How to PM Production Changes with Devin: Tutorial From Gumroad CEO, Sahil Lavingia

Sam Altman said one person will be able to create a billion-dollar company such that one person could ship the entire product. The nice thing about Gumroad is it's basically just me. It's a dictatorship, right? That's kind of why we can move super fast.

Sahil Lavingia has one full-time employee and he's taken Gumroad to a $10 million ARR and a $100 million valuation.

From Slack to code, it'll go and build this and then you can actually see based on your PRD, what did the designer think they were supposed to be designing? All of a sudden this is now a feature in production without us having to really do anything.

That's Crazy. Weeks of coordination. You guys just decide we want to do this. Devin, address it.

We are leaving CSS behind to migrate every single one of our CSS files and delete them all.

You can go straight from Slack to Devin.

This is like the first step I tell everyone to do if they're moving to start to use AI more. Oh wow.

Honestly, I think that's the new dream though. Everybody wants what you have now. And how many dividends have you paid yourself in the last year?

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Sahil, welcome to the podcast.

Ed, thanks for having me.

I was telling you off screen that I have been fanboying about you for a while. I once saw you in person 4 years ago, but I was too shy to actually come up to you. So this is a dream come true to be recording with you. What are we going to do We are going to be cooking.

We're going to be making 3 things, walking through how we, you know, we use AI. I guess small, medium, and large. The first thing will just be kind of how we sort of use it to small, like, you know, to solve like a really small issue that comes up in Slack where we have Devin just kind of take care of the issue so that we don't have to get bothered by some small fix, some small feature, feature requests that normally an engineer, designer, PM would have to tackle. The second one is going to be like sort of how we walk through building a feature, scoping out the PRD for an existing product of ours called Flexile. And then finally, we'll sort of try to build something totally from scratch. To one and see how that goes. We don't know what we'll build, I guess. So to be on that—

Truly live, everybody. Awesome. So can you show us this first one? I was pretty mind blown when you even just told me about this. From Slack to code.

Yeah, sure. This is an example of how we would use something like Devin to solve a problem. So, you know, we have Slack, like many companies who use Slack. We have an internal customer support tool that we've built called Helper, helper.ai. And we had a feature request from somebody basically adding this kind of assign yourself button when something is not assigned. So if you use something like GitHub, it just basically instead of two clicks where you have to like first click on a sign and then click your name. It's one click. So you save, you know, your customers one click, which is awesome.

Yeah.

Uh, and so this was reported by one of our customer support staff and she explained exactly why. This is very great. This is like exactly like the perfect feature request, which is like what you want and why you want it. And so I just said, hey, Devin, solve this, address this. And Devin reads the Slack thread, sees the two images. And then sort of explains its planning and keeps you up to date and then eventually opens a pull request. And here you can read the code as you should. You should probably test it, make sure it did what you want it to do. Obviously, if you have tests, you should make sure the tests are up to date, all that kind of stuff. So Devin, this is kind of, you know, kind of goes through and creates this and then I do it and review it. So this is a good example of something that like no one had to really spend too much time thinking about, but it was solved. It was deployed. It was and all the deployment and all that has long been automated. So all of a sudden this is now a feature in production for people to use and benefit from without us having to really do anything. So yeah, that's one, one example.

That's crazy. So the original process at a larger company that most people are living through right now, they are going to get that request in Slack. The PM is going to take note of it. They're going to investigate it. They're going to see, oh, how many people is this affecting? Is this a big enough request? Then they're going to prioritize it. Once they prioritize it, there's going to be a request for create a PRD about this. They'll create the PRD about it. Then engineers engineering is gonna create their engineering spec about it. Then finally it'll get prioritized in a sprint and an engineer will actually work on it. Weeks of coordination. You guys just decide we wanna do this, Devin, address it.

