SEASON 2 - EPISODE 172 - NOVEMBER 5, 2025

The itch for a new version

In software development, there are updates, and then there are complete overhauls. This week, Jason Fried joins Kimberly Rhodes to talk about how the team decides when it’s time to rebuild from the ground up. They dig into the transition between versions, how customer feedback fits in, and even drop a few hints about what’s coming in Basecamp 5.

Watch the full video episode on YouTube

Key Takeaways

00:10 - A walk through of Basecamp’s evolution
03:00 - How to recognize when it’s time for a new version
05:52 - Pricing considerations
11:42 - There’s no perfect moment to ship a new version
13:16 - How and when to evaluate customer feedback
18:58 - A sneak peek at Basecamp 5 features

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, joined by the co-founder and CEO of 37signals, Jason Fried. As you guys probably know, we are in the process of building a new version of Basecamp, Basecamp 5, and although we can’t share a lot about that now, I did think it’d be interesting to talk a little bit about why we’re making a new version, but not only this version, but why we choose to make new versions of our products versus just adding new features. So Jason, maybe we start a little bit with the history. Basecamp started as Basecamp back in the day, and then we made Basecamp 2 onto Basecamp 3, which then became 4. As you’re doing this kind of process, what kind of things are you thinking about on making something completely brand new, a brand new version, a new number at the end versus just adding features?

Jason (00:52): Yeah, I mean when we started this we didn’t have any idea that we would be making big new versions. We just make Basecamp, which is now called Basecamp Classic, but just Basecamp. And we did everything we could to make it the best thing it could be. We added a bunch of features and refined it and updated the interface and all the things, and there comes a point or there came a point, I shouldn’t say there comes a point, this is not always the case, but in our case there came a point where we had a new idea that would not fit on the chassis, let’s say, of the existing product. It was a new interface idea. It was a radical departure from what we had done initially and when we come up with that, you can’t really graft that kind of thing on to what we had because it also came with new technology ideas, new structural ideas, infrastructure ideas on how to build some of this stuff, and I guess we could have technically grafted it on, but it would’ve been such a radical departure that it made sense for us to say, let’s start from scratch here.

(01:50): Anyone who’s renovated an old house, well maybe you understand what I’m talking about. It’s actually easier to build a new house.

Kimberly (01:54): Yeah.

Jason (01:55): Than it is built, to renovate down to the studs an old house because you’ve got all sort of things that you’ve got to deal with versus starting over from scratch. So it was like we’d done a bunch of renovations in the existing place and that was enough, and then we’re going to decide to build a new house. Now, part of that was leaving the original house standing, so Basecamp Classic still stands today and it’s still used by thousands of customers today. So no one was forced to change from Classic to what became known as Basecamp 2. We’ve changed our mind on that over the years with future versions, which we can get into, but we built a new version. And it just felt like the right thing to do. It’s similar to the way car manufacturers do things. They might have a model, a design, Porsche 911. It’s been around since 1963, but they have the original one, I think it was called the F Body. Then after that came, the G Body after that came the 964, then the 993, then the 997. They have these generations. It’s still the 911, so it’s still Basecamp, but they have these different generations because at some point you just can’t bolt on what you want to do anymore to the old generation. It’s time for something new. So that’s how we approach it as well.

Kimberly (03:02): Okay. Let’s go back. Let’s kind of put this in terms of a timeframe.

Jason (03:06): Yep.

Kimberly (03:06): When did Basecamp, the original Basecamp come out? And then I’m asking, it’s kind of a quiz. I don’t know if you’ll actually remember these dates, but Basecamp come out to Basecamp 2. I’m just thinking, how long in the process was it before the discussion kind of started of maybe it’s time to build a new house?

Jason (03:25): Basecamp came out in 2004, February 5th, I think it was 2004. So actually it was more like eight years, but it really didn’t get rolling until we knew we had something about a year, year and a half later. So 2012 we did Basecamp 2. I don’t remember how long that was out, and then we did Basecamp 3 and then from 3 went to 4 and now 4 we’re going to 5. Now, the difference is is that from one from Classic, from original to 2, brand new version at 2. From 2 to 3, brand new version for 3, meaning from scratch brand new, nobody had to switch over from 2 to 3 unless they wanted to.

Kimberly (03:59): And consequently that means we’re still supporting all of these different versions.

