SEASON 2 - EPISODE 161 - AUGUST 20, 2025

Building with LLMs, finding a co-founder & other listener questions

Jason Fried and David Heinemeier Hansson sit down with host Kimberly Rhodes to field a fresh round of listener questions. They share perspectives on when coding assistance makes sense, finding a co-founder to compliment your skills, business succession planning, and more.

Watch the full video episode on YouTube

Key Takeaways

00:17 - When AI coding tools help vs. when they get in the way
05:44 - Does start-up success require a co-founder?
10:02 - Small business succession planning
15:46 - Honing the skill of coming up with new product ideas
21:41 - New ideas are often just solving existing problems

Links & Resources

Transcript

Kimberly (00:00): Welcome to REWORK, a podcast by 37signals about the better way to work and run your business. I’m Kimberly Rhodes with Jason Fried and David Heinemeier Hansson, co-founders of 37signals. This week, we are knocking out some listener questions. We got some video questions in, which we love to receive. The first one is from Ryan.

Listener - Ryan (00:17): This is Ryan Chitwood. I’m an independent iOS app developer on the side, and since I work by myself, I’ve been wondering about adapting your setup of one designer and one developer comprising a team. What do you think about these days with the advent of LLM tools like Claude Code? You know these are getting pretty good at coding at this point. What do you think about teams of one, that being a designer with some development skills, using a Claude Code or something like that as filling in the developer portion there? I don’t know if y’all are ever thinking about moving to that model at 37signals, but what do you think about for an independent person like me? Thanks.

Kimberly (00:53): David, I’m going to start with you and then Jason, I’m sure you have some things to add on the designer side.

David (00:59): I think this is one of the most amazing things about the LLMs and it’s something we’ve seen already at 37signals in a big way. JZ in particular have been really good on our team of just running ahead of programmers, and he’s able to produce so much more, so much faster with the LLMs than he was before. Now, it all depends on what kind of fidelity you need. At our scale, the number of customers we have and the criticality that we’re dealing with, we can’t usually ship a bunch of LLM code into production. It’s still just not good enough for that yet. There’s obvious errors, obvious mistakes. There’s barely a day that goes by right now without someone getting exposed online for shipping some LLM slop that then left a huge security hole. There was just this whole bit about Tea. I dunno if you saw this app where…

Kimberly (01:51: Oh, that Tea app

David (01:52): Women could talk about their experiences with men, and apparently it was done by this guy who literally had six months of experience as a programmer on a bootcamp and I’m sure used a bunch of LLMs and everything was basically just wide open. So here you had a runaway success app that spilled the tea on 2 million women because it basically wasn’t locked down. And that’s of course sort of the nightmare scenario. Not that these things can happen with quote, unquote real programmers, human programmers, whatever you want to call it, but it’s far less likely that it’s going to happen. So I would look at what kind of apps are you working on? Are you working on things where if user data got leaked, it’s potentially a major, major problem? Then maybe I would think about having someone more skilled come in and review it, at least at the end.

(02:41): But if you are working on say, a game or something just fun and frivolous, maybe something that doesn’t collect user data at all, who cares? Use LLMs all the way. Get some experience, get something out there. See your ideas in action. I mean, half the enjoyment with LLMs is not necessarily that you’re going to ship it, but that you get to see your idea actually work. And half the time when you see your idea actually work, you go like, well, that’s not quite what I meant. Bam, in trash it goes, and then you build something else. So I do think it’s going to be more and more feasible for single teams. I mean, I’ve experienced the same thing on the other side, that putting a quick design together. All the first Omarchy, Omakub, and Omacon websites were all almost one shot LLM productions. They were kind of a little bit janky, but good enough, and I just hit launch and then I had Sean, one of the designers we have here at 37signals, come in afterwards, spruce it up, tune it up, make it better, make it nicer. But the ability to just ship something and see if there’s something there is incredible. I mean, I absolutely love it. So I would feel no shame about it, again, unless you’re actually dealing with personal information that can’t stand getting leaked, then you shouldn’t do it.

