27. Sahil Lavingia: The Minimalist Entrepreneur (A New Way To Build A Sustainable & Profitable Business)
01:18:33 Share

Hey everyone, it's Alex from Alex and Books, and you're listening to The Reader's Journey, the podcast that takes you on a journey to meet amazing authors, discover brilliant books, and learn valuable lessons along the way. Now, let's get started. Hello everyone, and welcome back to another episode of The Reader's Journey podcast. Today we have Sahil Lavingia, author of The Minimalist Entrepreneur. Sahil, thank you so much for coming on the show today. You're welcome. Thanks so much, Alex, for having me.

So I think a good place to start would be the title of your book. A lot of people know what it means to be a minimalist. A lot of people know what it means to be an entrepreneur. But what exactly is a minimalist entrepreneur?

Yeah. I mean, I think it's, it's kind of taking the two ideas and trying to combine them. And just so, just to recap what those, you know, what those ideas are like minimalist, right. Generally means like back to basics, the, you know, the bare minimum, the essentials and kind of nothing else. Right. Um, just kind of the simplify, simplify, simplify with the last two simplifies crossed out. That's kind of like the mental image I have in my head when I think minimalism, what do you really need? Right. Um,

And an entrepreneur, obviously, is someone who starts and runs a business that they own. And I think those two ideas are both really important to me specifically, and I'll kind of tackle them in reverse order.

entrepreneur, I think is essential because ultimately in this world that we live in today, I think it's sort of the most guaranteed and that doesn't mean fast or certain, but it's the, I think the most guaranteed way to, to get to sort of financial freedom, financial independence, um, this sort of the sovereign individual, like all, all these sorts of ideas. I think that that sort of the, the, the clearest path that I see, um, is, is entrepreneurship, right? Um,

And to make entrepreneurship as accessible to as many people as possible, I think the idea of minimalism is really important because what I find is that when I talk to people about building businesses or running a startup or raising money or hiring people or doing payroll or like all of these kind of business quote unquote concepts, like the vast majority of people don't ask for minimalism.

empathize with any of those things. They don't, they don't associate themselves. They don't identify with any of these things. They think of an entrepreneur as like someone, you know, wearing a suit with a briefcase, right? That's what I thought entrepreneur was. Um,

like almost like its own career path like oh i'm going to become an entrepreneur right um just like you might become a writer right uh but now the beauty of the internet is that you can kind of do all of these things you can kind of do build a portfolio career where you have all of these different experiments that you're trying out um and i even think just the idea of like full-time quote-unquote employment is a kind of strange like what does that what does full-time mean right like it's obviously not 24 7 it's like there's it's like what you know it's so i think i i i

I just like the idea of minimalizing what it means to be an entrepreneur and trying to make it as accessible as possible for anyone to consider themselves as such. Cause I think that's really kind of an important step to getting to a world in which everyone feels empowered to be able to start a business, run a business, earn equity, you know, build capital, have compounding wealth, all of these sorts of things that I think are really important, uh,

To do all the other stuff that's also important in life, right? To spend time with your family, to get healthy. Like all of that stuff becomes a lot easier in a world in which you have a business that you're running. You get to choose who you work with, how much you work, where you work.

And hopefully you build up some sort of like, you know, some super linear returns that you can kind of invest in things to save yourself time so you can spend more time doing what you really want to do. Right. And so anyway, that was kind of a long winded answer. But that's kind of like the reason behind the title. And it kind of alludes a little bit to kind of the four hour work week mentality in terms of like,

What do you actually need to do? Let's just be clear about that. I think of this as an extension almost of that post-COVID, post-remote work. A lot of these things have really been proven to be true. No code, creator economy. How does all of these new ideas that have happened in the last, Stripe,

That sort of building business today is very different. It's actually a lot easier today than it was 10 years ago. And 10 years from now, by the way, it's going to be even easier. Right. And so, yeah, just trying to get all those ideas across in three words. And that was the best the best that we came up with. So.

Yeah. And I think of this book very similar to your company, Gumroad, where Gumroad is really ahead of the curve, you know, going fully remote, working like part time, very open, building public. And this book kind of gives that framework of like business and no longer work 40 hours a week in office. It's build something small, you know, find the community, you know, become profitable early on and scale from there. And it's very interesting just to see like this new form of business that's emerging. I think you're really like ahead of the curve here with your book.

Yeah, I mean, it's funny because, you know, I agreed to do the book with Penguin in 2019. They had read Reflecting on My Failure to Build a Billion Dollar Company, an essay that I wrote on Medium and about kind of detailing the history of Gumroad. And initially in 2019, the book was like, you know, basically like,

what happened to Gumroad and what are my takeaways from that. And that's not too different from what happened, what the book ended up being in a broad, abstract sense. But then that was pre-COVID. And one of the really interesting things that happened in March of last year was everybody was like, what do we do? What happened to the offices? Basically, everyone was having a quarter life or midlife crisis. And

And I literally gumroad, we didn't do anything different. We were already remote. We were already kind of in this async culture. Literally, like we had our COVID kind of midlife crisis in 2015 when we failed to raise the series B of venture capital. And we made all these decisions then. And that really kind of like was evidence to me that this book should exist. And I was kind of glad that I was in the process.

in the process of writing it, even though like I had to kind of rewrite a lot of the book because COVID kind of changed things. So, so significantly. But yeah, it was like, we, and that's a lot of what this book is about. It's like, we, we, you know, we, or I, or what have you, like, we kind of did these things, you know, based on first principles for what made sense for us as a company. And now it feels like the world is, is kind of catching up or, or, or what have you. And, and like, boom, like I have a book like that, that, you know, hopefully addresses, um,

some of these, some of these ideas, like how do you move to remote work? Like, why is that? Why is that so important? How do you, how do you talk to employees? How do you hire? Like, how do you do, how do you do some of those sorts of things? Um, and, and yeah, you're right. Like it's starting, starting small, I think is essential, right? Like, I think, I think one of the big problems that I find is that people, people have like a very high bar for like what step one is, right? They're like, Oh, step one of being a writer is writing a book. And it's like, well, that's tough. Uh,

like maybe start with a blog post, right? Or like step one is like raising a, you know, a million dollar, you know, seed round or getting into Y Combinator or, and it's like, no, no, no. Like step one is like, you know,

buying a domain and like having a website, you know, like that's, and like the more that you can, again, minimalize like what it takes to start this journey as an entrepreneur, the more people will hopefully actually make that step. Right. Because most people will not, you know, quit their jobs, move to San Francisco, raise venture capital, you know, maybe somewhere in there and go to Stanford. Right. Like the, the, the path, the common path, like 10, 15 years ago, it's just not going to be followed by the vast majority of people. Right.

Right. And so what does that path look like without gatekeepers, without VC, without a degree, without an office in San Francisco? Like what, what is that path? And, and, and that, yeah, I'm just super, super excited about it. And yeah, it's kind of funny because Gumroad, like it is very, when I explain Gumroad to people, it kind of, they're like, that's it, you know, like 11 or 12 million and, you know, annualized revenue. And we have zero full-time employees where, you know, 48 plus part-time people, no office, no,

Really, Gumroad is just like a website. GitHub hosts the code. We use Slack and Notion for our discussions and maybe a couple other internal tools for deploy pipeline stuff or what have you. We have Stripe to process payments. We use PayPal for some stuff.

And we pay taxes, you know, every year. And like, that's the business, like that's Gumroad in a box, you know? And, you know, it could be a hundred million dollars a year and be roughly that, right? Like a few more instances on Amazon, right? Like, like it wouldn't, it wouldn't fundamentally change. And that's like the power of software is that it's, it scales beyond your time, which is kind of a key concept here, right? It's like, how do you move past,

charging for your time, right? That's like the first one of the first steps is kind of scaling yourself. So yeah, yeah.

Yeah. So you just covered, you know, a ton of topics right there. I think one beautiful thing you mentioned is that you could start small when you're starting a business like Gumroad. I believe you started it because you need to sell like a pencil icon. And that's what led to this incredible business. And it's like you only had to do this tiny thing. But, you know, that's the truth about every giant business. It's like it all starts small. And wasn't that true for Gumroad as well?