Yeah. Well, you know, I have a big reason that companies like that are, they do that is because they need buy-in from so many people, right? So the nice thing about Gumroad is, is basically just me. It's a dictatorship, right? Uh, so that's kinda why we can move super fast is you don't have to kind of like put together all this sort of work that's really just to get like internal buy-in. It has nothing to do with actually shipping the change. The, the hard part is like in aligning all the people to kind of get behind that specific decision. Uh, one other reason I really like AI is because I think it sort of is quite good. It's sort of like 99th percentile at many things. Uh, and so generally the decisions it makes are pretty good ones. And actually like things like design and code, it's, it, we just kind of defer to the AI, right? And so it should come up in that sort of PRD, something that's important should, should show up in the spec conversation itself. And if it doesn't, that it's not that important. AI can, can decide however to tackle the problem. You know, as long as it meets the criteria and the spec, it's going to, it, we, you know, it's correct, quote unquote.

But could bigger companies adopt this for features that are a little bit less contentious that don't need buy-in? Like, I feel like there's going to be a future world where some companies are taking more of how you guys are working, maybe creating a bar for certain features and that way shipping much, much faster.

Yeah, I mean, I think the way that a, you know, a bigger company would probably do it, I don't have a lot of experience working at big companies, so I don't know, to be honest, like the mechanics of them, but basically you would just do it on a team basis, right? So you would pick a specific project, uh, you know, microservice architecture is quite popular in these big companies for this reason, right? Where you can sort of, people get frustrated that they have to move at the slowest pace of the large organization. And so they think that, oh, if they like factor off and they just have like a small API microservice that they can now all of a sudden move much faster, they can make different technical decisions, they can make different architectural choices. It's true to some degree, but that introduces like a lot of other complexity that you then have to think about. And I think my bias is, is to tend towards like, what's the right approach such that one person could ship the entire product? Like, so a lot of the way that big companies move faster makes it impossible to get smaller. Like their process actually is probably quite fast, but requires like a number of people that you can't, like you need a PM, you need the designer, you need the engineer, like the way they work, you can't without refactoring the process, you're not going to be able to get, and that's largely why these roles even exist. This, people talk a lot about automation and unemployment and stuff like that. But most of, most of that unemployment, like it's one, it will happen to these kinds of jobs. It'll be mostly these kind of like producer-like jobs. But two, they're going to persist a lot longer than people think because the production process is quite rigid in most of these organizations. You're not going to see companies all of a sudden decide to get rid of like 3 steps in their process. It's very difficult once you have process to get to unwind it unless you have some sort of like, like what happened recently with, was it EA, I think, which just went private. They were acquired. So in the case of EA, EA is a good example. Like, they probably have built up like a ton of bureaucracy over like the last 30 years that in the next 5 years is going to get chopped, right? Like, the bureaucracy is going to get massively sliced. Better or worse, it's going to lead to a much higher volatility in what EA as a company is going to ship instead of just like FIFA 26, FIFA 27. People, you know, they're not doing much, right? Like, they're, they're really beholden to this bureaucracy which basically exists because FIFA was such a successful game that they basically haven't had to do anything innovative for 30 years. That will now sort of start to happen, which I, I'm very, I, I think, I think that's like sort of a, I'm actually more interested in that. Like how does AI, can you revitalize these existing businesses and brands, not necessarily new businesses and new brands. I'm actually, I have like zero interest, frankly, almost in, in like new things right now.

So we saw the dictatorship workflow, maybe not portable to other companies. I think this second workflow might be portable, especially some of those microservices, those smaller teams who want to pilot it.

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I wanna talk a little bit about Gumroad because it's just, it's gotta be one of the most fascinating companies out there. Tell us a little bit about how you guys are structured. You have only one employee, but you have contractors. How do those contractors get work? You pay them. What is the structure for getting work done at Gumroad?

