20VC: Basecamp CEO Jason Fried on His Relationship To Risk, Money, Vulnerability and Self-Doubt, Fantasising About Being Fired, How To Optimise Decision-Making and Minimising Regret

Jason Fried is the Founder & CEO @ Basecamp, the project management and team communication tool trusted by millions. Over an incredible 22 year journey, they have scaled to over 3.5M accounts and in 2020 they went back to being a multi-product company with the launch of their integrated email client & service, HEY. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few. In Today’s Episode You Will Learn: 1.) How Jason Fried made his way into the world of startups and came to found one of the leading project management and team communications tools in the form of Basecamp? 2.) How does Jason analyse and evaluate his relationship to money? Why does Jason believe that he has this inherent downside protection when it comes to money? How does he structure his personal finances between stocks, cash, crypto etc etc? What have been some of Jason's biggest lessons when it comes to tying happiness to monetary levels? 3.) What does Jason mean when he says, "I have a fantasy of getting fired"? How does Jason think about knowing when is the right time to step away from the business? What would he like to do with that time? How does Jason feel about the challenge of tying his identity to his company? What are the dangers of doing so? 4.) How does Jason approach decision-making frameworks? What does Jason believe is the right way to respond when a decision does not go as planned? Where do many make mistakes here? Does Jason feel regret with decisions? How does Jason try and minimise regret? 5.) How does Jason feel about his biggest insecurities as a leader and CEO today? What are Jason's views on a CEO's ability to have self-doubt and be vulnerable? How have his views on this changed over the years? In what way has having kids impacted Jason's operating mindset? How has it changed what he values and appreciates? Item’s Mentioned In Today’s Episode Jason’s Favourite Book: In Praise of Shadows As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome back. This is 20 VC with me, Harry Stebbings. Now, you might have noticed that the last few months of shows have been a little bit more personal. They've been focused on the traits and mindsets of great leaders, and the best of these shows always go off script. Now, there is no greater example of this going off script totally than today's episode with the one and only Jason Frye. Luckily, he was okay with my wayward questions, but to Jason, he's the co-founder and CEO at Basecamp, the project management and team communication tool trusted by millions. Over an incredible 22-year journey, they've scaled to over three and a half million accounts. And in 2020, they went back to being a multi-product company with the launch of their integrated email client and service, Hay. Jason's also the co-author of the widely acclaimed Rework and has made several angel investments in the likes of Intercom, Gumroad and Hodinky, to name a few.

• 0:45Harry Stebbings?

  I'd also want to say a huge thank you to his wonderful co-founder, DHH, for some fantastic questions and suggestions today. David, I really do so appreciate that. But before we move into the show today, I have to say I just love using AngelList's fund admin platform to manage my investments. The team and platform at AngelList takes care of all my back office needs so that I can focus on working with great founders. Leading fund managers have made over 10,000 investments into 6,000 startups via AngelList, all online and all in one place. And with recently announced Rolling Funds, you can easily find and invest in these top fund managers on angellist.com/rolling. And speaking of amazing products there with AngelList, last month I had Jeff Seibert and Wayne Chang on the show from Digits. Simply put, they're two of the best founders I've met, and they're creating the most intuitive financial software you've ever used,

• 1:30Harry Stebbings?

  automatically analyzing your company's spend and visualizing it for you as it happens, honing in on recent activities, trends, anomalies, or any question you have in just a few clicks. And unlike every other financial software, their integration is not weeks, it is just a few clicks. I have to say the product is just beautiful and you have to check it out, and so you can do that on digits.com. And finally, I've always been a big history man, and so I want to talk about Cooley, the global law firm built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Cooley's formed more venture capital funds than any other law firm in the world, with 50-plus years working with VCs. They help VCs form and manage funds, make investments, and handle the myriad of issues that arise throughout a fund's lifetime.

• 2:11Harry Stebbings?

  So to learn more about the number one most active law firm representing VC-backed companies going public, head over to cooley.com, check out cooleygo.com also. But that's quite enough from me tonight. I'm very, very excited to hand over to Jason Frye, co-founder and CEO at Basecamp.

• 2:31Speaker 01

  You have now arrived at your destination.

• 2:35Harry Stebbings?

  Jason, this is such a joy to do. I've wanted to see this for such a long time. I heard so many great things from your wonderful co-founder David, but thank you so much for joining me today.

• 2:42Speaker 02

  It's wonderful to finally be here and talking to you. We've traded emails and a bunch of things, so it's great to chat.

• 2:47Harry Stebbings?

  It really is, but I do want to start today. 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?

• 2:56Speaker 02

  Well, let's see. So originally we were 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 was 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.

• 3:37Speaker 02

  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 of working on my own. Carlos wanted to get into the web, so we all just said, 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 go. We all worked in Carlos's office around the same desk because he already had a space. And we just sat there and said, we have a company now. You know, we didn't like incorporate it. We didn't like call a lawyer. We didn't do anything official. We just said, like, let's sit together and see if we can land some business and go from there. So that's really, I mean, there's more to it, but that's really how it all started, just on a whim.

• 4:11Harry Stebbings?

  I love that as a start. It's always nice to hear those kind of origin stories and I'm diving straight in. Normally I quite like to, like, you know, ease the guest in and have that warm chat. But fuck it, I'm going straight in for this one because I heard you speak on Clubhouse a little bit about finances and how you think about it. And I think a lot about actually relationships to money and it's one that I'm kind of twiddling with myself a lot right now, which is why I spend so much on therapy, but. But like, how do you think about your relationship to money today? And how has that changed over time?

