The Exchanges

Q Now, for people that missed the first show, quick intro, one to two minutes. How did you come to found Basecamp now, 23 years ago?

A 23 years ago. So, uh, I was working on my own freelancing, doing website design, and, um, I'd been doing that for a few years and got bored working on my own, frankly. I mean, I, I was just in my apartment, you know, got out of bed, rolled to my desk, did work, rolled back to bed, not really what I wanted to do long-term. So I hooked up with a couple of friends who were also looking to start a business, website design business, and that's where we started the business together. Um, and then a few years later, we started making Basecamp, the, the software that we're known for today, primarily. Um, because we needed it for our own business. We were doing a lot of website design projects. So I had a lot of clients and we couldn't really keep things in order. We were dropping the ball, you know, missing deadlines. Clients didn't know what we were doing. We didn't know what we were doing. And so we built this thing, which eventually became base camp to manage that, those projects and that work. And we started using it with our clients and they said, well, what is this thing? Like, we need this for our own business. And we said, ah, okay. So we turned it into a product. Put some prices on it, put it out in the market in February of 2004. And about a year later or so, it was doing more, generating more revenue for us than our website design business. So we stopped doing website design…

AI assessment note: “we built this thing, which eventually became base camp to manage that, those projects”

Q What's the biggest disagreement you and David have had around a core decision? Um, and how did it get resolved?

A Yeah. One of the biggest recent ones was, um, when we launched Hey, David was really adamant about launching the business version first, which is what was called Hey for domains. And I was pretty set on launching the personal version first, which is just at Hey.com. And we battled over this for, I don't know, a month, you know, not like every day, but like it was up in the air for a month. And, you know, strong, strong calls either way and whatnot. And in the end we decided to do, to do the personal version first, which I think was ultimately the right call. Um, but that was a, that was a pretty big, big one. And David's point was that like launching a personal email service that people pay a hundred bucks a year for is a massive like risk because like people don't pay for email. Email's free, right? Businesses pay for email. Businesses are already used to paying for email. So why don't we make something that they're already used to paying for? And my angle was, I think we can make something good enough, great enough, whatever, whatever you want to call it, that people are willing to pay for. Um, and so that was the battle. How do we resolve it? In the end, you make arguments and then a decision is made one way or the other. And a lot of it has to do with who, who's, who believes in it more essentially, like who really wants this more. Um, and then we, we do what we call trade.…

AI assessment note: “David was really adamant about launching the business version first”

Q Um, what is the secret to a successful business partnership in the way that you have when you think about your relationship with David? So few partners are together as long as you are.

A Yeah, I think it's a couple things. Um, one, we do different things. So David's an engineer. He's more on the technical side. I'm on the design side. So we're not battling over how to do the same thing. So I think that's important, first of all. But we, we see business about the same way. I'd say we have like an 85 to 90% overlap on like our business point of view. So you need to have something core that's shared and in common. And I think the actual work itself, you need to have separate skills on. I think that's very important. Second, I think we're able to just, I think we have strong enough senses of ourselves that we're able to battle hard and not take it personally. Um, that's something I think that's important. Um, I think also just fundamentally seeing, you know, again, like business fundamentals in the same way, uh, is very important. Also the fact that we don't see each other very often is very important. Um, David lives in Denmark.

AI assessment note: “one, we do different things. So David's an engineer. He's more on the technical side.”

Q What's the biggest disagreement you and David have had around a core decision? Um, and how did it get resolved?

A Yeah. One of the biggest recent ones was, um, when we launched Hey, David was really adamant about launching the business version first, which is what was called Hey for domains. And I was pretty set on launching the personal version first, which is just at Hey.com. And we battled over this for, I don't know, a month, you know, not like every day, but like it was up in the air for a month. And, you know, strong, strong calls either way and whatnot. And in the end we decided to do, to do the personal version first, which I think was ultimately the right call. Um, but that was a, that was a pretty big, big one. And David's point was that like launching a personal email service that people pay a hundred bucks a year for is a massive like risk because like people don't pay for email. Email's free, right? Businesses pay for email. Businesses are already used to paying for email. So why don't we make something that they're already used to paying for? And my angle was, I think we can make something good enough, great enough, whatever, whatever you want to call it, that people are willing to pay for. Um, and so that was the battle. How do we resolve it? In the end, you make arguments and then a decision is made one way or the other. And a lot of it has to do with who, who's, who believes in it more essentially, like who really wants this more. Um, and then we, we do what we call trade.…

AI assessment note: “One of the biggest recent ones was, um, when we launched Hey”

Q Um, what is the secret to a successful business partnership in the way that you have when you think about your relationship with David? So few partners are together as long as you are.

