The Tim Ferriss Show - #195: David Heinemeier Hansson: The Power of Being Outspoken

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Starting point is 00:03:15 whether that be sports, military, entertainment, business, finance, or otherwise. And this episode, we have the fearsome Dane himself, known as DHH, David Hannemeyer Hansen, lots of vowels and a double S in there, just like my last name. This is a multifaceted character, and we delve into a lot of stories and details that I don't think he's discussed at length anywhere else. He is the creator of Ruby on Rails, and we'll certainly dig into what that means for those of you who are not in technology. He is a founder and the CTO at Basecamp, formerly known as 37 Signals. He is also a bestselling author and known for being very, very outspoken. We also, I suppose, meander into a discussion of the power of being outspoken. And he's also a world-class race car driver. He is a Le Mans class-winning racing driver, despite the fact that he didn't even get his driving license, his driver's license,

Starting point is 00:04:21 until he was 24 or 25. You can find him a number of places on Twitter at DHH medium, where he writes longer form content at DHH as well. And on Instagram, he does spend a lot of his time taking photographs at DHH 79. That might be lesser known, but certainly check that out. And we really bounce across quite a few different subject areas. We talk about tech. We talk about running a profitable business without venture capital for more than a decade. We talk about his 13 years of open source with Ruby on Rails. And we talk about stoic philosophy. We talk about flow states. We talk about racing. And I will warn you in the very beginning for the first, I don't know, 15, 20 minutes, we have a lot of racing talk. It is

Starting point is 00:05:09 relevant to what comes later because we're looking for, again, parallels across disciplines and first principles. So I'm not going to dig into a bunch of stuff that you've heard a hundred times about DHH before, if you're familiar with him on Wikipedia or in his books, for instance, we wanted, or I should say I wanted, that's the royal we, to dig into his rules. What are the rules he follows? The philosophies that he uses as his personal operating systems for creating excellence on this planet. What does beautiful code mean to him? How does that translate to other areas, et cetera, et cetera, et cetera. So without further ado, as I always say, please enjoy my conversation with DHH. David, welcome to the show. Thanks, man.

Starting point is 00:06:00 It has been a long time since we've chatted. And we were, of course, talking before we started recording. And I couldn't pin down how we first came in contact. And I think where we arrived was somehow through Seth Godin, when you guys were first considering publishing rework, we connected to talk about all sorts of things ranging from split testing titles to the entire publishing process. And that must have been what, six years ago? Yeah, I think 2010 was when we started shopping our manuscript around. Or maybe that was even when we published the book. It's so weird. It feels like it was just yesterday and then six years later, here we are. But I mean, it started in part in the same way that I started on learning a lot of things.

Starting point is 00:06:50 I try to identify whoever in that domain I want to learn from and then figure out a way if I can either learn from them directly or indirectly. And, of course, if you can have a direct link, that's the best. And I had read For Our Work Week sometime in advance of that. And so I had Jason, my business partner and co-author of Rework. And we were both just impressed with that. And we're like, hey, this is kind of the path we want to take. Let's see if there's a way we can learn from what you've done. And oh, here's a connection.

Starting point is 00:07:21 Oh, Jason knew Seth and Seth knows. And there we go. So we're going to get into certainly programming and everything else. But since you talked about seeking out experts, I don't actually know the answer to pretty much any question I'm going to ask because that would be boring for me. But you, I'm just looking at some cliff notes that I have here to go off of, but I didn't know this part. So you did not have a driver's license at 25. Is that right? Around that? That's right. Okay. And then let's flash forward. What happened at 34?

Starting point is 00:07:58 I got to stand on the podium after 24 hours of racing in a town in France called Le Mans, in the greatest endurance motor race in the world, fulfilling my dream of not only just completing that race, but winning our class there. And all that in nine years, from not having a driver's license to getting a driver's license, learning how to drive a normal car, and then getting into racing and climbing the ladders of racing until you're at the top. So if we were to try to find the parallel example to you reaching out to me, and I'm sure other

Starting point is 00:08:41 people about publishing, two questions. One is, how did you decide? Was there a moment or a dinner or a conversation where you decided, yes, this is what I want to do? And then second, how did you start trying to figure out how to go about it? Sure. So one thing I'd, since the mid nineties, I, on Danish television, just tuned into this race, the 24 Hours of Le Mans, caught it a number of years, and I was just fascinated by the speed, the teamwork, the endurance, just the whole process of driving around in circles for 24 hours straight and making the machine last, making the humans last, and found it that absolutely fascinating. And then in the late 90s and early 2000s, a fellow Dane, we're talking about Denmark here, there's a population of 6 million people,

Starting point is 00:09:33 6 million Danes total. So when another Dane does something remarkable on the world stage, other Danes take note. Maybe that's true of all countries, but I think it's especially true of small ones because we just don't expect it, right? You don't expect that out of such a small country, you're going to have someone who reaches the peak. And we had Tom Christensen, who now goes by the name Mr. Le Mans because he's won the race nine times, started winning races and started winning the 24 Hours of Le Mans just over and over and over again. So that, of course, piqued my interest, too. I was already sort of interested in the race. Then the Danes started winning it all the time.

Starting point is 00:10:11 This is still before I even have a driver's license. But this just plants the seed, right? I'd already been playing lots of racing games. I loved racing games all the way from the Commodore 64 to Sega and Nintendo's and Amiga and all sorts of video games. Probably racing games was one of my favorite genres. So played a lot of video games. Then all of a sudden at 25, I want to go on a vacation. And I go, actually, if I go to Brazil or the United States and I don't have a driver's license, that's really annoying. Like you want to arrive there and you want to rent a car the funny thing is I wouldn't even think about

Starting point is 00:10:48 driving around Copenhagen because that seemed like such a foreign concept I'd already made it 25 years in Copenhagen on rollerblades and the occasional bike in between them getting stolen and that seemed to be well sufficient Copenhagen is not that big of a town it's very well equipped for people who want to bike or rollerblade or whatever So it wasn't even to use it in my own country. It was like, I want to go on vacation and I want to be able to rent a car. So I learned how to drive a car in Copenhagen, which was in itself a funny process because most people, even in Copenhagen, I think if they learn how to drive a car, they learn how to drive a car at 18 or whatever, right? So it's kind of like new and exciting or what have you. And here I am, 25, I'm trying to learn how to drive a car. And I, at that point,

Starting point is 00:11:34 I already knew programming. I had already worked on a number of domains that I had taken sort of a methodical approach to. And I took a pretty methodical approach to learning how to drive the car too, to the point where the guy I was doing the exam with was remarking on the fact I was self-commenting. I didn't even realize that at the time. The guy was rating me whether I pass or I don't pass it right next to me in the car, right? I'm driving around and I'm like, oh, I should have turned in a little sooner there. Oh, I should have turned on the blingers there. And it was funny. He told me, oh, you pass, of course. But what was really remarkable was that you were narrating the whole process. I was like, oh, yeah, actually, I don't know.

Starting point is 00:12:14 Maybe that wasn't so smart. I guess it worked out. I was basically pointing out all my own flaws because that's how I learned. So that's how I learned how to drive a car. Then skip forward just a little bit. I'm actually, you know, David, I'm sorry. I'm going to interrupt just for a learned. So that's how I learned how to drive a car. Then, um, skip forward just a little bit. I'm actually, you know, David, I'm sorry. I'm going to interrupt just for a second. So two things. The first is, do you do that self commentary for a lot of things? Yes, you do. There's like a running narrator, just running in my head when I'm trying to learn

Starting point is 00:12:41 something constantly pointing out, Oh, you could have done that a little better, or let's try this next thing on the new run around. And I mean, in racing in particular, you get that enjoyment a lot because the lap isn't that long. It's usually two minutes. So every two minutes you get to reset. You have a take two. Yeah, exactly. You have a take two and take three and take four. And by having that running commentary, I'm kind of taking notes on this is what I have to tweak next time around. And I do the same thing in programming too. I mean, I'll look at a piece of code and I go like, okay, let's get this working. And then I go back. Okay. Take two. Let's make this right. Okay. Take three. Let's make this beautiful. Okay. Take three or take

Starting point is 00:13:22 four. Let's simplify this. Okay this okay take five like just having that commentary all the time about where can i improve where can i get better that's i don't know where it comes from but that's just how i've always gone about learning things did either of your parents do that or any i don't know if you have siblings but a lot of these things on learning techniques i've talked with other people around them like these things have been codified and I would go like, oh, that's interesting. I just, I didn't know that that either had a name or that was how people were doing it. That somehow, I think I just stumbled over the fact that,

Starting point is 00:13:53 oh, if I do this, I learn faster. Oh, let me just do more of that. Right. Of course, that makes perfect sense. So I interrupted you there. Oh, the other second part, I apologize, was what did you do differently compared to other people when learning to drive for that initial driver's license test? Is there

Starting point is 00:14:12 anything that you recall doing differently or focusing on in particular? Yeah. Yeah. It's funny. One of the things that I, and I had these things with programming too, where I'm actually a slow learner at the beginning because when I don't understand how something works, I have a very hard time putting it into action. I can't just, oh, let me just clone whatever it is you're doing. I don't understand it and then do it well. And I remember in Copenhagen, all the cars we were being taught to drive on were all stick cars, manual cars. So you had to operate the clutch yourself. And I could not get my head around the fact that clutch engagement, lifting the pedal from the floor was such a fuzzy process. Like he couldn't tell me how much do I have to lift my leg to get

Starting point is 00:14:55 the right clutch engagement. He's just like, Oh, just go on the feel of it. And I'm like, no, no, I want to know like, is it 30 degrees? Is it 70 degrees degrees like how far does the clutch have to come up the floor and i must have saw that car a hundred times um because i just kept going like i'm not just going to do it if i don't understand how it works i'm going to figure out like how this clutch thing works because then i mean i'll know how it works and and that will help me move forward but it just other people would walk in right and they'd just go like oh you just go how to feel and they put in in the clutch and they'd let it out and just give it a bunch of gas and somehow it'd work and they'd get off the writing quality of the of the text so we would have both the practical part where you go out and drive the car and then you'd have like the theoretical part where you learn about the rules and so forth and just remember being remarkably impressed by the narrator of this

Starting point is 00:16:02 incredibly dry material right like oh if you see this sign then like it means this and that and the other thing and the narrator was just entrancing because every single word had just been picked to perfection in a very bureaucratic stilted way but still i was just oh this is just so fascinating so it actually helped me learn the material that much quicker because i was just paying so much damn attention to how the guy was telling us how these signs were and how far from the curb you had to stop. And it's just like, wow, everything can be interesting if you find a way to look at it the right way. And if you have a way of telling it in the right tone, even if it's the driest material in the world, and he wasn't trying to make it peppy, it wasn't like the narrator was being funny or whatever, just being ultra precise with every single word weighed and picked to perfection. three example of making your code beautiful. I think that it seems to perhaps relate to why

Starting point is 00:17:07 you're entranced by the precision of the language and the elegance of the language in that presentation for driving. Exactly. Same thing, right? Ever since I've tried to strive to write code the way that whoever wrote that instruction manual for how far away from the curb you should park could write, which I actually think correlates pretty well to programming. We do a lot of things in programming that aren't inherently interesting. If you read some of the programming grades, they talk about, oh, we were building a salary compensation system for Chrysler or something, the C3 system, which is kind of legend now in agile world. And you go like, that's got to be the most boring domain in the world. Like you're programming a system to come up with all sorts

Starting point is 00:17:49 of deductions and exceptions and so on. How is that interesting? And oh, little do you know, once you dig into it and you unravel the mechanics that go into it is just fascinating. And I think that some of those experiences have taught me that anything that looks boring on the surface, you just haven't scratched far enough. Keep scratching and everything becomes interesting. No, I could not agree more. And two things came to mind. The first was, and I'm going to be wading into dangerous territory for me because I'm getting outside of my competency real quick, but it seems like the instructional videos that you were watching are almost an algorithm for human beings, right? So you're still, it was imparting instructions and steps and so on to human operators who are going to be interacting

Starting point is 00:18:37 then inside this machine. The second is my personal litmus test for good writers is, at least in the world of nonfiction, those people who can make topics you assume to be boring, absolutely riveting, right? Because anyone can take the most exciting topic in the world. And even if they just throw together the equivalent of spaghetti code, right? It's just like sloppy prose as long as the story is really strong and they were given kind of a Willy Wonka golden ticket in terms of subject matter you don't have to work very hard on the words and the precision but then you take someone like John McPhee for instance anyone who hasn't read his stuff should MCP HEE he's written entire books on oranges he's written entire books on hand-carved canoes.

Starting point is 00:19:28 He wrote one on Plymouth Rock. He wrote an entire book on a single tennis match between Arthur Ashe and I'm blanking on the second competitor named Levels of the Game. But his ability, he can take any subject you could assign him and make it much like Michael Lewis, right? I mean, he wrote a thriller about credit default swaps and just make it riveting. So coming back, I know I'm prone to making us digress, but so you pass your driver's test. At what point do you decide to race? It's funny, I didn't even decide. I had a friend who I'd actually met online again. I mean, the whole reason I came to the U.S. was because I met a guy online, Jason Freed, through a blog and an email. And we got working together. And a couple of years later, I moved to the U.S. to work with him full time. And here's another guy I met online on a forum discussion board for cars who said, hey, I know of this racetrack. That's just 45 minutes out of Chicago. Do you want to come?

Starting point is 00:20:35 And it's like, cool. It sounds interesting. Let's go down there. And we come down to the track and he had set up with another friend that I could try a race car. Up until that point, I don't know, maybe I remember, maybe I had driven once with like a street car on a course or something. But this was a real race car. This was a single seater. You sit in the middle of the car. The wheels are exposed. They kind of look like miniature Formula One cars. And I get a chance to ride in this thing. And I just remember, first of all, these sessions were about 30 minutes long. You get out on the track, you drive around for 30 minutes or maybe it was even just 20 minutes.

Starting point is 00:21:13 And it felt like it took 30 seconds because I would just see the flag right away and I'd be like, wait, what? I have to come in? I just started. So time was already being distorted, which is when you know you have a good time, is when you can't keep track of time, right? And not only that, I was just absolutely fascinated

Starting point is 00:21:32 from the get-go about this whole closed system, that we have this track, a lap around the track was about a minute 30, and you would get instant feedback on how well you were doing every single time you came around. There was a clock telling you, oh, this time you did it in one minute, 31.4. Then you go around one more time, and it's one minute, 30.8. And you go like, man, I just shaved off six tenths. This is the most exciting thing in the world. And I mean, that's even taking it beside the fact that it's exciting.

Starting point is 00:22:02 It's a loud car, and it's's shaking and there's the element of danger. You could go off course, you could hit something. But just the closed loop system of improvement was absolutely intoxicating. It was kind of like you just had like a bottle of flow. You could just go open your fridge and like, oh, I'd like some flow, please. Can you get me into the flow state where you lose track of time and where you just have such a great experience learning and getting better? Like that's how I felt the first very, very many times I got into a race car was I could just switch on flow, which was something I had discovered in programming a fair amount. But

Starting point is 00:22:39 I find at least in programming, it was a little more elusive. It was like the best programming sessions I'd have flow. But then I'd also have a fair number of other programming sessions where I wouldn't have flow. When I stepped into the race car, I just felt like, oh, I could just... You turn the ignition and flow comes. And that was just magic. Why do you think it was more elusive in programming and can you identify any common factors for the sessions that had flow or that didn't have flow? I think part of it with racing was just the

Starting point is 00:23:14 intensity level was at a hundred percent right away. You had, as soon as you stepped into the car, you had maximum danger. Actually, you had more danger in the beginning that you will have later on because it's much more dangerous to drive a car on the track when you don't know what you're doing than it is later on. Versus with programming, I didn't get flow until I was, I mean, I shouldn't say that. I didn't get great consistent flow in the quantities that I'd like to enjoy it before I was actually a fairly well-developed programmer because that was when I had enough of an eye for the whole scope of programming to really dive into, oh, let's make this beautiful.

