious before I ask for something. And that default, to be helpful to other people, and say yes when they put something on a free spot on your calendar, defeats a lot of our inner purposes.

**Jake Knapp** (00:34:20):
And one core idea I don't think we've mentioned yet is that we strongly believe in people's intuition about how they should spend their time if they have the chance. What really is important. And that is true. We're talking about running this VC fund, or writing books, which are obviously very like, well, we're in charge of those things.

**Jake Knapp** (00:34:39):
But this is also true, we've been employees in big organizations, I also believe it's true that if you have a boss, and a boss's boss's boss, that you have great insight about what, if you had a window of time, would be the highest leverage thing for you to do. And it might not show up on your OKRs, it might not be on your boss's radar, your boss's boss's boss's boss's radar. You have great intuition, and we want to create space for you to do that thing because you're going to feel better about it, you're going to be more satisfied, and also good things are going to happen.

**Lenny** (00:35:10):
We're spending a lot of time on this highlight, but I think it's because it's so powerful. It's such a simple idea, but so effective. So, just to kind of give people tactical advice for how to actually implement this, just a couple things that I'll summarize.

**Lenny** (00:35:23):
One is, to pick the highlight, you had a couple of questions I have here, for how to help you pick one for the day. So, you either ask which highlight will bring you the most satisfaction? Or, when I reflect on today, what will bring me the most joy? Maybe that's the same question. But I-

**Jake Knapp** (00:35:39):
Slightly different, slightly different.

**Lenny** (00:35:41):
Slightly different. That's true. Okay, good.

**Jake Knapp** (00:35:43):
Satisfaction could be like, "I know this thing has to get done, and I got it done."

**Lenny** (00:35:47):
Good point.

**Jake Knapp** (00:35:47):
Joy could be like, "Man, that was great." And they're in the same family, but they're cousins.

**Lenny** (00:35:55):
Great point, great point.

**John Zeratsky** (00:35:56):
Yeah. And I mentioned, a lot of my highlights, personally, are very much in the urgency or satisfaction camp. They're these big chunky projects. I got it done. I finished that deck. I finished writing that thing.

**John Zeratsky** (00:36:11):
But I also try to stay attuned to when I need something else in my day, when I need... I need some joy. I need some fun, some play. I need to prioritize going for a run, or going for a walk, or cooking a big dinner. And so, I trust my gut on those things, and I say, "Okay, what's most important to me today is not to be productive, but to do something else."

**John Zeratsky** (00:36:39):
And sometimes that's the best highlight for me. For other people, maybe that's their highlight every single day. Maybe they work as a... I don't know, I've talked to a lot of people who work in healthcare settings about this. They're a nurse or a doctor, and when they're at work, they're at work. They're not bouncing around between meetings and emails and Zooms. They're on their feet. There's no time to do anything else. So, their highlight is probably something they need to do at the end of the day to unwind, or take care of themselves.

**John Zeratsky** (00:37:11):
So, you have these three different strategies that we talk about, urgency, satisfaction, and joy, as being three different places you can look for the right highlight for you each day. But ultimately, I think it comes down to just trusting your gut and sort of asking yourself, like you said, "What do I want to look back on and have said, yeah, I'm glad I made time for that"?

**Lenny** (00:37:33):
Awesome. So, you touched on the third. So, it's basically, what would give you the most satisfaction? So, in the morning, you essentially ask, or the night before. I think one of you, I forget, because when I was listening to the audiobook, I don't know who's talking. But one of you is like, "I like to do it the day before." Is that right?

**John Zeratsky** (00:37:48):
Yeah, that's me.

**Lenny** (00:37:50):
Okay. Okay.

**Jake Knapp** (00:37:51):
That's John talking.

**Lenny** (00:37:52):
Okay. So, the questions you asked either the night before or in the morning are, "What would give me the most satisfaction today, or the next day? What would give me the most joy? Or what's the most pressing thing that I need to get done?"

**Lenny** (00:38:03):
So, you do that, and then the advice is either write it on a Post-It... I actually bought these tiny little Post-Its by accident. I was trying to buy regular Post-Its, and they're actually really great for this specific use case, so it's perfect. Write your highlight, stick it on the monitor.

**Lenny** (00:38:17):
So, that's one way of doing it. The other is stick it in your calendar, where you have focus time. In theory, it's like every day, here's my focus time, where you have the most energy. Is that the general advice?

**John Zeratsky** (00:38:28):
Generally, although I think that that's probably more important for a certain kind of highlight. I have focused time most mornings. To be really specific and nerdy about it, Monday, Wednesday and Thursday mornings I have focus time. Tuesday and Friday mornings I have meetings. But on a Thursday night, my highlight might actually be to have friends over and cook dinner. And that's not the same as focus time, but it's this pressure release valve where I'm like, "That's the thing that I want to make sure..." I want to make sure I wrap up email at 5 so that have time to get everything ready, but it's not necessarily that peak energy moment in the way that we might think about being productive or getting things done or getting into that flow state.

**Jake Knapp** (00:39:22):
Awesome.

**Lenny** (00:39:22):
So, there's a lot of ways to do it. So, maybe you just take away, if you're listening to this, is just think about what could be your highlight for today or tomorrow?

**John Zeratsky** (00:39:30):
Yeah. And I would say, go one step further and make sure to write it down. Don't just think about it, because there's something really special that happens when you write things down, even if it's on a sticky. Even if it's in your notebook, your journal, even if it's a note on your phone. Take that step as well.

**Jake Knapp** (00:39:50):
Even if you don't see it again, just writing it down is a big deal.

**John Zeratsky** (00:39:55):
Yeah, that's a really important point.

**Jake Knapp** (00:39:56):
I can give you a concrete example of a highlight, and a failed highlight, from yesterday, actually. And so, most days these days, my highlight is around making progress on the book. John alluded to working on a book, and so obviously it's a huge project. I heard it said that if you are writing books, it's like having homework forever. You always feel like there's always more to do. And so, that's mostly been my highlight.

**Jake Knapp** (00:40:24):
But yesterday, I wanted to prepare for this podcast. I knew that was going to be satisfying, to feel like I was ready. We don't think about talking about Make Time all the time, like we said, it's sort of like a side project for us. So, I wanted to be ready and somewhat coherent. And I knew I'd be satisfied, but I also knew it was urgent. We're going to be doing the recording today. So, that was my highlight. Write that down. "Get ready for podcast."

**Jake Knapp** (00:40:50):
And I had two focus blocks, one in the morning, one in the afternoon. It should be easy. Focus block number one, kind of just didn't do a good job. I was distracted, I was in my email, I was doing everything that I would say you shouldn't do, I was doing. Feeling down on myself. I've become a loser. I didn't get anything done.

**Jake Knapp** (00:41:10):
Okay, second focus block. Man, now the pressure's on. I got to do it. And so, I finally get into the zone. And my wife thinks I have a pretty serious case of undiagnosed ADHD, so a lot of it is just, if I really do have a deadline, then I really will click in. So, now I have a deadline. I'm doing it, and I'm making notes, and getting there, but I feel like there's still a ways to go.

**Jake Knapp** (00:41:32):
And my 12-year-old son bursts into the room, and it was, "Oh gosh, you're invading me right when I'm at peak focus." And he is like, "Hey, I'm going to do one more trip outside to sled in the snow. Do you want to come?" And I'm like, first reaction, "No, absolutely not. I can get this thing done. It's my highlight. This is the one thing I need to do today. I can do it max level of quality if I can just stay in this precious zone of focus."

**Jake Knapp** (00:42:02):
But then I was like, "Wait a second, what's really going to be the highlight of my day? What's really going to be the highlight, the thing that I might actually remember in the future?" We rarely get snow here. I live on this island in Washington state. We maybe get significant snowfall once every two years. We've only lived here for a few years. He's 12. He loves snow more than anything in the world. He loves snow. But he grew up in California, so he hasn't had many days, and he's 12. He's on the cusp of being a teenager. There's not, maybe, any more days in his life that he's going to want me to get on the sled with him and wrap my arms around him and go down the hill.

**Jake Knapp** (00:42:38):
I was like, "I got to get out there." So, okay. Pause this, ran outside. We did it. And man, it was magical. And I didn't know we were going to get one more in, because the snow was supposed to be melting already. We went down the hill, we went down the hill, we went... It got dark, we had to stop. But it was so magic. And I remember the very last end of the sled run, and it's like the last one, and he's like, "Man," he's like, "That was a great last sled run. So glad we did it."

**Jake Knapp** (00:43:10):
And I was like, "Yeah, so glad we did it. It's great." Come back inside, 15 minutes. I try to hustle and get this done. So, I was like, maybe it was like 80% or 75% to where I wanted to be on this. I couldn't check off that highlight as being the most important thing. But because of the framing of, it might be wrong, what am I going to remember, all this stuff, it just felt natural to me to switch modes and say, "Oh my god, that actually is a highlight. That's this thing that's going to be really, really precious. That's where the joy and the satisfaction are most for today."

**Jake Knapp** (00:43:47):
And still, because I had written down the other thing, I still did it instead of churning on email the entire day. But I screwed up twice, but it still turned out pretty good. So, anyway, that's kind of what it can look like at its best. And a lot of times, it doesn't make that much sense, and a lot of times I miss the special moments, or I miss the key work moments, or the key time when I could have gotten the most done. But I just feel better about it, which is a lot of what this is about. I just feel better about it because I feel more intentional.

**Lenny** (00:44:17):
Well, thank you for sharing the real talk. I think you made the right choice. I feel bad for having you have to decide between your kid and this podcast.

**Jake Knapp** (00:44:24):
You didn't have anything to do with it. No, no, no. I just wanted to... It's selfish for me to want to be prepared. I just want to look good. I just want to sound like I know what I'm talking about.

**Lenny** (00:44:32):
Well, it's working out. It all worked out. That's a great story. It reminds me, in your book at some point, I forget who it was of you that had to... You're like, "Here's my priorities in my life right now." And it was like family, writing, Make Time, something else, and then you're like, "Okay, actually Make Time is more important right now than my family," because you just have to get this done, and I wonder if this is a counter.

**Jake Knapp** (00:44:51):
Well, yeah. I mean, I think that part of what people have found useful about Make Time is that John and I come at this from different perspectives. And I have kids. I have a twelve-year-old and a twenty-year-old, sons, and dealing with being a dad is a big part of how I try to figure out how to make sense of what to do.

**Jake Knapp** (00:45:13):
And John doesn't have kids, and so he has it easy. No, he doesn't, but that's just a different frame of mind. And I think sometimes I read something that people without kids wrote, and I think, "Well yeah, sure. I am sure that's wonderful for you, but what about X-Y-Z?"

**Jake Knapp** (00:45:34):
And although, I'm sure a lot of people who have more kids, or when they have young kids, it would... But that's a real part of it. And whether it's your family, your significant other, anything that's going on in your life that's not part of your work, there are times when you, on a day, or in a moment, you have to shift those priorities. And it can help to just be this idea of stack-ranking things, and being clear about it, can help you just come to terms with it. "I'm making that decision right now. It makes sense to make right now." Or at least, I can see that I did it, and if it seems like I screwed it up, I'd flip it back. I know where it happened.

**Jake Knapp** (00:46:14):
A lot of this is just like if you were designing a product or writing code or whatever, you can see that's where the bug happened. I'll just try to fix that line.

**Lenny** (00:46:23):
Yeah. I love how real you're getting, and it also reminds me of... We just had a kid. He's seven months old, so I'm going through a lot.

**Jake Knapp** (00:46:30):
Oh, congratulations.

**Lenny** (00:46:31):
Thank you.

**Jake Knapp** (00:46:31):
That's busy times. Seven months old is busy times.

**Lenny** (00:46:34):
Yeah, that's great.

**Jake Knapp** (00:46:34):
People always told me, told us, when we had kids when they were babies. They're always like, "Oh, just you wait." I just feel like this is a thing that people want to tell other parents. "Just you wait until this happens." And then one person said, "You know what? Generally speaking, it gets easier and easier and easier. Every month, every week, generally speaking, it gets easier." And I think that is true, so just keep that in mind if you're ever feeling like it's overwhelming.

**Lenny** (00:46:59):
No, I think that is true. I've experienced that. It also gets more amazing. That's what I'm finding, too.

**Jake Knapp** (00:47:03):
Yeah, yeah.

**Lenny** (00:47:05):
**John Zeratsky** (00:48:37):
Yeah, the basic principle with laser is that willpower is never going to win, and there's great research on this, but for now just trust me, you're not going to white-knuckle your way through not looking at Twitter when you're trying to work. So it's all about making it hard, creating barriers to getting distracted. So a few things for me, I'm not on Instagram and I'm not on Facebook. I was on both of those things and I left both of them, I disabled my accounts. I am on Twitter and LinkedIn, but I don't have either of those apps installed on my phone. I stay logged out of those sites on my computer, except for when I want to use them for some specific purpose.

**John Zeratsky** (00:49:22):
LinkedIn I need to use all the time, because I'm a VC and I have to look people up and stuff, so I found this Chrome plugin, or Chrome extension, I guess is the right word, that disables the feed in LinkedIn. So when I go to LinkedIn.com, it's the search bar at the top but there's no feed, which is amazing because I can use LinkedIn as the phone book and then not get distracted. So those are some of the very, very concrete specific things that I do, all, again, with the goal of putting a speed bump between me and that thing so that if I go, and I don't do this much anymore but I used to, literally my hands on the keyboard would just be like, T-W-I, like Twitter.com, and then you see that log in screen instead of my juicy feed and I'm like, oh yeah, right, okay, I did that on purpose, great, I broke that feedback loop a little bit.

**Lenny** (00:50:18):
I did a similar thing with Twitter/X, where I deleted the app and I just used the mobile website. I think this point of logging out is really powerful, I think people haven't heard that idea as much, because it's not like you can't log in really easily, you just click a couple things and you're back. But to your point, it reminds you, okay, I see, I really shouldn't have done this.

**John Zeratsky** (00:50:37):
Well, I also signed up for two-factor authentication for everything, not because I care about somebody hacking my account, but because it's another speed bump. Because that way, even if your browser remembers your password, or I use one password, so even if the browser extension is going to fill it in for me, there's still another step, so it's sort of reverse engineering my own distractibility.

**Lenny** (00:51:03):
That feature that everyone's always talking about that Apple built of the code being automatically there in the keyboard, that's counter to this friction that you've created.

**John Zeratsky** (00:51:11):
Yeah, yeah, that's true.

**Lenny** (00:51:12):
Okay, so it's interesting is I had this, and then I just like, goddammit I really just want to be on Twitter. And so I just re-installed it again recently, and I need to fight that again.

**John Zeratsky** (00:51:22):
Well, I go through cycles like that too, and I go through that a lot with email. Jake, you still don't have email on your phone, is that right?

**Jake Knapp** (00:51:33):
No, I would be on the floor checking email right now on this call if I did, on the floor.

**John Zeratsky** (00:51:38):
I used to do that, Jake inspired me a long time ago to remove email from my phone, and so for years and years that's been my default. But more recently I've had more reasons to install it, mostly related to travel, if I'm on the go and I just want to stay on top of things. And something that Jake and I have talked about a lot is you go through these different cycles of, hey, I need this thing, or I want this thing, and then part of the reflect step, part of paying attention and reflecting on how it's going is to recognize, oh wow, I've actually been spending a lot of time on email on my phone, or a lot of time on Twitter, maybe I'll just uninstall it for a while. Maybe I'll just reset and do that for a while. And then there'll be some other thing that happens that causes you to reinstall it, and that's totally fine, because you're being deliberate about it and you're paying attention, rather than saying it has to always be this way forever and it's set in stone.

**Lenny** (00:52:35):
That's a great tip of just coming back to it, not feeling like you're defeated, it's like, all right, let's try this again.

**Jake Knapp** (00:52:40):
Yeah, I think a big part of it is if you can experience the feeling of not having it on your phone. Like I'm old enough to have lived in a world building products where there were no smartphones, and we got a lot done back then, things happened. I mean, for God's sake, they designed the first iPhone without being able to use iPhones while they did it, you can do a lot. So this idea that we have to have it or everything's going to fall apart, that's just not true for 99.99999% of everyone.

**Jake Knapp** (00:53:16):
It's interesting to see what it feels like if you delete all of the infinity pools off of your phone, and this is something I did out of rage at myself in 2012. It was another situation where I was with my kids, who were much younger at the time, and I was spending time with them, we're playing wooden trains, and all of a sudden my son's like, "Dad, dad, dad, dad, dad," and I'm like, "God, what?" And I didn't even realize it but I was on my phone, and I don't even remember what I was doing, email or something, but I think I told him, he's like, "What's on your phone?" Because to him, he was like, we're doing something really fun, so if you're on your phone it must be something really cool, maybe it would be a cool thing to share, because this is great, so it must be another great thing. He wasn't trying to shame me or anything.

**Jake Knapp** (00:54:06):
And I was all defensive, I'm like, "Well, I need to do this for work," which was, I think, my internal monologue of why I was doing this thing that actually was just a really low-friction dopamine hit. And then I thought, God, this is not what I wanted, this is not why I worked so hard today so I would get done with my work so I could be home in time to do this before my kids go to bed. And I was like, screw this, so I just started deleting things on my phone, and I deleted email and I deleted Facebook and I deleted this, everything that had an infinity pool, everything that had an infinite amount of content. News is like this, anything streaming.

**Jake Knapp** (00:54:44):
When we wrote this book, it came out in 2018, I think we said we thought it was going to get worse, and it has. But at that point in time there was really Netflix, and now there's all these streaming services. At that point in time there was Instagram and Facebook, but now there's TikTok, the best part of every video available instantly right here. This stuff, it only gets harder to resist. When you clear all that stuff off of your phone, it's painful, the idea of deleting all this stuff, and each time the phone's going to ask you, "This is going to delete all the data and settings, are you sure you want to do that?" It doesn't want you to. And when you do that though, what does that feel like? And it's usually a feeling of discomfort, but also relief that I don't have to check this, this thing, I don't have to check it, I don't have to.

**Jake Knapp** (00:55:34):
And if you've ever felt like your phone was in the Lord of the Rings, how Bilbo, I guess, yeah, Lord of the Rings, they want to put their hand in their pocket and touch the ring, or put the ring on without even knowing it, Frodo's like, "I didn't even realize I did it." That's what this thing is like. And when you take those off, just that feeling of relief is, to me, so powerful, that having done this for a decade now, and yeah, there's exceptions, like I'm traveling, God, I have to check my email for X reason, and I install it and I check it. And then it automatically, because I'm aware of it, I'll just feel this static.

**Jake Knapp** (00:56:11):
There's this notion of attention residue, and I think the researcher who coined this term is Sophie Leroy from the University of Washington. Anyway, you can look that up, I think I learned about that from Cal Newport. But this idea says, it makes a lot of sense, that you pay attention to some things and they just stick in your head and they create this static, those apps just create this static. The idea of email being on my phone and accessible at any time creates a discomfort, a disquiet that now that I've seen it and felt what it's like to not have it, I could not imagine experiencing it.

**Jake Knapp** (00:56:44):
You do give some things up. You're not going to be as responsive. John and I don't have as many Twitter followers as we'd have if we used Twitter. There are these things that you look at other people, and I just saw a post on LinkedIn because I haven't used plug-in yet, but I looked on this post and it was a colleague that I used to have and she was saying, "Yeah, I posted a few tweets last year and a couple of them went viral and I gained 30,000 followers." And I was like, man, all I have is 30,000 followers, and that was from years and years ago, I thought I was a pretty big deal, oh jeez, maybe I should... And I was like, oh God, don't do it, because I know when I'm doing it, then I'll be thinking about it all the time and the attention residue will spoil my life.

**Jake Knapp** (00:57:28):
So yeah, anyway, sorry, that's just a rant, but you should try it. The distraction-free phone thing is just worth trying, if you can take off everything, if not just try taking off the thing that's your kryptonite. What's the thing that is the hardest for you to resist, sucks your attention the most, makes you feel not good? Take it off for, try it for a day, or try it for two hours, just to feel that feeling. And then once you've felt the feeling you'll always know, I could release that, and I think that's powerful.

**Lenny** (00:57:57):
And I think when you delete it, it's important to know nothing's being deleted when you're deleting the app, you can reinstall it, you log in, it's all the same.

**Jake Knapp** (00:58:04):
It's all the same, that's an important point. They make it sound like, oh my God, this is a big deal. It's not.

**Lenny** (00:58:09):
Yeah, just have to remember your password or Google auth, or whatever you're using. This metaphor of The Lord of the Rings and the ring is so good for how it feels to just say, I'm just going to check Twitter, what's the problem, I'm just going to check it again, I'll just check it, check it. That's so good. And then in Lord of the Rings, the way they resist the ring is they hide it, they put it somewhere else, they give it to Frodo to take it, right? That's the same solution, it's just like, I can't get access to it, it's over there.

**Jake Knapp** (00:58:36):
Right, right. Yeah, you got to be like Gandalf. Even if that ring would do great things for you, you got to give it to Frodo for a while, maybe show up at the end with an eagle.

**Lenny** (00:58:45):
Just too eerie, yeah, yeah, the eagle.

**Jake Knapp** (00:58:46):
Scoop them up.

**Lenny** (00:58:47):
Yeah, oh man. So the key tips here are find the apps that are sucking your attention, could be Twitter, could be LinkedIn, could be your email, and delete them and/or log out of them. What else?

**John Zeratsky** (00:59:00):
There's a few tactics that Jake and I both use that are related to TV, watching TV, and a really simple one, which is also kind of a luxury one, but I think there are ways to do it that are pretty universal, is just not having a TV in your main living space. Again, not having the default be like, I'm home, the TV is on, what are we watching? And so for me and my wife, that's always been the TV is just in a different room. And Jake, do you use a projector where if you want to watch something you have to get it out, set it up, and make a decision to watch something?

**Jake Knapp** (00:59:40):
Yeah, so it's a bit of a project. And it doesn't take that long, but you definitely are not just click, and you don't see it when it's not set up. So we have a projection screen that's all folded up in the corner, and the projector's in a cabinet, so you got to get it out and get a chair and put it on there. If you're motivated enough you can do it, but it takes a few minutes.

**Lenny** (01:00:06):
You need an old-timey camera that you have to wind.

**Jake Knapp** (01:00:06):
Yeah, right.

**Lenny** (01:00:07):
Someone has to sit there.

**John Zeratsky** (01:00:11):
Here's another one that-

**Jake Knapp** (01:00:13):
[inaudible 01:00:13] in the back.

**John Zeratsky** (01:00:15):
Yeah, right. Another one that's really helpful for me that actually is sort of a bridge is the laser section and the energized section, because it relates to sleep, is I don't keep my phone in the bedroom. The phone doesn't come in the bedroom. And not only that, the place where it charges, the MagSafe little charging place for it, is downstairs. It's on a different floor, it's in the kitchen. So when I put that there at the end of the night and I go upstairs, I might still be awake for an hour, I might read, I might get ready for bed, all those things, but the phone is a way to make sure that the last thing I do each day is not on my phone. That's super helpful to me, and I think there's a bunch of ways, whether it's in a drawer or in a cabinet, there's a bunch of ways you can implement that tactic that I think could make a big difference.

**Lenny** (01:01:07):
My wife and I have been talking about that actually, but the issue is to watch our kid with the Nanit app we need our phone. I know that you can get other devices that aren't on the phone, but we just like the Nanit, and so we've stuck with that.

**John Zeratsky** (01:01:20):
Yeah, one tactic that's related to that that a lot of people have told us they've had success with, and not specifically with the Nanit app, but some people have said, "Oh, I can't uninstall those apps because," Twitter, LinkedIn, whatever, "because I do social media for my work. Literally my job is I do marketing at the company, I have to be on social media." So what some people will do is they'll have a separate device. So it's almost like the old days of your personal phone and your work phone, they'll just have a work device, like a work iPad, that those apps are only there, and when they're working they're on it, when they're not working they put it away. So you could have another device that's the Nanit device and that's all it does and it's in a nice little stand by the bed, that can create some separation as well.

**Lenny** (01:02:09):
That's a great idea. I think there's a company, I think it was Arianna Huffington made a thing where it's a little bed for your phone, where you put it somewhere in the living room and you put it to bed and you charge it there and it's outside your room.

**John Zeratsky** (01:02:21):
Yeah. There's a company, I can't think of the name right now, but I can look it up and send it to you, there's a company that makes a cool box that not only you put your phone in, it charges, but it has some sort of way of, it interacts with the phone, it puts it into Do Not Disturb, or there's some cool integration that it does. So yeah, those things are a little bit gimmicky, but if it helps you create that default, I think it's worth it.

**Lenny** (01:02:48):
Here's the trick my wife wanted to share with you guys as she was reading the book, she's like, "Tell them about this thing that we've been doing," which is with TikTok. She doesn't install the app, and she basically relies on me to send her TikTok videos I like to her account, which she then checks on my phone.

**Jake Knapp** (01:03:04):
You're Frodo.

**Lenny** (01:03:05):
Yeah, yeah, I'm holding the TikTok, my precious. And so the trick there, there's two wins, one is she only sees the best stuff. She respects my taste of videos to watch. And then two is I'm always like, "Give me my phone back," and so there's limited time where she can watch them, and that keeps her from getting addicted to TikTok.

**John Zeratsky** (01:03:27):
Yeah. My wife and I have a similar dynamic, but in reverse and with news. I spend very little time reading the news, and I don't have any news apps on my phone, but my wife's pretty into the news. She has a healthcare background and she studied journalism in school, so she loves particularly those two topics in the intersection of those two. And so she gives me a news digest. When we're chatting at the end of the day, or when we're doing something together, she'll just, it's not structured, it's not some official thing, but she just shares what she was reading about that day. It's nice, it gives us something to talk about, I think it suits both of our styles and our preferences. It's good for her, it's good for me, so it's fun to think about how you can implement some of these ideas in a relationship as well.

**Lenny** (01:04:23):
How do I subscribe to this feed of your wife sharing the news every day? It sounds like a great podcast we all need.

**Jake Knapp** (01:04:29):
Really, really good stuff, or really important stuff, will find us. I think there is, part of the busy bandwagon, or part of the infinity pools thing, is this feeling inside that I'm responsible for staying up to date with the most important news in the world, or the most important news in my inbox, or my company or my team, work, and I'm responsible also for getting the very best of entertainment that's out at this moment that's the most topical and the funniest, or the most interesting, whatever, at this moment.

**Jake Knapp** (01:05:04):
And it's okay to let go of that and, the good stuff, it'll come to you. People will share it with you or you'll hear about it. If it's a really big news story, you'll hear about it eventually. If it's going to affect you, actually, you'll hear about it. And with most news, and most entertainment, we don't play a role, it's hard to admit, but we don't actually play a role in what happens, and so the idea that we're responsible for being on it all the time, that's a job that we can quit, or at least take a sabbatical from.

**Lenny** (01:05:38):
So Tim Ferriss talked about this in The 4-Hour Workweek, is way back in the day is just like, I wait for people to tell me what I need to know, exactly what John just shared before this, and I find this with, so first of all you find that when you delete Twitter, LinkedIn, you go week without it, and nothing is any different. You still know everything you need to know, your job, everything's going great. You missed a bunch of stuff that had no impact on your life. And so I think doing that exercise helps you realize that and I don't need to be on Twitter all the time.

**Lenny** (01:06:08):
And not to get political, but with news about Trump, there's always these headlines, "Trump, look what he did in this lawsuit today, it's over." I just feel like there's so many posts about all these things Trump is doing every day, and none of them, nothing happens. It's just the same thing, just keeps going. If something actually happened there I would hear it from a lot of people, the New York Times would send me a big push. So it's like, I don't need to know all these things he's doing every day.

**Jake Knapp** (01:06:36):
Well, it doesn't matter what your political affiliation is, that is true. Trump is always going to be in the news, and it's always going to, that's the constant, that's the third constant, death, taxes, and Trump will be in the news.

**John Zeratsky** (01:06:51):
A related tactic that I've been doing for a long time is my main source of news is the Economist magazine, which is far too highbrow for what I need, but the main feature of it is that it's weekly, because at the end of the week, the zillion stories about Trump, or whatever, if there was something of consequence, it gets distilled into this really good summary. Really, really good. The Economist has some of the best journalists in the world, they're just absolutely fantastic, and so not only does it have this really nice cadence of once a week, if something matters it's going to get rolled up there, it's going to get summarized. And so that's one of my most durable habits related to these tactics, is reading the news once a week, reading the Economist. It fits my brain, it fits my life rhythm really well.

**Lenny** (01:07:54):
Yeah, it's the opposite of Twitter, basically.

**John Zeratsky** (01:07:58):
Yeah.

**Lenny** (01:07:58):
So yeah, let's hear a couple more tactics and then let's touch on the other two parts of this framework.

**Jake Knapp** (01:08:03):
Well, first a pairing, and then one more. The pairing is reset expectations and slow your inbox. So these are two tactics related mostly to the email and messaging. So resetting expectations is just about having maybe a conversation with people you work with, but it can be as simple as a signature in your email. And so one great example of this is a signature that says, I'm checking email two times a day as an experiment to improve my focus, or I'm checking email once or twice a day, you decide how spicy you want to get with this option, because I'm working on an important project. And just a simple line that people will see passively as you send emails that will reset their expectations of how quickly you'll respond. And if you like you can say, I'm checking email once a day because I'm working on a big project, you can text me if it's urgent. Feel free to text me, you can invite people to do so.

**Jake Knapp** (01:09:11):
But that very act of just putting it in there, you can also do it as an out of office autoresponder, so just like, hey, instead of I'm actually out of the office like, hey, I'm going to be slow to respond to email because I'm working on an important project. That because is really important, and we talk in the book about this, a funny study about the power of because and this case where people would make up bogus excuses, but they'd say, "Because to cut a line," it's an old study, they're making photocopies, but they would cut the line and say, "I need to cut the line because I need to make copies." And just saying because dramatically boosted the percentage of the time that a person would let them cut the line. We're suckers for explanations, all of us. So if you say because people will feel better, and you can feel better about saying it.

**Jake Knapp** (01:09:58):
But this idea that you're just going to put up a placard, basically, that says, hey, I'm slow to respond because I'm working on a project, and maybe give people an escalation path, or don't, that's a huge deal. And it seems like it would be a huge deal because it changes others expectations, and that is true. But the real power of it is in changing our own expectations about what we are going to do and what we are expected to do. Most of the stress comes internally, from our feeling that if we don't get back to people right away, we're not enough, we're not measuring up, we feel some kind of shame or guilt about not doing it and not being fast and not being responsive. And so doing this statement is just about renegotiating with ourselves.

**Jake Knapp** (01:10:46):
The other one is to slow down your inbox. This is a simple one, if you start to do that, if you start to just check your email once or twice a day, or even less frequently, or even if you check it a little bit more frequently but you aren't responding to emails, you don't hold yourself accountable to this idea of an empty inbox, then the whole loop slows down. If you respond to emails really fast, you respond to messages really fast, people respond back to you and then there's more to respond to. And if you slow down that little hamster wheel, it slows down. And so that's powerful too. So those two around email I think can be really helpful, they help me with this, my default feeling about email and messaging and everything is I should be as responsive as possible, and I have to constantly renegotiate that with myself, and those are ways I do it.

**Jake Knapp** (01:11:36):
This other one that's pretty extreme, that I only just tried for the first time, it's in the book but I hadn't actually tried it, but this was a reader of our blog told us about this. Her name is Krissa, I think she allowed us to use her first name but not her last name. So Krissa, if you're listening, shout out to you, this turned out to be a great tactic, but it's to cancel the internet. And she had canceled the internet at home, which is wild. But what I did was I have an office, a very small office in this small town here where I live, and-

**Jake Knapp** (01:12:00):
Small office in this small town here where I live and I canceled the internet there so that I could, when I went there, all I can do are tasks that you can't do with the internet, which is a lot. I mean, you can use a lot of apps in offline mode and it's a great place for me to write. It's a great place for me to do focus work, design something, presentation, but any kind of focused thinking, reading, writing can happen there and now the whole feeling of stepping into that room where I cannot access the internet is insane.

**Jake Knapp** (01:12:32):
To create this kind of a thing at home, you can do things like put a timer on your internet. You can actually buy one of those vacation timers, plug it into the wall, plug your router into that, and it will actually switch your internet off at a certain hour or hours. There's also software that'll let you do this selectively, but the big notion of just having there be a time when you are off and it's a fairly significant pain to get back on again, it's more than just clicking wifi on, wifi off. I find for me that's not enough of a speed bump. It's pretty powerful.

**Lenny** (01:13:07):
Just the way you're describing the feeling of walking into an office that has no internet, I totally feel that. Just imagine, just like, "I have no internet here. I could do so many things. I could read."

**Jake Knapp** (01:13:19):
It might be a coffee shop where you don't find out what the wifi password is and there's just this amazing, amazing feeling. Maybe it's just you go to a park where there's no wifi, just whatever it might be, finding a place where you can't, you just can't get that stuff. Leave your phone at home if you can't bear to delete all the apps. It's so great. It's so great. And then you're not fighting the battle.

**Jake Knapp** (01:13:46):
A lot of this stuff, there's a visualization I think of where I've got the highlight in front of me. It's right there. This thing I can see that I want to do, but it's like five feet away or 10 feet away, and right next to me just kind of vibrating are all of the... You can imagine all the app logos, they're just kind of vibrating right around my head.

**Jake Knapp** (01:14:07):
They're right there and touching any one of them, it's like they're little pieces of candy. It's all going to feel good. There's this really good meal, five to 10 feet away is this great sandwich, but these little pieces of candy are right in my face and it's going to be hard to resist just popping a little Sour Patch Kid or Laffy Taffy in my mouth, but if I could push them away, if I can just push them far enough away so that there is far away or farther away than the sandwich, I'm going to eat the sandwich. And Mike, if that's what you do basically with these barriers to these distractions, then you can get into laser mode and it's easy. You want to. Once there's space, you'll want to do the thing that's most important. It's just it's hard because the candy is right in our face.

**Lenny** (01:14:50):
Such a good metaphor. You also have this metaphor of Odysseus sailing past the sirens. If folks know that story where there was a siren, I don't know, cliff thing where he's just sailing.

**Jake Knapp** (01:15:01):
I know well, in eighth grade I played Odysseus in school play, so I can tell you all about it.

**Lenny** (01:15:06):
Man, what a character to play. Yeah. And in that story, he wanted to experience these sirens who nobody could resist, but he forced his sailors to tie him to the ship and not allow him to do anything, even though he's like, "Let me go. I need to go there." Because everyone crashed into the sirens. Anyway, I'm doing a bad job explaining this story, but I think it just comes back to the same point again and again that you can't rely on your willpower to not go towards these vibrating candies all around you that you need to set up these systems.

**Jake Knapp** (01:15:41):
I think there's this notion that we will use willpower maybe comes from the fact that some people can, maybe some people are just using willpower or they're on Twitter, they're on Instagram, they're on TikTok, they're on Facebook, they're doing all these things, and they're also functioning just fine, or at least what we see from the outside is just fine. But maybe internally too, it's fine.

**Jake Knapp** (01:16:07):
It just seems that everybody I actually talk to and certainly my personal experiences, all that stuff makes me feel bad and actually undercuts my ability to do the things that are meaningful. The meaningful contributions I can make through my work or through my life, whatever. They're all undermined and undercut by the bad feelings and the distraction that come from all of social media, all of the news and almost all of my email. And so if that's true for anybody, if it's even remotely true for us, we have to just radically rethink what we're doing.

**Jake Knapp** (01:16:42):
This thing, I think we basically are steered toward becoming reaction machines and this notion of, "I'm going to have an empty inbox. I'm going to do every task. I'm going to be a fast responder, I'm going to be in every meeting. I'm going to do that because I want to help other people, and that's the way it works." I think this desire to be helpful is a big driver of it. I think we want to alleviate our stress and other people's stress, and that seems like the right way to do it. It's candy. Some of the stuff is candy and easy.

**Jake Knapp** (01:17:12):
We also see this modeled by people in power, so like CEOs and bosses, it works for them because they're applying their influence through being constantly reactive and being in meetings all the time. That's just how they do what they do. That's how they apply their influence. But even for them, I think it has limits as a way to apply influence. At the bare minimum for the rest of us. And for those of us who again, I think is the vast, vast majority for whom all of these things create problems and we're not able to easily willpower and self-esteem manage all this stuff, if we're a reaction machine, we're not doing meaningful work, no Project A's and we're not really alive as humans. We're just chat bots. So it's worth experimenting if you don't want to live your life out as a chatbot.

**Lenny** (01:18:00):
I think the point you made there around the feeling is just a really important point that even if you feel really productive enough and you're getting things done, is if you're feeling bad, it's still an important thing to focus on. This idea of, are you spending time on things you want to spend time on? You also reminded me of this app I'll mention briefly that I think you guys will love, I don't know if you've heard of this. It's called mailmanhq.com. It shuts off your Gmail for periods of time. So you could say, "Only allow my email through at these times of day." And so instead of email whatever, it's just like you can batch your release of email.

**Jake Knapp** (01:18:35):
That's beautiful. Mailman HQ?

**Lenny** (01:18:37):
Mailman hq.com.

**Jake Knapp** (01:18:39):
Okay, I'm writing that down right now.

**Lenny** (01:18:40):
Yeah, I go on and off it because sometimes I just want on an email, but it makes a big difference. It's wild how just not even knowing your email makes a big difference.

**Jake Knapp** (01:18:49):
Yeah.

**Lenny** (01:18:50):
Okay. Let's touch on the last two parts of this framework, energize and reflect, and then let's spend a little time on Sprint for people to get a sense of what this method is all about. For folks that haven't read the book.

**John Zeratsky** (01:19:03):
So to replay the system overall highlight is about the thing you want to make time for today. The most important thing today, laser is about creating barriers to distraction so that you have much your energy or as much of your attention as possible to focus on your highlight on that one thing. Energize is sort of like a booster to laser.

**John Zeratsky** (01:19:29):
It's sort of like the big idea is that our brains and bodies are connected and our ability to pay attention and to focus and to do those things that we care about only works when we are well and we have slept, we have eaten well, we have exercised, we have talked to other people the right amount, not too much, not too little and so we put this as part of the make time framework because we don't think you should go crazy, try a million biohacker type of things, but we do think it's worth applying this same philosophy of pay attention to what's working, what's not, have a system, try some new things, pay attention to those things, run these experiments. We think it's worth doing that for your health, for your energy as well, because it really does make a difference.

**Lenny** (01:20:27):
Maybe share one or two tips there real quick for people to energize to create a little more energy during their day?

**John Zeratsky** (01:20:33):
In the year since we wrote the book and as my life has just continued to change and I've gotten a little bit older, I've realized that sleep is probably the single most important thing. I mentioned earlier, not having my phone in the bedroom, no TV in the bedroom, hopefully that goes without saying, but just being able to really construct an environment that allows me to sleep. I started wearing an eye mask recently.

**Lenny** (01:21:01):
I do that.

**John Zeratsky** (01:21:02):
Yeah, really helps me fall asleep and stay asleep and then the other thing is exercise is a big source of energy for me, but I realized that I was making excuses about why I didn't need to or shouldn't exercise in any given day. So even though this is not what we recommended in the book specifically, I ended up signing on with a personal trainer so that I have accountability, I have a schedule, I have somebody who's thinking about what I need that's not just me and those two things have kind of been the pillars of how I build energy over the last few years.

**Lenny** (01:21:47):
I use this app called Future, I'm a investor, quick disclaimer, but it's basically a personal trainer through an app that's like a real person that helps you design a workout for you, and then they give you the workout on the app and you just follow the instructions and that's the thing that got you working out three times a week.

**John Zeratsky** (01:22:03):
Nice. Yeah.

**Jake Knapp** (01:22:04):
That's awesome.

**Lenny** (01:22:04):
Killing it. Okay. And then within reflect, maybe just briefly talk about the importance there and then one thing people could do to reflect on how things are going.

**Jake Knapp** (01:22:14):
Reflect is just simply the act of looking back on the day and treating the day. It wasn't marble gravestone of your successes or failures, it's just a experiment that you ran. What happened in the experiment? Taking note of it in that lens, what did it look like? There's a template in our book that has some questions you can answer, but really it's pretty simple.

**Jake Knapp** (01:22:44):
If you write down your highlight in the morning or the night before, if you're draw it and you stick it somewhere visible, then at the end of the day you just look at it and just like, "Okay, did that happen or did that not happen?" If you stick it somewhere visible, you won't even have to do anything. You'll just come across it and you'll know if did that happen or not? So that's the simplest part of it is writing it down, sticking it will create a reflection loop for you.

**Jake Knapp** (01:23:14):
Another thing that I think is quite powerful at the end of the day is to write down, keep a notebook by the side of the bed and write down one or two or three things that you are grateful for during the day, just like a simple gratitude journal. And you'll start, this keeps you in this frame of mind of what was cool today, what happened that was satisfying or joyful, what brought me joy and then if you start the day thinking about what you'd like to happen and then you look back and say, "What was great?" Your brain is just starting to look for those good things. Look for those big highlights, and that's a great way to live your life day to day saying, "This is what I hope will happen. This is what did happen. Now I'm more tuned into what it might happen tomorrow. Oh, now I'm more tuned into what happened today." And again, and it's just a really nice loop. So was there a connection between what you hoped would happen? Did you manage to do your highlight? If so, what helped you do it? What worked or didn't work? What made it hard? It might be an energy thing that suggests a tweak to when you drink coffee or if you take a walk or whatever. It might've been a focus thing. So maybe I'll try another barrier for this thing because that undercut me. Whatever it is, it's just basically, in summary, curiosity about your day instead of self-judgment about your day.

**Lenny** (01:24:30):
I think we've covered Make Time and tons of depth if people want to practice these things, highly recommend getting the book. It's called Make Time and it's really quick to read and it's basically just a long list of things you can do and we talked about a lot of them. There's a lot more. And I think part of the premise of the book is try stuff, see what works, see what doesn't. Keep reflecting, iterating, some of these things, even if you find two things that change how productive you're, that's a huge win.

**Jake Knapp** (01:24:55):
I highly recommend people get the book. That's great. And it's our best attempt to put together a how-to guide for doing this stuff. For what it's worth, we're not really motivated to try to create a self-improvement empire. This is not our full-time job. We just hope it works for you and is useful. So if you don't want to buy the book, we get it. Go to maketime.blog and just check out some of the experiments and things that are available there or just try one or two of the things that we talked about today. Try the highlight. If you're going to do one thing, just try right now writing down what you want your highlight to be, either for today or if it's late in the day for tomorrow on a sticky note and put it somewhere that you'll see it tomorrow.

**Jake Knapp** (01:25:41):
Just that is a great step in the right direction. Try having a conversation with your colleagues or putting a signature or an autoresponder in your mail that says you're going to slow down or talking to them about slowing down at character. At our VC fund, we had a conversation and decided we're going to try to have our main communication happen in Notion so that if we're talking about something, it's in a form, it becomes a document, and the expectation of how you react and respond there is going to be different than in a tool that's designed to get you responding as fast as possible, like an email inbox or Slack.

**Jake Knapp** (01:26:16):
So just have a conversation about that. Take a couple apps off your phone. You don't have to buy the book or become totally bought into the system to do those things, but that's what we really want. We just want you to have more time for what matters for you.

**Lenny** (01:26:30):
Amazing. So I've used up basically all our time talking about Make Time. I think we should have a follow-up episode just to talk about Sprint. What I think we do is let's cut off the lightning round and whatever stuff you guys would've shared there, we'll include in the show notes. I'll send you those questions asynchronously, but let's just talk about Sprint for a few minutes just to give people a sense of what is this framework, it's extremely popular, lets a lot of really successful products, and then we'll wrap up and point people in the direction that you recommend.

**Jake Knapp** (01:26:59):
Cool.

**Lenny** (01:27:00):
What is this framework of Sprint? When do people use this idea, this framework, this approach? And what are some examples of what has come out of somebody applying Sprints?

**Jake Knapp** (01:27:10):
The big idea with a design Sprint is to go from a zero to a prototype and a test of that prototype in just five days. And it's a recipe, it's a scripted set of activities that we developed over a number of many years. First, started with some projects I was doing at Google and I run some experiments with the way I was working. I was a product designer on Gmail in the 2000's, and I also co-founded Google Meet. And in the sort of week where we really catalyzed what had been a project that was going nowhere, this 20% project of people who were familiar with Google, like a side project was going nowhere for a year and a half. It was really on the rocks. And in one focused week working together, we decided me and these two other folks we're going to clear everything off.

**Jake Knapp** (01:27:59):
I visited them in the Stockholm office where they were. We created a working prototype. Instead of trying to come up with the perfect plan, the perfect PRD, the perfect pitch to executives we're like, "Let's just build a prototype and put it in front of our colleagues and get them using it." And we did that and that was the thing that stuck. And so from there on, I was like, "I need to recreate these kinds of moments for teams because that's powerful." So we ran hundreds of these at Google Ventures with startups, tweaked and refined the process, wrote this book called Sprint.

**Jake Knapp** (01:28:28):
We run a venture fund today, John and I and our colleague Eli, called Character. We help teams find and expand product market fit with Sprint. It's a tool for doing that and it uses a lot of these principles we talked about with Make Time to change the defaults, but not just the defaults of the way an individual works, but the ways teams work, the way people make decisions, the way we evaluate what's a good idea, a good strategy and worth pursuing based not on just a hunch or a guest, but based on something we can actually see with customer reactions. So all of that kind of in a nutshell is what Sprint does.

**John Zeratsky** (01:29:07):
This idea of getting unstuck and turning maybe some abstract ideas or some concepts that you've been discussing, turning that into a concrete prototype, something that you can look at and you can click around and you can actually try. It works in a lot of different contexts, and we've heard amazing stories from people who read the book and have run Sprints at companies that have a hundred thousand people and governments and all sorts of different organizations, but the stories that are in Sprint are about working with startups.

**John Zeratsky** (01:29:45):
We think this is especially valuable for startups because typically you've raised a certain amount of money which buys you a certain amount of runway. You have a certain amount of time to prove that you have product market fit to prove that the thing that you're making is the right thing for some customers. And so the faster you can do that, the more quickly you can find out if you're on the right track, the more quickly you can learn and you can course correct and ultimately you can get to a better place faster than if you spent months working on that prototype or that first version of the product before releasing it.

**Lenny** (01:30:22):
I think what's awesome about it is as a product manager, the idea of containing a new idea experiment to five days versus this ongoing teams distracted on this idea just like, "Cool, we're going to spend a week, see where this goes. They're not going to spend months exploring. We're not going to talk about it. And just in theory, let's just try it." I think it's really powerful. And so for folks that may want to explore this until we do a follow-up episode, is it just by the book, is there anything else you could point them to think about this idea and implementing it?

**Jake Knapp** (01:30:49):
Yeah. Well, if you are thinking about, or in the very early stages of starting a company, a great thing to do is to get in touch with us at character.vc. And actually we're just opening up applications to our labs program. So character.VC/labs. Our labs program is an intensive program for startups, and we will run a sequence of Sprints including some new formats that are not in the book, but are excellent.

**Jake Knapp** (01:31:20):
This will be our third time running through this. We found that it's especially valuable for AI startups. So it just turns out that a lot of the complex issues you have to figure out with turning something that may not initially be trustworthy may require a big behavior shift to customers who aren't used to working in this way and sometimes artificial intelligence can produce things that feel kind of alien to people.

**Jake Knapp** (01:31:45):
And so making this stuff actually useful, more than just a chatbot with little stars that's in the corner that says, "Hey, would you like to ask the AI a question about this?" But something that's really meaningful, doing this kind of repeated and we'd run a sequence of Sprints doing it again and again, you work with directly with John and I, we find a really powerful way to get started.

**Jake Knapp** (01:32:04):
Anyway, that's a big advertisement for Character Labs. But yeah, in general, check out the book. Also, would say if you're not quite ready to dip your toe in the whole book, you can go to the sprintbook.com. And we have a ton of resources on there, including a new thing, which is a Miro board, a Miro template that I created that has step-by-step instructions for every single step as well as 30+ videos of me explaining each step and actually I think I'm wearing the same sweatshirt in those, so if you're watching this on YouTube, you can see more of me in this sweatshirt in that template. And that's free, that's free and there's a bunch of resources on the website that are free as well. So anybody, everybody should be able to access this stuff.

**Lenny** (01:32:51):
Stuff. Amazing. And again, for folks that may want to check out the Labs cohort, is there anything other than AI-oriented that would be ideal? Just how early stage, any other markets that are ideal for the Sprint process and the way you're approaching it?

**John Zeratsky** (01:33:05):
Yeah, it's a four-week Sprint program for pre-seed software startups. So we only invest in software startups at Character, and this program is really ideal for companies who they know what they're doing. They're not just like, "Oh, I want to start a company." They have an idea of an opportunity that exists, a market that they're focused on, but they definitely haven't reached product market fit.

**John Zeratsky** (01:33:31):
They may not even have a product to test that hypothesis with. So it's very early stage, and we are pretty flexible on the sector, the industry that you're in. But what we find is that the more there's kind of a big behavioral risk, the better this stuff works. So if you're just trying to make a slightly better version of something that already exists, and maybe it's going to be a little cheaper or a little faster, a little easier to use, you probably don't need this stuff. You can probably just do it and probably going to work.

**John Zeratsky** (01:34:06):
But if you are like one of our portfolio companies, they make AI that controls the industrial facilities. They came from Google DeepMind and they did this for Google data centers before, something like that where you have to convince plant operators who are wearing hard hats and dealing with huge equipment, you have to convince them to trust AI. That's a big behavior shift. That's a big behavioral risk. Or in healthcare, in education, places where it feels like the technology can really make a big difference for people, but it can be hard to get over that hurdle of trust and understanding. Those are the types of opportunities that we think we can really help with.

**Lenny** (01:34:50):
Playing on hard mode, these sounds extremely difficult. I love it.

**John Zeratsky** (01:34:53):
Yeah.

**Lenny** (01:34:54):
So if you're thinking about starting a company or if you're in the process of starting a company, check out character.vc/ labs. John, Jake, thank you so much for being here and for making time for this podcast conversation.

**John Zeratsky** (01:35:06):
Thank you for having us. This was great.

**Jake Knapp** (01:35:08):
Yeah, thanks for having us.

**Lenny** (01:35:09):
Absolutely. My pleasure.

**Jake Knapp** (01:35:10):
It was really a pleasure, Lenny.

**Lenny** (01:35:10):
The pleasure is mine. Bye everyone.

**Lenny** (01:35:15):
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.

---

## [12/19] How Netflix builds a culture of excellence | Elizabeth Stone (CTO)

**Elizabeth Stone** (00:00:00):
We can't really have any of the other aspects of the culture, including candor, learning, seeking excellence in improvement, freedom and responsibility if you don't start with high talent density. And in some ways, it's very reflective of Reed Hastings as founder of Netflix. So when he founded Netflix and grew the company over time, it was with a belief that there could be a different approach to building a company that would make it a place that people thrived in and loved being and would feel different than other places, both in the quality of that talent density, but even more importantly, the excellence and the outcomes. And that that's where people would derive a lot of sense of fulfillment. So it is very deeply seated at Netflix from its original days. And in order to do that, you have to really hold yourself to a lot of stuff that doesn't feel like natural human behavior.

**Lenny** (00:01:06):
Today my guest is Elizabeth Stone. Elizabeth is chief technology officer at Netflix, and as far as I can tell, the first economist to ever be named CTO at a Fortune 500 company. Prior to this role, Elizabeth was vice president of Data and Insights. Before Netflix, she was vice president of science at Lyft, COO at Nuna, a trader at Merrill Lynch, and an economist at Analyst Group. In our conversation, we cover a lot of ground. We talk about how an economics background has helped Elizabeth in her career and why she expects to see more economists rise in the ranks of tech companies. She shares some of her secret sauce for rising so quickly at so many companies so consistently. We delve into Netflix's very unique culture of high talent density, radical candor, and freedom and responsibility. We also talk about the structure that Netflix has for their data and user research teams, which she believes is a part of Netflix's secret to success. We also get into what biking and triathlons have taught Elizabeth about life and how she brings that into her work and so much more.

**Elizabeth Stone** (00:04:41):
Thank you. Thank you for having me.

**Lenny** (00:04:43):
So when we booked this conversation, you are VP of data in Netflix. And since then you got a promotion, you're now the CTO of Netflix, which feels significantly more fancy. Question for you, what is life like now that you are CTO versus VP of data? How is it most different? I'm imagining more meetings.

**Elizabeth Stone** (00:05:01):
I would say the biggest thing that changed is probably the amount of context switching and the degree to which I feel behind or I have a lot to learn. And I felt like I had a lot to learn in the VP of data and insights role that I was in before in part because we cover a lot of different areas of the business and there's always people to learn from, but the engineering organization just takes that to 100 basically. So more people to get to know, more problem spaces, aspects of technical expertise that I'm just not as deeply familiar with. And yeah, a lot more meetings.

**Lenny** (00:05:41):
I imagine many higher stakes meetings as well.

**Elizabeth Stone** (00:05:44):
Yes. So thankfully not a lot of meetings that Netflix feel like now you're really in this scary room, but it does feel like the role has more consequence, which is actually an exciting thing.

**Lenny** (00:05:57):
Kind along the lines of what you just talked about being a CTO. Your background is actually unusual. You're a trained economist, you got a PhD in economics. And from what I can tell, you're the first CTO of Fortune 500 company that is an economist trained in economics. First of all, is that true? I don't know if I think that's true, but you tell me.

**Elizabeth Stone** (00:06:16):
I have not checked the list. That was one of the things I did not do after getting the title. It might be unusual. I've heard a lot of feedback on that, so I don't know if I'm the one and only, but I will definitely say it's probably unusual.

**Lenny** (00:06:30):
Yeah. So I guess the question is just, do you think this is an anomaly and going to continue to be really rare? Do you think this some are going to see more at tech companies? And generally do you think tech companies should hire more economists?

**Elizabeth Stone** (00:06:41):
Yes to the last question. That's the easiest of it. But one of the things I observed even with the focus on data science where I've been deeper for a period of time is that economics is a flavor of data science. So it is a set of technical skills for sure. It's a way of framing certain problems or solving challenges.

**Elizabeth Stone** (00:07:06):
And so when I was first switching from economics into tech, it was before there was a lot of sort of the frenzy around data science that we've seen more recently and it was harder to make that argument that economics is a flavor of data science and maybe complimentary to other versions of data science. And I feel more strongly about that now that I've seen it up close. And so maybe by extension I would say just like I think data science can be helpful for a lot of different problems that you might not immediately think, "Oh, this is something that we should bring data to," I think that economics is generally valuable for a lot of different challenges and it's a useful perspective to add to things, especially in a business context and especially in how we want to simplify problems in a way that makes them feel tractable.

**Elizabeth Stone** (00:08:00):
So I feel like that's been a benefit to me to have had that type of formal training and then bring that perspective or way of thinking to different roles. And so I don't know that many people at Netflix think of me as an economist, but I find it comes out in the way I think about things. So to the extent that that's true generally, I think it's useful in a lot of companies. And I feel like even since I made the switch towards tech, I've seen it become much, much more common to think about the value of having economists on teams.

**Lenny** (00:08:32):
Just to pull on that thread a little bit more, is there something very tactical or concrete that you can share that you find helpful with that background that you found helpful in your career?

**Elizabeth Stone** (00:08:42):
Other than the dismal dry science of it all? So one example would probably be in an understanding incentives and thinking about unintended consequences. I think that that is true both in terms of internal leadership, so being part of a management team that's thinking about how do we clarify priorities or motivate a company or define the problems we want to solve. And then part of it is more externally oriented. How do we want to think about what Netflix is to consumers and how we want to think about competition?

**Elizabeth Stone** (00:09:24):
There can be a rational way of thought, which is one version of economics of shouldn't rational intelligent people behave in the following way. And then there's the, well, if given certain incentives, what might you see that we didn't think was optimal or we weren't expecting to happen but could be a consequence or repercussion here? And so I think that that type of framing, I don't know if it's unique to economics in a way because it has elements of psychology to it as well and planning ahead has become really useful for thinking through cause and effect. So that has come up in a lot of different spaces in Netflix and in other roles I've been in.

**Lenny** (00:10:08):
I was looking at your LinkedIn and looking at your career over the years. It seems like you've had a meteoric rise at four different companies. And I'll just walk through them briefly. So at your first job, you went from associate to vice president in three years. At the next company, Nuna, you went from manager of data science to COO in two years. At Netflix you went from VP to CTO in three years. I think that's really rare. I'm curious what is your secret sauce to being so successful at so many places and especially in the context of what advice can you share with folks earlier in their career?

**Elizabeth Stone** (00:10:46):
This is one of those questions that sparks the reflection that I wouldn't normally do, so that's great. I really don't think of it as a secret sauce, but maybe I can walk through some of the things that I think have been instrumental. As you listed that out, it sounds like the two to three year point is the real sweet spot, so maybe there's something about that timeline. But I think some things almost feel trite in how I would say them, which is I'm very dedicated to the work and to the teams I'm part of. It's been part who I am for a long time that I give everything I've got to the job that I'm in. And I think that dedication and that I get joy out of that has mattered. It matters because I enjoy what I'm doing. I do the best work I possibly can, less so for myself and my own ambition and more so because I think of myself as being part of a team and so I really need to deliver for that team.

**Elizabeth Stone** (00:11:52):
I think that framing in my mind and that motivation has helped me in a few fronts, which is the way in which I build partnerships with people I work with that I really care about setting other people up for success and being someone that people want to work with, so I learn from them, they learn from me, and we get better outcomes for the business together, I have found that part of that is being someone that people can leverage to translate from technical to non-technical and non-technical to technical. So that I do think has been a relative advantage in my role. So while I was often sitting in more technically-oriented teams, a lot of the advancement in my career was to roles that required that type of communication fluency. It grew out of being able to partner with people across the businesses who didn't necessarily have the same background, but where we needed to really connect spaces so that we could be more effective.

**Elizabeth Stone** (00:12:57):
That was something that I think really the training for that came from analysis group where it was a very quantitative set of work that we had to find a way to communicate to judges and juries for economic cases. So that was something that was trained in other roles and I think I've been able to leverage. I'm a relatively introverted only child, so I observe a lot, which means that I learned from other people. And in each of these roles I have tried really hard to watch what other people are doing, think about how could I learn something from them, whether it's the thing that I want to be able to do myself or it's the thing that I think, "Oh, that doesn't quite fit or feel authentic with my style." And I do a lot of that introspection. So I have been surrounded by amazing people in all these roles and I have a feeling that I learned a lot by osmosis and observation and then have been able to leverage that to be stronger in the roles I was sitting in.

**Lenny** (00:14:00):
I took a few notes here. A few things you mentioned is just like, dedication, essentially working really hard and taking your work seriously, being part of a team and setting other people up for success, translating complex tech language and problems to non-tech people, and then being really good at observing and learning from other people around you. Is there an example or two that you could share of some of these to make it even more concrete for people? Like dedication. Is that just like working many hours, being part of a team? Anything along those lines to share a story maybe to help people put this into practice.

**Elizabeth Stone** (00:14:35):
No, and it's a good clarification because the dedication piece really isn't about long working hours. It's more about how much I care about excellence, I guess. So giving it my best in those situations. And that might not mean that I work really wild hours or I work weekends or I'm the one who's willing to sacrifice the vacation. I've actually tried to avoid setting that as an expectation, but more that I hold myself to a very high standard.

**Elizabeth Stone** (00:15:13):
So an example would be, especially as I've gotten more senior in roles, there can be an expectation that it's okay for other people to wait on me. So whether it's the timing for a meeting or providing input on something or reviewing a document or following through on something I said that I was going to do, and I really try to avoid that, which means that if someone sends me something, I try to be very responsive about it. If I know that I said I'm going to do something, I follow through on it in the timeline that I said I was going to do. If I have a meeting, I try to be on time to that meeting.

**Elizabeth Stone** (00:16:01):
Those are all flavors of dedication to the work that show up in, "Oh, it seems like Elizabeth works really hard," but the motivation factor is other people are relying on me and I want to show up for them. And so that's when I say dedication and it's related to the second point around showing up well for the team, those would all be examples of I feel urgency in responding to people and doing high quality work.

**Elizabeth Stone** (00:16:27):
For the other parts of technical to non-technical, I think a great example is actually a very timely one at Netflix, which is, we are making strides to offer live content types. So live events, live TV shows. We announced this week that we're going to be hosting WWE starting later this year and early next year, 2025. That is easier said than done. I know that there's a lot of entertainment companies that have live content. But Netflix has really been in the streaming content business, so live content is something new for us and it's something that's going to require a really close partnership between our content organization and our products and technology organization because there's a content strategy to it, there's a business strategy, there's a technology strategy to it. A big part of my role is, can I explain how we're going to approach those technical problems in a way that builds competence with the content team? Can I try to understand their content strategy in a way that sets the technical teams up for success and we understand what we need to be able to deliver on here in terms of requirements.

**Elizabeth Stone** (00:17:46):
I don't think I'd be able to do my current role well if I wasn't able to do that type of translation for something that's going to be a big bet for the business and something we want to invest in jointly. And then to set my partners up for success in that. So I am going to do everything I can to make sure we deliver well for my content partners because I feel like that's what's best for Netflix in the business.

**Lenny** (00:18:09):
Amazing examples. In terms of life content, I think about the Love is Blind. I think it was for premier, whatever, reunion that we got sucked into that show. So good job. And I think there were some issues with that, right? That reunion streak.

**Elizabeth Stone** (00:18:24):
Well, yeah, that was about a little less than a year ago now. So the amazing thing about failure is you learn a lot. We learned a lot. We've taken notes on it and we had a couple successful events after that, including the Netflix Cup last October. And we've got some exciting events coming up. So I think that's something that strengthened us, but did reveal that we're tackling a hard problem.

**Lenny** (00:18:50):
Yeah, the Twitter feeds during that, Love is Blind premiere were hilarious. People are pissed.

**Lenny** (00:18:57):
Okay. And then in terms of the, keeping a high bar for yourself, I love that. I think about a quote that... There's a VC, Ann Miura-Ko, at Floodgate and she did this interview with Tim Ferris. She shared that her dad always asked her, "Are you doing a World-class job with this? Are you doing a world-class job with your homework? Are you doing a world-class job with your piano recital?" And that's the bar that he always had for her. And I feel like that's a really good way to think about work and life in general if you can.

**Elizabeth Stone** (00:19:28):
Yeah, my mother used to describe to me, probably still does, though it required more repeating when I was younger, that the last 5% is the 5% that really mattered. And so it is that framing of the extra effort you put into something to make it world-class or to make it excellent. And so I do like to push myself that way and I hope it sets a good example for other people too. It's very consistent with especially the company cultures that I tend to thrive in where that's the general expectation of the culture. So you don't feel like you're doing it alone, because then I think you can start to feel frustrated by that.

**Lenny** (00:20:15):
I know that this is a big part of Netflix culture and I want to get into it. But before that, I'm curious just what that looks like with people that report to you. How do you help them level up in this skill of having a really high bar? And an example I'll give as you think about maybe an example is the way I described this to my PMs was, you want to have this aura that you've got this that, "If you give Lenny something, he's got this. He's going to follow up, he's going to close the loop, he's going to get it done. If he can't get it done, he'll tell me, I feel like this thread will not disappear. He won't drop this ball." Is there anything that you've learned as a good way to help someone learn this kind of skill, understand why this is so important?

**Elizabeth Stone** (00:20:53):
It shows up for the people who report to me, is one part example setting. So if I don't do it, why would they do it? I treat that very seriously that we should all be held to the same standards.

**Elizabeth Stone** (00:21:12):
And as a second thing, I give feedback when it's not up to the standard. So I think one of the things I've observed especially with people on my teams is that the expectations aren't always clear and you can't assume that they're clear if you don't share them. When something's not meeting expectations or really showing up as excellence, I think it's a combination of both giving the feedback on that and being direct about it and being specific about what would it take to get this to the bar that I am expecting or to show up in the way that I'm expecting.

**Elizabeth Stone** (00:21:55):
And then the third and probably most important thing is help them fill that gap. So that would mean... Let's take an example. It certainly has happened frequently in many jobs. A document is okay, it's not great, it's not going to be easy for people to follow, it's not as crisp as it could be. There's things that would strengthen it. I can both give the feedback on that to make sure like, yes, it's going to take another round of iteration, yes, we're going to have to work another week on this and not be done with it, but pushing people to get there, and then jumping into the document and helping.

**Elizabeth Stone** (00:22:32):
So I feel very strongly about, and that's kind of what I mean by setting an example of like, "Let's work on this together," and then through that, help people uplevel themselves so the next time around they know the expectations and they've had help getting there in the past. So that's probably happened a thousand times in my career where I jump in with both feet because something needs to be better and I think the teams are better for it afterwards, or I hope they are.

**Lenny** (00:23:00):
I think that's such a good framework just to kind of mirror back what you said, "Set expectations that the bar is going to be really high and here's what I'm expecting from you." Give them very specific feedback on where the gap is and then help them fill that gap. I think a lot of people may feel this and hear this and they're like, "Oh man, I don't want a manager that's like this high of an expectation person and it just feels really stressful." But I've had these managers and I feel like that's when I've learned the most and leveled up the most, is having someone that had really high expectations and then helped me understand, "Here's where you're not doing as well as you can. I know you can do better. Go back and work on this." I know that sounds annoying, but I think in practice it ends up helping you most in your career. I imagine you've seen a similar result.

**Elizabeth Stone** (00:23:45):
I think so. I mean you'd have to ask some of the people on my team. So I might look at it differently that they look at it.

**Lenny** (00:23:51):
[inaudible 00:23:52] differences.

**Elizabeth Stone** (00:23:53):
It's a hard skill because it's not always easy to give feedback, especially if you feel like you know someone's put a lot of effort into something. And so I give a lot of thought to how I deliver that feedback so it feels like we're on the same team and I'm trying to help them be successful, not to help encourage failure. And that's where I think that third piece of the framework of jumping in to help can make people feel like, "I'm in a safe space. My manager wants me to be successful. My manager's helping me here." I do often do that behind the scenes. So maybe that's another flavor of this, which is, I don't do it live in the big meeting in front of all the people where the presentation doesn't go very well. I do it afterwards where it feels like a safer space to say, "Here's a way this could have gone better. Let's think about this differently next time." So it gives people a little grace and a little bit of an ability to absorb that feedback without feeling like it's kind of on a stage.

**Lenny** (00:25:02):
Another thing someone may be feeling when they're hearing this is like, "Oh my god, it's going to take me so many hours to just get it to a place Elizabeth is happy with." And I know you said that this doesn't mean necessarily many hours. Do you have any advice or thoughts on just how to avoid burnout and working all the time, but also keeping this really high bar and high expectations?

**Elizabeth Stone** (00:25:21):
It truly is not about time. I even found myself in a meeting earlier today saying, "If we're clear on the objectives of something, it might be that the last 20% of polish on the document is a really bad use of time. So if we're going to come together to talk through..." Like quarterly business review was the example, what were the highlights? What were the low lights? What were the learnings from the quarter? Where are there places of misalignment? The reason we're doing the quarterly business review is to have a really candid conversation about how we think things are going, to have a debate about things where maybe we're stuck. It's not to have a perfectly polished document for that conversation.

**Elizabeth Stone** (00:26:08):
So my feedback in that instance would be, I would much rather have someone spend the time thinking about what's the conversation we really want to have? "How do I tee that up?" Not, "Could I spend another 20 hours to make it look like everything's perfect in this document?" And so I think in that sense it's not just excellence, like you wrote the perfect document, I should probably be careful to not use that as the only example, but instead we really got to the outcome we wanted to get to because we were thoughtful about it and we put a lot of energy and time and iteration into making sure we got to that outcome.

**Lenny** (00:26:43):
And is this an example where you gave someone feedback that they spent too much time on the polish or is this earlier? And to give the pyramid of this framework you kind of shared of set expectations, give specific feedback, help them fill the gap and then do it in private, is this the expectation setting in this example or is this feedback you spend too much time on this?

**Elizabeth Stone** (00:27:01):
This is expectation setting. So one of the things in my new role is that there's some practices that the team has had where they're trying to understand, Are we still going to have those practices? What's going to be the same versus different about those things?" and get an understanding of my expectations. So it's great that people ask that question so that I can be clear about, "Oh wait, if you're on the last 20% of this polishing the dock, I'd rather spend time over here. And here's how I would like the conversation to go so we all get something out of it instead of it feeling like it's just a leadership reviewer on my behalf." So in this specific situation, it was setting expectations ahead of time so that we can set everyone up for success.

**Lenny** (00:27:44):
Awesome. Okay. So we've kind of been talking around this, but this is an important part of the Netflix culture. Just broadly, Netflix has a really special and unique culture. Even though it's been around for I think over 25 years now, it feels like the culture has come up many times. There's that initial culture deck that came out that blew everyone's minds. There's a recent book, No Rules Rules I think it's called. And it feels like Netflix has done a great job at maintaining its culture.

**Lenny** (00:28:10):
It feels to me there's these three important elements, and maybe there's more. One is very high talent density and a focus on high performers. Two is candor and being really direct. And then three is giving people freedom and responsibility and getting rid of useless processes like vacation time and things like that. So maybe just to dive into that first one of high talent density and this focus on high performance. I guess the question there is just like, what does this look like in Netflix? And I imagine part of it is hiring, part of it is performance reviews. And then just why is it so important? Why is this such a focus on Netflix? What happens when you have such a high talent density?

**Elizabeth Stone** (00:28:51):
It's just so intrinsic to who Netflix is as a company. And in some ways it's very reflective of Reed Hastings as founder of Netflix. So when he founded Netflix and grew the company over time, it was with a belief that there could be a different approach to building a company that would make it a place that people thrived in and loved being and would feel different than other places, both in the quality of that talent density, but even more importantly, the excellence and the outcomes and that that's where people would derive a lot of sense of fulfillment. So it is very deeply seated at Netflix from its original days.

**Elizabeth Stone** (00:29:37):
A big piece of that talent density is definitely hiring. So who are the people coming in and joining the team? But a lot of it is, we can't really have any of the other aspects of the culture, including candor, learning, seeking excellence and improvement, freedom and responsibility if you don't start with high talent density.

**Elizabeth Stone** (00:30:03):
And so in some ways it's not the end, it's the means to the end in what Reed and the rest of the leadership team has been trying to build. And so in order to do that, you have to really hold yourself to a lot of stuff that doesn't feel like natural human behavior. What I mean by that is giving the feedback, this gets into the second bucket. So giving feedback, being candid around your expectations when they're not being met, what could be better in helping people improve, and be able to receive that type of feedback yourself in order to keep talent density high? Because no one comes to Netflix as a perfect human being and stays a perfect human being the whole time. We all have ways that we could grow and improve. And so in order to keep that bar high, you have to be willing to have those types of very uncomfortable conversations. It's an uncomfortable amount of candor and feedback in order to keep that bar high.

**Elizabeth Stone** (00:31:10):
And then the other piece of it is another thing that doesn't come naturally to humans, which is making a call in pretty timely fashion if someone's not able to meet the bar, and to say either, "I don't think the role you're sitting in is the right role, or I don't think that Netflix is the right place for you," and to make that something that is part of best practice to get to a point where you could make that decision. And that's where we refer to the keepers test, which is really just a mental framing to make sure we hold ourselves accountable for this. Where if I'm asking myself the question, "If this person on my team came to me and said, 'I'm leaving today. I have a different opportunity and I would like to take it,' would I do everything I could to keep them at Netflix?" If not, then I should be having that tough conversation about, "Should you really be here? Are you in the right role?", if I might be a little bit relieved if you said you were leaving.

**Elizabeth Stone** (00:32:20):
The reason the keeper test and that question is useful is because no one wants to think that way. It's very hard to say to someone, "I think this isn't the right fit. I think you should move on from the company." So we have to introduce some of those reflections in order to encourage the behavior. And we also then want to get to a place where when you're having that tough conversation, people aren't surprised by it. That is easier said than done. But you can only get to that conversation around, "I don't think Netflix and you are the right fit for one another" if you've been giving feedback along the way. And so it feels like in its most ideal state, it's a mutual observation. In practice, it's not always that smooth. Obviously we are humans. But that all feeds on itself in order to make sure that we're really holding ourselves to what we say our behavioral norms as part of the culture.

**Lenny** (00:33:17):
How is that operationalized? Is that just mental model that you should have in mind? Or is it like every quarter you should go through this exercise? Is it part of the performance review process? How does that actually operationalize at Netflix?

**Elizabeth Stone** (00:33:29):
It's definitely a mental model. So when we talk to managers about what does it mean to be a manager at Netflix, it would mean you should be with some frequency asking yourself this about the people on your team. People ask me frequently, "Am I passing your keeper test?" So it becomes part of a regular manager direct report, one on one. And it is just another way of saying, "Am I meeting your expectations? What's going well? What's not going well? How are you thinking about things?" And that can sometimes be a very awkward conversation to have. So in the middle of a lot of like, "We have to talk about this project or that deliverable or this thing that's happening," to take the time to step back and just say, "How am I doing?", can feel loaded sometimes. And the keeper test, while it feels like a very heavy concept, creates a lightness around being able to have that conversation regularly. So we do operationalize it. A point that you made, I'll just clarify, we don't have performance reviews.

