The Learning Leader Show With Ryan Hawk - 583: Jason Fried - Growing Without Goals, Earning An Investment From Jeff Bezos, Making Tough Decisions, Keys To A Great Partnership, Hosting Leadership Retreats, and Creating A Writing Practice

Episode Date: May 19, 2024

Our new book, The Score That Matters, is a USA Today National Best-Seller. Buy it here: https://amzn.to/3Qw9Mu0 Full show notes at www.LearningLeader.com Making decisions – Decisions aren't hard ��� it's the moments after that are. Whenever I make decisions, I don't think about now, I think about eventually. How will this feel then, maybe a year from now. When it's real, not raw. When the complications around the concern have cleared, and distance has done its job. Goal setting - 37 Signals does not set long-term goals. Jason (as the CEO) helps set the direction and they work in six-week sprints. Think, "What am I optimizing for?" 37 Signals does not have a board of directors or advisors. Is it more helpful to have a chip on your shoulder to prove someone wrong or to be motivated to prove your supporters right? Both can be useful. Keys to a great partnership? Jason works with his co-founder, David Heinemeier Hansson (a previous guest on The Learning Leader Show). Mutual admiration Have complementary skills (Jason is design, DHH is engineering) A company is essentially two things: a group of people and a collection of decisions. How those people make these decisions is the art of running a business. Maxims: Decide what you're going to do this week, not this year. Whenever you can, swap "Let's think about it" for "Let's decide on it." Momentum fuels motivation. Just ship it. You'll figure out what needs to be fixed as you go. Mark Zuckerberg is coming into his own... There are lots of reasons for it. One of them (maybe)? He's working out, in great shape, fighting MMA style, and surrounding himself around others who are doing the same. All leaders should have a writing practice. Hopefully, you don't feel the need to send it to a lawyer or a comms team before publishing it or sharing it with the people you're leading. Write like you talk. Write what's in your head. Think about what you want to say, and say it. You never know who is watching: Jeff Bezos sat in the front row for one of Jason's keynotes and was so impressed that he asked to invest in his company. When you have the guts to put your thoughts and beliefs out into the world, it can work as a magnetic effect to attract people to you. It's refreshing to hear Jason talk about one of the core qualities he loves most about Jeff: he is overwhelmingly optimistic. The world is built by optimists. You don't create culture. It happens. A company's culture is a 50-day moving average. It's what you've been collectively doing as a company over the last 50 days. How do you treat people? Who have you hired (or fired) and why? Company off-site events: They do two per year (one in the United States, and one abroad). Members of Jason's team meticulously design them. One day of business followed by time for the team to hang out, do activities together, eat together, and bond. Does Jason have plans to sell 37 Signals? "No, that would be the demise of the company."

I don't like the pro-con list thing because it's never a complete list. A lot of people are nervous about making decisions because they feel final. I'm after the statistics. I'm after the feeling. I'm not a company as a founder. 37 signals, base camp, hey, wants.com. I tend not to set goals. I set directions.

I don't think putting a target in front of you makes you do better work. What makes you do better work is being proud of the work itself. Earlier in your career, you caught the eye of Jeff Bezos. Well, it's cool about Jeff. He wasn't looking for control. He was looking to support. I love to hear more about the importance of writing from a leadership perspective. I hated writing growing up.

I hated it until I got to write what's in my head. There's no way in hell I could ever run a company where I couldn't speak for myself. It's sort of been ingrained in us to think about writing. I'm just trying to think about communicating. Welcome to The Learning Leaders Show, presented by Insight Global. I am your host, Ryan Hawk. Thank you so much for being. here. Text Hawk to 666866 to become part of Mindful Monday. You, along with tens of thousands of other

learning leaders from all over the world, will receive a carefully curated email for me each Monday morning to help you start your week off right. You'll also receive details about how my book, The Score That Matters, will help you become a more effective leader. Text Hawk to 66866. Now on to tonight's featured leader. Jason Freed is the co-founder and CEO at 37 Signals. 37 Signals is a privately held company committed to building the best web-based tools possible with the least number of features necessary. Jason is an amazing writer, one of my favorites.

He's a co-author of Getting Real, Rework, Remote, and it doesn't have to be crazy. at work. During this conversation, we discuss Jason's framework for making hard decisions. He also told me why he doesn't set goals, as well as why he doesn't think they're needed to accomplish what they want to do at his company, and it may make you rethink your goal-setting framework. And then we talked about the importance of leaders having a writing practice. He shares how he's maintained an excellent relationship with his co-founder for the past 25 years. And I think the advice Jason shares applies really to all relationships. And then, an amazingly cool story about Jeff Bezos sitting in the front road during one of Jason's keynotes in 2005.

And how that led to Jeff investing in 37 singles. So cool. Jason, as I said before, is one of my favorite writers. I love his books as well as the essays he publishes online. I highly encourage you read his work. Please enjoy. my conversation with Jason Freed. Jason, hey man, it's awesome to have you back on the Learning Leaders Show.

Welcome. Good to be here, Ryan. I want to talk about decision making. I've seen you right about this because I think decision making can paralyze some people. And you've written that decisions aren't hard. It's the moments after that are. Whenever I make decisions, I don't think about now. I think about eventually.

How will this feel then, maybe a year from now, when it's not real, not raw? When the complications around the concern have cleared and distance has done its job. As a leader of a company, as a founder, as somebody who's creating new products, you have to make decisions all the time. What is your overall philosophy on making the right decisions long term? Yeah, I do. It's kind of, it is basically my job is to make calls or decisions, not calls. I'm not on the phone most of the time. First of all, it's not to try to make the right one because I don't know what the right one is.

and I don't want to worry that I'm making the wrong one. Right? So the opposite of right is wrong in that sense. And then that's where people get nervous. Like, oh, my God, what if I make the wrong decision? I'm basically trying to place a bet, essentially. And the bet is never going to be 100% right. It could be sometimes, I suppose.

But really, it's about probability. It's like, how close to right can we get? Like, how does this feel? How do we feel about it? What are the things we're considering? How important is this really? because, I mean, if it's not that important, let's not like deliberate forever on it. And let me not like beat myself up over it.

And also how, how, what's the likelihood that we could make a different decision about the same thing in two weeks if we need to? Like, I'm trying to always reduce the criticality and seriousness of the decision. So it's not as big of a deal. That way we don't get paralyzed and not wanting to make it. So those are the things. But really, I'm trying to, I'm trying to feel my way. through what seems to be the best possible choice out of out of the things that I that I

can choose versus trying to be right. Is there a framework you use? Let's use a different example when it comes to decision making. One of the ones is, okay, you know, I'm thinking about taking this job or leaving my company and going over there. Let's make a pros and cons list, right? You've heard this before. I'm curious when, let's say you're advising somebody and they come to you with a question

like that or maybe it's somebody who works for you. because I know you guys are so open with everything. I'm sure those types of conversations probably actually happen when they probably wouldn't at most companies. What's an overall framework somebody could use, you think, to help them make decisions? Yeah. So I don't like the pro-con list thing because I think that here's why I don't like it

personally. I'm sure it works for some people, but it's never a complete list. It's nowhere near a complete list. It's just the things you can come up with. But there's probably hundreds of other things that are at play that you may be aware of or may not be aware of. And so I'm not,

it's not like balancing the list because you're just balancing the things you can come up with. What I would usually think or feel is like, what does it matter? That's honestly like, what does it matter which one you choose? And because oftentimes both are probably okay. Like there's different outcomes probably or maybe the outcome might be the same. But both branches can lead you somewhere interesting. So I just try to get away from the right and wrong thing in terms of, I mean, there are, of course, like a moral right and wrongs, perhaps.

