What's up, everyone? This is Anthony Pompeo. Know most of you know me as pomp. You're listening to the pump podcast. Simply the best podcast out there. Now, let's kick this thing off. So he'll love being gay is the co-founder and CEO of gumroad. The technology platform that helps create a journal living selling the stuff. They make directly to Their audience. He is the author of the new book, The minimalist entrepreneur and a prolific investor. Sahil was previously. The number to employ at Pinterest as well. In this conversation. We discussed asynchronous workflow open sourcing a
Isn't it hiring people without talking to them? Decentralizing ownership and work and investing. I really enjoyed this conversation with him and I hope you do as well. Before we get this episode though. I want to quickly talk about our
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So he'll when you think about the asynchronous element, I want to start there because this sounds insane. And I think, you know that, but it seems to be working. How do you operate an entire business? Basically
asynchronously? Yeah. I mean, I think the simple, the simple analogy that we use whenever we kind of onboard people to come Road. And when I talk about it, write about it publicly is it's like working on an open source project except you get paid for it and it's not actually open source, right? And so,
It works. There's all these sort of these parts of different industries that work in this sort of a synchronous way. I just read this book The Cathedral and the bazaar. I think it's called about sort of the origins of Linux and how everyone was. Like, there's no way you're going to build this thing. And this way where everyone's just kind of hacking on this thing. And it's chaotic, right? It's super, super chaotic, but and crypto I think is the other one that I've sort of paid a lot of attention to I think cryptos a great example of an industry in which a lot of people have never met each other. They've never heard each other's voices. They never seen each.
Her in person or even over video. It's a you know pseudonym - Etc. And I think I don't know. I find that incredibly incredibly inspiring to be honest. And the reason that I think is so interesting is because I just don't think you need to bring your whole self to work. Right? Like if you can provide value, if you can create value, if you can, if you can do the job. Like, to me, it's sort of, you know, the other stuff doesn't really matter. And I think in the era of, you know, diversity, Equity inclusion.
You know,
people sort of spending a lot of time thinking about race and gender, and all these sorts of things. I think one answer is potentially, it will look just, it doesn't even show up. Right? Like everyone, I come road is like a cartoon, you know, Avatar and maybe their first name, but they can select any nickname they want and it won't like, why it? Why do I care? You know, we pay everyone in the world, the same rate, no matter where they work. So, you know, in theory, lamp beside sort of taxes. There's no reason for me to know, you know where and when people work and that
Another big reason we went a sink was, you know, as we started to hire people. In all of these different time zones. We now have people in 17 different countries. Any anytime you say. Hey, we're meeting at this time, where we have this sort of schedule. You're inherently creating sort of this like hierarchy, right? Where you're going to say. Oh, you know the sort of I live in on the, on the west coast. So now all of a sudden Pacific Coast, you know, PST is now like the default time. We're going to speak in PST and I just don't, I don't like that. You know, I just I'm not a huge fan of that. I
I move to Provo, Utah journalists would be like, hey, you know, which coaster you will run, like they would just assume that, you know, you must either be on, you know, in this time zone are--that's time. So there's like no other options and I'm like, actually, I'm in like the middle and so I just I don't know, maybe that was part of my sort of life experience, you know, growing up in Singapore, perhaps, where I just felt like constantly not, you know, the sort of like people weren't talking to me. And so I felt like I wanted to build a company where, you know, if it's a sort of 11 level playing,
Feel for for everybody would certainly means it's you know, maybe not as ideal for someone who is in San Francisco and wants to work at a start-up with an office, you know, and bean bags and then ping, pong tables and all these sorts of things. But but yeah, that's kind of some of the some of the reasoning behind it. It's what
changes for somebody on a day-to-day basis, right? If I'm an employee. I work at the business. Do I just not go to meetings? Is there like some of the workflow or system that's in place. Like, what is my day-to-day experience in an asynchronous work
environment? Yeah. I mean, I can, I can speak to
And it probably, you know, translates pretty well to a lot of the other folks in the company, because effectively in this way of working, everyone is almost like a CEO right where they have their own sort of, set of priorities. They have a ton of things coming at them, and it's kind of their job to communicate to, you know, let's say they're bored, which may be me in this case or other folks on the team. You know what they're working on, what their kpi's are, how their work is actually going to make those things happen. And if they do that in this sort of,
Ambient way, and I think Twitter is a really good analogy for this, right? You no longer have to say, hey, what are you up to today? You can kind of go on Twitter and, and learn about all the stuff people are doing. So it's like think about an internal kind of Twitter right where everyone is constantly sharing. If people are doing that super effectively than, I don't have to spend any of my time and nobody else has suspended. And in any of their time, kind of like what's actually happening, right? What's actually going down? And so I think that's, that's really, really important for me. But yeah, I wake up, I could wake up. It doesn't really matter.
And you know, one great perk about this way of working. Is you can take vacation. You can travel, doesn't really show up to anybody. I'm in New York right now. No one company really knows. I wake up. I answer all of my inbox, right? So slack GitHub and notion is like, where 99% of the communication happens. So those three channels, I make sure that I answer any of those things. I have a sort of a 24-hour SLA, which means, I basically get try to get back to everyone within 24 hours, which is a, you know, quite a long time. You have to work assuming that. And then once I do that,
that then it's kind of deep work for the rest of the day. You know, I just pick one or two different things that I'm working on and I just sort of, you know, I write or I designer I code or or whatever I may be doing but there's no meetings to distract me too. You know, I frankly suck at working when I know there's like a meeting even in three hours of, you know, at my brain can't like every five minutes. I'm like, is it, you know that my missing the meeting? And so, I find that I just just so much more productive. If I know that I do.