Starting point is 00:23:52 Let's make this as simple as possible. When in the beginning, I was just focused on, oh, let's get this to work. Can the PHP page render? Oh no, I get an error. Let me try something else. That was fun. There was glimpses of flow

Starting point is 00:24:06 but the real moments of flow uh i wouldn't get until i was much better where would with stepping into the race car you're kind of forced into a situation really early on where developing your eye for this domain just was i mean it putting a putting it a little bit on a pin, but it was life and death, right? You're going 160 mile an hour. If you don't get this next turn right, at the very least, it's going to be expensive. And then it only gets worse from there, right? Either it's going to hurt or it's going to be really, really bad, or there's going to be an ambulance involved or something else like that. And I think there's just a survival instinct

Starting point is 00:24:48 that sharpens the mind in that sense. That, I mean, when I'm trying to make a PHP page work, if I make an error, it's not like I have to write off a car or go to the hospital, at least not the kind of software I was writing. Maybe you get that if you try to write a pacemaker on your first go or something, but I was just writing information systems and web pages. But

Starting point is 00:25:10 as things progressed, they became more the same. When I got sort of well-versed enough into programming that I had developed an eye for and developed opinions about what was good code and what was bad code, what was smelly code and what was clean code, it became a lot more fun to try to go from, oh, this is just something that just works, which to me then became uninteresting. Any programmer worth their salt, generally speaking, can get something to work,

Starting point is 00:25:39 can get the program to roughly perform the task it's supposed to do. At least in information systems where the domain itself isn't that novel, perhaps, or it's well-established enough that getting things to work, okay, that's the baseline. But beyond that is getting to make it clear, picking the right names, making the code beautiful, making it succinct, simple, all these other pleasures you derive from code as pros code as writing not code as putting mechanical things together and with with racing you you had the

Starting point is 00:26:14 sort of interest right from the get-go because you had this criticality really high criticality but then as you developed it became more of the same like once you start understanding grip and slip angle and all the mechanics of setting up a car in terms of uh caster and rake and right height and you start appreciating the differences between two millimeters up front and two millimeters on the rear or tire pressures it becomes becomes really interesting in a deeper level than just like, oh, I'm just holding on for my dear life. I'm trying to survive. Both things provide flow, but they're different kinds of flow. And perhaps the later part is the more satisfying part, because it's, as you say, when you can write a whole book about a single tennis match,

Starting point is 00:26:59 you've really understood the problem. You've really understood the details that matter. And with programming and with race car driving, once you get into those nitty gritty details of, as I mentioned, all the particulars of the mechanics of a car and slip angle and wear of tires and so on, there's just so many factors. And again, it becomes system thinking, system optimizing, and just a riveting thing of trade-offs and optimizations and so forth that just is the path to flow, is the path to flow. Details, developing an eye, that's for me the most reliable way I've found to cultivate flow. And like you said, if you haven't found something that grabs your interest about a given topic, just keep scratching, right? You haven't dug deep enough.

Starting point is 00:27:48 For instance, I wanted to get involved with archery for a very long time in a serious capacity. And I only started doing it about a month, let's see, three months ago. And part of what triggered it was an Olympic archery coach who suggested I get a book called Shooting with Back Tension. I think I'm getting the title right. It's an entire book about how to use mid-back tension to fire more accurately and make the process more replicable. And for whatever reason, I just found this so fascinating that that is what enabled me to finally take it seriously because that was the hook.

Starting point is 00:28:32 That was the lure that I needed to buy it. Let's rewind the clock a little bit because we've alluded to it, but there are people who won't have the history necessary to put some of this in context. The story of not wanting to be inconvenienced in, say, Brazil or US by not being able to drive, that sounds like at least one of the primary catalysts for getting a driver's license, that sort of potential frustration. Correct me if I'm wrong here, but the programming came out of starting a gaming news website. You mentioned the racing games earlier. Is that, how did that come to be?

Starting point is 00:29:18 How did you start coding? It was actually exactly the same thing. As I said, like I learned how to drive a car because I didn't want to be in Brazil or in the US, stranded or reliant on buses or whatever that would make it hard for me to enjoy that vacation. With programming, I came to the same conclusion, actually. I had almost consciously avoided becoming a programmer for a long time because I grew up with a lot of programmers as friends.

Starting point is 00:29:51 And I was involved with computers, not as a programmer, but around the edges of it. I ran what was called a ware site, a BBS, a bulletin board system before the internet, where we trade pirated software and so on. I was well involved in the scene of computers, but I wasn't a programmer. And I had kind of decided at some point, I don't know, 13, 14, when I had these programmer friends and I saw what they were doing and I thought like, that's not for me. Like programming, it kind of looks like math and math is interesting, but it's not really what I want to spend my time on. Programming is not for me. So it took several years after that until I started working with the internet. I started working on these gaming websites and I

Starting point is 00:30:29 would pester my friends, my programmer friends, hey, can you help me make this happen? Can we make a content management system before things were called that? And they would help me and I would kind of just get frustrated because I felt a little helpless. I felt I couldn't be self-sufficient. I couldn't just make the things happen that I wanted to make happen in much the same ways that I wouldn't want to arrive in the US or in Brazil or whatever I had imagined of these destinations that required a car and feel helpless, like I was dependent on someone else. And I think that's a thread that goes through a lot of things and why I choose to do certain things. I have definitely a streak for wanting to be self-sufficient. And that self-sufficiency then led me to think like, oh, okay, fine.

Starting point is 00:31:14 I'll learn ASP or whatever the Microsoft thing was that we were using at the time. And then after that, okay, fine. I learned this PHP thing just such that I can make the other thing that I really want happen. I wanted to make this game. So it wasn't a decision to become a programmer. It was like, all right, you know what? I will just figure this out so I can do triage so that I don't have to wait for A, B, and C person to get this done a week from now.

Starting point is 00:31:36 Exactly. That was it. It was a tool thing. It wasn't like, oh, this is my new pursuit. I'm going to be a programmer. Absolutely not. It was, I wanted some programs. I wanted some websites, actually. And I found out, oh, you kind of need to do some programs to do that. I

Starting point is 00:31:50 taught myself HTML and CSS and JavaScript to do some of those other things. And I just resisted learning programming for a long time simply because I thought, oh, it's math. It's hard. I had these notions about what programming was because I had observed the programming friends I had make demos and 3D graphics and games and all sorts of furniture together. Which screwdriver do I have to use? Okay, that one. And then let me just read the instructions. Let me just try to put it together. It's not because they're trying to become a carpenter, right? I just want this desk put together. I'm not trying to make a career as a carpenter. I just want a desk put together and Ikea has some instructions and I need a screwdriver. That was how I felt about it. And I felt that way about it for several years. And it was just funny because it was kind of one of those things that snuck up on me where when race car driving, for example, like there was a

Starting point is 00:32:53 lot of intent. I did the first thing and I immediately got hooked with programming. No such thing. I did the first thing and I actually didn't enjoy it at all. I didn't enjoy programming very much. I thought it was just kind of an inconvenience, but I just kept doing it. And as you say, you just slowly start unpacking the onion and the further you get into it, the more rings you get into it, the more interesting it becomes. So fast forward a couple of years in 2001 or whatever, I'm done with this gaming website i had been building for a danish incubator there was a lot of danish um dot com inspirations going on at the time and one of the things was incubators who would throw money at kids like me to build things with no idea of profits or a business model or anything else just because eyeballs um anyway i kind of saw the writing on the wall um painted pretty clearly when dot com bubble bursted in the u.s and i thought yeah let

Starting point is 00:33:53 me just go back to university for a while i had stopped after high school went straight into building these gaming websites of various kinds done that for what three years or so and then the whole bubble thing went pop and I went, I'm not a hundred percent sure what else I'm going to do. I'm not going to keep just spinning around the scraps here. Let me just try to learn something. And I got into a program for business administration and computer science. But at that point, like the snowball was already rolling. I had already gotten enough now of a taste of programming, again, not because I wanted to, but because I had to,

Starting point is 00:34:28 that it was kind of getting more interesting. And I was getting more fascinated by just building information systems of various kinds. And these gaming systems, that was all they were, right? Like they were content management systems, they were message boards, they were all these kinds of information systems. And it had just really piqued my interest.

Starting point is 00:34:46 And I hid away in university for three years getting this degree. And at the same time, then I really got into it, right? Not so much because of the schooling, because schooling was all about some nonsense Java stuff. I guess it was good to get exposed to that. That did provide influences for later work. But it wasn't the schoolwork that was interesting. It wasn't because we were getting assignments that I thought was so, so fascinating.

Starting point is 00:35:12 It was all the stuff I was doing on the side. And one of the things I was doing on the side to catch the tales of the story here was I started working with Jason Fried, who I would end up becoming a business partner with. And that stuff then went from, oh, okay, I guess this is kind of interesting to like, oh, this is actually pretty interesting to all the way until 2003 when I finally find the love of my programming language life in Ruby

Starting point is 00:35:38 and go, oh, actually, this is what I want to do with my life. How did you experience those jumps? In other words, what made it interesting? Because there are certain moments in time where I can pinpoint for different skills or topics. It went from not interesting to interesting, right? It's kind of like not boiling, boiling. There was a really clear shift. For you, what was that for programming? And then why? I mean, I'm sure you might be sick of explaining this,

Starting point is 00:36:12 but so the first is why programming generally? When was it like, oh shit, this is really interesting. And the second is why Ruby? Sure. So the first thing certainly came first, which was why is this interesting? And the first big certainly came first, which was why it's interesting. And the first big aha moment I had was when I reached self-sufficiency, when I got to a level

Starting point is 00:36:34 where I could make a whole thing, a whole feature, a whole part of the site without having to consult someone else, without having to stumble through it, where I could actually just put this desk together. And it was a pretty good desk. It served this purpose. I could put things on it. It wouldn't fall down. And I'd go like, huh, that's actually pretty cool. You can take an idea, and you can start writing things in a text editor, and all of a sudden,

Starting point is 00:37:00 you have an information system? Wait, that's actually pretty cool so that was the jump point from the standpoint of i like the outcome that wasn't a jump of the i like the activity itself i just i really like the outcome i really like the self-sufficiency and i like the idea of taking nothing and turning it into something and then i had perhaps uh another jump when i started working with other people um i started working with jason uh jason fried um as i said was not only a business partner at base camp but he was also the first guy who paid me to program all these other endeavors i had a program were more like side shifts.

Starting point is 00:37:47 They were not the main thing I was supposed to do. I was doing this program for the gaming websites, not because someone had hired me as a programmer, but because they had paid me some money to run it or I was just interested in running it. And then I just, through that, gotten self-sufficient enough that I kind of knew my way around PHP at the time. And then Jason, I ended up connecting with him and he ended up hiring me paying me the grand sum of 15 an hour which um i was gonna say back when the dollar was worth something um now the dollar is actually worth a lot more again um but i mean again my comparison frame was okay i could either get 15 bucks an hour working for some strange american i had only met online from copenhagen denmark or i could go do another

Starting point is 00:38:33 student job of i don't know filing papers in the library or something so hey that seemed pretty good to me right like i get to do some programming stuff which i'm getting more interested in and someone is paying me 15 bucks an hour which which by the way, funny anecdote on that, it wasn't even 15 bucks an hour because back then you couldn't really easily send money. So you got like a 20% transactional cost. Exactly. He would send goods. He would send Apple goods. So he would send me like the very first iPod was part of my payment. I got an iBook, a bunch of kind of stuff like that. Anyway, just wanted to think back about it.

Starting point is 00:39:09 And then I worked with Jason for a couple of years on a variety of client projects. 37 Sickles, which was the name of the company before we changed it to Basecamp, was doing client work, mainly design work. And I would team up with them and work on the programming stuff. But the big jump where I went from just liking the output to loving the activity itself really came with Ruby. And Ruby, I discovered, I think maybe late 2002, I had a small look at it. And then again, in the mid of 2003, I really dove into it because we started working on Basecamp, our first sort of major product together, Jason and I. We had worked on some other stuff earlier, a site to keep track of your books called Single File that I had made in PHP. And that was good fun. It was a good learning experience.

Starting point is 00:40:03 It never really took off. It didn't go anywhere. So we scrapped that a few years later. But then this Basecamp thing came up. We wanted to keep better track of our customers, all the clients we were working on. We were doing everything over email. We just kept dropping the ball. All the same stories of when you try to manage projects and people over email.

Starting point is 00:40:21 You go in the beginning, oh, this is wonderful. You can just send an email. And then at the end of it, you go like, ah, shit, where's that email? I can't find it. Oh, did you tell Peter about this? Oh, no, I thought you. And he doesn't have the right version of the file. All the usual stuff you get when you try to do that you still get today when people try to coordinate projects over email, right? So we thought, hey, we're building websites for clients. Can't we build a piece of web software that would make this stuff easier? And so we did.

Starting point is 00:40:48 So as we started on the project, I went, hey, this is not a client project. No one is saying you have to use PHP, you have to use ASP, you have to use Java. No one is mandating technology we have to use about this. And I had read about Ruby from some other programmers that I respected, Dave Thomas, Martin Fowler, and others had been sort of writing in industry magazines about this wonderful language that they also couldn't use at work, but they used it to explain various concepts. And I thought, hey, here's a chance. I can use a brand new programming language. Let's just give it a try. And I set myself this challenge, basically.

Starting point is 00:41:26 If within a week, I felt like I could get things up on the screen that talk to a database and so forth, it'd be enough to continue. And if within a month, I felt like, okay, I can build all the things that I realistically would need to build something like Basecamp, we're going to do it. And of course, it took like three days for me to be like, oh, I can make things come up on the screen, I can make everything happen. And then it took another, what, four days to go like, yeah, I don't think I need to programming it in any other programming language ever again, if I can help it. This is wonderful. This is like, I liken it to sort of you take LSD or something. I have this gif of the guy that just goes like, where his mind is blown and he sees the galaxy and so forth.

Starting point is 00:42:13 That was a little, without over-dramatizing it even more than that, what I felt like, right? That this is what I've been waiting for. This was the glove. And it just fit my brain so perfectly i just went wow this is something else and it's so deep i can keep pulling on the thread i this was easy enough to get started that i didn't get frustrated but deep enough that i couldn't even see the bottom i just kept going and going and going i read more and more of the standard library for Ruby.

Starting point is 00:42:46 I read basically every library that had been released at the time. I just went, this is truly something else. And then I started building. I just started building, building, building, building. And the purpose in the beginning was just to build Basecamp. And what I found was I was trying to put this desk together. And, okay, I could see this of like this is a beautiful tree. Like this is the sort I want to use for it.

Starting point is 00:43:09 But like there's no hammer. There's no saw. There's like I have to build a bunch of these tools first. But I go like, oh, no problem. This is wonderful. I'm having such a great time. I don't mind that I have to build all my tools for myself first. So I started building all these tools, which then became the web framework

Starting point is 00:43:25 Ruby on Rails. And that was basically my first project in Ruby. And I'd been a professional quote-unquote programmer and someone paid 15 bucks an hour for two years at the time. But it was just that aha moment where you just go like, this is next step.