You might argue that's a philosophical conversation. But in most of these sort of business decisions, you're just making a call one way or the other. And unless it's highly, highly, highly critical, like something that we call internally concrete, if you're pouring concrete, you better make sure you're putting it in the right place and pouring it the right way because it's going to be very, very painful to bust up. So recognizing, like, are we dealing with a concrete conversation here or a decision or mostly just like, are we moving dirt around?

So we're moving dirt around, like you can move it around a bunch of different ways and the outcome might be fine either way. So I just, again, try to reduce the criticality so people don't get too caught up in how serious this is when it isn't. That's basically my framework because I'm trying to get to the point where I can tell someone, I don't know, like, what do you think makes sense? And, and like, well, I think this makes sense. I go, that sounds pretty good. Why don't you try that? You know, it's more of a try than it is like a, I'm going down this branch no matter what. Now, to your point, like, there are times in life where you're like, do I move to New York or do I go to L.A.?

Or like, there's some big things. But still, even in those things, which are big things, you could say, like, you could pick either one. You're just going to have a different, the life, your life might be different, but they both might be great outcomes. So pick the one you feel is right versus, like, New York could be wrong for you. How do you know? So I guess I'm not, I know I'm not like in some ways giving people actionable advice in a sense, but the only thing that would be actionable about this is try to reduce the severity and criticality of these decisions so they're easier to make and you don't feel regret if you

pick one and not the other. Well, speaking of a decision that you've made, I saw the dream home you built for yourself and your family in Chicago, looked through the listing a few times, amazing pictures. It's just, it's unique, it's different. It looks like almost a commercial building, but then it's beautiful. It's amazing, but you're selling it, right? So I know you decided to move. That's a huge decision, right?

A guy with a family, you built a dream home. It's very expensive for most people. And you decide to move. What went into that decision? It's so funny that you mentioned this because it is like the way you mention it, it is a pretty big decision. But strangely, we didn't treat it that way. So this is like during COVID.

So I built the house 10 years prior. love the house. House is great. During COVID, we're like, we don't want to be locked in Chicago because it's really cold. Winter's going to be bad. We're all going to be stuck inside. And a few years before that,

we bought this place we had to renovate in California. It was an old house from the built in the 50s and it needed some renovation. So we were working on that kind of slowly on the side. And it turned out that it was sort of kind of ready to go, like right in the middle of COVID. Like I guess maybe it was its 20, July of 2020 or so or August, something like that.

And we're looking forward like winter's coming in Chicago in a few months. Maybe we'll just go out to California for a bit and figure it out and see what happens. No one kind of knew what was happening at this time. You know, now you can look back on that. But back then it was like, who knows what's the few, is this going to be a 10-year thing? Like, no one knew anything. Like, are people going to be dropping like flies everywhere? We don't know.

So let's go to California and be outside at least, you know, and not feel cooped up inside. And so we did that. Now, we had a place, but we could have rented a place. There could have been other ways to deal with this, perhaps. But we had a place to go. And as we were here, we just decided never to go back to Chicago. It wasn't like there was a moment where we decided to move. It was just this transition between like, we kind of like it here.

Let's keep staying. And even now, I'm like, do we live here? I mean, we're living here now. Does this mean we're going to be here forever? I don't need to make that choice. I mean, we have kids in school, but they're in school, that's fine. I can work remotely.

My wife does what she does. She can do that remotely. And it's like, we'll just keep doing this. So strangely, in my mind, it didn't feel like a decision as much as it felt like, let's try something, which I guess is a decision, but it didn't feel final. I think maybe this is sort of what, as we dig into this, a lot of people are nervous about making decisions because they feel final. Yeah. And it could have been that like we stayed here for a year or six months and decided to go back to Chicago and that would have been fine too. We could have done that.

Could have done all the different things. There were different outcomes that were possible. We just felt like this one made the most sense for us right now. And here we are. We're still here. So I know it's yes, now I'm selling the house. That means we're like now at this point we're like we're leaving Chicago and we're making that decision if the house sells. If the house doesn't sell, I still have it.

But now that a few years have passed. we can sort of stretch the decision out over a few years in this case because we didn't know what we're going to do and now we feel comfortable that we can make this decision versus like freaking out about leaving home and going somewhere else where it would feel so final. Like we are saying goodbye to Chicago like three years ago. We didn't say it that way. We're like, we're just going to go out here for a while and see what happens. Is that helpful?

I don't know. It's kind of amorphous, but it really is how I think about it. You know what it is, Jason, is the fact that most of the elements of life are very nuanced. than gray. They're not black and white. And I think sometimes we try to say bifurcate everything. It's either a pro or a con. It's a yes or a no. But in reality, with most things, including even a decision to move or whatever, it's not a yes or a no. It's just we're going to go try this. We're just going to go do it. We want to be outside. You know, like we don't need to overcomplicate the thing. And it's almost like in alignment with how you run your business as well. Like we don't

need to overcomplicate this thing. We're just going to go do it and then kind of figure it out. And that feels because let's transition to goal setting because I feel like you guys, I loved reading about your process when it comes to goal setting. Okay. I'll pause. And I want you to describe your overall philosophy, both personally for yourself, as well as now running a company when it comes to the idea of goal setting. Yeah. So I'm not a goal driven person. I tend not to set goals. I set directions. So like I'll go in a direction.

We'll take an idea in a direction. We have an idea for where we want to head with this thing. And I mean, the goal, of course, is implicit in a sense like we want to ship this thing and make it great. But that's not like a, it's not like we need to do it

and measure it based on revenue or number of customers we signed up in the first three weeks or any of these sort of numbers that really frankly most people are making up. And then you, got to hit these targets and you set these targets out for you that are so precise that you either hit them and you feel good or maybe you should have made it had a more ambitious target or now you just set another target. Like you just keep setting target after target after target after target versus like

how about just doing the best you can and seeing where things end up. That's kind of how I've always approached these things. And this whole thing kind of came to me through running actually. So I was trying to run a six-minute mile or something, whenever this was. And I remember, like, aiming for this time. And then I'd run, and I'd run, I'd run, what it was, 605 or whatever, 606 or something. And it kind of dawned to me that, like, I was actually upset. I was upset. Like, why? I didn't get my, I didn't hit my goal. Now you could say, well, that's more motivation to hit it next time. But, like, okay, so let's say I hit it. Then what? So what I realized was that hitting the goal is, for me the wrong thing to aim for. The real questions I should be asking at that point is not did I

get a run a six minute mile. It's like, did I enjoy the run? How do I feel? Did I get some fresh air? It's my heart pumping, is my heart rate up. Did I get some good exercise today? It's all of that. And that is true at 604 and it's true at 557 and whatever. Those are the kind of questions and those are not goal-based things. Those are, again, like, result-feeling-based directional things that are amorphous to some degree, but also very, I can answer those questions. Yeah, I feel pretty good. I'm glad I did this today. Like, I feel like I got a good workout in. Yeah. Did I, how do I measure if I got a good workout in? I mean, some people would measure with their Fitbit or their garment or their Apple Watch. Like, I just like, yeah, I feel like I worked out pretty well today. That's good enough for me.

So I don't wear the things that give me the statistics because I'm not after the statistics. I'm after the feeling. Again, same as business, same as decisions. I'm after a feeling. And I know when something feels right or when something doesn't feel right, I think we all actually do. But for some reason, when things are easy to measure or easy to set a target on, we tend to want to do that and aim for this degree of precision that I think is unnecessary and perhaps not even helpful. So the real question we should be asking ourselves, I think it feels like from what you're saying is, what are you optimizing for? Yeah.

Like when you think about running, the question is, what are you optimizing for? And you can answer that question. And that becomes the goal, so to speak, right? Of heart rate or how you feel or getting exercise as opposed to a six minute mile. Yeah. And so you could say. that the goal is to have a good workout, right? I wouldn't call that a goal, though.