Free day ahead of me. And so that's kind of how everyone works. They wake up. They kind of do this. That's the stuff they're assigned and then they start working on whatever they feel is most important. And then they communicate that, you know, to the rest of the company asynchronously be a slack or an ocean or GitHub. And then if I feel, you know, every once in a while like hey, I haven't heard from this person a week or two. I'll go check. Slack first. That's kind of the cash. Right? And so I go check so I can check it out. I check all of the places first before I interrupt them before I require that.
That to contact switch because I think it's just super expensive. It just super expensive. Ask someone to say. Hey, stop what you're doing. And focus on me. Focus on what I want. If the assumption is, everyone is doing what they feel. Is most important that, you know, inherently. What I'm suggesting to them is, is not going to meet that are right? And so I should avoid doing that as much as possible. So
and when you think about the downsides of this, like, the benefits are very obvious, right? Deep work, no meetings, you know, he probably can recruit all kinds of people. Now, what are the downsides?
In your mind or like what have you seen so far? They like, hey, we still got to figure out one or two things.
Yeah. There's there are quite a few downsides. I'll be real. One of the downsides is that it's much, you know, there's a lot of hard conversations that I think are just easier to have it in person, right? You can really coach, someone, you can sort of be a therapist psychologist. You can, you can help the people in your company grow, which I think of your hiring, a lot of Junior people. Like, I would not recommend this way of working at all. And so, yeah, that's definitely a downside is we I kind of, you know, there's this sort of the saying,
Higher for white, why slope? Right? Or slope? Not y-intercept, right? You want to hire people based on where they're going to be in six months, not may be where they are today, and I found that just at a company like gumroad. We just we obviously care about slope but intercept is also really important. You have to start out an incredibly High bar because things like, you know, if you're not motivated to work and you need an office and you need to team, you know, you're going to struggle here like that motivation really has to come sort of intrinsically. There has to be a lot of self-motivation, which is great if you have those.
Characteristics. But I think and you just want, you know, what you want to do, just want to work. But if you're not then, you know, I would say it is pretty, pretty difficult to sort of find success. I come Road. And then, I would say just mental health. I think this is the, you know, it's sort of a big topic of conversation right now, and I personally believe that your workplace is not responsible for your mental health. You should find professionals. You should find people in your life, to have friends and family and all these. Sorts of things outside of work. I don't think work is a great.
Great place to find a lot of these sorts of things, but I do think it's a struggle for people generally, especially in a pet demick. And so I think that's one of the things we have to figure out is, you know, how much support quote unquote. Do we want to provide to our qualified employees or contractors? Right? And so that's that's a big one, you know, when someone, you know, passes away, you often, you know, or it's your birthday, often those needs are met, you know, for better or worse, by the company, right? Sort of lack of religion, lack of neighborhoods. A lot of people find that at work.
So I think that's something that we have to figure out like, you know, right now we're sort of a very extreme in terms of. We don't do any of that sort of stuff. There's no even social channels and slack but we might introduce that depending on if we continue to scale and we feel like some of those things are sort of necessary. The other thing I would add is is there's not a lot of like career growth, right? There's no ladder to climb, you got a job at government. As an engineer, you do an amazing job, you get paid an extra 25 bucks, an hour or 50 bucks an hour, or you get a spot bonus in the form of equity and the
Company or something like that, but it's not, you know, like L1 L2 L3. You can't really map out the next five to ten years working at this company. Like, you might be able to do at some of these other, some of these other places.
So obviously the work environment is very different than most places, right? And there's a lot of people who are attracted to this. You also are also experimenting. I don't know how you describe it with the hiring process as well. Talk me through this. I saw this the other day and I forgave him looked into it enough. So I feel like I'm going to hear right from you. Now, you guys are trying to
Hire people without ever talking to them.
Yes. Yes. So, yeah. It's weeded out a couple days ago, you know, you can now get a job at gumroad without talking to a human, which is kind of a joke in the sense. It's true, but it's a joke in the sense that, you know, like people complain. You can't cancel your nerd time subscription without talking to a human, right? So I said, well, why can't you get a job without talking to a human? You should be able to do all the things in life without having to talk to it to a human. And so, yeah, I mean the the reason I did it is because we were almost there, right? We basically had
This, you know, you have a job post. Then you have like a phone interview. You might have a coding challenge, might have like reference calls with other people when you put them on a trial period. You know, that takes three or four weeks once they succeed they got a job at the company, right? That's sort of the traditional workflow and I felt like, well, the trial period is the job. Like, if you can do the trial period Then I don't. Why do I need reference calls? Like, why do I need to even talk to you on the phone? If you can, like provably do the work and I had this other tweet which I again.
Inspired by crypto proof is greater than trust, which is if you have proof that you can do the job that I don't need to even trust you. I don't, you know, you don't even have to tell me anything. If you can just give me a URL and say, hey, I built this right? That's how I got the job at Pinterest. I said, here's an app that I built you. Download the app you use it. You don't need to interview. You know, anybody, you don't have to talk to anybody. And so I just felt like what if we work this way internally? Where we have no meetings, you know, I basically don't talk to anybody on the phone, you know minimal meetings Etc. Are like why?