Starting point is 00:43:41 And it really, seriously, it didn't take that long, maybe a couple of months into it where I just went, this is some of the most fun I've ever had in my life. This is some of the most rewarding, interesting challenges I've ever had to tangle and deal with. And there's just more every day. I simply just could not wait to get back to the keyboard and develop my eye dig deeper get better um

Starting point is 00:44:07 it was just i i really felt like i'd found something like you're not supposed to as in like this is almost too good here this is like i i knew programmers i knew they could have fun but i didn't know it could be this good, especially because I'd been doing some version of programming for years in advance, and I never felt like that. Now, you mentioned there are a bunch of things I want to dig into because I love this story. The first is, and for anyone who's wondering, does Tim program? I am not a programmer, but I did have, as an aside, a very fun experience with Chad Fowler. He's not related to the Martin that you mentioned, is he? Nope. Nope. But I know Chad quite well as well. And he was one of the early Ruby guys and

Starting point is 00:44:58 really great guy. And he sat me down to walk me through, this was probably, this is after we first met at RailsConf. He sat me down to walk me through the basics of Ruby, comparing it to a language that he speaks, which is Hindi. And because I have some human natural language experience, he was able to walk me through it doing that. And it and it it made sense i mean the way he presented it my question to you is you uh had talked about three days to be able to get it to talk get something to talk to a database right and then four days five days to know that you can build things is that a typical timeline or is that a sort of a beautiful mind timeline for going from one language to another because if i think about say going from maybe spanish to portuguese maybe because it's they're very very similar right but if you're going from spanish to japanese you kind of start from scratch and it would take a lot longer to get conversant in a new natural language. But how do programming languages work? And are you an anomaly in having picked up

Starting point is 00:46:12 Ruby so quickly? I don't think I'm that much of an anomaly because like natural languages, they're kind of families of languages. And so Latin languages or whatever, you can jump from one to another with much greater ease than if you jump to a completely different family of languages like Japanese, for example. So all from the get go, most of the concepts in programming tend to be there's this core set of concept that once you understand conditionals and variables and so on and so forth, you kind of have a good baseline. Right. Perhaps that is kind of like learning Latin and then trying to learn other languages from there um and then ruby really was interesting in the way that it wasn't it didn't come up with a single new idea and as far as i really know what it did was it was like the the master mixtape it was the greatest hits of all the programming languages that went before it mixed together by the the most amazing DJ you've ever heard.

Starting point is 00:47:08 And you go like, oh, yeah, I recognize all the individual numbers here, but I've never heard them composed together like this. I've never heard like, oh, if you speed up the beat like this so they just flow together, it's a new experience. So I kept recognizing all these angles of it. Oh, this is kind of similar to that. But whoa, what a way they've chosen to express it. So the onboarding was quite easy. And I think that's one of the areas of real success that Ruby has had is that for a lot of programmers who've had some experience with programming, it instantly feels familiar. Right. The switching cost is really low.

Starting point is 00:47:45 Yes, it's quite low to at least get started. I mean, to become an expert at anything still takes a long time. And I certainly have thoughts on unrealistic expectations that people have, especially these days about how long it takes to become an expert. But to get started and to get a hold of something and get a taste, get a preview of what this could be. It was like getting sit down and then watch the world's greatest trailer. Like you're like, oh, in two minutes, I really want to see the rest of this movie. Like it's not going to take two and a half hours to watch the rest of the movie. But like just those two minutes was enough to get me fanatically excited about what was going on. And I think in terms of learning that new language,

Starting point is 00:48:28 when you see something that's both the Hessemer condition and it also challenges you in some ways, I didn't certainly know all the concepts that were mixed into Ruby, but I knew enough that it wasn't totally foreign. It wasn't a brand new concept. I didn't have to throw out everything that I knew to adopt it i think that's where perhaps some other programming languages that were more radical like uh lisp or even small talk and the way those languages work they're far more radical right which in some ways is more pure ruby is not a very pure language it's uh as i said it's a dj language it's a remixed language it's a mix-up

Starting point is 00:49:08 of just all the greatest hits ruby didn't come up with very much original content in that sense but that's really how the world at least that i operate in works that when you try to apply sort of that perfectly singular idea it usually doesn't fit because it doesn't doesn't bend doesn't stretch ruby really bends ruby really stretches such that it covers all sorts of different scenarios with just an elegance and a grace on the long timeline you can take any one individual language and you say, oh, Lisp or Smalltalk, and you can apply it to one problem that fits it really well.

Starting point is 00:49:52 And you go like, okay, for that one problem, this probably is the best language in the world. It's just probably a little narrow. And then if you try to apply that same best in the world idea to another problem, it becomes sometimes the worst best in the world idea to another problem, it becomes sometimes the worst ideal idea in the world or it becomes just kind of awkward. Where with Ruby, it was just really, really good. Never perhaps the best in the world on any individual task, but so flexible, so well remixed that it was just exceptionally good at a lot of different things.

Starting point is 00:50:26 And I find that trait to be something that runs as a line through a lot of things I get interested in. With Basecamp, for example, the product that I built with Ruby, we were never the best at any individual thing. Basecamp is a DJ remix of the best tools. Like, oh, we've got chat, we've got message boards, we we got all these different things then they'd fit together and then it offers a solution right not just like i'm just going to be the best in the world it's one thing thought the same thing with ruby on rails ruby on rails as a framework isn't the best in the world at any one thing but it's a dj remix master tape for like oh let's have a great evening and it's really going to fit well and

Starting point is 00:51:05 it's going to work out great. And to tie it to the racing we've been talking about, if I look at the strengths I have as a race car driver, they were never like qualifying. I could never put together the one perfect lap in part because I kept having that damn dialogue running in my head of how I can improve things, which sometimes mean I step over the line and I actually regress. But where I was really good was long form endurance racing, where I had to race in traffic, where I constantly had to deal with something new and have to alter my line or vary things. That was when I got much closer to the peak of the racing community rather than just being singularly good in that one thing. And I've tried to apply that in my life in general, as in I don't just have one thing

Starting point is 00:51:49 that I'm really passionate or interested about. I'm not like, oh, it's all about work and I have to work on Basecamp 120 hours a week and it's all that. Nope. I like working on Basecamp. I like working on Ruby on Rails. I like driving a race car. I like spending time with family.

Starting point is 00:52:04 I've gotten into photography. There's a lot of things you can do. Well, driving a race car. I like spending time with family. I've gotten into photography. There's a lot of things you can do. Well, not a lot of things. There's some of things you can do, and then you can do those things really well. I think the 80-20 thing where I'd much rather have... You can get 100% for 100% of the effort, right? Okay, fine. If you want to be the very, very, very best in the world, you have to spend 100% of you to get there. I just find that uninteresting. I'd rather have five things where I'm in the top 80th percentile. I want to underscore that because I think it's a really important point. And it's something that a number of folks have spoken about with me. And it's a pattern I think worth highlighting for those people

Starting point is 00:52:47 listening. And that is if you want to, and Scott Adams, the creator of Dilbert, wrote about this on his blog as I think it's just career advice. He said your options for achieving greatness, so to speak, are sort of number one and number two. Number one is trying to become the Michael Jordan of one specific domain. And that's extremely difficult. And your probabilities just don't look very good. And I'm paraphrasing, of course. But option number two is to combine unusual skills where you're in the top, like you said, the top, say, 20% or 15%. Then you become extremely valuable, right? And that can apply to racing, that can apply to not only people, but tools, like you mentioned, Basecamp,

Starting point is 00:53:30 Ruby. And Marc Andreessen has also talked about this, who's of course created more than a handful of impressive things and has reinvented himself as an investor. But the CEOs in this particular case, in his example, being combinations of, say, top 15%, top 20% in a number of fields that might be viewed as disparate, right? So perhaps they have a physics degree, undergrad, then an MBA, or a physics degree, and then a law degree, or whatever the combination might be, econ and computer science. Quick thing, what you said about Ruby made me think of gaming, actually, and I'm going to bastardize this, I'm sure, but the easy to learn, hard to master, and I believe that's also Bushnell's law from Atari, which was a good game, is easy to learn, hard to master. And Ruby itself, I had a question on what is, and I could look this up on Wikipedia,

Starting point is 00:54:35 but since I have you here, what or who is Ruby? And then why did you use the words on Rails? Yeah, so first, I'd say that I absolutely agree with that. That is the ideal, both for Basecamp and for Ruby and for Rails, all the things I'm working on, this notion that things should be welcoming. There are so many good ideas in the world that are good ideas, but require an immense amount of effort to penetrate lots of german philosophers come to mind where like there's some truly profound ideas about philosophy buried under an almost impenetrable description of them in non-human language form right like it

Starting point is 00:55:20 really has to be decoded by people to extract that wisdom. I find that to be just unnecessary. The best things, the things that I get really interested in, they're approachable. You can get into, say, programming Ruby or even driving a race car or any of these other things that I've gotten into, photography. They're quite approachable and they've never been more approachable, but they're still really hard to get good at, right? And that's the fun part, that you're encouraged enough in the beginning to keep pulling on the thread. And then it just goes deeper and deeper and deeper.

Starting point is 00:55:54 And I'd say that some of those domains that I left behind, that for me didn't pull all the tricks were like I had worked in PHP, for example. PHP is exceptionally approachable and even more so at the time, probably the most approachable of all the programming environments if you want to work on an information system. Just absolutely spectacular. It really aced that, right? Best in the world on that aspect of it. But then I found just for me at the time, this is not a reflection because I know just

Starting point is 00:56:24 the firestorm that's going to start is not a reflection because i know just the firestorm that's going to start otherwise uh reflection of how things are let's just say that that's cavitated to how things used to be the threat wasn't that deep like you you didn't you couldn't pull for that long until you kind of felt like okay i i reached the the end of the bucket here that was what really inspired me with with ruby and and to keep going with that was you could just keep pulling and it would just it would keep getting better right like it already started out with this amazing trailer and like the movie just never stopped um now i totally forgot the original question well that's because my question was like a 17 parter i asked you the uh the at the

Starting point is 00:57:02 very tail end i asked about the origins of ruby like who or what was it named after and then how you used on rails why you used on sure sure yeah so it's funny because it really ties there's so many of these trends that are overlapping and interlinked even when they're applied at different scales in the different domains the name ruby itself is a kind of a remix and so is rails actually but let's take ruby first i know that uh matt's the japanese creator of um ruby was inspired by pearl um the language that went before it uh served as an inspiration but even the name itself served as an inspiration right yeah exactly yeah um went like, oh, it's a short name.

Starting point is 00:57:46 That's cool. It's kind of a precious, I guess you'd say stone, even though I guess a pearl is not a stone. But it's a precious stone of some sort. It's still another word like that that's also short that's kind of in the same family. It was kind of paying homage and respect to the things that went before Ruby and where Ruby drew its inspiration. So Ruby was born, I think, in 95. Maybe I seem to remember. Maybe he even started working on it already in 93.

Starting point is 00:58:17 But the first release, at least, I believe, was 95. So it's been around for 21 years and Ruby for 14. I mean, you're looking at endeavors that like most of my adult experience have been with these tools. I've been even, even race car driving now. It's like on the one hand, yeah,

Starting point is 00:58:55 I got started quickly and got going, but I've been going at it now for 10 years. It's still a key hobby and pursuit. I really like just digging deep and keep scratching as we said, right? Like I just keep scratching, keep finding new things that are more interesting. Anyway, the same thing with Rails.

Starting point is 00:59:11 So obviously we had Ruby, right? And I was like, okay, let's play off that. Let's pay some homage to that with an R. Like I want to have something that starts with an R too. And one of the inspirations at the time of Ruby was actually a Java web framework called Struts, which in some ways was more of a negative inspiration, perhaps than a positive inspiration. It was like, oh, this is really interesting, like the concept of frameworks in general, but I really don't like how this is done. I really want to do basically the opposite of what this is doing in a whole different lots of areas.

Starting point is 00:59:41 But I find that's often just as valuable inspiration as the things you want to clone. It is just as valuable to look at something and say, oh, that's what I don't want to do. That's what I don't want to be. I've learned perhaps more about running, say, a company from working at companies that did things that I thought were absolutely boneheaded, stupid or whatever than I've learned from trying to emulate good companies. So in some domains, I think it's even more important to look at things that don't work and try to extract lessons from that rather than to look at things that do work. In any case, struts have kind of this construction feel to it, right? And I mean, like, oh, that's kind of cool. And then with R, like, oh, Rails, like, that's kind of similar. Like, it has some fun plays on, like, oh, you kind of put your development on Rails that it kind of just goes. It's fast and so forth. And then I went to whatever site I was using to reserve domain names back then.

Starting point is 01:00:35 I went Rails.com, taken. Oh, damn, I can't get Rails.com. Rails.org, nope, taken. Rails.net, nope, taken. Rails. all sorts of other things? Taken, taken, taken, taken, taken, taken, taken, right? Like, all those singular words were already taken

Starting point is 01:00:51 long since. And then I went like, oh, okay, well, I guess I need a domain name. Ruby on Rails, then. Oh, free. Ruby on Rails.com. And there you go. So that's how it ended up with the name, not out of any other...

Starting point is 01:01:06 I mean, I ended up actually liking it even better because it paid even more homage to Ruby. It was even more differential to it in the sense that Rails for me really is about introducing the rest of the world to Ruby. That was the main mission. The Rails part was a vehicle to get people to discover what a wonderful programming language that Ruby is. So love that I could fit that as part of the

Starting point is 01:01:31 name and that kind of became a thing. You mentioned learning from bad examples. This can be applied to a lot of domains, of course. And I know people, in fact, who teach writing in high schools or even colleges by having their students read examples of really bad writing, because it's easier to identify what they don't like as opposed to figure out why the good writing works. Let's look at business. So you come to the US, you're working with Jason, and at the time, 37 Signals, now Basecamp. What do you guys do differently? That's a broad question that I'll try to answer in a meta way, where by saying that one of the early inspirations for wanting to do this, wanting to work at my own company with Jason, where we would call the shots, was that we would get a chance to

Starting point is 01:02:25 reevaluate everything from first principle. That I felt that there was so much of the mechanics of the businesses I had worked in before that was just mindlessly copied from, oh, that's just the way things are. That's just how we're doing things. That's how other companies do things. That's how you're supposed to do things. And I just saw enough of those misapplications or wrongful copies where I just went like, I don't think so. Like, maybe this was a good idea somewhere at some time in some context, but it's lost all connection to goodness. And now it's just a really terrible idea. So when we're going to run our own company, we're going to evaluate everything from as much as we can from first principle, everything from like how we hire, how we grow, how we do marketing, how we work on products, how we decide what we're going to work

Starting point is 01:03:15 on. It's not that we can't be inspired by others, but let's just try to keep peeling back until we get to the first principle. Is this, in first principle, a good idea? Do you have any principles here at all, right? Like a lot of people just clone techniques. They don't clone principles. So they don't examine principles and they aren't clear about what they want those principles to be, except if they're these overly broad, oh, we want to do good work for the world or whatever, meaningless things that anyone would agree to. The only kinds of principles and direction that I care about are the things where reasonable people could disagree, generally speaking. I think that those are the interesting

Starting point is 01:03:58 points. Where reasonable people can disagree. Could you elaborate on that? Yeah. I think where you're saying something that is meaningful because someone else would take the opposite side of it. Like if there's not an opposite side of this bet, I'm not saying something interesting. If I'm saying like people matters most, okay, who's going to disagree with that? Like basically anything that's on a corporate Fortune 500 motivational poster, like you'd go like no one would say the opposite right like you read these mission statements and you go like you're not saying anything because you're not constraining your view you're not constraining the world and if you're not constraining the world like what are you doing why are you trying to draw this up well not yeah i was just going to say not not only that but in a way i mean you're acting as a scientist, right? And I think that good engineers and good programmers tend to have that lens through which they view things in so much as if it's not a falsifiable hypothesis, it's just like, what are you doing?

Starting point is 01:04:56 You're just kind of… Exactly. I think that has been one of the driving principles, at least for me. And sometimes we do argue about this internally, but the scientific method, for me, is just such a gold standard. It doesn't apply for everything in all cases always, but for me, it applies for most things most of the time. And if I cannot find ways where either what we're doing or what we believe has a falsifiable version of it, where it's like, oh, well, what you believe actually didn't work, right? If we can't arrive at that conclusion, it's not an interesting thing

Starting point is 01:05:32 to believe. Because then either anyone would believe it, or it's not actually driving your actions. Because if this principle can lead you to both sides of the coin, then it's not helping you make decisions. And that's really what I want. I want a framework to help me make decisions. And especially the tougher the call, the more interesting it is, because that's where we make progress. And that's always been what I've been interested in, in sort of refining Basecamp, the company, as being a product in itself that we could tweak and tune and optimize and make better for Jason and I owning the company, for all the employees that we have, and for all the customers that we have. And again, it's this system thinking that we're

Starting point is 01:06:17 trying to improve the system and optimize it in such a way that we do more good for more people more of the time. And if you're not measuring that, if you're not being scientific about it, you might stumble into it. Lots of people stumble into, quote unquote, a great company because they have just one idea or they have some luck or they have something else that just works. And then kind of the rest of it doesn't matter. That's not so interesting to me. I mean, sure, we've had our fair share of luck. Of course we have.

