Sahil Lavingia: The Pros and Cons of Setting Your Own Goals

Sahil Lavingia discusses why and how he runs Gumroad with no full time employees, no meetings, no deadlines and no company perks.

NB, This was a talk that polarized opinions…

Sahil is a fascinating individual. There’s no question what he’s done in his career and his approach to running his life and business has led to significant success for him. He shares some perspectives that run counter to the orthodox approach to running a company. For example, the team at Gumroad are less motivated by the mission and the team – there are no perks, company retreats, social activities and slack. No health benefits. Nothing besides cash for work, or equity if you want. A very transactional approach. This works for the people who work there. There is no single path to building a successful business. There is a lot to provide food for thought and it was refreshing to hear from someone who has chosen his own path.

On the other hand, you may find some of the things we discuss towards the end of this discussion aggravating or offensive. The comments about why Elon Musk or Jeff Bezos should have hundreds or even thousands of children left many of us feeling uncomfortable. Sahil has an unshakable belief in the power of technology that means he is not worried about climate change because tech will sort it out. Life is more complicated and that perspective may have some merit but is dismissive of the effect of climate change on humanity and the global ecosystem as we wait for that to happen for example.

We will not always agree with each others point of view, that’s part of humanity. A fascinating talk nonetheless.

Transcript

Mark Littlewood
Welcome Sahil, Yeah, you’re one of those entrepreneurs that works pretty much all the time. So you’ve probably been up for hours.

Sahil Lavingia
No, My goal is to work as little as possible. I try not to work at all. So I’m done with my work day, actually. And it’s -what time is it? 10am?

Mark Littlewood
Wow, that’s very impressive. Can you give us a little bit of background and a little little bit of insight into what you’re doing before we kind of dig into? What’s the history? Why are you here? Why did I invite you?

Sahil Lavingia
Yeah, that’s a good question. So I got my start at Pinterest – I was employee number two at Pinterest – where I designed and built Pinterest for iPhone, among some other stuff that I did there. But I was stupid so I didn’t invest any stock, I ended up leaving and starting a company. So I started Gumroad in 2011, raised a bunch of money for it, tried the venture backed startup route from 2011 to 2015. Failed that that one as well. Had to downsize the company from 20 people to five people, and then from five just to me.

Got to profitable not hard to do when you do that. And then basically, I’ve just like been running the business, just like the way that I want to, since since then. So in 2016 or 2017, I left San Francisco and moved to Provo, Utah, where I learned how to paint and how to write – science fiction and fantasy from this guy, Brandon Sanderson. And, Gumroad just kept doing its thing, you know, the beauty of software is, make money while you sleep, they say, right. So it kind of kept doing its thing. And then 2020 happened. That kind of whole crater economy thing is now kind of a buzzword and you know, just we saw a lot of growth in 2020, we roughly doubled, which was pretty, you know, we didn’t have a team or anything was just like this, it was kind of crazy. I had to work again for the first time in a while.

And so I took a break from painting and writing science fiction and fantasy. And then there’s a couple, I guess, notable things that I’ve written recently that people like, one is this thing called ‘Reflecting on my failure to build a billion dollar company’, which is kind of about the Gumroad journey, and kind of my new approach. And then I recently wrote an article called, ‘No meetings, no deadlines, no full time employees’, which is how Gumroad operates. Today, we’re doing $12 million ARR, we just raised $6 million at $100 million valuation. And actually more than that higher valuation soon that we may or may not announce who knows.

But uh, that’s generally why people ask me speak is for those two things. And then recently, I guess I also this crowdfunding round that $6 million, 5 million of it was via crowdfunding, which is this kind of new thing that we were relatively early on as well. So now, people have a lot of questions around crowdfunding. But generally, I just like, you know, I, I kind of do things my way. I don’t have to answer to anybody. I don’t have a board. I have, I guess what you would call fuck you money. And I also now have a fuck you audience. So I can kind of do whatever I want. I have a rolling fund as well that I launched last year. That’s now it launched at $5 million a year. And now it is $12 million a year that I get to invest in startups. That’s kind of a side project for me- a side hustle. And I’m writing a book or I just finished writing a book for Penguin which comes out October 26, called ‘the minimalist entrepreneur’, which is kind of like my playbook for how I would start a business today, if I were to do that. Which I am doing, I started lots of businesses. So yeah, and then but mostly I write that’s kind of my primary thing that I like doing. So yeah, anyway, that was kind of a rant. That’s my two minute spiel.

Mark Littlewood
Rants are fine. And you didn’t start out like this. You started out and you went down this classic silicon valley you raise a tonne of money and you had a tonne of money. And VCs, so you had quite a conventional start where there sort of any particular things that happened to make you realise what a big or why was that such a mistake for you? Is it just you really want to do your own thing?

Sahil Lavingia
Yeah. Well, I mean, I think the thing with venture is that, and you know, and I can, I am a venture capitalist now. So I can I kind of play both sides of the argument. I’m a hypocrite, I guess. But, uh, you know, I think that the thing with Ventures is, I think venture is great. I mean, I’m a huge fan of venture capital. But I think it is fit for very, very few businesses. And so I think generally, when you have, you know, when you, I think what you’ve had recently, both in this sort of the zeitgeist, but then also sort of actual capital allocation, you have a lot of money that flows into this world that, like, has to get invested basically, right. So you end up investing in like, a lot of things. And that works, generally, for the VCs like me, because, you know, we’re making a lot of bets, right?

So we’re investing in dozens of companies, hundreds of companies, and so it’s totally fine if 90% of them die, like that’s just the nature of the game. But as a founder, you know, you’re kind of taking one shot every five years or every 10 years, right. And so, the risk profile is very, very, very different for these two groups of people that you both need them to, for Silicon Valley, or whatever, to kind of work. And so I think, as a founder, you kind of, it’s easy to get swept into, you know, get higher on supply and think that you’re going to be the exception, every founder thinks they’re gonna be the exception, obviously, Otherwise, they wouldn’t be doing it. And so when reality hits you in the face, you know, the VCs don’t really care. I mean, that’s part of, you know, part of the game for them. And so you’re kind of left if you rely if you kind of have built yourself kind of a certain kind of identity. It can be really dangerous, I think, just for your personal well being because, you know, you realise you’re just like, you’re like a, you know, I don’t know, a basketball player that gets traded or something like, loyalty is not a thing, right? Loyalty does not exist. It’s it’s a very capitalistic system. And so yeah, this is some of the stuff that I learned, I think, you know, I don’t necessarily regret raising money or anything, but I probably raise too much too quickly, because raising money kind of forces you to accelerate, right? And when you accelerate just like a lot harder to make changes. I think, generally, you should be pretty confident that like, the direction you’re going in, is the right way to go because it’s virtually irreversible. Especially when you have burned, right. It’s kind of like rebuilding, you know, trying to change, you know, rebuilding a plane in midair kind of thing, right.

