#98 Sahil Lavingia: Observing the Present

Sahil Lavingia is the founder and CEO of Gumroad, an online marketplace for creators. In this conversation Sahil and Shane cover building a billion dollar business, the most critical skills for success, how he hires, his worst mistake, the patterns of success and failure and so much more. -- Want even more? Members get early access, hand-edited transcripts, member-only episodes, and so much more. Learn more here: https://fs.blog/membership/ Every Sunday our Brain Food newsletter shares timeless insights and ideas that you can use at work and home. Add it to your inbox: https://fs.blog/newsletter/ Follow Shane on Twitter at: https://twitter.com/ShaneAParrish Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I wish I knew earlier that like my company was still my responsibility. No one was going to fix my problems. They were investing because they believed in me and they believed in my potential. But it was up to me to still sort of take that potential energy and turn it into kinetic energy. It wasn't a handout. It wasn't like, you know, you're going to get these people to come into your office and help you solve problems day in, day out. No one's going to make you rich. Like, you know, people are busy solving their own problems.

• 0:43Shane Parrish?

  Welcome to the Knowledge Project Podcast. This is Shane Parrish. This podcast and our website, fs.blog, help sharpen your mind by mastering the best of what other people have already figured out. If you're hearing this, you're not currently a supporting member. If you'd like early access to the podcast, ad-free episodes, transcripts, and other subscriber-only content, you can join at fs.blog/podcast. Check out the show notes for an easy-to-click link. My guest today is Sahil Lavingia. Sahil was the second employee at Pinterest and left to start building Gumroad, a service that's helped creators earn more than $300 million. We talk about the hardest skills to succeed in business, what he looks for when hiring, what it's like to try and build a billion-dollar business, his worst mistake, patterns of

• 1:27Shane Parrish?

  success, patterns of failure, and so much more. It's time to listen and learn.

• 1:37Shane Parrish?

  You were born in New York, but you grew up in Singapore. What was that like?

• 1:42Speaker 00

  Yeah, it was interesting. Singapore is a very unique place. A lot of people who visit describe it like a city playground where it's just insanely safe. It's super clean. You know, people joke about the fact that you, you know, you get... Beat up for chewing gum or whatever, um, which is not true, but not inaccurate either. Kind of it's it's a it is. It is a good heuristic to describe Singapore, I think. But yeah, it was just, I think, living in a place that felt so different from everywhere else. And Singapore, because it's such a young country, it doesn't have the same sort of, you know, identity almost issues that a lot of other countries have in terms of like, this is the way

• 2:24Speaker 00

  that we do things. Singapore, if you read about Lee Kuan Yew or any of the founding story of the country and things like they just pick and pull ideas from everything, you know, libertarians I know describe it as like a utopia because there's no minimum wage, zero. There's basically a flat tax. I think it's around 15% flat. No matter how much you make, there's no capital gains tax. Uh, and so libertarians love it. Uh, but then, you know, there's sort of more progressive socialist kind of people that I know also love Singapore because it's sort of, you know, they they 80% of the housing there is built by the government. Uh, it's it's a very sort of top down centrally planned country. It's

• 3:05Speaker 00

  a single city state country. And so I I just love it because people love to use it as an example of their viewpoint. Like it's a really interesting kind of Rorschach test for like the for the things that people like. But, you know, it's young, it's small. And so in terms, you know, it's never been in a in a war. And so I think there are just things that allow it to do to do things, quote unquote, better than than other folks. And then I would say the other thing that I just, you know, took away from Singapore is just it's pretty ruthless. It's like a very pragmatic as a country place. They're very strategic about how do we grow this thing, right? Like, how do we structure this place in a way that if you look at the GDP of Singapore over the last like 50, 60 years,

• 3:47Speaker 00

  it's like the fastest growing startup you've ever seen, you know?

• 3:51Shane Parrish?

  Well, that was the from third world to first, right? Lee Kuan Yew and and sort of like his unprecedented taking a country in a generation and basically making it wealthy.

• 4:02Speaker 00

  Totally. And, you know, there's a there's a lot of things you can't control, like they're just, you know, where it's located on the map is really important in terms of the trade routes. Singapore is sort of like the largest port in the in Southeast Asia. But it took a person, I think, just like George Washington, right? Like you need the ingredients, but then you need kind of the chef as well to kind of put them together.

• 4:23Shane Parrish?

  How long were you there?

• 4:25Speaker 00

  I was there from age five to seventeen, so most of my childhood.

• 4:30Shane Parrish?

  What was school like there?

• 4:31Speaker 00

  I don't know. I don't know how to compare it because I that's the only context I have. I I think it's relatively similar to to schools here, though certainly like doesn't have some of the same issues around, you know, what you've been reading about racism and antisemitism and sexism and all these things. Like Singapore, it doesn't feel like it has much of the same bag. It has other other issues for sure. I would say the the emphasis there was so much on getting a secondary education. It was like everyone knew without any doubt that they would go to college. And it's a very it's a very sort of financially motivated place. And so typically, people will pick the jobs that will make them the most money. It's sort of very, uh, very capitalistic in that way.

• 5:14Shane Parrish?

  It's interesting how those expectations shape outcomes to you, right? It's like you're expected to go to college there. You're expected to perform academically, I believe.

• 5:22Speaker 00

  I think expectations cannot be underrated, and I think in your peer group also can't be underrated. Like, I I think there's so much emphasis on on sort of the system that you're a part of, uh, your sort of your set of teachers, et cetera. But honestly, I think the biggest thing is just like you're kind of the average of your five friends, you know, and if you hang out with certain people, you're going to end up in a very, very, very different place. Based on based on that kind of like that osmosis that you'll go through and the sort of like this this sort of socialization, you know, that that you'll have as as a kid. And I think that happens super early. And certainly, yeah, Singapore, it just, you know, it's it's a pretty ruthless. It's a pretty ruthless place, like the idea that

• 6:06Speaker 00

  there's no fat people, for example, in Singapore. It just like doesn't really exist as a concept. And I don't mean that in any sort of derogatory way, but there's just people in general there aren't overweight. And part of that is in in the local school system, if you are overweight, you go through a program like you as part of you skip lunch. And you go through a program that you basically run around a track instead of eat lunch. I mean, it's like a sort of a regulatory, a regulatory system. And, you know, there's also a national service. Everyone who's Singaporean, if you stay in Singapore, I chose to leave and go to school in the U.S., you have to go through national service, right? So you spend two years becoming, you know, sort of like a, a perfect adult, quote unquote, right?

• 6:49Speaker 00

  Like you learn these things, like in general, people who go through that are less likely to, to get into trouble and, and things like that. So there was a lot of, it's, it's hard to unpack exactly like, oh, you know, if we took this and applied it here, you know, it would fix this problem. But there's just so much culturally around just holding, holding the people to a very high bar. And then when you do that, like the next generation, you know, is brought up with these sort of values and is willing to do that for the, sort of for the next generation, et cetera, et cetera, et cetera.

• 7:15Shane Parrish?

  I want to explore something you said there about sort of the, you are a product of the five closest people you hang around. How do you use that information to consciously choose the people that you're hanging around?

• 7:28Speaker 00

  I'm really mindful of, of that, of, you know, like in terms of the books that I read, the people that I listen to, the tweets that I follow. I think it's, it's super important to, to really, you know, it's sort of like you are what you eat, right? The, the companies that you work for, I think, like I've never read a book and, and, and come out of it being less convinced of the argument, even though I was not on the side of the argument. Like when you spend that much time sort of looking at a subject from a specific perspective, you just end up becoming more empathetic to that point of view. And it's like doing that en masse, right?

• 8:09Speaker 00

  When you go on the, on your phone, you're kind of seeing the way that a certain group of people see certain things. I think this has actually sort of been accelerated with COVID because you don't have maybe some of the back and forth. You're just, you can't, you know, it's sort of this very asynchronous medium. And so you end up just like absorbing all of this content and your perception is your reality. So I think you just inevitably. Inevitably kind of become closer to those sorts of people, which I think can be a great thing. If you want to be a great business person, for example, you can read books by great business people. And of course, they're selling things like you kind of have to be mindful of maybe what their incentive structure might be. But you'll get closer to figuring

• 8:52Speaker 00

  out like, what are the sort of attributes that make someone like Jay-Z Jay-Z, or someone like Steve Martin, Steve Martin, right? And I spent a huge amount of my time reading those sorts of those sorts of books as well.

