Longevity Over Hypergrowth: A New Vision for Startups with Sahil Lavingia (Gumroad)

The people who are successful are the ones who are always there, right? Like, they're not the people who are like, oh, I'm going to go to like Greece for the next 3 years because there's a pandemic. They're like the ones who are— by the way, it's fine to do that, but generally the people who want to succeed, you need to be there. You kind of need to be the first person to read the blog post. You know, you kind of need to be the first person to reach out to the engineer who just said they're free. You know, you need to be there when like someone has a birthday party with all these people and you're like, I need to go because I need, you know, and that those are the things that end up like getting you to the next thing.

Welcome to the Eric Ries Show. Today's conversation is with Sahil Lavingia, the founder of Gumroad, and it's a story that challenges everything we think we know about building successful companies. Gumroad is now a thriving e-commerce platform connecting creators directly with their customers, doing $175 million in volume last year, by the way. But what makes this story interesting to me isn't just the numbers. It's how Gumroad found success by breaking almost every rule in the Silicon Valley playbook. After a near-death experience that would have ended most startups, Sahil made what seemed like a radical move, relocating from San Francisco to Provo, Utah. What looked like retreat turned out to be strategic genius. By stripping away everything but the essentials, Sahil discovered something profound. Gumroad's true value proposition emerged only when he stopped trying to force conventional growth metrics and started focusing on something else. Here's the counterintuitive part: it was only when Sahil accepted that Gumroad might not survive that the company found its path to thriving. Leaving the pressure cooker of the tech ecosystem behind freed him to focus on what he calls eternal features—the kind that drive sustained growth over decades, not just quarterly spikes. This philosophy has led to some fascinating experiments in company building. In 2021, instead of taking traditional VC money, Gumroad raised through crowdfunding. They've pioneered an innovative incentive structure where employees have a voice in their equity split and receive yearly dividends, essentially borrowing wealth from the future to motivate creating that future. It's a model that's already inspiring other companies to rethink their approach. In our conversation, Sahil shares his unconventional wisdom on everything from product development to company culture. We explore why he believes in building prolifically rather than perfectionism, why finding product-market fit should be embraced as "the fun part," and his "surfing theory" of company building—that it's all about positioning yourself correctly and having the patience to wait for the right waves. What emerges is a different vision of entrepreneurship, one that's more sustainable, more human, more long-term, and potentially more successful than the growth-at-all-costs model we've come to accept as the only way forward. I hope you'll find it as thought-provoking as I did. Here's my conversation with Sahil Lavingia.

Sahil, thanks for coming on.

Really appreciate you taking the time. Thanks for having me. Excited to be here.

I heard you say the other day that you spent a lot of your childhood in Singapore and you described Singapore as like the ultimate high-growth startup as a country. What did you mean by that?

Yeah. Oh man, I don't know if I would agree in the same way living in America now. I think America is like maybe the ultimate high-growth startup. I think in a way, you know, Singapore is just like very efficiently, like very focused on like what they knew they had, uh, you know, in terms of their unique geography and their sort of unique history of the, of the country and what that meant for like the people who lived there. And Lee Kuan Yew, I think, was just like very focused on that idea of like, okay, what, what can we actually do here? Uh, if you've ever read Isaac Asimov's Foundation series, it talks about sort of these, uh, this sort of merchant prince, uh, that you know, doesn't run the largest, uh, the largest army in the galaxy but has to sort of survive. And, and, uh, and I find that that's kind of what startups have to do, right? They're— you're competing with literally trillion-dollar companies. Like, FAANG are, you know, I mean, it's insane. Uh, they can squash you at any second. And so how do you actually basically get to that scale without them noticing you or like something like that? And I don't know. So I think you just have to be really clever. And, and, you know, the first like 10, 20 years of your life, you're sort of like a baby outside the womb. You can't really do anything, um, except in this case, your startup doesn't have any parents. You know, you're just— no one's really rooting for you, right? Everyone's invested in the, in the existing system.

So I love that idea. I'm a big believer that, that really organizations of all kinds, but especially startups, they're, they're literally alive. They're like superorganisms, and they're not created so much as born, and we don't manage or control them so much as parent them. We try to guide them, we try to give them, infuse them with some level of protection until they can stand on their own. When did you first encounter entrepreneurship?

I mean, I think the first time I remember making any money independently, which maybe is what entrepreneurship is, I was selling my time as a freelancer. I was basically messing around with Photoshop as a kid. I think I was like 13 years old. And I was learning Photoshop just because I thought the effects looked really cool and fun. And the school that I was going to had Photoshop and I was like, "Oh, this is cool. This is like an expensive piece of software I get to mess around with for free." And would just Google like teardrop tutorial, fire, realistic fire in Photoshop tutorial. And someone just noticed, I think, and said, "Hey, basically, there's this, this, this need for graphic design. We have all these teachers that need websites for their books, or we have like a charity auction and we need a little website. And basically, like, I think they didn't want to spend any money. And so, you know, it's like, hey kid, can you do this for us? And that's kind of how I got into it. I think my first client was my social studies teacher, and I think she paid me $15. For a website for her book, you know, and I don't know how many dozens of hours I spent, you know, actually, like, I had to learn. I would basically design these things in Photoshop, so they were like websites that didn't move, basically. And so that doesn't— that's not compelling, right? And so I was like, I had to learn Dreamweaver, I think, at the time to build out this website for her. And you're really dating yourself now. Yeah, I feel like freelance, I don't know, I feel like freelance is so underrated in like the path to entrepreneurship. A lot of people talk about like selling lemonade or something, but for me it's always been like, I think that's hard. I think building and selling products is like really hard. It's much easier, I think, to just say, well, like, can I just like help you carry a box for $5 an hour? You know, like it's a lot easier to start that way. And then over time that like you'll realize, well, like if someone's paying me to do something, then they're sort of getting some margin on me, right? Like there's something else that there's something I'm contributing to. And then you sort of, I think, slowly learn like, oh wait, like I'm part of this supply chain and I'm a freelance designer, but like I could actually write a book. Like, you know, I'm designing a book website, but I could actually just write the book and then I can design my own website. And I think that's kind of how I got into it.

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I can really remember that the first $15 I got for first computer programming, like, very vividly. It was such a trip, the idea that you just straight from your mind onto the computer and into somebody's life creating value for them. It's a rush.

It is a rush. It is a complete rush. It might be almost like this kind of almost unnatural rush, right? Because you're so used to having to expend physical energy in order to create value. You had to physically move somebody from one place to another or physically make a piece of clothing or food. All of these things require insane amounts of movement back and forth. And then you're like, wait, I just created a ton of value that someone paid me for, but I didn't have to leave my bedside. And it is almost like it is a rush of like, wait, that's Crazy. And yeah, I think that's only going to continue, you know, that— Oh, it's going to get—

it's about to get really wild. Yeah. Yeah. But I can remember it wasn't that long ago, I feel like even in our parents' generation, there was kind of like you would work by making or you would kind of do what you might— now we would call knowledge work, you know, being a doctor or a lawyer or something where you're working with your mind. But if you said, I want to make with my mind, that would conjure up for people a very narrow range of careers. And I'm sure I don't know what your parents were like. My parents, I think, were a little bit concerned. What are the career prospects for someone who's wired this way? And now, I really felt like it was like learning magic. Literal sorcery is how it felt to me that you were literally conjuring things out of nothing and bringing them to fruition, not constrained by the physical limits of what you could carry or what you could sew or construct. It was a really new experience. Think there was a lot of precedent for it. It's not like you read, grow up as a kid, at least I didn't read books about people who did that except in science fiction and fantasy. That's funny you start with Foundation because that's how I felt like. I felt like I was a protagonist in one of those books, you know, who discovered he has a superpower, create things with his mind.

Totally, 100%. And I think you're right. I mean, it's always been around, this idea of knowledge work. There's some percent of the population who's paid to think and paid to sort of participate in some storytelling, mythos creation of intangible platonic objects or some such that don't exist in the real world. I think my mom was a CPA and that's sort of a form of that and that has existed for so long. You've had accountants, the Silk Road days, thousands and thousands of years of of people who've had to sort of store these things in their head and they maybe felt like magicians and mages and superpowers where they're able to sort of help economies flourish by trading and being the center of trade. But still, that required all of this movement of goods. And when that sort of moves online and you say, "Wait, all of a sudden we can create value without having to burn all of this fossil fuels to just transport this piece of paper." I'm filing for an international driver's license. And I have to print out a piece of paper. And so, I bought a printer which will be useful for other things, but I bought a printer to print this piece of paper and then I have to walk down like 20 minutes to the AAA and maybe I even have to take the subway. And then, I have to get passport photos taken that requires the production of a camera in a factory. And instead, I should just be able to have an iPhone app that just allows me to do this and the amount of just carbon that would, you know, the benefits I think are just still tremendous in terms of unlocking what happens when you move this stuff into the cloud per se.

Yeah. After you lived in Singapore, you came to the US. Just how did you come to this country? And you were talking a little bit about America as the ultimate startup. Now, having been here for a little while, I feel like that's such a common perspective among immigrants who actually see America much more clearly sometimes than those who grew grew up here. What was your impression of it coming back and tell us that story?

