SEASON 2 - EPISODE 170 - OCTOBER 22, 2025

Revisiting the good old days

Time has a way of reshaping what we believe, and sometimes, what we’ve published. In this week’s episode, CEO and co-founder Jason Fried chats with Kimberly Rhodes to explore one particular chapter of REWORK that no longer rings true. Jason reflects on their current stance on having multiple products vs. just one, what company’s should consider before they expand, and why knowing your limits still matters.

Watch the full video episode on YouTube

Key Takeaways

00:00 - Episode highlights
00:23 - The change in perspective on multiple products
03:49 - The team needed for the company’s expansion
06:18 - Recognizing when you’ve taken on too much
10:38 - The real value of writing ideas down
14:21 - Advice on launching new products while maintaining previous ones

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 from the 37signals team, joined by Jason Fried, co-founder and CEO. This week, I want to dive into one of the chapters of It Doesn’t Have To Be Crazy At Work. This is written back in 2018. Things sometimes change. So I want to go back to, Jason, one of the chapters which has changed significantly. I’m going to read just a little passage from it and then I want to get your thoughts on where you stand now.

Jason (00:28): Yep.

Kimberly (00:29): So it is a chapter called The Good Old Days, and you write, “Just a few years ago we made a number of different products. Today we make just one, Basecamp. We gave up everything else and the potential of millions more in revenue so we could focus in rather than pan wide.” And then you and David also write, “Rather than continue to invent new products, take on more responsibilities and grow more obligations, we continually aim to pare down and lighten the load even when times are great.” Okay. Obviously this is not recent. We’re not just Basecamp.

Jason (01:03): Yep.

Kimberly (01:03): We have HEY, and now we’re creating all of these other products. So kind of talk me through that, how that perspective changed back from 2018 when you guys wrote that to now.

Jason (01:14): Well, like they say, what to everything there is a season basically. I think that when we first launched the company, there’s a grand expansion. We made four products in four years and a few more after that. And then we realized we had too many things going on at once and we don’t want to grow our staff. So we said we can’t do all those things at once. So we contracted, contracted for a while and then we’re like, you know, we have this itch to make something else. It originally started by making a new version of Highrise, which is our CRM tool. That eventually turned into HEY our new email thing. We didn’t set out to make a new email thing. We just kind of found ourselves there and then we actually kinda looked in the mirror and essentially said this is kind of fun. We actually like making new things.

(01:53): This is actually what we do. And maybe we’ve been suppressing ourselves or repressing ourselves essentially by not doing this. But it was good. It was good to compress for a while and contract, and then we expanded again. So now we’re in this expansion mode again, right? And the expansion mode, it was HEY, we’re now building this thing called Fizzy. We’re doing Basecamp 5. We built Campfire and Writebook under the ONCE label. We may make some other things. We’ll see, but we’re back in this expansion thing. And so I think all things are true. There’s times when contraction’s good, there’s times when expansion’s good. I think you need to follow your own feelings on this. When we felt like we had too much going on, it felt good to not do as much stuff. And then at some point you get an itch and you realize you like to make things and you make more things. So I can feel both things at once too. In some ways I feel like we might be doing too many things at once again, but I actually still prefer that feeling. I still prefer making new things. I have new ideas. I want to see these things out in the world. And so we’ll see how that all pans out. We might be four years from now, we might contract it. I have no idea what’s going to happen, right?

(02:57): We don’t think that far ahead. It’s also like, you know what? We have this rare opportunity to have a chance to make new things, to have a cash cow like Basecamp allow us to support us in a way where we can make new things. We should take advantage of that obligation, in a sense, to explore. And that’s what we’ve done.

Kimberly (03:15): Okay. So you mentioned Basecamp, cash cow. I feel like we also have the benefit of the type of people who can be working on multiple things, like the infrastructure to be working on multiple things, the size of team to be working on multiple things. Tell me a little bit about that and our ability to be able to expand in this way.