Don't we just, you know, eat our own dog food and make that part of the hiring process and my guess is, there's some people who are like and there are some tweet responses that were like, really, like you want to work with people. You've never talked to in your life. Like that seems weird seemed very transactional, but the answer is. Yeah, like, I'm some of the, some of the people. I feel like I'm closest to. I just have a totally text-based Communication channel with, you know, we're both busy. We can, you know, text and and we respond when we respond, I assume this is how a lot of people talk to their friends in this era. And so, you know, applying
To work didn't feel like too much of a stretch, a stretch to me. And so yeah, basically, now you it's funny. We have this internal notion dock which is it's called a phone call in quotes because it's basically and this is part of what I realized was. I would do this phone call with every candidate and I would I would answer the same like five to ten questions over and over and over again. And so instead I just basically the next time I had a phone call, I wrote out our entire conversation. I answered every question. I wrote it all down and then I created a
Sort of text macros that anytime someone applies for a job. And I want, you know, they complete the challenge and I want to hire them. I just sent them this notion doc that says, hey instead of a phone call, we're going to do it, you know, here's an asynchronous version of a phone call. If you really want to talk to me on the phone. I'm happy to do it. But it turns out when we like higher this way and we're very public about it. Literally, you know, in the last two weeks. Maybe, you know, from that tweet alone probably like a, you know, a dozen people have applied to gumroad. Zero percent of them have asked.
You know, to talk on the phone, it turns out that people just don't want to, you know, people want to get that, you know, people want to do the job. They want to write code. They want to get paid to write code and then generally, they want to turn off their computer. Go for a walk, go for a hike, spend time with their family, friends, do whatever the hell they want to do. Right? We have rock climbers. We have professional Marathon, you know, ultra marathon runners, like there was a bunch of things out there to go experience that you know that you know, that that isn't work. That isn't the stuff around work. And so yeah, that's
That's sort of the process now is you do the challenge, you succeed, you do this asynchronous, phone call and then you start the trial period at you. Start, you know, you just start doing the work or my goal is. How fast can we get you to actually doing the work, right? Because ultimately that's the depths the true test. It doesn't matter. I mean, there's I mean, you know this like in you know that Facebook and all these comes, you all of this work to make sure you're hiring the right kind of people and then you still make mistakes like an insane amount of time, right? Everyone says that the recruiting process is broken. So my
My feeling is like well, then just get rid of the recruiting process. Just give everyone a job and see how it goes. And and that's probably you know, my guess is if we sort of draw the line out into the future again, kind of expired by crypto. My guess is a lot of this will look like Will Open Source cover of people will cook. You know, we'll get a job just by like contributing to the code base, fixing a bug or two if they do. Maybe let's say two of those, they automatically get into the trial, period. Get paid a hundred bucks an hour for three or four weeks. And then if they succeed, they get the job at Governor it, right.
And so, I think there's even for, it's funny because people think I'm extreme, or what have you? But and I'm like, no, there's, there's a whole world out there that we haven't even gotten close to. You know, if you think about, you know, we've been doing this remote work, a sink thing for, you know, as a society for, like, 18 months. Now, you know, like it's been. It's a very short amount of time compared to, I don't know when we started working in factories, right? Like in the, you know, eighteen hundreds or
how important is it, how important is it for people to be able to communicate well, like all of a sudden right? If you and I were on a phone call.
Even a mom. I'm a bad Communicator. Like you can ask some questions and kind of quickly iterate to. Okay. This is what he's saying, but now all of a sudden asynchronous I think of it almost like shots on goal right in the conversation. Every time I speak or you speak that's like a shot on goal and maybe there's I don't know normal conversation 500 shots on goal between the two of us. But if I send you one slack message and then you know 18 hours later you respond with one message back and then I respond again, we hit three shots on goal. Has a 24-hour period. It's way harder. If one of us is a bad Communicator. So what have you seen there or are there things that you guys?
Do to help people become better communicators in this environment.
Yeah. No, that's totally true. I mean, you know, the friend right where you like, text text them like, you know, I think. And they just like, hey, do you wanna hang out on Thursday and you just goes back and forth and back and forth. And then there's certain people who are like, hey Thursday 5:00 p.m. At this place. Does that work for you? Right? And so you just have to find those kinds of people who minimize those feedback loops because you're right. They're insanely expensive at Governor. I mean, if you say, hey saw idling need this. I'm blocked on my work. I need an answer from you on this A or B and then
It's me 24 hours to get back to you. I mean, that's just not going to work. Right? And so yeah, you have to find people who are the way that I think about it is you basically have to predict the questions that people are going to have, right? If imagine, you know, you write an essay. What do you do? You send it to a bunch of people? They read it. They have a bunch of questions. You make the essay better, right? And so, when you ultimately hit publish on that blog post about nlts, like it's a very sort of thought through peace and it means that all the questions people like people will still have questions surely, but they're going to be better questions, right?
Because like you've answered the first second, third order of questions that they've had and the conversation. And if you jump on the phone with them, after they read that sort of thing, like your conversation with that is going to be so much more productive. Right? And so it's kind of a similar thing at gumroad. Is I just asked everybody in the company and we used this sort of mnemonic is save people time. But basically you should do as much as possible. So that when you do send that message, it's kind of like almost like publishing a blog post, right? Instead of a tweet like you've done a little bit more work, you thought through some of the back and forth.
Would have happened, you know, if Silas has a, this is what we're going to do next. So this is B. This is where you just like lay it all out. As far as you feel like you want to go and it just yeah, you want to save as many people as much time as possible and you want to be. Yeah, you want to minimize that back and forth. The rally tennis or what happened, right? Like and it is expensive and there's certain people, I would say the number one reason besides just competency at the job. The number one reason that people don't succeed at a company like Governor. It's because they just, they're just so unfamiliar.