Yeah, we've been through a lot. You know, we started out as as like a sort of traditional venture-backed startup in 2011 up until 2015 when we failed to raise our Series B. That's when I sort of did our first sort of major pivot as a, the product stayed the same, but as sort of operational pivot. So we downsized, we went to about 3 or so people, got to profitable and sort of ran the business myself for a while. Did customer support, product support, you know, fraud risk, customer support, fixing bugs, not that many new feature shipments, uh, but you know, basically just try to kind of keep the site up and respond to customers and stuff. Uh, then we started growing a little bit. COVID happened. That was a big boon, crowdfunding round. So all of a sudden we had some more cash. We started growing the team again, but this time sort of differently, primarily contractors, hourly, uh, part-time remote. Uh, and we have a core team now that's like full-time. So me and Urshad, and we have maybe 3 or 4 people who work like 30 hours a week or so. And then, uh, then we have the bounties that we do with the open source community now. So all of our code is open source, which means we don't actually need that many engineers on the team because You don't have to be on the team to work on the code, right? So in theory, you need a lot less, uh, less people and that's kind of how we work now. So, so it's sort of a, you know, small team, uh, and it's hard. We have an office that could fit 11 people, but it's just tough to, uh, you know, our bar is really high and AI is so cool and there's so many, so much opportunity for everybody out there that's hard to, hard to find the right, the right people.

So. So you aimed, it sounds like at one point to build a billion dollar VC backed company. What is your current goal for Gumroad?

I mean, very practically, very boring, but we're trying to get to $10 million in EBITDA. It's just nice to have a goal, nice to have a short-term goal for the year where the team and everyone can align on like what we're trying to do and the changes we're trying to make and the sort of order of magnitude changes we need to make to make that goal happen, which I think we'll get to. It'll be tight, but that's a good goal. I think pushes you at the very end to work a little bit harder. Beyond that, I haven't thought about it too much. Like open sourcing everything was a goal, but To be honest, like, we don't have a lot of goals because like if we have, if we want to do something, we just do it, you know, like there's not like a long lead time to doing stuff. So, um, we just started doing more frequent on-sites. So, so, you know, try to sort of one week a month where we get together in person and build stuff together. Uh, so, you know, well, I think a lot of my focus over the next couple of years will be on like, now I have a kid, I have a 5-month-old. So balancing the two and structuring the company and the culture is such that I can be really productive and I still do stuff with a team. Uh, but then also like. Not have it be as intense and as all-consuming as it can be sometimes. And so that's kind of like the sort of balance that I'm trying to strike. But yeah, nothing too crazy, to be honest. I feel like for the first time in a long time, which is the nice thing about having a profitable business doing dividends, is I'm not like looking at the future and the, like, I get dividends every year. So I'm not, I'm actually, I'm trying to like operate the business, you know, slightly better, like, like almost like as a perfectionist, like, can we just perfect the current business instead of like do other stuff all the time? So we'll see. Flexile is fun to work on. Growing, you know, chip away at that, you know, fix bugs, improve the product. I just want to like work on software, make the software better, have people use it, you know, and just like be proud of the work we do. I have some cool people to do it with, so I have some structure in my life, you know, stuff like that.

Honestly, I think that's the new dream though. Everybody wants what you have now, like a business working towards $10 million in EBITDA. Where are you guys at so far in the progress towards that?

Yeah, I think we're at like $7 or $8 million, so, you know, still Still work to do. Like, it's not gonna be a walk in the park, but, uh, that's pretty amazing. I think, I think we'll get there by the sometime next, next year.

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And how many dividends have you paid yourself in the last year?

Uh, last year I got about $2 million.

That's really the life, right? Living, uh, building a profitable software business, having a 5-month-old, controlling your schedule, paying yourself $2 million. I think a lot of people want to aspire to that. When you talk to people, you know, outside of when they're not in the VC-backed realm and they're just hiring like crazy, but they are trying to stay bootstrap profitable, they are growing, they're trying to take on AI tools. What are the things getting in their way? Where I see you very freely just using AI tools, what are the unlocks those founders need to hear?

Yeah, I mean, maybe their businesses are just doing super well, uh, and so they don't need to reinvent themselves. I think that's a big part of it, you know, like I think people underestimate like like, if you're doing fine, like there's no reason to like investigate the future. So yeah, so I would say that's the biggest one. You know, just like P0, right? Like there's only so many priorities you could actually have. So, you know, if it's not your number one priority in the business, like you have one more priority, like let's say it's hiring someone, you're going to be spending all your time on that. So that's kind of just like the way it goes. Hmm.