Jason (04:03): That’s right. We still run Classic, we run 2 and we run 3, but 3 became 4. So we didn’t do a new version for 4. We morphed 3 into 4. So now we’re running just to go through the… we’re running Classic, 2, and 4, and 5 is going to also be a morph from 4 to 5. So we’ll be running Classic, 2, and 5 essentially. So if you were on Basecamp 3, you’re now on Basecamp 4. If you’re on Basecamp 4, you’ll now be on Basecamp 5. And so part of the challenge with that is we want to make sure that these new versions are substantial enough that they feel like a new version. They’re familiar enough because we are morphing them, so you will get them. There’s not a choice of whether or not you want it or not. It’s a transition to a new version. Between Classic and 2, we could be a lot more radical because we could say you could stay where you are. If you don’t like this new thing you can stay where you are. We’re not saying that anymore for now, for 3, 4, and 5 are all a transitional upgrade, basically.

(04:59): So it has to be familiar enough but still fresh and new enough to be new and to do new things. And so this is always a delicate balance of how do you inject enough new, enough better, enough fresh utility, but not upset the apple cart or whatever the thing is, or pull the rug out from… whatever metaphor you want to use or whatever analogy, so people don’t totally freak out. Some people will because some people, whenever you change anything, they don’t like it. Totally understand that fair. We’re changing more than just a little few things. We’re changing a lot of things, but we’re also keeping it familiar enough that it feels like, oh, okay, this is a new coat of paint, but the furniture is not that moved around. I still recognize this room. I know how this room works and how this house is set up, but oh, I have to learn this new thing. I have to learn this new thing. And we expanded the kitchen a bit. So now the powder room that was over here is over here and things have moved around a bit, but still feeling familiar enough. That’s the thread we’re trying to pull here.

Kimberly (05:52): Okay, so what’s interesting about not making a completely new model, if you will, like morphing from one version to another. I would think there’s also some financial implications to that, meaning when you spin up a new version, you have to opt in. You’re also opting into a new price point.

Jason (06:12): Right?

Kimberly (06:13): As it is now you’re not. You just stay on the same thing. So is that part of your decision making process as well or does that not really factor into it?

Jason (06:20): I mean, look, if we have a radical, radical new idea that’s really, really different that would not fit on the existing chassis, we will start over. Maybe Basecamp 6 is from the ground up. I don’t know. We’re not thinking about that now. We’re just working on 5, right? So in some cases that’ll dictate business model changes and other things. It is just easier to transition where people don’t have to think about an economic decision. They just go, do I still like this? Do I want this? Do I like the new things? Do I like most of the new things? Am I going to be able to get used to the new things? All the things, yeah, great, okay. That’s all they have to think about. Pricing models and change on ‘em. They get to keep their existing price, the whole thing. Now, we could also introduce a new pricing model for new customers.

(06:57): That’s always an option, but that’s also an option for an existing product. So it doesn’t really mean that a new version requires a new business model, but it is a smoother situation and there’s also no migrations that have to happen. Sometimes, you know, between versions we’ve always allowed people to move between 2 to 3 or Classic to 2 or whatever, and features weren’t in parity, so data didn’t really transfer in the smoothest way because some things weren’t the same and other things were new. And so it worked, but it was kind of a messy process, and so we’re just finding that it’s way more valuable for us at the current time just to deliver a whole bunch of new features where no one has to make any other major decisions. We dabbled with the pricing model over the years, even within versions. So we had no free version then we had a free version, then we had longer trials and shorter trials.

(07:39): We’ve tried a bunch of different things. What we try not to do though is change things for the most part on existing customers. You’re not locked in for life at a certain price point, but we really try to respect the fact that you came in at this price and that’s where we’re going to keep you for the most part. There are situations where there’s a long-term transition to a new price point, but for the most part we keep everyone where they are. And if we’re going to play with new prices, it’ll be on new customers. They won’t feel like anything’s changed because they’re coming from scratch, so it’s new for them.

Kimberly (08:03): Right. Okay. So you mentioned knowing that maybe some people won’t like the changes. Talk me through that because I’m sure anytime you’re making a new version, there’s that risk. How are you thinking about the risk/reward or are you trying to hold on to customers who might want to leave? What does that kind of look like for you guys?

Jason (08:23): Well, I mean anytime you change anything, there’s a number of people who don’t like it, understandably so. I think people are actually very comfortable with change in general, what they’re not comfortable with change being forced upon them. So that’s always just something in the back of my mind, which is like, are we changing this too much? Okay, let’s say we are. Is it worth it? Sometimes it is worth it to go, we have a new idea here, it’s going to take people a long time to get used to it. There’s a short period of time, who knows? But people are going to get used to this, but the trade-off we believe is worth it. And there’ll be some things in Basecamp 5 that are like that or we’re moving something around or changing the way something works or radically modifying a specific screen that will initially be jarring for people, understandably so, especially those who’ve been used to the way things have been and the way things are currently in Basecamp 4.