**Lenny** (00:34:33):
Oh, wow.

**Elizabeth Stone** (00:34:34):
So we don't have a practice that a lot of other companies do where we would think about reflecting on a rating of how things are going. We do have an annual cycle of 360 feedback where you request and receive feedback from a lot of people, but it's not an input to some output, it's just for the value of the feedback and to make sure we're keeping that muscle. And we have an annual compensation cycle where we reflect on how are people doing? And so you think about performance as part of both promotions and as part of compensation, but in that way it has to be part of the day-to-day and part of the operating rhythm because we don't create a process where that would come to the surface.

**Lenny** (00:35:20):
Interesting. I didn't know that. So the idea there is just ongoing, like the whole... So what many people dream of, no performance reviews, we'll give you ongoing real-time feedback. We don't have to wait six months. I feel like people talk about this but rarely do this, but that's how you guys operate.

**Elizabeth Stone** (00:35:36):
In ideal.

**Lenny** (00:35:37):
In ideal, yeah.

**Elizabeth Stone** (00:35:38):
In practice. It's like you have to keep reminding yourself, "This is our ideal" because it's really easy to rely on the annual 360 cycle. And all of a sudden I do get about 300 pieces of feedback. And some of those things are on things that happened six months ago and I think, "Oh, I wish you had told me this at the time, that would've been more living the Netflix culture." So we have to push ourselves to do it that way. But yeah, that is if working well, it's very timely direct feedback. The 360 site goal is sort of the annual check-in on, "Let me get the full picture. Let me be able to distill some themes. Let me tee it up for a conversation with my manager." And then it does remove the sort of crutch of an every six month performance review or something like that.

**Lenny** (00:36:31):
When you talked about this example of someone asking you often, "Am I meeting your keeper test?", it makes me feel like someone's just super nervous. They're like, "Am I passing your keeper test?" And it makes me feel like it could create a culture of just like a lot of stress and worry and this hunger games mentality of like, "I got to compete and worry and I might die or get fired any day." I'm guessing the solution to that is partly cultural. This is just the way we work. You don't need to stress all the time, but you may be let go if you're not meeting this keeper test. How do you avoid this just constant worry that you might be fired any day and that you may not be hitting the bar?

**Elizabeth Stone** (00:37:08):
In my personal experience, I have felt a lot more at ease by having these conversations than by not having them. So in many roles I've had, I haven't been sure how I was doing or things I could be doing better on, and I didn't quite know how to get that information. And that made me feel much more stressed or nervous or at risk than having it be part of the culture to have those conversations.

**Elizabeth Stone** (00:37:45):
So the thing that I think can be nerve wracking, and I feel it myself, is the high bar for excellence at Netflix and if we're doing this while you're surrounded by amazing people. And that can feed a sense of, "Am I doing well enough compared to how everyone else is doing? I know the bar's high." For the most part, that can drive people and in a good way, but in some ways it makes people nervous. And that's where I think it's helpful to know we expect to have these conversations so you can just kind of let your shoulders relax a little bit of, "Yes, the expectations are high, but my manager says I'm doing a great job, or my manager says I'm not doing a great job, but they gave me concrete things that I could do better." And so I think knowing is better than not. And so in that sense, it's the culture combined with the conversations around performance I hope take a little bit of that stress out of it. But I've certainly heard it a lot that without that conversation, people can be nervous.

**Lenny** (00:38:49):
That's such a good point and such a good example that I feel like every company wants to have a high bar and have only high performers and keep the bar really high for every person they hire. I'm curious, I know this could be its own podcast and book, but just in terms of hiring people that are amazing and keeping this bar of excellence, is there anything you can point out that might be helpful to other companies hiring to help identify amazing people and make sure that bar stays high? One thing I know is you guys pay a top market for salary. I think that's one unique thing about Netflix, is we just pay people. So maybe that's an part of this answer, but just what advice do you have for people to keep a really high bar in their talent?

**Elizabeth Stone** (00:39:33):
Yeah, I mean on the compensation point, we pay what we call personal top of market, meaning we want to be highly competitive in the pay, but we don't want pay to be like the golden handcuffs of Netflix sets market rather than paying people a strongly competitive compensation. So I think that that's important for attracting and retaining talent and has been a big part of the culture, but almost more importantly, we hope we don't have to rely on that to want people to want to be at Netflix or for us to be able to assess whether people are going to thrive at Netflix.

**Elizabeth Stone** (00:40:20):
The way that I've thought about hiring with that context is we know we're going to offer you very highly competitive compensation, but are you going to come to Netflix and help us identify the right problems to solve or new ways to solve existing problems? And that's a different way of hiring than you might think about, especially at scale where you're saying, "Does this person have this skill, this skill, this skill? Check they're going to fit in this box and they're going to deliver this work that I need them to do." I'm being intentionally simplistic. I recognize a lot of people don't hire actually that way. But at Netflix we try really hard to say we're looking for the new perspective or the person who's actually going to make us stronger as a team. So thinking about additive skills, additive perspectives, people who are going to push our thinking on something. That tends to help us with thinking about talent density because you're constantly introducing people to the team who uplevel.

**Elizabeth Stone** (00:41:25):
So then the questions you have to ask in an interview might be different because yes, we're trying to assess do you have the baseline skills to be successful here, but we're also looking for the things that make people exceptional or even stronger than the team we've got. And then you think about making the magical teams comprised of all those amazing minds and what can you get out of that. And that feels like more that the talent density and practice.

**Lenny** (00:41:50):
Got it. So the advice there essentially is, don't look for someone just simply great. Look for someone that raises the bar for the whole team, brings in a whole new perspective.

**Elizabeth Stone** (00:41:58):
Yes. That's a great way to say it. Yeah, it's a good way to say it.

**Lenny** (00:42:00):
I think what's great about this idea of just maintaining excellence consistently is that the best people want to work with the best people. And as soon as there's one person that sucks and the company allows for that, it just brings everyone down because they know, "Hey, we can be okay. We'll stick or no one's going to do anything about it." And when you make it clear, we only want the best and only hire the best and only keep the best, it keeps the best there, right? I imagine that's part of the strategy.

**Elizabeth Stone** (00:42:29):
Yeah. It's definitely the goal. And I think understanding that having gaps in the team and people's skillsets or their behavior can be really toxic for other people on the team. So it's a cost.

**Lenny** (00:42:42):
**Elizabeth Stone** (00:44:15):
That is freedom and responsibility in a nutshell. So let me explain that. It's a good question. It's kind of related to what I was saying earlier, that talent density is a prerequisite for a lot of the other ways we operate. So if we want to create a work environment where we are not prescriptive about how people solve problems or the scope of problems that they could tackle, assuming they're highly impactful for the business, and we don't have a lot of process around that work, so think about being able to make large innovations to our engineering systems or introducing new ways to think about metrics and experimentation, we get a lot of those things because we give people the freedom and the space to explore and question things and experiment in a way with solutions. I think that that would be very hard if not dangerous if we didn't have a high talent density.

**Elizabeth Stone** (00:45:32):
It's really not a top down do A, then B, then C. Even in how we go through some of our planning processes or thinking about how we think about priorities, there is a lot of room for contribution across all levels of the team and that requires talent density. And then there's things like you have to have amazing people if you're not going to have really strict guardrails that would influence the consumer experience or business stakeholders experience. We do give people a lot of responsibility on those things. So I think the lack of process and prescriptiveness is all hinging on we've got amazing people who are smart, but even better have strong judgment.

**Lenny** (00:46:18):
This is kind of what you always hear from people giving founders advice is, "Just hire amazing people, get out of their way and let them do their job," which is often not a successful experience. What are examples that either things that came out of this freedom, I don't know, products or features or ideas that came out of this or policies or processes you don't have that everyone else might have? So I know there's no vacation time, there's unlimited vacation time, I assume. Is that still a thing? Unlimited vacation time?

**Elizabeth Stone** (00:46:48):
Yeah.

**Lenny** (00:46:49):
Okay, cool. All right, great. And I know performance reviews, you talked about that. So I guess in either direction, is there an example of something that came out of this freedom or some process that which surprised people that you don't have or a framework or system?

**Elizabeth Stone** (00:47:05):
We've been able to deliver... I'll speak to my own team around innovations in our content delivery network or innovations in encoding or innovations in discovery and personalization. We're not driven by some leader saying, "I think this is a priority." They were driven in many cases by individual contributors who had great ideas for innovation. So a lot of the stuff that Netflix has succeeded in, came from creating space for people on the team. So there's probably thousands of examples of product features and things like that that came out of creating this space. And right now, the trick is finding the sweet spot so that we can operate efficiently at this type of scale without snuffing out some of that, what was kind of the core beauty of the culture.

**Lenny** (00:47:55):
Maybe a last question around just the culture. We talked about candor a bit. I'm just curious if there's an example that comes to mind of an example of candor that you recently saw or had to be the candid person that might be interesting to share where it's like, "Oh wow, that's what you mean when you say a culture of candor."

**Elizabeth Stone** (00:48:15):
There's a couple things that come to mind. I am generally a transparent leader, meaning I share information freely and openly. It's part of the culture to context, not control, which means part of my job is to make sure that people have the context they need to do their jobs well. And in practice, that means I take notes in leadership meetings and I share those notes with the whole organization. And that is sometimes it includes candor around reflections on things that aren't going well or problems we need to solve. Sometimes it's just letting people know, "Here's what leadership's talking about so that they have a sense of what's top of mind." But it's a version of transparency that I feel strongly about, doesn't exist a lot of other places. I think it's a version of candor too in being able to share... I can't always share every detail of everything that we're talking about, but I do try to share things that probably push the boundary a little bit in the team, feeling like they understand what's happening across the company and what I'm thinking about.

**Elizabeth Stone** (00:49:22):
And then there's a second example that comes to mind, which is, until two years ago, individual contributors didn't have levels at Netflix. So all engineers were just senior engineers, all data scientists were senior data scientists, and we did not have a leveling system. We introduced IC levels two years ago almost exactly. And it was a big, big, big shift because it was seen as something that was sort of sacred of it. A lot of people came to Netflix because we didn't have it. We didn't have process around promotions. This is probably part of why we never had performance reviews, because promotions really weren't at play. And it gave people a sense of freedom of not having to worry about that type of structure. But when you get to a scale of an organization, we needed some type of scaffolding to say, "We want to talk about how we compose teams. When do we need the person who has 30 years of experience? When do we want to have a new grad?" Because that's what the work requires. We didn't have a language for it.

**Elizabeth Stone** (00:50:27):
So I introduced Levels a couple of years ago and we had quite a change rollercoaster is the only way I can describe how it went.

**Lenny** (00:50:38):
That's a good phrase.

**Elizabeth Stone** (00:50:40):
Yeah, it was sort of like being the tumble dry machine for a few months, and so really talking through it with the team. That's just context and backdrop. For an example of candor recently, which is, we had kind of a postmortem or a retro on how has it gone with IC levels. So it's kind of like wells, not wells. And I would normally think in a lot of cultures it would be like, "Well, we got past that change. We're living that change." Don't reflect on it. Because that kind of opened some of that early debate. And I felt differently about it. I think it's a good example of being candid about, this was a big change for us. It hasn't all gone perfectly. There's a lot that we can do better in how we implement levels at Netflix. And I would rather share that information than pretend it's all gone swimmingly and we achieved every objective. So I think that I try to build examples like that because I do think that level of candor and reflection helps build the sense of community and trust across the team.

**Lenny** (00:51:44):
That's an awesome example. Kind of along the lines of that, but also this category of freedom and responsibility, something Netflix innovated long ago, and I'm curious if this is still a thing, is this idea of Chaos Monkeys, which essentially are a program that runs on your infrastructure that just kills random processes and things and just to see what breaks and make sure things are stable when things actually start falling apart. Is Chaos Monkeys... Was that what it's called? And then is that still a thing? Is there still some Chaos Monkeys running around the servers?

**Elizabeth Stone** (00:52:19):
Not unbridled Chaos Monkeys. No.

**Lenny** (00:52:22):
Okay. Contains chaos and niche.

**Elizabeth Stone** (00:52:24):
Bur no, we carry too much responsibility, speaking of freedom and responsibility for the member experience to inject pain, though we do do a lot of experiments to test resilience, and that does probably mean injecting things that we're not quite sure whether A is better than B. And so that happens across engineering systems really at scale. But it is not for pure chaos, it's for intentional learning and so we can avoid making bigger mistakes. And then as we go into new efforts like cloud games, we have a beta that's out now, Live would be another example. We do try to come up with intentionally low profile examples where we can test the bounds of our systems in a way that's unlikely to damage the member experience. But that's less randomness, more by design. And so we're doing that in a few places that feels mostly good engineering practice so we can understand when it's really showtime and we're going to really test our systems, will they be able to perform like we want them to.

**Lenny** (00:53:42):
RIP Chaos Monkey.

**Elizabeth Stone** (00:53:45):
Yeah.

**Lenny** (00:53:47):
So kind of along these lines of data, so data itself has always been at the heart of Netflix. My understanding is the way the data team and the insights team is structured has been one of the reasons Netflix has been so successful. And that's the team you led before you moved into this new role. Can you just talk about how these teams are structured and why this structure is so effective?

**Elizabeth Stone** (00:54:14):
Yeah. I certainly like to think of it as being special. It's unusual. I can explain why. So the scale of company that Netflix now is very often data oriented teams are embedded in other parts of the business. So it could either be they're embedded in a business line like ads or games, or they are organized more functionally separating data engineers from data scientists, from analytics engineers, from consumer researchers. We've resisted that and kept a centralized team that is both functionally diverse. So across all those types of functions that I just described and works on nearly every area of the business from within the team. I sort of understand why a lot of companies move away from this because it really does require basically extraordinary partnership that we would have people working on data problems that don't report into the teams that are relying on them.

**Elizabeth Stone** (00:55:30):
But the benefit we get is we get to think about our functional expertise. So are we really world's best data engineers, world's best data scientists? And how do we continue to be ever better from a functional and technical perspective? It gives people better career paths because there's more mobility across the teams. It feels like a team that has a functional expertise with a lot of different problems to solve. And so I think it enables more cross-pollination of ideas in a way.

**Elizabeth Stone** (00:56:03):
It also allows us to be really objective. That is probably the most important thing, that our job is not to tell the story that someone wants to hear with the data or to solve the problem that someone thinks is most important. It's for us to have our own perspective about things. I think that that uplevels the whole organization because it means that we're able to be truth tellers or to be curious in a way that might not fit if we had a different organizational structure. We have to balance, that would be a good partner, deliver on the things we agreed were priorities, be flexible with how we're spending our time, but it gives us agency and responsibility beyond that. And I feel like the team takes that very seriously. So I've seen examples of that in how we bring data to a lot of spaces, including how we partner with engineering on data-related topics or how we partner with content that I'm not sure we would've gotten to if not for having that kernel that's sort of a center of excellence around it.

**Lenny** (00:57:10):
And it's Data and Insights, that was the team that you ran. Insights, is that describing user research or what does that have function actually?

**Elizabeth Stone** (00:57:19):
So part of Data and Insights is a Consumer Insights team that includes a lot of different flavors of research really. So in some ways, consumer is even a misnomer because there's parts of the team that do internal research, for example, on tools and products for our studio productions. So that's more of a user research-oriented versus consumer. And then the parts of that team that are consumer-oriented do things all the way from content screenings to make titles the best version of themselves before they're on the service to more traditional UX research to think about how can we deliver the best title discovery experience or how can we think about things that improve accessibility? And then that team has a global remit. So there's also teams that are more local or regional expertise in understanding consumer needs and entertainment.

**Elizabeth Stone** (00:57:12):
So Consumer Insights and a team, formerly known as still kind of known as a shorthand, data science and engineering, combined together to create data and insights probably about two years ago. That's another piece that's unusual. It becomes truly a full-stack data and research expertise. And so we could tackle a problem like, what's the right way to think about recommendations and how best to surface them in a way that combines attitudinal research, qualitative and quantitative with behavioral research on more of the data science, data engineering analytics side.

**Lenny** (00:58:51):
It's super cool because I think it's really rare that what people think of user research is within the data org. And I think that might be a solution to some of the backlash a lot of user research teams get where they're like, I don't know, what are you guys doing all this anecdotal evidence if it's under the same org. I feel like that leads to a lot more credibility and avoids this like, "Oh, data's telling me this thing. This user research team is telling me this thing. What should we do?"

**Elizabeth Stone** (00:59:17):
Yeah, I mean, Consumer Insights is one of the newer teams for me; it wasn't in my background to lead a team like that and not in my individual training, but they are critical for making sure we keep a consumer orientation, a member orientation on things. I have loved to watch the teams collaborate on problems because we talk about it as a superpower internally in combining those skill sets. So I think the Consumer Insights team at Netflix has had a lot of credibility in a certain area of expertise and we took it to the next level by combining it with other functional expertise. So it's not required in every problem space. So we try not to overdo it and say we need to be collaborating everywhere because that just feels like the wrong expectation, but we try to make the most of it in spaces where we really benefit. So yeah, it's worked out really well.

**Lenny** (01:00:12):
Awesome. Okay. I want to ask two more questions before we get to our very exciting lightning around. And they're both skills that [inaudible 01:00:08] have told me you're very good at. One is that you are very intentional and thoughtful about staying close to individual teams and individuals within the company, even though you're higher and higher in the org. I'm curious how you do that, how you actually practice this skill of staying really close to teams at the bottom of the ladder and individuals that are working on things on the ground basically?

**Elizabeth Stone** (01:00:45):
A lot of it is how I spend my time and fighting to preserve opportunities to connect with people. So examples would be, I still have biweekly office hours, people sign up for slots. It can feel a little like speed dating for 20 minute slots, but I get to meet a whole bunch of people and hear about work, hear what's top of mind. People book them out many months ahead and it's just an opportunity to stay in touch. And then I do Ask Me Anything sessions with teams of different sizes depending on how intimate we want it to feel, but truly anything is fair game as a way to get to know me as a person, for me to hear questions, to try to be candid about what I can answer or can't answer. And so those things have helped me maintain connection, but both of those examples are about making the time for it.

**Elizabeth Stone** (01:01:50):
So what I have found as my role has changed is that it just wouldn't happen if I didn't make it a priority. And then through those types of sessions, I do think I become or I hope to become more approachable so people know, "You can send me a Slack message, you can send me an email. Like I mentioned earlier, I'm going to respond to you as quickly as I can because I want to hold myself to that bar." And so that builds a flow of communication between me and the team that I really value... I don't think I would want to do my job if I didn't have those points of connection, so that helps too.

**Lenny** (01:02:24):
And you also send that email to everyone after every leadership meeting, so they're like, "Oh yeah, Elizabeth."

**Elizabeth Stone** (01:02:28):
Yeah, they hear from me. Yeah.

**Lenny** (01:02:31):
Kind of related to this, so we have a mutual friend, that's how we got connected. Ali Rao, she was a data scientist at Airbnb, now she's at Uber. She had a question that she wanted me to ask, and it's about how good you are at being present. So her question is something she's noticed about. "Something I've noticed about her is how 100% present she is no matter who she talks to. Do you have any advice for people to get better at this? Because it's so hard in the day of email and iPhones and Slack." Her questions like, "When does she respond to stuff if not sometimes in meetings?"

**Elizabeth Stone** (01:03:05):
I actually think I'm the most present when I'm having conversations like this one. I do preserve a lot of time to have one-on-one conversations where I'm genuinely curious about how someone's doing, how I can help them, what they're excited about that's authentic. And so while my EA would probably cringe at saying I like to spend time doing a lot of those one-on-ones, it is relatively easier for me to say the human connection is part of what I enjoy about this. I think that's true for a lot of people in what we get out of work and life, but I try to live that in those meetings. I'm probably not as good when we're talking about meetings of 30 people and I'm multitasking, so I'll admit to doing that for sure. But I think the one-on-one conversations I treat as being pretty sacred.

**Elizabeth Stone** (01:04:09):
One of the things I've noticed that helps me continue to invest in that and maybe is helpful for other people is some of my greatest friends and connections, including people like Ali, are people I met along the way professionally. So I worked very closely with Ally's husband, Keith Henwood, at multiple places, both Analysis Group and at Lyft. And that means that it's created opportunities and it's been points of connection. And so you get back what you give basically.

**Elizabeth Stone** (01:04:45):
There are people in my life who are part of my life because I worked with them or because I crossed paths. And I like to think that if I can make a positive mark on them, it'll come back and be at some point too. So I think to distill that is that I truly enjoy it. It's what I get out of especially work. And then it's my community. And that's served me really well over time. And so I have given people advice of, "This is a small community, think about what you're investing in other people because that will matter down the line for yourself too" and I try to live that myself.

**Lenny** (01:05:22):
Yeah, that's such good advice. There's kind of two things that come to mind there. One is treat people the way you want to be treated. Someone once said that maybe. And I think you've come back to this a couple times, this idea of just pay attention to what gives you energy and that you're good at and just almost double down on that. Just make that more and more of a superpower.

**Elizabeth Stone** (01:05:41):
Yeah, that last part resonates. It's been a big part of my personal and professional practice to reflect on how I'm feeling, what I'm excited about, what I'm enjoying. I do think it helps me be more grounded, which maybe helps me be more present or helps me be a better manager or leader. That might be part of the secret sauce too, but it is part of my practice.

**Lenny** (01:06:11):
I can't help but ask, is this an actual practice? Do you do this on a regular basis or is this just something you think about like, "I should reflect back"?

**Elizabeth Stone** (01:06:18):
I wish I was so advanced to say I meditate and I create all this structure. It's more that I think I mentioned maybe I'm an introvert, so I do spend some time alone. That's how I recharge. And early mornings, especially people who know me sometimes are horrified at the time of day I send emails, but early mornings are a quiet time for me where I do try to have a daily check-in of just how are things going, why am I feeling anxious, why am I feeling excited. And it's kind of a muscle you build. So while I don't write in a journal, I don't have a meditation practice, I do have a time of day when I try to keep it protected from other things so that I can think for a second.

**Lenny** (01:07:05):
What I think about there is Jeff Bezos has this approach in the morning. He just calls, he putters around. He has no meetings until I think 10:10 or something. He just wants to putter around, read the newspaper, see what's going on in email, which I'm trying to do. I really like that. That feels really good. I'm just going to putter around. I have no responsibilities in the morning.

**Elizabeth Stone** (01:07:22):
I've never heard that. I'm going to adopt that language.

**Lenny** (01:07:27):
I'm just puttering and puttering. Elizabeth, is there anything else you wanted to touch on or leave listeners with before we get to our very exciting lightning round?

**Elizabeth Stone** (01:07:38):
No, I'm ready for the exciting lightning round.

**Lenny** (01:07:40):
Well, with that, we've reached our very exciting lightning round. First question, what are two or three books that you've recommended most to other people?

**Elizabeth Stone** (01:07:50):
It's probably a little recency bias, but I've been recommending What I Talk About When I Talk About Running by Murakami, which talks about introspection about the similarities between running and writing as sort of flow states and very meditative things. So I had read some of his fiction books and the autobiographical reflection on these types of either professions or hobbies I think is very insightful. So that's one. And then one of my longtime favorite books is A Fine Balance by Mistry. And that is just a great story of human complexity and challenge and relationships. So I'm drawn to both books and TV and film that are about humans.

**Lenny** (01:08:43):
Speaking of TV and film, this is maybe a high stakes question for someone that works in Netflix, do you have a favorite recent movie or TV show?

**Elizabeth Stone** (01:08:52):
I'm not going to name all Netflix. That feels too much like an advertisement. Film, Triangle of Sadness is phenomenal if you haven't seen it. And then I'll go Netflix for TV, Beef was I thought hysterical. I'm an Ali Wong fan, but also just a pretty unique storyline.

**Lenny** (01:09:18):
And I think they just won a bunch of Emmys.

**Elizabeth Stone** (01:09:20):
They did.

**Lenny** (01:09:21):
Amazing. Good picks. Next question. Do you have a favorite interview question that you like to ask candidates that you are interviewing?

**Elizabeth Stone** (01:09:29):
High talent density. I'm usually looking for the person who would be better in my role than I am in my role. So I often ask people what would their priorities be, what would they do differently if they had my job.

**Lenny** (01:09:45):
Next question, do you have a favorite product that you recently discovered that you really like?

**Elizabeth Stone** (01:09:52):
So while I carry the CTO title, I live a pretty analog life. So my most recent product is a Fellow pour-over coffee maker, which is actually part of my morning ritual, which I'll now call puttering around, where I take great lengths in my coffee-making process because I find it calming. And then it's not a recent find, but I have to shout out that my Peloton is probably the favorite product I own.

**Lenny** (01:10:22):
The bike or the treadmill?

**Elizabeth Stone** (01:10:24):
Bike. I'm a recovering outdoor cyclist, so it's also kind of questionable if I can even admit to this, but that's why I would admit to I love the Peloton despite being ideally an outdoor cyclist.

**Lenny** (01:10:39):
I have questions about your cycling, but before that question, do you have a favorite life motto that you often come back to or share with friends or family that you find useful either in work or in life?

**Elizabeth Stone** (01:10:50):
My mom said something to me that has stuck with me. I don't know if I live it very well, but the phrase was, "Something good happens every day." And the reason she said it was because she was encouraging me to be more mindful about enjoying the small things in the day-to-day rather than letting myself get caught up in the busyness.

**Lenny** (01:11:13):
Beautiful. Final question. You're a big biker and triathlete. I am curious what that sport and time has given you in your career or in life. What benefits have you found from spending so much time and energy, running, biking, being an athlete?

**Elizabeth Stone** (01:11:32):
Certainly by mental resilience. So while those sound like physical strength, I've found especially endurance sports are much more mental and how you go through the highs and lows and sustain and then coming back from challenge. So those sports have had their highs and lows and from the lows I've really learned how to recover and bounce back. So those feel like universally applicable skills.

**Lenny** (01:12:04):
You have such an interesting mix of athleticism and then Netflix, what a good balance for life. This is going to give me permission to go watch Netflix recording this on Friday afternoon. Elizabeth, you're awesome. Thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out and maybe follow up on things? And how can listeners be useful to you?

**Elizabeth Stone** (01:12:24):
You can always find me on LinkedIn, so definitely reach out or ping me if you have questions or comments. I think the way the listeners can be useful to me is being maybe curious about how they can show up even better in their lives now that we've done this reflection on Netflix culture and how we show up for other people. I would like to ask listeners to pay that forward to people that they're working with and how they show up for them.

**Lenny** (01:13:02):
Amazing. I love that. If you end up doing this and you're listening, maybe leave a comment on YouTube or in Substack with something that you haven't covered about yourself. Elizabeth, thank you so much for being here.

**Elizabeth Stone** (01:13:16):
Thank you, Lenny. I hope you have a great weekend.

**Lenny** (01:13:18):
Same. Bye everyone.

**Lenny** (01:13:20):
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.

---

## [13/19] How to discover your superpowers, own your story, and unlock personal growth | Donna Lichaw (author of The Leader’s Journey)

**Donna Lichaw** (00:00:00):
When superheroes discover what their superpowers actually are, they wreak havoc and they make a mess, and it's uncomfortable. And even Superman tries to get rid of his superpowers. It's hard to know what you're really great at.

**Lenny** (00:00:13):
How does somebody identify their superpowers, their strengths?

**Donna Lichaw** (00:00:17):
Pull your superpowers out of your stories from your past, your present, and then eventually figure out how to apply them and transpose them to your future.

**Lenny** (00:00:27):
The person's story; this is central to becoming a better leader.

**Donna Lichaw** (00:00:31):
The most effective stories are the ones that we tell ourselves. They may or may not be true; our brain doesn't know the difference. Once you can really understand that, you may as well leverage it to be that hero.

**Lenny** (00:00:46):
Today my guest is Donna Lichaw. Donna is an executive coach, speaker and bestselling author. She helps founders, CEOs and executive teams level up their leadership skills and scale their impact while staying true to their mission, their purpose and themselves. Donna has worked with leaders at companies like Google, Disney, Twitter, Microsoft and Adobe, and she's also the author of the book, The Leader's Journey, which is what we spend our time on.

**Donna Lichaw** (00:04:29):
Thanks, Lenny. It's exciting to be here.

**Lenny** (00:04:31):
We connected through a former colleague of mine who could not stop raving about how much value she got from working with you. Also, you have a new book app right here that I have, The Leader's journey, and so I thought it would be awesome to bring you on and share your wisdom with a wider audience.

**Donna Lichaw** (00:04:50):
Love the podcast. My clients love your stuff and newsletter, everything.

**Lenny** (00:04:54):
[inaudible 00:04:54].

**Donna Lichaw** (00:04:54):
Very excited to be here.

**Lenny** (00:04:55):
Amazing. And congrats on the book, by the way.

**Donna Lichaw** (00:04:58):
Thank you.

**Lenny** (00:05:00):
You actually were a product manager in a previous life. You're also a designer in a previous life. These days you're an executive coach. Just briefly, I'm curious what pulled you from product management design and the things you did before this life into executive coaching. And maybe another way to ask this question is what's your origin story? And this is a little foreshadowing to the stuff we're going to be talking about later.

**Donna Lichaw** (00:05:25):
Actually, it's funny, like all origin stories, there were actually multiple episodes, multiple moments that led me to an epiphany, but the biggest aha moment was when I was working several years ago, almost a decade ago at this point, with an executive team in Silicon Valley. And we were at a leadership retreat, and we were supposed to... At the time, I was a program on effective product leadership, how to be a great product leader, product executive. And the biggest thing that companies wanted at the time and teams wanted was their teams to be better storytellers. And it's still something we hear today, which is, "To be a great product leader or leader in general in any industry is you got to be a great storyteller." And so at the time, I was teaching and facilitating storytelling workshops and exploring that with teams. And it was a few people on this team specifically who I so appreciate their honesty and candor here, which is what this giant tech company is known for, very blunt people working there. And they pulled me aside halfway through the offsite, and they were just like, "Honestly, storytelling is not going to fix our problems. This is silly."

**Donna Lichaw** (00:06:56):
And what they were able to tell me is that their leaders wanted them to be more effective by having greater influence. And these are terms that we throw around all the time. Be more influential and be a better leader, whatever that means. And what was happening on the ground with these executives was that they were all fighting. I'd hear, "Oh, the head of engineering is such a jerk," or, "This person won't listen to me," or, "My team is demotivated. And I get it, but they need to step up and work more." And there was just a lot of conflict going on here and there that storytelling wouldn't fix. When that happens, and I talk about this in the book a bunch, no one wants to hear your stories. You have to actually be able to connect with people and to work with people and feel good as a leader in order to really step up and lead. I didn't have an answer for this team at the time, and I left this offsite just honestly feeling terrible and not knowing what to do about it except telling them, "I think you got to go work with a coach because this is beyond my pay grade."

**Donna Lichaw** (00:08:05):
But when I left that day, I just couldn't stop thinking about this team because I had a hunch that stories were still a part of something but not what they needed. Telling stories was not the answer, and so I ended up spending what now is the next decade figuring out, all right, how do you become an effective leader? And of course because I can't do anything lightly, once I went down that path, I ended up switching up my entire business. And now that's all I do is help people be better, more effective, confident leaders who really make the impact that they want to make.

**Lenny** (00:08:39):
Along those same lines, what's interesting is you actually found that this idea of storytelling was actually much more effective in your coaching practice. Instead of helping them figure out the story of the product, it's the story of the person. And so transitioning into the meat of your approach to coaching, I think you call it story-driven leadership. Essentially, your finding is that story and the person's story is extremely important and powerful in helping them level up as a leader and also seeing them as the hero of their story. I guess just with that foundation, can you just talk about why that is so powerful, the idea of figuring out your own story and why you need to be the hero of your own story and just what all this means?

**Donna Lichaw** (00:09:21):
We all as humans want to be the hero of our own story. It's how we live our lives, it's how we make choices, it's how we understand the world around us, and it's how we communicate back to the world. With leadership, it's much the same, which is we have a mission that we want to accomplish. No matter how big or small, it's something; we're driven to do something. If you're a leader, you want to be a leader. You have to be taking yourself and you have to be taking people somewhere.

**Donna Lichaw** (00:09:55):
We also have obstacles, so that's a part of any great story. There are challenges. It shouldn't be easy. It shouldn't be so hard that you fail, that's a tragedy, but there are challenges, and it makes life more exciting. You don't do it alone. It's rare that a story just has a single individual. It happens, but that's not most of life. And there are other elements that I ended up uncovering when I looked deeper into what makes the most effective leaders effective, and the biggest thing is stories that we tell people, it's like the tip of the iceberg. And if anything, it even doesn't matter, I've worked with a lot of folks who their teams say, "Stop it with the storytelling. Stop talking at us." And they don't want any of that.

**Donna Lichaw** (00:10:43):
But the most effective stories are the ones that we experience as we live life and that we tell ourselves as well because we have the ability by saying things like, "Oh, I'll never succeed," or, "Oh, she'll never go for it," or, "He's such a jerk." Or whatever the stories are, these are all stories. And they may or may not be true, they're usually not true, but our brain doesn't know the difference. It's the most powerful ability our brain has is to understand and see stories everywhere. And so once you can really understand that, you may as well leverage it to be that hero in your life. And even as I say it out loud, it sounds so cheesy, but it's true. This is neuroscience and psychology. We just want to be the heroes, and that's what our focus is.

**Lenny** (00:11:36):
I want to delve deeper into that idea there. People listening to this might feel like, "Okay, cool, let me think about the story of my life. This sounds like a fun thing I could do." But I think your point is this is central to becoming a better leader, figuring out the story of you and that changing in your perspective on yourself and giving you more... Unblocking you I think is a big part of it. Can you just talk about more just the power and why this is so important? Because it not just like, "Cool, I'll sit around and think about, oh, here's my story. I was born here, I did this thing." Why is this so important to do?

**Donna Lichaw** (00:12:12):
And it's a little antithetical in a way because it goes against what a lot of us believe, especially if we have I'll say product backgrounds or just business backgrounds or tech backgrounds or anything where we've built things for people. For years, we've had this idea that we build companies in a user-centered way where, all right, build for the customer first and all else will follow. And there's some truth to that on the one hand. And I used to think leadership was the same, which is, well, it's not about you as a leader, it's about who are you bringing along on your journey? And how do they need to be heroes? So how do you enable everyone you work with and everyone you want to follow you to join you and feel amazing with it? That's the user-centered approach where it's not about you, it's about who you're bringing with you and the impact you want to make.

**Donna Lichaw** (00:13:13):
But what I learned is that it doesn't work that way. And you need to flip that, which is when you start with you first at the center of the equation, and then I'm going to do... Everything for me is a diagram. I'm thinking of concentric circles. Ken Blanchard has a great model for this where you start with you, it's the inner circle, then you are able to lead yourself, then you can lead others. It extends to one-on-one relationships. Then once you've got that, you're able to lead groups, teams, and then outward towards the business.

**Donna Lichaw** (00:14:00):
When you figure that out and you come from the inside out, it's much, much more powerful because it's not selfish like I would've thought years ago, but it's purposeful. You, as human, we all are driven by a mission, by purpose, by a reason for what we do. And when we're able to have that power us, it then empowers us to connect with others so that we can bring it to life. And especially in a business context, but this is the case in anything, communities and family, but especially in business. It has to start with you. You need fuel from somewhere. And if it comes from without, it's like an eggshell that's just ready to crack. It's not sustainable if it comes from outside.

**Lenny** (00:14:49):
Can you give an example of someone you worked with that changed their story and what impact it had on their career to make this even more real?

**Donna Lichaw** (00:14:58):
I can think of a CEO I worked with a few years ago who on the outside was so put together. He was the CEO of a billion-dollar company, successful, raised money like no one's business, was able to get people excited about what he was building, join him. And when we started working together, he had recently hired members of an executive team that were just superstars from Silicon Valley and just incredible. And they were so excited to work with him. He was so excited to work with them as well.

**Donna Lichaw** (00:15:42):
But on the inside, the story he kept telling himself was he's too nice. Nobody listens to him was another story. "People don't take me seriously," was another story. And then there were what I call horror stories. This is not a scientific term by any means, but horror stories that he told himself were things like, "We're never going to make it," or, "They're never going to listen to me," or, "I'll never learn to be a real CEO. And the problem with stories like that is they end up taking over your identity, they shadow and cloud your every day and actions you take and interactions you have with people. And when you focus on them so much, they very well will become true. That's one example. I could tell you a little more about that, what we did about it.

**Lenny** (00:16:45):
Yeah, that's exactly what I was going to ask. Yeah, if you could share what you did to help shift his story, and then also just how do people do this for themselves?

**Donna Lichaw** (00:16:55):
Perfect. In this case... And this is like everyone I work with. And this is absolutely something that everyone listening and everyone in the audience can absolutely do is take a data-driven approach to the stories that you tell yourself. For example, the story, "I'm too nice," it could be true, it could not be true. How did we get down to the bottom of that? In this case, what we did is I went out there and talked to his team. And this is something you can do for yourself as well. If you're extremely busy, you can have someone else do it for you. And I found out how people actually experienced him and his leadership. And I didn't hear he's too nice, I heard he is so heartfelt and so caring. And that's a really cool thing. How rare is that to hear about a CEO, especially a founder? Oftentimes you hear the opposite, which is not really true. Usually when founders are not nice people, they're insecurity's at play. But in this case, yeah, people were like, "We love him. He's wonderful. That's why he recruited us." And so great, all right, validated and a little debunked. Really nice, but not too nice. That was not a problem for anyone.

**Donna Lichaw** (00:18:31):
Then we'd hear things like... Okay, one story he told himself was, "People don't take me seriously. They don't listen to me. What's going on? I need to command respect and they need to just do what I say." And I hear this all the time. I'm using this one example, but this could be anyone that I've worked with. And what we heard from people instead was it's not that they weren't listening to him, but when you're hiring super senior, whip smart executives to work for you, they don't want to be told what to do, they want to have a grand vision that they're excited about, they want maybe some goals to latch onto and help possibly with a strategy to get there, although probably they can got the strategy all on their own. And they want to then show you how they can help you and the business meet your goals and align towards that vision so that you can build the company that you want to build.

**Donna Lichaw** (00:19:35):
That story, "No one listens to me," it was the wrong story to be telling. What the actual story was is that people wanted him out of their business and wanted to feel empowered doing their C-level and super senior executive level work. "But we don't want him to be absent because when he does that, it doesn't work. And it's very frustrating when he just disappears for two weeks. So we need him involved, but want him to give us problems to solve. Give us a vision, give us problems to solve and let us do it for you."

**Donna Lichaw** (00:20:10):
And so they were able to write a better ending of that story together. It was exactly like user research of any kind or customer discovery, which is you find out what could be possible from your customers and then ideally you co-create a better ending together. If you're building products or services, that's how you do it. If you're a leader, you do it by showing up and helping others do what they need to do in a way that feels good for you and that aligns with how you want to be doing things.

**Donna Lichaw** (00:20:44):
And so this is one example, but I find using real research and data and actually talking to people is most effective. There are other ways to take best guesses, and I'll use the product metaphor again, which is you can try things and experiment and then see how it works and not talk to your users, but you should probably talk to your customers, in other words, your colleagues and everyone who works for you, and really find out what is the true story and what is possible.

**Lenny** (00:21:19):
There's all these stories that people believe about themselves, and to your point, many of them are not true when you actually look at the data, you talk to your customers, AKA your colleagues. I imagine many are actually true or there are feedback you get that is like, "You are not clear enough about stuff," there's things that you actually hear from other people. Does this approach help there as well? Or is there a different tactic for something's actually, okay, you are actually too nice. It's not just a story in your head?

**Donna Lichaw** (00:21:48):
Absolutely. There are times when the stories that we tell ourselves are true. And when we go out and find out what's possible, it is something that we're doing that needs to change or isn't working. And so one example is, and this comes up sometimes as well, one executive who I worked with once kept getting this feedback that she was too quiet. And when we went out and got feedback, it was true. People were like, "She needs to speak up more." And this is becoming a problem because she was so quiet that her team thought she was not interested in them. And she would just sit back in meetings, not say anything, and they were like, "God, she sucks. This is the worst boss ever. I don't even want to be at this meeting. And why is she here? Why am I here?" And it really was detrimental to them all working together.

**Donna Lichaw** (00:22:57):
And then she was frustrated because she was always wondering, well, why are they not performing? They're not stepping up. And so it was frustrating all along. And it was true, as far as they saw it, her not speaking up was the problem. But when we got down to the bottom of what was really going on for her and not speaking up at these meetings is she was just listening. Her processing style was she had to listen, and then maybe a few hours later she'd have thoughts. And so even though the team said, "We do want her to participate," what they really needed to know was it didn't have to do with speaking or not speaking, what they really needed from her was to know that she was listening to them and that she actually heard them and was going to do something about it, and that she was quiet in these meetings, she was not checked out. And so simple solution for that, she could start trying to yell more and talk over people and be obnoxious, but nobody wants that either, and so she just started communicating with them more about, "Hey, this is my style. I'm a little slower. I often need a couple hours to really process things. I'm here, and I want you to know that."

**Donna Lichaw** (00:24:12):
And the irony of establishing those lines of communication with your team when they're not getting what they need is that you often end up doing the thing that you've been trying to do but failing to do anyway. Because she ended up talking more with her team just in communicating with them about her style, and then they started communicating their styles with her and with each other. And this is something that, it's not in the book, but you might've heard of this idea of a personal OS that a lot of us like to have, which is, "Hey, these are my work styles. This is how I process, this is how I do things. These are great ways to work with me, and here's how I'd love to work with you." And they ended up doing a lot of that, and worked out really well. But it was true, she was not speaking up, and it was having a detrimental effect. But the answer was not talking more, it actually was listening more and just having a better relationship with people.

**Lenny** (00:25:09):
That's an awesome example. By the way, on the personal OS, an another term for that I've heard is README, like your own personal README file.

**Donna Lichaw** (00:25:15):
Oh, I like that too.

**Lenny** (00:25:17):
Yeah, isn't that great? It sounds like there's these two buckets, it's probably more buckets, but one is a story of yourself that is not true that you can disprove by looking at data, talking to people, and then there's almost a story people have about you that they don't quite get what's going on. And then you could change their story by communicating, "Here's what I'm really doing. I'm actually just listening and I'm actually really deeply paying attention."

**Lenny** (00:25:41):
If we pick an example, say imposter syndrome, which comes up a lot on this podcast where people feel like, "I am an imposter in this role. I have no idea what I'm doing. It's all going to crumble if I mess up." Say someone has that in their head, everyone can tell I am an imposter and it'll all crumble. How would you recommend someone that this is real or not to understand is this a story in my head or is this real? And what do people actually think? Do you go talk to people? How do you recommend people go about that?

**Donna Lichaw** (00:26:15):
Certain stories we tell ourselves are actually quite functional and do not necessarily need to be rewritten. Imposter syndrome for an example, if you're going around saying, "I feel like I'm an imposter. I can't believe I'm doing this," you can try to fake it till you make it, you can try to... I always think of... I'm totally dating myself here, but Stuart Smalley in Saturday Night Live in the '80s and '90s, he would look in a mirror and do his affirmations and say, "I'm smart, and I'm whatever." And Doug-

**Lenny** (00:27:00):
I'm good enough, I'm strong enough, and gosh darn it, people like me or love me.

**Donna Lichaw** (00:27:08):
There you go. It's like you could do that, and it's all very mechanical, and there's ways to prop yourself up, but what if you took a counter-intuitive approach and looked at that story, I'm an imposter, and instead asked, "Okay, that's a good story. How is that serving you?" Imposter syndrome, it's something everyone has at one point or another. When we default to these behaviors of, "Oh God, I'm an imposter. Okay," over and over and over again, I know it doesn't feel good, but we default to that because it's serving us in one way, otherwise it wouldn't become a habit. And I always think of habits as an itch. If you have an itch, you scratch it, you feel better. There's a reason why we scratch itches; it feels better. If you do it too much, it hurts.

**Donna Lichaw** (00:28:09):
And something like that, telling detrimental stories, have that impact. But when you can intercept them at just the right time and say, "Okay, what if that is true? How does it serve me to constantly say, 'I'm an imposter whenever anything gets hard?'" One co-founder I worked with a while back, she did this whenever things got too hard. And then she was convinced, and founders have this a lot, "Who am I to be running this company? And what am I doing here? And oh my God, I can't be doing this." But when we looked at how that habit of calling herself an imposter served her, what she realized is that every time it kicked in, she worked harder. And it just meant she was hitting some kind of a growth edge. When she would jump into action, she would learn something new, she would read 20 books, she would go out, take a class, she would listen to podcasts and on and on. And she would get better at this new thing, it was fun for her, and then she would feel less like an imposter over time, so it was a very functional thing for her.

**Donna Lichaw** (00:29:32):
The problem is when she did that too much... I work with a lot of women who this is the case for. She often did way much work. And so she took on emotional labor for other people. She did 10 times as much work as she needed to do, actual work. In her role, she was playing COO and CFO and CEO. And it's just like she didn't need to be doing all of that. And so on a spectrum of it's actually helpful, give yourself a pat on the back for jumping into imposter zone every time things get hard to the other side of the spectrum, which is, okay, but when it's too much, you burn out. You're doing way too much work for other people. You're falling into these unfortunate conventional gender roles that doing extra work you don't need to, so you want to find a happy medium. But I think that the trick is, with imposter syndrome, to not deny it, to embrace it as much as you can, but not embrace it so much that it ends up holding you back. Yes, functional. Even things that we think are bad for us are actually good.

**Lenny** (00:30:49):
I love that advice. It's so much easier to just, okay, yep, it's true. Maybe I am an imposter, but here's how he can maybe help me while I feel this. And this actually reminds me of another coach who did a guest post on my newsletter a long time ago, and her advice is, "Yeah, you probably are an imposter. You're in a role you've never done before. And that's pretty normal, and that's okay. And here's how you should approach it."

**Donna Lichaw** (00:31:12):
Yeah. Especially in tech where half of the roles we have are all made up. You're probably the first person ever to have your role anyway, whether you founded the company or you're doing something else at your company. Yeah, it's a great thing. Embrace it.

**Lenny** (00:31:28):
The takeaway advice there is essentially ask yourself, "Okay, this may be how I feel. How is it helping me?" And don't try to push it down and convince yourself that you're not necessarily an imposter, but how is this feeling helping you?

**Donna Lichaw** (00:31:42):
How is it serving you? I have a whole chapter on kryptonite in the book, which is... It's what I call kryptonite. And I use superhero metaphors pretty heavily in the book because I'm I guess a grown child and I like comics and superhero stories. And so are my clients, so I think because I work in tech, I get to do this. But I liken it to kryptonite, which is the things that we think harm us, actually when we look at how they serve us, they can serve a function. Like kryptonite for Superman, it's how people are able to operate on him. They use a little kryptonite so they could get in there and do some surgery and then get out. It serves a function, but when it's too much that can be detrimental. Yeah, how does it serve you? It's a question that it's so important and so, so powerful.

**Lenny** (00:32:37):
What are some examples of other types of kryptonite that you find leaders have? And how do you find that it ends up maybe serving them and being useful?

**Donna Lichaw** (00:32:45):
They're the kinds that you should avoid and can avoid. For example, scheduling things is my kryptonite, but I do meetings for a living. And I love being in meetings, strangely, and so not scheduling is not an option, but there are ways around it. I automate everything. And some people hire assistants. And there are ways to do it. That's the kind that you're better off avoiding. There's nothing that serves me about having to schedule things or my inability to schedule things properly. How is that serving me? You know what? I don't care. It doesn't matter. Just the kind that you need to avoid.

**Donna Lichaw** (00:33:30):
Or you could say toxic people or people who just don't add anything to your life. There are kinds of just like, "All right, done. Moving on." But then there are the kinds that it's usually on the inner kryptonite side where you can look at, "Okay, well how does this serve me?" And so wide swath of people example is dyslexia. I work with a lot of founders, CEOs and senior executives who are dyslexic. It's very, very, very common, especially for CEOs. You could say, "Well, that's kryptonite, having to read things or do things with text." And it can feel like that to a lot of people, yet when you look at the science of something like dyslexia, it's not so much an impairment, it just means that your brain is operating at a different level in a different way than most people.

**Donna Lichaw** (00:34:42):
Same thing with ADHD. And you could extend it to autism and ton of other things as well. But when you're dyslexic, you're thinking spatially, you're thinking big, you're thinking visually, you're not... Yes, you mix up letters or you're struggling with big blocks of text; that's fine. If you're founding a company, you're not in documents all day long anyway probably, so that ability to think big and spatially and visually is probably how you created your company in the first place, or if you work at a large corporation, how you catapulted into executive leadership that way because you're a visionary and you do all these things.

**Donna Lichaw** (00:35:23):
I think kryptonite, the inner kind of kryptonite, that's how I like to think of it, which is you think it makes you weak, but when you can look at how it serves you, it's often not the case. It could be something that is often classified as a disorder like dyslexia, ADHD, and it could be quirks like the one earlier, "I'm too quiet." Well, no, she was just a really good listener. She just didn't realize that she had a poker face on when she was listening. And no one knew she was listening. Everything, just look at how it serves you. It's the kind you need to avoid, the kind of kryptonite that you need to really look at and embrace. And once you embrace it, just like with the superheroes, it becomes ideally something that's useful in small doses like Superman, or it could be something more like Hulk, which is you could say his kryptonite is his anger, but that's also his superpower. And he can't get rid of it, or if he does, he becomes Mark Ruffalo being really boring like in the latest Avenger movies and he is all meditating.

**Lenny** (00:36:31):
Just moping around.

**Donna Lichaw** (00:36:32):
Yeah, I don't know what the point of that is. Yeah, that's how I see Kryptonite. It's actually a really, really amazing, amazing tool that we can all leverage.

**Lenny** (00:36:41):
The flip side of kryptonite is a superpower. And I definitely want to spend time here. I'm a big believer in this, you are too, of just how important it is to lean into your strengths and identify what you're better at than most people and use that as your way of getting ahead versus trying to, say, just remove these kryptonite/things you're not good.

**Lenny** (00:37:06):
For me, it was really a big deal. I actually worked with a coach while I was working. And this was in the biggest step changes for me is just realizing I'll never be amazing at X, Y, Z, but it turns out I'm really good at these things, and so let me just use those things to achieve the things I'm trying to do. As one example, I'm never going to be an amazing public speaker. I hate that stuff. Even though I do this podcast, it's not my strength. And it turns out I much prefer writing and sitting there and thinking, and that's what led to this newsletter. I started doing the thing that was pulling me and was easier for me and ends up being really successful because that's another way of achieving the same thing, it turns out. Here's the question. Why is it so important to think about your superpowers? How do you identify your superpowers? And just how do you think about this area?

**Donna Lichaw** (00:37:53):
On the one hand, there's so many studies that show that when we play to our strengths, we're much more effective than when we try to fix what's broken. It's a waste of energy to fix what's broken for the most part. But when you can amplify your strengths and figure out how to use them productively so that you can fulfill your purpose, meet your goals, do what you need to do in life and bring others along with you, it's just that you're such a bigger impact that way.

**Donna Lichaw** (00:38:31):
I'm going to give you an example. And it's funny that we're here talking about this because a while back, I remember we first met over email. I was thinking of resurrecting my newsletter. And I hate writing. And I've written two books; I hate writing. But more than hating writing, I hate email. I hate sending emails, reading emails. I really struggle with it. But yet I have this newsletter that people love and people were begging me to send more of over the years. And at the time, I was like, "Oh, maybe I'll dusted off." And I remember emailing you about this and asking if we could have a call because I had questions about newsletters. And your answer was, "No, no, no, no, no. No calls."

**Lenny** (00:39:23):
I don't know if it was that. I don't know if it was that.

**Donna Lichaw** (00:39:23):
Something like-

**Lenny** (00:39:28):
It was just I prefer to avoid calls whenever I can.

**Donna Lichaw** (00:39:31):
Yes, there you go, "Prefer to avoid calls whenever I can." It was very polite, right?

**Lenny** (00:39:32):
Okay, yeah.

**Donna Lichaw** (00:39:35):
But it was, "Happy to answer any questions you have. Can you shoot me an email?" I don't remember if this was my answer, but I think my answer to me was, "No, no emails. I can't give you my questions written. Maybe if I can record them for you, I'll think about it." And I think in the end, the irony is I ended up resurrecting the email list a while later, and now I do send occasional newsletters that I actually like writing and people enjoy. But I knew, okay, it'll take me like five hours to write down my questions for you over email; and I knew that was not right for me. You knew having a meeting was not right for you. That was fine. That was great because in the end, it was easier for me to write an entire book than to write that email to you. It probably was faster to write my book than it would've been to write the email to you. And in the end, here we were having that first conversation, which is really fun, but it's in a way that feels good to both of us. Play to your strengths and good things happen. I could get better at writing emails, but you know what? Not worth my time. And you could have more meetings, and not worth your time either.

**Lenny** (00:40:55):
**Donna Lichaw** (00:42:15):
Gosh, I see this all the time. I especially see this with founder CEOs because there's this very heavy misconception that when you are again catapulted into some kind of senior leadership position, that you're supposed to be a certain way and you're supposed to be loud and opinionated and controlling and tell people what to do, but I've worked with some amazing CEOs who are just incredible listeners instead. And it's the same thing, which is they embrace what works for them and they don't try to be what they're supposed to be. Well, they have to learn that.

**Donna Lichaw** (00:43:01):
Bob Iger as an example from Disney. I haven't met him. I know people who've met him. And I just always hear, "Such a sweet person. So nice and such a great listener." You can control the world and do it in your way. And so yeah, I see this all the time, any of your strengths, they operate again on that continuum with kryptonite. But if you can figure out how to leverage them and really be comfortable with them, cool things happen, cool things happen.

**Lenny** (00:43:31):
The big unlock for me was realizing that you can achieve all the same things using different strengths. You can be an amazing CEO being very loud, charismatic visionary. You could also be great CEO, being very quiet and thoughtful and deliberative and working in small teams versus like, "Hey everyone, listen to what I have to say."

**Donna Lichaw** (00:43:52):
Exactly.

**Lenny** (00:43:53):
Okay, how does somebody identify their superpowers, their strengths? I know there's some tests they could take. Very tactically, what do you recommend people do? What do you send them to figure out here's what I'm really good at?

**Donna Lichaw** (00:44:04):
There are tests out there. I have personally not found them as helpful, but some people love them. And so if you've ever taken a StrengthsFinder test or there's a V-I-A character strengths test I think it's called. Those are the two most popular. And you can just take a multiple choice quiz and it'll tell you what your top five strengths or characteristics are. And I don't find it useful because if I just get a list of things, I will never remember what the list is. And it also has no context for me, and so what I do and what I find works better for my clients as well is to pull your superpowers out of your stories from your past and your present, and then eventually figure out how to apply them and transpose them to your future.

**Donna Lichaw** (00:44:58):
But if you look at your peak experiences from life, from work, but especially from life... Because even if you want to be a better leader in a work context, there's a difference between work and life. It's very blurry, so you're better off not separating them. But if you look at your peak experiences from your past, I would go back to when you were a kid, what's something you did when you were a kid, like a project you worked on or something you were a part of that completely, totally lit you up and that you were so excited about? And I would then look at something from your more recent past. What's a project or something you worked on in the last maybe 10 years that just jazzed you up and you were just so excited to do? And then I would also look at just how did you get into your line of work, the thing that you're doing now? What's that meandering path?

**Donna Lichaw** (00:45:59):
And when you can look at these three stories as moments in time and you can lay them on top of one another, what you see at key moments is your superpowers popping through. And they're the things that empower you to make an impact, they are the things that do make an impact. And so an example I'll give you is one of... God, another executive I worked with a while ago, she kept being told in this dreaded 360 reviews at her company, they were obsessed with... This is another big, big tech company. They were obsessed with superpowers at this company. And so she would get these 260 reviews from her team telling her what her superpowers were. And so they kept saying, "Attention to detail." And she was like, "What on earth? I hate details. That's my kryptonite. I cannot deal with details," yet they kept telling her, "Wow, you're so great. You have this attention to detail." And then they kept giving her more detail-oriented stuff to do. And she's like, "I should be doing strategy and high level stuff. What is happening here?"

**Donna Lichaw** (00:47:22):
And she could say, "My strength is strategy." And I hear that all the time. "I'm a strategist." What is that? It doesn't even mean anything. That's not a superpower. I don't know, that means nothing. But when we looked at her past and her stories, what we were able to pull out is that she was really great at connecting things together, connecting themes, connecting pieces, trends and connecting people; connecting ideas together, and then connecting people to ideas. That's when she was happiest and that's when she was most effective.

**Donna Lichaw** (00:48:04):
And so eventually, that being a connector, it was a superpower, one of her superpowers. It also became part of her identity. And then over time, she was able to shed the great attention to detail thing as she just started embracing that ability to connect. And it made her much more effective at her job in the end. Yeah, look to your past and you can pull out key moments and see what your superpowers are.

**Lenny** (00:48:30):
We'll link to these tests that you recommended just for people to explore. I took a couple of them, and they were actually really useful to me, so I think if nothing else, it's a good little context to have while you do this other exercise. And I don't know if I got this right, but one is think about peak experiences in your life, including childhood or mostly adult life, do you recommend?

**Donna Lichaw** (00:48:50):
Yeah, I would go back as far as you can. Definitely childhood, childhood.

**Lenny** (00:48:55):
And peak meaning amazing, happy experiences? Is that what we should look for?

**Donna Lichaw** (00:48:59):
It doesn't have to be happy or sad, it's just you were at your best. It lit you up. And so for example... I have a few, but... Well, no, let me ask. Enough about me, so other people can hear this in action, when was the time when you were younger or a kid or anytime in the past when you were just at your best, really lit up doing something that just fueled you?

**Lenny** (00:49:31):
To me, I guess I think of not necessarily an specific example, but just accomplishing things always gets me energized. I did this hard thing. Selling my startup, that was a peak experience. There's one.

**Donna Lichaw** (00:49:48):
Selling your startup.

**Lenny** (00:49:50):
Yeah. And starting the startup.

**Donna Lichaw** (00:49:53):
And starting the startup. What compelled you to start the startup?

**Lenny** (00:49:59):
I always had this goal of I want to start a company, which is a terrible reason to start a company, but I had a goal I wanted to start a company. I had set this goal, in two years I'm going to leave this job and start a company. And two years later, that's exactly what I did.

**Donna Lichaw** (00:50:13):
What was it about starting a company that made that something that you were so interested in doing?

**Lenny** (00:50:19):
I wanted to prove to myself that I could do it, I think is the core of it. I keep reading about startups. All these people are doing interesting things. I want to just see if I can pull this off.

**Donna Lichaw** (00:50:30):
Okay. You wanted to just see if you could pull it off.

**Lenny** (00:50:33):
Yeah. And I also felt like I had the skills to do this compared to other folks that were starting companies and trying their hand at a startup.

**Donna Lichaw** (00:50:42):
You wanted to do it because you wanted to see if you could do it and you thought you could do it.

**Lenny** (00:50:47):
Yes.

**Donna Lichaw** (00:50:48):
What's so cool when you do this exercise, if we were to do it, we are not going to do it now, it'd take a little while. But if you were to unpack enough of those stories, even if you can't go far back to your childhood, because sometimes you don't have those memories. If you could unpack at least three of those scenarios, you would find themes. For example, it could be that one of your superpowers is doing things because you can do them. And that's really cool when applied in the right ways. You said you did the exercise. I'm curious to know what you came up with.

**Lenny** (00:51:35):
What I'm thinking about as you talk about this is I was very shy my entire childhood, and I think people didn't expect me to achieve big things because I was always just this nerdy, shy guy. I think there's always this chip on my shoulder of I'm going to show people what I could do. I want to show that I'm capable of more. I think there's a lot of that there.

**Donna Lichaw** (00:51:55):
When you can look at that in context, what you could see is you could see how it's helped you through life, even if it came from adversity. I'm sure you can also see times when that has not served you and when over indexing on, "I'm going to do it just because I can do it," has actually done a disservice to you. And so that's how you end up using them, which is you really look at, all right, from here to where I now want to go, how can I use this? And what do I need to watch out for if I'm going to over index and use this too much? Yeah.

**Donna Lichaw** (00:52:40):
Another blanket example that I'll give is problem solving, this keen ability to solve problems. I work with a lot of high achieving especially founder CEOs who are amazing at solving problems. And that's how they got to where they are. It's usually why you start a company. Well, for the rest of us, you do it because you want to see if you can do it. Otherwise, it's just to solve a problem. But when you're a super senior executive, at some point you can't be solving problems for everyone. And if you're just in the weeds solving problems all day, that's when you're not doing your real job and you're going to be the whole team and your whole company nuts. And so you have to figure out, okay, if this keen ability to solve problems is a superpower, how do you apply it differently?

**Lenny** (00:53:37):
Yep. That super resonates. A lot of times, you just are interested in the problem. It's like a puzzle and pulls you in. And that gets you in trouble.

**Donna Lichaw** (00:53:46):
It can.

**Lenny** (00:53:46):
To answer your question, what these tests told me my number one strength was adaptability, that I could just adapt to situations, which has pros and cons, but I super resonates. I find that I could just fit into things and adapt.

**Donna Lichaw** (00:54:00):
And it's a perfect example. And, as you see, it has its pros and cons.

**Lenny** (00:54:06):
Again, just for people to think about, because I really think this is such an important topic and it makes me want to write a newsletter post about this, just how powerful it is to identify, here's the things I'm very strong at and why it's important to double down on those versus think about solving your weaknesses. Your advice here is maybe take these quizzes that'll give you a sense of maybe your superpowers, and then think about your peak life experiences when you're the most yourself I think is how you describe it.

**Donna Lichaw** (00:54:34):
When you're at your best.

**Lenny** (00:54:34):
At your best.

**Donna Lichaw** (00:54:38):
At your best. Yep.

**Lenny** (00:54:38):
And there's an element of also when you're energized, which came up a few times on this podcast. Look for things that give you energy because there's something there.

**Donna Lichaw** (00:54:46):
Yes. Yep. Because then if you subscribe to... I'm sure your audience is familiar with this idea of managing your energy, not your time, which is great for managers, great for anybody, this will help you do that. If you're using your superpowers, you will have more energy. If you use them too much, then it's going to detract. But you want to be doing more of that, more of what lights you up, more of what you love, and figuring out how to manage the rest, whether it's outsourcing or sometimes fixing. But, I don't know, we're all grown adults. It probably is a matter of outsourcing or getting help or supplementing. We don't have to fix everything.

**Lenny** (00:55:32):
There's this guy that we'll link to in the show notes, but another executive coach, Matt Mochary, who we had on the podcast who is just like a walkthrough of how to do an energy audit on your day so that you can identify what gives you energy. And this is actually exactly what led me to this path. When I left my job, I specifically paid close attention to what gives me energy after a meeting I had, after a call, after things I did in the day, and what zaps me of energy? And I just decided I will do more of the things that are giving me energy. And that ended up being this newsletter and eventually this podcast, so it really works.

**Donna Lichaw** (00:56:06):
There you go. And I know Matt Mochary works similar to me with a lot of founder CEOs where you have to do that. You have to do that because chances are you're exhausted, you're burnt out; you are spending your energy in the wrong places. And so it applies to anybody, but especially when you are leveling up in leadership and doing something new and hitting that growth edge, you got to be doing it. It's just, yeah, you'll run yourself into the ground otherwise.

**Lenny** (00:56:39):
I imagine many people listening to this or feeling like, I wish I could not be in these dumb meetings that I'm in all the time and these stupid reviews. And there's a lot of stuff you have no control over that also are very energy zapping. What advice would you give to people thinking that?

**Donna Lichaw** (00:56:55):
Well, okay, let me qualify this with this is why I'm not a career coach, by the way. I don't help people navigate how to change jobs or leave jobs because I think if you're spending most of your time in your day doing things that are zapping your energy and you hate things you're doing in your job, maybe you're not in the right job. I don't know, if I was a career coach, I would just tell everyone, "Oh yeah, quit your job. I don't know what you're doing there." But there's a lot of truth to that, which is if there are things that you can control energy wise, great. Manage your energy, not your time. If there's really nothing you could do about it and it's the context and it's the situation, then your next best thing is trying to figure out how to change the context or the situation. I'm pretty ruthless there, I think. This is what I still bring from product management, I'm ruthless when it comes to prioritizing things. And so-

**Lenny** (00:57:58):
I love it. This is prioritization.

**Donna Lichaw** (00:58:00):
Yeah. There you go.

**Lenny** (00:58:02):
This reminds me of a Steve Jobs quote that I love of... His advice is just, "If you wake up every morning and you're feeling dread for the thing you're doing, it's okay to wake up sometimes and feeling that and feel like, ah, I'm not excited about this day, but if it keeps happening over and over and over and over, that's a sign that maybe you should make a change."

**Donna Lichaw** (00:58:21):
Yeah. I think there's something there. And actually, to bring this back to kryptonite, if it's something little, like let's say Zoom fatigue for example, I know it became definitely a topic when the pandemic hit a bunch of years ago, but I've been working remotely for, God, years, years, and even pre-pandemic. And I'm in meetings all day long. I love it. I love working with my clients. And they're all over the world, so we can't always travel to be with them. We do sometimes. They can't always travel to be with me. But the video's the next best thing, but it can be exhausting. And so does that mean I'm not just never going to have video calls ever? No, because I love what I do, and so I've discovered little hacks for that. One, which is don't schedule too many meetings a day. Great. Do lots of active stuff in between gym walks, whatever, try to get in-person social time, no meeting days.

**Donna Lichaw** (00:59:34):
And for during meetings, right here, I've got one of my squishies. There's the neurological thing with Zoom where we're just getting stimuli through our eyes and through our brains, but we're not getting physical stimuli, the same I would be getting if we were in a room together hanging out. Even having you just be on the other side of the room and we were chatting, it would be a very different physical experience that would close that circuitry for me and leave me more satisfied as opposed to on Zoom, my brain's on the lookout for something. And so I, a lot of my clients do this too, fidgets help ground me when I'm on Zoom calls. And it's like, okay, great. There are things you can manage, but yes, like that Steve Jobs quote or idea is if, God, if you really don't like and are getting energy sucked for most of what you're doing and it's constant, you got to change your situation.

**Lenny** (01:00:43):
I really like that tip. That's very practical. And buy something that you can play with with your hands. I use this pen, actually, is what I'm playing with usually with these podcasts. I need something squishy maybe.

**Donna Lichaw** (01:00:51):
Yeah. Well, there's-

**Lenny** (01:00:52):
If there's anything you recommend, let's link to it in a show notes.

**Donna Lichaw** (01:00:56):
Oh my God, I know, I know. One of my superpowers that's actually my kryptonite, but if I'm humorous about it, I'll call it a superpower is starting things that I don't finish. And so I think I have a picture of it somewhere on my website, a superhero supply kit that I prototyped a while back that has all these different types of fidgets and chocolate and all these things to get you through your meetings. And there are pointy fidgets that give you energy in the morning, and then there are squishy ones for the afternoon. And I've done way too much research. I should send you one at some point. I have a few boxes prototyped, and I never ended up doing anything with them, so I just send them to clients sometimes. But-

**Lenny** (01:00:56):
I'll take it.

**Donna Lichaw** (01:01:46):
Good. I'll put that on my list of things I-

**Lenny** (01:01:49):
[inaudible 01:01:49] finish.

**Donna Lichaw** (01:01:49):
... need to do, just also my kryptonite.

**Lenny** (01:01:51):
Okay, there's just a couple more things I wanted to touch on and then I'll let you go. One is you have this interesting approach of using product frameworks that people know in their day-to-day building product to translate that to personal growth advice. And so in your book, you use that design thinking double diamond framework for helping people think about their own life and career. Is there a couple you could share that people can maybe think about and use of just here's something you know in product. Here's how you can actually use this in your life, in your career.

**Donna Lichaw** (01:02:23):
I trained with Gestalt coaches and therapists when I moved into coaching. Gestalt psychology and Gestalt therapy, the idea is that... Well, it's a lot of what I talk about and especially in the book, this idea of when you want to create real lasting powerful change, you don't do it by forcing change to happen, you instead do it by embracing what is and what's working and then figuring out how to leverage that. And so it works for individual therapy, it works for coaching. It also works more broadly for organizational change and giant transformational development projects or initiatives or any kind of change. But one of the theoretical underpinnings there is when you do understand what's working and you start to get an idea of what's possible or something that you want to go try or do or create or make happen, you don't just go and change everything or do it all at once, you take one tiny step and run a little experiment to get data.

**Donna Lichaw** (01:03:41):
And so the way I work and the way I learned to work, at least through Gestalt coaching and Gestalt therapy, was you don't leave a session with me without having tried a little experiment first. The analogy there is we would call it an in the room experiment versus then get out of the building and do an experiment. And if you subscribe to, I guess I'm going to call it lean methodology. Although I feel like these names change all the time, and oh, that's so 10 years ago. And I don't care what anything's called, but the idea of experimenting and getting data and then using what you learn to make informed decisions on how to change things and then how to build things and how to make things even more successful, it works for the digital products that we build, it works for the businesses that we build, and it works for ourselves. And ideally, you do it for all the above. And so anything you think is true or you want to do, it's a hypothesis until you test it. And you go out, get data, and then you can do a bigger version, bigger version, bigger version. It works with human psychology and all the things we want to create and learn in life just as well as with products.

**Lenny** (01:05:08):
Is there an example of one of those little experiments you ran in a session?

**Donna Lichaw** (01:05:10):
Bring us back to the example of that one executive from earlier, to keep the continuity here, who thought she was too quiet and her team was complaining about her. And actually the irony, often when people come to me with things that they're embarrassed by, on the outside, she was actually quite loud. As a person, she was really loud and brash and all these things, it's just that in terms of her team, they didn't like how quiet she was in meetings. Especially that dissonance there was confusing to them because she was so loud and boisterous and energetic. But using that as an example, I remember when we first realized that the reason why she was so quiet in meetings is because she was spending a lot of time doing deep listening.

**Donna Lichaw** (01:06:04):
She started to chill out a little bit about it and stop beating herself up as much and started realizing, "Oh, that's a good thing. Why am I so insecure and getting so angry at myself for doing this all the time?" That's good. She started to chill out a little bit, but then the idea of a bigger experiment was in your next meeting later this afternoon, see what it feels like to sit there and just listen for an hour, just see what it feels like. And then see what you make of it, and then we'll figure out what to do about it. But just see what it feels like to listen and be in awe of, "Wow, I'm really listening."

**Donna Lichaw** (01:06:47):
And so that would been a get out of the building experiment. But the idea of doing that petrified her, because she's like, "I can't sit for a whole hour just being like, 'Yeah,' patting myself on the back. 'I'm a good listener. I'm a good listener. Look at me.' Or not even good or bad, but wow, I'm really listening." That's all I ever want from people is just this radical appreciation, this awe of, wow, I'm doing this. Everything changes when you figure that out.

**Donna Lichaw** (01:07:17):
But we decided to run a little experiment because why waste a whole hour of her life when we could just do something in 30 seconds in the room right now? And so we tried a little role play of, all right, what would it be like to just sit here for 30 seconds? And I talked about I don't know what. And just listen to me. We're having a meeting. What does it feel like for 30 seconds to do that? And we did that. And her answer was, "That was terrifying. That was God awful. Oh my God, I have to do that for a whole hour?" And eventually over time, it got easier. It was very uncomfortable.

**Donna Lichaw** (01:08:05):
This is where I'll bring up the whole superhero analogy. Again in superhero stories, when superheroes discover what their superpowers actually are, they don't just say, "Oh, thanks for this gift," and then run and save the world. Every superhero has a really hard time accepting, "Oh, this is my gift? Hell no." Or, "Wait, what do I do with this?" And they wreak havoc and they make a mess and it's uncomfortable. And even Superman tries to get rid of his superpowers often because he doesn't like being super. And so it's hard to know what you're really, really great at.

**Donna Lichaw** (01:08:45):
But when you can run little experiments that get bigger and bigger over time and really learn how to... Whether it's embracing your superpowers or anything. Let's say there's something you want to try, something scary. Or look at me with my superhero supply kit. And I was like, "I really want to build a gift box. Let me prototype that." Okay, fine. Five years later, have I done anything with it? No, but I built it. I saw what it's like. It felt good. And then as I got bigger with my experiment of thinking about how can I mass produce this? Where would I sell it? What about taxes? Oh, God. And not for me. And that's fine, so I give them away as gifts. But whether it's product or you or your business, small experiments, get data, go bigger, adjust, iterate, all of it. You will accomplish incredible things.

**Lenny** (01:09:39):
And I think a lot of the power there is you feel like, "Wow, there's something new here I didn't expect. And this is a new interesting learning. Let me see where else this can go."

**Donna Lichaw** (01:09:49):
Yes. And I think the biggest difference that took me a long time for me to learn is that as opposed to product development, you're testing things not just how is it working and what are the numbers? Well, even with product, we're not just looking at numbers all the time, but when you're experimenting with yourself and with people you work with and with your teams and with your companies, you run it through three filters. And this is not my term, but I'll say head, heart, hands is what I like to think of, which is head, okay, how's this going? What are my thoughts? You might think, yeah, okay, I'm listening. That's fine. Okay, next. Emotionally, how is this going in your heart? Wow, I'm terrified. This feels awful, or this isn't so bad, or whatever it is. Or it might be, no, that's fine. I hear that a lot. "That was fine."

**Donna Lichaw** (01:10:52):
But then how does it feel in your body? Our bodies are ultimately where we take in our stimuli and then store all of our experiences. And our body also tells us what next action we should take. And if you run an experiment and scan your body and it's like, "Yeah, that felt fine. And then how do you feel in your body? "Oh, numb." Well, that will tell you something.