Yeah. I mean, I have a weird background, which is I was actually born in the US. I was born in New York and then when I was 4, my parents immigrated, emigrated to Hong Kong and then Singapore after a year. So, I grew up in Singapore but I'm sort of American the entire time but never really lived in America, didn't go to public high school in America, et cetera. And then I went to college for 4 months and then I started working in the startup industry. So, I have a view on America, right, which is living in cities, living and participating in the industry, being born here, being a citizen, but then also having an American accent even that people probably wouldn't tell that I didn't grow up here, but then not having. And so, having some sort of outsider's view in some ways, I have a lot of pro sort of Singaporean sort of probably biases, but then also always feeling like I'm American in Singapore and I'm going to go back. And yeah, I mean, I think, I think, you know, America at the end of the day is, is, it's just like the best attempt at managing a bunch of concerns. I think Singapore is amazing, but Singapore, it's almost has like these unfair advantages, right? It's a very young country. It's an island. It's a very small island, which basically means that it's very easy to say no to people coming here and sort of highly regulating the sort of supply and demand. And I think America is like the best at just realistic progress, which is creating a system in which people disagree, right, a lot. And finding a way to, to grow within that framework— I think living in New York is a sort of even a microcosm of that, which is just like, it's insane to me how safe it is, how like there was no broken windows, there's no— like, there's just such a safe place. Um, things happen, but there's just like a— I think the amount of trial and error that this country has gone through to figure out all of these things, and I also just think it got lucky. It's kind of like when you pick a programming language early and it really benefits you or it doesn't, but you don't really know. The ecosystem is still developing and you might regret the decision and you're like, "Oh, God, we got to do this big migration." And countries basically can't do that, right? You're kind of stuck with whatever the constitution is for better or worse because the alternative is violence. And I think America just nailed it in many, many, many ways. The fact that it's still standing so so much later and help the growth and the fact that all the FAANG companies are here and not in other places. I think it has just figured it out and in ways that are kind of, it's not ideal in certain ways, maybe people would want changes, but I don't know. It's kind of magical that almost it's impossible to change. It makes it very difficult for someone to come in here and say, "Hey, I want to run the country this way." The country, just as its own organism, similar to a startup, just revolts and says, no, sorry, like, you can't go that way.

For all its looseness and work, there's a certain underlying stability that we take credit for.

Yeah, I mean, I really feel like I can say anything and build anything, and as long as I'm not doing, you know, like, like punching someone in the face, basically, I can get away with it, and it's sort of supported. In a way that it just doesn't exist anywhere else. And Singapore and all these other amazing democracies do exist, but you still don't have like the— it's sort of like in theory versus practice. Like in theory, a lot of places should have the ingredients and the recipe to like produce what we have here, but then it's just like, well, then just go out and do that thing. And everyone's like, ah, it's allowed, but like, you know, you're allowed to do it if you really want to. It's kind of like—

I've traveled to many countries. When I first became an innovation expert, whatever that means, a lot of countries would ask me to come and speak and wanted to talk to me about how they can build their startup ecosystem. And of course, I think that's really important work. But I got to the point where at a certain point, people would ask me, "What should we do?" And I would have to answer, "Look, it's actually well known what you should do and I'll tell you, but after I tell you, you're not going to want to do it." And then, I've been in so many eyes like, "No, no, no, we totally are going to do it. We totally want to do it." And then at the end they're like, "Oh yeah, I guess you're right. We're not going to do it." It's easy to say but it's very difficult to do.

Yeah. And I think it's also just a question of what the mass population wants and at scale, it's not only about what are the successful entrepreneurs interested in, right? But also what are the fishermen really interested in, right? Yeah. What are the rice farmers interested in?

People don't realize the extent to which the non-entrepreneurs have a tremendous influence over whether or not entrepreneurship happens in a country or culture, even in a certain city. At the risk of giving some spoilers for the rest of your story, when I kind of look at the arc of your career, I kind of think of you as the man who walked away because you've done it multiple times. You know, you were in college for a short time, you had this incredible experience at Pinterest, and of course in your leadership at Gumroad, you know, you were on a very defined path and then took a really different path. And I'm curious, I want you to kind of tell us those stories and and walk us through what happened, how you got to the incredible success you have now. But I'm curious if that resonates with you as somebody who has kind of been willing to like deviate from the path that was expected of you, like when most people frankly I don't think have the courage to do that.

Yeah, I mean, I've never heard it framed that way as the, you know, the man who walks away, but sort of something I need to talk to my therapist about. But, uh, well, I don't mean it in a negative way. I really admire it. Yeah, I mean, I can sort of go through maybe, yeah, the specifics, and maybe we can kind of generalize why I tend to do that. But at, in school, I felt like I knew what I wanted to do. I wanted to make stuff. And I remember going into an academy class with 300 kids, you know, CS freshmen, and being like, hey, does anyone know what Hacker News is? Does anyone want to build stuff for fun? And like one other person was like, yeah, let's like build some stuff together, right? Out of 300. And I'm like, I moved to California. I moved from Singapore to California. Like, I'm right next to Silicon Valley and nobody— like, what? This is 2010. This is not like 2001 or something, you know? And being like, yeah. And then I was like, okay, well, I guess I got to move to San Francisco. How do I do that? I got to start working at startups and things like that. And the way I pitched it to my parents was like, hey, look, like, If this doesn't work, I can go back. But like, if this— like, if— like, how do I even know that this is what I want to do without doing the thing? Like, I'm getting a job— like, I'm getting a degree to get a job that I haven't done yet. And so that, you know, why not— why not try and go back? And so that was that. And then Pinterest, I— it was kind of similar. So I was like, it sort of just feels— maybe I'm there now, which is like, it always feels like there's— I'm getting closer to the thing. But I'm not at the thing that I'm really looking for, which is I want to just build stuff with almost unlimited flexibility. And, it's just hard to do that when you are working for somebody else who has their own vision or enrolled in an education system that has to sort of justify its nonprofit status and needs to have all these— there's just stuff, there's all of these other stakeholders in your life. And I think being a founder of a business was my way of trying to kind of get to that place. And even now, as I work on what I work on, and as you mentioned, in 2015, when we failed to raise the round of funding, basically continuing to run the business basically by myself. So it was just me for about 2 years or so, about 2015 and 2017. I just did support and kept the site up, fixed bugs, cause bugs as well. I remember causing a few. And then, when I started hiring people, I was like, "This is actually fun. I get to do what I want. It's not like making a gazillion amounts of money, but I have time to write and paint and travel and make stuff." And I just really spent a lot of time thinking about what do I actually like to do, just observing myself. And I just like making stuff. Like, I just like making stuff that— and if it solves other people's problems, that feels really good too. And if it makes money, then all of a sudden I have this like almost like perpetual motion machine in which I can just keep doing it and keep investing in that thing, maybe even hire people that I can learn from and do it together and stuff like that. And yeah, I just felt like you don't necessarily need the school, that you don't need the boss, you don't need the VC in the room. And now there are tools that did not exist before. And honestly, I don't know exactly what I was doing. I remember I was like, I guess I'll sell the business for $25 million. At some point, that was kind of when I was just running it and I was like, maybe in 10 years it'll continue to just trickle along and grow and some PE roll-up fund will eventually buy it, but I'll be like 45, years old. And this way of running the business will allow me to like have hobbies and spend time with my kids and all that kind of stuff. And then COVID happened and, you know, we had just been running the business in this way and that created all this opportunity. And then in 2021, Regulation Crowdfunding had a bunch of rule changes go live that allowed us to raise up to $5 million from the crowd. And I was like, wait, I can like double down on Gumroad. Without having to sign up for this VC journey. I still, you know, there's tons of benefits to raising money. You get to like over-invest in certain things. You can hire people you may not have been able to afford that would be able to like drive a lot of value for the business. And they kind of just came out of nowhere and I was, you know, I was like, yeah, let's do it. That sounds like, that sounds great, you know, great to me. And I almost feel like it was like a, sort of certainty at this, you know, like the internet basically would eventually lead to crowdfunding. Like it's just, it has to be litigated and all of these parties that care, you know, as we talked about, like most people are not entrepreneurs. So like the non-entrepreneur stakeholders in the country are like crowdfunding, like just going to be used for scams basically. A bunch of people are going to scam a bunch of other people. It's going to be like gambling and stupid and like doesn't make any sense. And you're like building like, and then you see crypto and you're like not that excited about what, you know, like it's unfortunately, yeah, but, but yet it has happened like yet, like the federal government has implemented regulation crowdfunding and the JOBS Act and is continuing to actually make it better and easier and cheaper to slowly do these things. It's just slow, right? It's just a, it's a big, big, big startup of 300 million people. And a massive army that they have to feed and all these other things or whatever. And so we took advantage of that and that kind of, and then finally one last thing, we did a dividend. So in 2023, we got profitable. And once we got profitable, I was like, this is fun. I don't really want to sell the business now. Can I just pay myself and the rest of the stakeholders, all the 7,000 crowdfunding people a dividend?. And if we can do that, then all of a sudden I can continue to do what I get to do. I can maybe one day buy a house in New York and I can motivate the team with equity that's worth something because it's intrinsically worth something because of the cash flow of the business that they're going to help increase hopefully. And then maybe most selfishly, save the company money basically, right? Because there'll be less less cash going out of the company for people's salaries. And so I think it's sort of a win-win-win. And it's just about, I don't know, just now finding other people who are interested in this idea and telling them about it. And maybe they'll tell me why I'm too idealistic or something, but I'm not too worried about that.

Let me take you back. How did you break into the startup ecosystem? I feel like that's like a classic thing people want help with. And And they think it's so difficult. You know, you were back in the USA for only a few months and you were already in the middle of it. Just tell us how that happened.

