How To Run A High Flow, Zero Meeting, Fully Remote Company | Flow Research Collective Radio

But I also think flow state is solitary for me. I don't believe the right way to come up with these great ideas is to have a meeting or have a discussion or have a brainstorming session. Personally, I find that the best ideas are literally one person comes up with them and actually spends a lot of time with them before telling anybody else. And ultimately before shipping, you do want many more people to give feedback. But I find that in the real creative ideation stage, The best ideas are kind of one person's ideas. Like Harry Potter is one person's ideas. Game of Thrones, it's one person's ideas, right? Squid Game, my guess is, was one person's idea. So I think that's also kind of pretty important and fits really well into this kind of async working model.

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This was like a really weird thing that happened is my workday started ending at 2. So then somewhere in Zero to Dangerous, there was this idea that I needed now an entirely new category of things to do just because I enjoy them, which is, you know, entrepreneur for 23 years, it never occurred to me to make a list of things to do for the sheer pleasure of doing them because I had gotten all my work done. Like, it never occurred to me to do that. It was really, really weird. I enforced the deadline. Like, it had to be real. I had to create the output to really have the experience be valid. And I was watching my productivity go up and up and up, and I was like, What do I do now? It's 2 o'clock. And it was just so weird. Like, when you have, you know, 20 or 30 people who have weird experiences like that and you can put them in a way that somebody can kind of scan through those, it allows somebody to self-identify and be like, oh God, that's really meaningful to me. Because some person's going to be like a 40-year-old dad who's going to go through Zero to Dangerous and make enough time to go see his kids play baseball. Or whatever. That's going to be somebody.

Go to getmoreflow.com, getmoreflow.com. Pop an application through, takes 30 seconds. We will be excited to speak with you to see whether it's a good fit. So that's getmoreflow.com.

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Our mission is to decode the neurobiology of flow and cognitive peak performance, access the minds of maverick scientists, groundbreaking innovators, and world-leading experts to understand what it what it takes to achieve ultimate human performance so you can feel your best, perform your best, and accomplish your boldest goals. I'm your host, Ryan Dorris, and together with bestselling author Steven Kotler, I present to you Flow Research Collective Radio.

Hey there, Ryan Dorris here with Flow Research Collective Radio, and today we've got Sahil Lavingia on, who is the founder and CEO of Gumroad. He's also an angel investor, a writer, and a painter. If you are into startups, if the name Y Combinator sounds familiar to you, you are probably going to know Sahil. He's very well known within the startup community. Prior to founding Gumroad, he worked as a designer and an engineer at a virtual DJ website, turntable.fm. He was one of the first employees at Pinterest, with a focus on both front-end and back-end development. And he attended the University of Southern California's Viterbi School of Engineering. And Sahil has just come out with a book called "The Minimalist Entrepreneur: How Great Founders Do More with Less." And his company Gumroad is really, really well known for pioneering new ways of working in both a remote environment, but also in an asynchronous environment. They have a radical, way of approaching things like meetings, things like communication, company policy, company off-time, recruitment, with many of these principles that Sahil has really innovated at Gumroad being very, very conducive to flow and peak performance, which is why we wanted to have Sahil on. He's really at the cutting edge of playing with some tools in the real world within his organization that are radical from a flow and a peak performance perspective. And we had a really fun time diving into that that and many other related topics about how to run a high-flow organization and lots more. So enjoy this episode with Sahil. I enjoyed it a ton, and I think you will too. I'll see you on the inside.

Sahil, welcome to Flow Research Collective Radio. It's great to have you here. Appreciate the time.

Thanks for having me.

Got it. One of the ways I first came across your work was through Gumroad, and I'm sure you've given the breakdown of what Gumroad is thousands of times, but I to start with you just describing what Gumroad is, what you guys do and work on, and then from there, I'd love to dive into some of the specifics of how you operate and run Gumroad because I know it's very asynchronously run and there's some really interesting things you do from a working structure perspective.

Thank you. Yeah, so Gumroad is an online, I guess, sales platform. We help creators of all stripes sell digital products, memberships, courses, et cetera, to their audiences. Started the company in 2011 to solve my own problem. I wanted to sell an icon that I designed to my audience and realized it was not easy actually to sell stuff on the internet for some reason. And yeah, that's kind of what we've been up to for the last sort of 10 years, have had our fair share of trials and tribulations, but we're in a pretty good spot now. We just redesigned the entire visual aesthetic and we have a lot more fun stuff coming. But yeah, that's kind of the on-ramp to the online economy is kind of how we're thinking about the next 10 years. How do we get as many people to start selling stuff on the internet? Because I think it's a pretty good thing.

What are the specific ways Gumroad helps people get into the online economy?

Yeah, so we help people, you know, we want to be the easiest way to, you know, spin up a bank account and start accepting credit card payments on the internet. So we help people in all sorts of different countries, Create an account, get a little homepage and a URL that you can share with people. You can collect emails, you can sell digital products one-off, or you can do a membership kind of membership model, subscription membership model, like Patreon-esque. You can do a newsletter, you do a hybrid of all of these sorts of things. One of our kind of core tenets is that we don't want to tell you the right way to make money on the internet. Most services pick one thing, which maybe is smart for them, but I think our Our strategy is we want to provide you the tools and Lego blocks that you can kind of play with and, and figure out what, what really works for you, whether that be a premium podcast or, or a newsletter or membership or selling digital one-off products or cohort-based course or a self-directed course. Or there's just a lot of different ways, I think. Now with Web3 and crypto, like, it's getting even more crazy. So we just provide all these tools, we make it sort of super easy. I guess people call it no-code, but effectively you just go in type some text, upload some images, and then you have a sales page that you can format the way you want, share it with your audience. They can pay, download whatever assets or get access to whatever things are linked to the product. And all of this is ideally automated, so the creator doesn't actually have to do anything. It's sort of a set and forget sort of model. And then we provide analytics, email marketing features, discovery, and other things on top of that. But that's kind of like the core product offering.