**Donna Lichaw** (01:11:19):
Or I hear this all the time, "How do you feel?" "My hands are on fire." Or I was working with one client yesterday, and I think she said something like, "That was fine," and her whole face turned bright red. And then after a minute we were able to say, "Okay, what's going... Fine versus your face turned bright red. What happened there?" And then she realized, "Oh, I'm burning up. This is not okay." Yeah, run it through head, heart, hands. Life is like product thinking and it's also not. We have to go deeper and more broad with our experiences, and then we'll learn the most and be able to make the most informed, amazing decisions. And this is so cheesy, but live a good life and make an impact and be a great leader and do all the things you want to do that way.

**Lenny** (01:12:17):
Beautiful. The point you just made about how much of our thinking is driven by our body, we just had a whole episode on this a few episodes ago with Johnny Miller where we talk about the nervous system and how most of our neurons go up to our brain versus down from the brain and our body's telling our brain what we're feeling, so there's a lot. If you want to explore that as a listener, that's a great episode. We'll link to it in the show notes.

**Donna Lichaw** (01:12:40):
Okay, good, good.

**Lenny** (01:12:41):
Okay, let me ask you a question that my colleague suggested. She gave me a few suggestions to ask you. And I imagine this is what worked for her in you two working together. Question she had is how as an executive coach do you help identify/bring out goals or wishes that people have in their subconscious but are unable to realize or articulate?

**Donna Lichaw** (01:13:06):
Start with the ending. Come up with how you want things to turn out, and then work your way back. And start as far out as you want. It could be decades from now, it could be five years from now, it could be three years from now, it could be a year from now, it could be a quarter from now. It could do all the above. And really imagine. Close your eyes; imagine you're there. Engage all your senses. What do you hear? What do you smell? What do you see? Who do you see? What do you feel emotionally, physically? And what are you doing? What have you accomplished? What's amazing?

**Donna Lichaw** (01:13:45):
And then if you've got something exciting, go back to the beginning and then imagine how you got there and just write that journey out. If you think of it as an experimental roadmap, then start thinking, all right, what's the first thing I need to learn to know if this is right? Work your way towards that and onwards.

**Donna Lichaw** (01:14:15):
If you do that and you're like, "I have no vision," which I remember is what happened in this case, you sit with it for longer. You can't write that journey if you don't have that ending. And so you sit with it for as long as you need until you get it, and then you create it. And again, it sounds so cheesy in a way. It's not like I'm subscribing to this anything you want in life, you just say it and accomplish it. I know life doesn't exist like that, but dream it, see it, and then start taking steps to get there. What you end up creating will very likely be very different than you ever imagined. But this is what's going to fuel you. We're human, we're visual creatures. And so yeah.

**Donna Lichaw** (01:15:08):
And I have the whole mission section of the book and I have lots of choose your own adventure options for troubleshooting and the pitfalls to look out for. But yeah, that's my long-winded answer. Envision it, then figure out how you might've made it happen and go make it happen.

**Lenny** (01:15:27):
I was going to say this is a great tease for a part of your book we didn't get too much, so a good reason to go buy the book. Something I was going to say as you were talking is with this coach I worked with once, we did this exercise. And I was like, "Okay, five years or maybe 10 years, I'm not working anymore. Here's what I'm doing. I'm living here. Family." She's like, "Everyone in tech is like in five years they're not working anymore. They're just done, they're retired." Everybody's in that. That's their future, which is not obviously realistic, but it's hilarious.

**Donna Lichaw** (01:16:00):
Yeah. I remember years ago, 10 years ago, I was like, "10 years from now, I'm definitely not working in tech, definitely not working in tech." And then here we are. But it's funny how things end up. But what matters is that you're clear on the impact that you want to make. And how you make it, who knows what'll end up being the case. And that you're doing it true to yourself.

**Lenny** (01:16:23):
And impact is another chapter in your book, which we also didn't get to, so there's a lot of context.

**Donna Lichaw** (01:16:27):
So many teasers. Yes, go buy the book.

**Lenny** (01:16:29):
So many teasers. Donna, is there anything you wanted to share or leave listeners with before we get to a very exciting lightning round?

**Donna Lichaw** (01:16:36):
No, no. It's been so delightful chatting with you. No, nothing else.

**Lenny** (01:16:44):
Well, with that, we've reached our very exciting lightning round. Are you ready?

**Donna Lichaw** (01:16:47):
I'm ready.

**Lenny** (01:16:49):
First question, what are two or three books that you've recommended most to other people?

**Donna Lichaw** (01:16:55):
Here's a funny thing is I used to have all these different books for different topics. I'm going to give you the worst answer, but it's true. All these different books for different topics. And similar to when I was working in product, I had all these different books and whatever. And then eventually I realized I need to write the book that I really want to recommend, and so I did that with my last book, The User's Journey, which is all about product development. This sounds so conceited, but I really believe it, I now recommend my book the most. And it combines all my favorite ideas, philosophies, books out there. And you can check out the bibliography to see all the 30, 50 books that you can read otherwise. But man, I sound like such a jerk.

**Lenny** (01:17:40):
No, I get this because this is what my newsletter was originally is I'll just do my best to define an answer to this question I get often and put it together and make it really good so that I could send people, "Here's my best answer to this question." But every time I do that, they're like, "Oh, brother, just sending your own blog post to me. Just tell me an answer." I'm like, "But I've written the best version of it here. This is going to answer everything you're looking for." I go through the same pain. Okay, next question. Do you have a favorite recent movie or TV show that you've really enjoyed?

**Donna Lichaw** (01:18:15):
A show I've been watching recently, and I feel funny saying this because the fourth season was on recently, and I didn't enjoy it as much, but the first few seasons were so much fun, was For All Mankind on Apple TV. Have you seen it? The-

**Lenny** (01:18:32):
Yeah, yeah.

**Donna Lichaw** (01:18:34):
It was so much fun. It was all like what if the space industry was in an alternate reality and the last few decades were different than what they were? That was very fun. And for work stuff, a lot of my clients love watching Ted Lasso for all the leadership stuff. And it's just such a sweet show. But yeah, For All Mankind is recent. That's really fun.

**Lenny** (01:19:00):
Next question, do you have a favorite interview question that you like to ask? Usually this is meant for people interviewing candidates, but is there anything that comes to mind when I ask this question?

**Donna Lichaw** (01:19:10):
The question I always ask when I'm interviewing clients. Because if I'm not excited about what you you're doing, we're not going to work together. Yeah, I want to know what that is. And so imagine it's a few years out and you've had the best however long, year or three years of your life, what would you be telling me? And I like to add a twist to that, which is from Benjamin Zander in a book called The Art of Possibility, where with his students, he used to say, "Give yourself an A. If you could give yourself an A at the end of the semester, what would you be writing? Write the ending." And so I love doing that with clients, just seeing what could be possible that we could create if we work together?

**Donna Lichaw** (01:20:10):
Same thing with job candidates, although it's reminding me, one of my first jobs I ever got out of college, this is in the early .com days, I remember my then who became my boss, he asked me that question when he was interviewing me, where I saw myself in five years. And I remember at the time, my answer was, "Not here, and hopefully making documentary films." And this is like a .com job, but in hindsight, I can't believe I answered it that way. I was like, "Yeah, I'm going to be doing something else in five years." And he loved it so much that he hired me on the spot. And we're still friends many decades later. Yeah, that's my favorite interview question all around.

**Lenny** (01:20:55):
It's similar to question people often using product of just what is the ideal experience that... What's the perfect version of what we're building? And let's work backwards from that. Or what's like the 10 X version?

**Donna Lichaw** (01:21:05):
Exactly. Or if you want to add to that, if you could wave a magic wand, it's the same kind of thing. What could be possible?

**Lenny** (01:21:13):
I love the leveraging of product thinking into coaching. I love it. Next question, do you have a favorite product that you've recently discovered that you love? Maybe you already mentioned the squishy thing. Maybe something else comes to mind.

**Donna Lichaw** (01:21:28):
My fidgets, all my fidgets. I have so many; many different kinds. They're so much fun. I'm sure I have a better answer somewhere. But yeah, I would say my fidgets.

**Lenny** (01:21:38):
Well, if you can point us to your favorites in links, that would be awesome. I'm sure people are curious what you've discovered.

**Donna Lichaw** (01:21:44):
Yes. I curate them. I will definitely do that.

**Lenny** (01:21:48):
How amazing. I'm going to [inaudible 01:21:48] that.

**Donna Lichaw** (01:21:47):
Yep. And there's also the long one, the sticky monkey noodles. So many.

**Lenny** (01:21:48):
Beautiful, purple.

**Donna Lichaw** (01:21:52):
So many.

**Lenny** (01:21:53):
Amazing. Do you have a favorite life motto that you often find yourself coming back to sharing with friends or family, either in work or in life?

**Donna Lichaw** (01:22:04):
It's a phrase that I got from one of my mentors, and I teach it to all my clients, which is... Her catchphrase is, "Isn't that interesting?" And I have it as a sticky note, a physical sticky note on my computer monitor to remind me, which what it reminds me to do is get into what Gestalt folks call an optimistic stance. And I'm a chronic, serious, acute pessimist. Anyone who knows me, I'm cranky, but I love this reminder to be in this optimistic stance. Again, not that Stuart Smalley, "Wow, everything's great. Woohoo," but it's a kind of radical appreciation. Not isn't this good or bad, but wow, I just stubbed my toe and it really hurts. Isn't that interesting? Let me feel that throbbing toe. Or, wow, someone on my team just talked over me in a meeting 20 times in the last hour.

**Donna Lichaw** (01:23:14):
Actually, this happened with a client recently. I was there at an executive team meeting, and someone kept talking over the CEO over and over and over again. And often when that happens, you bark right back or you get angry or you get quiet or whatever it is, but when you can really fully appreciate, isn't that interesting? My shoulders are really tensing up right now. Wow. Whatever's going on. You often have more informed... Not often. You will always have more informed, mindful actions that you can take or not take. You can't pay me to meditate or anything or do yoga, but mindfulness, yeah, if you could just think to yourself, isn't that interesting? anytime something extreme happens in life, you will be shocked at what you learn and at what you do accordingly.

**Lenny** (01:24:10):
Very Buddhist, non-judgmental awareness.

**Donna Lichaw** (01:24:13):
Exactly.

**Lenny** (01:24:13):
Similar.

**Donna Lichaw** (01:24:14):
It's exactly that.

**Lenny** (01:24:15):
Not deciding it's good or bad.

**Donna Lichaw** (01:24:16):
Yep.

**Lenny** (01:24:17):
Final question. I'm surprised you haven't used any Dolly Parton quotes in this conversation. Clearly in your book, you're a big fan.

**Donna Lichaw** (01:24:25):
That's right.

**Lenny** (01:24:25):
I'm curious, what's a wisdom or quote that comes to mind that you think of from Dolly Parton that might be helpful?

**Donna Lichaw** (01:24:34):
Yes, and thank you for reminding me, because that was originally what I was going to say, which is one of my... There's so many Dolly quotes. And I think all my favorites are in my book, of course, but one of my favorites is, "Find out who you are and do it on purpose." That's amazing. Another one, "You don't like the..." I guess my two favorites. "You don't like the path you're walking on, pave a new path." What more in life do you need than that? There's all, yeah, Buddhist and Gestalt and mindfulness or whatever, but you could just do what Dolly does and you'll be all good.

**Lenny** (01:25:14):
Donna, thank you so much for being here. Two final questions. Where can folks find you if they want to reach out, maybe work with you? And how can listeners be useful to you?

**Donna Lichaw** (01:25:25):
Great questions, as always. The best way to find me is through my website, donnalichaw.com. And that'll be in the show notes as well. And reach out to me for a conversation. One of my superpowers that's also my kryptonite is accessibility. I'm that author who will always email you back, even though I hate emailing, always email you back within a day if you send me an email about the book. Same thing about working together. I always make time. Or even just conversation, I make time for any conversations with interesting people if it is exciting to both of us to make it happen. Find me on my website, donnalichaw.com. I've also got tons of free stuff there that you can download as well. Everything that we talked about today, a lot of the things that we talked about today are available there to play with as well.

**Lenny** (01:26:21):
Amazing. I think we're going to create a lot more superheroes with origin stories, superpowers, kryptonites, missions, impact, all the things you've written about in your book. Donna, thank you so much for being here.

**Donna Lichaw** (01:26:35):
Thank you, Lenny. This was a treat.

**Lenny** (01:26:37):
Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [14/19] Making Meta | Andrew ‘Boz’ Bosworth (CTO)

**Lenny** (00:00:00):
You were basically the 10th engineer at Facebook. I imagine there was a lot of pain and suffering that people don't often hear about.

**Andrew ‘Boz’ Bosworth** (00:00:07):
I didn't sleep for more than four hours at a time. I'd wake up every four hours and check the report and see if anyone was attacking the site. They don't tell you about that stuff in the movies.

**Lenny** (00:00:14):
You worked 120 hours per week., you had no hobbies.

**Andrew ‘Boz’ Bosworth** (00:00:17):
I don't want to take away from the romanticism of it. It's just that most often, we hear those romantic stories from the successes. It's a healthy thing for people to want to throw themselves into something and take that risk, but it is not glamorous at the time.

**Lenny** (00:00:29):
The newsfeed. That was one of your early projects at Facebook. People did not want it. They were wrong, clearly.

**Andrew ‘Boz’ Bosworth** (00:00:33):
Now, newsfeed was an easier case than people suspect. Everyone was outraged at the same time as they immediately doubled their usage of the product.

**Lenny** (00:00:40):
In terms of the economic utility, the Venn diagram of Boz, of newsfeed and ads created $1 trillion of value.

**Lenny** (00:00:48):
Today, my guest is Andrew Bosworth, or Boz, as most people know him. Boz is the chief technology officer of Meta. He joined what was then called Facebook in early 2006 as one of the first engineers, and during his 18-year tenure at Meta, he created some of the most impactful and important products in internet history, including the Facebook newsfeed, which was the first ever algorithmically ranked content feed of any social network, and is basically what people think of as Facebook today.

**Lenny** (00:01:17):
He also built the original Facebook mobile ads platform, which he then ran for another four years. He also helped build and scale the Facebook messaging system, the profile, the timeline, Facebook groups, and even the internal engineering boot camp. Most recently, he served as VP of ads and business platform, where he led engineering product, research, analytics, and design. And in 2017, he created the company's AR/VR organization, now called Reality Labs.

**Lenny** (00:01:42):
These days, Andrew leads Meta's efforts in AR, VR and mixed reality, along with consumer hardware across Quest, Ray-Ban, Meta smart glasses, and more.

**Lenny** (00:01:52):
In our wide-ranging conversation, we touch on so many important lessons and stories, what it was really like in the early days of Facebook, why you should be asking your manager for help more often, why communication is the job. Lessons from Meta's turnaround over the past couple of years, Boz's thoughts on the Apple Vision Pro, a bunch of leadership and career advice, what it was like to build the very first newsfeed, and lessons from that experience, and stories of failure and stories of success, and so much more.

**Lenny** (00:02:22):
If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously.

**Andrew ‘Boz’ Bosworth** (00:04:55):
Thanks for having me. I've been a long-time fan of your program and all the things that you've been putting out, so I'm glad to finally get a chance to join.

**Lenny** (00:05:01):
Same. I'm really excited to have you here. I have at least a billion questions I want to ask you. But I want to start with a few fun facts that I've found about you, and what if I go through them and then just pick one that stands out, and then tell the story behind it? How does that sound?

**Andrew ‘Boz’ Bosworth** (00:05:17):
All right, sounds good.

**Lenny** (00:05:18):
Okay. You went to 14 proms.

**Andrew ‘Boz’ Bosworth** (00:05:22):
Yeah. It's true.

**Lenny** (00:05:22):
Okay, I'm going to keep going. Okay.

**Andrew ‘Boz’ Bosworth** (00:05:25):
Wow, that's a strong opener.

**Lenny** (00:05:27):
That might be the one. You were a national Taekwondo champion in college. You were Mark Zuckerberg's TA in college in a class on AI, which isn't actually how you landed at Facebook, from my understanding. Harvard was recruiting you to play football for them. You were very active in the 4-H Club, and you raised animals and showed them at county fairs when you were growing up. You once shared a stage with David Copperfield.

**Andrew ‘Boz’ Bosworth** (00:05:52):
That's true.

**Lenny** (00:05:52):
MC Hammer once told you that your outfit was stylish. And president George W. Bush complimented you on your shoes and the shine of your head.

**Andrew ‘Boz’ Bosworth** (00:06:03):
Yeah, these are all true. I want to say, wow. First of all, I got to make sure that people understand, I was a national collegiate champion, in as a green belt, which that's like being the JV champion. Just so everyone's clear on what that is.

**Lenny** (00:06:15):
W's a W.

**Andrew ‘Boz’ Bosworth** (00:06:16):
Heavyweight sparring. I'll tell... The prom story is a funny one. It's related to the 4-H story. I was a big-time 4-H'er, National 4-H Hall of Fame, did all this stuff there.

**Lenny** (00:06:29):
As a comeup to that, 4-H is a wonderful program, youth program, it's coed program, and I was all over the state, all over the country, doing leadership events and doing these conferences, and doing a lot of public speaking.

**Lenny** (00:06:39):
And almost every 4-H event has a dance. People don't know that. At the end of a conference, at the end of the, literally camp, you'd go camping for a week, at the end there's a dance.

**Lenny** (00:06:49):
And so, as a consequence, the most important thing, if wanted to go to a lot of proms, I was a good dancer. And it turns out, the high-level bit, at least in the 1990s, for girls selecting who they might want to go to prom with was, will he and can he dance? And the answer with me was yes. And combine that with the fact that I knew a bunch of girls who went to different schools, that's the recipe for success right there, if that's the goal that somebody has. Two my junior year and 12 my senior year. I once went to three in one weekend, a Friday, a Saturday, and a Sunday night.

**Lenny** (00:07:21):
Another fun fact about you is you were basically the 10th engineer at Facebook, initially, way before it was a clear success story. I imagine there was a lot of pain and suffering and struggle that people don't often hear about those early days. They see a movie like The Social Network. It looks like, "Oh, that was so much fun. I've got to start a company. It's going to become a trillion-dollar success story." I'm curious just what those early days were like. Are there memories that stand out to you?

**Andrew ‘Boz’ Bosworth** (00:07:47):
Yeah, there's a bit of a joke in the 10th thing, which is me and five other guys all joined at the same time, and there was nine engineers before us. We joined the same day, so we're all the 10th engineer. So, somewhere between 10 and 16, depending on how you want to do the numeration on that.

**Lenny** (00:07:59):
I've written about this in my blog, and I tell this story a lot, which is it was fun, and there was tremendous camaraderie and memories that were formed, but they were formed in a kind of forge of really intense times.

**Lenny** (00:08:13):
At that time, almost all of us lived within one mile of the office. We ate most of our meals together because we were working, not to say we weren't also friends, but because we were working, it's like, oh cool, you just roll into a meal and roll back into work.

**Lenny** (00:08:26):
And there's little things that you don't appreciate, which is like there was nobody to help you. There was no expert. And so, it wasn't like, "Hey, I'm struggling with this one tricky problem. Who should I talk to?" It's like, nobody. You should talk to yourself and figure this out. Or it's like, "Oh, man. My servers are out of capacity." It's like, "Cool. You should go to Fry's Electronics, you should buy a bunch of components, you should build a new server, and then you should run it. Maybe drive into the colo, rack it, and then get back and run it."

**Lenny** (00:08:52):
People really undervalue the fact that when you go to work, even a moderate mid-size corporation today, especially with the tremendous growth of startups supporting startups, things like payroll and finance and IT and HR, these things are professionally handled in many cases.

**Lenny** (00:09:10):
That was just not the case in the early 2000s. It was just you, and your personal car, and whatever you wanted to do with your time.

**Lenny** (00:09:18):
So, I don't want to take away from the romanticism of it, it's just that it's most often we hear those romantic stories from the successes. We so rarely hear somebody who went through really sacrificing a lot of my 20s from any kind of social or outgoing, fun environment.

**Lenny** (00:09:37):
It paid off for me, so no one feels bad for me, nor should they. But there are other people who do the exact same thing, maybe they worked harder, maybe they were smarter, maybe they did better, and it didn't play out for them. And it's a big sacrifice.

**Lenny** (00:09:48):
And so, I love the enthusiasm for startups, I love startup culture. I think it's a healthy thing for people to want to throw themselves into something and take that risk. But it is not glamorous at the time. In retrospect, it's like, "Oh, it can be..." We have a little halo around it. But at the time, it doesn't feel glamorous.

**Lenny** (00:10:06):
Yeah. In this post you mentioned, you said that you worked 120 hours per week.

**Andrew ‘Boz’ Bosworth** (00:10:07):
Yeah.

**Lenny** (00:10:10):
You had no hobbies, and you gained a lot of weight.

**Andrew ‘Boz’ Bosworth** (00:10:15):
Yeah. We drank a lot to make up for it, so I gained a lot of... And you weren't eating healthy. It was crazy.

**Lenny** (00:10:22):
I think I've told this before. There was a time where one of the first things I built was an anti-spam, kind of anti-scraping defense mechanism. But we didn't have any ops support. There was no 24/7 online support.

**Lenny** (00:10:35):
So, I built this tool. I had to wake up every four hours. For about two years, I didn't sleep for more than four hours at a time. I had to wake up every four hours and check the report, and to see if anyone was attacking the site. And if they were, I was up, and I had to go battle back. And if they weren't, cool, I'd go back to sleep. But that's the thing, they don't tell you about that stuff in the movies.

**Lenny** (00:10:55):
That's almost worse than having a kid, a newborn.

**Andrew ‘Boz’ Bosworth** (00:10:59):
And nobody asked me to do it. Nobody even asked me to do the anti-spam, anti-scraping stuff. I just thought it was a problem, and I went and did that, and that was the solution I come with. If I was a better engineer, maybe I'd have solved a better problem.

**Lenny** (00:11:11):
So, maybe just to close out that thread, when you talk to founders, what advice do you give them along these lines?

**Andrew ‘Boz’ Bosworth** (00:11:18):
I want to be cautious about this, because what I tell founders... The first thing I tell founders is that I've never been a founder, and I want to recognize the difference. I joined January 9th, 2006. That's almost two years after Mark started the company. I wasn't involved with fundraising, I didn't have to do any of that side of the things, and I didn't even have to deal with the board or the business side of things. I really was lucky, in a way, to have joined when I did.

**Lenny** (00:11:42):
But the first thing I tell founders is like, "You should take my advice with a grain of salt. I have not actually been in your shoes."

**Lenny** (00:11:47):
If I can compliment you, really, one of the things I like about your program is, there's a whole system of professionals in our industry. And when I grew up in technology in the valley, you always heard about the ACM, right? The Association of Computing Machinery. You heard of these legendary professional organizations that supported people in our fields.

**Lenny** (00:12:09):
And by the nature of the rapid pace of change in the technology, and the nature of the engagement of those institutions, even academics, even academia broadly, kind of are out of touch. The tools that you got from those places weren't useful in our field.

So, I do think the mentorship that we give each other has been a critical and sustaining resource. There is, today, now, resources like your podcasts and your newsletter that are actually really designed to help people who are professionals in our industry in a way that is almost kind of missing for 15, 20 years, and I love to see that. Because if you're an up-and-coming [inaudible 00:12:45], literally you used to have to know somebody and ask them a question.

**Lenny** (00:12:48):
And so, a lot of times what I'm helping founders with, I can help them with the strategy, I can help them think through the technology choices, I can help through business, I can think through the management, the organization structure. But I also try to be very clear, there's a bunch of stuff that I just was never exposed to.

**Lenny** (00:13:00):
So, even as we just talk about how tough it was for the average engineer joining Facebook in 2006, man, it was even tougher for Mark Zuckerberg in 2004, probably. And that's a story that's been told, I'm sure, but still. So, I think these are both... It's almost all scale and variant. No matter how far you dial back, the challenges are interesting and are worth talking about.

**Lenny** (00:13:22):
One of maybe your most popular posts is this quote that you share about the advice you often give. What you say is, "The advice I find I have to give more frequently than any other in my career, as a manager, a board member, an advisor and a friend, is for people to more directly leverage their leaders." Can you talk about that and what that means, and what that looks like?

**Andrew ‘Boz’ Bosworth** (00:13:40):
It's such a normal and natural healthy thing. And by the way, we do it in our personal relationships. Like I said in the post, we want to do it ourselves. We want to do it ourselves to prove to everyone that we can do it ourselves.

**Lenny** (00:13:52):
And we think in our heads, "If I ask for help, haven't I already given up that goal? Haven't I just admitted defeat on one of my top level goals, which is to demonstrate that I can do it myself?"

**Lenny** (00:14:04):
But what so often we forget is, more often than not, your job is not to do it yourself. Your job is to get it done, is to have the thing done, done well, done right, done competently. And a lot of times, the tools that you need to do that live with your manager, with your partner, with your advisor, with your mentor. That's where they live.

**Lenny** (00:14:25):
So, how many times as a manager have I gone through, and somebody's told them, "Here's the job." They're like, "I got it." They go off, they come back, it's done, it's wrong. And I'm not blaming them for it being wrong. They didn't check in with me. They misunderstood. We miscommunicated. I'll take the L on that. That's no problem.

**Lenny** (00:14:42):
But here we are, six months later, it's not done right because they misunderstood the brief. We miscommunicated with the brief.

**Lenny** (00:14:49):
Or they come back, and it took a year. And I'm like, "Why did this take a year instead of six months?" And they're like, "Oh, man. I had all these things I had to deal with." Where, if they had emailed me, I could have bulldozed that stuff. I could have cleared the path. I could have said, " Oh, no, no, no. Don't worry about that. This is the thing." And then we'd have been done six months sooner, and they would've been less frustrated. And so, light touches.

**Lenny** (00:15:09):
Now, I do think as a manager we also have a job to say, "Hey, that's kind of the work, so you got to kind of go figure that out." And one of my things I always tell my managers, one of the most powerful things we do is refuse to rule. Someone will bring me a thing. A lot of times we feel obligated to weigh in and help. I'll be like, "Nope, but look, I think you've got it. I think the challenges you're facing are the right challenges. I think you're approaching it in the right way. Just do your best there." And that's what it is. And so, there is a responsibility as well for those of us who are leaders, mentors, advisors, board members to do that.

**Lenny** (00:15:39):
But, by the way, we do this... Personal relationships. You're with your partner, and you're trying to do something the right way, but you're not talking to them about it. You're just taking a huge risk there, and for very little reward. They're not going to be mad if you ask them, like, "Hey, is this how you wanted it done? I don't know."

**Lenny** (00:15:56):
And so, I do think it's kind of funny how much we build these castles in our mind, these little silos that keep us from engaging the structures that are built around us, that are designed to help us succeed. I saw this great quote, actually just yesterday. I saw Patrick Stewart, who is one of my favorite actors of all time, and whose characters I love, and he talked about people going on casting calls. And this is a brutal thing for actors, right? You're going on 30, 40 things, you're getting rejected. It's tough. Everyone's kind of heard about this. And he said, "No one wants you to succeed more than the person you are auditioning for, because they want you to be awesome. Because as soon as you are awesome, they're done. They want you to be amazing."

**Lenny** (00:16:37):
That's like your manager. Nobody wants you to be more awesome than your manager does, because when you're amazing, your manager, his life gets easier, her life gets easier. So, I just think that's the mentality we get into is like, "No, no, no. They're testing me." They're not. They are rooting for you. I promise you that.

**Lenny** (00:16:53):
I love that advice. I imagine the reason people don't do this, as you said, is they don't want their managers to think they don't know what they're doing, or they can't solve it. Do you have any advice and guidance for when it makes sense to go reach out and ask?

**Andrew ‘Boz’ Bosworth** (00:17:06):
One of the things I think, for people who are timid about this especially, is I think you can put a framing around it that's really easy for your manager to engage with. You can say, "Hey, I'm making progress on this. This is what I'm blocked on, this is the current program." And I'll even say, "Hey, if this all looks good to you, no response required. If there is something here that you want me to do better, different, that you think you could help with, let me know."

**Lenny** (00:17:32):
I love a typed, five-, 10-sentence email, "No response required. Here's where things are." Even if everything is going really well, I'm like, cool, this person understands the urgency, they understand the assignment, and they're giving me a little heartbeat, a little ping back.

**Lenny** (00:17:53):
And then also, if two weeks later, let's say the blocking issue is bad, then you say, "Hey, I am sorry, but I do actually need your help now. I'm actually blocked on this thing." I have the context. I have a mental model of you toiling away on the right thing, on the thing I asked you to do over there. Even then, when you're blocked, you can make my life super easy. Like, "Hey, what I'd love for you to do, if you could send an email to this person, here's a draft with this thought, that would help."

**Lenny** (00:18:23):
Or it's like, here are specific questions framed up. "I think this is what you want. Is this right? Yes or no? If no, okay, we'll come back and we'll spend more time. If yes, we're all good." So now, not only am I up to speed, I have a mental model, I'm engaged. Also, you've made it super cheap for me to help you. And people are always surprised. People who work for me are always surprised when I tell them how big a part of my job is doing these little types of things.

**Lenny** (00:18:53):
It's a little spinning plates at my scale. I've got 10,000 or 15,000 employees, depending on how you want to count different things. And so, you're just like, every now and then I got to get a whole new plate, a whole new rod, and just really put the effort into it. But for the most part, I'm just trying to touch everything and keep the momentum going. And so, if something falls, and somebody didn't tell me that "Hey, we're losing rotational velocity here. We're losing momentum." Oh, I'm bummed. I'm like, "Ah, now that plate fell. I got to start a whole new thing over here now."

**Lenny** (00:19:22):
So, I think people underestimate. They think of my job differently than my job actually... My job is actually tons of little touches.

**Lenny** (00:19:29):
So, I think a key takeaway here is, one, index more towards asking your manager and leaders for help. And I love this way of framing it of, it doesn't always need to be like, "Here's what I need from you." It's, "Here's what's happening. Here's things that might be blocking me. Here's questions I have. Here's things that are going on."

**Lenny** (00:19:44):
This is actually similar to something I found really powerful that I'll share real quickly, this idea of a state of... I call it the State of Lenny email. And I sent this email to my manager every week. The State of Lenny. It's kind of like State of the Union. And it's, "Here's my current priorities, here's what's on my mind broadly, and then here's blockers that I need your help with.

**Andrew ‘Boz’ Bosworth** (00:20:02):
We actually used to have a format for that we called HPMs. Highlight, people, me. And every manager at Facebook from like 2008 to like 2014 would send to their manager, or even their leadership group. I mean, at one point when I was running what we called comm apps, I just sent it to Zuck and the whole leadership group.

It's like, what's the highlights include? And it highlights [inaudible 00:20:27] flow. What's the big ticket things you need to know? Where are people? Like is somebody in trouble? Is somebody at risk? Is somebody doing really amazing work that needs a shout-out? And then me, how are you personally doing? HPMs, we called them.

**Lenny** (00:20:39):
Actually, it's funny. I hadn't thought about that in a long time. But yeah, no, I think this kind of thing can work. And look, every manager is different, so even at the Meta level, by the way, is another success. I think what people do is they want to treat every manager the same, and that's not going to work because every manager is different.

**Lenny** (00:20:54):
But every manager, you can ask, "How do you like to get updates?" You can ask them when you first start working with them. Like, "Hey, what's your cadence? How do you like to stay informed?" And so, for me, I do regular one-on-ones. As the org's has gotten bigger, those have gotten more distant, so people have replaced those with more written things.

**Lenny** (00:21:11):
But no manager will get pissed at you if you're like, "How do you like to get information about me?" That's a totally reasonable thing to ask.

**Lenny** (00:21:18):
I love the specific idea you shared of just drafting the email to say the other team leader, "Here's what I need you to tell them. That would really unblock this thing." And that's such a cool idea.

**Andrew ‘Boz’ Bosworth** (00:21:27):
By the way, I always put my own... I don't take that copy paste it. I'm always looking at that and be like, "Okay, I understand." A lot of it is actually not about what you want the other person to hear, it's about the voice, the tone.

**Lenny** (00:21:41):
It includes a lot of history. I don't know. Have you been going back and forth with them for 12 rounds, and this is going to feel to them like I'm really coming over the top? Or is this like, "Hey, first time you're hearing about this, my bad. Here's what we're doing. Need your help."

**Lenny** (00:21:54):
So, a lot of that isn't even about making my life easy because I want to copy paste. A lot of it is, actually, there's a rich set of information in how you tone and how you draft that note that's going to help me land it correctly and not feel like I'm just out of band, heavy coming in.

**Lenny** (00:22:11):
This touches on something that I often hear is very core to the way Meta works, which is transparency. Anyone can ask Zuck questions at the Q&A's. People are encouraged to post constantly internally of what they're thinking, what they're working on. All the data is shared publicly. Which often leads to leaks, which I hear you hate, and that is a pet peeve of yours.

**Andrew ‘Boz’ Bosworth** (00:22:32):
Just feels like a violation of the team trust. Just feels like... I grew up with playing sports, right? I was football, soccer, track. And you just can't imagine one of your guys calling out the play to the other team. Can you imagine what you would do in that case? "You're off the team. I'm sorry, you can't be here." Anyways, sorry. Carry on.

**Lenny** (00:22:48):
Yeah, and there's so many more people, it's hard to find. Who is this? So, with this downside as an example, and I imagine there's other downsides also takes a lot of work, and it puts people on the spot a lot of times, what have you seen as benefits and why is that such a big part of Meta's way of working?

**Andrew ‘Boz’ Bosworth** (00:23:05):
Yeah. This kind of comes back to, I think, the principle that really good, talented people, you want to leverage them fully. You really want to make sure that they are fully leveraged. And so, anytime they have the wrong information, or they don't have the information, you've now blocked one of the economically most valuable things that your company possesses, which is this person's time, attention, talent. Not only that, you've also made them more frustrated, and now they are more likely to leave.

**Lenny** (00:23:35):
If the lifeblood of any company are the people inside of it who collectively commit to some kind of a goal and a mission and work together, then you want to maximize that potential. And creating this really open information ecosystem is one of the ways that we do that. So often, great, phenomenal work that has happened at our company has not come from this one top-down mandate, but has come from people understanding not just what we're trying to accomplish top down, but also having way more information at their disposal to be able to act on it.

**Lenny** (00:24:16):
People talk about top-down or bottoms-up culture, and it's a bit of a myth, in my opinion. If you've ever met Mark Zuckerberg, it's not a bottoms-up thing. The ideas that we're pursuing are Mark Zuckerberg's ideas, first and foremost. That's not to say that he's not open to new ones, and of course he is, and that's a form of bottom-up, people can bring ideas to him and he internalizes them and acts them or not. But when he brings things top-down, he's not micromanaging, he's in the details. I'll be careful on that.

**Lenny** (00:24:44):
But he does create the space for you to bring back three or four versions of the thing that he's talking about, and then he shapes it from there. And you can't do that if there's... If you don't have degrees of freedom, sure, but also if you don't have the information. Otherwise, if you don't have the information available, what we're trying to accomplish, why we're trying to do it, what the infrastructure is like, what the availability is like, what the performance is going to be like, well, you just are stuck. You're just going to have to follow the script. That's very boring for high-talent, high-creativity, high-engaged people.

**Lenny** (00:25:15):
Now, it does come at a tremendous price. You have to get really good at managing information on the incoming. Most people at most companies consume all the information that's given to them, but the information itself is carefully managed. They're getting all the information they're intended to get.

**Lenny** (00:25:32):
We've turned that on its head, and it sounds great, but it's not free. Even somebody senior coming from outside of the company to the company, one of the things I have to coach them on is, how do you find signal amongst all the noise?

**Lenny** (00:25:45):
You have to have a system for managing your information. You have to have a system for triaging the incoming, getting rid of a bunch of stuff that is on the wrong channel, or it doesn't matter to you, figuring out what's the... groups that you want to be a part of, but you consume only when you choose to and-

**Andrew ‘Boz’ Bosworth** (00:26:00):
... groups that you want to be a part of but you consume only when you choose to. And where are the things where you're getting push notice? Like that's the real time thing, and that takes some time.

**Lenny** (00:26:08):
This point you made about bottom up versus top down is really interesting, because, when I think of Meta, I think it's a very bottom up culture. I hear everyone comes up with their ideas, runs experiments, is very encouraged to just try stuff, and it's really interesting to hear that. And it makes a lot of sense that most of the big ideas actually do come from the top.

**Andrew ‘Boz’ Bosworth** (00:26:26):
It's of these mythology things. I don't think it's the wrong... As a contract, it's more bottoms up than many other companies, because you do have these degrees of freedom within the construct. But make no mistake, like Mark or me or Chris Cox or Javi, they have very strong opinions about what we should be doing as a company, and your bottoms up-ness works within that framework. But it is true that you can ask Mark any question, and he's going to answer it. Same with me, same with Chris, same with Javi and also that we certainly take inspiration from the discussion that we have with employees. So I don't know, it's just not as black and white as people tend to paint it.

**Lenny** (00:27:02):
I think one of the biggest lessons here is making it at least feel like you have a lot of say, even though a company is very, "Here's the big strategic [inaudible 00:27:10]," you're very good at making people feel like they can have an impact and a say.

**Andrew ‘Boz’ Bosworth** (00:27:14):
And can I tell you, the most important thing is just giving people clear guidelines so they know where they... Like, "Where do they have space and where do they have no space?" One of the things that we go in these reviews with Mark or my team with me I'm sure, and I'm like, "For this part of the UI, it is going to... Like, I will draw it for you. It's going to be like this." And this other part. I'm like, "Cool, that's important, too. I don't have a clear vision of it. Why don't you do it?" So there's just really clear guardrails of like, "Okay, where are we just on assignment? And where do we have more flexibility?"

**Lenny** (00:27:45):
Is there an example of that that comes to mind where you were just very in the details and drawing the screen?

**Andrew ‘Boz’ Bosworth** (00:27:51):
Over the course of time, there's been quite a few examples. I think early on, when we were working on News Feed, mark was absolutely whiteboarding every single pixel that the team had to put on the front end. On the back end, he was like, "Make it rank, have some ranking." So I felt like I was lucky there. I was just like, "Cool, I'm off to the races on some ranking stuff." And Chris Cox and all these other guys are having to really pixel-match these things. But it's not always that way by the way. So now fast-forward and we're talking about ranking, it's not like Mark is always hands-off on that. When we got into modernizing our ranking systems, which we've done over the last five years, Mark was heavily involved and like, " Hey, what's the mix shift and how are you weighing different things?"

**Lenny** (00:28:33):
And so it can go both ways. For me personally, I've gotten really involved in some relatively esoteric things. I was really adamant, for example, that hand tracking and mixed reality make it into the headset. Let's just say that there weren't any supporters in the team. Obviously we had a hand tracking team, which is phenomenal, mixed reality team, but there was a lot of people who were like... They did not feel those features were going to be critical for this to become a mainstream device. I always believed that they were for ease of use and for... So I just really forced the issue and didn't give anyone any room and held really high standards for the performance benchmarks we were going to hit on the hand tracking. And teams told me it was impossible. And it wasn't. It did great.

**Lenny** (00:29:11):
This touches on something that comes up a lot on this podcast. And there's this debate between how in-the-weeds founders and execs should be, whether they delegate, empower, versus, "No, we're just going to do it this way. I'm going to be very involved in every mock." And there's always this up and down that happens where it's like, "Okay, cool, we're going to let people run and do their thing," and then things start to not work as well often. And then, "We're going to take back control." You have just a perspective on when it makes sense to go deep, how founders execs should think about that?

**Andrew ‘Boz’ Bosworth** (00:29:41):
Such a useless answer for founders, it depends on the weeds. There are some weeds that really matter and there's some weeds that really just don't, and I should say, that doesn't mean they don't matter at all. You have to do them, but they aren't the hinge upon which success or failure will happen. Yeah, there's people I really respect, Brian Chesky's been on and said, "Look, the Airbnb is going to work only on the things that I can work on. It's that's the extent of what it's going to do." And that's a super extreme form of it. I have a lot of respect for him and how they're working things. I think that if you have great super talented people that you can trust who can own bigger pieces, that's one option. If there are ways to structure it so that you can check in effectively and make sure that it's on track, that's another way to structure it.

**Lenny** (00:30:27):
And there probably is still work happening at Airbnb, that has to happen, finance and accounting and HR, that Brian isn't personally managing. So there are clearly non-technical areas that we do. Or legal. There are areas that we do trust that this is happening at. And so I think a lot of founders regret delegating too much, from my conversations. And I totally get that. Or they delegated something critical that really turned out to be the most important thing. For me, the judgment is like, "How do you, most important, determine what is what matters the most?" And so Mark, we joke inside of Meta, to this day, we call it the eye of Sauron. When Mark has determined that the thing that you're working on is the most important thing, there is no detail too small for him to notice.

**Lenny** (00:31:17):
He will be in a review, and in the same review. We'll be like, "Strategically, I think we're off course. And also, this one pixel is definitely wrong. You have to fix that." That's a big range. Frankly, I'll be a little bit self-congratulatory, I pride myself on being able to do the same. And I think people who work with me often comment that the style of leadership that we have, and I think Chris Cox is the same, is where it's like we will go where hide a low on the things that matter a ton. And there's a bunch of other things that certainly matter. We're glad we're doing them, but either they have pretty clear roadmaps, pretty clear examples in the industry, or it's like that's a feature that you have to have but isn't going to determine success or failure. So getting it into rough shape and then iterating on it is fine. And so I think it really does depend on the weeds, how deep you want to get.

**Lenny** (00:32:08):
It's so funny, I use exactly that same metaphor, the eye of Sauron, when I talk about working on things that Airbnb that matter a lot to Brian. And my advice to people is, "You don't want to be in that eye of Sauron for too long in your career, because you're just going to burn out if you're working on the most important thing all the time, but want to be close. You don't want to be in the Shire, but you want to be around the [inaudible 00:32:26].

**Andrew ‘Boz’ Bosworth** (00:32:26):
That's right. They're both... So I worked for years in ads. From 2012 to 2017, I ran ads in a business platform, this big ads group, and it was an area where certainly it was very important, but Mark had so many other things going on with the transition to mobile, he did kind of delegate it to me. And it was awesome, and it was so cool to have that kind of trust from him. And also, you're constantly terrified, because like, "Mark does not know. What if this is all..." My leads would be worried, because they just hadn't had a review with Mark in a while. And it's like, yeah, you suffer in the intensity of the gaze of Sauron. You also suffer in the shadow of its absence. There's no perfect place to be.

**Lenny** (00:33:09):
That's hilarious. I'm trying to think of the part of Middle Earth that is a metaphor for that.

**Andrew ‘Boz’ Bosworth** (00:33:14):
Yeah.

**Lenny** (00:33:15):
Okay, so you talked about the News Feed, which was one of your very earliest projects at Facebook. Here's a couple fun facts I know about the News Feed. One is that it was the very first algorithmic News Feed of its kind of any social network and maybe of any sort of product like this. And two, it was the very first AI code that was written at Facebook to rank the actual News Feed. So there were a lot of firsts, and clearly this became a huge deal. The News Feed is essentially what people think of when they think of Facebook now, but it was super controversial when it came out. People were very against this. They did not want to be sharing this much information with people, or so they thought, and then they realized eventually, "Oh, this is actually exactly what I want." What did you learn from going through that experience of building something that people initially reject and then later realize that they actually do want this and this is exactly what they're waiting for?

**Andrew ‘Boz’ Bosworth** (00:34:08):
This is a story that you tell a lot actually through your interviews, which is just like, "You have to have conviction in what you're building." You're choosing your customers as much as your customers are choosing you, is one way I think about it sometimes, and one mistake that you do see sometimes startups make is they get an early cohort of users whose needs actually take them kind of orthogonal to a larger market. And so they become kind of held hostage by their earliest customers now. So time and time again, we've had a vision for what we thought this should look like, and it wasn't the thing we were delivering right now. And so people who were using the thing we currently had were not sure that that change was what they wanted. But we had a confidence that over time they would, and we're not always right, but in these cases we were right. Now News Feed was an easier case than people suspect, because everyone was outraged at the same time as they immediately doubled their usage of the product.

**Lenny** (00:35:05):
So we had a few advantages there, which was, it was literally like everyone was like, "I hate this so much." And they would refresh, refresh, refresh. And so we were like, Okay, wait, there's cognitive dissonance here between what the stated preferences and what the revealed preferences are in the economic sense. So News Feed was a little easier than people suspect, to us, to stick with. But people sometimes misunderstand that. They think, "Oh, the lesson is don't listen to your customers. Not at all." And we certainly care a tremendous amount. And even with News Feed, we did actually screw some things up. I kind of always make this joke that it's almost like... You know when you're at the party and music's loud, you're talking to somebody and the music cuts out right when you're saying something at a super high volume, and so everyone in the party hears the last thing you said?

**Lenny** (00:35:42):
Now you were saying it in a public place, so it wasn't like it was a private comment, but you also didn't mean to broadcast it at that volume. We kind of did that to the entire user base. We took what had been wall posts, which sure, anybody could have gone to that profile and seen and then put it kind of on blast, on Main, as the kids say these days, "Put it on Main," and someone's like, "Ah." So we did that. I don't want to say it like... We did screw things up. It wasn't like, "Oh, this is a clause execution." So another thing to know is like, "When did you screw something small up, and when did you do something big up?" When is the thing itself wrong, versus when were the details wrong? That is an art. That is a real art, and you don't always have user data to determine it like we did.

And so a lot of that is, "Do you have a clear vision and intuition for what you expected to happen?" And then what happened instead and can you diagnose the delta there? So in the News Feed case, we made a bunch of little mistakes. The thing itself was right, and I really am quite proud of the work we did there. Me and Chris Cox at the most core probably in the engineering side, which you saw as the PM, there was no ranked feeds before that. We did have some AI that I built before for the anti-spam, anti... things, but it was pretty rudimentary, but it was probably the first consumer AI that was in a website of that kind around content. And we built the most efficient monetizing surface in history outside of Search, I think. [inaudible 00:37:04] for those who are curious, I don't use monetization because I think money's the most important thing. I do think it suggests the economic power you've created, which I do think correlates very strongly with human utility. Although obviously I respect that some people may disagree.

**Lenny** (00:37:17):
In terms of the economic utility, the Venn diagram of Boz, of News Feed and ads, create $1 trillion dollars of value.

**Andrew ‘Boz’ Bosworth** (00:37:24):
It's not-

**Lenny** (00:37:24):
Well done.

**Andrew ‘Boz’ Bosworth** (00:37:25):
It's not nothing, not nothing.

**Lenny** (00:37:27):
[inaudible 00:37:27].

**Andrew ‘Boz’ Bosworth** (00:37:27):
We're proud of that work.

**Lenny** (00:37:28):
You have this quote in one of your posts about the News Feed where you said, "It consumed me more fully than anything in life had ever consumed me. It opened up to me the truth that when you're passionate about something, you do better work, you do smarter work and you're, in order of magnitude, more productive."

**Andrew ‘Boz’ Bosworth** (00:37:43):
There's no substitute for it. One thing I've learned about myself since that post actually is just the degree to which I am somebody who is inclined to be passionate about things. And it's a gift that I'm lucky to have, and I understand that's not every person. And so actually the ads thing is a good example. When Mark told me to go work on ads, I was like, " No, I don't want to. I don't think I have a passion for that." I had this idea of myself. I had a very strong identity of myself as this AI infrastructure product guy, and I was working in this space and nope, I was wrong. I just am a guy who gets excited about things. Once I get into ads, it's like, "Oh, this is fascinating. It's a three-sided marketplace, and there's all these different..." It felt like I was playing chess times in terms of the moves with the other players in the industry, and I was super pumped about that.

**Lenny** (00:38:26):
And then when he wanted me to work on hardware, I was like, "No, I'm not. I'm a software guy. I'm a software guy, Mark." And now, I love this work. That's such a fascinating space that I've learned so much. So I do think that's right. I do think what I find something I'm passionate about that's good. What I have learned since then is to give myself a space to understand if I can get passionate about it. Now, there are parts of jobs that I've had before where I just never found the passion, and after six months I just have to move on. Literally it's like I'll either quit, get fired, I'm doing bad work, I don't care about the work. And so I do have a self-awareness. It's not that I can get passionate about anything, but I do have a pretty broad palette, it turns out.

**Lenny** (00:39:01):
I think that's a really interesting career lesson of, "Don't assume you won't be excited about something that may come up." Is there anything there that you'd share with folks of just like, "Explore it, give it six months, see if you can get excited about it?"

**Andrew ‘Boz’ Bosworth** (00:39:14):
Absolutely. So I have a very unusual career arc in some ways, which is I really almost changed jobs every six months for a long time. I was working on this integrity stuff with News Feed in the background. Then I was working on News Feed for about a year. Then I worked on site speed and infrastructure and detecting SAVs and issues. And then I worked on Bootcamp, and then I worked on messaging and groups. I had this really funny thing. I was kind of joking it was like, for those who are old enough to remember Karate Kid, I felt like I was painting a lot of fences, waxing a lot of cars, and at the end I knew karate. I was like at the end, at the end I had the payoff, because I'd gone through and I'd met a lot of people and I'd worked in these different areas and I understood different dynamics. Well, other people who joined in my cohort were getting promoted, but they were in a single track. They just stayed in one place and they got promoted, whereas I kept moving around. And it probably at some point early in my career felt like I was moving more slowly relative to my peers. And then when I finally turned the corner, really with the ads appointment, which I did for five years, I went vertical. I just like my career went vertical. And since then I've kind of been on that trajectory. And so advice I most often give people, for me at least, the lesson that I take from this, is I just was willing to learn aggressively. I would move because I wasn't learning enough. I was bored, and so I wasn't learning enough new stuff. And what was cool about finally getting to the ads job, and likewise in the job I'm in now, is those jobs, I learned a ton for five years. I'd never stopped learning in those jobs. You will occasionally find those jobs where they're super deep and you can just keep learning.

Meanwhile, a lot of my friends whose careers were on a better trajectory [inaudible 00:40:55] then earlier, they literally got bored of what they were doing, but they didn't have any place to jump to. There wasn't some other... They'd become domain specialists in a domain that they'd kind of exhausted for themselves. And maybe they'd even stuck around longer than they wanted to because it was comfortable or because the company wanted them to. And it ended up kind of being a hindrance to them in the middle of their career. And so for me, it's like, "Jump into new things, give it six months. If it's not the thing, no problem. You just built a ton of new skills that's going to come in handy, I promise you that. Keep going." And likewise, when you do make that jump early career, optimize for learning, optimize for... Think about a compound interest. It's like the first 10 years of compound interest don't look that impressive. It's like after 10 years it starts to look good.

**Lenny** (00:41:43):
I love that advice. It's similar advice I always give of, "Variety of experience often ends up being the most valuable thing you build over time," just trying to bunch of stuff, doing some internal tools, maybe working on customer support, I don't know, trust and safety, user-facing products, infrastructure. I'm thinking from a PM's perspective, maybe an engineers, and other functions. One question along those lines. So we talked about the eye of Sauron and working on the most important thing at the company. Do you have any advice on how much of your career you should be working in that center?

**Andrew ‘Boz’ Bosworth** (00:42:12):
Yeah, listen, [inaudible 00:42:12] being equal, I think there's two really good places to be. I think one is carrying a lot of water in areas that the company's not paying attention to but you are important. And it needs to be a lot. You got to own that stuff and really move mountains over there, because I promise you, as an executive, when there's a huge dam holding up the floodwaters, you respect the heck out of the person who is holding that dam up. You're like, "You keep doing that, Atlas, that is good work over there." The second-best place to be, or maybe equally, is on the most important thing. And on the most important thing, that's where you get to the advice that Eric Schmidt gave Sheryl Sandberg, which is like, "Hey, it's a rocket ship. Get on. Don't ask what seat I'm in. Just get on."

If it's the most important thing, you're going to get a smaller piece. Everyone wants to be there. Get the piece. If it's the most important thing, get the piece that you can crush, kill, do a great job at and grow from, because you're going to get a ton of visibility, you're going to get a ton of experience. You're going to see what it looks like in the fire, in the fire, and that is invaluable. You will use that everywhere. And so I say that. That's at project selection time, but now I'll be cautious. Understand, projects that start in the fire, hopefully, are forged in some manner of metal that cools and is no longer in the fire, like God willing. And likewise, things like dams that are holding up floodwaters have a tendency to crack or break or floods overcome [inaudible 00:43:42]. So I think you do want to be at selection time in one of those two places, but then you also... You're going to stick with the ride.

And again, to my point, if you're not engaged, if you aren't doing great work, if you don't love it, then move on. If you've exhausted it, you used to love it, but you don't anymore, move on. If you still love it and you're engaged, great. That's cool. That's a great thing. You deserve to go from the forge to the dam and back over time. You don't have to always just keep jumping onto the latest fire. I tried to do that once, after the ad [inaudible 00:44:14]. Actually, so I spent six months and we built the first mobile ad product in 2012 and kind of saved the IPO, which had gotten pretty grim [inaudible 00:44:23]-

**Lenny** (00:44:23):
Yeah, I remember that.

**Andrew ‘Boz’ Bosworth** (00:44:24):
... that point. And I told Mark, I was like, "This is so fun. Maybe you can just keep doing this, just putting me on the biggest fire every six months." And he turns to me, he said, "Buzz, that's not a real job."

**Lenny** (00:44:32):
He's like, "I need you to stay here and usher this forward," which I did for the next four and a half years. And it was amazing. It was amazing. And again, I do give him such... It's funny, I'm going to get a hard time in this. One of our biggest critics as well as being one of his biggest fans. I have both those jobs, but today we're talking about stuff that I think Mark really demonstrates really well. And he did a great job of pushing me in my career to different places where I didn't think I could succeed. And he saw the opportunity that made it happen.

**Lenny** (00:45:01):
What have you learned about that, giving Mark negative criticism, anything that he accepts? What do you learned about that?

**Andrew ‘Boz’ Bosworth** (00:45:08):
Mark's voracious for all information and all points of view. One of the things that's pretty interesting, I talked earlier about how much, as a founder, I think especially, you have to have tremendous conviction. You just have to have a tremendous degree of confidence. And I think Mark is somebody who is maybe the strongest willpower of a person I've ever met, just in a pure willpower sense. One thing that's interesting about Mark is you'll give him feedback, he listens. He's a kind person to work for, so you'll give him feedback, and he'll listen. Truly. He'll most often tell you that you're wrong, why you're wrong. That's just like most often. And what will happen is... It's uncanny. It's like over the course of the next week or two, you'll just see shifts. And I don't think he's doing it...

**Lenny** (00:45:55):
I've always joked that the information gets to him. So much information every day gets him. And then at night, he re-compiles the whole world with all that information and comes back. And by the way, this is not just true about product work. In my head, I was thinking about product stuff where he was like, "Hey, I think this product is doing this wrong." He's like, "No, no, that's why it's not that way." And the product will start to shift. Also to give him feedback just on his own presence in a meeting or delivery, he'll be like, "Oh, well here's why I did it that way." And then a couple weeks later, you'll get in a similar situation, and he will moderate how he shows up. So I actually find him somebody who's really satisfying to give him feedback. It really works. It's very effective, but you do have to take the long view on it. And he will have a... The things he did, he didn't do an accident. He will have a reason why he did them the way he did them.

**Lenny** (00:46:39):
It's a great example of strong opinions, loosely held.

**Andrew ‘Boz’ Bosworth** (00:46:42):
Yeah, that's right.

**Lenny** (00:46:44):
It also makes me think, I think you used the compiler analogy. I'm thinking the model training. He's retrained his model overnight.

**Andrew ‘Boz’ Bosworth** (00:46:50):
Yeah, that's right. It's funny. One of the things that's so funny about Mark is if you give him some feedback in the morning, the next six meetings he has, whether it's about that product or not, he'll ask people what they think of that feedback. He won't attribute. He's just like, "Hey, what do you think about this in this product? And so you'll be in a meeting with him and you'll see him doing it. He'll come to the meeting with you about some other topic. He'll be like, "Hey boss, what do you think about this product and this idea?" And so he will, over the course of the day, take that little note and kind of pressure test it, and he loves to triangulate. Where are all the points of view on this that maybe you didn't see? So he really values a broad perspective on each thing that's being discussed, which is really fun.

**Lenny** (00:47:29):
Trying to get more training data for his model. I get it.

**Andrew ‘Boz’ Bosworth** (00:47:32):
You can't get me to call Mark an LLM. That's not fair. That's [inaudible 00:47:35].

**Lenny** (00:47:35):
We could all hope to be as smart as Mark. As you were talking, I noticed your tattoos, and it reminded me that you've got at least two tattoos that I'm aware of.

**Andrew ‘Boz’ Bosworth** (00:47:35):
Oh, yeah.

**Lenny** (00:47:45):
One is of California, which I completely understand. California is a very special place, but you have this other tattoo that is just the words Veritas. Can you talk about what that's about and why that's important to you?

**Andrew ‘Boz’ Bosworth** (00:47:58):
The funny thing about tattoos in general is I came out of high school, I was like... I don't know if there was an archetype for me, but I didn't drink until I was 21. I was a very rule-following person. I was like, "Why are you going to get a tattoo, affect your body? "Why would you dye your hair? Just let it be what it was." And some of this was I think I was somebody who was privileged and had a great deal of self-confidence in who I was and what I wanted to be, and that was fine. But in some ways I was also weirdly judgey about other people in a way that's kind of off- brain for me, certainly today it would be, but at the time, getting a tattoo is a big deal for me. I was like, "Oh, this is just the vehicle for my life and you can do whatever you want with it. And it's not like a... It's something that you possess, and if you feel like if you want to decorate it, you can decorate it.

**Lenny** (00:48:47):
And so getting a tattoo was a big deal to me actually, and I completely shifted my mindset of how I thought about my body and how I thought about people's body and their presence and their time, maybe to some degree, even an understanding of mortality. Like, "Hey, can't take it with you. It's all going to go..." When you're 18, you think you're going to live forever, and by the time you're 22, a grizzled 22-year-old veteran, you're like, "Ah, tattoo that bad boy up. It's all going down." And so yeah, that's why I got the Veritas tattoo, which is Latin for truth, which is... I will say it's a little cheesy, because it's also Harvard's motto. But I got it in a monotype font. This is the programmer's font here.

**Lenny** (00:49:28):
The other thing that's interesting to me about tattoos was it's also part of a generational shift. We grew up in a time when tattoos were really seen by adults as gangs or bikers or sailors or certain types. Now my understanding, I saw a stat recently that more people in my generation have tattoos than don't have tattoos. And so I think we also just culturally shifted positions in a way that... I find richness of self-expression wonderful. I really think it's great. And so I'm here for all of it.

**Lenny** (00:49:56):
My assumption from what you're describing is, this idea of truth is very important to the way you think and work.

**Andrew ‘Boz’ Bosworth** (00:50:01):
My reputation does precede me on this point, I'm afraid, which is... I think when I was young, I saw being honest... And I was wrong by the way. I saw being honest as kind of a get out of jail free card. You could say whatever you wanted as long as you're being honest. That's just not the case at all. I've written about this before, but by far my biggest professional regrets were me not being kind. And I used to think... I wrote this note a while back called Be Kind, where being nice, that's like patronizing, or telling somebody things that are half-truths or just getting by. And I'm against that. But being kind isn't that. Being kind is like, "Hey, how can I deliver this feedback in a way that is actually productive and helpful, in a way that is going to help them and not cause them just to feel bad and helpless?

**Lenny** (00:50:50):
And I think I did that wrong a lot as a kid, as a young man. And so being honest is still a big part of my personality. No one would ever accuse me of being dishonest who knows me. And I think people understand and respect that I'm pretty direct, and if I have concerns or issues, I'm going to bring them up. I'm just much better at bringing them up now and expressing a true care and belief. I wouldn't bring it up if I didn't think we could do better, if I didn't think we could fix it, if I didn't believe in this situation. And so being honest is still a huge part of my identity, and I think that's something I'm very proud of. But I will say the contextualization of how I'm honest has changed immensely since I got this tattoo.

**Lenny** (00:51:29):
That seems reasonable. This touches a little bit on something I definitely wanted to talk about, which is one of your most classic pieces, and this is the way I first learned about you, is a piece that is called Communication is the Job.

**Andrew ‘Boz’ Bosworth** (00:51:40):
Yep.

**Lenny** (00:51:41):
I know many people have read this, many people haven't. I'd love for you to just talk about what this means and why this is important, why this is something that you wanted to share.

**Andrew ‘Boz’ Bosworth** (00:51:49):
Yeah, it's one of the things that, especially if you aspire to be a leader... And leadership isn't management, and leadership isn't being the only person responsible, it's not even always the same as accountability. But if you want to have an impact...

**Andrew ‘Boz’ Bosworth** (00:52:00):
It's not even always the same as accountability, but if you want to have an impact on the world around you, it is exclusively done through the creation of artifacts or verbalizations that affect other humans. That is all there is. That's all there is if you want to have an impact, if you want to create some kind of a lasting change. And it could be in your little relationship, it could be in your team, it could be in your company, it could be in the world. It is down to communication. And so often you hear people saying, "Oh yeah, I wrote that up a year ago." It's like, "Yeah, but you did a bad job of writing it up a year ago, or we would've not wasted a year not doing it."

**Lenny** (00:52:47):
People always think that's, "Oh, I had that idea," and that's means anything. It means nothing. It means absolutely nothing. Or it's like, "Oh, I wrote this post." Well, you didn't break through with it. That's on you. It's not on the audience. People want to blame the audience. Well, the audience is just there. I mentioned this even earlier, and I hope people caught it, when I said, "Hey," I give somebody a piece of work and they come back six months later and they have done the wrong thing, I'll take the L. I will take the L on it. It's not great for them. They'll be pissed they wasted their time, but like I said, that's my responsibility. I did not communicate clearly what I wanted, what the expectations were.

**Lenny** (00:53:25):
Could they have also helped themselves? Sure, they could have, and that's a thing that takes all sides. We should work on this problem for both angles. I have another post called Listening is the Job, which is the other side of this. But communication is the job is, I really believe... Actually, it's the relationship to this idea that came out of the US Marines and the SEALs of extreme ownership, which is... So whenever thing goes wrong, I ask myself, "What could I have done differently in terms of how I communicated things for this to have gone better?" Could I have set priorities better? Could I have set expectations better? Did I need to have a better metric that I pointed the team at? Did I put the wrong people on it?

By the way, the thing I talk about is org charts are communication devices. They don't exist. There's not a physical string between you and your manager. They're just communication tools that are supposed to give people a rough sense of how things are organized and where to go with who. And so all these things are communication. Silence is communication, me not reaching out to you to check on you, to check on your project. We talked about the [inaudible 00:54:29] earlier. What does that mean? That means trust. That means responsibility. The absence of check-ins has meaning. You cannot not communicate. You are always communicating something with your face, with your clothes, with your body. What are you communicating?

**Lenny** (00:54:45):
I'll give you a funny example, which I hope we get to put in the podcast, because if you're watching this on video, you will have noticed that my camera cannot stop adjusting light. It's just constantly too dark or too bright. I'm trying a new camera. I'm a nerdy guy. I try a lot of camera gear, I try a lot of microphone gear. I love to have all the latest gadgets and gizmos, so I'm trying something new. It's not working. And in my head I'm like, what is this communicating about me? People are going to think that I don't care or that I'm not competent.

**Lenny** (00:55:15):
That's what I'm talking about. And now, I felt compelled to explain it in the podcast so that I can communicate clearly that that's not the case. I really just think so much of what I try to do in my professional life is understand the mental model of other people. Where are they right now? And I mean specific people, like my managers or my key technical leaders, and I mean general people like teams, and I mean broadly just the average human. Where are they at in this conversation? And how can I craft my language, my presence, my persona, everything to usher them from where they are to where I want to get them?

**Lenny** (00:55:52):
And that requires me to have a very clear idea of where I want to get them, have to have a clear idea of where they are. And I want to tell you, it's not as much work as it sounds like. I think no one would accuse me of having this big fabricated persona. It's not that. But it is having tremendous empathy for where people are starting. That was the lead for me. All the rest of it, all the rest of how I show up in meetings trying to smile more, because I'm like a big scary guy, those things are little things that you work on and they become second nature and they're easy. The hard thing is just having the empathy for your audience and being, "Where are they? Where are they starting?" And when you miss taking responsibility for that, extreme responsibility for that.

**Lenny** (00:56:31):
There's so much good advice in that. There's so many threads I want to follow, but let's just follow this last one of trying to understand how someone is best communicated to. Is there an example to make that a little more real for people of just what you've done to, "Oh, here's how I'm going to communicate with this person?"

**Andrew ‘Boz’ Bosworth** (00:56:46):
I'll give you a couple. One is multimodality. There's an old saying, repetition never spoiled the prayer. And I think most experienced communicators, whether they be writers, whether they be public speakers, talk about the importance of reiterating a point several times and in several different ways to make sure that people have a chance to internalize it. You want to use it, you want to say it directly, you want to use metaphor. And so for me, I will give an all-hands and then write a post with the content of the all-hands, because different people are going to respond differently to these modalities and are going to absorb information at different rates on these different modalities. That's a trivial one.

**Lenny** (00:57:23):
Another one that I think of all the time is making sure that you address people's fears and concerns. People will not listen to you if they think you don't know what's going on. And so, one of my favorite things to do when we're talking about some kind of issue is right up top and say, "Hey, let me be clear. This is the issue we're having. I know we're having it. I know what matters." And then I'll say the same thing that I would've said, but they would've literally ignored me, because how can they trust my conclusions if they don't accept the premise? You know what I'm saying? I think there's a whole piece there. Obviously when you're in person, it's a lot easier because you're reading facial expressions. Even on this, I'm reading you nodding on that. I'm like, "Okay, he's with me." And then I throw in a, "You know what I mean?" Whereas if you give me a cocked head, I then bring a second example to try to drive the point home. But you build yourself up. Most people are going to realistically start in their careers trying to influence one or two people. That's where you start. One or two people. That's who you got to communicate with. Your manager, one teammate, that's who you got. And then you build up and build up and build up a skillset to do it at a larger and larger scale.

**Lenny** (00:58:36):
I love so much of this advice. I think it's also helpful for relationships. "Here's what you're upset about."

**Andrew ‘Boz’ Bosworth** (00:58:42):
Totally, a hundred percent.

**Lenny** (00:58:43):
"Here's what I think we can do."

**Andrew ‘Boz’ Bosworth** (00:58:46):
Again, the work that I've had so graciously supported to do on myself at Meta with great mentors, Sheryl Sandberg, Mark Zuckerberg, a bunch of others and coaches absolutely made me a better partner and husband, and my wife. And then by the way, vice versa. Having kids and getting deep in the literature around raising children. Congratulations to you, by the way. Getting deep in that literature made me a better manager. Absolutely made me a better manager in terms of thinking about how people are managing their emotions and how to engage with them in those times.

**Lenny** (00:59:16):
Amazing. We need a second edition of this Boz's Parenting Advice.

**Andrew ‘Boz’ Bosworth** (00:59:19):
That's right.

**Lenny** (00:59:20):
And relationship advice.

**Andrew ‘Boz’ Bosworth** (00:59:21):
It's all the good stuff. No bad kids, Lansbury, it's good inside, Dr. Becky. It's all-

**Lenny** (00:59:28):
I like Dr. Becky.

**Andrew ‘Boz’ Bosworth** (00:59:28):
I really think that the modern parenting canon is really rich.

**Lenny** (00:59:33):
**Andrew ‘Boz’ Bosworth** (01:00:57):
Actually, Mark and I tried it together and I want to say, first of all, when the headset came out, we breathed a little sigh of relief because the stuff inside of it didn't represent a fundamental breakthrough. Everything inside of it was something that we probably could have gone and done, with the exception of Apple silicon, which is a marvel, but it's worth nothing. Apple Silicon is like a 2X marvel when doing things like scaling display resolution is unfortunately a quadratic proposition, and so a 2X linear scaling advantage doesn't buy you as much as you might expect when you're trying to scale resolution. And so that was step one. But we still assumed at that price point, with their legendary attention to detail and polish, they probably produced a great product. And the line that I said actually my own podcast with Matthew Ball a week ago was, "Look, I was prepared to come to market and say we have the best value headset. If you want an outstanding, best possible headset for the money, we've got it. It's the Quest 3."

**Lenny** (01:01:55):
And I was so thrilled when I tried the AVP next to Mark, we were like, "No, we think we have the actual best headset." Now, we're not saying it's the best at all things. If you're sitting still and watching a movie a high-res movie, Apple Vision Pro is really great. It's really great. The resolution shines. The way they've tuned the pass-through shines if you're stationary and looking straight ahead. And they've done some really nice things with the UI. It's one of these things that we do get annoyed about, a mile aside, we get a little bit annoyed about as product people.

**Lenny** (01:02:31):
I know that this happens to all of us. It happens to Apple, happens to Google, happens to us. We have a bunch of internal things we've been playing with, which will at some point ship and we will be accused of having stolen them when we actually did not steal them. If you want, you can go see my Quora answer on the history of the like button where this happened previously, where we had built the like button internally before it was launched elsewhere. Anyways, it's a whole thing. This happens in our industry a lot, and I really shouldn't care as much. It's a little bit of my ego peeking through, which I should control and tamp down, if I'm being responsible.

**Lenny** (01:03:03):
The beautiful UI polishes, they did a tremendous job with eye tracking. One of the things that's interesting about the eye tracking is, to do it the way they've done it, that's why you have to have the prescription insert, so it doesn't support your glasses. You have to get prescription inserts. They're expensive. And they can shoot the cameras that track your eyes through the lens as well as the light around it. Ours go from the side on the Quest Pro, and that allows you to wear corrective lenses.

**Lenny** (01:03:27):
And so different choices like that have trade-offs, but it's still cool. It's great that they got that in there. At the same time, our hand tracking is better. Obviously, the app library we knew was going to be better. That's not totally fair to them. They've just launched and they have small volume still, but I just find the comfort... The thing that really got me the most, the field of view is really small on the Apple Vision Pro. And some people are characterizing it incorrectly on the internet. They're doing a characterization up close to the lens. Once you factor in the eye relief, the distance between where the lenses are and your eyeball is, their field of view gets pretty narrow for almost all faces relative to ours, which I find distracting.

**Lenny** (01:03:59):
Their displays are much dimmer than ours, and I find the motion blur really distracting when I'm in mixed reality use cases. And as I mentioned earlier in the podcast, I'm a huge mixed reality buff. I'm a huge fan of that potential for exactly the same reason that they are, by the way, which I think hands and mixed reality make it feel much more accessible to more people. I'm pretty glad we have the controller in our set though, because it really expands what you can do. And we don't just operate our computers with just one thing. We have a keyboard, we have a mouse, we do multiple modalities all the time. I really feel like the comfort, the lack of persistence and motion blur in our pass-through, the brightness of our displays, I was like, "Oh man, if you gave me one to take, I would take Quest 3."

**Lenny** (01:04:40):
Now, people have rightly said, "That's pretty biased." Of course it is. Go get your own opinion. But what kills me is most people haven't done that. They have not tried the Quest 3. That's what kills me the most. If you go and try Quest 3, ask yourself if you'd rather have seven of those, one for you and six of your best friends, or one Apple Vision Pro. I'm sure the answer isn't Quest 3 for every person. There are people for whom there are use cases that really fit their life, the Apple Vision Pro, I'm cool with it.

**Lenny** (01:05:05):
But people don't even know that the Quest 3, you can do Remote Desktop. You can do it both through an app called Remote Desktop, which is very popular, or you can go into workrooms and you can have three monitors surrounding you streamed from your machine. I think some of this is just people have not even done the work. They haven't even tried it. I welcome all of you who think I'm biased to prove one way or the other what you think, but don't do it without putting the Quest 3 on and giving it through its paces, because it's a pretty great device. And you can do a lot with $3,000 extra dollars.

**Lenny** (01:05:38):
How did they get away with that, by the way? We launched a headset that was $1,299 and people lost their minds about it. They're like, "Ah, $3,500, it's fine. This is fine. No one cares." I don't know. Fairness is too much to ask, and I don't care about that. Apple has earned the great brand that they've built. They truly have. I think it's tremendous. I certainly celebrate a large number of Apple product. I'm a huge fan of their work. I'm a huge fan of what they do. That's probably why I expected more from the AVP.

**Lenny** (01:06:06):
Well, I'll show you my favorite AR device, which is these Ray-Bans. I actually bought them.

**Andrew ‘Boz’ Bosworth** (01:06:13):
Yeah.

**Lenny** (01:06:13):
Here, I'll put them on it. Here, what I'm going to do is I'm going to record. I didn't tell you I was going to do this. I'm going to record this as we're talking. Look at this.

**Andrew ‘Boz’ Bosworth** (01:06:20):
I like that. They look so good on you too. This is a good fit.

**Lenny** (01:06:23):
My mother-in-law's like, "You look so sophisticated. You look really smart with these on." And we bought these actually to film our kids, or our kid, instead of having Cameron's face. And it's been awesome.

**Andrew ‘Boz’ Bosworth** (01:06:34):
It's really the best. It is so hard to look at a phone screen and have the real thing be in between you. No, the glass is the way to do it.