(09:08): But we believe that if we explain it clearly and we give people a chance and people give us a chance, they’ll see why we made these changes and they’ll feel good about them in the end. Not everyone will, though. Some people always want things the way they were, and it’s always been interesting for me as being around in this business for a long time to see the things that people would argue against then being the things that those same people will defend. So for example, when people move from 2 to 3, there was things in 3 that were radically different than 2. Some people hated those changes in 3, but then they finally got used to them in 3, and then we changed them again in 4, they were clinging onto the things in 3 that they initially hated when we moved from 2 to 3, but now they love and they don’t like the new thing we have in 4.

(09:49): So it’s totally natural, normal, and this is just a human condition. It feels evolutionarily accurate for a lot of different reasons. So I get it. Part of this is understanding that some people are going to react negatively to change. Some people are going to react negatively, very negatively, a little bit negatively. Some people are going to not like it for a few days and then see it and then dig it. Some people will never like it, whatever. The key to me is never to when you launch something brand new is actually not to pay attention to feedback for probably the first 30 days.

Kimberly (10:18): Oh wow.

Jason (10:19): Unless there’s something that’s like busted. This doesn’t work anymore, this is a bug, different story. But as far as like, I don’t like this or I like the way it was, or I don’t like where this moved or I don’t like how this works or whatever, I get all that. I have the same reaction to new things too sometimes, and so I think it’s just good to go, yeah, I hear that. Let’s see what the feedback looks like 30 days from now versus the, this is going to sound negative, sort of the knee jerk reactions

Kimberly (10:48): Yeah, yeah

Jason (10:49): Initially. I have ‘em too. We all have ‘em, so I want to ignore my own as well. When I was switching over to Omarchy, David’s thing and Linux, this is a whole new world to me. It’s totally awkward and strange and I got to use the keyboard for everything and I can immediately go, I don’t like this, but I can also go, okay, there’s something here, probably, other people seem to like it. Maybe I just need to get used to it. And so I recognize my knee jerk reactions as such and go, you know what? Okay, yeah, this is awkward, this is weird. I’ve got to get over this hump though. I’ve got to give myself a chance to get over this hump so I can see what’s in the valley beyond, and if I don’t give myself that chance, I’m just going to push back. So I try to give everybody that chance by not being reactionary and just hearing, but kind of ignoring in a pleasant way and go, let’s see what this looks like in a few weeks.

Kimberly (11:43): I mean, as a previous customer who was on Classic and moved to 2 and moved to 3, like I get it because there were times where I’m like, this is just hard. It becomes hard for a short period of time until you figure it out. And hopefully that period of time is very short.

Jason (11:59): And I also recognize that everybody’s in the middle of things. You’re in the middle of a project, you’re delivering a wedding for someone, and eight days before the wedding, all of a sudden the interface is totally different and you’re like, oh my God, this is crunch time.

Kimberly (12:12): It’s the worst thing ever. The worst timing.

Jason (12:14): The worst timing. It’s always going to be the worst timing for somebody and for many people when you have a customer base as broad and large as we do. So I just recognize that that’s the case. What we try to do with new releases is give people a really nice heads up. That said, it’s never the same as things changing on you, but I mean I will do probably some extensive video previews. I’ll walk through some features, maybe you’ll make some stuff ahead of time, whatever it is, and this is what’s coming.

(12:41): This is what’s coming soon, here’s what we’ve done, here’s why we’ve done what we’ve done. Here’s some great advantages to what we’ve done and why we’ve did it, and this is the idea behind it and this is how you can adjust to it. And so we want to give people all those heads up, but understanding still that not everyone’s going to watch those and not everyone’s paying attention to that. Everyone has their own life and their own things they’re paying attention to, and at some point someone’s going to be in the middle of something and something’s going to change on them, and I can’t prevent that from happening unless we have a brand new version from the ground up, which introduces its own set of challenges. So it’s all about trade-offs and recognizing that you can’t make it right for everybody.

Kimberly (13:17): Okay. So you said you kind of ignore feedback in the beginning. At some point, I assume you start looking at it. Have there been times in the company’s history that you can think of where we’ve changed something because of negative feedback?

Jason (13:33): I don’t look at any feedback as negative.

Kimberly (13:36): Oh. Good perspective.

