The Exchanges

Q I would, though, love to kick off today, David, with a little bit on you, so tell me, how did you make your way into the world of tech and startups, and what was that founding moment for you and Jason with Basecamp?

A Sure, so in the mid to late nineties, I was doing gaming journalism online, uh, learning about the internet. And in 2001, I had learned just enough PHP, HTML, and whatever else to be dangerous or overconfident enough to write Jason when he posted a blog posting on the company website Signal V Noise in 2001 asking for some help. I was just me, David, sitting in Copenhagen, Denmark, seven time zones away, a fan of the company, and I wrote him an email explaining how to do something in PHP. He decided it was It's actually easier just to hire me than it was to learn PHP, and we started working together. And then we worked for a couple of years on client projects together. We built one SaaS app before we got going on Basecamp, but in 2003, we started working on Basecamp together. And 2004, we released it. 2005, I released the extraction Ruby on Rails, the toolkit from Basecamp. And I've pretty much been working on both of those projects ever since.

AI assessment note: “in 2003, we started working on Basecamp together. And 2004, we released it.”

Q I would, though, love to kick off today, David, with a little bit on you, so tell me, how did you make your way into the world of tech and startups, and what was that founding moment for you and Jason with Basecamp?

A Sure, so in the mid to late nineties, I was doing gaming journalism online, uh, learning about the internet. And in 2001, I had learned just enough PHP, HTML, and whatever else to be dangerous or overconfident enough to write Jason when he posted a blog posting on the company website Signal V Noise in 2001 asking for some help. I was just me, David, sitting in Copenhagen, Denmark, seven time zones away, a fan of the company, and I wrote him an email explaining how to do something in PHP. He decided it was It's actually easier just to hire me than it was to learn PHP, and we started working together. And then we worked for a couple of years on client projects together. We built one SaaS app before we got going on Basecamp, but in 2003, we started working on Basecamp together. And 2004, we released it. 2005, I released the extraction Ruby on Rails, the toolkit from Basecamp. And I've pretty much been working on both of those projects ever since.

AI assessment note: “in 2003, we started working on Basecamp together. And 2004, we released it.”

Q to you is, you know, This is, you know, spawned a rise that no one else has, you know, a lot of people haven't seen or experienced before. A big question for me, and I think a lot of leaders would be, how do you combat the mental health, the loneliness, and the isolation, maybe, for a generation that haven't experienced it, and what would you advise in that perspective?

A It's really tough, and it's real, and the first thing you have to accept that this is real, and this is something people do struggle with. Different people struggle with it in different proportions, but you have to deal with it head-on. So the way we deal with it at Basecamp is that instead of Mixing it together with the work. We say our social connections, our human connections are really important. They need to be replenished frequently, often, and let's just do that explicitly. One example of that we just instituted recently is Fridays at 10 a.m., we have an hour of game time. It's a open video conference and call where anyone who's interested can jump on during work hours to simply hang out with their co-workers and play games. It has no work purpose. It's not like the games are about the work that we do. They're simply there for the social connection. Another example of this that we've done for many years now is something we call five by 12, where in normal times, once a month, five people plus Jason and I will get on a call again during work hours for an hour to talk about everything else except work. What's going on in our lives, what's going on in the world, all that kind of stuff, and using those opportunities to sort of top off on the social connections. We do the same thing in asynchronous form using Basecamp. We have these automatic recurring questions in Basecamp t…

AI assessment note: “the way we deal with it at Basecamp is that instead of Mixing it”

Q know, you never got on the Silicon Valley VC treadmill. And so I guess my question to you on that one is, you mentioned the commercial pressures. What do you make of the immense surge in activity we've seen over the last five years in VC fundraising, the requirement that you have to raise VC money? And how do you think about that, having had the perspective that you have?

A Well, having had the perspective I've had, which goes all the way back to the first.com boom and bust, is that I don't think there's anything novel in the past. Five years. Maybe the valuations got higher, but these pressures have been in software for a very long time, and I don't think they're, they're any more widespread. In fact, if anything, I think the opposite is true. It's never been easier to start a new software company than it is today without raising money. It's never been easier to build a nest edge working for someone else for a short period of time, making copious amounts of gold doing that, and then taking that gold and starting off on your own path. This idea that you need Venture capital. You need outside money is, is complete bunk and bust. And this goes back to, to a lot of things. As we talked about remote work, the fact that you don't have to live in Silicon Valley or New York or Seattle or any other high priced metropolitan area to collaborate, to launch something new, you can live wherever and it's going to be fine. And it also goes to the example that we've been trying to set at Basecamp is you just, you don't need a thousand people. In fact, when we started Basecamp, we were four people working part-time on this side project that was Basecamp, and it took us about a year before that side project was making enough money to pay our salaries, and it wasn't…

AI assessment note: “This idea that you need Venture capital. You need outside money is, is complete bunk”

Q determine between the meetings to The tape versus the meetings not to. I, I must admit I,, I suffer victim to this where I take all of them because I never know which serendipitous good thing could come out of them. So I always take everything and then I spend my time zoomed out of my mind. So how do you determine it and what advice would you give me?