• 4:39Speaker 02

  I've always wanted to have what I needed to buy what I wanted. And in fact, the way I used to price things early in the day, like when I was first getting started as a website designer, was I want a new car. That car is thirty thousand dollars. Let me see if I can make thirty thousand dollars off this project. Or let me see if I could put together two projects to make thirty thousand dollars. And never price per hour, or I just like, what do I want out of this? Can I get it from that? And that's how much it costs. So like, that's kind of how I've always felt about this sort of thing. So that's how I always thought about money was like, I wanted something. And so money was a means to get that thing. It wasn't like I want to amass money to have wealth or to be able to do things in the future. It's like, what do I need right now? And that's kind of how I started with it. And, you know, over the years, we've made a lot more than I can ever imagine. And I have more than I need.

• 5:23Speaker 02

  And so now, of course, like, money is no object for day to day living, which makes it a different kind of thing, something more that I prefer to share. I mean, I still, of course, make more than I need because that's just how the company is. And I'm fortunate. But we do a lot of sharing in the company and I do a lot of sharing outside of the company. And I think of it as a way to help others who sort of need something that they might not otherwise get. So I've done a little bit of investing, but not much. Mostly investing I've done is to support others and to help others. And I typically don't have any expectation of getting anything back from it.

• 5:53Harry Stebbings?

  We are going to touch on the investing side. And just while on this, I have to ask, you said about kind of charge on a project because you want to say that car or that house or whatever that is. I do the same, but my trouble is I don't actually gain the pleasure when I get that house or that car. And I'm just.

• 6:07Speaker 02

  You never do.

• 6:08Harry Stebbings?

  Did you have any lessons from like tying the happiness to the object?

• 6:11Speaker 02

  So I think you're right. You don't really get happiness from objects, certainly not. You get a temporary boost. But for me, when I was younger, it wasn't so much, I wasn't looking for happiness. That's not what I was looking for. I'm still not because money doesn't get you that. I mean, money can provide some things, but it doesn't really bring you anything lasting in that respect. But at the time, I was just into stuff. It wasn't happiness. It was like, I was into cars. So I wanted a cool car for myself, just to have, to play with, to go fast or whatever I wanted to do. Or I wanted before that, before I could afford that, I wanted a new car stereo because I liked car stereos. I just liked. them and I wanted a cool one with cool lights on it and it was more like a little bit of a lusty want kind of thing than it was happiness.

• 6:50Speaker 02

  I wasn't looking for like if I get this radio or if I get this car, I'm going to be happy. No, it's like I'm going to be satisfied and excited to enjoy this thing. That's all it was. It was like there was an envelope around the experience. It wasn't going to make me happy in life. It was going to make me happy around the thing. And that was cool and I was into that, but there are diminishing returns on anything like that at some point. You have what you need. You have what you want. You can buy things that you enjoy. Like for me, a lot of it is I'm getting to experience something. It's not about long-term happiness, but getting to experience something is kind of fun. So I don't know. I don't think about it that much anymore, I guess.

• 7:26Harry Stebbings?

  You mentioned the investing there. How do you think about your personal portfolio? Cause I heard you a little bit on a clubhouse the other night and about 1am, you know, when I was sitting there listening to you. But like, how do you think about the personal portfolio? You mentioned investing. How do you think about that with the capital base that you have now?

• 7:40Speaker 02

  So I'm very, very conservative when it comes to investing. All my risk is tied up in my own business and my own business is a machine that makes me the money. When I invest in something, it's because I want to support the thing. And if there's a return in the end, great, but that's all gravy and bonus for me. I make money through my work. So for example, I've invested in a handful of small companies that my friends run. I don't care if I ever see any money from that. It wasn't about that. It was about helping. Like for example, a personal trainer I used to go to for a long, long time. He wanted to start a new business. He wanted to start a training business and I for years I've been saying, dude, go off on your own. Please, you're so good. Go off on your own. And the biggest hurdle for him was like, I can, but I can't afford the rent. So I'm like, look, I'll pay your rent for the first two years. Here, here's a check for the first two years of rent. It's a gift. I don't want anything back.

• 8:24Speaker 02

  I just want you to do this because I want you to succeed and I know it's going to be great for you and your family. And hopefully one day you can pass that on to someone else. Like that's how I've been thinking about this sort of thing. So in that case, like I'd like to frankly do more things like this. Like I'm trying to think about this idea, which I'm calling hurdle investing. Although I haven't formalized this yet, still in my head, which is how can I help people who need to get over one hurdle? To be able to run the rest of the race, basically. So for him, it was like, I need a space, but I can't afford the rent upfront. So if I can clear that hurdle for him, then he can go off and do the rest of his business. So I like this idea of, I don't even like the term grant because grant comes with this idea of writing for a grant. It's a gift. It's a hurdle gift to help people who are just on the brink but can't get over it because of something like that. Maybe I can help. Maybe that's where my money can be useful to others.

• 9:08Speaker 02

  So that said, I've also invested in other companies that it's not like that. I get shares back and whatever. But these are all companies run by friends that I just want to support and be there for them and help as much as I can. And sometimes an investment is the way to help. So that's how I think about it. But like my personal trading portfolio is like boring index funds, like S and P 500 in NASDAQ, the Dow, that kind of stuff. I've owned Apple for many years, split adjusted down to like $2. So I've done quite well on Apple over the years. So I've got like a handful of blue chips, boring stuff, index funds, and then a few like things that I know that I explore, play with. But my business is what makes my money and that's the only way to look at it.

• 9:45Harry Stebbings?

  Can I ask, when you think about your conservative mindset, I actually, weirdly enough for a VC, share the same like risk mitigation mindset around money. And mine comes from like my family lost everything when I was younger. And so I'm always very protectionist around what I have because I know how bad it can be to lose everything. Where do you think your conservative and risk mitigation mindset comes from?

