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

1. 0:00 – 2:31

   Sahil’s background

   1. SLSahil Lavingia0:00

      Can you do something that used to take two weeks in two 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 one hour.

   2. CVClaire Vo0:14

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

   3. SLSahil Lavingia0:21

      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, is like there is this part 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.

   4. CVClaire Vo0:42

      [upbeat music] 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 a billion dollars 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 Enterpret. Enterpret 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. Enterpret 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 Enterpret 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 enterpret.com/howiai. That's E-N-T-E-R-P-R-E-T.com/howiai.

2. 2:31 – 4:08

   How soon will AI do most engineering?

   1. CVClaire Vo2:32

      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 set?

   2. SLSahil Lavingia3:04

      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, I would say, like, by the end of next year, I would suspect that, like, every engineering team in 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 many organization adapt such that those people can do so, right? Like, the bottlenecks are- are show up in other places, like Tobi just tweeted about, you know, his Shopify 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, uh, to try and fail, and cross-share learnings, you know, all that, all that kind of stuff.

   3. CVClaire Vo3:57

      Okay, so we're gonna do it one at a time, which is you're gonna 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

3. 4:08 – 9:30

   Live demo: redesigning with v0, Devin and Cursor

   1. CVClaire Vo4:08

      things.

   2. SLSahil Lavingia4:09

      Awesome. Yeah, I mean, so I think the, 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, like solving customer problems. And for this product that we built, it's called Flexile, and it's, uh... You know, you can think of it like a, like Gusto or 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, uh, 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, tomorrow or the next day, will then do a, 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 two weeks or something, right?

   3. CVClaire Vo5:21

      Yeah.

   4. SLSahil Lavingia5:21

      And so, like, can you do something that used to take two weeks in two 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 one 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, uh, uh, saying, "Oh, it's so terrible," but there's always room to, to, to improve. And even on this one screen, which is the, 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.

   5. CVClaire Vo6:08

      Yeah.

   6. SLSahil Lavingia6:08

      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-

   7. CVClaire Vo6:15

      Yeah

   8. SLSahil Lavingia6:16

      ... have, like, a nice date picker. You know, if you go to, like, shadcn, and this is the beauty of open source is, you know, and the 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's, it doesn't really re- really need that much scoping. It's kind of just, like, replace date widget, you know, date picker in contractor invitation screen with, uh, shadcn date picker. We might as well. I mean, the cool thing with Devin is you can, like, let do that [chuckles] while you do other stuff, so there's- there's no risk, really. So I can select the Flexile 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 somebody 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-

   9. CVClaire Vo7:19

      Mm

   10. SLSahil Lavingia7:19

       ... 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 had a cool demo like this, where they have more like a natural language, something like this, and you could type in-

   11. CVClaire Vo7:34

       Yeah

   12. SLSahil Lavingia7:34

       ... in one 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-

   13. CVClaire Vo7:44

       Yep

   14. SLSahil Lavingia7:44

       ... 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-

   15. CVClaire Vo7:54

       Yeah

   16. SLSahil Lavingia7:54

       ... versions of them. We can take a look at how far it got on them. 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."

   17. CVClaire Vo8:06

       So you're, you're putting into v0, you know, use this form using the very descriptive, great requirements. Magical! [chuckles] So... And then you're gonna use v0 to get a prototype?

   18. SLSahil Lavingia8:20

       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, uh, 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 d- 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-

   19. CVClaire Vo9:02

       Mm-hmm

   20. SLSahil Lavingia9:02

       ... is just getting set up. You know?

   21. CVClaire Vo9:04

       Yep.

   22. SLSahil Lavingia9:04

       Just getting your admit, your, your developer environment set up, your end variables, local host.

   23. CVClaire Vo9:10

       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, um, how easy your... it is for an- any new engineer to get started, whether

4. 9:30 – 11:03

   Using the right tools

   1. CVClaire Vo9:30

      or not AI. So you have v0, in theory, going... There it goes.

   2. SLSahil Lavingia9:34

      Yeah.

   3. CVClaire Vo9:35

      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 out of the box, or was that something you were looking at before?

   4. SLSahil Lavingia9:53

      Yeah, it was, it was a huge reason to switch and try to adopt a lot of these tools, both... I, 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. 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-

   5. CVClaire Vo10:13

      Yeah

   6. SLSahil Lavingia10:14

      ... good at certain things. It's really good at front end. It's really good at React. It's really good at tailwind shadcn 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 background, back end, and, like, Hotwire or whatnot in the front end, like, these j- it just doesn't exist. Like, you, you would have to spend all your time just getting this to work, [chuckles] you know, some jQuery calendar thingy thing. You know, that's how Gumroad was for a long time.