A Great question. I think there's a good set of tactical rules you can adopt. The first one being that what are meetings good for? In my opinion, meetings are great when you have two or three or four. That's probably the limit. If you get into five, it's already starting to be problematic. But let's just say four people who are very well informed about specific set of issues, and they're not on the same page. They share all the same information, they've read all the facts, and they're at opposite ends of it, and they need to come to a conclusion, if not a understanding, shared understanding, shared acceptance of where we're going to go, and they have to hash that out. I think meetings are great for vigorous debate. Now, people use meetings for a thousand other things. They use meetings to announce things, They use meetings for status calls. They use meetings for just general introductions. They use meetings for pitches. They use meetings for all these things that are really about one person delivering information to another person. I think meetings suck for that purpose, and I think we're much better off when we use anything from email to Basecamp to other ways of asynchronous communication where someone can write something up, be considered In their thought, using full sentences, forming paragraphs, comprising entire ideas, convey those in writing, and then afterwards, if we are…

AI assessment note: “I think there's a good set of tactical rules you can adopt.”

Q know, you never got on the Silicon Valley VC treadmill. And so I guess my question to you on that one is, you mentioned the commercial pressures. What do you make of the immense surge in activity we've seen over the last five years in VC fundraising, the requirement that you have to raise VC money? And how do you think about that, having had the perspective that you have?

A Well, having had the perspective I've had, which goes all the way back to the first.com boom and bust, is that I don't think there's anything novel in the past. Five years. Maybe the valuations got higher, but these pressures have been in software for a very long time, and I don't think they're, they're any more widespread. In fact, if anything, I think the opposite is true. It's never been easier to start a new software company than it is today without raising money. It's never been easier to build a nest edge working for someone else for a short period of time, making copious amounts of gold doing that, and then taking that gold and starting off on your own path. This idea that you need Venture capital. You need outside money is, is complete bunk and bust. And this goes back to, to a lot of things. As we talked about remote work, the fact that you don't have to live in Silicon Valley or New York or Seattle or any other high priced metropolitan area to collaborate, to launch something new, you can live wherever and it's going to be fine. And it also goes to the example that we've been trying to set at Basecamp is you just, you don't need a thousand people. In fact, when we started Basecamp, we were four people working part-time on this side project that was Basecamp, and it took us about a year before that side project was making enough money to pay our salaries, and it wasn't…

AI assessment note: “This idea that you need Venture capital. You need outside money is, is complete bunk”

Q I ever could have expected when I started this from my bedroom as an eighteen-year-old, but, you know, my mother's MS doesn't go away, the loneliness doesn't go away, the vulnerability doesn't go away, and I remain hungrier than ever, ending up wanting just More and more, and, and not essentially being happy with what I have. How am I seeing this wrong, and how would you think about it?

A Well, I can tell you, and, and I will guarantee you that that path will continue to bind you in unhappiness, because there is no point where you suddenly wake up once you're on that treadmill and think, oh, that was it. That extra million, or that extra ten million, or that extra billion, that's the tipping point where true bliss lies behind. No, it's not. You have to simply change your entire worldview of what is important. And thankfully, we have a treasure trove of humans who've pondered this exact question for thousands of years. And if you dive into that treasure trove of wisdom, I think it is possible to change your worldview and change your angling and your ambition to be something more than just the chase of money. And I would recommend that Starting with a 20th century author who's probably my, one of my favorite authors of all time. His name is Eric Frum. He wrote a great book called To Have or To Be that explores this exact topic of defining who you are in terms of what you have or in terms of who you are. It sounds simple as we talked about. Some of these simple things are not hard to explain, but incredibly hard to internalize and live. So Eric Frum is, is great And I recommend him these days more than, than the Stoics, even though I'm also a fan of the Stoics, and I think you can get a lot out of Stoic perspective, but also not all. You have to augment that somewh…

AI assessment note: “You have to simply change your entire worldview of what is important.”

Q to you is, you know, This is, you know, spawned a rise that no one else has, you know, a lot of people haven't seen or experienced before. A big question for me, and I think a lot of leaders would be, how do you combat the mental health, the loneliness, and the isolation, maybe, for a generation that haven't experienced it, and what would you advise in that perspective?