Yeah. So when I was at USC, I started building, I mean, I was, I guess, continuing to build stuff and putting iPhone apps in the App Store and submitting them to Hacker News. And I basically had this tribe.

What was your first iPhone app? Do you remember?

The first iPhone app I ever built was in Singapore. It was called Taxi Law, which is what people say. When they want to hail a cab in Singapore. And basically it was a way to call a cab using an iPhone app. Like, you hit a button and it calls a cab. And before, you had to call a number. That was the innovation, from going from calling a number to clicking, tapping a button, right? So nothing crazy, but that was the first thing I built. I sold like 4,000 or 5,000 copies of that app or something like that. I had a meeting with like the Singaporean taxi cab company or whatever about building something. And eventually Uber launched. And I mean, many people have tried to solve this problem, but that was the first thing I built. I built a color palette manager where you could take a photo, it would generate color palettes. You could just mess around with the hue saturation sliders and I don't know, I was just building stuff, just building stuff. And then one app, the app that did the best that actually got the attention of Ben from Pinterest, the CEO at the time, founder, CEO. He, uh, I built this thing called Dayta, D-A-Y-T-A, and where you could basically track data points in your life and push-ups or glasses of water or hours slept or happiness score or whatever. Uh, and, uh, I put on Hacker News about like 70 upvotes or something like this, and he saw it and sent me an email and said, hey, I work on this thing called Pinterest. We're a website We need an iPhone app, obviously, that's where the future is headed. And looks like you can do that. Looks like here's evidence that you can do what we need. Can you help us out? And so, I basically started freelancing for them. I think I charged them $4,000. It was my first invoice for Pinterest for iPhone. It took $8,000. I don't know. It took a bit more than that, but I just built it. I was basically a student at USC and I would maybe spend 20 hours a week building Pinterest for iPhone. And very quickly realized, one, uh, I was already good enough to get a job, and so why was I in school? And then two, there was tons more where it came from, like the amount of demand for that skill set. Like, once you know what— basically what happens is you start like interacting with these people that you basically work with on social media, uh, and then you kind of just— the algorithm starts just kind of noticing, I think, that Hey, you're friends with Ben from Pinterest and he's friends with this founder of this and you just kind of like, that's social networking, right? Social networking, I guess, is where that came from. And so I just kind of built up, I don't know, a few hundred followers on Twitter and that's kind of how I got into the ecosystem. But really getting your first job is just the best way, I think, honestly. I think so many people are like, I need to be a founder of a tech company. And it's like, yeah, you do, but who's the founder of a tech company you admire and go work for them? And then they'll make your life a lot easier because you'll see them make all the mistakes and get all the learnings.

I really remember that gold rush feeling of the early days of the App Store and the new mobile web. You know, like the— there had been mobile web for a long time, but with the iPhone, it was completely reinvented. And there were all these new opportunities, people, both for freelancers and startups. It was very exciting. And I think part of what makes your story so interesting is you just inserted yourself right into that rising tide and then allowed that to carry you into all these opportunities. I'm sure there are many people who are listening right now who are thinking, wait a minute, we're at the same moment in AI right now, the GPT store, and there's all these new opportunities and it's so easy to— so what advice would you give someone who wants to take the lessons? Imagine there's a student right now at USC trying to replicate the experience that you had.

What advice would you give them? Yeah, honestly, I think it's similar, which is to make a list of the companies that are participating in this important change, right? At the time, it was Pinterest and Instagram and GitHub and Slack and Snapchat, all of these companies that— Instagram was the big one though. I remember talking to Kevin from Instagram and Adam from Quora and Drew from Dropbox and people. My bias has always been product. It's always been, I love talking about how do you make really good— like this sort of cult of Steve Jobs. Great. And so, it was almost like a glorified book club of trying to meet people who really read everything Steve Jobs wrote. And I think similarly, I think it's about finding like who are the interesting personalities, who are the interesting people who are at the bleeding edge of this new technology. It's not going to look the same because it's, for example, it's much more sort of engineering-focused whereas maybe the iPhone was much more like sort of design and UI-focused. Maybe that will change and it'll become more UI-focused. I don't know. But I would do what I did back then, which is find a small company working on this problem that has a founder who's obsessed with product and improving the customer experience. I use this new app called Cursor all the time that I basically became a daily active user of like a month ago. And now, you know, I use Yes, the online code editor, AI-powered.

Yeah, Cursor.ai. We'll put a link in the show notes. It's amazing.

And, you know, I'd probably send him an email and be like, hey, can I help? Can I make, you know, I was actually honestly thinking about doing this anyway, even now, and just saying, hey, do you need help with like a cursor for iOS, right? Like, why can't I, if the AI is doing all the work for me, I don't even need a keyboard, then maybe I don't need a, you know, a laptop or something like this. And so, yeah, just kind of trying to be, you know, rub shoulders with people and then actually try to add value. I think a lot of people, you know, I get a lot of emails from people who are like, hey, do you need a PM? Or like, do you need an ops person? Or do you need a— it's like, not— I don't need any of those things. I'm sort of relatively self-sufficient. But what I want is people who can look at what I'm building and say, hey, I can help you build that thing faster and better. And that takes, you know, design sensibility, product sensibility, taste sensibility, which I think all of those things come from basically building small little things for people. And, you know, like I built this pizza lot. Yeah, just, and I think a lot of people, they have one idea and they marinate on it and they marinate on it and it's like they're going to be their magnum opus sort of when they, when it comes out for the first time. And it's like, no, just like it's garbage. It's a garbage idea. That's okay. Like put it out there and make it, make it as good as it's going to be, fail to get any real customers and then like take all of those learnings that you have in your brain and then make something else. And 10 times from now, you'll have something really novel that will be unexpected. One reason we have 4 products is because I don't know which one is actually going to drive the most impact. I would like to believe I have a sense of it, but you just don't know where things are going. You don't know how good the next model is going to be and in what dimension. So, I don't know. I think it's underrated to just build more stuff and not take the idea you currently have so seriously. Even Gumroad, I think, is evolving so much in what it does, what it offers people, the types of customers. So, people are so scared of churn, for example, but it's like if you're growing fast, then everyone is churning in the sense that all of your users are new. Therefore, all of your old users have sort of churned, quote unquote. And so, I don't use Snapchat. Snapchat's a massive company. I don't use Facebook. Facebook's a massive company. And by the way, I might train for 30 years, then I come back. I think a lot of things people just underrate, they think they're— but yeah, I don't know. I think it's a lot just doing stuff and building your own training dataset that no one else has access to, which is just about trying things. I think a lot of people read and try to get answers that way. They try to understand a population, but they've never been to that country, right? And it's like— Yeah, you have to try it.

You have to go there and try it yourself. Yeah, I do think that's really underrated. So what I think is so interesting about your story is the typical startup advice, you know, I mean, the best startup advice out there is to find a wave like you did, to put yourself out there, do experimentations like you did, to form connections with the most product success, you know, companies that are most likely to be able to surf that wave and capitalize on it, and then go work at those companies, be an early employee at those companies, and ride up with them as a career accelerator. You did all that stuff. You wound up at Pinterest, one of the most successful companies from that era. You were— how big was the company when you went to work there?

Yeah, I was the second employee. So it was—

yeah, yeah, you're employee number 2 at a massively successful company. And you could have— I think a lot of people would have said should have just stayed there and rode it up. Why not?