Jason (03:36): We built a company where we can have small two-person teams basically working on things. So one programmer, one designer. And so we have about 60 people in the company. They’re not all designers and all programmers, but we have a good five or six product teams, basically, that are able to work simultaneously. So we’re able to do more things at once now across more products at once. We can also decide to put a product on hold for a little bit, redirect some energy somewhere else to make something new and then redistribute again. So we have that ability. Plus we have teams dedicated to infrastructure now. Before it used to be like the people making the products, were also doing a lot of the infrastructure work. It was a long time ago, but that’s the way it was.

(04:13): And that was just very hard because there’s infrastructure required and when they’re working on that, they can’t work on products. We can now do multiple things at once, simultaneously, different departments, different groups. And we’ve just become very, very, very efficient with building products. Rails is part of that, Shape Up is part of that, the talented people we have here is part of that, the way we run things here is part of that, and we’ve just figured out a way to make a lot of things simultaneously with a relatively small company. There’s a lot of companies that their mobile team is bigger than our whole company, right? So we’re just very efficient in that way. Plus, we produce a lot of open source, tons of open source stuff as well at the same time, infrastructure stuff that we extract out of our own development from our own products and put that stuff out there. And David’s doing a whole new Linux distribution with help from lots of other people. And Open Source has been very helpful in that way in that we can get a lot of stuff over the finish line and then a bunch of people can come in and contribute to that after the fact.

(05:06): So that’s another part of the strategy in a sense. And mostly it’s just we like it. It just feels right. It feels good to make new things. People are energized by making new things. It’s also exhausting sometimes. Even within these expansion seasons, it should be a little bit of contraction from time to time so you catch your breath. We don’t push people too hard over long periods of time, so they burn out, but it’s going to take on some challenges and kind of establish new PR in a sense every once in a while.

Kimberly (05:29): And how can you tell when you’re getting stretched too thin, like when there’s too much going on?

Jason (05:33): Everyone would probably have a different answer here.

Kimberly (05:35): I’m asking for yours.

Jason (05:37): Yeah, some people might feel stretched too thin as it is, and I might feel like we’re not stretched too thin, there’s other times… I think mostly it’s when there’s bigger ideas that we can’t seem to get to that we know we need to do, but we just don’t have the time, people, resources, energy, attention to do it.

Kimberly (05:54): Yeah.

Jason (05:55): I think for example, we couldn’t launch another product right now. We’re launching Fizzy. We originally were doing two things at once, Fizzy plus another product.

Kimberly (06:03): Right.

Jason (06:03): And then we lost somebody. And that was another example of like, well now we’re down one and now we certainly cannot do this two things at once. So sometimes it’s just a physical reality of not having enough people, or you had enough and then someone left and that changed the equation

(06:19): Because our teams are so small. If you have 18 people working on something and you’re down to 17, doesn’t matter if you have three people working on something and you’re down to two or two down to one, huge difference. So that stuff’s pretty obvious. But I can imagine there’s some people in the company think we’re doing too much right now. And they might be right also, but it’s also still fun. And again, we’re not doing it in a way we’re making people work 80 hour weeks and weekends. It’s none of that. So I think we can handle what we’re doing.

Kimberly (06:45): Okay. This is a little off subject, but because that viewpoint was shared in It Doesn’t Have to Be Crazy at Work, tell me about rewrites. Are you rewriting this book or writing a new book? I feel like there’s things in there that are dated.

Jason (06:59): Yeah, I think there are things that are of the time versus dated in that they’re old. I think they were the right decision at the time.

Kimberly (07:07): Sure.