A hundred percent. Yeah. Gumroad initially was, it was a Friday night. I designed this icon, this pencil in Photoshop and I was like, it took me four hours and I was like, I should sell this for a dollar, you know, four hours per dollar. I mean like that's worth that for me. And I had an audience on Twitter on, on dribble, like, and there was no way for me to do it. And it was in the book, I called them like toast up moments where I like wanted to do something. And I was like, ow, I can't like kind of shock. Yeah.

Um, and then, yeah, luckily I had a community. I, I, I had kind of trained myself through these other kinds of small experiments to be like, I can, I cannot just like be like, oh, that's annoying. I'll just move on with my life and never sell that pencil icon, which is a kind of, but I'm sure many people have encountered this problem before and decided to do. It was like, oh, I have a weekend. I have nothing to do.

I can build a little mini app. And that source code is open, by the way. So anyone can Google Gumroad V1 and find that weekend. The commit history literally from that weekend is still there. And it's ugly. It's terrible code. It's one Python file, literally one file.

um, for basically the entire application, tons of copy, paste, you know, not optimized, like, but, but most important, it worked, it worked right. Um, it did the job. Uh, and, and yeah, I, I think starting small pick, you know, thinking of these things like side projects instead of companies or toys instead of apps, like as the, the lower, the tinier you can make that the better. And, and James clear, you know, atomic habits is, is a great book. And that has a similar idea, right. Which is,

atomic habits. Habits are made of these tiny atoms of behavior change, of identity change. In that way, this is very similar, which is if you want to be an entrepreneur, if you want to start a business, you just figure out how can you take this one step, break it up into two steps? How can you take those two steps, break it up into four steps? How can you take those four steps, break it up into eight steps? Then once you have 10,000 steps, what's the first step? What is that? My guess is you can do it.

If you know you want to start a business, you know what the name is, go buy the domain. Go create the Twitter account. Go create an Instagram. Just start moving. In physics, rolling friction, I believe it's called, is much less powerful than sliding friction or whatever. I don't know exactly the terms anymore, but when something's at rest, it's much more hard. It takes more energy to move.

Right. But once something is moving, even just a little bit, it's a very different, you know, the rolling coefficient or whatever, like it's very different. The sliding coefficient, like it's, it's way cheaper, way faster. Right. And so it's kind of similar if you can start moving just a little bit, like, you know, the next step is going to be a lot, a lot easier. Right.

Yeah, totally. So yeah, I see your book as kind of like a framework or like a guidebook to like starting a minimalist business. And yeah, one important part you just mentioned is like starting as small as possible. And another great tip you have is to actually be a creator first before you be entrepreneur. So why do you recommend that path?

Yeah. Yeah. Creator first, entrepreneur second is definitely kind of a theme. And it came out of just what I observed at Gumroad, which was I saw literally thousands of people

That I would identify as entrepreneurs, as business owners who never would have considered themselves such. They're like, oh, I'm not an entrepreneur. I make a couple hundred thousand dollars a year selling e-books. That's not, I'm not an entrepreneur. And I'm like, what? I do make more than some people that do call themselves. It was just kind of funny. And what I noticed was to be a creator, you have to learn a lot of skills. It's a sort of a multifaceted process.

sort of skill set. You have to learn how to write, communicate, market, maybe design, you know, edit video or audio. Like there's all of these things you have to learn. And literally, basically everything you need to be an entrepreneur, you kind of have to learn to just be a creator. But for some reason, creator, you know, like, just like I mentioned before, like people don't really identify with the word entrepreneur.

They really identify with the word creator, right? You look at all the surveys of like, Oh, 70% of kids want to be YouTubers or what have you. Right. We'll see if that actually happens, but, but, but, you know, they're clearly being pulled to that for a variety of reasons. Right. So if I can use that as almost like the Trojan horse, right. Of like, Hey, become a creator, learn all these skills and then apply them, make money, do all that, build an audience, et cetera, you know,

you will be far more prepared to be an entrepreneur. And actually, like you may have already become one without you realizing it. And I think that's sort of really, really important. Like it's kind of like the difference between like writer and author, right? Like everyone's a writer. Not everyone considers themselves an author, right? An author is some, you know, you have to have a published book or whatever, whatever like that feels to be. And so

And so I just like, you know, creator to me, creator is just entrepreneur, right? It's just the same kind of word even. Maybe it's just shorter. You know, we were tired of saying entrepreneur, spelling it out or something. But it's really kind of the same. And I see it, you know, they're really, they're both CEOs. They both run a brand and built, you

built that brand from scratch, have an audience or selling some product to them. So like a lot of the, a lot of, a lot of it is the same. Um, but yeah, I find, I find it to be like incredibly compelling to people when I say, Hey, you know, you should be a creator. And everyone's like, yeah, I want to be a creator, you know? I'm like, okay, cool. Like if that's what you want to do, like, great. Like let's start there, you know? Uh, and then once you're, once you feel like, you know, you, you have a solid base that we can move on to step two. Right. Um,

That's why I came up with that, create first, entrepreneur second.

Yeah, that's such a great way of putting it. One is kind of like a rebranding, like kind of entrepreneur is kind of like, you know, it's been overused or like too many people say or still has that business, that old school business context. But if you say creator, it's like futuristic. It's like, you know, you create for a living. And like you said, it's kind of like a Trojan horse. It's like something in disguise and also just sounds a lot more fun to be a creator than to be like entrepreneur in a sense. So that's really great way of putting it.

Thank you. Yeah. And words matter, you know, like what I've noticed is like a lot of people want, like one of the hardest things to do is to get, to get everyone to agree on something, right? Like that's one of the hard things to do about any movement, right?

You know, you have to kind of rally the troops somehow and get millions of people to decide this is the path forward. That's really, really, really hard. And you see this with like, you know, crypto, I think, had a hard time until NFTs and Web3. And now everyone's kind of like, oh, this is the term that everyone's kind of agreed upon. Right. And it feels like it matters because it aligns everyone on kind of a common path.

sort of mission that everyone is kind of getting, it's more clear, right? It's, it's like, Oh yeah, cool. If I want to be part of the web three movement, like here's a framework in order for me to do that. Um, and, and creator, I think does a very similar way, which we've kind of taken all of these ideas around social media, around user generated content, uh, you know, and, and, and, and,

and said, okay, what do we call this set of activities? So, you know, Gumroad was the third company that I know to ever use the word creator to talk about our users. It was, and I can tell you kind of the history because I was there trying to figure out, like, what do we call our users? We literally didn't know because they were writers, they were authors, they were comedians, they were filmmakers, they were photographers. There was no word really to describe them. And what I found was,

or what we found was YouTube called them creators. They were the first company, I believe. And Kickstarter was the other company that we found that was

call their users creators. And it kind of makes sense, like, you know, in those two contexts. And we were the third, we were the first and the first sort of, you know, where our primary function was just to help creators digital content, which now has kind of become more popular, which is great. But yeah, it was literally because like, on our homepage, it used to show like, you know, we are for writers, comma, filmmakers, comma, all of these things. And it was kind of a cool design or whatever. But

Now there's a word and you can just say creator and everyone knows what that means roughly, right? Which is you create content for an audience on a variety of social media platforms and

And then you might monetize via either a SaaS product or digital content or premium membership or community or one of these, or advertising sponsors, et cetera. And so that, yeah, it's great because it's like, cool, creator, got it, move on. Whereas, yeah, 10 years ago, it was not the case. I said, when we started using creators, people would ask us all the time, what is that? What's the difference between a creator and a creative company?

or a creator and an artist, you know, like what, like, and, and now no one asks that anymore. Yeah.

Which is nice.

Yeah. Yeah. I mean, I think, you know, first off, I think building business is just hard and it's lonely. Right. And it's it's it's always going to be some degree of lonely. Right. Because there are certain things that only you as the founder, CEO of the company are going to be able to do. And that's that's great. That's kind of the job you're signing up for. But it is it is tough. And I think I think having a community, ideally multiple communities that you are a part of.

in a way that you really are vulnerable and you're sharing like a slice of yourself, like I think will just make that journey easier for you. Right. It's kind of like, you know, if you want to go fast, go alone. If you want to go far, go together sort of thing. Right. Like only kind of do do things together as a group and succeed together and fail together, et cetera. Right. I think that's important. I think so. That's kind of like this sort of more.

like high level reason, right? It's just like, it gets, you know, it's social, it gives you some peer pressure, some collaborative competition, et cetera, right? It's really helpful in those sorts of ways. But even in the, you know, in the business context, purely strategically, it makes a lot of sense, I think, because the hardest thing about, you know, I think once you've built the product and you have something you want to sell, like a lot of what people run into is like, who do I sell to?