With this way of working and they're like, hey, so I need to talk to you about, you know, for five things about why, you believe this is the right approach. And what kpis instead of going to notion instead of going to get up instead of reading my blog post on the internet and getting a sense of, okay. This is probably what you think, right? And you can even say that another thing, this is probably the answer. I think you're going to give me, let me know if that's true. If not tell me, why not. And so I can incorporate that into my quad mental model B, right? Because ultimately scaling, a company is kind of like scaling your judgment, right? It's like if you if you can teach people how to make the same.
Should you would have made. That's ultimately the way that you kind of get free from your own business, which I think is kind of an important step for a lot of Founders and entrepreneurs. So you can be free to tackle any problems within the company or outside of it. So, yeah, that's it is super super important like the ability to communicate and specifically to communicate in writing, right? Which doesn't mean you have to be like an amazing. You know, you don't need an MFA in English or anything like that, you know, you can have broken grammar. You can have all these sorts of things, but your ability to think, and then communicate those thoughts.
So effectively, I think is super super, super essential. And my guess is that it's essential in life today. Right? In the more that we spend time in the metaverse, or Twitter, or all of these different places. Like I think the more important those skills just broadly are great. So I think it's important to learn those skills. Even if you don't you don't you don't plan to work at a company like gumbo in your
life. Do you think at all about like remote work and this asynchronous workflow? It actually increases the odds that people will have two or three jobs. They may work at gumroad in other places one. Do you think that will happen and then,
Are you worried about that? Do you encourage that? Or is that a company policy that aren't allowed to do that. How do you think about
it? Yeah. I mean, I love it. I mean frankly I run gumroad and then if we you know, we both have funds that we run on the side and I wrote this book with penguin random house. So like certainly it would be hypocritical for me to say, you know, you should stay focused on government government should be your primary focus. A lot of the people like Governor is specifically choose to work at guard because they have another thing that frankly, they think is more important than gumroad Circle. That Soo is a great Community platform.
Sid, who started? That was VP product for governor. Oh, he left teachable. And there was kind of 2-2 with two things. He could have done, right? He could have signed up for another job or he could have started the company, you know, basically burned through his, you know, his savings and hope that it worked out, right. And he found this new Third Way, which was working at Governor. He did, I think around 30 hours a week, you know, Monday through Wednesday, Thursday, ish, and then he would, he would work on the side project circle with his co-founder, which he also brought into gumroad. So they were to part-time people.
Ruth and the co founded this company Circle and they just closed this mask around. So look it's it's it. I think it does work for those kinds of for those kinds of for those kinds of people. But yeah, there's a lot there's a lot of people who just would freak out but I encourage it. I think it's great. If you want to start a company, you know, I would love to help you do that. You can work in Gummer and you can be incredibly productive here. You do it, 20 hours a week and then you can spend 20 hours a week on your, on your side project side, hustle podcast Book Company, start up, whatever it may be.
Be are people actually doing that. Honestly, I think know, like, it's so draining. Like, I think very few people are really truly capable of like clocking in at some place and then also doing other stuff. It's it's, you know, I think the bottleneck on that is not going to be companies allowing. It's going to be how many people have the energy and actually want to do these sorts of things. Right? But I would love to see it. Honestly. I would love to see more people, you know, the way that I think about it is that every employer effectively has a monopoly on their employees, right? You can work and
You know? And and that was sort of mandated by the office. You can only you know, you only have one body, one physical body, but the minute that goes away then you know, why do employers have a monopoly on your time? Why can't you work 20 hours here? 20 hours there? I don't see why not, you know, especially in startups, right? Like imagine you work at one startup for five years, you know, you're getting one to use your your your thing like one shot and goal. Right? Like you want to build a diversified portfolio of startups because startups are incredibly high risk, right?
And and and so Founders can kind of do that by Angel Investing BC is going to obviously do that. That's kind of the Crux of the job. But employees can basically, you know, you know, get build a portfolio over decades like, you know, one or two or three, four years at a time. And I just think that doesn't make sense. It just, you know, obviously you're seeing a lot of employees. A lot of people are now investing. I think that's sort of, because they want to build this portfolio of investments in Betts. And so, I think they should be able to do that with Sweat Equity as well and and II.
Imagine a world in the future which like and maybe crypto is again, like, kind of, you know, the future is, you know, it's already here sort of thing where people are already doing that, right? They might be contributing over here, getting some token, allocation for this project doing something over here. Doing, you know, and building a portfolio. And obviously, they, all of these things are fully liquid, so they can actually invest if they just have the capital to, as well. And startups are, did you just don't have that, right? That, you know, they're not liquid. You can't just invest the only way to get Equity is by working on gumroad. For example, you can own equity in the company, by being, you know, by putting in 10 hours, a week or 20 hours.
Weak like where else in the world. Can you do that? Right? It's just not not there and my guess is 5 years 10 years from now. We're going to look back and be like really like the only way to earn equity and like the greatest wealth generation machine on planet Earth. Not only, you know, Not only was to work full time. But you know in 2019 was to like literally move to a single place and work in this company, you know and commute for an hour and a half or whatever, whatever. All the all the bundle of work that you have, you had to sign up for before. I just think it's going to go away.
Talk to me about the idea.
