SEASON 2 - EPISODE 201 - August 26, 2026

One-way Doors

Not every decision deserves a long deliberation. In this episode, co-founders Jason Fried and David Heinemeier Hansson look back on 25 years of running 37signals, the handful of decisions that were truly irreversible, and why keeping a loose grip on most business calls has served them better than any spreadsheet ever could.

Watch the full video episode on YouTube

Key Takeaways

00:11 - The single one-way door decision at 37signals
05:49 - Why most decisions barely take five minutes to make
08:05 - How the sum of right choices matters more than any single one
13:51 - Recognizing when the business stops moving forward
16:41 - Letting go of decisions that didn’t pan out

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 back again with our co-founders of 37signals, Jason Fried and David Heinemeier Hansson. This week I thought we’d talk a little bit about the idea of one-way doors versus two-way doors. We’ve talked about that before from Jeff Bezos’ famous quotes. But it’s funny because I’ve been thinking, over the last 25 years that this business has been a business, you guys often say no decisions are that big of a deal. We can change our mind at any time. I thought we would talk about that because I don’t think most companies feel like all these decisions are irreversible. Are there any decisions you guys can think about in the last 25 years that were big decisions, hard decisions that you couldn’t come back from?

Jason (00:44): Well, we’ve made a few. Selling a piece of the company to Jeff Bezos in 2006 was one, and that just changed the cap table a little bit.

Kimberly (00:53): Okay, let’s talk about that really quick.

Jason (00:55): Yeah

Kimberly (00:55): When that happened, was that a, we need to think about this for a long time and discuss it and write the pros and cons? Or was it like a quick decision for the two of you?

Jason (01:07): I don’t recall exactly how many conversations we had about it, but we’d had not a hundred, but we had many, many, many, many people ask us if they could buy in and we said no. And then Jeff felt different. We met him a couple times. We went out to Seattle to meet him. It just kind of felt right and we just had to find a way to do it. I don’t remember if we sat around debating it that much still. I don’t remember. Do you remember, David? I felt like it was just kinda, ultimately just sort of made sense and we figured out could we do this or not?

David (01:38): I don’t recall any pro and con lists, but I also don’t recall any pro and con list about anything we’ve ever decided to do.

Jason (01:43): Yeah, we don’t work that way.

David (01:45): We don’t work that way and we don’t think that way. But I do think in terms of the decisions, if you tally them all up, this one would be in the top five, maybe top three of most consequential decisions that we at least at the time contemplated a fair bit. Now we’ve contemplated other things even more since that seemed even less consequential. But at the time it was clear that if you let someone buy a slice of your company, well ta-da, they’re now your co-owner. And co-ownership comes with a lot of obligations and responsibilities to those owners. And in theory, at least a bunch of restrictions on what you can and cannot do. And I think that more than anything was what held us back for a hot moment and why we said no to so many others, that we were not willing to sell that independence and ability to do whatever the hell we wanted, whenever the hell we wanted.

(02:42): And I think this was also why the Bezos deal eventually ended up closing was that Jeff was not actually interested in buying our independence. He was not interested in buying into a set of rights of telling us what to do, which would characterize, I think, most of the VCs we talked to at the time otherwise. But it was also just a fact of, hey, this is a big check. And neither Jason or I, and even less so me at the time had much money to our names. And I think we had the humility to think, do you know what? This could very well end. Most things end very quickly. The mortality rate of startups in the early years is extremely high. You’re far more likely to die as a startup than you are of almost any disease in the world you could catch. It’s a very difficult thing to make work.

(03:37): So if you have some humility about that, you obviously should apply that to yourself and go, do you know what? This could not pan out. And right now we have something that’s hot that people are interested in, and they’re talking about big sums. And if we just go and we don’t do any of it and then it all blows up tomorrow, well, we’re going to have to find another job. And I would very much prefer not to have to find another job. So here’s the way out of that, but it clearly meant also giving up a lot of things. But again, I actually also think for both Jason and I, even when the stakes are as high as they can get for what we do, the decision usually comes quite quickly because there is this pre-processing that’s happening in your gut that tells you this is where it should go.