   7. CVClaire Vo10:40

      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, um, compared to those who are maybe using some of these, these libraries and technologies natively.

5. 11:03 – 19:45

   Prototyping and iteration with AI

   1. SLSahil Lavingia11:03

      I, 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, 'cause if you think about it, what are they doing, right? They are thinking about what the features 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-

   2. CVClaire Vo11:42

      Yeah

   3. SLSahil Lavingia11:42

      ... but you wouldn't design, like, all the little interactions in here, right? Like, you would just design, like, like, without... 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'd, like, didn't consider it mobile.

   4. CVClaire Vo11:56

      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-... 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?

   5. SLSahil Lavingia12:19

      You know, normally I would have a few back and forths here. You know, you could spend, like, three or four prompts, like 10, 20 minutes-

   6. CVClaire Vo12:25

      Yeah

   7. SLSahil Lavingia12:25

      ... 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.

   8. CVClaire Vo12:34

      Yeah.

   9. SLSahil Lavingia12:34

      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.

   10. CVClaire Vo12:47

       Yep.

   11. SLSahil Lavingia12:47

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

   12. CVClaire Vo13:04

       And you reuse the exact same prompt?

   13. SLSahil Lavingia13:06

       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-

   14. CVClaire Vo13:13

       Mm-hmm

   15. SLSahil Lavingia13:13

       ... like, I'm like, for example, this-

   16. CVClaire Vo13:15

       Yep

   17. SLSahil Lavingia13:16

       ... 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 have 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.

   18. CVClaire Vo13:34

       Do you use any of the code from v0?

   19. SLSahil Lavingia13:38

       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. Uh, this is for a different repo, so it doesn't have shadcn, but it would basically like, you know, slot that file in, and then I could reference the file. And then, and, uh, you can also, I believe, just like, you know, you could, you could, uh, you could, uh, share it, and you could literally, like, just give the, the URL effectively, right? Like this. And you could just say, like, you know, mimic, 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 in line. 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."

   20. CVClaire Vo14:45

       Yeah.

   21. SLSahil Lavingia14:46

       I love putting... [chuckles] I don't know what this does, but for some reason, if, if I feel like I'm vibing with this person, like, they know what I mean when I say note. I mean, like, slightly-

   22. CVClaire Vo14:55

       Yeah

   23. SLSahil Lavingia14:55

       ... smaller font size, like grey, 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, uh, to Devin, and, and then it would, it would, you know, run off and, 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, 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 they-- 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 going to be able to execute ... Like, sometimes you don't want to 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-

   24. CVClaire Vo15:42

       Yeah

   25. SLSahil Lavingia15:42

       ... little bits that would make the customer feel really good. Uh, the user experience would go up, but the developer experience would go down, right? But if you know an [chuckles] AI is going to be implementing all of that stuff, and they're going to do it at a, 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, two 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 to happy accidents. Like, AI may just take your, your spec and actually do it better with it-

   26. CVClaire Vo16:29

       Yeah

   27. SLSahil Lavingia16:29

       ... than, than you would have. Uh, and so yeah, that's kind of how I use it, and then I, 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-

   28. CVClaire Vo16:43

       Yep

   29. SLSahil Lavingia16:44

       ... uh, like a preview branch, right? Where-- And I lo- I mostly love doing front-end 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 back-end stuff too. Uh, but, you know, with preview branches, like, I love making changes to antiwork.com-

   30. CVClaire Vo17:01

       Yep
6. 19:45 – 24:50

   Incentivizing AI adoption in teams

   1. CVClaire Vo19:45

      checklist. You know, I see you as an individual being able to add this and fix that, and update, you know, the, the homepage and all those things, and use Devin sort of asynchronously. I'm curious how you've made this work at the team level. Like, what are the actual operational pieces that have to be in place for this to not degrade into chaos? And then, what about just culture makes this work for you all?