A It's really tough, and it's real, and the first thing you have to accept that this is real, and this is something people do struggle with. Different people struggle with it in different proportions, but you have to deal with it head-on. So the way we deal with it at Basecamp is that instead of Mixing it together with the work. We say our social connections, our human connections are really important. They need to be replenished frequently, often, and let's just do that explicitly. One example of that we just instituted recently is Fridays at 10 a.m., we have an hour of game time. It's a open video conference and call where anyone who's interested can jump on during work hours to simply hang out with their co-workers and play games. It has no work purpose. It's not like the games are about the work that we do. They're simply there for the social connection. Another example of this that we've done for many years now is something we call five by 12, where in normal times, once a month, five people plus Jason and I will get on a call again during work hours for an hour to talk about everything else except work. What's going on in our lives, what's going on in the world, all that kind of stuff, and using those opportunities to sort of top off on the social connections. We do the same thing in asynchronous form using Basecamp. We have these automatic recurring questions in Basecamp t…

AI assessment note: “So the way we deal with it at Basecamp is that instead of Mixing it together with the work.”

Q Can I ask, we mentioned delivering happiness earlier. This isn't in the schedule, but I'm just, what's, what's your core problem with Zoom? Sorry, David, I think that's really blunt.

A Well, I think we need another, perhaps, uh, 30 minutes for that, but I'll make the short spiel. I don't like people who, who lie. When, when the things came out about Zoom claiming to be end-to-end encrypted, for example, and they weren't, you just go like, why are you saying that? Why are you pretending that? All the shit that they've done that's kind of on the sly, whether it was last year when they installed this uninstallable web server, just because they wanted to save a click, right? And then Apple all of a sudden had to release this emergency fix to, to remove the huge security vulnerability that came of that. There's just so many things in what Zoom does that seems so short-sighted into sort of KPI level. I can totally imagine that there's this Zoom product meeting where they go like, they count the number of clicks it'll take for someone to join a meeting, right? And then they just, they focus myopically on getting that number from, I don't know, whatever it is, four to three. And they think like, this is what matters. This is really the most important thing we can do is to reduce the number of clicks it takes from four to three. Which rules do we have to bend? Which security things do we have to cheat to get there? And you just go like, ah, fuck, it is so unnecessary. You have great Underlying video tech. You don't need this. And I think that this is so true in so man…

AI assessment note: “I don't like people who, who lie.”

Q Can I ask a kind of personal question, but I am intrigued by it, and do say if it's too personal. How do you think about your relationship to money, given the stance that you take?

A I think I had a unique blessing growing up in a country like Denmark that has an incredibly well-functioning democratic socialist state. Where the basics of human needs and flourishment are taken care of by a democratic welfare state. And those things for me growing up lower middle class, probably working class actually, was that A, I didn't really get to think much about class until I became much older because it just wasn't something that was holding me back. I wasn't deprived of things. I got a great education through the Danish education system. I got great healthcare when I needed it without ever having to think about Oh, what does it cost? So I had that blessing of growing up in a country like that, that showed me how little money can mean. Doesn't mean it doesn't mean anything. And I have plenty of memories from us growing up where getting towards the end of the month, there was no more money. And that was that. And then you sort of just found a way to, to make do until it was the first of the month and the paycheck would come in. And yet money did not dominate my upbringing, right? So when you get that exposure to an entire society, That does not revolve around money to the extent that happens in the US. You just end up with a different perspective. So that perspective was then augmented by the reality of becoming a millionaire in my twenties and realizing that even hav…

AI assessment note: “showed me how little money can mean”

Q the autonomy. I guess my question to you is, is it difficult balancing the accountability, but also letting them know that it's okay to fail? I think a lot would suddenly feel with the accountability on their shoulders, almost this massive fear of failure and the reper Percussions. How do you think about creating that culture of it's okay to fail and try and not be scared of the accountability?

A By not being an asshole, that's a good start. By not sort of cutting people's heads off when they do make mistakes. I think you can say everything that you want. That's not how culture is created. That's not how sort of a safe working environment is created. No, those things are created through actions. What you do and what you don't do. So when you reprimand people in public or otherwise, when they make mistakes, or when you fire people after they Have a single mishap. You're creating the culture that, that is actually there. The culture that's there is not the one you write up in your damn mission statement or your memos to the company. No. Uh, people are smarter than that, and they look at actions and heavily, heavily discount your words. So we try to have good actions, and some of those actions are that, um, there is a framework for steering this. There's a clock frequency, essentially, at Basecamp. And that clock frequency runs on six-week cycles. Every six weeks, we stop for a week or two and take stock of what we've done in the past six weeks and what we're going to do next. And again, it runs in the same principle that everyone or all teams are responsible for essentially reporting what they worked on and then telling the rest of the company what they plan to work on next. And that mechanism alone requiring people to account for what they've done and what they intend to…

AI assessment note: “By not being an asshole, that's a good start.”