Mark Littlewood
Can you just say how much you raised?

Sahil Lavingia
We raised $10 million. I think we raised a $1.1 million seed round from Chris Sacca from lowercase Max Levchin from PayPal, Excel partners. First round, collaborative fund, Danny rhymer, Seth Goldstein, navall, maybe some other folks that I’ve forgotten and then we raised a Series A a $7 million series A from Kleiner Perkins. And we ended up raising a little bit more than that, we raised a bridge round from Kleiner and Mark Cuban and some other folks, I think, first round, put in a bit more money then. So yeah, over the course of those three or four years, we raised around a little over $10 million.

Mark Littlewood
Yeah. And that forced you down a route that you weren’t necessarily comfortable with. But it’s actually quite unusual to walk away from that kind of old cliche, it’s the kind of rocket ship but you know, you walk away from the rocket ship. And you’ve still got a kind of car that’s working. I’m mixing my metaphors . The company, it was still there, but, how did you get rid of them in the nicest possible?

Sahil Lavingia
Yeah, I mean, honestly, I mean, this is one of the reasons I think that article resonated so much with people was that it’s just not that common. And it’s not that common, because like, you generally can’t choose to do it.

It’s not your choice, the VC has to say, you know, this is not working for me. And so I’m going to write off my investment. I don’t know still to this day, exactly why that happened. And it’s a little bit like the Heisenberg uncertainty principle, like, you can’t observe position and momentum at the same time, like, you know, this sort of effectively observing anything will change, change what you’re observing, right. And I think that’s kind of what happened. Gumroad I think for them, basically was a dead company.

And it was kind of a zombie startup and they were fun going through changes, they probably wanted to simplify their books take a tax write off, right? They basically, you know, venture firms can kind of put their losses against their wins and, and save a bunch of money when they pay taxes. So they probably had a good year with Uber or Slack or whatever. And, and they saved $7 million, or, you know, $9 million. However, $8 million was how much Kleiner put in, you know, so they got an $8 million tax write off, presumably. And, you know, it’s kind of like heads we win, tails we win too, for them.

They really just sent me an email and said, Hey, we’re, you know, we’re interested in writing off the investment, basically, Gumroad, you know, we’ll buy back our shares for $1. And so I said, Yeah, sounds great to me. You know, I’ll look and you know, find some couch money or whatever. And so we did that.

But I think part, you know, the lesson, maybe, you know, because one of the hard things about writing that article was like, I’m like, I don’t know if this is going to teach anybody anything, right? Like, how do you use this to your advantage as a founder, but I would say the one lesson is, like, I was just in very transparent with them, and with all my investors, and eventually with the, you know, with the rest of the world, and I think it made them more comfortable, right, with, like, what writing it off would mean for them, right, like, because in so a lot of founders, if the company’s not doing well, or whatever, like, they just pretend that it is, or they just don’t say anything, they don’t respond to the emails, or they don’t send updates or whatever. And so the VC is just like, they don’t have trust in the founder, they kind of lose that sort of relationship. And so these just these really friendly decisions ultimately, just don’t happen.

Versus with me, I was like, I’m moving to Provo, I’m laying everybody off, because we got to get it profitable, I’m, you know, doing XYZ, and I would always say, at the end of every single email, like, if you have feedback, or concerns, or whatever, like, hit me up, you know, I’m a pretty open person. And so I think that gave them like a little bit more certainty that like this government, this company is basically dead. It’s like, obviously dead this person is pretending that it’s dead or whatever,

Mark Littlewood
There’s nothing more you could do to kill it.

Sahil Lavingia
So like, let’s give him the company back. You know, it’s a small business, like it’ll do its thing. And, and because they did that (Heisenberg uncertainty principle) that actually gave us the momentum to like, you know, gave me the renewed energy. And so like, people, you know, sometimes say, haha, like, Kleiner wrote off this investment that now would be worth, you know, four to five x. But what they bought in at probably.

But the truth is, like, it wouldn’t be because they required them to do that for it to be worth all this, you know, whatever it’s worth today, right? So so I think it’s, it’s kind of a tricky thing. I don’t think they regret. I’ve talked to the team since then. And they’re like, Yeah, it’s amazing to see what you’ve done. The truth is, like, you know, Kleiner is, is managing billions and billions and billions of AUM. So even Gumroad at its current state is not considered successful for them. Right. So it’s kind of a weird, weird thing to kind of grok but it is what it is. I’m grateful.

Mark Littlewood
So, you know, welcome to the BoS way of thinking albeit belatedly, I think, you know, that kind of independent thinking, one of the things that really kind of struck me about that, you know, the things that you were talking about there, and the conversations that pad around that you kind of had a reset about what is good, and what your objective and what your goal was for Gumroad. And there’s no way you would have been able to do that without or with those investors. Tell us a little bit about how that how that happened, and what the big change was?

Sahil Lavingia
Yeah, yeah. So you know, when when, when you have investors, like the generally the way that this world works is liquidity, right? So you have you buy shares at a certain price, and you share shares at a certain price later. And that’s how you make the vast, vast, vast majority of your money. There’s no such concept really as profit sharing or dividends or anything, right? And so, you know, it basically set yourself up for this billion dollar plus exit. Otherwise, it’s, it’s effectively zero. So, you know, everything you do is kind of to maximise that, right? Like, it’s called the growth at all costs kind of mentality. I called it in the reflecting our goal, “capturing value”, basically, like your goal is to capture as much value as possible, because that’s the venture, you know, that’s generally why people are investing in, you know, where the where the returns are coming from because, like, you know, you’re going to be valued at a multiple of earnings or revenue or whatever. You know, and growth is kind of the biggest part of that equation. And you see this with even with public companies, right?