Right. How do I you know, where do I find my customers? And it's like, well, should have done that before. Like, you should kind of have known that. Like, imagine like I wrote this book and I'm like, OK, who's who should I find? You know, it's like, no, I kind of knew who I was writing to, et cetera. And and yeah, so I think I think starting with community really helps with that, where it really helps you start.

doing a lot of the learning and talking and building those relationships and building real trust, not fake trust. Oh, I'm going to sell a business to these people. So I need to like meet all of them, you know, not like that kind of trust, but really building real relationships. And this is not a fast process, right? Like you, you might read chapter one and be like, start with community. Cool. Like see you in two years. Right? Like that's again, this is like not the, not a get rich quick sort of book. It's a, it's kind of a get rich process.

slow and methodically book. I remember when I was writing the chapter about sales sell to 100 customers, it was the hardest thing to get anyone to

want to get interviewed for like no one wanted to talk about sales and i think it was because like people just have this very negative idea of what sales is which is the kind of the used car salesman right uh and the reason we don't like that is because there's kind of a lot of information asymmetry you've never met this person before they're going to sell you a car and they never see you again you're not going to buy a car another car for a while so like they don't have like the right incentives and it just creates this like

less than ideal relationship right you don't really trust the car salesman you're you're actually told to kind of verify everything that they say right uh and that's just what what it is um but i think if you start with community then it's unlikely that you're going to do that right you're not gonna if you have a relationship you've been in the part of this group of people for a long time you're friends with them you're probably not going to sell them a crappy product right you're actually going to be too scared what i find is you're going to be too afraid of

Of trying to involve this community in your business because you don't feel like you've done a good enough job yet. And that's actually becomes, which by the way is a far better problem to have, right? It can help you work through that. But saying, hey, I built this product. I don't know who my first customer is going to be. Like that is a very difficult thing.

spot to be in, right? It's not easy to go from zero to one, but if you have hundreds, if not thousands of people who know who you are, who've already, by the way,

received value from you. Right. And so sometimes like they'll even have asked you like, Hey, can I, like, do you have money? Like, do you need, like, do you have a book? Like, like, how do I support you? What, you know, like, I mean, I get DMS like this all the time. That's like, Hey, do you, you know, and like, it's surprising. Like there have been people who like, you know, have read the book and been like, there's no, like, there's no, you're literally just telling me to like contribute value for free and never ask for money.

And then like two or three months later, it's like, Hey dude, like I did the thing that you said. And like, here's a screenshot of someone that just DM you randomly saying, Hey, you have a course that I can buy, you know? And I'm like, this happens because these people are here. They don't join communities just for fun. Like they're, they're there for a reason. You know, all human behavior is problem solving, right? Like they're there for something. There's some job to be done as Clayton Christiansen says, or said, like,

They're there to learn a skill or make more money or meet people or get fit or whatever it is. And if you're helping them do that, then like there's probably a business there. Right. And so, yeah, I think it's a really helpful framework to start with. Start with community. And again, it feels, you know, one thing I try to push back on a little bit is is.

This obsession with follower numbers and social media engagement and going viral, right? And these are great things to do eventually, I think, right? But not where you want to start, right? Because you can't go create a Twitter account and then have an amazing tweet storm and it's going to go viral. That's just not going to happen.

What happens is you, you build relationships one by one, literally in the beginning, you build an audience that way. And then, you know, the kind of social media algorithm will, will do its magic and you will kind of grow in some sort of compounding way. But that's great to go from, you know, a hundred to a million or something like that. Right. But to go from zero to a hundred, no, like I'm sorry, but like Twitter, YouTube, Instagram,

Maybe TikTok, I guess, nowadays people say that's possible. But to me, it's like you're betting on an algorithm liking you, which is a lot of this book is about

Not relying on external parties, not relying on VCs, not replying on office, like not replying on degrees, universities, like not relying on, you know, capital, like any, any, basically, can we just get rid of all the excuses here? Right. Like what excuses do you have? Like, okay, I need a million bucks. Well, like, no, you don't. Let's get rid of that. Right. Let's, let's pick a business that is, you know, can meet you where you are. Right. It's like, oh, I don't have customers. Like, well, okay. Don't worry about customers. Just like build relationships, help people.

And it's like, if you can't help people, then maybe you shouldn't start a business yet. First, help people one by one.

And then what is a business to build a business is kind of just like the productized version of what you were already doing. Right. And not, not all businesses, but certainly a business. And you can always see other things. A lot of people, I think it's really stuck on their first business idea. They're like, no, I can't build that business because it's not my life's work. It's not what I, and it's like, that's fine. It's, it's not like I, you know, this book comes out and it's like, I cannot write another book. Like I'm done. Like, this is it.

Right. No, I can do whatever I want. I mean, you know, it's totally fine. There's nothing holding me to my past self. Right. And so but I think a lot of people get stuck on that. Right. And it's like, no, just literally start a business like that. You know, it doesn't matter what it is because you will learn the skills you need to learn and you will have better business ideas.

Literally, as soon as you start your business, right? Like a lot of people think that they need a better idea to get started. But what I found in practice is you don't need a better idea to get started. What you need to do is you need to get started and you will have better ideas over time because you will be in the environment and sort of the mind state to have ideas, which is you're trying to solve problems that are in front of you. And you're having a harder time than you thought you would because it turns out like the tooling still sucks, right?

The picks aren't sharp enough and you can make better ones. And that's how the vast majority of business ideas come about, I believe, is that people have problems and they want to solve them. And a great way to have problems is to start a business first.

Because starting a business is still quite a painful process, even in the US where people would say it's pretty easy. It's still annoying. There's still parts like get a bank account. It's not fun. I have to go to FedEx later today to ship some forms. I literally still, this is 2020, October 2020, I'm still 21. I'm still notarizing documents, going to a...

Like, I think one thing, you know, when you're when you're in tech or in startups and you're excited about this stuff and you're on Twitter, et cetera, like you think that the whole world is here and you're like, oh, I'm super late. Every problem has been solved. Everyone has a huge audience. Like, what am I here? Like, what's left for me? Right. It's like the gold rush. It's over. It's like, believe me, it's like I still I literally still teach people about Slack.

You know, like, like literally this happened a week ago where I was like, Hey, I'm working with Penguin on this book. Guess what? Penguin random house doesn't use Slack. You know, um, they publish these books, but you know, and this is another thing I learned about the creator economy is like, you talk to a lot of creators at Gumroad. We realized this like, wow, like a lot of these people are not technical at all. They're not, they're, they're filmmakers. They're incredibly skilled at that hard skill.

but if you said, Hey, you know, uh, start a blog, they're like, I don't, what? Like, I don't know how to do that. Like, that's too daunting. And it's like, well, you can just literally Google like how to start a blog. Uh, like just like how you probably learned skip filming, you know, but, but I think that there, there's kind of a lot of imposter syndrome or, or what have you. It's scary. It's uncomfortable. Um, so, so yeah, that's some of my observations. Yeah. Well,

Well, you just covered a lot of great points there. So I just want to like recap a little bit. One is like anything you want to learn is like available on the internet and it's most likely free. So you can just find it if you search for it. Two is like community is probably one of the most important assets you could have. And there's no real way to like hack it. Like I know this, I've been running Alex books for almost five years now. And people always ask, how do you get to like this many thousand followers? And the truth that they don't want to hear is that you have to show up every day. You want to respond to people. You have to answer your DMs.

And although the longer it takes for you to build this community, the stronger it will be and the longer it will be around. I've gone viral lots of times, but it's like that virality expires and it doesn't build a strong relationship with people. Just like in real life, if you meet someone for a day, even if they're a great person, they're not going to be automatically your best friend. So you have to see them every week or every month to build that strong relationship with

I think people undervalue how hard it is to build a community, but also how valuable all that work will pay off in the future. So it's just really great to read in your book that you do want to build a community or at least join a community to like just, you know, there's so many benefits to it, especially if you're starting a business. Yeah, I would say one last thing I would add is that it really highlights how all of life is these kind of incremental atomic processes.

one at a time, one by one sort of steps, right? Like nothing goes from zero to two. Everything kind of goes through that intermediary step and audience building is like that where a lot of people see, oh wow, you have 50,000 followers or 170,000 followers. And like, that's crazy. You must've had all of this growth in like a single day. And it's like, no, literally it's much, it's like every day, you know, a little bit, right? And that number grows. And like, even when I announced the book on Twitter, I said, DM me for the intro and first chapter.