Kimberly (04:00): Jason, anything to add?

Jason (04:01): Not a whole lot. I mean, I think it’s great to be able to get quick momentum on an idea and see something come to life. My question with all this stuff is always that like, then what, now what? You can get yourself in a position where you’re overextended too far out, you built this thing, you don’t really understand how it works. You’re the only one around and now something goes wrong and you ask the LLM to fix it and it can’t. It just can’t for whatever reason or it’s fixing something that’s not really the problem and it creates another problem. And now you’re in this place where you’re over the cliff already and you’re going to fall and you don’t know what to do and you freak out. That’s a dangerous place to be. I think with anything, is beyond your own competence and your inability to deal with reality at that point.

(04:45): So I think that’s the threshold for me is, how far can you take this? To what degree? And then are you comfortable putting this out there for real people to use? And what happens if something goes wrong? Because things will go wrong, software has bugs, all of it does, and when you don’t know how to fix it, it’s a real problem. So that’s it for me. But I agree with the criticality is also obviously a huge factor, primary factor here, but still, even if it’s not that critical and something breaks and you don’t know why, you don’t know how you can’t fix it, and this happens with LLMs, they get sort of in this loop where you can’t quite get to the thing that’s actually broken or you don’t know how to ask it, how to fix the thing that’s broken. You don’t even really know what’s broken and you describe it in a certain way, but it doesn’t quite do it. Then what? So just keep in mind that that could happen and maybe it’s a good problem to have. I don’t know. Maybe it’s not, but it’s a problem you’re going to have probably, and if you don’t know what you’re doing, I can imagine it can really inject a whole bunch of anxiety in the project.

Kimberly (05:41): Yeah, great feedback. Okay, the next question, also video question is from Anton.

Listener - Anton (05:44): Hi there, Anton here. I’m trying to learn more about starting a business and sampling knowledge from both aisles of the dispute. And so I did start-up school and now I’m reading REWORK. So my question to you is how do you guys think about finding a co-founder? Y Combinator strongly recommends it and you two also have a nice team, but is it possible to go as a solo entrepreneur?

Jason (06:10): I mean, it’s obviously possible. A lot of companies are run by one person or founded by one person. I mean, we didn’t find each other in that way, so we didn’t set out to find someone else to do something with. It just kind of evolved that way. This is my bias, which is work with someone first to get a feel for who they are, what they do, how you work together, and then maybe something else can develop versus going out there and trying to find your wife. It’s like you got to date first. And so the problem with business is that people sign contracts, and this is I guess not that different from getting married in a sense, but no one would just get married because they found someone at some conference. I mean, I guess you could do that, but most people don’t. So you got to find a way to date through work in a sense and see how it plays out.

(06:55): That’s kind of my big thing. I would say though, that to me, this idea that you must find a co-founder, I don’t understand that. I mean, I get it from YC’s point of view and VC’s point of view, which is like, well, if one person leaves, we haven’t lost a whole damn thing because that’s a huge risk for solo founders and someone who’s investing in a solo founder is if that person dies, leaves quits, whatever, the whole thing could be over tomorrow in a sense. So I get why they actually want a back up in that case. But I guess if I’m going to shift gears just for a second, if you are going to look for a co-founder, I think you want to find someone who does something different than what you do. You probably don’t want other technical co-founder or designer co-founder necessarily.

(07:33): You probably want someone who could do something else. There’s a big overlap on maybe the business side of things or general values and philosophy, but make sure if you have two people, that you’re getting two people’s worth of stuff and more surface area coverage versus just trying to find a clone of yourself to kind do what you already do. I don’t think that’s really valuable and it probably is going to end up, you’re going to end hating yourself in that case because you’re going to butt heads all the time over the same kind of work, and I think that’s going to be a problem.