**Lenny** (01:06:43):
Look at this, my new look. I'm just going to have glasses on all the time.

**Andrew ‘Boz’ Bosworth** (01:06:46):
We got to get you the multimodal. I've been playing with that since December, where you can use the camera to ask a Meta AI assistant about things. It's really good. I was in a ski village recently with my family and I had them on. I'm just like, "Hey, take a look. Tell what you see." And I had found a sign and it gave me directions. "Hey, the bathrooms are down those stairs to the right. Do you want food? It's over to the right." It couldn't tell what village I was in, but it was like, "You're in a ski village somewhere. Here's the amenities." And I was like, "Wow." There's something real magical here.

**Lenny** (01:07:18):
I feel like I need this for my podcasting interview so I could just have a little voice tell me questions to be asking and where I'm at.

**Andrew ‘Boz’ Bosworth** (01:07:25):
Right, totally. Yeah.

**Lenny** (01:07:26):
How helpful would that be?

**Andrew ‘Boz’ Bosworth** (01:07:27):
Okay, I'm going to cheat on this one and say, obviously we've been talking for a while, but playing with glasses that have full AR capabilities, and we've got one that has rumored to be coming internally soon, so heavily rumored in fact that you might even say it's almost been confirmed. And what's been really fun is being able to play with these time machines, really, in terms of what they are. It's amazing technology. People were giving us speeches, big company-wide speeches, and had all their notes on the glasses. And they could control the slides just using a gesture.

**Lenny** (01:08:05):
Oh my God.

**Andrew ‘Boz’ Bosworth** (01:08:07):
There's exciting things afoot. The future's looking pretty bright.

**Lenny** (01:08:10):
Something that I wanted to touch on, which is when Mark put out this whole video of, "Here's what I think of Apple Vision Pro versus the Quest," a lot of people are just like, "Oh man, because he's putting out this video, he must be so afraid of what's happening and it's not the right move." What went into thinking? Was there strategic thinking there? Was it just him, "Here's what I think?"

**Andrew ‘Boz’ Bosworth** (01:08:29):
This guy does [inaudible 01:08:30] about the modern era. Everyone's in their Meta head about everything. Everything's a four-dimensional chess. That was just what Mark thought of the thing. That's what he thought about it. I think he wanted to make sure people remembered, hey, Quest 3 is literally a better device, and people haven't even tried it.

**Lenny** (01:08:46):
And so we're not always playing four-dimensional chess over here. Sometimes we're just like, "Here's a thing that I believe is true. I'm going to say it out loud with my mouth." That's what he did. It's not that hard. When I do it, everyone expects it because of my persona or brand or whatever the thing is. I guess people are surprised when a CEO does it. All right, I get that. That's cool. There's other sets of societal expectations there.

**Lenny** (01:09:08):
And we're all familiar with Apple putting the Welcome IBM ad in the New York Times, and then Slack doing the same thing with Microsoft and the Ballmer iPhone comments. None of those were true discussions of the technical merits of a product. Those were all just big, rally the troops gestures. This is not that. Mark is deep. He's an expert in this stuff. I'm an expert in this stuff. I feel great about our choices.

**Lenny** (01:09:39):
By the way, when I've used it, I could get myself completely into the head of the person who designed it. I can tell you from using it what instructions they were given, that team was given. I can tell you what they were optimizing for. I can tell you what constraints they were under. By all the choices they made, I can tell you all those things and I understand it coheres in that way. We made different choices. It shouldn't surprise anyone. We like our choices better. We could have made those choices. We didn't make those choices. We made these other choices.

**Lenny** (01:10:06):
And so for me, the weight, the wire, which just always brushes against my ear, the pocketable thing, I get it. That's not what I would've done, and I know that because I had the chance to do it and I chose not to. I don't know. I don't know why people are surprised. This wasn't some big, savvy strategic move. This was just, Mark's got a chance to use it. He's like, "Oh man, I think we should tell people what the real story is here." And we did.

**Lenny** (01:10:34):
I love that insight. And I know a lot of people watching are like, "Oh, shit, he's right. Wow. I didn't think of it that way." And so I think it had a lot of that impact.

**Lenny** (01:10:41):
I want to zoom out a little bit and talk about Meta's journey over the past couple years. It feels like there is a huge downturn in public perception of Meta and the stock price, and then over the past couple of years there's been a huge turnaround. And it feels like there's always a lot to learn from these periods. Just as an example of the stock price, I was just looking at it, it was down to $80-ish, and now today it's $487.

**Andrew ‘Boz’ Bosworth** (01:11:05):
Yeah.

**Lenny** (01:11:06):
I'm curious just what you've learned from going through that downturn and turnaround. And I know it's still in progress, but just what have you learned from that journey?

**Andrew ‘Boz’ Bosworth** (01:11:16):
Yeah. Well, there's a lot to take away, I got to tell you. I think we had the largest single day stock drop in history, followed 18 months later by this largest single day gain in stock market history.

**Lenny** (01:11:27):
Oh my God.

**Andrew ‘Boz’ Bosworth** (01:11:27):
As the legendary Lou Holtz said, " You're never as good as they say you are when you're winning, and you're never as bad as they say you are when you're losing." Mark has always brought that quote out to guide us internally to try to insulate ourselves a little bit from the vagaries of external opinion. And that's not just true with stock prices. That's true with media and press. It's true across a lot of things.

**Lenny** (01:11:53):
One of the things I told my team, and I still have to repeat it to them, is, "One of the things that's hard to remember when you're in it is that you know more than the critics do. You know more than the analysts in the marketplace do. You know more than the media does. You know more than the podcasters do. You know more than the Twitter does. You know more about what's real and substantial of value about our company than they do. That doesn't mean ignore them, because they have a different perspective and you need to understand it. Even if the totality is less than what you know, it may contain parts that you do not know." I'm a huge fan, I read the criticism of everything, and I read it very carefully, looking out for confirmation bias, looking out for things that I might be inclined to resist but are maybe true. I invite all critique, but I also don't accept the critique blindly. I don't just say, "Yes, this is obviously true."

**Lenny** (01:12:55):
Gell-Mann Amnesia is a great concept for everyone to understand. Gell-Mann Amnesia is this property where you'll read a newspaper article, let's say newspaper, why not, about a thing about which you are an expert, and you'll be baffled because here is an article that is not just wrong, it's inverted causality. Michael Crichton, I'll steal Michael Crichton's quote on this, "It's a wet sidewalks make rain story." And you'll be like, "What a terrible, bizarre story."

**Lenny** (01:13:22):
And then you will turn the page of the newspaper and it will be another article about a topic about which you know nothing, and you will read it as if it is the gospel truth. You'll figure it's, "Oh, no, look at this information about this foreign situation." Like I said, perfectly true. We should be smarter than that. And so does that mean you don't read the thing? No, you read it. You just read everything with that perspective of, "Wait a second, this is another point of view. And how do I integrate that into a whole perspective that I can have and be informed about?"

**Lenny** (01:13:55):
The first, the macro thing is taking the long view, realizing that when you're in the dumps, it's not as bad as you think, when you're at the top, it's not as good as you think. It's somewhere in between at all times. The second thing is communication is the job. We really did not communicate effectively, I think, with the market around our future investments. And listen, we've had two 10-year long huge investment areas. One has been AI, one has been reality labs. And AI's looking pretty good today. I can't think we can all agree with Lama 2, with Fair, the breakthroughs that we've had.

**Lenny** (01:14:33):
People don't notice that Fair, our AI research lab, is the second most cited research lab in AI behind Google. We've been doing this work. We didn't come here casually. We've been doing it, and so that's looking pretty good. I don't think we did enough to explain those best to people. Previously, the core business was going strong enough and they were willing to ignore them. And with the old Warren Buffett quote, "It's only when the tide goes out, we see who's not wearing swimming trunks." And so when the tide went out, when you have the Ukraine war and an interest rate hike and recessions, now everyone's scrambling for that incremental dollar and they're like, "Go get rid of this stuff."

**Lenny** (01:15:15):
And we had to tell the company, "You don't want to work at a company that, when times are tough, kills all future growth and just shores up in the core business." That's a company that's just committing itself to dying at some point, a little later than expected, but dying at some point. You want to work at a company that has a balanced portfolio of investments, which we had. We didn't explain that well, and so we spent that time explaining that to the market, to the press, to everybody.

**Lenny** (01:15:38):
And now, I think as people understand the size of it and the scope of it, and of course it helps that the core business has overcome its challenges there from ATT and the other kinds of stuff, it's looking pretty good. I do think one part is, as an internal person, really moderating your attachment to the external narratives and swings, that's super important. And you do that based on understanding your own expertise. And the second part is understanding why is there a delta. What is there? And grab that. It's usually communication.

**Lenny** (01:16:10):
There's also a big flattening of the org. This was something a lot of people talked about, where managers became ICs. Is there anything more there that you've learned of just how to adjust the org to be more efficient?

**Andrew ‘Boz’ Bosworth** (01:16:22):
Of course, and I should have included that in the first section. I was a bit eager to wrap it up elegantly in the two. But you're right.

**Lenny** (01:16:27):
I appreciate it.

**Andrew ‘Boz’ Bosworth** (01:16:29):
We made significant shifts in how we operated the business, which was super painful. And listen, this goes back to the boom times of COVID, when it looked like there was a real lasting secular shift in things like e-commerce and in working remotely and these tool sits, which are exactly what we build, and it's primed us. And so we built up a huge workforce to pursue those opportunities. We still believe in those opportunities, but they're back on their original timeline. And actually, literally, if you look at a bunch of graphs that we have internally, it's literally the COVID boom and then, not bust really, but as it receded, everything's back on its original trajectory.

**Lenny** (01:17:16):
We didn't lose ground or lose time, but the pull forward didn't happen. Well, that means your economics don't make any sense anymore. Now, you made a bunch of investments that are going to yield too distant in the future, and getting there faster isn't going to help you and you're carrying a much extra cost. That sucks, man. It sucks. And we don't feel great about it. We really don't. It's a business, it's awful, and it happens.

**Lenny** (01:17:41):
I do think one thing that was interesting about that time was, for those of us who grew up and saw the .com boom firsthand, I was born and raised in the valley, so that was all around me when I was graduating high school and going to college, and then in the 2008 major recession on the housing crash and on the market and all that stuff. Now, let's imagine you graduated college in 2009-

**Andrew ‘Boz’ Bosworth** (01:18:00):
... all that stuff. Now let's imagine you graduated college in 2009 and got a job. Well shoot, you're 15 years in your career, you could be a director and you've never seen a downturn. I think we also had, in addition to what was very unfortunately conventional mis-forecasting in the business that caused us to over hire, that we had to correct for. You also had a workforce that was just not at all of a mentality that this could ever happen. This felt like it was an act of God when in fact it's like a cyclical nature of all businesses that this will happen at some time and you hope it doesn't and you wish it didn't, but you have to deal with it. And so I think we have a bit of a tough storm there for the whole industry and we're still feeling it. I think we're still feeling it.

**Lenny** (01:18:45):
Certainly we're happy at Meta to be beyond that point and we're growing again and executing at a stable rate and feeling really good about that, but quite a few of our other companies in the industry. And it's a very uncertain time for engineers, for PMs, for designers, for everyone and all the support functions around them. I'm super sympathetic for that. I think obviously the mis-forecasting that happened inside of Meta's walls happened everywhere and now that you have, especially with higher interest rates and cash isn't as cheap, runways are tighter. People are just making those pragmatic calls. I think we'll rally back from this. I think this is a normal thing that happens to industries, but it doesn't reduce my sympathy and empathy for those who have been affected by it or who live in fear of it.

**Lenny** (01:19:29):
I was talking to a friend who works at Meta and I was asking them what it's like to work at Meta and she was just like, "It's intense, and it used to be more chill. There were people that were coasting here and there," and now she's like, "No, all those people are gone now. It's just only the intense people left and we're working really hard." Does that bring up anything?

**Andrew ‘Boz’ Bosworth** (01:19:48):
Yeah. I don't want to comment on people who left. People left Meta for all kinds of different reasons and likewise role elimination happened in many cases because we just decided not to do this work at this point. We were going to do it two years from now and don't need to carry a team to do it. I think it's really hard to generalize because each of these is a specific person with a specific life and a story that is rich and deserves to be told. But I do think that if there was somebody coasting and you as a manager have to make tough calls on who you're bringing in which way you're going to bias my profound suspicion, and again, I don't know your friend who you spoke with, my profound suspicion is that person's probably already working hard. You know what I'm saying? That person's already probably working hard. I don't think we changed how hard any individual worked. I really don't believe that.

**Lenny** (01:20:35):
I do think there was a selection bias as to what was going to happen, and I think that's probably what you saw play. In fact, if there is a generality that can be found.

**Lenny** (01:20:43):
Maybe as a last question, I have this segment where I call Failure Corner where I ask people to share a failure of their career and what they learned from that experience. Is there something that comes to mind?

**Andrew ‘Boz’ Bosworth** (01:20:55):
I've failed tons of times. I've built products that nobody used. I've built technical architectures that didn't scale. I've failed all kinds of times. I don't regret most of those. Almost every one of those I learned from. It was a stop on the path to a better solution or it was a recognition that this thing wasn't going to work ever, which is its own kind of a gift. All the failures that I regret, that I take seriously are personal failures where I affected a person in a way that I'm not proud of, maybe wasn't proud of the time because I wasn't in control of my own emotions or mood. I was feeling fearful, I was feeling scared, and there's a bunch of these one or two that stand out that I don't feel comfortable sharing because the person affected, I think would prefer I didn't share.

**Lenny** (01:21:46):
I'll share one that was... I think the person's and I are tight now. We have this really silly discussion. I remember it so vividly. In the early days of client server architectures, which Facebook obviously is a website, so you're calling to a server to get the webpage, but then that server is going to call the other servers to gather things and that was one of the major clients of remote procedure calls because newsfeed ranking was all done on this other set of servers that had its own special requirements and special build and how it was put together. And so your main web server would put a call-out over a remote procedure, call to the remote server and get a response back. And we had this really janky RPC system that, I won't say who built it, but it was built and it was just a piece of garbage constantly failing. It was not robust at all. And one of our best engineers, Mark Sleek, built a new one called Thrift. It was a great, really great RPC infrastructure.

**Lenny** (01:22:47):
And one of my best friends, Dave Federman, one of my really good friends and a brilliant engineer, we were talking about how to do the encoding and I was like, "I want it to be binary encoding." I was like, "You should binary encoding. I want it to be super efficient on the wire," because I'm storing these RPCs. They do two jobs for us, one of which is the active RPC, but I also store the RPCs in a log and replay them to do the work that we were doing in newsfeed ranking. That's how it was done back in the day. It was all kind of asynchronous offline and so I wanted to be as tight as possible. My memory bandwidth was very limited and memory was so expensive back then and Dave Federman was like, "No, no, no, that's short-term thinking Boz, we should be using Linux style descriptors that are plain English language. Then you could look at the log, you can see what it is. It's possible memory bandwidth will get cheaper, but these logs being scrutable to development is going to be a better thing." This is nerd bait.

**Lenny** (01:23:42):
Those of you who have been engineers in this call, this is like Vim EMX. This is nerd bait. This goes deep. This is like a long old thing.

**Lenny** (01:23:51):
I love it. Keep it coming.

**Andrew ‘Boz’ Bosworth** (01:23:52):
It's a room full of engineers at the company and the company's not that big, and so there's probably half the engineers of the company in this room. I was yelling. Literally I'm turning red, I'm sweating. I'm so angry at Dave Federman for countermanding my proposal and I'm the major RPC customer. A couple things. This is so dumb. Mark Sleek just built two encoders. It's not that hard. You pick which encoder you want for your things. That's the easiest solution ever. Second thing is Dave was right, by the way. Within a year, the memory bandwidth definitely didn't matter relative to how inscrutable it was to try to get into these logs. I had to build a ton of extra custom software to parse the logs and understand what what's going on. But also it was a case where my identity was caught up in being right. And for those who don't know, identity threat is just the biggest... Your worst behavior is always going to come out when you think you're under identity threat.

When you feel like some core part of how you see yourself is in question, you will react with every ounce of your fiber to defend that conception of yourself because it's so expensive to reconceptualize who you are that you defend yourself. So my identity was being right. [inaudible 01:25:08] on the wrist. And it caused me to take one of my best friends, one of the best engineers I knew, a guy I literally lived with and getting a really embarrassing for me conflict, which everyone was just scratching their head like, "What is going on with Boz right now?" I looked like an unhinged crazy person. I remember the room, I remember where I was standing in the room. I remember everything about that moment and I had to go home and be like, "What the fuck was that? What happened?" I'm asking myself like, "What happened there?" And that was one of the many steps in the journey to recontextualizing what it was was not to be right and what meant to be open-minded and curious and how to engage in this competition.

**Lenny** (01:25:47):
I was 22. I don't make excuses for it now, but I remember there was a couple other examples like that in things that were less technical and more personal that I won't share, but I remember each of them vividly and those are the real failures for me.

**Lenny** (01:26:01):
I love how this story is so long ago at this point and it's still stuck with you and such an impact, I think.

**Andrew ‘Boz’ Bosworth** (01:26:06):
Oh, my god, I'll never forget that. It was embarrassing. And for those, that's the old quote, it's really one of the truest quotes, and I know it's cliche and sometimes cliches are cliches because they're good. It's like, "People, they don't remember what you said. They just remember how you made them feel." That's all anyone remembers is how you made them feel, and I think in that room, I made people feel unsafe, maybe. It was bad.

**Lenny** (01:26:27):
I like this concept of identity threat. They call this podcast episode identity threat.

**Andrew ‘Boz’ Bosworth** (01:26:32):
There you go.

**Lenny** (01:26:33):
Boz, we started this episode with a billion questions. I have a billion and one questions now. I wish we could keep going, but I know we have to wrap this up. Is there anything you wanted to share or leave listeners with before we get to our very exciting lightning round?

**Andrew ‘Boz’ Bosworth** (01:26:46):
Well, in the off chance that we do end up labeling this episode, identity threat, let me give you what really was... I made a lot of breakthroughs with coaching, learning about the feeling inside of my own body when I was feeling that identity threat and learning techniques and tactics to reduce the likelihood I would feel it and how to deal with it when it happened and how to repair when I did, I went through all that stuff. I would say the greatest lesson I learned would come years later and it was just from observing somebody. Ami Vora who was a legendary, long time came in and worked on our development platform, then worked with me on ads for a long time and then was the PM lead for WhatsApp for a long time. She's since gone on to do even more great things outside the company. Working with her, it was like watching an alien because her and I were so different in our approach and she approached...

**Lenny** (01:27:38):
She could have the most profound disagreement with somebody in the world and they would say the thing that she thought was not just wrong, but crazy wrong and she would respond. She would say, "Fascinating. You have to tell me more about why you think that." And I can't do it justice, she meant it from the core of her being. She saw this schism between her and that person and it could have been personal, it could have been professional, it could have been anything. She saw this schism and how they saw the world and how she saw the world and rather than reacting as if it was a threat that somebody saw it differently or rather than reacting afraid that maybe she was wrong and had done things wrong before, she reacted with the most genuine and profound curiosity. I just watched it absolutely tear down walls between points of view. People felt immediately her genuine heartfelt curiosity and would lean in and that would cause them to be open-minded.

**Lenny** (01:28:36):
And if she was right, which by the way she usually was, then they would leave being like, "Oh, okay, I was wrong about that," but she also would change her mind and that was the key. Ever since then, I really have tried to model that. When I have a strong internal clinch, I try to embrace curiosity like, "Wow, we do not see this thing the same way. That is fascinating. Tell me why you see that." And that can be by personal feedback. Someone's like, "Hey boss, I don't think you talk enough." "Wow, you don't think I talk enough? That is unexpected. I would love to hear more about that because no one's ever said that to me," so I wanted to give that to anybody who might recognize this behavior in themselves. There's lots of things that you can do and you should do that work.

**Lenny** (01:29:22):
The work of improving yourself is always fruitful and satisfying and it pays off, as we discussed, in every aspect of your life with your family, with your friends, and professionally. This is one that I really thought was so great was just curiosity. Embracing curiosity in those moments of challenge has really completely changed my life and I owe that to Ami Vora.

**Lenny** (01:29:40):
Wow, I love this example. It's basically an example of, "Yes, and?", but in a really... no one's going to be like, "Yes, and?" It's a really nice way of saying it, "Just fascinating. Tell me more."

**Andrew ‘Boz’ Bosworth** (01:29:50):
Fascinating. You've got to tell me why, I want to understand it.

**Lenny** (01:29:54):
I love that. Maybe that'll be the new title, fascinating.

**Andrew ‘Boz’ Bosworth** (01:29:56):
There you go.

**Lenny** (01:29:58):
Anyway, with that, Boz, we've reached our very exciting lightning round. Are you ready?

**Andrew ‘Boz’ Bosworth** (01:30:03):
I'm ready.

**Lenny** (01:30:04):
First question, what are two or three books that you've recommended most to other people?

**Andrew ‘Boz’ Bosworth** (01:30:09):
The Dream Machine, which is a tremendous history of pre-history, really of modern computing ostensibly following the life of J.C.R Licklider, but really it's much broader than that, is a tremendous missing piece of history in my opinion. I think in my discipline, in computer science, we were not properly educated. We learned about Alan Turing and we learned about some of the technical underpinnings of computer science theory, but the modern computer and the path to it is a profound and fascinating one, and it has particular resonance today as J.C.R Licklider's observation was human in the loop computing and I think we are now in human in the loop AI, and I think there's a tremendous resonance there. The second one is Good Inside, which is Dr. Becky's book, and again, I think it's a tremendous parenting book, but more than that, it does contain lessons for how we think about our own emotions and how we manage those, which I find to be useful in any context.

**Lenny** (01:31:00):
Amazing recommendations. She's also got an online community for people that-

**Andrew ‘Boz’ Bosworth** (01:31:03):
She has a wonderful online community, she's very engaged in it. And for those parents out there, you're a little early for this Lenny, but you'll get there. Having little scripts that I'm reading on Instagram that when I'm in a moment of tremendous emotional challenge with my children, I have the words handy. They're just top of mind for me. They've been cashed in, right? They're primed, is a big game changer.

**Lenny** (01:31:24):
This will be for our parenting episode down the road.

**Andrew ‘Boz’ Bosworth** (01:31:27):
That's right.

**Lenny** (01:31:28):
Is there a favorite recent movie or TV show that you've really enjoyed?

**Andrew ‘Boz’ Bosworth** (01:31:32):
Yeah. This is super conventional, but Mandalorian. One of the things that's been fun about that is really my kids again is we watched it with my kids, so we had a chance to go on the Galactic Star Cruiser. Again, y'all know I am a genuine and true nerd through and through. Huge fan of Scott Trowbridge and his work at Star Wars service lands in Disney and also of that. And so before that we got our kids who were nine and six and watched all the movies together, and then we were watching Mandalorian together as a family, and it's super fun and it's fun to have that kind of lore, a connection. So it's not just the classic kids movies, but there's something more, and I think for them they feel like it's an adult kind of conversation they get to be a part of. I've really enjoyed that. And I think the world of Dave Filoni and John Favreau and the team that's building that universe out.

**Lenny** (01:32:19):
This is the way.

**Andrew ‘Boz’ Bosworth** (01:32:19):
This is the way.

**Lenny** (01:32:20):
Do you have a favorite interview question that you like to ask candidates that you're interviewing?

**Andrew ‘Boz’ Bosworth** (01:32:25):
One of the most important things that I always ask people is what people who've worked with them would say are their greatest strengths and weaknesses. I like this for a couple of reasons, not least of which is I often do follow up with references and I like to triangulate their awareness of how other people calibrate though. And also how they respond to criticism. Sometimes candidates surprise me. They say, "Hey, you'll hear this critique a lot from me. I don't think it's fair." That can be an okay answer, but they've got to be a pretty robust there. Or it's like, "Hey, this is something I'm working on, here's what I'm working on." But I also like to hear what they think their superpowers are. And too often a lot of attention in interviews is paid to weaknesses, which I care about because I want to know what the downside is. But way more important to me is like, "What are you awesome at? What is the thing that if I can just hitch a wagon and ride, that's what I want to know. Where's the superpower that you're crushing it at?"

**Lenny** (01:33:22):
And what's funny is people are pretty rarely give my reference checks. They're not that often accurate about what the critiques are, but they're usually pretty accurate about what their strengths are.

**Lenny** (01:33:31):
Interesting. I'm also a huge proponent of strengths and not worrying too much about your weaknesses.

**Andrew ‘Boz’ Bosworth** (01:33:36):
But asking people to contextualize their performance through the team, that's so important. We do not achieve very much on our own.

**Lenny** (01:33:44):
Communication is the job. Amazing. Is there a favorite product that you recently discovered that you love? And Meta products are acceptable answers.

**Andrew ‘Boz’ Bosworth** (01:33:55):
The Ray-Ban Meta glasses would be a tempting answer. The multimodal stuff, which I'm going to get in trouble because I've been teasing this for months on social media and it's still a closed beta, and it's like, "We're growing the beta slowly," but it's like, "People already really badly want it." It was probably one of the most magical things I've gotten to try recently. It's not totally fair because it's also not you can buy the Ray-Ban Meta glasses and very soon, I won't say when, but very soon they'll have this capability, but it's more fun to think outside of the box. All right, this is such a... I'm going to get in trouble for this answer because it's a bit of a pretentious one. I'm not a car guy, let me say that right now. I don't like cars. I don't care about cars. I want a car that works and doesn't break. All my cars growing up, had over a hundred thousand miles in them because we only ever had used cars.

They were constantly breaking down and the power steering would go out while you're driving and you have to [inaudible 01:34:43] the thing and the brakes would go out or you'd throw a rod. I've done it all. I just wanted a car. And so then I drove a Honda Accord that I bought for 10 years and then I drove a Tesla Model S for 10 years. And a Tesla model S had a thing happen to it while it was parked, I will get into that. I get a new car and again, I'm like, "I want to get an electric car." And I was like, "I'm going to get something nice. I'm going to get something nice. I want to get something nice." I'm driving a Mercedes-Benz AMG EQS, and I didn't know cars could be this nice. I grew up driving used cars and whatever, I did not know it was possible. It is the best augmented reality product I think you could buy in the market today.

**Lenny** (01:35:29):
With the heads of display, it puts your turn in three-dimensional space. It's got cameras facing your eyes, so it's positioned correctly on this display relative to your eyes, the turn. And so when you come up, it's like you're hitting a little wall, you got to turn before you hit the wall. And I was like, "Oh my God, I think this car has a great augmented reality." Not a car guy, and I'm not trying to flex on this car or whatever it is. I like it a lot. I didn't know they could be that nice, but the thing that I thought was so impressive was they did an amazing job with augmented reality in this car.

**Lenny** (01:35:58):
Wow. Mercedes-Benz, a player in the augmented reality, mixed reality space.

**Andrew ‘Boz’ Bosworth** (01:36:01):
Big time. They're out there, they're in the lead.

**Lenny** (01:36:04):
I sometimes think about having a contest where I give away products people mention in this segment, and now you've blown my budget way out of proportion.

**Andrew ‘Boz’ Bosworth** (01:36:12):
Ray-Ban Metas, you can afford that.

**Lenny** (01:36:15):
That's an amazing, I'm going to have to check that out. I think we're going to increase some sales for Mercedes. Next question. Do you have a favorite life motto that you often come back to think about, share with friends and family, find useful?

**Andrew ‘Boz’ Bosworth** (01:36:27):
Yeah. We have a funny actually how we came about this. The motto my family has, my immediate family, me, my wife and kids is just trust yourself. Just trust yourself. Actually, the reason we have that motto is when we have a house, we have a few nice art pieces and one of them is a Tracy Amen, a famous UK based artist, and she does neon pieces and it says, "Trust yourself." And so it's in our bedroom hallway where me and all the kids and my wife are, it says, trust yourself and every morning the neon lights up and it's trust yourself. And then I had the chance to have a crest made in the UK and my family's English from way back. And so in the crest it says, "Trust yourself." And I always talk to my kids, especially. I really think people, when you're experiencing peer pressure like, "Who do you trust? Them or yourself? When you're having a lot of self-doubt and uncertainty, you have to trust yourself."

**Lenny** (01:37:17):
I just think so much of the success I've had, I think this is probably true of most people who went to startups and succeeded, was like, "I just had faith that I was making good decisions." I mean, this comes back to the conviction point I made earlier about how you do things like newsfeed or controversial things or how you make big expensive changes, just conviction. You have to believe you, your eyes, ears in an intellect have combined to give you a point of view that has intrinsic value and deserves your respect as opposed to reading that newspaper article about your company and believing it over what your own eyes and ears have told you. That's the motto that we go with.

**Lenny** (01:37:57):
And I think it's also important to say you won't always be right and that's okay.

**Andrew ‘Boz’ Bosworth** (01:37:59):
Totally. That's right. Trusting yourself also includes taking risks because you trust that you can deal and handle with what happens when the risks don't pay out.

**Lenny** (01:38:07):
Beautiful. Final question. I know that you're an amateur photographer, maybe semi-pro photographer, a lot of travel photography.

**Andrew ‘Boz’ Bosworth** (01:38:13):
Amateur. Amateur, amateur.

**Lenny** (01:38:15):
Amateur. Okay. You also have this website that I came across that I don't know if people know about it, it's this funny name. I'm not going to mention that. I don't know if you want people...

**Andrew ‘Boz’ Bosworth** (01:38:22):
Warden Shortbow, it's an anagram of my name. Warden Shortbow, an anagram of Andrew Bosworth, wardenshortbow.com. I love photography. I love it. It's a real passion of mine.

**Lenny** (01:38:30):
So here's the question. What's your favorite photo that you've taken?

**Andrew ‘Boz’ Bosworth** (01:38:33):
Art is actually a great place to talk about trusting yourself, by the way. And I know it's cheesy to say it, but I think Rick Rubin's recent interviews on what art is and how people make it is spot on. You have to make it for yourself and you have to love it. And if someone else loves it and it finds broader resonance, that's awesome, but that's not why you do it. And if you start to try to do it for broader resonance, then you're kind of chasing something else. It's media, it's entertainment, but it's not art. It's some other thing. And I say all this to basically tap dance and say, I kind of love a lot of my photos and it's very hard to pick a favorite. The one that is popping to my head, which has more emotional [inaudible 01:39:12] is a picture I took of my son playing in the street and just jumping in a puddle, wearing a rain boot, rain slick kind of a thing. And it's not sharp, it's not in focus. It's a vignette, it's an idea.

**Lenny** (01:39:27):
And I really do think Ansel Adams talked a lot about how the goal of the photographer is to create a capture that expresses to the viewer what it felt like to be there. And people forget that he was a master of the dark room even more so than maybe than the capture, the print. The print was where he did amazing work. And I've had the pleasure to go to his dark room in Big Sur and spend time with his son and watch them do development in that room. And he had elaborate scripts of how he would highlight, dodge and burn different parts of the photograph to get it to have the resonance that he wanted. And he fought for photography to be accepted as an artistic medium, which it wasn't, which I find so resonant in today's AI art conversations where once again, we're trying to gate keep what is art and you just don't get to do that unfortunately.

**Lenny** (01:40:20):
So this picture of my son, no one would call it a technical marvel, but as a vignette of it capturing for me personally, but also I think in general for parents, the ephemerality of these tremendously touching, charming human moments that you have with your children, that's the one that comes to mind.

**Lenny** (01:40:39):
Amazing. We're going to try to find it and link folks to it. And on the point of Rick Rubin, something he says along the same lines is that you think of art as your diary. I am just describing what I find interesting and important and nobody can come to me and say my diary is wrong. It's my diary, this is how I see the world, and that's okay. And that's where the best art comes from is just emboldening to this... there's an awesome video of him saying exactly this that I was recently watching actually. Boz, this was so much fun. I am so thankful we made time for this. I'm looking forward to our parenting and relationships podcast in the future. Joking, not joking. Two final questions. Where can folks find you online if they want to follow what you're up to and how can listeners be useful to you?

**Andrew ‘Boz’ Bosworth** (01:41:19):
Sure. I'm @boztank on Instagram and on Threads and also on X, facebook.com/boz. And I also have my own podcast, which is a technical deep dive, so it's pretty different, I would say. It's a technical deep dives to try to go deep on one or two topics each time. That's called Boz to the Future. You can find that on Spotify or iTunes.

**Lenny** (01:41:41):
Boz to the Future, buy some Quest stuff.

**Andrew ‘Boz’ Bosworth** (01:41:44):
Get yourself a Quest 3. Let's be honest. Dude, treat yourself.

**Lenny** (01:41:48):
There you go. Or these Ray-Ban sunglasses. I'm a big fan. Boz, again, thank you so much for being here.

**Andrew ‘Boz’ Bosworth** (01:41:52):
Cheers. Thanks, brother.

**Lenny** (01:41:53):
Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [15/19] Inside TikTok: Culture, strategy, monetization, and more | Ray Cao (Global Head of Monetization Product Strategy and Operations)

**Lenny** (00:00:00):
We rarely get a peek into what it's like to work at TikTok. What are some core principles or values or just how TikTok operates?

**Ray Cao** (00:00:07):
The number one thing is context, no control. That's the reason why we're always encouraging people to see themselves as a business owner.

**Lenny** (00:00:14):
You give them all the information they need and then let them just do things without specific instructions.

**Ray Cao** (00:00:18):
How do you actually solve the puzzle by connecting all the dots together? Just like how I see some of my friends, their kids playing Legos, if you don't really see the full picture, you won't be able to make the Lego as one thing at the end of the day. You have to see the other pieces.

**Lenny** (00:00:31):
What else are important cultural values of TikTok, of how TikTok operates that everyone always has in mind when they're building?

**Ray Cao** (00:00:36):
We always have this mentality we are a startup, we're a young company, we're always hungry for growth. And a very wacky way is like, "How can I run my second half of my marathon faster than the first half?"

**Lenny** (00:00:49):
Today my guest is Ray Cao. Ray is the global Head of Monetization Product Strategy & Operations at the Global at TikTok where he has been for over four years. Prior to TikTok, Ray spent six years at Google helping scale Google shopping globally.

**Lenny** (00:01:05):
TikTok is interesting for two big reasons. One, it's one of the most successful businesses in history, last valued at over $80 billion. And its parent company is the most valuable private company in the world, last valued at over $200 billion.

**Lenny** (00:01:19):
Two, TikTok is quickly becoming one of the biggest advertising platforms alongside Meta and Google, and generated nearly $10 billion in advertising revenue just a couple of years ago. So for both these reasons, TikTok is a really interesting business and team to learn from. And I've seen very few podcasts and even media get a peek inside how TikTok operates.

**Lenny** (00:01:39):
In our conversation, we discuss TikTok's culture, their core principles and values, how they hire, how they move so fast, their emphasis on working hard, how they do OKRs and planning. We also get into how to succeed on TikTok's ad network, why you want to be testing at least 10 videos a week, how it's different from running ads on Instagram, how to make content that does well on TikTok, and so much more. This episode has a lot of interesting lessons and insights. Obviously TikTok is at the center of a lot of debate globally. Some people love it, some people hate it. But no matter your opinion of TikTok, there's a lot that we can learn from their success.

**Ray Cao** (00:05:00):
Thank you Lenny for having me. It's a pleasure.

**Lenny** (00:05:02):
It's my pleasure. I am really excited to have you here because it feels like we rarely get a peek into what it's like to work at TikTok, how TikTok builds product and operates, also how to be successful in TikTok as a business, as an advertiser. So I have all these kinds of questions for you, and so I'm really happy to be chatting. I wanted to start with a little bit about your time before TikTok, which was at Google and comparing that to TikTok. So, you're at Google for six years, I believe. Now you're at TikTok. I'm curious on what stood out to you about the cultural differences between how Google operates and TikTok operates.

**Ray Cao** (00:05:37):
Three major things, I would say. Number one is really how these two company thinking about innovation. So, I think Google has a very strong philosophy of we're engineering lab and that there's a lot of technology-driven, and a lot of pieces. They are not necessarily always trying to, I would say, cope with the market even, right? However, I think at the TikTok, I think besides the technology part, we do have a very keen, I would say, appetite to really understand what the markets really want and also how can we really service our clients in a better way and the clients here is not necessarily only for advertisers including our user and also creator altogether. So that's one of the things I think it's very different in terms of TikTok way of work. It's very customer-centric in a way, and again, the customer here is not necessarily only for the business partner but also for our regular user and creators on the platform.

And the second one is really thinking about how we take approach on product development. So a lot of times that we take a very rigid approach in terms of product development and oftentimes you see us that experimenting a lot of different things all the same time. And also we do have a lot of engineering and [inaudible 00:07:04] project in the backend to really understand how can we optimize better for the platform. So a lot of time, these are the things that I think TikTok is doing really, really well.

**Ray Cao** (00:07:14):
The last piece I have to say is the approach for global prioritization. A lot of times that you see a US-born company go global and oftentimes still they are really rooted with the US market and there's nothing wrong with it to be honest, because this is the biggest market for them as I would say for East-born company. I think a lot of times that we can take approach with truly how do we think about globalization and for example, we launched a lot of product not necessarily first in North America. We launched it in South Asia for example, for our shopping, really very big initiative internally for shopping and we launched our really creator fund here in North America. We launched our gaming approach, really serviced our EUI gaming advertisers. Really, really strong over there. So there are a lot of different approach in terms of how do we prioritize our go-to-market and also product development. So that's the part I feel like we're very unique in the market or unique to some of that was the tech company born in the US.

**Lenny** (00:08:24):
It reminds me there's this piece by this smart guy, Eugene Wei who wrote a few things about TikTok over the years and just why it's been so successful and one of his really big points is that TikTok can work really well in other markets 'cause it's basically... you don't need to know a ton about the market because it's this algorithm that figures out what people in each market want. Is there anything along those lines you've seen that just has been really fundamental to it working so well in many different markets?

**Ray Cao** (00:08:51):
The algorithm is definitely helping because it is basically the machine is doing a lot of heavy lifting. That's actually I think across the board on a technology company today. The difference is actually how much you are willing to take the heavy lifting over there in the market. By that I mean really sending your troops into the market, hiring your local talent, understanding the culture and really understanding the behavior from those users. I understand the machine can do things, but also at the same time that we need to actually get local talent to fine tune the machine. So there are a lot of conversations about how I would say technology is able to change our life, but I do think that at the end of the day, I do believe technology is a tool.

**Ray Cao** (00:09:34):
So if we do have a ambition to go global, you have to do one more thing is actually take your step into global. Rather than having the machine do the heavy lifting, you have to really understand in local culture. I had a fun background for my first job is to really doing go-to market research in the Southeast Asia area. I think there was only one thing opened my eyes after a year and a half in this career path is different market have totally different, I would say, culture and these market behaviors are actually coming out of this culture. One of the fun example I always been using was I was doing market research for one of the suppliers for toner and also these ink cartridges for Thailand as a go-to market research. One of the things is always concern to my, at that point, the client was they cannot figure out why their premium product cannot sell in Thailand and then we just figure out because the quality of their printing machine and also their ink cartridges are premium and the quality of the paper and everything is very good.

**Ray Cao** (00:10:51):
But when you actually do talk to those consumers in those market, the answer is very eye-opening. They literally told me at that time is I don't care. I don't care if your ink cartridges or your printer is at the premium quality, maybe the printer I can use, but I can use compatible ink cartridges or toner for that because my consumer won't care about your printing quality or the majority of my consumer won't care. So in that case you should not necessarily worried about if you are a premium product, it's actually more about how durable, how reliable you're able to print things and people can read.

**Ray Cao** (00:11:30):
So I think these are the insights I think a lot of times it will be neglected from some of clients or the manufacturers or even the owner of the business because they think that we want to serve this segmentation, but, however, this segmentation is that big in this area. So that's reason why the culture is really the key part from the market. If you don't understand the culture, you won't be able to understand the behavior over there. It's more about that, I think, when we say about globalization or take the product go to market in a global scheme or even build it apart, you have to get your hands dirty and to really understand the local culture so that you can understand local behavior.

**Lenny** (00:12:16):
I love that advice, the way you described it, which I love also is that you kind of have to fine-tune the algorithm and the product to work in different cultures. Is there an example of how that was done with TikTok, like a tweak that had to be made or some kind of fine-tuning that happened for it to work in a different market?

**Ray Cao** (00:12:32):
Yeah. I think we did a lot of fine-tuning on our user product side to really think about content. So that's the number one thing going to be super different coming from each of the market and also from each of the culture. For example in Japan, how do you actually get more content that relevant for the culture? A lot of people may think, okay, are you guys only doing dancing or doing singing for Japan? The answer is not. It is actually more food on the TikTok side, like how do you actually introducing new food restaurant or new recipes and also sometimes that you're introducing a new technology. I would say 3C like consumer electronics product over there. So these are the content get really popular sometimes in Southeast Asia or even Japan area and versus in the US as everybody knows that we're starting from really lip-syncing at a very early stage but now really we're expanding to shopping behaviors and also a lot of people using us as a main platform to acquire new discovery for the product.

**Ray Cao** (00:13:40):
So these are the things I think different market definitely deserves and demand different kind of treatment and if you are able to do this a lot, you're able to find success over there.

**Lenny** (00:13:53):
That's really interesting because you could think it's just this algorithm that figures everything out for you, but I think what you're pointing out is you have to seed it with the right sorts of use cases that that culture is most excited about.

**Ray Cao** (00:14:04):
Another good example will be creative, so it's a very good example how human can work with technology together. We have a ton of creatives and we have a ton of content so, of course, we use machine to label those content use metadata to analyze those content. However, a lot of times you can find that when we're really thinking about how creative can help advertisers? Humans actually make a more interesting or more, I would say, influencing decisions over there. For some of the verticals we can say that, "Oh, you know what, maybe we can try a coupon image with a new product like a sticker on the top?" This maybe actually work better compared to some of the price promotion even. So a lot of things really depends on how do you actually interpreting the numbers and interpreting the data points but also at the same time your business acumen is going to be very important here to make a judgmental call for some of the situation like that. I think we're still rely a lot on both machine and also our own experts to analyzing those trends and give it the recommendations.

**Lenny** (00:15:11):
Awesome. Okay, so there's a few threads I'm going to follow later. You talked about the product development process, so I'm going to want to spend time there, also about how to be successful in TikTok both as a creator also as a business, I'm excited to hear your advice there. But I want to spend a little more time first on just what it's like to work within TikTok and the culture of TikTok. What are some core principles or values or just how TikTok operates if you had to identify, here's the ways that we all think about what we want to do and the most important to your day-to-day work, what words and concepts come to mind?

**Ray Cao** (00:15:43):
The number one thing resonating really, really well with me is context, no control. Oftentimes when we are looking around companies different sizes, we're looking at how to collaborate. Oftentimes we see the behavior that a lot of people just working on a smaller piece based off their job description. So hey, you're working on go-to-market and you're working on data analytics, and you're working on this book of business and commerce, and you're working on auto industry for example. A lot of times that these human-made silos is actually slowing things down because humans are not, or our talent, they're not supposed to be categorized into different basket. They may have their own majority responsibility for sure, but we don't want to cap them into this kind of a box we created. That's really why we're always encouraging people to think out of the box and think more and think themselves as a business owner rather than a piece of machine that keep the machine running.

**Ray Cao** (00:16:49):
Oftentimes that will say context, no control. That means you actually can go above and beyond to really think about your whole business problem as your own problem and your piece is maybe one part of it to solve the puzzle, but how do you actually solve the puzzle by connecting all the dots together, we're encouraging all the people to think like that way and by that I think we kind of mentally break out those walls. So encouraging our team members to do a little bit more thinking is very important. It's a little bit more thinking because the think part is very important.

**Ray Cao** (00:17:23):
And then, now in terms of getting things into behavior or changes or getting to action, then you need to really collaborate with other teams because we don't want to necessarily creating, hey, you're on other people's working group now you're actually stepping on other people's toes now. It is not the situation we're trying to encourage in, but where it's encouraging more is context, no control, think more about how you can change it and then we you do really actually take some actions, be active. You reach out to who's supposed to be the owner of that and then have a discussion so then you you're able to connecting the dots altogether.

**Ray Cao** (00:18:00):
So that's one thing I think it's very unique to our culture. I think it's very, very important for us to continue to grow at this speed because everybody have a, I would say, full visibility towards our full ownership to their mindset, how they can contribute.

**Lenny** (00:18:16):
And the key there is context implying you give them all the information they need and then let them just do things without giving them specific instructions, "Hey, I need you to hit this goal, work on this project, launch this thing. Here is what we know, do the things you think are best, roughly." Right now, I know it's not just like anyone does anything, but I imagine that's kind of the implication there.

**Ray Cao** (00:18:35):
Yeah, I think it's context, no control plus proactive thinking and reactive doing so you have to do more proactive thinking with these contexts. Now reactive doing means that you need to collaborate, but when everybody has this kind of mindset, the collaboration should be very smooth because people have the context altogether. The part that I see maybe some of the other company are facing challenges is actually there's too many IOs in between and you have people that are just protecting their own thing and working their own thing and then I'm delivering. But just like how I see some of my friends, their kids playing Legos, if you don't really see the full picture, you won't be able to make the Lego as a one thing at the end of the day. You have to see the other pieces. So that's the part I think it's really powerful and reasoning really, really well when we're really thinking about product development and also product go-to-market. So it's a pretty full cycle. People have to see this and then they have the context.

**Lenny** (00:19:35):
I love this, and this has come up actually a few times recently when I was talking to the CTO of Netflix and also OpenAI. They're very similar in culture where it's give people a lot of autonomy and freedom and not a lot of do this, do this, do this. The key there is to hire very high quality people and very high caliber people because if not, then things won't work out too great. Is there anything along those lines that you can share just like yeah, the kinds of people you end up hiring and how you hire people that can work well in that environment?

**Ray Cao** (00:20:05):
I agree with you. So the caliber of these people is actually pretty important to support the structure I just talked about, and oftentimes I can see some people that with the quality of always curious. Curiosity is a very important quality when I'm actually talking to my interviewers because I want to see that they are naturally curious to new things. They want to learn more about the new things and don't really get stuck with their own things. That's one thing. And the other thing is the discipline because like I said, it is actually a double-edged sword in this case. So it could potentially introducing some of the chaotic situation in a company because everybody is thinking everything. The discipline here is actually how you are really following the guidance on reactive doing, be always thinking about how to collaborating, and the discipline here and also the rigorous approach here is also going to be very important.

**Ray Cao** (00:21:07):
One of the good example that is the ability to prioritize because I don't believe one thing is everybody can do everything. You have to prioritize properly so that you're able to push the right agenda. So I think that's more of the quality of the people we're looking for is... it is hard, don't get me wrong. It is really hard to say that we can find everyone like that, but we would love to believe that we can train our employees like that so that they're able to even do better in their longer-term career.

**Lenny** (00:21:38):
Essentially what you look for when you're hiring people is making sure they're always curious, they have high discipline, and that they prioritize well. Coming back to the cultural pieces of TikTok, so the main one you've shared so far is this idea of context, not control. What else are important cultural values of TikTok, of how TikTok operates that everyone always has in mind when they're building and new meetings, making decisions?

**Ray Cao** (00:22:04):
Yeah, another internal thing that we always say is always day one, we want to make sure that we always have this mentality we are a startup. We are a young company. We're always hungry for growth. We don't want to fall into the trap that people may think, "Oh, you guys are very successful in the market and then you are not necessarily need to worry about your existence anymore." I think it is actually something we're trying to avoid. We always want to make sure that in our team members always think like, "Okay, if this is actually a new day for you, I know what other things that you always want to keep in your mind you want to do." And also to keep that spirit is very important.

**Ray Cao** (00:22:42):
A lot of times that I can see some of the mature company, they're not necessarily losing the edge of, I would say this competition or losing the edge of being innovative. I think it's more about some of the culture has been shifted because you have a lot of new employees that live in your culture. So not necessarily it's not going to be like the old days that the co-founder is sitting among you, but I do think this company has a very interesting behavior. I see there is I can talk to anyone at any time via our internal communication system. I can ping Shuo right now. I can ping the co-founder if I want to tomorrow.

**Ray Cao** (00:23:24):
We always keep this kind of mentality internal is that we're still a young company, we want to grow and you can feel free to talk to anyone. We don't have a limitation for that as long as you have a good opinion, I would love to hear from you. Is that creating some of the, I would say chaotic situation? It might be, but I do think that this keeps the company very energetic. People are willing to share, people are willing to engage. That's very important.

**Ray Cao** (00:23:50):
I want add one more thing. We just talked about, you asked me what is actually the uniqueness of TikTok versus the other company. It's very tied up to that is I have never seen a company, the engineering team and the product team and the sales team are so close. That's definitely one of aha moments I had because if you're thinking about if your engineer does not really know what the market wants and if your PM doesn't really know what is actually the client's feedback, they won't be able to get a right product in the market. They just won't be. And they won't even tell a good go-to-market story to advertisers or even to our users because they just don't know what the end users are thinking.

**Ray Cao** (00:24:39):
So I think it's a very secret sauce for us is that our sellers and our engineering team and our product team and also data scientist team, we're all collaborating really, really closely and that's very much, I would say a such big advantage for us compared to when a company becomes too big and nobody talks to each other. So I do hope that it is the thing that we're going to continue reinforce along the years where we'll continue to grow the company.

**Lenny** (00:25:09):
What does that actually look like? I imagine people hearing this are like, "Yeah, we're going to make sales and product and hinge very close." I imagine many people don't actually do this too well. How do you actually execute that? Is it they report to the same leader, they sit next to each other or I don't know, zoom next to each other? What actually makes that work?

**Ray Cao** (00:25:28):
Yeah, I think a couple of things. Number one is a structure. Everything has to go at a structure. So we do have a meeting structure that we called it... it used to be by month and now it's actually a quarterly level. We get everybody together, engineering leader, product leader, and also not necessarily only the leader level. Some of the team members, we're joining the force together to have a big meeting. That meeting is 180 people-ish. It's crazy to have a meeting at that size, especially that there are different kind of functionality there. But one thing we keep really well is actually we are using a reading format of meeting. So it's a doc reading. We just read in comments and understanding the context again. It is the doc, bring everybody together, and then we discuss the things that we want to make a decision with or the things that we feel is a blocker or things that we need to celebrate.

**Ray Cao** (00:26:24):
So that meeting structure keep everybody together and consensus, again, not necessarily only for the top leaders. It's normal for the engineering leader and product leader and sales leader at the company level, they talk to each other, but we made that happen for their core team members. And the very beginning of my time here, that was literally getting to the IC level. So it is pretty eye-opening for me to join that meeting first time because I was get so used to their level of different meetings at Google, but here it's like, okay, everybody read one documentation and then you just understand what are people talking about or thinking about. It is intentional. But I do think that that structure is a very big secret sauce, I would say, not necessarily we invented it, right? We also learned from the other companies. So it is actually one of the things that we actually deployed pretty well today here to keep that structure running.

**Ray Cao** (00:27:22):
And the other thing is really feed those, I would say, first-hand market information to our PMs and RDs. That means we took them out with us. We're just inviting them together to join the force together to meet the clients and a lot of the company, if you want to meet APMs, if you want to meet the engineering leaders, it's literally once a year maybe, and also if you're investing a ton with some of the platforms. For us, I think it's always on to junior PMs, senior PMs and engineering leaders. We invited them together to these immersion trips recorded to really get face time with our clients, to really feel the heat. They are actually really facing a challenge by using our own product.

**Ray Cao** (00:28:07):
So that kind of, I would say, the aha moment is bringing a lot of, I would say, insights to them and also get them to feel the heat of the pains the sellers may feel. So that worked really well, too. I think oftentimes it is a battle. It is not necessarily the general, you have to stay in the back, you sometimes have to go to the front, but we just make sure that the general go to the front quite often in our company to do that.

**Lenny** (00:28:36):
I love that concept of having them feel the heat. An interesting trend I've noticed is there's a lot of Amazon influence on the way you all operate. It's always day one idea. There's the memo culture you just described. Any idea where that comes from? Is there like a senior Amazon person that came in and helped influence those sorts of things? Is it just hey, Amazon's killing in there? I've noticed interestingly, Amazon has influenced the most companies in all of their ways of working, so it's not a surprise. I'm just curious if there's anything else there that's interesting.

**Ray Cao** (00:29:04):
I think we have the benefits to standing on the shoulder of all the giants. So we learned definitely always there when the culture that Amazon was always championing, I think we learned from them. So this is something that we, I would say, always trying to listen and trying to learn from industry. The dark fashion is also learned from Amazon, so we kind of studied, oh, this is maybe one of the best practices we can employ here, how we deploy here. So we tried it, not even mentioned we have the OKR system, so it is actually a very good learning from our early stage from Google. So all these, I think definitely we do have some of the, I would say, benefits being the newcomer to the market and then learn a lot of the best practices coming from our industry peers and really deployed here hopefully successfully.

**Ray Cao** (00:29:53):
And some of the things that we just tweaked. So for example our culture always day one is definitely very similar to Amazon, but the implementation of that could be different. And also the context, no control piece is, I believe other companies may have the similar idea, but for us I think we just really need to implement it in a way that's going to be fitting to us. I happened to listen to your podcast with the Airbnb co-founder the other day. He also mentioned that how he break out the IOs. I think it is very similar approach among industry right now trying to really make sure the team is able to talk to each other because I think a quote from him, "If your PM doesn't know how to sell the product they're creating, you won't be able to do your job better." So this is literally how we're thinking about it, too, in a lot of way.

**Lenny** (00:30:40):
I know that you all move very fast and I want to actually talk about that next. And with that it feels like your value should be, it's always the first half of the day instead of it's always day one. It's always the morning of the first day.

**Ray Cao** (00:30:53):
I think the value, if I put it in a very reactive way is, "How can I run my second half of my marathon faster than the first half?" So that's how I think about it and how do we really continue pushing for it.

**Lenny** (00:31:09):
Wow, that sounds very hard and painful, but I like that metaphor. Okay, so let's talk about how you set up the product org to move as fast as you move. I think there's this idea of just running fast. I don't know if that's a phrase you use, but just how is the product org set up, especially different from other teams that you've seen that allows it to move as quickly as you move and innovate as often as you all innovate?

**Ray Cao** (00:31:34):
Our product teams are setting, I would say, very importantly is global. So we want to actually, like I said, the number one step is if we really want to do global business, we have to go global. So we set up teams really across the board in the global locations to really acquire global talent who knows the market and who knows the competition, too. So we're able to really getting the, let's say jumpstart, in the local market. So for example, we have the majority of the engineer and also PMs currently located in the west coast of North America, so Los Angeles and also San Jose. These are the key hubs we have for our tech folks and also for North America wise we do have our majority of the go-to-market leads sitting in New York to get closer with our seller and also with our clients at the same time.

**Ray Cao** (00:32:27):
Also, it is not necessarily only for North America. Like I said, we heavily invested in Southeast Asia, so you can see that a lot of our engineering and also PM resources are deployed over there in Singapore to enable them to get closer to our clients over there as well. So really deploy your resources globally and also focusing on the key markets you want to penetrate. That's the commitment. I think we're doing pretty good in this case. And the second one is to really, again, I think the PMs and the product team of settings are oftentimes I would say because we're growing so fast, oftentimes we have to do a lot of minor team adjustment to catering for that. So it is very usual or common for teams to do a little bit of work on an annual basis or even on a two years or three year cycle. The stability is important, don't get me wrong, but I do think that as a faster growing company, we need to consistently to reiterate not only the product but also our teams.

**Ray Cao** (00:33:33):
So how can we do reiteration on the PM side, on the go-to-market side, it is actually something that I have seen this company doing really, really well. Not necessarily we're bonding to one team structure. We're actually bonding to the market need and we're bounding to the growth we're looking for. So we're not afraid to break our seams. And actually I literally break out my team last year to make sure that my team having more go-to-market mindset to actually embedded them with seller directly. So these are the things that very, I would say conventional to a size of this company, but I do think that's necessary and also that's a good mentality for the team to really run faster with this kind of a rigid approach. So yeah, these are the two things I think very unique to us, I think could also be continuously helping us in the next phase of the growth.

**Lenny** (00:34:33):
**Ray Cao** (00:35:51):
Yeah, when I joined the company, there were only two people on the go-to-market side.

**Lenny** (00:35:57):
For the advertising business.

**Ray Cao** (00:36:00):
There are only two people and by that time the US and plus, I would say, Europe business together, we're having less than 80 people, but the business needs to grow and we need to hire really fast. The first mistake I made was... By the way, the goal is to hiring 100 people in a six month to support the go-to-market. That is the speed we're into. So that is early 2020 to middle of 2020. So within six months I need to hire, I would say, 100 people to supporting the global go-to-market structure and build everything. Then the first mistake I made just at the right point because we're trying to grow too fast and sometimes as a hiring manager I have to compromise the standard we're trying to hire. So that's the mistakes I think I made first and I think nobody should repeat that mistake is you need to always run for the quality rather than the quantity. So it's a easy mistake. You can fall into the trap because the business demands you to go faster. If you don't have the manpower, you won't be able to.

**Ray Cao** (00:37:11):
But I would say, believe me when I say this, this is a pain, right, when you have the wrong people on the team, it's not necessarily going to make you move faster, it's going to actually slow you down. So that's one of the biggest mistake I made for my first year when I created the team and not necessarily myself only. So also the managers reporting to me, they're facing the same pressure and then it's cascading down. So it's definitely the mistakes we made at early stage.

**Ray Cao** (00:37:43):
The second thing I can think about is really on the context, no control. It is not necessarily I'm born into, to be honest, because I was trained really like, "Hey, this is your box, finish your work here and then you're good." But the reason why I value that really the attitude more today is literally I failed at the very early stage of my time here because I was trying to creating that kind of a very black and white discipline for my team, "You can do this, you cannot do that." But technically speaking, that's literally slowing things down because a lot of times you can see that, "Hey, we're delivering our go-to-market strategy and we're good." But literally what you don't know is your goal is not to deliver the go-to-market strategy. Your goal is to land your go-to-market strategy with sales together. So if your job only is delivering, no, you're failed oftentimes because you're not really getting the market context, you're not even talking to your clients. So that was literally another mistake I think taught me how to really embrace the culture. Here is context, no control.

**Ray Cao** (00:38:52):
And the third piece, I think, it's also a mistake, really a hard moment for me as well is, for the past couple of years now, I've been managing a such big global organization, oftentimes even not myself, my managers, they don't have time to go detail and to go talk to the clients, which is very scary because again, if you don't know, you don't hear what is happening in the market, you won't know the details in the market, you won't be able to take the right movement or take the right approach to go to market or even give the feedback to the engineering team.

**Ray Cao** (00:39:32):
So it's very important that the leader at any level needs to be situational. You cannot always down to the wheat and you cannot really distance yourself from the reality. So you need to find the balance to really get engaged and also see yourself out there to getting, I would say, getting deeper into the problems, to identify the problems, and then you're able to perform even better. Because I don't believe one thing is you are the pure, I was the people manager. You cannot do that because when you do that, you're very, very at the very, I would say, position to really thinking about your career because you're losing your competitive edge from the other, I would say equivalent talents in the market.

**Lenny** (00:40:18):
I love these stories. I love stories of things not working out, so I appreciate you sharing these things. When someone doesn't work out at TikTok and they have a bad time and they get let go or they leave, what's the most common reason other than just they're not good enough? Is there something that just doesn't stick with people that often leads to this is not the place for me?

**Ray Cao** (00:40:36):
Yeah, I would try to really thinking about this in a different way. I can tell how people can be more successful here. So I definitely can see we're just talking about people being very curious and people are very, being nimble. They can be more successful here. At the same time, I think we have to admit one thing, join a start-up and join a rocket ship is a lifestyle. It is not necessarily a job you are working on from 9 to 5. So it is a different lifestyle and it is not built for everyone. So if you are not able to adjust your mentality towards some of the work that we are here to do and it's maybe not right fit for you. I'm not saying that that candidates is incapable. I think they could be capable in the other scenario for sure, but is the right fit? I think that is, I would say very much towards the situation or the company status in the market.

**Ray Cao** (00:41:33):
I can see a lot of people that they left and become very successful, too. So it is not necessarily that, "Oh, we think you're not good and then you're going to be not good for every single other company." That's not the case.

**Ray Cao** (00:41:46):
And one thing, and also this is my team culture I try to create is, I'm happy to say that when an employee reach out to me, say, "Hey Ray, I'm actually leaving the company," as long as they're telling me that they're going to a better place or a place that they can continue to grow their career, I'm happy for them because oftentimes my last question during my interview is, "What is actually your goal in the next three to five years?" And also I'd be really honest with them, say, "Hey, I don't think this is the job for you forever. Nobody going to work in this forever. If you can, great. But what is really your North Star?" I think that's the part that I would love to co-partner with you because I always believe one thing is it is not only about achieving the company goal, it's also achieving really the career goal or your employee's career goal together.

**Ray Cao** (00:42:41):
So I want to creating that culture here as well. So yeah, I think I'm doing so far so good. Most of my team members when they actually are moving on internally or externally, I'm able to say that, "Okay, that's a good choice. If I were you, I may probably do the same thing." It is actually a very good culture, I think, I would love to champion across.

**Lenny** (00:43:03):
On that first point, I'm also a huge advocate of just, "You'll be successful if you work very hard." I know there's a bit of a backlash at working along and thinking too much about work-life balance. And I feel like it's actually really important to work a lot and work long hours often to be successful, especially at a company that's going through this 'cause that's not going to last forever.

**Ray Cao** (00:43:22):
I think at the end of the day it's a personal choice. It's very much like a personal choice. If you are excited about this, if you want to grow together, yeah, this maybe is a good thing for you. And also depends on the life stage. So some of the people they want to actually getting more family time, I think that's also the right choice, too. But it just depends on your, I would say, your personal choice rather than if the company demands that. I mean, I cannot force my team to working long hours. I don't want them to working long hours. I think it's more about if you are able to deliver, right? If it requires a bit, a longer time to contribute, I think it's okay, but you'll also get rewarded very well too. So what's get in, what's get out. So I think it's, again, I do believe that this is the quality and also the value we're evaluating here as well.

**Lenny** (00:44:19):
And even though it's hard in the moment, I find that those are the times you remember most and most fondly in your career, when you just go all in, "I'm going to work really hard and do the best possible job I can do." Assuming that doesn't last forever, those end up being the most impactful, helpful to your career. Most proud moments when you're just like, "Look what I had accomplished." And so I'm on the same page. I want to talk about being successful on TikTok as a creator, as a business, as an advertiser. But a couple more questions real quick on how TikTok operates. You mentioned you do OKRs just briefly, is there anything that you've learned about being successful doing OKRs within TikTok? Maybe is there anything different that you all do versus how other companies think about OKRs?

**Ray Cao** (00:44:59):
It is definitely a company alignment that we are using OKR as our basically the system to make sure that everybody is working towards the same goal. I think definitely we have a lot of room to improve. So how often do you actually see your team able to go to OKR at the end of a quarter and also putting OKR really two weeks or one week before the beginning of a quarter? I have to say that shame on me. I sometimes delay it a little bit, but I think the goal is always there to using OKR system as our North Star to drive the behavior and also to align. Again, it's very important to align on the OKRs because I can see a lot of times the OKRs are putting in, but they are very siloed and that is not really necessarily helpful for the company want achieving really high growth. So I think it's very important that we know we don't take OKR as a shell, but we take OKR as its core is cross-functional alignment, cross-functional goal silo. So these are the things we're still continuing improving.

**Lenny** (00:46:06):
Is the way that OKRs work at TikTok, is there an OKR per team and they all kind of trickle up to a company level OKR? Is it less structured that way and teams decide if they want to use OKRs or not? How does that roughly work?

**Ray Cao** (00:46:17):
The structure is, basically the guidance is, using the key result to evaluating and then you put the steps in between. So that's how at least my team has been using this. I think the things that we can improve is the input and output. So the output is very clear, but what is actually the input sometimes is debatable, sometimes I have to say. And also oftentimes your output is other people's input. Are you able to connect the dots over there, too? Then that's actually the part that requires a lot of, I would say reinforcement alignment. Definitely we're getting better, don't get me wrong. We're totally not perfect, for sure. But I do see there is a lot of, I say momentum, to leveraging the system better. If you know other companies doing this really, really good, please shoot them my way. I would love to learn from them.

**Lenny** (00:47:07):
One last question here. You do planning, you have OKRs. Just briefly, how often do you all do planning? Is there a yearly plan that you put together and then a quarterly detailed plan?

**Ray Cao** (00:47:16):
Yeah, we do have annual planning cycle, but I have to say that our annual planning cycle is the baseline. We often do a lot of iterations in the middle of the year and also on a quarterly basis that we're able to pivoting really nimbly to really catering to the things that we see in the market. Some of the longer term strategy won't change, just like the platform we want to always creating, inspiring and also frictionless and immersive experiences for users. This won't change, but anything into the core of how do we realizing that you're always a consistent experiment over there. I cannot speak for the user product side, but at least from advertising product side that this is always the approach we're taking. And for the go-to-market part, that's also creating a very different behavior for us because oftentimes if we have a solid and kind of a static product roadmap, you can do go-to-market relatively easy, I would say, because everything is planned. But with a environment like that that basically make the go-to-market and also the product feedback loop much more short and faster.

**Ray Cao** (00:48:23):
So there's a lot of, I would say, pressure or actually put it nicely, there was a lot of innovative things that on the go-to-market side. Also on the sales side, the company or the teams need to actually do to make sure that we're able to catering for that. But again, this is a teamwork rather than only one side of the work. So far so good, I would say. A lot of things that we've been able to achieve within the past couple of years has been already proven that this approach has been working for us, but not necessarily they're always is perfect already, always room to improve, to make sure that we have more structural approach as well so that the market able to keep the pacing with us. We don't want to overwhelm our advertisers or our users either. So that's also the other part that we need to continue optimizing, too.

**Lenny** (00:49:12):
Okay. Let's talk about a different topic which is being successful on TikTok. So the way I think about it in my head is, there's how to be successful is just a regular human creator person. How to be successful as a business, trying to just create viral content and then being successful as an advertiser, which I know is where you spend a lot of time. So let me just ask, is there a tip you could share for someone to be successful, say aka go viral on TikTok? I imagine your answer will be just produce something people love and want to share and like. But I guess is there anything that could be tactically useful when you're creating content in TikTok to help you go viral?

**Ray Cao** (00:49:47):
I think if I know that I definitely will already become a very successful creator, I have to say. Our system is very much smarter than I am. I cannot trick the system, but I have seen a couple of good cases. So number one thing is that you have to really be unfiltered. I mean, you don't really need to be perfect on this platform. I mean that's the beauty of it. You can be yourself, you can really share the things that you like. And if you're really master at one thing that you're really, really good at and you want to showcase, this is the platform for you to shine because not necessarily that we are fully saturated and also all algorithm distributing the content in a very different way. Some of the other platforms they are, I would say like a people-based or friend-based.

**Ray Cao** (00:50:32):
I think for us it's purely based on actually you're creating something that everybody want to see. So let's see if we can distribute it more. So I think continuously to bring new content to this platform and testing and finding your own competitive edge going to be very important as a successful creator. And most of our creators have been doing that. And I can see some of our biggest TikTok stars, they're literally practicing this every single day. And I do think that creativity and that part of, I would say, getting the nuances is the key part that to be more successful on the T TikTok community.

**Ray Cao** (00:51:11):
And the second thing is it's including also for brands as well, because I consider brands as our creator as well. They really need to embrace the culture and the community here to really listen and understand what are the user behaviors on the platform to understand what do they like to see. And also the messages or the presence could be very different from your other media channels, or as a creator, it could be very different from your other, I would say, platforms.

**Ray Cao** (00:51:40):
So that's the other thing that it's going to be challenging because for them to shift in the mindset. But I do think that definitely was trial. Some of the, I would say, our early adopters has already been proven that when you do embrace the culture here, you're able to acquire a ton of different kind of a user or the audience to your channel and you can show a different side of yourself as well. So yeah, I've been trying to do that. I have not really finding my competitive edge I have to say, but I'll keep trying.

**Lenny** (00:52:14):
Is there an example you could share of someone that has done that really well, either be really authentic and also embrace the community of a business specifically that has done this really well and has taken off not as an advertiser?

**Ray Cao** (00:52:25):
There was one creator I remember called Sheba. She's a singer and she is able to caught my eyes because she was able to basically rap and also during some of the songs cover in a very different way because she's a minority and she was able to basically using her minority identity as actually everybody was thinking, "I'm supposed to be doing Bollywood music, but actually, you know what I'm not. I'm doing a lot of very just hip hop and also the music that people may think like I'm not good at."

**Ray Cao** (00:52:59):
So it is pretty fun to watch that kind of a comparison or the contrast between a creator and also she's able to put a lot of original music on the platform to really inspire more people to do the same thing. There's another music, I would say TikTok creator. So he was pretty big on the other platforms, but the total approach from him is he's basically changing the lyrics, make it very relatable as a personal life. Because for example, he can totally change the lyrics from a old Backstreet Boys song or Nsync song to make it related with his daily communication with his wife. Make it really relatable and fun. So these are the things I think is very unique to us. If you are able to test and find something new like that, you're able to find a new batch of audience and even go viral on the platform.

**Lenny** (00:53:49):
So then switching to the advertising network, a lot of listeners here are thinking about, I imagine, advertising on TikTok. There's kind of classically been Facebook and Google are the two places to do run paid ads. Paid ads are a huge growth driver for tons of companies. It's one of the easiest you could say, or one of the most traditional way to grow. TikTok obviously is emerging and has already emerged as one of the newer advertising networks. So there's a lot of people thinking about how do I succeed as an advertiser on TikTok. So what advice do you have for people? One, who's it best for? I imagine TikTok isn't the best place to advertise for every sort of business. So what sort of businesses are best aligned to be successful on TikTok? And then just what advice can you share to do well as an advertiser on TikTok?

**Ray Cao** (00:54:37):
Yeah, I see a lot of really different type of advertisers already find their success on the platform. One thing that they actually can do that is really due to a couple of things that they're doing. Number one is, like I said, they're embracing this platform. They actually do a lot of things is TikTok first. I have a couple of advertisers. They have actually creating their own internal creative team just dedicated for TikTok. So they actually produce a ton of creative every single day to actually test and learn to understand the platform and understand the community they are engaging with. So I would say leaning in is the first part. It's harder, but it is not that hard. As long as you try it, you'll feel that every single day is getting easier. And also we make a lot of tools to make things easier for them as well. Like creative, we have also a lot of resources on the platform, the creative hub and also we have creative analytics to help you. So these are the things that we're able to basically help the advertiser to leaning in more.

**Ray Cao** (00:55:42):
The other angle to leaning in more is test and learn. A lot of times that people don't know how to really run ads on this platform. Google is very much search, like search fronts. They are really leading on the intent graph. And Meta is really on the people graph they're making. I mean TikTok is the content graph. It's very different, I would say machine compared to the other two. And it requires different way to optimizing and to leveraging the tools we have. So if you're applying the same logic from Meta or Google into TikTok, not necessarily you'll be able to see a great success, I have to say.

**Ray Cao** (00:56:27):
So you have to really get to the detail and to learn how you're operating this platform at the very beginning. Of course, like I said, we're trying to make things as simple as possible because we strongly believe that an advertiser's job is to taking care of their own business and our job is to service them. So we definitely make things a bit easier and along the way, but still it's a little bit learning for advertisers to change their mindset when they engage with us the first time. And I can see that again, for example, last Q4, I can see a lot of advertisers taking this approach to really listen to us and understanding what is our best practices. They actually see a very successful Q4 on the platform. So I do think that if you want to do more, just do more test and learn with us and to really understand the impact from TikTok.

**Lenny** (00:57:17):
Just to understand this point about versus Instagram, I think a lot of people probably run on them on both platforms and try to see which one's working better. Your point is the same content won't work as well on one versus the other. So just so people understand what the main difference there is. I know you talk about there's the friend graph versus TikTok just spreads it all over and anyone can see it. You don't have to be friends and it's really good at getting content out. So what is it that you would do differently if you're making an ad video for Instagram versus TikTok?

**Ray Cao** (00:57:44):
I think the TikTok video, it's more about the backend settings, right? So how often do you actually changing creatives? I think for us it is actually pretty... you want to actually test more creatives on this platform and see which one is actually working. And then we also have really detailed guidance on how do you set up your campaign structure to make sure that you're able to be more successful on the platform. So these are, I would say, the basic hydrangeas we talked about. You can see these guidance are very different from what Meta has today or even Google has today because we're just basically different platforms. And oftentimes you can also hear that we requires a bit more real time react on the platform due to some of the trends we have seen.

**Ray Cao** (00:58:30):
So that is the part I feel like if advertiser wants to engage more with really the sales team and they're able to provide more guidance to you and you're able to see more success there. But a lot of things will be counterintuitive I would say, because the intuitive you have learned is coming from the other platforms, but technically we're not. So a lot of things that, "Oh, this doesn't make sense to me, but why don't you try it?" And we make actually that really easy because we are sharing a lot of, I would say added credit to intensify incentivizing our advertisers to try it at the end of the day that hopefully they can see the result is proven itself.

**Lenny** (00:59:11):
Got it. I think that's such an interesting point, this idea of testing more, which basically you're saying with Instagram certain people will see it and that's not going to be shown tons of random people. So you basically have one shot at getting this in front of the Instagram crowd versus TikTok just tries it, this explore and exploit kind of approach is like, we'll just keep trying stuff until something sticks.