Great breakdown. I believe it was the first post of yours I read was titled Reflecting on My Failure to Build a Billion Dollar Company, which is a phenomenal title, by the way. So nice one on that. Before we dive into the specifics of how Gumroad currently operates, I would love for you to give folks a little bit of a synopsis of what you covered in that article. And then I believe you did a follow-up as well last year to the Reflecting on My Failure to Build a billion-dollar company first article?

Totally. Yeah. So the first article was kind of a summation of the first 8 years of Gumroad. It was not meant to go viral. It wasn't meant to be dramatic. It was literally just, I want to write a sort of chronological list of things that happened at Gumroad just for myself, just to send to other people. Because I felt like what had happened was I kind of peaced out of San Francisco in 2017 when things had not gone super well. And I'll kind of recap for folks what the actual history was. But I left San Francisco and I learned over the next couple of years that everyone had like a different story in their head about what happened to Gumroad. And I just felt like, okay, I need to write something because some people thought it died, some people thought it got acquired. Like everyone had a little bit of a telephone game going on. So I started writing it for that purpose and realized 2 or 3 weeks into writing it that the theme and the point that I was trying to make was that I started Gumroad with this kind of very binary goal, which was to build a billion-dollar company, turn it into a billion-dollar company. That was just probably not the best idea I've ever had. Generally, I think binary goals are not great in thinking so dramatically in terms of success and failure. So that's kind of what the piece became was, chronicled Gumroad's life from beginning to where I was at in 2019 when I hit publish, but also had this undertone of, I started out with this billion-dollar idea, it didn't work, I ended up finding some sort of peace with it anyway, and talks about that journey. The journey is I moved to Silicon Valley to be employee number 2 at Pinterest, had a bunch of equity in the company, left, before my stock vested to start Gumroad, raised a bunch of money for that, raised around $8 million from a bunch of Silicon Valley investors, hired a team, shipped the product. The growth was good, but not great. In 2015, we went out to raise more capital, a Series B, failed mostly because our growth was not good enough, downsized the company from 20 people down to 5, and then 5 down to 1. Basically, I ran the business myself. For maybe a year and a half, 2 years. That's kind of when I bounced San Francisco and when I started building the company. Actually, that's kind of where that article ends basically is Gumroad at that point was maybe doing $2 or $3 million in revenue, was like a great business, was paying my bills, was supporting creators, but wasn't maybe the billion-dollar outcome that our investors and I wanted when we kind of started the business in 2011. And then I had a follow-up article, No Meetings, No Deadlines, No Full-Time Employees, which is the update. So 2 years later, actually 2 years to the day, I believe, I published this thing, which was how do we work now? And I think that was pretty surprising to people because I think this whole time I had one story that I told, but there was a whole other story that I had been working on, which was Gumroad was still going, but we were building Gumroad in a very, very different way than what was pretty usual and expected. We didn't get an office again. We didn't hire a bunch of full-time employees again. Like maybe other people would have. I wanted to run Gumroad in the way that was best for effectively like the long term. Like I wanted to build a business that I could see myself working at for a very long time. And that was one without meetings, without deadlines, without calendars, without schedules, just people being able to come in, do their work, and then leave and bill for that amount of work, whether that's a bunch of work or a little work, but allow for that flexibility. And I just also just dislike meetings. I dislike talking internally. I like going into, if I do have a meeting, I like going into it knowing everything there is to know as much as possible. And so I just love writing. Obviously that's kind of a theme for me with the blog post, with the book. I love writing. And so I just built a company that values the writing kind of above all else. And That's kind of how we run Gumroad today, no meetings, totally async. We use GitHub, Slack, Notion to do all our work. For example, no one knows how many hours I'm working today. I don't know. I'll do as much work as I have free time for, but I have this podcast and we have a bunch of other stuff. And it's great because it allows for that. It allows for people to have these other things in their life and it doesn't really matter to anybody else in the company because we all work with the expectation that no one is putting in a 9 to 5. And is going to be available on call if I have a question. And it takes a little bit of work, but it works pretty well for us. And we're still learning because we've only been doing it for now 2 or 3 years. But yeah, we are trying to figure it out. We're kind of on the bleeding edge, which sometimes you bleed. So we're learning.

The structure that you use actually reminds me of crypto Web3 in a sense. It's sort of this decentralized fashion where you pick up work and you bill for what you've actually done. I'm curious, what some of the biggest challenges were at the beginning, moving to pretty much fully written, fully asynchronous, and without deadlines, which I think is one of the big things I imagine people wonder about. So what some of the challenges were in the beginning, and then what some of the biggest benefits have been.

Honestly, there were not as many challenges as I was expecting. I think, you know, the sort of perennial challenge is that you have to hire a very specific kind of person. Someone who writes a lot. And there are many people who don't or think they do, but don't. And that was, I think, it took time to sort of figure out, okay, how does our hiring process look like and our marketing kind of function around hiring look like so that we're able to hire the right kind of people if and when we need to. And that took some time. For example, we now do these trial periods. So the only way you can get kind of a job at Gumroad is You know, at some point in the hiring process, there's like a month-long trial period, which is actually great for us because you can do it in 10 hours a week. Right. And so it's actually, I think, better because it allows for people to do it while they have another job or, or, or whatever, without having to quit before they join your company. And then it doesn't work out. So I love this model of a trial period. I think we'll stick with it. Um, but that was one big learning lesson for us is we needed a very rigorous, like really just do the work. We'll pay you to do the work, but we just need to see you actually do it to know if you can. So that was a big one. Two, we have to work in a very incremental fashion. So for example, if there are people all over the place and people are asleep and wake up working or not, you can't say, hey, everyone's going to sit in a room and we're all going to test this thing and then we're all going to ship it to the world. There's that bulk. For example, a Tesla is probably not an iterated thing. They probably perfect a single vehicle. And then they ship it, right? And they make, you know, 100,000 of them or whatever. And that requires like a lot of in-person, a lot of meetings, a lot of approvals, checklists, et cetera. And so we ship Gumroad very incrementally. Like even this rebrand, we ship the new logo and font and now we're shipping like sections of the rebrand to every single page independently, which requires like a very good engineering team actually. It's a lot easier to just code freeze for a year, redo the whole product and then ship it all at once. but we're actually doing it kind of, we're kind of redesigning the airplane in flight, which is hard, but possible. And so just the ways that we work, smaller PR, smaller improvements, more atomic, modular, we need to hire people who are very good at kind of product managing themselves effectively. Like everybody at Gumroad is kind of a product manager. Even our marketing person is a product manager first, really. I think of myself as a product manager. Daniel Vassallo is a product manager, et cetera. Like every engineer is a effectively a product manager. So I don't think we'll ever have a product manager role, but it'll be a component of everybody's job. And that's just broadly, I think, something I've learned is I need to hire CEOs effectively, which is scary to many people. Many people don't want to be CEOs, but that's pretty necessary. I think for the way that we work, we need people who are, to your point about crypto, very autonomous. The way that this organization works is that we need to hire people who have a very high degree of autonomy and You have to trust them to do the work well.