And I probably DM literally at this point, like three or 4,000 people. Right. And I still do like, and it's like funny, but like people, someone asked me, they're like, how do you, like, how do you have the time to do this when you have 200 and whatever, 40,000 followers? Like, there's no way like, and I'm like,

No, no, no, you've reversed. I have 240,000 followers because I do stupid things like this. You seem stupid. They don't seem like they make sense.

But three to four thousand, like imagine if half of those turn into book buys or readers or YouTube subscribers or or followers or whatever, like that's literally doubt. I mean, that's already in the thousands. Right. And and I think communities, it really just reminds me of that. Like if if this book sells like thousands of copies or millions or whatever, like.

it doesn't happen in one swoop. It happens literally every single person on their own decided to do it. Right. And so I just really, you know, it does get easier to kind of say, Oh, I'm not going to do that stuff. I can just tweet and like, well, like, you know, thousands of people will see it and I can move on with my day. But I love community because it just reminds me that like, yes, you can do that. But ultimately a lot of the really important things,

Parts of running a business, scaling, starting again. All of these things are these kind of micro-interactions where you just have them.

Yeah, you're right. There's just no shortcuts. Everyone wants to hear that you have some hack and it's like, "I'm going to learn what the hack was." It's like, "Sorry, you won't." It turns out if there was a hack, there probably are some hacks and those hacks have just been integrated into the way that you just start. Starting a Twitter account might have been a hack 10 years ago, but it's now commoditized or democratized or what have you.

if that, you know, the, the hacks don't really exist because they, you know, the internet is a very efficient market, right? Like things think, you know, there are some secrets, you know, but like, you know, I won't say, I won't deny that completely, but like,

they're, it's unlikely that, you know, there's like your one YouTube video away from, right. Like, uh, or one Twitter scroll away from reading a book. Right. Um, and, and, and yeah, a lot of, a lot of, a lot of, at least my personal philosophy is like figuring out like, what's the most important thing I could be doing and literally everything else doesn't really matter. I can still do it, but I, like, I kind of think of it like I'm either like for writing, for example, writing this book, literally I had two buckets of activities.

writing the book and everything else and it doesn't you know it doesn't matter how good i am at all of the other things the only thing that really matters right now is if i'm writing or not right um and and so i just i like to like i think community a lot of these things just remind me constantly of that which is in business it's like how do how do i just help people and and generally like helping people often is like a manual one-by-one process uh

And over time you can scale it. You can hire people certainly in all of these sorts of things. But it's, it's, you can't get there until you do the hard work of doing this all yourself, you know, for a while. Right. Yeah.

Yeah. So, yeah, as you mentioned, there's no like one giant hack to building community or like really any of any of those like, you know, secrets to like building a strong business. But one like small hack that you do and Gumroad does is like build in public because it kind of works as a marketing tool. It also works to tell people about what you're doing and also helps strengthen like that community. Could you kind of share like kind of the advantages of building in public and why you started first started doing it?

Yeah, honestly, I think I first started in 2008 or 2009 on Twitter. And there's some of my tweets from back in the day where I like committed to building an app in a week, one week app dot com that I'm sure does not exist or if it does probably redirects to a place you don't want to go. So please don't visit it.

But you can Google it and there's some articles or what have you about it. But I was like 17 or 18 or something. And I was like, I just want to build it. And I'd only been doing iPhone app stuff for like a year or so at that point or maybe even less than that. But initially it was just about, it wasn't about like community. It was like, how do I find people who are like myself? This is like iOS development in 2009, 2010. It was super nascent.

you know, the, the, there may be like less than a thousand people who could probably like ever built and shipped an iPhone app to the app store. Like I needed to find my tribe, find like-minded people. And this is by the way, how I met this Pinterest CEO, Ben, you know, like I met like a lot of my network kind of goes all the way back to that. Uh, but, uh,

But yeah, initially it was like finding my tribe. And then the other reason was, or there's three reasons. One, yeah, find my tribe. Two was just, I was going to do it, right? Like I think some people hope, like they might see my Twitter or like what I'm up to. And they're like, wow, he must just love what he does. And he's super productive and he wakes up early and blah, blah, whatever, like mental image that they have of someone who's productive. At least that's kind of the vision that I had of a lot of these kind of other people. Yeah.

when I was a kid. But the truth is, no, what I do, what I do is I say, yes, I can do that. I commit, you know, in public. And then it's like, oh, okay. You know, like I know I'm going to do it. It's like, it's like signing up for a half marathon, right? It's like, okay. Like, I guess, you know, I've never run more than four miles in my life, but have a half marathon in a month and a half. And guess what? Like I guarantee a lot of people, many people, maybe even most,

do it. They do it. And there's a variety of reasons that it works, but it works, right? And this is the same thing just applied to like building software. And then the last sort of reason to do it, the third reason is it gives you a audience and a potential set of customers right when you launch, right away, right? And the truth is like, even with this business book, frankly, like

There's lots of business books. Like it's a book launch. It's a new, like, it's not that compelling, right? It's not that interesting. But if I say, Hey, I built a new business over the weekend, I live streamed the whole thing. There's 15 hours of it on YouTube where you can go through if you want literally all 15 hours of me building a totally new business from scratch using Stripe, like everything, you know, like zero to one.

That is much more interesting to most people. Why? Because it's different. It's unique. It's real skin in the game. It's risky. I could fail at this. I'm doing it in public. I could not finish in time, et cetera. It's more exciting. There's a whole variety of reasons, I think, that it's more compelling. And I learned this with Gumroad. How many people care, oh, Gumroad launched a new feature today?

I mean, some, right? But not the broad world, right? But if I said, hey, Gumroad failed to raise a Series B and this is how we reacted to that situation, that is, you know, many people are curious about that. They want to learn. They want to feel seen. They want to know that like, oh, this journey isn't as simple or as easy as I thought it was based on these TechCrunch headlines or whatnot. Many, many more people are wanting that information versus, you know,

what featured in government chip recently, right? Like, and so lean into that, lean into what do people care about? They care about other people. They care about stories. They care about struggles, right?

You know, those sorts of things and use those to your advantage. Right. And you can still do all the other stuff. But I think generally, you know, focusing on on on the vulnerability side of things like generally, that's what people really, really want. And it's not it's not easy. Right. It's not easy to say, hey, tweet out your revenue numbers in public or they're obviously. But but that's why it works. It works because there aren't a lot of people willing to do that.

And you may be surprised if you are one of the few willing to do that, be willing to do that. Like all there's tons of people on the other side who want that information. And boom, now you're, you're the one providing it, right? Like on YouTube, you can go find a video where I walk through my contract with penguin. And I go through the economics, like the advance, it's $115,000. It's split over two or three years. Like there's just, you know,

facts of the, of the agreement and of the industry. Uh, but it just, I tried to find a lot of this stuff when I was doing, and it just wasn't really there. Uh,

And so, you know, that who knows, will that sell books or not? I don't, it doesn't matter to me really that much, but, but I just, yeah, I'm constantly trying to teach people, uh, learn myself. And the side effect of it is like building hopefully real trust, real relationships, um, with this, with this audience. And it's very like low information asymmetry, right? Like,

this model wouldn't really work if they were all these things that I wasn't proud of, right? Like building in public is, it doesn't really work if you're building a product that people don't like, right? Uh,

So, so, you know, it, it almost like forces me to, to be like better in a sense. And it's like, okay, well I need to fight for an agreement with penguin that makes me look good. You know, like I think about, I obviously, I don't think that should totally inform the way that you live or anything like that. But I do think it's a helpful sort of heuristic for me is like, if someone was watching over my shoulder, would I still be comfortable doing what I'm doing? And a great way to gut check that is to share what you're doing with the world. And it's like, Oh,

like, okay, you know, Gumroad people generally like as a company, right? Like, um, would it have worked if we were like, you know, I don't know, doing like, you know, helping like the U S military, like, you know, with drone strikes, like probably not like the Gumroad crowdfunding round probably would have been received slightly differently. Right. Um, not to have a position on that. I'm not familiar enough to know, but, um,

But yeah, I think it forces you to kind of, and again, this goes back to community. Like you have to pick the right community on the other side. They're going to like agree with you on a lot of these things, right? There are certain people that probably they're like, oh, I want to write a business book for Penguin, like click that thing. And they're like, oh my gosh, this is, this person swears. Like I'm not, you know, and that's fine. Like you have to find your people, right? Or maybe this, you know, long Penguin contract thing does exist. It just exists in a format that isn't for me.