• 10:03Speaker 02

  Probably my parents. My parents made me work ever since the day I could, which was in my neighborhood where I grew up or my town. It was 13. At 13, you can get a work permit. The only thing they've given me past that was they paid for college and they gave me $5,000 after I got out of college to buy a computer to start like a business. Everything else I've had to earn myself. And I think when you have to earn it, for me at least, it makes me sort of understand what went into it and I appreciate it perhaps a bit more. And my parents were always conservative with spending. My grandparents were conservative with spending and I think it's just part of me. Maybe it's a Midwestern upbringing. I grew up in the Midwest in the US or tend to be more conservative in terms of what we're willing to do and what risks we're willing to take. So I like taking risks, but I've never been one to put myself at risk.

• 10:43Speaker 02

  And there's a big difference between taking one and putting yourself at one. I don't do anything that could end me. I would never bet the company on something. I would never bet the farm on something. Like I'm willing to take a risk, but if I lose it all, I'm okay with that. So for me, whatever I make from my business goes into this pile of don't lose it. That's where it goes. It goes in the don't lose it pile. Because I put all the work in to earn it. I don't want to lose it now. It's not worth it for me to try to double it. I don't need to do any of those things. The business keeps me okay, keeps me flush with what I need, and so I just don't want to lose it. And then I can do things with it. And frankly, like, most of my money is sitting in cash, which most people would go, that's the stupidest thing in the world. But for me, liquidity, optionality, yeah, I'll technically lose a little bit on inflation or whatever, but like, I'm again, okay with that.

• 11:27Speaker 02

  Versus going into the latest trend or going into something and losing 20%. When you lose 20%, you gotta go up, what, 50% to get that even back, however the math works out. So I'd rather just lose like a percent or two a year if I had to on inflation. But just know that there's money there that I can preserve for the most part, share with my kids, share with my family, share with friends, that sort of thing.

• 11:44Harry Stebbings?

  I'm totally with you and I share a lot of that mindset. I do want to touch on your leadership, especially though now. Because, you know, you tweet some brilliant things which allow me to go off on tangents. But one of them was you said like, being CEO is almost never worth it. And I saw that and I was like, huh. I wonder why did you say that and what made you tweet that?

• 12:01Speaker 02

  Yeah, and it's funny because the reaction I got was not what I expected, although I probably should have, which is like, you're lucky that you can say that. And it wasn't about that. Actually, it wasn't about me. It was an observation, actually, about others. Primarily high-profile CEOs, like, it must be incredibly stressful to run a public company. It's one of the hardest jobs to do because you're scrutinized over pretty much everything. You're almost always misunderstood. You have very few peers. And I forget what it was at that moment, maybe it was like Elon Musk or someone had said something and everyone jumped all over him. And I'm like, man, it's almost not worth it. What are you getting out of it, kind of, is the question at some point. To me, it has to be about like the product and making stuff. And most CEOs aren't involved with that anymore. They're involved with other things. They're involved with complicated things. They're involved with conflict. They're putting out fires all the time.

• 12:43Speaker 02

  They're doing all these things. It just seems like, is it actually worth it anymore to do that? And so that was what was going through my head. I've also personally occasionally wondered that myself, like, how long do I want to do this for? And there's moments when you're like, that timeframe gets really short. You're like, not much longer. And then the other things happen, you're like, forever. And it's probably a little bit of observation on the outside. Plus, like, maybe something happened recently at work. I'm like, I don't know what it was, but like, I'm a little bit tired of making these kinds of decisions or whatever. And so I just like, you know, Twitter's that place where you can throw an idea that's in your head and make it more concrete, whether or not. It was the right thing to do or the right thing to say or what I really believed. At the moment, it was, and that's sort of why I put it out there. I don't draft tweets. Something pops into my head and I go, let me put that out there and see what happens. So, but like, for example, I think another one of this was like, remember when I was watching the antitrust stuff?

• 13:27Speaker 02

  Like Tim Cook and Steve Jobs and who else was there? Microsoft and Facebook, you know, Zuckerberg. And I'm like, that must suck. Who would want to be Mark Zuckerberg right now? I can't imagine anyone would want to trade places with Mark Zuckerberg right now. So like, that must just be the worst job on the planet, actually. Even though he has so much power, it must be a terrible job. Do you think he's happy doing this job? And then I just started extrapolating that out to other people doing that job. And a lot of CEOs aren't very happy doing the job.

• 13:55Harry Stebbings?

  I think one thing that always strikes me when I look at a lot of the CEOs that we mentioned and any CEOs like you, Bluntly, which is like, you know, you often speak with this conviction and with this unflappability. And I sit here and do loads of things. I'm going, fuck, I have no idea what I'm doing and I'm just riddled with self doubt. And I honestly, I really love your advice here. As I do more and more stuff where I have no idea what I'm doing. How do you deal with self doubt? And how would you advise me to deal with it?

• 14:20Speaker 02

  We're the same, and I think everybody is, actually, which is nobody has any idea what they're doing. Some of us just sound like we do. I think there's sort of this quest for certainty. It doesn't exist because every moment is different than the last. There's so many variables you can't control. There's so many things you'll never know until you try, until you do. And so it is all uncertain. And I think I've just come to terms with that. What I'm saying in the moment, it doesn't have to be right forever. And it could be wrong right now and it might be right later. I don't even know, and I don't even really care to think about that. It's just like, right now, this feels like the right thing to do, given how I'm feeling. And this is, part of this is because I'm a very gut-driven, feel-driven decision maker. I don't look at numbers, I'm not looking at metrics. I try to feel things out. And so feelings are very uncertain.

• 15:03Speaker 02

  I could have slept poorly the night before and my feelings are going to be different than the next day where I get a good night's sleep. It's so variable that I just tend not to worry about whether or not I'm right or wrong about something. It's like, just in the moment, does it feel like the right thing to do? Do I think I'm doing the right thing? And we'll see what happens.

• 15:18Harry Stebbings?

  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?

• 15:27Speaker 02

  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 have 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.