A Yeah, I think it's a couple things. Um, one, we do different things. So David's an engineer. He's more on the technical side. I'm on the design side. So we're not battling over how to do the same thing. So I think that's important, first of all. But we, we see business about the same way. I'd say we have like an 85 to 90% overlap on like our business point of view. So you need to have something core that's shared and in common. And I think the actual work itself, you need to have separate skills on. I think that's very important. Second, I think we're able to just, I think we have strong enough senses of ourselves that we're able to battle hard and not take it personally. Um, that's something I think that's important. Um, I think also just fundamentally seeing, you know, again, like business fundamentals in the same way, uh, is very important. Also the fact that we don't see each other very often is very important. Um, David lives in Denmark.

AI assessment note: “one, we do different things. So David's an engineer. He's more on the technical side.”

Q It really is, but I do want to start saying, you know, it's been 21 years since you co-founded Basecamp. Incredible journey, but take me back to the founding moment for you, and how did it come to be?

A Well, let's see. So originally we were at 37 Signals. That was the name of the business. We were originally a web design firm, and I had been freelancing as a web designer by myself in my one-bedroom apartment for a handful of years, and I just got tired of working by myself. I liked working for myself, but I was tired of working only with myself. So I said, maybe I should just get a job somewhere. I don't know. So I went to interview at some places, and during that process, I met a fellow named Ernest Kim, who is currently the creative director at a big web design shop in Chicago called Organic Online. They were opening their Chicago office, They had a big San Francisco office and we hit it off. I didn't want to work there ultimately, but we hit it off. So we stayed in touch. And then we had a mutual friend, a guy named Carlos Segura, who's a graphic designer, traditional graphic designer, print work. And about a year after I'd interviewed with Ernest, Ernest wanted to leave organic. I was still trying to figure out what to do. I was bored working on my own. Carlos wanted to get into the web. So we all just had like, why don't we just do something together? I don't know. Let's just do something together. Ernest is going to quit. Carlos wanted to do something. I want to do something with some other people. So let's do it. So we each put 10,000 bucks in. So we had something to g…

AI assessment note: “we all just had like, why don't we just do something together?”

Q It really is, but I do want to start saying, you know, it's been 21 years since you co-founded Basecamp. Incredible journey, but take me back to the founding moment for you, and how did it come to be?

A Well, let's see. So originally we were at 37 Signals. That was the name of the business. We were originally a web design firm, and I had been freelancing as a web designer by myself in my one-bedroom apartment for a handful of years, and I just got tired of working by myself. I liked working for myself, but I was tired of working only with myself. So I said, maybe I should just get a job somewhere. I don't know. So I went to interview at some places, and during that process, I met a fellow named Ernest Kim, who is currently the creative director at a big web design shop in Chicago called Organic Online. They were opening their Chicago office, They had a big San Francisco office and we hit it off. I didn't want to work there ultimately, but we hit it off. So we stayed in touch. And then we had a mutual friend, a guy named Carlos Segura, who's a graphic designer, traditional graphic designer, print work. And about a year after I'd interviewed with Ernest, Ernest wanted to leave organic. I was still trying to figure out what to do. I was bored working on my own. Carlos wanted to get into the web. So we all just had like, why don't we just do something together? I don't know. Let's just do something together. Ernest is going to quit. Carlos wanted to do something. I want to do something with some other people. So let's do it. So we each put 10,000 bucks in. So we had something to g…

AI assessment note: “So we each put 10,000 bucks in. So we had something to go.”

Q Pretty much exactly the same family story. Yeah, exactly. Um, listen, the child psychologist within me, clearly I have too much free time, but tells me that, you know, we're all a function of our histories. Okay. And so that means we're all running from something. And we're all running towards something. When you think about first what you're running from, what are you running from, Jason?

A What am I running from? Um, I would say I'm, if I had to pick something without really thinking about it, is, um, I don't like structure. I don't like, um, requirements. I don't like, um, waking up and working for other people and doing what other people tell me to do or what I'm supposed to do. So I think my sort of entrepreneurial independence streak is a, is an example of, of me sort of going in the opposite direction of that. Um, running my own show, um, not really, you know, not taking money, so I'm not beholden to anybody. We don't have a board of directors. All the things we do as a business are very much centered in independence and being able to do what we want to do our own way. I'm guessing that is tied somehow, somewhere to my past where I felt sort of maybe tied down or, um, limited. And so this is sort of my way to be unlimited, perhaps.

AI assessment note: “I don't like structure. I don't like, um, requirements.”

Q that kind of detachment from the business. I don't like going on holidays now, Jason, because I've done mine for eight years. I don't know who I am when I'm on holiday, when I don't have my business. It's such a part of me. Do you not worry that actually when it comes to your attachment to your company, you have an inability now to detach yourself from your company?