So you have some other things you're working on, like Antiwork, you talked about Flexile. I think you guys acquired like SmallBets. How does it all fit together, the picture for you? Yeah.

How did it fit together? Um, I don't know, honestly, I just kind of did like a retrospective on like COVID and everything else like that and just felt like, just felt like, uh, why not make a bet? And what was like the best fit? It wasn't like, is this the right fit? It's just like, well, let's just make a bet on the best fit. So that's what we did. Uh, and now we're in, you know, nice to have a community, you know, nice to have a place that's kind of like our default, like community of small-time creators. And so that's kind of like why we did it. And you know, I was thinking a lot on like, okay, we built this like big, you know, like last month, like 35,000 people sold at least one product on Gumroad. Gumroad. So there's like a huge number of people, but Gumroad is kind of plateaued and we sort of have what we want. We're incrementally making it better, but I don't think that's like more features isn't really what creators want. Like community advice, stuff like that, I think would be better. And so that's kind of like where we, uh, where we kind of decided to say, oh, maybe there's this like community and we can upsell. And so there's like the base Gumroad SaaS and then there's like the community that can actually help you like with legal, finance, business, marketing, sales, tax advice, hiring. That's where I think people, creators sort of tend to need help getting to the next level, going from like one person to a team, for example. Like even me, you know, I technically only have one employee or whatever, but like, that's who cares, right? Like what matters is like, are you, you know, doing the things you want to do? Are you, you know, do you have a great— the reason we don't have $1 billion single person companies is not that we can't, it's just that we don't want to. Like Google has 3,000 billion dollar companies in Google alone. It's like probably, I can't imagine how many PMs run a billion dollar company by themselves, you know? So It's probably pretty common, uh, within FAANG, there's probably thousands of examples. It's just outside of FAANG, if you're doing it all yourself, like then, like I have to do the bookkeeping, I have to do the, you know, like it's just not, not what most people want to do. Uh, so it tends to be more of like a marketing gimmick, like, oh, one person, you know, so yeah, that's kind of how I, I mean, maybe that's different. Like we have true, true AGI where you really don't need any accounting, like all sort of tasks you can sort of have a robot do. But in my mind, if that's possible, then like the robot will automate you too. You'll kind of have a zero employee business. Business. You won't have like a one-person business, right? You'll just go straight to zero. You'll still own the business, but there will be no people working on it. You know, it'll be kind of like a smart contract or something, something like that.

Yeah. I feel like that's what I discovered too, scaling my business. After a while, it's like, what, what was the point of being a solopreneur? Like, I just, so I could put the label solopreneur. I think I'm gonna switch over to entrepreneur and hire somebody to help me with taxes, with sales, with all these different activities that you don't want to do. There's, you don't have to stick to a solo business.

Yes. Yeah, exactly. I think that's a big part of it. Like, I think there's just so much— there's sort of like the pro-VC, anti-, you know, like pro-VC cult and that sort of a lot of the indie hacking is kind of like a response to that. But I think it also is a cult in a way, right? Where it's just like there's nothing wrong with having a team. There's nothing wrong with like working in person. There's nothing wrong with like being acquired and there's nothing wrong with having a job. Like, there's like we're all basically trying to manage our time and money equation and like the way that ends up looking for people is going to be different and it is very dependent on like your personal background, right? Like, like for example, I don't invest in public stocks. Most people would say that you're insane. Like, that's like crazy. Like, I just get $2 million in dividends. I just hold it in cash, 100% in cash. But the reason I do that is because I have access to deals that no one has access to. Like, the public does not have access to startups, right? So it's sort of like a lot of these, you know, these things are sort of dependent on that. Like, like, why would I invest in Figma as a public company if I could invest in Figma as a private company? So all this stuff matters when you're making decisions for yourself that, you know, that's just kind Part of things. So yeah, I think you don't want to be extreme. Like one person, you know, company is not necessarily the goal. It's sort of a vanity metric, right? It's kind of cool, fun. It definitely gets eyeballs. So like if there's ever like a Time cover of me, it'll be something along those lines just because that's kind of like what people read and click. I think having a team is great. Like the one of the nicest things about having profitable business, you can hire people, right? You can be like, oh, I really want to work with this person. Boom. I now can talk to this person for an hour every month because I hired them to do this task and I get to talk I'm going to talk to them about this specific thing. And it's, it's like kind of almost like a, like a hiring a therapist or something, you know, to, to, to, to some, to some degree.