Like, to me, a goal, typically, most people think of it as like a six-minute mile. Like, I'm aiming for something, a singularity. I'm aiming for this point. I need to get to this point and hit it exactly. That's a goal.

That's how most people I think think of goals. I think, like, did I have a good workout? Now, I can still push myself harder if I want to. I go, yeah, I had a good workout, but I think I got some left. And if I put it, I pushed myself and I ended up, if I did time it and I was under six, that'd be great too. But it wouldn't be, it wouldn't feel any better to me.

It would just feel like, because the time and the precision isn't the feeling. It's like the action, the act of the thing, doing the work or the workout in this case is the result. It's not the time or the number. Now, if I'm training professionally for, which I'm not, but like for like a marathon or a race, and there's targets you got to hit that other people set or you set for yourself. I can totally see how that would be very, very, very useful. So if someone's, I'm running a triathlon, I want to finish the top core tile. I got to get past this number.

I'm going to train a certain way to get past this number. Totally understand that. I don't do that. So for me, I don't want to act as if I do that. I'd rather just, you know, do the workout and push harder if I feel like I have some left. What type of impact or effect, I guess, I should say, do you think it would have on your company if all of a sudden January 2nd, you have a town hall or whatever, you gather everybody together and you say, okay, here's what I want us to accomplish by the end of the year and you

have a revenue number and you have a profit number and you have some other things about how you're doing in the market against competitors, whatever, the stuff most CEOs do. What type of impact or effect would that have on your company if you did that? I don't know. I mean, it could work. We could. Why don't you choose to do that? I wouldn't enjoy it. Frankly, like honestly, I wouldn't, I wouldn't enjoy working for that. Yeah. Like, I just, it doesn't, it doesn't matter in a sense to me.

Like, I want to, what I want to get to and what I think, where I think we are and where I hope we stay, is that we just want to do the best work we can. Yeah. And, and I don't think putting a target in front of you makes you do better work. I think what makes you do better work is the inherent motivation of caring about your craft, caring about the people you're working with, understanding what you're making, being proud of the work itself. And you're going to take that as far as you can.

And we're going to end up in a place and the market is going to tell the truth. Like, did we do good enough? Yes or no. And again, it's not to beat the competition because the competition can have their business and we can have our business. I don't need to beat anybody. I'm not out for domination. or taking market share.

Like, there's enough for us. There's enough for them. Of course, there are zero-sum game businesses. We're not in one of those. There's lots and lots of tools in our world that people use that are not ours. We can build a great business. They can build a great business.

So it's all like, it's very insular in a sense. Like, what do we need to do to function well, to sustain our business, to be profitable? That is the one goal, I would say that we have, but there's not a number attached to it. It's not like we need to be this profitable. or have this exact margin, but we want to be profitable

and have healthy margins. Again, range. It's about a range, you know. And we've been doing that for 25 years straight. Every year for 25 years. Doing it without targets, without specifics to aim for, but instead kind of going inside,

let's just do the best work we can together. Now, there are moments where I'm like, we need to ship this. So, like, we're going to ship this by January 1st. And so is that a goal? It's more of a deadline, Like we are going to do this and we're going to take some things out if we can't get it done because we need to get this thing out the door. So there are most it's not like this as long as it takes kind of mentality.

It's certainly not that. There's more discipline here, but fundamentally it is about doing good work that we're proud of and letting the chips fall where they may. At one point earlier in your career, you caught the eye of Jeff Bezos and I believe he came to you and said he wanted to invest. Can you take me back to that moment? What caught his eye and what was it like working with him when he decided to do? to invest in your company? Yeah, so historically, we had been approached by a lot of different investors, and it was never interesting to us. It still isn't today. To this day, we still get approached all the time.

I was speaking in San Diego at this conference called E-Tech in 2005, and Jeff was speaking there also. And, well, it's cool about Jeff. I don't know if he still does this, but when he goes to a conference, he actually attends the conference, which is cool. A lot of people kind of come in and leave, especially like someone like him, you think he's in out, but he was sitting in the front row, listened to all the speakers. And I think he liked what I had to say. And I think a few of his companies that he'd invested in was, were using

Basecamp at the time. Base camp was only a year old at the time, basically, when I was giving this talk. And I think he just kind of liked our irreverent point of view, which is kind of sort of how he is in general. And so his people reach out to us, hey, you know, Jeff wants to catch up and kind of had an inkling that this was about an investment of some sort. Otherwise, like, Why, what do you want to do that? And I was hesitant, but it's like, it was Jeff Bezos. It was 2005. I mean, yeah, sure.

Let's get together. I'd love to. And my God, I'd be honored to do that. So flew out to Seattle. We had a conversation and really going into it. I'm like, in my head, I'm like, we're not taking anyone's money. But he's money. Not even his money.

I didn't, I didn't want the money. I don't need the money. And I don't want what the money costs. Right. Having to answer to somebody else, right? Yeah. There you go. So people think like you get money.

Well, guess what? You pay for that. You pay for that money in other ways. You lose your independence. You're on someone else's schedule in a sense to sell the company or go IPO or whatever. Like funds need their money back. Investors need the money back, understandably so. So I went in not wanting to do this.

But we just had some really good conversations. And what became clear was like he was just interested in supporting a handful of entrepreneurs that he thought we're doing interesting things. He was not looking for an exit. He didn't want it. We don't have a board. He didn't want a seat. We don't even have one, right?

And he didn't want to create one. So he wasn't looking for control. He was looking to support some people. And part of the support was liquidity. So Jeff didn't really invest in our business. What he did was he bought secondaries. He bought some shares from me and from David. And we put that money in our own personal bank accounts.

So we took some risk off the table early on. But none of his money ever went into our business. Our business is 100% always has been funded by customer revenues. So it was kind of this ideal situation where he didn't have a board seat, didn't really have any controls, a very straightforward, simple thing. We got to take a little bit of money off the table early on when we're like, this thing could be a fluke. This base camp thing is taken off, sort of, but like, I mean, I don't know what's going to happen.

Like, we could get crushed in a year. I'd like to have something to show for the effort we made. And it all just kind of like magically came together in a way where he was sort of the ideal partner. And what's interesting is, so he still owns a piece, the same piece, although he had to split it up with his ex-wife. Like, there's just that those are the rules. So, but anyway, still owns a slice and she does. And we're an LLC. So we make distributions every year to member unit holders. He is one, she's one. So he gets paid every year on this investment without having to exit the company. So he's made his money many, many, many, many times over. And he's made his money, many, many times

We still has all of his equity. And it turned out to be a pretty good deal for him. So that's great. But he's, to your other point, he is the most positive person I've ever met in my life, like by a long shot. And that really made an impression on me. I've never been around someone so optimistic, ever. And I've been around a number of optimistic people.

He just has a can-do optimistic spirit about him that it's always sort of anchored in like, Humor and like the silliest ideas are the most interesting. And I just loved that about him. We really got along in that way. So we went for it. Most positive person ever. Yeah.

How did that come out in the meetings in your conversation? Like how did you sense this over? I mean, what a great trait, by the way. But how did you sense it in him through your conversations? Yeah. And I wish I had that because I'm not maybe inwardly. I feel optimistic and confident about things, but I don't have that cheerleader spirit that he has in a sense.

First of all, if you ever seen any interviews with him, or met him, I don't know, but massive laugh. Like just deep, fun, fun laugh. His laugh is fun, and it's never faked. You can tell it's super genuine when he does it because it's so deep. You could imagine a fake version of it, but when you hear the real version, that, that's real. That's all in. And every time we asked him a question about, like, what would you do or whatever? he's always like, what would you do?