Like it's like some, you know, super long blog post or a newsletter posts, you know, somewhere out there. Right. But it's not for me because I didn't find it. So so here's my contribution to my, you know, part of the part of the part of the Internet. Right. Yeah. Yeah. I think I just want to kind of we just mentioned that.

And building in public, like a big bonus of it is like you kind of get to see the behind the scenes and you got to get to know like more of the personality of not just the person, but also like Gumroad as if it was a person. Like I know you have a whole PowerPoint about like this is what Gumroad like design looks like. This is like how we talk to customers.

And like, I could kind of imagine what Gumroad would be as a person. And also, like you mentioned, I watched that video of you going over your Penguin contract. And I watched a couple of YouTube videos of you kind of discussing with like board members about like where Gumroad was heading. And like seeing all that, I feel like I already established a relationship with you even before I never met you as a person. So it feels like, you know, that level of trust is already built there. And it's like, you know, it's like we've been friends forever.

This whole time while you've been building public, even though we never actually met.

Yeah, it's pretty cool. Right. Like, I think it's a, it's an amazing feeling. Like if I was in the same city as you, I know we could hang out and it would be totally, it would be easy, fine. And we don't even have to intro each other. Like, it's funny. Someone was like, wow, like you must be so extroverted. You're sharing so much on the internet and stuff. And I'm like, I'm actually kind of the opposite where like, I love sharing stuff on the internet because like, I never have, like, we can just get to it. Like we never, I never say, oh, this is what I'm working on. I don't know. It's like, no, you know what I'm up to. I know what you're up to. Like, let's talk about,

crypto or whatever, you know, whatever the topic of the day is. Right. And I love that. Like, I love the fact that like, if you're curious about these sorts of things, obviously you're not obligated to, but like, you can read all this stuff about me and then boom, like we can just skip to like the second or third or fourth conversation we would have had instead of

the first one, right. Which I'm happy to do. I'm happy to tell people about gum, right. Like all these sorts of things that I've been up to in my life. But, but like, I find that like the conversations get a lot more interesting, you know, over time. And if you can kind of skip some of those steps, like, I think it can really help. But yeah, I think just like planning these breadcrumbs right around of like, this is who I am and what I believe. And yeah, you can totally, you know, I kind of learned this from, from the base camp guys as well. Right. Like you can almost tell what,

Like if they said, Hey, we're building an email client. I could almost design it for them. You know, you know, it's good probably, but I, you know, I could use, I know their sort of value system and their opinions and the way they write so well. Um,

Then I can kind of say, okay, well, they probably care about simplicity and like, you know, like getting rid of a bunch of crap that you don't actually need. And like, you know, big fonts and big type. And like, they probably have a way to not see all the emails because their whole thing is about kind of like minimalism and, you know, only seeing what's important and not letting people take your time without your permission. And, you know, you can almost, and that I think is really powerful, right? Because if you say, hey, I'm building a new startup, we help creators sell stuff on the internet. It's like, okay, you and 50 other people now.

people now. But if I say, "Hey, Gumroad, it's this weird company, we're all part-time, we don't have an office, we haven't had one in a while, we were VC, but now we-- There's only one of those. If you're interested in that, if you're interested in this idea that, oh, you don't really like venture capital and you're more interested in this bootstrap for creators by creator, independent movement, you like to Daniel Vassallo, portfolio of small bets.

you like transparency building in public, there's only one of those. You can win on these other dimensions. I actually think

My theory, or at least my prediction of what will happen in the next 10 years is this stuff will actually become even more important because the products will be less differentiated because it's going to get easier and easier to build higher and higher quality experiences. It will become almost more like, why are you using Gumroad versus this? It might be as simple as I want them to succeed more than I want. I associate, I like these people more. This is my tribe.

Right. Um, well, like, I mean, this happens, right. Like Uber versus Lyft, right. Like almost has like, people can, to your point, like almost see like Uber is like, you know, it's more like, you know, square edged and like, you know, kind of like a, like a Trump figure in my head, you know, versus like Lyft is kind of like a cool, like hipster biker, you know, like you kind of almost see that play out in your, in your, you can't help it. And that maybe that's just the phenomenal brand marketing teams, right. That really helped him find that. Um,

But it, like, it matters. And I, I guarantee you, like, I know they're friends of mine and I can tell you what company they support, right? I can tell you, I know that they're Lyft, right?

writers and they hate uber or they excuse you know like you just kind of know uh it's it's like owners with their pet dogs or something right like there's some sort of some some hint of of connection there um so yeah just kind of i think it's really really important and and sort of strategically will really really matter in this world of just like noise overload you know

Yeah. And so I was going to ask you because yeah, building in public is a great strategy for the minimalist entrepreneur, but I feel like some people might be thinking like, like especially gummers, like you guys share your financials, you share your strategies, like aren't you giving away too much to competition? And do you think maybe just your brand protects all that or how do you look at that? Yeah, it's definitely a risk in the sense that yeah, our, our, our competitors could kind of like look at a roadmap and see what we're shipping and, and,

and, and these sorts of things. But, um, or yeah, maybe our financials could like reveal, you know, if we're like negotiating with VCs or something like that, we may not want to like be super forthcoming with some of these figures immediately, at least. Right. Um, this kind of goes back to like the used car salesman approach, right. Which is like, um, a very salesy, you know, it's kind of like you're, you're using a lot of these kinds of sales tactics to optimize for like the short term, which is fine. Like no value judgment on that. Um, but,

But yeah, I mean, the way that I justified it to myself was like, look, there are plenty of public companies. They say all of this stuff every quarter.

And yeah, it probably is helpful to their competition. I'm sure their competition looks at it and analyzes it. But those are probably not the competitors you need to be worried about, right? The people you need to be worried about are like, for Gumroad, for example, it might be something like, oh, these people are building like a decentralized crypto web three version of Gumroad. And that's actually the future. And like none of our competition actually survives this. Like the people, you know, like...

I always try to think slightly larger. Even when I was at Pinterest back in the day, people would ask us, who do you compete with? We could say Supply, Delicious, this kind of old school bookmarking sites, basically. What we said was, no, we complete with Netflix because

ultimately like people are have time and they want to spend it being entertained and, uh, in, in a sort of pseudo productive way. And, uh, you know, that's who we're really competing against. We're competing against like browser time, right. With, with, with, with Netflix. Um, and, and, and so, yeah, I think, I think it's really kind of important, um, to kind of

To to frame who are you really competing against? Right. Which is like customer indifference is maybe number one. No one cares. And then and then it's like, OK, well, how do we get people to care? And that's probably a much riskier risk to mitigate, you know, via this method. And then honestly, the other the other thing that I just really after I wrote reflecting on my failure to build a billion dollar company, actually before I published it, I was like, what company do I really want to run?