David (07:58): I think what’s interesting about this question, where do I find a co-founder is that it’s often premised on like I’m sitting here at home, where are they? Why aren’t they showing up? Where are you showing up? Where are you going out? And what I’ve seen in the Danish startups that I’ve invested in is that a large percentage of them have co-founders who met in college, and that alone seems to be a great reason to go to business school, to go to programing school, go somewhere where you’re going to meet other people. And if it’s not going to be that, then you got to involve yourself in some communities where you’re likely to see that. I think open source is another option, especially if you’re working on something deeply technical and in that scenario you might actually have multiple technical founders, but you got to get out in some of that.

(08:46): This question of I’m just going to meet someone is in my opinion delusional, that just doesn’t happen. You have to put yourself in the kind of situations where you would meet someone, and I think college is actually one of the best options that you have. When I went through Copenhagen Business School, I had several people in that class that I worked with. Well, I could have imagined we could have started a business together. I then ended up meeting Jason over the internet and that worked out pretty well, but I think that’s probably the minority case. The majority case is you’re going to find someone more local to you that you actually get a chance to spend some substantial time with, that it isn’t just this speed dating encounter. You got to know someone for several months before you know it. Because I’ve also seen plenty of times that someone do get started with a co-founder and it turns into shit. It turns out terribly because the people are not aligned, they’re not compatible, they’re not, I guess now we’re into the perils of marriage there too, that seems to happen sometimes not aligned, not parallel, all these other things, but there’s no silver bullet. There’s no magic recipe where you… you got to get around other people for substantial amounts of time. It’s quite unlikely that someone’s just going to fall into your lap either in business or marriage.

Kimberly (10:02): Okay, question. I’m going to read this one to you guys. You can tell me you don’t want to answer it, ‘cause we’ve had a lot of people ask similar things in the past. This one is a YouTube comment. It says, do you guys ever think about the next generation? And by that I mean what happens when both of you decide to step away for good? I don’t need a business plan, but do you guys ever think about the transition or how to find the people to fill your shoes?

Jason (10:25): I don’t think we would find people to fill our shoes. I think if we decide that we’re done or when we decide we’re done, because at some point that’ll happen, I think we’ll sell the business and that’ll be that. I mean, anything could happen, but it seems unlikely that we would transition the business. There’s a variety of reasons why. Part of it is the way our ownership structure is set up that David and I would still have to be involved, and that doesn’t work. I don’t think you can have founders involved in a business on the sidelines. I think if the structure was totally different where the majority of our income didn’t come from profit distributions and whatnot, it might be a different story, but the way we’re set up, that’s just the way it is. And I think it would be unfair to another team frankly, to have us anywhere in the ballpark around because I don’t think it would work very well. I’m of two minds here.

(11:12): There’s something nice about continuity beyond the original founders. I think there’s also something really beautiful about companies that are run by founders that when the founders aren’t around, the company is over. I think things can just should end at some point. It’s like a band. You don’t replace the band. I mean, you can I guess replace the band members. You have three people in a band or two people or five people. Sometimes someone comes in and replaces a singer, ‘cause they die, or the guitarist who gets stoned and doesn’t show up anymore for practice. For the most part, the founding group is either there or they’re not. And if they’re not, it’s not the same band. And it would’ve been better off had the band just stopped. So I think ultimately that’s probably how this will play out. But I don’t know. And we’re not for sale at the moment, so I can’t say for sure, but that’s what goes through my head at least, honestly.

David (11:59): I think what really brings me to Jason’s conclusion is the fact that we’ve gotten some trial runs. Both Jason and I have been involved with other businesses including things that we had spun out from our own business along the years. And what I realized is I am uniquely ill suited to sit in the passenger seat of any car that I feel I have ownership of. If I’m not driving, I’d rather drive that fucking thing into a wall, and that’s a character flaw. I prefer it to be, otherwise, I’d prefer it to be able to just sit patiently in the passenger side and just offer sort of little nuggets of advice. And then I don’t care where we’re going that all turn out. That’s just not who I am. And I think that is the reality of a lot of founders of our size businesses. Because I do think that when you get to a certain size, certainly by the time you’re a public company, it is different.