• 9:04Shane Parrish?

  What about the people you physically hang around with? Like, do you call sort of friendships when you're like, this isn't serving me? Or how do you think about that?

• 9:12Speaker 00

  Yeah, this is something I struggle with a lot. I think there is a large expectation around friends and like what friends mean. And, you know, Silicon Valley is kind of funny, because there's this concept of we're friends. And I like to joke that we're startup friends, because it's such an overused word. And what it means is like, we met once in person for coffee. And if they, you know, I need something from them, I'll send them an email and they'll reply to my email. It's not like we hang out at the bar, you know, like, you know, like all these sorts of things, unless it's sort of some situational thing that arises typically from some sort of business reason. And that might just be a differentiator between friends in school and friends, you know, in adult life. I'm not really sure

• 9:53Speaker 00

  because that's the only sort of career path that I've sort of taken. But yeah, it's, it's, I always struggle with with that idea that we need to be friends with everybody. There are people that I talk to all of the time, but I wouldn't consider them even friends of mine. We just happen to be valuable for each other, very symbiotic relationship. And then there's other people that I'm friends with that I would consider close, close, close friends with, that I haven't talked to in in months. And so I really, I think those can be separated. But yeah, I spent a lot of my time thinking about how do I spend more time with certain people, which I think can be a trap, because you don't want to, you know, get into this, this place where you're just like, how do I meet this person? I don't think that's the right approach. But it's more like, how can I figure out

• 10:37Speaker 00

  how to become closer to the type of person that this kind of person is? And in general, if you do that over time. I feel like opportunities to meet these kinds of folks will come up and show up in your life organically.

• 10:49Shane Parrish?

  Where did the idea from Gumroad come from and how did you get started?

• 10:53Speaker 00

  Yeah, so Gumroad, I wanted to sell this pencil icon that I designed for a Mac app. And I had a Twitter account, I had a Dribbble account, I had a few thousand followers. This is 2011. And I just wanted to sell them this thing, I kind of called it like a lemonade stand. I just, I don't need a whole storefront, like I didn't need all of this infrastructure. I just needed like a little table and, you know, I wanted to sell this icon for a dollar. And, and, and, you know, these people who are already following me, you know, I can just share it with them and they can choose to buy it or not. And, you know, they, they enter in their credit card information, they get an email receipt with the download, or they get the download maybe in line even, and just made it super easy. And so I thought that would exist and it just didn't exist.

• 11:35Speaker 00

  It, it felt like a very large disconnect where I was like, oh, I'm going to go sell this icon to this audience. And then it wasn't possible. So, you know, that was Friday night and then I ended up building Gumroad that weekend and then launched it, launched it Monday morning on Hacker News and it did well, I think. And then, you know, a few months later, I ended up starting, starting to work on it full time, raise, raise some money from folks like Naval, et cetera. That's what I've been doing since.

• 12:02Shane Parrish?

  What was the process of raising money like?

• 12:04Speaker 00

  I mean, this is a, this is like, I don't know, a really good example, I think of like figuring out how you get to spend, you know, time with certain folks, like the way that I structured my life before, before even I wanted to fundraise or thought about it as an idea, I felt like I wanted to be a founder. And so I spent a lot of time hanging out with founders, hanging out with early employees, working at an early stage startup. I think that's sort of the best thing that you could do. You know, I left USC to go do that. And so I had a network just from building stuff, meeting with people, people wanting to recruit me for their companies. I'd started to build a relatively strong network of people like Naval and Seth Goldstein from Turntable and, and Simeon Shah from Haystack VC now.

• 12:47Speaker 00

  And when I sort of had the opportunity to raise money, when one, one investor suggested like, hey, this thing looks really cool, have you thought about? Doing this full time, I know you're at Pinterest, but you know, this is certainly something you think, you know, you'd probably be able to raise money for. And I was like, I really, really had no idea that I could do that. It was not in my mind at all that I could be a founder that early, that quickly. Uh, and so I said, yes. And then I just told all of these people that I had met out of the context of raising money. It was like, hey, we met about this three months ago or six months ago, or, or, or what have you. I have a startup, like, you know, I'm, and I'm going to raise money for, are you interested? And it was honestly a relatively smooth transition because I built up these relationships with people around just talking about product and talking about, there was no agenda.

• 13:32Speaker 00

  I wasn't selling them anything. So I'd sort of already effectively sold them on my abilities to build stuff. And be really committed to that path. And so when I decided to raise money, it, I'd almost done all of the work, you know, accidentally. And then it was just sort of like going through like, okay, what are the terms? You know, what are the sort of the like, the legal paperwork side of things, but it was a relatively smooth, smooth process. What do you wish you knew about raising money that you know now? I mean, I, I, I would say, I, I think every founder thinks that raising money is going to change their life. Like you're going to get all of these phenomenal people on your cap table and you're going to hang out with them all the time. And they're going to help you, you know, recruit and build product and figure out go to market strategy.

• 14:15Speaker 00

  And the truth is like, all of these folks are very busy. Some of them are running their own companies. Uh, many of them are in many, many, many companies of which you are at least not in the beginning. One of their sort of top few and, and the way venture returns work is it's sort of a power law. So if you're not, they're Uber, you know, it's a different, the way they think about you might be a little bit different. So I, I wish I just knew that. I wish I knew earlier that like, my company was still my responsibility. No one was going to fix my problems. They were investing because they believed in me and they believed in my potential. But it was up to me to still sort of take that potential energy and turn it into kinetic energy. It wasn't a handout. It wasn't like, you know, you're going to get these people to

• 14:57Speaker 00

  come in to your office and help you solve problems day in, day out. And this is an experience I've talked to so many founder friends where they feel like, because the sales process is so good, that's what they do, right? They're selling cash to get on your cap table and they're really good at that. But it's like the second they sell you the car, they've sold you the car. I mean, they, you know, they've done the 90% of the of the of the work, you know, to sort of precede investors. It does change a little bit later on, I think. And so I just wish I knew, not in any, in any, you know, way that says, oh, these people aren't helpful or whatever, but just the incentives. And it's just a model in which they operate. And so I can understand, okay, this is as

• 15:39Speaker 00

  a founder, what you expect from me, what I owe you, quote unquote, and how I should sort of go about it. But you learn, you learn pretty, pretty quickly that, that, that was the expectation and that you just need to, like anything, like no one's gonna, no one's gonna make you rich. Like, you know, people, people are busy solving their own problems.

• 15:58Shane Parrish?

  Were the expectations on you that you would become sort of like this billion dollar business that you, you haven't accomplished yet?

• 16:06Speaker 00

  Yeah.

• 16:07Shane Parrish?

  And what's that been like?

• 16:09Speaker 00

  Yeah, it was, I think. I mean, Silicon Valley is, is a game of finding these crazy outsized returns. It's, you know, the, the sort of common adage is, you know, 30% of your companies die, 30% of your companies return less than one X. And so you kind of need the last third, and really the top 10% of, of the best that you make to return over 10x of the sort of initial principal capital. And often a lot more if you want to return any meaningful returns to your investors, because this is an illiquid asset class, right? You're giving money. To a venture capitalist as an LP and they're going to hold that capital for 10 plus years. Right. So you kind of expect more than market returns if you're signing up for that.

• 16:52Speaker 00

  So yeah, that was totally the expectation and that's not just the expectation. I think some people really focus on venture capitalists and the zeitgeist, but it's also the expectation for the early employees because the early employees might only have half a percent of the company, 1% of the company, 2% of the company. And so they also are looking for, I mean, they're turning down offers from Facebook and Google and Uber at like, you know, for hundreds of thousands of dollars to work at your rinky dink startup. There's a, there's a whole system I think is modeled off of for this to be worth it for everybody that you need to get signed up to even get to any end result that's interesting. You need the promise of or the potential of there needs to be a billion dollar plus outcome here.