Whereas in this new world where I no longer had investors, or like a lot fewer, at least of them, I could focus on creating value instead of capturing value. And so my thesis was like, How can I create as much value as possible, which is building a very different kind of company, and recruiting in a different way? And like kind of changing everything fundamentally about how we operate, which means much less about, you know, sort of like long term IPO, exit strategy, m&a, and more just about like, how do we serve our existing creators today?

It’s actually kind of like, anti growth at all costs, like, I don’t care about growth at all, really? Like, I’m just, you know, it’s kind of ironic, because, like, I raised money from, like, a new set of 7000 investors recently. And a lot of their questions around growth, and I’m like, I’m sorry, if you invested because of growth, like, you know, it might happen, but it’s, I don’t even think about it, you think about it more than I do. So I don’t feel bad about that whatsoever. Because I’ve communicated that, in my view, I’ve, you know, my superpower is that I’m super open. So like, I don’t feel bad about the way that I operate. Because I give people plenty of opportunities to know that.

So I think that’s also gives me a lot of power, quote, unquote, to kind of do things my way, you know, um, and yeah, so it’s sort of been about just like talking to customers. And, you know, serving them just figuring out, okay, how do we make the product better, right? And that doesn’t mean, not growing, necessarily. Sometimes you have to grow the team to do that. But it’s about serving our existing cohort of people. It’s not about selling to new people, it’s not about how do we grow the business faster? How do we make more money? It’s like, how do we help the existing creator base, earn more money. And generally, if we do that, the other things kind of happen.

But I just think in terms of like stress levels, and things like that, like, and also just like focusing on what you can control versus what you can’t control, it’s not necessarily up to you, how fast you grow, right?

If it were, like, everyone would be running fast! I mean, I don’t know. Yeah, you know, the truth is, like, a lot of these things are out of your control. And so I just generally think it’s healthier if you can take a long term view of it, but you know, to just work on the stuff that you can control, make things better, improve the product, you know, optimise the things in your life that you care about. And make sure that the sort of the base case is, is pretty healthy for you.

And then if any of these things happen, like COVID really accelerated the company and other things, that crowdfunding was like a regulatory change that I didn’t predict, you know, I was just able to take advantage of it, because I’d done the other things, right. Like I had invested in the things that I cared about, like building an audience being open sharing. And so when I did the crowdfunding round, like, we raised $5 million in 12 hours from 7300 people because I had invested in all of these other things with no real goal in mind, right? Like, my goal wasn’t like to raise a bunch of money from a bunch of people in this new way. I was just living my life the way I felt like I wanted to, and then ended up serving Gumroad.

So now I just want to keep doing that. Because like, clearly it works, right? Like, clearly, like, there’s seems to be some sort of these trends, I seem to be at the forefront of at least a couple of them, the creator economy, future work, democratisation of VC, whatever. And so like, I can just kind of double down on my interests. And, and it seems to be the best thing I could have done, because if I put together a business plan, it wouldn’t have included COVID, it wouldn’t have included crowdfunding. So it seems just pointless to me. Right? Like, why predict the future? Like why try? It’s, it’s not doesn’t work. Crypto, who knows what’s going to happen!

So I always tell people we’re just trying to build a faster horse. Like, everyone loves to say that quote from Steve Jobs, or Henry Ford, or whoever it was right. The truth is, the car was only invented once, like, you know, and then you just make the car faster and more efficient. And like, you know, actually, like, most people are building faster horses. Like, that’s generally what you should be doing. Very few people are actually reinventing a new wheel, right? Like, this happens very, very, very infrequently.

And it’s, by the way, it’s never predictable, right? Like, it’s not like Newton was like, I’m gonna discover gravity. Right? Like knowledge creation is inherently unpredictable. It’s if it were predictable, we would already have all the things right like and so I just think even even when I when I think founding stories of big companies, very rarely was it like the goal in the beginning. We want it to be $100 billion company like Stripe did not start out with that in that motivation. Once it became a possibility, they may have optimised for it. But like generally, very, very few companies actually start with that in mind. And I think that’s kind of the some of the toxic kind of thinking, I think that happens these days is people think they can wish it into being. But it’s just not true.

Mark Littlewood
Well, it’s more than NFT thing. So let’s talk about Gumroad. And how you run it. It’s, and this is the sort of second article that you had, which was about how you’re how you’re running the company. So just to confirm no full time employees.

Sahil Lavingia
Yeah, except for me. Yeah. No, no full time employees. I’m a salaried employee. Yeah.

Mark Littlewood
No meetings. No deadlines.

Sahil Lavingia
Yeah. No, no social activities and slack. No retreats, no perks, no equipment, no internet connection, no phone. No health benefits. Nothing besides Cash for Work, or equity if you want to, but yeah, those two things, you know, it’s very, very, very transactional.

Which is amazing. I think it’s, it’s like the best way I’ve ever worked. And so far, we have not had any, I don’t know, any real issues like unionisation, or any of these things. Generally, people like this, this way of working, I found.

Mark Littlewood
So is there a particular kind of person that appreciates that culture and is bought into it?

Sahil Lavingia
Yeah, yeah, definitely. I mean, I think you know, generally the Basecamp, kind of attitude, people really, you know, that jive with that jive with this generally. Basecamp just announced some changes today actually, the way that they work, which are kind of interesting. A lot of people want to build their own companies, right. Like, that’s, it’s really appealing for them, because it’s very hard to build a company if you’re working in another company. But at Gumroad, you can do it quite comfortabl; you can work 20 hours a week at Gumroad, and then 20 hours a week on your own project or whatever.

So that’s, that’s another popular archetype. There’s people who just want to maximise the time, the free time. And so Gumroad is one of the few places where you can work 20 hours a week, in a consistent way, most companies don’t even allow you to do that. So if you just care a lot about surfing, or rock climbing, I talked to somebody the other day is like, I just love rock climbing, I want to work two to three hours a day. And then I want to go climb, or you know, vice versa, go climbing and work or whatever. So I assumed like ski bums, like, you know, a lot of those kinds of people, surfers like this way of working will be quite appealing to those kinds of people.