(04:21): I don’t think either of us really believe in long drawn out deliberation sequences. In fact, I always consider the smell. If we can’t make a decision quite quickly, it’s usually because there’s something right under the surface. It’s not lack of information. It’s some fear of some thing that if you just address that directly, the decision becomes obvious. So in this case, it was like, do you know what? Yeah, it’d be nice to have a couple million bucks in our bank account and therefore the confidence to go all the way and not be tempted by the VCs next month when they come with a bigger check or whatever, even if that means someone is on board with us. And the funny thing even with that decision was it could have gone back on it. In fact, I think 10 years ago, Jason and I seriously thought about, should we go back on it?

(05:11): Should we buy Bezos back out of the business? Because we could have done it. And ultimately it just didn’t matter enough. The attraction to that idea was almost purely aesthetical. What if just the cap tables were just to the two of us again, would that not look nice or feel nice? It was not because we were like, “Oh my God, Jeff, keep your nose out of our business.” That was never the thing. We’ve had essentially the most idyllic, perfect, silent partner setup you could possibly imagine with Jeff along the way. But yeah, it was a one-way door. I think it qualifies.

Jason (05:49): I do think people would be absolutely shocked at how little we deliberate over pretty much anything. I mean, this really would surprise the hell out of people, I’m sure. It’s like when we make a call, we literally will have a five minute conversation about it. And sometimes there’ll be another one that’s seven minutes, but it’s kind of like, should we do this? Should we not do this? Yeah, yeah, no, yeah, whatever. We either get to both yeah or both no, and sometimes there’s a little bit of debate, but literally it rounds to zero for the most part. We just make decisions and we go for it because most everything can be reversed anyway. We’re rarely making massive decisions that are so filled with risk, so dripping with risk that we really have to be careful about it. And that’s by design. We try not to make those kind of decisions.

(06:36): We try not to be a business that’s in that position. Sometimes you can get backed into a corner and force into that position. So far we haven’t been luckily for the most part, but even if we were, I think we’d make the call really quickly. If we decided at some point to sell the whole damn thing, honestly, it’d probably be a 15 minute conversation. We’re like, you know what? Fuck it. We’re done. Really, literally David, let’s say I said it first, David would be like, I’m feeling the same way. Or whatever. Or if he’s not or I’m not, we’d have another conversation, but it would not be months of deliberation about this and pros and cons lists and persuasion and it’d be like, yeah, let’s just move on or whatever. That’s kind of how it’s always been. I think that’s how it’ll always be. And I enjoy that very much.

(07:22): It’s fun to just make calls and move forward fast and not get weighed down by things because ultimately at the end of the day, most things probably don’t matter. Basically, pretty much every decision you make in the business doesn’t really matter. It could have gone a hundred different ways and would’ve turned out the same way or differently. But the idea that this one decision you’re making was the only possible decision you can make at that time and that led to whatever else happened, there could have been a hundred other paths that led in the same way or not. Who knows? Nobody actually knows, but you’re better off just finding out by making a quick call and moving and seeing what happens, taking that next step and seeing where you are. That’s at least our perspective on it for the most part. So there’s nothing. There’s almost nothing that happens when we make a call.

David (08:05): Now, I do think it’s important to stress that while the individual call is not that important, it’s because the net sum of all the calls really are, and that’s the moving average that we’re optimizing.

Jason (08:19): That’s right.

David (08:20): And what we have found in optimizing that moving average is that a great deal of humility must be applied to our intellectual ability to analyze a situation upfront that in almost all the cases, whatever the decision is, is usually one that asks reality for the check. What’s going to happen if we do this? And then we will adjust if that’s not quite right or that’s a little bit off. And that’s how we sort of go a little too high, a little under, and it averages out to a string of good decisions. I actually would take great pride that if you summarize 500 decisions we made, none of them had this sense that this was make or break, but the total sum of them totally did. If you make 500 decisions in a row and they all suck, you’re going to go out of business.