What would you do? And we'd sort of get in this conversation. He's like, I love that. You should do that. Because if you guys think that that's good, you should do that. Like, he's very, now, I don't know what it's like to work for him in his own company. So I can't comment on that. I heard he can be quite tough as you'd expect.

But with us, he's always been very supportive and positive and, like, encouraging and an extraordinarily good listener. And this, again, one of these people who are, when you're talking to me, You feel like you're the only person in the room and he just has that quality. But it's it's always like, it feels to me always rooted in genuine curiosity and excitement for novelty and cleverness and fun ideas. And we were, we were kind of spinning those kinds of things out early on and we still do that.

But like back then especially, we were kind of new on the scene. We were very irreverent doing things totally different than everybody else. I think he just kind of came into that and loved that. And it just, we felt that vibe from him. So it's also got to feel good. I would imagine to prove early supporters right. Yeah, that was early in the game. Yes.

You give a speech. He supports you. And what a great feeling, especially now what he's become too. But proving early supporters right, I think is, it's just a really amazing. Because like now he's made all of this, not that he needs the money, but he's made it all back in a lot more. and you prove that person right as opposed to, I think that's more fulfilling than proving haters wrong or proving doubters wrong is proving supporters right.

That's a good way of thinking about it. I mean, I've always been fueled by people who don't think I can do something for a reason like that. Yeah, that has always kind of been a bit of a chip my shoulder kind of feeling around that. It started out when I was a web designer way back when I first started my career. I'd submitted some work to this award. thing that was like kind of the preeminent like web design award guy at the time. David Siegel was his name. I forget what what the award was called at the time. But anyway, I submitted some work

to him and he wrote me back. He's like, you suck. He's like, you should get a new job. Like, this is not your career. He's like kind of a real, you know, chippy guy. And I loved it. I honestly just loved it. Like, I'm like, okay. All right, let's go. And I think this comes from like, I'm five foot seven, so I'm not a tall person. And I've always been good at basketball and I can jump. And I used to be able to touch the rim and I can't do that anymore. But I used to be able to. And so I love this sort of notion, like someone looking at me thinking I can't do something

and then doing it always has fueled me. But so haters, like, I kind of don't, a hater is kind of fueling when a bunch of people gather or pile on, like I don't really pay attention to that. Yeah. But I do agree with you, though, that it's nice to people who are. really by your side in the early days who believed in you, who saw something others didn't. It is very rewarding to, to your point, prove them right or more so like find a deep satisfaction in making them feel good about their decision. So I'm with you on both sides here.

I agree. And as you know, there are so many great, great examples of the Michael Jordans of the world and very Tom Brady's where they, Aaron Rogers, have this permanent chip on their shoulder. And if there isn't a person there to put it there, they'll create it. They'll make it up. And so I do think, I mean, we're humans. Like we're human beings.

We're not perfect. Like I think there is something real. Like I still think about people when I was in college, I played a quarterback and I got beat out for a starting quarterback job by a guy who ended up being really good, played for the Steelers named Ben Rothersberger. And I remember people from my hometown, when I transferred, because I after I got beat out for that job, saying, yeah, he's a really good high school player,

just not good enough to start in Division I college football. I still remember the actual names of some of those people that said that to me when I transferred. And yeah, I thought about it when I was not only the starter, but team captain and had a chance to play after college. Like I thought of some of those people. I wouldn't approve my parents, right, right? My supporters, people would love me. But yeah, dude, like, there's a little bit I'm thinking of those that's saying like, yeah, good high school, not good of playing college. I was like, well, what's up now? You know, like, There is a little bit of that that happens, you know. I think it's healthy on both sides.

And I've always been, you know, I grew up in Chicago. So Jordan was like kind of, you know, my, my idol kind of guy. And he is like all the way at the end of insane when it comes to chips on your shoulder. I mean, which is amazing for someone who's so accomplished, of course, to remember every single slight ever that anyone ever slited him, talk shit, whatever it was, anything. Like a little shove, a little, like, and you know, if you, if you've. So pay attention to him. He'll always talk about the, I remember that one thing,

and that one guy said this thing to me, and I dropped 60 on him. Like, that's how I've always felt I couldn't drop 60 on something. Like in that way. But I do, I do look for those things. And they do give me some momentum and some sort of purpose in a sense. Kind of,

not really purpose, but enjoyment, frankly. And we've done, you know, I think this manifests itself in our business. And that we've been very early on a lot of things. So we were very early on remote work.

We're very early on four-day work weeks. We're very early on small teams. They're very early on bootstrapping, although, of course, many companies have bootstrapped over the years. But in our industry, like pitching bootstrapping and talking about it seriously, we're very early on SaaS. You know, now we're very early on this thing called Once, which we're doing, which is one-time payment software, not subscription-based anymore. And people like, but that's stupid. And I go, yeah, it is stupid. Let's, you know, it is stupid.

Right now it is, but let's see where it is in five years or whatever. And, like, we're going to put some products out and see what happens, you know? So I do like that. But yeah, I mean, I also think about like my parents being at every track meet I ran track. So every track meet I was ever at. And my dad yelling at me in a positive way about get your knees up and all the things he would teach me about running, speed, you know, I was a sprinter. And finally being really damn good at that and like being really happy to just.

I know how happy he was that I got really good. And so you can play both sides of it. I think it's, look, you got to look for motivation. anywhere you can sometimes. Yeah, no, no, 100%. Being early, I think, feels to me like a skill, something you've developed.

How does one, this is a tough one, how does one develop the skill of being early? Well, I think part of it is not second-guessing yourself when you have an idea that you want to pursue. I think it's, I'm not suggesting where the, first ones to think of any of the things that we were, let's say, early on. And we weren't the only

ones, but there was a collection of companies that were early. And I think those are the ones that just do the thing and not like worry about what everyone else thinks they're going to do or be or how it's going to work out. But they're like, we believe in this. We're going to go for it. So I think a lot of it's just like allowing yourself to do the thing. And sometimes you're really early and it doesn't work. I mean, for example, we made this, this product, this group chat tool back in in 2007 or six called Camp Fire, which we've since re-released as this under this once umbrella, but back in 2006, I couldn't shove the idea of group chat down people's throats. Nobody understood it.

They're like, why would we chat like at a company? Like, what? I don't, we can just talk to each other. Like, why would, so no one understood this at all. We couldn't sell it. It was like our least worst selling product we've ever made, essentially. essentially, and then along comes Slack, you know, I don't know, it was eight years later, or whatever it was. And we'd sort of given up on it because, like, we just couldn't move it.

And they just crushed it, right? Now, essentially the products were the same. They did a few things really, really well that really, really mattered. They deserve all the credit in the world. But that idea, literally, if Slack had launched Camp Fire in 2006, it would have died on the Vine, too, essentially. It just was too early. So you can be wrong. Sometimes it takes a while for something to make sense. And sometimes it never makes sense. But I do think it's not being afraid to just try something because I think most people talk themselves out of the early ideas they do have.

Like it's not ready for prime time or no one's going to buy it or it's not going to work. And so they just don't. So I think we just do. That's kind of maybe how you are early with things. One of the other unique parts about your story, I feel like Jason is your relationship with David. You mentioned David earlier. To some, he's known as DHHH.

I've had him on the show. Super interesting, dude. What's been the key to you guys having a good partnership? So a few things probably luck, number one. The fact that we even met, he was in Denmark. I was in Chicago. We met on the internet because I had a programming issue. I didn't know how to solve.

He wasn't a programmer, but I was trying to learn PHP. And he happened to read our blog somehow and happen to see my question. And that's how it all happened. So that was super unusual. Shouldn't have happened. But it did. So let's say the connection was made, then what, right? Well, first of all, he's on the technical side.

I'm on the design side. So we are primarily doing very, very different things. So we're not stepping over each other and constantly headbutting over the same thing. Well, headbutt over other things that are on the business side or product side, because we both kind of share that. We're about 90% aligned on many of these things, but there's some differences there, and we both have to make some of these decisions.