I mean, to be honest, I got fired. So that made it a little bit more complicated. But the more nuanced conversation that we had was basically I wanted to build stuff really badly and I basically couldn't not do that. And I don't know, call it credit anxiety or something, I don't know. But basically I just had the personality of someone who wanted to build stuff all the time. And even I noticed the more product market fit Pinterest had, which is the goal, by the way, of founders to really seek that. The more boring it kind of got as an employee of the company because you were just like doing the thing that you're like copy-pasting, like, okay, we need comments, okay, we need reporting and flagging, and just wasn't that fun. The fun part was getting to that point. And so yeah, I think I just felt like that, you know, to me that like I really just wanted to be the best at making stuff and getting from sort of a group of people that have a problem and being like, okay, or even just looking at a population and saying what is worth solving for them right now. And I think I just needed the reps that basically no company would really be able to provide you. And honestly, I think I still think it's underrated. I wish more people— you're totally right, by the way, that you want to surf a wave, but just like surfing, waves don't come around all the time. I was watching the Olympics and Sometimes there's 10 minutes without anything and they have to add another 10 minutes onto the clock or something. And this is, by the way, they picked the place on Earth for maximizing this thing. And I think, yeah, I was talking to actually a former Gumroad employee about this and he's doing very well. He started a company with and raised multi-hundred million dollar valuation since. And he was saying basically it's about treading water more than surfing because you are surfing every once in a while, But it's really about being on the, you know, being there. And most people will basically show up, wait, and leave, right? Go home. And if you can basically— in Gumroad, I think kind of similar, like we did definitely like landed in SF at this sort of like surfing period. And then maybe if I had landed in 2013 to like 2017, it was a bit quiet and then it kind of got a little bit more exciting. And then COVID was crazy and And then interest rates went up and it was a bit quiet. And then now AI, it's kind of become crazy again. But the people who are successful are the ones who are always there, right? Like they're not the people who are like, "Oh, I'm going to go to like Greece for the next 3 years because there's a pandemic." They're like the ones who are, which by the way is fine to do, but generally the people who want to succeed in that way, you need to be there. You kind of need to be the first person to read the blog post. You kind of need to be the first person to reach out to the engineer who just said they're free. You need to be there when someone has a birthday party with all these people and you're like, "I need to go because I need—" And those are the things that end up getting you to the next thing and unlocking some insight. It's not just sort of thinking about it and sort of just like, "Oh, I have a thing on the back burner. I want to do a startup and currently I'm here doing this." But It's like, no, you kind of have to be thinking about it all the time. Right now, which is honestly kind of crazy, I'm 13, 14 years into this and this happens every once in a while, but I basically go to bed thinking about what I'm working on and I wake up thinking about what I'm working on, which is very not good for my health, frankly. So, I'm a little bit of a lull. I'm going to the gym twice a week instead of 5 times a week, but it's amazing because it does feel like we're at this kind of cuspa moment. And, but it's also now having the experience of having done it for this long, it's like it comes and goes, right? You know, they're going to be more of these and this will also fade eventually. And then there will be another crazy wave. And it's just the nature of reality, right? That this continues to happen and things get, you know, things will continue to cycle as technology gets invented and certain problems get unlocked and certain scales get achieved and your computer gets a million times more fast and energy one day is free and internet is everywhere and robots are doing your laundry and all that stuff is probably— Probably a lot of waves between here and then. Yeah. And there's going to be a lot of waves and a lot of, as you said, magical moments. Where you're like people will all of a sudden wake up with some superpower and they're like, wait a second, I had 4 fingers, now I have 5. Like I unlocked, I had almost everything I needed but I was missing, like for me, I'm not good at rhythm. I like my musical abilities are lacking. But if somehow AI like solved that one thing for me, maybe I would pick up an instrument or something like this. And I think there's just like there's certain people who get unlocked when paperback books unlocked a whole wave or the camera or canvases for oil painting or even in music like Auto-Tune. There's certain people who are just amazing but they can't sing. And I think AI in all of these ways will do that over and over and over again. I would never be a farmer But, maybe I would be if there were sensors were really good and help me be like, "Hey, Sahil, you got to do this thing. This thing fell over and this thing's getting too hot over there and you got to pour water on this thing." I don't have the sort of perceptive ability to notice that where I'm just too absent-minded, I'm in my own head, I spend my own career focused on other things that I happen to pick up on. But, if we can these things will sort of assist us in many ways. And it's exciting, I think. And so, I don't know, I think a lot of people, they're so concerned about catching the next train because it's like the last one. They think it's over, you know, it's over, or like this is the apocalypse. But it's like, no, there's many more trains where you're at the trains. Just make sure you're at the train station, right?

That's like the important thing. I can thoroughly and vividly remember in 1999 feeling like I'd missed the internet. It was too late. I'd missed the wave. And I do think that's one of the underappreciated lessons of the concept of product-market fit is that there's the long, slow staying alive part before the hypergrowth part. And it's very difficult to keep a company alive, keep a career, keep your foot— like, it's very difficult because you just don't know how far from the goal you actually are. And a lot of, you know, Lean Startup, a lot of bootstrapping, a lot of like that, the The kind of guerrilla tactics of entrepreneurship that get passed between founders, you know, and investors like that are really serious about it are really about longevity, just figuring out how to keep true to that vision during those very long dark periods. And it's been a recurring joke in these conversations that, you know, we often meet someone who's like an overnight success, 10 years in the making. And we tend to collapse the 10 years into a very brief photo montage because it's really boring. The staying alive part is boring. It's the success is what's exciting. The hockey stick is what's exciting. But the long flat part is where the really painful, difficult art is. So I appreciate you kind of talking about that. I hadn't thought about the surfing metaphor of it, like being in the right place to be able to catch the wave as they come and then to have the judgment to know which wave you're like, "This is the time to double down and go all in." Yeah.

And I think something that makes it even more difficult is that you have to convince others too., right? It's rarely that you're going to do it all by yourself. And so, not only do you have to motivate a bunch of people to work hard every single day and show up, but, you know, when there's a drought, you know, like there's nothing happening and everyone wants to move and you're like, "No, we got to do this," and you have to somehow come up with something reasonable too, not just make up something, but really come up with a sort of a thing that will keep the company alive for the next 2 to 3 years, a set of customers that you just need to sort of as a stepping stone to the next one or like some really hacky technical integration. And yeah, it happens over and over again that there's sort of like very deeply unsexy, you know, because you want to believe that you build something, you have the right idea and it just, it's like fire and it just catches and it's, you know, but it's like, no, you just like for like 5 years. And then it turns out Lightning is what does all the work, but everyone else you were competing with like went home. And so, you know, you just, you just got it all right. And like, it often happens when like the, when ChatGPT, when ChatGPT came out, it was not a race to build ChatGPT. Right.

It was, no, I know several different teams that had the technology of ChatGPT in the lab long before OpenAI did and made the conscious decision not to release it. So it's like the opposite of a race. People were putting it off and it took— yeah, somebody have the, the— I don't know what the right word is, but the decision to do it, the conviction to do it in spite of all the obstacles and all the reasons not to do it, and then to let it, let it catch fire like that.

Yeah, the, the example I always think about to humble myself is AWS and how surprising AWS was, but then still, like, how long— it was out for like 10 years and everyone consistently said it was like not the future, it was too expensive, it would not work, wouldn't scale for Dropbox or Netflix. And then, you know, now it's like the largest business on earth is basically cloud computing. And Google could have done it, Microsoft could have done it, and eventually they did, and their businesses are massive too. But it took them so long, uh, to actually actually react. And that's why I think it's so important. Like, I think the thing that Amazon probably had is like customers, right? They were like, well, our customers need it and they're paying us a lot of money for it.

And so the original, original AWS is one of the, one of the greatest MVP stories ever. I remember when it came out, it was so absurdly bad. It had almost no features to it. You had to package your own ISOs and upload it. For those that know what that is, you take an image of a CD-ROM with your software on it and then upload it to the the server, and it was, it was very minimal what it could do. Now, now of course it's super fully featured, but it, it was seen much too difficult, and there were a lot of competitors at that time trying to build a much more fully featured, fancier, more automatic cloud. And ultimately AWS ate their lunch because the MVP was done sooner, it was quicker, it was cheaper, it was just, it was simpler for customers to understand, it worked better for early adopters. And from there they were able to do that process you're describing of just getting the reps necessary to figure out what customers really wanted and needed and figure out how to grow Yeah.

And I think when that is clear to the world, because eventually it's figured out, the science is replicated and people are like, "Okay, this is how you do it," you're going to win because you're the one with the best team who's thought about it the longest and you've had the most reps. And yeah, I find that it's very rare that the second, third, fourth, fifth place person gets there. So, it's It's really important to be lonely and be okay with that.

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Now, I want to take you back after Pinterest. I appreciate being really honest about this. You get fired from Pinterest. You had this kind of hyperactive desire to keep building and not just to confine yourself. And listen, I totally relate as a founder and as an early employee. I've been on both sides of that tension. It's like, as a founder, you want everyone to just start— it's like, we finally found it. Okay, everyone just needs to row in the same direction. And yeah, there are people for whom, like you're actually taking something away from them by doing that. It is a little bit boring. And so you want to build a lot of stuff.

That must have been a low moment for you.

Like, take us from that moment, how you were feeling then, you know, how did that ultimately lead to founding Gumroad?

Yeah. So yeah, I mean, it was tough. I was like, I guess I'm starting a company. Like, you know, it was not that exciting. But, through even just the 4 months of living in Mountain View, Palo Alto, I had met all these people and I all of a sudden had all this time. I had no job. And so, I just emailed every single person I met, DM'd every single person who followed me on Twitter, maybe not actually, but a bunch of people and said, "Hey, I'm starting a company." I kept it very vague, like, "Let's grab coffee." And so I just spent, I think it was maybe 3 or 4 weeks just meeting people and just saying what I wanted to do. I wanted to make stuff. I got some advice. So very quickly I started to get a sense of like, oh, this is the kind of things that people are building. This is the stuff that's getting funded. And I wasn't trying to raise money. I wasn't trying to do that necessarily. It was more just like, telling people like what I was up to. And eventually you do that in like the right place and people are like, hey, you know, like if you ever want to start a company, I mean, I do this to people, I'm like just riffing with someone, by the way, if that you're serious about that idea, like let me know, you know. And so that started happening and someone offered, you know, $100,000 check or something. And I was like, oh, that sounds cool. Like I'll let you know once I have, like, I don't know, I get that far. And they're like, like, you know, if you want that, you have to like put that, you have to like do that yourself. And yeah, basically, I just kind of fell into it. I just sort of like almost got told that this is how you do the thing. And there were a couple of people who were really key, Seth Goldstein, Sahil Lavingia, who were really kind of helpful at like, this is how you put together the round. And if I had gotten advice maybe from different people, I would have done the wrong thing, but they helped me like basically say, you know, you should probably raise like a million dollar seed round that will give you the space to just build what you want to build. And I really wanted certain people like Naval and Max Levchin on the cap table. And they were very clear they wanted, you know, to like invest at a reasonable valuation. And so I just said, okay, cool. Like I'm going to raise $1 million at $5 million post-money, 20% was the sort of standard dilution at the time. Single founder, so fine, reasonable. And what was the vision at that time? It was just to build Gumroad into, I think at the time, like Amazon for digital content or something like that. You know, just like knew that it was pretty uncertain, but that we were going to unlock, like make it so easy to sell stuff and basically see what that would, what people would sell, like what would people actually do with that. And it was pretty unclear. And it was, but it was, it was a relatively like, we'll see kind of bet. And then if this starts to resonate with people, we will continue. But if this doesn't work, we'll do something else or start another company and, and, and, and all of that. And then basically 4 or 5 months later—

It's a very Silicon Valley story, I gotta say, from being fired to like people immediately pouncing on you to say, listen, we'd like to give you a million dollars to do this new company. I've lived through that. But for people who have not— people from outside Silicon Valley, it must sound very strange. And I wonder how you reconcile this. Like, in so many parts of the world, having a failure on your resume would be a big problem. Here, people viewed it as a success. Why? Like, what was it like? I guess I think I know the answer, but I want to know what was it like for you at the time? Did you have that kind of cognitive dissonance about like, wait a second, How come people see this as an opportunity? And like, how did you get into like learning the, just the mechanics of it? You found these mentors. How did you figure out you wanted Naval and Max on your cap table? Like, you have all these pieces. I feel like you're kind of like swimming in this milieu. It's a very Silicon Valley thing from that time. Just share a little bit more like the story of how it came to be and just how did it feel?