Q determine between the meetings to The tape versus the meetings not to. I, I must admit I,, I suffer victim to this where I take all of them because I never know which serendipitous good thing could come out of them. So I always take everything and then I spend my time zoomed out of my mind. So how do you determine it and what advice would you give me?

A Great question. I think there's a good set of tactical rules you can adopt. The first one being that what are meetings good for? In my opinion, meetings are great when you have two or three or four. That's probably the limit. If you get into five, it's already starting to be problematic. But let's just say four people who are very well informed about specific set of issues, and they're not on the same page. They share all the same information, they've read all the facts, and they're at opposite ends of it, and they need to come to a conclusion, if not a understanding, shared understanding, shared acceptance of where we're going to go, and they have to hash that out. I think meetings are great for vigorous debate. Now, people use meetings for a thousand other things. They use meetings to announce things, They use meetings for status calls. They use meetings for just general introductions. They use meetings for pitches. They use meetings for all these things that are really about one person delivering information to another person. I think meetings suck for that purpose, and I think we're much better off when we use anything from email to Basecamp to other ways of asynchronous communication where someone can write something up, be considered In their thought, using full sentences, forming paragraphs, comprising entire ideas, convey those in writing, and then afterwards, if we are…

AI assessment note: “that filter will cut off at least 80% of all the meetings”

Q before I heard you say, and it was the big challenge of parenting is not to get kids to do as you'd like, but to resist the temptation to make them. I guess, how do you balance the being much more hands-on and in the weeds than maybe a lot more executives would be with resisting the temptation to make them and the micromanagement? How do you balance the two?

A I think the easiest balance is I try to do the work myself. I mean, I'm on a team and we're all moving forward, but I have enough. Just doing my own stuff, such that I don't have to worry so much of the time telling other people what to do, because one of the big principles we have at Basecamp is this notion of managers of one, that everyone at Basecamp should strive towards being a manager of one, that they get sort of an overall pointer in which direction to go, but they got to figure out how to get there, and they shouldn't need someone to check in on them every day or every other day. If that's happening, that's either because they're a junior and they're on an on-ramp, and that on-ramp is eventually going to And they're going to graduate out of that junior status, or because something is wrong. The majority of the people who've been here at Basecamp for a very long time, my involvement in their work is profoundly optional. I try to think of my presence in the company as a bonus. The entire operation should be able to run, whether I'm here or not, and then when I am here, I'm contributing and doing my slice of the work, and I am perhaps chiming in and doing some editing on other people's work, But if we take that away, no one's blocked. No one sort of looks up and have no idea what they need to do. Everyone just continues on doing the work. So that sort of comes back to a w…

AI assessment note: “I think the easiest balance is I try to do the work myself.”

Q I ever could have expected when I started this from my bedroom as an eighteen-year-old, but, you know, my mother's MS doesn't go away, the loneliness doesn't go away, the vulnerability doesn't go away, and I remain hungrier than ever, ending up wanting just More and more, and, and not essentially being happy with what I have. How am I seeing this wrong, and how would you think about it?

A Well, I can tell you, and, and I will guarantee you that that path will continue to bind you in unhappiness, because there is no point where you suddenly wake up once you're on that treadmill and think, oh, that was it. That extra million, or that extra ten million, or that extra billion, that's the tipping point where true bliss lies behind. No, it's not. You have to simply change your entire worldview of what is important. And thankfully, we have a treasure trove of humans who've pondered this exact question for thousands of years. And if you dive into that treasure trove of wisdom, I think it is possible to change your worldview and change your angling and your ambition to be something more than just the chase of money. And I would recommend that Starting with a 20th century author who's probably my, one of my favorite authors of all time. His name is Eric Frum. He wrote a great book called To Have or To Be that explores this exact topic of defining who you are in terms of what you have or in terms of who you are. It sounds simple as we talked about. Some of these simple things are not hard to explain, but incredibly hard to internalize and live. So Eric Frum is, is great And I recommend him these days more than, than the Stoics, even though I'm also a fan of the Stoics, and I think you can get a lot out of Stoic perspective, but also not all. You have to augment that somewh…

AI assessment note: “You have to simply change your entire worldview of what is important.”

Q I ask, is it wrong to have legacy as one of the reasons? And what I mean by that is, like, I've always said I want to be 70 with grandchildren and have them running around me in an armchair and say, hey, our family is part of building something special with this, in terms of what I've built. Is it wrong to have, like, legacy as a core driver?