New moms, too, you know, like, if you have a kid, and new dads, I don’t discriminate, like, you know, like, you have a kid like meetings suck. I mean, like scheduling this stuff, like it’s not, it’s a huge time suck for everybody, and is stressful and annoying. So I think there’s a lot of reasons where, you know, people don’t want to sit in meetings all day long. So there’s, there’s a wide array, I would say that the profile of people who don’t want to work at Gumroad are the people who, you know, they want to work a tonne of hours, right, like I used to do back in the day. So they may be young, they may want to put in like, they they’re single, they just want to, you know, especially during the COVID, like what is there do, you might want to work 50-60 hours a week, if you if you believe that you’re going to get paid, you know, 200 300 or $400,000 a year to do that, that can be you know, a decision that someone can make, they might want a bunch of stock in like a fast growing rocket ship like Stripe, or, you know, one of the one of the many startups.

So that’s another reason that you want to go that path where they, you know, you really care about startups, that’s another one, right? Like, you just want to be in the ecosystem of startups and venture capital and blah, blah, blah. Like, that’s also appealing to a lot of people. So there’s a few reasons but honestly, my guess is like, most people don’t care about any of those things. Most people don’t want to work 40+ hours a week, most people don’t care that much about Silicon Valley in San Francisco. Most people don’t need to make $400,000 a year, if it means working, 60 hours a week or the hours week or whatever, right? Like I think they just those were the options, right? Like you get it you get a degree in finance. There’s not that many options to work even 40 hours a week, like you get into New York, and then you you know, you’re working from like, seven in the morning till 2am. And that’s just the norm. It’s just what it is.

And so, yeah, it’s it’s a very, you know, different way of thinking about things. But it’s a huge competitive advantage, right, because like, we win those people, like there’s a lot of people who want that. And there’s not that many companies who offer it. So we can hire like, really amazing people who like, you know, we wouldn’t have been able to get if we were like, sorry, you have to be in SF in an office for 40 hours a week, they just never would have worked at Gumroad. And we’re starting to win people that I think like, you know, if stripe were to win them, it would be like noteworthy, you know, because it’s because of the the model and things. So it’s gonna be really interesting.

I think the sort of last missing piece of it is if Gumroad actually succeeds even better, faster because of it, right? Because Gumroads still in like kind of the weird startup mode, like we’re kind of an outlier. But if we can grow significantly, if we can really compete in the crater economy and say, Hey, we’re actually pretty competitive with substack, or Patreon, or teachable or whatever else. But we’re, by the way, no, no one who works full time. Like, that would be pretty interesting to a lot of people. So I think a lot of people are watching Gumroad. And I think if we can execute in the next year or two, it may change a lot of minds. So it’ll be interesting to watch and see

Mark Littlewood
How many, not full time people, but I mean, I guess how many individuals are working on a part time?

Sahil Lavingia
I mean, some sometimes it’s hard to track. But at least 30 right now. 30, and we on boarded six people today. So 36 now, and we’ll probably grow to around 50, by the end of the year is my guess. So yeah, you know, a sizable sizable chunk of people. 50 people is not a small, small number.

Mark Littlewood
How do you think about the contract – or the arrangement – that you have with them? Because it’s pretty, I mean, I know you’ve written about this, but if we could just talk about it a little bit. You’re saying I will do this for x amount of time? This is my availability? How does that kind of work? How do you how do you build that into the model that you have the business?

Sahil Lavingia
Yeah, totally, so when we went remote, we went to remote, sort of by force, right? Because we were gonna die in an office was very expensive. So it was like one way for us to save $25,000 a month. And so basically, you know, once we did that, I had to, like document everything, I had to put everything in notion, I had to put everything and github, like everything, there’s no tribal knowledge, like I had to kind of document everything. And even like I was thinking about selling the business at one point. And so I had to document everything for that, to make it as attractive as possible to an acquire, I had to minimise anything manual anyway. So so it was a big, it was a big focus, to kind of automate everything, and then anything that we could not automate, you know, document.

So that kind of force that sort of, we call it the discipline, I guess, of, of asynchronous communication, right. So when people started joining the company, I was like, here’s everything, like, here’s notion, like, here’s everything that we, you know, that we that we have, and I wanted to make my life easy. And so anything that only I know, is work that I have to do, because people have to come to me to get it, right. Like, for example, if I need to make an offer to an engineer, like, if only I know how much engineers make, then I have a job, which I don’t like jobs. So like, we have a internal document, we pay by the way, we pay everybody in the world, the same rate. And it’s all documented internally within the company, so anyone can look at and see how much everyone is making and roughly how many hours people are doing and stuff like that.

So that’s kind of like the you know, a lot of a lot of why it operationally people join the company, they go through an onboarding process, which you can see if you go to www.jobs.Gumroad.com just a notion doc kind of outlines how we how we hire, there’s a coding challenge, there’s like 30 minute phone call, normally a 15 minute phone call, to be honest. And then they start a one month trial period that’s paid 10 hours a week or so. And then if that goes, well, they start working for us indefinitely as long as they want to.

And then basically Monday, they get added to GitHub, slack, and notion, you know, and then they’re free to work, you know, they see all the stuff, they can kind of pick what they want to work on. And if they need help, they can ping me or Daniel our head of product or anyone else and you know, but generally like and then you know, they invoice us like every week or every two weeks every month, they just send us an invoice saying, hey, this how much work I did. This is my hourly rate. I hit pay or approve, actually, and then they get paid. And that’s it.

And so, you know, it’s funny, because there are a lot of questions people have about this, like, what if people don’t work or like how do you you know, how do you check this and like, how do you budget and like, you know, how do you make sure that like for example, one very, very common question that engineers asked is like, is there an on call rotation like how do you have a company that processes hundreds of millions of dollars worthty of payment like in this way? And my answer is like, I don’t do anything. Like it just works. Like it just, it turns out people care. People are accountable. People want to work on Gumroad. They want to serve our creators. There’s no other reason really to work at Gumroad. To be honest, like, if you don’t care about serving on creators, like there’s better places you should be at. And so there’s no need for me to do a lot of this stuff.

How do I know people are working? I don’t they they seem to be like, I trust people. Maybe at some point, I will not be able to, I will have to make some changes, I will might have to add some process. But you know, they, they really just add them to get up slack a notion. And then they start working, they invoice I pay them, they quit, they don’t like it. But generally our churn is like insanely low, like it’s too low. Like, I thought our churn would be high, which would be good, because we get a lot of new blood and people start companies but like, you know, it just seems to work.