So sometimes we'll argue there, which is totally healthy and good, but the majority of the work we do is different work. So we compliment each other rather than get tripped up. So that's number one, or number two, I don't know what number of this is, but the other thing is like, and I'll speak for myself, you'd have to ask him,

but I just admire David's abilities. I admire him as a person, his skills, his writing ability, his technical ability, his ability to make decisions, his ability to see things other people don't see, his ability to be early on technical stuff, it's willing to just go for it and just be able to simplify. Like, I admire that. And I think in any partnership, you must admire your partner. Like, you should like them, but you should also admire them and be like, wow, they're good.

They're really good at what they do. I admire their skill. I'll never have that ability. I'm not that. They are, and I admire that. So I think there's this admiration, different skill set, but they're a good. then we see enough eye to eye on the core business side of things and how to run a business. So we're not constantly arguing about that either.

Neither of us want to raise money from the outside world. Both of us want to keep the company as small as possible. Both of us believe in profitability. You know, both of us don't think growth is the be all end all. So like all the real things that matter that founders often hit their head over or but heads over in a painful way, we don't have those interactions. We'll argue about the execution of something or the quality of something, whatever. but that makes it better.

We never come away from that feeling like hurt and injured. Like I know a lot of founders do and they just radically disagree about fundamentals in their business. Most people out there want to scale and grow at all costs, do whatever it takes. And so it's interesting that both of you are fully aligned when at the beginning, there couldn't have been any way of knowing

that you would have been both against like growth at all costs or not, or both so focused on profitability and building a, a company that's going to do that every single year and not just try to raise money and build, build, build, big exit, right? So is that part of the luck? Or have you influenced him more about that? Has he influenced you more about that? Or were you guys just perfectly aligned from the beginning? Well, I'm sure we've influenced each other in many different ways, clearly. So David was a fan of our company in the early days. And our company was based on ideas. So if you were to look at our early

website, if you actually go to 37signals.com slash manifesto, I think is the original site that's still available. You have to double check that. I'll get you the right link if that's not exactly that. I think it is that, though. That was the original site. And we were a web design company, and the site was black and white, and it was text only, and it was 37 weird ideas about stuff. So if you're a fan of the company after looking at that, like all that stuff was about being small, focusing on quality, the value of design, people who inspired us, good writing, all these things. And David fell in and liked that stuff. So I think we had this shared understanding of what we thought was good to begin with, which was helpful. But yeah, we didn't like talk about

profitability or any of these things early on. But I think like the sensibilities were there because the foundational, our foundational interests were aligned. And then that, and then, And then I think, I mean, it's pretty hard to probably be in a business that is profitable and throwing off cash to the owners and think it's a bad direction. So I think like you kind of ultimately fall in behind each other in a sense. And then you push and pull each other in different ways. And we've been influenced by one another in a lot of different ways. But yeah, like if he would have come from a world, also I would say he had similar experiences.

So he'd worked for a VC-backed company. I think it was in video games or something like that and just saw like the sort of the the tragedy that that was. And I had done the same thing. I'd worked on a contract basis for a company called Quaka Sports in San Francisco. And I was only there for a few months. And in those few months,

I think they doubled or tripled their headcount like that ended up having hundreds of people that raised a bunch of money. And I could just see waste everywhere. And like, this doesn't make any sense. And everyone's like, no, this is the future. And like, they went out of business in a handful of years. It was like so obvious to me that was going to happen.

And David, so David has similar experience. I had a similar experience. we came to this. He saw the kind of our point of view that was very clear and in out front. And so I think we had enough in common early on to make it all kind of coalesce. You mentioned one of the important things was good writing. I read everything you write. You're one of my favorite writers, both online and books too. And that, I think great writers make it look easy. I read it. I read it. I'm like, yeah, that's easy. I could do that. And then you go try to do it. You're like, that doesn't look the same.

I love to hear more about, one, the importance of writing from a leadership perspective, right, and how you view that, as well as beyond repetition, how you've gotten so good at it. Well, first of all, I'll take the second part first because I hated writing growing up. I hated it. Absolutely hated it. And I hate it because I was asked for write things I didn't care about. Like I had to write a report on, you know, I don't know, Rome or something. I mean, like Rome's cool now. But when I was 15, I could. care less, right? You know, all the things, whatever, right? You're asked to write these reports, and they have to be 10 pages, and it's like, oh, about page count and subject you don't care about. Or maybe you get to pick a subject, but what do you know when you're that age and you just, whatever. I just hated it. I hated the formality of it. I hated the process around it, the length requirements, like the whole thing, the way it was supposed to be done, which is like you write a draft and you hand a draft and the teacher gives you feedback and you're

doing another. I don't write that way. I don't like that. So anyway, hated writing until I got to write what's in my head. You and I are having a conversation right now. We're not struggling to have this conversation. You're asking great questions. Hopefully I'm providing decent answers. If you could just write what you want to say, then writing isn't that hard.

What's hard is when you think about having to write something. So the way I do is I just think about what I want to say. Instead of saying it, I write it. And so my writing is very conversational and my head is always like, write it like you'd say it, write it like you'd say it. And this is true in business writing too. Like when I'm trying to come up with the marketing, like I write all of our marketing sites, so all the copy on our pages and the headlines and everything.

And I can find myself sometimes falling into that trap of trying to like write a marketing e headline or something or describing the product in a way that like, you know, is it like a marketing description of the product? I feel like you should say for like this grand audience when it's like, actually that probably doesn't work as well as me just saying like what I think. Yeah. And also like one thing I always catch myself doing when I'm in this rod is being like, would I ever say that?

Would I ever say that out loud? Would I ever say Basecamp is a project management tool that's apt for. Like no, I would never talk that way. So I try to make sure I'm writing the way I would actually literally speak to a human being if I was talking about our product or if I was talking about. an idea or like I am right now with answering your questions, you know. That's how my writing would sound just like I'm talking. And I just know, I know this because I've talked to so many writers about this who struggle with this. They can't quite, and I'll, I'll get, they'll send me a draft

of a of a blog post or something like, what do you think? And I'm like, would you ever say this out loud? If you were to read this out loud, would this sound like you? And they're always like, no. I'm like, well, then why, why are you writing it like that? Like so, and I know why. It's sort of been ingrained in us to work to like think about writing. I'm just trying to think about communicating and I don't care if it's verbal or written. It's going to be the same for me. So that's kind of I'm not going to call it a secret. It's certainly not a secret,

but that's like my approach that I think works well for me, at least other people are going to write in different ways, but that works well for me. Do you ever actually speak and then just have like transcripts written out and then you like edit the transcript? So it's literally you speaking? Yeah, I don't do that. But what I will do sometimes is I'll use the voice memo app on my phone to just, if I have an idea that I think is interesting, I'll just like speak it and just record that.

So I don't forget the idea. And then I want to say it versus writing it because I can just kind of like freewheel and just kind of go free associate for a little bit and not like worry about grammar and all the stuff. And it's just faster to talk it out loud. So I might talk for 45 seconds into the mic just to record something. And then I'll come back to it and I'll write it. But I've never tried to dictate an entire piece. I think I would probably be spend more time editing out the ums and the aze and the and the weird structure because speaking is still a little bit different than writing in a sense.

That it's easier for me to just write the thing. And I also, by the way, I don't write in drafts. So I don't write a whole thing and then go back and revise the whole thing and then go back and revise the whole thing. I'm writing and editing as I go. So I will finish a thing and then read it and go, I don't like this and like where can I tweak it? But I'll write a sentence or two and I'll come back and quickly modify that without moving on. So it's not a whole complete draft thing. I think that I found that that is a waste of my time to do it in that way.

