Gumroad CEO's playbook to 40x his team's productivity with v0, Cursor, and Devin | Sahil Lavingia

Can you do something that used to take 2 weeks in 2 hours? And that's like a 40 times speed increase. So that's kind of like the number that I have in my head generally, like what's the most optimistic case if you kind of remove all the bottlenecks, something that would take 40 hours would take 1 hour.

If you're suggesting to us that AI is going to raise the bar on what's possible to do, you are certainly setting the standard.

The majority of human engineering will be removing tech debt such that AI engineers can actually ship features. It's also scary, I think, which is why I think so many people shy away from this stuff. It's like there is this part of why change is uncomfortable is that change can kill you. There's like a fear of change. It's like job security, right? But at the end of the day, I think it's sort of also job insecurity.

Hey everyone, welcome to How I AI, a podcast on how AI is transforming how we get things done. I'm Claire, product leader and AI obsessive here on a mission to help you build better with these new tools. Today I have an absolute powerhouse guest, Sahil Lavingia, CEO and founder of Gumroad. If you don't know Gumroad, it's the platform that has helped creators sell over $1 billion of products directly to their audiences. Sahil's been at the bleeding edge using AI to transform how companies build products and write code, doing everything from open sourcing the entire Gumroad repo to paying his employees thousands of dollars if they can write more AI-powered code than he does. Today he's gonna show us exactly how he does it. Let's dive in. This episode is brought to you by Enterpritt. Enterpritt is a customer intelligence platform used by leading CX and product orgs like Canva, Notion, Strava, Hinge, and Linear to leverage the voice of the customer and build best-in-class products. Enterpritt unifies all customer conversations in real time, from Gong recordings to Zendesk tickets to Twitter threads, and makes it available for your team for analysis. What makes Enterpritt unique is its ability to build and update a customer-specific knowledge graph that provides the most granular and accurate categorization of all customer feedback and connects that feedback to critical metrics like revenue and CSAT. If modernizing your voice of the customer program to a generational upgrade is a 2025 priority, like customer-centric industry leaders Canva, Notion, and Linear, reach out to the team at interpret.com/howiai. That's interpret.com/howiai.

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Hey, so I'm super excited to have you here. And before we dive into the demos, I wanted to call out something that you said a couple days ago, which is Devin, the AI engineering agent who I also love, is writing 41% of your PRs right now, and you expect it to go to 80% by the end of the year. So do you think that's the baseline that we should all be shooting for? Do you think you're way ahead of the curve? Where should we all be compared to that benchmark that you just said?

I feel like I tell the team constantly, like, we have a lead, you know, but the lead is getting shorter and shorter every, every day, every week there's a new model coming out. So I would say like by the end of next year, I would suspect that like every engineering team at any company is You know, using Cursor and Devin and v0 and all these tools to ship, you know, multiple times faster. And the question is, is mostly like, how do we organization adapt such that those people can do so, right? Like the bottlenecks are, are showing up in other places. Like Togi just tweeted about, you know, his S Amplify AI stuff today. And I think that becomes the question is like, how fast can you actually change your organization, your culture? Especially when you're remote, it's harder to make these big changes across the org, to get people to learn new stuff, to try and fail and cross-share learnings, you know, all that, all that kind of stuff.

Okay, so we're going to do it one at a time, which is you're going to show us how you actually redesign or build something using these tools. So we'll get your screen up and you can walk us through how you think about things.

Awesome. Yeah, I mean, so I think the coolest thing about all this AI stuff is that you get to spend more time doing what you really enjoy, which to me, and I think you as well, like solving customer problems. And for this product that we built, it's called Flexile. And it's, you know, you can think of it like a Gusto or a Deel, but built specifically for the way that we run the business, which is like hiring a bunch of people, a lot of project-based, a lot of hourly-based, monthly retainers, all sorts of different types of people, remote, in-person, full-time, let them choose their equity split, manage your cap table, all of that stuff in like the same product. And one of the reasons I love AI is that I can basically just use the product and instead of running into some issue and being like, hey engineer, can you go solve this? And then spending all this time like writing up a spec, you know, then putting that into, you know, sending that to a designer, that designer will then do like, you know, tomorrow or the next day will then do a mock, there'll be some back and forth, and then it'll go to like next week on Monday, it'll go to an engineer. They may have some questions that goes back to the designer. And by the time it ships, you know, it makes it to production, even for something like relatively trivial, you know, it's been 2 weeks or something, right?

Yeah.