A Um, I don't know. So I'm taking my first sabbatical, um, in January, January and February, about six weeks, um, which isn't that much of a sabbatical according to some sabbaticals. But for me, it's, it's the first time I've been away. I'll have been away from the business for that long. I'm looking forward to that because I think it's going to be quite clarifying for me. You know, what is it like not to do this? Um, Can I not wait to get back? Do I like the distance? I don't know. Um, but I feel like I need to know. I should know. And this is the first step towards that. Personally, even though I've been doing this for a long time, I have this fantasy of basically, uh, also not doing this, closing my laptop and not opening a computer again. I don't like looking at computers all day. Um, I like making things, which is what I get to do at work, but I don't like the Mechanics of sitting in front of a computer and looking at it all day. So I would love, whenever I am done with this, I'd like to close my laptop for at least a year. I'll have my phone. I can connect with people if I need to, but I don't want to be looking at a keyboard and looking into a screen for a while.

AI assessment note: “I don't know. So I'm taking my first sabbatical, um, in January”

Q Actually, every VC has a boss. It's our LPs. Every founder has a boss. It's pure, uh, investors. If you're a venture backed company, um, you don't have a boss. And so this set of questions I'm really intrigued for. We've seen a generation of SaaS companies now That are unprofitable, and heavily venture funded, and now we have a macro turning. What happens to them? Heavily unprofitable, heavily funded.

A It's going to be hard. I think there's a lot of risk baked into this that people haven't thought about. They assume that companies will be around forever. Big companies will be around forever. Um, you know, they see brand advertising all over. It makes people think there's stability there, but, but there just simply isn't. If a company can't make its own money, they require outside money. Outside money dries up. Things have to change. I mean, there's gonna have to be late. There already is. It's not like this is news, but layoffs, deep cuts, some austerity measures. Um, you know, these companies are gonna realize they probably have too many people, um, and they've been spending wildly on things that don't work. Um, they've been just in a, in a market share grab. So they're, they're, they're, they're, they're losing money on every customer, but they need to grab them because otherwise someone else will grab them. There's this whole mentality out there that I think is gonna shift. It has to shift. It's not even that I think it will. It has to. There's basic, it's basic physics at some point. It's basic economics. If you don't make more than you spend, and you don't have a lot of cash sitting around, and you burn through it, you've got to cut costs, uh, and you've got to be a different business. And I think that's creeping up on a lot of companies right now. Uh, and, and the probl…

AI assessment note: “layoffs, deep cuts, some austerity measures”

Q How do you measure success? Is it pure profitability? Is it innovation? Is it team morale? What's your metric for, are we doing a good fucking job?

A Well, profitability is important to us fundamentally, right? Um, but the other part of it is simply, would I want to do this again? Like, is, is what we're doing on a daily, weekly, monthly basis? Like, are we enjoying doing that? And would I want to do that again? If I could choose, would I want to live that month over again? Would I want to live that work month over again? That's kind of what it comes down to. Cause if we're making a pile of money and we hate each other, Not interested in that. If we're wildly profitable and every project sucks and, and people don't want to be here and I don't want to be here, that's not worth it. So it ultimately has to be about, do you want to keep doing this? Is this a place you want to spend your, your creative time and your, and your, you know, your, your craft? Is this a place you want to hone that and enjoy that and work with great people that you like and all those things like that has to be number one. Um, but profitability has to be like one a, because if you can't, if you don't maintain profitability, You have to rely on outside sources of money, and then you're beholden to all sorts of realities that you don't control. Not that you really control any of these things, but it just becomes a lot harder. And I don't want to, um, I don't want to spend my days worrying about, um, how I can make some fund a lot more money. Like, I just g…

AI assessment note: “I don't, we don't have financial targets. We don't have financial goals besides being profitable.”

Q No, I get you totally. And I like that kind of respectfully laissez-faire attitude. You could almost be a European. Um, but my, my question would be like with goals, if you don't kind of Not agree, but if you don't love executing in that fashion, how do you think about performance management, performance reviews, and ensuring getting the best out of people and measuring them against something?