• 16:09Speaker 02

  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, or they make up their own reasons, which are almost undoubtedly worse than the actual reason why you made it. Then you start to spawn off rumors and conjecture and all these things that aren't good things. So just admit like, I don't know how this is going to work out, but here's how I came to it. And I'm getting repetitive, but that's how I do it.

• 16:46Harry Stebbings?

  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?

• 17:01Speaker 02

  What I think about is when I make 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? 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.

• 17:44Speaker 02

  Like sometimes we do stuff that doesn't seem 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? In the moment, right there at that time, if you just knee jerk and go back to the way it was, you're never going to make anything new. What happens is people want to put the fire out right there because there's a fire. But sometimes a fire will burn itself out. So what I tend to do is like for any like immediate change based feedback. I say, let's just sit on this for a while and let's see what happens in a few weeks. Because once the moment goes away and people start to get used to this thing, maybe they'll end up liking it.

• 18:29Speaker 02

  Right now, they can't like it because their body won't let them, their mind won't let them. It's too different at the moment, but in three weeks I might go, you know what? I like this now. And it's a very similar thing with decision making, thinking like whatever decision I'm going to make in the moment. I might be able to put out the temporary fire now, but what am I putting in place that I'm going to regret down the road? So I always try to think about down the road, if I could look back, what decision would I make? One of my favorite books is very short. It's called The Manual. One of the essays in the book, which I really like is it's something about like if someone breaks something that you own, you react one way. But if someone broke that same thing that someone else owned, you'd react a different way. You go, oh, it's just a mug. They just dropped the mug on the floor like big deal, right? But if it was your mug, you might be like, what the fuck? This is an important mug to me or whatever.

• 19:10Speaker 02

  So his suggestion was like, remove yourself from the situation and try to react more as if it was a situation you were observing where you're not involved. How would you actually react in that situation? So I try to do that by adding distance to a decision. So I can look back on it and go, how would I react if I was just not involved in the moment? What's the right thing to do overall?

• 19:28Harry Stebbings?

  Yeah, I can understand that. I think a big decision as CEOs though is like what to engage with versus what not to engage with. And you said before, you know, there's so much not to do. How do you think about how to determine where to spend time versus where to not spend time? Given the plethora of options that you Have at your disposal.

• 19:45Speaker 02

  It comes down to a couple of things. Feel, again, what excites us? What's exciting? Sometimes you have to deal with things because they are persistent, you know? Like, you've got a little pain in your shoulder and you're like, eh, it's fine. But it's still there two weeks later, now I gotta deal with it. Sometimes it goes away in three days and you're glad you didn't have to deal with it. Like, I could have gone to a chiropractor and I could have, like, made an appointment. I could have changed my whole schedule around to get this thing done. But actually, it just worked its way out in a few days anyway, so I'm glad I didn't go through all that. So, sometimes it's about persistence, like, things that keep scratching at you, you gotta deal with. It could be things that are important to other people that might not be important to you, that you have to, of course, put your head in someone else's head and go, "This is worth dealing with now because enough other people really are concerned about it." Or something isn't clear. But ultimately, it's what feels like it's worth spending time on? What gets us excited? How do I get goosebumps?

• 20:28Speaker 02

  Like, for example, working on this new feature for Hey right now, our email system, that has never been done before in email. It doesn't belong in email, but it totally will seem like it belongs once we do it. It's like, no one's gonna expect that we're going to be doing this. Hopefully, we're gonna launch it next week. And it was purely because this idea came up and we had goosebumps. And it's like, we gotta do this. This has to be done. And so, that's what we put our energy into. You know, we're following the things that excite us because when we're doing things that are exciting, we're gonna do them better. We're motivated, intrinsically motivated, to make them great because we want them, we're excited about them. You do your worst work on things you don't really wanna do. So, we try to do the things we mostly wanna do, as much as we possibly can, recognizing that in life and in business, you can't always do the things you wanna do. But we try to do more things that we wanna do than things that we don't wanna do.

• 21:12Speaker 02

  So, it really is a feel thing. It's not like, "Let me look at this dashboard and go, 'Oh, 33% of people want this, so let's do that.'" Well, like, we don't have a dashboard like that. I wouldn't wanna make decisions that way. I wanna feel the desire to do it, so we can do it well. We're getting things wrong all the time, probably, in that, like, there might have been a better thing to do. But, okay, like, the other way to look at it is, we've been doing this for 21 years. It's worked out so far. It'll probably, hopefully, keep working out for a while. What happens is, sometimes, companies, as they get bigger, they start to get serious. And they start to put in all these rules, and, "Well, now that we're bigger, we need to be more systematic about this." And, like, you start to just dull the company. And you forget the reason you're still here is because of the way you've always done things. So, I just try to remember, like, as uncertain as it might seem, like, we've always made uncertain decisions.

• 21:57Speaker 02

  We've always just figured out what to do based on what we wanna do. Let's just keep doing it that way.

• 22:00Harry Stebbings?

  I am with you in that thinking, but I do struggle from like regret. And so I always go through like regret minimization frameworks. How do you think about regret? And is it something that blights you when decision making? Or do you remove it entirely?

• 22:12Speaker 02

  I can't remove it entirely. I minimize it like you and Bezos, who came up with that or whoever else came up with it. Part of it is, again, making decisions by trying to look back on them versus look at them right now. So how will I feel about this later? I've also found that I regret far more things I say yes to than the things I say no to. So part of what I've done is I've tried not to say yes to things far in advance. I've just looked at like, this is a bit of self-awareness, basically, and this is just my own thing. But I tend to regret things that I book far in advance. I like an open schedule, being able to have space and time to think things through and to do things that make sense at the time. What I don't like is if I looked at my schedule on Monday and go, I have no time this week for anything interesting that comes up. Because I've pre-booked it, I booked it months ago, this is happening at 10, this is happening at 2, and this is happening at 3, and I've got no time.