Jason (13:37): I look at it as just like this is…

Kimberly (13:38): Feedback

Jason (13:38): …what someone has to say. Yeah, it’s like they don’t like it. Okay, great. I don’t see it as negative, actually. Don’t like doesn’t mean negative to me. It just means they don’t like it. I try to remove the value judgments from it and go, what’s actually happening here is something isn’t jiving with them, something doesn’t work as well as they think it should. Or maybe they don’t realize they could do this thing that we do have now and they just need to learn about it. Or maybe they simply just don’t like it. There’s things I don’t like in the world that I use. Nothing’s perfect as they say, obviously. So I’m trying to remember. I think one of the things that we did, I can’t quite remember what decisions we made around this, but with Basecamp 3, we introduced Pings, which was direct messages, didn’t have that before. And we separated the Ping menu from the Hey menu. Hey menu is notifications for new messages, comments…

Kimberly (14:23): Tasks

Jason (14:23): To do, assignments, that kind of thing. Tasks, right? Schedule, eventually schedule stuff. And then Pings were separate from that, and we made them separate even though they’re both notifications because we felt like someone’s trying to directly get in touch with you, and we want that to be something that is not hidden behind other notifications because people tend to leave a lot of notifications around in general. So we wanted to kind of separate these out, and I remember there was a lot of tension around that even internally initially. And I can’t quite remember if we made some fundamental changes to that after we launched, but I just remember that being a contentious thing. Some people are like, I want one menu for notifications. Some people understood the reason why we separated out. We also had a separate menu for campfires. This is actually something we did do, I believe.

Kimberly (15:05): Oh

Jason (15:06): Chat rooms were different. So we had Pings, Hey, and then chat I think. And then we had that for a little bit and we then unified those under the Hey menu after, you know… And it’s not just customer feedback, that’s part of it. It’s also like how do we feel about it.

Kimberly (15:22): ‘Cause we’re using it

Jason (15:22): Yeah, we’re using it and we’re not always sure ourselves. There’s some things you just don’t really quite know about. And after use it for a while, you realize that, you know what? We could bring this over here and unify this and it actually be a better experience. And these things shouldn’t be as precious as we’re treating them. But in general, there’s always little things. We’ve changed the notifications block at the bottom of messages and documents many, many times based on not like, I hate this because no one hates a notifications block. It’s more like it’s hard for me to sub-select just a few people and not everybody. And then we eventually introduced groups and we had to rework that because the way we did that wasn’t quite working. So it’s just a continuum of things. And products are living breathing animals or entities or whatever you want to call them really. And so some stuff just sort of piles up in the back of your head and then pushes forward and you’re like, it’s time now. Some stuff you get annoyed with. But yeah, I don’t recall a groundswell of negative feedback for something initially and then us changing it radically fast. I think we may have done that in the past, and I realize that was not a good idea. So that’s why we kind of wait on this stuff.

Kimberly (16:28): Nice. Okay. And then tell me when we have a new version of a product like we’re building now, feedback is coming in.

Jason (16:36): Yeah

Kimberly (16:36): You might not be looking at it, it’s coming into support. At what point are you looking at it?

Jason (16:42): I’m just getting it somehow. I’m not looking at all the email tickets.

Kimberly (16:47): People find you.

Jason (16:48): It just finds me. People email me. First of all, my email address is all over the product. It’s public, so people send me notes. People write stuff up on LinkedIn, people write stuff up on X.

Kimberly (16:59): When you post videos, people are going to comment.

Jason (17:01): We put videos up, people comment. And then customer service has a really wonderful job categorizing things. And sometimes Chase who runs customer service will get in touch with me about some stuff or I’ll look through some things. They log a bunch of really well-written complaints that are detailed in a project. I’ll see those come through in the latest activity stream in Basecamp. I’ll check those out so you’re not insulated from it if you’re paying attention. I don’t have to go out and seek it. It really just does bubble up in a variety of different ways and a variety of different places. And our own other folks who work here will bubble stuff up because hear it from somebody. So it’s just around. And it’s kind of nice to take the temperature that way actually as sort of a broad spectrum of feedback versus just looking at tickets because the people who write in tickets are people who directly express a frustration, praise, whatever it is through official channels. But there’s a lot of people who don’t do that and they share it elsewhere and it’s just as meaningful. So I’m just trying to pay attention broadly and not just go digging into one type of source.