(09:09): That is guaranteed. But if you don’t grip that hard on any individual decision, I actually think you are so much more likely to end up with a good string of decisions. And this is, Jason, remember you had this metaphor for loose hands for playing the drums. And I find that a lot of businesses and business owners and perhaps even more so executives have incredibly tight hands. They are really just gripping those Excel spreadsheets like their life depended on it. And in part, especially when they’re executive or they’re an owner who has owners, that is they’re an entrepreneur who has taken funding. So much of the decision making process is deliberation for show. I need the people who are watching me to feel like they’re going to have confidence in me because I have checked all the boxes and I’ve done all the spreadsheet and I’ve done all the analysis.

(10:03): So if it goes wrong, can’t blame me. I did the math. I did the spreadsheet. So I mean, that’s just unforeseeable, right? And the great benefit for us is that we don’t have that second layer. There’s no one looking over us going like, did you do the math? No, we just get to hold the grips of the company really loosely. And I think it’s been that way since the beginning, but perhaps for me it’s gotten even more that way because you realize now that moving average that we’ve been playing on for 22 years, we have racked up so much that holy shit, we’ve probably, I don’t know if we could make 500 bad decisions in a row, but we could at least make 20. Twenty bad decisions just cold streak. We’re just batting out one thing after another. We’d still be here, still be allowed to do the business and run the things because we’ve created so much buffer over time.

(10:57): And that has given even more of loose hands, even more of an ability when Jason and I in rare instances don’t actually agree on something where I just go like, you know what? Yeah, I probably would’ve rolled it the other way, but who cares? Let’s just try it your way. And if it’s not working, I know as Jason does with me, reality’s going to tell the tale and we will just adjust. And therefore we can just have this incredible give and take and generosity of let’s just see where it goes. And then we don’t have to waste time in the deliberation room. And as Jason says, neither of us like that. I actually really like this sense of running right on the edge where I don’t know what the fuck I’m doing. Just slightly veering to the reckless side of being totally fucking ignorant about where it is and then just trusting I can hold my balance. Like you’re on a damn surfboard and you’re just going like, I don’t know why I’m still up here. I guess it’s something about micro movements one way or another. Man, it is bliss when it just sails through the ocean like that. And occasionally you wipe out it’s so fucking what? Get back onto the board.

Jason (12:08): Can I actually add something really quick?

Kimberly (12:10): Yeah, go ahead.

Jason (12:11): This may be a bad example, but I think when you’re driving a car, you’re going somewhere, do you know how many decisions you’re making? You’re making a thousand decisions.

Kimberly (12:21): Without even thinking.

Jason (12:23): You’re just making decisions. And if you had to really think about every decision you make, you’d get nowhere. But we’re so comfortable with that idea. I feel like that’s how we run the business for the most part. There are a thousand decisions that we’re making all the time about a feature, an idea, how to respond to a customer, how to respond to… how to play with price, all the things. But we do it in a way where you’re driving, you are moving, you are not stopping every time you have to make a decision, you’re moving and making decisions. That’s how I think we do it. And I think if you start to think of your business as a car that’s moving and a deliberation is stopping, you’d be like, why are we stopping so frequently? Let’s just move and call, move and make calls, move and make calls, move and make calls.

(13:07): And I think that’s how you end up with a smooth curve essentially, which is kind of what David’s like… There’s errors that kind of maybe, ooh, that was close. I was tailgating this guy and I probably should have turned left when I turned right, but I’ll go around the block and get there anyway or wow, that was close or whatever. Or I scraped the tire when I was parked. Whatever it is, there’s things that go a little bit wrong. But for the most part, the curve is pretty smooth. You’re going in the right direction, you’re getting where you want to go, things are turning out all right. And it’s not that you don’t care about what you’re doing, you do, but you’re not stopping every time to make calls. I think that’s how I tend to at least think about it. I hate stopping the business is the way… I hate that. I don’t like that. We can’t do anything right now. We can’t do anything until we make this call. No, we’re going to keep doing things and we’re going to make calls as we go. That’s the way I like to think about it.