• 17:33Speaker 00

  That's, it's kind of like when you look at the music industry, you know, or the NBA or anything. It's not that everyone has the expectation that they're going to become LeBron or Kanye West or anything like that, but the idea that it's possible and that one person is going to win the Hunger Games is going to really kind of, it drives the level of competition and sort of work ethic that I think you frankly just don't get when you don't have those crazy outcomes as a possibility. Right. Like Jeff Bezos doesn't need $200 billion or whatever he has now, but for some reason, and no one does, I don't know what you'd do with that much money.

• 18:11Speaker 00

  But for some reason, it's still like America, I think it still has like this phenomenal culture of innovation that I think is largely driven by this weird relatively abstract number on the wall that everyone can see, you know?

• 18:28Shane Parrish?

  Did you feel any sort of disappointment or did they make you feel disappointed in terms of not accomplishing that as quickly as maybe it was anticipated? I mean,

• 18:37Speaker 00

  Yeah, I mean, there, there definitely was some disappointment. I mean, I had, I had so many wins so early, I dropped out of school and then I was the second employee at Pinterest at 18 and then I started a company at 19 and raised a bunch of money from really great investors and, and, you know, raised like 10 million bucks by the time I was 21 or something like that. So I just felt like, If this was gonna work, these are sort of the things that you need to see, right? But that's kind of a delusion. It's like when your team gets to the semifinals. Like you still have to, you're still less than halfway there, right? Like there's still work to do, but you have so much evidence that you're like, oh, this might, you kind of start believing something that might not be true. But it was mostly internal disappointment.

• 19:21Speaker 00

  The nice thing about the portfolio theory that VCs have is they don't care that much about you if it doesn't work either, right? So they're all, they're sort of focused on, on other things. They're kind of content to let you figure it out. At least the good ones are, they kind of understand that, I think. But it was certainly, I mean, it was certainly disappointing. I think to admit when we did the layoffs, that was like the big moment that, you know, there's really no going back from that, right? Like you're sort of saying, hey, this thing that we all signed up for, like we literally cannot possibly keep going on this path. We need to, you know, we cut 75% of the staff from 20 down to five people in 2015. And then TechCrunch wrote about it. And so, you know, it just like, oh, wow. Like the, you know, you, we really, we really failed.

• 20:05Speaker 00

  And, and even though failure is such a meme almost at this point, and it's something you read about when it happens to you, when it really, you know, even though you knew the odds coming into it, when it, when you realize like, oh, you're a part of history, like this is, you are the example that other people might be referring, you know, when the, it feels very, very different.

• 20:27Shane Parrish?

  Do you actually feel like you failed?

• 20:29Speaker 00

  I did for a long time. Yeah. I mean, you know, I was living in San Francisco. Everyone's raising money and everyone's talking about how many employees they have and how much revenue they're doing and how fast they're growing. So certainly in that cultural context, it feels like you show up and it's like, how's Gumroad going? You know, I mean, that's the, those are the questions. It's not malicious. These are the questions that people tend to ask when you go to these house parties. Like, you know, like how much have, you know, what are you doing? Oh, where do you work? What do you do for them? You're just sort of gauging your sort of like where you are.

• 21:01Shane Parrish?

  Where are you in the hierarchy? How useful are you gonna be to me?

• 21:05Speaker 00

  Yeah, something, you know, this is, I assume it happens in any boom town, right? Like people are there for a specific reason, typically sort of accelerating their career. It definitely, when you hear that question a lot, you're kind of responding to it a lot, you kind of end up sort of conflating that with your whole identity. And it took me leaving San Francisco and Moving to Provo, Utah, and there the questions were very different. You know, it was like, hey, are you married? Where are you from? Do you go to church? Just different, different kind of questions. It's maybe a similar thing's happening. They're also trying to figure out where you stand on the, in their own journey. Where do you fit in their journey? Right. And they're, they're also trying to form a connection around the common topics that you both are probably interested in.

• 21:49Speaker 00

  But after a while of that, you've, you, I kind of forget, oh, I'm, I am a CEO of a company. Like I bet all kind of like, I almost forgot about. And really that I think distance was what got me to write that article in the first place. Because I think if I hadn't, I wouldn't, I would not have been able to write that article like sitting at a coffee shop in San Francisco. Right? Like just the, the ego, the, the self consciousness of it. I think I needed that distance to be in the middle of people who didn't really like to, to be so outside of that. To, to, to really kind of look at it, you know, and feel like I'm, it was almost like an out of body experience. Where I was kind of like analyzing the life, like I was writing a biography of, of somebody else, you know? It was so foreign at that point.

• 22:34Shane Parrish?

  There, there's people that sort of ascribe your value to your position and what you do and what you can do for them. And then there's people who want to know who you are and sort of have a, a relationship with you. And then I think if we hang out with people that ascribe value to our, our rank or position or some sort of authority or knowledge that we have, then we become wrapped up in that. We, we have to see ourselves as that. And that can be a very, very bad thing over the long term. I'm curious as to what your worst mistake was, like what led to it? How did you recover from it? And how did you learn from it? What happened?

• 23:11Speaker 00

  Yeah, I mean, I think, I mean, to your point, just quickly, like, you know, it kind of goes back to what we were talking about in Singapore and like the average of your five friends and stuff, right? Sort of the same thing. The questions that everyone in your group is asking of themselves ends up being the question that you're going to start asking yourself to. In terms of the worst mistake. Definitely like one that is very raw because it has like a very specific number tied to it is we we started raising the series B. We started talking to investors about it. And so for context, like we raised a seed round of a million bucks. We raised a series A of seven in 2012 from Kleiner Perkins. And then in 2014, 2015, we're growing 60% a year. We thought we had, it wasn't going to be easy, but we thought we had a shot.

• 23:57Speaker 00

  And we started talking to investors around the series B. We wanted to raise maybe 15, 20 or so million dollars to keep going. And very quickly realized like this was going to be a pretty hard, a hard path if if we were to succeed at all. And concurrently, our office lease was expiring. And so we had this 33,000 square foot office. We were spending 10 grand a month for. And we had the, you know, and we were growing, you know, startups like you have to signal that you're growing. You can't say, hey, guys, we're going to take a break, figure this thing out because everyone's going to look at that. And say, oh, these like as a venture capitalist, you don't want those people. You don't want to back those people. So you're you're you're sort of it becomes a self fulfilling prophecy when you do that.

• 24:40Speaker 00

  So you have to kind of keep going, assuming that things are going to work out for at least a certain period of time. And so that's what we did. We signed a lease for a new office so we could scale from 20 people to 40, 50 people or so. It was $25,000 a month. We paid a big deposit, six figure deposit on it. And moved and then, you know, a few months later, it was like, we're probably not going to raise money. We're not, we certainly are freezing hiring now. And what are we going to do? I mean, the office was just this overbearing thing. You like walk into a cavern. It felt like, you know, it was, it was brutal. And then when we, we went down from 20 to five, guess what?

• 25:20Speaker 00

  We're still in this office. This office could hold 40 plus people and there's like four or five of us a day. It was painful. And so ultimately, I, I had to make the decision to kill the lease completely. And we lost, you know, a couple hundred thousand dollars. And luckily, we, we found a, we found a new tenant to come in, but we, you know, we still lost. We ended up still losing, yeah, probably a hundred or so thousand dollars through that, through that process. And what I should have done in hindsight, of course hindsight's 2020, but what I should have done is told the team, hey, we're not moving offices. We're just going to renew this lease. But then again, if I followed that, you know, that advice, who knows what would have happened. Feces might have pulled out even sooner and, you know, it could have been, it

• 26:04Speaker 00

  could have been worse. But that definitely very painful. And that really that taught me this very deep lesson of like commitments and debt and like really feeling like you owe someone something. Like, I really don't like being in that place where I have to establish. This almost goes back to what we're talking about before, too, where you have these friends and you kind of, there's sort of an expectation that like you're going to be friends with someone for life, or it's bad that you kind of go separate ways, you know, something must have gone wrong or something. We still have, you know, in marriage, divorce is still, maybe that's fine. Maybe it's just what happens, you know, that might be the right thing. I think we definitely have a lot of attachment to these ideas. And that's

• 26:45Speaker 00

  another one of them, I think, you know, it's the same thing. It's like, I really try to form build relationships with people that feel at will. They feel like we're both re-upping to keep this thing going on a very frequent basis with my employees, with, with my investors, with, with other folks that I talk to. It should feel very, not transactional, it feels transactional. And maybe, maybe that, maybe it is transactional. But it doesn't, I don't know, it feels just voluntary. It feels like something we're signing up for. And that makes, that makes me feel a lot better about it.