I'd rather just kind of edit as I go and get somewhere good as I'm going. And then, you know, proof rate at the end and maybe revise it a bit more or usually cutting it down a little bit wordy sometimes that way. So that's my much. The Morgan Howsell style of his writing, that's what he said. Sometimes he won't even read the thing. He'll edit as he goes, press publish. And he's like, the quickest way you'll find a typo is just hit publish. Because all your readers will tell you, they'll tell you. And then you just clean it up. He's like, and I just fix it afterwards. And I'm like, he's a really good writer. But I read all of his. this stuff too. I've done that too. And it's funny because that is really how software works as well. So just briefly, there is nothing better than shipping something to figure out if something's working or not. You just ship it and like at that moment, you actually figure out what's really worth fixing and what really isn't worth fixing versus like laboring over for three weeks to get it just right before shipping. I feel like you're better off shipping it and spend those three weeks

if there is even work to do over the next three weeks, refining and fixing the things that really needed fixing and refining and not just fixing and refining things that didn't actually need it. And shipping is the best way. It's just like publishing. That goes for life. Yeah. 100% great. If you like just ship it, you'll, you'll, I mean, we learn who we are in practice, not in theory, right?

The hermereo Barquite, but it's so true for pretty much everything. Like we learn by doing, we learned by that. One one more point on writing from a leadership perspective, Jason, is that some leaders that I work with, they have like comms teams and you know, like, they're they have something they want to say, then they got to go with the team, and they go through it. And by the time the draft gets back out and it's sent to the whole company,

it's like, what is this? Like, it's plain and boring and generic, and it's obviously not from the voice of the leader. Two things. One, I think writing is the ultimate tool for clarity. Like, you don't fully know what you think until you get out of your head onto the page. And then two, for the reader,

especially if you're leading a company like you are, if they sense it's not your voice, you might as well just delete it. actually has like a negative effect, I think, because it's inauthentic, it's not real. And they're like, well, what is he actually thinking as opposed to when they read your stuff? You're like, oh, I can hear Jason saying this stuff. So now I know exactly what he's thinking. So I know there's two parts of that when it comes to getting clarity of thought as the writer.

But then from a reader's perspective, it's actually getting your real thoughts as opposed to some like comms team edited draft that I think could have negative consequences. consequences for a leader. Yes. Oh, my God. I mean, so David and I will often talk about how, like, the worst thing in the world would be to have, like, a ghostwriter or a comms team or anyone that has to filter our words and write something for, you know, for our behalf and put our name on it. Like, there's no way in hell ever.

Anything that comes out of this company with my name on it is not written 100% by me. Or, like, I might run it by somebody that I choose to. Like, David can give me some feedback, whatever. But, like, no one's writing this for me. Absolutely not. Same thing is true for David. Same thing is true for anyone. There is no one writing things for anybody here. And there's no filtering through legal or we don't have a PR team. We don't have a PR. We don't have a comms person. We don't have a lawyer on staff. We don't have many of those things. We write what we write. And that's what we do. For us, now, can you do

that at a company with 60,000 people? I don't know. In your public company, maybe you can't. Maybe you're not allowed to. But I'll tell you what's very interesting is like Mark Zuckerberg's sort of transformation, I think recently. Like he's doing a lot more first person sort of rough cut stuff. I find it really endearing. And I could imagine maybe there's somebody at the company who's nervous about that. I don't know, whatever, but he's not. And I think he realizes that like he needs to connect with people.

And the best way to connect with people is to communicate directly to people in your own style and your own way that is so 100% your words out of your mouth. So I'm a big fan of that. And if that was ever to change here, like I wouldn't be here. There's no way in hell I could ever run a company where I couldn't speak for myself. Speaking of Zuckerberg, I mean, talk about a transformation. I mean, I think a big part of why he's gone from a guy that a lot of people did not like and hated to now. I think a lot of people respect and like is because he's like, yeah, I'm just going to say it.

It's like the end of Kobe's career. You remember when Kobe kind of made that shift where he's just going to tell the truth all the time. And we all like, I just wanted to hear every single time a microphone was in front of his face because he kind of got comfortable enough to just say what he thinks. I feel like that's where Zuckerberg is. And when he has his buddy with the goggles on filming him and he's just speaking directly to camera. And it's like he's MK, a B, HD, you know, where he's just doing like the YouTube reviews. But he's doing it of his own product versus Apple. I mean, you're like, this is wild.

I mean, this is wild that this guy's doing it. And it's so connected with people. I think it's so worked because we felt this is genuinely, he's really smart, but this is genuinely what he thinks and it's a little bit raw. And yeah, there's a little editing, but not much. It's pretty much just him to camera giving you a product review. And I found it super compelling. Yeah. And he's doing more of that.

I think he's coming into his own right now. It's interesting. He's been doing this for a long time. But I feel like he's having a resurgence in a second, second wind in a sense. And partially because like the industry is in the place that it is. He's finding himself as an opportunity. I mean, there's nothing wrong with being an opportunist. I feel like he's a bit of an opportunist right now.

Like Google, Apple is sort of maybe fading a bit in some ways. I'm clearly like huge powerful company making great stuff, but like their reputation is sort of taken a hit. Google's reputation is taking a hit. All those companies are trying to do like a lot of closed stuff. And he's like, well, I'll take the open road. I'll go the open route. And which has not historically been actually their approach.

But I think you kind of want to root for that. And you're kind of glad that he exists. And I think it's great. I think he wasn't the most comfortable communicator, like early in his career. I think he was pretty stiff and maybe not comfortable in front of a camera. But he's been working on that clearly. And I think when he's at his best when he's just not scripted. And when you see him do scripted stuff, it's still cringe-worthy, in my opinion.

And you're like, dude, just talk. Don't read a script. You know your stuff. You know your product. You know your pitch. You know how this goes. Just be yourself. you can really feel when someone is just going off the cuff versus reading a teleprompter,

as good as they might be at reading a teleprompter. It's the cadence, the tone, the timing. You can tell when someone's reading and you can tell when someone's speaking. And he would be better off and I think it's proving true that he's better off just speaking, just being himself. Tim Cook would never do this. Like, he's just not like, or maybe he would, but he's just, he's too disconnected from the product in a way that Zuckerberg is very connected.

I don't know him that well, but you think so? My sense is that Cook is definitely, I mean, probably an outstanding, not even probably is an outstanding operator. Yeah. But he's not a product person in the way that Zuckerberg understands his product, he uses his product through and through and through and through. Like, I really feel like he's in there with the teams working this stuff out and has great product instinct.

And I think that comes from just starting a company that was a product company. Like Tim Cook was an operator, a COO, extraordinary, supply chain genius. And it's clearly run Apple really, really well in a lot of ways, obviously. But he doesn't have the product, in my opinion, for whatever it's worth, which is not much. But it's just my observation. Like he just doesn't have that product gene in him. So when he talks about the products, it's like there's a translator in the middle somewhere. Yeah.

And I think you can, even if he was to go off the cuff, it still feels like there's a translator. Also, back to Zuckerberg, and I think some people think this is really stupid what I'm about to say, but I would not discount the fact of this dude's like working out hard in the gym and he's fighting. And I think it's built confidence. And you can build confidence in certain areas of your life that then show up in other areas of your life. I'm a big workout guy, athlete, right? You're running and all this. I think that stuff will help you in way more ways than just being a healthier person because you're exercising. And I don't know if enough, if that's enough of the story.

I think you see this guy with a shirt off and he's kind of jacked, you know, and he's at UFC fights. I think that plays a role in the guy showing up more confident for these podcast interviews that he's doing as well as the straight to camera stuff. That is a part of leading. And we have to find ways to build confidence so that it kind of inspires people to say, yeah, I can get behind this guy, you know, and I feel like that's part of his story. 100%. I think it's a great observation. And I don't think it's stupid at all.