A I don't know if it's wrong, but I, I don't know if it's the thing that should be at the top of the list. And the number of seventy-year-old miserable fucks who don't have their grandchildren running around them, but have them alienated and estranged because they were always chasing more, and they never had enough, and they end up being these stereotypical misers who focused on that legend, right? Like, it's a stereotype for a reason. The number of seventy-year-olds who end up on the other side Um, sitting in their rocking chair, looking back on a life well spent. You know what? Money is probably not the top thing on their list. In fact, it is assuredly not that. Uh, Howard had a longitudinal study called the, I think it was called the Human Happiness Project, uh, that looked on upon Harvard graduates for a hundred years or something like that. The question they were trying to, to answer was like, what makes for, for good living? Like, what makes people happy? Do you know what? Money wasn't even on the list. Right? And again, maybe there's some privilege here. This is studying Harvard students, so they weren't probably in need of the basic necessities, but at the end, what was the conclusion? It was human connections. That was it. The people who had the greatest, strongest, most loving human connections were the happiest people, and those were the ones with the least regret. And…

AI assessment note: “I don't know if it's wrong, but I, I don't know if it's”

Q What would you most like to change about the world of tech and startups, David?

A The narrative around money and the importance of big, the importance of, of the unicorn chase , I think that is probably one of the most damaging strains of mimetic viruses floating around. If we could liberate more entrepreneurs and founders to think less about what the excess is going to be and what the ultimate size is going to be and more about just like, hey, am I working at a place I want to work with people I want to work with working on something that's good? In, in sort of a more basic sense than changing the world, I think far too many tech entrepreneurs are obsessed with disruption. You know what? A little less disruption and a little more fixing.

AI assessment note: “The narrative around money and the importance of big”

Q bland and You know, boring mission that is applicable to every single company, and really everyone would just want anyway. And you've said before, when it comes to mission statement, if you're not constraining the world, what are you trying to do? And so I guess, how do you think about that principle setting, and what makes the best in your mind, and what separates the good and the great?

A Yeah, man, this is just a topic that continuously riles me up. Before we hit record, we were talking briefly about Zoom, and I just Fell over this yesterday, and I think the Zoom mission statement is deliver happiness or some bland shit like that, and you're like, this is exactly what I'm talking about. Any organization that has as their mission statement to deliver happiness, unless that is, I don't know, fucking clowns at kids' birthday parties, it's just vapid, right? Like, there's nothing there. There's no content. The mission statement, if it is to have any effect At all is a way of weighing trade-offs between two things that you want both, and then deciding which of the two you want more. If it's not providing that function, if it's not putting a hand on the scale in those weighings, it's useless. And who is going to deliver, what, sadness? Is any organization going to be, we're here because we're trying to deliver sadness. If there's no opposition to your term, it's useless. So we don't even try. Hmm. I think we have some general principles we've written up in our handbook, but I can't even remember them off the top of my head, and, and the ones that are there will be extractions, where we look back upon the actual actions that we took, and we try to provide a narrative around that. We don't try to invent sort of some fantasy about, like, what kind of company we are, wan…

AI assessment note: “is a way of weighing trade-offs between two things that you want both”

Q before I heard you say, and it was the big challenge of parenting is not to get kids to do as you'd like, but to resist the temptation to make them. I guess, how do you balance the being much more hands-on and in the weeds than maybe a lot more executives would be with resisting the temptation to make them and the micromanagement? How do you balance the two?

A I think the easiest balance is I try to do the work myself. I mean, I'm on a team and we're all moving forward, but I have enough. Just doing my own stuff, such that I don't have to worry so much of the time telling other people what to do, because one of the big principles we have at Basecamp is this notion of managers of one, that everyone at Basecamp should strive towards being a manager of one, that they get sort of an overall pointer in which direction to go, but they got to figure out how to get there, and they shouldn't need someone to check in on them every day or every other day. If that's happening, that's either because they're a junior and they're on an on-ramp, and that on-ramp is eventually going to And they're going to graduate out of that junior status, or because something is wrong. The majority of the people who've been here at Basecamp for a very long time, my involvement in their work is profoundly optional. I try to think of my presence in the company as a bonus. The entire operation should be able to run, whether I'm here or not, and then when I am here, I'm contributing and doing my slice of the work, and I am perhaps chiming in and doing some editing on other people's work, But if we take that away, no one's blocked. No one sort of looks up and have no idea what they need to do. Everyone just continues on doing the work. So that sort of comes back to a w…

AI assessment note: “I think the easiest balance is I try to do the work myself.”