Kimberly (13:51): Okay. To go along with your analogy, has there ever been a period of time where you’ve been like, oh, we’re now not going in the right direction. We need to make a change because things are not going in the right direction.

Jason (14:00): Well, yeah, there was at least one. I mean, back in 2021 when we had the no politics move. That was a moment where actually the business felt like it stopped.

David (14:08): It was in reverse.

Jason (14:10): Yeah. Well, yeah, it was going. Let’s carry the metaphor. Yeah. It was rolling down the hill. We’re up a hill. The clutch was in. We weren’t engaged and we were rolling back. We were about to hit someone behind us. That’s how it kind of felt. It’s not a good feeling and it kind of felt like it was chugging. It’s starting and stopping and starting and stopping around. There’s very staccato, which is a really shitty feeling. I think that’s how it feels. When the business is running its best, it feels like it’s moving forward. There’s wind in our hair and it’s a cool breeze. And this was a very stagnant moment and it didn’t feel right.

(14:43): You know when you’re in traffic and you’re just stuck in traffic and it sucks and you hate it and it’s hot and there’s no wind and your air isn’t working, whatever it is. But the moment the traffic breaks and you get to go again, it’s just one of the best feelings, like open road again. That’s where we eventually got to, but we were in traffic for a long time and stuck with nowhere to go and it felt really terrible.

David (15:05): But it also stands out because I don’t off the top of my head can remember any other moment that felt that stuck, that felt that gridlocked. I mean, we’ve certainly had moments where a product launch or feature launch didn’t go as well as you might have hoped or someone might have hoped. We try not to put too much hope into these things, but never to the point where it just felt like, oh man, I’m learning how to drive stick again and I’m constantly stalling the damn thing. That, now we’ve really tortured the metaphor to do. We can let it go now. We can let it drive off into the sunset. I think this is a good signal. It should not feel like that. That’s not normal. The normal thing is that the thing is moving and if you feel like you are stuck in this staccato moment and you got to change something, you’re going to burn out the clutch otherwise.

Kimberly (16:02): David, no more.

David (16:03): It is going to pop. You can’t stay in that moment. So it’s worth, if you are in that moment, to do something a little, I mean, reckless, maybe driving over the greens there to get on a different road. Okay, I’ll stop. And yeah, just don’t accept it. Don’t accept that. Do you know what? Most of the time in the 20 plus years we’ve been going, it has been smooth. Micro adjustments all the way as always. A little bit of, ooh, okay, maybe I should keep a bit more distance, but … don’t accept that. That’s not a way to live.

Jason (16:41): The other thing is we’ve made some decisions that haven’t panned out. I just don’t care. I’m not going to dwell on them. I’m not going to look back on them and do a postmortem. I’ve written about this where like, well, what went wrong? And you try to make up a reason. You don’t really know the reason. You find a reason and then you think that’s the reason and maybe it is and maybe it isn’t and who knows and who cares anyway? The next moment is going to be different than the previous moment. All these lessons aren’t really applicable necessarily. There’s probably some big picture directional things that are, but like, oh, next time we won’t do this. This happens all the time. David, we’ve talked about this. The outcome for these kind of meetings is we need to communicate better. It’s a communication problem. Had we just told the other team. Whatever. That was not the problem.

(17:25): That was the easy thing to grab at because they go, yeah, we didn’t talk enough. Obviously if we talked enough, it’d be better. It probably wouldn’t have been any different. Who knows what the difference is? But this idea of dwelling on things that didn’t go well or didn’t go quite as right as you wanted or didn’t work out exactly as you’d planned, who cares? What are you doing now? Where are you now? What are you working on now? Learn moving forward. Don’t look back. Learn moving forward. The next thing, make it better. Take your lessons from the things that work. And even those aren’t even totally clear because those are also a product of a moment, timing, market conditions, variables you don’t control, variables you don’t even know exist. Just do the best you can in the moment you’re in. Keep doing that as often as you can and it’ll play out the way it plays out.

Kimberly (18:11): Okay. That is a great place 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 leave us a voicemail. You can do that at 37signals.com/podcastquestion, or you can send us an email to rework@37signals.com.