I think it's probably, we're guessing here, but probably very true. If I had to wager, if I had a place a bet, I think so. Mind and body are connected. You know, you feel good about your body. You feel good about your strength, yourself. He's been very high-achie person in the software world. And now clearly he's like a legitimate, what is he black belt now or something? And a few things.

I don't even know. He clearly worked hard and is committed and disciplined and pushing himself. And of course, why wouldn't you feel good about walking through the space, walking through the world that way? It's going to show up in some other way. I know, like, for me, I've been doing CrossFit for like a few years now. And I feel better in every way because of it. I've always been an athlete.

I've always been in shape. But I've been pushing myself a lot harder over the last few years in ways that kind of surprised me. And I feel incredibly strong and solid in a way where I feel like foundationally, I have more stability mentally as well. You know, and so I've not surprised at all if that's the case with him. And it's cool to see. It's really good. It feels good to feel strong.

Sure. It feels good. It shows up everywhere. It feels good. It feels good. It feels strong. One of the things, not to pivot too much, but I think that's also part of like the word culture is used constantly now and in your work rework you write about a culture and you said you don't

create culture it happens and so i would love to hear more about how you think about the culture at your company and how it has happened over time my feeling basically is that culture is essentially moving average it's not something you create actually it's something that creates itself uh it is the result of consistent behavior in an organization. So it's how you treat each other, how you treat your customers, the focus you have or the focus you don't have, the decisions you make or the decisions you don't make

or how you're making decisions, how you speak to the public, how you show up in all of these different ways. And it's just the result of all of those things. So you can decide to want a certain culture in a company. You can say that we're going to be honest and we're going to be open, and we're going to be transparent,

or we're going to really care for each other, or whatever it is, whatever your things are, right? It doesn't matter. I mean, it can matter that you want to go in that direction. You're going to make efforts to go in that direction. But ultimately, it's what are you actually doing? It's, you know, actions speak a lot of words, essentially in the most basic form here.

And I would take the last 50 days. I always think of a 50-day moving average. That's the culture. And the good news there is, like, it can get better and can get worse quickly. So it's good and bad. But it's relatively easy to correct if things aren't going well. And you also can't rust in your laurels because if things are going well, they can go bad too.

If you just start to be, you know, ters with each other or, you know, you're not helpful, whatever. Like pretty quickly, people recognize that very, very fast and it's going to take your trend line down. So I think of it as, yeah, as a moving average of results. And not financial results, but like all the results of what a team does to and with, one another. Would you and DHH ever consider selling? Well, so right now, no, but the truth is, like, businesses don't last forever. Yeah. So what happens to a business? It either goes out of business. It either goes out of business rapidly because something goes terribly wrong. It sort of fades away because it's irrelevant or you just mismanage it. It gets acquired or it can go public,

or whatever, right? It can merge with another company. There's like a handful of outcomes eventually, right? And I can tell you, like, going public would be a no. I'm not interested in that, right? Hopefully we don't crash and burn because we really screw something terribly bad up. I don't know where, I mean, can happen, but hopefully that doesn't happen. Or competition can come in and crush us in some way, whatever, all possible.

But we'd like to probably have control over our demise. in a sense. And I do think selling the business would be a bit of a demise, actually. It'd be the end of something. Not that that's a bad thing, by the way. Things end and everything does, and I don't think it's bad. So I'm using the word demise, which sounds like a negative, but it's really just like the end of something, essentially. So most likely, when that happens, it'll probably be a sale, because that's hopefully, we're, still doing well at that point. And that's sort of the natural,

that'd be the natural end. I think that another end could be, like David and I could decide to leave and bring in a whole new team to run the place. But I don't think we'd want to do it that way. I think we'd probably want to sell the business. But yeah, right now we're really thrilled to run the business still.

We're about to kick off some pretty ambitious stuff, things we've never done before. And I think this next year is going to be pretty spectacular and really, really fun. and hard. And so, you know, I don't think much more than beyond that anyway. But yeah, realistically, that's, that's probably what we would, what would happen. What are some of the, the things that you've never done before that you're, like, going to do? You're going to get this out of me, aren't you? Well, I don't know. I'm not going to try. Well, I would tell, one of the

things we want to do is we have more product ideas that we want to do. Sure. And we want to try to do two of them simultaneously, which we've never done before. We've only, like, built one product at a time, which is how, you know, we only have 75 or so people. So like, it's a tall order to build, to build a product anyway from scratch, do it well in the way, in the way we like to do it. So we'd like to do two at once. And that would be pretty amazing. And like to build a launch them at the same time would be pretty amazing, pretty fun.

And then we have, you know, might want to offer them in multiple different business models. There's just a bunch of stuff we're going to play with and see what we come up with. But I think we want to make two things at once. We've never done that before. and launched two things at the same time. We've never done that before. So that would be pretty spectacular if we can pull that off

in a relatively short period of time as well as what we want to do. So that's something we have done before. These also would be categories we haven't. We've sort of, they're adjacent to what we're doing, but not, we've never done these kinds of products before, but they're adjacent. So it wouldn't be a stretch to do these.

And I would say that. And then we might want to write another book this year at the same time. So we kind of want to take on a lot of work We're actually feeling right now like creative, we've got a good momentum, got a wonderful, extraordinarily good team, good size. Like, let's make sure we take advantage of this moment. And also, this is our 25th year in business. Like, why not?

If we destroy it because we do too much or whatever, like, okay, not a bad run. I mean, that's hopefully not going to happen. But like, if you're not willing to do this now, especially after we have this incredible history behind us, like, when are you going to do it? Let's do it now. Let's just get extra ambitious like 25 years in and have to be. some fun and see what happens. 25 years in, 75 people, fully remote. How often you guys get together in person? Twice a year. So we just got together a couple weeks ago, actually, in Atlanta.

So we pick usually a city in the U.S. and a city in Europe. And we kind of, in the spring, we do one, and fall we do another. It's not always the case. Sometimes there's two North American cities or whatever. So we were in Atlanta. Before that, we were in Barcelona. Before that, we were in New Orleans. before that we were in Amsterdam, we kind of go back and forth. We have half our companies outside the U.S. We kind of want to make it travel fairly easy on one half and hard on the other and then the opposite. These get-togethers are one week,

basically four days. So everyone kind of comes in on Sunday. We meet Monday through Thursday and we all leave Friday. And the first day or first day and a half is pretty much like business stuff, like state of the company, big picture ideas, Q&A, a little bit of a town hall kind of style, all hands sort of thing.

And then the rest of the time is primarily social. People get together in small groups. They have small meals. We also have a big company meal, but small meals, outings, you know, to do this or that,

or hang out as teams or just hang out, you know, and just kind of hang out in a city or a place or whatever. It's very replenishing. It's very refreshing. It's wonderful to see everybody. And surprisingly twice a year for a week at a time is enough.

It's enough. We look forward to doing it. And then when it's over, we look forward to getting home because we're a bunch of introverts. And it's, it's, there's always like this post meetup like exhaustion just because everyone has to see each other for a lot. But it really fuels us. And during COVID, we didn't do this for a few years. And it really hurt the company, I think.

Not being able to see anyone at all literally for a couple of years, which is not unique for us. But we really rely on these just simply two weeks a year. And when we didn't have them, it hurt. How much involvement do you have in design? like the entire experience when you're at these off-sites together? None anymore. No.

So you have like a team of people that are pros at that? Or you hire somebody or what? Two people. So Andrea and Bethany internally, they book all the venues, handle all the flights, all the catering, all the dinners, all the events. And you just show up? Everyone just shows up. They are magical at this.