• 27:16Shane Parrish?

  And you guys are profitable now, right?

• 27:18Speaker 00

  Yeah. So we, in 2015, we, we, we sort of, January, we knew this was going to be brutal. We spent nine months, we raised a small bridge round, $2 million, at four exclamation preference from, from Kleiner and, and Mark Cuban and some other folks. And spent nine, nine or so months really trying to make it work, like sort of focusing almost completely on, what can we do to grow the business faster? And then we, we failed to do that. And so luckily, I told the team, like, you know, they had full awareness that this was likely the path was going to lead to mass layoffs to save the company. And that's what we did in October, November, we, we downsized from 25, got rid of the office, finally founded new tenant, and, you know, got profitable, made $10,000 one month, and

• 28:02Speaker 00

  it was like a dream. Because not only do you make $10,000, your runway goes from You know, a certain finite number to infinity, right? And Excel starts erroring out and you're like, yes, like this, we can, we can do this forever if we need to. And that's roughly where we've, we've been since where we're kind of growing. We're doing it in a way that we think we can do sustainably without betting the company to, to do anything. Uh, certainly means we have to, you know, we're constrained in many ways. We can't just say, hey, we're going to launch this totally new product, put a team of 20 on it. Um, but so far it's, it's worked, worked pretty well for us.

• 28:41Shane Parrish?

  Do you wish you would have done that sooner?

• 28:44Speaker 00

  Yeah, that is, that is a decision that I think, yeah. Uh, I, I, and this is, as I sort of do more investing, it's something I communicate to, to founders a lot too. It's like, look, this is what you need to stay on this path. This is the venture back path. It's actually relatively objective. You need to be growing in the article, I say 20% month over month, but it can be 10%. It just needs to be sort of exponential or, or so, or polynomial, or whatever the correct math term is. And if you're doing that, you can stay on this path. If you're not doing that, it's going to be tough. It really, you know, maybe it's pre-seed, seed A, a little bit different.

• 29:24Speaker 00

  But if, you know, at sort of, at some point around series A, series B, that becomes sort of like the end all be all. It becomes the most important thing in which all of the other things can't outweigh that. And I, I knew that, I, I, I saw that in the numbers, like, oh, that was evident to me. But I didn't make the connection with how important it was, how fundamental it was for this path. And I wish, you know, a year before I did or so, you know, we said, hey, look, we're not growing as fast as we need to be growing. Like, let's pause. We don't have to do anything drastic because it's still early, but let's pause, let's recalibrate. And you know, and let's, let's figure this out. And certainly, yeah, I certainly wish I would have done that.

• 30:06Speaker 00

  We would have avoided a lot of, a lot of pain, but it is what it is.

• 30:11Shane Parrish?

  I've spoken with a few entrepreneurs who've sort of been VC backed and then one way or another got off that train and then came to a path to profitability that was sustainable. And it's almost unanimous that everybody wishes they just would have done that from the get go instead of, and maybe that's just a, you know, an outcome bias, right? So you didn't hit the sort of like big massive unicorn, you know, 30x win. And so you're left with profitability, but lots of companies die trying to get to that stage too.

• 30:43Speaker 00

  Yeah, totally. I do think there is a level of outcome bias there. I think there is also a level of, one of the reasons to raise money is a social one where it gives you a sort of credential that is very useful. I can still to this day go into a room and say, hey, I raised money from Naval, Max Lechon, Kleiner Perkins, Chris Saka, first round, and people will take me seriously for that. Right?

• 31:07Shane Parrish?

  Just because of that, yeah, the signal value.

• 31:10Speaker 00

  And so there is like this kind of, I think people might sort of forget when you, when you get through the whole thing, that you're still taking advantage of some of those things. And maybe, you know, it's kind of like, maybe you should get into Harvard and, and put this, you know, the acceptance letter on the wall, but not actually attend, especially now. Right? It's sort of that, like, maybe you should like say that you, they were gonna give you the money and not take it or something. I don't know how you would frame that in a way that doesn't make you sound bad, but, or maybe you raise a small seed round or something. But again, like being that strategic about it because it feels manip, you know, like venture is such a long-term game, you can't, you can't think like that and I wouldn't recommend it, but there is an outcome bias.

• 31:52Speaker 00

  I mean, I do agree with you, almost every single person I meet who runs a profitable business, especially one powered by software. They wouldn't trade it for the world. And frankly, like their cash flow, it looks better than most folks that I know who are on paper worth a lot of, a lot more money. I still haven't resolved that for myself because I still feel that sort of aspirational quality, right? Like, I still feel there's something about Stripe, like there's something about Airbnb, there's something really cool about building something so meaningful. And I think part of that for me is it's a, it's a unique experience. There are a lot of these other businesses and they're great and they give you like a phenomenal quality

• 32:35Speaker 00

  of life and tons of freedom and time. And, and, and certainly if you're, if you are running one of these other companies, you don't have a lot of those things. You don't have a lot of freedom. You don't have a lot of time. Like you're living in San Francisco, regardless of what happens with COVID and remote work, because you need to be there. But yet there's still something about that. And I think it is that like you, you have a certain set of experiences when you get to this place that people like me just frankly want, like we want to hang out with these sorts of people and have these interesting conversations. And it makes it easier to do that. But it is weird. It, it, it, it does feel like even, even acknowledging it, like being aware of it doesn't make it go away, you know?

• 33:17Shane Parrish?

  What do you think is the hardest skill to transfer to other people that's necessary for success in business?

• 33:24Speaker 00

  Yeah, the, the skill that's been really top of mind for me right now is the ability to save other people time. Basically, what I mean is there are certain people that go about their lives. I try to be like this, but they just operate in a way that requires less of everybody else for them, for the equivalent amount of success in that relationship. Right? So for example, someone who sends calendar invites, someone who's very diligent about taking notes and following up and, you know, people like you, you put like the link to, to have this conversation right into the, the Google calendar invite. A lot of people like they'll just put in the email, go find the email. Like there's just a level of care.

• 34:06Speaker 00

  It feels like you're, you're almost like, it's like a concierge service for like getting to spend time with this person. And then there are other folks that, you know, they're just being responsive. Like, there's just things that like lead to a less, less level of stress in everybody else around their lives. And it's so rare, it's so rare, I've found. And I think it's because everyone else is also trying, you know, is very time sensitive too about their own time. And so they end up sort of operating in a way that's saving them time by sort of maybe pushing that burden on to other folks. Right? You're sort of like playing hot potato with the task that no one really wants to do. But it's the people who are like, I'll do that. I think that, I think people underrate, and you're that type of person, you know, as a, as a, as a CEO, as a founder,

• 34:49Speaker 00

  those employees that do that will win. Like, they will get whatever they want because those are the folks I really want to surround myself with because I care about, you know, my quality of life and my time. And as a, as an investor, and as, even as a, I don't know, as all of these other roles, I really, like, how can I save you clicks? How can I save you time? Like, when I send calendar invites, I put my name first instead of the other person so that in their calendar it shows up. You know, and otherwise you have all these calendar invites, just your name, and you can't see who you're actually talking to. It's just like small things where I'm like, how can I just really streamline everybody else's life? And the beauty of software is you can now use a lot of software like Calendly and Zapier and these Airtable, et cetera,

• 35:31Speaker 00

  and these tools to like hook up these things so that everyone, I think, can operate like as if you had a full-time EA running your life for you. You just now pay a couple hundred bucks to three or four different tools that give you that. That's actually an even better experience because software is often a little bit more foolproof than, than, than a human being.