Q the autonomy. I guess my question to you is, is it difficult balancing the accountability, but also letting them know that it's okay to fail? I think a lot would suddenly feel with the accountability on their shoulders, almost this massive fear of failure and the reper Percussions. How do you think about creating that culture of it's okay to fail and try and not be scared of the accountability?

A By not being an asshole, that's a good start. By not sort of cutting people's heads off when they do make mistakes. I think you can say everything that you want. That's not how culture is created. That's not how sort of a safe working environment is created. No, those things are created through actions. What you do and what you don't do. So when you reprimand people in public or otherwise, when they make mistakes, or when you fire people after they Have a single mishap. You're creating the culture that, that is actually there. The culture that's there is not the one you write up in your damn mission statement or your memos to the company. No. Uh, people are smarter than that, and they look at actions and heavily, heavily discount your words. So we try to have good actions, and some of those actions are that, um, there is a framework for steering this. There's a clock frequency, essentially, at Basecamp. And that clock frequency runs on six-week cycles. Every six weeks, we stop for a week or two and take stock of what we've done in the past six weeks and what we're going to do next. And again, it runs in the same principle that everyone or all teams are responsible for essentially reporting what they worked on and then telling the rest of the company what they plan to work on next. And that mechanism alone requiring people to account for what they've done and what they intend to…

AI assessment note: “By not sort of cutting people's heads off when they do make mistakes.”

Q Can I ask a kind of personal question, but I am intrigued by it, and do say if it's too personal. How do you think about your relationship to money, given the stance that you take?

A I think I had a unique blessing growing up in a country like Denmark that has an incredibly well-functioning democratic socialist state. Where the basics of human needs and flourishment are taken care of by a democratic welfare state. And those things for me growing up lower middle class, probably working class actually, was that A, I didn't really get to think much about class until I became much older because it just wasn't something that was holding me back. I wasn't deprived of things. I got a great education through the Danish education system. I got great healthcare when I needed it without ever having to think about Oh, what does it cost? So I had that blessing of growing up in a country like that, that showed me how little money can mean. Doesn't mean it doesn't mean anything. And I have plenty of memories from us growing up where getting towards the end of the month, there was no more money. And that was that. And then you sort of just found a way to, to make do until it was the first of the month and the paycheck would come in. And yet money did not dominate my upbringing, right? So when you get that exposure to an entire society, That does not revolve around money to the extent that happens in the US. You just end up with a different perspective. So that perspective was then augmented by the reality of becoming a millionaire in my twenties and realizing that even hav…

AI assessment note: “I had that blessing of growing up in a country like that, that showed me how little money can mean.”

Q know, for the impact that you have as a company, the team is still remarkably small. And you've said before, the complexity curve is not linear when adding new people. Can I ask, what did you mean by this? I was listening when I was on my run, as I said. What did you mean by this? And how do you think about necessary versus luxury additions to the team?

A Well, first in terms of the complexity, it's, I forget, what is it, Conway's Law or something about the number of connections between people or is an exponential function? Maybe I'm getting this wrong. But just the difference between an organization of five people and an organization of 10 people or one between 10 and 20, it's not twice as hard. It's far more than twice as hard, and the amount of coordination overhead that it requires when you double your headcount is, again, not double. It is far more than that. So for a very long time, since inception, we've tried to keep Basecamp as absolutely as small as possible, because one of the things that both Jason and I enjoy working at Basecamp is doing the work ourselves. So we're the two executives at the company, and perhaps most other companies at the size of 56, the executives Aren't as hands into the work as we like to be. I love programming. I try to make as much as my week about programming, which means that I have to make room of my, on my plate for, for that, right? I, we work 40 hour weeks, eight hours, five days a week, right? So there isn't just this time where I can smash in programming on top of a full 40 hour work week doing executive functions. So I have to fit it in on that plate. And One key way we do that is to keep the organizational complexity low, uh, less coordination that requires sort of syncing up of a bu…

AI assessment note: “the amount of coordination overhead that it requires when you double your headcount is, again, not double”

Q know, for the impact that you have as a company, the team is still remarkably small. And you've said before, the complexity curve is not linear when adding new people. Can I ask, what did you mean by this? I was listening when I was on my run, as I said. What did you mean by this? And how do you think about necessary versus luxury additions to the team?