This is not their full-time job. They do other things in the company, but they do these. And they're super good at them. everything goes off perfectly. It's sort of an extraordinary thing to like coordinate, literally flying in, you know, 70 some odd people. Not everyone shows up with these 60 to 70, let's say, from 60 to 70 different cities around the world,

essentially kind of not. And there's some people live in the same city, but it's a lot of flights, a lot of coordination. Everyone shows up at the same time. All the rooms are booked. Foods there. Everything's set up, A-V, the whole thing. So it's great.

I used to be more involved in where we would go, but I don't want that responsibility. I'd like it to be a surprise. I mean, I have suggestions. Like, I didn't suggest the last two, and I'm glad we went to those. I suggested the next one. We'll see where we go. I don't know.

The reason I asked is because with the changing setup of how people work, a lot of hybrid stuff, a lot more remote stuff, especially with sales organizations, which is, I've worked with a lot of sales leaders. And so their people are all over. They don't see each other very much. I think it is really important to be intentional about getting together. And to have a team of people who think about that a lot about how do we design a really good experience for us to be together if we're remote or if we're hybrid where we're not together very much. And that's changed a lot over the last few years.

You guys have been doing it for 25 years, but that's changed a lot for most companies over the last few years. So it's worth it as leaders to be to be thinking about this and to be really intentional. 100% agree. And it's it's really immeasurable. Like the value is there. I mean, first of all, it's very expensive for us to do this, but we don't pay rent because we don't have offices anymore. So basically all the rent money we'd be spending

goes into these two events. And they're very well thought out. And we adjust them. We've been now inviting a customer usually to each one to sort of talk about how they use Basecamp, for example, or hey or something like that. So that's kind of nice to see. And sometimes they're a little bit,

some of them are a little bit too booked up with events and things. So like we loosen up the next one so people have more free time. And then sometimes there's too much free time enough structure. And so we're very much paying attention to this. They're not formulaic, except for like a couple things. There's a company-wide dinner. There's an all-hands thing on the first day, usually, or sometimes a second day instead, depending on some people can't make it in on the first day. And there's suggested events and group things that you can sign up for,

small group dinners, small group events. There's a sign-up sheet and there's like six slots for this one and four slots for that one and sign up if you want or if you don't want to, that's fine. So there are things available and there are things to do and they're very thoughtful things. And I just can't recommend doing this highly enough. It's, it is expensive and it's going to seem like a huge lift just to get people together. You're like, why can't we just sit over Zoom? It's just not the same. You got to share a meal with people. You got to smile. You got to be, you got to see everyone's humanity, breathe the same air. It does matter. Yeah. Love it. Jason, man. Thank you so much for doing this. We didn't come here to promote anything. I just, again,

you're one of my favorite thinkers and writers. So any opportunity to talk to you to me, I treasure. it, man. Where would you send viewers, listeners to learn more about you online? Well, first all, it's very kind. And I'm glad we could line this up. I know scheduling was challenging on my side, not on yours. So I'm glad we could do this. So primarily a couple places. So I'm on Twitter, or X at Jason Freed, F-R-I-E-D. I'm on LinkedIn. Also, you can find me there. I write stuff there, too. And then I have my own little newsletter. So if you go to world.com slash Jason, It's my little email newsletter and personal blog thing. You know, that's kind of me.

And then, of course, check out our stuff, 37 signals, Basecamp, Hey, Once.com. You know, we've got a lot of stuff going on these days. We've written a bunch of books. You can check those out too. I'm sure you'll link those up. So, yeah. And you can also email me. My email address is public.

Jason at 37Signals.com or Jason at Basecamp.com or Jason at Hay.com. You can hit me up. If you email me, I will write you back. Sometimes I might take a while. I would say if you want to respond sooner, keep the email shorter. The hardest emails to respond to are like, you're like, God, this person put like an hour into this. I can't be flip it and write a quick response.

I have to really take time. And then it's hard to find the time. So my general suggestion, if you want to write someone and you want to get a response, short emails will almost always get a response. So you probably don't remember this, but you had posted on Twitter, this might have been two years ago, year and a half ago. I don't remember how long it was. And you said, man, I wish people would just say, hey, do you want to record a podcast right now as opposed to like having to schedule it? So I remember I waited like a week, did a lot of research, you know, got my outline ready to go.

And then I emailed you and I'm like, do you want to record a podcast right now? And then you couldn't. And then I did it like again and again and again. And then I was like, would you just want to schedule it? So we eventually scheduled it because I, I'm with you. Like there are some times where I would would say, you know, someone wants to say, hey, can I get some time to do whatever? And I'm like, yeah, now. Right. Now. Right now.

Let's do it. I don't want to put on my calendar. I hate putting on my calendar. I want my calendar to stay clean. I got to think and I got to write and I got to prepare. I, yes, right now. Right now. Like I almost do that every time.

I'll wait to respond and say yeah. Now. And I guess that's, I don't know. That's a little power imbalance. But to me, I'll say yes, but I would rather just be now. You know? Yeah. It's funny how many times I tried to actually record this podcast by just saying,

dude, you want to do it right now? You want to do it right now? It's funny because I happen to be in a weird time where my schedule is really messed up. It's like taking the kids to school and there's one of the things we're working. So like the right now's weren't working, but usually they totally do work.

But my schedule's a bit scattered. So I'm glad we could line this up. And I think you sent me a note a few days ago and like, yeah, how about Friday? So like it was close to now. It's more like I hate scheduling things like, let's say right now or in April. Like someone's like, can you do a interview

on June 9th. I'm like, no, it's too far away. I don't know what I'll be doing in June. So I appreciate the persistence and thanks. It was really fun to chat. No, I appreciate it, man. Thank you so much again for doing this. And I would love to continue our dialogue as we both progress, man. Yeah, let me know. Happy to come back on and chat. Thanks so much, man. It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learningleader.com. Let me know what you learned from this great conversation with Jason Freed. A few takeaways from my notes, you don't create culture. It happens. A company's culture is a 50-day moving average. It's what you've been collectively doing as a company over the last 50 days. How do you treat people? Who have you hired or fired? And why?

Thinking of culture as a moving average is a much more useful way as opposed to putting words up on a wall. Culture is about what, you actually do. It's what's happening. Then how about that Jeff Bezos story? You never know who is watching. Jeff sat in the front row for one of Jason's keynotes and was so impressed that he asked to invest in his company. When you have the guts to put your thoughts and beliefs out into the world, it can work as a magnetic effect to attract people to you. And it's just so refreshing also So to hear Jason talk about one of the core qualities that he loves so much about Jeff is that he is overwhelmingly optimistic. The world is built by optimist. And then I will beat this drum forever.

All leaders should have a writing practice. This is how I became aware of Jason. If he wasn't publicly writing, I would not know that he exists. But he ships work on his website, on Twitter. He writes books. And I think it's another reminder of when you hear a clear thinker, it's probably because they have a writing practice. They're regularly getting the thoughts out of their head onto the page. And in his case, he's regularly sharing this with his company.

And I think if you're leading a company, hopefully you're writing a lot. And hopefully you don't feel the need to send your writing to a comms team or a lawyer before sharing it. Now, I know there's different situations depending on the size of your company, but we even talked about Mark Zuckerberg doing this right now, and he's leading a massive company, and it's working. It's working really well because it's genuine and it's authentic, and I think that's what people want. So write like you talk, write what's in your head, think about what you want to say, and then say it. Once again, I would say thank you so much for continuing to spread the message and telling a friend or two. Hey, you should listen to this episode of The Learning Leader Show with Jason Freed. I think it will help you become a more effective leader.

And because you continue to do that, and you also go to Apple Podcasts and Spotify, and you subscribe to the show and you rate it, hopefully five stars and you write a thoughtful review. And by doing all of that, you are continually giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so much. Talking soon. Can't wait.