Yeah. I mean, I, Honestly, don't know exactly. I feel like I was just looking for examples of people that I liked, like their personalities and mostly their writing on the internet and they were informing me and what I was building even though I was not like a startup founder or anything like that. I was still building stuff and designing stuff and that was based on principles I learned from blog posts and things. I always felt like, and I still feel like there's such a value to doing that that most people don't take advantage of, you know, in terms of writing online and publishing what they've learned. And so yeah, I basically sort of had like, oh, I like these kinds of people, they're older than me, so maybe I can like learn from them. And it felt like this place that I was at, this was just kind of like the way that you did that. You know, it's like if you grew up in Singapore, like, and you met someone really interesting, you would try to get an investment banking job with them or something like that. And just in the Bay, it was just like, oh, you would start a company and get them on your cap table. That's kind of what you would do if you wanted their advice, you know? And so it kind of just like kind of developed into this. I think just the process is just so institutionalized, you know? That it just sort of— there's enough people who almost like it's their job to make that happen for you. And it's just like when you move to New York and you just get invited to parties and you're like, why am I invited? Like, they're like, no, this is like you're a person in our area and we throw parties. So, and I'm like, okay, cool. You know, and I think there's just— I remember going to Burning Man, I'm like, this doesn't make any sense. Like, I'm not doing anything, but this thing is happening. And they're like, it's fine. You don't have to do anything. You may not even have to do anything. For 20 years, but we believe in this thing that we've built. So, we're going to like fund it and be the grandparents and the parents of this community until like you guys are the people who do retain and some of you will be us one day, right? But not even really being aware of that, I think is similar to like the startup ecosystem where it's just this living organism that breathes. And once you kind of get into it and you sort of have good intentions and you're like, oh, you're a kind of person who wants to build stuff, we like that. We want people who build stuff. We're going to help you do that. And I've always prioritized that. I mean, I feel like so many people optimize for valuation or optimize for whatever the amount of money they're raising. But for me, it's always been like, who can I be next to on this universal, this ride through reality that we're on? And everything else is secondary to that. And I think when people see that, I think there is such a transactional— any industry town, there's probably a lot of transactional people and people who are just trying to like make money, which I'm sure is part of what I want to do. But yeah, I feel like it's— people can detect that and they're like, they want to help people who are really trying to help other people and they don't want to help people who don't really want to help other people, you know? So yeah. Yeah, I don't know.

So you started the company in 2011. You did a pretty high-quality seed round that would, you know, this dates you a little bit because that's— that was for good seed terms for that time. Things obviously have gone a little crazier since then. Do the seed round and you're kind of like on the high-prestige, like accelerated venture track. Everything seems like it's going amazing. And I can even remember you wrote this— I fast forward, I think it was like 7 years, 2018. You wrote this blog post about how you failed to build a billion-dollar company. And you were kind of going a different route. So like, I kind of want to understand the Gumroad story, like with that first like story arc where you were like on the venture-backed track and then something happened, you know, like you did something differently. And then of course you must be the only person in history to write one of those how I failed to build a billion-dollar company posts and then have to follow up a few years later with how I actually have built a billion-dollar company after all. So we can get to that story arc too. I just, I love the symmetry of that. Yeah, but first, like, tell us how you failed to build a billion-dollar company the first time and then we'll talk about how you actually succeeded.

Yeah. I mean, I think the first thing you got to do is you got to think you can do it, right? And that's the first step to failure is thinking you can succeed. So, somehow part of this, you know, pool that I was in, you know, also got me thinking not just about building products but about building massive things that could change the world. Steve Jobs, like, you know, the term being dent in the universe that everyone would sort of, you know, everyone wanted that. And I think a lot of people have this desire. I don't think it's too unusual. And so, you know, I had raised the money and then basically 5 months later, I met a partner at Kleiner who was like, hey, what would you do with $7 million more? And I talked to one of our existing investors, Josh Kopelman from First Round about it. And he said, look, most companies don't get this chance. You know, you're already at— like most companies, he specifically said there's nothing like numbers to fuck up a good story, which is like you're so early that you don't have the numbers that say that this thing is not going to work. And if you really believe in this, at least for the next 5 years, if you want to work on this for the next 5 years, if you don't, then don't. But if you want to do this, then, you know, raising some more money when things are looking really good for you, you know, the wave is here. So do you want to surf or do you want to wait for the next one, right? And so I raised this round, it was $7 million on $28. So about 25% of the company got 2 term sheets and basically just, I'm kind of in hindsight, I think I just basically was so focused on basically using that capital to build Gumroad and build the product. And I just didn't have any feedback loop with the industry anymore. I just was like, awesome, I got the thing I needed from the I'm going to go build my thing. As long as things go up and to the right, like, things will be great. Things were up and to the right. We grew 80% a year for 3 years, something like that. In hindsight, sort of like the narrator, not good. But I was like, oh, up and to the right, we're building a great product and VCs and all these people were saying good things and were excited. No one was upset and no one was telling me I was doing anything wrong. And then, you know, and then I basically went out to raise money after 3 years. I was like, "Oh, we're ready for Series B." It's 2015, 2014. It's been 2.5, 3 years. We still have 18 months of runway, but, you know, we're starting to get to the next phase of the company. And basically, I remember like the first conversation I had with somebody, he was like, "You're not going to have an easy time raising money. You're going to be able to, but it's going to be tough." And that is the worst you could ever hear from someone who writes checks. They're telling you your hair's on fire sort of thing. And that, yeah, basically that was the point I realized this whole thing works when you're growing really fast, when there's this crazy expectation for growth. There is this level of transactionality to Silicon Valley. It's just so long-term infused that you don't think about it when there's dirt or when there's like, you know, sort of things on the other side of the rainbow. And all of a sudden you realize like you're in The Hunger Games where you may not win and you're like, you're all of a sudden like on the other side of the story, of the Hollywood story. And you're like, oh, I might be like the third place winner, which is, by the way, you die. You know, like, and that, you know, I think that sort of Yeah, that was tough, but it just is what it was, right? I think at the end of the day, I think there is this level of entitlement I think I had to like, oh, I'm part of this narrative and this is like what it is. And as long as I like do the right motions and get the office and hire the team and like all of the things in my control, I was doing, I think, the right way. But what I didn't realize is like even that may not be enough, right? If Patreon is growing much faster and they raise a mag around, you never really know what's really at play. And I think that stuck with me. I think since then, it's always been about, well, how do I always tread water? How do I run the business such that I never need to raise money? Because needing to raise money was why I had to let everyone go. I had to raise the bridge from Kleiner that put the company in a difficult spot. That. It's not great, right, when you're trying to make decisions, like make, you know, someone being like, make it now, now, now. Like, like, generally, you know, try doing that to a friend, right? Being like, where do you want to eat? Tell me, tell me. It doesn't work, right? Like, they, they basically just look at you funny. So it's kind of what happens, you know. And so, but I also think, I don't know, I do think it was a, it was almost like a good, a really good learning experience because you learned that, like, the industry doesn't care that much about you. The industry is also just like this thing that has its own priorities. And when you don't align with the vector, you know, it doesn't shoot you forward. It just like, you just spiral out of control. And at the end of the day, it was your fault for, you know, like getting into it in the first place to some degree.

And so yeah, now I just— Yeah. It's a pretty common mistake to confuse success with venture. Success with fundraising for business success. And to kind of get high on your own supply so much that you, you start to hire people because you have the money, because you know you're going to be a success because you have the valuation. Like, that's a very common treadmill that people get onto. It's a very common trap, especially during the boom times. You know, we go through these cycles. What I think is really unusual about your story is I've obviously been around a lot of people who've gone on that treadmill. I've been on it myself. Generally speaking, you get on the treadmill, you start to overinvest, your burn rate goes too high, you start to run out of money, you can't raise more money. Usually that's the end of the story. Company goes under, you declare bankruptcy and, you know, maybe decide entrepreneurship is not for you or, you know, you go on and start a new company. What's so odd about Gumroad is you're still here. So like, how— just what happened? How did you manage to survive what is for most people a catastrophic fatal mistake?