Would you ever turn gumroad into like a dow or any of these kind of new structures you're talking about open source kind of methodology, right? Even though it's still a company from a legal structure standpoint or you thinking about this because it kind of feels like that's the natural extension is that you would say, hey, we're actually going to open source code. We're going to create the economic structure incentive around like these dowels that people are talking about like, what's what do you optimizing for? Where do you see this evolving
to? Yeah. No, I think that's a that's super prescient.
I think so. Yeah, I mean, I think what's happening with Dows is that, you know, and this is this is a thing that I've seen generally happening in software, right, which is you build something, you do what you, you would invent, you know, some new product or technology, you innovate. There's a sort of a lot of creative destruction that's happening. But you know, don't words, 10 years old. We're still innovating, we're still doing a bunch of stuff, but I'm not making as, you know, risky as risky bets. I'm not, you know, we're not launching new products all the time, and this is the case for tons and tons of software.
Businesses, you got to solve the problem and maybe the best thing to do is to kind of keep solving the problem instead of trying to like, you know, add features and and charge more and all these things that your customers, frankly don't really even want you to do. And so, yeah, I think, I think extra extra creating yourself from the business makes a lot of sense, right? And I think about, what do I actually need to do a car like truly actually, you know, need to do otherwise, the got otherwise, the business would fail as CEO, and there's really only two or three,
Three things that lie there I have a Google doc of this because I'm trying to get it to zero and one of them is I need to make sure there's enough money in the bank accounts, right? Which might be moving money from strive to pay and that no one should say that that's something a CEO should do right? Like that should be purely automated. It's insane that I have to log into Wells, Fargo like it's stupid. And so that's obviously going to get, you know, automated at some point in the future. The other thing is, you know, like sort of tiebreaking right? Like governance effectively, right? Which is like hey, you know, should we roll back the site? Because we have a Blog. Is it bad enough or not?
Should we D platform is creator for posting this kind of thing, you know, a lot of these kind of like decisions that that feel like only I can make. And I think I Dow is like a phenomenal sort of way of thinking about those sorts of things. Like if 10 out of 20 employees. I got murdered whatever the numbers. Maybe decide we showed her should not do this or maybe the craters on the platform, right? They can decide, who else? They want to be able to join their Community or not. Right? Look, why do I get to decide? Oh like this greater, you know, offends my sensibilities.
T so that they don't get too used to murder. They don't get featured on them. Like, well, you know, these are all the kind of opinions that, you know, effectively just reflect the opinions of the founder CEO of the company. And so I could totally see a world in the future. I don't know exactly how we get there. But I would dream to have gum red, be a doubt to have gum would be a place where I can just Empower people to make their own decisions and and, you know, and then all and then obviously, like I would love to sort of liquidity of it to write. Like I think, what, you know, another big issue you have with these.
But he is, is you basically run this thing and get saw. Like 10 million are Arts, a great healthy business, but you don't, you're not at that. Scale to IPO. You probably don't want to. You also don't want to like fully liquid a, I don't want to sell gum right entirely. I don't want to sell it to another business, but I would love to take a little bit of money off the table, right? Buy a house or what have you and into you know into by some Salon or whatever and so I would lie. Think Dad Krypton does also solve this sort of problem where as you know, you can kind of fully liquid, you can kind of take some money off the table. You can kind of delegate, you know, your duties over.
Time until you have none left and then all of a sudden just like a ins and outs I think today, right? Like they're like they have it there setting up and down and boom. It's you don't even have a company. You can, you can shut down the company, right? Right. Now, in this Society, we have Visa, Mastercard. Like what Innovation is Visa Mastercard really doing today? I have no idea, but they're effectively charging, a three percent tax on the entire credit card economy, right? Hundreds of billions of dollars a year. Like why, right? Like what are like, it's just doesn't make any sense, but it's a skyscraper. We're building on top of this.
Incredible amount of infrastructure. And maybe the answer is that we don't destroy these masks are but we just you know, all of the value gets accrued to all of the stakeholders that company you got to get this with public companies, I guess, you know, in the US but you know, going public is, you know, should be a click of a button, right? Which in and and effectively I think crypto has that promise built into it, right? Which is I should be able to hit a button and boom. There's now gum token, you know, maybe the equity Maps into this token sale initially and then boom. You like, you know, now this this place votes and obviously a lot
Lot of the mechanics have to be moved on chain. Like it would be pausing on how do we D platform? All these sorts of things would have to get there. But I think that's, you know, the writing is on the wall and I pee like it's going to happen. I don't know if government was like too late, maybe we won't be able to switch Gummer to this new model, but certainly like a lot of the companies, frankly, a lot of our competitors. My guess is that they're going to just build, you know, with a lot of these things just built in from the, from the beginning, right?
What else are you in investing in in crypto or like, what else? Do you find? Fascinating? Talk to me a little bit because you've got a fund, right?
You run gumroad, but you'll have to find you at the book on the fun side and from an investment perspective. It feels like you're spending much more time in crypto that you were, you know, two years ago. What is fascinating to you there? Where you putting Capital?