I don't care how big it is. I don't care how small it is. Like I wrote, when I hit publish on that piece, it was like, I'm content. I'm happy with Gumroad. I almost like wrote it off. I called it reflecting on as a, you know, kind of a way to signal like, this is my goodbye, you know, to this chapter. Obviously I hope Gumroad does well and grows. And like, I, I, I think it, it will, but you know, I was like, whatever happens, I want to run Gumroad the way I want to run Gumroad. And hopefully all the good stuff,

you know, numerical quantitative stuff happens as a side effect of that. And that's just what I continuously remind myself of. And sometimes I'll even go back to that essay and be like, oh, damn, I'm really glad I wrote this because all these VCs are knocking on my door now asking me what I would do with a bunch of money. And it's nice to be able to point to this thing and say, look, you go read this. This is my set of values. If you still think we align, like happy to talk,

but just know that this is where we're coming from and we raise this crowdfunding right in public and you can like go consume our board meetings and like you're actually going to get more knowledge about gumroad and my sort of and the future of gumroad and the way that i think then actually i would argue most traditional fundraising processes actually right because you get there's a way more hours of content than like a one-hour resume or something like that um and by the way every single time like they come back and they're like never mind not

not like clearly not a fit. And it's like, awesome. Like you would have, you know, just the last email from you was like asking for an hour long zoom meeting. Right. Uh, so boom, like time saved. Right. Um, we don't have to do that anymore. And so I, I think that's also kind of an important thing is I want people to watch that board meeting and say, Hey, I actually don't agree with the way that you run gum road. I want to go support Patreon. And it's like,

You know, I'm glad that you found out now. Right. Versus later on. So I think that's also part of it, too, is like I'm trying to really optimize for the long run. And the way to do that is just to be super honest and hope, you know, or not even hope, but just like see what happens. Right. And it's yeah, it seems to have worked so far. So I'll keep doing it. And that's, I guess, another important thing in my back pocket is I'm like, well, this worked.

Right. Like I have data that shows like nine, 10, 11 years in that, like a set of decisions that I made that I think a lot of people wouldn't have made the same way seem to be the right set of decisions. And so, you know, I should probably just double down on those. Right. Like it would be, it would be stupid. I think at this point to say, actually, I'm going to do everything the way everyone else does because Gumbart is now successful. And, and imagine if Gumbart doesn't work after that point, then it would be so easy to be like, oh, wow, I really,

fudge that one right so yeah yeah one of the things i love about gumro is how like forward looking you are and how you're willing to like try different things like so you guys build in public you know you share like your financials online your strategy but you also do some other really cool things like you mentioned a lot of your employees just work part-time 20 30 hours uh you're fully remote do you see more businesses heading this way and also like what's

What made you want to kind of pivot and shift to like that kind of strategy? Because I think anyone who works in corporate business today would be like working part time and still paying people like, you know, high wages. It's like, why would you do that? But Gumroad has done that. It's been super successful. And that's also, I think, one of the reasons why people love working there. Yeah, totally. There's a few reasons. Honestly, the first one was purely marketing.

existential, which was like the business is going to die. We don't have enough money coming in. And so the only way we can build a team is in this very flexible kind of part-time contractor basis, hiring people

abroad to do that. And so it was really initially, and this is like, let's say 2015 was the layoffs and the failure to raise VC and sort of the path to profitability, just really me running it was, you know, took up until probably 2016, 2017. And then 2017 to 2019 was when we

you know kind of grew but in this very part-time way and i was kind of just doing other stuff i was i was kind of disconnected i was like i need a break i've spent a lot of my time working like 60 hours a week or whatever uh on this project i need a break i moved to i like left san francisco and i was like i don't want to think about work i kind of went totally the opposite right i was like four i was like four hour work week can we do two hour work week right um

And so, yeah, it was just like, okay, I'm going to like just use Notion and Slack and everything, GitHub, and everyone kind of will talk to me through one of these tools. And that allows me to kind of respond on my own time. And, and, and just kind of, it was really just like, how do I not have to think about this thing for a while while I kind of reset and reflect and blah, blah, blah. And, and literally just like didn't stop. Like, it was just like,

oh, this other person wants to work here. I'm like, well, this is the way we do it. We pay hourly. You know, it's maybe not what you look. And like, there was enough people that like, it's like, oh, maybe there, we can just continue to do it this way. And we kind of just got to a point and who knows, like, you know, a year or two, five years now, uh,

what Gumroad looks like, it will probably be somewhat this, maybe we'll add some other stuff as we grow. But yeah, it just seems to have worked. It seems to work really nicely. And I think the way the kind of one liner behind it is, before we were focused on kind of growth at all costs, which is what most startups are probably focused on, like their number one North Star metric is generally growth, some sort of percentage relative growth generally.

Because they want to raise more money and obviously they care about profitability, but it's sort of

deferred generally. And in our model, it's like freedom at all costs. Like how do we build a culture? Or I would say maybe now I would say flexibility at all costs. Like how do you build a culture that allows for the flexibility of work that I believe should be present again, like not full-time, right? Like what does full-time mean? And so, yeah, I just wanted to really lean into that. And it seems to have worked. It seems to be working.

There's a lot of stuff to figure out. And it honestly, it gives me like a renewed purpose because

Because it almost feels like a meta mission of the company now, where we're not only trying to unlock flexible living and work for creators, which is kind of what the creator economy is, right? It's like all these people trying to exit full-time employment through content creation and things like this. But it's almost more broad than that, which is like, well, even the people who aren't trying to exit the traditional industries, they also shouldn't be working 40 hours plus a week. How do we get those folks out?

And the current model is just, well, we can write about it. We can build in public. We can show people that this works because I think ultimately

People just don't believe it yet. Just like people didn't believe remote work would have worked like in 2019 for most companies, even though there were some examples of it. And now get lab is, you know, IPO thousand employees. They don't even have an office, right. Multi-billion dollar, maybe over $10 billion company publicly traded down. Right. Like it's clearly happening. And I do really believe that the next step is no full-time people. Why do I believe that so strongly? Well,

It made sense when you had an office because you can only be in one place at one time. You have one body, right? And so effectively, every company had a monopoly on you because you could only be in one place at one time. And so you had to pick a place and you could only be there. And that was the one job you could have. And the office went away in 2020. And my guess is there's a lot of other things that went away that we haven't really seen yet. But one of those is, well, you can now work

for two companies at the same time in theory. And there's a kind of jokes or whatever, you know, people will say, Oh, I have a friend who works at Google and Microsoft or whatever makes double the money, you know, and just like sits in on both meetings or what have you no idea if it's real or not. But,

I believe that's the future, right? Because ultimately, like the sort of macro view I have is that people should get paid for the value they're creating, right? And that means ultimately, even like Gumroad's not perfect at that because an hourly rate is also not the exact measure of that, right? But

If that's the case, then yeah. You know, people like, why does it matter how much or how little you're working? Right. Uh, if you generate a million dollars in value for gum road, you should be able to, in theory, get paid 999,000. I mean, the math still works for us. Right. Um,

You see this in the economy today, it's inequality, the rich get richer, people who own capital are doing better, everyone else is getting destroyed by inflation, etc. The way I think you fix that is you make companies smaller, you have a lot of them, you allow

You kind of allow your people to have more leverage. And the best way to do that is to give them the information. Everyone at government knows how much everybody else in the company is making. There's nothing I know besides maybe the password to a bank account.

like that right like that that you know that that you know any any person who works at the company uh doesn't know and i think that just makes it honestly just saves me time too it's like hey you want to negotiate for a raise these are the eight other people that you're also negotiating on behalf of which is you know great but like just so you know this is like you know where i'm coming from this is the math that i'm doing and if you can make a compelling case like

awesome. You're doing my job for me then. Right. Which is great. That's my goal here. So, so yeah, I just, I kind of just apply that sort of philosophy, you know, even building in public, like kind of even internally, you

Because I also kind of want to be almost like non-essential. What is the most minimalist entrepreneur you can get is not even running the company. So yeah, I think a lot about how do I kind of get there. And yeah, Gumroad kind of almost serves as this beacon for folks, kind of like Basecamp I did over the last 15 years around this kind of new way of working. And we'll see. Yeah.

How it plays out, I do think that what you're seeing with crypto, with DAOs and tokens, it seems to be a harbinger of what's going to play out, which is no one is employed, quote unquote, in crypto. You just own tokens, which is effectively startup equity or the equivalent of that. That is your incentive to contribute to these communities, et cetera. That to me, it's very liquid. It's a very flexible. It's weird.

There are a lot of ideas there that I think will make their way into the traditional economy. I like Gumroad because it feels like I'm living in the middle a little bit, where I'm still definitely in the traditional Web2, fiat, whatever you may call it world, but I can take some of these ideas and seal them and be like, oh, this idea from crypto is really interesting. How do I apply that to Gumroad today? One of that is pseudonymity. Why do I care who you are? If

If you can do the work, going back to what I said before, if your work is valuable, it shouldn't matter your gender, your age, your degree, your zip code, your country, you know,

Obviously, there's still KYC, so I still have to know where you live and we have to pay taxes and things like that still matter. But at least let's paint a picture of the ideal world and then we can work within the current regulatory framework to get close to it and then almost have a to-do list of, "Well, these are the things we will change once they're possible whenever they happen to be possible."