We do the same thing with trial periods, by the way. It's been very fruitful as well. Two follow-up questions to that breakdown. One is, you mentioned the incremental nature of how you ship and work at Gumroad versus a model that would be more waterfall, such as, you know, Tesla, for example, or assuming construction companies and things like that. How much do you think people can adopt this sort of decentralized model if they have, you know, a business or within an industry that just functions in more of a waterfall fashion rather than agile fashion?

I mean, I think everyone has to figure out, you know, the kind of right working style for themselves. And ultimately, it's, it's also a function of your customers, right? Like, what kind of product experience do they want? And, you know, you have to kind of serve them and their needs, and they may not align with this way of working. But my guess is at least parts of companies should be able to operate this way, right? Like companies that are very highly, you know, built on top of software, have people scattered all over the world. Cuz that's really how this started was, you know, the fact that we have people all over the world, right? Because the minute you have people all over the world, you can't really have a schedule. It's really hard to have a calendar. It's really hard to have meetings. So a lot of this kind of started with that in mind. Like the first engineers I started rehiring were from India. Literally 12 hours away. And so getting people on the same page was just virtually impossible. But I think really, I think anyone can look at their existing work culture and say, these 5 meetings we have, do we need them, right? Or do we need them to be done synchronously via video or audio? And my guess is many of those meetings could be done better via text. You know, 99.9% of the conversations I have with people are asynchronously over text. And I think they're great relationships that I have with them. And it's great because it means I can actually do my own research. Like you can ask me a question and I can go spend a day thinking about it and then come back to you with a really good answer instead of just what comes to mind immediately. Right. And so I think the quality goes up. That's like a great place to start is just to look at all of this stuff you currently already do. Where are you constantly context switching and then figuring out, can I make these, can I bundle them up into one thing or can I only do these on Mondays or Fridays or can I get, for example, we used to do standups at Gumroad every week. I think we did a 15-minute standup on Mondays and literally one week I was like, I just asked the team, hey, could we just do this all via text? Why are we talking? This update. And everyone's like, yeah, sounds good. We'll try that. And that was like, and it worked the first week. And I'm like, cool. Like no standups anymore. Right. And now we have an updates channel on Slack and people just go in and whenever they wake up on Monday or whatever, like they just go in and say what they're working on for the week and what they did last week. And we don't need a meeting. And if I need to give feedback, like I just put it in the thread or I DM them on Slack. And so I think it's, it's just kind of a cultural choice. Like to look at the way that you currently work and decide, hey, I don't need everybody to be in the same room at the same time, or I don't need everyone to approve everything in this way. But my guess is many companies could run this way and will run this way over time. I think, I think it's less a technology problem. It's more just cultural, right? Like if there are a lot of people that enjoy meetings, that enjoy the social aspect of it, I was talking to a friend who works at Nike and he says he has roughly 40 hours a week of meetings, literally. Everything he does at Nike is in a meeting. It's not easy to make those changes, but I do think it's certainly possible.

Yeah. I think one of the benefits of being asynchronous is increased access to flow state. As you're mentioning, someone asks you a question asynchronously and you can go and do a deep work immersion to come up with an incredible answer that would absolutely not be possible if you're interacting synchronously live.

Exactly. It's also just less stressful, right? Because sometimes I find that some of the dramatic moments in your company happen on this kind of like someone says this, you reply, they reply, you reply. It's kind of like a fight with a spouse or something like that. You kind of get off track and then you end up arguing about the argument instead of what you're at, you know, like, and that happens in companies that are kind of a smaller, less personal kind of scale. But yeah, I found that if you have this barrier and you can't reply after, you know, you have to wait a certain amount of time, I think a lot of that kind of the heated emotion kind of just goes away. Like, I don't fight fires at Gumroad. I really truly don't. Like, when I remember, like, the number one job of a CEO, when I was CEO of an in-person company based in San Francisco and an office was like literally dealing with internal Politics might be a stretch, but like internal, you know, personal issues, kerfuffles. Yeah. Let's use kerfuffles. And literally today I would literally zero, zero. I haven't dealt with one of those in years. And so why? Because you don't have a bunch of people in an office. Everything is in writing. So it's a lot harder to politic, right? Like it's kerfuffles don't really exist in writing. Like you don't, you generally don't want to I don't know, connive to get to a certain place within the company in writing. So generally when you move to this medium, like the kind of level of accountability, I think goes up quite a lot. Like I say a lot of stupid things when I'm talking. Like for example, I said stupid. I would never say stupid if I wrote it down. I would have said it on my first draft, but before I typed it, I would've rephrased that word. Right. And I'm just a far better communicator when I write because you're, I'm editing everything. And you're totally right about flow state. I'm in flow state almost all the time because I don't have any meetings at Gumroad and I block off my time very effectively. Today, even though I had a book just come out and I have a venture fund to run, I have 3 hours of free time because I can just drop it in my calendar. I just say buffer and it means no one can book any time with me. And this is not Gumroad meetings, this is external book-related meetings or what have you. But it means I can do 3 hours of deep work without anyone, you know, needing to check Slack for, you know, if anyone messaged me, or breaking for like a 15-minute meeting that is really an hour-long meeting because of, you know, of all the context switching that's required.