Yeah.

As soon as you build that one-person company that is making like $500K or a million, I think everybody will cross that point. They'll realize it as well. Being a solo per business is kind of overrated, but I don't think what's overrated is embracing AI in every part of your business and being at the front edge of how to use AI in your business. Like someone I was talking to, he has a huge consultancy. So what he's done is he's created a bunch of AI agents that take the notes, that take the advice he's given his prior mentees, and then simulates for him a draft of what he would want to say after a meeting. So there's all these different workflows, whether you're in a consulting business or a product business, like we just demoed all day today, where I think being on the edge of AI is still really useful.

Totally. I mean, at the end of the day, it, it is like the technology of our time. So like I would've learned to drive in 1920s, and now you have to learn to use AI, right? So if you want to be in tech, that's like what being in tech is definitionally.

So you have a legendary Twitter account. That's what made me a fanboy back in 2021 as we were talking about. It's a lot of people. I think you have over 360,000 followers at this point on Twitter. So it sounds like that's helped you in a couple different ways, right? It's helped you with your deal flow, it sounds like for your angel investing, which is the major thing you're doing with those dividends. It's obviously help you grow Gumroad and you probably get some creator monetization. Are those the 3 main areas of benefit or how else do you think about that?

I, I, I think it's really good feedback. So I think most people don't have access to the number of people to give you feedback. So like imagine you have an idea, your idea's gonna be somewhat reasonable, but like if you have 100 people give you feedback on the idea, whether it's a book or a chapter or a web application or a product idea or a startup or a business or philosophy or politics or whatever, I just think I, my ideas are better because I just get so much more feedback about them. Mm-hmm. So I think that it's sort of like market feedback in some kind of way. Um, you just have a lot more of that. Uh, and so that's a really, really helpful thing. I think it's really helpful if I move to a new city, I sort of have like a built-in social network, which is really nice. Generally a lot of really cool, smart, hardworking, successful people. Um, I can sort of like pre-filter them just based on what they say on the internet, like whether I would like to hang out with them or not. So that's cool. But to be honest, that's about it. Like I actually think it's like never been less useful. It's actually really, and that's because the algorithms are are really good these days, right? Like you can sort of think about it like the better the algorithms get that like more useless your audience is because in theory, a really good algorithm means that like a new person with a really good piece of content, but no audience will get significant reach, uh, which can happen. So I think now more than ever, like the sort of incumbent advantage is very low for content. Uh, for other things, it's still high, but like for like being like, for example, if you're a new musician today, it's like the best time ever to be a new musician. It's never, never been a better time. Yeah, music, filmmaker, are you kidding me? Like, a new filmmaker today, the only problem is you have so much competition because so many people also have access to the same tools. So just like the number of people, but, but most people frankly don't actually compete that seriously. So you're not really like— the pool of people like doesn't grow proportionally to the how much easier it is, right? So even if it's 1,000 times easier to build web applications today than like 5 years ago or 10 years ago or 20 years ago, whatever, you don't see that number of people doing it, right? Like roughly a similar number of engineers today than 10 years ago, even though it's much easier to deploy something to the internet today, like a lot easier. And that's because people just have personal preferences, what they want to do, what they want to work on, how they want to spend their time. Uh, so I think a lot about that too. Like, how does AI like change things, but also how does AI not change things, right? Like if AI makes it incredibly easy to code, you're not going to see more software engineers. You may, you're actually probably going to see a decline in software engineers because the people who wanted to become software engineers already did. So like actually the hardness may be something that attracted them to it that like, if it's no longer hard, they may not. Be attracted to it anymore. Uh, so yeah, fun stuff to think about.