Someone asks about how do you know they’re not having secret meetings? I don’t I mean, they’re welcome to have meetings if they want. I don’t know, I don’t care. I don’t like meetings, so I don’t have them. But if they have secret meetings, I’m not going to say hey, sorry, I saw this, I heard that there was a secret meeting. So you’re fired. You know, it’s like, we don’t have social channels and slack, none of them. Not, because we’re apolitical that we probably would be considered that in, you know, in this climate. But like, you can start like a group. I don’t know, you can start it, you know, there’s just no, I think the oversight required is insanely minimal. When you have like a well defined product, well defined vision.

Yeah, it takes care of itself. Like, there are a lot of these things that that people really obsess over. But like, they just don’t seem to matter. And I always say, Look, if there’s a problem, like we fix the problem, I mean, I don’t have to brainstorm problems ahead of time. Like, you know, I can move very quickly. I don’t have to ask anyone for permission, I just do these. I just, you know, I decide to do things. What I do is I just I say, I’m going to do this, then I tell the team I’m thinking about doing this, is this stupid? Most of the time people say yes, it is stupid, and then I don’t do it. And then 10-20% of the time, they say this is awesome. This is a great idea. And then I do it, you know.

And by the way, like the other weird cultural thing that I find a lot of companies is they rely only on their company, right? They rely on these people who work 40-50-60 hours a week for them to do the work. Because there’s this kind of more graduated kind of people who work at the company people don’t work at the company people get paid Baba blah, like, they you know, I can I can ask anyone in the world for why am I only asking my people, you know, my 10 full time employees or whatever for for feedback on what Gumroad is doing. I can ask our creators, I can ask anyone on clubhouse, I can ask Twitter, you know, I can ask 10s of 1000s of people, you know, for advice, and that’s what I often do, which, you know, makes Gumroad a much, much, much better product, because we have far more ideas, than most probably companies have at our at our stage in our scale,

Mark Littlewood
Are the crowds always wise?

Sahil Lavingia
Well, the beauty of it is I never have to listen to them, you know? Right, like, I’m a dictator, I’m fully 100% A dictator

I mean, even with my rolling Fund, which I’m very open about, I’m probably one of the few funds in which you can actually read all of the LP updates for, like, every single person basically can calculate how much money the fund is making, which is like very rare in Silicon Valley. Like if you, you can’t find that information out about basically any fund. But it’s one person, it’s just me making decisions, I make decisions, basically on the spot, I wire $100 – 250,000 in 30 minutes. And then I move on with my life. And it’s a rare, it’s very rare, I’m deploying $12 million a year this way.

And that’s, you know, roughly the same scale is like basically any early stage fund that has partners and employees and staff and and like all of this stuff, I have none of that. Because I just think it’s bullshit, to be honest, like it’s unnecessary. It’s things that you do because you feel like you have to do them. And that’s the way it’s been done for a long time. But if you have served some of the things that I have now, you actually don’t really need to do a lot of this stuff. And there’s a lot of data that actually says this. It’s just, it’s just most most people don’t have what I have, so they can’t do what I do. You know,

Mark Littlewood
So, come to the investment piece as we go. There’s some great kind of questions kind of coming in quite a lot of them. You’ve been out You’ve been dealing with as we as we go, which is great, but how do you kind of do the stuff at Gumroad that you don’t really want to do? And I suppose he’s one, one example, as it says, you know, in some sort of instances of people saying, hey, this maker, is this creators using my work. That’s my copyright. I should be paid for that. These guy’s have stolen… And that piece, the sort of policing of that seems to be.

Sahil Lavingia
To give you an even more loaded example, it would be like someone maybe, I don’t know, they believe it’s art, but it’s like, offensive to a certain group of people. Right. Like, and this group of people wants to deplatform this creator. Basically, my rule is always is I have a sort of a – I haven’t written this down, necessarily – but like, you’ll, you’ll kind of figure this out. One is openness, right. So like, the way that like, the process, the way in which we handle these things is very open. So everyone knows how we work. Two, it’s automated, it’s a process. So it scales. And so anyone can submit sort of, let’s say, in this example, like they can file a report effectively. And because of the openness, they kind of, they should really know ahead of time, if this is going to result in a suspension or not, right. And then it makes my life incredibly easy. Because if they’ve given me the stuff that I require, and by the way, if they don’t give me the stuff, they don’t get deplatform, they ignore the request. And you know, and that’s on that’s on them if they want, if they want me to take action, it’s on them in my view, just the way I think about it, to do it the way that I want them to do it.

But then, you know, it makes my life incredibly easy, because it’s literally a 10 second decision, because I know I have a very clear framework, which by the way, anyone can do my job, too. Because the way I do my job is written down, I literally like I have it open, I’m like, Does this match this thing?

For example, you have to provide content on Gumroad, you have to provide evidence that’s on Gumroad hosted by us, right? If you provide evidence of a tweet that they have, that’s offensive, or it doesn’t even matter, it’s irrelevant to us. We do not look at that we don’t care. Or it’s not even that we don’t care, certainly I care, I have my own views on a lot of this stuff. But the way our process does not care. And that’s different, right. And that way, when employees have a concern, they’re like, I don’t like the way that you’re handling this or whatever. It’s not about that. It’s about the system, it’s about the process, they can make a suggestion, they can open a pull request, they can give feedback to a process that we have. But they cannot argue with the decision.

And so I think that’s kind of a clear distinction that I think a lot of people there’s, you know, Twitter, for example, I think, doesn’t really have a clear set of guidelines. And so that causes them a huge amount of headache. Because the truth is like, you know, there’s a few people in the organisation that can decide who gets to post and who doesn’t, that’s just the truth. But they don’t admit that, so they have to, like, obscure it and all of these things, and it just makes their life hell. And I’m not saying they should admit that right. Like, they’ve, I’m sure they have thought about it. And it just doesn’t make sense for them. And they won’t. But Gumroad is, I think, also lucky in that regard, that we’re not big enough that like, I can kind of work this way, and it’s fine, right? Like, if someone raises a bunch of money on Gumroad, and then like, kills 10 people or whatever, like, then yes, we will likely have to revisit some of these things. And we’re always open to that idea.