Yeah, the Swiss cheese schedule is what we call it, is kind of the nightmare from a flow perspective where you've got, you know, maximum of an hour, usually 30 or 20 or 45-minute increments between meetings. Incredibly difficult to get any meaningful creative work done. So the asynchronous model, I'm assuming— I'm curious what your calendar looks like, but I'm assuming it's just pretty much clean blocks of work without interruption. And I imagine it's the same for your team here.

Yeah, I mean, my calendar— I mean, it depends on the week. And honestly, the biggest thing is I run this venture fund and I invest in 100 companies a year. So that's actually the bulk of my meetings. But like, for example, like next week, Oh, and then I guess with the book launch, I have some of these podcast interviews. So like maybe the week after, cuz that's when it starts to clean up. Yeah. Like my Monday is free. Like go to the gym in the morning, pick up my wife from work and then therapy after work. And that's it. Like literally no, nothing right now. And I believe it's, I mean, yeah, it's, you know, it just, it's just free. It's just free time, which is, can be its own kind of stressful, but But yeah, in the void, you know, it's necessary for me. Like, I just find that if I really want to do something awesome, I kind of have to work on it for 7 hours straight. Like, that's just my working style. Like, if I'm writing a blog post, generally the first draft, I just have to sit there and bang out the whole thing. And it might take, you know, the first, that first version of Reflecting on My Failure to Build a Billion Dollar Company was, I think, like 6 or 8 hours or something like that on a Saturday. Where I just like literally sat on the couch and just like wrote this whole thing out. And then obviously like the editing took weeks on top of that. And the other thing, by the way, that I'll note is that I actually think also not only the time, but I also think flow state is solitary for me. Like I don't believe the right way to come up with these great ideas is to like have a meeting or have a discussion or have a brainstorming session personally. I find that the best ideas are literally one person comes up with them and actually spends a lot of time with them before telling anybody else. And ultimately before shipping, you do want many more people to give feedback, but I find that in the real creative ideation stage, the best ideas are one person's ideas. Harry Potter is one person's ideas. Game of Thrones is one person's ideas. Squid Game, my guess is, was one person's idea. So I think that's also kind of pretty important and fits really well into this kind of async working model is that I believe the best work is done alone, actually. I don't know if that's a hot take or not, but that's at least how I think about it.

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This was like a really weird thing that happened is my workday started ending at 2, so then Somewhere in Sort of Dangerous, there was this idea that I needed now an entirely new category of things to do just because I enjoy them, which is, you know, entrepreneur for 23 years, it never occurred to me to make a list of things to do for the sheer pleasure of doing them because I had gotten all my work done. Like, it never occurred to me to do that. It was really, really weird. I enforced the deadline like it had to be be real. I had to create the output to really have the experience be valid. And I was watching my productivity go up and up and up, and I was like, what do I do now? It's 2 o'clock. And it was just so weird. Like, when you have, you know, 20 or 30 people who have weird experiences like that and you can put them in a way that somebody can kind of scan through those, it allows somebody to self-identify and be like, oh God, that's really meaningful. 'Cause some person's going to be like a 40-year-old dad who's going to go through Zero to Dangerous and make enough time to go see his kids play baseball or whatever. That's going to be somebody.

Go to getmoreflow.com, getmoreflow.com, pop an application through, takes 30 seconds. We will be excited to speak with you to see whether it's a good fit. So that's getmoreflow.com. I actually, yeah, definitely would double down on that. I mean, there's a, there's a concept which more research is needed around called group flow. There's a great book on it by Keith Sawyer, who's a researcher at University of North Carolina. And group flow very much so is possible. It's just in most organizations a meeting structure and the culture and the politicking is going to be very, very anti-group flow. So if you're in a group setting, you're less likely to get into group flow. Whereas even in a poor culture, if you're solitary and you're just working on a single chunk of creative work, you are likely or more likely at least to get into individual flow because of the fact that when you're solitary, the negative impact of policies or communication styles or culture can't get you, essentially. So I definitely think that's one of the big, big benefits from a flow perspective of being asynchronous. You mentioned writing. I'm curious, so Steven Kotler is my co-founder here at Flow Research Collective Radio. He's a New York Times bestselling writer, and he always advocates for us to put writing at the center of a skill set for anyone that we bring on as a proxy for clear communication and a number of other things. And I'm curious, you know, why you heavily index on writing in the hiring process and how heavily you actually do index on writing ability.