**Ray Cao** (00:59:33):
Yeah, I think exactly like that 100%. I think a lot of times that I think advertising, especially when digital advertising becomes a thing, so we kind of think everything can be calculated because you have the data, but the beauty of advertising is never like that. The core value advertising is to tell people don't know you exist and tell them that what you're doing for them and then creating these demand, right? Discovery is the core of advertising to me because I was never expecting my wife telling me that what she going to buy when she walk into a shopping mall, if I know that I'll stop her already. She oftentimes that get out something different. So this is not planned. I think that's literally one of the behavior I would love to emphasize more is you want to be open up your door to more consumer.

**Ray Cao** (01:00:26):
Because we are a digital version of word-of-mouth, I always compare us to that because it is the way that how the digital era becomes more human because it is actually helping user to discover new things, just like what they used to do. There's a new place in a certain area, you just go explore. It is just like that. So I think that's the reason why I think at the very beginning, continue doing this kind of open-minded testing with us will be a very good approach to get some early learning and eventually that you can refine your approach. But at the beginning I would highly recommend that just be open up and also take some risks with us together and we're able to show you how much we can actually benefit in the business.

**Lenny** (01:01:15):
Awesome. And on that point, that was the other piece of advice you shared is pay attention to the trends so that you can connect your ad to things that people are already laughing at or finding really interesting. I feel like Duolingo is incredible at this. Their videos are hilarious and I think they're all just organic videos and a lot of them connected trends that are-

**Ray Cao** (01:01:34):
Yeah. It's funny you brought up Duolingo because I'm actually now become a heavy user of Duolingo myself because-

**Lenny** (01:01:39):
Me, too.

**Ray Cao** (01:01:40):
I watched the video on the TikTok. I think just basically kids just randomly learn a different language and make a lot of mistakes and it's really funny. And then I just download the app because I didn't know. I've been using Duolingo for the past 40 days as a New Year resolution. I'm convincing myself to learn Japanese.

**Lenny** (01:02:01):
Wow, 40-day streak?

**Ray Cao** (01:02:03):
Yeah.

**Lenny** (01:02:04):
Amazing. I'm at 25 days.

**Ray Cao** (01:02:06):
Okay, great. We're on par pretty much.

**Lenny** (01:02:09):
Are you in the Ruby league or Emerald league? Which league are you in right now?

**Ray Cao** (01:02:09):
Emerald, right now.

**Lenny** (01:02:13):
Emerald. Okay. I think I'm in Emerald, too.

**Ray Cao** (01:02:15):
So we're on par here.

**Lenny** (01:02:17):
Just to close the thread on this, so you're talking about one of the benefits of TikTok ads is awareness-building basically more top of funnel. I know you also focus a lot on taking action, not just brand awareness. There's also a lot of, so maybe talk a bit about that, just like that's also a big part of advertising and TikTok.

**Ray Cao** (01:02:35):
Yeah, I think the beauty of word-of-mouth is actually that word-of-mouth leads to actions. So I think TikTok, we oftentimes people are thinking that, oh, TikTok is really good for building awareness, building upper funnel or some of the discovery funnel. But I really want to say that we want to prove, and also we already proved that from the studies we have seen from third parties that we're driving actions at the same time, and this is literally the ambition we're trying to really talk to out of the advertisers, especially on the commerce front, that shopping and TikTok shop and shop ads. It is actually the proven points that we see. And also, this is not necessarily coming off of our illusion, right, because we see there was a biggest trend on TikTok is "TikTok made me buy it." We have billion level views on that.

**Ray Cao** (01:03:27):
It's continue growing and this literally inspire us to do this product. Like I said, one of the very important things here is we drive our product by listening to our user and see the behavior from them and we see the behavior and now we're trying to capture that and provide the best service to our user and also help advertisers to reshaping their product. So I do think that this year people will see us more as a full funnel solution platform rather than only building the brands because we want actually impacting on full funnel for our advertisers. Again, driving their business result is more important to us.

**Lenny** (01:04:03):
Say a startup is starting to think about advertising on TikTok, maybe they've done some Google ads and Facebook ads. What do you recommend they plan for in order to just see if this could work for them? How much time should they give it? How many ads should they run? How much budget should they allot to just explore this as a growth channel for them?

**Ray Cao** (01:04:23):
I would say at the very beginning, the investment will be coming from their leaning into creating a business account with us. So this is actually how you're engaging with your community. But even before that, I think just do some research on a platform and be the user as a TikTok to really experiencing it and see the differences. And then you are thinking about how can you actually connecting your behavior or your desired behavior coming from a user with your business and then you're creating content around it. And that's the moment I think this first step is creating your business presence on the TikTok.

**Lenny** (01:05:00):
And the idea there is just an organic account you create, let's say Lenny's Podcast, which I actually have... my Lenny's Podcast is on TikTok, so we can use that as an example maybe. So you're saying start off just creating free business accounts on TikTok and posting videos just to see how it feels and how it goes?

**Ray Cao** (01:05:15):
Yeah. Just see how it feels, right? So maybe some of the videos you don't get any views and some of the videos, you get more views. At the end of the day you can test some of the advertising products, drive those awareness and see if it's actually driving impact for you. And then you have to do more maybe testing with us or AB testing or geo-splitting testing eventually, depends on how big the investment is. You can see there is actually a directional impact on your business and also we are giving you reporting and insights on how you're doing on the platform, so you can optimize in towards that.

**Ray Cao** (01:05:50):
But obviously very important part is trying to get a feeling of the platform by creating your organic presence and then try to launch the ads account to make sure that you're able to drive more traffic to your desired destination or to a desired actions that you want user to take and continue refining that. Along the way, there are a lot of things that you're going to learn. For example, how can you leverage in automation solutions on the platform and how can leveraging some of the, I would say, creator trends you detected on the platform and also some of the tools that we're creating to help you to generating those scripts.

**Ray Cao** (01:06:24):
So these are all the things that you can learn from the platform. In terms of time investment, I think at the beginning of the month, definitely it's going to be, I hope it'll be a little bit more intense of learning so that you're able to get a rhythm in there and along the way that as long as gets become more automated and also get more understanding towards the business, you're able to actually creating, I would say, more relevant content for the platforms by leveraging our creators or by leveraging some of your own, I would say, resources from their third party, for example. So I think, yeah, it takes a little bit a learning curve, but I do think that the result will surprise you.

**Lenny** (01:07:02):
And was the implication there, give it a month? Like spend a month of running ads or is that not what you're saying?

**Ray Cao** (01:07:07):
I think oftentimes we'll say a month minimum to run ads because I think it's actually a learning curve for advertisers to really get into understanding the behavior and the platform.

**Lenny** (01:07:17):
And how many ads would you suggest, and I know there's not a rule of thumb, but just how many ads would you suggest they try to run in that month, to give you a real sense of this could work or no?

**Ray Cao** (01:07:27):
The more, the better. I would say at least 10 different ad creatives will be ideal per week and the more the better.

**Lenny** (01:07:37):
10 per week. Oh, wow. Okay. So 40 potentially.

**Ray Cao** (01:07:39):
Yeah, 10 per week. Also, I would say we can see that it is a little bit of, I would like nuances there because a lot of, "Oh, I don't have that resources," but as simple as possible, it can give you a tool. We have CapCut as a tool. I created my anniversary video for my wife by using that tool. Don't tell her one-minute now everybody knows, but she thinks that-

**Lenny** (01:08:04):
She might not listen all the way this long to the end of this episode.

**Ray Cao** (01:08:06):
She thinks it takes a lot of time. Literally the production is amazing. We are creating that tool specifically for our creator and also for our monetizer and the user in general. So you're able to do a lot of, I would say, automated and customized way in the app so you're able to generate those content on your fingertips. So it will be a really good help for advertisers that want to be more self-service. On the other hand, we also have third parties, certified TikTok service providers on the creative side to help you as well. So depends on the level of how advertiser you are.

**Lenny** (01:08:42):
Is there a most common mistake people make when they try this out where you're just often being like, "You fool, here's what you did wrong?" Is there something in there that's just like, "Just don't do this thing because a lot of people make this mistake and then they fail on TikTok?"

**Ray Cao** (01:08:53):
Yeah, the first one is I can see a lot of advertiser instantly they want to do remarketing or they want to do a very small niche targeting on the platform because you're limiting yourself. Like I said, it is more about getting to the rhythm to understand more about platform. So a broader targeting approach is actually recommended at the very early stage and most of advertisers are already doing that today because previously I can see for the first two years in the business, especially when we acquire new advertisers, oftentimes they get on the platform, say, "Hey, I want to do this and that. I want to really refine my targeting, et cetera." And then we just recommend, "Hey, why don't we do this comparison? You have a campaign set up like this going on, but this is our recommendation and you can see the difference." And literally most of them, they'll see a very big difference over there on it.

**Lenny** (01:09:44):
Amazing. Ray, I know you have to run, I'm going to skip the lightning round, but let me ask you just one question from lightning round. Do you have a favorite TikTok account that you've been just really loving these days? I'll share mine real quick and then see if anything comes to mind. There's this lady who I found recently who does silent baby product reviews where her baby's sleeping in the room and she is like, "Shh." And then she just goes through 20 different baby products very quietly and it's hilarious. I'll link to it in the show notes. If you have a kid, you'll love it. Is there anything that you love or want to highlight?

**Ray Cao** (01:10:18):
I do have one creator I am actually active following is on. He's a magician. He basically uses very, I would say, very normal things, just handy around him to make something that look very cool magic. I always were like, how did he make that? So I'm actually following that and getting more inspiration on myself is like, "Can I do that? No." I think that's more about my personal hobby to see something like that. It's very, very cool to see people can do these kinds of tricks by using normal stuff around them.

**Lenny** (01:10:54):
Ray, thank you so much for being here. Two last questions. How can folks reach out if they ever want to learn more about this stuff, if they can, and how can listeners be useful to you?

**Ray Cao** (01:11:03):
I think feel free to reach out to me on LinkedIn if you want to discuss more about some of the go-to market challenges you're facing. I think we're facing a lot of, I would say similar challenges every single day. And also in terms of on the product standpoint, different companies have a different product philosophy. I don't think we are always right. I was always recommending to receive a lot of feedbacks or recommendations and that would be really, really nice to have to form these kind, leveraging your audience, be my community to teach me a lesson sometimes. That'll be even better.

**Lenny** (01:11:39):
Amazing. Ray, again, thank you so much for being here. I feel like people don't have a ton of insight into the way TikTok operates, and I appreciate making time to do this.

**Ray Cao** (01:11:47):
No, it's a pleasure, Lenny. Thank you very much for having me.

**Lenny** (01:11:50):
Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny'spodcast.com. See you in the next episode.

---

## [16/19] The happiness and pain of product management | Noam Lovinsky (Grammarly, Facebook, YouTube, Thumbtack)

**Lenny** (00:00:00):
You've worked at so many great companies. At YouTube, when you joined, my understanding is YouTube was losing a lot of money.

**Noam Lovinsky** (00:00:05):
There were many times where Google leadership reconsidered the acquisition and, "Should we sell YouTube?" if you can believe it or not.

**Lenny** (00:00:11):
At Thumbtack, it looks like you went from 1 to -1 and then back to 1.

**Noam Lovinsky** (00:00:15):
I remember in a board meeting, the new model really started to show legs and one of the board members, Brian Schreier at Sequoia, said it was the prettiest smile graph that he had ever seen.

**Lenny** (00:00:23):
When you were at Facebook, you built what is called the New Product Experimentation team trying to create a startup within a startup.

**Noam Lovinsky** (00:00:29):
You're thinking on a different time horizon. If you're a large organization and you do some performance management process twice a year and you're 0 to 1 incubator, you've already killed it. It's the wrong incentive.

**Lenny** (00:00:39):
As the chief product officer of Grammarly, I'm curious what word you most often misspelled?

**Noam Lovinsky** (00:00:47):
The.

**Lenny** (00:00:47):
You do T-E-H?

**Noam Lovinsky** (00:00:48):
T-E-H. Yeah, exactly. Yeah, yeah, yeah.

**Lenny** (00:00:49):
Oh man.

**Lenny** (00:00:53):
Today my guest is Noam Lovinsky. Noam is currently chief product officer at Grammarly. Previously, he was an early PM at YouTube where he spent five years leading the creator product experience and then the broader YouTube consumer product experience. He then went on to take on the chief product officer role at Thumbtack, which involved helping the company reignite growth after a downturn caused by some changes Google made in SEO. He then went on to Facebook where he created the New Product Experimentation team whose charter was to incubate big new ideas protected from the larger Facebook org.

**Lenny** (00:01:26):
Noam has such a unique set of experiences taking products from 0 to 1, from -1 to 1, from 1 to 100, and even starting his own companies. He's never really been on a podcast before and he rarely ever tweets or post anything online, which we actually talk about. In our conversation, we walk through the lessons that he's learned through his amazing career at YouTube, Facebook, Thumbtack, and at Grammarly. We talk about when it makes sense to kill your project at a company, when it makes sense to ask to be layered at a company, why you should be keeping a nose out for which products matter most at a business and to find those products, why you need to diversify your growth channels at your business, why you should be finding work that is going to most stretch you to help you advance in your career, a bunch of advice for creating space for innovation within a large company and so much more. Noam is such a gem and I'm really excited to share his wisdom with you.

**Noam Lovinsky** (00:04:25):
Thanks for having me, Lenny.

**Lenny** (00:04:27):
It's absolutely my pleasure. I've heard so many great things about you from so many people. I think you're friends with a lot of guests that have been on this podcast. Something that I find really interesting about you and really respect about you is that you've worked at so many great companies and you've done so many big things in your career, but you barely ever tweet. You don't have a newsletter. I don't see many things on LinkedIn. I don't think you've even been on a podcast before. I think the only evidence I can find that you exist is you have this YouTube channel that's just like you go-karting and kids and people wishing you a happy birthday.

**Noam Lovinsky** (00:05:00):
Oh gosh, I should go monitor that. I forgot about that.

**Lenny** (00:05:05):
You might want to go find it now.

**Noam Lovinsky** (00:05:09):
Yeah, yeah, yeah that's funny. Yeah, it's funny. I think about that a lot, like am I doing something wrong? Should I be putting more effort in that? I mean, it's funny that you mentioned newsletter. I spend a lot of time with the Substack team's. I've been a very active advisor there. The team is fantastic by the way. And I think about it. Am I doing something wrong in my career by not doing that? But just to be honest, it doesn't come authentically to me. It doesn't come naturally to me. I get really focused on the thing that I'm working on and get really deep in the thing that I am working on and I have a hard time kind of multitasking a lot outside of that to be totally honest. The way that I kind of get to know the industry and other teams or whatnot is just through working with people.

**Noam Lovinsky** (00:05:58):
I'm not a very big networker. I'm not saying that there's anything wrong with that. I wish I were better at that. I get to know people by doing work with them, by helping them. And it doesn't necessarily scale in the same way that Twitter does, but it's served me well so far and it's more kind of authentic and it's what comes more natural to me. And so that's how I do it. So I'm doing a lot of coffees. I'm meeting people that way. I'm not doing a lot of tweeting or writing of newsletters. Maybe one day, but that's not me today.

**Lenny** (00:06:31):
So I think this is an awesome example of you can be incredibly successful as a product manager and as anyone in tech not investing time posting online. I am going to incriminate myself here, but I feel like the advice I always share with people is the best people are not spending time tweeting and talking online and sharing on LinkedIn. They're just doing the work. They don't have time for that sort of thing. And I think you're a great example of that. Is there anything along those lines that you share with folks that are just like, "Hey, should I be investing time here?"

**Noam Lovinsky** (00:06:59):
I think everyone can chart their own path and has a way that is sort of authentic to them and leans on their strengths. What I often coach people is, do what you like. You're generally going to be a lot better at the things that really fill you up that really get you excited. Life is short. There's so many things to be doing out there. We're so lucky. The number of interesting waves of technology that I've experienced, it just makes me feel like it's going to keep happening for a long time. We're very fortunate to be born in the time that we are and have the opportunities that we are. So why spend your time doing something that doesn't feel good because you think that it might lead to some success, where if you lean on what's authentic to you and what makes you happy, chances are you're going to be one of the best people at those things?

**Lenny** (00:07:49):
I love that advice. And I think it's so important. I think there's a lot of pressure on people too. "I need to do this, I need to do that."

**Noam Lovinsky** (00:07:49):
Totally.

**Lenny** (00:07:55):
"I need to tweet, I need to share content to be successful." This comes up a lot in this podcast, that the more you could just stick close to what gives you energy and what you enjoy doing, oftentimes that leads to things you wouldn't expect in a lot of success.

**Lenny** (00:08:07):
Speaking of that, looking at your career arc, I noticed a really interesting pattern and a really diverse set of experiences. So just kind of talking through places you've been. At Facebook, you worked on 0 to 1 stuff. At YouTube, the way I see it as you almost went from -1 to 1. At Thumbtack, it looks like you went from 1 to -1 and then back to 1. So it's like a really unique turnaround story. And then with Grammarly it feels like it's like, I don't know, 1 or I don't know, 5 to 100, or wherever you end up taking it. So I thought it'd be fun to talk through each of these experiences because they're such unique approaches or such unique experiences and see what lessons and wisdom we can extract from your journey.

**Noam Lovinsky** (00:08:51):
That sounds great. Yeah.

**Lenny** (00:08:52):
Okay, sweet. So I'm thinking reverse chronologically, we start with YouTube, which the way I see it is it's kind of -1 to 1. When you join, my understanding is YouTube was losing a lot of money. When you left, they were not losing money. And I was actually just looking, they're valued apparently at $200 billion today, YouTube as a business. I know you haven't been there for a while, but great work. What lessons did you take away from that journey? What stories come to mind from that part of your career that might be helpful to people?

**Noam Lovinsky** (00:09:21):
Maybe first to start looking with why hop around these experiences. I always tell people I feel like I'm an IC trapped in a manager's body sometimes. Fundamentally, I like to build, that's why I do this. I like to make things. And so sometimes the more fun way to make things is to start something and sometimes the better way to make things in the situation that I'm in is to try to support teams and lead through teams.

**Noam Lovinsky** (00:09:50):
And so I joined YouTube through an acquisition of a company I started. In the beginning, what I was doing there is just rebuilding that product on Google infrastructure and for YouTube customers. And maybe the first lesson was actually to look around at what the rest of the team was doing and be really honest and open about the relative priority of the thing that you're working on even if it might lead to your project getting canceled.

**Noam Lovinsky** (00:10:26):
So one of the things that I remember doing really on is actually talking to the leadership team and being like, "I don't think we should be putting 50 engineers on this project. Looking at the rest of the roadmap and the rest of the priorities, excuse me, I think this team would likely be better served elsewhere." Even though that was likely negotiating my way out of a job in month three, I don't know, I kind of felt like that was the right thing for the team and for the business.

**Noam Lovinsky** (00:10:57):
And then that started a very interesting journey because from there, basically the leadership was like, "You're right. We're going to wind that down and build some of those features into the existing product. And now you, you come and lead this focus area, we're calling the creator focus area." So I went from basically rebuilding the product that our startup had built to leading one of the three focus areas at YouTube. There was the viewer team, the creator team, and the advertiser team. And Hunter Walk, who's amazing, was leading the viewer team. And Shishir Mehrotra, who's also very amazing, was leading the advertising team.

**Lenny** (00:11:39):
What an alumni community.

**Noam Lovinsky** (00:11:41):
There was me. I was sort of like 29-year-old startupy guy working with these guys who were awesome. And YouTube in general, and continues to be, an incredible team. And so I think that was a first really good lesson. That in the right organizations, even in large organizations, advocate for what's best for the team, advocate for what's best for the organization even if that means that it puts you at a particular difficult moment. If it is a healthy team that rewards those sorts of decisions and actions, good things will happen. If it's not, that's good to know too. That's good to know early. So that's one thing that comes to mind.

**Noam Lovinsky** (00:12:32):
Maybe one other I would say atypical career choice that I made shortly thereafter is then when I was put in that role, I really struggled in that role. I was reporting to the CEO at the time, a guy named Salar Kamangar, who's also awesome, Google's 6th employee and just learned a ton from him, like an incredible strategic thinker. But he was asking me questions that I felt like they were from a different planet. I was like, I didn't know what they meant and he just thought in a different way, a different level or different scale and that's still something that I was learning. Eventually I figured it out, but I was really struggling in that moment. I had a really good relationship with both Hunter and Shishir and they really helped me through that. And eventually, I went to Salar and said, "Hey, I think I should actually report to Hunter. I think this would work better if we kind of combined the organizations this way and then we divided and conquered this way."

**Noam Lovinsky** (00:13:41):
And again, very atypical, no one has ever come to me in my career and said, "I would like you to layer me in this other person." But in that moment I was just like, "This is how I will do better work. This is how I will get better support. I will be happier and more productive and it'll be better for the team." And you know what? For me anyway, I was right. We made that change. Hunter was a fantastic manager and support at YouTube. I learned a ton, grew a lot. And then eventually when he moved on, Shishir took over the organization and then I moved into the viewer part of the organization, which is where I spent the rest of my time there, which was leading and supporting the viewer PM team at YouTube.

**Lenny** (00:14:32):
These stories are amazing. It connects to your point that you're kind of an, I see, an inner child I see, where you keep trying to kill your career by accident. Like, "Now, let's kill this project I'm working on. I'm going to demote myself a little bit." But clearly it's worked out. Is there anything that you saw that gave you that confidence that, "This is actually going to be okay"? Because again, people don't normally think this is how you get ahead in your career, is you kill your team and you layer yourself.

**Noam Lovinsky** (00:14:58):
Yeah, I mean I think having a broader view of the company strategy, having an instinct for what we should be doing and why and how I might prioritize all of these investments if I were given the opportunity to do that, I think internalizing that and understanding that and then trying to align whatever is under your influence towards that overall goal is very helpful and made me feel like, "I'm pretty confident this is going to be okay because it will lead to better results for the organization given what we're trying to do. And so as long as I'm trying to push decisions or actions that actually lead to better results, if it's a healthy culture and organization, I should be okay."

**Noam Lovinsky** (00:15:47):
I think that the other thing is, just over the years, I got extremely lucky. The first job that I got out of school was an incredible group of people and it gave me a nose for talent. It gave me a nose for what great feels like and what a high functioning team feels like. It's hard to know that without experiencing that. And so in the moments, YouTube was also one of those teams, Grammarly is one of those teams, Thumbtack was one of those teams. Being able to sniff that out when you're trying to choose the next team is very important. But I think that's another thing that gave me confidence. I learned these people well enough, Hunter, Shishir, et cetera, to have the instinct that the right thing will happen, like this will be better for me and the broader team.

**Lenny** (00:16:49):
Got it. So the key there is just you have to trust that the team around you is good enough, that you're not going to be pushed off into a corner. I think you made a really profound point here that a lot of people don't get about the job of a product leader and a product manager, that a big part of your job is to think about what is best for the business and work backwards from that. Not necessarily what's the best thing for the user is the highest priority, not necessarily what's the best thing for my team and how do I hit the goals that I'm obsessed with. It's what is going to be best for the business broadly and then make decisions there. Is there anything more you can say there about just how powerful that is as a way of thinking about prioritization and decisions as a product manager?

**Noam Lovinsky** (00:17:31):
Yeah, it's a great question. I mean, I think ideally, things that are best for the customer, there's high overlap with that with things that are best for the business, but not always, right? And I think figuring out some principles that help guide those sorts of conflicts can be really, really helpful. At Thumbtack, we had principles about which sides of the marketplace we wanted to serve in which order and when we serve Thumbtack. So it was customers first, pros second, and then Thumbtack last. And that's actually the first two... Saying Thumbtack last is the easy thing to say. Actually doing it in action I think is a very different thing. But that first one of like, should we... Especially when you're starting a marketplace, as you know well, Lenny, supply is so critical. Many marketplaces live and die by the quality and liquidity and supply. And so why would you focus on customers first and the Thumbtack perspective and supply are the pros, the people that you hire?

**Noam Lovinsky** (00:18:41):
Well, we always just felt that what the pros need from us is more customers. What the pros need from us is high quality customers. And so if we really try to make a great customer experience that attracts more customers, helps them find the right pros, provides the highest quality customers, then that will therefore be better for the pros. And so that's how we should prioritize. If we do those things right, then the business will benefit, right? And so doing things like raising prices because we think it's good for the business, even though it causes liquidity issues in the marketplace might be a little bit of a local maxima, locally optimizing rather than globally optimizing. So I think sometimes in these sorts of questions, trying to establish some set of guiding principles that help navigate some of these more ambiguous or thorny questions can be really helpful.

**Lenny** (00:19:38):
I want to circle back to this first point you made, an experience you had convincing people that your first project shouldn't be something you work on. How long do you stick with something that isn't going well and then decide, "Okay, let's convince people this is something I should move on from," versus you don't want to give up on a project quickly, you want to give it a shot?

**Noam Lovinsky** (00:19:56):
I mean, look, I don't know that it's a perfect answer, but I think the reality is just that what kills most projects most early companies is stamina. And I think that we all need to work on being more resilient about kind of like, I remember at Thumbtack, Marco, the CEO, we used to say that it feels like we're running uphill and chewing glass, and you're kind of like, "That's right, we want to do that. That's good for us. Take our medicine." So you want to practice that sort of resiliency. But ultimately, I think that what starts to happen is you start to lose the stamina and you're just not bringing your best self to the situation.

**Noam Lovinsky** (00:20:42):
And so many of these things that are so high ambiguity where you don't know exactly what to build or you don't know exactly, you're not getting the signal you need or the feedback you need to be able to hone it in and know that you're doing something well. They require just an ungodly level of faith and stamina. And so that's sort of what I look to. When you see a team that is motivated, that is building something like they're really excited about, I mean just the inertia, the quality, it's like a whole different game where when you see a team that's sort of down and out and they've really been hitting their head against the wall for a long time, sometimes they just need a change of scene, a change of pace, and they get to a much better situation. So my honest answer is, yeah, it's the, when do you run out of steam is usually the question. I think that happens usually like in the startup case, a lot of times before you run out money or these other things.

**Lenny** (00:21:48):
We've talked about Thumbtack a couple of times now, so let's talk about that. I love this description of running a pill, chewing glass. My understanding is when you joined, things were going well, and then things started to go much less well, and then you helped turn things around. Talk about that part of your journey and what you learned from that time.

**Noam Lovinsky** (00:22:05):
Yeah, sure. Again, really fantastic team and really strong founders. That company was just on the bleeding edge of things like SEO and growing by SEO. It was one of the best organizations that are driving growth through that channel. But I think a thing that I learned really early, which Lenny with your background you probably know as well, SEO is a sort of a live by the sword, die by the sword channel of growth. I think that one channel growth company is always a no-no. And so that's a little bit of what we had at Thumbtack.

**Noam Lovinsky** (00:22:44):
So it was funny, because I remember when I joined and Marco and I had an agreement where it's like, "Okay, I'm going to do my three months of onboarding, listening to our new leader inheriting a team." I've always gotten advice that that's what you should do. And Marco being an entrepreneur and a hard running founder is like, "Yeah, yeah, yeah. Sure, sure." And then a month in, it's like, "All right, we got to run 2024 planning. Go." Or not 2024, sorry, at the time it was. And yeah, in the early days when I was there, Thumbtack was seeing triple digit growth. Then we had a couple SEO hits that got us down to double-digit growth. And then not too long after that, we were actually, for the first time in the company's history, seeing negative year-over-year growth and Google was just really coming down on our category as we were, by the way, trying to rebuild the whole product and change the monetization model and everything in between.

**Noam Lovinsky** (00:23:50):
So it was a really a tough moment of how much do we kind of spend to reinforce the old model while we're sort of building the new model, kind of changing the engine while the plane is flying. I think I remember in a board meeting, once we kind of turned that around and over time and also the new model really started to show legs and really started to work, one of the board members, Brian Schreier at Sequoia, said it was the prettiest smile graph that he had ever, ever seen. It was obviously a really proud moment there.

**Noam Lovinsky** (00:24:24):
But I think that the thing that I took away from that, which I tell PMs quite a bit, is growth masks all problems. You don't really have a, I think, true understanding of what is working well and what is not working well when you have incredible growth. YouTube was a great example of that. And at Thumbtac, it had incredible growth for quite some time, but it was essentially burning through a lot of demand. It was just dropping a lot of demand on the floor because there wasn't sufficient liquidity on the supply side to really meet that demand. The team knew and was trying to work on that problem, but it wasn't as urgent or high priority because you're having triple digit growth. What's wrong? Everything's going great, right?

**Noam Lovinsky** (00:25:11):
And then the moment growth starts to slow or certainly when growth starts to be negative, all of a sudden the tenor in the organization really changes and you start looking at things very differently and trying to understand what's actually going on. And so I think it's actually a very healthy thing for businesses to go through as they turn into long-term sustainable businesses to have those sorts of moments, because I think otherwise it's just really challenging to identify where the true issues are. And I think as a PM, if you've only ever worked on things that grow and you've never felt the other side of that and how to help turn that around with your team, I think you lose a lot in your career if you don't experience that.

**Noam Lovinsky** (00:25:58):
I'm kind of naturally paranoid. And especially as I manage growth, I often look at things and ask myself like, "Okay, what do I do right now if it went negative? How would I prioritize things if it went negative?" Having gone through that experience, I just look at things in a different way of urgency. I look at things at different levels of priority having gone through that experience.

**Lenny** (00:26:25):
With this Thumbtack story, I think it's rare that a business gets the smile graph that you described, this prettiest smile graph that this board member has ever seen. I think that is rarely the case. Usually, it doesn't come back up. Can you share what you did to help Thumbtack turn things around? I know it's very particular to Thumbtack in the business, but just anything there that would be useful to people?

**Noam Lovinsky** (00:26:46):
Sure. First of all, this is very much the team. It's not just things that I did. So I mean, first was turning on multiple channels of growth. Up until then, Thumbtack had tried and stopped paid channels, other organic channels like referrals, all of the typical things. And so, we just went back to first principles on a lot of that and also just kind of reformed a team around that and basically got an amazing team together. One of them, Whitney Steele is running marketing at Descript now. Another one, David Schein is running a product at HIMSS. But basically I went back to first principles on some of those growth channels and experiment on our way to much, much better results.

**Noam Lovinsky** (00:27:42):
I think that one of the things that we were doing incorrectly at Thumbtack is Thumbtack is actually a marketplace that is actually made up of thousands of marketplaces, right? Like DJs in Philadelphia is one marketplace, DJs in Atlanta is another marketplace, contractors in Sonoma is another marketplace. And then Thumbtack is obviously the container of all of those marketplaces. I think we were just bifurcating our targeting and our growth efforts a little too narrowly, assuming we had to grow in that way market by market rather than targeting more broadly, providing the more aggregate data to Google and others, and then optimizing from there. The fact that we already had really good showing in SEO and really good patriarch and SEO helped to bolster things like SEM and then eventually Facebook as well.

**Noam Lovinsky** (00:28:40):
Those were kind of the growth levers, but the core issue with the Thumbtack product was that it was just a very high friction customer experience that really left customers waiting. So the way that Thumbtack worked basically was a customer would find them through a search query, they would come in and they would answer a number of questions about the job they needed done, and then Thumbtack would say, "Okay, great, we'll get back to you in 24 hours." And this is a modern day experience, right?

**Noam Lovinsky** (00:29:17):
And then what Thumbtack would do is they would take that job and they would federate it out to as many of the pros that might match the criteria, and then the pros would pay to quote to show up as a potential provider for that job. Now, I don't want to take anything away from that team because that worked phenomenally well for a really long time. And actually it's a perfect case study in like, "|Just do the scrappy thing that works to grow." And they did that very well, but the stage and size of the business when I joined it had kind of outgrown that. And the team knew that. That's obviously a very high friction experience. The idea that the customer, they're super excited, they want to hire someone, and at that moment you'd be like, "Cool, talk to you soon," not the best experience.

**Noam Lovinsky** (00:30:06):
And the fact that you're asking your supply to put up money to even show up to customers in the first place, well, what the customers want to see is the supply. Like, "Tell me who I can hire." Also, a lot of friction on that side and also in some cases some unfair revenue on that side because if folks are paying to be seen and maybe they're looked at, but there's not really high intent, then they're not going to get the customers they want, they're going to be spending revenue, they're not going to be getting revenue back. It turns into just a bad loop obviously.

**Noam Lovinsky** (00:30:40):
So the main thing we did is to rebuild that whole loop, change the monetization model, build a system where essentially pros could provide instant quotes. Lenny, I'm sure from Airbnb, this is very familiar, the move from request to book to instant booking. It was a very similar thing in a different kind of category of service and supply obviously. But that shift and doing that shift across those thousands of marketplaces and then finding the right friction point for monetization and when and what to charge people for and all of that change, that is what really, at its core, turned the growth engine around at Thumbtack. And it's just a real testament to those founders that they believe that, saw that, and were willing to run a pill and chew glass to get to that point. I don't know the details of the business anymore. And if I did, I wouldn't speak to it. But from what I hear, things are going well, so I think that that served the company well.

**Lenny** (00:31:45):
Yeah, as you were talking about that, that's exactly an experience Airbnb went through. I actually led that effort at Airbnb. It took three years of my life.

**Noam Lovinsky** (00:31:53):
Oh my gosh, we should talk about that one day.

**Lenny** (00:31:57):
Yeah, I've written about it here and there, but honestly very quietly is one of the biggest transformations Airbnb went through, shifting from I'm going to go request a book to basically every book now on Airbnb is instant. And that was a very difficult and painful journey. But looking back, I don't think Airbnb would've made it if not for that. And unlike Thumbtack, we did it before things were starting to fall apart. And actually, I was going to say the lens that we used that I find really helpful here is, you should be asking yourself, "If somebody was to come into our space and disrupt us and start now to become the new Airbnb, what would they do?"

**Noam Lovinsky** (00:32:33):
Yeah, totally.

**Lenny** (00:32:34):
And it was obvious that it'd be be make it instant, just the way it works. Welcome to Airbnb disruptor. And so, yeah.

**Noam Lovinsky** (00:32:40):
Another learning there is any product you work on that involves bits and atoms is exponentially harder than products that just involve bits. But it's amazing how something as seemingly simple as make an instant ends up being so incredibly deep and complicated. And especially on an existing business, making that transition while still growing is just very, very complicated. Fantastic learning I'm sure you had as well.

**Lenny** (00:33:07):
Very difficult to change people's expectations and behavior. This could be its own podcast episode, just changing marketplaces into an instant experience.

**Lenny** (00:33:14):
I wanted to circle back real quick to the first lesson you had there, which is adding new channels. I think this is a really interesting takeaway here. So essentially Thumbtack was reliant on SEO. Google slash the sword, as you described, started changing things so traffic stopped coming. I think a cool lesson here is just if you're reliant on one growth channel, which I think most companies actually are, I think most companies have one main driver, I think a lesson here is potentially before things start to fall apart, especially if you're SEO-driven, start to explore more practically paid referrals.

**Noam Lovinsky** (00:33:46):
Totally. I mean I think maybe it's, again, it's kind of living through that. Now, anytime I look at a product or look at a team, it's one of the first things that perks up the paranoia of just like, "Oh no. You don't want to be in that situation. Let's figure out now how you start to diversify because you just never know, like you say, when one of those might dry up."

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**Lenny** (00:35:29):
Is there anything else from your time at Thumbtack that stands out as an interesting lesson or takeaway that you bring with you to the work you do now?

**Noam Lovinsky** (00:35:37):
I would say this, I think especially at the leadership level, the team that reports to the CEO, that group doesn't always have the opportunity to do a lot of project work together, right? You've got your CFO, you've got your head of sales, you've got your product and your engineering. There's just not as often as natural ways for that group to work together. And then when something happens like growth goes negative, that group is very important. And that group's ability to tackle hard things together is very important. I think that one important lesson from that is, no one can be a bystander on product strategy. Just because you've got product in your title doesn't mean you're the only one that should be thinking about product strategy certainly at that level. Certainly not in engineering.

**Noam Lovinsky** (00:36:39):
The CFO, the head of people, everyone needs to have a seat at the table when it comes to product strategy, what the company's doing and what they're going to do to grow out of the situation that they're in. Because otherwise, in those hard times it can kind of be like a, "What have you done for me lately?" sort of a dynamic. And that's just not the right dynamic to have on that team. I'm not saying that at Thumbtack we had the right dynamic, but I think it was a really important learning in that moment of how that team, even if they didn't typically get as involved in things like product strategy and what we're building, how everyone had to be all hands on deck and really thinking about those sorts of problems because it's the only way I think you can get a whole company and team out of those situations by everyone getting involved in doing their part and pulling on the levers that they have in their area in order to do that well. I don't think it can work in any other way.

**Lenny** (00:37:38):
So there's a lesson there. Build a relationship with the leadership team before things start to go awry.

**Noam Lovinsky** (00:37:44):
That, yes. Certainly that, but I think it's also incumbent for people in our roles and engineering roles to bring strategy to that discussion, to that group, in a way that it is possible for everyone to engage and everyone to internalize and understand what it means for their area and to even have obviously a say in because they're on the leadership team at the end of the day. They should feel like their fingerprint is also on the company strategy, and as soon as it starts to feel like that's their world, that's our world. And I think that's true for any of the functions. It's true for what's happening in sales, it's true for what's happening in marketing. As product managers, we naturally need to be the connective tissue across all of that, but I think the whole leadership team at that level should feel like connective tissue across all of those functions.

**Lenny** (00:38:39):
Okay. Let's transition to Facebook. This is I think an example of 0 to 1. So when you were at Facebook, you built what is called the New Product Experimentation team. I actually thought it was called the New Product Experiment Experience team, but I think it's New Product Experimentation team. My understanding is the idea there is, instead of Facebook having to buy the next Instagram and WhatsApp and all the things basically incubate startups within Facebook in a stabled concept, a startup within a startup, create all these startups within a startup. And as an outsider, it feels like it was really fun for a while, but it hasn't let any amazing new businesses for Facebook. Correct me if I'm wrong. I'm curious what that experience was like, what you took away from it, how it went, what you think about when you look back at that part of your journey.

**Noam Lovinsky** (00:39:28):
I was one of the few folks that kind of joined that team early and help build that team. How it ended up and how it closed down, I am not familiar with because I wasn't there. But I think in terms of was it a success or not because it didn't build the next Instagram I think is a little bit of the wrong bar to set for things like that. To some extent, it's like, "Did the group win the lottery or not? And let's judge there. Let's judge their success." Obviously I'm not saying that discovering something like Instagram is just winning the lottery, but you get what I mean in terms of the rarity of those sorts of discoveries and those sorts of products.

**Noam Lovinsky** (00:40:12):
I think that that team was very realistic about what I would say would be the champagne level outcomes and/or more like the kind of beer, nice dinner kind of level outcomes.

**Lenny** (00:40:28):
Your wine.

**Noam Lovinsky** (00:40:29):
Yeah, the wine. Yeah, thank you. That's a better analogy. I think we built knowing those sorts of outcomes would also be very beneficial to the organization. So as an example, one of them is, at Facebook scale, doing things that don't scale or doing things that start out small was just a muscle that was really hard to come by, right? It's like any community product that you build, any kind of social where there's community density that's important early on, any product that you build that way, starting with a million users is a really hard way to do that. At places like Facebook and Google, it's like it's hard to run an experiment with a hundred people. It's not hard, it's impossible, right? And so this idea that you would have to get real small, that you would have to start very targeted, that you would have to start with things that clearly don't scale and don't have a chance of being big from the get-go is really, really hard in an organization like that.

**Noam Lovinsky** (00:41:47):
And so creating that space for NPE to be able to do that, to be able to help remind the organization what are the mechanisms we need to be able to build and learn that way was very beneficial. Even simple things. At an organization of Facebook size, maybe experiences at an Airbnb, it is really hard for product managers, engineers and designers to talk directly with customers. It is basically impossible. You're almost always talking through some third party, some recruiting agency and getting reports and you're not always in the room. Imagine building a startup, like a product from day one and not being able to sit right next to your customer and being like, "Show me how you do this or show me how you do that.' It's incredibly hard. You're looking for such faint signal.

**Noam Lovinsky** (00:42:48):
The idea that you would try to get it through layers of indirection and games of telephone is crazy, but at that scale, that's what you have to do because there's all of these legal concerns and many other realistic concerns about what you can say to who and who you can talk to and what you can tell them about what you're doing and all of these things. So creating an environment where those sorts of constraints were lifted and were different was very beneficial, I think, to the organization and started to shed a light on some of the things that were broken that make it hard to build 0 to 1 in those sorts of environments.

**Noam Lovinsky** (00:43:31):
I also think it was a really fantastic recruiting tool. It did build a really great group of folks, many of which have left to go start interesting companies. But I guess what I'm trying to say is I think when you're an organizational leader, and Schrep was the org leader that was supporting NP at the time and he's fantastic and really did a good job of firewalling that team, I think you're looking at a set of objectives and a number of ways that you might help the company and the organization. Even if you set that light on the hill to be like, "Go find the next Instagram," many of the things that you would do along the way to find the next Instagram end up being very beneficial to the broader organization. We saw a lot of that in PE.

**Lenny** (00:44:28):
That's a really interesting perspective. There's a lot of other goals with something like this, it's not just find the next massive business. It's the way I think what I'm getting from this is shine almost a mirror on the organization, like, "Here's the things we can't do with the regular business and we have to do something. We have to set this up in order to try something totally new and radical recruiting tool" I think is interesting.

**Lenny** (00:44:49):
There's actually a team at Airbnb, the way I described it was, I don't know how many people know about Burning Man and how it works, but there's this trash fence around the side that catches all the trash so it doesn't go into the desert. And I feel like there's teams sometimes that are the trash fence of the company.

**Noam Lovinsky** (00:45:04):
That's funny, yeah.

**Lenny** (00:45:04):
Where someone's about to leave and they're like, "No, go work on this coal stuff over here in the fringe," which is really interesting. But just instill within the company and maybe help with that. Just keep people that are awesome at Meta. [inaudible 00:45:16].

**Noam Lovinsky** (00:45:16):
Yeah. You're right that the team didn't discover the next Instagram. For what it's worth, things like Threads and ideas like Threads were in that team all of the time. I think that if that team caught the wave of generative AI and all of the opportunities and new technologies there, I think things could have also... Because those are certain moments where you having small, really motivated, dedicated teams that aren't thinking about anything mainline can lead to faster discoveries, I think that can also help. But there were a number of things that basically ended up becoming features in other products and they were just easier, faster ways of validating and building them because you didn't have the constraints of the mainline product development organization, right?

**Lenny** (00:46:07):
For someone that is thinking about trying to create a startup within a startup, something a lot of big companies are trying to do, is there a piece of advice or two that you'd share for helping this be effective? Maybe one is just the goal may not be build the next big business. There's these sub goals also. What comes to mind?

**Noam Lovinsky** (00:46:26):
God, there's so many. Schrep did a really fantastic job of removing a lot of these constraints. So one is I would say think really hard about the incentive system. Smart, good people, even if they're not trying to, they end up kind of gaming things towards the incentive system. And so think long and hard about that. So for instance, if you're a large organization and you do some performance management process like twice a year and that's how you're going to evaluate and incentivize people in your 0 to 1 incubator, you've already killed it. It's the wrong incentive, it's the wrong timeframe. It creates adverse selection, problems for the sort of people that you bring in. And so it's hard in an existing organization to say, "We're going to take all these company processes around even how we level people and pay them and motivate them. And we're going to throw them out the window for this group."

**Noam Lovinsky** (00:47:27):
How you build the infrastructure you use, this is something that the NP team did really well. Everyone got to do their own thing from an infrastructure perspective. Just do what is best for the problem you're trying to solve in this moment, knowing that you're likely going to throw away a lot of this code anyway. Being able to do that in an organization like Facebook or Google, if you ask anyone that works on those things, is really hard. It takes someone like a Schrep to be like, "Nope, they're going to get to do this. Sorry." And so I think that's really helpful.

**Noam Lovinsky** (00:48:01):
For what it's worth, one of the organizations that we talked to that I felt like was doing this in one of the best ways was Nike. Nike has this incubation lab. It's a completely different operating model. They recruit a completely different type of person, very different incentive system. And essentially, where they end up plugging them into Nike is that when they have something into the distribution marketing kind of growth arms of Nike. But for the product discovery process, they're doing their whole different thing. Once they find some fit, then kind of Nike comes in and goes, "Boom. I'm going to help you explode your fit." But I think that the number one thing I would think about would be the incentive system and the adverse selection that that can cause.

**Lenny** (00:48:52):
To me, the most important element of the incentive system, and maybe I'm reading between the lines, is you're basically competing against them starting their own thing. And having upside if things go super well feels really important versus, "I'm just going to get a cool salary at Meta and work on this thing." That doesn't lead to the same experience as a startup where everything's on the line.

**Noam Lovinsky** (00:49:10):
Yeah. And also what time horizons, right? When you're starting a company, you're not thinking like, "In the next six months, I'm going to get a promo and I'm going to get a good rating and things are going to go well." You're thinking on a different, excuse me, time horizon, and you're thinking about an outsized impact or an outsized incentive. And so I would think about that if you're starting things internally as well.

**Lenny** (00:49:34):
Awesome. Okay. Let's move to the final bucket, Grammarly, which is where you're at now. The way I'm thinking about it is this kind of like a one, two rocket ship or I don't know, 10. It's further along than one, but that's where you're at now. To me, Grammarly is interesting because it's one of the very few successful B2C subscription businesses. There's almost none. There's Duolingo, Grammarly. And I know you're doing B2B also, but there's so few. There's so many dead bodies trying to build a business on top of consumer subscription. And so I'm just curious. What the current state of Grammarly? How are things going? What do you think has been the key to it being successful all this time and continuing to grow? And what lessons have you learned? I know you just joined relatively recently, but anything you've taken away from that journey so far?

**Noam Lovinsky** (00:50:26):
We don't talk about it often, but Grammarly is a much bigger company from a revenue perspective than I think people realize. The company has been around for 15 years and was profitable from day one, and continues to be quite profitable. So it's a very, very healthy business that is much larger than folks might realize. And that is actually quite intentional because the company was trying not to be noticed for a long time, very intentionally. The fact that you would have grammar and spell checking in Google Docs or grammar and spell checking in Word. People would often write off the company that like, "How is that a business? How is that a feature? These products already have it." And that was very convenient for Grammarly because they could kind of navigate between these giants in tech and grow a very phenomenal business on this use case that people had written off.

**Noam Lovinsky** (00:51:30):
Now, come the advent of LMS, it's no longer a use case that people are writing off and sort of the dream of the founders that machines can assist us in communication in this way that they've had for 15 years, I feel like now the whole industry is like, "Well, this is obviously how we're going to communicate and machines are going to do all these things for us." And Grammarly is now sort of in the center of that hurricane. And again, I think it's a similar thing where it's like, "Well, there's ChatGPT. There's Microsoft Copilot. How is Grammarly going to have a chats?" But yet things still seem like there's the future. The future is bright.

**Noam Lovinsky** (00:52:14):
And so to your question, I think what has made it work, I've only been here for 10 months so please kind of take this with a grain of salt, but my instinct is that people really love Grammarly because of how it works and where it works. And what I mean by how it works is Grammarly is one of the few products where you just install it and it makes you better. You don't have to configure it, you don't have to manipulate it, you don't have to change anything about what you're doing. You carry on and across all of your applications, across all of your tabs, you'll start getting pushed assistance to you in the right moment. You could ignore it if you want, no big deal, but it takes a very, very small amount of effort to tap on one of those things, get some value and keep going.

**Noam Lovinsky** (00:53:04):
I think that a product that is that easy to use, that easy to extract value from, but then also that prevalent, how many different text boxes do you write in a given day? I mean, it is not less than 10, it is tens or potentially hundreds, right? And so it is everywhere and it is very, very low effort to get real value from it. And then the where we work is what I said, you don't have to change anything about your workflow. Grammarly meets you where you are and you get value from it. Doing that really well at this level of quality for a user base of this scale, essentially it's like a huge AI achievement masquerading as a little UX innovation, right? But that experience, that UX that sort of brings AI to the masses has obviously served Grammarly really well. I think those are some of the strengths that we're going to continue to lean on to now provide a very different type of assistance and value that we can because of where the technology has moved.

**Lenny** (00:54:21):
The other thing I've heard a lot about Grammarly, and Yuri was on the podcast and who led growth for a long time at Grammarly, is just how scrappy the business has been and the founders have been from the beginning, the fact that they've been profitable from the beginning. That feels like one of the threads through all of the successful consumer subscription companies, is super scrappy, not raising money for a long time. Is there anything there that you found to be really interesting or helpful for other folks that are maybe building the space?

**Noam Lovinsky** (00:54:46):
When you're a team that kind of starts out of Ukraine and you're not thinking that there's any chance that you're going to raise money and why would you do that, I mean it really... Back to our previous conversation of what happens when growth goes negative, it really forces you to focus on the important things. And so, like many of the early engineers who are still here because the company has done so well over the years, they think in like, "How is this work going to translate into revenue?" They think about the impact on the business from even very deep technical work that they're doing because I think they were brought up in this culture where the business doesn't really invest ahead of its profitability because it was a bootstrap business from day one. So that enforces everyone to think about their projects and their prioritization and how is what they're doing over the next two months going to actually turn into more revenue and keep the company growing and sustaining. So I think that culture is prevalent and help Grammarly get to where it is.

**Noam Lovinsky** (00:56:00):
Now, I just want to be really honest that in moments that we're in like today, that can also be detrimental because the business gets to a certain size, you start getting to law of large numbers. You need to start thinking about are there other products? Are there other use cases? Are there other channels of growth? How do you invest ahead of some of that growth and start to diversify? Because at the scale and size that we are and aspire to be, we're going to have to do many more things and service many more different types of customers. And as you mentioned, we're going to have to pull off the motion of B2C to B, kind of get that product-led sales motion going. So all of those things are happening. And thankfully the business is as strong as it is where we can invest ahead now in those things while still maintaining profitability and a really strong business.

**Lenny** (00:56:57):
That's amazing that they're still team members and maybe I think you said engineers from the beginning, 12 years later. I think that says a lot about the business. And before we started recording, they're based in Ukraine and you were saying that they're going to Zooms, there's bombs going off, they have to go into bomb shelters and then jump on a meeting. It's incredible that team continues to operate and the business continues to do this well in spite of all that.

**Noam Lovinsky** (00:57:22):
Yeah, the team in Ukraine at Grammarly is... I mean, it's something else. It's a really fantastic team. When you speak to many of them, I think actually the work provides sometimes a very useful distraction, but they obviously feel a lot of pride in the business. They built a lot of this business. There aren't yet many businesses of this size that kind of come from Ukraine. I think that that team is incredible and continues to deliver a ton of impact to the company even in the circumstances that they're in. I know for the founders, a lot of why they want Grammarly to succeed and be the generational company that it can be is for Ukraine, and especially in this moment and it's awesome to see how that motivates them and 15 years on the same project is not nothing. That's some serious resilience. And so I think even in moments like that, using them as a way to motivate and strive for something greater I think says a lot about the founders and the team in Ukraine.

**Lenny** (00:58:40):
Absolutely. Hopefully there's a happy resolution soon there. I don't know if you know this, I was actually born in Ukraine.

**Noam Lovinsky** (00:58:47):
Oh wow.

**Lenny** (00:58:48):
I know Odessa.

**Noam Lovinsky** (00:58:49):
Oh, nice.

**Lenny** (00:58:49):
I don't want to talk about that much, but it's true. And I just realized we both have skys in our last name. Lovinsky and Rachitsky.

**Noam Lovinsky** (00:58:56):
So for what it's worth, my dad was born in Ukraine. He is from Kiev. My mom was from Lithuania, so yeah, I also have some Ukrainian background here.

**Lenny** (00:59:05):
All right, so Ukrainian episode.

**Noam Lovinsky** (00:59:07):
Yes.

**Lenny** (00:59:08):
Let me zoom out a little bit and get to the final couple questions. So thinking about your career broadly, I'm just curious if there's any general advice you share with people to help them have a more successful career. Anything that just generally you find is really important to do well or mistakes they make. And this is a big broad question, but anything come to mind of like, "Here's something you should really try to do more of or less of?"

**Noam Lovinsky** (00:59:37):
Look, when you're thinking about career opportunities and what job to take, it's really, really hard to sniff out really well in a high degree of certainty like success. I think that having a good nose for people and the sort of people that you can be successful with is something that you can develop. What I found is I always try to prioritize putting myself in positions that are going to cause a lot of growth and learning. And growth and learning can be very painful. And you kind of got to be okay with that and go into that because on the other side of that pain I think is the promised land.

**Noam Lovinsky** (01:00:21):
And that's just served me really well, is I can't necessarily predict with high degree of certainty that this thing's going to hit, but I can get a sense of the people around me and I certainly can find situations that are going to stretch me, that are going to force me to do things that I haven't done where I'm going to grow and learn significantly. And over sort of the arc of my career, I feel like that's served me well. So that's usually what I tell people, is focus on on that if you can.

**Lenny** (01:00:53):
I love that advice. I've used this quote a number of times on this podcast, but something I always come back to is this line, "The cave you fear contains the treasure you seek." I'm curious if there's something you have found about when the pain is too much, that you shouldn't pursue that. A lot of people get into these places where their mental health gets hit, their physical health is hit, they're just doing work they should not, it's too much. Is there anything there that you find it's just like, "Okay, maybe this is too much of discomfort"?

**Noam Lovinsky** (01:01:24):
I mean, I think about a couple of things. I think in any situation you should be able to lean on one or two things that you're really strong at. That can be the foundation that keeps you going while you learn the other things. So just be wary of situations that are too net new.

**Noam Lovinsky** (01:01:44):
There should be one or two important things as part of that job going into where you're like, "I got this. I know how to do this portion of it." So as an example, if you've never inherited a very large team and you work through how that works, but the product area that you're working on is one you're very familiar with what's necessary to be good in that product, whether it's really good sense of design or really good sense of analytical thinking, recommendation systems, what have you, there should be a couple of those things where you're like, "I got this. These things are going to be a stretch, but these things, I feel like I've got a handle on how to do this. I can always get better, but I feel like they're in my wheelhouse." And I think that tends to allow you to balance the pain with the areas that you already know and manage through in a more balanced and healthy way.

**Lenny** (01:02:48):
It reminds me of that chart I think from flow of you want it to be challenging but not too challenging, and that's where you end up being most successful. Is there anything else, Noam, you want to share or leave listeners with before we get to our very exciting lightning round?

**Noam Lovinsky** (01:03:05):
Yeah, I just think that maybe going back to where we first started, Lenny, work on the things that make you happy, that fill you up. Life is short. We're all very lucky to be in this moment. There's no reason to spend time on things that don't give you energy. There's so much to do out there. I think that's the main thing I would focus on.

**Lenny** (01:03:29):
Amazing. And even though there will be things that you have to do, I think it's important to try to find as much of that as you can because not everyone can just like, "Nah, I'm not going to do this work thing. I'm just going to go on a walk." But I think that's such an important point. And we've talked about this actually a bunch on recent podcasts of just doing this energy audit where you pay attention to what gives you energy and what doesn't and try to do more and more [inaudible 01:03:54]-

**Noam Lovinsky** (01:03:53):
Totally.

**Lenny** (01:03:55):
... willing to do that again. With that, we reached a very exciting lightning round. Are you ready?

**Noam Lovinsky** (01:03:59):
Yeah, I'm ready.

**Lenny** (01:04:00):
First question, what are two or three books that you've recommended most to other people?

**Noam Lovinsky** (01:04:06):
I'm going to cheat on this one and I'm only going to give you one. I'm only going to give you one because I don't want to cloud with any other. I recommend Build by Tony Fidel. Other than it being a good book, one of the main reasons I recommend it is that my wife wrote it. So she wrote it together with Tony. And I got to see that experience. She's a fantastic writer and Tony has a lot to learn from, so I recommend that book. I think that the part of it that was particularly inspiring to me to hear even more of the details that are in the book is just how many times he met failure before he made discoveries that are now driving so many of the things that we do. It's just a good reminder to keep at it and do the thing that really gives you that energy because eventually you can make that incredible discovery.

**Lenny** (01:05:00):
Next question, do you have a favorite recent movie or TV show that you've really enjoyed?

**Noam Lovinsky** (01:05:06):
I really like For All Mankind, if you've seen that on Apple TV. And then I just finished the last season of Fargo. Every single season of that series I think is fantastic.

**Lenny** (01:05:19):
Amazing. For All Mankind though, last season, not as amazing a consensus that I agree with, but worth watching.

**Lenny** (01:05:26):
Next question. Do you have a favorite interview question that you like to ask candidates?

**Noam Lovinsky** (01:05:32):
I generally like interview questions that allow us to kind of do some work together, so I'm a little bit less on the behavioral "tell me about a time when" sort of stuff and more on the "Let's work a product problem together." It could be anything from like, "Let's design an alarm clock for children." Or lately I've been using one. "Given where technology is at, if we were to rebuild email, how might we do that?" I just feel like getting into it and getting into the details and really watching each other exercise our craft I think is really important. I have a whole podcast one time, if you're ready, about how most people don't know how to do leadership recruiting. And I feel like as I've advanced in my career, the interviews for some reason get easier and actually I can evaluate less about who I am as a product leader and whatnot. But yeah, those are the sorts of interview questions that I typically like.

**Lenny** (01:06:30):
Amazing. Is there favorite product you've recently discovered that you really love?

**Noam Lovinsky** (01:06:36):
It's not recent, but I was a very early user of Arc and I really love Arc.

**Lenny** (01:06:43):
Your window right now is inside Arc. I also love Arc. We had Josh on the podcast.

**Noam Lovinsky** (01:06:48):
Nice.

**Lenny** (01:06:49):
Just watching the onboarding experience of Arc alone as a product person is worth your time.

**Noam Lovinsky** (01:06:53):
Totally. I love the animation when you download something. I mean just like all of the little things. And if Josh is listening, we would like to get Grammarly to work better with Arc, so please hit me up because I think there's a few things that the Arc browser is doing that make it hard to get Grammarly to work either on the client or in the browser.

**Lenny** (01:07:10):
Two more questions. Do you have a favorite life motto that you often repeat to yourself, share with friends or family either in work or in life that you find useful?

**Noam Lovinsky** (01:07:18):
Gosh, for those that know me, this is going to share so much of my personality. I think the first thing that comes to mind is, we are meant to struggle. I just feel like through struggle is how we get better, how good things happen, how bonds form, and so I don't shy away from that kind of life experience.

**Lenny** (01:07:39):
I'm going to guess that you're Jewish. I'm also Jewish. That feels like a very Jewish thing to say. I love it.

**Noam Lovinsky** (01:07:43):
How would you guess, Lenny? It's literally written on my face. Yeah.

**Lenny** (01:07:48):
Perfect. Last question. As the chief product officer at Grammarly, I'm curious what word you most often misspell?

**Noam Lovinsky** (01:07:57):
The.

**Lenny** (01:08:00):
You do T-E-H?

**Noam Lovinsky** (01:08:01):
T-E-H. Yeah, exactly. Yeah, yeah, yeah.

**Lenny** (01:08:04):
Oh, man. Well, I find I misspell every word.

**Noam Lovinsky** (01:08:04):
Oh, that's funny.

**Lenny** (01:08:06):
I'm a terrible speller. I'm thankful for my... Oh, sorry. Go ahead.

**Noam Lovinsky** (01:08:09):
I was about to say I have a product for you that can help with your spelling if you want.

**Lenny** (01:08:13):
I am an active Grammarly user. Not only that. I use every product you've worked on, I realize.

**Noam Lovinsky** (01:08:17):
Oh, nice.

**Lenny** (01:08:17):
Obviously, Meta and mostly Instagram of the Meta products. And obviously Grammarly now and YouTube. I have a YouTube channel. Check it out. Subscribe and follow. And Thumbtack. My wife is a big Thumbtack user. We found many pros on Thumbtack from all kinds of parts of the world.

**Lenny** (01:08:35):
Noam, thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out and how can listeners be useful to you?

**Noam Lovinsky** (01:08:42):
Yeah. I'm pretty much @noaml everywhere online, so Twitter is probably the easiest. My DMs are open. And then how people can be useful to me is please use Grammarly, provide any feedback that you might have. And honestly, if I can be helpful in almost any way, feel free to reach out. I often will take those conversations and build those connections, and that is always very helpful for me as well.

**Lenny** (01:09:05):
No, thank you again so much for being here.

**Noam Lovinsky** (01:09:08):
Of course. Have a good one, Lenny.

**Lenny** (01:09:09):
Bye everyone.

**Noam Lovinsky** (01:09:10):
Bye.

**Lenny** (01:09:12):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

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## [17/19] The ultimate guide to PR | Emilie Gerber (founder of Six Eastern)

**Emilie Gerber** (00:00:00):
No one ever gets this tactical in PR. There's just so much theoretical conversation and examining the big blunders, but at the end of the day, if you're a startup that wants to get coverage for your company, you need to know actually the steps to take to do it.

**Lenny** (00:00:13):
You mentioned a bunch of amazing companies you've worked with, Ram Perplexity. Most products won't have this interesting of a story to tell. How do you help find something that is a nugget?

**Emilie Gerber** (00:00:21):
You can get so in the weeds with your own messaging that you want to set up this massive problem statement, you want to make it a huge trend story, but if you're very straightforward and you're pattern matching, it's generally actually going to work.

**Lenny** (00:00:32):
So I asked you to bring some examples of pitches that are great and also examples of pitches that could be better.

**Emilie Gerber** (00:00:39):
I want to read one to you and then I want to see if you can tell me what this company does.

**Lenny** (00:00:44):
Deal. Today, my guest is Emilie Gerber. Emilie is the founder and CEO of Six Eastern, a PR agency that has worked with over 100 tech companies, from stealth startups to publicly traded companies, helping them get press, build awareness, and level up their PR and comms strategy. Before starting her own firm, she worked at Uber where she led PR for the business development team and B2B programs. Prior to that, she worked at Box on product communications with a focus on product launches and partnership announcements. In our conversation, Emilie shares so many golden nuggets of advice on how to get press that I lost count.

**Lenny** (00:01:23):
We talk about which publications to target depending on your market and story, how to craft your pitch and your outreach to reporters, how to actually reach reporters, and also how to craft your product story for people to pay attention to what you're doing, why warm introductions to reporters aren't actually that important, how to find podcasts and newsletters to pitch that might be even more effective than traditional media, how much it would cost you to work with a PR agency instead of doing it yourself, and how much lead time you need if you do that.

**Emilie Gerber** (00:04:59):
Yeah, thank you for having me.

**Lenny** (00:05:01):
So we're going to be talking about press. A lot of people say that trying to get press isn't really worth your time. It doesn't drive signups, it doesn't drive growth. You could spend your time on other things and have a lot more impact there, and I know that you have a really interesting perspective on second order effects of press and other benefits. So I'm curious to hear, what's your perspective on this idea, that press isn't really worth people's time and how can press be helpful?

**Emilie Gerber** (00:05:27):
Yeah, when we were emailing about it, talking about some of the articles that you were in, some of the coverage that you got, I was thinking about how, in your case, you have multiple audiences. You have your customers, which in a way, are your listeners and the people that are engaging with your content. So in a way, you're a B2C business, but in another way, you're a B2B business. Obviously, you have sponsors and you're trying to attract really great guests to come on the show, and so there's a second order piece of the press is validating that you're something that a software company wants to sponsor. So internally, they're making those decisions. Not everyone might know Lenny's podcast, but they could send around a CNBC article and see that this is something very legit and something that people care about. It just signals that third-party validation that I think is really important, and that ties back to, when you look at a SaaS company or something and they're making decisions, having that validation, I think, and that credibility goes a really long way.

**Emilie Gerber** (00:06:24):
Especially for a company that might be early stage, they've raised a little bit of money, I think sometimes the buyers are skeptical of engaging with new tools, because they're worried they might not raise more funding, or it might go away tomorrow, and so the more that you can validate the business through things that's not just you doing personally that other people are doing, I think the better. So I think, yeah, that's the value from the B2B perspective and it's not necessarily going to directly drive signups, but when that AE is sending their sales emails and they can link to a story, I think that really helps. Also, candidates too, when you're reaching... If it's a recruiter reaching out on LinkedIn and they only have 100 characters to make their pitch, linking to that story can be really powerful.

**Emilie Gerber** (00:07:03):
So those are some of the second-order effects for B2B. And then, on the consumer side, it's a much more complex issue. There's affiliate marketing, which is this whole world of paid, where you're getting product reviews and that sort of thing, and that's not really an area that I'm an expert on, but we do work with some consumer companies where press is a major driver of growth. So for instance, Perplexity, they have invested essentially zero in any paid marketing, they don't have a marketing person even, but they do do PR. And so essentially, after their most recent announcement, they saw a massive spike in growth, a massive spike in signups, pro users, all of that. And I think, in that case, the reason PR works so well is...

**Emilie Gerber** (00:07:47):
First of all, it's something that's very easy to grasp. Google alternative. I know how to use Google, I've used Google a million times, you can go to perplexity.com. The barrier to trying the product is very low, you can quickly type in a query, get the answer, and then see the power of the tool. It takes one time to see the power of the tool. So in that case, I think just organic press is enough to generate that. There's not a long process to get the customers interested, so... Yeah. I mentioned very case to case, but in those instances, it works well,

**Lenny** (00:08:18):
Man, there's so many threads I want to follow here. That was such an interesting answer. And by the way, I love Perplexity. I once tweeted a result I had when I was using Perplexity, and that was one of their default questions you could ask about strawberries. Apparently, strawberries are not one fruit, strawberries are a bundle of fruits and every little piece of a strawberry, those little red things, are individual fruits all bundled together, which blew my mind. I was like, "I need to share this," and so I wonder how much of their growth just comes from crazy things like that.

**Emilie Gerber** (00:08:45):
Yeah, it's like the kind of tool where your mom could try it and instantly know how to use it. Yeah. It's good for weird questions, like what you just shared. That's where it comes in really handy.

**Lenny** (00:08:55):
You did a great job just defaulting, "Here's weird questions you could ask," and then, wow, what an answer. Okay, so on the B2B side, I think this is really interesting. When people are thinking about doing the calculus of, "Is it worth investing and trying to get press for a B2B business?" Related to what we were talking about offline. So when I got these stories in Fast company, I got a story in CNBC, I got a story in Entrepreneur Magazine, and I was telling you I've seen zero growth impact from all these stories. And you'd think like, "Wow." I had a story in the magazine, Entrepreneur Magazine, print edition, and nothing comes from it as far as I can tell.

**Emilie Gerber** (00:09:30):
Yeah.

**Lenny** (00:09:30):
And your point, which really stuck with me, is the real benefit isn't that first order growth impact, it's... And I've been doing this, it's when I'm emailing potential guests telling them, "Hey, check out my work or my profile in these magazines." And just having those little logos is really powerful, and that's why you see those logos on people's websites. So is your advice here, basically, for B2B businesses than most? If the pie chart of impact of press, most of that percentage is just having a logo of an awesome publication on your website and your outbound emails, and things like that?

**Emilie Gerber** (00:10:06):
Yeah, the logo is a piece of it and then also the storytelling part. Maybe they're not going to read eight paragraphs that you wrote about your business, but if it's in the format of an article, I think they're more likely to take the time to do it. One other, I guess, aspect of it is content. So for instance, the articles that people want to write about you are not about necessarily how great your podcast is, which it is, but more about how you created this business. And so it's more through the lens of you're an entrepreneur, you have built this media empire, and so that's not necessarily the kind of story that's going to drive your core audience to sign up, and so contents is part of it, too. And so we work with companies where we get them great stories about their company culture and cool initiatives that they're doing, because reporters are interested in that topic. That's not going to help their sales, but it might help with something like recruiting. And so yeah, I think thinking... That's the other piece of it, is thinking through the content.

**Lenny** (00:11:03):
That's such a good point, because the story they're going to write about you isn't, "This is the best product you've ever seen," this is, "Look at this interesting journey this startup has gone on," and that's not going to convince your customers, it's going to convince other people just to read this publication, but the fact that they wrote about you is really beneficial. And then you're saying B2C, most of the benefit is actually driving growth and you've seen lots of examples of press driving significant growth.

**Emilie Gerber** (00:11:27):
Yeah, I think it can be and I think this is one where, yeah, it's a little more case-to-case, because we have some clients where they need to invest heavily in affiliate, because product reviews are what they need or they want to be on lists of the best vacuum cleaner, or whatever category, and it's less about getting them big features. And so there's different ways of doing it for B2C. But yeah, I do think it's like... Yeah, there's two camps, affiliate or not affiliate.

**Lenny** (00:12:00):
Can you actually explain this affiliate bucket? Because I'm not actually that familiar with it.

**Emilie Gerber** (00:12:00):
I can. However, we actually don't do affiliate marketing, so there's probably going to be a lot of people that have a much more insightful perspective on it, but affiliate is essentially when you work with a publication to give them a percentage of any sales that come from the piece of the article. And so if you look at Business Insider's list of best personal finance tools, it'll say at the top that they're getting commission. So they track the links, they figure out a certain percentage, and then they basically get a percentage of all the sales that come in, and it's very common. I would say most consumer companies are doing this, but yes, there's entire agencies that are dedicated to that field.

**Lenny** (00:12:38):
Wow, I didn't actually know that was such a big thing. I've heard of affiliate marketing where you get paid for promoting something, I didn't know Business Insider did this as a revenue.

**Emilie Gerber** (00:12:48):
Yeah, and I don't want to call out just... I mean, I would say every publication that's doing product reviews for the most part, I believe, it's a very common practice.

**Lenny** (00:12:58):
Wow. All right, already learning a lot. Okay, so I definitely want to start talking about how to actually get press for your product, but one quick question about fundraising announcements. So I'm an investor in a lot of companies, very often, they email me and ask for advice how to get press and, most of the time, it's a fundraising milestone. When is it worth investing trying to get press and fundraising? Like always worth trying, rarely worth your effort? Does it have to be some really impressive fundraising moment? What do you suggest?

**Emilie Gerber** (00:13:32):
I also think not all PR people are going to agree with this, but I do think funding rounds, you can always get a reporter to cover if you go about it the right way. I mean, we scope out projects that are just for funding announcements, we've never had to not finish that project or we've never... I wouldn't do that if it wasn't possible, so I think there's a couple of reasons that it sometimes doesn't work out. But I guess just to take a step back on funding stories, a lot of founders automatically think that, "I raise money, so TechCrunch will cover this." The reality is... Someone tweeted, actually someone from another agency, I should... Propeller PR, they tweeted that they counted how many funding stories TechCrunch did in a week, and it was nine, so they had written nine funding stories in one week. And then they counted how many funding rounds actually happened that week by looking at Axis Parata and Fortune Term Sheet, and it was like 50.

**Emilie Gerber** (00:14:26):
So it seems... When you go to TechCrunch, it looks like, "It's all funding stories, so mine should be one of these." That's not the case at all. But I do think, if you go about it the right way, you can be one of those nine. And I'm talking about TechCrunch specifically here only because the reality is they are the publication that's going to be most likely to write your funding story, that's just kind of the way it works. And it's not a bad thing, they're actually... They don't have a paywall, they tend to do a very good job, they understand it. It's a well-oiled machine, and so we know if you've done a story with them, it's going to pretty much go how you want to plan it. So when you go to pitch a funding story, I think the first thing that founders, or whoever is reaching out on behalf of the company, does wrong is they convolute the message.

**Emilie Gerber** (00:15:10):
When we pitch a funding story, we make it very clear, "Hey, we're reaching out with a startup launch or funding. We're offering this to you as an exclusive, meaning we're not going to pitch anyone else if you take the story. Here's the amount that's raised, here's the space that... Here's the space they're in and here are the investors." I think you can get so in the weeds with your own messaging, that you want to set up this massive problem statement, you want to make it a huge trend story. You don't really say what you're trying to accomplish from it, but if you're very straightforward and you're pattern matching, "Hey, this TechCrunch reporter is the one that covers FinTech. I have a FinTech funding round, here's the reason my FinTech funding round matters." It's generally actually going to work and now it does 100% takes follow up.

**Emilie Gerber** (00:15:50):
You're not shooting off one email, you are respectfully following up. When I follow up, I like to come in with some new information, whether it's something they had tweeted in the past couple of days, a new article that they wrote, very respectful. I try to wait three or four days. If it's not going anywhere, then try someone else. Do that three or four times with the most relevant reporters. Generally, I think it works. Yeah, I think if you can just be really concise and direct and say what you're looking for out of the relationship, it tends to be a pretty easy process. And yeah, TechCrunch is one publication, but this actually goes for a bunch.

**Lenny** (00:16:24):
Amazing. I love that we're already getting into tactical advice for how to actually get press. So that was essentially for fundraising and the notes I took is keep it really simple, "Here's how much we raise, here's our investors. Here's one line about why this matters." I want to talk later about how pitching press is different for customers, because with customers, I think this is probably the mistake a lot of people make, and we don't have to get into this just yet, but you want to paint the picture of the market and trends and, "Here's where the market's going and why this is huge and why this is a solution to your problem," versus, "Bam, this is interesting for this reason," and that's it.

**Emilie Gerber** (00:16:56):
Exactly.

**Lenny** (00:16:57):
Okay. I want to talk about publications to target and what each one is best suited for. So you're talking about how TechCrunch is essentially really good for fundraising. When I think about other publications, there's like Axios and Verge, I don't know if they do press stories like this. Wall Street Journal, New York Times, things like that. So I guess, what are the different publications people should have on their list of target? And then, what are each of them most aligned to, story-wise?