• 22:57Speaker 02

  That's what I regret. It's not the individual things, it's the collective calcification of my time that I created in the future because I kept saying yes to too many things down the road. Those are the things I regret most, is saying yes to things down the road. So what I've tried to do is I've tried to follow as best I can Warren Buffett's thing. I don't know if you're familiar with this. If you ever want to meet with Warren Buffett, what his secretary will tell you, call the day before and ask. So Warren Buffett's schedule is open. I mean, certainly there's a few things on his schedule that he has to plan. But for the most part, it's totally open and he keeps it open so he can figure out what he wants to do on a daily basis. And if you want to meet with Warren, you call the day before. You go, is Warren available for a call tomorrow? Not is Warren available four weeks from now on Tuesday, the answer will be no, call back the day before.

• 23:40Speaker 02

  And that's how I want to try to live, and that's how I've tried to live. And it's helped for me to minimize my regrets because my regrets are mostly founded in the fact that I don't have enough time to do things I want to do because I've already said yes to too many things in the past about the future.

• 23:53Harry Stebbings?

  One of my big regrets is always tying my identity so much to my company. Because it means I struggle to go on holiday because like when I lose one, I lose the other. And I really struggled to know who I am without the other. How do you think about like identity tied to your company, especially given, A, bloody, as you said, feel, you've said feel so much. You are so intertwined with your company, one. And two, it's 21 years, this is such a seminal part of your life. How do you feel as like company and identity?

• 24:20Speaker 02

  I really love that you asked this question because this is something I've been thinking a lot about lately. I don't know. I have never taken a long break. David did last year. He took, I think, something like three months off. I have never really taken any time like that off and I'm actually really excited to try to do that this year. What I hope happens is that better things happen when I'm away because I think what can happen is you think that you're necessary. And you are probably at times, but most of the time you're probably not. And I think it'd be a really good wake up for me to recognize that I can step away for a while. And I think only then will I be able to really feel how that feels. I also feel like, and David and I talk about this all the time, if we went out of business next year, for whatever reason, let's say,

• 25:00Speaker 02

  something crazy happened and we went out of business, I tend to look at what's happened already versus what's just happening right now in this case. So for example, I go, well, we had a 21 year run. That is amazing. I am thrilled with the fact that we had a 21 year run and if this all went away, so be it. Like it'd be okay. Everybody at base camp would be able to get wonderful jobs somewhere else. Like everything would ultimately be okay. We wouldn't have our company anymore, but like we had 21 years. That's pretty damn good. Nothing lasts forever. You know, so I try to think about it that way, but I don't walk around every day feeling like I'm the CEO of this or that. I'm a father of two, you know, I have like two young kids. There's more to life than the work, but I do enjoy the work. I'm not sure if I got to the answer there, but it's a great question.

• 25:39Harry Stebbings?

  I think the interesting thing is like probably the company will be okay. My question more is probably what I'm thinking on is that, yeah, would you be okay?

• 25:45Speaker 02

  I absolutely think I'd be okay. In fact, I have, this is gonna sound weird, I have like fantasies about being fired. I know this sounds weird. It's a very privileged position to be in, but I'm envious. Again, I recognize how this sounds. I hope people don't think it's odd, but there's two groups of people I kind of envy sometimes. People who get fired who can get another job. So if you get fired and you can't get another job, that's really terrible. But what I sort of have these fantasies about is people who quit or get fired, there's a moment right there where they completely unburden themselves of all responsibility. There's something about that that's extremely appealing to me. Forgetting the financial impact of getting fired and the social impact, I totally understand all that, but like stripping all that back. The moment that you can one second walk away from everything that burdened you or like took your time or was on your mind.

• 26:30Speaker 02

  That is a fantasy moment for me that I think about sometimes. The other group that I've always found interesting is our athletes who simply have to give it up. You can't be an athlete, for the most part, at an elite level, past your mid 30s, basically. And I know, again, like, that's probably scary for an athlete. But there's something, again, if I can just step back from it and like, just get factual about it. There's something appealing about saying like, it's over, like, you have to do something else. What's hard for me is that I'm the co-founder and CEO, meaning I cannot be fired. I mean, there's, I guess, scenarios where I could somehow be pushed out, but like, basically, like, I have to quit. I have to quit.

• 27:04Harry Stebbings?

  But my question to you is, if you found, and just truly that, if you fantasize a little bit, even a thought about being fired, man, you could put in a great CEO who's a friend of yours, not like a professional CEO that we, you know, every type hates, but like, a great CEO who'd run it beautifully, and you could be exact chairman, come in for product sessions, live a great life. Like, that sounds good to me.

• 27:23Speaker 02

  That'd be fun. You know, it's funny, so there's a company called Hodinkee, which is a watch.

• 27:27Harry Stebbings?

  Kevin Rose.

• 27:27Speaker 02

  So I'm a big, yeah, well, Kevin used to be CEO, but Ben Clymer is the guy who started it. I love Ben, I love Hodinkee, been on the board for a while, I'm not anymore, but I was on the board, I'm an investor, like, full disclosure. Ben just left as CEO, installed a new CEO, he'd started the business, so he'd been CEO for 10, 12 years, whatever it was. And now he's executive chairman, and I gotta tell you, I'm completely jealous. I'm completely, completely jealous. That said, I don't want to do that right now, but there's something about, at this point in my career, there would be a lot of joy in seeing someone else run what I've built, but I still love doing it so much that I'm not ready. But I do have these fantasies, and I didn't have these fantasies five years ago. I'm using the firing and quitting and whatever as like a description of a moment that I can't have happen to me.

• 28:09Speaker 02

  I could, I guess, somehow, but like, for the most part, I have to make that move. And, I don't know, it's just something I think about, the massive relief that would come with it. Like, all the responsibility I have would be gone in a second, and there's something really appealing about that.