Yeah. I mean, honestly, I would love to do more. It's tough to like I'm I feel like I'm definitely playing playing catch-up, but I really like ten ten percent of my portfolio, you know, the goal would be to get it up to 20% of my portfolio. It would be in crypto, you know, Dows, web, 3 crook, you know, no,
For crypto educational stuff in crypto. I think there's just there's a lot of stuff to get built the way that I like to think about. It is like, I am an engineer. I'm a designer. I can build gumroad all day long. I still have a hard time, wrapping my head around crypto. So I'm really interested in. How do you really lower the barrier of Entry, you know, lower the activation energy required to actually ship value and create value in the crypto kind of ecosystem, right? That's why I think so long. Like, yesterday on the plane. I was spending a lot of time reading about Solana and I think,
That's really interesting to me. Just generally, how do you make it easier for people to actually like, you know, ship their first? Their hello world, right? I think that's that's pretty compelling. I'm also obviously with Gummer to think, you know, I spent a lot of time talking to creators lot of artists, a lot of musicians, a lot of painters. Lots of people in the entertainment industry and Publishing. I just published book. So I'm assuming a lot of my time thinking about like, is this really the final form, right? Like, is this, how we consume content, right? A film, a video? My guess is no.
I guess is like there's more right and maybe that's you know in The Meta Mercer or some sort of a rbr thing or what have you. And so I'm just trying to think about okay? What like who was actually thinking about those problems who has the experience actually solve these problems really really well and then who has the credibility, right? Like who one thing I've noticed is there's you know, I get so many pitches out of crypto stuff. I would say even though 10% of my Provo is crypto. I probably get like 80% of the pictures. I hear nowadays are like have some crypto component to it. And so
Worry a little bit that there's just a lot of people who are chasing, you know, chasing the Zeitgeist chasing the puck. They probably won't be able to get there fast enough. So I try to find people who have like kind of, you know, had some of these ideas or thoughts or have invested in this kind of stuff earlier to kind of just because I do think that's kind of important to be interested in something, you know, before it's sexy before it has the potential to make you a lot of money. I think is pretty pretty important. Otherwise, like I think you're just going to get out Ron, you know, the nft market places that are doing. Well, today are not the ones.
We're started in 2021 right there. The ones that were started in 2017. 2018, you know, busy, I think, was the first makers place was in 2018. Like, it's very early, or they were very, very early and they have this insane, you know, moat, I think because of that. And I also think that the crypto Community rewards those kinds of folks. They want to take bets on people who are, who are early. And so, yeah, that's kind of how I think about it. A lot of picks and shovels, a lot of crater economy, really interested in no code.
And then some interesting hook, like a lot of people are building like the same sort of thing. Right? Like it's like, hey, we want to help creators who aren't technical like, you know, selling and empty collection, right? And it's like, that's cool and interesting and certainly isnít necessary. But you know, what's the hook? Like, what's unique about you? Right? And it can you get more specific? Who are you starting with? Who is your first customer? I think those sorts of questions. I think are really important and often drive like my investment sort of decision making
process. So I've got to my brother's here.
With me, what questions you guys have? So my question would be your company is obviously gone. A hundred percent remote now, and you mentioned earlier that you're now hiring people without ever talking to them. I think that is probably a relative for some people in shock, some other people. So have you been asked by other Founders, or CEOs of companies kind of about this process and if we were to, you know, go to sleep and wake up in five years. Do you think a substantial amount of more companies will be doing this?
Yeah, I would I would say I don't know if it'll be a majority. But yeah, I certainly think like 10 20 %.
Companies that get started, we'll probably pursue this sort of thing. They're a couple things that I've noticed in learn in the last last year. One is a lot of Founders have ping me, not necessarily because they want to adopt our way of working, but because they're like, look, I'm spending all my time into meetings all day long and going for walks, you know, four or five hours a day with with my friends and like grabbing coffee and lunch, and that, you know, you could do that when you're starting in front, you know, staring at a computer for like, four or five, six, seven hours a day, like just brutal. So, a lot of people
Were asking me like, how do you, how do you know, how do you replace the heating? Like, what takes the place of this meeting? Which the answer is like, a lot of documentation, a lot of writing, a lot of essays, right? And and, and so that, that sort of definitely a through line in terms of what people ask but will people actually adopted completely in the way that we will or we have? I'm not so sure. But I think, you know, I think a hybrid like, I think, you know, instead of eight hours of meetings a day. Why not one?
Of meetings we write like I think ultimately, the answer is somewhere in the middle and I think it's important for governor to specifically be the Overton window kind of Pusher, right? I'm say, hey, look, we're going to run the company and this way because we think it's really important to have an example, right? Say, hey, just like Basecamp, kind of, did you know ten years ago like to show people? This is possible. If you choose to work this way, like, is it is possible, not just in theory, but in practice and certainly it may not lead to the, you know, the highest speed, the highest throughput.
You know, if you, if you really just want, you know, if you're, you know, in a supersaturated competitive space and you want to grow like crazy like, yeah, you probably shouldn't switch to know meeting Sprite. But if you have a comfortable business, you're not, you know, you know, your hair is on fire. Every day you wake up and you really feel like you want to optimize for Freedom, then, you know, perhaps this way of working, I think will be much more appealing, and I hope that that's true. I hope that in the future people realize like they can get paid twice as much or they can work half as much and my guess is
A
lot of people who would love to work 20 hours a week and and like I've you know, I've I find that that the you know, when I work 20 hours a week, I have 20 hours. I can work some of that I can work on new projects, but I don't know. I'm just a much happier, more content person when I get to do that. So, you know, my guess is more and more and more people as they reach that sort of like post economic or what-have-you phrase. Like I think will speak this way of working. The other thing I will add is, you know, a lot of people and I try this, you know, Tim Ferriss.