But yeah, even at Gumroad, I, you know, I'm like, yeah, use pseudonyms. Like, you know, I know one at the company has first name or has, sorry, last names kind of list. Obviously it's not hard to know what my last name is, but I just like the precedent of like,

Going back to minimalism, you only bring what you need to bring. What you need is some way to identify who you are, some way to mention you on Slack. It doesn't have to be your name necessarily. I don't need to know the name that your parents gave you 35 years ago. That's not...

relevant necessarily to me right so anyway i like to play with a lot of these ideas and then honestly sometimes some people have been like you know probably like why why bother like what's you know and i'm like i don't know it's fun like ultimately like this is an important part like it's fun you know why do i build in public like well i enjoy it you know so uh i do think there are reasons to do it but but like yeah ultimately you know you should find the things that

hopefully make strategic sense for you, but also happen to align with something you just kind of enjoy doing and would maybe potentially do anyway, even if there wasn't like a, you know, a bucket of money at the, on the other side. Yeah. Yeah. I really appreciate gumroad. Like,

kind of taking the charge and like taking all these new like kind of work policies because i really think that is a future like i spent a lot of time on twitter i'm like oh wow the world is changing so much and so futuristic and i talked to my friends like you know that aren't on twitter and it's like these guys like 20 years behind meanwhile on twitter everyone's like 10 years ahead in the future um so i really do believe that's gonna be like the future work it just makes so much more sense it's a lot better way of working and um so i see like gumroad as like uh you know

really trying new things and it's like just really cool to see like what you guys are implementing and I like to tell the team like look we're we're on the bleeding edge which does mean that we might bleed every once in a while right like there are there are some costs and risks to operating the way we operate because like we're just it's just new you know there isn't as much precedent we we will make mistakes and

you know, some lawyer from Australia might say, Hey, the way that you employ people here is not, you know, like these sorts of things will happen, but kind of going back to the minimalist entrepreneur framework, like start, then learn. Like, it's like, you know, people like what, you know, people ask a lot. They're like, well, what happens if blank? I'm like, I don't care. Like, we'll figure it out. Like, I don't think the business will die. And you know, we have some money and we have smart people and we can pay lawyers. Like we'll get through, you know? And I really believe,

In like, I don't know, like I have a lot of trust in the system and I really believe that like if you have good intentions, people will help you succeed and make them a possibility. Like my goal isn't to just say, oh, like the government's evil and 40 hours a week. No, like they have reasons for putting those things in place. And and there are there, you know, the world is different now. And like as long as we show people what we're trying to do.

and we do it incredibly transparently, which hopefully, you know, inspires trust, then we will, that's how we win the argument, right? It's by showing people that this is possible instead of just saying it, you know, this is the way it should be done, or this is better. No, it's like, look, this is the way we run the business. And like, you know, uh, hopefully we can go public and, you know, do all the things that will, you know, people think successful businesses should do, but this, in this weird way, um,

You know, in order to promote this kind of, this kind of mission. But I, yeah, I do hope as well that like this does, this does become kind of the default kind of future of work because it just doesn't make, it doesn't just, it feels like too anachronistic, right? 40 hours a week. I mean, it just, it's strange to me. Anything that looked the same pre-internet and post-internet, I'm like, there's something up here. Like,

we, you know, in the thirties and forties, we went to the factory and, you know, commuted and worked there for, you know, whatever with an hour long lunch break, like all these things like don't really make a ton. They didn't make a ton of sense even in 2019, you know, but certainly, you know, remote, you're like, why am I working nine to five at home? Like, that's weird, you know, like, uh, so, so yeah, I, I am excited for kind of like the, the kind of

second third fourth order changes that will start to to kick in and hopefully gumra can contribute to them yeah definitely going to be interesting to watch that happen and so style you're one of the people that you know i follow on twitter and love reading your tweets and another person i follow a lot is nival and i know you guys shared a lot of clubhouse uh conversations and your friends are there one or two lessons you learned from him could be about business could be about life or like uh any one or two lessons stick out that you know he taught you

Yeah. Oh, man. A lot. Naval's...

an awesome, awesome human being. Um, one of them is writing in public. Like I think people sometimes forget, or at least maybe if they just learned about him on Twitter, like don't realize that this person has been doing this kind of thing, which is kind of learning and sharing his knowledge in public, you know, pre Twitter, right? Like pre early pre Twitter. Uh, you know, he had a blog called venture hacks. I believe it's still there. If you just go to venture hacks.com, which was kind of the predecessor to angel list. Like, it's kind of funny because he

It is the minimalist entrepreneur framework, right? He started a blog. He started contributing to a community, teaching what he was learning over time, trying to increase more information symmetry in these kind of venture capitalist areas.

entrepreneur conversations. And then he productized it with AngelList. It's kind of funny how cleanly... So very much an inspiration, I think, in many ways. And then I think I really... And so that's kind of like the broad kind of career, maybe strategic one. And then I just really like how he...

doesn't focus on anything that doesn't feel important like it really feels like he's really just focused on what matters to him and he's just very honest about that even in ways that might make you uncomfortable you know um like if i'm like hey like what's up you know i probably won't respond you know like he's very kind of focused on uh and then that's great and i i like

The word transactional has a negative connotation, but I like the fact that I kind of go into those conversations wanting something, getting it incredibly quickly, and then moving on with my life and vice versa. I like that. And I really believe when I talk to founders and when I talk to people who DM me on Twitter, my goal is literally to just help you solve whatever problem you're trying to solve at the moment.

And then move on because then I can go help somebody else and you can go do what you really, I assume you don't want to just talk to me all day. And just being honest about that, like being honest about just the fact that everyone has like a thing that they want to do. Like they don't follow me on Twitter because they think I'm a genius. They have some problem. They think that I might be able to help them solve it. And, and that's like, I don't know. It just,

It lowers my ego almost, right? It's like, I try to kind of keep that in mind where like no one, everyone has their own concerns, their own problems, their own stuff that they're obsessed with. And I can help them. But ultimately it's not about me. It's not about like, Hey, I wrote a book and it's awesome. And I'm a,

Penguin published author. It's not about that. It's about, hey, I wrote a book that I think can help in these ways. Hopefully, it does. I think it's anti-hype in that way. Even AngelList, now it's pretty big. It's pretty important. It's a fundamental pillar of the startup ecosystem. It's a 13, 14-year-old company. It took a long time to get there. I don't think Novol's ever said anything like, this is

He barely even talks about it. I'm sure a good chunk of his audience doesn't even know that he started AngelList. Maybe he doesn't even know what AngelList is. I really like that. I really want to focus on my ideas. That's why I love Twitter. I can focus on my ideas and less so about my resume, my credentials. The book doesn't say founder of Gumroad, 11 millionaire, whatever. No, you'll get that from reading the book. It's just the minimalist entrepreneur. This is my name.

And really trying to sell based on what's in front of you, the cover and those ideas themselves.

Yeah, definitely. He's, he's, he's definitely inspiring. And the other thing that I would say that is kind of a meta observation is that you don't even need mentors in today's world because you can learn like everything that I've learned from him. Like none of that was learned by me, like grabbing coffee with him, you know, like whatever, like it's just, no, I just follow him on Twitter. Like I had, yeah, I hung out with him a few times first or whatever, but like, you know, it's just like, you can get a lot of this stuff. Just listen to him talk on Joe Rogan podcast or, or,

or whatever, and you'll get a lot of this stuff. And then it kind of is like, oh man, it turns out there are no shortcuts, right? Like that's like the big, that's always the ultimate lesson I get. Oh yeah, it's just hard work. You know, it takes time and it is high risk and you will likely fail it. But like, luckily it's okay if your business fails, ultimately who cares, right? Like what matters, you get what you want eventually, right?

Yeah, it's such a cool time to live in where you don't have to be best friends to Naval to read his tweets, listen to him on his podcast or read the almanac of Naval Ravikant. It's like there's so many ways you could find the mentor today without ever meeting the person. So it's just a great time to live in.