A Yeah. Yeah, I think, um, first of all, management is really sort of the art of the individual. Um, so I think that you, when you evaluate people, we do performance reviews like, like every company does, but we don't have metrics that we match people up against. Um, because I don't think a lot of people actually have the power to change a lot of these things, and nor do I, nor is that the point. So we know if someone's doing good work, their team knows that they're doing good work, their team knows where they're deficient. They should know where they're deficient. We should know where they're deficient. And we talk and, and, and discuss and encourage people to improve in this area or, or, or reward them, not financially, but like praise them or, or support them if they're doing well in this area. There's a lot of recognition that happens in the company. So I think it's, it's about knowing the people you work with. And part of this is that when you have a relatively smaller company, we have about 80 people, you, you can pay pretty close attention to the work people, individuals are doing, and, and, and you have a pretty good sense of how they're doing. And there is a relative nature to it because there's other people at the company who do similar jobs. So there's some contrast there, but it's, you know, you look at the work, you look at the work and you don't look at the, at the,…

AI assessment note: “we do performance reviews like, like every company does, but we don't have metrics”

Q Holland at F.A.S.T. just after F.A.S.T. One Click Checkout's company went bust, and I, I got many death threats, um, it was horrible, um, and it really, really hurt me. Did it hurt you, and how did you actually get through that? I, I get still a lot of hate. Advise me, you're the wise elder, Jason. How do you get through The hate that you and I will get.

A Well, um, it, it did hurt. Um, and it's still from time to time hurts. Um, when people say things about you that, you know, you just are so extreme and so, you know, just completely unnecessary at the extremities. But one of the things I've just learned simply is that, you know, and this took a while, you know, I, I built up some thick skin prior to this, this sort of eroded some of it, and then you build it up again, is you just, you cannot let other people, uh, tell you how to feel. Um, and, and this is just a, you know, lifelong practice to figure out how to go. Yeah. Okay. No, that's, that's a pretty strong opinion. I know me. I know who I am. I know what I believe. Um, I know why I made these decisions and they weren't for those reasons. And you just have to go, okay. I mean, part of this too, is, is not paying attention, frankly. Like after this whole thing went down, I didn't look at Twitter for four or five months. Um, because Twitter is just really where all the like vitriol and hate hatred, deep hatred was, was happening. I got tons and tons of emails from people who are supportive, but people didn't want to say anything on Twitter because you know how it goes. Not many people are going to stand up to your defense when, when, when people are attacking. And so, but I also, I understand the, the, the, the passionate, uh, uh, sort of, I don't understand the hatred, but I…

AI assessment note: “Well, um, it, it did hurt. Um, and it's still from time to time hurts.”

Q I'd love to, Bastardize, you know, a lot of your hard work, and ask, if you were to summarize your, like, decision-making processes and frameworks today, how would you describe them?

A When I make a decision, I typically Don't make it for now. I think about what will that probably feel like in a year. This is sort of one way I do this, which is looking back on this decision. What I try to project and imagine what it will feel like. There's a lot of decisions that you make to make sort of short term pain go away or to make conflict go away or to make some disagreements go away. Um, and in the moment it feels good to get that out of the way, but then what are you stuck with? What do you have to live with after that? So I tend to think about what are you, what are we going to live with on this decision? So this comes down to even like complexity in software. Like we could cut some corners right now and shortcut this just to get this thing done. But now we've got this shitty code in the code base. We've got this, this thing we're going to have to live with. We're not going to want to go back in that area and mess with it. Cause it's, it's all messed up. And it in the end was not worth it, even though in the moment it felt like it was. So I, I tend to think a lot about that. Um, I also think like, why are we even making this decision at all? That you can find yourself making a lot of decisions that don't need to be made. Um, that's something I'm always wondering about. Like, why are we even deciding on this? Or like, what if no one decides what will happen? Like, …

AI assessment note: “When I make a decision, I typically Don't make it for now.”

Q Like, how often do you do them? How does it make you feel?

A Not very often. I've only really done them. I've done them, um, Twice. Uh, I, I've done a high dose twice and then a low dose twice. Basically high dose, meaning like five grams, like you have a blindfold on and it's completely inner experience for about six hours. It's a complete journey trip thing, um, which was absolutely profound. And, um, I came away from those experiences a different person. Um, and also, uh, um, a, uh, um, I, I, I feel like everybody should do this once in their life is kind of how I felt after I came away from those experiences. We can go into more detail on that separately if you want, but, um, I've done some low doses and just listen to music, like real low doses, just listen to music and just kind of relax. And what's really interesting is that you just, you, you, you recognize that, um, um, again, there, there, there's a lot more nuance to things than you typically would, would imagine. And that our brain, our waking brain right now, if we're, you know, both not on anything, Is really a filter. You're filtering the world into a way that you can perceive it on a day-to-day basis and live normally. But this is not necessarily the way things actually are. Um, there's, there's more to these things, but we kind of down sample everything so we can manage. Um, and so it's kind of interesting when you take mushrooms, it kind of upsamples in a sense. It, it …

AI assessment note: “Not very often. I've only really done them. I've done them, um, Twice.”