And so like, can you do something that used to take 2 weeks in 2 hours? And that's like a 40 times speed increase. So that's kind of like the number that I have in my head generally, like what's like the most optimistic case, if you kind of remove all the bottlenecks, something that would take 40 hours would take 1 hour. And that's pretty awesome. So even in this form, like pretty simple, and I built the software, so I'm like, you know, I'm not like saying, oh, it's so terrible, but there's always room to improve. And even on this one screen, which is the contractor invitation page, there's like already a couple things that I noticed that like aren't big enough to like really ask someone to do. Everyone's busy. They have their own stuff that they're working on. But there are like a few things that I noticed. Like for example, the date picker is kind of terrible.

Yeah.

Like it just uses like the, you know, the native date picker. It's not humanized. You know, you can't type in like next Monday or this Monday or have like a nice date picker. You know, if you go to like ChatCN, and this is the beauty of open source is, you know, and why AI is so good is there's a lot of open source. You get like a nice date picker like this, right? It's like nicely humanized and you can do all sorts of cool stuff. So that's like one thing I noticed that I think is like a really good candidate For this, I would go straight to Devin. I would, you know, it's, it doesn't really, really need that much scoping. It's kind of just like replace date widget, you know, date picker in contractor invitation screen with Chad's end date picker. We might as well. I mean, the cool thing with Devin is you can like do that while you do other stuff. So there's, there's no risk really. So I can select the FlexCel repo and, you know, say for this specific page, like update the date picker. From the browser native, you know, input to ShadCN import if required. I've never actually used this button, but again, this is a good example. Like even someone who's using this stuff, like you have to constantly like up your game to learn more. You know, basically I think this should be really like a, a rich text like this. Like you can just type into it and you could type in like next Monday, I think resend. at a cool demo like this where they have more like a natural language, something like this, and you could type in, yeah, in 1 hour tomorrow at 9:00 AM, these sorts of things. Um, or Slack actually has something similar where if you go into a canvas, you know, this is our roadmap. If you type in like Thursday, right? This is kind of like what I think would be really cool. So I think this is also like, I'm gonna have Devin do multiple versions and then we can take a look at how far I've gone on them.

Yeah.

But this is kind of how I would generally work is I would just take these forms and say like, you know, build this form.

So you're, you're putting into V0, you know, use this form using the very descriptive, great requirements. Magical. So, and then you're gonna use V0 to get a prototype?

Yeah. So generally my flow is.

v0, Devin. Cursor?

Is probably how I would say it. Like, generally, I, v0 is my prototyping tool of choice. And once I have like a really good prototype that I'm happy with, then I, I go to Devin and if Devin sort of fails to completely finish, then I open it up in Cursor. Though I did, I think last week Devin launched this pairing mode where you can actually like jump in. And so I haven't really experimented with that yet, but that's presumably— I would use something like that going forward where I could actually just jump in and fix the changes. The nice thing is Devin actually runs— you know, one of the most annoying things about being a developer is just getting set up, you know, just getting your admin, your, your developer environment set up, your env variables, localhost.

One of the tips I have for engineering organizations that are large, which is if you can make your environment easy to set up for AI, it's probably a lot easier to set up for new hires. So it pays off to sort of use that as a testing ground for how easy your— it is for any new engineer to get started, whether or not AI. So you have v0 in theory going— there it goes.

Yeah.

Okay. So you have v0 going on building you a prototype. I have a question here, which is, you know, you mentioned ShadCN as your component library. Was that driven by you know, using these AI tools and, you know, those, those component libraries being outta the box, or was that something you were looking at before?

Yeah, it, it was a huge reason to switch and try to adopt a lot of these tools both. And, and I think it's, it's one reason that I think many people haven't really, it hasn't clicked, I guess, the AI stuff. They're like, oh, I tried it, didn't really work. It's not that good. It makes a lot of mistakes. It's, you know, basically it's faster for me to do it than to have AI do it. And I found that that's like a lot of it is just like AI is Yeah. Good at certain things. It's really good at frontend. It's really good at React. It's really good at Tailwind, ChatGPT, and stuff. So if you're not using those sorts of tools, you're not gonna get the value. Like trying to ship something like this with like Rails in the backend and like Hotwire or whatnot in the frontend, like these, it just doesn't exist. Like you, you would have to spend all your time just getting this to work, you know, some jQuery calendar thingy thing, you know, that's how Gumroad was for a long time.