• 28:21Harry Stebbings?

  I mean, I think the thing is like self-awareness, if I'm not going too deep, and it's like, I didn't have self-awareness before, and kind of burning myself out on things. Do you think you have the self-awareness when that time does come, which is obviously not now, but when that time does come? You know what, I want to be more like Ben.

• 28:35Speaker 02

  It may be now, and it may have been five years ago. I'm certain that somebody else could come in and technically run the business. Business better than I can. I don't really know how to run the business. I just know how to do what we've always done. So someone else could come in here and double the revenue. Someone else could technically be a much better CEO than I can. So I'm under no illusion that I'm the best at what I'm doing here. I'm just like the one who's doing it. There are interesting things to think about and I've been thinking about it more and I think it's like, maybe this is part of the reason why I'm like, it's almost never worth it in a sense. But almost, meaning that it is more than it isn't.

• 29:03Harry Stebbings?

  What does your wife say? Like, your wife knows you better than anyone. She sees you in the evening at dinner. You have pillow talk, you have baby talk, yeah, yeah, everything. Like, what does she say? I'm fairly non-in relationship because I didn't know what talking would is.

• 29:16Speaker 02

  We don't talk about business hardly ever. I mean, really, we don't talk about it. It's just not something. I mean, I'm really good about my hours. I work eight hour day. I'm done at five, five thirty roughly. Sometimes I'll put in a little bit of time at night if I took some time off during the middle of the day. So it's not like this all-consuming thing where she's like, Jason, you're working your ass off. You're working too much. You're not seeing the kids. Like, it just, none of those things come up. So therefore, we just don't talk about it very often, actually. I mean, I think that she would encourage me to take some extended time off and she would be right. I just haven't found the moment to do it, but I'm kind of thinking this year at some point might be the right time.

• 29:47Harry Stebbings?

  Do you visualize what you'd do? Because I, I do visualize what I do. I visualize Portofino. I visualize a mojito overlooking the coast. This is what I'm thinking. What's your visualization?

• 29:58Speaker 02

  Having nothing to do at all would be really spectacular. I would probably like to learn something new that I don't have time for. Like, I like to play drums, but I'm terrible at it. I would love to be able to spend four hours a day practicing or like taking lessons. Or ceramics is something I've always liked, which I don't do, but I'd like to like just throw some clay on a wheel and explore. But mostly, I don't want to have anything to do, so I can figure out what I want to do.

• 30:23Harry Stebbings?

  I totally get that. To read a book and not worry that it's a waste of time or it may be shit. Like, that is luxury.

• 30:30Speaker 02

  To me, that is actually ultimately the real luxury. It's not having the things or doing the things. It's having the space to decide that whatever you want to do is worthwhile. That really is ultimately what I think is worth it. Now, I was talking to David about this because David just took those months off and he's like, the first few weeks were glorious. A few weeks in, he's like, I would hate. Hate retirement and I think I would probably ultimately feel the same way, but it would be nice just to have the space to just have nothing to do truly. Or like I'd probably go on a lot of walks. I would just observe and whatever. I don't know. I want to not know. Actually, what I don't want to do is plan time. My whole point earlier was like, I don't want full schedules. I don't want a full calendar and I pretty much don't have one, but I want to really eliminate everything from it.

• 31:11Speaker 02

  And just figure out what I want to do or do nothing. But I love building product. I love making something that doesn't exist in the world. And I can't do that alone. So I love working with incredibly talented, wonderful people of great character who do great work. Who are kind to one another, who build something together. So that is the thing that makes me want to keep doing this. It's not all the other CEO responsibilities. I don't like most of those to be honest, but like I'll do them. I'll do them because I get to do the other stuff. So I'd rather still do this.

• 31:39Harry Stebbings?

  Question, you mentioned the kids. I'm always fascinated, especially you know, not having kids, but like how did having kids maybe change? How you think about operations, how you think about how you spend your time and kind of change you, I guess.

• 31:51Speaker 02

  Yeah, I mean, it changed me a lot. I never really wanted kids because I'm selfish with my time and I could have lived without them. But now I realize I couldn't have lived as well without them. It's so special to see young brains learn without being taught. That's the thing that's so interesting to me is like you don't teach a kid how to talk. You don't teach a kid how to walk. You don't teach a kid how to be curious. I mean, you can kind of help them along, but these things are innate and they figured out and it's just incredible to think about what you can figure out. We're always like, we want to be taught everything, especially as you get older. It's like, well, I want to take a class on this. I want to listen like sometimes it's like get in there and do it. Like a kid and you figure it out on your own. And that's been a really wonderful thing to see and it reminds me that you can figure things out.

• 32:31Speaker 02

  Coming at things with an empty mind, ignorant mind, like not understanding how something works is actually a really wonderful way to come at things. I've tried to stay as uninformed as possible about a lot of things. So I don't come in with preconceived notions. Kids don't have preconceived notions. They don't have any notions. That's a wonderful place to be. It's hard as an adult to really embrace that, but it's something I aspire to be more like them in that way. It also just reminds you that time takes on another meaning. And that you don't have a lot of it. You don't have a lot of it on a daily basis. You don't have a lot of it necessarily on a weekly basis. That life is both short and long. It's all just kind of relative, I guess, but mostly it's that you can pick things up and you can figure things out. And sometimes that's the best way to learn anything.

• 33:14Harry Stebbings?

  Because thinking about upbringing and being that parent for your children, you mentioned earlier, your parents supporting you, but gave you the five thousand dollars for the computer and on your way.

• 33:22Speaker 02

  Yeah.

• 33:23Harry Stebbings?

  Your kids have a different upbringing, but with the wealth, how do you think about ensuring they have that same appreciation for money and hunger and ambition? And kind of have that when the wealth is there?