I’m a very reactive person, like, I will not proactively tackle a lot of these issues. And I just make that up front. Everybody who joins the company, I think that’s the most important thing you could do, right, is to just communicate to people like I’m doing now, or like, you know, with a hiring process like this, these are the reasons you may hate working at Gumroad. Right? Like, you mean, if you really care about a certain political issue, or if you you know, that’s great. I mean, I do too, about certain things. But like, you know, just make sure that you’re, you’re a good fit for the way that we work. And, again, the growth at all costs, I think leads to a lot of these problems, because you’re trying to grow so fast that you aren’t super, maybe upfront with a lot of these things, right? So you end up having all these people and then later on in their life, the company, you’re like, Oh, these are actually not the people I want. And then that creates so many of these headaches, right? You have to filter this stuff out as soon as you can. And so I always think openness is like a really great way to scale because it means you just have to make less decisions, less things in your control. But yeah, certainly there are things that I don’t enjoy doing. And I’m always thinking about, How do I open this up? How do you know these 15 minute phone calls? I have to do 15 of them a week right now, because I’m going through a recruiting sprint? Do I have to? Like, can I write like the top 15 questions and say, Hey, if you don’t have any questions, you can just start the drop period. You know, now, you don’t even have to talk to me.

And I’m sure that seems to me like an inevitability. Can we open source the whole product, so you can actually start contributing to the code base, maybe that’s the way that we hire is like you have to contribute something to the code base or something. And that’s the kind of first level filter, but there’s like this kind of power law, right? Where like, there’s like so many people who who are at step one, like there’s so many people who want to write a book. And then there’s like, only 5% of them actually write a book, or write even a first draft of a book and have that

Mark Littlewood
5% of them have a title, its a smaller number for the actually writing the book.

Sahil Lavingia
So you know that so as long as you have some blockers and some filters and and like, my goal is always to have a filter that alienates most people, but anyone if they want to can get over it. So I don’t think filters are good if they discriminate, or if they have, you have to be an SF or like something like that, that really does force people out of the out of the system. But you can say, everyone has an hour of free time, hopefully, right? So like, you can ask them to do something that takes an hour. And so that’s kind of how I think about and that generally gets like a tonne of the cruft out and then my life, it’s kind of like my inbox is a lot cleaner for it. Right? And then I can I generally reach Inbox Zero, I’m pretty public on the internet, my emails public by Twitter’s open DMS, blah, blah, blah. And like, People always complain about Inbox Zero; I’m at Inbox Zero, like all the time, basically, like, an inbox zero by 8am. Every day. And and that is all the inboxes and maybe 9am, and then the rest of my days, you know, basically doing whatever I want. But that’s because of these other things that I’ve done. Most people aren’t, most people do not have the same level of openness that I do.

Mark Littlewood
So very interesting. And I know, I’ve got a couple of channels, the best way to ask is in the chat, and we’ll bring you up on screen to ask as well. But when you’re investing, or who are the other people running companies in this bizarre, weird, strange, crazy way that seems to work for you?

Sahil Lavingia
Yeah, honestly, not many. It’s very, yeah, it’s I tried to find a bunch. Generally, they’re a lot smaller. I think a lot of people have started running companies this way. It just they haven’t reached scale yet. And so they’re not as well known.

I think, ironically, what makes Gumroad really compelling to a lot of people is the fact that we used to run the company in a different way. Right. And so that this, the reason that, you know, Gumroad is interesting to people is kind of the reason a lot of these other companies are not yet interesting, because the truth is, like, you know, many companies are run this way, right? Maybe most of them, but like you just don’t know it. Like the whole music industry, for example, runs this way. Basically, no one is an employee of anything, everyone, everything is kind of like project based. And like, you know, Kanye West hires a bunch of people for the album, blah, blah, blah, like, this is just the way the music industry works and has worked for a long period of time.The film industry is actually quite similar too.

So there’s a lot of these, these kind of the things that we just don’t think of them, they don’t match the kind of the archetype, so much. Basecamp is probably like the most famous example of it. WildBit as another one, Panic is kind of a little bit like that. But like, I think it will take five to ten years to for a lot of these companies that started this way; this way was only possible, like 2015 onwards, because a lot of these, these toolings didn’t exist yet to grant notion figma. You know, github’s product quality is improved a lot, like a lot of these things weren’t even possible, you know, a few years ago, and so it’s gonna take time for these companies to get built in this new world and reach scale in this new world. But my guess is, the number one economy that has a million of these companies, crypto.

Crypto is full of them. Literally every company in crypto is basically decentralised. No office, everyone kind of works, you know, as a contributor to the company, there’s really no full time employees. Everyone works gets paid based on how much work they’re doing. Not everyone, obviously, but like, you know, it’s quite common in crypto, and actually, that’s kind of how I look at the creator economy is like, traditional economies over here. Startups are over here. Gumroad is kind of over here, Creator economy is kind of over here. And then cryptos like the crazy libertarian, whatever you call that, you know, and they’ll meet in the middle. Most companies will end up are kind of in the middle where they’ll have some full time employees but they’ll have like tonnes of contributors. That’s kind of like So, where a lot of companies will end up long term, my guess is WordPress looks a lot like this, Automatic. They’re probably a pretty good example. But it takes it takes two things.

One is you have to do it. But then two, you have to have a founder CEO who’s willing to like, talk about it a lot. And that’s kind of a personality thing that a lot of people just don’t have Matt Mullenweg talks a lot. He speaks a lot. So you know, Jason Fried, DHH. They’re very outspoken people. And so there’s just not that many. You know, it’s surprising to people sometimes, because it’s like, but the truth is, like, those are the people you listen to, because they talk. But the vast majority of people I know, as an investor, I’m always telling my founders, like, talk, like, do this, it works. All I do is post like little banter on Twitter, and I have 200,000 people that like my hiring my entire hiring process, like, the hardest thing that my my investments deal with generally is hiring people. That’s like the hardest thing about startups. And my hiring process on Gumroad is I tweet once, and then I’m done for six months. And I hire really good people. And you know, I do it all myself in like, but you know, it takes a huge audience, you know, the value is there. I just think a lot of people don’t see it, or they don’t want to do it, which is fine. You know, more more cake for me. Right. But uh, it is a, it is very advantageous.

Mark Littlewood
Do you think you’ll get to a point, I mean, we’re talking with Amir and Wade from Doist and Zapier just earlier on, and both of them had been talking, I mean, they’ve got these to a degree, greater or lesser degree, asynchronous ways of working. Amir went for absolutely no meetings and was like, this is perfect, this is what I want. And it didn’t work. And he had to bring them back. Just beyond a certain certain size, is there a kind of an optimal thing for you? Or do you think this can scale?