One of the things I wonder is if, you know, engineering leaders will decide on particular transitions or migrations to make just to power this stuff so that their teams can move a little bit faster because they're just seeing themselves be left so far behind compared to those who are maybe using some of these, these libraries and technologies natively.

I actually think that like the majority of human engineering will be Removing tech debt such that AI engineers can actually ship features. Basically, like, designers will be shipping features because if you think about it, what are they doing, right? They are thinking about what the feature should do. And then engineers are just basically setting up the groundwork, the framework, the defaults, the standards, the linting, the CI pipeline, the infrastructure, the dev setup such that designers actually are, more and more capable over time of like basically taking their idea. Like if you were a designer, you, you know, you would like just design this part, you know, you'd design this, but you wouldn't design like all the little interactions in here, right? Like you would just design like that because it would just take too, too long. Or you wouldn't even consider it because you didn't play, you know, you didn't, for example, like often you'll have a designer and they like didn't consider mobile.

Okay. So you got this design. Let's take a look at it. It looks pretty good. It has the magical date creation, which is type— there you go— type a magical date and it works. So it's not just the design, it's the functionality. And you said the next step for you from v0 is into Devin. So how does that transition work? What are you doing?

You know, normally I would have a few back and forths here. You know, you could spend like 3 or 4 prompts, like 10, 20 minutes, like really nailing like the interaction, right? You may say like, You know, add a, add a, add a clear button, or, you know, when you hit delete, it should actually delete. And this stuff will get only faster and faster and faster. But once, you know, once you're happy with what you have, normally I would take like the final prompt and I would just paste that into Devin, you know, and I would basically do similar to what I was doing before.

Yep.

And I can see Devin doing its thing, having lots of fun, and I could start a new Devin. And basically do that, right? So like on here, on this page.

And you're reusing that stuff a lot.

And then I would go here, build this form. Yeah, it's often, I mean, sometimes if I'm going back and forth and I learn stuff, like I'm like, for example, this.

Yep.

I may just add here, you know, like all the, these are kind of like learnings where I could, it's basically, I'm like, oh, my spec could have been better. Like this, these are things a human engineer also would've maybe not done, you know, like I basically just kind of go back and forth and like build, basically I'm like, the, the v0 is kind of clarifying my spec in a way.

Do you use any of the code from v0?

Sometimes I do. Like sometimes I'll take this and just use this command. And if I put this and I went into Cursor, uh, if I had Cursor open on something, if let's say I had it open on this, for example, I would just go to terminal and I would just paste this right in and it would put in this component. This is for a different repo, so it doesn't have ChatCN, but it would basically like, you know, slot that file in and then I could reference the file. And you can also, I believe, just like, you know, you could share it and you could literally like just give the URL effectively, right? Like this. And you could just say like, you know, mimic this, right? You know, and you could say more things, you know, for example, I noticed that like in this thing, like I probably don't want the date to change inline. I like this parentheses is kind of weird. I'd probably add like a little note, you know? So I'd be like, the putting the date in parentheses is kind of weird. Put it below the input as a note.

Yeah.

I love putting— I don't know what this does, but for some reason, if I feel like I'm vibing with this person, like they know what I mean when I say note, I mean like slightly smaller font size, like gray, you know, like note. Like I feel like a designer would get it. So, you know, this is kind of like what I would give to Devin and, and then it would, it would, you know, run off and do its thing. It'll wake up and it'll do all these things. All, but all the stuff that I would basically do, right? Open cursor, get the thing. Find the files that need to get changes. But I personally, one of the things I think is really, really important is spending more time in V0. Like, I think many people just like, they do a first pass and basically I think MVPs are no longer enough. Like, you can actually spend like 10, 20, 30, 40 minutes here if you know that Devin is gonna be able to execute. Like, sometimes you don't wanna spend too much time here because it just creates work for the engineer, right? You're like, oh, now I have to think about this and that and this and like all these like, Yeah. Little bits that would make the customer feel really good. The user experience would go up, but the developer experience would go down, right? But if you know an AI is going to be implementing all of that stuff and they're going to do it at like a very high level of conscientiousness, you might say, oh, by the way, redesign it to like have this, or like, you know, different roles, for example, right? Like different roles have different amounts, show a preview in the dropdown, you know? So one may be like $200 an hour, one may be like $2,000 pay per project, et cetera. You know, one may be $250K a year. Just for fun, I might say like one may even have multiple pay rates because I've been exploring this idea generally. And I think part of the beauty of not doing it yourself is the happy accidents. Like AI may just take your spec and actually do a better job with it than you would have.