**Emilie Gerber** (00:17:28):
I really love this question. I feel like no one ever gets this tactical in PR. There's just so much theoretical conversation and examining the big blunders and... It's all so high level, but at the end of the day, if you are a startup that wants to get coverage for your company, you need to know actually the steps to take to do it. So yeah, I appreciate that question. I'm going to answer it, but also answer it with the caveat that media changes so much and so fast. For instance, just a couple weeks ago, TechCrunch decided they no longer accept op-eds, which is... It's actually huge news for us, because we love doing op-eds in TechCrunch, and so things change all the time, but I will talk about it in its current state. So yes, TechCrunch, a go-to for a lot of funding announcements. A go-to for some product news, too, even sometimes.

**Emilie Gerber** (00:18:15):
I would say the areas where they don't have dedicated beat reporters, where we tend to end up not working with them, are health tech-related companies and even MarTech, too. We've struggled to find the right folks to cover those kinds of stories. So not everything, but generally, if you do your digging, you're able to find a relevant beat reporter or a couple of relevant beat reporters, and it's not just about getting coverage there. They have TechCrunch Disrupt, you can apply for speaking at that conference, and that sometimes actually directly turns into coverage. They have The Found Podcast, which interviews founders, and so if you have a really compelling founder story or topical founder story, that can be an excellent avenue to go as well. They have The Equity Pod, which is investment advice, so it's not just thinking about getting that one funding story with them, there are other ways to work with TechCrunch.

**Emilie Gerber** (00:19:02):
And I actually have heard really great feedback from clients on TechCrunch driving website traffic, the day of the announcement, especially... I haven't really been able to pinpoint when that does or doesn't happen. I'm trying to figure out if there's trends among that, but I have... Clients have sent me screenshots from the day of the announcement and they've seen a nice pickup from TechCrunch, so I think a lot of that comes down to the fact that they don't have a paywall, but their stuff tends to do really well. So it's a great spot, especially for that first piece on your company. Axios is really strong on the FinTech side, on the healthcare side, they have some really great beat reporters. The one thing I'll say about them is they're very deals-focused, so 100% would need to either have funding. If you're announcing a partnership that has a monetary component, that they would cover that. An acquisition they would consider covering, but they're not going to be... You should never pitch them on a product announcement.

**Emilie Gerber** (00:19:58):
And I think they might just get annoyed. There's a couple exceptions, a couple of the reporters might have little columns where they feature product-related things, but that's just not their bread and butter. And actually, Axios recently launched, or I guess has been launching over the past year or so, local editions. So they're really branching into local news, and so that can actually be a really nice way to get an Axios hit if you have a region-specific story. So I highly recommend checking that out. Another publication that we work with a bunch is Business Insider. If you struggle to pitch your funding story but really want it out in the world, they are big on the pitch deck stories. Those are a little controversial. Some founders, they're like, "This is not what I want my story to be about, I do not want to share my pitch deck."

**Emilie Gerber** (00:20:44):
But if you are in the camp of... You're open to that and you can redact, it does not need to have all the financials, it does not need to have the growth metrics, that can be a really great way to get a piece of coverage on your business. And the way that I explain it to clients is you're just getting all your core messages out there in a very direct way. You're sharing exactly what you shared with investors, that's not necessarily a bad thing. And sometimes clients will put in some customer slides, too, and so you can really make it a little bit more like what you're looking for. So yes, if you're looking for a funding story, TechCrunch passed, others passed, that's a good option. They also are huge on the entrepreneurial journey pieces, similar to the CNBC article that you got, but they really want metrics, they really push for metrics, so how much you're making, how much you're spending.

**Emilie Gerber** (00:21:35):
They love those kinds of stories, so it's not necessarily about how much you raise, but for people that have really built a business. And then the last thing for Business Insider, they do a bunch of these lists of top startups, of top professionals in the field. We love doing those, they're generally a really light list, and they put out a call for submissions. Takes five minutes and it's a way to get into Business Insider. There's so many of them, it's become a joke within my newsletter, because every week, there's five more and it's the most obscure different categories. Like top sports marketing professionals helping TikTok stars. I don't know, it's always a very niche ask, but those could be really great. Then a couple more.

**Emilie Gerber** (00:22:16):
VentureBeat is huge for AI news. We pitch them all the time for any client that we work with that is building AI capabilities, has a new offering related to AI, perfect publication for that. Fast Company is perfect for anything related to future of work, how people work. Really great for design, media, I would say perfect for any company that fits in those categories. They're also really open to op-eds, especially with leadership advice in them. And last but not least, on the list of ones that we work with most often, I would say is Forbes. Especially on the award side, they have the FinTech 50, AI 50, Forbes Under 30, all of that. And you're not going to get a feature with one of their main reporters until you're a bit further along, but they do have that really strong contributor network, which is much... A lower bar in what they'll accept, in a way. They're more open to covering earlier stage companies, so that's worth checking out, too. So those are my top ones, I'll stop there.

**Lenny** (00:23:15):
That's amazing. And those are the most commonly requested and the ones you mostly go after?

**Emilie Gerber** (00:23:20):
Yeah, they're the most realistic for most startups. There are ones like The Verge, and they're a little more gadget-focused and just areas that we don't necessarily touch, but could be good for some companies as well.

**Lenny** (00:23:33):
Got it, and then... I was going to say this for later, but there's obviously New York Times and The Wall Street Journal. Thoughts on going after those?

**Emilie Gerber** (00:23:42):
Yeah, we do get those questions all the time. I would say it comes up on calls with founders, "I want one out of every five." And really, when you look at... I make a joke sometimes like, "If you want those, just have a crisis and they'll write about it." Fire your CEO or do really intense layoffs and have some regulatory issue.

**Emilie Gerber** (00:24:00):
Playoffs and have some regulatory issue and you'll get a story there.

**Lenny** (00:24:04):
Uber got a lot of stories there.

**Emilie Gerber** (00:24:06):
Yeah, I can show some examples there. When you look at earlier stage companies that are getting coverage in those publications, that's what's happening.

**Emilie Gerber** (00:24:13):
Now, let's say you're a tiny bit further along and you're series B, series C, maybe even series C, and you're looking for coverage in those publications, there's a couple criteria that they're always going to want if it's to write a feature on your company. One is your valuation, so that needs to be something that you're sharing on the record. Two is your hard business metrics, usually revenue, sometimes something else. And so oftentimes they'll tell founders that and immediately they're like, "Oh, well we're not sharing that." So I'm like, "Okay, well that's kind of the end of the conversation." Sometimes it can be shared on background, but as a general rule, you're expected to share that sort of thing. So that's kind of a nonstarter a lot of times.

**Emilie Gerber** (00:24:51):
I totally think it makes sense to build relationships with the relevant beat reporters and ideally shoot for... When I say build relationships, I just mean shoot for an intro meeting on behalf of the clients, or they can reach out directly with those kinds of reporters, but they're just not going to write a feature on your company. If anything, you are going to be one or two sentences in a larger story of something that they're writing about. And yeah, that's just the nature of their coverage.

**Emilie Gerber** (00:25:16):
And then when you look at something like CNBC, they're targeting people that want to learn about public markets. And so if you're not a public company, they have their CNBC Disruptor 50 list, which is focused on companies that will soon be at that stage, but it's not going to be a place for early stage companies.

**Lenny** (00:25:32):
When I have these pieces in past company and CNBC, it was such a weird experience where I chat with them for half an hour and then it just comes out, and I have no idea what they're going to write about. Could be a complete tear down of everything I'm doing and you have no idea. How do you help try to avoid that sort of story? I know you have no control. Obviously reporters can write what they want to write about. Do you have any advice for how to avoid them writing something really negative about you?

**Emilie Gerber** (00:25:58):
Generally, if it's something that you're being briefed in advance, unless it is around something negative that's going on, it's just not their intention, it's just not going to happen. But what is a bigger issue is it not being the angle or the messaging that the company wants. And so part of that, there's absolutely nothing that we can do. Reporters are not our employees. We're not paying them to write these pieces. They have to maintain their editorial integrity.

**Emilie Gerber** (00:26:25):
And so I consider it my job to educate the founders and spokespeople that we work with that we cannot change anything the story says. What we can do is correct any factual inaccuracies, and we do that all the time. If something is factually wrong, we can get it replaced. But if they don't like that they were called, put in a category of software that they don't identify with, that's not something that we can fix.

**Emilie Gerber** (00:26:50):
Another thing that you can do though to prevent that from happening is just really ensuring that the spokesperson before talking to the reporter is going to nail the messages that they want. The more that you can reiterate over and over again how you want the article to be, I think the more likely that it'll land in the reporter's head and make sure that the reporter really understands what you're building and what your goals are. And all you can do is really use the briefing and the materials that you provide to kind of sway and influence, but there's not much beyond that.

**Lenny** (00:27:20):
So we've talked about all these publications. These are ones to consider going after. You also mentioned podcasts and awards as something people go after. Is there a tip you could share of how to find aligned podcasts or awards, like how you find a list of here we should go after these?

**Emilie Gerber** (00:27:35):
We use Google. We just use search engines basically for finding everything. And the way that we go about it is first figuring out who their customers are and what vertical they're in, and then just doing searches for podcasts that are within that vertical.

**Emilie Gerber** (00:27:48):
But it's not as easy as just reaching out to the ones that pop up first. The next step is a qualitative analysis. First of all, do they have vendor CEOs or vendor executives on their show? Let's say your product is sold to product managers. Maybe they only have product managers on the show. So instead you don't put the CEO forward and you put the right spokesperson-

**Lenny** (00:28:11):
Who could that be? What podcast might that be referring to?

**Emilie Gerber** (00:28:12):
Yeah, right? But this could be for CFOs. So let's say you sell into CFOs. Don't pitch your CEO for that podcast. Get a CFO and then pitch your CFO for that podcast. I'm very for companies hiring folks, or hiring so the roles that they sell into, it helps us a lot. So if your audience is a CFO, it really helps if you have a CFO. If your audience is a CMO, it really helps if you have a CMO, and that actually when your earlier stage isn't always the case, and so it's a lot harder to pitch. So I think that's the second part of the qualitative analysis.

**Emilie Gerber** (00:28:48):
The third is, podcasts really come and go, make sure... It sounds obvious, but make sure it's one that's actively producing. When you Google ones, half of them are not going to be active podcasts. And then the third is actually listening to at least part of one episode, making sure the quality is high, making sure it's the kind of thing you even want to associate yourself with. And then just looking at who the past guests are, is that the kind of peers that you want to associate yourself with?

**Emilie Gerber** (00:29:14):
And then one other thing that you can do is just in conversations with customers, find out what they're listening to, find out what they're watching, find out their media diet. And it doesn't have to be a big crazy survey that you send to your entire customer base. It can be casual. If you're farther along, it's great if you can make that a more formal sort of process, but it doesn't necessarily need to be.

**Emilie Gerber** (00:29:33):
And then in terms of reaching out, I highly recommend figuring out who the host is, just doing the research, figuring out who the host is, and then just sending them a casual note. I'm a big fan of just reaching out on LinkedIn and saying, "Hey, love the show. Are you open to guest ideas?" I don't even mention the client or anything, just opening the door. I just feel like that's so much more approachable and friendly than starting with a big pitch. And I think so many people start with this very long email introducing themselves or going really deep and you don't have to do that. And especially because maybe only one out of every 10 replies, it'll also save you a lot of time if you just start with something really lightweight.

**Lenny** (00:30:15):
I think that actually works really well. That's what I find is if it's a simple little message, I'm like, yeah, let me know what you got in mind. Even though 99% of the time it doesn't work out, sometimes it works out great. And so I find, sure, let's just see what you got. And then usually I'm just like, "Nope, sorry, not a fit."

**Emilie Gerber** (00:30:28):
And you get the reply that way. If you send the initial pitch and the reporter or podcast host isn't interested, chances are they won't reply. But if you just start with something friendly and they reply, they'll feel like, I guess a little more of a connection there, and so at least you'll get an answer. Whereas otherwise, you might not get an answer at all.

**Lenny** (00:30:48):
On the survey piece I think that's a great idea, and I've seen a few of my sponsors do this where they ask their customers, what podcast do you listen to? What newsletters do you read? Which is such a simple idea, but I think people don't do that. And just from that you could figure out, okay, here's the podcast we got to get on. Here's the newsletters we want to run after.

**Lenny** (00:31:06):
I want to talk about how to actually pitch well. But before that, we've been talking a bit about who to reach out to and how to do that. So there's a few questions here. It's just like how important is it to have a warm connection to a reporter? If you don't have that, what's the best way to reach out to them? Is it LinkedIn, is it Twitter DMs, something else? What advice do you have about, just before we get into the structure of the pitch, figuring out who to pitch and then how to get to that advice?

**Emilie Gerber** (00:31:34):
Who are your relationships question comes up on a lot of our calls with founders as well. I'd like to pose the question to you. Did we have a relationship before this?

**Lenny** (00:31:43):
Nope.

**Emilie Gerber** (00:31:44):
Exactly. I'm of the belief that it does not matter as much as many people think it does. And I explained this on calls where they ask, "Oh, tell me about your Rolodex, or who is your relationships with?" First of all, media's changing so fast. So sure, maybe there is a reporter that we worked with recently. They might have a completely different beat in six months. They might be at a very different publication. So it's not sustainable to build an entire career on having relationships with certain publications.

**Emilie Gerber** (00:32:17):
And media is changing too. Now, podcasts and Substack and newsletters, it is just changing too fast. And so I think cold outreach done well is just as effective. The only thing that a relationship will get you is an open and an answer. And so any good reporter is not going to be making their editorial decisions based on who their friends are. That's just not the nature. It shouldn't be the nature of the industry, and it's not. Maybe it'll get you an intro coffee, but that's about it. It's not going to get you coverage. They're not going to cover your news because there's a relationship there. I think the much harder and more important part is being good at writing really thoughtful notes to the right people.

**Emilie Gerber** (00:32:57):
And in a way, now we do have a relationship, and so it can come from a cold email, but now it's easier for me to pitch you because you know my name and we've spoken and we've worked together. And so for me, I'm a big fan of being helpful to reporters, and I tend to just keep it professional and pitch them on stories. I don't necessarily feel like going to drinks or having coffee all the time is crucial to building those relationships. A lot of the reporters that I work with regularly, I've never met in person, and that's okay, but it can be great for getting answers I would say. That's where the relationships can be helpful.

**Emilie Gerber** (00:33:35):
And then once you have worked with a reporter on a story, it's true that maybe they'll be more likely to come back when they're working on something related, use you as a source, quote you in articles that are relevant. So once there's something there, that's great and you should totally nurture it, but it's not all about calling in favors.

**Lenny** (00:33:52):
Awesome. Okay. And then in terms of how to reach reporters, what do you find most effective?

**Emilie Gerber** (00:33:59):
Yeah, I'm pro all platform approach. So sometimes reporters will tweet that they're working on a story about something, and rather than me sending them an email with my pitch, I'll say, "Hey, 10 words on why this person is the person you should talk to," and then send a link to an article on them and that's my entire pitch. And honestly, it's sometimes more effective than when I spend 30 minutes writing a really thoughtful email. So I'm a fan of that. I'm a fan of DMs, short, concise, direct DMs. Sometimes LinkedIn, although for whatever reason I feel like that works better with on the podcast side with hosts.

**Emilie Gerber** (00:34:38):
And then of course email, we totally email. When I email a reporter, I love to make the subject line just as clear as possible as what the goal is and why I'm emailing them. And so let's say it's for a recurring column that they have, I'll put the name of that column and the person that I think should be included in the subject line. And even that for a reporter, it's like, oh, they actually know. They actually know I write this column and they're suggesting a guest for this column. It's so direct, it's so clear.

**Emilie Gerber** (00:35:06):
I think just saying what your intentions are right away. Are you trying to get a Q&A? Are you trying to get a story? Are you trying to get a funding story, like I mentioned before, is very crucial, and keeping it short. I would say my most successful pitches are three sentences and anytime... Sometimes it needs to be longer than that, and generally I feel like my pitch is weaker for that reason. Attention spans are short, and so the more concise you can make it, the better. And then just sometimes I'll start with one platform. I'll start with an email and that doesn't work, so I'll go somewhere else. But I try to make it very human and respectful. So using language like, "Hey, I know your inbox is probably slammed. Sorry to annoy. Trying you one more time here."

**Emilie Gerber** (00:35:49):
Another thing that actually can work really well is pointing out gaps in their coverage too, and talking about things that they should be talking about. Like, Hey, my client's noticing this trend. I know you've covered it from this point of view, but no one's talking about it from this point of view. That can be really helpful because it shows that you are actually paying attention to what they are writing, but in a way that you're demonstrating that you have some critical thinking going on, not just, I liked your article on X, which is a common practice that PR people use is I like this, and then jump to your pitch. So yeah, giving it a little more thoughtful, pointing out gaps in coverage.

**Emilie Gerber** (00:36:25):
And then the last piece is, especially if you don't have hard news that you're pitching, having something pretty controversial to say.

**Emilie Gerber** (00:36:33):
So we work with a lot of AI companies. If nine of them have one stance on something happening in the field and one has the other stance, chances are that one is going to be the one that a reporter wants to talk to because they are getting so many pitches on this topic, but they want to write a balanced article, they need that opposing view. And so we really push our clients to have something unique and different and bold to say. And it obviously has to be a strategic decision for the business. You don't want to go commenting on regulatory things if it sounds like you don't want to necessarily be a part of that conversation, but there are I think instances where it can make a lot of sense to say something that's a little bit bold and controversial.

**Lenny** (00:37:15):
That last piece is really interesting. Is there an example that comes to mind where you had a controversial contrarian pitch?

**Emilie Gerber** (00:37:23):
Yeah, so we work with a company called Clockwise, which essentially manages your calendar and allows time for focus time within your workday. They move things around for you. And a couple of months ago, Shopify got tons of positive press for essentially canceling all their recurring meetings, and everyone was very intrigued by this strategy. Press was generally quite positive towards it, and so we knew that if we just wrote another piece saying, "Oh, this is great," no one would want to publish that. It had been said in a million different ways. So we looked at the topic a little more critically and we're like, okay, is this actually enough to change meeting culture within a business? And we kind of identified all these other things that we think need to happen in order to really change the culture in a way that's going to be sustainable and long-term versus just blanket deleting of calendar meetings.

**Emilie Gerber** (00:38:14):
And so we ended up turning this into an op-ed, so something that together we wrote and then pitched a publication. And yeah, the title was "Shopify's Meeting Cost Calculator Does Not Address the Issue of Wasted Time". And so it wasn't necessarily saying it was a horrible idea, but it was putting a little bit more of a critical eye towards it. And Fast Company was interested in the idea and they posted the piece by the CEO, Matt Martin, and it was a great thing for us to comment on. And so yeah, I think it doesn't necessarily need to be something where you're coming out against it, but just proposing something that's a little more thoughtful on the topic.

**Lenny** (00:38:53):
Just hearing that it sounds like such an obvious thing to do. Basically a reporter is looking for an interesting story to write about. If you tell them something interesting that they could put out, that's a win-win for everybody. So makes a ton of sense. Let me try to summarize the advice you've shared so far when you're, say DMing a reporter, your advice so far is basically be very direct. Just tell them, "Hey, I'm looking for..." What's an example of being direct? Is it like I'm looking for a story on this fundraising announcement?

**Emilie Gerber** (00:39:19):
I wouldn't say I'm looking for. I don't know, just I would say if it was a DM, I would say, "Reaching out from X company. Would love to offer you the launch story alongside their funding if you're open to it." And usually I'd either say the amount and the investors or the company name. If you give them both, you're kind of just giving them the story and they could run with it right away. That's actually an important distinction. And so you could either say, "Reaching out with this Martech company that's raised 8 million from X Investors. Really interesting approach, they're taking on X incumbent. Do you want the exclusive?" That's kind of how I would phrase it.

**Lenny** (00:39:59):
Okay, awesome. Then, try to keep it to three sentences. And you're saying sometimes when you go longer, you actually end up backfiring each time. Sometimes include a link to a story they've written or some other story about the company that might give them some context. Is that right?

**Emilie Gerber** (00:40:15):
Yeah. And a caveat on that is, if a competing publication just wrote a bigger similar feature on that, they're not going to want to see that. And so I would use that strategically. If it's a piece from a while ago on a different topic that does share a lot of info, I'll include it, but I'm not necessarily going to include something that might seem like why would I cover this when this was just written about.

**Lenny** (00:40:37):
Good point. You also talked about how try to acknowledge their inbox is probably slammed, and this is taking some time maybe in follow-ups, especially like, Hey, I realize your inbox is slammed, just thought I'd come back to this. Then you talk about this idea of identifying gaps in the writing, like, Hey, it seems like you cover Gen AI. There's this trend that we've been noticing that maybe it would be interesting to cover. And then something controversial or something a little contrarian that would get them. Oh yeah, this could be a really interesting story.

**Lenny** (00:41:08):
Awesome.

**Emilie Gerber** (00:41:08):
Yeah.

**Lenny** (00:41:09):
Is there anything else broadly in terms of pitch advice to get the attention of a reporter that comes to mind? And I know this is a lifetime of experience and it's hard to summarize all of it, but anything else?

**Emilie Gerber** (00:41:24):
Well, one topic, maybe this would be covered elsewhere, but one topic I think is talking about incumbents that this company is taking on. So a lot of companies want to position themselves as category creators, and I actually hate that. It doesn't work. It doesn't land with press, and most of the time it's not totally true.

**Emilie Gerber** (00:41:46):
And so instead, it's actually really great when you can talk about how you are doing what X household name does, but better for X reasons, and that works so well. I'll put that in subject lines. I'll put company taking on whatever Salesforce with X approach. It's so successful because instantly it gives the reporter a frame of reference. And so it gives the reporter, oh, I know what Salesforce does, so I can understand how this solution would be better. And a lot of companies really want to position themselves as the first to do anything in a certain space. They love the idea of category creating, creating these little marketing phrases that they use for the new category. And that's fine if perhaps that works on the sales side, but on the PR side, I would never have put that in a pitch.

**Lenny** (00:42:35):
There's just going to be a meta comment, but the two topics that are most controversial in this podcast that I have both sides of opinions on is the power of category creation and jobs to be done.

**Emilie Gerber** (00:42:48):
Oh, really?

**Lenny** (00:42:49):
There's a lot of passion on both sides.

**Emilie Gerber** (00:42:52):
I mean, sure, you can point to examples of the two companies that have done category creation well, but it's two out of what, thousands?

**Lenny** (00:43:06):
I love it. I'm going to keep poking this hornet's nest. I love it. Okay. But you're saying in your experience doesn't work when pitching reporters?

**Emilie Gerber** (00:43:10):
For PR. Yeah, simply for PR. In other areas of the business I can't comment on, but for PR, it's just not a useful tactic.

**Lenny** (00:43:18):
**Emilie Gerber** (00:44:35):
Sure. Sounds good. I guess since we're on the topic of category creating versus not category creating, I'll start with an example that's very relevant to that. So we worked with RAMP in their very early days, and one of their first product announcements that we did together was the launch of their bill pay offering. And so at the time, I think they were like a three billion dollar company, something along those lines. So big, but not as big as they are today. Product news rarely gets big feature coverage, especially for something along the lines of a bill pay offering for B2B companies.

**Emilie Gerber** (00:45:09):
And so essentially the way that we framed the story was how RAMP was now able to take on Bill.com, which at the time I'm not sure if it still is, was one of the best performing FinTech IPOs public company that really had still only captured two percent of this market overall. And so by positioning it as allowing them to take on this massive incumbent that was getting a lot of press, we actually were able to get a CNBC story on the launch of this product. Generally they won't even consider product stories, but they really liked the angle of this underdog doing something that could take on a piece of market share from them.

**Emilie Gerber** (00:45:47):
And the next day there was actually another story about how Bill.com stock had gone down and they did make mention of RAMP's news in that story. So it ended up really just, it was a very powerful way of telling the narrative there.

**Emilie Gerber** (00:46:02):
And another way, if we hadn't pitched it like that would've just been RAMP brings simple, seamless, streamlined ability to do vendor payments and new finance offering, first of its kind. All these things that might be how you would talk in your customer emails, but if I had pitched it that way, probably wouldn't have been a story. So if we had pitched it as them creating a new category of this all in one software, which I mean, yeah, it could be argued, that's another way to tell the story. I don't think CNBC would've been interested.

**Lenny** (00:46:34):
Awesome.

**Emilie Gerber** (00:46:36):
So, okay, another example, we work with a company called Column Tax, which is embedded tax filing software. So essentially they work with other FinTech's to allow people to file their taxes within the tools that they already use. And last year they partnered with a company called Propel that offers SNAP benefits. So essentially for low income families to receive the government benefits to offer tax filing directly within the app that they've created.

**Emilie Gerber** (00:47:04):
And that was one thing that they were doing amidst many other customers, that they had lots of different threads we could pull on with them, but we decided to really just focus our press strategy on that one initiative because it allowed us to tell macro story about TurboTax had to pay all these fines for practices that many considered unsavory around calling themselves free but not really being free. The IRS is building a free filing system, but it's in its very early days.

**Emilie Gerber** (00:47:35):
So the fact that they were having this offering that was supporting a lot of low income families, and I believe 40% of the people that filed their taxes with Column hadn't filed taxes in the previous year, so hadn't gotten a return. It's like identifying the piece of the story that's most interesting and then doubling down on that. So we were able to get a great fast company piece instead of pitching this macro here are Column Tax's latest growth metrics, and they're announcing a partnership with Propel. And so it's like...

**Emilie Gerber** (00:48:00):
Growth metrics, and they're announcing a partnership with Propeller. And so it's figuring out how to tie it to these things that people actually care about, and not just the company's messaging I think is our job.

**Lenny** (00:48:12):
Amazing, is there any other examples? Otherwise, I'll share your pitch of someone coming on my podcast, and what worked about that.

**Emilie Gerber** (00:48:20):
I do want to share one more, because it's my favorite. I want to share my favorite funding story that I worked on. And so I'm actually going to pull it up, because this one is very graphic, in terms of how we went about showing the product. So we worked with a company called Gamma, which is essentially bringing a PowerPoint into something that's much more modern, and interactive, and usable. So when we did their launch, they were a seed stage company, we tried to get really creative with how we could display or talk about the company. And so instead of doing your standard company blog posts, we actually made a Gamma presentation, and we kind of included all these fun elements that made it really interesting to reporters. So firstly, it's a visual platform. So we created... Or actually I don't want to take credit for this. The Gamma team created this great visual.

**Emilie Gerber** (00:49:11):
And we kept it very to the point. Every year, half a billion people create presentations in Google Slides and PowerPoint. We're not using marketing language here, we're talking in a very direct way, we're including fund visuals. We talk about Gamma's mission, pretty short, this is not a long essay on why the company exists. And then we include some customer love, so they're early stage, so we didn't really have necessarily growth metrics that we wanted to share. So we tried to make it a little bit more personal, and focus on actual users and what they're saying, while also showing the product capability here. And then instead of doing a long thing on each investor, we just bulleted who the investors are, which is very to the point, easy for a reporter to repurpose.

**Emilie Gerber** (00:49:55):
And then the fun part that I really loved, is we did a video from the lead investor talking about why she invested, instead of including an investor quote. So it's a little bit different than what you expect. And their videos are fun, because they have all these interactive elements. And yeah, team photo, make it a little more personal. And that was about it. But anyways, it was a very successful story, and I believe the title of the TechCrunch article that we got as a result was Gamma Brings PowerPoint into the 21st Century. Exactly, that's exactly what we're talking. Maybe they are creating a new category, we weren't talking about it then, we're talking about how it's better than the existing solutions. And so yeah, I guess the piece of advice there, is feel free to get kind of fun and creative with it, and don't just follow the typical issuing press release format.

**Lenny** (00:50:42):
And is that something we could link to for people to check out? Is that just on their site?

**Emilie Gerber** (00:50:42):
Yeah.

**Lenny** (00:50:42):
Okay, amazing.

**Emilie Gerber** (00:50:46):
Yeah, I actually had to for some reason do some digging to get it. But yeah, I have it now, so I can give it to you.

**Lenny** (00:50:52):
Okay, great. And the way that you use that is when you sent emails or DMs to reporters, you included this link?

**Emilie Gerber** (00:50:58):
After they had that they're potentially interested, because again, if I had shared it right off the bat, it would be their prerogative to just publish it essentially or share it publicly. And I guess one important note, is everything you say to a reporter in an email is on the record, and so that's why I make the point on not sharing the entire story right off the bat.

**Lenny** (00:51:19):
Got it. So many companies won't have... They're not a deck product, so they can't do something like this. But the takeaways for other folks here, is be just very human in the language, the investors are just bullet points, make it fun, add some visuals, don't just have blurbs, and paragraphs, and things like that.

**Emilie Gerber** (00:51:41):
Yeah. I think reporters are used to getting the same thing all the time, and so this one obviously worked well for the format. But I think we try to always think of, what can we do that's slightly different for this one? Or how can we make this a little more fun? I guess the one exception, if the product is very technical, and you have a very technical audience, and you're probably going to work with a very technical reporter, it's totally fine to talk to your audience in those cases, and you don't need to necessarily dumb it down so everyone can understand. But that doesn't mean... I mean, you can do that while still using clear and concise language.

**Lenny** (00:52:18):
Okay, so let me share the element of the pitch that you sent me, that convinced me to bring this guest on. So this is going to be the chief product officer at NewBank. I barely know anything about NewBank. And so in your email to me, you basically had just two bullet points, and the way you put is, "Two fun facts about NewBank, growth has been 80 to 90% organic because of the way they try to make customers fanatical about the product." And to me that's like, "Wow, that's very rare, is 80, 90% of your growth being organic." So to me is like, "That's an interesting story." And then the other tidbit is, "NewBank is bigger than Coinbase, Robinhood, Affirm, SoFi, and Lemonade combined. Seriously, so much bigger than people in the US realize." Which I 100% did not realize. So to me both were just like, "Okay, this is an interesting story to tell, I think people would be very curious to hear how a company like this operates." So now I'm going to start getting all these emails from people, all these couple bullet points.

**Emilie Gerber** (00:53:15):
They're going to combine a bunch of companies, and see which they're bigger than.

**Lenny** (00:53:19):
Yeah, or use AI to help them figure this out. But I think what you identified here is just what I get excited about. Is there any advice there of just what you did there that other people can learn from?

**Emilie Gerber** (00:53:32):
Yeah. I mean, I think with pitching you, speaking to the audience, it's not just about having... You don't want the most well-known CEOs all the time, you're not looking just for the biggest companies and the most well-known people. You're looking for the things that they can talk about, and how the things that they can talk about are relevant to your audience. And with the first bullet, it was indexing on that. The second bullet was more so like, "Hey, you might not know about this company." And it's a little bit of a unique one, I wouldn't necessarily always include that. But to me the first bullet was really what mattered, because it wasn't just about the fact that they were a huge company, it's that they grew in a unique way, and I knew that was the kind of thing that you'd be interested in.

**Lenny** (00:54:13):
And how did you figure that out? Is it from emails we were exchanging ahead of that? Is it listening to some podcasts? How did you get to those conclusions?

**Emilie Gerber** (00:54:21):
Yeah, listening certainly helps. But I do think just figuring out... If you even just scrolled the names of all the episodes that you've done, it would be pretty easy to spot a trend there. And so you're not talking about product launches, you are not talking about entrepreneurial journeys, you're talking about tactical lessons. And so pitching people based on those sort of things, I don't even think you necessarily need to listen to a whole bunch of episodes most of the time, maybe occasionally you want to gut check something before you reach out. But yeah, you can tell a lot just by doing a little bit of research.

**Emilie Gerber** (00:54:53):
And then we did have a little back and forth, because I will take responsibility, I did try pitching you on a CEO at one point, which I know you don't have on as guests.

**Lenny** (00:55:03):
Once in a while, very rarely.

**Emilie Gerber** (00:55:08):
Yeah, actually, there's obviously some exceptions. But I had known the subject matter you were looking for, but I did not spot the trend that you've never had CEOs on. So I think my pitch was actually okay, but the spokesperson was not the kind of person that you would want on. So maybe you won't get it right 100% of the time, but you can tell a lot just by doing some searches.

**Lenny** (00:55:24):
And oftentimes I just reply, "Here's my policy." And then, "Okay, good to know." Kind of along these lines, something I wanted to ask earlier, you mentioned a few publications to go after, and then how to pitch people. Obviously the way that you're describing takes a bunch of time. How many people are you often emailing, DMing per attempt to get a story? Because it sounds like it's not a ton, and so you have time to do these sorts of custom pitches. Or is it a lot higher than it sounds?

**Emilie Gerber** (00:55:51):
I would say for hard news, funding, the startup launch, those sort of things, less, and I try to really stagger it because we're offering exclusives, and I highly recommend offering exclusives. So the worst thing that can happen is two reporters reply, and are both interested, and you have to go back to one and say, "Nevermind." And sometimes that's okay if they left you, if it's been a week or something, they hadn't gotten back, and they'll understand. So it's fine to move on without getting an answer. So I would say, yeah, with the funding story, it could be anywhere from one to six reporters on average, sometimes more. With stuff like general just outreach, relationship building, trying to get on podcasts, it kind of is a numbers game, and you really have to balance quality and quantity.

**Emilie Gerber** (00:56:38):
And that's why I love starting with the first note and not saying much, and just saying, "Hey, you open to guest ideas?" Because it allows you to do more. I'd rather do that than send a bad pitch, and not have it be targeted to the right sort of audience. And so that's kind of a way to play the numbers game while still being respectful. But yeah, I mean, with some clients maybe they get one opportunity for every 20 or 30 things that we send. And so yeah, we try not to do... We don't do blasting media, it's not about sending the same pitch to a single list of people. It's figuring out, which ones do I want to really double down on because they're the perfect target? And you'll keep trying, you'll be really custom, which deserve maybe a slightly higher level note, which deserve a DM, and just figuring out your strategy from that.

**Lenny** (00:57:27):
Awesome, okay. Do you have examples of pitches, announcements that were not as effective as they could have been, and advice for how they could have been better?

**Emilie Gerber** (00:57:37):
Yeah, I have some excerpts that I pulled from press releases where I think there's room for improvement. So Lenny, I want to read one to you, and then I want to see if you can tell me what this company does. Okay, "Today X announced their workflow automation product, which combines AI assistance, human in the loop collaboration, and a robust multiplayer experience to help teams save time."

**Lenny** (00:58:03):
Absolutely no idea what's going on.

**Emilie Gerber** (00:58:05):
You kind of gained something from workflow automation, and then after that it's like, "Wait, what?"

**Lenny** (00:58:05):
Just a bunch of things.

**Emilie Gerber** (00:58:10):
Okay, now let me read to an excerpt from the TechCrunch article, and this is how TechCrunch positioned it, "A new automation startup is setting out to eat Zapier's lunch. It helps people tackle mundane and repetitive tasks, and goes beyond the triggers and actions popularized by similar platforms like Zapier." So to me, yeah, it's a better version of Zapier, where they aren't just doing triggers and actions, and there's a little more substance and depth to it. If you know what Zapier is, you can kind of start to figure out what they do based on that.

**Lenny** (00:58:41):
Yeah, it comes back to your point about referencing incumbent to help you understand what the heck you're talking about

**Emilie Gerber** (00:58:47):
And you wouldn't necessarily need to do that in your press release, but I think they could have been a lot clearer, and not use... Because terms like robust multiplayer experience, that makes it sound like a game. Are we talking about just collaborative multiple users? Human in the loop collaboration, isn't all collaboration between humans, and we're all in the loop? AI assistance, that just means they use AI. So yeah, sometimes I push my clients to like, "Okay, let's talk through what each of these phrases actually means. And if you can't articulate it, then let's change it to the way that you just articulated it, and it might be more successful." So yeah, that's a good way to do it. And just read it out loud, read it out loud and see if someone understands it.

**Lenny** (00:59:34):
Someone hearing this is like, "How could possibly anybody think that was great? How did these come about, these really bad descriptions?" I know it's hard to come up with something really short and pithy, but where do these come from?

**Emilie Gerber** (00:59:49):
It's just a culture within marketing and comms, of this is how we're supposed to write. And I just think that's a majority of how people do it, and they think it sounds smart, or they think it sounds more professional. I just think it's just how people are trained. And so even when we bring on someone new, part of my job is stripping away at a lot of that, and getting people... Everyone's capable of talking like a human being, we do it every day. But it's stripping away that thing that goes off in your head that you're supposed to be writing in a very marketingy way. Because I would say at least 50% of releases are like that, it's not a small problem.

**Lenny** (01:00:30):
Right. I love the advice you shared of just trying to say it out loud, hearing yourself, what does it sound like? Do you have any other tips for trying to make it something people get and connect to? I know that, again, it takes a lot of time to really do well and it's very context specific, but is there any other tricks that you find help you communicate what you're actually offering?

**Emilie Gerber** (01:00:48):
It's talking through the basic questions, what does this product do? Who is it for? Who are your customers? If you can answer each of those in one sentence... What product launch are we talking about here? If you can just answer each of those verbally, chances are you're not going to be far away from what you're looking for. Because when I talk to marketers, and founders, and teams, generally in the conversations I have no trouble understanding what they're talking about. They can articulate it just fine, it's only in the writing that it gets that way. So actually I think it's kind of easier to solve than many might realize. And then also I think there is some skill involved in removing words, not over explaining, you can make things more concise. But at the bare minimum, just strip out all the jargon, that's the first step.

**Lenny** (01:01:36):
I love it. So one way to think about it is, just think about, what does it do? Who is it for? Who are the customers? Is there something else along those lines that you shared there as a bullet point?

**Emilie Gerber** (01:01:45):
Well, I mean, if you're talking about what makes this business interesting? Why should people care? And not over indexing on that. I think that's just one part of the overall story, is why people should care about this business. And then what's new? Is it growth metrics? Is it the customer piece? Is it product? What makes this timely and relevant right now?

**Lenny** (01:02:08):
Okay, awesome. There's actually this awesome Twitter thread from a couple of days ago, where the CEO of Product Hunt did this thread where he asked people, "Share your tagline, and I will give you a much better version of the tagline." And he's really good at this. So I'm going to link to it in the show notes, where he can give you an example of what it looks like from bad to good.

**Emilie Gerber** (01:02:26):
I love that. That's exactly the kind of thing I would love to do too, because it's so fun and so easy.

**Lenny** (01:02:33):
It's easy if you're good at it, most people are not great at it. You mentioned press release in this example, you shared thoughts on value of press release, traditional press release versus not.

**Emilie Gerber** (01:02:44):
Press releases came about because reporters would be checking news wires for ideas of what stories they want to write. No reporters do that anymore, or a very small percentage, I don't know any reporters that do that anymore. So now it's this thing where you go to one of the PR distribution services, you pay them anywhere between 300 to $2,000, that's literally what it costs, and they put it on the wire. And for the more expensive services, it does get syndicated to this press release section of some business websites. No one, in my opinion, goes there for their news. I've personally never read an article, like a Yahoo Finance article, that was a press release syndication. So in that sense, they are not helpful for getting eyeballs. They also require... Going back to that more marketing form of writing, they require that you write like that.

**Emilie Gerber** (01:03:39):
The standard press release format, it's so formulaic, and I think it actually encourages that more marketing speak. The benefit is that you're getting all the news details in one place, so it's relevant for a reporter. However, you can do the exact same thing in a blog post. And the blog post can be this first person piece of content that's written by either the founder, or the product lead, or whatever executive, that has a lot more flexibility in the style. You can kind of write it however you want, it can still include all the same news elements. And it's much more shareable on social, you're not going to share a link to a press release on your Twitter or on your LinkedIn, but a blog, for sure. You can add your own graphics, it's great.

**Emilie Gerber** (01:04:21):
And you're also encouraging people to go to something that lives on your website versus this black hole of a newsletter. I should be fair, so I think that the reason that people say that they still do them, is that it helps with SEO. However, I've read a few articles that have said that Google no longer does prioritize press releases in SEO, so I don't know how much that holds up. And that it signals to the market that the company is more serious, so that's a perception thing. I personally think that blogs actually signal a more modern, kind of cool company than a press release. But at a certain stage in your growth, public companies, they do press releases for earnings, makes 100% sense. There are certain rules around when companies do need to issue press releases, so there's still a use case for them, I just think your average early to mid-stage startup doesn't need them.

**Lenny** (01:05:10):
This mention of blogs is where I wanted to go next actually, so it's a good segue. But before we do that, is there any other examples that you wanted to share of less than ideal ways of pitching a product?

**Emilie Gerber** (01:05:21):
One sentence I found in a press release that a lot of companies want to include that I always try to remove is... Well here, I'll give you the sentence, "Since exiting stealth in May, we've witnessed a 700% increase in organizations using our product." You're saying that since you were in stealth to now you saw a 700% increase, so you could have had one customer, now you have seven. And it's every company wants to do these percentage growth stats when they just launched, and I've never seen reporters include that in their stories.

**Emilie Gerber** (01:05:50):
And so there are ways to give signals of how fast you're growing without being that kind of disingenuous. One way that you could put something similar is, "Our revenue hit six figures at the end of last year, and has been growing about 30% each quarter, with 40% of adoption coming from the enterprise sector." So you're giving color to the growth, and you can kind of play with that, it doesn't need to be exactly something like that. But if you can make it a little more specific, I'm not against doing percentages, but I think there's a way to balance that with something that seems a little more realistic.

**Lenny** (01:06:25):
Or, "We went from zero to six figures in ARR in X months."

**Emilie Gerber** (01:06:29):
Yeah, no, totally. And it doesn't need to be huge, especially if you're doing your first story, they're not expecting that you're necessarily going to have massive revenue. And so I think founders might sometimes be concerned that it's not going to seem big enough or significant enough, whereas from working with a lot of companies, it's kind of the case across the board.

**Lenny** (01:06:49):
You mentioned a bunch of amazing companies, you've worked with Ramp, Perplexity, a few others. And people may feel like, of course you're getting pressed, those are amazing. Ramp grew to a 100 million AR in two years, Perplexity is this killer AI product, everyone's talking about AI. Most products are not that, they don't have as interesting of a story to tell. Is there either an example you could share of a company that didn't have an amazing story to tell, that you created an interesting story out of? Or just any advice for, how do you help find something that is a nugget that gets people excited?

**Emilie Gerber** (01:07:23):
So some of the examples I gave, so Clockwise and Column Tax aren't as big as some of the other brands I mentioned. So that's certainly actually the bulk of our business, I would say 80% of the companies we work with are at a stage where they haven't reached that kind of mass awareness yet.

**Emilie Gerber** (01:07:40):
Another really great company that we work with is Entropy. And so essentially they work with transaction data, they're an API. It's a very technical tool, it's not something that necessarily every reporter is going to instantly understand. But for them, we've actually really leaned into the founder story. She's this incredible woman who moved to the US, and actually struggled with getting her first apartment here because of the way that our credit scoring system is set up. And one of the use cases for what she's building actually directly relates to how our credit system could change in the future, and so we've been really leaning into that angle. And her personal story is really powerful. And so maybe sometimes the product isn't going to be something that you can easily pitch, but you can kind of find those other personal angles in or pull on certain threads.

**Lenny** (01:08:33):
And there it connects back to find the publication that cares about these sorts of personal stories, because TechCrunch probably won't.

**Emilie Gerber** (01:08:40):
Yeah. But she spoke at Money20/20, so it's useful for speaking abstracts too. Actually it was on a panel with Column Tax, we got them on together at Money20/20.

**Lenny** (01:08:52):
What a win.

**Emilie Gerber** (01:08:56):
No, and we love doing that, it's so fun when you do have multiple companies that you can connect. Actually, that's kind of a good macro point as well. It doesn't always need to just be about you, if you have an idea for a conference session, reaching out to colleagues that you've worked with at other companies, peers, people that are building other things that maybe don't compete better in a similar space, and packaging that up as like, "Hey, this could be a really strong panel." It's actually way more successful than just pitching yourself.

**Lenny** (01:09:24):
Awesome, okay. So you've mentioned a couple of times the rise of newsletters and podcasts. So there's kind of two buckets of questions here. One is going after these kind of non-traditional media platforms, and then the other is building your own following, and building a following on Twitter, for example. I know you worked closely with the CEO of Vox who's really good at this, and basically doesn't need press. Elon is amazing at this, maybe that's why he bought Twitter, he has this huge platform to talk about all the stuff. So maybe in the first bucket, talking about when you're trying to decide, should I go after traditional media, Vox, and VentureBeat, and Axios, and all these guys? Versus I'm going to go for newsletters. As an example, Ramp got a lot of benefit from Not Boring, that newsletter with Packy, who wrote about them constantly and loved it. And they're sponsored posts, and organic posts. So I guess the question there is just, how do you think about going after podcasts, newsletters, Twitter, LinkedIn, influencery platformy people versus traditional press?

**Emilie Gerber** (01:10:31):
I think of newsletters and podcasts actually in the camp of, if we're pitching traditional press, we're 100% pitching those. Social is its own ball game, but I would not leave out newsletters and podcasts from any core PR strategy. To me, it's now just a part of any PR program that we're going to run, because it's just part of media now. And to me, it's just a very important part of media. In terms of social, I think doing social well is very hard. So you gave Aaron from Vox as an example, that was all 100% him. I think I helped with one tweet once about a Microsoft partnership that we did, and I was so excited.

**Lenny** (01:11:10):
How did it do?

**Emilie Gerber** (01:11:11):
Actually really good. A publication ended up writing a story on the tweet about Microsoft and Vox partnership because of it. Yeah, so that was fun. But generally it's not always something that you can just turn on by hiring an agency. And I've seen many companies try doing that, and not necessarily see as much success as they'd hoped for. So if a founder is naturally good at that stuff, lean into it as much as humanly possible, go for it. If they're not, and you're trying to outsource it, it can be done to some success. But I don't necessarily think it's as easy as just posting three times a week on relevant topics, there has to be more going on there. I think that if the spokesperson or the executive that you're trying to build the presence of is willing to... Going back to what I said earlier, kind of push the limit.

**Emilie Gerber** (01:12:00):
... Presence of is willing to, going back to what I said earlier, push the limit on opinions that they have, be bold, be controversial, then it could be worth potentially investing in. And I have seen it play out where reporters have seen those posts and used and quoted things in their articles as a result, so it can tie to your traditional media strategy a little bit, they're not necessarily fully siloed, but I would say if you're considering investing in social to just do corporate channels and not think about executives, you're really leaving a lot on the table. Corporate channels, it's very hard to build a following.

**Emilie Gerber** (01:12:39):
To get someone to follow a brand and care about a brand, you have to be bringing something new to the table, because they don't want to read your latest blog post, they don't want to read a relevant article that your social person just decided to put out there. When you have an executive, you're following a personality, you're following a person, ideally there's more flexibility with tone, all of that sort of stuff. And so I think it's important to think about it from the people perspective and not just the brand perspective.

**Lenny** (01:13:07):
So just to make it clear, the CEO or some execs should be the people tweeting and LinkedIn, and not the company as a brand?

**Emilie Gerber** (01:13:17):
Yeah. And I don't know. I think that it can be a little industry specific as well for where it makes sense to be investing in the corporate channels. And you certainly can do that sort of thing. But I also think if you're going to do that, have an exec that you're also trying a social strategy with. Don't just do the plain corporate channels.

**Lenny** (01:13:36):
When I think of a brand doing this really well, it's Duolingo. They're just so hilarious and so ridiculous in there. And I don't know if the key is just funny is the way to go, and that's how you get any attention, but they're so funny and creative in their videos, especially TikTok.

**Emilie Gerber** (01:13:50):
It's interesting though, we're getting to the point where even brands having a personality on social is becoming its own meme. People are making fun of how all the fast food brands all are like these Gen Z like TikTok-

**Lenny** (01:13:59):
And they're all replying to each other on Twitter threads.

**Emilie Gerber** (01:14:02):
Yeah. And so things change quickly. So, yes, that was a good strategy, but you just have to stay on top of it.

**Lenny** (01:14:11):
So you talked about how if this comes naturally to you as a founder, obviously do it. I'm guessing for most people it doesn't. Do you find that it can work if you're just like, "I know this is important, I need to tweet often and share things," have you seen that work or is it just like it's just probably not going to be something that works great for you?

**Emilie Gerber** (01:14:31):
Yeah, I think it can work to some extent. Maybe you're not going to necessarily be going viral or getting hundreds or tens of thousands of followers. But for me personally I push myself to post on LinkedIn at least once a month, because every time I post we get at least one client inbound and maybe a candidate inbound. And so if you test it and you start to see value, push yourself to do it even if it doesn't come naturally. And that's, I guess, the nice thing about social is it's easy to test out. You can try doing it, you can post for a while, even for a month or two, see how it's going, and then adjust your strategy accordingly.

**Emilie Gerber** (01:15:06):
But, yes, I think for a lot of execs that we work with, it does feel like it's something that's really hard, there's a lot of overthinking, making sure it's right. You can get really in your head about it, and I totally understand that because I feel the same way. And so if it's taking up so much of your time and bandwidth just thinking about your social strategy, then I guess you can weigh if it makes sense to do that, but I think pushing yourself to try it is a great idea.

**Lenny** (01:15:31):
And then Aaron specifically is very good at this, is there anything that you learned from his approach to tweeting specifically? I don't know if he uses other platforms. That works really well for him.

**Emilie Gerber** (01:15:42):
I actually think I just learned so much. So it was my first in-house job, so I had worked in an agency, I hadn't worked internally at a company before, and I think I just learned so much about comms best practices from him in general, just even beyond social. He was so good at figuring out how to comment on things happening in the news, having just the right stance that was both interesting to the reporter but not necessarily threatening to the business, and just capitalizing on all those moments. And I just watched how that worked and I was like, "This is how good PR is." And it's like the space that they're in is not necessarily one that reporters are all writing about, but he was able to insert himself in those conversations really well. And I think also at the time that I was there at least just really valued press and was willing to put the time in and do the briefings.

**Emilie Gerber** (01:16:34):
And so just getting to hear how he speaks over and over again was really helpful. And then on Twitter, I think it clearly just comes naturally to him, and so it wasn't necessarily something that needed to... Like I mentioned, how some execs will spend all this time thinking through to the point where it could get in the way of other things. I think that's not the case there. And if anything, it just helped the business. And actually with his Twitter presence, I would say it's a good example too of stuff getting included in articles, like I mentioned in that Microsoft article. So it helps the PR strategy as well.

**Lenny** (01:17:10):
Amazing. And we'll link to his Twitter account. This is Aaron, CEO of Box, by the way. I think I mentioned at the beginning and then we just started talking about Aaron. Also, I realize, he tweets about this sometimes, he actually makes money from Twitter, and now the Twitter pays you for views and things and they share ads, he makes thousands of dollars also from X now, by the way, not Twitter.

**Emilie Gerber** (01:17:29):
That's so funny.

**Lenny** (01:17:30):
Yeah, it's pretty ridiculous. I think I've gone through every question that I had for you. I'm curious if there's anything else that you think might be helpful to share or cover or leave listeners with.

**Emilie Gerber** (01:17:43):
I can leave with one very tactical media opportunity that I love.

**Lenny** (01:17:51):
Amazing.

**Emilie Gerber** (01:17:52):
Okay, so here it is. It's a way to get a morning brew feature pretty somewhat easily. So they have this series called Morning Brew Coworking series, and they have it for Emerging Tech Brew, they have it for HR Brew, all their verticals. I think there's a CFO one, marketing one. And essentially if you go to the series, the coworking series, either at the top or the bottom, there's something where it's like, "If you want to be featured, click on this link and fill out this form," and it's about 10 questions. If you keep your answers interesting and fun and not too self-promotional, we've had, I would say, 50% success rate with getting execs featured that way. And all you have to do is submit through a Google form. And it's just one of my favorite media opportunities right now. It doesn't need to be CEO, actually probably shouldn't be a CEO in a lot of instances, but it's basically intended to help readers understand what the day-to-day looks in certain jobs and just get a little insight into the people that are in these jobs. And so I guess I just wanted to share that as something that you could do today for over 10 minutes and potentially get a story. Although, maybe not after you post this, so we'll see if they get an influx.

**Lenny** (01:19:03):
We're going to take down Mailbrew. Funny enough, they have an interview with Zuck today that they published on Morning Brew, so it could be you alongside Zuck.

**Emilie Gerber** (01:19:10):
There you go, yeah.

**Lenny** (01:19:13):
Maybe before we get to our very exciting lightning round, it might be fun to chat about how to pick a PR agency. Obviously you run one. When people are trying to decide who to work with and also when to decide to pick and work with a PR agency versus doing it themselves, what advice can you share when they're trying to make that big decision?

**Emilie Gerber** (01:19:33):
I think there's an assumption that bigger, more well-known agencies are going to do a better job. I think a lot of those bigger, well-known agencies are used to working with a lot of household brands. And so their strategies tend to be very reactive, focus in the messaging, maybe have to turn down a bunch of opportunities, control what people say. That is the polar opposite in my opinion of doing startup PR. Startup PR, you got to experiment, you got to try new things, you got to be scrappy, you got to be fast. We actually personally love diving into pitching right away rather than spending several months on messaging just testing and market right away. And so don't assume just because they have the huge logos... To your point, you're like, "Oh, well, you work with [inaudible 01:20:16] Perplexity, does that mean you know how to work with all these tiny companies?"

**Emilie Gerber** (01:20:19):
That's not necessarily a good thing, so don't just go buy the big logos. I would say that's my first piece of advice. My second piece of advice is find out what month one looks like with them. If month one is them just doing intake calls and learning about the company, and you're a startup that's still really paying close attention to how much money you're spending, you're not going to necessarily want to partner with an agency that needs a three-month ramp up cycle. And so really tactically understand what those first few months look like. I think that's something that I've noticed is a lot of agencies take a while before they get their hands dirty and start doing things. My third piece of advice would be writing recent writing samples. To the point of all those press release excerpts I shared, is that how they write? If it is, maybe they're not the right agency. So ask them. That's so easy. That's so easy to do.

**Emilie Gerber** (01:21:14):
Just ask them for a couple recent blogs or releases, whatever they tend to go for, and read those. And, of course, wins too. You want to see what kind of stories they're getting, but that's a little more obvious. A lot of people have already talked about this, so I'll just mention briefly, it's important to meet with the actual team you're working on, not just the founder of the agency. So asking who's our day-to-day going to be? Can we chat with them really quick? One thing I would say don't do is an extensive RFP process. We actually as an agency don't participate in RFPs. The two times I've done it, I have regretted it just because of the amount of work going in versus the value that's there. And it's you're asking a team to do a lot of free work for you, and generally I think the best players are not going to do that, so you're going to weed out some of the best players if you're asking them to do a lot of free upfront work. So those are a few considerations.

**Lenny** (01:22:06):
Perfect. And then just two more questions, because I imagine this is what people are thinking about when they're trying to decide should we find somebody is how long ahead of time they should find someone before something big is happening? And then just what's a budget they should have in mind for something like this? What's a minimum or a range, whatever you think would be helpful for people to understand here's how much you're probably going to be investing here?

**Emilie Gerber** (01:22:27):
Start times can vary from agency to agency. I think we can get started the week that a client needs us to, so maybe I'm not best equipped to answer this, but I would say before an announcement happens, you probably want to kick off six weeks in advance. So when we start with the company, it's like we're working on the blog, we're doing a media training, we're doing the media outreach, we're getting quotes from investors, or coordinating with all the parties, making sure images are being created so it's not just pitching and securing the article. So I would say buffer with time to pitch, make sure that the reporter is actually able to cover it. Six weeks is ideal. I would also note I highly recommend not having a firm date that you think you need to announce something and going instead with when a reporter is able to cover your story.

**Emilie Gerber** (01:23:12):
We get so many clients that come to us and they have this set date in their head, but there's not usually a real reason for it. It's like they're planning around it, it's like they have other comms they want to go out that day, but if you can optimize for the reporter over the timing, you're going to see such a better outcome because getting the first choice reporter is going to drive way more for your business than announcing it four days sooner. So leaving a little bit of flexibility for that agency is key. And I've even seen companies like issue a press release for big news with no coverage because they had stuck to a certain day and were very rigid about it, and they didn't get any stories for that reason. And so I think a good agency would counsel to offer that flexibility.

**Emilie Gerber** (01:23:54):
So six weeks I think is the ideal amount of time. And then budget, I would say the lowest end would probably be about 10K a month for an agency. You can find consultants, I think the best ones would be at least 8K a month, but for a small boutique agency starts at 10. I'll just be transparent, I'm very open about our pricing, our rates start at 15K a month for our retainers, and actually that's for a series A companies generally what they're at. And then I would say unless you are a global business that needs basically different teams for different product lines, which happens when you're a Microsoft of the world, that's another story. But if you're just a series C startup that's getting a lot of attention, I wouldn't go beyond 30K probably. There are plenty of agencies that go into the 50s and 60s a month, but that's just a whole nother world, and I'm not an expert on that part.

**Lenny** (01:24:56):
Amazing. Thank you for sharing all that. What if you're going for just a one-off, just help me get one story, what's a range there for budget you should expect?

**Emilie Gerber** (01:25:04):
I would say between 10 and 20. And you might be able to find a consultant that'll do it for eight.

**Lenny** (01:25:12):
Amazing. So helpful. Emilie, is there anything else you want to share before we get to our very exciting lightning round?

**Emilie Gerber** (01:25:19):
No. I'm ready.

**Lenny** (01:25:20):
Well, welcome to our very exciting lightning round. I've got six questions. Are you ready?

**Emilie Gerber** (01:25:25):
I am.

**Lenny** (01:25:26):
First question, what are two or three books you've recommended most to other people?

**Emilie Gerber** (01:25:32):
I have one that's very top of mind right now, so it's How to Change Your Mind by Michael Pollan. Actually, I leave tonight for a week long psilocybin retreat.

**Lenny** (01:25:46):
We should have done this... N [inaudible 01:25:48]

**Emilie Gerber** (01:25:52):
I know. I would be getting much more philosophical maybe.

**Lenny** (01:25:53):
Wow.

**Emilie Gerber** (01:25:56):
So very excited, I'm going to Jamaica.

**Lenny** (01:25:58):
Amazing.

**Emilie Gerber** (01:26:00):
And ever since researching that field, there's the whole concept of changing your neural pathways is just very fascinating to me. And just opening up and shifting perspectives is something that I think will actually help me a lot just even in running a company, being a better leader, I think we're at a stage in our growth right now where we're hiring a lot and there's a lot of pressure and I just want to make sure I'm bringing my best self forward every day. And so I'm really excited about it.

**Lenny** (01:26:27):
What an amazing answer. This is going to be part of your set and setting this interview, but hopefully you can get it out of your mind.

**Emilie Gerber** (01:26:34):
No, totally. I was nervous. I'm like, "It's actually really great that this is happening and then I can completely unplug after it. And so I think it's actually good timing.

**Lenny** (01:26:34):
I'm excited to hear how it goes.

**Emilie Gerber** (01:26:45):
I'm not a big book recommender. I have ADHD and reading full books is very hard for me, and so I'm just going to leave you with that one. I can do the occasional beach read I'll really focus, but it's not my main format of content consumption.

**Lenny** (01:27:01):
Amazing. All right, great answer. One's plenty. Do you have a favorite movie or TV show you've really enjoyed?

**Emilie Gerber** (01:27:08):
My favorite genre is post-apocalyptic, end of the world survival. I need to mention my all time favorite show, because it would be bad not to. So Walking Dead is my comfort TV show, I can watch it when I'm going to sleep at night, but my most recent favorite was Yellowjackets. Are you familiar?

**Lenny** (01:27:30):
I've seen the poster on my TV, but I've not watched it.

**Emilie Gerber** (01:27:35):
Nice. I discovered it a little late. I think the second season finished and they're working on the third. But it has plane crash, and it has just shocking moment after shocking moment like cannibalism, very weird stuff. And it's one of those shows that sticks in your mind, which I like where you're thinking about it afterwards. It's kind of creepy.

**Lenny** (01:27:59):
Wow. I thought you were going for Last of Us, but I now have to watch this show.

**Emilie Gerber** (01:28:05):
No, I watched Last of Us and I didn't feel like it had enough survival elements to it. It was like storytelling in that environment, but it wasn't actually a survival post-apocalyptic show in the way that I was looking for.

**Lenny** (01:28:17):
Hardcore. Do you have a favorite interview question you like to ask? And you could take this in any direction you want.

**Emilie Gerber** (01:28:25):
Yeah. I have a new one. We actually just revamped our interview process, so I wanted to make it harder. So my new favorite question is if a client comes to you and they're convinced they have something that's press worthy, like an announcement that they think should be, I don't know, in the Wall Street Journal or something, and you know for a fact that it isn't, what steps do you take? What do you do next? And I like that question because they can handle it, one, from the client relations standpoint, how do you communicate with the client when they say something like that, but it's also a critical thinking and creativity question of how do you take a no and turn it into a yes? How do you take what they're giving you and make it into something interesting? And so I like to dig into that, and they can use a real example if they want, but I also think a lot of our job is pushing back in a way. And so that also shows if they're able and willing to push back.

**Lenny** (01:29:17):
I'm so curious to hear people's answer to that. Do you have a favorite product that you recently discovered that you love?

**Emilie Gerber** (01:29:24):
I was very skeptical of Apple Vision Pro and I was making fun of it at the beginning, and the first time I tried it, I completely changed my tune, I'm so into it, I'm ordering one, and I'm very excited for actually using it for work. I think it could be a really good use case for just my day-to-day at work. After I had tried it, the next day I messaged a bunch of clients that I thought could have relevant applications for it. I'm like, "Do we have an Apple Vision Pro strategy? Are we billing to talk about it publicly yet?" Because sometimes it's tying back to the PR conversation, I love if you're willing to push the envelope on stuff that you are building or are going to do and getting ahead of those conversations, so that's a lot of conversations I'm having right now is trying to convince clients to talk about that.

**Lenny** (01:30:10):
So you have an Apple Vision Pro strategy, amazing.

**Emilie Gerber** (01:30:13):
And then my other one, which is very self-serving, because they are a client, but I do use them every day, is Perplexity. I find it so helpful even just for like I'm working on an award submission, I forgot how much funding a client has raised, asking them that instead of opening five different Google links and trying to find the answer, it's just huge for quick information. Or writing a bio for an executive, getting just the TLDR of what they've done in their past, it's so good for PR use cases, and I actually think marketing and PR is going to be one of the core work applications for them.

**Lenny** (01:30:52):
I've also already shared how much I love Perplexity, I have the Chrome extension installed. I probably use it at least once a day for podcast interview prep along with a bunch of other stuff. So good find for customer. I think they're going to do great. Wish I was an investor.

**Emilie Gerber** (01:31:07):
I'm the happy investor. I rarely angel invest and I was...

**Lenny** (01:31:12):
Drinks on Emilie someday.

**Emilie Gerber** (01:31:15):
There we go.

**Lenny** (01:31:16):
That's awesome. Good job.

**Emilie Gerber** (01:31:18):
Thank you.

**Lenny** (01:31:18):
Okay, two more questions. Do you have a favorite life motto that you often come back to, share with friends or family, either in work or in life?

**Emilie Gerber** (01:31:26):
Strong opinions loosely held, I'm a very opinionated trust my gut kind of person, but that doesn't mean I'm not willing to change my mind on things and be wrong. I first heard it from an influencer [inaudible 01:31:38] and then I Googled it, and apparently... What was it? Jeff Bezos also said it at one point, so I have no idea the origin of the quote, but I think that's a good one. You can still be really opinionated in life, but that doesn't mean you always are going to be right.

**Lenny** (01:31:52):
Emilie, this was everything I hoped it would be. I feel like this is going to help so many people get awesome press. Thank you again so much for being here. Two final questions. Where can folks find you and reach out if they want to learn more or work with you? And how can listeners be useful to you?

**Emilie Gerber** (01:32:06):
Our website is sixeastern.com and our email is hello@sixeastern.com, so you can find us there. And actually I have a newsletter called On Background. It's on Substack. And really what it's intended to be is a place for people to find these tactical opportunities, so it has media moves, it has reporters that are working on stories, it has awards that are open, all of this stuff that basically an intern in an agency would spend their days researching we put into a newsletter. And so its main audience is PR people, but I actually think it could be a great resource for people within companies that don't have PR teams to stay on top of stuff. So I guess to be helpful, feel free to subscribe. And then other than that, we're hiring, so if you happen to be a PR person that got this far in the episode, always looking for great people to bring on.

**Lenny** (01:32:57):
Amazing. Is there anything specific you're looking for in people you're hiring for people that may want to reach out other than they've been in PR?

**Emilie Gerber** (01:33:02):
Ideally some B2B experience. I think doing B2B PR is very different from doing consumer PR. If you work with startups, that's a huge plus, you know how to be kind of scrappy and fast. And also people that just love to be really hands-on and doing the actual work. We're very flat, so we're not a place where there's much managing of teams. So it's really much more like a consultancy than anything else.

**Lenny** (01:33:24):
Amazing. Emilie, thank you so much for being here.

**Emilie Gerber** (01:33:27):
Yeah, it was so fun. Thank you so much.

**Lenny** (01:33:29):
Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

---

## [18/19] Kunal Shah on winning in India, second-order thinking, the philosophy of startups, and more

**LENNY RACHITSKY** (00:00:00):
Microsoft, Adobe, Alphabet, IBM, Palo Alto Networks, even Starbucks, the CEOs of these companies were all born in India and immigrated to the US.

**KUNAL SHAH** (00:00:08):
A lot of CEOs have done well because they follow the “dharma” of the founders quite well.

**KUNAL SHAH** (00:00:13):
“These are the principles that were given to me and I'm going to sustain this and make it even bigger.”

**LENNY RACHITSKY** (00:00:16):
I want to keep talking about India and how it's different and how to build products that are successful in India.

**KUNAL SHAH** (00:00:21):
No Indian has ever been paid an hourly salary in their entire life.

**KUNAL SHAH** (00:00:24):
The concept of time is not the same.

**LENNY RACHITSKY** (00:00:27):
What do you see as the biggest opportunity for Indian startups?

**KUNAL SHAH** (00:00:30):
India is changing because now, for the first time, we are seeing founders being respected and unicorns being celebrated.

**KUNAL SHAH** (00:00:36):
We have a National Startup Day, and probably the first generation that will have to prove ourselves to be very large profitable companies.

**KUNAL SHAH** (00:00:42):
I wouldn't want to be anywhere else building.

**LENNY RACHITSKY** (00:00:48):
Today my guest is Kunal Shah.

**LENNY RACHITSKY** (00:00:51):
Kunal is one of the most well-known and respected entrepreneurs and product leaders in India and around the world.

**LENNY RACHITSKY** (00:00:58):
He shares endless wisdom on Twitter and LinkedIn where he has over 1 million followers.

**LENNY RACHITSKY** (00:01:03):
He's the CEO and founder of CRED, a FinTech startup based in India, which was last valued at over $6 billion and as of couple years ago processed over 20% of all credit card bill payments in India.

**LENNY RACHITSKY** (00:01:16):
Prior to CRED, he founded three other startups including Freecharge, which he sold for over $400 million to Snapdeal.

**LENNY RACHITSKY** (00:01:23):
Kunal is a deep thinker, both about product and about life.

**LENNY RACHITSKY** (00:01:27):
His background is actually in philosophy, which comes across very clearly when you hear him share his advice.

**LENNY RACHITSKY** (00:01:34):
In our conversation, we get deep into what makes working and building in India different from the US markets and other markets, including why trust is so essential and why so many people are so much more risk-averse in India.

**LENNY RACHITSKY** (00:01:46):
We talk about the biggest challenges and opportunities within the India market, why there are so many successful Indian immigrants in CEO roles across tech, and what we can learn from that.

**LENNY RACHITSKY** (00:01:56):
Also, why companies in India can quickly grow DAUs but not ARPUs, and what that means for building products in India.

**LENNY RACHITSKY** (00:02:03):
We also talk about how to stay curious and open-minded and the power of second order thinking.

**LENNY RACHITSKY** (00:02:07):
Also, stories of failure, lots of contrarian takes and so much more.

**LENNY RACHITSKY** (00:02:13):
If you enjoy this podcast, don't forget to subscribe and follow this podcast on your favorite podcasting app or YouTube.

**LENNY RACHITSKY** (00:02:18):
It's the best way to avoid missing future episodes and it helps the podcast tremendously.

**LENNY RACHITSKY** (00:02:23):
A big thank you to Cyan, my ET, for making the connection to Kunal.

**LENNY RACHITSKY** (00:02:27):
**LENNY RACHITSKY** (00:02:33):
**LENNY RACHITSKY** (00:02:36):
If you're building a SaaS app, at some point your customers will start asking for enterprise features like SAML authentication and skim provisioning.

**LENNY RACHITSKY** (00:02:45):
That's where WorkOS comes in, making it fast and painless to add enterprise features to your app.

**LENNY RACHITSKY** (00:02:51):
Their APIs are easy to understand so that you can ship quickly and get back to building other features, and hundreds of other companies are already powered by WorkOS including ones you probably know like Vercel, Webflow and Loom.

**LENNY RACHITSKY** (00:03:03):
WorkOS also recently launched AuthKit, a complete authentication and user management service.

**LENNY RACHITSKY** (00:03:09):
It's essentially a modern alternative to Auth0, but with better pricing and more flexible APIs.

**LENNY RACHITSKY** (00:03:15):
AuthKit's designed is stunning out of the box and you can also fully customize it to fit your app's brand.

**LENNY RACHITSKY** (00:03:21):
It's an effortless experience from your first user all the way to your largest enterprise customer.

**LENNY RACHITSKY** (00:03:26):
Best of all, AuthKit is free for any developer up to 1 million users.

**LENNY RACHITSKY** (00:03:31):
Check it out at workos.com/lenny to learn more.

**LENNY RACHITSKY** (00:03:35):
That's workos.com/lenny.

**LENNY RACHITSKY** (00:03:39):
**LENNY RACHITSKY** (00:03:42):
As a business, you care about revenue, but as a product team, the last thing you want to do is delay a product launch or a pricing change because your team has to rebuild billing from scratch.

**LENNY RACHITSKY** (00:03:52):
Orb is a flexible usage based billing engine that lets you evolve your pricing with ease.

**LENNY RACHITSKY** (00:03:57):
The fastest growing product teams at companies like Vercel and Replit trust Orb to power their pricing changes and launches.

**LENNY RACHITSKY** (00:04:04):
Use Orb to ship product faster, stop worrying about billing, and evolve pricing with ease and control.

**LENNY RACHITSKY** (00:04:11):
Check it out at withorb.com/lenny.

**LENNY RACHITSKY** (00:04:15):
And skip the line for demo or Sandbox by using promo code Lenny, that's withorb.com/lenny.

**LENNY RACHITSKY** (00:04:25):
Kunal, thank you so much for being here and welcome to the podcast.

**KUNAL SHAH** (00:04:29):
Lenny, thank you so much for having me, and a huge fan of everything that you do.

**KUNAL SHAH** (00:04:35):
And like I said before, India is a huge beneficiary of what you do.

**KUNAL SHAH** (00:04:40):
We are all people who have learned the art of product by just figuring it out, and watching some content here and there and reading some stuff.

**KUNAL SHAH** (00:04:49):
So kudos to everything that you do.

**KUNAL SHAH** (00:04:51):
And like I said earlier, you do a fabulous job of taking the information asymmetry of the art of product and  making it accessible to many of us across the world.

**KUNAL SHAH** (00:05:02):
So thank you.

**LENNY RACHITSKY** (00:05:03):
Wow, I really appreciate that.

**LENNY RACHITSKY** (00:05:04):
This is already feeling great to me.

**LENNY RACHITSKY** (00:05:06):
I have a huge.. so it turns out this podcast has a huge audience in India, as do you.

**LENNY RACHITSKY** (00:05:12):
And so I feel like this conversation is going to be really special and really meaningful to a lot of people.

**LENNY RACHITSKY** (00:05:18):
I wanted to start with something very tactical.

**LENNY RACHITSKY** (00:05:21):
There's a product framework that you came up with that I absolutely love, and I've shared it with at least 30 founders over the last couple years. And this is actually how I discovered you initially; I heard about this thing, and I'm like, who's this guy Kunal Shah?

**LENNY RACHITSKY** (00:05:34):
And look at us now, chatting.

**LENNY RACHITSKY** (00:05:36):
Could you explain this framework briefly and then just how you've used it or how you recommend people apply it?

**LENNY RACHITSKY** (00:05:43):
Oh, and by the way, it's called Delta 4.

**LENNY RACHITSKY** (00:05:44):
I don't know if I even said the name.

**KUNAL SHAH** (00:05:46):
Yeah, it's called the Delta 4 framework, but I think it's actually quite simple.

**KUNAL SHAH** (00:05:51):
If you think about it, a lot of people say that your product has to be 10x better and it's not very measurable.

**KUNAL SHAH** (00:05:57):
You don't know if you are 10x better or not unless you're delusional.

**KUNAL SHAH** (00:06:01):
And the trigger for me was actually, I'm the unusual tech founder in India.

**KUNAL SHAH** (00:06:06):
I'm the only humanities/philosophy major founder in India who's got into tech.

**KUNAL SHAH** (00:06:12):
And I often wondered if most people who were my peers, or people who were ahead of me, were significantly smarter academically or otherwise.

**KUNAL SHAH** (00:06:21):
And why did I become successful with my first startup, Freecharge, which I exited in 2015 for nearly $450 million?

**KUNAL SHAH** (00:06:28):
And I was like, “What would make this happen?”

**KUNAL SHAH** (00:06:31):
Because I would not qualify into this super league of really top IIT rankers that exist in India.