   2. SLSahil Lavingia20:11

      Yeah, I mean, first off, it's not easy. Change is uncomfortable, right? Uh, 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, c- colleges and cl- classes are 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 [chuckles] than, like, at home in your bedroom, right? Part of it is doing it myself, too. You know, like, if your manager or 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, uh, Josh Pigford on YouTube, which is, like, three hours long, and I basically did it because I wanted to-- I was like, "This isn't..." You know, it got a lot of views, actually. Like, I, I-

   3. CVClaire Vo21:00

      Yeah

   4. SLSahil Lavingia21:01

      ... That's how important I felt [chuckles] it was, not just for me, but for everybody. But I was, like, 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 if once we switch 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. Uh, 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 30, uh, $33,000, uh, 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. Uh, and I actually did pretty well. Let's, uh, see the results. So I got s- I got fourth. I opened, uh, 27 PRs with Devin, and then three people beat me. So it's, uh... And I, you know, I do a lot of easy wins, you know, so, like, it- props to all the engineers who, 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," like, I'm just trying to, like, help people be more productive. I didn't know that was so controversial. But, you know, there's, like, a lot of small things, like remove this part of the homepage. There's this, like, recap that we do in Slack that's generated by AI, uh, that recaps, like, everything that shipped last week. And so I said, "Hey, Devin, could you..." You know, uh, like, for example, these two things don't really need to be here because there's nothing under them, right? So I just said, "Hey, uh, Devin, like, could you, like, you know, only show the products that actually have shipments and, like, hide the other ones?" And also, like, some of these aren't really shipments. Like, this one is only the back end. The front end hasn't shipped yet, so, like, make sure, you know, the pr- 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, uh, what this one is, right? So it found the Slack weekly, you know, recap, and it, it, uh, you know, it, it, it made these changes, and it created this PR. So we can actually go in and see this PR, uh, and we can, uh, confirm my-

   5. CVClaire Vo23:08

      Mm

   6. SLSahil Lavingia23:08

      ... 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, [lip smack] uh, 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, da, da, da. 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, 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 you- 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, uh, write all this code, right? Like, look up, like, for example, you know, like dot filter versus dot trim, or dot 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,

7. 24:50 – 31:47

   “Magical” date picker component development

   1. SLSahil Lavingia24:50

      you know?

   2. CVClaire Vo24:51

      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 little bit document doc strings 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-

   3. SLSahil Lavingia25:15

      Mm-hmm

   4. CVClaire Vo25:15

      ... replaced with the shadcn one.

   5. SLSahil Lavingia25:18

      Yeah, so the p- core problem I have here, which I guess, uh, is I need to make sure it works.

   6. CVClaire Vo25:24

      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, in the IDE. So you can actually-

   7. SLSahil Lavingia25:38

      Mm-hmm

   8. CVClaire Vo25:38

      ... 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.

   9. SLSahil Lavingia25:50

      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 s- watch it on this one, right? It's, uh, it's doing its, its little thing. So because I had used magical, it, in quotes, it- [chuckles] ... presumed that I wanted to call it magical. And you can see, we actually open sourced it recently, so it's, uh, it's working on an old repo-

   10. CVClaire Vo26:35

       Running locally

   11. SLSahil Lavingia26:36

       ... which is my guess of why it's not working exactly right. Um, so now there are two things I decided. So, you know, replaced this input, the standard input, with the type date, with this new component. That's definitely correct. And then it, uh, created this, uh, this component where it goes through, and it, it, it, uh, replaces it. So the thing that looks wrong here is it doesn't feel- 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 pr- this probably wouldn't work if I said, like, three 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-

   12. CVClaire Vo27:29

       Yeah

   13. SLSahil Lavingia27:29

       ... like, it's a better engineer-

   14. CVClaire Vo27:30

       Yep

   15. SLSahil Lavingia27:31

       ... than human engineer would be. So you ha- 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 correct approach. I would probably call it natural language date picker or something like that, 'cause magical doesn't really give you any insight into what's magical about it. Uh, but besides that, my guess is, like, this code, this parse natural language, uh, is actually, like, probably really, really robust, really good. Uh, even this magical look- like, 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. Find index, it's getting all... You know, it's basically figuring out, like, when you type next Monday, it's like three 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, two years ago, this would be, like, a so impressive-

   16. CVClaire Vo28:38

       Yeah

   17. SLSahil Lavingia28:38

       ... for, like, this would be almost like-

   18. CVClaire Vo28:39

       Ab-

   19. SLSahil Lavingia28:39

       ... an engineering challenge, [chuckles] you know? Like, I would hire an engineer based on this, which is... Now they would just go to ChatGPT and be like, "zzz," 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 a, 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 in, uh, to the code base. So you could kind of, like, do a lot of this, like, customer-focused iteration, you know, uh, on the, uh, in a WYSIWYG way, basically, like Dreamweaver, [chuckles] you know, uh, 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, brain power, and it just hurts my head.