Yeah, I mean, I think one, I think I was very honest with the team. And so, we prepped, right? I think a lot of companies are really in denial and they're in denial in every way and they die, right? Because if you're in denial that you're going to crash, your plane is going to crash, right? If you know 9 months ahead, like, "Hey guys, this plane is not going to make it. We're not going to get over there, but we can prep for this other condition." most of us aren't going to make it. But luckily this is not life and death for you. You can get another job and try again. But for Gumroad, it's, we're probably not going to get that billion-dollar outcome out of this specific try. And that allowed us to basically make all of these changes in the company, the process, the tech stack, the way we did support, the way we did risk fraud to just optimize the crap out of the business such that I could basically run the business myself for 2 years, basically just doing customer support every Friday. And that allowed me to realize the business continued to grow and was continuing, that it was worth investing in because the users were pulling it and I was just basically fulfilling their needs. But I think most people honestly, I think they don't really, they get so attached to the company, the office, the team size, they can't go to zero. They can't. They just would rather almost perish. And for me, it was like, well, no, I really want to keep working on this. There's something here. And the team was like, yeah. I mean, we— and yeah, I also think we maybe got lucky in the sense that we picked something in which it was possible to run it this way. I think there are a lot of business models that maybe wouldn't have worked, but because we worked on a marketplace business that was helping people sell digital content, like it was we were able to do it in a way that was unieconomic positive as long as we had a really, really small team. I think certain people, I talked to some founders who are like, "I'm in a similar position to you, but have lots of customers that love the product, but we're losing money." And it's like, "Well, first fix that." And they're like, "Well, I can't. We sell it for $800, but it costs $2,000." And it's like, well, How long have you been doing that? Like, you know, like you have, like, there has to be sort of a reality check too of like, hey, we can't, we have to charge more money, you know, if we want to stay alive, right? Or we have to downsize the team if we want to stay alive. And I think a lot of people have sort of just sunk cost fallacy on certain decisions. Like, oh, we can't do that. We need to, like, we have this customer base, they expect this thing from us. Like, there's nothing, we'd rather, you know, die than change our mind on that. And I think that's also kind of important to realize is that like, stay, you know, at least on the front perspective of the company, staying alive is like the most important thing, right? And so at the end of the day, if you're really trying to stay alive, you have to prioritize it and do things that are sort of almost contrary to other values you have. Like you have to be willing to say, hey, like this thing that I thought was really important is just not actually that important or still is, but like You know, we can, we will be in the fullness of time, but first we got to make it there.

Give an example, like making those kind of hard decisions is something that a lot of people shy away from. What was one of the hardest decisions you had to make during that time that you remember where you really felt like for the sake of the survival of the company, you got to do something that maybe at other times you really wouldn't want to have to do?

There's a bunch. I don't know if there's any one major one, but there's so many small ones. There's things like kicking customers off the platform. Platform who are causing too much customer support burden and just saying, "Hey, we need the team to focus on these other things. We're not making any money from you because you're using the platform in this way." Things like telling that using a third party instead of hiring, instead of retaining the team and being like, "Hey, sorry, it's just not that important to do QA right now." I remember moving from Wells Fargo to Stripe when we were exploring marketplace stuff. We were spun up all this effort trying to get onto Wells Fargo. And when I was like, well, we're probably not going to be able to do that. And so let's just go to Stripe for everything. And that means these two roles don't exist anymore. But that's the reality of the situation. And when I started doing risk every day, I was like, this cannot be someone's job because I have other stuff to do and I'm going to go crazy. So we need to automate it and it's okay if we have a little bit more, if it takes 5 minutes instead of 5 hours, right? Like, they're like, I think, I think there's like a sort of a, a search for perfection. When you have money, you're trying to nail everything perfectly. You're trying to do the best job ever and being okay with not doing the best job is also, I think, really hard for people where you're like, oh, all of a sudden, you know, I'm deleting features, right? Like saying, hey, Gumroad used to help people do preorders, but like only like 1% of the GMV was preorders and it cost like tons of support time and it was really buggy and Kickstarter really takes all that volume anyways. Let's just really be honest about what people use Gumroad for and focus on that. And maybe that means we can charge more money in the future. Tons of those sorts of decisions, getting rid of the office, even tweeting, right? Let's say we need to sell a bunch of furniture. If you're not willing to tell the world where you are as a company, you're not going to be able to find buyers for your furniture. There's all of these functional things that I think our bottleneck by just the ego of not willing to admit. And the biggest one, honestly, I would say the biggest decision was leaving San Francisco, was basically being like, "Wow, San Francisco's expensive. I don't need to currently hire any engineers. I currently don't need to raise any money nor can. Provo's cheaper, so I'm going to go move there for a bit, tell my landlord I'm not coming back within 30-day notice." And then, I have to tell my friends that I'm going to be gone and if anyone wants my furniture, they can have it. And that was the most important thing, I think, because it really reframed working on Gumroad and trying to have an impact on a long time horizon for a broad group of people in a way that wasn't making a dent in the universe or some sort of more manic depressive episode or something. And also it just gave me the distance, right, from the culture and like all of the learning of like the way to do things, right? Also, now there was like a lot of unlearning and stuff I had to do. And it's hard to unlearn when you like, you're surrounded by students, right? Like you kind of need to go somewhere else and not be asked like, how's Gumroad doing? How's Gumroad doing? What's up? Are you, you know, like, so I think that was very, very, very helpful.

It's a spiritual lesson that goes back millennia. Yeah. Yeah. I think it reflects a lot of personal growth. Do you feel like you were able to leverage kind of the best of Silicon Valley and to take some of that thing, take your builder instinct and learn to build a company, but you also kind of got to see the dark side of it too? Here you had to forge your own path in a new place. Tell us how it's going now.

Things are going great now. I mean, I think they're— that— I think it's, it's super helpful to spend time in, in industry town and to, you know, to like see how the craziest people who are the most bought into it really act, you know, and real what they do and what they think about, because there's a lot to learn from them. But also, I think if you really want to have an impact on the the world that you said you want, like, to be honest, you have to leave. Like, you have to actually be of the world and like participate in it and be empathetic to what people actually want and their actual views on technology and AI and robotics. It may not be as exciting as yours. You probably have— probably haven't read Isaac Asimov's Foundation 7 times or whatnot, you know. And so I think it really just kind of mellows you out, um, But it also, I think, widens your aperture and allows you to have a larger impact. And frankly, I think it— honestly, I think it makes you realize that Silicon Valley is wrong about a lot of things and just like any large social mass of people is, right? Because at some point you start sort of doing things to perpetuate the thing and there's a lot of cargo cult behavior and you can keep doing what you want to do and you just have to revisit every single decision of like, do we really need to do things the way that we used to, that we did it when we were based in SF. Even now, we're having conversations in Slack about, "Hey, we have this thing that do we need? We may not actually need this anymore." And being able to do that when you're outside of the venture capital raising ecosystem and saying, basically you're just saying, "Is this the right thing to do forever?" I think in VC in San Francisco, it's like, "Is this the right thing to do because we need this thing?" next week. Well, we need this thing next month, or we have this board meeting coming up, or fundraising, or this or that, or we have investors who are coming by the office. I mean, I was hanging out with a friend who has an SF-based startup and it's like his phone's going off with demands and requests for what he has to do to just function in this ecosystem. But for me, I can just build based on what I think is important forever. What's the right feature that deserves to exist for Gumroad for eternity, right? The fact that I was able to go through and delete all these features for Gumroad, it was like, basically was because I was making all of these kind of short-term growth-minded decisions in order to sort of pump GMV as fast as possible. Now, it's like, hey, what should we build so that our numbers go up over the next 30 years? And the decisions you make are very different, right? When you have that long view. And it's very much informed by the fact that most people around me don't care, right? I have to have a long view because no one cares right now. The stuff that we're working on is still very early, it's very nascent, we're still trying to figure a lot of it out. And yeah, I think when you're in SF, you kind of get deluded, you think everyone cares, and then you're surprised you fail because everyone around you was obsessed with what you were building. And it turns out like, no, sorry.

I really want to get to one of my favorite things about the Gumroad story is how you solve some of the financial and structural problems that come with being a really like high— but both a fast-growing but also highly profitable company kind of off the IPO venture unicorn track. I think that also took a lot of courage to do something very different. Talk a little bit about how you've structured the company solve some of the classic problems people say you could only solve by going the venture route?

Yeah. I mean, I think the biggest thing that venture solves is that you get a huge team of awesome people that you wouldn't have been able to get otherwise. And then you get to focus on building stuff. And in theory, if you have equity that could be worth a lot of money someday, then you basically can pay people much less, right? And we couldn't do that because the government's in a kind of different place. And so, but I really felt like there was something to that. There was definitely something to giving people equity and ownership in the business and then framing their decision-making like, how do I increase the equity value of this whole pie? And so, I just was like, okay, I have this workforce of hourly contractors all over the world that I had built up over that sort of 2017 to 2020. 22 period, how do I get some of that value? And honestly, it was very simple. It was like basically everyone gets an hourly rate and they get to choose their equity split. It took a lot of time to get to that solution, but basically that's kind of how it works is we have a valuation of the company. It's currently $100 million. You get $200 an hour. You can choose to get $200 an hour or you can choose to get $40 an hour and then $160 an hour and in equity, right? And that equity is basically options that vest as you bill your invoices. And then at the end of the year, we actually give you the exercise price of those options as a cash bonus. So you're kind of cash neutral if you choose to exercise, or you can just pocket the cash, keep it as an option. But the cool thing with Gumroad is we're profitable, we issue dividends. And so in theory, you're basically— it's like a 401 in a way, right? You're sort of trading cash for equity and you get dividends at this sort of 5 to 6% rate. And if we do amazing, hopefully that's 9% and then 12% and then 15%. And if we can pull that off, Gumroad will be a really great business. We'll have a team of people who are thinking about what can we do over the next long period of time. I want people who are like, work here for 30 years. I don't see why not. I think people somehow separated out long-term employment and like freelancing or like startups or like equity, right? Even like, but it's like not necessarily like NVIDIA is like, it started in the '70s, right? And they're still going. And the reason they're going, by the way, is because they gave people equity. Because eventually like the people who get rich, you know, who have equity get rich and tired and lazy. And so you need a new generation of people who have equity who are excited about like keeping it going and going and going. And everyone needs to be incentivized for that. No one is doing it purely out of their own charitable interest.