Yeah.

And so yeah, that's kind of how I use it. And then I generally, If you're hosted, you know, depending on the project, uh, our newer projects are all Next.js hosted on Vercel. So they'll even give you, yep, uh, like a preview branch, right? Where, and I lo— I mostly love doing frontend stuff with, with Devin. Actually, now with, they have this pairing thing, I could actually go in and like run Rails console and like check the backend stuff too. Uh, but you know, with preview branches, like, I love making changes to antiwork.com.

Yep.

Because I can test them almost immediately, right? I can be like, you know, let's say a new person joined the company, you know, I can just say, hey, add this person who joined the company. This is their motto, by the way.

Yeah.

Pick a fun icon that matches for them. Like, I didn't pick any of these icons. I would not have made myself a king, for example. I just said, like, I basically just asked everyone in Slack, like, tell me if you want it to link anywhere. and what you're— what you want your, you know, your, your slogan to be. And then I asked Devin to actually do it and pick an icon for each person.

That brings me to something I was thinking about, which is when you were in v0 and you were asking it to add on features, I was playing the product manager in my brain and I was thinking, oh, in past lives people would say, no, that's scope creep. We're just focused on the date picker or we're just focused on Updating this component, we can't kind of scope creep and add more and more features. And what I think, I think is interesting, I'm curious your point of view, is you can really start to go to the edges of some great user experience and it's less about how much time will this take or is it too complicated? It's more about what's actually gonna work and be, be useful.

Yeah, totally. And like, I often, like, I mean, maybe this annoys some people at the company, but like as I'm doing v0 stuff, like on other things, I'll be, I'll like go into the issue and be like, Let's see if I have one here. Like, I wanted to improve the multiple pay rates per role, as I mentioned, right? Like, this is— and I'll, you know, I'll be like, I'll just go in here and be like, you know, like this one I had, I was like doing something with Gusto and I kind of liked it, you know? And I was like, did I turn on this? And it's just free. People can ignore it if they want, but it's like free design research, you know? So all of a sudden they have an example of this.

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Yeah, I mean, first off, it's not easy. Change is uncomfortable.

Right.

It requires work and energy. And biologically, I feel like we're trying to save our energy all the time. So you have to, you know, you have to motivate people. You have to make it exciting. You know, there's a reason like colleges and classes aren't in person, right? Like there's a— it's like fun to train together. You know, it's easier to go to the gym in a gym than like at home in your bedroom, right? Part of it is doing it myself too. You know, like if your manager, your annoying boss is telling you to do something, it's different than like leading from the front a little bit. I often do like screen shares. Actually, like I recorded these videos and I recorded this one with Josh Pigford on YouTube, which is like 3 hours long. And I basically did it because I wanted to. I was like, this is, you know, got a lot of views actually. Like I—

Yeah.

That's how important I felt it was, not just for me, but for everybody. But I was like, I basically recorded it for the team. I had my team in mind as I was doing it. Like, check out how cool it is. Like, Imagine once we switched to Tailwind, like how fast we can, you know, do this kind of thing and like how, you know, it sort of is part of that, bringing the energy. We also financially motivated people. So there's a couple times here, I'll find you an example of a Devin competition we did. So we did this competition where we did $33,000 split amongst whomever opens and merges more Devin PRs than me over the course of May. So, you know, it's a kind of a fun way to like motivate people to learn. It's time-bound. And I actually did pretty well. Let's see the results. So I got, I got 4th. I opened 27 PRs with Devin and then 3 people beat me. So it's, and I, you know, I do a lot of easy wins, you know, so like props to all the engineers who, who did it. But yeah, I, this is all my, all my Devin PRs. A lot of people are like, there's no way you use Devin. Like you're making it up. You're just trying to like go viral or whatever.

I'm like, not really.