And Sahil, so I know your book will most likely impact like the future generation, like business creators, entrepreneurs. But were there one or two books that you read as a young adult that had like a huge impact on your life and how did those books change you? Yeah. Oh, my gosh. There's a long list of books that and I can send you a link to.

because there's a list of 50 or 40 or 50 of them. I feel like we're really essential for, for, for me. And I'll just pick a couple randomly. One is moonwalking with Einstein, which was a really important book for me. It's about,

three different things, but primarily around memory and how memory works and some tactics around increasing your memory. But to me, what was most interesting was this idea that we live in this world of you don't actually need to memorize stuff because everything is a Google search way. But I just like this reminder that no, there are certain things that you want in your brain.

as close as possible where you don't want to be, you know, if you have to Google, if it's a Google search away, like it's too far. Like you're not going to be able to use the information as like, for example, like Steph Curry is not going to go Google for like how to report it from this way. Like it has to be innate to your, to kind of your being almost. Right. And so I really liked that. It talks about how like back in the day before libraries were commonplace, et cetera, like people would literally just pick a couple of books and memorize them.

and just literally just memorize and so your personality became like three books right like you pick three books you know one of them is probably the bible or the quran or something right and and then you pick two others and that's kind of 80 of your personality um but so i kind of just i don't know i like reminding myself of that in this age that like it is still important to read to internalize these lessons pretty deeply to reread over and over again um and then uh

I'll avoid beginning of infinity. Cause I know we've all talked about that like 50,000 times, but that is a great one. But, but, uh,

but my version of it would be Ishmael. So Ishmael is a fiction book. I like fiction a lot for these lessons because it feels like I learn more almost because my guard is down when I read fiction. I'm surprised and delighted more often, but also disappointed as well. But with Ishmael, one of the lessons I took away from that, there's this conversation that happens in the book and basically it's like a gorilla talking to a human or something like that.

The gorilla basically just makes the observation that genetically, we are very, very, very similar. We are 99% similar to an ape or even like a banana, very, very similar. We are obviously capable of 100x, 1000x, an infinite amount more creativity, technology, innovation, what have you, observation of the universe, et cetera, than a banana.

And I really, it just got me really thinking about, oh, we are not done. We are not done. It's so easy to think that we are at the end of history, right? This is the end. Like, and, you know, this is kind of like the religious observation, right? Is that like kind of, and I was sort of born and raised Muslim, you know, basically Christian, right? With different words or whatever. But, you know, like the, like basically like, you know, the vibe that you get is basically like, this was all created for us, right? And you kind of just assume that like humans are,

kind of the end state of-- you don't think, oh, like a billion years from now, we're going to have like six arms, right? You kind of think we're kind of done evolutionarily. And Ishmael really, for whatever reason, really convinced me that no, just like tiny change to monkeys made us humans, like tiny sort of genet-- as a percentage, very, very small.

changed everything. And like, what does that mean? Right? Like, it probably doesn't mean that we're just apes with like nicer houses. Obviously, you look around, that's not, you know, but like, we are probably still under appreciating the future, right? You're still very, very, very early in like the sort of grand arc, the beginning of infinity, as David Deutsch calls it. We are still very, very, we're at the very, you know, there's that hockey stick, right? We're at the very tip. And guess what?

we're always at the tip, right? Because as long as we continue, continuously innovate, invent technology, you know, sort of execute on science and research, like we will continuously learn more stuff, do more things. And, you know, like the kind of example I think David Deutsch uses is like, you know, space factories, right? And it's like, that is a concept that like most people probably never even heard of, but like, like reading it, it's like, obviously we're going to have space factories in like 20 years, right?

And if we have space factories in 20 years, why can't we have this, you know, in 50 years? And it's like, I don't know. That always, you know, that always gets me excited because what it, what it, what it means to me is as long as I don't die, like as long as I continue, continue to function, I will be around to see some awesome, awesome, awesome stuff. And that gets me, I don't know. That just makes me feel good. It makes me excited about contributing to that future. Like if I believe climate change was ending the world, I would probably not do as much for the world. It's like, why would I put in a bunch of time and wake up early and sleep late and

for the world to end anyway, right? Like, but if I believe no, actually, like we're early, early, early days, you know, we're in the first 1% of humans who will ever be born or less, then my impact is going to be a lot more, right? The ripple effects, the network effects of what I accomplished today. Most people will never even connect the dots all the way back. Just like I don't connect the dots even more than two or three generations ago, right? Uh,

But that's fine because my sort of the value that I'm creating is like incomprehensibly large, right? And all of us, right? Not just me, right? Like broadly, like our generation is just very, very consequential. And of course, like,

you know, the beginning of infinity could be wrong. Like we could nuke ourselves tomorrow and boom. Right. But, but like, I don't know of, of the, of the views that I like, you know, of the, of the possibilities. I like thinking that we're on the, on the kind of the simulation argument one, right. We're on the, on the Elon Musk track. Um, to me that, that is more exciting and gets me fired up, uh, more than anything else. So anyway, that was really long, but Ishmael and moonwalking with Einstein are both, both great books. Hmm.

two books i'll definitely have to check out and it's really interesting how uh just like yourself and also like elon musk a lot of these like you know founders and ceos like they've really been influenced by fiction books where it's like you think it's like sci-fi but eventually it's going to happen and that's kind of like an opportunistic uh way to like have things like hey like eventually everything in these sci-fi books will become reality and it's only a matter of time before that happens yeah i mean

Some of these things are obvious in the sense that they will happen. They're not even that hard to predict in the sense that, yes, I think a lot of people probably predicted that once the internet came about, that eventually you'd be able to buy stuff on the internet. Solving that problem is much harder. I love reading these books and being like, yeah,

this will, why not? You know, um, I have zero pessimism around like visiting Mars or going to space. Like, yeah, like, of course, like I have zero, like zero doubt in, you know, the physics are clearly, it's possible. Like you're just shooting something up into space. Like,

And once it's in space, you can kind of point it anywhere and, you know, it's effectively free almost to get there. Right. Like the hard part is getting into space. That's that's expensive. Right. Overcoming gravity. And then you're kind of good for a while until you have to land again. Right. Just like flying. But taking off in the landing is the hard part. Like the flying is actually easy. It's like driving, except you can't run into anything.

Uh, uh, is what a friend told me, but, uh, yeah, it's, it's, it's, I don't know. I, I really, I just, I, I, yeah, constantly just love being reminded that we are very early. Um, and yeah, just stay alive and things will just improve. I, I, I really believe that.

Yeah, totally. Same here. So Sahil, that's a wonderful conversation. I really enjoyed talking about the business entrepreneur. I'm sure listeners did too. Where should they go to kind of learn more about you, you know, find your book and just, you know, come across more of your stuff?

Yeah. I mean, I think Twitter is probably the best jumping off point. Uh, my Twitter handle is at S H L and, um, yeah, from there you can, you know, probably find links to my book or Amazon or audible or all the, all the places, uh, you know, ultimately like I think Google, right. Uh, uh,

And, but yeah, Twitter is probably the, the kind of the best place to, to kind of, to, to, to look at my stuff or reflecting on my failure to build a billion dollar company, which is generally my tweet, unless I'm coming out soon, uh, is, uh, it's kind of like probably the best long form to kind of get a quick hit of like, okay, this is kind of like,

who he is, right? And like why he's the, you know, ultimately, like, the beliefs that we have, I think, are a result of our experiences to a larger degree, like, it's kind of hard to avoid that. And that's, you know, a good kind of summary of my experiences and may inform like, why my worldview is the way that it is.

Yeah, I really enjoy following you on Twitter and I highly recommend other people do too. And I just want to say thank you for starting Gumroad, for kind of, you know, leading the future of work, for writing this wonderful book. And of course, thank you so much for coming on the Reader's Journey podcast today. You're very welcome. Thanks so much for having me. Hey, everyone. I hope you enjoyed this episode of the Reader's Journey. You can learn more about what's covered in today's podcast in the show notes below.

If you enjoyed this podcast, the best way you can support it is by subscribing and leaving a positive review. If you're looking for reading tips or book recommendations, head over to alexandbooks.com. If you want to join my reading journey, you can follow me on Instagram and Twitter by searching for Alex and Books. That's all for now. Thank you so much for listening, and I hope to see you soon. Read on, everyone.