Starting point is 01:06:48 But I also think that the thing that keeps me going after all these years was not just like, oh, we got lucky once. It's the interesting part of we keep scratching. How can a company be better this year than it was the, well, if you take it all the way to the origin of 37Signals 17 years ago. And what's interesting in that too is that it's not just a straight line either, right? There are regressions. So it's been fascinating for me to go from the four people who built the first version of Basecamp to the 50 people who today run the company, which it's funny because, I mean, most people would look at that like, oh, you're 50 people running Basecamp. Like that's a laughably small company. And to me,

Starting point is 01:07:28 it's like this huge organization because my origins was, and perhaps to some extent, my preferences are a smaller thing put together really well. And do you, so I'm definitely going to come back to the beauty and elegance or just beauty and elegance as concepts. But I want to ask you first, since you brought it up, and this was going to be one of my questions anyway, do you guys have a cap on the number of employees that you want to have at the company? In other words, base camp not to exceed X number of people? Or is there any thinking along those lines? And if so... I think it's more a principle of, let's try to stay as small as we possibly can while still not feeling negligent about the things that we cannot do. It's all good and well to say, oh, you're 50 people now. What if we we were 30 people and we just like didn't answer customers emails? You can be a smaller company if you just don't want to respond to feedback and you might still sell your product and so forth. But that seems

Starting point is 01:08:33 negligent. So I want to be as small as is not negligent to be. And of course, like that, I mean, to some extent, perhaps that's not a scientific statement because how is that false viable? But there's just a sense that we can be much smaller than what the standard operating procedure is for a company of our number of customers, for the amount of work and output that we produce for all the open source that we're involved with. We are definitely far, far smaller than the norm. I see lots of companies, many times our size, where I go, where's that effort going? Like I'm not seeing, it's not visible. Maybe it's behind the scenes

Starting point is 01:09:18 and it's always easy to compare yourself in flattering ways to stories where you don't know the full backstory. But I think there's still something to be said from the idea of just trying to optimize your company to be your best product. And if you do that, then rejigging it. And I look at, for example, when I write code, right? Like one of the chief principles of writing good code, as it is about writing good prose is to remove needless words remove needless paragraphs remove needless complication and for example with with companies

Starting point is 01:09:53 there's let's just say policies for example um lots of companies have all sorts of elaborate policies on on spending on how you can justify um uh expense reports and so on and so forth. Is there a way we can get away without that? And one of the enduring policies we've had is when you get hired at Basecamp, you get a credit card and the policy is spended wisely. The end, right? Right. And then, OK, forward your receipts if they're on email to this email address that we have that no one looks at.

Starting point is 01:10:28 But just in case we get audited or something and then that's not a perfect solution, doesn't track every expense to the ninth degree. And if we do get audited, there might be some discrepancies where things don't line up 100 percent and you deal with it then compared to what you sort of just save and overhead and complexity of and it's not just about this thing that's just one small thing but imagine making that choice on 100 things all of a sudden the amount of complexity you get rid of just compounds and the whole thing ends up being so much easier, right? Because if you look at companies and you look at company growth, if you're four people and you hire four more people, maybe you get close to 100% improvement in productivity, but probably not. Probably more like 50% or whatever, right? If you're already 50 people and you hire another 20 people are you getting like another 50 again absolutely not you're getting what five percent seven percent like the complexity

Starting point is 01:11:32 curve is not linear when you make your company more complex either through people or processes or policies um the marginal benefit to sort of the overall thing you're trying to accomplish just drops really quickly. So that's one of the things that I've just on a personal level has been interested in, like, how can we maintain maximum efficiency? And to some extent, and in some situations, that's gone too far. Like I've been pursuing maximum efficiency sometimes beyond the point of what's reasonable. You can say like when in the beginning we had zero money at all and we had to be just four people and so forth. We had to be maximum efficient because we didn't have anyone else's money to spend.

Starting point is 01:12:19 We had to spend our own revenue. So we could only grow accordingly to that. But now we're at a different place. So now perhaps you can afford a little bit of slack. And I appreciate that idea. Again, I appreciate generally ideas that sort of stretch and bend. And a maximum efficiency at all times does not stretch and bend that much. But having that at least as some sort of platonic ideal, something you always have at the back of your mind is something you try to drive decisions from still leaves you to a very different place

Starting point is 01:12:49 than where we would have been if we had gone the standard route of, oh, here's a new software company with a product that's taking off. Let's get a lot of venture capital money invested. Let's hire a bunch of people and staff up to 100 as quickly as we can. Let's just start blowing it out right away. That's the standard model. And lots of people have followed that and some have succeeded and lots and lots and lots of others have gone up in spectacular flame.

Starting point is 01:13:14 And I just looked at the situation and went, what am I trying to do here? What am I trying to do with Basecamp? Why Basecamp? Well, first of all, I'd like to set up a company that I would want to work at in 20 years. Like I actually, to be honest, I don't like learning tons of new people all the time. Like I'm an introvert. I like working with people for the long term because I get to get to know them and you get comfortable with them. You fall into a groove where things are just so much easier and you need to say so much less to get the same amount of work done. And there's just a reliance and a trust in that competency.

Starting point is 01:13:55 And if I want to do that, then I can't install all sorts of time bombs in my business. I can't install like, OK, if I take X amount of money from these people, then they want it back in seven years and they want a 10 X. So we have to shrink for the fences to get that. Otherwise we're going to blow up. Well, so that's one thing, right? Like I want a stable long-term work environment because that's just where I find that I can get access to these flow States as much as possible. And that's, what's a lot of fun and so forth. Then secondly, um, I want to do this because I want some modicum of success. I don't need to be a billionaire. I don't need to be even a hundreds millionaire. I just need to be comfortable in knowing that like, okay, we got

Starting point is 01:14:39 to some baseline, right? I like to compare the fact that the difference between having zero dollars and a million dollars is extremely large in terms of basic comforts of living. The difference between having a million dollars and two million dollars vanishingly small on the same scale. Right. And the further up the chain you go, the less marginal benefit there is, at least within my hopes, dreams, and aspirations. Yes, if your biggest dream in the world is to own the New York Jets, as Gary Vee wants to do, or you want to send people to Mars, like Elon Musk, or any of those kind of wild dreams,

Starting point is 01:15:16 okay, fine, you need billions of dollars. And you should pursue strategies that are compatible with that. I perhaps have more, it sounds funny, but modest. It's only in comparison to those outliers modest ideas of it so i want to optimize my chances for that so part of that was like i want to optimize my chances when i'm running a business of how can i just become like a millionaire like just a basic run-of-the-mill millionaire which is still like look at the world's stage like

Starting point is 01:15:42 incredibly rare thing right and extremely blessed uh position to be in but still infinite well not infinitely far far far more likely than to become the next billionaire right like the number of millionaires in the world versus the number of billionaires in the world like that's actually been one of the things i've been driving a lot of how i approach where do i want to be like if you take where do you want to be in programming, where do you want to be in racing, where do you want to do in business? I'm like, it's such an oxymoron, but I feel like I modestly just want to be in the top 5%, right?

Starting point is 01:16:14 I don't need to be, again, as we talked about, I don't need to put in 100% to be Michael Jordan. I don't need, because it's even worse than that, right? And that's the reason I don't want to do it. I don't want to put in 100% to have a really, really poor chance of becoming Michael Jordan. So I'm going to be Michael Jordan. Lots and lots and lots of other people who, if you just take the baseball or basketball metaphor, that are good basketball players, right? And can make a good living and get to play in the NBA. And that's pretty amazing, right?

Starting point is 01:16:43 I just want to make it to the NBA. I don't have to be Michael Jordan. No, definitely. And I want to just emphasize something that I think you said. I mean, this is how I think about it or have been trying to think about it more and more in the last, say, five years is that you have to, or you should strive to have compatible goals, right? In the sense that a lot of the folks I meet, and I live in San Francisco, I live right in the belly of the beast. And you run into folks who maybe they have hundreds of millions of dollars and they're completely miserable. And when you really dig into it, if you have the chance to do it over wine or whatnot, very often you find that they have incompatible goals. In other words, like what they need to feel fulfilled and calm or in flow is not compatible with the other ambitious,

Starting point is 01:17:36 say business or financial goals that they have. So it's doomed to fail, right? I mean, if you succeed and you accomplish all of your goals, if they're incompatible, you're basically just sowing the seeds of your own destruction. And so I wanted to ask you, do you consider yourself a happy person? Yes, you do. Absolutely. And part of it is because I work at that. Like that is one of the explicit goals of a higher tribe to die. The decision is this is going to make me a happier person um jeff bezos has sort of the reverse of it which is his regret minimization framework which sounds like just something jeff bezos would come up with where he's like i'm just going to try to drive my life in such a way that i have the least regrets i don't know if that's the path that i'm taking but happiness is also sort of a fuzzy term, right? Like one of the things I know that you've been interested in too, and has really spoken to me is stoicism.

Starting point is 01:18:31 And this notion of tranquility, to be in this state of contentment and tranquility. It's happiness have some sort of like connotations as though i'm running around all the time laughing my ass off this wonderful life right like that's not i don't aspire to that that's not how most days are but i do have a sense of deep tranquility and contentment with the situation that i'm in and part of that is actually going all the way back to the beginning. My key takeaway from the four-hour work week was the concept of lifestyle design. That there's so many people who just follow, who are on rails in the negative sense of the word of like how things are supposed to go. Okay, first I get my, this education,

Starting point is 01:19:24 I perhaps don't even really care that much for the subject, it'll lead to a good job then i'll get the good job then i'll get married then i'll like that and then at 65 i'll retire and then i can really live life what are you crazy um first of all good chance you won't make it to 65 and then everything was wasted between getting born and not getting there. Second of all, why would you waste or wait until the worst decades of your spirit in general in the US and in Silicon Valley in particular, this notion, let's compress working life. If you could just work like a madman or a madwoman for 120 hours a week for seven years straight, then Nirvana will be waiting on the other side. And you can take all your millions in winnings and you can sit down on a deserted island somewhere and drink a mojito. And you're like, you know what? I know people who've gone exactly through that.

Starting point is 01:20:34 And after two weeks on the beach, they went like, wait, what? Wasn't this supposed to be winning? This is miserable. I hate it. I don't want to be here. That was not actually my destination. The thing I gave up all sorts of valuable things

Starting point is 01:20:50 to arrive at is a miserable place to be. It's easy to trivialize these things, especially when you actually already are a millionaire, to trivialize the struggles and the aspirations of someone where money can make a big difference. But when you're talking about people who've already made it and want to make it more, right? It's incredible

Starting point is 01:21:11 how often that people end up sucked into this notion that like, oh, if I just make it to the next step, then I'm going to be happy. Then happiness awaits me. When just a false treadmill, it's not only is it a hedonic treadmill and that it keeps moving further and further away from you, but it's also just false. It really does not pay out that way. The, as we've talked about a bunch on this show already, flow, the striving, the getting better,

Starting point is 01:21:38 like that's where living is. That's where happiness is. And it can happen whether you're at the beginning or at your end of that journey. Like I think back of when someone asked me, are you happy? I think back of when I sat in Copenhagen in 2001 in my, what, 350 square feet apartment, tiny, tiny little apartment in Copenhagen, I was going to school at the time. I was learning PHP. I had all sorts of things I was worried about, like rent and so on, not on an existential level, but still in a normal sense of it, right? All sorts of things. I was still happy.

Starting point is 01:22:17 I was within margins of where things are today. And if you look at those two situations, otherwise from a level of possessions or quote unquote success, like they're pretty different places to be. And yet they don't feel that different. And part of that is to have that focus on the inner journey, on the inner stride of this. Another quote I love just pulling out whenever context fits or not is Coco Chanel, the best things in life are free and the next best things are very expensive. And I like that because it sort of it recognizes that the next best things are still pretty great. It's just that there's so many of the very best things that you can focus on that whatever is on the next best thing and which does happen to be very expensive, it's just so far down the ladder that once you adopt the philosophy of life that allows you to view it from that angle, it really puts things into perspective.

Starting point is 01:23:15 It gets it so much easier to get to tranquility. And I think that tranquility is in a lot of respects a better goal than happiness which has been, the word is so overused to have become almost meaningless. I want it to use it just because it's a more straightforward term and more familiar term. But it seems to me also that if we're talking about say flow states, if we're talking about tranquility, It relates to developing an internal locus of control or an internal metric is probably too quantitative a term, view of progress. So you're competing against yourself as opposed to in some positional economic sense, competing against the Joneses, right? Which you're never going to win because there's always going to be another Jones who's willing to sacrifice more than you are if you're kind of

Starting point is 01:24:11 chasing, as you said, this pot of gold at the end of the rainbow. All of which relates to stoicism, but I wanted to also reiterate one thing that you mentioned, which is this seven to 10 year sprint that you see so often in Silicon Valley and the misconception that you can then automatically just park up and sit on a beach and praise God, here's nirvana. The disconnect, I think for a lot of folks or the question that they'd be well-served to ask is, am I developing attributes now that I can use in multiple states, in multiple endeavors? years, the work habits and so on that you're going to have to develop are completely incompatible with sitting on that beach and being diametrically opposed. And just automatically switching those gears is not as easy as one might think. In fact, it's exceptionally difficult. You have to completely reprogram yourself. So coming back to the stoicism, and you mentioned Jeff Bezos, I've been reading some of your

Starting point is 01:25:27 articles, and there was one line that jumped out at me is really profound and applicable in a lot of contexts. And I think this is from the day I became a millionaire post. And it is, expectations, not outcomes, govern the happiness of your perceived reality. And I was hoping you could talk a little bit about that, but also talk about, because I genuinely don't know the answer to this, how did you navigate the decision to take money from Jeff Bezos in 2006? Yep.

Starting point is 01:26:01 Let me start with the first thing. I keep having to relearn this lesson very often, and I feel like it's one of the lessons I've practiced the most. But as most of the most profound, important lessons in life, you can't just read the text and then internalize it. It takes practice time and time again and this notion that it's the expectations not the outcomes themselves that's what matters is really about looking inwards and seeing like whether something is good or bad in a lot of cases not all cases but in many of the challenges we face whether something is good or bad that's just you deciding that and it it doesn't happen by random it happens because it flows through your habits and it happens because it's flow through your expectations if i take one example just um i got we've talked a bunch about racing in my 2013 season we had a stellar season we finished second in the championship and we finished second at the 24 hours of lamar like absolutely amazing right it was probably one of the worst years i've had in racing. It was absolutely miserable on all sorts of levels.

Starting point is 01:27:07 And the key reason why it was miserable was exactly because of this expectation. We came in from the get-go with a lineup, a backing, a car that said, this is supposed to be the frontrunner. These guys are supposed to win. And then when we didn't win, finishing second didn't feel like finishing second. It felt like being a complete loser. And what was funny was just the year before, 2012, right? I started, this was my first year at the 24 Hours of Le Mans, and I was thrilled just to finish the race. It was wonderful, right? One of the magic experiences of all the time I've been in racing was to finish the race in 2012. I don't know what we finished, seventh, eighth. I don't even care. That wasn't

Starting point is 01:27:50 the expectation. That wasn't the goal, right? And then already the year after, somehow I got suckered into expectations that said, you're supposed to win. And when we didn't win, it felt like a ton of brakes on us. And I've had this over and over again. Whenever I feel like I've personally done a good job at the racetrack, it's all about my internal competition. It's not about where we end up finishing up. Some of the best races I've ever had, we finished last. Some of the worst races I've ever had, we finished first. They're all about whether I felt like I progressed and I did everything in the best way I could possibly do, whether I disappointed myself.