Jason (07:07): And a book represents that alone. I can’t write a book for the future, write a book for then. And by the way, eight years from now, that book might be current again because we might be back to that, so who knows. But we are working on a new book. It’s not like a rewrite, it’s just a different kind of book. It’s more about the general philosophy of making it up as you go,

(07:28): Which is probably not going to be short essay based like our previous books, but a little bit more like a philosophy book, much longer chapters around a handful of topics and then probably backfilled with a bunch of FAQ style answers to questions that people would have after reading the first half of the book. That’s kind of the new format we’re playing with right now. And in that, it’s not the same kind of thing. There’s some shared themes because there’s just some shared points of view across that are all tied to the same thread back from when we started the business in ’99, but it’s a little bit more about decision making and approaches to things at a much higher perspective than specifics. I think our previous books would be things like, here’s what you should do. This book is really about here’s what we’ve done, here’s how we think about things. It’s not telling you what to do at all. This is not a book to tell you what to do. This is a book to read and understand how another company thinks about things. And that might spark some ideas in you, might help you see something you hadn’t seen before in yourself, might give you a perspective you hadn’t considered before, but it’s not like a how-to book.

(08:32): Not that other ones were that how-to, but there are more how to I would say.

Kimberly (08:35): Well, and I also said this is dated, but to be fair, I was able to find that chapter because it felt like such an outlier, compared to everything else that is like this is still what we believe as a company. This is still the philosophy that we have. That one was an outlier.

Jason (08:52): Yeah, there’s 10% that may not be as accurate today as it was when it was written just because times have changed and things are different. But the majority of that book stands, as does REWORK written in 2010. So all those ideas, I would stand by all of them with the exception of I dunno, maybe there’s a few essays there. I’m like, I don’t agree with myself anymore on that. So what? That’s not a big deal. The bulk of that is still exactly what we think, yeah.

Kimberly (09:16): Yeah. Okay. So let me go back to this renewed energy and new products. Is there a way that you are cataloging ideas that you have that we don’t have time to build yet? I feel like you guys always have new ideas. Are you writing those down on a list? Are you just thinking they’re going to float back up? How are you managing all of these ideas that you guys want to do at some future date?

Jason (09:41): Yeah, no, there’s no list. I mean there’s idea for what we’re working on right now, like Fizzy, there’s feature ideas that we might write down because we’ve thought about them and want to document them, but it’s not so we remember them later. It’s so we can pitch them now, and if we decide not to do them now, then that’s that. Maybe we’ll do ‘em again later, but just because we wrote ‘em up doesn’t mean we’re going to do ‘em. We write things for now, not write things for later. They just happen to be later also because they’re written down. But it’s not to refer to down the road. As far as bigger product ideas, I have one other product idea at the moment and I wrote up a pitch internally to a few people and that’s sitting somewhere on the sidelines right now because we don’t have time to do it.

(10:21): We’re not doing it right now. If we decided to build up that product, we’d probably do it next year at some point. But we’ve made no decisions whatsoever on that and it’s not been developed beyond just the initial, hey, we have a need for this. I have a theory here about this. Here’s how I think this thing could work and why I think it’d be good. And it was one writeup, like 800 words, 600 words, something like that. And that’s it. I think there’s maybe one sketch or two sketches in there. The sketch is a three second, here’s a box and here’s the things, whatever, and that’s it. So whenever we write something down that’s a little bit different, I just want to get this idea down in my head and write it down and just have it.

(10:57): But there’s not like 15 of those. There’s one which we might do next year. Otherwise the things we write down are all about things we would like to do now if we can. And if we can’t, they don’t get preferential treatment just because we wrote ‘em down before. New ideas bubble up whenever they bubble up and they are as valid as anything that we already wrote down or put down, but there’s not a long backlog or list of things we have to pull from ever. Like in Fizzy, for example, in Fizzy we have a collection called Fizzy Ideas. The Fizzy ideas though are for like, can we do this now? We’re building it now. These are some ideas we want to log and write down and discuss, but it’s not a backlog to pull from. These are just things that we could choose if we chose to choose them.

Kimberly (11:37): Well, and what’s interesting about that is there’s a Fizzy Ideas collection and there’s also a Fizzy Issues collection. I found myself the other day writing up a card on Fizzy Issues, and I was like, this isn’t really an issue. This is more of an idea. So it is, kind of, deciding between what actually needs to be fixed versus just something that would be nice.