For example, if we're hiring an engineer, like the number one thing is their ability to code. And then their number two is their ability to write and communicate. And number three, I can't even tell you, I don't even know. Like, it literally comes down to those two things generally, competency and the skill and then communication. Sort of hard skill, soft skill, right? A kind of simple kind of dichotomy. And the reason I think it's so important, it kind of goes back to what I was talking about. Just like, it's your ability. It just is your ability to communicate. Like, I really think, what is an organization? An organization is a bunch of people who have certain skills that they're contributing to the organization, whether it's code, design, product management, support, whatever. And then there's the interpersonal side, right? There's like, there's kind of like the nodes and then there's like the connections between the nodes. And so I think writing is the connections between the notes. Like, how good are you at communicating? For example, if you apply to Gumroad and you say, hey, I want a job at Gumroad, here's my resume, let me know, right? Like, you're not gonna get the job at Gumroad. But if you say, hey, I think Gumroad's really cool. You know, I played with it. I found a bug. You know, I think it's this journey that you've been on is interesting. How do you think about this? Or, you know, like, I would love to do this at Gumroad. Here's a little prototype that I built of it, or here's something else that I built. You know, this is why I built it. This is what I care about. You know, would you be interested in talking? Right. That I find is much, much, much more effective. It shows that you've done some work. I call it proof of work. You've done some proof of work. You've shown me how you can add value to Gumroad, and you're already putting yourself in the top 5 to 10% of people who email me generally by doing that. Like, it's kind of astonishing how, how few people do it. And yeah, I think if you're able to communicate then, and your ability to, you know, you're able to do the work that you're hired to do, like, I don't see what else I need from you. You know, I don't do reference checks. I don't care about like culture fit, like all these startups care about. Like if you can communicate well and you can do the job, then you deserve to get the job and get paid to do the job. And so, yeah, I just, and I also find that it's like pretty easy to vet for. I don't have to talk to you. I can literally just read your email. Or I can read your Twitter account and I can say, okay, this person is smart or not. Right. They have it. They pay attention to details or not. They have typos or they don't, you know, they have a story that they're telling, you know, or, or they have an ego. Like these are all pretty evident when you read someone's work. I find like I can read a book and be like, I know I'm going to get along with this person or not. Right. I think it's pretty easy to tell. So yeah, I find that that's just, it's just, it's just kind of a no-brainer for me filtering that in that way. It's also fast. Like I can skim an email in a minute. I can't do that to an audio, like a 30, you know, a 30-minute phone call is like 30 email screens. Right. So I think just in terms of my own personal efficiency too, I think writing is, is it's much higher quality. And especially when automation and more of this stuff gets into the picture. All of that stuff is going to make writing even more valuable, right? Because what— it's far more easy to have a robot look at a bunch of text and make sort of decisions based on that than audio or certainly video, right? Writing will only become more and more and more valuable, I think, over time.

Within an organization as well, it's also archival, which makes a big difference, as you were mentioning, to politicking and stuff like that. You know, everything's in writing, so you don't have to do the whole let's get this in writing as our next step thing. It's just, it's are already there. What are a few first steps you would recommend to, you know, leaders or even people working within organizations that are very meeting heavy? What are some first steps you would recommend to both sides of that spectrum? So someone running or leading a team and someone within a team to move their organization toward the kind of structure and decentralization you're emphasizing that, you know, I think we're both saying is, is likely going to be higher flow for a lot of people.

Yeah, I think I remember talking to an Instagram PM who said that they have a rule at Instagram, maybe all of Facebook, but at least at Instagram. And I would always recommend start small. Like you don't have to like switch to this immediately, like start as small as you can and make some small change and see how it goes. Cause it might, maybe, maybe it doesn't work for you, but yeah, Instagram had this rule where, or has this rule where basically I think it was something like you couldn't schedule recurring meetings. Or at least like the maximum amount of time you could schedule recurring meetings for was like 3 months, which basically meant that every 3 months you had to kind of recalibrate and say, do we still need this? And I think that's like a really easy way to start is to just think about like, do you have a meeting that is literally just goes forever? Like every Monday at 9:00 AM, we're gonna do a standup and that just literally goes forever and just say, well, let's do it for 3 months. Like let's do it quarter by quarter, allow people to suggest. Meetings like on an individual basis. Like if there are two people that meet on a regular basis, like make it irregular or yes, take this one meeting and say, hey, can we do this over the next time we do this or pick a holiday, right? The December is a great time to experiment with this stuff. Cuz people are out of office and stuff all the time traveling. And I think this is a great month to say, hey, if anyone wants to turn a meeting into a Notion document or a Google Doc, you know, you're welcome to, to do that on, you know, kind of a, you're at kind of at-will basis. And then, you know, in January you can reflect and say, hey, did anyone do that? How did it go for you? What do you think? And it's also just important to say like, this isn't a one-way door. Like if it doesn't work, you can always go back to the way it was before, right? Like you can do one asynchronous standup and if everyone hates it, you can go back. And you can just make that clear. Like everyone has veto rights, you know, everyone in a meeting has veto rights over turning it into not a meeting. But if everyone in the meeting thinks it should not be a meeting, then, you know, it probably shouldn't. I think it's pretty simple. I don't think it needs to be overcomplicated. Just give it a shot, turn one or two meetings into this asynchronous way and, you know, celebrate it and celebrate it as something worth trying. And then if it works, you can decide to figure out how you want to, you know, make it more of a standard.

Are there other changes outside of meetings that you recommend? Like, for example, it always surprises me when I interact with founders or employees working within organizations that don't use any form of, you know, project management system or software and don't use Slack or anything like that. And manage workflow through email and meetings. So I'm curious if there are other things you recommend people stand up, like for example, you know, a really strong system for managing workflows.

Totally. Yeah. So we've never done email at Gumroad, like literally since 2011 when I started Gumroad, we'd never done email internally. We all, you know, BD, sales, et cetera, we need emails, but yeah, internally never done emails really. And so yeah, I forget that that's even a thing people can choose to do. Why? I don't know why you would, but yeah, no emails, no meetings. Everything is, you know, for us, I would highly recommend using a service like Slack. I would highly recommend using a design tool like Figma. I would highly recommend using a wiki tool like Notion and a code version control system like GitHub. Those are our tools. That's literally it. Like that's how the entire company runs is like on those 3 or 4 tools. They're the only tools that I really interact with when I need to work on Gumroad and that, you know, that, that kind of enabled collaboration. I guess there's like my code editor and stuff. So yeah, definitely do all use all of those tools, all of those tools, just inherently by using them. One, they'll make you feel awesome because they're really well built and designed, but two, they'll give you documentation for free. Everything just in, there's no save buttons in any of those things that I mentioned, right? You just type and it's automatically version controlled, page history. It's all there. It's all collaborative. You can, you know, everything comes with a URL that you can send to somebody else. You can save it, bookmark it. Like you get that, you know, people talk about composability in Web3, but like all of these tools are super composable, right? You can, everything has a URL. You can link someone to a Notion, they can comment on it. That's saved. You can take that comment, you can link to it from Slack. You can take the Slack thing, link to it from GitHub, et cetera, et cetera. So everything is kind of a spider web of knowledge. And first step, even before you try to get rid of meetings, is try to get rid of emails. Just switch to GitHub, Slack, Notion, Figma. Get rid of all local software. You should only be using cloud-based collaborative software. I would also say you should only be using really good, high-quality startup-built tools. Like don't use Photoshop, use Figma. Don't use Google Docs or Microsoft Teams, use Slack and Notion. Use the best tooling available to you. That's a real big perk of working async is you can use all of these ridiculously amazing tools. Like the way that Gumroad runs today honestly wouldn't have been possible in even probably 2018 because the tooling just wasn't good enough. And the, you know, Gumroad in 2025 will be stupidly amazing, like unfathomable compared to the way we work today. When you choose to invest in a tool like Notion, GitHub, Figma, Slack, maybe not Slack so much, but the other three, the tools are getting better all the time. Right? So it's kind of like you wake up every day and your life is just better. Like it's just more efficient. You can be more productive. It's kind of like your iPhone gets better, right? So when you, when you use crappy tools like email, Email hasn't really changed in 20 years. And so you're not— your quality of life isn't really improving. And which, you know, motivates me, like the more my life gets better, the more energy I have to make my life even better. Right. It's kind of a nicely compounding thing. And so I think that's also really, really, really important.