I'm just trying to help people be more productive. I didn't know that was controversial. But there's a lot of small things like remove this part of the homepage. There's this recap that we do in Slack that's generated by AI that recaps everything that shipped last week. And so I said, hey, Devin, could you, for example, these 2 things don't really need to be here because there's nothing under them. So I just said, hey, Devin, could you only show the products that actually have shipments and hide the other ones? And also, Some of these aren't really shipments. Like this one is only the backend. The frontend hasn't shipped yet. So like make sure, you know, update the AI prompt that we're using for this, which by the way, I've never seen. Like I have, I just, I just know that there's an AI prompt that's, you know, involved and, you know, it'll, and that's actually what this, what this one is, right? So it found the Slack weekly, you know, recap and it, it, you know, it, it, it made these changes and it created this PR. So we can actually go in and see this PR. And we can confirm my, my suspicion or not, which is, oh, turns out there is a prompt. Focus primarily on shipments, feature improvements, and bug fixes, right? Prioritize these categories. And then it also did something here, which is, if we looked, it did this. It added a filter. So, you know, basically only the projects that have more than one. The thing that I would critique about myself is that ideally we would have a test, and maybe there is a test that I don't know about. So this is when the human would come in. I don't normally just hit merge on these things. You know, I would normally send this to somebody else and be like, hey, I did my best shot at this. And you could see here for the Slack recap, don't include product names. And then I, I pasted, uh, pasted this, uh, the link to the, to the update. You know, I would normally like say, hey, uh, well, can you make sure this looks good to you? And if there are any tests that need updating. And personally, I think this is way better that like someone has done most of the work for you. And basically, I think humans will start the process. I think of it like flying a plane, like humans will take off, decide where to go and land typically, you know, do QA in the, in this context, but, you know, not actually build, write all this code, right? Like look up, like, for example, you know, like .filter versus .trim or clean, or, you know, like every language is different, right? But overall, I know rough amount of software architecture that like, this is, you know, this is the right solution, right? To this problem. You're just adding a simple filter that removes the things. And ideally there would be a test, so I would have even higher confidence that, that this, uh, that this has done what it, what it should, you know?

One thing I was gonna call out on the code you just wrote, showed was I find that these AI engineering tools are pretty good engineering citizens in that their code is well commented. They call out when, you know, there's a little bit document docstrings and things like that that make it easier to parse some of those, those changes. Okay. So this is what we kicked off with. It's the native date picker replaced with the ShadCN one.

Yeah. So the core problem I have here, which I guess Uh, is I need to make sure it works.

Okay. So you're showing the time-lapse of Devin here, which is basically a screen recording of every single step along the way. Right now you're in the, in the terminal and the IDE, so you can actually replay step by step how Devin got all this code done. It looks like it has in here, you know, reasoning and thought and planning.

Exactly. And then the part that I'm looking for, and hopefully it did it, is that it would run, it would run the app locally. And it often does this, but sometimes if you have a complex app and we just open source this so that it may have like broken, uh, but it would actually run the browser in its little local box and then it would test it. So let me ask it to do that. Run the browser. And it's awake, so it should pretty quickly start doing. doing that. And it's, this is Devin right here, Devin Box, Mr. Devin. Uh, and also we can watch it on this one, right? It's, uh, it's doing its, its little thing. So because I used magical in quotes, it presumed that I wanted to call it magical. And you can see we actually open sourced it recently. So it's, it's working on an old repo, which is my guess of why it's not working exactly right. Um, So now there are 2 things I decided. So, you know, replace this input, the standard input with the type date with this new component. That's definitely correct. And then it created this, this component where it goes through and it replaces it. So the thing that looks wrong here is it doesn't, it doesn't look like there's any AI magic. So some, it's sort of making, which maybe it doesn't need to, maybe it's smart enough to know if I just type in today, tomorrow, or yesterday. But, you know, it, this probably wouldn't work if I said like 3 Sundays from now, but maybe that's fine. Maybe that's not actually what anyone would, would really do. This maybe even is a good example of something that, to your point, like I think AI has really good hygiene, engineer hygiene, where it is on a, on a micro level.

Yep.

Like it's a better engineer.

Yep.

Than human engineer would be. So you have to spend more time on like the architecture and like the planning aspect of it, making sure your execution is correct. Like calling it magical date picker maybe is not the approach. I would probably call it natural language date picker or something like that, because magical doesn't really give you any insight into what's magical about it. But besides that, my guess is like this code, this parse natural language is actually like probably really, really robust, really good. Even this magical, look, check out the math on this guy, you know, like, whoa. Pretty simple, but like, how long would it You know, how many times would you have to tweak it to like, oh, I, you know, like I got it wrong. This like fancy addDays function, like it's pretty, uh, pretty clever how it's doing, how it's doing that. FindIndex, it's getting all, you know, it's basically figuring out like when you type next Monday, it's like 3 days and you're adding the days to get to the right, right day in the calendar. And it's parsing the day based on, it's like, that's like, this would be like a You know, 2 years ago, this would be like so impressive for like, this would be almost like an engineering challenge, you know? Like I would hire an engineer based on this, which is now they would just go to ChatGPT and be like, and you know, it would, it would, it would work. So what you could do is to go back to the v0, if you really wanted to enhance this, you know, you could just sort of take this component and they're actually working on a way to like embed it, you know, bring a component back into v0 and then you could like iterate on it. and the UX, like a designer could even do that with v0, and then you could then pull it back into the codebase. So you could kind of like do a lot of this like customer-focused iteration, you know, on the, in a WYSIWYG way, basically like Dreamweaver, you know, versus like, like in code. I mean, like this, you have to think so hard to understand like what, how do you improve the user experience? looking at this, right? The amount of like brainpower we're in, it just hurts my head.