Q that kind of detachment from the business. I don't like going on holidays now, Jason, because I've done mine for eight years. I don't know who I am when I'm on holiday, when I don't have my business. It's such a part of me. Do you not worry that actually when it comes to your attachment to your company, you have an inability now to detach yourself from your company?

A Um, I don't know. So I'm taking my first sabbatical, um, in January, January and February, about six weeks, um, which isn't that much of a sabbatical according to some sabbaticals. But for me, it's, it's the first time I've been away. I'll have been away from the business for that long. I'm looking forward to that because I think it's going to be quite clarifying for me. You know, what is it like not to do this? Um, Can I not wait to get back? Do I like the distance? I don't know. Um, but I feel like I need to know. I should know. And this is the first step towards that. Personally, even though I've been doing this for a long time, I have this fantasy of basically, uh, also not doing this, closing my laptop and not opening a computer again. I don't like looking at computers all day. Um, I like making things, which is what I get to do at work, but I don't like the Mechanics of sitting in front of a computer and looking at it all day. So I would love, whenever I am done with this, I'd like to close my laptop for at least a year. I'll have my phone. I can connect with people if I need to, but I don't want to be looking at a keyboard and looking into a screen for a while.

AI assessment note: “I'm taking my first sabbatical... it's going to be quite clarifying for me.”

Q Holland at F.A.S.T. just after F.A.S.T. One Click Checkout's company went bust, and I, I got many death threats, um, it was horrible, um, and it really, really hurt me. Did it hurt you, and how did you actually get through that? I, I get still a lot of hate. Advise me, you're the wise elder, Jason. How do you get through The hate that you and I will get.

A Well, um, it, it did hurt. Um, and it's still from time to time hurts. Um, when people say things about you that, you know, you just are so extreme and so, you know, just completely unnecessary at the extremities. But one of the things I've just learned simply is that, you know, and this took a while, you know, I, I built up some thick skin prior to this, this sort of eroded some of it, and then you build it up again, is you just, you cannot let other people, uh, tell you how to feel. Um, and, and this is just a, you know, lifelong practice to figure out how to go. Yeah. Okay. No, that's, that's a pretty strong opinion. I know me. I know who I am. I know what I believe. Um, I know why I made these decisions and they weren't for those reasons. And you just have to go, okay. I mean, part of this too, is, is not paying attention, frankly. Like after this whole thing went down, I didn't look at Twitter for four or five months. Um, because Twitter is just really where all the like vitriol and hate hatred, deep hatred was, was happening. I got tons and tons of emails from people who are supportive, but people didn't want to say anything on Twitter because you know how it goes. Not many people are going to stand up to your defense when, when, when people are attacking. And so, but I also, I understand the, the, the, the passionate, uh, uh, sort of, I don't understand the hatred, but I…

AI assessment note: “Well, um, it, it did hurt. Um, and it's still from time to time hurts.”

Q How would you describe your attitude to risk today?

A I'm very comfortable taking risks. I'm actually more comfortable taking risks now, but I'm not comfortable risking the business. So there's this idea of risk and then putting the company at risk. I'm not interested in putting the company at risk, but I'm interested in taking a whole bunch of risks and trying a whole bunch of things. I think this comes from, you know, like David and I talked about this actually, when we made that decision about the no politics thing, we said, you know what? Um, It could happen that, um, this like sinks the business. Like this could sink. This is before we made the decision. Like we thought it'd be controversial. We didn't know how much, but it could sink the business. And we looked at it. We go, you know what? If that is the case, that would actually be okay. It would suck. People would lose their jobs. That would all be bad. I'm certain people who worked here could get other jobs. We'd help people get jobs. It would suck for everybody, but it would also be okay in that we had a, at that point, a 21 year run. Um, a wonderful business. We made a lot of impact in the industry. We took care of lots and lots and lots of customers. We generated lots of revenues, lots of profit, all the things we've, we've put up books. We've done all the things. If it came to an end at that point, it would be okay. And so that's something I always think about. Um, ag…

AI assessment note: “I'm very comfortable taking risks. I'm actually more comfortable taking risks now”

Q Actually, every VC has a boss. It's our LPs. Every founder has a boss. It's pure, uh, investors. If you're a venture backed company, um, you don't have a boss. And so this set of questions I'm really intrigued for. We've seen a generation of SaaS companies now That are unprofitable, and heavily venture funded, and now we have a macro turning. What happens to them? Heavily unprofitable, heavily funded.