A Well, first in terms of the complexity, it's, I forget, what is it, Conway's Law or something about the number of connections between people or is an exponential function? Maybe I'm getting this wrong. But just the difference between an organization of five people and an organization of 10 people or one between 10 and 20, it's not twice as hard. It's far more than twice as hard, and the amount of coordination overhead that it requires when you double your headcount is, again, not double. It is far more than that. So for a very long time, since inception, we've tried to keep Basecamp as absolutely as small as possible, because one of the things that both Jason and I enjoy working at Basecamp is doing the work ourselves. So we're the two executives at the company, and perhaps most other companies at the size of 56, the executives Aren't as hands into the work as we like to be. I love programming. I try to make as much as my week about programming, which means that I have to make room of my, on my plate for, for that, right? I, we work 40 hour weeks, eight hours, five days a week, right? So there isn't just this time where I can smash in programming on top of a full 40 hour work week doing executive functions. So I have to fit it in on that plate. And One key way we do that is to keep the organizational complexity low, uh, less coordination that requires sort of syncing up of a bu…

AI assessment note: “the amount of coordination overhead that it requires when you double your headcount is, again, not double.”

Q Did you have a snap moment or was it a realization over several years?

A Well, I think first I had a good foundation again coming from a society like Denmark that kind of put a bunch of lessons into my brain that perhaps I didn't appreciate when I was 22, but they were there. And as I started unearthing more of sort of the long-running human wisdom that is available to anyone who cares to read, those lessons were dug up, and they were made accessible, and they were kind of being pieced together until I had more of the pieces of the puzzle. I'm not Sort of claiming I have any final solution here. In fact, I'm just pointing to other people who helped me on a direction of coming to these realizations as I've come to them. So no, I don't think there was necessarily just like that one snap tipping point, but it was a slow boiling until to the point where you can recognize it over time. I look back of 20 years earlier, and I look back at my Copenhagen Business School critiques of Danish social democratic society, and I just shake my head in disbelief of how naive and, well, frankly, stupid They were. So I can see it over a long period of time. I can't pinpoint like, oh, it was on that day, everything changed. And I think that's also just unrealistic, and it's not even helpful to think it's just a switch you have to flip. That's not what it is. This is a spectrum. This is a marathon of insight.

AI assessment note: “no, I don't think there was necessarily just like that one snap tipping point”

Q I want to finish, though, on the next five years for you and for Basecamp. What does that look like in your mind?

A It's one of those questions I hate, and I don't mean that personally. I mean that in the sense of not living in the moment Not living in the moment, not living and dealing with the problems you have right now, and constantly living in tomorrow land. I try not to do that. So my best extrapolation of what is going on in five years is just to say, I hope more of the same. I'm a quite content person, even though it may not appear so on Twitter, because Twitter is sort of my spleen, my outlet for sort of all the gall that otherwise would build up in the system. But in terms of a life-work balance, things are good. That's why I've been working on the same shit for 15 years, right? Things are good. I enjoy what I do. I enjoy writing Ruby code, and making Rails, and making Basecamp, and now we're making this new hey.com email service, and I'm excited about that, and I hope I still get to do that in five years. I hope I still get to do that in 10 years. I hope I still get to do that in 15 years. Do you know what's not at the top of my list of what to do? Is to have more money. So one of the things I'm really happy to have arrived at is the sense that, like, you know what, I have enough. I don't need more in that sense. I need to be.

AI assessment note: “my best extrapolation of what is going on in five years is... more of the same”

Q Did you have a snap moment or was it a realization over several years?

A Well, I think first I had a good foundation again coming from a society like Denmark that kind of put a bunch of lessons into my brain that perhaps I didn't appreciate when I was 22, but they were there. And as I started unearthing more of sort of the long-running human wisdom that is available to anyone who cares to read, those lessons were dug up, and they were made accessible, and they were kind of being pieced together until I had more of the pieces of the puzzle. I'm not Sort of claiming I have any final solution here. In fact, I'm just pointing to other people who helped me on a direction of coming to these realizations as I've come to them. So no, I don't think there was necessarily just like that one snap tipping point, but it was a slow boiling until to the point where you can recognize it over time. I look back of 20 years earlier, and I look back at my Copenhagen Business School critiques of Danish social democratic society, and I just shake my head in disbelief of how naive and, well, frankly, stupid They were. So I can see it over a long period of time. I can't pinpoint like, oh, it was on that day, everything changed. And I think that's also just unrealistic, and it's not even helpful to think it's just a switch you have to flip. That's not what it is. This is a spectrum. This is a marathon of insight.

AI assessment note: “no, I don't think there was necessarily just like that one snap tipping point”

Q weeks with COVID and we've seen the world and the world's largest company shift to work from home overnight. Can I ask, given your kind of insight into it for so many years, kind of being ahead of the curve, is it what you expected it to be in terms of the world shifting to it? And what have been some of your core observations as people move to remote?