(12:51): Not that they all pan out well once the founders leave. In fact, they’re endless stories about how they don’t pan out well. I think both Howard Schultz at Starbucks and Michael Dell at Dell tried to hand over the reigns to someone else, realized they didn’t like at all where that person took it and came back to it, even though those are two of the biggest companies in America. So clearly the risk is there even at that scale. But there are also clearly, of course, other companies that have managed to create that transition. At 60 people, 40 people, 80 people I think is a lot rarer that the ship can just keep sailing in the way where someone is replaced, the founder is replaced by someone else who just happens to have all the same qualities and urgency and judgment and taste and whatever that made the business work originally, they just slot in and it just all works.

(13:44): I actually can’t think of a single example off the top of my head. I can think of a fair number of examples where those kind of businesses end up getting rolled up or bought out by someone else. And in some cases it even works . In a fair number of cases also a doesn’t, but it seems like that’s the main realistic door out. What I certainly don’t want is when the day comes, and as Jason says it will at some point where we no longer run the company, I don’t want to be associated with it at all. Whatever, it’s got to be a million miles away. And if the next owners of the business choose to do something that I could not tolerate the whiff of if I was in the car, I can just go like, well, ain’t my business anymore. And then that’s that. So yeah, I think we’re very much on the same page about that. It’s got to be someone else’s. I was about to say headache. That’s not even true. This isn’t a headache, at least not most days. This is a pleasure, this is a privilege, but at some point the privilege is going to end and then it’s got to be a clean separation.

Kimberly (14:45): So no Fried, Heinemeier Hansson children taking over.

David (14:48): Do you know what? It’s funny. I was just thinking about that when I was saying I haven’t seen it pan out. Well, I do actually think family run businesses do pan out well.

Kimberly (14:56): That’s exactly what I was thinking, yeah.

David (14:58): The economy is full of them and in some countries it’s even a majority way of running the Mittelstand kind of businesses.

Jason (15:04): Germany, yeah.

David (15:05): But I also think that, I don’t know if I’ve seen it in tech. I actually wish it was different. Jason, you made the point the other day about what if we were making knives. I can totally imagine the son of a knife maker becoming a knife maker. I have a little bit of a hard time imagining my children sort of wanting to do exactly what it is that I do with computers.

Jason (15:25): Same. Yeah, that’s an interesting thought. I haven’t seen that. Have there been family run software businesses that have transitioned between generations? That’s an interesting question actually.

Kimberly (15:35): I mean, there haven’t been a lot of software companies that have been around for generations.

Jason (15:38): Well, that’s true too. But there have been a number that have been around for 50 plus years. I don’t know. That’s interesting. But yeah, I don’t see it either.

Kimberly (15:46): Okay. Let’s go to this question. This came as a text from Brent. It says, “I am a long time fan of Ruby on Rails, but only recently started listening to the podcast. I never realized that 37signals has produced so many products over the years. Question for Jason and David. How do you come up with new product ideas and validate them before investing a lot of time in building them? I know you two are not fans of MVPs. Do you see this ability to find new product ideas as being an innate gifting or something that can be cultivated?” So kind of two-part question. How do you come up with the new ideas and is that just a natural talent that you guys have?

Jason (16:24): Well, just to be very humble about it, we haven’t had a lot of huge hits. We’ve had Basecamp. It’s been a massive, massive hit. Highrise was another big hit. HEY has been a good hit, but we’ve done a dozen things. So our record, we have a decent record. Luckily we have one massive, massive hit, which is Basecamp, but we can shake ideas out of our sleeve, but most of them don’t work. And I think that’s just the reality anyway. But I think it’s fun to just keep making new ideas and trying new things occasionally. And some things come from direct needs that we have. Primarily, it’s that. It’s like we need this thing or we have this idea for something we want to use that we don’t have. We’re talking about a new product right now. We’re building something called Fizzy, which is the bug thing, and we’re building a new version of Basecamp.