What I think about is imagine that an engineer took this and went a week away and came back and said, here, I built your magical natural language, you know, date picker. And you said, no, that's not really what I want. It feels like such an expensive iteration to throw out that code and do something new. Whereas you, you can iterate that on that You know, in a couple minutes or a couple hours over and over and not feel like you're wasting, you know, time and expense and people's, honestly, people's like motivation and energy. I think about that a lot as well. Yeah.

If you, if you spend 2 weeks on something and you're, you know, your annoying CEO is like, nope, that's not what I meant. It's like, you know, and then you gotta spend, you gotta go for a long walk and a coffee break before you're back to work.

Right.

So, Uh, it's so much better to like really spend time, you know, here before.

Yeah, I just leaned in. So we got a redesign from V0 on this new employee onboard— onboarding, and not only did it get new features, but you got a beautiful update on the, um, date picker with some suggested common timeframes in there.

Yeah, this is super smart. Like, and all I did, by the way, I just said build a really dope natural language date picker for an HR product onboarding form. So probably the critical piece is like HR, right? So it's like building it in the context of the problem you're trying to solve, which is, you know, if you're, if you're, if you're building like a, like a party planning tool, you probably have like Christmas or, you know, like whatever, you know. But in this case, yeah, next Monday, in 2 weeks, you know, probably it's going to be next Monday. That's my guess is that is the most common. You know, but you could say, actually, we're, you know, we're, we're based in a, you know, a country in which like we work, we start on Sundays or Tuesdays and boom, you know, and you could do all sorts of interesting things or we're in a, you know, a place in which our date, you know, we put the day before the month or whatever. And so, yeah, just, it's just, yeah, just a great opportunity to like really push the envelope and just like really spend more time. Even, I love this, they put the first name and last name next to each other.

Yeah.

So you can read it out nicely.

So we just watched you ship in a new component, build a magical and now dope date picker for your employee onboarding tool. You've shown us how to get this done across your org, and you prove that you're at least in the top 5 people shipping PRs with Diem or with Devin at, at the company.

Oh, by the way, this is merged. We got it merged. So it looks like, uh, looks like it made no mistakes. So yeah, next week it'll be better. Like, think about that, would've been like, you know, at least 24 hours. So that's like a nice 10x speed increase.

This is a lot about engineering at Gumroad, and you said, you know, 41% of your PRs are being written by Devin. You're writing code. You know, who— what org is AI coming for next? Where the 80% of the work you think is going to be started by agents?