(18:07): But it’s always obvious, you just hear about it. Brian who runs product strategy here, oversees the products in a big way. He talks to customers more frequently than I do. He’s in touch with Chase more frequently than I am. He’s paying attention to different levels. So there’s a bunch of different people paying attention at different levels, and it all filters up to who needs to hear it. And much of the feedback is right. It’s like, yeah, this thing is a little clunky or should be better, or yeah, we should put a notification on that or we’re not doing it here, or this should have a preview when it doesn’t. There’s great ideas that come from all of this stuff. I just don’t want to react in the first 30 ish days because it tends to be pressure based feedback versus once you get used to things and things settle in. That tends to be, to me, more accurate feedback of the state of the system, then the pressure that’s applied on a change.

Kimberly (19:01): Okay. Last question before we wrap it up, and you don’t have to tell me something specific because I know we’re not sharing everything. But in general, what are you most excited about with this new version?

Jason (19:10): So with Basecamp 5, one of the things we’re trying to aim for is as I’m calling it a direct experience. For example, in Basecamp 4, if you want to see your assignments, you have to go to the homepage and scroll down to the bottom, they’re down there. Or you go to a menu called My Stuff, then you select assignments. Then it’s there. So there’s like

Kimberly (19:31): A couple clicks.

Jason (19:32): Yeah, it feels like it’s at arm’s length. It’s not like right next to you. So in 5, there’s this way to basically have your assignments always right there or have your upcoming events always right there. So when you need them, they’re right there. It’s almost like you have four arms instead of two. It’s like, I can work and I can also see, or I can use this other arm I have to pull something up without leading where I am. It’s this sense of more things being surfaced in a way where they’re not in your way, but they’re right where you need them when you need them without having to leave to go do something else. As I mentioned with 4, yeah, it’s a couple clicks away. It’s not like a lot of couple clicks, clicks is a bunch, but you have to leave what you’re doing to go somewhere else. So we’re trying to reduce that urge to have to leave. Same thing is true with Pings. With Pings where people direct message, you go up to the Pings menu, you select a Ping, everything’s gone, screen’s replaced with the Ping. You say, cool, great. Now you got to go back to where you were.

(20:28): Screen changes again. So in 5, Pings are in a sidebar basically that you can open up and have conversations with people while you’re working on something else, so you don’t have to leave what you’re doing. So you have that alongside. So this idea of having things alongside and you can check in on those things without leaving your place. So that’s one thing. The other thing is we’re trying to really highlight activity and progress more. So trying to get rid of a more static feeling sometimes. There’s some screens in Basecamp that are kind of static and we’re trying to make sure every screen is kind of active and then it always has, here’s the latest thing, here’s what’s been happening. Here’s who’s actually working on stuff, not just who has access, but who’s actually been working on things. So it’s a little bit more current in that way as well.

(21:13): And also just slightly better use of screen real estate, and we’re bringing a full blown calendar back to Basecamp. So we had a great calendar in 2.

Kimberly (21:20): You’re making all those Basecamp 2 people really happy.

Jason (21:23): Yeah. We had a dot calendar kind of thing we called it, and we’re coming back with a full blown calendar in 5. So that’s another major change that’s been primarily pushed from customers. They’ve been asking for that. We used to have a really great one. We went away from it and we’re bringing that back. So there’s a lot of big banner features, like big new things. There’s a lot of things that are just a little bit closer at hand. More direct. Things are going to feel more active, so you feel more informed about what’s actually going on and who’s involved. And so it’s a bunch of subtle things and a bunch of banner things, and we’re very, very excited about it. What we’re trying to do now is draw, actually talking with Brian a lot about this. Where do we draw the line? So what makes it into 5? And then what waits for what we call 5.1, which is like…

Kimberly (22:08): Just regular feature releases.

Jason (22:10): Yes. And that ties into like, when could we get this thing out? I mean, we could get it out much faster if we draw the line earlier. We want to get a few more things in. There’s some deep infrastructure stuff I still want to consider doing. And that would be a hard thing to do after the release because it’s fundamental to the way users work, and it’s better to do that now than later. So some of that still we’re kind of moving that stuff forward, pushing some other stuff back, holding a few things maybe that we might release after we’re not really sure yet. So that’s kind of the place we’re in right now.

Kimberly (22:39): Okay. Well, you gave me a lot more spoilers than I thought you were going to say, so I’m sure you made a lot of people happy.

Jason (22:44): Yeah, people have to imagine though. So we’re good.

Kimberly (22:47): 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 on YouTube. And if you have a question for Jason or David about a better way to work and run your business, please send in those questions. I literally love receiving them. You can make a video recording at 37signals.com/podcastquestion.