Yeah. And I think it's worth noting as well, especially for non-technical folks, that there's a skill acquisition step there where you've got to learn how to use Notion or Airtable or whatever it is. Slack's pretty obvious in how to use, but there's definitely, I think, some skill required to be able to properly utilize tools, especially at scale across a team. So I want to switch gears slightly here and touch on The Minimalist Entrepreneur, which is your new book. How Great Founders Do More with Less is the subtitle. One of the quotes from the book is, "Start as soon as you can. Start before you feel ready. Start today. You don't learn, then start. You start, then learn." That is something, by the way, that I find myself emphasizing to people personally if they're asking for advice or mentorship so often, it is unbelievable. It's probably the number one piece of advice or thing I underscore. But I'm curious what the rationale you have for that statement is and if you could expand on it a little bit.

Yeah. Honestly, I think it's in large part because I think generally people know enough to get started. They already know enough to get started. Even when they consistently do more and more research and listen to podcasts and read books and blah, blah, blah, like consume YouTube, Wikipedia, like you kind of already know what you need to get started. And I think people are almost like doing too much pre-work for like situations that don't yet exist. It's like hypothetical, right? It's like, oh, if I go for a run, and my shoes break, I need to make sure that there's a solution for that and all these kind of stuff. It's like, look, as long as you have an iPhone, you're fine. You'll be fine. Like, you can book a flight to Mexico City, and as long as you bring your phone and your wallet, you're good. Seriously, you're good. You know, you can book an Uber. There's Uber, there's Airbnb. People will accept your credit card generally. Like, you're totally fine. You don't have to do any research, any planning whatsoever. You can do it all there. It's easier when you are there. You can ask people, you know, and so I would say like, yeah, I think that the reason I really emphasize starting then learning is I just think there's just this idea that people need to know everything before they get started. But truthfully, you need to know very little to get started. And I find that the people who consider themselves quote unquote perfectionists are actually making an excuse. To not ship. Right. They're basically saying, oh, I need to, like, this thing's not good enough yet. And I just find, I just get tired of all these excuses. Like, selfishly, I want the world to get better and the world doesn't get better because people have amazing ideas in their heads and they're improving their ideas in their heads over and over again. Like, my life gets better when people ship things and real improvements and, you know, art and culture and, and that all requires taking the ideas in your head and putting them out there. And I find that if you do that, you're going to realize very quickly that actually all of the ideas you have are kind of shit. Even the best ideas, even the ones that you spend years thinking about are pretty bad because you just don't have the muscle. You just don't have the experience to have really, really good ideas yet. It takes time. It takes real experience. For example, I don't think anyone thinks that they can become a world-class soccer player By watching someone play soccer, right? Or watching, I don't know, a million tapes. No, everyone knows how do you get good at it? You have to kick a ball around, right? You have to show up and you have to do drills, but mostly you have to play the game and lose and win and lose and win. And like your brain will pick up the right instinctual sort of response to certain situations, which is ultimately what you really need is you're really training your instinct. And that's the same in business, the same design, same in engineering. It just doesn't feel the same because the muscle and the intellectual organ, the brain is still in the same place. Like your leg and your brain are in different places. You're like, oh, I need to train my leg. But no, you don't actually need to train your leg. You're actually training your central nervous system, muscle memory, et cetera. So it's the same thing with business. Like you're just training your central nervous system in a sense. Like I can, someone can tell me about their business idea and I can give them I can say that's not going to work in like 10 seconds. Why? Because I just have a million times more experience than they do. And unfortunately, their answer is like, well, I can do more research on the market or I can look at competitive analysis or I can do this. But the truth is they can't. They just haven't been through what I've been through. And the only way to get there is to actually just say, I don't need the idea to be perfect. It's good enough. I want this thing to exist. So I'm just going to start building it now. And I'll learn why this business will fail, because it will fail. It doesn't matter how much research you do, it will almost definitely not work if it's your first business. But the only way you're going to find out what's not going to fail is to fail and be like, "Oh shit. Okay, never mind. I did that wrong. New idea. That failed. New idea. That failed." And you basically make a different mistake every time until the mistakes that you're making are better mistakes. I learned this painting too. Like if I, if you wanna be a really good painter, it's pretty easy. Like you make a bad painting and then you make the painting less bad 10,000 times and then you have an amazing painting. It's not like, you know, Da Vinci like paints the Mona Lisa, like he spent fricking years working on that thing. He made a bad painting and he made it better and he made it better by making the worst thing less worse until it was a good painting. Right. So I think same thing goes with business. Same thing goes with improving your brain. It's all trial and error, right? And like, emphasis on error. Like, you will make errors.

I love the painting example of the fact that it's about making it less bad over time. And that's one of the things I find myself sometimes in exasperation emphasizing to people who are paralyzed about getting started is just, you know, make it as terrible as you possibly can because that beats not acting in almost every case. Another quote of yours that I loved is hard skills get you in, soft skills get you far. So I'm curious if you could break that down for folks.