• 35:51Shane Parrish?

  Yeah, I like how you, you said that. That's something I've thought a lot about. And, and I find myself lacking in some areas, but definitely there's a lot of people who are more thoughtful about how they approach it from the other person's point of view, which is how do I make this easy for them? Especially if you're, you're asking them to come on the podcast or you're asking them to do something for you. Like, you're doing me a favor. I don't want to send you 55 emails trying to schedule it. I definitely don't want to, you know, make it hard for you to hop on board and follow the instructions and like do all of that stuff. But there's a lot of people in life, like I remember going through this before when people would be like, let's go for coffee. And you know, it's like 35 emails to go for a 30 minute coffee. And you know, at the end of the day, you're like, that's ridiculous. Like, I don't

• 36:35Shane Parrish?

  want to do that anymore. I just stopped replying to this.

• 36:38Speaker 00

  Yeah, it's like when people ask you, even people who I know, they're like, hey, do you want to catch up next week? And I know that they have a reason for this, but they won't tell me the reason. And I always, I just ask people now, I'm like, hey, what, you know, what do you want to talk about? I don't know, it's like a power, information asymmetry thing. But I think it's mostly just time. It's mostly like, I want to, I need to do something. Hey, so how can you talk about this next week? Not really maybe even thinking about the fact that like, you know, exactly, you're going to show up and know exactly what we're talking about. And I'm going to show up and know nothing. And by the way, if you tell me, I'm happy to do the work ahead of time. Like, I'll go read stuff. I'll like, I will get you the answers. So when I show up, I can, and then the other great thing is, maybe we don't even have to have the meeting. Like, maybe

• 37:23Speaker 00

  everything that you need from me, I can just give you. But you don't give me that opportunity. And so there is this like, interesting, like, people who view time as the thing that they're trading, and then to people who sort of like, can can transition to value. For example, there's a, if you're a founder, you want $100,000 from me or something like that. You know, as you mentioned, like, you're doing me a favor. And it's like, how can I, like, how easy can you make it for me? How easy can I make it for you? And there's certain founders who make it so easy for me. I just reply to the email. And I just say, I'm in for, for that. Like, CCing, you know, Angel List to wire the money. Like, they made it so easy for me. They gave me all of the things that I would want. And then there are other folks who are like, hey, I have a great idea. Do you have time next week?

• 38:07Shane Parrish?

  Sign this in.

• 38:07Speaker 00

  Very different. Yeah, sign this in.

• 38:10Shane Parrish?

  There's also another level to this, which, like, outside of maybe professional relationships, but there's people who make it difficult. And then there's people who actually like, it's not a conscious process, but they make it exceptionally difficult. It's like, they want to go to dinner with you, but they want you to convince them to go to dinner with you. You know what I mean? Like, there's a, there's another layer to this, which is like, it's not easy, and it's not middle of the road. It's actually quite complicated. Like, you're put on the, now I have to convince you sort of side of this.

• 38:40Speaker 00

  That is weird.

• 38:42Shane Parrish?

  I want to talk to you. What other skills do you look for when you're hiring?

• 38:46Speaker 00

  Communication is a huge one. It's similar to that, but people who over-communicate, people who are always thinking about, you know, the next day, the next week, the next two weeks, the next month, the next year, and telling me what they need from me, how they feel about our relationship. People who are very good at doing that. It's low-stress. It lets me solve their problems before they need them solved, potentially. It makes me feel confident that they're in a good place and that they have what they need. It's like static electricity, where like, you know, you ever go too long without touching something, you hit something and you're just like, your skin fries for a second. It's like, but if you did that all the time, it would never happen. Like, that's how I think about communication, especially within, within sort of like a high-stress,

• 39:30Speaker 00

  high-functioning organization, where that's going to happen very quickly and you need to constantly be like tapping and like being like, hey, this is what's happening now, this is what's happening now, this is what's happening now. And so I think people who are really good at sort of ambient signaling, saying like, I don't need to ever go to them and say, what's going on? Like, I just know. I wake up, I check Slack, I do whatever, I just know what they're doing. To me, that's the dream. That is just like a phenomenal, phenomenal thing. I think an ability to write really, really well is key to that. Part of that is just the medium in which so much of this communication happens is via writing, especially now with remote work, etc. But in general, I just love when people, when people do the work of, you know, not just sending me the email, but writing the email, revising the email, revising the email, sending that email.

• 40:15Speaker 00

  Like, the, the, the, the brainwaves that they, they've sort of like spent on that with the context they were already in is going to save, net-net, save so much time for everybody involved. And then the, the level of conversation is so much higher, because instead of going like,

• 40:30Speaker 00

  it's just like, I'm going to spend five minutes on this thing, but when you get it, it's already going to be at like level 10. Because it's already at level 10, I can get it to level 50. And I'll give you the time that you gave me. Like, I'll, I'll, I'll pay you back very, very quickly and we'll build a very high-quality relationship. I would also say like, I like people who are very... Kind of transactional, frankly. Like, I like people who are like, I'm here to do this job. This is what I came here to do. I'm really excited about speeding up the site. That's all I care about. And like 99% of our conversations are around that. And I spend, you know, I might be working with these people on a daily basis. And so I think I like that, too, when people don't feel the need to package up

• 41:11Speaker 00

  or bundle a relationship and say, hey, we're coworkers. So we need this, this, this, this, and this. We need, you need to come to my birthday party. You need like, I like, you know, and that's definitely a change for me sort of 10 years ago, but I like people who are like, this is the way that we interact. Like, we talk every day, but it's about investing, or it's about, you know, we talk every day, but it's about this other thing, or, you know, and, and, and sometimes it's just like totally random stuff. Like, there are people that I would never consider quote unquote friends of mine, but like, when I need to talk about like oil painting or something like this is the person that I talked to, and we'll talk for hours about it. And then it might be like six months until we talk again. And it's, it's fine. Like, we might even forget that the other person exists. And, and I actually think like a life built of relationships like that, it gives you way more relationships.

• 41:56Speaker 00

  And it, you know, it's sort of like having a friend group of thousands of people, or having a company of all these sorts of people. So I really like people who think like that, where they're very sure about what they want. They feel, they feel very good about where they're at in life. And all they're looking for is this, like, is our relation to feel like one thing that they need. They're trading X for Y. And I just, I really like knowing that that's what someone is expecting of me. And I can just offer that and feel, you know, and, and feel really good about that and, and focus on that, you know? And so it's like when someone's like, how can I help? You get nowhere. But if you say, hey, I need help with this very specific thing, an intro to X, I can do that. Like, that's, I'll do that, you know, just forward me an email, you know, with the blurb and the deck, and I'll forward it and ask for an opt-in.

• 42:39Speaker 00

  Like, that's, that's purely automated. I mean, that's, that's purely a, a process that I go through. I could, I could at some point and will automate that completely.

• 42:47Shane Parrish?

  Agree that, that's also making it easy for you, right? Through investing and through Gumroad, I mean, you've dealt with probably thousands of entrepreneurs at this point. What are the common patterns of success and failure that you've seen?

• 43:00Speaker 00

  Yeah, I think one big one is is they build stuff. They actually build stuff. In the early days, it was the it was the only group of people that I hung out with. Like, I wasn't just hanging out with startup people. I was hanging out with the people who went through some stuff to get there. It's like often the people, the best people in the industry are the ones that didn't go to school for that industry, because it it means that they had to cross all of these things to get into it, if that makes sense. So people who people who build stuff, I think I was surrounded by those people when I get it started getting into it more and meeting thousands of people. Realize a lot of people don't actually build stuff. They don't know how to build stuff. They need help. This kind of goes back to what we're talking about again, like, you know, there are people who need all of these things from other people, and I don't like those people. I like the people who are like, I I want this for my life.