I was going to ask after that, and since we're at time, this is pretty much our last question here. Would you recommend people who are trying to create, you know, a really lean AI-first team to be investing in building a personal brand and building in public?

I mean, I think the most important thing is to get to know your customers, right? If your customers are there and that's a way to reach them, fine. Uh, if you're doing venture, fine, because your customer is the VC to some degree. So that's important. But I would say most people doing it, like they're doing it because they want to. They're not doing it because there's like a business reason to do it. Right. Like I'm not tweeting because there's a business reason. I didn't like come up with my, you know, like some sort of strategy. Right. Like I was just having fun. I was like a young kid in high school and I wanted to talk to other people building stuff. And the only way to do that was Twitter at that time. And I was literally in Singapore. There's like no way to hang out with these people in Singapore. So, you know, I created a Twitter account and there's like 100 people from Singapore on Twitter or something. And, and maybe it's not Twitter today. Maybe it's some something else. I think the most important thing is you want to get to, you want to build a reputation of someone who is helpful and smart, right? Like, like this person helped me in this way, right? Uh, that's generally, hopefully why I have followers. I don't have followers because I said something witty. Hopefully I said, I assume like people are like, oh, Sahil Lavingia like wrote this essay and it helped me clarify my thinking in this way and I'm going to follow him. Maybe he has some other interesting stuff, right? Like, so I think it's sort of like, that's kind of how I think about follower counts generally. It's just like this person helped me. And so I, that's kind of how I think about it. It can be in-person help. It can be offline help. It can be parental health, friends. The goal should be just like to help people. And like, if you help people, then you will have an audience, right? You may not have a follower count, right? Like you may not even have, uh, but like more people will show up to your birthday, right? Like more people will show up to your book launch. Like I think people, you know, there's, there's a big difference in like people, not followers and, and, and like genuine, like fanatics, you know, like, like if I walk down the street at Times Square, no one's going to notice. Famous, even though I may have a lot of followers. And then someone with very few followers, but is famous, you know, like, will, you know, people will notice, right? Like George Clooney. I don't know if he has a Twitter account, but like he would probably be recognized on the street. And so I think, you know, sort of there's like fame and I think people sort of proxy like followers on Twitter fame or something like that, but there's zero correlation, right? It's, it's, uh, it's kind of a weird, I think of it like you're kind of like on the other side of, of the Vegas strip. You're like on the production line. You're not supposed to see, but there's like all the creators are hanging out and all the, you know, business owners and all the, like grabbing a drink at the bar, all the cab drivers. Like, that's kind of like Twitter. So again, it's like, how many of those people know who you are? Right? Like how many, it's sort of this like meta, the meta world. It's sort of like the, it's sort of the deep state almost. Like it's just the people on Twitter are the deep state basically.

Or maybe they're all just really shy like me. And when they do see you in person, they just don't go, hello, how are you?

Yeah, that could be true to some degree. I do notice like if I wear a Gumroad shirt, I get recognized a lot more. But my guess is I get recognized somewhat similarly, but people feel comfortable because I'm wearing the Gumroad shirt that it's kind of like, it's okay to say, you know me, 'cause I'm the one saying I'm okay with this sort of, you know, this identification. So yeah.

Yeah, totally.

Yeah, it's funny.

We could talk for hours. Thank you so much for your time today, Sahil.

You're welcome. I really appreciate it. Hopefully it's helpful to people.

All righty.

See y'all later.

Bye.

So if you wanna learn more about how to shift to this way of working, check out our full conversation on Apple or Spotify Podcasts. And if you want the actual documents that we showed, the tools and frameworks and public links, be sure to check out my newsletter post with all of the details. Finally, thank you so much for watching. It would really mean a lot if you could make sure you are subscribed on YouTube, following on Apple or Spotify podcasts, and leave us a review on those platforms. That really helps grow the podcast and support our work so that we can do bigger and better productions. I'll see you in the next one.