• 33:33Speaker 02

  I worry about that frequently. I think it's just about values. I don't know, like I'll have to see how they turn out, to be honest. I don't know. This is again, like, I don't know. I can't be certain, but I think instilling the right values, that things are earned, you work for things, that you have to respect things. That time is important to spend on important things that are worth doing and you should be curious and all those kinds of things that my parents taught me. I still don't know to this day, like, do my parents have money? Do they not? I don't know. I have no idea. My parents never talked about it. We had a few nice things, for sure. But we had a pretty much probably middle, upper class upbringing, but like my parents were never flashy. They don't show off and I tried to be the same way. And I think that hopefully those are the things that rub off, that even if you have something, you don't flaunt it. That's disrespectful. You don't put it in someone else's face.

• 34:18Speaker 02

  Like, there's nothing wrong with wealth. There's nothing wrong with having things. And that's just probably gonna be the reality for them. It's just about, you know, how you treat others and how you treat things and how you respect yourself. And it's that sort of stuff that you hope, that you hope, you hope that you instill. Like, you just don't know, though, until kids become adults. Because I'll tell you that I'm a very different adult than I was a kid. Like, I got in a lot of trouble when I was younger and did a bunch of stupid things. And I guarantee you, there were moments when my parents looked at me going, holy fuck. Like, we've raised a fucking crazy kid, like a hoodlum, like, he's gonna be a criminal or something. Like, I could see them thinking that. And then adulthood comes and you figure things out on your own. And the values that they instilled grew, the seeds they planted eventually grew. So it's, a lot of it's about timing, too. You don't really know when someone's gonna blossom. So you just kind of have to plant the right seeds.

• 35:03Speaker 02

  And then also recognize that they are individuals, they are themselves, they are their own person, and they're going to do what they're going to do. But you have to sort of. Sort of just hopefully infuse them with enough stuff and plant enough seeds that they grow into great wonderful people.

• 35:15Harry Stebbings?

  Really personal. Do you tell them that you're proud of them and that you love them a lot? I find that to just be, you know, when I think back to my parents, that was so transformative to me, just believing in myself.

• 35:24Speaker 02

  Constantly, to the point where like my six year old, my two year old loves everything, but my six year old is annoyed by it. Theo's in a, Theo, I love you, you know, I'm so proud of you. And he just like hates that, but that's okay.

• 35:34Harry Stebbings?

  Tell me, there's an age when they say, keep it coming, keep it coming with the debit card, with the credit card.

• 35:40Speaker 02

  Yeah, yeah. But I, but I, but I say it all the time. My wife says it and I think we're very, very loving in that way and supportive. And one of the things that really left an imprint on me is my parents, I was an only child. So like they gave me a lot of freedom and also gave me a lot of attention. But when I was in high school and junior high and into sports, there were some sports I was really, really good at. So I was like extremely good at track. I was very fast. I loved basketball. I made the team for the freshman year, but I barely played because I wasn't good enough. But my parents came to every basketball game, even though I didn't play. I sat on the bench. They still came to every game. And then when I was really great at track, they were at every track meet. But it's easier to come to every track meet when your kid's great. And it's probably harder in some ways to come to something when your kid doesn't play, but they were every single thing I ever did where they could be supportive.

• 36:19Speaker 02

  And seeing them in the stands and knowing they were there meant everything, even though probably at the time, you know, when you're a teenager, you're like, eh, parents, you know, whatever. But looking back on it, it was very formative and very important. So I want to be there for my kids in all those same ways.

• 36:33Harry Stebbings?

  Uh, but I do want to move into my favorite, Jason. It's the quick five. So I say a short statement and you hit me with your immediate thoughts. So you ready to dive in?

• 36:40Speaker 02

  Let's do it.

• 36:40Harry Stebbings?

  Okay. So the favorite book and why?

• 36:42Speaker 02

  Currently in Praise of Shadows, which is mostly about Japanese toilets.

• 36:48Speaker 02

  And it's just like, but not like the modern Japanese toilets, but about light and shadow and texture and materiality. And consideration of space and feeling. And it's just, it's such a wonderful short read. And every time I read it, I love it. I just love it. It's fascinating.

• 37:03Harry Stebbings?

  Tell me, what's the hardest element of your role with Basecamp today?

• 37:06Speaker 02

  Managing 60 people is just hard. This is the biggest we've ever been. It's just hard and I don't like it most of the time. I don't like that part of it. I don't like that people maybe sometimes don't know where I stand on something, even when I explain it. And this is my fault, not theirs. It's just harder. It's Harder to communicate, it's harder to be clear. I feel like there's a lot of more explaining myself than I'm used to. But that's the deal and that's fine, that's part of the role. But that's something I just struggle with, to be honest.

• 37:29Harry Stebbings?

  You said managing a team of sixty there, again, I've got your tweets in my head.

• 37:33Speaker 02

  Yes.

• 37:34Harry Stebbings?

  You said never manage a team, you might lead a team.

• 37:37Speaker 02

  I should have said, leading a team of sixty people and explaining everything. Like, what ends up happening is that it used to be that you could sort of say something and everyone sort of understood what you meant. And now it just takes a lot more to explain exactly every decision and why. And it's ultimately a good thing, it's just harder, that's all.

• 37:53Harry Stebbings?

  No, I totally agree, and your words have more weight. And I think you need to be conscious of that.

• 37:58Speaker 02

  For sure, yeah, no doubt.

• 37:59Harry Stebbings?

  What three traits would you most want your children to adopt?

• 38:02Speaker 02

  Respect for others, respect for nature, and curiosity.

• 38:06Harry Stebbings?

  Tell me, which leader do you look up to and why?