A It's going to be hard. I think there's a lot of risk baked into this that people haven't thought about. They assume that companies will be around forever. Big companies will be around forever. Um, you know, they see brand advertising all over. It makes people think there's stability there, but, but there just simply isn't. If a company can't make its own money, they require outside money. Outside money dries up. Things have to change. I mean, there's gonna have to be late. There already is. It's not like this is news, but layoffs, deep cuts, some austerity measures. Um, you know, these companies are gonna realize they probably have too many people, um, and they've been spending wildly on things that don't work. Um, they've been just in a, in a market share grab. So they're, they're, they're, they're, they're losing money on every customer, but they need to grab them because otherwise someone else will grab them. There's this whole mentality out there that I think is gonna shift. It has to shift. It's not even that I think it will. It has to. There's basic, it's basic physics at some point. It's basic economics. If you don't make more than you spend, and you don't have a lot of cash sitting around, and you burn through it, you've got to cut costs, uh, and you've got to be a different business. And I think that's creeping up on a lot of companies right now. Uh, and, and the probl…

AI assessment note: “layoffs, deep cuts, some austerity measures. Um, you know, these companies are gonna realize”

Q How do you measure success? Is it pure profitability? Is it innovation? Is it team morale? What's your metric for, are we doing a good fucking job?

A Well, profitability is important to us fundamentally, right? Um, but the other part of it is simply, would I want to do this again? Like, is, is what we're doing on a daily, weekly, monthly basis? Like, are we enjoying doing that? And would I want to do that again? If I could choose, would I want to live that month over again? Would I want to live that work month over again? That's kind of what it comes down to. Cause if we're making a pile of money and we hate each other, Not interested in that. If we're wildly profitable and every project sucks and, and people don't want to be here and I don't want to be here, that's not worth it. So it ultimately has to be about, do you want to keep doing this? Is this a place you want to spend your, your creative time and your, and your, you know, your, your craft? Is this a place you want to hone that and enjoy that and work with great people that you like and all those things like that has to be number one. Um, but profitability has to be like one a, because if you can't, if you don't maintain profitability, You have to rely on outside sources of money, and then you're beholden to all sorts of realities that you don't control. Not that you really control any of these things, but it just becomes a lot harder. And I don't want to, um, I don't want to spend my days worrying about, um, how I can make some fund a lot more money. Like, I just g…

AI assessment note: “profitability is important... but the other part of it is simply, would I want to do this again?”

Q No, I get you totally. And I like that kind of respectfully laissez-faire attitude. You could almost be a European. Um, but my, my question would be like with goals, if you don't kind of Not agree, but if you don't love executing in that fashion, how do you think about performance management, performance reviews, and ensuring getting the best out of people and measuring them against something?

A Yeah. Yeah, I think, um, first of all, management is really sort of the art of the individual. Um, so I think that you, when you evaluate people, we do performance reviews like, like every company does, but we don't have metrics that we match people up against. Um, because I don't think a lot of people actually have the power to change a lot of these things, and nor do I, nor is that the point. So we know if someone's doing good work, their team knows that they're doing good work, their team knows where they're deficient. They should know where they're deficient. We should know where they're deficient. And we talk and, and, and discuss and encourage people to improve in this area or, or, or reward them, not financially, but like praise them or, or support them if they're doing well in this area. There's a lot of recognition that happens in the company. So I think it's, it's about knowing the people you work with. And part of this is that when you have a relatively smaller company, we have about 80 people, you, you can pay pretty close attention to the work people, individuals are doing, and, and, and you have a pretty good sense of how they're doing. And there is a relative nature to it because there's other people at the company who do similar jobs. So there's some contrast there, but it's, you know, you look at the work, you look at the work and you don't look at the, at the,…

AI assessment note: “we do performance reviews like, like every company does, but we don't have metrics”

Q I'd love to, Bastardize, you know, a lot of your hard work, and ask, if you were to summarize your, like, decision-making processes and frameworks today, how would you describe them?

A When I make a decision, I typically Don't make it for now. I think about what will that probably feel like in a year. This is sort of one way I do this, which is looking back on this decision. What I try to project and imagine what it will feel like. There's a lot of decisions that you make to make sort of short term pain go away or to make conflict go away or to make some disagreements go away. Um, and in the moment it feels good to get that out of the way, but then what are you stuck with? What do you have to live with after that? So I tend to think about what are you, what are we going to live with on this decision? So this comes down to even like complexity in software. Like we could cut some corners right now and shortcut this just to get this thing done. But now we've got this shitty code in the code base. We've got this, this thing we're going to have to live with. We're not going to want to go back in that area and mess with it. Cause it's, it's all messed up. And it in the end was not worth it, even though in the moment it felt like it was. So I, I tend to think a lot about that. Um, I also think like, why are we even making this decision at all? That you can find yourself making a lot of decisions that don't need to be made. Um, that's something I'm always wondering about. Like, why are we even deciding on this? Or like, what if no one decides what will happen? Like, …

AI assessment note: “When I make a decision, I typically Don't make it for now.”