• 43:44Speaker 00

  I want to build a company. I want to build an app. I want to be a musician. Like, it could be, I want to write a book. I need all of these things from other people in order for me to do that. I mean, that is a very uncontrollable way to live your life, right? Like, to to say, I it would be the equivalent of saying, like, I want to make a movie. I have a great idea, right? Like, and and the world is full of these kinds of people. And so that's a big one. It's like, well, make a movie. You have an iPhone. Like, show me, show me, like, a cool thing that you've made. There's TikTok now. I mean, like, there's things you can even put this stuff on. Like, show me what you've made. There's a great book Rebel Without a Crew by Robert Rodriguez, who directed Elite Battle Angel, Taxi Driver, and he it's it's basically, he talks about his journey.

• 44:27Speaker 00

  And it's it's like, it's like the Lean Startup applied to filmmaking or something like that, where he just, he literally says, okay, I live in this town. These are the things I have in my town. I'm going to make a plot that involves these things, because that's what I have right now. And then I'll make another movie, you know, like, we'll we'll take it, you know, it won Sundance or whatever. Like, it that's what got him started. And and that, those are the people that I look for, the people who want something so badly that they just figure out how to do it. And they're okay with, like, not maybe sort of having their first thing be just like the dream project. They just get started, and then they they figure things out as they go. And so building stuff, people who don't ask for permission, people who have hard skills, people who really try to save people time and are are really feel grateful.

• 45:09Speaker 00

  You know, like, they they feel like, wow, I'm so lucky to be in this place. Like, how can I make it as easy as as possible for everybody? People who don't think of it like a numbers game where I just need to send a hundred emails and what three people are gonna say yes. It's like, I'm gonna send three emails, I'm gonna spend three hours on each one, and all of them are gonna say yes. So I think that's possible. I think a lot of people underestimate how possible that is. And people who read a lot, I would say this is the other thing, is people who, and it again, it sounds, I don't know, like, when I say these things, it makes, I'm like, these are just basic expectations I have, almost, but it, but you might be surprised at like, how few people deeply read about anything, let alone their subject. I mean, their own industry, their own, the own, you know, the the set of problems that they're interested in.

• 45:55Speaker 00

  Someone might say, hey, I'm really interested, like, I, from their tweets, it seems like they're really interested in healthcare. Like, they think healthcare is fundamentally broken, it's totally messed up in the US. We need to go, and by the way, this could be someone who's like, we need to go this way or that way. Like, I don't know exactly what, you know, this is a abstract example, but if you said, hey, okay, cool, what's the best book that you've read on healthcare in America? And like, why it's gone to the way it is and and what the right answer is? I, a lot of them will say, I haven't read a book, I haven't read a book about it. I've read a lot of tweets, I've read a ton of tweets, I've read a lot, I've listened to a lot of podcasts with politicians about this and celebrities about this. I've read some, you know, Atlantic thought pieces or something like that. I have, I'm subscribed to a few subsects, but to like, have you deeply like, gone into the subject?

• 46:38Speaker 00

  And the the filter that I use is, if you remove the social incentive, so much of this you've done because of the social incentive, it's to comment, it's to go to work and talk about something. It's, you know, the reason I think people don't often read a lot of these old books is because like, that social incentive goes away. You know, you read this book, and then you're smarter, but that's it, you know?

• 46:59Shane Parrish?

  But I can't signal that easily to other people.

• 47:02Speaker 00

  Yeah, I can't, yeah, exactly. Yeah, it's like, oh, man, like, I read this phenomenal book on, like, I'm reading a book right now on whales. Uh, I don't know why, like, someone I like tweeted about the book, and it seemed interesting, and it's quite, it's interesting, it's a very interesting book. I don't know why I'm reading it, I haven't talked to anyone about it. It's full of really fascinating stuff, but like very, very few people I think do that, you know, and but but ironically, almost almost in this sort of paradox, when you do stuff like that, short term, I think that's true, but long term, over time, I really think that's clearly I'm doing it like there is still a reason I'm doing it, just like a much larger, longer time horizon. And I this has happened so many times, or I'll randomly run into somebody,

• 47:45Speaker 00

  someone who maybe is exactly the perfect person to like propel me in my career. And they'll be like, what, you know, what book are you reading? I'll be like, oh, I'm reading like a face like glass. It's like young adult fantasy thing or whatever. And they'll be like, that is my favorite book. That is my that has happened to me so many times. And guess what? I'm now there. They want to hang out with me all day long, and not to talk about this other stuff, but just to talk about, you know, like they finally have someone else that they can talk. So I do think it's it's it's sort of that sort of impatient with, you know, impatient patience, you know, kind of sort of thing impatient. You want to be impatient with results, I guess. But I definitely noticed that in people like there. It's very rare to meet someone who's genuinely just like exploring things that are at the sort of limits of their interest to kind of figure out what's new

• 48:27Speaker 00

  and different. And it's selfish of me. I like those people because they can teach me about all of this new weird stuff that I can go explore myself. But I find that sort of innate curiosity that isn't tied to a social thing or a financial thing is is relatively rare. And maybe that's just quote unquote privilege, right? Where it's like, oh, you've achieved XYZ thing is sort of the philosopher king thing like now that you're here, you can spend all this time messing around and figuring out these things. But regardless, I mean, that is something that I I look for in the in the people that I hang out.

• 48:58Shane Parrish?

  That's interesting. I want to dive a little bit into that. What's your ideal ratio of sort of exploring broadly to diving deep into a certain subject, do you think, for reading?

• 49:07Speaker 00

  I would say I spend almost all of my time exploring broadly, like I go deep very, very, very rarely. Even with authors, like it's pretty rare where I find an author where I am like, this person is so good, I need to read everything that they've written. That's happened a couple times. Like Matt Ridley recently was one of those people for me. But even like when you read his books, it's like every book is different. One's about genomics, one's about risk, one's about virtue, one's about evolution, one's about innovation now. And there's clearly a thread, right? Like you can kind of see the rational optic, you can see like what's, what's, where he's coming from and certain, his sort of fingerprint is certainly on those books. But even he is, it seems to me, is just exploring these things broadly. Because I think like,

• 49:53Speaker 00

  it makes those connections when they happen, like just so much more satisfying. When you find a connection between, I don't know, the way that mole rats like resemble, like the way humans used to be, and maybe like they're sort of, we figured out that there's this sort of like middle ground of social, you know, there's like packs, there's pack animals, and then there's like, you social animals, the colony animals that are like bees, ants, and mole rats, for some reason. Mole rats are also part of this group. And then there's humans, and there's all, you know, it's just interesting. I just think it's like, oh, maybe, maybe there's a way to apply, like, this is like a startup, and this is a midsize company, and this is a large company. I don't know. But I think so, for me, so many of the insights, like the easy insights have already been solved. If I just go deep, it's gonna take,

• 50:35Speaker 00

  like, literally, you have to go to the bottom of the ocean to get, like, if you go deep in quantum theory, there's a lot of books you're gonna have to read to get to really the frontier. But if you go broad, I feel like, I feel like there's just so much more avenue there. Like, there's just so much more freedom. Like, it doesn't take that far to, to end up in like totally unknown territory. It's, and even if, if there are other people there, there's like four of you. You know, there's like four people on Twitter that are talking about, like, the, the commonality between, like, yeah, like, animal relationships and like, company organization dynamics. It's, yeah, so I always think that, like, that's a better, that's a better approach. I frankly, very rarely go deep on, on reading, at least.

• 51:17Shane Parrish?

  What are some of the books that have had the biggest influence on you in terms of your thinking around entrepreneurship or investing?