I mean, I think you could see, you know, if you think about what are the orgs that exist, you know, it's like design, product engineering, customer support, sales, marketing. And I really, I don't know, I actually was probably more optimistic on like full automation. I don't think we're going to really get there for a long time. There's just always like a higher level of abstraction that you get to operate at. So, you know, there will be, for example, like I think there's a lot more marketing automation that could happen in terms of like suggested tweets, like You know, it could just watch what's happening in GitHub. It could like suggest, hey, this thing, we, you know, we have a content framework, we should post about this feature, right? Right now I notice myself having to like, you know, say, hey, this thing shipped in GitHub. By the way, only half of it shipped, only the backend. There's still all this nuance that I think, you know, marketing could get like a lot more efficient. Sales too, I think like, for example, there are all these people who sign up, you know, they show up in our database basically, right? And they're just emails, right? You go to Flexisle, you sign up, but there's, I think, a lot more automation. If someone signs up to Flexisle with like sawhill@newyorktimes.com, you could sort of queue up an email to them. There's so much focus on customer support. We even built our own customer support product with AI, which is great. You can talk to AI and it'll help you out, but this is all reactive. Well, What if I'm just browsing the page and, you know, it knows that I'm in New York from my IP, you know, and you could wave at me and, you know, it could be like, hey, what's up? How's New York? It's kind of cold out there. It's kind of rainy, you know? And you'd be like, oh yeah, it is. It is raining in New York. Why do you care? And you could have a conversation and, you know, you're like, well, you know, it's kind of nice to be able to like talk about the problems customers are facing. So yeah, I mean, there's, there's, I think sales, like making it more, making support more about sales, making it more proactive. I think making design more about product, making engineering more about architecture. You know, I think there's always going to be more and more stuff to do. Maybe even like, like, like prioritization. I think I spend a lot of my time, like, you know, for example, like going through GitHub and saying, okay, we have all these tasks, we have like 27 things, like what do we build first? And right now it's like in my head, basically I've seen all these things go live or maybe even a better example more people would relate to would be Gumroad. You know, we have this big roadmap and, you know, I basically, I think I'm pretty good at this, but the reason I'm good at this is because I've seen every single thing ship. And so I kind of can very quickly sort of be like, okay, this is, this is, you know, going to generate like, you know, maybe $100,000 to $200,000 in value for creators, creator earnings. This will probably generate like $300,000, $400,000. But then I have to also put on my engineering hat and say, okay, this is going to take like 40 hours of an engineer's time. This is going to take 300 hours of an engineer's time, you know, and like do all this math, which you can go to business school and learn about byte and like all these things. And I could totally imagine like, you know, a button here that's like magical rank, right? And then it just like sort of goes through and maybe you should actually know that because you missed out this fact, it's actually much harder to ship or— We don't yet use ChatGPT until actually you're underestimating this and it could like reprioritize it, right? And you could do all sorts of interesting things. That's like a huge— I mean, think about how many people at these large companies, especially like they're spending so much of their time on strategy, quote unquote, which is really just prioritization, right? And what we do is we just email all creators and we just put together a list of things. And I just, we just sent this Google Doc to like our top 200 creators in 2024. And we kind of like ranked this based on what they wanted from us. 'Cause it turns out like they're the ones paying our bills. Right. And we started shipping it and imagine AI could take all it in all that data. I mean, all their sales volume we have access to, right, in our database. And you could somehow kind of like get a good, good sense of like, okay, what feedback should we be listening to? And, you know, you can imagine like you just hit a button that says like, you know, assign to Devin, you know, and then boom, it's done. I mean, that's another weird thing though, right? Is like, well, if AI gets so good, why do you need to just do everything? Like, why, why, what's the point in prioritization? Prioritization is a function of like limited resources. So that's a whole thing. It's like, I really, I mean, I would love to be in a place where I come into the office and I have no idea what's going to happen. Like, I have no idea what we should even be building. And we spent time as a team, like, thinking about, like, what should we build? Like, we go, like, there's nothing, there's no issues in GitLab.

Cleared. Yep.

Like, because every issue is solved. So, you know, it's cleared, we're at inbox zero. And so it's like, okay, well, what do we do? And then we sit around and talk and pontificate and eat lunch. And, you know, we really have to think hard about, like, Oh yeah. We should do something totally radical, like open source the whole thing, you know, like things that, like an AI probably wouldn't suggest that it wouldn't be in the, in the next token prediction or even in the reasoning models or like, okay, we should do really advanced content customization options. Okay. Like what, what is that? Okay. Let's go design and v0 a bunch of that and do a lot of research. You know, I think research is obviously gonna get a lot better with, with AI, but, but still humans have to go talk to people. ask them questions, user research, design research, market research. I think sales will always be important. I think marketing, like, I think marketing will be one of those things where like the average marketing, like AI will get so good at marketing that like the level of what's interesting to a human, like kind of like the, you know, that meme of the Saratoga Springs guy drinking the water and whatever, obviously like putting banana on his face. Like to me, that's like a sign of how good AI is. That like that level of content production is now necessary to go viral. Like, it's insane. I can't imagine like how long that video took to make. It just, it's so funny. Like, it's so thoughtful and so many funny different little like Easter eggs, you know? And I think that like, that's kind of what will need to happen is just like, you have to like up the game more and more and more. Like, you know, right now artists can post like a painting on Instagram and people will be like, oh, amazing painting. But like in 5 years, it's going to be like, you need to like post the freaking movie. It's like, that's just what people will expect. Like, hey, we just want to see your like 30-minute sci-fi movie that you did. And that's just like, for free, sorry. It's just like, that's what our dopamine, you know, that's what's happened to our dopamine system. Or we can spend like a whole day talking about like, how do we get better at recommending products on Gumroad? Is there a totally different kind of recommendation experience that's like much more AI-driven and much more natural language than just like— a marketplace of, you know, a feed of products where you can, it can remember things about your tastes, your preferences, you know, it can learn from you. We're launching a community feature, pretty excited about this next, later this week, which is pretty big. But we, you know, there's just tons of, yeah, I mean, who knows? I mean, it's exciting. It's also scary, I think, which is why I think so many people shy away from this stuff. It's like there is this like part of why change is uncomfortable is that like, Change can kill you, you know, like there's like a fear of change. Like, you know, it's like job security, right? But at the end of the day, I think it's sort of also job insecurity. Like, we don't know if like what we do will continue to be valuable.