And it's a really powerful way to align incentives and to do things over long time horizons. So you actually— I think of it like you're literally borrowing wealth from the future and giving it to people now in order to give them a stake in a motivation to reach that unrealized future, since of course the wealth is not worth anything if that future doesn't come to pass. And there really isn't another thing like it in terms of creating that sense of buy-in and shared ownership.

It's quite powerful. Yeah. I mean, I think it's such a fun— I was— it was funny, I was talking, I was at a meetup and we were talking about how like the word equity and like what is, you know, what is like, what is that word in other languages? And like, I think it is a— there's a reason we have a word for that very specific thing. And we looked it up and Basically, it's like ownership in a thing and it's like fairness. It's like fairness via ownership is something like that. It's not truly fair if you don't actually can't participate in, right? You can say, oh, the country, we live in a not 100% equitable country, but if we did, it would mean people would kind of get what that meant, which is everyone has a stake, everyone gets benefits when things go well. And if everything goes badly, we all suffer in some equal proportion, right? It doesn't necessarily mean equal, otherwise we would just use the exact same word. But yeah, you're right, there's no other way to get it. A lot of people are like, oh, why don't you just do profit sharing, right? It's like, well, what if 50 years from now we sell for a trillion dollars? It's like, but that's not going to happen. But I'm like, yeah, but the what if is inspiring. Imagine, you know, like it's a human desire, it's a human thing, and it's a— it's— it could be real. And, and I, I just think, you know, I love bootstrapping, but I do think like, you know, if you can give equity in your thing to other people and you have a huge number of owners, I think it's phenomenal. I think it's— I don't know, I think for sure it's a huge force multiplier. And I don't think it's a coincidence that the most valuable companies in the world are publicly owned. Right? And we can all own US dollars. We can all— America allows people to come in and buy our land. You can't do that in Singapore, by the way, right? Very cool place, but it's too small. There's not enough land and they don't let you buy it, right? So, it's never going to get that level of equity, quote unquote. And I think stock is like land for a company. It's this sort of fundamental ownership unit that can't really— it can only be diluted, cannot be created without this dilution. And it's like the fundamental, the cells of the organism.

What was it like having that negotiation with your VCs when you told them you wanted to go on a different path?

Honestly, It has always been easier. It's like so much of the pressure comes from you and it comes from like, it's kind of like a piano recital or something, but it's like the audience is just happy to be there. All the pressure comes from you and almost like the test wasn't picking the right person who would be self-intrinsically motivated to be obsessed more than the audience would be. Yeah, I mean, I don't really know where I was going with that thought, but I really just put together like, hey, this is why I think this is a good idea. I read a book, The Intelligent Investor. In it, it mentions that when interest rates were 10%, people would do a 60% net income dividend. This was kind of the way that economy ran, you know, for a long time. I read about, I didn't, No, I didn't live at that time. All I knew was ZERP, but it seems like a historical book. And basically, it seems like also like all these profitable— walking around New York, there's lots of profitable businesses. They don't raise money. They're coffee shops, they're construction development firms, they're gas stations, restaurants, right? All these businesses exist. They all just seem to do dividends. And so, can I just do that? And they're like, sure. And basically, I think a lot of, you know, it's like, as long as you put in the work and formulate an opinion letter basically of why I think the business should do this and say, by the way, if you disagree, let me know. I'm happy to do a buyback or pay myself more money if that's really the only option or I'm open to ideas. Certainly, but everyone was like, hey, yeah, it's kind of weird. It's not normal. Someone told me it's the first dividend they've received since 2020, since 2003. And I'm like, okay. But at the end of the day, I'm doing all the work. I have to implement the dividends. They were just saying yes. But yeah, I think a lot of founders, honestly, they kind of get caught up in the negative what-ifs. They're like, what if they all hate me? I'm sorry to say they're not thinking about you. Like, they're on a beach or they're fighting with their parents or like, who knows what they're dealing with. But my guess is you're not near the top of the list. And so, if you can just do the work for them, really come up with like why, you know, the business should do this and make it really easy for them to say yes, they probably will. I think, you know, I think they support you. They back you. And I don't know, as an investor in companies, I want my founders to be high agency. I want them to experiment and do weird things. And when we raised the crowdfunding round in 2021, one of our lead investors in that round, Naval, was like, just don't do anything normal. Don't feel like you have to get back on the same path because you'll literally just die because all of a sudden, maybe not die, but the thing that is the reason anyone is paying attention to you would basically go away. So, Even though I'm in an office in New York, it's still important to lean into the stuff that got you here and the stuff that basically the personality that got you here, most people's personalities would have led to not here.

They would have sold the business. Don't forget that being weird is how you got here.

And so, just sure, maybe being weird is the thing that gets you killed too, right? It gets you.

Yeah, there's the good weird and there's the bad weird.

As it's kind of becoming, you want to be, you know, you can't hate on social media right now. Yeah, yeah, you want to, you know, check yourself before you wreck yourself. But generally, like, yeah, don't let the sort of success get to your head now. And like, I think it's important to— I honestly, like, I think like that, like, I think of like almost like a near-death experience where you're like, oh, now I can live the life I wanted to live. Because like, you know, in one parallel universe, Gumroad died and now I'm in this one. And so, I should honor that. Yeah. You're—

bonus time, the extra time you got from not dying.

Yeah. A lot of great companies have that near-death experience in there.

It's interesting, an interesting commonality.

Yeah. Apple, I think, you know, it's like, I think it unlocks this like, let's really— and honestly, sometimes it's not the best thing for you, it's not the best thing for the team, it's not the best thing for the company, but It's the best thing for the world to have people like that who are experimenting and trying stuff out and then reporting back, right? And being like, hey, yeah, here's, here's, here's, here's what happened.

Well, you guys have not only pioneered this approach yourself, but you started to help other companies adopt this model. You could help someone complete a transaction like relatively recently, right?

Yes, we helped Elemental. They raised a, they raised a crowdfunding round and around the same time we did 2021, 2022. From about 2,500 people and they wanted to do a dividend back to them similarly. And we were super excited because going from 1 to 2 is a magical moment. It's like, okay, we're not the only crazy people here. So we help them—

How do you do a dividend to 2,500 people just logistically?

Logistically, you basically get all of their information in a big Google Doc and then you import it into your database and you trigger an email to 2,500 people. And it honestly made me realize, like, wow, like, if doing this 30 years ago, which is how people used to do dividends, like, you would literally have to write that many checks. Humans would do it, mail them out, lick some envelopes, and you would do this once a quarter or whatnot. And the first time it felt that painful, but for us, but then the second time for us, and then the first time for Elemental, like, it was much easier because all of a sudden it's the software is doing it. So the software sends out the mail and then people type in their information and then we send out the, they type in, they connect their bank account. That's now really easy to do. And we send them a wire and we were able to do the whole thing for $5,000. So 2,500 people, average wire fee of $2. This is, by the way, a worldwide, like anywhere in the world, we were able to do. And it was— it— we'll see what happens, but the fact that we were able to pull it off and for such a cheap price, and I'm like optimistic for what this could mean for making it more accessible to other people. Because a lot of people, they're like, oh, it's going to cost like $30 a person to do a dividend, and then you're issuing a $10 dividend to every person, so what's the point? But if you can get the costs super, super, super low in terms of manual labor and then actual payment wiring transfer fees, I think it could just like Gumroad. I'm getting back into— I also admit that I've not fully escaped the desire to build a billion-dollar company, which is I think there's something here. And if you can make it super easy and super cheap and help people understand this way of of working and making money and, you know, build the software that allows people to do it, maybe there'll be a large opportunity and many, many, many people will benefit. But only one way to find out. So that's Flexile. So that's our— yeah, that's the second product we started working on after Gumroad, flexile.com.

We'll put a link in the show notes. Can we just do a lightning round?

Yeah, let's do it. Okay.

I just like— I, I— one of my— this is one of my favorite parts of each of these interviews because I get to— I get to do all this research. I don't get to read other interviews you've done and things you've written and think back on some of our conversations. And then I just want you to go say a few things I've heard you say, and then just you react and tell me what you think, or, you know, why'd you say it, or say anything you want to say. You were telling me about these new AI tools. You feel like for the first time Gumroad has achieved a velocity where, like, you could be— even though you're a larger organization now, you be comparable, like, to a YC startup. How you— how have you accomplished that?