• 51:24Speaker 00

  How to Win Friends is my, my sort of top recommended book. It's almost, you know, kind of a cliche, I feel like at this point to recommend that book. But it is like the canonical example for me of this saving other people time. Like that whole book is about like, how do I operate in a way that makes everyone else's life just really clean, really stress free, really easy. And so then everyone's going to want to work with you and be your friend. And, and so I think that is a really great book. Thinking Fast and Slow is a, is a really great one. All of the Matt Ridley books, I think, are really, really, really good. I think understanding your mental prison almost, like understanding the constraints

• 52:06Speaker 00

  of your brain physically and your body, like just where you came from, like what led to this moment, I think is just so helpful in terms of like feeling like, oh, these are the things you have control over, these are the things you don't have control over. David Deutsch's books I just read, The Beginning of Infinity and The Fabric of Reality, those books, it's actually currently the thing that I'm thinking the most about is, is The Fabric of Reality. It's like, I, you know, I'm, I don't know, you learn about, you know, parallel universes and sort of quantum mechanics and things in high school. You take, you know, an elective or what have you, and you kind of get it intellectually. But like really spending hundreds of words, like or hundreds of pages, like in this person's

• 52:51Speaker 00

  head and the way they think about it and how that relates to like free will, and it's just like really been interesting for me. Cause that's one, you know, one, one question I always, I, I think about a lot is like when you decide to do something like, you know, like when I decided to leave San Francisco and moved to Provo, was it the stuff in Provo that made me open minded? Was I open minded when I decided to move? Like where did I have the learning? Where is that? Like, is it a discrete system? Is there a point? Is it, you know? And so I've just been thinking a lot about like, you know, like when I have an idea, when I decide to respond to a question you have, where is that even coming from? Like I just speak. I don't, I can't tell you like where, you know, it's very weird. And so I've been like really interested in like, in this sort of parallel universes and, and quantum mechanics to, because I really think like,

• 53:33Speaker 00

  When you, when you learn the answer, like there, there is an answer, like what you gotta believe that I think uh to keep, to keep pursuing this kind of stuff. But when you figure it out, like when you realize like, oh, the reason that, you know, like, I don't know, like a hot water cleans stuff faster than cold water. Like when you know the physical reason behind that, it feels good. It feels like you have a grip on that your life, you know, like you can actually apply it in a, in a way, you know?

• 54:00Shane Parrish?

  Wait, why, why does hot water clean stuff faster than cold water?

• 54:03Speaker 00

  So I think it's because, you know, temperature and heat is just, the particles are moving faster. There's just more things moving around bouncing stuff. So I think when you're cleaning stuff, like you just like have more particles like hitting stuff off that, you know, ends up dislodging these molecules or, or what have you from the, from the material. And so I think it's literally just like colla, the collisions are happening at a faster rate, I think.

• 54:27Shane Parrish?

  That's interesting.

• 54:28Speaker 00

  But you know, just like things like that where you're just like, I don't know, it, it feels very satisfying for me to know. Uh, life is weird. I mean, like life is very strange. And I think you go through this middle where you, you, you, you're born and you're like, the world is flat and like the sky is above us and, you know, and gravity just makes sense. You can like, obviously flying would be weird, like what, you know, like you just kind of take these, and then you learn all of this weird stuff. Like we're on a ball of fire, just like shooting through like the void, like right now, we're like, what? You know, it's just crazy. And luckily we have like some rock around the ball of fire. The sun doesn't even have that, you know, just like, just weird stuff. And then, and then I, you, I feel like just, I'm just like floating, like I have no grounding in reality. I'm just like learning all these things.

• 55:13Speaker 00

  My life is like, what is death and this and that, like, it's just crazy. And then it, you know, once, once you start to read that stuff, I feel like I'm going back to that first place where it's all actually incredibly simple. It's just a bunch of dots moving around and, you know, bouncing off each other and at, you know, different levels of abstraction. You can use the phenomenon to explain different things, just like the earth and the sun. They're just two particles in space, just like when you're cleaning something, yeah, it's just two particles in space or whatever. And then Adam, you know, there's like, it kind of goes all the way up and down and it's like a fractal pattern. It just ma, makes me feel like I understand and I can like move forward without like. Walking through a wall accidentally or something, you know, like it just something like that. I don't, I don't know where I'm going with this, but I, I, I do enjoy like really

• 55:55Speaker 00

  feeling like I understand. And that goes back to the entrepreneurship stuff too, like just figuring out like what I can, what I can deeply understand, like reading the PayPal wars, reading in the Plex. A lot of these books are just really important because you, you are building a company, you're hiring folks. It's like, why start from scratch, right? When you have all of these resources from people who've done it before and, and, and the lessons aren't that, like the world hasn't changed that much. In many ways, you can sort of like straight up apply a lot of this stuff and copy paste it.

• 56:23Shane Parrish?

  There's a lot of timeless lessons from that. As you were, you were talking, I was saying, I was thinking that maybe you can just appreciate the beauty of the, the world in a different level with, with that sort of understanding. And I think that that's really important to be able to do in terms of quality of life. Maybe I want to come to happiness later, but switching gears a little bit here, what are you most insecure about?

• 56:45Speaker 00

  I, I am definitely insecure about like wanting stuff. I mean, I, I still think I am driven by a level of, of ambition and want for something, even though I have read all of these books and I feel like relatively good about what I understand about the world and how little it really matters. Like it, there is something satisfying about it. And, and so I'm definitely kind of like insecure about the fact that I have those wants and desires. Like I think, I don't know if they will go away, but I'm, you know, I always try to, try to figure that out and unearth like why, similar, why like, why am I like this? I don't have to solve the problem, but just understanding where this comes from. It just gives me a level of sort of like closure almost like, okay, that's just the

• 57:28Speaker 00

  way I am. That's because of this thing. I can't change it. I can't get taller. I can't do that. Right? Like there's just certain things that that's, that's, that's fine. So that's, that's, that's, that's probably a, a big one. And then just like figuring out, I'm, I'm sort of insecure with how much I worked, like how I, I, I work a lot. I enjoy it a lot. I am insecure about the fact that I enjoy it so much even, you know, like I go on Twitter and I talk about maybe not working so much, but I just genuinely really enjoy, enjoy it. And so, yeah, there's a, there's a lot of things like wanting a nice house or whatever too, right? Like the basic things that people, people seem to, seem to want. And then, you know, starting a family like that's a that's a scary prospect as well that I

• 58:12Speaker 00

  I hope to make like the focus of my life in the next like 10 years or so.

• 58:15Shane Parrish?

  Why is it scary?

• 58:16Speaker 00

  It just feels like it. It feels like I'm I've been so self centered my whole life. You know, it's it's basically everything I've done was for me. And, you know, I got married in last year in December, and that was like the first time that I, you know, I was like, OK, this is like we're signing up for, you know, something pretty big. This is very different from the the the the ideal relationships that I like with most people for me.

• 58:40Shane Parrish?

  Just email me every six months.

• 58:42Speaker 00

  Yeah, exactly.

• 58:43Shane Parrish?

  We'll check in, see how the marriage is going.

• 58:47Speaker 00

  And, you know, like, I moved up to Portland, Oregon recently. That's the first time I'd ever moved to a place as a group decision. It wasn't just me just saying, hey, I'm gonna go do this, you know, because I want to. And so that was like, that's a there's a set of learnings that I need to go through. I think having children like I think that will be really meaningful. And but yeah, I think it's just like important for me to figure out like, how do I live a life that sort of like the vision of what's important is is is slightly larger.

• 59:17Shane Parrish?

  Children are amazing, man. Yeah, it's just so incredible.

• 59:20Speaker 00

  I'm excited. I'm people ask me like, what are you excited about like Gumroad? And I'm always like having kids like honestly, like five years from now or so like that that's definitely like what I am aiming aiming for. And I think everything else is sort of like a kind of a distraction almost like just to keep me busy until I get there.

• 59:39Shane Parrish?

  Well, I'll talk a little bit about your writing process. You're pretty prolific on Twitter. That changed about, I don't know, 18 months ago or something. It's just your style sort of changed a lot. And ever since then, you know, I think you've got a lot of traction on there. So I want to I want to learn about your writing process a little bit, how you come up with ideas, how you. Put them into pithy sort of like tweets and talk to me about that.