• 38:09Speaker 02

  I know this is kind of a cop out, but I mean it, like, it's more of a hybrid. I don't look at a person, I look at character traits of different people. And I respect those individual bits of different individuals. So there's not like a leader. That said, like, I like leaders who are very straightforward. So when I think about that, I think about people like Charlie Munger. Jeff Bezos is a very clear thinker and explainer. Anyone who can just, you hear what they're saying or you're reading, go, I got it. That's the kind of general leader that inspires me. But also the other one, I guess, would be somebody who helps people get better at what they do. That's what I'm trying to do more now is, is trying to help people grow versus like me growing. I grow by helping other people grow. That's not a great answer to your question because it's not specific. But that's all that came into mind, to be honest.

• 38:51Harry Stebbings?

  What do you think of the current VC ecosystem? We see these price rounds at, you know, billion dollars for pre-revenue companies. We see huge funding rounds, we see just so much, frankly.

• 39:01Speaker 02

  This is a softball. I mean, I don't understand it. I'm very much like an economics one-on-one kind of basic guy when it comes to this. Like, companies that make money are, I think, great companies. I mean, they can do bad things, but like economically, great companies. Make more money than you spend, I'm into that. Figure out how to make money later, not so much into that. And I really don't understand those kind of valuations. So it just doesn't make sense to me. I'm sure I've missed many opportunities getting involved with some of them. For example, like, Clubhouse is a great example of this right now. I am exceptionally bullish on Clubhouse.

• 39:30Speaker 02

  So than I've been about any company I've seen in a long time yet. They don't make a penny. They're probably losing a ton of money because like it's expensive to do what they do. And I know they'll probably figure this out down the road, but they are a company I would actually bet on. Even though they go against my fundamental principles of like, come on, a business model is part of your business. Figure that part out. So there's always exceptions, but generally I don't get it. I don't get it. It doesn't make any sense to me.

• 39:55Harry Stebbings?

  Did you invest in 12 house?

• 39:57Speaker 02

  I would like to, but I haven't because I don't know if I could. I've never been asked to and I'm not an investor, so I don't go after it. But I would, if I had the chance, I would, and I'd actually probably make a very big bet on it. So if you can help me with that, let me know.

• 40:08Harry Stebbings?

  Tell me, what about the one, what do you believe the most around you disbelieve?

• 40:11Speaker 02

  I would say probably that sleep is going to be one of the most important topics over the next decade. Now, I don't know if people disagree with that or not, but I don't hear enough people talking about it.

• 40:21Harry Stebbings?

  Do you sleep a lot?

• 40:23Speaker 02

  I try to get eight hours a night. Yes. And I tend to get somewhere between seven and eight. Sleep is the most important thing you can do to improve your life and improve everything. And I don't think it's yet mainstream enough, even though we all do it. There's a book I read, a wonderful book. I highly recommend you read it called Why We Sleep by Matthew Walker. And when you read that book, it actually is one of those books that will change your life if you follow the ideas in it.

• 40:47Harry Stebbings?

  Next decade, what does that look like? Next decade for you and for Basecamp, how do you think about it?

• 40:52Speaker 02

  Don't know. I don't think about it. I don't think about it. I think six weeks at a time. I think six weeks ahead of time and that's it. We're pointed in a direction, but it's six weeks at a time. That's the only thing I think about. It's the only thing I plan. I mean, I've got like random ideas in my head about like this year, but like it's six weeks at a time. That's it. And that allows me to keep thinking. What I don't like about long-term planning is you kind of stop thinking. It's like you thought something and now you live it out, but like, I don't know what the hell is going to happen next year in five months. I don't know. Like, why would I ever set myself up to have to do what I thought? How about can't I do what I think? So that's what I try to do is to do what I think, not do what I thought. The only way to do that is to keep making it up as you go. Make it up as you go and don't worry about the fact that you have no idea where you're going.

• 41:35Harry Stebbings?

  Jason, as I said, the things that give me energy is like, honestly, is things like this where it's like completely unscripted. But this was so much fun. So thank you so much for doing it.

• 41:43Speaker 02

  My pleasure, man.

• 41:46Harry Stebbings?

  That was just one of my favourite shows to do, as you heard, just such a natural conversation. I had this brilliantly worked out schedule, it was very precise and then we obviously just completely went around it. I want to say huge thank you to Jason for being so accommodating there. If you'd like to see more from us, you can on Instagram at H Stebbings 1996 with two Bs. I always love to see you there. But before we leave you today, I have to say I just love using Angel List's fund admin platform to manage my investments. The team and platform at Angel List takes care of all my back office needs so that I can focus on working with great founders. Leading fund managers have made over 10,000 investments into 6,000 startups via Angel List, all online and all in one place. And with recently announced Rolling Funds, you can easily find and invest in

• 42:27Harry Stebbings?

  these top fund managers on angellist.com/rolling. And speaking of amazing products there with Angel List, last month I had Jeff Sibber and Wayne Chang on the show from Digits. Simply put, they're two of the best founders I've met and they're creating the most intuitive financial software you've ever used, automatically analysing your company's spend and visualising it for you as it happens. Hone in on recent activities, trends, anomalies, or any question you have in just a few clicks. And unlike every other financial software, their integration is not weeks, it is just a few clicks. I have to say the product is just beautiful and you have to check it out and so you can do that on digits.com. And finally, I've always been a big history man and so I want to talk about Cooley, the global law firm built around startups and venture capital. Since forming the first

• 43:09Harry Stebbings?

  venture fund in Silicon Valley, Cooley's formed more venture capital funds than any other law firm in the world, with 50-plus years working with VCs. They help VCs form and manage funds, make investments, and handle the myriad of issues that arise throughout a fund's lifetime. So to learn more about the number one most active law firm representing VC-backed companies going public, head over to cooley.com, check out cooliego.com also. As always, I so appreciate all your support and I can't wait to bring you an incredible episode this coming Thursday with David, the founder and CEO at New Bank.