Yeah, I mean, I think, you know, as you grow, you hire more and more specialists, and that allows you to, like, do things you weren't able to do before at scale, you weren't able to do before, and build things any one person wouldn't be able to build. But eventually what that means is you have so much overhead in shipping stuff, which is why big companies ship so much slower than smaller companies. Smaller companies can't do as much as big companies, but they can move faster. But what AI is doing, it's basically creating this almost like verticalization in every single person's head where all of a sudden the designer is now able to write more code and all of a sudden the engineer is able to do more design because they don't have to learn every single little nitty-gritty thing about how Figma works. They can sort of use this like wrapping around it to get most of the way there. And I think all of a sudden it feels like the company is a tiny early stage startup where you only have generalists again. And when you only have generalists, it means the designers can, instead of saying, hey, we're going to discuss this in Slack, then we're going to flesh this out in Notion, we're going to design it in Figma, then we're going to put in the design system, and then we're going to have an engineer, and then we're going to have a conversation, then we're going to build it, and there's going to be a back and forth, the designer and the engineer, and then the marketing person gets in the loop, and then it goes to production. And that feature may have been, the engineer might have spent 1 hour on it,, but then the entire thing took 20 hours or like 2 weeks, 20 hours over 2 weeks. But when you have this massive verticalization, the designer can just go into GitHub and say, hey, build this feature, add this undo button. Today, for example, we have like little toast thing that comes up and it says undo and we want to add a visit next to it so you can actually visit it instead of undo it. And this would've been this 20-hour, 2-week process and instead I opened up Cursor. I said, I know which files need to be edited. There are 3 different files and do this. I just copied the thing from Slack, our conversation in Slack that we were already having and said, hey, basically we want to add a visit link next to the undo link that basically visits the conversation instead of undoes the send or whatever and just hit enter, watched it do some magic and then committed the code and put it in the Slack and said, hey, if any engineer wants to take a look, it looks— I think I did this. And all they got to do is test it, do QA, and then merge. If it's not done, maybe they have to do a little bit more work. But all of a sudden, instead of the 20 hours of which 1 hour was the engineer, it's now 1 hour of which 30 minutes was me and the designer and then 30 minutes is the engineer. So, all of a sudden, that 19 hours of back and forth I think is gone. So, that's a 20x speed improvement in terms of shipping stuff. And, at the end of the day, as I get a little bit older and I'm not as spry and I'm constantly scared honestly of what happens when two 18-year-old kids or NYC just outship me. And just build like a 30 times better Gumroad? What do I do? And now I'm like, oh, this is what I do. I take the 20, 30 people we have and I turn them into YC founders. I give them the skills using AI to allow them to ship, even though they're only working 10 hours a week, 60 hours of work. And if they can do 60 hours, then they're on par with someone who's working 60 hours. And if I need 60 hours, then I hire 6 people who work 10 hours a week. And all of a sudden, I would love to believe that this basically unlock— the hardest thing about remote work and async and all these things is like you lose when speed matters. When speed really matters, you still lose to the in-person whatever. But if all of a sudden you're able to get— what if it's actually better? What if I go to bed and then someone picks up the stack, uses AI and gets it all the way because they're able to use AI to do what I was trying to do, but with their skillset? And then they go to bed and somebody else wakes up. And all of a sudden, I think sort of this part-time async bootstrap, all these companies that are more novel and more weird, I think will have a lot more power, I think, in this war against these in-person SFYC mega VC-funded startups. I actually think that the VC-funded companies have basically raised all this venture capital to take their most prized resource and give it away to everybody, which is like AI engineers on demand, right? And that I think is a huge gift that people should not underrate.

A shocking percentage of the AI research labs and the biggest AI companies are managed very conventionally behind the scenes and they don't actually use AI in their own day-to-day work. That really surprised me.

That's crazy to hear. Honestly, that's crazy.

Is that crazy? Yeah, it's really wild. They're using headcount for things that you would think they would be using AI for. But make of that what you will. Okay, you said, "If you want to be an artist, be a capitalist first." I think so many people, they love the starving artist.

They love the idea of like the way to do art is to like, it sucks, it's not fun. And it's like, no, the way to make art is to like find a way to make art, which is to like have something that pays the bills, that doesn't take all of your time, and then you can make art. And so capitalist first, artist second, much easier than, you know, going the other way around, I think. All right.

I got to read this one because it's a little bit long. And I think this shows your real optimism, although people may not see it that way at first. You said, being a founder is hard. Being an early employee is hard. Being a VC is hard. Being a politician is hard. Being an engineer is hard. Being a writer is hard. Being a friend is hard. Being a partner is hard. Being a parent is hard. It's all hard. Life is hard and then you die. Things being hard has been a recurring theme of these conversations and having the courage to do hard things. I just thought this really spoke to me. Like, it sounds like people think that means that you must be a really grim and depressed person, but you're actually very optimistic. You do a lot. You're really a builder. So how can you— how do you reconcile this, like, idea that everything is so hard and then you die with all the things that you do that are really regenerative?

Yeah, I mean, I think it's— I don't know, I think, you know, life is a paradox. And I think some of the most amazing things, like, for example, you have like the most amazing relationship with someone, it's also going to hurt the most when that relationship ends, right? For one of you, at least. And so I just try to be really mindful, I think, of like, things that are good also mean that things are bad, and you can't have one without the other. There's actually a Mormon line that says like, men must have misery to have joy. And I think it's just, I think some people like love to just think that they're like everything is dandy, but to me that's just like not true and doesn't really even lead to the good feelings that I want. What leads to what I think is good is like get being given a hard hand doing well, right? Like personally, I think I would much rather be the most improved than the most valuable. Like I think it feels better for me to be the most improved than the most valuable. I don't need to be number one. I don't— maybe I do, but I don't think I do. But if I sort of get the, as my therapist said, the notoriety associated with doing something important for some people, you get a lot of value out of that. And I think it doesn't absolve the difficulties and the hardship that life has. But I think a lot of people, yeah, they just kind of— they think this can sort of solve all their problems if they build a billion-dollar company. And it's like, look, you can do all the things. I can do all the things I want to do and still yet there will be moments where I have to deal with grief and trauma and that will never really get resolved. And I think also people, I don't know, it gives me empathy for generally when people are angry or doing something I don't like, it's because life is hard. It's not because they're evil or they're really just out to get me. It's because life is hard. That means we live on a very small island and there's 5 million of us. And so, that's why we are fighting, not because we're evil enemies. And, that's true for founders, it's true for politicians. And, I think so many people, they just, I don't know, it's easy to think that like— and honestly, sometimes it's cynical because I think when you say that, it's like, "Oh, no, otherwise, I should be more successful. It's their fault." And, it's like, I'm sorry to say, it's actually life is fair and you're in this position that like we're all in this tough spot, you know. Obviously, like we're also in a good spot. I like to think of it like we're, you know, life is a roller coaster and people like roller coasters generally. So, it's not all bad, it's all good, but you know, it is like the thing that makes a roller coaster fun is like the fear, you know. Alright.

You don't learn then start, you start then learn. Yeah.

I don't know where this came from, but I really like it and I think it's I think I just may have been— I was probably annoyed or something. And someone was like, just really like learning, you know? And there's just these people who just are so good at learning. And I was just like, you don't learn, then start. You start, you start, then you learn. You know, it's kind of like something you would tell a 1-year-old or something like that. But it's like one of those things that like would be useful to hear at all ages. And it's a— the cool thing is it never goes away. Right? Because you can, you can always start. You can always start something new, right? Like, if you're LeBron James, you can start playing tennis. And it's just a reminder that the right way to do that is to start. It's not to like read a book on how to play tennis. It's like pick up a racket and hit a ball. And, uh, and also to realize, I think it's a good reminder that like, if you don't want to start, that like, why would you bother learning, right? Like, what's the— the whole point of learning is to start anyway. So if you can just start, like, What are you waiting for? And maybe you should just admit you don't want to start, and that's the best gift in the world because you can go do something else with your life and your time.

This has got to be your most controversial one. You said that full-time employment is modern-day slavery.

Yeah, this one I was testing out a marketing slogan for Flexile, which I don't know if we're going to go with that one. It's a bit edgy, probably a bit too edgy, but You know, it's obviously not slavery, but modern day, right? Which is not slavery. It's the— but what is the modern— you know, it basically is the question of like people ask, what do we do today that 50 years from now we're going to look back on and it's going to look so bad? Like we ate meat, like what? Or we drove cars or like we rode horses.

Yeah, we let human beings drive cars. It seems hilarious, I think.

Yeah, it's just like, wait, like Like 30,000 people a year die in these things and they're like weighed 10,000 pounds and like you're basically like transferring a burrito using a 30,000— well, like what? And so, I was just like, I just think about that and it's hard. It's hard to come up with good ones, I think good answers to that question that are not obvious. And I think one of the non-obvious ones is just like the concept of full-time employment generally. Even the word, if you think about it, like full-time, it's just kind of dystopian, right? 100% of my time employed. Obviously, that's not what it means. It just means, you know, you qualify for benefits or whatnot. But I think the idea of like, we will look back and sort of think, oh wow, this was kind of just like at some point, like certain things that we now look back heinously on, like many people were like, wrote books, like would write PhD theses on like why this was actually fine. You know, like, it was like you would go to school always in every era.

Yeah, it's amazing.

So yeah, just, I think, you know, I don't think full-time employment will go away, but I do think it's— it is a— it feels like very close to this thing that we, we, we really don't like, but then we don't admit that it's kind of close to the thing that we don't like.

Well, Sahil, thank you for, um, coming on the show and sharing the raw, honest experience of the high highs and the low lows. I just think it's really important for people to hear. I really appreciate it.

Thanks. Thanks. And thanks for all you do. And I'm excited to keep working on this stuff together.

I'm looking forward to it.

You've been listening to The Eric Ries Show. The Eric Ries Show is produced by Jordan Bornstein and Kiki Garthwaite. Research by Tom White. By White and Melanie Rehack. Visual design by Reform Collective. Title theme by DB Music.

I'm your host, Eric Ries. Thanks for listening and watching.

See you next time.