Sahil Lavingia
I mean, you know, the truth is, like, I hate meetings. And the reason we do this is because I hate meetings. So like, if we need meetings for Gummer to get to the next level, that’s fine. That’s more important than what I care about. But like, the beauty of it is like, I don’t need to work at Gumroad. Like, you know, who says I need to be the one running the ship? Who says I’m running the ship now? You know? I’m not really to be honest, it’s a kind of runs itself. Like, I feel like I’m the kind of like the the person like adjusting the rudder once in a while. But like, there doesn’t really need to be like a strong leader. There’s so much momentum at this point.

I certainly think what will happen is like, there’ll be parts of Gumroad that will need meetings, right? Like maybe the design team needs meetings or something like that. And like, they can have meetings if they want, right? I’m just like, I’m not going to enforce meetings on anybody. Mostly because I don’t want to enforce them on myself. Right? Like, I just think like the rigidity of it can be can be really bad. You know, for my own personal life, I need free time, I need to be able to react quickly to new projects that are interesting, like crowdfunding rolling funds. Like the reason I’m so fast, and that and not onlyam I fast, but like I kill it when I do like, I don’t just have it like, and why am I able to do that? The truth is, because it becomes my full time job, right?

Crowdfunding was my full time job for two weeks or three weeks. So like, it looks effortless, because it’s like, how is this person maybe doesn’t look effortless? If it looks effortless it may be because I’m running a company writing a book, crowdfunding running a rolling fund that’s bigger than most funds, all at the same time. But the truth is, like, I’m only doing one of them at a time. And like the rest is kind of delegated or automated, or, frankly, just not that much work. If you’re willing to, if you’re willing to be open about how little work it is, the truth is running a $12 million fund is five hours a week for me. For less, it’s just not a big deal.

Because what do I do I meet with founders, and I give them money. That’s pretty easy. I was doing that anyway, for free. Except I wasn’t giving them any money. So like, now I just give them $100,000. You know, and so, you know, a lot of these things, if you’re willing to admit that like a lot of VCs are not willing to admit that the vast majority are not willing to admit that because it would put their job at risk. And why are you paying this much money? I mean, like, that’s insane, like, you know, but if you’re willing to admit that like the world, like, you can live a very, very different way. And, and the truth is like, eventually the truth will come out. Like eventually the truth will be clear to the LPs and to everybody in the world. That’s kind of the nature of it. And then the people who you know, were the most upfront about it will win, quote unquote, right like the Vols of the world that Jamaats of the world, the people who have clear eyed and are willing to take bets in public. Generally people want them to win.

Elon Musk is a great example of this. Elon Musk is one of the best people on planet Earth, in my opinion. Because he takes bets, he goes all in, he ties it to his brand. He does it publicly, you know, how many how much money Tesla has spent on advertising? Zero, they’ve never spent $1 on advertising. They’re the best car company in the world. They probably get more free advertising. Everybody else. People hate Elon. Yeah, of course. Hate is zero customer acquisition costs outrageous free. You know, he’s on SNL, like what other car companies do whatever post, you know, that’s like, brilliant. That’s priceless. And so like you got I think you just got to respect the game, you know, like, it’s a, it’s incredibly impressive. But it requires things that just most people are not willing to do. Hmm.

Mark Littlewood
Yeah. Do you invest for impact? And I’ll explain what I mean by that or return and by impact I mean, you’ve got this thing about, hey, that these different ways of running businesses? If your business Gumroad, three years ago, came to you now and said, Hey, this is what we’re sort of doing. We don’t do meetings, blah, blah, blah, give me some money. What would you say?

Sahil Lavingia
Yeah, I mean, I like to say that there are two kinds of investors, investors that invest for returns and liars. Like, you’re not an investor, if you’re not investing for returns, like definitionally, what your job is, is to take capital and allocate it in a way that increases the value of that money, and you’re hopefully doing it for institutions or individuals in which you believe that them having more money is a good thing.

An investor that says they don’t care about returns is like, I don’t know, that’s like, that’s the point. I mean, what do you do, like, you’re just admitting that you suck at your job or something, I don’t get it. You know, which is, again, this is a truth that like, a lot of people aren’t willing to admit. They say they care about impact. But like, I don’t know, I you can see the behaviour. Behaviour is pretty clear that most people care about returns, the people who don’t care about returns, care about returns, they just suck at getting them. So yeah, I invest purely for returns, I would never invest in Gumroqad, I would never invest in Gumroad, I would never invest in a CEO. That’s like me. And I’m very open and clear about that.

Mark Littlewood
What are the top three things that make you uninvestable to yourself?

Sahil Lavingia
One Gumroad is not my number one priority. That’s like, that’s game over, like I would never invest in someone who, you know, has other things that they care about too much. I know what starting companies like, right like, and by the way, like, you know, Gumroad is also hold, right. So like a lot of the things I don’t have to do anymore. If I was starting a new company, I would not be running the company the way that I’m running it today. So that’s a big one.

Two I’m Angel investing a lot in other companies. So my bet is incredibly hedged. At this point, gumert could go to zero, and I would still be quite financially well off. So that’s another reason I would never, you know, I want I want people who are really in like, they have real skin in the game.

And then three, probably, it’s pretty clear like that I’m not willing to play the game that much anymore. And like, I’m too smart. Like, I know too much. Like, you know, I think to build a startup, you kind of have to be a little stupid. Like, you know, you have to be naive, you have to be, you know, willing to sacrifice a lot of your personal health, to be honest, to make it work. Sometimes you have to be set, you know, you like, you have to be willing to sacrifice a lot of your personal relationships, etc. You know, like, I didn’t go on a date for five years in San Francisco, like, these are just things you have to do.

The Steve Jobs reality distortion field, right? Like, how do you do it? You? Well, first you have to apply to yourself, right? You have to be a little bit delusional. To see a world that doesn’t exist, and then you know, make it exist. And most people fail to do that. So like, those are some of the reasons I would not invest in myself.

Mark Littlewood
What’s your ultimate personal goal? How do you want to be remembered?

Sahil Lavingia
Have kids I mean, that’s, that’s my own. That’s all. That’s my only goal right now is to have kids, which will happen in three to five.

I tell people like if you go to my bitcloud profile, which is like, my true personality is like, I’m just killing time. I’m just killing time until I have kids. Like I’m just messing around. I’m just doing what’s fun. Which I think is why a lot of people sometimes get pissed off at me is like, I do their jobs for fun. And I do it better than them with less time investment.