• 1:00:04Speaker 00

  I have a lot of conversations. I would say my life is sort of pretty distinct in two distinct buckets. I'm either like having an interesting conversation with someone or I'm spending time totally alone. Especially with COVID, there's no kind of like in-between or social events or other background noise. Like it's really just like, we're talking or we're not talking, like sort of feels like that. So a lot, a lot of the tweets, like when I started learning how to, how to oil paint, I realized like the fundamental skill in painting was observation. It wasn't like paint application and like knowing color theory. It was like, can you even see what's in front of you well? And if you can do that, then like copy pasting that onto a piece of paper with some dirt and oil. It's actually the easy part. And I, I, I think the same thing with, with writing.

• 1:00:46Speaker 00

  It's, it's like living a life, like having a conversation with someone. It's almost meditative. You're like having the conversation, but you're also listening to yourself have the conversation. And I think that's really important because you're, you're sort of like your own editor where you, you can't change what you're doing and saying in the moment. But like, maybe you can note it for like the future use. And that's how you improve as a communicator and a conversationalist. And I think writing is kind of similar where like I'm, I'll be having a conversation with someone. And I will somehow like subconsciously sort of pin that little moment, like bookmark it of like, I, I said a sentence within a rant about a certain topic that's, I should tweet. I should just literally take that sentence and go tweet it. And, and that's a lot of my tweets. And then a lot of them are, you know, those sentences that I save.

• 1:01:31Speaker 00

  And then I just like stare at for a long time. Or there, there are things that I just can't stop thinking about there. I often feel like it's like food poisoning or something where it's just like in my system and I can't get it out. And I can't stop thinking about it. Every day I wake up and I like, for some reason this stupid, it's like a song stuck in your head. It just comes up again. And I found one of the best ways to, it's, it's, it's like resolving a, you know, a problem in, in therapy or something like that. Like, once you figure out like what it is, why it is, you package it up in a way that gives you clarity. It's kind of like untying, you know, a certain, like a string with a bunch of knots in it. You finally can see this thing for what it is. And then I would, I often share it and the sharing is, is really cathartic for me because

• 1:02:13Speaker 00

  it sort of gives it to somebody else. It's like, that's your food poisoning now. Like you go, you go, you go think about this for a while. I'm done. I did the work for myself. I, you know, I've digested this thing. Here you go. Have fun with it. And that's a lot of how I kind of, how I sort of like to think. And I would say the other insight that I think has really worked for me is I always try to figure out like, does this apply to a lot of the things in my life? Like, I think if you take, if you take it from a very sort of entrepreneur business focus, you're going to end up with like a very kind of narrow set of thoughts. But if you, if I often will, and, and that's a lot of the conversations that I'm having, but also as a writer, as a painter, as an investor, as a husband, as

• 1:02:54Speaker 00

  other things that I do now. If I can take the same lesson and apply it to these other things, and it sort of feels like a universal truth, then I often like, like those are, those, that's sort of, sort of a filter that I use to like, vet the quality of, of something that I, that I would share as well.

• 1:03:12Shane Parrish?

  One of the things that you said there that struck me was observing and talk to me a little bit about how we can become a better observer of the present.

• 1:03:22Speaker 00

  Yeah, I mean, I think a lot of it is, is, is paying attention and taking notes. This was the, one of the first times I had this experience was I was painting a rock. I was in Southern Utah with like an oil on canvas and I was painting a rock. And I spent three hours, it takes me roughly like two to three hours to like, paint something. And I remember like, for months, I could, probably even today, I could draw, I could draw that rock out for you. Like the, the angles and the shape and the proportions, you know, roughly. If, if I asked you to draw a dollar bill, like you wouldn't, I wouldn't be able to do it. You wouldn't be able to do it. We've never spent that time, like genuinely staring and paying attention to a dollar bill. I know what you would draw. I know what I would

• 1:04:07Speaker 00

  draw. We draw this rough thing with like, A one here and a one here and like a circle on this side, something.

• 1:04:14Shane Parrish?

  But like we had, we had the silhouette almost like that. We have the shape and the, yeah.

• 1:04:18Speaker 00

  Yeah. It's like when you have, when you're a kid and you draw the sun and you have the rays, right? Like there's a symbol that you're storing. You have the almond eyes. You have, you know, like the nose. That's like three, the kind of three semi-circles. But you've never actually like studied what this thing actually is and looks like. And so I think a lot of it is just doing that. I think you can improve like the, the time that you're taking. And that's what being present is to me is like just really focusing on the present moment and like noticing as many things as possible, which sounds easy, right? And it, it's almost paradoxical. Like you're obviously here. Like, what does that mean? You're obviously looking out through your eyes. You're smelling things through your nose. But like, if I said, okay, like, how many times did you blink in the last three seconds?

• 1:05:03Speaker 00

  You wouldn't even remember the last time you blinked. Clearly you blinked somewhere in the last, like your eyes aren't drying out, right? But like, this is something that you literally saw, like you saw yourself do that, but it's gone. Like your brain didn't even remember any of that stuff. And so I think that's a big part of it is your brain, unless you, you tell the brain, you signal to it, hey, this is important, like make a note of this because I'm going to need this later. To survive or, or, you know, to like some of these very fundamental biological incentives. It's going to forget because guess what? Like you have a finite number of neurons. You have energy and you know, it to energies being expended, like, you know, there's the sort of the, the famous adage of the sort of like the chess players that burn like eight, nine thousand calories a day.

• 1:05:47Speaker 00

  Like doing this insanely intense exercise effectively. And so I think that's a big part of it is like, you need to figure out like, what is the uncomfortable? What is like the, the exercise version of what I'm doing, right? Where I'm not just, you know, like, I don't know, drawing dragons out of my head, but I'm actually like figuring out like, okay, what are, what are the fundamental building blocks that lead to me being able to do a certain skill? And then, and then, you know, kind of a tree structure and then figuring out, okay, that means I need to learn perspective. That means I need to draw hundreds of boxes in, in perspective. Once I can do that, then I can draw ants, because ants are a little bit more structural or something like that. Then I can draw maybe like looser, looser animals, like, uh, you know, things with fur and, and things like that. And then I can, I can do cars and blah, blah, blah. Like you can scale that up.

• 1:06:33Speaker 00

  And then you, like a dragon is sort of like a cat with wings that breathes fire. Like it has the, the body proportions roughly of a cat. And that's where the dragon like comes from. But like some people, I think they just look at, they, they don't do the work of figuring out like, what is the path that leads to this? They just say, oh, that I want to do that. Right? So it's kind of the same thing. It's like the way you, you have to learn what you need in the moment and you can't really, it's like, you know, you got to learn addition to learn math, uh, to learn multiplication. You got to learn multiplication, learn division. You got to learn both of those things to learn algebra. You got to learn algebra to learn geometry. I think you need those things to learn trigonometry. You need those things to learn precalculus, like et cetera, et cetera, et cetera. And if you miss one of those things, you, you can still get by in life. Right? Like you can still like ace the tests and, and draw the things when you need to, you

• 1:07:18Speaker 00

  can memorize, but you don't really have a, a deep understanding of that. And it's kind of the same thing with, with being present. It's just like, I think some people go really far and they just, they feel like they need to do all of these things, but the truth is you just need to be there and you need to stop thinking about other stuff and you just need to like really, like it has to hurt almost like you have to be so focused, like you're working out, like I'm spending an hour trying to figure this problem out. Um, and I think most people, they, they, they might think about it like, oh, I just need to meditate, but meditation is, is almost work. Like it, I think it is, it is like a, you know, like exercise, physical, physical activity.

• 1:07:54Shane Parrish?

  This has been awesome, man. I really appreciate you taking the time to talk today.

• 1:07:58Speaker 00

  You're welcome. Thanks so much for having me.

• 1:08:06Shane Parrish?

  Hey, one more thing before we say goodbye. The Knowledge Project is produced by the team at Fernham Street. I want to make this the best podcast you listen to, and I'd love to get your feedback. If you have comments, ideas for future shows or topics, or just feedback in general, you can email me at [email protected] or follow me on Twitter at Shane A. Parrish. You can learn more about the show and find past episodes at FS.blog/podcast. If you want a transcript of this episode, go to FS.blog/Tribe and join our learning community. If you found this episode valuable, share it online with the hashtag The Knowledge Project or leave a review. Until the next episode.