Jason (11:57): That’s right, yes. I’m actually looking at the Fizzy Ideas collection right now, and these are mostly ideas, but there also are some things that are issues. And if you go to issues, it’s definitely more issues. It’s nice to have these things separate, but of course it’s nice to look at both because logging something that this can be subjective. If something doesn’t work the way I want to, is that an issue with it or is it an idea for it? And it doesn’t really matter. You put wherever you feel like it matters and we’ll find it anyway. But the fundamental thing I want to get across is that just because you wrote something down does not give it any preference over a future idea that you might have.

Kimberly (12:35): Yeah. Okay. And my last question, for people who are listening who maybe are software developers or just have their one thing that they’re working on, thinking about a second, what are some things that you would consider or have them consider if they have the capacity? Are there some guidelines that you might give them to think about when it’s too early versus yeah, dive into a new product. It seems like a lot to have more than one product when you’re very small.

Jason (13:02): Yes, it really is a lot. And the reason why I think people get into that so quickly, and we did this too, is because when you’re new at something, building is really fun.

Kimberly (13:12): Maintaining?

Jason (13:13): Maintaining stuff is not as fun. Once you built it, you’re building it is fun. You don’t have to listen to anybody. You build whatever you want.

(13:21): You put it out there in the world. Now you have to listen to a bunch of people. And that can be frustrating, it can be exhilarating, it can be all the things, but now you have a responsibility to others. And I would take that responsibility seriously. And this is my point is if you just jump right into building another thing, that first thing you made, you’re no longer probably going to have a lot of time to improve it and make it better. And so the bet you’re making is that that wasn’t good enough. I got to make another bet. I got to keep making bets. I think initially you should probably focus on the thing that you made for a while, for a few years, hopefully, unless it clearly doesn’t work at all. And I can’t tell you when that is, but there’s a point where this is not actually going to pan out. You might need to work on something else. But littering the market with 1.0 products that you just move on to the next one, move on to the next one, move on to the next one, move on to the next one. At some point it’s going to make people think, I don’t know if I should be using this, anything this person makes because they don’t pay attention to it after it’s been released.

Kimberly (14:19): Yeah, it’s a good point.

Jason (14:20): So I think you got to give things enough time. You got to keep reinvesting in them and developing them. And there is something very special about something that’s been around for a long time and been nurtured and cared for and improved over a long period of time. Something like Basecamp for example, in that you’re able to really, really, really, really hone and polish some experiences that are really meaningful for people who use the product. And you would never get to that if you just kind of jumped onto the next thing.

Kimberly (14:44): Yeah

Jason (14:45): So another way to think about this, if you’re going to build a business out of this, you best probably not jump around too much initially, unless what you’re doing is just not going to pan out at all. And then you should probably think about why did this first idea not pan out at all? Is this next one going to pan… like what did I get wrong here? Maybe? I don’t know. I mean, here’s the other thing. I could argue the other side, which is make a bunch of shit. There’s people who do this. Pieter Levels is a famous, what people call him a hacker anyway, not in a negative sense, in a very positive sense, where he’s made dozen, I think he’s made close to a hundred products.

Kimberly (15:16): Oh gosh, yeah.

Jason (15:17): One guy very fast, not very polished, his products aren’t super polished, they’re just like great simple products that do one thing really well, for example, or a couple things really well. And then like four of them, I don’t even know what the number is, maybe a dozen, maybe three, have kind of hit. And so his point is like, throw a bunch of stuff out there. Make a bunch of small bets, and then you can do that too. It just depends on what you’re kind of building and what you want to build. So there’s just different ways to look at all this, but I think you got to be careful, not just leave a bunch of unfinished work all over the place. That can be very, very messy and hard to get back into and hard to improve. I like the question because I can give a bunch of different answers and whenever I can give a bunch of different answers, the answer really is always, it depends on you. It depends what you built. It depends who you are. It depends what you’re selling. And don’t listen to anybody tell you how to do this.

Kimberly (16:06): Well, if that is a perfect place for us to end. 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 at 37signals.com/podcastquestion.