   20. CVClaire Vo29:33

       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.

   21. SLSahil Lavingia30:06

       Yeah, if you, if you spend two weeks on something and your, you know, your annoying CEO is like, "Nope, that's not what I meant," it's like, "Oh!"... you know, and then you gotta spend, you gotta go for a long walk-

   22. CVClaire Vo30:19

       Yeah

   23. SLSahil Lavingia30:19

       -in a coffee break before you're back to work, right? So, uh, it's so much better to, like, really spend time-

   24. CVClaire Vo30:26

       Oh, wow!

   25. SLSahil Lavingia30:26

       -you know, here before.

   26. CVClaire Vo30:27

       Yeah, I just leaned in.

   27. SLSahil Lavingia30:28

       That was kind of cool. I like this idea.

   28. CVClaire Vo30:28

       So we got a redesign from v0 on this new employee inbo- 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.

   29. SLSahil Lavingia30:44

       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."

   30. CVClaire Vo30:52

       Yeah.
8. 31:47 – 36:50

   AI’s impact on marketing, sales, and support

   1. SLSahil Lavingia31:47

      so you can read it out nicely.

   2. CVClaire Vo31:50

      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 proved that you're at least in the top five people shipping PRs [chuckles] with DM or with Devin at, at the company.

   3. SLSahil Lavingia32:13

      Oh, by the way, this is merged.

   4. CVClaire Vo32:15

      You did it!

   5. SLSahil Lavingia32:15

      We got it merged, so it looks like, uh-

   6. CVClaire Vo32:18

      That's good ROI

   7. SLSahil Lavingia32:18

      ... looks like I made no mistakes.

   8. CVClaire Vo32:20

      Amazing.

   9. SLSahil Lavingia32:21

      So yeah, next week it'll be better. Like, think about it, that would've been like, you know, at least 24 hours, so-

   10. CVClaire Vo32:26

       Yeah, totally

   11. SLSahil Lavingia32:26

       ... that's like a nice 10X speed increase.

   12. CVClaire Vo32:29

       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 gonna be started by agents?

   13. SLSahil Lavingia32:44

       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 gonna really get there for a long time. There's just always, like, a higher level 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, we, you know, we have a, a, 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 back end." 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? Uh, and they're just emails, right? You go to Flexile, you sign up, but there's, I think, a lot more, uh, automation. You know, if someone signs up to Flexile with, like, Sahil@nytimes.com, you know, 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 know, you can, you can talk to AI, and it'll help you out. But this is all, like, reactive, you know? Well, what if I'm just browsing the page, and, you know, it, it knows that I, I'm in New York from my IP, you know, and it 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 raining, you know?" [chuckles] 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, you know, if 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. Uh, may- maybe even like, like, like, prioritisation. 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 ha- can very quickly sort of be like, "Okay, this is, this is, you know, gonna generate, like, you know, maybe $100,000 to $200,000 in value for creators, creator earnings. This will probably generate, like, 300, 400K." But then I have to also put on my engineering hat and say, "Okay, this is gonna take, like, 40 hours of an engineer's time. This is gonna take 300 hours of an..." 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 the, because you, you missed out this fact, it's actually much harder to ship or we don't yet use shadcn, so actually, you're underestimating this, and it could, like, reprioritise 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 prioritisation, 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. Uh, and imagine AI could take all it- in all that data-

   14. CVClaire Vo36:37

       Yeah

   15. SLSahil Lavingia36:37

       ... 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, what feedback should we be listening to?" And, you know, you can imagine, like, you just hit a button that says, like-

9. 36:50 – 40:02

   Deciding what to build when AI builds everything

   1. CVClaire Vo36:50

      Yeah

   2. SLSahil Lavingia36:50

      ... you know, "Assign to Devin," [chuckles] you know, and then boom, it's done. I mean, that's another weird thing, though, right? Is like, well, if d- if AI gets so good-

   3. CVClaire Vo36:59

      Yeah

   4. SLSahil Lavingia36:59

      ... why do you need it, well, just do everything? Then why, why, what's the point of prioritization?

   5. CVClaire Vo37:04

      Yeah.