Yeah, I was proud of that one. Yeah, thank you. Yeah, I've been thinking about that idea and I've had a bunch of tweets about that overall kind of hypothesis, but that was the, that was the one that I was like, okay, I finally summed it up in a, in a, in a sentence, which is basically that You know, there, there's a lot of emphasis on, I guess there's emphasis on both things, but I think generally there's not enough emphasis on both at the right kind, right time. Like I think there are a lot of people who focus on the soft skills when they just don't have the hard skill yet. Right. Like I tell this all the time when people say, oh, I'm like, I wanna do what you did. Like I wanna move to the Bay Area or I wanna work at a startup or I wanna start a company or whatever it may be. And I always tell them like, learn to code. That's always my first 3 words to them, learn to code. And the reason is I learned to code because I wanted to learn a skill that the industry that I wanted to be a part of valued, because that's how you get in the door. You don't get invited to a party because you're, you know, unless you have something to offer, right? Like you're an interesting, funny person or whatever. Same thing goes with getting into any skill, getting any job, like ultimately you're getting the job because you can do the skill. And that's not easy, but I think it is quite necessary. Like Elon has a CS degree. Naval from AngelList has a CS degree. It's not a coincidence that these people know how to code. And so I think that's pretty important. And so, yeah, I think that's the first part is hard. You need a hard skill to get you in. Hard skills get you in, but once you have hard skills, I think the people who really excel and get really, really far are the people with tremendous soft skills. For example, Naval and Elon are probably not coding every day anymore, but they've really developed their soft skills, their ability to manage people, write really tight emails, be responsive, don't be late, do what you say you're going to do. These things that are actually very easy to learn in a sense, there's no physical barrier between being responsive, I think. Or maybe there is, maybe again, it's like a muscle that you need to train. But yeah, I found that in my life, when I look at the people who found really, you know, a lot of success, however you may define that, it's the people who were really focused on a very specific skill, a hard technical skill generally. And then over time they developed their soft skills and they got really, really good at these kind of soft skills. And so I find that there's like kind of two groups of people that I, that Tweet was meant for. One is the people with who think hard skills are everything and don't care about soft skills. And then the other group is soft people who think soft skills are super important and don't really care about hard skills. And I think you really need both. You need something to get yourself in the door and then you need to kind of be a charismatic, personable person that people trust. And those are the people who end up climbing the, the, all the ladders in the world that exist.

One of the things we constantly emphasize to people when we're helping them build a life and set of routines that is conducive to flow is distraction management. And another quote of yours that I love, this one's from Twitter, is, "Don't let Web3 distract you from how early Web2 is." And I know that a lot of our clients are struggling with the distractions occurring from the crypto Web3 hype machine. So I'm curious, you know, what underscores that sentence?

Yeah. So I love Web3. I'm a huge fan of it. And it's kind of a both tweet, not an or. It's an and, not an or tweet. I never said don't do Web3. I said just don't let it distract you. So do Web3 stuff if you want, but just make sure it doesn't obscure the fact, these other truths. Two truths can be true at the same time. And Web3 is awesome. Web2 is awesome. By the way, Web1 is also awesome. And you can work on all of these at the same time, or you can pick one. It was really a tweet about FOMO, right? There's this idea that there's a train leaving the station and it's the last train, and if you miss it, you're screwed. And it's just not true. There's trains leaving the station all the time. There will be more and more trains leaving the station over time, only going forward. It will only get easier and easier to board one of these trains or whatever. And yeah, I find that with all the emphasis on Web3, which is fine, it's kind of a new cool thing with a lot of money associated with it, it makes sense that there's a lot of people who are feeling like they're missing the boat. But ultimately Web2 is so early, literally there's still pen and paper and notaries and just too many humans in all these manual places that just don't need to be there. I just hope that people just don't find themselves so distracted by Web3 that one, they don't do anything in Web3 because they're not ready. If you're not actually building in Web3 already, you're not going to really be able to do much. And so you're only going to feel bad. And I hope that it also doesn't distract you from Web2. It's kind of like the worst of both worlds where you get distracted by Web3, but you don't do anything in Web3. But then it also distracts you from Web2, so you don't do anything in Web2 either. That I think is the biggest risk that you could have is if you just choose neither. And so I think that's just really— and I find that that happens. I know a lot of people who just— imagine it's like trying to catch 6 balls at the same time. You end up catching 0 of them instead of 1 or 2 of them. If you focused on catching 1, you'd have caught 1. And so I think I have a lot of friends that are like this, that are just kind of almost have ADD or something, And I just find that it's kind of like the buying and holding of investing. Pick a thing, get really good at it. And if you do that, you will be insanely successful. The top 1% or 2% or 10% of people in Web2 will make more money than the bottom 90% of Web3. So ultimately, where do you want to be? And wherever you choose to be, you should work on being the best. And if that happens to be Web2, I don't think there's anything wrong with that.

Second last question here. So I believe you invested in HelloSign after cold emailing Paul Graham, who's the founder of Y Combinator, and then going to the demo day. I think that is correct. If so, that sort of initiative I think is just such a valuable asset. And I'm curious how you would advise people to dial up their initiative to be able to you know, pull off things like that? Because where I read that, you know, you emphasize the point that anyone could have done that, but almost no one does do that sort of move.