These are in the 4-Hour workweek. Right? Like they decide to go all the way into basically, you know, the digital Nomad lifestyle or like retiring on a beach, or what have you and I'm just never found that works for me. Like I do need to be productive. I do like having some level of social kind of almost accountability, you know, feedback loop. I like working with smart people. I like working on a product that improves over time. And so I don't think the answer is is kind of just like piecing out completely. I do think people want
Should be Justice ID and this sort of structured way. I don't think work is going to go away, you know, wouldn't robots kind of replace the world or what have you. I think we'll keep working on people will like to work, I think working as fun and should be fun. And so, you know, I think in that world like 20 hours a week to me seems much more sustainable for most people. Maybe, maybe the majority.
John. What do you got? So nice to meet you. Congratulations on all your success so far with gum. No, I know you found it around 10 years ago, so
Mike curious is there's been a hundred thousand around a hundred thousand creators on gumroad. What is the craziest thing? You've seen someone be successful on the platform with?
Oh man. There's the there's the few different ways to answer this. I will tell you, I have learned. A lot of people are very interested in a lot of different things. There's a lot of like softcore fetish stuff that does really, really well. There's a lot of like weird sports that I didn't really even know where a thing that people are really interested in. You know, people say that riches are in the niche.
Is I just have to learn that. There are a lot of niches. There are a lot more programming languages that I didn't know existed a lot more design Aesthetics. There's a lot of and then obviously there's like just a ton of like, you know, on the political Spectrum, you know, you see stuff from this culture, far left like that wouldn't even fit on the polite, you know, political spectrum of footer and then and then vice versa. One thing I have noticed, a lot of people D platforming doesn't seem to come up as much now, maybe everyone got what they wanted by getting rid of trump or something like that. But what I
See, is that the vast majority of people at form request? Actually, hit people on the left, like, people on the left have crazy, crazy views, obviously, given the right do as well. But they just don't get the nearly as much exposure. And so, I see a lot of those sorts of things. But yeah, definitely. People, you know, I didn't realize that you can get turned on by, you know, watching someone get punched in the stomach for 50 minutes straight.
So someone
they never say that. That's the, you know, why they're selling this video. Why people are buying a
place. So
Someone in the court, in the comments here on YouTube, had a good question and they were they were asking about how you build the trust with your employees long-term trust when you're not necessarily, when there's kind of that transactional feel to it that you're not necessarily meeting them in person every day. You're not having in-person conversations or meetings or coffees. How do you build that long-term trust that you're investing in their career and their future?
Also,
That's a good question. Honestly, I don't know if I am I think trust is like a very dense like loaded term and I don't like it. I don't like trust. I don't like loyalty. Like why do you know one thing I've learned, you know working in sort of the Fiat credit card payments were compared to crypto is that you you have to trust in Fiat because people can you know, issue a chargeback, you know, there's real risk to trusting, you know to accepting a payment from somebody a stranger on the internet crypto that doesn't exist. Right? And so I'm not
Worth trusses the right thing to optimize for look all I can tell you know, and obviously there's a sort of a track record of me doing this. But all I can tell, you know, the people who work on government is like look, this is the hourly rate. This is how much you get paid. As long as you're adding value to the company. You're going to get paid this hourly rate. It might go up over time. You get this Equity bonus. You can see how everyone else, how much everyone else in the company will make. I promise you that I will be insanely transparent. Like there's really nothing in the company that I know that you don't know besides.
Sighs I guess maybe some passwords and one password or something like that, but there's virtually nothing that only I know. And so I can at least say that, right? I can say look, you can effectively run the company if you want. If you can like if you send me an email saying, hey, I think I can be a better CEO. Then you based on all the stuff that I've read, please do. I'm sure I can find something
better. So it's almost like that trust is built their honesty.
Yeah, it's and I don't, you remember, I was talking to Ben. I worked at Pinterest pretty early on and I remember asking ban. Like how do you build trust with users? You know, in 28 2011 and he said something really profound to me which is like stuck with me literally 10 years later, which is you don't have to build trust with your users. You could have like a pretty website design and people will trust you out of the gate and it's yours to lose and I thought that was pretty interesting and pretty true. Like I think you can almost
Don't want just there. It's people can feel it. You know, you just know that I'm probably like authentic. I'm probably not censoring myself too much, you know, or I'm really good at it, I guess. But you know, I think you can just kind of get a sense that you know, like I'm probably not going to screw you over. I'm probably not going to, you know, fire. You, you know, immediately or you know, or sent you no censor anything or what have you. I think you can kind of get that vibe from people pretty readily. And I found that, you know, if you're not willing to be
A super upfront and transparent with all these sorts of things to me. That's kind of a red flag, right? If someone says, Hey, I want to work at gumroad, but then they don't have any paper trail of anything. They've ever done. Then I'm like, well, you know, how much do you like, what you do? Why is there no evidence that you like what you do? Can I read a blog post about some interesting thought that you've had? Like, I've just always done that. And so I think ultimately, you can go back to, I think I started using Twitter and 2008 or something like that. Right? So you can go back to 2008 and be like, one song was 17 or what have you like.
What did he think? Is that consistent? Probably not given that, you know, I was 17 but have, you know, can you see that? You know, that person changing grow and I think that's kind of necessary, right? If you think about, who are you friends with is generally, the people who are, you know, there's two things, right? One. It's people, you spent a significant amount of time with. I think it's hard to hack that, but then to vulnerability, right? It's people who are actually vulnerable who've actually shared their fears and struggles with you. It's very hard to be friends with someone who's never done that. And so, I think,
There's a paper trail of me, being vulnerable, for a long period of time. So I'm able to kind of build these relationships, you know, with people probably a lot faster. And, you know, than and this happens all the time. Like even when I was doing the phone calls, you know, actual phone calls with people. I would always ask like do you have any questions about me about gumroad about how we work? And besides like the logistical things, like everyone was like, look I already know everything about you, you know, because you've written about the, you know, all of these sorts of things. I'm not applying to this job.