   6. SLSahil Lavingia37:04

      Prioritization is a function of, like, limited resources. [chuckles] So that's a whole thing. It's like I th- 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 gonna happen. Like, I have no idea what we should even be building, and we spend time as a team, like, thinking about, like, what should we build? Like, we go- like, there's noth- there's no issues in G- in, in GitHub.

   7. CVClaire Vo37:21

      Cleared. Yep.

   8. SLSahil Lavingia37:22

      Like, because every issue is, 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 s- sit around and talk and pontificate and eat lunch, and, you know, we really have to think hard about, like-

   9. CVClaire Vo37:38

      Yeah

   10. SLSahil Lavingia37:39

       ... "Oh, we should do something totally radical, like open source the whole thing," you know? Like, things that a, 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 in 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-

   11. CVClaire Vo38:02

       Yeah

   12. SLSahil Lavingia38:02

       ... but still humans have to go talk to people, ask them questions, user research, design research, um, market research. Uh, 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-

   13. CVClaire Vo38:22

       Yeah

   14. SLSahil Lavingia38:22

       ... 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, that- it's insane. I can't imagine, like, how long [chuckles] that video took to make. It just... It's, it's so funny, like, it's so thoughtful, and so many funny, different little, like, Easter eggs in, 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 five years, it's gonna be like, you need to, like, post the fricking movie. It's, 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, that's what our dope- you know, that's what's happened to our, our, 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, you know, ex- recommendation experience that's, like, much more AI-driven and much more natural language than just, like, a marketplace of, you know, feed of products, where you can- it can remember things about your, your tastes, your preferences. You know, it can learn from you. We're launching a community feature, pretty excited about this, next, uh, 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, is, like, there is this, like, part of, 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, 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

10. 40:02 – 45:13

    Conclusion and final thoughts

    1. SLSahil Lavingia40:02

       to be valuable.

    2. CVClaire Vo40:03

       I can say for sure, if you're, if you're suggesting to us that AI is gonna 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 we 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 gonna 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 gonna operate in the future, if not, if not companies. So we're gonna, we're gonna wrap up with a quick lightning round. Two 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?

    3. SLSahil Lavingia41:00

       V0, honestly. I mean, it is a bias, I think, 'cause I spend so much time in product. I think of our 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, it will do this, is crazy. So I think a lot of it depends on, like, your role in the, you know, 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, you know, 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 [chuckles] UI for a bank than any bank has, you know? So I think that this is, like, something any- just, just anyone can do. Like, a kid could, like, have fun with this. So I would say, me, 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, you know, which is a kind of a nice, you know, Replit or Bolt.new or Lovable. Like, they- there, there's just so many.

    4. CVClaire Vo42:25

       ... 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've 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?

    5. SLSahil Lavingia42:48

       I mean, honestly, capital letters. Not in, like, a mean way, hopefully.

    6. CVClaire Vo42:52

       Yeah.

    7. SLSahil Lavingia42:52

       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 kinda old school, I guess. You know, you have, like, literally, like, lowercase and uppercase-

    8. CVClaire Vo43:03

       Mm.

    9. SLSahil Lavingia43:03

       -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, two 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 two or three, but you need 10. It's, it's kind of a nice way of, of letting, letting it, like, be more, more, more creative, so.

    10. CVClaire Vo43:34

        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 baking industry by generating [chuckles] an onboarding for a neobank, apparently, here, uh, in, in v0. I really appreciate you giving us a real look at how you're building with AI-

    11. SLSahil Lavingia43:52

        Yeah

    12. CVClaire Vo43:52

        ... both as an individual, as a t- and as a team. I think you're definitely gonna inspire tons of people to rethink how they show up at work, and I think a few folks are gonna be looking over their shoulder, thinking that you're about to lap them once or twice on some of, um, 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?

    13. SLSahil Lavingia44:13

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

    14. CVClaire Vo44:41

        Thank you so much.

    15. SLSahil Lavingia44:43

        Thank you. [upbeat music]

    16. CVClaire Vo44:45

        Thanks so much for watching. If you enjoyed the show, please like and subscribe here on YouTube, or even better, leave us a comment with your thoughts. You can also find this podcast on Apple Podcasts, Spotify, or your favorite podcast app. Please consider leaving us a rating and review, which will help others find the show. You can see all our episodes and learn more about the show at howiaipod.com. See you next time! [upbeat music]

Episode duration: 45:13