Starting point is 01:28:28 And disappointment is intrinsically linked to expectation. So being extremely careful about how you set your expectations, I think, is probably the number one key to tranquility for me. And there's a lot of stoic writing that addresses this point directly. And one of the things that I love around expectations is, and stoicism is this notion of negative visualization. Oh, my favorite. Yeah. Arguably the most valuable thing that I've taken from stoicism. You imagine all these terrible things that can happen, right? To set the context and set your expectations in a completely different light. Every day, probably, at least every week, I imagine what would happen if I went broke, if I had a major accident where I would lose some of my limbs, if all sorts of terrible things would happen to either my family or to my professional life or to the world at large. And then I process that and A, try to come to terms with those things.

Starting point is 01:29:35 And B, use it as a driver to be sort of thankful for the things I have without becoming attached to them. And playing those mental games, I think that's the number one thing. Like happiness, not happiness, in a state of tranquility, not in a state of tranquility, they're all about the mental games that you play to a large degree. I mean, obviously, there are some places in the world where it's a lot harder to be happy and in a state of tranquility than in other places. But if we're talking about Western developed worlds where you're not living on the edge of poverty, then I'd say the mental game is almost all of it.

Starting point is 01:30:15 And then in terms of sort of the mechanics. So in 2006, I had already been exposed long enough to the Internet industry and to the venture capital world to realize that's not what we wanted to do. That that was an incompatible goal to take a bunch of money from venture capitals with all the strings that that implies and getting the other things that we wanted, like running a company for 20 years, like calling the shots ourselves, like not having to go and sell our company or go IPO or being forced into some unsustainable or devious tactics for growth or any of all these other pressures that come from taking other people's money and trying to fuel them in as rocket fuel for your company. So what ended up happening was Jason and I looked at our sort of risk and we said like, okay, right now, 37 Signal Space Camp, like there's something, we have some traction as people like to call it, right? There's traction, that's valuable. There are people who want to give us millions of dollars

Starting point is 01:31:15 to put into the company in hopes that we can turn this company into being worth a hundred million or billion or whatever else that they're trying to get out of it, right? So we could do that, and then we could take some money off the table, or we could try to just swing for those fences to try to get that. Or we could try to see if we can find someone where instead of investing in the company, as in taking money and putting them into the company to use that money for growth, which is what VCs do, we could perhaps find someone to make a hedge bet with us where we could sell a small, non-control, no strings attached portion of the ownership that Jason and I each have and then just pocket that money.

Starting point is 01:32:01 Not put any of it into the company, not accept any of the strings that would normally go with a venture capital contract, not accept any of the timeline, not start any of the time bombs or any of the other stuff that goes on. Just say like, hey, Jeff, if you want to be along for the ride, we'll sell you a small slice of each of our share and simply take the money and use it as our hedge, just that if this Basecamp thing goes poof and turns into the next Friendster or whatever, then at least we've taken something off the table, such that we don't have 100% of the risk in just one basket. I'm a big believer in diversification and all sorts of manners and endeavors, as we've

Starting point is 01:32:43 talked about. I've tried to diversify my interests such that should the terrible thing happen, as I frequently negatively visualize that Basecamp collapses, it wasn't my whole identity wrapped up in that. I can go off to other things and be fine, right? So we took a little bit off the table, and's where that post I became a millionaire came from. And it's funny because even I felt like I was pretty well prepared for all of that stuff. our sort of civilization today to not be infected by the constant propaganda for like what happens when you get quote unquote rich that like milk is flowing and honey in the streets and like

Starting point is 01:33:34 certain things are wonderful and it's a fine thread to needle to thread especially once you made it to the other side to say like oh yeah yeah, it doesn't matter that much. And tons of people will actually say, yeah, okay, I didn't eat today. So tell me again what it is about doesn't matter, right? So that to me doesn't mean you can't talk about the topic. It isn't interesting. And I talk about it anyway. And the conclusion I basically came to was that even knowing all the things that I thought I knew, like my expectations were still too high. I still thought that it was going to have a bigger dent on my life than it ended up doing. Right. And it only reaffirmed my belief that where happiness comes from, where tranquility comes from are not those places that the very best things in

Starting point is 01:34:20 life indeed are free. And this, and I got to taste some of the second best things. And that was a lot of fun too. But at the end of the day, they were much more transient. And the things I've kept on doing, I still program Ruby almost every day. A day is better, generally speaking, when I get to program Ruby, because that's just what I truly enjoy doing. And if you look at lots of people who've made it very well, they still continue to do with it. Like we talked about Jeff Bezos. How long has he been running Amazon now?

Starting point is 01:34:50 Like 20 plus years, right? 20 plus years, yeah. He doesn't need to. He could retire to a beach somewhere and sit there and do that. He doesn't want to do that, right? Like none of the people, like everyone from Steve Jobs to like all the sort of standard list of heroes you can go through. Like most people just stick to the things that provide them flow and interesting new challenges and the striving that defines life and the purpose of it. And if you realize that you can prioritize that first and you can prioritize other things below that.

Starting point is 01:35:25 And I think that that's a really helpful way to guide your decisions. For us, it helped guide the decision that we didn't want to do that venture capital time bomb because it was completely incompatible with these other goals that we had and aspirations for life. And now I've got to play that out a bit, right? Like Basecamp would either have IPO'd or be sold or whatever. Now, if we had taken that money back in 2006 we're well past the deadline of um of when the money would be up and i'm sitting here on the other side and saying like you know what it's pretty good the other side's pretty good it's not as spectacular it's not as glamorous perhaps

Starting point is 01:36:02 there's not as much crystal champagne or private jets or whatever, but you know what? It's pretty good. And I get to do more of the things, more of the time than I would otherwise. Like I talked to lots of entrepreneurs all the time who either ended up with what they thought was success, right? Like they sold their company, then they did the beach thing for three weeks. And then they ended up even worse off than that, right? They realized that the beach thing was not where Tranquility was hidden. They came back and now they're like, what am I supposed to do now? Oh, I guess start another company. And oftentimes the second time around, it's not as good. It's not either as good of an idea or it's hard to do it again. You've lost something really

Starting point is 01:36:41 valuable that's hard to get back. And I see a lot of people at that other side, like worse off than they were when they were just that tiny startup, two people struggling to make things work, but striving in flow, in tranquility. Yeah, it's extremely common. And I think what I've at least tried to apply for myself is practice. If you want to be good and you hope to enjoy all of these things by using your time for fun, when you have money, you have to practice that before you have money. And it sounds ridiculous, but I think that money is like alcohol in the sense that it just makes you more of who you already are. So it's not like somebody who becomes a huge asshole when they're drunk has no amount of

Starting point is 01:37:30 asshole in them when they're sober. They just keep it under wraps. And money applies the same type of pressure to the vessel, right? And so it's going to amplify your strengths, your weaknesses, your neuroses. And so you have to practice the skills or the use of time, for instance, that you want to have when you have this influx of pressure. And I was going to mention, because you were discussing negative visualization, I highly recommend, and this is in public domain, anybody can read it. There is a letter by Seneca the Younger. Well, he has a compilation of letters called The Moral Letters to Lucilius, L-U-C-I-L-I-U-S. And there's a very specific letter, letter 18,

Starting point is 01:38:11 probably takes 10 minutes to read, but it's called On Festivals and Fasting. And it talks about not just negative visualization, but fear rehearsal effectively, where you set aside a few days each month to say, I'm making these up, but sleep on the floor in a sleeping bag in your kitchen for a few nights, or eat nothing but rice and beans or instant oatmeal for a few days, wear the same pair of jeans, whatever it might be, simulating the condition that you fear. In other words, if you lost everything, or if you had to take a pay cut because you needed six months to figure out your next gig, because you hate your current gig, whatever it might be, by removing that fear, it emboldens you to do many different things,

Starting point is 01:39:00 including one thing that you and Jason are very well known for, which is being outspoken. I mean, you can't do that if you're constantly in well known for, which is being outspoken. You can't do that if you're constantly in fear of having the rug pulled out from under you. On Bezos, just one last point on that. What does he get out of investing in Basecamp? Is it that he hopes at some point you guys will have a change of heart and look for or at least entertain a liquidity event or an acquisition?

Starting point is 01:39:27 So take Bezos first. He got his money back and then some, and he still owns a part of the company. We paid him back. One of the wonderful things of having a private company that's profitable is that you get profits. Money actually comes out of the equation, which I know is almost a foreign dirty word in Silicon Valley. Like, wait, what? There's actually comes out of the equation which i know is a almost a foreign dirty word in silicon valley like wait what there's money coming out of the company you're supposed to be in the red like what's going on here um but that's what happened like we've run a profitable company for 17 years like things compound and like what's not a big payday in year one like if you do that 10 years in a row, that's money. That's real money.

Starting point is 01:40:08 And he's been paid back. He's more than made whole, and he continues to earn his share of the profits every year. And I mean, these are rounding errors. Like the freaking dollar moves one cent, and he has lost more money in like two hours than he would ever gain or lose on our investment. So I don't think he actually does it that much for the money. I think the money is just an extension of simply him having fun with this, having fun with the investments and so on. So it's not perhaps as pure economical as someone like a VC who's investing other people's money, a fund in something and has to show certain things. I think Bezos has made a ton of investments in people simply because he enjoyed doing that and enjoyed seeing it. And he enjoyed

Starting point is 01:40:58 our sort of irreverent take on a lot of things and kind of wanted to support that. And again, it was pocket change to him to do it. Have you met him in person? Yeah, we've spent quite a, especially in the early years, a fair amount of time with him. Usually we would meet up with him about once a year and spend a good amount of time with him. And I always learned a bunch. And the funny thing is, of course, that one of the reasons I learned a bunch was that he wasn't just a version of Jason and I. He was in many ways the direct opposite. Right.

Starting point is 01:41:30 Like the way he runs Amazon as a public company is like 180 degrees the opposite of how we do things, which is, I think, part of the attraction. Right. Like that he wasn't just looking for little minions that were trying to do the same thing as him. He was looking for people who could challenge his thinking. And we've certainly had our thinking challenged by him as well. So I think that it's great to have those kind of associations in your life where it's not just like, oh, someone does exactly the same thing that I do, but better. But someone does something totally different than me. And I can learn something really important from that perspective. But I'd say too, as you mentioned with habits, that that has been one of the things I've been incredibly conscious about, that I've seen people just be trapped by their habits. Most people are, right? That's how we run our lives. So we've been extremely conscientious about getting the right habits, not just for ourselves, which for both Jason and I have meant like, hey, let's just work 40 hours a week, right? Not try to do the 80 thing

Starting point is 01:42:32 or the 120 thing just because we're bootstrapping or whatever else it is. We want to set habits that we can comfortably want to have on the other side as well and do that for our company as well and do that even for the product. One of the things we worked on for the new version of Basecamp was this notion that work can wait. That I think in this age of mobile phones and apps and so on, engagement has become this magic excuse for interrupting people all the time. 100% agreed. Well, it's also a vanity metric that venture-backed startups can use to Jedi mind trick their investors into convincing them that something is happening that's meaningful when nothing meaningful is happening. Yeah. Right. And I think that that's one of the things that we've been freed from, right? We don't have to maintain any vanity metrics.

Starting point is 01:43:22 Basecamp can actually be a better product both for us and for our customers if it doesn't have to maintain any vanity metrics. Basecamp can actually be a better product, both for us and for our customers, if it doesn't have as much engagement. If people can get the things that they need out of it when they need out of it, and then Basecamp can kind of go away. So for example, for Basecamp 3, we have this feature called Work Can Wait. You click it on and Basecamp won't send you

Starting point is 01:43:40 any notifications, won't send you any emails, won't bother you in any way once you're off the clock. By default, it's set to nine to five. But then after that and on weekends, if you have someone in your company, which in a company of 50, you usually do that, like sends an email on Saturday or whatever. You're not interrupting everyone. You're not broadcasting and blasting everyone all the time. And that's been one of the things that's been near and dear to me and i think in the u.s people kind of laugh that off as silly like way what like

Starting point is 01:44:11 um can't you just like figure out how to manage your own life and so on no i think these habits matter i think if you look at the french which also the reason to laugh at the french but this is not one of them in my opinion there was a proposal in their parliament last year, I believe it was, where they said, like, employees should have the right to disconnect, that they should have the right not to receive emails that their boss expects them to answer on Saturdays. Now, that's a truth with some modification. There are always disasters and whatever that can happen. Most of the time, they don't. Most of the time, your boss just sends you an email on something stupid on Saturday that is kind of implied that you have to deal with, even though it's not that important. There's just such an ASAP culture all over the world, but in the US in particular, where everyone thinks that it's their right to have access to everyone

Starting point is 01:45:00 else immediately all the time. And I think that's just incredibly corrosive. And I think in some ways it's just getting worse, right? Like mobile phones is one thing, the rise of chat applications in the workplace is another. There's a lot of new pressures bombarding us with interruptions all the time. And if there's one thing I've found is tranquility and flow is not compatible with interruptions.

Starting point is 01:45:26 If your day is chopped up and into tiny work moments of 40 minutes here and an hour and 20 there, you will get nothing interesting done. You can get routine work done. You can't get interesting creative work done. The only time I make progress of any material kind on anything that has ended up mattering really on the creative side of the company has been when I've had large stretches of uninterrupted time. That means no chat. It means no phone buzzing. It means none of these interruptions. You just need two, three, four hours to really sink your teeth in, scratch deep enough on the problem where you can really truly understand it and then make progress on it. And we've just made it almost impossibly hard these days. And in many ways, we're making it harder and harder. Like the number of unread

Starting point is 01:46:13 counters that most apps ship with, the default settings for blasting everyone all the time, the new expectation that you have to hang out in the chat room and respond to every meme within two minutes. It's terrible. It's just absurd in many ways, which, by the way, is another great book on philosophy in the current age that I'm reading right now, Michael Foley, The Age of Absurdity, that draws on a lot of these things we've talked about, stoicism included, and on this current and accelerating culture of just constant interruption and quote-unquote multitasking, which it really isn't. It's task switching. I think it's just terrible.

Starting point is 01:46:52 And we got to do something to push back. No, I agree. And I think it has to start at a personal level, right? Making decisions like you have in creating these blocks of time. Do you schedule those on a weekly, monthly, quarterly basis? How do you create that time or how do you schedule it? I try to have it every day. I get that question from people all the time where they're like, oh, how do you get so much done? And I look at them sometimes in bewilderment and I go like, I don't actually feel like I'm getting that much done.

Starting point is 01:47:20 I just happen to configure my life and my business in such a way that most of the time I have long, uninterrupted stretches of time. And when you every day can get like a three-hour block or whatever, you just get a lot of stuff done. And it doesn't feel like it. Well, it doesn't feel rushed. Crushed. It looks impossible when, if your day is this kind of standard corporate day where your, your day is just chopped up into these tiny moments, you're exhausted at the end of the day. And you're like, you feel like you didn't get a good day's work and you can look at someone

Starting point is 01:47:53 else and like, how did they get all that done? How did they create and maintain Ruby on rails? How did they keep base cam running with the millions of people that they have using it with that few people on board? How did they do all these things? And we go like, I at least go oftentimes. I don't know what we're looking at.

Starting point is 01:48:11 We can't be looking at the same thing. It doesn't feel stressful to me. I work 40 hours or less sometimes in the summer when we do Friday's office. We used to call it, now we just call it the four-day work week during the summer. We work like 32 hours a week and we still get a bunch of stuff done. So it's absolutely possible. It's how you configure and squeeze out the quality of time, not the amount of time. It's not about being eight hours in an office. It's about increasing the quality of the hours that you spend. And most people just produce really crappy quality, really shitty hours.