(17:13): But there’s another idea that David and I have been chatting about a little bit related to some stuff that he’s been going through with the Linux stuff he’s doing and this community building. And I’m like, god that would be really nice to have for our products. And so there’s a spark there. It’s not this, we have to drop everything kind of spark, but there’s a spark there and it tends to, does it ignite a fire? Does it ignite something? Is there heat there? And then sometimes you just begin to make it. You don’t put everything aside. You make it on the side and you see where it goes. So to this point about this question about validation, we don’t validate things externally in that way. I don’t believe there’s such a thing, frankly, because I think you can ask people all sorts of questions and it doesn’t matter because they’re not real answers.

(17:55): Would you pay for X, Y, or Z? Sure. Well, if you don’t have to pay for it, it’s not actually an answer. Or would you use X, Y, or Z if it did this? People are like, yeah, sure, I’d use that, but that doesn’t mean anything ‘cause I can’t use it right now. So I’m not a big fan of that. I’m a big fan of internal validation. If we’re going to build something, are we going to use it ourselves? Are we using it? What does it feel like to use it? And we’ve had a few things that have started and then died, and we’ve had a few things that have continued and then we’ve had a few things that have continued and continued and continued and continued. But I don’t think it’s a particular talent, frankly, to come up with an idea. The hard part then is to form the idea and to see it through and to figure out if you’re willing to bet on it, and if you think there’s something there, those are the things that I think you need ultimately to see something through.

(18:40): But I think a lot of people have ideas, and especially in this era, ideas are everywhere. It’s like, which ones make sense? How are you going to guide that idea? Where are you going to stop the idea? That’s the other thing, like an idea is naturally has no boundaries, so it can get as big as you want it to be. Where are the boundaries? I think that’s another thing, like where’s the discipline to say this is enough of this idea before we launch it to see how it works. Those are some of the thoughts that I have.

David (19:05): I think part of the problem here is seeing it as a issue of talent. Do I have the talent to pick these ideas? I don’t think it’s so much about talent as it is about exposure. If you work in a company, if you work for other people, if you work on something that already is a business, you will literally be forced to run into a string of issues of stuff that’s broken. You’ll be forced to use all sorts of systems that are crap, and you have all sorts of ideas of how to make them better because you have to use them for a specific purpose. It’s the exposure to real problems in real domains that give you the ideas. Now, we’re fortunate at 37signals that we have a relatively large company, 60 odd people. You just run into problems all the time, managing 60-some people managing the products we already have.

(19:54): It kind of just feeds on itself. But I don’t think anyone really has the talent that they could just sit down in a vacuum and come up with amazing ideas and then internally in their head actually decide and weigh them and see whether they’re good or not. I don’t think it works like that. I think you have to get exposed to the world and the world is going to tell you. Does this feel like something people would pay for? You’re working for someone else, would they pay for a better way to do this? They probably would. If it would save you a bunch of time on some drudgery that you’re doing anyway, or you’re dropping a bunch of balls, you just get a vision of what good is when you’re dealing with real problems. It’s not something you can just cook in your little noodle by yourself.

(20:36): You have to actually get exposed to it. So less about talent, more about exposure. And this is one of the reasons I find that folks who were a little bit too much in a hurry to start a business, I mean, I was totally in a hurry too, so I can very much relate to it, but why are you in such a hurry? Can you just expose yourself to a little experience first? I mean, now I really sound like an old person. And the reason I say it this way is actually this is, I think it’s a Hemmingway quote about great writers that to be a great writer, yes, sure, you have to have some fluidity of language. You got to have grammar down in some ways at least, so the rules, so you can break them. But then also you have to live a little, you actually have to have had life experiences that are worth telling other people about. Very few individuals are just born with this magic ability to tell interesting stories if they haven’t experienced anything in life. And I think the same thing is true in business. You actually get more ideas for business when you do business, and a great way of doing that is working for someone else.