Q So it helps that you don't see each other often?

A Yes. We rarely even, so we used to both live in Chicago for a while. Maybe once a week or every two weeks we'd see each other. We don't see each other very often. Um, I think that's helpful. Um, I think, you know, we talk all the time in base camp. We, we, we have a weekly call. Um, you know, that's enough actually. And I think that's a big part of it too, that we're both able to make decisions independently, that we don't rely on each other for everything, that we trust each other's individual skills and know that we're not necessarily great at what the other person does, but that Um, down the middle, um, we share, you know, 85 to 90% of the same.

AI assessment note: “Yes. We rarely even, so we used to both live in Chicago”

Q Well, I'm interested, you know, naturally, um, as a single dude, uh, looking, you know, to find love also, um, that's very different to being a great husband. Time apart in this way would be challenging for a marriage. Um, what have been your lessons on really being a great husband and having a great marriage?

A Well, um, you'd have to ask my wife. I'm a great husband. We've been married for nine years. I think we're doing pretty well. We have two kids. I think it's, you know, um, my, my parents, when we got married, my parents wrote this really little short letter to us. Um, and, um, and there was a little bit of advice in, in the letter and I'm trying to remember exactly what it was, but it was, um, give each other space is, is a primary fundamental thing. Um, and, you know, compromise, but also give each other space. Um, and, and, and that, that I think is a really important thing. Um, now, not everyone's that way. I think you have to know who you are. Um, but, um, you know, um, if, if you, if you're someone who needs quiet time to recharge, or your wife is, or your spouse is, or whatever, you need to give them that, even if that's not what you want. You know, really understanding what the other person needs is incredibly important in relationship. I think, you know, it's not really this idea of, Of, um, you know, we're, we're, we're, as humans, we're very egocentric, and we're always thinking about ourselves first, and relationship is really about us. It's, it's not about you.

AI assessment note: “give each other space is, is a primary fundamental thing. Um, and, you know, compromise”

Q quick fire because I'm aware I stupidly named it. But I'm going to say a short statement. You're going to hit me with your immediate thoughts in terms of like favorite book and all that shit. What was the last bit of content that actually really stuck with you? Could be magazine, could be TV show, could be movie, could be book, but that actually changed the way you think.

A I listened to, uh, I recently re-listened to Pink Floyd, Dark Side of the Moon. Um, on some mushrooms, and that was a really extraordinary experience actually. Um, I, I, I heard, it was interesting reminder that the thing that you, the thing that you think, you know, uh, you can, you can, um, experience in a different way. Uh, and, and that, that was just an example of that, but I've taken that experience and thought about that in terms of pretty much everything that I'm, you get very used to like the, the one note of something that you really know. And it turns out that there's, there's a lot of notes and a lot of angles on things that, that, that you're even, you know, that you think, you know, inside and out. So that was something that was a, a quite, uh, an interesting experience.

AI assessment note: “I recently re-listened to Pink Floyd, Dark Side of the Moon.”

Q Like, how often do you do them? How does it make you feel?

A Not very often. I've only really done them. I've done them, um, Twice. Uh, I, I've done a high dose twice and then a low dose twice. Basically high dose, meaning like five grams, like you have a blindfold on and it's completely inner experience for about six hours. It's a complete journey trip thing, um, which was absolutely profound. And, um, I came away from those experiences a different person. Um, and also, uh, um, a, uh, um, I, I, I feel like everybody should do this once in their life is kind of how I felt after I came away from those experiences. We can go into more detail on that separately if you want, but, um, I've done some low doses and just listen to music, like real low doses, just listen to music and just kind of relax. And what's really interesting is that you just, you, you, you recognize that, um, um, again, there, there, there's a lot more nuance to things than you typically would, would imagine. And that our brain, our waking brain right now, if we're, you know, both not on anything, Is really a filter. You're filtering the world into a way that you can perceive it on a day-to-day basis and live normally. But this is not necessarily the way things actually are. Um, there's, there's more to these things, but we kind of down sample everything so we can manage. Um, and so it's kind of interesting when you take mushrooms, it kind of upsamples in a sense. It, it …

AI assessment note: “Not very often. I've only really done them. I've done them, um, Twice.”

Q No, I totally get that. But when you're making those decisions and you're thinking about kind of showing the work, Another brilliant tweet, but you said before, in particular, when it comes to like decision-making, when I make a decision, I don't think about how I feel today. What did you mean by that? And then like, what do you think about instead?