Yeah, it's funny because I love stories like that where it's literally like, I didn't do anything that special. Like, I found Paul Graham's email, which I think isn't paul@ycombinator.com. Like, I don't think it's hard to find, or PG, you know, it wasn't secret by any means. And I don't think he knew who I was or anything like that. I literally just sent him a cold email and said, hey, I work at Pinterest. Maybe that helped. I don't know. I don't think Pinterest was that well known at the time either though. I think anyone who emailed him would've been able to get an invite to YC Demo Day. And I said, hey, I want to angel invest in startups. Can I come to YC Demo Day? And he said, sure, and CC'd his chief of staff or something, and she invited me. And even if I didn't get invited, I probably could've shown up. It's not like they checked IDs at the door or anything like that. I'm sure they do now. But yeah, I don't know. Honestly, people ask me that all the time. Like, how do you have the confidence to do something like that? And it's like, I honestly don't know how you don't have the confidence to do something like that. Like, I wanted to go to YC Demo Day, so I asked, right? Like, what's the worst that can happen? Like, he doesn't respond or he says, wow, this guy sent me a cold email. I'm gonna block him from everything and block him from Hacker News and delete his account. Like, I guess, I mean, That's a possibility. But yeah, I just find that like, there's just like almost no downside to trying. And I don't know, I seriously don't know why people don't do it more because I put examples like that in public view specifically to show people that it's possible and that like some of the best investments, like some people would think like getting onto the cap table of like Figma or Notion would've been hard, but like, no, it wasn't hard. I just asked. I was like, hey, can I? And they're like, sure, you know, and it's like, damn, I wish I asked about Stripe, you know, like, I think people just don't ask. Maybe it's a fear of rejection or something like that.

It's funny. Yeah, I got— I mean, I connected with Stephen, who I'm still working with 7 years later, and we've built this company together and everything through a cold Facebook message. And other opportunities I've gotten through just asking with cold emails or cold messages have just been mind-blowing. And I mean, just asking is so asymmetric, you know, there's no downside, there's potentially infinite life-changing upside.

Yeah. And it just goes back to the soft skills thing, right? Soft skills get you far. The hard skills got me the job at Pinterest and got me a job living in the Bay Area and allowed me to do these sorts of things. But those things were only possible because as an 18-year-old kid who'd never been invested in a startup before, was comfortable enough to email Paul Graham, who is kind of a legend. It was like a 2-sentence email and anyone could have typed those words really, but I just think it takes the confidence, and I think the confidence comes from trying and from it having worked prior with maybe at a smaller scale or something like that. I have full confidence that if I had an issue with my Tesla, I could email Elon and he would read the email. He'd probably read it within 15 minutes and he might even reply. And there's stories of this happening with tons of people, Steve Jobs, et cetera. Right? Like it's, it's, I think, you know, now being a CEO of a company, like I realized that like our job is responding to email, literally. Like that's what we do. Like we wake up, we check our email, we respond to the email. Like I guarantee you that that's what Tim Cook does 90% of his day. He's either in a meeting or he's responding to email. And if you know that, then what does that mean? It basically means that email is this insane superpower, which means you can get in front of anybody in the world instantly and they will read your words and they might respond, right? Like, that's kind of insane to me. You know, like you can just email, like, I don't know, Barack Obama and like, he'll see it. Or like maybe at his scale he won't, but my guess is honestly he would too. You know, even the most successful people on planet Earth, they don't get like 700 emails a day or something like that. It's pretty bearable. And again, it's literally their job. Like, this is literally what they do. It's communication. It's responding. It's saying yes, saying no. And all of this stuff happens over text, over email, but primarily over email. So it is really a superpower. It's like why I have my DMs open on Twitter and always will, right? Like, I read every DM that gets sent to me. It's very manageable. And every day someone says, I can't believe that you replied or saw this. And I'm like, I can't believe you can't believe that, you know? It's very doable. It's very manageable. We're not— I don't know what you think my life is, but it's not packed full of stuff and I'm flying around the world on my private jet. And even if I were, what would I be doing on the private jet? Probably answering emails, right? So checking my Twitter. Right.

Yeah, it's an empowering thing to believe.

Thinking more about it than just hearing my own answer, I think a lot of it is just people have a different conception of reality, I think is a lot of what it comes down to. My conception of reality is that everybody is in front of a laptop typing away, answering emails, distracting themselves on Twitter, YouTube, whatever. And I think my conception of reality is pretty darn accurate. And I think many people's conception of reality is that Jeff Bezos is, I don't know, doing some supernatural thing. And has meetings with celebrities and politicians and dinners and I don't know, is telling people, someone walks into his office and says, hey, what do you think about this? And he says, oh, it's like this in-person, like West Wing or something. But actually, no, it's like everyone's just emailing back and forth. And yeah, I think you need the correct conception of reality to be able to take advantage of reality. People who DM me and are like, "Oh my gosh, I can't believe you responded." It's like, I don't know. I wish I could tell them that their conception of reality is flawed if they think that I'm special in some way. Yeah.

No, I love that. Love that. I have this final question is just where can people learn more about you? And before you answer that, I just want to encourage people to check out The Minimalist Entrepreneur: How Great Founders Do More with Less. I know our audience will be a huge fan. I loved reading it. It was great. If People have liked all you've had to say here. I know they're going to love that. So I'll mention that. And then where else can people learn more and follow along? I also know you've got a fund and a syndicate as well, I believe. So feel free to mention that too, Sahil, if you're raising currently.

[Speaker:Sahil Lallani] Yeah, totally. So yeah, I have an AngelList syndicate. I think if you just Google SHL Syndicate, you'll probably find it. But I invest in lots of startups, around 100 a year, around $15 million a year. I have a Twitter account @SHL, and probably the best place to start is to just go there, read some of my tweets. My pinned tweet specifically is the link to reflecting on my failure to build a billion-dollar company, which is kind of like a long bio. If you read that, there's a bunch of things linked in there and you can kind of start perusing the spider web like Google does and learn more. If you, if you're curious.

Scanning your Twitter feed is a very high ROI activity, by the way. The one-liners are phenomenal.

So definitely, I try really, really hard. That is actually my primary goal, is like value per word, actually value per, value per character is my, yeah, my metric. Um, yeah, it's great.

All right, boss, well, thank you so much for your time. Appreciate it. If what you've heard on Flow Research Collective Radio has been helpful, please consider doing us a solid and leaving us a review on Apple Podcasts, Spotify, or wherever you are listening to this. Reviews help us connect to a wider audience so we can get these peak performance principles out to more people.