Jason (21:41): I agree with all that. The other thing I would add is there is something about a certain degree of awareness and insight that you can spot something that could be better and that you don’t just take for granted that this is just the way it is. So whether or not that’s a skill, I don’t know, or talent, I don’t know what it is, I don’t really care what it’s called, but I think it is important to go, wait a second, hang on that… no, no, no, this could be better. Or this whole category of thing is it’s been going on the way it’s been going on for so long that, wait a second, no one’s paying attention to this anymore. There’s a better way to do this. I think we did that with HEY, for example. Email had sort of been since Gmail had launched, was it 16 years prior or something like that?

(22:22): It just was a solved problem or considered a solved problem. We’re like, nah, there’s a lot of problems here that are not solved. And in fact, the solved problems that they have been solved have created new problems because things aren’t the way they used to be when they first started. So there’s this general awareness of going, wait a second. So you almost want to get snagged. You almost want to have hooks all over you in a sense to get snagged on something, go, wait a second, this is too hard. Or this could be smoother. Or there’s an opportunity here that no one else is seeing for some reason, or someone’s seeing, but they’re seeing it, I’m seeing it in a different way. I feel like if I had to really think about, I feel like I get snagged on things, and that’s where I’m like, what is this thing that caught me? How do I get rid of this? That’s where the ideas come typically, for me at least. It’s not like, yeah, it’s not sitting there and dreaming up in this empty state what to do next. It’s running into something and getting caught on it, usually that goes, what is that? What is that thing? And then you go with something.

Kimberly (23:23): Sarah Blakely, who’s the founder of Spanx, who sold her company for billions.

Jason (23:27): I’ve seen her on Shark Tank

Kimberly (23:28): Yes. And she has said, everyone has a million dollar idea. It’s taking action on it. And so I think this is part of it is you guys have ideas, but then you actually push them forward and don’t let them get stuck in that idea phase.

David (23:41): I do also think there’s a fair of survivors bias there. Yeah, everyone has a million dollar idea. It’s just stuck in a haystack of 10,000 bankruptcies, like potential bankruptcies. So you got to find the needle, and I try to always have the humility, as Jason mentioned, we’ve actually launched quite a lot of things over the years, and it’s Basecamp first and foremost that has sort of paid for the splendor of the bulk of it. We’ve had some other very nice hits that could have been their own successful businesses in their own right, but we would not have gotten to the level we are today without Basecamp. That was one fucking idea we had in 2003. We’ve literally been going for 22 years since then. We haven’t had a better idea. We haven’t had a more profitable idea. We haven’t had a, sort of, more uniquely well timed idea.

(24:32): So do you know what? It’s probably not that easy. We’ve really developed an eye, both Jason and I think we’re spotting all these things. We’re getting snagged on ‘em, and even with all of that, it’s quite difficult to replicate it. So I do think having some humility about the fact that you can be quite good at spotting ideas and that’s within your realm, and you can certainly develop that eye. You can certainly train yourself to get snagged on those problems. That’s how you get to play the game. But once the game starts, whether you end up all the way up here or somewhere in the middle or not at all, have some humility that a fair bit of that is outside of your control. That doesn’t mean you should stop trying, stop learning. Obviously you’re going to have more opportunities and you’re going to have a higher batting average if you practice and if you get better. But also some very good entrepreneurs, in my opinion, just never found a million dollar idea out of all the ideas they were. They couldn’t get it. So have that in mind too, and then do it anyway.

Kimberly (25:30): Okay, well, with that, we’re going to wrap it up. Rework is a production of 37signals. You can find show notes and transcripts on our website at 37signals.com/podcast. Full video episodes are on YouTube, and if you have a question for Jason or David about a better way to work and run your business, leave us a video question. You can do that at 37signals.com/podcastquestion. If we use your question, I’ll send you some REWORK merch.