**KUNAL SHAH** (00:06:38):
And that got me onto this philosophical quest to find out what makes things successful.

**KUNAL SHAH** (00:06:43):
So the simple framework is, an example I give often is that, imagine the old way of taking a cab ride and an Uber. And if I asked you to give me the score of efficiency on Uber and let's say getting the old cab, what would you say, Lenny?

**KUNAL SHAH** (00:06:58):
I'm curious.

**KUNAL SHAH** (00:06:59):
Out of 10?

**LENNY RACHITSKY** (00:07:00):
Yeah, give a cab three and then Uber like a nine.

**LENNY RACHITSKY** (00:07:04):
Yeah.

**KUNAL SHAH** (00:07:05):
So every time you see that the product efficiency delta is greater than or equal to four, three things happen.

**KUNAL SHAH** (00:07:14):
It is irreversible.

**KUNAL SHAH** (00:07:16):
Second is that you have a very high tolerance for it to fail.

**KUNAL SHAH** (00:07:21):
If Uber fails a little bit, will you say, “Oh my God, I'm going to really stop using it?”

**KUNAL SHAH** (00:07:30):
No.

**KUNAL SHAH** (00:07:31):
And the third thing is what I call the UBP, ‘Unique Brag-worthy Proposition.’

**KUNAL SHAH** (00:07:37):
Every time humans unlock a Delta 4 product or service, they cannot stop talking or sharing about it.

**KUNAL SHAH** (00:07:46):
And therefore all Delta 4 products will naturally have lower CAC or sometimes zero CAC because people, humans.. and think about it, Lenny, how you discovered Google, definitely not through an ad, definitely not through some performance marketing here and there.

**KUNAL SHAH** (00:07:57):
Somebody showed you the demo and you were like, “Oh my God, this is crazy.”

**KUNAL SHAH** (00:08:01):
And that's what I'm seeing right now, what's happening with everything on OpenAI and everything that is happening around LLM feels like magic and it's Delta 4 because the efficiency of doing things before and after is now showing that.

**KUNAL SHAH** (00:08:12):
But failure is the real problem.

**KUNAL SHAH** (00:08:15):
And making everything tech does not make things more efficient.

**KUNAL SHAH** (00:08:19):
Let's take an example.

**KUNAL SHAH** (00:08:21):
Buying a suit for yourself online versus offline, all tech, cool stuff, all the features built in.

**KUNAL SHAH** (00:08:30):
What would you say the efficiency of buying a suit online is versus, let's say, buying a suit offline?

**LENNY RACHITSKY** (00:08:35):
I've actually done that and it was a terrible fit. It did not fit at all.

**LENNY RACHITSKY** (00:08:39):
And so it's efficient, but the end result was not, it's probably often not great.

**LENNY RACHITSKY** (00:08:45):
So it's probably-

**KUNAL SHAH** (00:08:46):
Overall efficiency score, what would you give?

**LENNY RACHITSKY** (00:08:48):
Of buying a suit online?

**KUNAL SHAH** (00:08:50):
Yeah, versus offline.

**LENNY RACHITSKY** (00:08:53):
I'd probably give it five and five.

**LENNY RACHITSKY** (00:08:56):
Offline is actually probably a better experience.

**LENNY RACHITSKY** (00:08:58):
I give it a seven.

**KUNAL SHAH** (00:08:59):
That's crazy because you've broken the principle, this is a tech product, but the efficiency is better offline.

**KUNAL SHAH** (00:09:06):
And therefore when the delta is less than four, what you will discover is that it is reversible.

**KUNAL SHAH** (00:09:15):
You will not see people bragging about it and you have zero tolerance for it.

**KUNAL SHAH** (00:09:21):
So you're never going to buy a suit online. I can tell you that right now.

**KUNAL SHAH** (00:09:25):
So I think it's a simple framework.

**KUNAL SHAH** (00:09:28):
I believe that if many companies applied..  I know now many VCs in the US use this as part of the training program for analysts.

**KUNAL SHAH** (00:09:36):
omebody in Sequoia mentioned this to me that they have this as part of the thing, but in India we are not still applying many of these things.

**KUNAL SHAH** (00:09:46):
I think it's a simple framework to at least know. You can apply this to features, you can apply this to products, you can apply that to business.

**KUNAL SHAH** (00:09:55):
And oftentimes this is a longer concept.

**KUNAL SHAH** (00:09:57):
We can talk about it in many ways because it's derived out of some study around entropy and evolutionary biology, which is the root of how I discovered and thought about Delta 4, that “When does a species get disrupted ” or “what is entropy and why does low entropy require growth of high entropy?”

**KUNAL SHAH** (00:10:18):
It's a day long podcast on its own.

**KUNAL SHAH** (00:10:19):
So some other time.

**LENNY RACHITSKY** (00:10:21):
Okay.

**LENNY RACHITSKY** (00:10:21):
We'll save that for a future follow-up, just diving in on the psychology of Delta 4. Just to kind of summarize this, because I think it's such a powerful framework and I find it useful to convince founders why their product isn't taking off.

**LENNY RACHITSKY** (00:10:32):
They may feel like this is better than. The classic example, is a better Excel.

**LENNY RACHITSKY** (00:10:36):
Look, this is so much better than Excel.

**LENNY RACHITSKY** (00:10:38):
It can do all these things.

**LENNY RACHITSKY** (00:10:39):
You don't have to learn all these formulas.

**LENNY RACHITSKY** (00:10:41):
But the trick here that I love is just what people rate the existing solution 1to 10, what would they rate your solution 1 to 10?

**LENNY RACHITSKY** (00:10:48):
It has to be four points higher, otherwise no one's going to pay attention.

**LENNY RACHITSKY** (00:10:52):
And I think it's pretty simple.

**LENNY RACHITSKY** (00:10:53):
People are busy, they have enough things to do, they have enough products and apps, they're not going to take the time to really dig into something if it's not that much better.

**KUNAL SHAH** (00:11:00):
Absolutely.

**LENNY RACHITSKY** (00:11:01):
Okay.

**LENNY RACHITSKY** (00:11:01):
I'm going to go in a totally different direction.

**LENNY RACHITSKY** (00:11:03):
I want to talk about Indian CEOs in the US.

**LENNY RACHITSKY** (00:11:06):
Okay.

**LENNY RACHITSKY** (00:11:07):
So today the CEOs of Microsoft, Alphabet, Adobe, which is a $250 billion company it turns out, IBM, which is a $170 billion company, Palo Alto Networks, which is a $100 billion company, even Starbucks, also a $100 billion company, I was looking that up.

**LENNY RACHITSKY** (00:11:25):
And then also Twitter before Elon took over Twitter. The CEOs of these companies were all born in India and immigrated to the US.

**LENNY RACHITSKY** (00:11:32):
And I might be wrong, but I think this is the largest ethnic group of CEOs of tech companies other than just white dudes in the US.

**LENNY RACHITSKY** (00:11:41):
Okay.

**LENNY RACHITSKY** (00:11:41):
So I'm curious why you think Indian immigrants are so successful in business and in tech in the US, especially in these very high positions.

**LENNY RACHITSKY** (00:11:50):
And I'm most curious, just what can we learn from that?

**LENNY RACHITSKY** (00:11:53):
What can we learn from their success?

**KUNAL SHAH** (00:11:55):
It's a great question.

**KUNAL SHAH** (00:11:56):
I often wonder about it and I have had the good fortune to meet a fair bunch of these individuals, and had a chance to really explore with them what really went on.

**KUNAL SHAH** (00:12:07):
So there are a few things that pop out.

**KUNAL SHAH** (00:12:10):
And again, these are all conjectures, which I can't prove in any way, but it's a thought experiment to talk about these things.

**KUNAL SHAH** (00:12:18):
First is in general, immigrants that get out of the country usually have a chip on their shoulder in a very different way.  And the struggle that they have to go through to just get out and be successful, and that hunger that got them there. There was no privilege.

**KUNAL SHAH** (00:12:37):
They came from very, very humble backgrounds and literally no money to start with.

**KUNAL SHAH** (00:12:42):
So I think that this force is real.

**KUNAL SHAH** (00:12:46):
You can say that for many immigrants in general as well. But appreciation for math in general, or logic which came to society in a big way, kind of gave. Let's say for example, lots of engineering graduates come from only a few countries because society was bent towards early exposure to mathematics.

**KUNAL SHAH** (00:13:04):
And I think that kind of helps create status that will get appreciated.

**KUNAL SHAH** (00:13:10):
For example, being an engineer, a doctor...  As a philosophy major, I was a write-off for society.

**KUNAL SHAH** (00:13:16):
So the reason I'm the rare commodity over here, because you are not considered to be very bright unless you break into these very hard exams and do very, very hard things.

**KUNAL SHAH** (00:13:25):
So the filtering criteria on its own is big.

**KUNAL SHAH** (00:13:28):
But there's another interesting framework altogether, which I have actually learned from this gentleman, Devdutt Patnaik. He applies Indian mythology and management principles together.

**KUNAL SHAH** (00:13:39):
And it's an interesting thing. There are three major Indian Gods.

**KUNAL SHAH** (00:13:43):
One is Brahma, the God of creation, Shiva the God of destruction.

**KUNAL SHAH** (00:13:49):
I'm  generalizing here, but that's the classification.

**KUNAL SHAH** (00:13:52):
And the third is Vishnu, the God of sustenance.

**KUNAL SHAH** (00:13:55):
And their avatars-the word “avatar” comes from Vishnu who keeps changing avatars.

**KUNAL SHAH** (00:13:59):
So we have Rama, Krishna, all these Gods are avatars of his.

**KUNAL SHAH** (00:14:04):
So what you notice is that if you take a two by two of people who are high on values and low on values, are high on obedience and low on obedience, you make an interesting two by two.

**KUNAL SHAH** (00:14:19):
Now, Lord Krishna, who is one of the very popular avatars, which suits the entrepreneurial category,  is high on values but very low on obedience. He was known to be the naughty God and he could actually create lots of things.

**KUNAL SHAH** (00:14:36):
And there is Rama, who is known to be the one who follows principles and is obedient.

**KUNAL SHAH** (00:14:41):
So they will follow ‘dharma’ and scale on that.

**KUNAL SHAH** (00:14:45):
And then there are these notorious characters, there is Ravana who is low on values, low on obedience, and there is Duryodhana which he says that he is high on obedience but low on values.

**KUNAL SHAH** (00:14:55):
So these are the people that you don't want to be.

**KUNAL SHAH** (00:14:57):
And what you notice is that a lot of CEOs have done well because they follow the ‘dharma’ of the founders quite well.

**KUNAL SHAH** (00:15:05):
They have not diluted the dharma of the founders who have started these companies, and managed to sustain that.

**KUNAL SHAH** (00:15:13):
And a lot of CEOs have this need to say, "Oh, I'm going to change the company forever and it'll be my identity and I will change the logo and I'll change the name and I will do all sorts of things."

**KUNAL SHAH** (00:15:25):
But maintaining ‘dharma’, where I will say that “These principles were given to me and I'm going to sustain this and make it even bigger," comes from the humility of saying that there is something that was built with some pure form factor, and I think therefore that character stays on.

**KUNAL SHAH** (00:15:41):
And therefore we have the characters of Brahma and Shiva, the founder and destroyer.

**KUNAL SHAH** (00:15:47):
That's the thing.

**KUNAL SHAH** (00:15:48):
But sustenance is the harder one.

**KUNAL SHAH** (00:15:51):
And therefore our avatars keep happening over time and different hurdles come and then different levels come.

**KUNAL SHAH** (00:15:57):
But when you think about the archetype of, at least the Indian CEOs, I've seen that they are fabulous at moving between Krishna and Rama all the time.

**KUNAL SHAH** (00:16:07):
They can play this consistently, and therefore they keep evolving and keep making these companies bigger and bigger.

**KUNAL SHAH** (00:16:14):
And I think we'll see a lot more of this in years to come, because now they have the role models of these individuals who have done well.

**KUNAL SHAH** (00:16:22):
But the key principle is that if you ask the founders, they will love these CEOs if they're around because they maintain the dharma.

**KUNAL SHAH** (00:16:32):
For example, what Tim is doing is maintaining the dharma of Steve Jobs because if he had tried to change the dharma of Steve Jobs and the values of the company, it's very hard to imagine it sustaining itself forever.

**LENNY RACHITSKY** (00:16:45):
Wow, what an answer.

**LENNY RACHITSKY** (00:16:47):
What I love about this is this combination of using a two by two and Indian mythology. It is like the microcosm of you, which is philosophy and tech.

**LENNY RACHITSKY** (00:16:58):
And so I love that and it makes a lot of sense that that's where your mind goes.

**LENNY RACHITSKY** (00:17:02):
Something else this makes me think about is, I read this book a long time ago, Jim Collins ‘Good to Great’ or one of his early books about leadership, and he talks about level five leadership I think. Here level five leaders are ones where it's not about them, it's about the business and they can disappear in the future and things will work great.

**LENNY RACHITSKY** (00:17:19):
Yes.

**KUNAL SHAH** (00:17:20):
And I feel it is very hard if you believe that your identity needs to have its own position and legacy, and therefore a lot of time chasing status causes disruption because you will say that “Oh, this doesn't have my signature in it.”

**KUNAL SHAH** (00:17:37):
And therefore accepting the religion and trying to be the Pope of it or the father of it is better than trying to say, "Oh, I need to have my variant of religion."

**KUNAL SHAH** (00:17:50):
And that's where the creative destruction starts happening.

**LENNY RACHITSKY** (00:17:54):
Interesting.

**LENNY RACHITSKY** (00:17:55):
Okay.

**LENNY RACHITSKY** (00:17:55):
So you said that there's this good balance between Krishna and Rama that happens.

**LENNY RACHITSKY** (00:17:59):
Can you just summarize where they are in that two by two?

**KUNAL SHAH** (00:18:02):
Rama is high on values and high on obedience, and Krishna is high on values and low on obedience, but they both are high on values, which means they'll follow dharma, and they'll change sides.

**KUNAL SHAH** (00:18:17):
For example, let's say Satya during the OpenAI crisis played Krishna and got things out, but he'll switch back to being Rama and continue to keep scaling it up.

**LENNY RACHITSKY** (00:18:29):
Amazing.

**LENNY RACHITSKY** (00:18:29):
And just to close the loop on here, is your sense that they're actually thinking about this and they're religious, or is this just in the ether of growing up in India and this is just part of the culture?

**KUNAL SHAH** (00:18:40):
It's a great question.

**KUNAL SHAH** (00:18:40):
I don't think they consciously think about it, but I think if they ever heard this, they would agree with it, because that's what they grew up with and value systems are much more long-term.

**KUNAL SHAH** (00:18:51):
For example, I believe all bad behavior in humans comes from being short-term, and being long-term is a big choice to make.

**KUNAL SHAH** (00:19:04):
And a lot of times a lot of people argue that we have a 95% arranged marriages and less than 1% divorce rate, comes from this whole long-term thinking that people are married through values versus attraction or lust and all of that stuff. They’re more long-term oriented and about building a family, building values.

**KUNAL SHAH** (00:19:31):
Or low divorce rate is about “we'll fix along the way” versus trying to say “I need to evolve” and “I need to move forward.”

**KUNAL SHAH** (00:19:38):
So I think being long-term about that mindset, and that's why some cultures last for thousands of years, because of this need for everybody to be more long-term versus short.

**LENNY RACHITSKY** (00:19:52):
The US could use a lot of that these days.

**LENNY RACHITSKY** (00:19:55):
You mentioned this interesting fact about how in India, most startups fail. You said, I think, the classic stat is 90%, and that the risk is a lot higher to start a company and then fail.

**LENNY RACHITSKY** (00:20:08):
Can you just talk about what impact that has?

**LENNY RACHITSKY** (00:20:11):
How do people try to avoid that?

**LENNY RACHITSKY** (00:20:12):
Because that'd be amazing if you can reduce the risk of starting a company or is it just that it happens and people get super in debt?

**KUNAL SHAH** (00:20:20):
I think long-term societies are naturally more risk-averse. And not all great CEOs can become great founders for the same reason.

**KUNAL SHAH** (00:20:32):
In fact, I would say that it actually makes it very hard to be a founder if you've been a great CEO because you've turned into this sustainer versus destroyer or creator.

**KUNAL SHAH** (00:20:45):
The nuance I'm talking about is when you are thinking about risk appetite, India is changing, but now for the first time we are seeing founders being respected and talked about and these unicorns being celebrated and our Prime Minister talks about startups quite openly.

**KUNAL SHAH** (00:21:02):
We have a National Startup Day and so on and so forth.

**KUNAL SHAH** (00:21:04):
So I think there is a thing that has changed this, but let's understand the core human behavior.

**KUNAL SHAH** (00:21:11):
India still has a large number of arranged marriages.

**KUNAL SHAH** (00:21:16):
And if you are a founder and a failed founder, your chances of getting a person to marry is still hard to achieve.

**KUNAL SHAH** (00:21:26):
So if this is all true, then the appetite to take risk will be curtailed.

**KUNAL SHAH** (00:21:32):
Somebody gave me an interesting example that there's a very large, let's say CPG company in India, and let's say you do a zero to one over there and the CEO changes in four or five years and your zero to one fails, but you were the best person, that's why you were given the zero to one.

**KUNAL SHAH** (00:21:49):
The next CEO is like, “So what have you done in the last five years?”

**KUNAL SHAH** (00:21:52):
He's like, "Nothing.

**KUNAL SHAH** (00:21:53):
I just tried to launch it but failed."

**KUNAL SHAH** (00:21:55):
And you are neither given a promotion in the company, nor a new company will say, "Oh my God, I'm going to hire this talent."

**KUNAL SHAH** (00:22:00):
So the guy who stayed on this stable brand within the CPG company kept growing, but that has natural tailwinds.

**KUNAL SHAH** (00:22:07):
All he has to do is nothing in that brand.

**KUNAL SHAH** (00:22:10):
And then suddenly what you see is that he or she's managed to do well and this guy has done a zero to one has not done well.

**KUNAL SHAH** (00:22:16):
So we do not celebrate risk-takers as a country yet.

**KUNAL SHAH** (00:22:21):
And I think we'll change that.

**KUNAL SHAH** (00:22:23):
I think it's changing already, but we have a long way to go.

**KUNAL SHAH** (00:22:27):
One of the beautiful things I often talk about is that when I was in Portugal once and I saw, I don't know if you've ever been and seen this, but in the church normallyonly the Royalty are allowed to be buried or cremated. There is only one more category that is allowed-  the explorers.

**KUNAL SHAH** (00:22:47):
Vasco da Gama, all of these guys who explored the world and took risks and took the country forward, were given the same position as the royalty.

**KUNAL SHAH** (00:22:55):
So when we give the highest status to risk-takers, the country appreciates it because ultimately we're all looking for markers of social validation.

**LENNY RACHITSKY** (00:23:05):
Super interesting.

**LENNY RACHITSKY** (00:23:06):
I want to keep talking about India and how it's different and especially what may surprise people about the market, both building there and then how to build products that are successful in India.

**LENNY RACHITSKY** (00:23:15):
I saw in a different interview, you talk about how there's this big difference between DAUs and ARPUs. In India it's really easy to get DAUs, basically get lots of users, it's really hard to make revenue per user, and that changes the way you build products broadly.

**LENNY RACHITSKY** (00:23:30):
Could you just talk about why this is the case?

**LENNY RACHITSKY** (00:23:32):
Why is it so much easier to get DAUs versus ARPUs?

**KUNAL SHAH** (00:23:37):
I think ARPU is a function of per capita income of a country.

**KUNAL SHAH** (00:23:41):
You cannot make $100 per user from a country for a product when their income is let's say $2,500 per year as an average for the whole country.

**KUNAL SHAH** (00:23:52):
So what happens is many global companies love to come to India because we have the cheapest data, and very high smartphone penetration.

**KUNAL SHAH** (00:24:01):
So if you look at a lot of global giants, they'll have 500 million users from India, sometimes a billion users coming from Asia and they don't have huge ARPUs, but they help you show the user growth which helps you in your public market and therefore improves your valuations.

**KUNAL SHAH** (00:24:16):
For example, my guess is that, I don't know if this data is public or not to talk about, my guess is that Meta would not have more than $3 or $4 per user per year monetization in India.

**KUNAL SHAH** (00:24:28):
But if you look at the user growth in India, it is huge.

**KUNAL SHAH** (00:24:33):
So a lot of times for global companies, India becomes a great MAU farm but very low on ARPU. Therefore a lot of Indian founders who tried to copy the Western market saying, “I'm going to have a few hundred million users” make a terrible mistake because they will need to then go abroad to find their ARPUs to balance the act.

**LENNY RACHITSKY** (00:24:52):
You talk about how Netflix is a good example of that, where they launched in India, they got lots of users, but just couldn't make a lot of money.

**KUNAL SHAH** (00:24:58):
Yeah.

**KUNAL SHAH** (00:24:58):
Because forusers to find relevant content, pay for content, when we have tons of free data, tons of free content all over the place, like short videos that are competing with time, so much going on over here, people actually paying for that by design is going to be less.

**KUNAL SHAH** (00:25:17):
And I'm not saying that it'll not change in 10, 20 years, but the expectation that many global companies come over here saying that, “I'm going to have these tens of millions of users who start paying me as soon as I come”, for Spotify, for Netflix, or Amazon Prime for that matter has not panned out.

**LENNY RACHITSKY** (00:25:37):
So one of my takeaways here is just when you look at a startup as an investor especially, and you see “We've got 100 million users,” don't treat that the same as say 100 million users in the US or other markets.

**KUNAL SHAH** (00:25:49):
Absolutely.

**KUNAL SHAH** (00:25:50):
One more thing is the value of time as a concept.

**KUNAL SHAH** (00:25:53):
So one of the things you'll notice, Lenny, is that no Indian has ever been paid an hourly salary in their entire life.

**KUNAL SHAH** (00:26:00):
But let me ask you a question.

**KUNAL SHAH** (00:26:01):
What was your first ever job and how were you paid?

**LENNY RACHITSKY** (00:26:04):
My first ever job, I was tutoring women about computers and passing Microsoft certification tests.

**LENNY RACHITSKY** (00:26:10):
And I was paid, I'm pretty sure it was hourly.

**KUNAL SHAH** (00:26:10):
Now most likely you'll remember what the hour rate income was.

**KUNAL SHAH** (00:26:16):
And even though you've started making a lot more, you still have the concept of what the value of your one hour is.

**KUNAL SHAH** (00:26:23):
But if you ask most Indians, and if you ever come to India and do this exercise when you meet them, ask them “What's your income per day or income per hour?”

**KUNAL SHAH** (00:26:34):
Nobody will be able to answer, no matter what their job is.

**KUNAL SHAH** (00:26:36):
They could be staff, at the restaurant, to somebody who's doing really basic work, to anybody in any fancy job, because we've never ever been paid an hourly salary.

**KUNAL SHAH** (00:26:47):
So when you're not paid an hourly salary, the concept of time is not the same.

**KUNAL SHAH** (00:26:53):
And when the concept of time is not the same, paying for time is hard to do.

**KUNAL SHAH** (00:26:59):
And therefore you'll see a lot of Indians who make, let's say, I don't know, maybe $100 an hour, but still spend an hour to spend $10 on a flight ticket because that's what it is.

**KUNAL SHAH** (00:27:10):
And if you discuss that with many of the Indians in the West also you'll realize that this is a common joke that they will still fight for the $10 because the value of time is something that is harder to get used to unless from your childhood the unit of time was moved smaller and smaller.

**LENNY RACHITSKY** (00:27:29):
That is really interesting.

**LENNY RACHITSKY** (00:27:31):
And you're saying that comes from just the fact that people never get paid hourly?

**LENNY RACHITSKY** (00:27:34):
It's always a salary, and so people don't write down-

**KUNAL SHAH** (00:27:36):
The concept of valuing time.

**KUNAL SHAH** (00:27:40):
Many Indian languages do not have a word for “efficiency.”

**LENNY RACHITSKY** (00:27:44):
Wow.

**KUNAL SHAH** (00:27:45):
And that's true for many Asian languages, the word for “efficiency” does not exist.

**KUNAL SHAH** (00:27:50):
So then how do you value it if it's not in the vocabulary?

**LENNY RACHITSKY** (00:27:54):
Fascinating.

**LENNY RACHITSKY** (00:27:56):
There's something else along these lines of DAUs and ARPUs and efficiency that you talked about that I love, which is this idea that focus is a curse in Asian markets, that in the US there's often this advice.

**LENNY RACHITSKY** (00:28:09):
“Focus, build one thing that's amazing that everyone loves, try to make that work, scale that, and then, only then, build a new product or build something, build a new big feature.”

**LENNY RACHITSKY** (00:28:18):
And your advice is in India and Asian markets in general, it's the opposite.

**LENNY RACHITSKY** (00:28:22):
And I think it's because you make so little per user.

**LENNY RACHITSKY** (00:28:24):
Could you talk about that?

**KUNAL SHAH** (00:28:25):
Yeah.

**KUNAL SHAH** (00:28:26):
I think one is you make very little per user, so you have to do many things.

**KUNAL SHAH** (00:28:30):
But also all low trust markets, and let me define low trust markets as where consumers are a lot more wary of trying new things because there are no institutions that protect you against bad behavior done by a company.

**KUNAL SHAH** (00:28:44):
So for example, if I ever had a fall in a coffee shop in the US, I can think about suing them and making money off it.

**KUNAL SHAH** (00:28:51):
In India, you're only worried about “I'm going to pay for my thing.”

**KUNAL SHAH** (00:28:53):
You don't even think about suing the coffee shop or even hoping that you'll get any money for that.

**KUNAL SHAH** (00:28:57):
So what happens is in a low trust country, and all developing nations are low trust by design, because the institutions are not strong enough to really, really take care of many things.

**KUNAL SHAH** (00:29:09):
What happens is there is concentration of trust.

**KUNAL SHAH** (00:29:11):
So you will see that super apps, superstars, super companies all exist in low trust markets because the lack of trust creates concentration of trust, and therefore you will see one app can do 400 things.

**KUNAL SHAH** (00:29:24):
For example, we have a company like Tata that can do salt to car to jewelry to anything and people will buy it because it's a Tata brand, because it comes from a low trust society trusting the brand and not being, “Oh, I'm going to prefer this new brand.”

**KUNAL SHAH** (00:29:42):
The joy of trying new things is not so high in low trust nations.

**LENNY RACHITSKY** (00:29:47):
Wow, I'm learning a lot here.

**LENNY RACHITSKY** (00:29:48):
I didn't know all this.

**LENNY RACHITSKY** (00:29:49):
So essentially the brand is even more, exponentially more important in Indian markets.

**KUNAL SHAH** (00:29:55):
It's funny, but the oldest brand in the world is a brand called Chyavanprash.

**KUNAL SHAH** (00:30:00):
It's a guy named Chavan who built a “prash” which is a sort of paste that you can have for good health, and it was built in India many, many, many, many centuries ago.

**KUNAL SHAH** (00:30:14):
And lots of Indian businesses still have the name of the person behind it.

**KUNAL SHAH** (00:30:19):
Even the US is like that.

**KUNAL SHAH** (00:30:21):
JP Morgan, all these guys are not some fancy name.

**KUNAL SHAH** (00:30:23):
They're the names of people.

**KUNAL SHAH** (00:30:25):
And therefore in India, trust still comes from a lot of names of people who had a lot of trust behind them and reputation behind them.

**LENNY RACHITSKY** (00:30:33):
I want to zoom out a little bit before we go in a different direction.

**LENNY RACHITSKY** (00:30:36):
What do you see as either the most pressing challenges in India right now for tech and/or the biggest opportunity for Indian startups?

**LENNY RACHITSKY** (00:30:47):
And then just generally where do you think things will evolve in the next few years?

**KUNAL SHAH** (00:30:51):
Sometimes I wonder if the challenges and the opportunities are exactly the same.

**KUNAL SHAH** (00:30:56):
For example, one of the biggest challenges we have is, we have very low female participation of labor compared to many markets.

**KUNAL SHAH** (00:31:04):
But I also believe it's an opportunity because you can, let's say, use AI and create many new types of business and opportunities because now work from home is not an alien concept anymore.

**KUNAL SHAH** (00:31:13):
You can actually create very interesting businesses for that.

**KUNAL SHAH** (00:31:16):
Number two is we are low on per capita income.

**KUNAL SHAH** (00:31:23):
So what AI can do instead of taking our jobs away, is just make us brighter.

**KUNAL SHAH** (00:31:28):
Satya talks about how expertise is now available in the air. So you can actually just ride on that and really make the world very equal in many many ways.

**KUNAL SHAH** (00:31:40):
So that's a massive opportunity and also a challenge, because I often make this joke that the largest employer of the world is ‘inefficiency’, and if you take that away too quickly, we'll have a very, very jobless world.

**KUNAL SHAH** (00:31:52):
So the thing is that it can be an opportunity for a country like India and also potentially a threat because if we don't start becoming great at AI.

**KUNAL SHAH** (00:32:01):
I was actually just telling somebody today that maybe all of our interviews should be about giving a task that they can only perform if they are very good at AI.

**KUNAL SHAH** (00:32:11):
And no matter what the job is, you make that the minimum criteria that if they cannot use that, leverage that, they'll become a liability in 5 years anyways.

**KUNAL SHAH** (00:32:23):
And the last one is, we have a very young demographic, very well positioned with access to technology, access to smartphones and so on and so forth, a lot of hunger.

**KUNAL SHAH** (00:32:34):
But our challenge is that it's also the first generation that is truly learning what entrepreneurship is, what risk is, and we'll make all sorts of mistakes to get there.

**KUNAL SHAH** (00:32:43):
And I hope we don't go into a shell after having these large scale failures that we have not seen before.

**KUNAL SHAH** (00:32:50):
India is not used to layoffs.

**KUNAL SHAH** (00:32:53):
Like the startup world is used to layoffs, but in India, if startups do layoffs, it becomes the national news and all sorts of discussions happen over here.

**KUNAL SHAH** (00:33:01):
So we are not there yet.

**KUNAL SHAH** (00:33:03):
So we are stuck between being somewhat of a collectivist or somewhat of an individualistic society.

**KUNAL SHAH** (00:33:10):
We are somewhere.

**KUNAL SHAH** (00:33:12):
India is a great remix of everything.

**LENNY RACHITSKY** (00:33:15):
I love this line you just shared of “inefficiencies is the largest employer in the world”.

**LENNY RACHITSKY** (00:33:22):
I totally get that.

**LENNY RACHITSKY** (00:33:23):
Okay.

**LENNY RACHITSKY** (00:33:24):
So let's talk about CRED for a bit.

**LENNY RACHITSKY** (00:33:27):
So you had, I think three startups before CRED?

**LENNY RACHITSKY** (00:33:31):
Okay.

**LENNY RACHITSKY** (00:33:31):
And then you've been building CRED for about six years now.

**LENNY RACHITSKY** (00:33:34):
I'm curious just on this journey of CRED, what you've learned or changed your mind about, during this phase of your career versus previous phases.

**KUNAL SHAH** (00:33:45):
I think CRED's insight was actually quite simple.

**KUNAL SHAH** (00:33:47):
We realized that unfortunately the value of time and per capita income is concentrated with 25 million families and therefore focusing on them is important.

**KUNAL SHAH** (00:33:56):
And they are a lot more global in their approach versus the rest of India.

**KUNAL SHAH** (00:34:01):
So you have to build for them very differently.

**KUNAL SHAH** (00:34:05):
And I realized that the ability to focus on a customer set, which is not historically possible to do because every investor expected us to be the next China, and the only similarity of India and China was the population and nothing else was similar.

**KUNAL SHAH** (00:34:19):
So I think having that conviction that, “I'm going to build only for these folks and this large enough market.”

**KUNAL SHAH** (00:34:27):
Thankfully I had one success for somebody to bet.

**KUNAL SHAH** (00:34:30):
So our series A was $25 million.

**KUNAL SHAH** (00:34:32):
I would've not had that luxury if I had no success in the past because I had no product with any monetization to prove that I'm doing the right thing.

**KUNAL SHAH** (00:34:39):
It turned out okay, but I think I could get a lot of people to take a risk behind my insight or my thesis because I focused on the right customer category and built on it.

**KUNAL SHAH** (00:34:51):
But I think the few things I've learned differently is that companies that are very, very good at zero to one will not naturally become great at 10 to 100.

**KUNAL SHAH** (00:35:00):
There are lots of different lessons to learn.

**KUNAL SHAH** (00:35:01):
The founder has to evolve.

**KUNAL SHAH** (00:35:03):
That’s the biggest thing that has to happen.

**KUNAL SHAH** (00:35:05):
Most people at CRED are people who have not seen a bigger business than CRED, which comes with its benefits and costs.

**KUNAL SHAH** (00:35:12):
So you have to gentrify the org every now and then to make people understand the value of many of these reliable things.

**KUNAL SHAH** (00:35:19):
And I often tell people that entrepreneurs are uncertainty absorbers for everybody- for employees, for investors, for customers- and therefore they get rewarded for being those people who remove uncertainty from people's lives.

**KUNAL SHAH** (00:35:37):
But the kind of expectations keep changing at companies of scale.

**KUNAL SHAH** (00:35:41):
For example, if you have, let's say a seed stage investor, they are very used to very high uncertainty and they're happy with some absorption.

**KUNAL SHAH** (00:35:51):
But as you get a growth investor, and let's say you have sovereigns on your cap table, the amount of stability you need to provide is significantly more, and therefore you need to evolve very, very differently.

**KUNAL SHAH** (00:36:01):
So I think those are the few lessons that I've learned.

**KUNAL SHAH** (00:36:02):
Talent, you start realizing that not everybody can scale into everything.

**KUNAL SHAH** (00:36:07):
And you cannot expect that you can give up the 0 to 1 DNA just because you're building 10 to 100.

**KUNAL SHAH** (00:36:12):
So how do you kind of coexist with those things?

**KUNAL SHAH** (00:36:15):
How do you react to big changes in the market and not become this slow company?

**KUNAL SHAH** (00:36:19):
And every company goes through that.

**KUNAL SHAH** (00:36:21):
I mean if you look at what Zuck went through in the last three or four years was that.

**KUNAL SHAH** (00:36:27):
I often say that he had to play the Shiva, come and do a lot of destruction to become big again.

**KUNAL SHAH** (00:36:34):
So I think that's what founders can do, and it's not easy to do.

**KUNAL SHAH** (00:36:39):
One of the things I've learned is that profit pools of a country tell you a lot about what the country values.

**KUNAL SHAH** (00:36:48):
And trying to copy somebody else's profit pool to your country will not be a wise idea because the country's values are demonstrated in what profit pools exist.

**KUNAL SHAH** (00:36:57):
Let's take an example.

**KUNAL SHAH** (00:36:59):
In the thousand most profitable companies in India, the number of retailers would be probably two or three.

**KUNAL SHAH** (00:37:06):
But if you look at the Western market, you'll see a bunch of them because it's a consumption market, plus a very high divorce rate which means you're always peacocking again in the market, you're trying to be fit and be cool and all of that.

**KUNAL SHAH** (00:37:19):
India has a very low divorce rate, less than 1%, are arranged marriages.

**KUNAL SHAH** (00:37:24):
Fashion spends, and because we have a lower female participation of labor, India is probably the only market where female fashion spends is less than men's fashion spends.

**KUNAL SHAH** (00:37:33):
Everywhere else, it's probably five, 6x more for them.

**KUNAL SHAH** (00:37:36):
So what happens is you start appreciating what the country values.

**KUNAL SHAH** (00:37:40):
For example, I have noticed that many patriarchal societies have a very significant market cap in financial services versus consumption.

**KUNAL SHAH** (00:37:50):
And these broad patterns, you start thinking about very, very differently.

**LENNY RACHITSKY** (00:37:55):
So many lessons there.

**LENNY RACHITSKY** (00:37:56):
I love this idea of a founder being an uncertainty absorber.

**LENNY RACHITSKY** (00:38:00):
This other point you made about Zuck becoming the Shiva and destruction touches on something Brian Chesky and I chatted a bit about, how founders often start in control, very micromanaging, just driving the ship.

**LENNY RACHITSKY** (00:38:13):
And then as the company grows, they delegate and empower and then things start to slow down and then they come back, play the Shiva and take control again.

**LENNY RACHITSKY** (00:38:23):
Is there anything there that you've seen-

**KUNAL SHAH** (00:38:25):
Yeah, but that's the universe.

**KUNAL SHAH** (00:38:26):
The universe goes through the exact same phases.

**KUNAL SHAH** (00:38:28):
So if you study Indian mythology, you'll see that there's a Brahma, Vishnu, Mahesh cycles and every yugg As it’s called, goes through these three phases all the time.

**LENNY RACHITSKY** (00:38:38):
Beautiful.

**LENNY RACHITSKY** (00:38:39):
I see.

**LENNY RACHITSKY** (00:38:39):
So this is just inevitable.

**LENNY RACHITSKY** (00:38:41):
This is the circle of life.

**LENNY RACHITSKY** (00:38:42):
Absolutely.

**LENNY RACHITSKY** (00:38:43):
Amazing.

**LENNY RACHITSKY** (00:38:44):
I love how this all just ties back to your philosophy background.

**LENNY RACHITSKY** (00:38:47):
I love it.

**LENNY RACHITSKY** (00:38:47):
It's beautiful.

**LENNY RACHITSKY** (00:38:49):
**LENNY RACHITSKY** (00:38:54):
Are you working in a feature factory building filler that nobody wants?

**LENNY RACHITSKY** (00:38:59):
Probably, because the sad truth is that most SaaS features are rarely or never used, costing the industry billions every year.

**LENNY RACHITSKY** (00:39:07):
Let's change that.

**LENNY RACHITSKY** (00:39:08):
Product managers, Dovetail is holding their first industry conference, it's called Insight Out, and they want you to come over one day in San Francisco.

**LENNY RACHITSKY** (00:39:18):
The product community is coming together to learn how to better leverage customer insights and build products that people actually love to use.

**LENNY RACHITSKY** (00:39:25):
It's on April 11, and you can hear from product leaders from Uber, Twitch Meta and Netflix as they share their strategies for driving innovation, thriving in uncertainty and balancing customer centered work with business needs.

**LENNY RACHITSKY** (00:39:39):
And here's the kicker, it's absolutely free for online tickets.

**LENNY RACHITSKY** (00:39:43):
Just go to dovetail.com/lenny to register.

**LENNY RACHITSKY** (00:39:47):
This is thanks to Dovetail, the best way for product teams to get the most out of customer insights.

**LENNY RACHITSKY** (00:39:52):
Check it out at dovetail.com/lenny.

**LENNY RACHITSKY** (00:39:56):
Okay.

**LENNY RACHITSKY** (00:39:56):
So, on CRED.

**LENNY RACHITSKY** (00:39:57):
So here's a funny thing that happened.

**LENNY RACHITSKY** (00:39:58):
I asked people on Twitter what questions to ask you on this podcast, and one of the most common questions was “When do you think you'll become profitable?”

**LENNY RACHITSKY** (00:40:06):
Which is interesting because when I have other CEOs that are founding a company that is, and most companies aren't profitable, nobody's asking that question.

**LENNY RACHITSKY** (00:40:14):
So I'm just curious, why is that such a common question that comes up?

**KUNAL SHAH** (00:40:17):
It's fascinating.

**KUNAL SHAH** (00:40:19):
It's fascinating.

**KUNAL SHAH** (00:40:21):
As a country, most businesses were of trading, you buy something at low cost, sell at a higher price and you make profit.

**KUNAL SHAH** (00:40:30):
Most of our businesses, most of our family businesses were trading.

**KUNAL SHAH** (00:40:35):
But building a CapEx heavy distribution, monetizing it later on, focusing on high revenue growth rate versus trying to get profitability first, is not known to us.

**KUNAL SHAH** (00:40:47):
So when they see these large numbers of losses, there's a shock. “Why would somebody give you this kind of money?”

**KUNAL SHAH** (00:40:56):
And  by the way, my own dad wouldn't respect me till I was building a profitable company.

**KUNAL SHAH** (00:41:01):
So it's not surprising that people in India have these comments, but it also comes from not understanding how businesses are built in the internet world, where VCs are giving you the capital to build distribution, unique product edge, brand, all of that stuff, and then monetize later on and monetize big and then have very large profit pools to go after.

**KUNAL SHAH** (00:41:23):
But a lot of times this comes from not understanding this business, and I feel it'll change because many internet companies are now getting very profitable and public listed.

**KUNAL SHAH** (00:41:36):
So we'll have a decade.

**KUNAL SHAH** (00:41:39):
Let's understand one thing.

**KUNAL SHAH** (00:41:40):
In the US, maybe 27-30% of the US market cap is now tech companies.

**KUNAL SHAH** (00:41:46):
In India tech companies would probably make less than 2- 3% of the market cap.

**KUNAL SHAH** (00:41:51):
So we are mostly, and I'm not saying India has this fabulous history of building very, very profitable tech companies.

**KUNAL SHAH** (00:41:57):
We are probably the first generation that will have to prove ourselves to be very large profitable companies.

**KUNAL SHAH** (00:42:02):
But we are still figuring out what this means.

**KUNAL SHAH** (00:42:05):
And the fact that this question, by the way, I can tell you one thing that, I have been asked this question by people on Twitter way more than any of my investors have ever asked me this question. This also creates an arbitrage for entrepreneurs who can actually build businesses and have the ability to raise capital and prove their business model with very high revenue growth rate and build large brands and so on and so forth.

**KUNAL SHAH** (00:42:29):
But I find it fascinating as well.

**KUNAL SHAH** (00:42:32):
Also, one thing we see fascinating in India is that there is an immense amount of trolling and doubt that will come in your comments no matter what you do.

**KUNAL SHAH** (00:42:42):
So if you see any founder in India, they'll post something about the thing, the comments will rarely have appreciation.

**KUNAL SHAH** (00:42:50):
So it feels sad because, when you see global companies do stuff, Indians will lose their shit on Apple Vision Pro and all this stuff and Twitter will go gaga over it.

**KUNAL SHAH** (00:43:01):
But I think when it comes to...and I believe envy is hyperlocal.

**KUNAL SHAH** (00:43:08):
We do not envy Elon Musk for all the stuff he does because he's so far away.

**KUNAL SHAH** (00:43:13):
But we envy our own because they were just like us not many years ago.

**KUNAL SHAH** (00:43:19):
And therefore envy is like wifi.

**KUNAL SHAH** (00:43:23):
It's like a hyperlocal service.

**LENNY RACHITSKY** (00:43:25):
How do you stay positive and focused and not let that stuff bring you down?

**LENNY RACHITSKY** (00:43:31):
And do you have advice for founders in India that are dealing with the same sort of feedback?

**KUNAL SHAH** (00:43:35):
It's funny the number of calls I've got from founders who start getting hate. I’m the go-to person to get these call because they've seen me get it for many more years.

**KUNAL SHAH** (00:43:45):
And I tell people that we couldn't have made it this far if we cared about criticism of everybody versus people who've done better than us.

**KUNAL SHAH** (00:43:58):
If somebody who's done anything better than me gives me any amount of criticism, I will absolutely flip and make all the changes and evolve.

**KUNAL SHAH** (00:44:08):
And I seek feedback all the time from people.

**KUNAL SHAH** (00:44:12):
But if I start taking feedback from everybody who does not understand the nuance and empathize with what I'm doing, I'm not saying that we should not take customer feedback, that's very different.

**KUNAL SHAH** (00:44:19):
But let's say somebody commenting about your business, who does not understand the nuance of it, you can't be reacting to everything.

**KUNAL SHAH** (00:44:27):
And I often tell people that there's a reason elements with lower valencies are called noble gases because they're hardest to get reactions from.

**LENNY RACHITSKY** (00:44:38):
That's over my head, but I love it anyway.

**LENNY RACHITSKY** (00:44:42):
It's so interesting.

**LENNY RACHITSKY** (00:44:43):
I love all these elements you're pointing out of how different building in India is. I think people in the US have no idea about it.

**LENNY RACHITSKY** (00:44:49):
And so I appreciate you getting into all these little elements.

**LENNY RACHITSKY** (00:44:53):
Is there anything else around the Indian market that may surprise people before we go in a different direction about building a startup there?

**KUNAL SHAH** (00:44:59):
For all the challenges, India remains the most promising market that one can be building for right now because everything is going our way.

**KUNAL SHAH** (00:45:07):
We have all sorts of digital public infrastructure, government support, all these great people doing extraordinary things, apart from the Twitter noise.

**KUNAL SHAH** (00:45:17):
And Twitter is designed for outrage getting likes.

**KUNAL SHAH** (00:45:21):
So I wouldn't read too much into it.

**KUNAL SHAH** (00:45:23):
But I think all of us are doing well because we have an audience set, an evolved ecosystem that is fully supporting us and really taking it forward.

**KUNAL SHAH** (00:45:34):
So I think I wouldn't want to be anywhere else in building because of this extremely vibrant, crazy opportunity that one can learn from.

**KUNAL SHAH** (00:45:43):
However, I often wish that I could get a one month internship with Brian and learn how to do things.

**KUNAL SHAH** (00:45:51):
And I've never had the luxury.

**KUNAL SHAH** (00:45:53):
I can only watch his podcast with you to learn a few things, but what if I got a chance to be there?

**KUNAL SHAH** (00:45:58):
And I miss that part where I've never been really trained by these extraordinary product brains or even observed them make decisions.

**KUNAL SHAH** (00:46:08):
So I recently posted one thing that the word ‘operation theater’ comes because operating used to be a public process and people used to pay money to watch surgeries and see all the bloody gory stuff and even before anesthesia was born.

**KUNAL SHAH** (00:46:21):
And there's so much joy in seeing somebody do their action.

**KUNAL SHAH** (00:46:26):
And I wish there was a theater for Brian taking a product decision, Zuck taking a hard call on killing a product or seeing Tim rejecting all the ideas that they have before the GTM of a product.

**KUNAL SHAH** (00:46:42):
I think we could benefit so much from that.

**KUNAL SHAH** (00:46:45):
And unfortunately it remains in very small circles.

**KUNAL SHAH** (00:46:47):
And like I said, the reason I said you do a fabulous job of removing some of the information asymmetry and kind of making it more democratic.

**KUNAL SHAH** (00:46:54):
But there is so much more that we all could learn.

**KUNAL SHAH** (00:46:57):
And I feel extremely envious of many people who have the opportunity to work with the best of the best because, many of us from India never had the luxury. We had to figure out everything on our own.

**LENNY RACHITSKY** (00:47:10):
Wow.

**LENNY RACHITSKY** (00:47:10):
How cool would that be just to have a camera in some of those meetings just as a learning experience, because very few people are in those rooms and there's so much to learn.

**LENNY RACHITSKY** (00:47:21):
I think though people will find, “Holy shit, one, this is how decisions are made, what is going on?”

**LENNY RACHITSKY** (00:47:26):
And two is , “I don't want to work for this person.

**LENNY RACHITSKY** (00:47:29):
This sounds very difficult and stressful.”

**LENNY RACHITSKY** (00:47:33):
Those are probably some takeaways that will emerge.

**LENNY RACHITSKY** (00:47:36):
Kind of along these lines, something that comes up a lot in your talks and work is curiosity.

**LENNY RACHITSKY** (00:47:43):
You have a show called CRED curious.

**LENNY RACHITSKY** (00:47:46):
You often talk about the power of curiosity.

**LENNY RACHITSKY** (00:47:48):
I'm just curious, why is curiosity so important to you and why is it important for other people to always stay curious and what value is there?

**KUNAL SHAH** (00:47:57):
I think a curious person is somebody who is constantly demonstrating that they are not proud of their expertise, and they will demonstrate extraordinary amounts of excitement when they face a problem which they have no clue how to solve.

**KUNAL SHAH** (00:48:17):
And therefore a lot of people stop growing because they want to constantly demonstrate their expertise versus demonstrating their curiosity.

**KUNAL SHAH** (00:48:27):
Because, curiosity should come from security because imagine- I'm the founder, CEO of this company and this group of 60 people on WhatsApp, somebody posts something and asks a dumb question, “What does this word mean?”

**KUNAL SHAH** (00:48:41):
You need to have the security to feel okay with it, but a lot of people out off insecurity try to demonstrate expertise and do it or Google to not ask these people.

**KUNAL SHAH** (00:48:52):
And I think that slows down the compounding growth and I think it keeps you from being very good at adapting.

**KUNAL SHAH** (00:49:02):
So it's funny, I was recently. GPT is my favorite thing to keep asking random questions because now I don't need to really worry about Google having those questions answered around because I can ask the GPT.

**KUNAL SHAH** (00:49:12):
So I recently asked the question: which species or animals have survived for more than 100 million years without changing too much and what is common in all of them?

**KUNAL SHAH** (00:49:22):
So GPT came up with an interesting answer which says that sharks, horseshoe crabs, crocodiles, and all of these animals have survived to do this thing.

**KUNAL SHAH** (00:49:34):
So three distinct traits were, one, ability to reduce metabolism at will.

**KUNAL SHAH** (00:49:43):
It's fascinating.

**KUNAL SHAH** (00:49:45):
I can bring down my metabolism by 1:20 or a crazy, crazy scale that they can bring the metabolism down.

**KUNAL SHAH** (00:49:54):
By the way, ancient yogis have demonstrated this as well.

**KUNAL SHAH** (00:50:00):
It comes from the same yogic practice.

**KUNAL SHAH** (00:50:02):
The second thing is about, and if you think about companies, the context is the same.

**KUNAL SHAH** (00:50:06):
If COVID came, you could slow down your metabolism and survive, right?

**KUNAL SHAH** (00:50:12):
Or you burned your way out and disappeared.

**KUNAL SHAH** (00:50:16):
The second thing that was interesting was the very high conversion rate on every attempt to secure food.

**KUNAL SHAH** (00:50:25):
They don't go around chasing randomly and doing things.

**KUNAL SHAH** (00:50:27):
They have a very high conversion rate, which means high judgment and the deadliest bite.

**KUNAL SHAH** (00:50:35):
So they'll not chase many options, but if they chase something, they will have the biggest bite and they'll convert it.

**KUNAL SHAH** (00:50:41):
And the third thing that was more interesting was that they have survived all sorts of crazy environmental changes, just adapting. And adaptation comes from curiosity.

**KUNAL SHAH** (00:50:56):
And you could see those people.

**KUNAL SHAH** (00:50:57):
In COVID, there were two sets of people, who were completely gone into a shell and there were those who were curious.

**KUNAL SHAH** (00:51:03):
“Okay, so what do I do with this?”

**KUNAL SHAH** (00:51:05):
“What happens now?”

**KUNAL SHAH** (00:51:06):
“Do I need to change something?”

**KUNAL SHAH** (00:51:07):
“Do I need to tweak something?”

**KUNAL SHAH** (00:51:09):
So the ability to change very quickly.

**KUNAL SHAH** (00:51:13):
I often feel that curiosity is that demonstration of the ability to adapt and learn, and you only create more information asymmetry.

**KUNAL SHAH** (00:51:25):
To me, wealth is nothing but information asymmetry.

**KUNAL SHAH** (00:51:27):
All the best companies in the world have unfair information asymmetry.

**KUNAL SHAH** (00:51:33):
And that comes from curiosity. Because you're constantly collecting dots, connecting dots, collecting dots, connecting dots, and end up creating this unique edge for yourself and information asymmetry for yourself.

**KUNAL SHAH** (00:51:48):
And if you assume that “I have collected enough,” no human life is going to be enough to connect and connect all the dots.

**KUNAL SHAH** (00:51:56):
We'll never be able to get..

**KUNAL SHAH** (00:51:58):
And sometimes I envy the stuff that you do because you are efficiently connecting and collecting dots by having the luxury of all these people to talk to, and you are making more dots getting connected.

**KUNAL SHAH** (00:52:12):
So your information asymmetry is growing.

**LENNY RACHITSKY** (00:52:14):
Wait until you IPO, and then someday maybe leave CRED and then you could start this podcast with everyone like this and connect all the dots.

**LENNY RACHITSKY** (00:52:22):
And I think that's a reference to Danny Meyer who's the founder of all these fancy restaurants and big on hospitality and has this phrase “Always be collecting dots”, I think ABCD, I’ll link to that.

**LENNY RACHITSKY** (00:52:33):
Yeah.

**LENNY RACHITSKY** (00:52:35):
Okay.

**LENNY RACHITSKY** (00:52:35):
Wait, this is really interesting, this list of what are the common traits of the most long-lasting animals?

**LENNY RACHITSKY** (00:52:41):
They can lower their metabolism at will, they have a high conversion rate to get food, and they've survived many types of environments.

**LENNY RACHITSKY** (00:52:49):
And I think there's a lot you can transform as you've done, to startups and leaders.

**LENNY RACHITSKY** (00:52:54):
This could be its own…

**LENNY RACHITSKY** (00:52:55):
if you haven't written about this, this would be a cool blog post.

**LENNY RACHITSKY** (00:52:59):
I'm curious who you look up to in business, either in India and outside India.

**LENNY RACHITSKY** (00:53:05):
Who comes to mind where you're like, I really inspired, I'm inspired by these folks?

**KUNAL SHAH** (00:53:10):
I often tell people that I hate the word ‘favorite’ because it tells me to become limited in my mind.

**KUNAL SHAH** (00:53:16):
So I stay away from ‘favorite’, but I learn all the time from everybody.

**KUNAL SHAH** (00:53:22):
And there are so many people to learn from across the world and in history, in the recent past and every time you'll discover fascinating, extraordinary things about them.

**KUNAL SHAH** (00:53:35):
So I don't think I have a person.

**KUNAL SHAH** (00:53:38):
I am this person who thinks about about: ”How did they solve this hard problem.”

**KUNAL SHAH** (00:53:42):
So one of the things that we started doing recently and not very ritualistic about it so far is, I ask myself and my key reportees every month, we go around the table and ask ourselves, ”What are the hardest problems we solved last month?”

**KUNAL SHAH** (00:54:00):
And it's very hard to come up with an answer.

**KUNAL SHAH** (00:54:04):
And if you do this to the product leaders, just go around and ask, “What are the hard problems you solved last month?”

**KUNAL SHAH** (00:54:11):
You'll realize that we all stay very busy and displacement is hard.

**KUNAL SHAH** (00:54:15):
But if you notice extraordinarily successful people, they'll have a lot more content to talk about every month, every quarter because they're obsessed with making that big displacement and it does not come by being busy.

**KUNAL SHAH** (00:54:35):
And that's another thing that you cannot chase the big thing.

**KUNAL SHAH** (00:54:37):
You don't see a crocodile being busy.

**KUNAL SHAH** (00:54:40):
You see a crocodile just waiting patiently at the watering hole for that best meal and have the deadliest bite for that.

**KUNAL SHAH** (00:54:49):
So the beautiful definition of predators I read was “one who burns the least amount of calories to earn the most amount of calories.”

**KUNAL SHAH** (00:54:59):
So how do you become that?

**KUNAL SHAH** (00:55:00):
And I think when I meet people who are extraordinary at that, and it comes in all shapes and forms, I learn something from them.

**LENNY RACHITSKY** (00:55:07):
So in these meetings you have, are you judging people's success based on how many hard problems they solve?

**LENNY RACHITSKY** (00:55:13):
Now that they've heard this, they're going to be like, I need more.

**KUNAL SHAH** (00:55:17):
Because if you're a senior, what is the role of a senior person?

**KUNAL SHAH** (00:55:21):
You have to be the chief problem solver.

**LENNY RACHITSKY** (00:55:24):
I love that.

**LENNY RACHITSKY** (00:55:24):
I often think of leaders as professional firefighters who have just endless fires to put out.

**LENNY RACHITSKY** (00:55:31):
Kind of along the lines of people and where you learn from, are there any sources of content?

**LENNY RACHITSKY** (00:55:36):
This is actually an audience question on Twitter.

**LENNY RACHITSKY** (00:55:38):
Anurag Verma asks this, “What are your favorite sources of content to learn from in terms of what's happening in the world and what to pay attention to?”

**KUNAL SHAH** (00:55:47):
I wish I could think of an answer.

**KUNAL SHAH** (00:55:50):
My method of collecting information is mostly about, I come up with conjectures in my head and then I go all over the place to find out if there is proof if what I'm saying is true or not.

**KUNAL SHAH** (00:56:04):
For example, I recently came up with a conjecture that everybody who has been successful in the history of business of vices, historically has done a lot of philanthropy to create a good image for themselves, and therefore is being treated as a respected citizen versus being treated as a person who did vices to make wealth.

**KUNAL SHAH** (00:56:24):
And then I asked GPT to come up with 50 people who did that and what were their vices?

**KUNAL SHAH** (00:56:30):
How did they change the reputation by doing lots of philanthropy and all of that stuff?

**KUNAL SHAH** (00:56:36):
Then a thing happens.

**KUNAL SHAH** (00:56:37):
And then I research in all sorts of directions. And I have no boundaries if I go to chemistry or physics or human behavior to discover some universal principles.

**KUNAL SHAH** (00:56:48):
So my method of learning is to constantly come up with conjectures from the dots that you have connected and then absolutely work hard to find proof of it and then use that to connect to the next dot.

**KUNAL SHAH** (00:57:01):
So I often tell people that every book you read makes your brain poorer to read the next book.

**KUNAL SHAH** (00:57:10):
That's the purpose of books, but that's true for every single thing we learn.

**KUNAL SHAH** (00:57:13):
It makes our brain poorerfor the next thing that we are supposed to learn.

**LENNY RACHITSKY** (00:57:17):
Is there a recent example of that where you got super sucked into some topic?

**KUNAL SHAH** (00:57:20):
Well, it's my daily life.

**KUNAL SHAH** (00:57:22):
I get sucked into topics every now and then.

**KUNAL SHAH** (00:57:26):
For example, I've been thinking about second order effects of AI and what happens to countries and jobs and how to expect some of these things to change, not change, rate of change, rate of skill change.

**KUNAL SHAH** (00:57:39):
I got recently obsessed with what happens to lab grown diamonds if they become big?

**KUNAL SHAH** (00:57:44):
Does it kill diamonds?

**KUNAL SHAH** (00:57:44):
Does it make diamonds bigger?

**KUNAL SHAH** (00:57:46):
And then I looked at parallels.

**KUNAL SHAH** (00:57:48):
So, the pearl industry was very big before culture.

**KUNAL SHAH** (00:57:53):
Cultured pearls  came and the high status of pearls disappeared because everybody could have pearls.

**KUNAL SHAH** (00:57:59):
But not too long ago, pearls were a very royal thing . Every prince and princess used to have pearls around them, but as soon as it was easy to manufacture in a lab, it lost its value.

**KUNAL SHAH** (00:58:13):
So then  I think should I be shorting or going long on diamonds thinking about what happens?

**KUNAL SHAH** (00:58:19):
But there'll be a temporary period of making a lot of money on lab grown diamonds, which will kill... it'll become parasitic on the status of diamonds and destroy all of the profit pools.

**LENNY RACHITSKY** (00:58:31):
You heard it here first, time to buy some diamond futures.

**LENNY RACHITSKY** (00:58:35):
I feel like there's no one in the world ChatGPT impacted more than you considering how much you want to spend digging into random topics.

**KUNAL SHAH** (00:58:43):
I often wonder, Lenny, that if you took the most serious people and made their GPT searches public, a lot of people will learn because the problem of GPT is now it'll make the people with great questions do well, versus people who are looking for basic answers.

**KUNAL SHAH** (00:59:00):
So I think the world is going to be unfair to people who will ask great questions.

**LENNY RACHITSKY** (00:59:05):
Interesting.

**LENNY RACHITSKY** (00:59:06):
Okay.

**LENNY RACHITSKY** (00:59:06):
Well, I got to ask you, is there any advice you have for asking great questions that has helped you in your work and career and life?

**KUNAL SHAH** (00:59:14):
Whenever somebody has many choices and they make the right choice in whatever domain they have.

**KUNAL SHAH** (00:59:21):
For example, let's say you could hire anybody but you hired great people, or let's say you could have married anybody, but you married a great person and so on and so forth. Everybody has many choices to make.

**KUNAL SHAH** (00:59:32):
How do they make choices for that domain of expertise?

**KUNAL SHAH** (00:59:38):
And I think that is the most, and many times they're not going to be able to explain how they make great choices.

**KUNAL SHAH** (00:59:43):
They'll have to really go into that because they don't really have their mental models figured out.

**KUNAL SHAH** (00:59:49):
They cannot articulate, they cannot coach, they cannot explain.

**KUNAL SHAH** (00:59:51):
But if you can figure out how they make great decisions in general, in whatever domain of work they're doing, you'll find many interesting insights coming over there.

**KUNAL SHAH** (01:00:01):
The other good question to ask is about second order thinking.

**KUNAL SHAH** (01:00:06):
What do they think will happen to the world and why did they come to that conclusion?

**KUNAL SHAH** (01:00:11):
And you see that full chain of thoughts is very powerful.

**KUNAL SHAH** (01:00:15):
For example, second order thinking is known to be the most powerful trait to predict the success of somebody.

**KUNAL SHAH** (01:00:22):
But I often wonder what happened in the childhood of people who became great at second order thinking.

**KUNAL SHAH** (01:00:30):
And that question is not fully discovered or discussed yet.

**KUNAL SHAH** (01:00:34):
And I've found some loose examples such as if you played strategy games or only physical games as a strong correlation to building

**KUNAL SHAH** (01:00:42):
So rigor came from physical games, but second order thinking came from playing strategy games as a kid.

**KUNAL SHAH** (01:00:48):
And if you had both, you could do really well in general because you have discipline and second order thinking together.

**KUNAL SHAH** (01:00:55):
Then did you ever have an exercise of looking at history?

**KUNAL SHAH** (01:01:01):
For example, one of the things I recommend for parents to do with their kids, I call it the ‘Whyfi school’, is ask them  one ‘why’ question every meal and let them come back with answers the next day.

**KUNAL SHAH** (01:01:15):
For example, “Why do humans wear jewelry” and ”Why is something a certain way?”

**KUNAL SHAH** (01:01:23):
And let them go into the full depth of history and find out.

**KUNAL SHAH** (01:01:29):
Why is it so expensive to advertise in the Super Bowl?

**KUNAL SHAH** (01:01:32):
And so on and so forth.

**KUNAL SHAH** (01:01:33):
You just take one question.

**KUNAL SHAH** (01:01:34):
And if you train them on why, they evolve at a very different rate because how, what are the questions which do not evolve at a much higher rate, because ‘why’ is the deep question and it breaks a lot of things in your head.

**KUNAL SHAH** (01:01:48):
Or another question about origin stories that “How did elevators come into being?” and "what made your phones happen?”

**KUNAL SHAH** (01:01:54):
“What made microphones happen and why is it called microphone and why is it called a phone?”

**KUNAL SHAH** (01:01:59):
And if you just want to go into this depth, you'll see people build second order thinking automatically because either you go into history and see second order thinking coming along with that, or you play games that train your brain for second order thinking with the spectrum.

**KUNAL SHAH** (01:02:13):
But that's a broad range of things that I think people should be asking.

**LENNY RACHITSKY** (01:02:17):
I'm looking forward to Kunal’s children's raising book, like a book to help you raise kids.

**LENNY RACHITSKY** (01:02:23):
This could be your future.

**KUNAL SHAH** (01:02:24):
I don't have kids so I can run experiments on everybody else's kids.

**KUNAL SHAH** (01:02:27):
So it's a great thing to do.

**LENNY RACHITSKY** (01:02:29):
I feel like with these questions, I think the rule has to be you can't just ask ChatGPT for the answer if the block it-

**KUNAL SHAH** (01:02:34):
Actually it's not bad.

**KUNAL SHAH** (01:02:36):
I think you should encourage it because we have to assume that we are going to be all co-pilots of AI now.

**KUNAL SHAH** (01:02:42):
What you have to do is derive the second order insight that, “Okay, this is true.

**KUNAL SHAH** (01:02:46):
Where is the similarity of this in somewhere else?”

**KUNAL SHAH** (01:02:49):
Give me an example of this found somewhere else, and so on and so forth.

**LENNY RACHITSKY** (01:02:54):
Amazing.

**LENNY RACHITSKY** (01:02:55):
Okay.

**LENNY RACHITSKY** (01:02:56):
I have just a couple more questions before we get to our very exciting lightning round.

**LENNY RACHITSKY** (01:03:00):
First, let's visit the contrarian corner.

**LENNY RACHITSKY** (01:03:03):
I'm curious. What's something that you believe that very few other people would agree with you on and why do you hold that belief?

**KUNAL SHAH** (01:03:12):
Our understanding of wealth and what wealth is, is flawed.

**KUNAL SHAH** (01:03:16):
To me, wealth is nothing but storage of energy.

**KUNAL SHAH** (01:03:20):
And therefore the reason wealth is not zero sum is because energy is, and we are just finding  ways to convert energy to our advantage.

**KUNAL SHAH** (01:03:28):
We are the only species that has managed to convert all forms of energy to our advantage.

**KUNAL SHAH** (01:03:32):
Kinetic energy and fuel and sound and solar.

**KUNAL SHAH** (01:03:35):
No other species has done this.

**KUNAL SHAH** (01:03:37):
And therefore, since the industrial revolution, our wealth has gone like this and continues to be like that.

**KUNAL SHAH** (01:03:42):
AI and nuclear fission and all this stuff will kind of take us right there.

**KUNAL SHAH** (01:03:47):
So I have a strong view that we will never, never have equality of wealth.

**KUNAL SHAH** (01:03:55):
In fact, chasing that is actually a bad idea.

**KUNAL SHAH** (01:03:58):
But if you let people do well and chase wealth, they have enough wealth for everybody else and we could help a lot of people out.

**KUNAL SHAH** (01:04:06):
And I think it's complicated because we can have all these democratic arguments that wealth is concentrated and all that, but that's the physics of wealth.

**KUNAL SHAH** (01:04:16):
It'll always be concentrated.

**KUNAL SHAH** (01:04:18):
You change these mediums, companies, countries.

**KUNAL SHAH** (01:04:23):
To me, wealth is nothing but an entropic complexity that'll keep changing its form and shape.

**KUNAL SHAH** (01:04:29):
You can keep fighting it or accept its physics and reap the benefit of that physics.

**LENNY RACHITSKY** (01:04:34):
I think Elon had this interesting point that wealth is just a database where everyone's wealth I guess is just a row in the database and here's how much everyone has and you're just transferring numbers around and that's the whole economy.

**KUNAL SHAH** (01:04:49):
No, but the nuance that is important is that you can actually increase the database size infinitely.

**LENNY RACHITSKY** (01:04:54):
That's true.

**KUNAL SHAH** (01:04:55):
And therefore his vision of the sun's energy, if you really convert all the energy to our advantage, the amount of wealth we will create for humans is disproportionate.

**KUNAL SHAH** (01:05:04):
And all the species that are managed to collaborate and cooperate to create wealth, for example, let's define wealth as biomass.

**KUNAL SHAH** (01:05:12):
So let's say ants and bacteria and humans are the only few things that have the largest biomass on this planet because we figured out how to make energy work to our advantage.

**LENNY RACHITSKY** (01:05:23):
Wow.

**LENNY RACHITSKY** (01:05:24):
I love all the directions we've gone.

**LENNY RACHITSKY** (01:05:27):
Probably the last question, is there a story of failure in your career that would be interesting to share?

**LENNY RACHITSKY** (01:05:34):
Something that taught you an important lesson?

**KUNAL SHAH** (01:05:36):
It's a series of failures.

**KUNAL SHAH** (01:05:39):
I think there is no escape for anybody who's done anything in life, not failed a lot, like every day, every thing.

**KUNAL SHAH** (01:05:46):
But I would say that many initiatives, many products, companies that I've built have absolutely failed, hirings that have failed, trust broken, betrayals.

**KUNAL SHAH** (01:06:01):
So I think there is no end to it.

**KUNAL SHAH** (01:06:04):
But I think entrepreneurs have this weird ability to forget about failures and almost turn that into a lesson that you hold, and you forget the story.

**KUNAL SHAH** (01:06:21):
For example, COVID has literally no memory for me.

**KUNAL SHAH** (01:06:24):
I just don't remember what was COVID.

**KUNAL SHAH** (01:06:27):
It's just a blank in my head right now.

**KUNAL SHAH** (01:06:30):
And I think that humans are great at forgetting the memory of failure, but remember the lesson from failure.

**KUNAL SHAH** (01:06:36):
But I think I'm constantly learning, and I often believe that life is too short to make all our mistakes ourselves.

**KUNAL SHAH** (01:06:43):
So we should be learning from other people's failures as well.

**KUNAL SHAH** (01:06:46):
And a lot of times we don't do that because we believe that we are special, nothing like that will happen to us, but as humans, we should be learning.

**KUNAL SHAH** (01:06:55):
I would say that my life started from a failure.

**KUNAL SHAH** (01:06:58):
My family went through a severe financial crisis.

**KUNAL SHAH** (01:07:01):
I had to start working from age 15 and I feel till date, I'm just trying to escape that failure that happened in the family.

**KUNAL SHAH** (01:07:10):
So I think many of us are just fighting that initial large failure that we've had and don't want to be anywhere near that.

**KUNAL SHAH** (01:07:21):
And although we are significantly far away from that, the feeling is exactly that.

**LENNY RACHITSKY** (01:07:27):
Circles back to one of our first few questions about the chips on shoulders driving a lot of motivation.

**LENNY RACHITSKY** (01:07:33):
There's this phrase, ”Chips on shoulders drive chips in pockets.”

**KUNAL SHAH** (01:07:39):
That's interesting.

**LENNY RACHITSKY** (01:07:40):
Yeah.

**LENNY RACHITSKY** (01:07:40):
Is there anything more you want to share about that early challenge you ran into or is that something you've shared often?

**KUNAL SHAH** (01:07:46):
No, I mean I've shared that enough, but I used to not talk about it before because I used to think that I would get some sympathy for that.

**KUNAL SHAH** (01:07:54):
And only in the recent past did I speak about it because I want people to realize that I was not some gifted kid who had some rich parents who made me extraordinarily bright and put me in great schools and colleges and I made my way through that.

**KUNAL SHAH** (01:08:12):
I used to not talk  about it earlier because there's a lot of tendency to give sympathy to those people who say, "Oh, this guy had struggled."

**KUNAL SHAH** (01:08:17):
And I don't want to be given any credit for playing that poverty card or this card or struggling for food card.

**KUNAL SHAH** (01:08:29):
That's not an excuse.

**KUNAL SHAH** (01:08:32):
There are so many people in the world who've done extraordinarily well because they had the gift of struggle.

**KUNAL SHAH** (01:08:37):
And I often tell people that this is the biggest curse of successful parents, that that's the only gift they'll not be able to give to their kids, the gift of struggle that they had.

**LENNY RACHITSKY** (01:08:46):
Wow.

**LENNY RACHITSKY** (01:08:47):
I think about that a lot.

**LENNY RACHITSKY** (01:08:47):
We have a kid, he's eight months now, and so I'm trying to figure out the balance of struggle versus making life easy and great, a new challenge for me to figure out.

**LENNY RACHITSKY** (01:08:57):
Before we get to a very exciting lightning round, is there anything else, Kunal, you wanted to share or leave listeners with?

**LENNY RACHITSKY** (01:09:02):
Anything?

**LENNY RACHITSKY** (01:09:02):
Any last nuggets of thoughts?

**KUNAL SHAH** (01:09:04):
Well, I would love for the listeners from different fields of product to share what you're learning without being fearful of the judgment of your peers, because there are many, many people who are learning only because you share your evolution and your thoughts.

**KUNAL SHAH** (01:09:22):
And I believe that a lot more could be contributing.

**KUNAL SHAH** (01:09:25):
And a lot of your listeners are really bright people.

**KUNAL SHAH** (01:09:28):
If they all shared, many people from many places in the world would learn and achieve some amount of success.

**KUNAL SHAH** (01:09:38):
Thanks to your sharing.

**KUNAL SHAH** (01:09:39):
Amazing.

**LENNY RACHITSKY** (01:09:40):
With that, we've reached our very exciting lightning round.

**LENNY RACHITSKY** (01:09:43):
Are you ready?

**KUNAL SHAH** (01:09:45):
All set.

**LENNY RACHITSKY** (01:09:46):
Let's do it.

**LENNY RACHITSKY** (01:09:47):
First question, what are two or three books that you've recommended most to other people?

**KUNAL SHAH** (01:09:53):
It keeps changing a lot, but my books are usually around understanding human behavior.

**KUNAL SHAH** (01:09:58):
And I keep changing based on the person, but I think it's the biggest subject.

**KUNAL SHAH** (01:10:03):
All our customers, all our investors, all our employees, all our relationships are all humans.

**KUNAL SHAH** (01:10:08):
And the subject that we are weakest on is human behavior.

**KUNAL SHAH** (01:10:11):
And how do we live this life?

**KUNAL SHAH** (01:10:13):
We are playing life on extremely hard mode if you don't learn human behavior.

**KUNAL SHAH** (01:10:17):
So I would say that's one thing.

**KUNAL SHAH** (01:10:19):
The second thing, evolutionary biology, teaches a lot about how species evolve and how they make decisions and what are the core motivations that drive everybody.

**KUNAL SHAH** (01:10:28):
So that's another one I would recommend.

**KUNAL SHAH** (01:10:30):
And I don't want to make a recommendation because I can barely finish a book to be honest.

**KUNAL SHAH** (01:10:36):
So I believe in drifting and getting deeper into topics.

**KUNAL SHAH** (01:10:39):
So understanding the topics versus trying to say, give me these three books and I'm going to be good.