A What I think about is when I make it, especially a tough decision, I don't think about how it's going to feel right now. I think about how it's going to feel later. Reflection helps. I think here, sometimes there's a lot of heated things in the moment. And if you make a call right now, you might end up regretting it because like, Once the heat clears and dissipates, you're like, well, I wouldn't have done that if I hadn't been under pressure or whatever. So I tend to project out, how will I feel about this particular decision a year from now? Or how will I feel about this in a few months? It doesn't mean I'm always getting it right, but it helps me eliminate the current situation and stresses and sort of the blurriness of the moment and helps me minimize my regrets. I'll give you a quick example of this too, which is a slightly different version of this, but similar. Whenever we release a brand new feature in one of our products, it's really unusual. Like sometimes we do stuff that doesn't Seemed to make sense at the time, or it's a big change in some way. Naturally, people are going to react to that negatively in most cases because it's so different or unusual or novel, or it changes their behavior in a way where they're not comfortable with it, and I totally get that. Now, what you get is often a flood of feedback saying, change that back, or don't do that, or whatever, right…

AI assessment note: “I think about how it's going to feel later.”

Q Can I ask you, when you have a team and you need them to get behind the mission or get behind you, do you not need to present the illusion that you at least know? Can you show that self-doubt?

A I don't think it's a good idea to present illusions. I think it's just good to be honest, and what I try to do is, I try to explain how I, or we, or whoever's making the decision came to that decision. As long as you kind of show the work, people understand how you came to it. Whether or not it's right or wrong, we will never know until we do. This is the thing I think that's so important, and this is why, like, when we build products, we don't beta test them, really, and we, sometimes we get a few people in, but we're not, like, asking people what they think. Is this going to be good, or would you use this thing, or how much would you pay for it? Nobody knows. Until you make the actual thing and you put it out there. So like you have to do to know. And so when I make a decision that might seem strange or whatever, I'll try to explain how I came to that conclusion and it may or may not be right. And we'll often say like, this may blow up. This may not be right. This might be the wrong move. We don't know, but let's do it. And let's see. Cause that's the only way to find out. So I think that's all you need to do is explain your work. What people don't like is if you make a decision that seems unusual and they don't know why, And you won't tell them, or you lie to them, or you make up some narrative. There's no reason to do that. Then people end up not trusting you at some point,…

AI assessment note: “I don't think it's a good idea to present illusions. I think it's just good to be honest”

Q How would you describe your attitude to risk today?

A I'm very comfortable taking risks. I'm actually more comfortable taking risks now, but I'm not comfortable risking the business. So there's this idea of risk and then putting the company at risk. I'm not interested in putting the company at risk, but I'm interested in taking a whole bunch of risks and trying a whole bunch of things. I think this comes from, you know, like David and I talked about this actually, when we made that decision about the no politics thing, we said, you know what? Um, It could happen that, um, this like sinks the business. Like this could sink. This is before we made the decision. Like we thought it'd be controversial. We didn't know how much, but it could sink the business. And we looked at it. We go, you know what? If that is the case, that would actually be okay. It would suck. People would lose their jobs. That would all be bad. I'm certain people who worked here could get other jobs. We'd help people get jobs. It would suck for everybody, but it would also be okay in that we had a, at that point, a 21 year run. Um, a wonderful business. We made a lot of impact in the industry. We took care of lots and lots and lots of customers. We generated lots of revenues, lots of profit, all the things we've, we've put up books. We've done all the things. If it came to an end at that point, it would be okay. And so that's something I always think about. Um, ag…

AI assessment note: “I'm very comfortable taking risks. I'm actually more comfortable taking risks now”

Q How do you feel about kind of what is measured improves and also kind of driving teams with goals?

A Um, I'm not a goal driven person, so I don't drive teams with goals. Uh, I don't have goals really. I don't really believe in that. I know a lot of people do, but it's not my thing. It's never been my thing. My thing is like, do the best job that you can. And why wouldn't you just do that? Like, what is it about the goal that makes you do the best you can? I think you should be, you know, intrinsically motivated to simply do the best you can. Um, So that, that's sort of my approach. There's not like a thing that I would do differently if, if there was some number ahead of me. In fact, I probably would hate it more because now I'm chasing something that's arbitrary, ultimately. I mean, people set up these targets and that we've done in the past, you set up some target and you aim for it. It's like, why do we pick that number? Well, it happens to be a nice round number. So like, I'm, I'm, everything I'm doing now is, is based on some made up number that happens to be a nice pretty round number. Like, And, and the, and the stress I'm taking on and the challenges we have are all based on this thing that we made up. Like, how about we don't make anything up and just do the best work we can on a daily basis. And that adds up and let the chips fall where they may. I mean, that's kind of my, that's my approach, you know, for better or for worse.

AI assessment note: “I'm not a goal driven person, so I don't drive teams with goals.”