Starting point is 01:48:46 They have eight of them, but they're completely soiled and spoiled versus if, uh, you just have four of them that are in pristine, great condition, you'll run laps around the person who sits with four or eight shitty apps this is this is part of the reason why i almost never agree to let journalists uh follow me for any piece because it would be so boring and the reason i bring it up is that people might have this image of me like it's kind of like extreme snowboarding meets girls gone wild meets i don't't know, rock climbing like 24-7. And the reality is, I feel like I spend most of my time staring off into space, but I do block out, I try to block out the first three to four hours of each day for completely non-reactive activities, right? And that's it. And I was thinking about this yesterday, in fact, because

Starting point is 01:49:41 I had a day yesterday where I was like, I got to the end of the day and I was like, I don't really think I got anything done today. It doesn't particularly bother me, but I was just observing it. And I thought to myself, well, the good news is if I have those blocks of time, and this may sound odd, but it's like, I have those uninterrupted blocks of time and this is important. I'm focusing on the one or two force multipliers, right? The one or two things that are really going to make everything else easier or relevant. I only really need two days a week where I get my shit done properly. And it creates the illusion of having done a ton of other things because I'm hitting the right dominoes in the right orders. I have that feeling all the time.

Starting point is 01:50:21 I have days all the time where I feel like, really, there wasn't that much in this day. But I look at it on a timeline of like two weeks and I often go like, oh, wow, I'm very happy with that. I look at a timeline of, for example, what we got done at the company in a year. Like we just we released the Basecamp 3 and all new version of the software last year, a year ago. Right. And Jason just wrote up a summary of all the things we've worked on this year. And I go like, wait a minute, that's actually incredible. Like, how did we get all that stuff done when each individual week or each individual day, generally speaking, they're not like frantic, crazy death march rushes, right? But it's just the compound nature of good habits, compound nature of tranquility, compound nature of sustained,

Starting point is 01:51:08 sustainable progress. It's the same thing as we talked about with the business, right? We have never had a hockey stick business. Basecamp has never been a hockey stick business. It's just been a linear growth business. And if you keep drawing that line out long enough, that's still good. Linear growth is still pretty damn good if you can just keep drawing that line out long enough, that's still good. Linear growth is still pretty damn good if you can just keep drawing long enough. Well, it comes down to your expectations line, right? I mean, because you say expectations, not outcomes, govern the happiness, but it also governs a lot more than that. I mean, the timeline through which as a lens, you look at your progress is really important, right? Because if, if you are making like a lot of venture backed startups, I mean, look,

Starting point is 01:51:50 I'm, I'm a player and I have been historically a player in that game. So I'm not going to totally slam every aspect of it, but there are quite a few. Yeah. That's why you're here. And there, there are, but there are some like mass delusional activities that go on in that world. And one of them is being so focused on the short term that you basically just commit suicide over the long term. And you can do that even if you're a one-man show or a one-woman show, right? If you're not looking at the two weeks, you're looking at each day. And as a result, you commit to being busy instead of actually taking the time to prioritize which requires that slack that empty space of having three to four hours in many cases i wanted to ask you about another piece of yours um

Starting point is 01:52:36 and the inspiration for it because that i don't think the backstory is in there and it's called it's always your fault which is i think ties into stoicism pretty well in a lot of respects. And it brought to mind a question that I was asked once by a gentleman named Jerry Colonna, who's a coach of sorts at this point. I mean, he does a lot more than that, but he was previously a very successful investor, among other things. And one of the questions he likes to ask is, how are you complicit in creating the conditions you say you don't want? So this taking of accountability, what inspired, maybe you can give a sort of a synopsis of the piece, it's always your fault, but also, I want to know the inspiration. Why did that why did you write that was what prompted that yeah it's a it's a good question i think one of the uh things i've always tried to do

Starting point is 01:53:33 and we talked about this in multiple domains is to look at situations as systems as feedback loops and it's always your fault is recognizing that you're part of all systems. Well, it's kind of like a truism, right? You're part of all the systems you're part of. So at Basecamp, for example, I am in some way part of everything that goes on. Whether I'm involved in a project or not involved in the project, I set up some of the outlines. I set up some of the frameworks. I helped create some of the culture that led to what happened. It's one of the things I keep trying to hammer into race teams as well.

Starting point is 01:54:11 Race teams, a lot of times, they love these things of like, oh, yeah, just happened. I mean, it's just a bad luck, right? That's what people say, bad luck. And sometimes you have bad luck. And bad luck generally means like there's a very low percent chance of something going wrong and it went wrong anyway. That's at least, I think, a fair definition of bad luck. A lot of people use bad luck as there was a great chance of this going wrong and it went wrong and that sucks. You know what? That's not bad luck. That is bad planning, bad planning, bad design, bad all sorts of things.

Starting point is 01:54:44 That's your fault. And if you just write it off as bad luck, you're in the short term escaping some pain of accepting your complicity, as you said, in the outcomes. But you're also not learning anything. And if you're not learning anything, how are you going to make anything better? How are you going to prevent the quote unquote bad luck from happening next time? That is just one of the things I cannot take. I cannot stand for.

Starting point is 01:55:10 Like, I am all about we make mistakes and that happens. But when I make the same mistake twice, that is one of the most painful experiences that I go through. And that has happened enough in both company and personal life where I just like, wait a minute, this situation seems familiar. How did I get myself into this? Do you know what? This is my fault. This is my fault for putting myself into this situation. It's my fault for reinforcing the dynamics of this situation. It's my fault for enabling this situation, even when it's not technically my fault. Like the dynamics of this situation. It's my fault for enabling this situation, even when it's not technically my fault. Like, let's say something breaks on the car

Starting point is 01:55:50 because someone didn't set up in the right way. I mean, I didn't do it, right? Like, I didn't swing that wrench, but it's my fault for, let's say, getting on a team that doesn't have the budget that they need to have to do this, to not emphasizing the value and insisting on the stability of a team or of the people who are on the team, not doing enough work on debriefs and post-modems of trying to figure out what's the root cause of our problems. It's always my fault. There's always some complicity in any situation where I feel like, oh, that bad luck affected me. My fault. And it's just so much more actionable. That's one of the things that I like. I like things that are actionable, where I can actually do something, change something, act in a different way where now I'm better. We're better. We've learned something.

Starting point is 01:56:46 We moved forward, right? And we will make new mistakes. And as long as they are novel, that's fine. Just let's not make the same mistakes over and over again. I cannot stand repeating myself. I remember in the days before version control, before Git and CVS and subversions and so on, I would sometimes overwrite my files, right?

Starting point is 01:57:10 I would have spent four hours in a piece of code and then I would make a mistake and I would delete the file. I knew of nothing worse than having to redo that work. It was so physically painful to me that I can remember several features of both Basecamp and earlier systems I worked on where I had a working feature and I somehow killed it and I just never made it again. I simply could not stand to redo the work again. So that is carried over and it's just even amplified with mistakes because mistakes are just extra painful, right? These mistakes, especially as a company size of Basecamp, I'm not just responsible for my own mistake, I'm responsible for everyone else's mistake.

Starting point is 01:57:48 And I need to learn every single time that happens and change the system, change the dynamic, change the flow of the feedback loop, change the inputs, change the configuration of how things are installed in such a way that it's not like, oh, let's prevent this from ever happening again. Because I think that often leads you down a path of an overreaction.

Starting point is 01:58:07 But still just considering the whole system, considering you're part of it, not writing things up to bad luck. I mean, you hear that a lot in racing. I don't hear that a lot at Basecamp, and I think perhaps in part just because every single time someone has brought that up, I've weakness, kind of perhaps lost my cool a little bit on that, which in itself is a failure that you should learn from and correct from and so forth. It's certainly not bad luck. But, yeah, I just I can't take it.

Starting point is 01:58:37 And we've got to accept that responsibility and we've got to do it all. The closer you are to the system, for example, I tweet a fair amount about politics and I tweet mostly about U.S. politics. Why do I tweet about U.S. politics and not about the politics of, I don't know, Iran or Georgia or Russia or something else? Well, partly because I've paid millions in taxes. So I kind of have a vested interest in like this particular country. I happen to live here. I happen to have a direct line of influence to some extent at least even though i'm not granted the right to uh to vote uh i still feel like this is the closest area where i have complicity i have complicity in these actions and i have uh some chance of kind of affecting that it's so much easier to just call shit out when there's no personal complicity, right?

Starting point is 01:59:27 Like it's the speck in your neighbor's eye and all that stuff. So, yeah. Do you think your impatience, well, I shouldn't say impatience, your distaste for repeating work is part of what made you a good programmer? Absolutely. I think it's almost pathological, actually, that I have such an aversion to doing

Starting point is 01:59:53 the same thing twice that, I mean, not that it's that unique. I think that lots of programmers have it that I'll sometimes go overboard and just trying to prevent that from happening again. And that's where I need some restraint of saying like, okay, I've only seen this problem once. I might fear that I'll see it again, but until I actually see it again, let's not overreact here and build some huge honking framework to do it again. But I usually match, one of the things I like the most actually in terms of working on open source and on Ruby on Rails has been pattern matching in the work that I already do. So it's not so much that the thing is exactly the same,

Starting point is 02:00:28 but there's a pattern, there's an outline that's similar. And when I spot those similar outlines and I come up with an extraction that kind of makes that work go away next time that something has a similar shape and outline, that is really where I hit the jackpot in terms of personal satisfaction with the work. I love just spotting these things where I think to myself, hey, if I had to write Basecamp again from scratch tomorrow, I'd be so much better off

Starting point is 02:00:55 because I'd solve all these problems. I'd put all these tools into the toolkit of Basecamp. And this is one of the things with negative visualization where I have this, I don't know, nightmare of fantasy, however you want to put it, where like we lose it all. Right. I have to do it all over again from scratch. We have to write Basecamp again. It's just me and Jason and whatever. And like we don't have the 50 people anymore. We don't have all the money and like whatever. Like, where am I? Can I do it? I imagine this whole thing and I've packed this backpack. I gave a talk at the RailsConf, I think last year, about the survival kit that Rails is for me. I think of like if everything goes wrong and I have to start over from scratch, will I at least have the tools to survive?

Starting point is 02:01:36 And that's my mission for Rails. And it's always been. If I had to reboot fully, I don't have a staff. I don't have other programmers. I don't have anything. I just have myself. Self-sufficiency, as we talked about at the beginning, has been just such an important driver to the pathological level. on and depend on other people. But hey, I carry that cross and deal with that and just try to maximize the benefits and minimize the drawbacks of it. But one of the benefits have been just this focus on creating truly productive tools that allow tiny teams to do amazing things. Because I

Starting point is 02:02:21 want to enable other people who want to do it like we did it, tiny team, no external money to have a chance to compete because it didn't used to be that way, right? If you wanted to start a web startup in 95 or whatever, and you had to spend 200 grand on Oracle license just to get a database going, like that was a terrible time to get things going. Now it's never been easier. And I just love that. I mean, it's funny. We're lowering the barriers of entry, which in some sense makes it perhaps harder because there's more people competing.

Starting point is 02:02:52 But to me, it's just, there's something fairer about that. And I can imagine myself in that situation. I can imagine myself rebooting, doing all the negative visualization and thinking it's going to be okay. No, I mean, I've used Basecamp for the last three book launches and I'm going to be doing so again shortly in about a month and a half. And I'm asked all the time, how many people do you have on your team? And I'm like, ah, one, maybe two really full-time employees. And then the rest are all contracted and everyone's distributed. So I think it's never been easier from the standpoint of having a low barrier to

Starting point is 02:03:32 entry. And I find that encouraging because A, if you're not competing, you're not getting better. You should have some type of competition in your life, some type of pressure to improve. And second, it gives you the opportunity to compete in a game that you can rig in a sense, because like we were talking about earlier, if you are in the top 20th, like the top decile or even quartile in two or three areas, you can find a way to differentiate yourself. Whereas previously, if the cost entry was mediated primarily by finances, like if you don't have the money, you're fucked. So if you don't have 500 grand to start to buy or rent the infrastructure you need for that tech startup, like you do not pass go. That's it. You don't have a chance to use those

Starting point is 02:04:22 other abilities. But I could go on and on. I wanted to, you mentioned the age of absurdity. Do you have any other favorite philosophers or writers? Oh, a lot. I'll draw on some of the influence we talked about. In terms of stoicism, I think what really just got me turned on to that originally was sort of an introductory text that summarizes a lot of the work which is uh the guide to a good life yeah yeah that's uh irvine right william yep which is um not source material and perhaps if i knew known how approachable the source material was either seneca aurelius then you can you can also go straight to that but i just found it a

Starting point is 02:05:02 very easy easy again one of those things as we talked about what we like like uh easy to learn hard to master i found uh the guide to good life the introductory text was just an easy way to learn about it and recognize why this resonates and then i kept pulling on the thread and and kept reading from there um let's see what else um one of the things we haven't talked so much about is is i became a parent uh four years ago or so so now i have two boys and i've tried to treat that as a system too to some extent of like how can i become better at simply being a parent and being there for the two kids than we have. And the work of Alfie Cohen, he has a bunch of really good books.

Starting point is 02:05:51 The one that got me started was Punished by Rewards, which is actually a book all about motivation and how rewards basically don't work in most cases for developing kids or encouraging creative work or it kind of tackles both everything from students to works to kids um there's also a great book called the myth of the spoiled child um which is even more specific about um nurturing and supporting kids and so forth uh that's been very inspirational that has then led led to, I just read Daniel Pink's book Drive, which takes some of those same ideas about motivation and rewards and extrapolate them in a kind of a little bit of, I mean, I like the book, but kind of an obnoxious language of

Starting point is 02:06:38 businessy, like everything is business 2.0, this, that, and the other thing, which is a little grating, but the core concepts and points are really strong and very influential for how we try to run the business, which I'm kind of going just free association here. The other book is called Turn the Ship Around, which is a wonderful book about a guy, a naval, what do you call it? Not commander, but admiral or something that was running one of the worst performing U.S. nuclear submarines and turned it around to be the best performing U.S. submarine by infusing his staff with basically saying, they're not waiting for a command, they're saying what they intend to do. It ties into many of the same topics, but it's

Starting point is 02:07:24 very actionable and very approachable. I really like that. And we try to use that as aspiration for how we drive projects, motivation, and cultivate this idea of manager one at Basecamp where people are sort of individually both responsible and capable for doing the work and aren't waiting around to get permission.