I can say for sure, if you're, if you're suggesting to us that AI is going to raise the bar on what's possible to do, you are certainly setting the standard. I think you're showing an entirely new way for teams to build, You're showing an entirely new way for a leader to show up and actually contribute to the work product of the company, which I think is really inspirational. And then I think you're also showing, look, you just have to go learn these things and try things, and, you know, you're going to get in a loop, but over time you can actually become one of these leaders that's, that's on the leading edge as opposed to the lagging edge. So I, I think it's great, and I think you're setting the standard for how EPD orgs are going to operate in the future, if not, if not companies. So we're going to, we're going to wrap up with a quick lightning round. 2 questions. If you could encourage people to learn just one of all, all your toys here you just showed, just one that you think is the highest impact, which one would it be?

v0, honestly. I mean, it's a bias, I think, because I spend so much time in product. I think if I were more of an engineer, I think Cursor's agent mode is pretty crazy. I think if you're like a CEO of a company, I think Devin is like the most impressive. Like the fact that you can just be in Slack and just talk to it and it will do this is crazy. So I think a lot of it depends on like your role and what you value and what you think is the most important. But v0, I think it's just like the lowest hanging fruit. I think everyone is kind of familiar with Figma. And I think a lot of people think that like, okay, now people, no one questions that AI can code, even though a year ago people were like, say, oh, it can't code or whatever. But now people are like, oh, it can't design, it doesn't have taste, you know? And so it's just like really, you know, like design a really nice onboarding wizard for a bank, you know, and like watch it do a better UI for a bank than any bank has, you know? So I think that this is like something that is just anyone can do. Like a kid could like have fun with this. So I would say, yeah, I'd probably nominate v0. And then, you know, the cool thing about v0 is it shows you what's possible. And so then if you want to execute on it, then you have to like learn all the other, all the other tools. Uh, the other nice thing about v0 is that it comes with a URL. So you could build like tic-tac-toe and send it to your friend and play tic-tac-toe, which is a kind of a nice, you know, Replit or Bolt.new or Lovable. Like they, there, there's just so many.

We've talked a lot about how you are setting up incentives like bounties to get people to use AI or learn AI. But how do you get AI to do what you want? So I found that everybody has their own tactic, like they're mean, they offer money. What is your strategy for getting AI to listen to you when it's in a little bit of a loop?

I mean, honestly, capital letters, not in like a mean way. Hopefully, hopefully it doesn't take it the wrong way. But I just think it's like, it is, you know, kind of like, it's kind of old school, I guess. You know, you have like the Literally like lowercase and uppercase. And like, it's just a really easy way of saying like, this part is really important. Like, please do not ignore this specific part. There's another hack that I love called et cetera. So if you want a list of things, you, you can name like 2 of them and then just say et cetera. And it will often like riff. It's really fun to just like be like, it's kind of like a test, you know? It's like you've come up with 2 or 3, but you need 10. It's kind of a nice way of letting it like be more, more, more creative. So.

Well, this has been incredible and we have to wrap by showing you have not only redesigned your own product, but you've taken on the banking industry by generating an onboarding for a neobank apparently here in v0. I really appreciate you giving us a real look at how you're building with AI, both as an individual and as a team. I think you're Definitely going to inspire tons of people to rethink how they show up at work. And I think a few folks are going to be looking over their shoulder thinking that you're about to lap them once or twice on some of, on some of this building. So thank you so much for the time. Where can people find you and how can they be helpful to you?

Yeah, you can find me on, on, on Twitter/X. My handle is @shl and helpful. I don't know, just anytime you use see something I've said that you disagree with or think my thoughts could be improved upon, just reply, let me know, DM me. I'm always looking to get feedback and improve my, improve my thinking. So I just appreciate everyone tuning in and I'm excited to see what everyone builds.

Thank you so much.

Thank you.

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