A Sure. So we wrote a book, Jason and I called Remote Office Not Required back in And when we wrote that book, I thought I was already stating the obvious. Jason and I had been working together at that point for a good 12, 13 years remotely together, and had just taken it for granted that all companies would have gotten the obvious advantages of having a remote workforce, allowing people to work from home or wherever they were most productive, but in a series of conversations in sort of around 2010, 1112, I kept just having the same conversation over and over again with other entrepreneurs. And the conversation would go something like, oh, you guys are working remotely. Oh, well, that's interesting. That would never work for us. Because, hey, how would you replicate the magic around the whiteboard? How would you know whether people are working? All these sort of trite excuses for why remote wasn't going to work for them. I could just keep hearing the same one over and over again. And they were always shallow. They weren't very well thought out. And I thought, do you know what? Rather than having the same conversation a billion times repeated, let's just write it down. Let's write down the arguments for why remote work is actually a great idea. And then once we've made the argument for why your company should allow remote work, then let's teach you how to do it. Because even thoug…

AI assessment note: “seems like an historic inevitability that remote work is going to take off”

Q weeks with COVID and we've seen the world and the world's largest company shift to work from home overnight. Can I ask, given your kind of insight into it for so many years, kind of being ahead of the curve, is it what you expected it to be in terms of the world shifting to it? And what have been some of your core observations as people move to remote?

A Sure. So we wrote a book, Jason and I called Remote Office Not Required back in And when we wrote that book, I thought I was already stating the obvious. Jason and I had been working together at that point for a good 12, 13 years remotely together, and had just taken it for granted that all companies would have gotten the obvious advantages of having a remote workforce, allowing people to work from home or wherever they were most productive, but in a series of conversations in sort of around 2010, 1112, I kept just having the same conversation over and over again with other entrepreneurs. And the conversation would go something like, oh, you guys are working remotely. Oh, well, that's interesting. That would never work for us. Because, hey, how would you replicate the magic around the whiteboard? How would you know whether people are working? All these sort of trite excuses for why remote wasn't going to work for them. I could just keep hearing the same one over and over again. And they were always shallow. They weren't very well thought out. And I thought, do you know what? Rather than having the same conversation a billion times repeated, let's just write it down. Let's write down the arguments for why remote work is actually a great idea. And then once we've made the argument for why your company should allow remote work, then let's teach you how to do it. Because even thoug…

AI assessment note: “seems like an historic inevitability that remote work is going to take off”

Q Okay, so what book, you mentioned some amazing books, what book would you most recommend to the audience?

A Oh man, so hard. To Have a To Be would probably be one of my favorites for this particular audience, because it tackles head-on so many of the questions we talked about the chase. I was otherwise going to say another book of Eric Frum, actually, called Escape From Freedom, which explains a lot of what's going on with the political situation, both in the U.S. and much of the Western world right now. So perhaps if I tweak the question and say which author Would you recommend? I would recommend Eric Frum. I would start with To Have It To Be, and then I would work my way, as I have actually, through his very long history of books. I would take Escape From Freedom as number two, and then I would just keep on going. I don't think I have a superpower. I don't think there's anything supernatural about how we operate Basecamp or how I go to work. In fact, I think it's a misnomer when people think about it in that sense, because then it puts them off as something that they could learn. I picked up a bunch of skills and habits of how to run a company, but perhaps more than a specific habit or skill, it's a centering of my worldview. I think of myself as working for someone else. Whatever decision that I make or help influence at Basecamp at the executive level, I always try to think of myself on the other side, because I was on the other side. I've worked for plenty of terrible bosses, an…

AI assessment note: “To Have a To Be would probably be one of my favorites”

Q Okay, so what book, you mentioned some amazing books, what book would you most recommend to the audience?

A Oh man, so hard. To Have a To Be would probably be one of my favorites for this particular audience, because it tackles head-on so many of the questions we talked about the chase. I was otherwise going to say another book of Eric Frum, actually, called Escape From Freedom, which explains a lot of what's going on with the political situation, both in the U.S. and much of the Western world right now. So perhaps if I tweak the question and say which author Would you recommend? I would recommend Eric Frum. I would start with To Have It To Be, and then I would work my way, as I have actually, through his very long history of books. I would take Escape From Freedom as number two, and then I would just keep on going. I don't think I have a superpower. I don't think there's anything supernatural about how we operate Basecamp or how I go to work. In fact, I think it's a misnomer when people think about it in that sense, because then it puts them off as something that they could learn. I picked up a bunch of skills and habits of how to run a company, but perhaps more than a specific habit or skill, it's a centering of my worldview. I think of myself as working for someone else. Whatever decision that I make or help influence at Basecamp at the executive level, I always try to think of myself on the other side, because I was on the other side. I've worked for plenty of terrible bosses, an…

AI assessment note: “To Have a To Be would probably be one of my favorites for this particular audience”