Starting point is 02:07:47 That's been great. Another sort of just to fly all over the map, once I got interested in reading more about philosophy, I also got more interested in reading about sort of political science and the development of countries and authorities and so forth. There's a fantastic two-part book called Origins of Political Order by Fukuyama, I think is his name, and something about political decay, which traces back sort of nation states all the way back to 4,000 years BC and goes through all the case studies of the rise of China and so forth. And it's just a really interesting way of putting current events into a larger perspective. I think sometimes it's easy to freak out about things like the current election or whatever and like,

Starting point is 02:08:42 we're in a completely unique timeframe and all like all these challenges and so forth they're are you new and unique and no they're not right like history uh if not repeats and rhymes and if you know the pattern then it's both easier to cope because you go like this is not a unique punishment on me that we live through these times. People grappled with the same issues 2000 years ago, 4000 years ago, since pretty much the dawn of civilization. But it also gives you some idea of seeing the arc of time and seeing trends and seeing which way things point. And I think that's been very helpful. So I really like that. And as a parent, just to return to that, because quite a few people asked about this, are there particular ways that you quantify or assess whether you are being a good father or parent? And or are there mistakes you think that are very common among parents aside from the

Starting point is 02:09:48 over rewarding? Maybe they, yeah. Yeah. So I think, uh, I try to be quite direct. Like, uh, my oldest son is now almost four years old. And since he was at least two, he could actually tell me what he liked and he didn't like. And I know that that sounds like an overly permissive thing. You just have this kid commanding your parents around. But I think that's a stereotype, a cutout board that people use to excuse just forcing their will on little

Starting point is 02:10:16 people who can't really do anything about it. And that's one of the main things that I've sort of tried to just constantly put me myself in the shoes of my four-year-old boy right if I was in his shoes right now with his pressures and so on what would I think would be a reasonable course of action and of course it's not a perfect transplantation but I found that a lot of people I don't't know, they have a lot of, I mean, all functional parents love their kids, right? But that doesn't mean they always have empathy with their kids. And it certainly doesn't mean that they always act on that empathy for their kids. I think there's a lot of, it's not helicopter parenting thing. It's overprotecting and things that are convenient for the parent that, it actually be great for me right now if you did these things and then i'll couch it in

Starting point is 02:11:12 right language and justification as oh i'm doing what's best for you and i'll rationalize the convenience for myself yes and like oh it's best for me right now if you do what i say yeah of course that's best for you um that doesn't mean that's best for me right now if you do what I say. Yeah, of course that's best for you. That doesn't mean that's best for the kid. The other thing, trend that I've been sort of just alarmed about is this notion of basically criminalizing independence. And especially in the U.S., this war on kids basically being by themselves or doing anything that even looks remotely dangerous

Starting point is 02:11:47 that we've been at such a someone could get hurt which by the way is a topic of another good book um on this topic of parenting and letting kids um kind of free roam a little more um i think that we all have these romanticized version of oh when i grew up everything was wonderful and blah blah blah which i don't ascribe to that i don't ascribe to like oh everything is terrible now just because like i'm older and whatever right but i think there is a sense at least coming from denmark that um letting kids run risks and letting kids hurt themselves and letting kids learn the things they need to learn through personal experience, I think is so much more effective than trying to be a parent that tells your kids what's right for them. So just take one simple example. Sometimes like your kid

Starting point is 02:12:40 doesn't want to eat the things that they're supposed to eat, right? Like they just want to candy all day. Well, you can tell them if you eat all that candy you're going to get a stomachache right or well you can say that and then you can yank the candy away from the kid and the kid just goes like you're an asshole right you just used force to deprive me of this thing i wanted or you can just let your kid eat the bag of candy and get a stomachache and learn on their own accord that okay the next bag of candy maybe they'll eat that too maybe they'll eat the bag of candy and get a tummy ache and learn on their own accord that, OK, the next bag of candy, maybe they'll eat that, too. Maybe they'll eat the bag of candy after that, too. You know what? After the third time I found, well, sample size to exposure and sample size somewhat larger and indirect exposure.

Starting point is 02:13:21 But at least in my experience and observation of these things, like kids aren't that stupid and they take experiences that they have and they internalize lessons from them. And they do it a whole lot better if you don't try to do the pre-processing for them. If you don't try to basically chew their food for them and say like, oh, this is going to happen if you do that and then prevent them from doing that. that's not a very persuasive technique um so i've tried to perhaps to sometimes an extreme degree to say like hey by the way this is my assessment of the situation i think this is what's going to happen like one thing that a lot of people have been freaking out about screen time right you can't have your kid get an ipad and just sit on it for as long as they want because, then they're just going to be addicted to that. And they're going to sit on that eight hours a day. I don't, first of all, I found that to be categorically untrue with my sample size.

Starting point is 02:14:13 But I've also find it to be an unpersuasive argument in the grand scheme of things. I liken it to the article or the experiment of cocaine, right? Remember that famous experiment where they would have cocaine in a bottle for a rat and sort of the rat would just go over and eat cocaine until the rat died and everyone went like see that's what happens like if anyone tastes cocaine they'll just eat cocaine until they die scientific proof then i think in 2005 someone replicated a version of that experience experiment where they had an outlet of cocaine and then the rat or the mouse had a bunch of other activities too. There were other mice around. They could go in the wheel. They could

Starting point is 02:14:50 drink water. They could do all sorts of other things, right? Guess what? That mouse didn't just eat cocaine until it died, right? Oftentimes, if you think like, oh, my kid would just sit on the couch eight hours a day and just do the iPad, perhaps your alternatives suck. You're not providing ample, rich environment. You just want to engage. Perhaps you don't want to read to your kids. Perhaps you don't want to take them anywhere.

Starting point is 02:15:15 Perhaps you then just want to enforce this idyllic version of what you think, oh, they should just play with wooden blocks all day and that's really good for them. You know what? Fuck you. I mean, it's just i find it so lacking in basic understanding and compassion of like what would you want to do in

Starting point is 02:15:31 that situation and what then perhaps more interesting is that i've tried to then say like there's there's not really a limit on uh ipad use if uh colt wants to be on the ipad for eight hours in a day he'll binge for eight hours and that has happened right like that has happened one or two times like gets really into a game or a show or something else and really binges on it what happens the next day he doesn't want anything to do with that ipad because you know what kids are pretty good at self-regulating again sample size too um in my experience that if you have other interesting things and choices and opportunities that they can choose to partake in they will and this mania of like oh ipads with the new devil it's just i just find it hilarious there's a good um

Starting point is 02:16:19 twitter account i forget what it's called something about like uh terrors for the past or something where we go they pull out old newspaper clippings that go like, in 1895 people were like, books are really terrible. If people just sit all day and read books, then they'll get trapped in their own minds. And then it was like comic books are terrible, or

Starting point is 02:16:37 Dungeons and Dragons is terrible. Okay. At least there's a pattern of history here where people decrying new technologies and new forms of entertainment the kids choose to partake in as terrible haven't panned out that well um so perhaps there's a history there to be informed by and perhaps you don't need to freak the fuck out over the fact that your kid just binges a bit on an ipad like how can you say anything like didn't you just netflix binge the last time you had a babysitter and thought that

Starting point is 02:17:06 was a good time? Yeah, hysteria never goes out of style. The question of habits. So you mentioned a few things, empathy being one of them. I'll give you yet another two-part question because I seem to be, for whatever reason, too much caffeine maybe on the two-part thread today. But first is, there are a fair number of people who describe you as angry. And so part one is, do you think of yourself, do you think you're an angry person? Second is, what are the habits that have helped you to develop empathy? With your children specifically, maybe. Yep.

Starting point is 02:17:47 I think angry is a funny word to me because even when I'm going off, I generally don't feel angry. Sometimes I do. Let's be fair here. Sometimes I do feel that, but a lot of the times I think it comes off like that where that's not the inner mental state, the inner dialogue that's going in my head, right?

Starting point is 02:18:09 Like, I'm just processing these things, for example, and going through like, hey, this isn't right. Or I think this is, well, that's a version of the same thing. This is wrong or whatever. And I'm trying to process this and I'm trying to set up and decompose the system and as i'm decomposing the system of what is it that led to this um i'm pretty fired up but angry to me has this sort of residue effect where someone's just walking around with a grimace on their face and or they're shouting or whatever which oftentimes when i write perhaps the most indignant tweets, like none of the sorts is going on.

Starting point is 02:18:48 So I think it's one of those things where I forget what the novel was, but there's this concept of what you see in a person on the outside is often not the reflection of what's going on in their inner life. Sure. reflection of what's going on in their inner life sure uh and it's a valuable lesson to compare your own um outward profile sometimes uh and how you other people see you to to how you see yourself and like perhaps sometimes if there's a great disconnect you should change somewhat on one end of the other but perhaps more so it should teach you some empathy for other people and the fact that they probably live the same experience, right?

Starting point is 02:19:26 That there's a difference between the inner and the outer of the life. But another part of it, too, is sometimes things are just a release for me, too. Like, I don't have, like, things I walk around with a lot of anxiety about. I try to discharge sort of negative energy or whatever. And sometimes perhaps I should just shout into a pillow. But unfortunately, this invention of things like Twitter and so on has become a pillow for a lot of people, including me at times. When did you sign up for Twitter?

Starting point is 02:20:03 Yeah. Actually, it's funny because I totally didn't get twitter when it got started i got um on the first beta because they were using ruby and rails and i knew some of the people who worked on the very first version and then invited me to it and back then it was like an sms thing mainly sure i remember i don't understand this like what my friends are supposed to say where they're going and so on so anyway i didn't get it for like the first two years and i didn't really get into it until what is it 09 or whenever it was that uh a little while after it got launched um but then i totally got addicted to it of course right because first it is this pillow and it was what's funny is sometimes it's

Starting point is 02:20:41 that's therapeutic right the have the pillow just for yourself, even if no one was listening. Well, now I have like, I don't know. Millions of pillows. I have quite a few people who find that interesting. And I can understand that because I listen to other people's pillows too. And some of my favorite accounts are other people's pillows where they're just screaming into it. And sometimes it's just anger. And for the best accounts, of course, it's more than just anger. It's insightful commentary on things that should be better, right? Like, let's not make the same mistakes again,

Starting point is 02:21:14 or let's analyze the system and so on and so forth. So I absolutely adore Twitter in terms of personal therapy and the way it allows me to watch the therapy of others. I was just thinking, maybe I should change my Twitter bio to screaming into the pillow since 2009. And if you don't follow Patton Oswalt, he's a comedian and brilliant Twitter account. I mean, very insightful commentary, but hilarious at the same time. Lots of screaming into the pillow stuff. Very, very high caliber. I wish I could add that spice to the mix.

Starting point is 02:21:53 That was also really funny because sometimes it is just loud voices into the pillow. And that's not always a lesson to listen to. And I know, for example, Jason Freed, my business partner, for quite a long time he disconnected from twitter and i can totally understand that i can totally understand that certain people have a disposition where listening to people shouting to pillows all day long is not a great way for them to spend their time i don't know why but it doesn't affect me in that negative way like i can watch a lot of pretty negative shit going on. But if I feel like there's kernels of truth and, and there's, there's insight in that, uh, it doesn't, it doesn't transport. Like I don't sit in steam and get really angry, angry and ruin my night over it. Um, that's at least pretty rare. I'd say what, uh, just to jump to the habits, uh, because it's, I think a lot of parents have the

Starting point is 02:22:44 best of intentions. They read books. Maybe they even have some great first principles, but it doesn't cross the chasm from an abstract sentence in their head to regular practice. How do you do that? So I think perhaps one of the best practices we have is just about winding down for the evening and then always ending up like I often put Colt to sleep now. And Jamie, my wife, will put Dash, our younger boy, to sleep. And I just get to spend like, I don't know, an hour and a half, two hours from like dinner through reading books, through taking a bath or whatever at night and it's really a lovely ritual to have just those tasks okay we'll fight a little over not even fight i'll try all sorts of rational arguments for why he should brush his teeth and they'll all fail and i'll come up with

Starting point is 02:23:40 some funny story of like why we need to brush teeth on the whale or something and then all of a sudden like brushing teeth is the greatest thing ever um that was just a replay from last night however like we'll read the same books again or whatever and just having that um consistency in that pattern of it is just uh really nice and i think on top of that um the privilege of working from home affords me things like I take him to school most mornings. And yeah, that means I start a little later. And so what? Then I work a little later, too.

Starting point is 02:24:12 And it also means I'm here when he comes home from school and so forth. It's just I feel like I'm very mindful of thinking of things like life is long enough. Not life is too short, because I think that's when you're living it wrong life is long enough and if i pay attention if i do my negative visualization and if i truly make the hours count with colt with dash with the family then i'll be happy when it's over because i i do negative realization on that all the time. Like, I have a fantastic time right now where I have an almost four-year-old who really enjoys spending time with me, at least most of the time, when he doesn't call me a stupid idiot or doesn't want to see me again. Hopefully, thankfully, it doesn't last that long at the time. But of course, it

Starting point is 02:25:02 happens all the time too but i also look and think like in 10 years that that just won't be true there's just there's no version of reality well healthy version of reality where where that happens in the same way when he's 14 like then he's that's over right so i will make sure that the next 10 years or whatever where we go through this period where that isn't true and we have this kind of relationship that we have now, which is sort of very high intensity and many hours and so on, that's going to count. And I'll be happy on the other side. And then I can enjoy the other part of it, right? Then when he becomes a teenager and yells at me perhaps even more and in even more pointed ways,

Starting point is 02:25:47 I can appreciate that too, right? Someone finding their independence and so forth. And that could be a chapter and I can appreciate that too. Because I look back on, I've just turned 37, and I look back on my 30s or better part of that is done, and my 20s are certainly long gone. And I look back at those periods and think like, I got the most out of that. Well, not the most because it's not an optimization.

Starting point is 02:26:09 I got good out of that. I do not, there are no regrets here. I don't regret just spending my 20s just locked in a room working on some piece of software all the time because that's not how it happened, right? Like I set up in such a way that I can live through my 20s, my 30s, hopefully then my 40s, my 30s, hopefully then my 40s and my 50s and whatever. And then I can come and arrive and be 85 or 90 and say,

Starting point is 02:26:31 I lived a good life. And it's okay that that's at the end. And that's it. That's what we're here for. When I'm going to jump into, if you have the time, I'd love to go through some, some rapid fire questions. They don't, they don't have to be rapid fire answers at all. But when you think of the word successful or hear the word successful, who's the first person who comes to mind and why, or who comes to mind? Um, it's a bunch of names that come to mind. One's kind of trite is my is my mom um and the reason i say that is she is such an upbeat happy outlook like she is the perfect unknowing stoic she's actually a catholic but i think she's exceptionally good at many stoic principles of

Starting point is 02:27:23 tranquility and so on and dealing with sort of adversity of life in a way where like she's incredibly happy with very first order principles like the best things in life and doesn't care at all about the second best things in life and that's definitely an inspiration but i met many other people along the way um who aren't successful in any meaningful objective term from the outside of someone looking at either the job they have or uh the money that they make or the house they live in or the clothes they wear any other things of that kind and they just have a an inner life a mental life that where I just go like, oh, I'm jealous. I feel like I'm doing pretty good on that scale.

Starting point is 02:28:09 And I've certainly met people, friends where I'd still go like, you're really rocking it, aren't you? When you say internal life, what do you mean by that? I mean that they have that sense of tranquility, right? They've arrived at a point of like, wow, you have an amazing amount of tranquility and calm in your life, given the fact that in some cases, you face some real adversities, right? It's just impressive to me. And I mean, it's not to say that that doesn't happen on the other, too, that someone who does have outward success can also have that. I've just found that there's basically no correlation that I've found. Yeah, no, I agree. People have the best, most tranquil inner lives and contentness.

Starting point is 02:29:00 There's no correlation to where they are in that outward status. Some of them are. Some of them have made all sorts of money and whatever status. Some of them are, some of them are, have made all sorts of money and whatever. And some of them have made none of the sort. And some of them have made a little of it and everything in between. And I've been able to find no correlation there. So I'm still sort of searching for what that is,

Starting point is 02:29:16 but at least for me, getting conscious about that fact and being diligent about having a philosophy of life, having a framework and working on these things, I mean, that has made a difference to me. So maybe that's also, I mean, I should probably inquiry more about this because I find it endlessly fascinating,

Starting point is 02:29:35 especially since you can't find that statistically correlation like, oh, it's this one thing that they do. No, it's all inside the head. Is there anyone who, to counterbalance the critiques that you've had of, say, Silicon Valley and the venture-backed startup game, is there anyone in the business world you would really like to spend, you really respect and would like to spend more time with, or just spend time with? You're like, you know what? That person is either fascinating or doing it right, seems to be doing it right. I want to spend more time or learn from that person. Good question. One of the early business idols that I have that I'd still love to meet, I heard that he just mentioned Basecamp and something unrelated,

Starting point is 02:30:24 which made me all sort of fanboy flutter was um ricardo semler oh yeah from semco in brazil he wrote a fantastic book uh called maverick that um was a great inspiration to to me and i know to jason as well and to me as well. Giving the confidence of like, Jesus, if this guy with 8,000 employees running an industrial company producing pumps for oil tanks can be this radical and this incisive about how to design a company, like surely we as a software company

Starting point is 02:31:00 with no fixed assets in the 21st century can be just a little more radical than what we think is possible right so i think that that uh ricardo similar is definitely um high on that list um who else um in terms of a larger than life persona i've always had sort of a soft spot for richard branson um i know that like it's hard to know like what's actually caricature and myth and whatever once you get at that level but um absolutely fascinating character um warren buffett i know we're kind of sort of just going through a highlight reel that's kind of just easy like oh yeah i wish i'd also sat down with steve jobs when he was live.