I am just having fun like I’m running Gumroad or the way that I want to run it. writing my fund the way that I want to run it, I’m writing my book the way that I want to write it. And, you know, I don’t have to ask anyone’s permission anymore to do these things. I don’t have to, like anytime I need to raise money in the future, I can tweet. And I will have as much money as I want.

Anytime I need to hire people, I can tweet and I, you know, it’s, it’s, it’s an insane sort of leverage, you know, that I have now that allows me to work in this way. I like having interesting conversations with people. I like other things, but in terms of an ultimate personal goal, like I think having kids is definitely number one. And someone asked why. I mean, just because people say it is I mean, people say it’s awesome. Everyone I’ve met who has kids who said it’s like the best thing they’ve ever done. We’re human after all.

I want to have kids, I want to have as many of them as soon as possible, probably, you know, that’s not up to me. So, you know, probably won’t have 50 Unless I can figure it out somehow. Who knows, I don’t have to play by society’s rules to do it.

So, you know, I’m, yeah, I want a really nice house. I don’t know, like the basic things, you know, it’s funny, because like, all of these people have like, all of these different ways of going about their life. And that’s all great. But it’s funny, because everyone kind of ends up in the same place, which is like, you have like, a semi decent house, you eat good food, every once in a while. You have grandkids and you like, hang out with your friends. And like you barbecue like everyone, like, doesn’t matter where you know, like, how rich you are, like, those are the best things in life.

I treat money like a game, like I do want to maximise returns. But it’s just fun, just for fun. It just is. It’s just a it’s a game with a number. And I want to be the best. Why? It doesn’t matter. I mean, why do you want to climb a mountain? Like, you know, humans need challenges. And this is the challenge for now that I’ve picked for myself, but you know, like, they’re harder things. Like I’m writing a science fiction novella right now, that’s far harder than any tech thing I’ve ever done. You know, which is why I’m doing it just to do it because it’s hard.

Mark Littlewood
It’s interesting. So what kind of rules that you’d apply to having kids that the your rules rather than the ones that I will following? What am I doing wrong?

Sahil Lavingia
I don’t know. I mean, we’ll find out. I mean, one thing I think is weird is like how few kids people have, like, there are these people who are insanely affluent, right? Elon Musk, Jeff Bezos, for example. Like, I don’t understand why they don’t have hundreds of 1000s of children. Like why not?

Yeah, there’s, there’s you know, so I think there are a lot of interesting. I don’t know, society, society says you should do this or whatever. But like, I don’t know, I think it’d be really interesting to say, like, I can have a million kids, right.

I’m biologically capable of having millions of children. So can I like, is that possible? Obviously, you need certain, you know, technologies. And it’s certainly not possible today. But I but I, you know, it would be interesting to see if it is possible.

Mark Littlewood
Possible, I think it’d be harder to be a father to a million children.

Sahil Lavingia
It would be Yeah. It definitely would be, you know, I could I would only be able to Yeah, but like, I think there’s like a I don’t know, there’s there’s a way to do it. Who knows, I’m sure that these ideas are stupid. Most of the ideas I have are stupid.

But you got to try. I don’t know. It’s fun again, right. Like, I want to do new interesting things. Like, even though I think a lot of them will not work because like that’s how you find out, you know, if they work or not, like it’s very hard to kind of know a priority if these things are good ideas or not. Unless you actually like try it and like see.

Mark Littlewood
Well, kind of getting to wrapping up point before we before we go. I’d love to know if there’s anyone that wants to kind of come in and say something I can almost see Bridget bursting with excitement.

Sahil Lavingia
I mean, it’s funny. There’s a lot of comments around like, everyone assumes that you have to spend time with your kids. Like that’s also like another assumption that society makes like you can have a million kids without spending time with any of them. That’s not a requirement. Why would you treat your kids better than any other human being that seems discriminatory?

I think I have pretty good genes. I think I’m pretty smart. So like, you know, why wouldn’t I want my genes to be in you know, more people.

And by the way, everyone’s choice right. None of this is going to be his nonconsensual Of course, this is all. And this is just me bullshitting. I’m just having fun.

Mark Littlewood
Sure a lot some wasn’t where I was expecting this. It’s pretty thought provoking. Yeah. Okay, Sahil. Thank you very much. Anybody got any other things? Because I know there were the chat was moving at sort of quite a speed up.

Sahil Lavingia
someone says sustainability is everyone’s responsibility. Interesting. Yeah, I’m not concerned at all about the planet.

Humans are pretty, pretty darn smart at figuring stuff out. So I have zero concern that we won’t get through this. So far. We have every time. The planet will be fine on top of it. Everything is gonna go to zero at some point anyway.

Mark Littlewood
That’s entropy, man. He retorted two chemistry jokes in one talk how about that?

Sahil Lavingia
No, I think I think energy consumption is like a whole other con conversation. But like, I really, I think humans will consume more and more energy over time. And luckily, we have a sun. So like, we’ll figure it out. This is the beauty of technology is it’s unpredictable. By 2100, we will have less people on planet Earth and far better technology. I don’t think any of the issues that we think about today are are actually real, going to be real in 2100.

Which, by the way, everyone believes this, like both sides believe this. The left believes that it’s a real problem, and we’re gonna build the technology. That’s the solution. The right believes that, like, it’s not a real problem, but like the answer is the same for both sides, which is it’s not a problem between, you know, in 2100.

It’s not politics is the earth.

Mark Littlewood
Yeah, that’s interesting. That’s interesting.

Sahil Lavingia
If there’s 11 billion people in 2100 I will give you $11 billion

That’s definitely not happening.

Mark Littlewood
Brilliant. Really lovely to to have this conversation I think, you know, lots of different things going on that if anybody’s looking for quick cheap money from Sahil, what type of things do you invest in?

Sahil Lavingia
Yeah, I mean, I crypto is really interesting to me b2b SaaS, future of work stuff, ecommerce. But again, like, look, my goal is to maximise return. So I have zero real thesis, like, I will look at anything and everything.

Thesis, you know, theses are also made up mostly to raise money not to not to deploy capital effectively. Anything that you think, you know, as I mentioned, like, it should be your number one focus, you know, you have to be kind of stupidly delusional about it. If you are those things, then like, you know, hit me up, you can go to www.shl.vc and then there’s a form that you can fill out and I’ll get back to you within you know, within 24-48 hours or

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