You know, because you know, I already have done the work and so, yeah, I just find that incredibly freeing and it saves me time, you know, I don't have to have his funny. Be a lot of people think I'm an extrovert, because I write on the internet all the time, but it's actually kind of the opposite. Like, the more I read on the internet, the less. I have to talk to people one, one by one. Right? And so I think it's a actually yeah, it serves both people.
So before we let you go, I want you to talk about this book that you recently wrote called the minimalist entrepreneur. How great Founders do more with less and before you
On today, I went and I took a look at both the editorial reviews and also some of the comments on Amazon. I just want to read people very quickly. So Jason freed co-founder of base camp. He said so he'll knows knows not, he knows what not to do, what not to follow what, how not to waste and how not to get caught up in the hype. Then you've got Legion who said a timely hard-won guide for entrepreneurs, looking to build sustainable profitable businesses with real-world impact. And then Morgan housel who has one of the best selling
Oops, right now is sold. I think almost a million copies of this point. So few people can simplify a complex topic. Like, so he'll this book is as fun to read as it is informative. And then you've got Alexis Ohanian who says in a world where things have become grossly over complicated, the middle-east, entrepreneur teaches us, how to strip away the unnecessary and do more with less. That's like a murderer's row of people on the internet who who are giving editorial reviews. And then when you read through the various kind of reviews on the natural Amazon page,
His people are saying, you know, just absolutely hilarious stuff. But also there's just people who just don't like practical advice for entrepreneurs. Like just, it's such like a value-driven set of reviews, talk to us about. Why did you want to write the book? And then kind of what was the process for actually putting this together? What will people learn if they read it?
Yeah, totally well, so in 2019, I published kind of an essay on gumroad and the history that, you know, the starting the company, the raising of the money, the failing.
To raise the money, the firing of everybody, you know, all of a lot of sort of the eight, the first eight years of gumroad. At least, you know, and that sa did super. Super. Well, I think almost a million people. I ended up reading it. And you know, the one of the big questions I got was kind of like, well, this is kind of like a list of what not to do like, well, what should you do? Like what you know, what do you recommend? We do and so basically, if February 20 at 19, I started writing this book turns up, folks take a long time to write.
So I came out October 20, 21. And so, it was, you know, two and a half years, I guess of work, but really, you know, it was, it was trying to answer all the questions that people have asked me, you know, over Twitter, dams person, QA is after talks. All of the things that have to do with with starting scaling owning growing and ultimately exiting a business, you know, and it's really like, honestly, the biggest fear I had is like, is it just too boring? Like, is it just too? It's almost like to value packs. It's too.
Ooh, dense, like it's, you know, I just, you know, maybe people really and people always complain about fluffy books, but the truth is those books sell really well, right? And so maybe people want the fluffiness. But yeah, I just wanted to write a book. I wanted to put every single thing that I know about building a business into it. And therefore, like now anytime someone's like, hey, so what do you think about raising money? How do you, how do you sell your first customers? How do you think about marketing on Twitter? How do you think about, like what, you know, which Community should you build for? Which idea? Should you pick? Where do you start with the idea? What's the right, MVP? What? No,
Until should you use, you know, like, should I move to SF? Should I not like? How do I think about hiring and values and culture like all of the stuff? Like I wanted to put in a single place? Make it super, super dense and then, you know, similar to what I was saying before, save people time, right? So if I can give someone this book, they can go read the book and then they can come back to me with much better questions. I think everyone wins wins from that. And then the last thing I'll say about the book is, is I wrote it for my mom. Like I really wanted to write a book. There's kind of
Like the, you know, people say how I wanted to write the book that I wish I had, right? And that's not really for me. I was successful without this book, but there are a lot of people who need help. They like my mom. Like they don't know, no code. They don't know the Creator caught me. They don't know. No shit figma, you know, they don't know how to run a business. Like I brought a business and when you hear me talk about Governor of My Hope, Is that people think it's like, wait, this is it like that's all. It's a GitHub repo and like, deployed on Amazon web services, and people, you know, you know,
You know, spend 200 million dollars a year on it and then payouts go from Strike to our Wells Fargo account. And then I pay people, you know, all the contractors all over the world using build up. It's like, yeah, it's it a business is incredibly simple and, you know, I want people to be able to identify it as business owners as entrepreneurs because I think it's incredibly important, you know, if you want Financial Independence, you want to get free. If you want to control your time, your hours where you live, like honestly, I think the best way to do that is to is to start in an own, your own business, and I just wanted to
Write a book that I could give to my mom and say, hey, look, you can read this book and you can build a business. It might not be a start-up. It might be a yoga studio. It might be a resume. It might be in person. But all of the tools that you need to start your business, if you get to your first hundred customers to Market, to learn social media, to hire your first few, people, maybe even to raise money via crowdfunding, like, everything should be in this book. At least. That's the hope. It's still, you know, it's maybe it's been out for a week now, so hopefully
Is there and people apply those lessons and, you know, ultimately like what I want is that people started on their own businesses, you know, that's the reason I wrote the
book. I appreciate you coming on, and everyone go by the book will give away a couple here in a
minute. Awesome. Thanks so much for having me.
Sounds good, buddy. Talk soon.