**KUNAL SHAH** (01:10:43):
And the last one I would say, is that anything that can make you learn something about their journey versus their success.

**KUNAL SHAH** (01:10:53):
So sometimes autobiographies are too celebratory in some ways, but if you can just kind of understand how… any book that can teach you about how people recover from a setback in great detail is a great book to learn from.

**LENNY RACHITSKY** (01:11:11):
An audience member on Twitter actually asked a similar question along these lines, if there's one book that you could read over and over and over, what would that be?

**LENNY RACHITSKY** (01:11:20):
Is there one?

**KUNAL SHAH** (01:11:21):
I absolutely don't believe in reading over and over because I believe that we are evolving.

**KUNAL SHAH** (01:11:29):
You might discover the same stuff coming from different books and you would say, "Oh, I can categorize this in my brain again and again."

**KUNAL SHAH** (01:11:34):
But I think we tend to become believers, and it becomes too religious if you repeat.

**LENNY RACHITSKY** (01:11:47):
Yeah.

**LENNY RACHITSKY** (01:11:49):
Next question, do you have a favorite recent movie or TV show that you've really enjoyed?

**KUNAL SHAH** (01:11:54):
I love Oppenheimer because of the struggles and Nolan's craft of making the movies, but nothing in the recent past that I feel is right up there.

**LENNY RACHITSKY** (01:12:05):
Do you have a favorite interview question that you like to ask candidates that you're interviewing?

**KUNAL SHAH** (01:12:11):
I like to ask a hypothetical second order thinking question.

**KUNAL SHAH** (01:12:15):
For example, if everybody who has taken a COVID vaccine dies tonight, what happens in 12 months from now?

**KUNAL SHAH** (01:12:23):
Can you explain the world- from what happens to money, what happens to law?

**KUNAL SHAH** (01:12:28):
What happens to countries?

**KUNAL SHAH** (01:12:29):
What happens to the military?

**KUNAL SHAH** (01:12:30):
What happens to the stock market?

**KUNAL SHAH** (01:12:32):
What happens to the order of things?

**KUNAL SHAH** (01:12:35):
And I would say less than 10% of really smart people can have really good answers.

**KUNAL SHAH** (01:12:43):
So it tells you how good they are at second order thinking.

**KUNAL SHAH** (01:12:48):
But the questions can keep changing.

**KUNAL SHAH** (01:12:49):
For example, if you said that, what if arranged marriages were banned in India, and you got capital punishment for doing arranged marriages?

**KUNAL SHAH** (01:12:57):
What happens to the country?

**KUNAL SHAH** (01:12:59):
How do we change from there?

**KUNAL SHAH** (01:13:01):
Like some absurd scenarios, but then what happens after that?

**LENNY RACHITSKY** (01:13:05):
Not to give away your secret sauce, but what do you look for in an answer that gives you a sense there?

**KUNAL SHAH** (01:13:09):
The range of things that they could go into and think about-  if this happens, B happens and then C happens.

**KUNAL SHAH** (01:13:18):
The leaps they could make.

**LENNY RACHITSKY** (01:13:20):
And just so people understand, when you're talking about second order thinking, what's the simplest way to describe that concept?

**KUNAL SHAH** (01:13:26):
I think the simplest way to think about this is being able to correctly judge the butterfly effect of an event as close as possible.

**KUNAL SHAH** (01:13:37):
For example, a lot of people in the stock market use that to say how stocks will go up and down.

**KUNAL SHAH** (01:13:44):
There's something that has happened in the market.

**KUNAL SHAH** (01:13:46):
“Oh, there is a war now with Russia, then what happens to the market?”

**KUNAL SHAH** (01:13:52):
Can you be good at predicting that?

**KUNAL SHAH** (01:13:54):
But in everything in life, if this happens, a lot of people hate this because it's very taxing to the brain.

**KUNAL SHAH** (01:14:02):
The brain absolutely hates second order thinking unless you've trained your brain with second order thinking all the time that it looks forward to it.

**KUNAL SHAH** (01:14:10):
So you convert this into a hate versus a reward cycle, and that comes with probably doing it early on in your life.

**KUNAL SHAH** (01:14:19):
Later on, people hate doing second order thinking.

**LENNY RACHITSKY** (01:14:22):
It is.

**LENNY RACHITSKY** (01:14:23):
Yes.

**LENNY RACHITSKY** (01:14:23):
That sounds like a lot of work for the brain.

**LENNY RACHITSKY** (01:14:26):
Okay.

**LENNY RACHITSKY** (01:14:26):
Just a few more questions.

**LENNY RACHITSKY** (01:14:27):
Do you have a favorite product that you've recently discovered and that you really love?

**KUNAL SHAH** (01:14:32):
I'm looking forward to my Vision Pro coming soon.

**LENNY RACHITSKY** (01:14:37):
It's a future favorite product.

**LENNY RACHITSKY** (01:14:39):
We have actually Boz from Meta coming on as the next guest in my recording.

**LENNY RACHITSKY** (01:14:43):
I'm not sure when they come out in sequence, but we're going to talk about his thoughts.

**KUNAL SHAH** (01:14:48):
The most fascinating thing that I saw was Zuck talking about the utility of Meta being better than Vision Pro and their product.

**KUNAL SHAH** (01:14:59):
And that's exactly going to work well for Apple because when you try to make the product more utilitarian, it loses status.

**KUNAL SHAH** (01:15:08):
And if you study animals, you realize that the one which gets the highest mating success is the one which can demonstrate the ability to waste resources and not be very efficient with resources.

**KUNAL SHAH** (01:15:20):
And therefore people who are known to buy a product that is wasteful will actually own higher status.

**KUNAL SHAH** (01:15:26):
And I think Zuck made it actually quite easy for Apple to demonstrate their superior positioning by saying that, "Oh, we are not as efficient, we are not as cheap.

**KUNAL SHAH** (01:15:35):
We are not for everybody."

**LENNY RACHITSKY** (01:15:37):
Wow.

**LENNY RACHITSKY** (01:15:37):
Just continue to blow minds even on our lightning round.

**LENNY RACHITSKY** (01:15:42):
Do you have a favorite life motto that you often come back to share with friends and family, find useful in work or in life?

**KUNAL SHAH** (01:15:50):
It's not a favorite motto, but I think we truly are transient and we are very lucky to have this life that we have and we have to make the most out of it.

**KUNAL SHAH** (01:16:01):
And all these struggles will mean nothing.

**KUNAL SHAH** (01:16:05):
I often tell people that you should wish for your life to be so great that you have collected the highest amount of content when you are old, and you have no end to the stories that you can talk about.

**LENNY RACHITSKY** (01:16:16):
That reminds me of a book I once read that really had an impact on me where somebody was trying to make a movie of their life and the producer was like, "There's nothing.

**LENNY RACHITSKY** (01:16:24):
There's no good movie here.

**LENNY RACHITSKY** (01:16:25):
You have not done enough interesting things."

**KUNAL SHAH** (01:16:27):
I love it.

**LENNY RACHITSKY** (01:16:29):
And so he turned his lens of what to do in life, by thinking what would make a great story.

**LENNY RACHITSKY** (01:16:36):
And so he just started to do a a great story, something where you overcome challenges and achieve something you wanted.

**LENNY RACHITSKY** (01:16:41):
And so that became his life motto.

**LENNY RACHITSKY** (01:16:43):
“I'm going to try hard things and overcome them.

**LENNY RACHITSKY** (01:16:45):
And that's going to be my life.”

**KUNAL SHAH** (01:16:47):
I love it.

**KUNAL SHAH** (01:16:47):
I love it.

**KUNAL SHAH** (01:16:47):
I love it.

**LENNY RACHITSKY** (01:16:48):
I'll link to that book in the show notes.

**LENNY RACHITSKY** (01:16:51):
Final question, do you have this series on Twitter that you call Monday Motivations?

**LENNY RACHITSKY** (01:16:56):
I'm curious what's motivating you these days?

**KUNAL SHAH** (01:16:58):
I find the internet is filled with all these people trying to give fake motivation and make money off that stuff.

**KUNAL SHAH** (01:17:04):
And it's almost like a drug for people to feel, ”Oh my God, there's motivation, I'm going to do well.”

**KUNAL SHAH** (01:17:11):
I just wanted to remind people that all success comes from an extraordinary amount of pain and struggle and hard work, and there is no shortcut to anything material coming in life.

**KUNAL SHAH** (01:17:22):
And so the Monday  motivation post comes as the anti-motivation post because the world is filled with... I believe that the biggest profit making scheme that I've seen in recent times is to tell people to love themselves and they'll pay you money for saying that.

**KUNAL SHAH** (01:17:40):
And I think the best way to love yourself is to keep evolving.

**KUNAL SHAH** (01:17:44):
So my motivation comes from evolution, connecting dots, solving harder problems than I've solved in the past.

**KUNAL SHAH** (01:17:51):
And I think life is ultimately a game where you want to feel that your levels have changed and your skills have changed constantly.

**LENNY RACHITSKY** (01:17:59):
Kunal, you are wonderful.

**LENNY RACHITSKY** (01:18:01):
Thank you so much for being here.

**LENNY RACHITSKY** (01:18:03):
Two final questions.

**LENNY RACHITSKY** (01:18:03):
Where can folks find you online if they want to reach out and follow up on some of this stuff?

**LENNY RACHITSKY** (01:18:07):
And how can listeners be useful to you?

**KUNAL SHAH** (01:18:09):
You can find me on social media.

**KUNAL SHAH** (01:18:10):
Look for Kunal Shah, you'll find me everywhere.

**KUNAL SHAH** (01:18:13):
I usually have a different personality on each social media.

**KUNAL SHAH** (01:18:16):
And in terms of being helpful, keep tagging me on interesting things that you discover that gave you that moment of, ”Oh my God, I did not know this.”

**KUNAL SHAH** (01:18:25):
I would love that.

**LENNY RACHITSKY** (01:18:27):
Amazing.

**LENNY RACHITSKY** (01:18:28):
Kunal, again, thank you so much for being here.

**KUNAL SHAH** (01:18:31):
Thank you so much for having me.

**LENNY RACHITSKY** (01:18:32):
Bye everyone.

**LENNY RACHITSKY** (01:18:32):
**78**:
34Thank you so much for listening.

**LENNY RACHITSKY** (01:18:35):
If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.

**LENNY RACHITSKY** (01:18:42):
Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast.

**LENNY RACHITSKY** (01:18:48):
You can find all past episodes or learn more about the show at lennyspodcast.com.

**LENNY RACHITSKY** (01:18:54):
See you in the next episode.

---

## [19/19] How to speak more confidently and persuasively | Matt Abrahams (professor, podcast host, author, speaker)

**Matt Abrahams** (00:00:00):
Visualization is a really useful technique and you see yourself not just in the moment of speaking, but getting up to the stage, seeing it being well received, thinking about how you step off the stage. We see athletes do this kind of thing all the time, and there's good research to say that this desensitizes people.

**Lenny Rachitsky** (00:00:16):
Most of the public speaking we do is on the spot. It's not often you give a prepared talk.

**Matt Abrahams** (00:00:20):
You actually have to prepare to be spontaneous. And that's counterintuitive, but when you think about it in athletics or jazz music, it's like of course you would prepare and practice.

**Lenny Rachitsky** (00:00:28):
Are there any other techniques that you love that you find people find really helpful in calming their anxiety?

**Matt Abrahams** (00:00:34):
Strive for connection over perfection by daring to be dull. Just answer the question. Just give the feedback. Just be engaged in the small talk. By doing that, you dial down the volume of self-evaluation, freeing up resources that can be used to really help you succeed.

**Lenny Rachitsky** (00:00:54):
Today my guest is Matt Abrahams. Matt is a professor at Stanford University's Graduate School of Business where he teaches a very popular class on communication and public speaking. He's also the host of the incredibly popular podcast, Think Fast, Talk Smart; and the author of the very popular book, Think Faster and Talk Smarter. Matt also coaches people one-on-one on public speaking and communication skills. And in our conversation we focus on the two areas that people most need help with. One, reducing their anxiety before and during any form of public speaking, and getting better at speaking on the spot, including giving better toasts, giving feedback, doing Q&A, and even apologizing.

**Lenny Rachitsky** (00:01:36):
Like we talk about in the actual conversation, speaking well is a superpower in your career for interviewing, for being great in meetings, for pitching your manager on ideas, to leading teams. And the skill becomes even more important as you grow in your career. The good news is that you can get better at it with a bit of help. I've worked on this a lot over the course of my career and I still get really nervous before big talks and even before every podcast episode, but many of these techniques I actually put into practice and I share that in our conversation. If you pick just a couple things from this episode to put into practice, you'll become a better communicator, you'll be less nervous, and you'll get better at dealing with on-the-spot moments.

**Matt Abrahams** (00:04:54):
Lenny, I am excited for our conversation and thank you for having me.

**Lenny Rachitsky** (00:04:57):
Thank you for being here. I'm even more excited for the conversation. So what I want to do with our time today is there's two areas I want to focus. One is talking about techniques to help people manage anxiety when public speaking. And two is helping people get better at speaking on the spot, which you wrote a whole book about. And if you think about it, I think that's like most of the public speaking we do is on the spot. It's not often you give a prepared talk. It's usually like you said, Q&A or a or toast someone wants to give you or ask for feedback or things like that. So I'm excited to dig into those things. How do that sound broadly?

**Matt Abrahams** (00:05:33):
Absolutely, I look forward to that and those are topics I'm very excited to talk about, have done a lot of research in and look forward to sharing more.

**Lenny Rachitsky** (00:05:41):
I suspected as much. Okay, so let's talk about anxiety. You have a bunch of really novel techniques in your book and your podcast for calming your body down, calming your mind down when you're planning to give a talk, when you're actually about to give a talk, when you're giving a talk. And a lot of these I haven't actually seen anywhere else and I've used a few of them and they are really great. So what I was thinking we'd do is let me go through the ones that I found most useful and interesting and just share your advice on those and then see if there's any I missed and then maybe add those at the end. How's that?

**Matt Abrahams** (00:06:15):
That sounds great. That sounds great. I love that you've applied some of these techniques and found value from them.

**Lenny Rachitsky** (00:06:19):
I'll talk about this, I'll talk about this. Okay, first of all, just to catch on this, you're not a fan of the picture people in your audience naked approach, correct?

**Matt Abrahams** (00:06:27):
The Brady Bunch advice is not good advice. I don't know about you and I don't know anybody who could imagine seeing a bunch of people in their underwear and feel more comfortable with that. And I think if you do, there are other issues you need to be dealing with than beyond speaking anxiety.

**Lenny Rachitsky** (00:06:42):
Yeah, it feels like highly inappropriate now, just that idea, trying to picture everyone-

**Matt Abrahams** (00:06:46):
No, but underlying that if you'll give me a moment, there is some value. This notion of visualization as a tool of desensitization actually can be very helpful, but you're not visualizing the audience half naked. What you're doing is you're visualizing yourself in that space. You're visualizing the audience responding to you and what you're saying. So just like a pilot might do a flight simulator, having a visualization can actually really help you feel more comfortable and confident. It literally puts you in the room even though you're not there. And there's some tools and I'm fascinated by these tools that are virtual reality tools that can also serve to desensitize you. So this notion of seeing your audience in advance of actually speaking can actually impact your level of comfort. It's let's keep everybody clothed and let's keep them all focused on your topic.

**Lenny Rachitsky** (00:07:36):
Well, let's actually talk about this one while we're on it because I think this is a really powerful technique. An idea just to kind of summarize, you picture ahead of time, what it's going to look like and feel like. You talking, looking at the audience. You talk about that and just how to go about using that technique.

**Matt Abrahams** (00:07:50):
Yeah, absolutely. And this is some of the oldest research on public speaking anxiety. It was research done in the '80s from the University of Oregon. So visualization, what it does is it allows you to see the event in a way that you have much more control over it so you can think about it. So a good visualization involves some deep breathing to calm yourself. Either you close your eyes or you just look at a picture. Maybe you can get a picture of the environment you're speaking in. I often recommend speakers see the room even if they're not physically present, but get a picture online or some way envision yourself in the room, envision yourself in the room with the people you'll be speaking to. Often we know the individuals or some of them. We can also go online and figure out who they are.

**Matt Abrahams** (00:08:39):
So visualization is a really useful technique and you see yourself not just in the moment of speaking but getting up to the stage, delivering the presentation, seeing it being well received, thinking about how you step off the stage. And by taking yourself through that you in essence are a dress rehearsal even though you're not physically in the room. And there's good research to say that this desensitizes people. We see athletes do this kind of thing all the time where they'll do visualization to help them and it really does work. And like I said, there are virtual tools now that can help you do this where you can actually program it to have a certain size audience. You can even program some of these to have a responsive audience or a distracted audience. All of this in service of just preparing you for what you're really going to see.

**Matt Abrahams** (00:09:25):
And the bottom line is this, what you're doing for yourself is making sure it's not new and novel. It's something been there, done that, even though if it was virtual or visualized in your mind, to help you feel better about the circumstance. It gives you a sense of agency.

**Lenny Rachitsky** (00:09:42):
I've done this myself actually. I gave a TEDx talk once and it was probably the scariest talk I've ever given and I spent a lot of time doing this and it doesn't actually have to take that much time. It could be like a five-minute thing where you sit down, calm yourself, and then just picture the stuff. And ideally you do it a couple times, I imagine.

**Matt Abrahams** (00:09:57):
That's right. Good for you. And congratulations on giving a TEDx talk. That is a high-stakes talk.

**Lenny Rachitsky** (00:10:01):
Thank you. That was before TEDx became super uncool. It was still pretty early. It's out there in the internet in case people want to find it.

**Matt Abrahams** (00:10:09):
Don't say they're uncool. I'm doing one in two weeks.

**Lenny Rachitsky** (00:10:11):
They're so cool. That is, they are cool.

**Matt Abrahams** (00:10:13):
That's right.

**Lenny Rachitsky** (00:10:17):
They're incredible. I'm impressed.

**Matt Abrahams** (00:10:17):
I've done a number of them and I've coached many people and I think that there's a lot of value that they can provide people.

**Lenny Rachitsky** (00:10:21):
There is. There is. I think they've just become slightly less cool because now there's a lot of them, but they're still incredibly cool, I'm very proud.

**Matt Abrahams** (00:10:29):
Okay, thank you.

**Lenny Rachitsky** (00:10:31):
So on the visualization piece, I think we have a lot of techniques, but just on this one, part of it is continue to calm yourself as you're doing it. I think that's really important because you want to help your body not connect to the stress that you're feeling like you're going to experience.

**Matt Abrahams** (00:10:46):
That's correct. Any distance you can give yourself from the anxiety that you're feeling is helpful and there are lots of techniques that help give you a little bit of distance and visualization is one of those.

**Lenny Rachitsky** (00:10:57):
One of my favorite techniques that it might be in this bucket, it might be on the spot advice bucket, but I think it works great here is what you call dare to be dull. Can you talk about that because I love that?

**Matt Abrahams** (00:11:09):
Yeah. I really leaned into this with the spontaneous speaking work that I've been doing as of late, but it applies to anybody speaking. This is a notion that comes from the world of improvisation and when people hear improv, they often think of standup comedy, having to be funny. And that's not what improv is all about. Improv is all about being present, being collaborative, being open, and it's a wonderful tool just to help you get present oriented. Think of it as like meditation in action, but also it teaches lots of valuable skills for communication.

**Matt Abrahams** (00:11:42):
When we communicate, especially spontaneously, we want to do it really well. We want to answer the question with the best answer, we want to give the right feedback, we want to be the most interesting in small talk and that puts a lot of pressure on ourselves. And you can think of it this way, it's really taxing our cognitive bandwidth.

**Matt Abrahams** (00:12:04):
Your brain in many ways is like a CPU, a computer. It's not a perfect analogy, but it works. And if I am constantly judging and evaluating everything I am saying against some standard of perfection, whatever that is, it means I have a limited amount of bandwidth to focus on what I'm actually saying and connecting to my audience. If you have a laptop or a phone that has lots of windows and apps open, each one of those is performing less well because of the other ones being open. So I often say strive for connection over perfection by daring to be dull. Just get the task done, just answer the question, just give the feedback, just be engaged in the small talk. And by doing that you dial down the volume of self-evaluation, freeing up resources that can be used to really help you succeed. So dare to be dull is all about giving yourself permission to just be present and do what's needed. And when you do that you find that you actually do quite a good job at it.

**Lenny Rachitsky** (00:13:03):
The last point I think is really important, you talk about this in your book. Is when you start with, "Okay, I'm just going to say something, it'll be fine." Without that pressure, you end up saying something better and more interesting and more insightful because you're less nervous about it.

**Matt Abrahams** (00:13:16):
That's exactly right. We are often our biggest impediments to good communication because of the anxiety we bring to the party.

**Lenny Rachitsky** (00:13:23):
That's awesome. And I think this can apply to prepared talks too. When you're preparing a deck, don't put this pressure on yourself, "This has to be the best talk ever." Just like, "I'm going to do my best. Let me just start with something that's good enough." People learn something and then from that, their editing ends up leading to something great in my experience.

**Matt Abrahams** (00:13:39):
Right.

**Lenny Rachitsky** (00:13:40):
Awesome. Okay, let's go to the next technique, and this is another one I've practiced and another guest on the podcast actually suggested this and these two remind me of using this one, which is to tell yourself when you're going to be giving a talk. "I'm excited. This is going to be a lot of fun. I'm so excited to give this talk." And reframe it from, "I'm nervous," to like, "No, I'm excited. This is going to be amazing." Can you talk about that technique?

**Matt Abrahams** (00:14:04):
Absolutely. So this is one of many cognitive reframing techniques. It is often attributed to my friend and colleague, Alison Wood Brooks, she's at Harvard Business School who did some research into this. And what she found is...

**Matt Abrahams** (00:14:18):
Well, first take a step back. When you get physically aroused by anxiety, you're under that fight or flight threat response. It turns out that same response happens to your body when you're excited. The human body has pretty much just one arousal response. Our heart beats faster, we breathe more shallow, we get a little shaky, but the big difference is how we label that. So if I say, "Hey Lenny, guess what? Your colleague couldn't show up today and you need to go teach the class or you need to go give that presentation." You might feel your heart rate go up, get a little shaky, sweat on your brow and you're seeing that as negative. But if I said, "Hey Lenny, guess what? You just won the lottery." Same physiological response would happen, but you would see that likely as more positive.

**Matt Abrahams** (00:15:06):
So how we label the arousal matters and what Alison's research and others have followed up with suggests is that when we feel those symptoms of anxiety, rather than seeing it as negative, say, "This is exciting. I get to share my point of view. I get to demonstrate my value." And in so doing by seeing it as more positive, it causes us by definition to relax. And her research fascinatingly found that people actually were perceived as communicating better. And again that's because that pressure was taken off of them. So I challenge everybody to think about what are the exciting elements of the communication opportunities you have and really lean into those. And when you feel those anxiety symptoms, remind yourself these are signs of excitement. This is me being excited about sharing this information and it can really help.

**Lenny Rachitsky** (00:15:56):
This is another one I've done and it super works. It sounds so trivial and so like, "Why would this do anything?" But I find you just say that just like, "I'm going to have so much fun. This is going to be exciting." It does make an impact. So another one to try, even though it sounds really trivial.

**Lenny Rachitsky** (00:16:12):
Kind of along these lines, there's another technique you recommend which is a mantra, having a mantra that you repeat to yourself. I don't know if it's kind of the same general idea, but you have a couple mantras that you recommend to people like "I have value to add" and things like that. What advice do you have there?

**Matt Abrahams** (00:16:27):
Yes, thank you. And that's mine. The one that you shared is, "I have value to add." So if we were to really listen to the voice in our heads when it comes to communication, we say a lot of negative things to ourselves. We say things like, "I'm not prepared. I'm not going to be as good as this person. I'm an imposter." We carry around with us a lot of this chatter that actually sets us up to not do well or to be more nervous. So if we can actually change that talk track, it can help us.

**Matt Abrahams** (00:17:01):
I'm not saying you have to go to an extreme and say, "I'm going to be the best communicator ever." Rather you can simply say as I do and as you alluded to. What I'll say right before I speak is, "I have value to bring."

**Matt Abrahams** (00:17:12):
Often when we are in communicative situations, especially at work, people want to hear from us. We've been invited to speak, we're on the agenda for the meeting. There is value people can take from our communication and we just have to remind ourselves of that. So having some little mantra that you can say that's not over the top but just makes sense. It could be as simple as you've got this, or I'm prepared, or I know my stuff. And I actually encourage people to write it on a post-it note if you're old school, sometimes people put it into their phones as a reminder. So like a minute or two minutes before they're set to give the presentation or participate in the meeting, it flashes up. We just have to turn off or turn down the noise of that internal negative self-talk.

**Lenny Rachitsky** (00:17:58):
What are some other mantras that you found helpful or that people use?

**Matt Abrahams** (00:18:03):
They're very personal to different people. I was just coaching a senior leader the other day who his mantra was, "Last time this went well." He's a leader, he does a lot of the same presentations and just by saying last time this went well, reminds him that it's likely to go well this time. We are very susceptible to catastrophizing when we're very nervous about things, especially when we're exposed in front of people. Not in the Brady Bunch exposure we talked about earlier, but when we're out there speaking or communicating and simply reminding ourselves that often they go very well is helpful.

**Lenny Rachitsky** (00:18:36):
Yeah. There's another one that I think you shared which is, "It's not about me, it's about my content."

**Matt Abrahams** (00:18:41):
Yes, exactly. That's another one. That's a great one. It can be very helpful.

**Lenny Rachitsky** (00:18:45):
The one you shared about, "I've got this," reminds me, my wife took a course with the Artist's Way writer, Julia Cameron I think is her name. And she has this piece of advice where you name your critic, your inner critic that's always telling you to stop doing stuff. You name him or her. So I name mine Jim. And then when he or she is giving you things you don't want to hear, you're just like, "Jim, I got this. Jim, I don't need this advice."

**Matt Abrahams** (00:19:11):
There is a lot of evidence on personifying the things that challenge us and then having conversations with it. It's a way of rationalizing some of the things that we do that are quite negative. So something there for sure to be thinking about.

**Lenny Rachitsky** (00:19:30):
There we go. Bonus advice. That was-

**Matt Abrahams** (00:19:32):
Bonus advice, yes.

**Lenny Rachitsky** (00:19:33):
I didn't expect that.

**Matt Abrahams** (00:19:34):
And the cool thing that what you're highlighting is there is a lot of advice out there on how to manage anxiety. Many of us feel like we're the only people who feel this nervous because we see our colleagues, our friends or Ted talks as you were talking about, and we see these people communicating just so effortlessly. Often a lot of work went into that and we don't see that work. And sometimes just knowing that others experience it makes us feel better.

**Matt Abrahams** (00:19:58):
If you'll allow me, I'll tell this very quick story. I was in the San Francisco Airport, this was several years ago after my Speaking Up Without Freaking Out book came out, and my name was called over the PA system at the airport counter. The seat that I was supposed to sit in was broken and they wanted to talk to me about it. So when I came away from that, somebody came up to me and said, "Hey, you're the guy that wrote that book on speaking anxiety." I said, "Yes." And I said, "What do you know about it?" He goes, "Oh, I bought the book." I said, "Oh, was it helpful?" He says, "Incredibly helpful, but I didn't read it." I'm like, "This is weird. So you're telling me the book was helpful and you didn't read it?" And so I said, "Tell me more." And he said, "Just knowing that a book like that existed made me feel better because I don't know you and I know you certainly didn't write the book for me. So it implies that lots of people have this issue."

**Matt Abrahams** (00:20:44):
And just by normalizing the anxiety, which by the way is the normal condition. Those of us who study this believe it is innate to being human to feel nervous communicating in front of others. So sometimes just reminding yourself that you're not alone and that others have it can actually help reduce the pressure that we feel.

**Lenny Rachitsky** (00:21:01):
This is such an important point that I am kicking myself for not starting with this also because I think this is something people don't realize. They see all their execs at their company speaking incredibly well, so confidently, so articulately and just like, "Oh my God, how will I ever be someone like that?" Is there anything more you can share of just like you have tons of students that go through your class, you see these issues, they're more transparent, you think about their challenges, I imagine. Is there anything more you could share there to help people feel better? Like this is most people, even when you see someone amazing at speaking, they are also probably nervous.

**Matt Abrahams** (00:21:36):
With regard to that, I think we just need to talk about it more. We need to share about it. I mean, I always will share that I still have anxiety in speaking in certain situations and it's something that's taken me a long time to work on. I also help people understand that it's not a light switch. It's not like you either have it or you don't. It's a process. And so the idea is over time, we will feel less nervous if we apply some of these principles you and I are talking about.

**Matt Abrahams** (00:22:01):
A great technique to help people that often isn't talked about is many of us feel much more comfortable in conversation than we do in presenting. And conversation is a back and forth. So you can actually set up a lot of your communication situations, a presentation, a meeting, et cetera, as conversations. And you don't even have to have a conversation with the audience. You can simply have it with yourself. For example, what would it be like if you were to start a presentation by saying, "Today I have three questions I'd like to answer. Question number one is..." And you state the question and then you answer it. I am actually having a conversation with myself in that moment where I am asking myself a question. I happen to know the answer, I give the answer. This again, just like the reframing as excitement versus anxiety, this is a reframe. I'm not presenting, I'm having a conversation. And in so doing it ratchets down that anxiety.

**Matt Abrahams** (00:22:53):
So we need to talk about it. We need to share our experiences with developing anxiety management plans. We realize it's not binary, it's not I have it or I don't. And we start seeing where we feel more comfortable and how can we bring that comfort level into the types of situations that make us nervous, like simply having a conversation with yourself.

**Lenny Rachitsky** (00:23:13):
You have another technique I think that's different, maybe it's exactly the same, which is to ask a question of somebody else as you're talking, which is I think deflects attention from you. Can you talk about that?

**Matt Abrahams** (00:23:22):
Yeah. So we talked about the way we desensitize through visualization. The other thing we can do is distract.

**Matt Abrahams** (00:23:30):
I coached a very senior leader at Google who got very nervous when he was up in front of people, and what we did is we distract his audience. So he would start every single presentation saying these words, "Good morning, let's watch this video." And he'd show a 30-second video that was on topic about something they were going to talk about in the meeting. And when the video stopped, he would then facilitate a discussion of what that video was about and then he would ease into his content. So he went from being a presenter to being a facilitator or somebody who was having a conversation with the audience. That made him feel so much better.

**Matt Abrahams** (00:24:05):
And so all of us can do things that can distract our audience. Now when I say distract, I don't mean take them on a tangent that's not relevant to what you're saying, but maybe you ask them a question, maybe you tell them a story, maybe you show them a video or ask them to read something. So there are lots of things that you can do that will help get the attention off you for just a little bit so that you can then focus on what works for you or take that deep breath that'll help calm you down. All of these are very useful techniques.

**Lenny Rachitsky** (00:24:35):
Yeah, it's interesting once you start talking, it's okay usually. It's the beginning part that you need [inaudible 00:24:40].

**Matt Abrahams** (00:24:40):
Yeah, most people are most nervous one minute before speaking and the first minute of speaking. And if you can find ways to get yourself through that, then it becomes much easier for most people. There are some people who that's not true for, but for most people that's the way it works.

**Lenny Rachitsky** (00:24:54):
Awesome. Okay, next technique that actually another guest mentioned, and we spent a bunch of time on this, a guest named Johnny Miller, which is a breathing technique. And just to give a little context from what he taught us is that 80% of our neurons go from our body to our brain versus 20% is our brain telling our body what to feel. And so this research shows that what our body's feeling is what our brain's going to think. So if our body's acting nervous, we're going to think, oh, we're nervous. And if you change the state of your body, your mind feels different.

**Matt Abrahams** (00:25:23):
I love this stuff. This research, embodied cognition is what it's called, is fascinating to me. I'll share one of my most favorite studies in this. There was a researcher at Duke, I think it was Duke, who... The only experimental variation that he did is he had people hold something that was cold in their hand, like an iced coffee versus a warm coffee. And then he asked the participants to make ratings of people. And if you were holding something cold, you saw the person as a colder person, as more aloof and more distant, and if you were holding something warm, you saw them as more collaborative and embracing. I find this stuff fascinating. What our body feels, our minds think.

**Lenny Rachitsky** (00:26:03):
Awesome. So along those lines, there's a technique that you recommend that he recommended, but I think it's a great reminder of the double exhale where you breathe in and then you exhale twice as long. Can you talk about that and tell people about it?

**Matt Abrahams** (00:26:13):
Yeah. Breathing is very helpful in managing so many of our anxiety symptoms. It slows down the heart rate, makes our voice sound more normal because when we get nervous, we breathe shallow and that changes... Our voice is a wind instrument, it changes the way we sound, can reduce some of the shakiness. So deep belly breathing, the kind you do if you've ever done yoga or tai chi, qigong, really important to do and there are a whole bunch of variations on it. The one you're talking about is the double inhalation where you're taking an inhale in until you feel completely full and then you sneak in a little extra air and then you take a long exhale. People call it box breathing and other types of breathing.

**Matt Abrahams** (00:26:54):
The bottom line is this, what's critical to the relaxation response is the exhale. Lots of ways to inhale, lots of ways to exhale. You want your exhale to be longer than the inhale. The magic of the relaxation happens during the exhale. So I have a rule of thumb, I jokingly call it a rule of lung. You want your exhale to be twice as long as your inhale. So if you take a three count in, even if you sneak in a little extra air as we were talking about, take a six count out. And it is that way that you will feel... Not only will your body physiologically feel less stress, you'll be more focused in a present moment and not catastrophizing about all the things that might happen in the future.

**Lenny Rachitsky** (00:27:36):
Great. Yeah, so it's like another example of this sounds so trivial and why would breathing differently do have any impact on my nervousness? But one, there's all this research that shows that it does, and two, if you try it, and this is another one I use, is it actually works very quickly and you do it a few times and like, wow, I feel really different.

**Matt Abrahams** (00:27:54):
Absolutely.

**Lenny Rachitsky** (00:27:55):
It is interesting you put these together. From the way I've seen it, these are two different techniques, but I've never tried them together. One is... I think Huberman is big on this one. All his clips are always talking about this. One of you inhale fully and then you inhale a little bit more and there's some capillaries or something in your lungs that fill up that-

**Matt Abrahams** (00:28:12):
[inaudible 00:28:12]. Yeah.

**Lenny Rachitsky** (00:28:13):
And then there's the 4, 4, 8 is the way this other guest shared is like breathe in four seconds, hold it four seconds, breathe out for eight seconds. But I'm going to try both. Wow. That's going to double up my calmness.

**Matt Abrahams** (00:28:27):
You'll be so mellow, nothing will bother you.

**Lenny Rachitsky** (00:28:29):
So mellow. Okay. Are there any other techniques that you love that you find people find really helpful in calming their anxiety?

**Matt Abrahams** (00:28:39):
Well, so the first book had 50 techniques and not all 50 techniques work for everybody. One that I personally think is a lot of fun is getting present oriented because when I'm in the present, by definition I'm not worried about the future. And many of our anxiety comes from our fear of a potential negative future outcome like, "I'm not going to achieve my goal." So if I can do anything to be in the present moment, that helps me out a lot.

**Matt Abrahams** (00:29:02):
Something I do as part of my personal anxiety management plan is I say tongue twisters. Tongue twisters for me are a great way to get present oriented. You can't say it right if you don't say the tongue twister if you're not focused on the present moment. And it also warms up your voice. A lot of nervous speakers get so inside their head that they don't warm up their voice. And we all know if you've ever done any exercise or competed in any sports, you should warm up first. We have this mistaken notion that we can go from silence to brilliance without warming up. And I like saying tongue twisters out loud to get present oriented and to warm up my voice. So that's one that I often recommend. People think it's silly, but I have people who are like, that really works. It really helps me to get centered and to warm up. And so I like that one a lot.

**Lenny Rachitsky** (00:29:46):
Well, let's share a couple of tongue twisters. What are some recommendations?

**Matt Abrahams** (00:29:50):
I will only share my tongue twister, I say Lenny, if you promise to say it after me.

**Lenny Rachitsky** (00:29:53):
Absolutely. I'm so ready.

**Matt Abrahams** (00:29:55):
This is my favorite tongue twister. It takes five seconds to say, it's three phrases long. And if you say it wrong, you say a naughty word. So I'm going to be listening as for all your listeners. So are you prepared? So it goes as follows, I slit a sheet.

**Lenny Rachitsky** (00:30:10):
I slit a sheet.

**Matt Abrahams** (00:30:11):
A sheet I slit

**Lenny Rachitsky** (00:30:13):
A sheet I slit.

**Matt Abrahams** (00:30:14):
And on that slitted sheet I sit.

**Lenny Rachitsky** (00:30:18):
And on that slitted sheet I sit.

**Matt Abrahams** (00:30:20):
Very good. You didn't say that naughty word. I'm sure you can imagine what it would've been.

**Lenny Rachitsky** (00:30:25):
A lot of danger, a lot of [inaudible 00:30:26].

**Matt Abrahams** (00:30:26):
A lot of danger. But in that moment you weren't thinking about, what's the next question I'm going to ask Matt? Or how much longer do we have in the podcast? No, you were simply focused on what we were saying and trying to say it without saying a naughty word. So that's that [inaudible 00:30:39]-

**Lenny Rachitsky** (00:30:38):
And not have to censor this podcast.

**Matt Abrahams** (00:30:42):
I've only had to bleep one guest in all my years of doing this.

**Lenny Rachitsky** (00:30:46):
Okay, cool. We're going to link to that. Is there any other ones you want to share before we move on to getting better at speaking on the spot?

**Matt Abrahams** (00:30:52):
Well, the last one I'll say is, and this one is another one that falls in the kind of funny category, but there's research that says that when you swear, curse, it actually helps you reduce anxiety. When you curse, you release a flood of neurochemicals that blunt out the neurochemicals associated with anxiety, cortisol being a big one. So you get a big dopamine hit, for example, serotonin when you swear. So I'm not saying get up on stage and drop an F-bomb, but my students love this. I mean, it's like, "Matt's giving me permission to swear." And no, that's not what I'm doing, but it's an interesting technique that seems to help some people is to curse not necessarily in front of people, but that can help. And it also has an analgesic effect. It actually reduces pain as well.

**Lenny Rachitsky** (00:31:44):
That's interesting. I could see during birth women screaming curse words.

**Matt Abrahams** (00:31:48):
Yeah. Well, I'm not going to say what I heard when my kids were born, but...

**Lenny Rachitsky** (00:31:54):
But again, this could double up with the tongue twister where you just go for it and say-

**Matt Abrahams** (00:31:58):
Yeah, every tongue twister has to start with Nantucket and then we're good.

**Lenny Rachitsky** (00:32:05):
**Matt Abrahams** (00:33:39):
I see you said shift very carefully. I appreciate that.

**Lenny Rachitsky** (00:33:44):
Now we're going to be so, so careful, I don't want this podcast flagged and for adults only. Okay, shift to a new topic. You have a whole book about how to get better speaking on the spot. And I think why this is important is again, what I said at the beginning that I think most of our "public speaking" is not planned public speaking. There's people asking for feedback in a meeting, people wanting you to give a toast, Q&A as we talked about. So what I want to do is you have advice for broadly getting better at these things and then you have advice for very specifically how to get better at giving better toast, doing better Q&A, getting better at small talk and things like that. So I want to start with the broad advice and then get into each of these. That sound good?

**Matt Abrahams** (00:34:27):
Absolutely.

**Lenny Rachitsky** (00:34:28):
How about you share your favorite techniques for broadly getting better at speaking on the spot, and then we'll see where that goes?

**Matt Abrahams** (00:34:37):
Sure. So the first thing in helping yourself feel better, speaking spontaneously, which is the vast majority of our communication, the plan presenting, the practiced pitch, the meeting with agenda pale in comparison to the times that we are spontaneously speaking. And the first thing that is important for everybody to know is we can all get better at it. That's the fundamental bottom line. Many of us feel like we're either born with the gift of gab or we're not. And so the first thing we have to realize is we can get better at it.

**Matt Abrahams** (00:35:08):
The second big point to make is you actually have to prepare to be spontaneous. And that's counterintuitive, but it is through preparation that we get better at it. And if you think about it, if you think about an athlete, when an athlete is doing their sport, they are being spontaneous, they are responding to the conditions that present themselves to them. What helps them do well is all the preparation and practice that they've done. So there are lots of analogs to this, but when we think about it in of communication, it seems foreign, but when you think about it in athletics or jazz music, it's like of course you would prepare and practice. Those are the two big underlying principles to helping people get better.

**Matt Abrahams** (00:35:48):
The next level has to do with we have to attack both mindset and approach and the actual messaging itself. The only way I have found to help people get better at this is to look at how we approach it, our mindset, and then how we actually craft the messages through structure and focus that help us be better. So that's the gradual process from the broadest level about how we have to go about making this better for ourselves.

**Lenny Rachitsky** (00:36:14):
Maybe let's dig into the structure.

**Matt Abrahams** (00:36:17):
Sure.

**Lenny Rachitsky** (00:36:17):
What is your advice for how to think about structuring if you're on the spot, like, "Oh, shit, how do I share something smart [inaudible 00:36:22]?"

**Matt Abrahams** (00:36:22):
See, the bad word came out, so you're ready for my tongue twister. So structure is critical. In spontaneous speaking, most of us, because we feel the intense pressure, the anxiety we just talked about, we just spew out information, we list and itemize information. We take our audience on the journey of our own discovery of what we want to say as we're saying it, and our brains are not wired for lists of information. In fact, Lenny, how many items do you need to buy from the grocery store before you actually have to physically write it down? For me it's four. Anything over four, I'm going to forget something. Our brains aren't wired for lists, right?

**Lenny Rachitsky** (00:37:03):
Yeah.

**Matt Abrahams** (00:37:03):
And so-

**Lenny Rachitsky** (00:37:04):
I text myself.

**Matt Abrahams** (00:37:05):
Yeah, right, exactly. Yeah, no, I'm old school. I actually put it on a piece of paper, but the point is that we're not wired that way. Our brains are actually wired for story, for connection, a logical connection of ideas. So it's about connecting those pieces together. So a structure is nothing more than a beginning, a middle, and an end. A package of information. The structure that almost everybody listening in is familiar with is one that comes from the world of advertising. Most advertisements are set up as problem, solution, benefit. There's some problem in the world, here's how we solve it with our product or service, and here's how you benefit from it. That's a structure. It's a logical beginning, middle, and end. These items have a connection. So by finding a structure that you can rely on when put on the spot, it halves your burden.

**Matt Abrahams** (00:37:54):
When you're put on the spot, you have to think about what to say and how to say it. The structure tells you how to say it, and then you just have to think about what to put into it. So it's like having a recipe. If I have a recipe and I have good ingredients, I can cook a good meal. So there are lots of structures.

**Matt Abrahams** (00:38:10):
The whole second part of the book Think Faster, Talk Smarter is specific structures for specific situations, introducing yourself, making an apology, giving feedback. And I'm not saying every time you give an apology or give feedback that you have to follow these structures. It just gives you a place to go when you're in that moment where you're like, "Where do I go? How do I start?"

**Lenny Rachitsky** (00:38:33):
Cool. So we're going to talk about those examples. One of the structures that I liked that I wrote down is called prep, which is make your point, give a reason for making that point, give an example. And then what's the last one point again?

**Matt Abrahams** (00:38:47):
Yeah, restate your point. Review it.

**Lenny Rachitsky** (00:38:48):
Restate your point. That feels like something that say in product teams can come up a lot is just like, here's what I think, here's why. Here's an example and then let me just remind you again what the point I'm making.

**Matt Abrahams** (00:38:57):
That's right. Yes. I love prep and the structure I really like is a three-question structure: What? So what? Now what? And people on product teams I think could benefit so much from this. What is your product, your service, your offering, your update, your feedback? It's the what of why you're speaking. The so what is why is this important and relevant to the people you're talking to or to your company or to prospective clients? And then the now what is what comes next. So on a product team, if you're describing a feature, here's what the feature is, here's why it's important, and here's what we're doing about it. If you're giving an update in an update meeting, a standup that you're having, here's what I'm working on, here's why it's important, here's what I'm doing next.

**Matt Abrahams** (00:39:41):
By packaging the information up in what, so what, now what, it becomes much more digestible, much more memorable. Just like prep. Prep works really well for a point you're making. What, so what, now what works really well for a broader presentation, update, feedback session that you're giving. So having a whole series of these tools in your toolkit can really make a difference.

**Lenny Rachitsky** (00:40:05):
So we've talked about three structures so far. What, so what, now what; prep, which is make the point, give a reason example, and then restate the point; and then problem, solution benefit. So people listening to this it's like, "Oh, amazing, all these structures are great." Do you have any advice on how to remember these? You're like, "Oh, Matt, what do you think of this design?" Like, "Oh, shit, which one should I go with?"

**Matt Abrahams** (00:40:28):
I try to give each structure a catchy name. What, so what, now what rolls off the tongue. There's a structure in the book for giving feedback called 4Is for Apologizing AAA. So part of it is just coming up with a mnemonic that works for you and you can name them whatever you want, but really the way to get familiar with them and to have them at the ready is to use them.

**Matt Abrahams** (00:40:48):
When I coach people on what, so what, now what, I encourage them at the end of a podcast they listen to or something they read, take a moment and say, "What was it about? Why is it important to me and what can I do with that information?" And if you do that, not only do you get better and more comfortable deploying that structure, but you also remember the material better because there's a whole bunch of research that says when we interrogate the material that we listen to or read, we digest it and remember it more. So in 30 seconds you're really helping yourself at least in two ways by getting the structure down and remembering more. So you have to put it into practice.

**Matt Abrahams** (00:41:24):
The other way to do it in which we do a lot in my classroom is we have people dissect communication. So you listen to somebody or you see it and you say, what structure did they use? So it's about awareness building and then actually getting the reps. The only way you get better at communication, spontaneous or planned, is the way you get better at anything. Repetition, reflection, and feedback. You got to practice, you got to think about what worked or what didn't, and then you have to get feedback from others. We are not always the best judges of our communication. And in so doing, repetition, reflection and feedback takes your communication to the next level.

**Lenny Rachitsky** (00:42:00):
That's a lot of work, Matt. That's a lot of work.

**Matt Abrahams** (00:42:02):
It is work. There is no shortcut.

**Lenny Rachitsky** (00:42:04):
Got you.

**Matt Abrahams** (00:42:05):
But that's true with most things in life that are really important. There's no shortcut.

**Lenny Rachitsky** (00:42:09):
That's right. That's right. As people are thinking about this and listening to this, there's your course, obviously that you teach at Stanford and only Stanford students can take that. There's your book obviously. Is there anything else? If there's nothing, that's totally fine, that you point people to to actually practice these outside of the workplace? Are there courses that anyone can take that you recommend? Anything else you can point people to?

**Matt Abrahams** (00:42:31):
Absolutely. There are a lot of resources out there. One, I'm a huge proponent and a former member of Toastmasters. I think Toastmasters is a wonderful organization designed primarily to give you the reps. They do some teaching, but it's really to give you the reps. So I highly recommend Toastmasters.

**Matt Abrahams** (00:42:48):
Improvisation is another way to get comfortable with these skills. When people hear improv, they think, "Oh, I got to be funny and it's about performing," and it's not. Improv is really just about being more comfortable, being present, and really focusing on collaborating with others.

And then there are courses. You mentioned obviously that people have to be MBA students to take my MBA class, but Stanford and other institutions have continuing studies classes or extension classes that are open to the community. So I, every quarter teach a class that's open to anybody who registers all over the world. It's virtual. I have students this very quarter who take a class on a Monday night Pacific Time, 7:00 PM. I've got somebody in Egypt, I have somebody in China. So there are ways to take advantage of things happening at universities without being an enrolled student. So I would point people to all of those. And then clearly listening to podcasts, reading books, checking out blogs and videos can be really helpful.

**Lenny Rachitsky** (00:43:44):
I think to your point, it's like you can read about this and listen to podcasts all you want, but you're not going to actually get that much better. And with your course, I imagine there's practice you're doing as a part of the course.

**Matt Abrahams** (00:43:53):
Everything is applied. The only way to get better at communication is to do communication, to watch communication. And that's why in the books I write, I have this, try this. It's literally put the book down, go do this and then come back because that's how you learn communication. And so yes, any avenue to help you get the reps is going to be helpful.

**Lenny Rachitsky** (00:44:13):
I'll be honest, I did none of the try this. I'm just like, that's too much work. So I think that's why it's important to take something where you have to do it because it's too easy just like, yeah, yeah.

**Matt Abrahams** (00:44:24):
Yeah. You're not the first person to say that they don't take the time to do that. There are others who say they really appreciate that. And for people such as yourself, at the very end of my book, I have a QR code that takes you to a bunch of videos. So if you don't want to do it yourself, you can actually watch people do it or watch me do it. And so that's at least better than not doing any of it.

**Lenny Rachitsky** (00:44:46):
Awesome. I'll also give a shout-out to Toastmasters. I did Toastmasters for a while and two things there. One is there's a special focus on the spot speaking that's a part of the sequence.

**Matt Abrahams** (00:44:56):
They call them table topics.

**Lenny Rachitsky** (00:44:58):
Table topics, yeah. And that's like a 60-second, someone gets up and just has to talk on something. So it's a big part of that method. Also, I did it for a long time and all I did was I was the counter or the timer. You can do it without having to give any talks for as long as you want. And it's very cheap and they're everywhere. There's a local chapter wherever you are.

**Matt Abrahams** (00:45:17):
Absolutely. And many companies sponsor their own Toastmasters groups, so that's great. And they are very good at easing people into it. You're not forced to do anything. And the same is with improv. A good improv teacher never forces anybody to do anything.

**Lenny Rachitsky** (00:45:31):
Great. We went way off-topic, but let's get back to the agenda at hand, which is let's talk about specific situations and advice you have for getting better at these. So maybe we start with small talk and there's one that I love and I find so important and so subtle, which is have comparable levels of disclosure. And the question basically is how do we get better at small talk? And here's one technique.

**Matt Abrahams** (00:45:55):
Yeah, so let me get to that point in a second because that's a more refined point than some general principles. When it comes to small talk, many people dread small talk, they feel really awkward about it. I think small talk has a bad reputation, needs to be rebranded. I think a lot of big things happen in small talk. We learn about ourselves and others. We form and foster relationships. I challenge everybody listening to think about some of their friends, our closest friends. How did you meet them? Probably some component of small talk played a role, especially early in those relationships. So it does good things for us.

The best advice I have ever heard for small talk came from a guest on my podcast. Her name's Rachel Greenwald. She's an interesting person. She's an academic and a matchmaker, really fascinating. And her advice was this: Be interested, not interesting. Many of us go into small talk thinking we have to be super interesting. We have to spike the ball over the net every time. When in fact small talk is more like playing the game of Hacky Sack, where it's simply just set the other person up to be successful and get the ball back to you. So if we go in with that mindset, it makes it easier.

**Matt Abrahams** (00:47:06):
Now there's some rules that we can follow. One rule is the one that you shared that in small talk there should be a balance of disclosure or depth of disclosure over time. So if you're telling me about the first time your first pet died, and I'm telling you my favorite color is blue, there's a discrepancy in disclosure there. Clearly you've revealed a lot more than I have. And we have this notion of reciprocity that if you share something that is appropriate but is more disclosive, that I should at some point match that level or come close. And if we don't, then it feels very awkward and we feel like we're not jiving in that way.

**Matt Abrahams** (00:47:49):
I don't want everybody sitting with a little card that they're checking off, but having that general notion in mind can help. And the trick here is not to be too disclosive too quickly. So if we start small talk and we're talking about the I meeting that we're at, and you immediately jump into the fight you had with your significant other that might lead to divorce, that's a deep and big step that might feel a little inappropriate. But over time, if we continue to disclose, it might be perfectly natural for you to share that. So there's sort of expectations and we just have to be mindful of those.

**Matt Abrahams** (00:48:24):
Another thing we need to be mindful of that I think is really important is this distinction between shifting and supporting responses. In a conversation, I can be supportive. That is, you might say, "Hey Matt, I just got back from Costa Rica." I could say, "Oh great, did you spend time in San Jose? Did you get to any of the beaches?" Those are supporting responses. I'm asking you to keep telling me more. A shifting response would be like, "Oh, you went to Costa Rica. I went to Hawaii." And the goal in a good conversation is to have more supporting responses than shifting, but to have some shifting responses. Because if all I do is continually support you, it looks like I don't want to share. I'm not being disclosive at all. So there are these subtle things that we can be aware of to help the conversation go and to breed that intimacy and immediacy that we feel, but it takes a congruence, a balancing of doing that.

**Lenny Rachitsky** (00:49:16):
This is awesome. I feel like everyone needs this class to just like, how do I talk to people? What's the right way to talk?

**Matt Abrahams** (00:49:24):
Well, right. The point that you're bringing up there, Lenny, is we're never taught this stuff and yet we have to do it all the time. And that's why focusing on it I think really matters. And it can really, as you said, superpower, it can be a superpower because so many people don't do this or spend the time getting better at it. We all operate under this notion of... the definition of insanity, doing the same thing over and over again, expecting different results. And that's not good for small talk and other communication situations.

**Lenny Rachitsky** (00:49:53):
I love this balance you just shared of... So the primary piece of advice for small talk is be interested, not interesting, ask person questions, get excited about what they're telling you. There's a classic book, How to Win Friends and Influence People, which is very much about this. Highly recommend it. It's like very old school now, but there's so much good advice there. There's no better sound to someone's ears than their name. So just saying their name, they're like, "Yeah, I love that." And then just smiling. There's all these very simple things that that book shares. It sounds like you recommend and you're fan of that book, and it's something you've read, right?

**Matt Abrahams** (00:50:27):
I know the book. Some of that stuff has been true for a long time. Some of the stuff. I'm not a big fan of ingratiation and manipulation. I like authenticity and some of the advice in books like that can sound like smile, nod your head. And all of that can sound a little manipulative and inauthentic, but I think some of those principles are important. And if you can in an authentic, true, appropriate way, leverage some of that, I think it would help you.

**Lenny Rachitsky** (00:50:57):
Yeah, somebody once shared a story with their kid... Then they're 13. They read that book and it just effed them up for a while because they just started putting these into practice way too young.

**Matt Abrahams** (00:51:06):
Well, one thing... I mean, all of a sudden you're focusing on... You can get so wrapped up in doing these things that you're actually not connecting. It's like people who travel on a vacation and all they do is take pictures of where they are instead of experiencing where they are. And that's not where we want to be with this advice.

**Lenny Rachitsky** (00:51:23):
But I love this other component of... Because a lot of people hear this advice, ask questions, be interested, be excited, this version of it, but you need to have somewhat equal levels of disclosure is really important. Because I fall into this sometimes where like, "I don't care about myself. I just want to ask you questions. And this is going great, I'm just going to keep asking." And if you're not sharing anything by yourself, it gets really strange. Even when they ask you, you're like, "No, no, let's keep talking about you." You think they want that, but they don't. They actually want to hear about you.

**Matt Abrahams** (00:51:50):
Yeah, absolutely. And you do such a lovely job as a podcast... I mean, so podcast host is a great job for you if you like asking questions, but I bet you have found, because I have found this for me as being a host of Think Fast, Talk Smart is that sharing a little bit about your own experience actually makes the conversations go better. And so I think that's a lesson for all of us, and you don't have to have your own podcast to learn that lesson.

**Lenny Rachitsky** (00:52:16):
Yeah, I read this book on podcasting interviewing when I first started, and one of the big piece of advice is if you share more about yourself, you'll hear more stories that they can share. They're more vulnerable. Not that I think about that, but that's in my head sometimes.

**Matt Abrahams** (00:52:29):
Yeah. Well, you do a good job of it, even if it's just intuitive.

**Lenny Rachitsky** (00:52:33):
Appreciate it.

**Lenny Rachitsky** (00:52:33):
Let's talk about another version of on-the-spot talking, which is giving feedback. Oftentimes people listening to this podcast, they're asked, what do you think of this design? What do you think of this roadmap? What do you think of the strategy? What are some tips for getting better at on-the-spot feedback?

**Matt Abrahams** (00:52:48):
First and foremost, we need to look at and define feedback. Feedback to me is an opportunity to problem solve. Certainly there are some behaviors that we absolutely have to shut down. It's inappropriate, it's inexcusable, we have to shut it down. But often feedback is really an opportunity to problem solve. And if you take it as an opportunity to problem solve, then what you're looking for is collaboration with the other person, which means that we have to invite them to join us as we do this. So it's not me bestowing upon you my opinion, it's me inviting you to together work on whatever this issue challenge is that we have. And I am a huge disciple of Kim Scott, Radical Candor. I really like her approach to it. Kim's a friend. She's actually a neighbor.

**Lenny Rachitsky** (00:53:33):
Well, she's been on the podcast, by the way.

**Matt Abrahams** (00:53:35):
Oh, great. So you know Kim and your listeners know Kim. Yeah, she's great. Where I think I can add a little value to what Kim talks about, and she does talk about structure, but I think having the structure to package up the information to make it easier to digest by your audience, the person or people you're talking to, but also to formulate your thoughts can help. And we've already talked about one mechanism, one structure for feedback. It's what, so what, now what?

**Matt Abrahams** (00:53:59):
So imagine, Lenny, you and I come out of a meeting and you say, "Hey, Matt, how'd that go?" I could say, "I thought the meeting went really well, Lenny, except when you talked about the implementation plan. You spoke a little quicker than you did with the other parts and you didn't go into the same level of detail." That's my what. "When you speak quickly without a lot of detail, people might think you're not as prepared or you're really concerned about this part." That's the so what. "Next time I suggest you slow down and you include these two or three bits of data so that people see you really are knowledgeable on this area." So that's the now what.

**Matt Abrahams** (00:54:32):
So that what, so what, now what helps me very quickly structure information and package it in a way that helps me as the giver of the feedback, think through what are the things I need to say? I need to think through what's bothering me, what the consequences are of that behavior, and then what I think you should do.

**Matt Abrahams** (00:54:51):
There's a more robust structure I talk about in the book called The 4 Is, and each I stands for something starting with the letter I. But four eyes also like glasses. It helps you see more clearly. So in the 4 I structure, the first I is information. You're just setting the playing field so the person knows what you're giving the feedback about. The second is impact, and this is impact on you, the feedback giver. The third is the invitation that you make, and then the final is the implications or consequences.

**Matt Abrahams** (00:55:19):
So imagine I have an employee who doesn't show up to the meetings on time and prepared. I might say, "This is the third time that you have showed up late to this meeting. I feel you're not prioritizing this meeting the same way others of us are. What can we do to help make sure you show up prepared for the next meeting? Because if you do, we're going to finish the project on time and get a new cool project." So information, impact, invitation, and implications. Now, certainly I can vary the tone and the directness of some of those responses so it sounds very differently, but thinking through it in my mind, I have to level set what we're talking about. I have to share why it's important to me at least, make the invitation, and talk about the benefits or consequences. Makes a lot of sense. So there are lots of structures and lots of ways to communicate, especially in feedback. Find one or two that work for you so when you're put on the spot, you can default to it.

**Lenny Rachitsky** (00:56:13):
Maybe a big takeaway here is pick one of these structures that you want to use when somebody asks you for feedback. And the two you shared are what? So what? Now what? Or these four Is. Give information, show the impact that it had on you, invitation and then implications.

**Matt Abrahams** (00:56:30):
That's correct, yeah.

**Lenny Rachitsky** (00:56:32):
Okay. Let's talk about another category, which is not a work category, but I suck at toasts and I am always trying to get better at this. And you have a bunch of awesome advice for how to give better toasts. Can you share some stuff?

**Matt Abrahams** (00:56:45):
Yeah. We have all been victimized by bad toasts. The toast that goes on too long, the toast that's more about the person giving the toast than the event or the person. And when I say toast, I don't just mean at weddings, bar mitzvahs, quinceaneras. We give tributes at work all the time. Congratulations to the team or somebody's anniversary or somebody's retirement. So we give toasts and tributes all the time. In fact, I heard a statistic once that it is the most frequent public speaking event across people is giving toasts and tributes. So we should learn how to do these well.

**Matt Abrahams** (00:57:16):
So I have an acronym. It works. It's called WHAT. W-H-A-T. The W stands for why are we here? Now, if I'm at a wedding, I don't have to tell the audience why we're here. We get it. But if we're doing an all hands and I'm called up to speak, it might be in my best interest to share with everybody, I'm here to celebrate the release of this product that that team put out. So you might have to say, why are we here?

**Matt Abrahams** (00:57:42):
The H is how are you connected to the event? So if I'm at a wedding, people might not know who I am. I could say, "Hey, I've known the groom for 25 years." And people are like, "Oh, okay. Now that makes sense." If you're giving a tribute at work, you don't have to say, "And I'm the boss." Everybody knows your position. So again, these are choices you make. So why are we here? How are you connected?

**Matt Abrahams** (00:58:02):
The A stands for anecdote. Tell a story or a quick example that is relevant and accessible to everybody. There's no insider knowledge and keep it concise.

**Matt Abrahams** (00:58:16):
And then ultimately the last part is the gratitude, the thank you. So express gratitude, express some kind of thanks. In a toast at a celebratory event, you might say cheers or whatever's appropriate for the culture you come from to signal closure. But again, why are we here? How are you connected? Anecdote or two, and then the gratitude or thanking at the end. And if you follow that structure, it can navigate, just like a GPS, your way through the toast.

**Lenny Rachitsky** (00:58:45):
This is such an easy structure to remember. There's so much of it that I love. What I want to understand is where do you put the actual content of the tribute and the toast? Is it the anecdote expands into, "Here's what I want to say?" Like there's an example or story and then it's like-

**Matt Abrahams** (00:58:59):
Exactly. So it is typically part of that. You might do it as part of the why we're all here. "We're here to really celebrate the Herculean effort of this particular team to get this product launched. I'm so honored to have supported it. I'm the manager of the team. Here's a story about how Lenny worked overtime to get this done. Let's raise our glasses and give them a salute." So yes, you could do it in the why are we here or through the anecdotes.

**Lenny Rachitsky** (00:59:29):
Okay. And then one of your other piece of advice, which connects to what you just said is be brief.

**Matt Abrahams** (00:59:33):
Yes, yes. So nobody has ever complained about a toast that's too brief. I'm sure it's possible, but the majority of complaints are the toast went on forever.

**Lenny Rachitsky** (00:59:46):
Do you find that it would ever make sense to give a couple anecdotes or make a couple points in a toast?

**Matt Abrahams** (00:59:51):
Yeah, and it depends. Toasts are opportunities for teaching and learning as well, especially in a work environment. So it might make sense to tell a couple anecdotes. I'm a huge fan... I mean, your listeners know, you know minimally viable product design, agile development, really critical. What is it about? It's about understanding your audience, your users, and it's about rapidly prototyping and iterating. I believe in minimally viable communication, trademark pending, where it's the same principles. Know your audience, put together a rough draft of what you want to say, test it out. So if you're going to give a big toast in front of a company all hands, run it by a few people and say, "Is it too many anecdotes? Would it benefit from having another story?" Get people's feedback. We are not the best judges of our communication. So the answer is yes, but test it out.

**Lenny Rachitsky** (01:00:45):
Another element of a great toast that you recommend is to be emotional. Can you touch on that?

**Matt Abrahams** (01:00:50):
Well, so emotion connects with people, and as long as it's genuine and authentic, it's really important. I've been thinking a lot about emotion and communication. My father recently passed away and everybody in my family said, "Well, Matt's going to do the eulogy." It was like, I had no choice. What do I do? I'm the guy who teaches communication. So I felt added pressure not only to honor my father's life, but everybody's like, "This is the way you do a eulogy." And so I wanted to do some research on what's all the advice out there on eulogies, and there wasn't a lot. So I actually wrote an article on my experience, and hopefully it'll help people. But the point is, in those circumstances where there's a lot of emotion, it's important because it connects to the audience, it makes it human, but sometimes the emotion can get in the way for you as a communicator. I mean, I was very concerned that my emotion would cover up or overshadow the honoring I was trying to do of my father. But the same thing can happen in any kind of toast situation.

**Matt Abrahams** (01:01:48):
So think about emotion. Emotion is a tool to use. The best way to convey emotion in a toast is through the anecdotes you use. The anecdotes reveal the emotion. It's one thing to say, "I am so sad." It's another thing to tell a story that is sad.

I was very fortunate to interview for my podcast coming up soon, a one-panel cartoonist. So she has to create everything in one panel. And her advice is: Don't tell, show. In that don't tell somebody you're angry, show that you're angry in the panel she writes. So showing the emotion through story and anecdote is the way to do it.

**Lenny Rachitsky** (01:02:22):
Have you had Matthew Dix on your podcast?

**Matt Abrahams** (01:02:26):
So it is so funny. I have not, and I want to. His name comes up more than anybody else's. And I know of his work and his advice, so I might ask you to connect me.

**Lenny Rachitsky** (01:02:35):
Absolutely. I thought of him as you were talking because he helps people create their eulogy ahead of time before somebody passes away, before you get really emotional and you have to rush it. So that's one of his services is he helps to write eulogies for people.

**Matt Abrahams** (01:02:50):
Yeah, yeah. No, I'd love an introduction. His work is very influential.

**Lenny Rachitsky** (01:02:53):
Absolutely. He's amazing. We'll link his episode about storytelling.

**Lenny Rachitsky** (01:02:57):
Okay, let me talk about a couple more. Q&A, getting better at question, answer at the end of a talk, whether it's on the spot or not.

**Matt Abrahams** (01:03:05):
Again, I always start with approach. Many of us see Q&A as threatening or challenging, and in fact, we need to see Q&A as an opportunity. It's an opportunity to extend, expand, connect, learn. Even in the most hostile of situations where people are really coming at you with a lot of spice or hot and heavy, you can get a lot of value out of it. So we have to come to the approaches. These questions are opportunities. We have to make sure that we take the question in without interrupting or over-validating the question.

**Matt Abrahams** (01:03:36):
I have two pet peeves about Q&A sessions. One is saying good question to every question. And two, at the end of answering the question saying, "Does that make sense?" Because in both cases, you're trying to validate the asker when you say good question. You're also trying to buy yourself time. And there are other ways to do that. And at the end when you say, "Does that make sense," you've got a laudable goal in mind, which is, "Did I answer your question?" But I'd much rather you say, "Did I answer your question? Can I tell you more? Do you have a follow-up question?"" Because if you keep saying, "does that make sense, does that make sense," people are going to start thinking, "Maybe he doesn't make sense because he is always asking." So some pet peeves there.

**Matt Abrahams** (01:04:15):
Once the question comes in and you have to answer it, I have yet another structure. This structure is related to the what, so what, now what structure. It's called ADD for adding value. You answer the question cleanly and concisely. You then give an example to reinforce the answer, and then you explain the relevance or significance of the answer so people know it. Would you mind role-playing an example of this with me, Lenny?

**Lenny Rachitsky** (01:04:43):
Absolutely.

**Matt Abrahams** (01:04:44):
Okay. Imagine you're hiring me. You're a hiring manager, and I'm interviewing to be what I do for my day job. I'm a lecturer at Stanford's Business School, teach strategic communication. You so happen to have a position open for a strategic communication lecturer. I show up. What is a reasonable question you would ask that doesn't just have a yes no answer?

**Lenny Rachitsky** (01:05:07):
Wait, so you're interviewing for a role to be a lecturer in my school and [inaudible 01:05:11] communication.

**Matt Abrahams** (01:05:11):
Yes. You're the dean. You get to hire me. What's a reasonable question? I mean, you could ask a super hard one, but I want people to hear how ADD works.

**Lenny Rachitsky** (01:05:19):
This might be too simple, but just how many students have you worked with and taught over the years?

**Matt Abrahams** (01:05:23):
Okay, so I'm going to morph that question because I could just say thousands, which is true, but I'm going to turn it into a question about experience, because really what you're asking me is what's my experience? So because that I can give an ADD answer too. If it's just a numeric answer, just give a number. So I might say, "I've been doing this for 25 years and I have taught over thousands of students. I've taught both in the academic world, but also in the corporate world. What this means is I can tailor my material to be relevant and useful to your students."

**Matt Abrahams** (01:05:56):
So I answered the question. The question was, what's your experience? 25 years, thousands of students. I then give an example. I've done this in the corporate world, I've done this in the academic world. So I ground it in something tangible. And then I show the relevance. What this means for you as a dean hiring me, is that I'm going to be able to tailor my experience. We often assume that people can connect the dots. If I give my answer, you're going to see, "Oh, that's why this is relevant and important." But we need to actually connect those dots for our audience.

**Matt Abrahams** (01:06:24):
I had a psychology professor once who said, the funny thing about common sense is it's not so common, and we often make the assumption that people will connect the dots. So answer the question, give a detailed example, and then explain the relevance. And if you do that, it will help. And I challenge every one of your listeners working in companies that have FAQs, frequently asked questions, go back to those FAQs and put them in this structure. Not only will it help you digest and get familiar and comfortable with the structure, anybody looking at those answers begins to see that this is a way to give a complete answer. This is how our organization answers questions. And that can be so helpful to building consistency and helping yourself answer better.

**Lenny Rachitsky** (01:07:06):
Just to clarify, the acronym is ADD?

**Matt Abrahams** (01:07:09):
ADD. Answer, detailed example, describe the relevance.

**Lenny Rachitsky** (01:07:12):
Describe the relevance. I see how you snuck that D in there.

**Matt Abrahams** (01:07:16):
Yeah. Yeah. I mean, you can come up with whatever acronym you want that helps you remember. ADD because it adds value.

**Lenny Rachitsky** (01:07:24):
Awesome. Okay. And maybe one last quick one, apologizing. What's a couple tips for getting better at apologizing on the spot?

**Matt Abrahams** (01:07:33):
First and foremost, we need to take the time to apologize. Many of us don't. And when we apologize, we need to make sure that we apologize for the transgression and not for how we made people feel. So often people will simply say, "I'm sorry that you feel bad." Well, that's not an apology. You're not assuming responsibility. So we need to first start by talking about the issue that we are addressing or the problem that we caused somebody. So we need to think about apologies in that way. So an apology to me, I have a AAA, like roadside repair service here in the United States, AAA. It's three steps, acknowledge, appreciate, and amends. So I have to acknowledge what I did.

**Matt Abrahams** (01:08:23):
So imagine we're in a meeting and I interrupted you. You were in the midst of speaking and I interrupted you. So I might say, "I'm very sorry for interrupting what you were saying. I over-spoke when you were talking." I'm acknowledging what I did.

**Matt Abrahams** (01:08:36):
Then I appreciate. "I can imagine my doing that made you feel bad and you feel that you didn't get your fair share of sharing your point of view." So that's the appreciation.

**Matt Abrahams** (01:08:46):
The amends part is, "I will work not to do this. In fact, I will wait till you're done, and I will actually paraphrase what you said before I contribute my point." So I'm signaling I understand it, and here's the very specific thing I'm going to do to try to remedy it, which of course you can comment on. You can say, no, I don't think that's enough. I think you whatever, or thank you, I think that's even more than is needed, whatever. So you acknowledge the actual behavior and offense, not how you made the person feel right away. You then express appreciation for the difficulty you might've caused, and then you make amends. And the AAA approach, I think can really be helpful to people to be better at in-the-moment apologies.

**Lenny Rachitsky** (01:09:29):
Amazing. Matt, I think we've packed this episode with so many tactical golden nuggets to help people become better communicators, especially on the spot. Is there anything else you want to share or leave listeners with before I ask you how they can find you online and things like that?

**Matt Abrahams** (01:09:45):
Again, I want to go back to how we started the second part about spontaneous speaking. Everybody can get better at communication. And I encourage, I challenge people to take the steps that they need to take to do it. So it starts with initiative. It's followed by grace and a lot of compassion, it takes time. But in so doing, you can improve your communication and help others. It's not just about you finding your voice, it's about you sharing that voice with others. So taking the time to work on your communication is critically important, and I encourage everybody to do so.

**Lenny Rachitsky** (01:10:18):
All right. I'm hoping people will follow that advice. And if not, think back to what we talked about at the beginning of just how much impact these have and how many people are also going through the same challenges you're probably feeling speaking and being on the spot. All right, where can folks find your podcast, your book, and also how can listeners be useful to you?

**Matt Abrahams** (01:10:37):
Oh, I love that last question. So mattabrahams.com, great place to go to to find things. So at mattabrahams.com you'll find a whole bunch of resources. My own and others. I've curated a bunch of resources. You can find Think Fast, Talk Smart wherever you get podcasts and on YouTube. And then the book Think Faster, Talk Smarter is available everywhere. I'm a huge user of LinkedIn. And to answer that last question you asked, I invite people to connect on LinkedIn. I'd love to hear their stories and find ways to collaborate.

**Lenny Rachitsky** (01:11:06):
Awesome. And your podcast is ranked higher than this podcast. You're in a different category, which is a very competitive category. The business category. I've moved myself to the technology category, which feels more natural to me, but your podcast is killing it, so congrats.

**Matt Abrahams** (01:11:06):
Thank you.

**Lenny Rachitsky** (01:11:21):
Thank you for sharing your wisdom with us. That's it. Matt, thank you again for being here.

**Matt Abrahams** (01:11:27):
Great pleasure to have the conversation with you, Lenny. I enjoyed it thoroughly.

**Lenny Rachitsky** (01:11:30):
Same. Bye everyone.

**Lenny Rachitsky** (01:11:34):
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.

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