Starting point is 02:31:46 Okay, yeah. You started with a Hick artist similar. I bet a lot of people don't know who he is. But yeah, I think those are some of the characters that I'd love to meet. But the thing is what I found in a number of cases were

Starting point is 02:32:03 and I'm sure this goes for me too on the episode. And like when you meet your heroes, then sometimes it's better just to have the idealized version. Yeah. I agree that you took away when you read their book or saw their talks or listen to their podcast or did anything else like that. I've at least found that it's been a rare moment where I've met someone and where it then exceeded that and went above that.

Starting point is 02:32:29 Well, I would say that A, that's true. And B, I used to think that was because they were flawed in some way that... Because I would meet the heroes with clay feet, as they say, right? And then I realized, I thought maybe it was because they're flawed in some way that I would meet the heroes with clay feet, as they say, right? And then I realized, I thought maybe it was because they're flawed in some way that wasn't portrayed or wasn't reflected in how they portray themselves. And then I realized, you know what? It actually relates to your point about expectations and why you were unhappy coming in second place, which is silly in retrospect, but you came into it or most people come into it let's say having read a book or listened to a podcast which is really the highlight reel of that person so then

Starting point is 02:33:13 you meet them and you're like wait a second i thought all 90 minutes was going to be like the fucking 60 second trailer what is this bullshit and then you're like oh wait it's a human being too and uh exactly uh and it's you know i think about this sometimes when it's like, I'll have, I had this guy come up to me, this happens surprisingly often, which is part of the reason why I stopped investing in startups, but where I'll be like in a bathroom at an airport and some like 22 year old startup founder will come up and start like breathing on my neck, pitching a startup right behind my head. And I, and I clearly not the best time. It could be the most amazing pitch mankind has ever heard.

Starting point is 02:33:48 Not the best time. And on top of that, I'm probably running to a flight. So I'm like, you know what? I'd love to talk, but number one, you're breathing on my neck and making me uncomfortable. Number two, I have to run to my flight and I kind of run off. And they're like, wow, Tim Ferriss is such a dick. I had no idea. And forever, that experience will have contaminated whatever view they might have had of me. So yes, I mean, I think there's always a risk in meeting your heroes. And I think it's exactly that point that someone who reads Rework or whatever, we get a fair amount of email, often very flattering, right? And it's really great. It's great that someone read sort of the highlight reel of 10 years of thinking, right?

Starting point is 02:34:28 And then sometimes I get the follow-up question of like, oh, can you then tell me like, what's the one thing you'd like for like a startup founder to do or something? Like, dude, you just read my highlight reel. You think like I'm on the spot going to come up with something brilliant? Like that's just not how material works right like it's like walking up to a comedian like hey say something funny right it's just like you can't just walk up to someone and like oh be brilliant please can you be brilliant for me for like 30 seconds on command right here like most people just most brilliant people aren't brilliant most of the time. It takes a long time to develop the material and develop the thinking and so forth.

Starting point is 02:35:11 And when they put it out, that's it. That's the best stuff. The best stuff isn't hidden somewhere else. I guarantee you, if I had a ton of other super brilliant things sitting in the back of my head, I'd publish them, right? They aren't just sitting there waiting, oh, they're just waiting for this guy to write me and say like, hey, do you have something brilliant to say about this one specific thing? And so I get how people sometimes write me and I'll write back and like, I'm sure they're disappointed, right?

Starting point is 02:35:39 Because it wasn't brilliant. All they saw was this condensed little version of it uh and i think about it in the same ways that the like startup or um comedians they go on the club circuit and they work for years to come up with enough to fill an hbo special right all the stuff in between just wasn't funny dude like they develop i don't know 30 minutes of material and they probably spend 300 or 3,000 hours of shitty material to get there. No one has killer shots all the time. That's part of the reason I love to go to – I enjoy stand-up comedy, but I love to go to small venues where well-known comedians are working on their material. Because you see half of it bomb and they have a little notebook and they take notes on it. And I love watching that. If people listening

Starting point is 02:36:28 have never seen that process, there's a documentary called Comedian that tracks Jerry Seinfeld and another up and comer as they are working the circuit and as Jerry's working on new material. And you see Seinfeld bomb, I mean, crickets. And it's reassuring and I also think realistic to check that out. And it informs a lot of other areas. Speaking of documentaries, do you have any favorite documentaries or movies? Let's see. I like The Big Short.

Starting point is 02:37:08 I had read the book already. That was a good one um let's see what else um i just saw what was it called a montage of heck about uh nirvana guy um which was interesting too i the funny thing is with kids i don't know what it is there's like a cut off at about an hour where like we can devour tv shows no problem because they fit within the hour and that's good. But a movie that's two hours often feels like, oh, that's impossible. We'd have to get a babysitter. It's got to be on a Saturday. It's got to be this special thing because it's not that often that you get the two-hour stretch to fit into your life versus the the tv show like one hour like fits perfectly for me which is why when it comes to non-fiction stuff um i love catching sort of again the highlight reels like belmar and his new rules segments i find to be

Starting point is 02:37:58 some of the most he's wrong on a lot of things as most people are and i mean he's very right on a lot of things which then when you disagree with him makes it feel like he's that on a lot of things as most people are. And I mean, he's very right on a lot of things, which are then when you disagree with him, makes it feel like he's that much more wrong on the things that he's, you disagree with him, which happens with a lot of people. I'm sure lots of people, I get this all the time on,

Starting point is 02:38:15 on tweets. I get these backhanded compliments. Like I usually think that DHH is an idiot, but like, Hey, this one thing was really great. Like without realizing that, you know what like

Starting point is 02:38:25 there's a lot of people who kind of have that emotion about just different topics right so maybe like no one is just that brilliant all the time and if they say something you find really spot on and excited insightful when they talk about another topic where you aren't in agreement like it's going to sting just as hard the other way um yeah i don't know if that was that was a good answer i find more that more than documentaries what i sometimes get a little i get a little impatient with documentaries because i kind of find like the point they're trying to make could be made in like 10 minutes right and we're stretching it to an hour and 45 with pictures and unless those pictures are amazing um there's a lot of other things I'd rather do. I'd rather watch Game of Thrones and then spend the other 45 minutes reading a book where I feel like the compression of ideas and condensation of content is greater. for when we wrote Rework that every idea should be expressed

Starting point is 02:39:25 preferably in one page. And if it had to, two. And I think there's only a handful that's three pages. Because I hate reading business books and watching documentaries where you're like,

Starting point is 02:39:37 okay, I got the point. Right. This is a 15-minute TED Talk that is bloated into 400 pages. Exactly, right? And I have that problem too. Sometimes I'm sure some of my own content where I

Starting point is 02:39:45 go up on stage and like, I have 20 minutes of content, but my slot is 45. Shit. Alright, let's just jam a pack of memes and funny pictures and try to make some jokes. I think there's a lot of really

Starting point is 02:40:01 important things to know and learn that just, they are as long as they are and and that's it like we got some negative feedback on we worked something like oh i really love all these ideas and like the person would rattle off like i don't know how many ideas right and they'd say but the book is really too short and like wait a minute um most business books i list like one two or three things that really stick. And they're like 400 pages. And you just rattled off 12 things. And we got it to you in like two and a half hours.

Starting point is 02:40:31 Like, how is that not a win? Yeah. Yeah. I mean, I think the key there is to respond with, well, you realize the important point is not just ingesting the information. You have to actually do something with that. But what books have you gifted most to other people if you've gifted books? I haven't gifted a lot of books. I made a lot of recommendations for books. But part of it perhaps

Starting point is 02:41:00 is that I don't really buy physical books anymore. I'm all Kindle all the time. I love Kindle. And then on top of that, I'm all Audible. So I've been traveling a fair bit since I started racing internationally. And that sometimes includes driving for long periods of time, not on the track, but to and from destinations. And I find Audible is just a wonderful way to read books without reading them, like getting the information of the books while

Starting point is 02:41:30 you're doing. So that's how I'm, that Fukuyama book, The Origins of Political Order, 24 hours. Wow. So if you wanted to get somebody hooked on audiobooks, which audiobooks might you suggest to them? The one I'm listening to right now, The Age of Absurdity, is really good. Not just because I think it's a great book and funny. It's also because the narrator just is perfect. I can just imagine sort of this crotchety old guy sitting in his rocking chair, just rattling off sort of curmudgeon ideas, which is exactly what this book is. But that's also just really funny. And I like that a lot. And then if you do have sort of the stamina of sort of a major tone, that Origins of Political Order book, I thought was pretty great. Some other books, like for example, the drive book, I got that on Audible as well. Didn't love that as much. It's funny how much the narrator can really taint or lift up

Starting point is 02:42:34 material. And obviously that's a personal preference, but that's why before I get anything on Audible, I always, even if I know I want the book, I'll listen to the preview and go like, eh, I don't know, maybe not that guy. Yeah, you need to hear the narrator first. But outside of even Audible, there's also podcasts, obviously. And my absolute favorite podcast is, well, I have two, but Dan Carlin. I was going to ask you if you'd heard Wrath of the Khans on Hardcore History. Yes, that's what got me hooked on Hardcore History. So Wrath of the Khans I thought was just absolutely amazing. His work on the Second World War, on Rome. I've pretty much devoured most of it, and it's all just stellar.

Starting point is 02:43:19 But then, of course, that's what got me hooked. And then he reeled me in with his common sense which is his political podcast uh which i just find absolutely wonderful it's we talk about therapeutic uh experience of twitter this is a very therapeutic experience of digesting things like the current election because i find his observations and his viewpoint, not only does it match enough with me that I can go, yeah, yeah, yeah. But it's also novel enough that I go like, oh, I haven't actually thought about that angle. And that's really the most rewarding kind. Maybe that's not always the most challenging kind, but it's the most rewarding when you both generally agree with the vantage point.

Starting point is 02:44:01 And you also are continually bombarded with novel takes on the subject. Yeah. Dan's amazing. He's been on the podcast as well. Yeah, I've had him on the show. I got to go and listen to that. Oh, he's great. Yeah. I mean, he talked a lot about, as he called it, copywriting your faults. And he talked, for instance, about how he would always get criticized for jumping into the red. He would whisper and then he would talk really loudly and he got chastised forever. Everybody wanted at the time, this very classic kind of deep voiced radio personality. And then it flipped like five or 10 years later. They're like, wow,

Starting point is 02:44:40 it's so great that you have this unique personality on air. And he's like, yeah, okay. That liability has now become an asset and a great, great story. Really sweetheart of a guy too. I'm going to ask a couple of questions that sometimes hit, sometimes don't. They don't always have a ready answer, but what purchase of a hundred dollars or less has most positively impacted your life in recent memory? And it doesn't have to be exactly $100 or less, but just a non-expensive purchase that is really positive. I have the question ready right here.

Starting point is 02:45:14 Okay. I bought a skateboard about two months ago, which has a funny story in itself. I watched Casey Neistat. Is that how you say his i watched uh casey neistat is that how you sure yeah casey neistat um his thing on um on the um those new electrical um skateboards oh the boosted boards boosted boards that's what it was right and i thought like oh my god this is awesome i need to get a boosted board and i went on to the site and first i was like what why what i can't buy it there's like a version two out or something and like it took forever to find out that just they had a lot of demand and they weren't shipping right now anyway okay i signed up for that and then they're like oh yeah

Starting point is 02:45:53 we'll ship it to you in three months and i went like shit i was excited about skateboard now so i went online and found a manual version so to speak. I used to skateboard back when I was a kid, but literally had not skateboarded in 20 years, right? But I happen to live right now out here in California where I'm just the perfect distance away from lunch that a skateboard is just what I need. Like if I walk, it's like just over 15 minutes and I don't always want to spend like half an hour on the road and back. And it kind of also is too short to kind

Starting point is 02:46:32 of take a car that feels ridiculous. But a skateboard is just perfect. Like I can get there in like five minutes on the skateboard and it's just fun. And the skateboard was like 120 bucks or something. And not only is it a lot of fun it's one of those things where you're like okay i haven't skateboarded in 20 years first of all like the basics are the same but the skateboard is still a good bit better i don't know what happened in in wheel technology and whatever but the free rolling nature of a good skateboard today is just amazing um they really just don't require that much effort but still just enough effort that you actually feel good about it because you're like hey this is actually kind of exercise and

Starting point is 02:47:09 i'm stretching so which actually the boosted board wouldn't so i don't even know if the boosted board when it arrives now i i take it maybe i wouldn't even do that right i just landed here because and also even better a skateboard is 100 bucks and a boosted board is i don't know a thousand bucks it's up there Yeah. I have a booster. It's not exactly the same thing. If you want to commute on a skateboard, um, like you're not going to go 10 miles on a, on a manual version.

Starting point is 02:47:32 At least most people wouldn't. And a boosted board, you realistically could do that. So I'm still kind of curious about it, but I've just loved that skateboard. And it's funny because I'm a pretty big car nut. And like, I've had the good fortune to enjoy all sorts of cars and have all sorts of opportunities to do that still.

Starting point is 02:47:51 But since I got that skateboard, I've not really touched them. I work from home, so I don't get a lot of opportunities to otherwise drive. I get to take my son to school sometimes in the morning, and that's about it. Otherwise, I don't need to otherwise drive. Like I get to take my son to school sometimes in the morning and that's about it. Otherwise I don't need to be anywhere. Right. So lunch was usually the one time where, okay, I'll just go somewhere for lunch, just in part for the fun of it. And now I don't have that, but because I just, I skateboard, I just skateboard to lunch every

Starting point is 02:48:18 time. And it's awesome. What kind, do you know offhand what kind of skateboard it is? It's like a short, it's kind of like an oxymoron. It's a short longboard. Okay, got it. So it's made like a longboard in terms of it's not for making tricks and so on. The wheels are relatively large.

Starting point is 02:48:31 It is for making, actually not commuting, but it is for transportation more than tricks and so on. But it's not so long that it kind of feels like a huge thing. Like a surfboard, yeah. Exactly, exactly. I just, I can pick it up up it doesn't weigh very much and it's just perfect for skating over to uh to a restaurant sitting down eating a sandwich in the gorgeous southern california sun and skateboarding back yeah the boosted board i so i think that first of all you've uh accidentally done some very good prep work if you do decide to use the boosted because you do not want to be... I know a lot of 30-something, 40-something-year-old guys

Starting point is 02:49:11 who have not touched a skateboard and they go straight to a boosted board, which is... And they fall out and break their arm. You have to be... It's a high-powered vehicle. I have one about 50 feet from where I'm sitting and it's a fantastic device. But what I've realized is I don't have enough self-preservation instinct nor... To not get to an hour. Yeah, yeah, exactly. To realize just what I'm doing. And I also just have a history of flashing back to when I was 16 and trying to do things I did then and ending up hurting myself. So the coolest, most surreal use of the Boosted Board for me is finding a very gradual hill

Starting point is 02:49:53 and carving uphill because the danger is really low and it's just the oddest feeling imaginable. It's kind of like surfing up a wave without having come down at first. It's a very surreal, fun experience. So that's where I would start. And definitely do not set it at the fastest setting when you first get on it. I got to get a helmet too. I don't really have a helmet for this small board. I'm not driving where there's really any cars and so forth.

Starting point is 02:50:23 But I remember I tweeted about a boosted board and some guy was like, dude, be careful with that. I'm not driving where there's really any cars and so forth. But I remember I tweeted about a boosted board and some guy was like, dude, be careful with that. I just cracked my skull. Yeah. You had a helmet as a must have. Yes. What is the, this, no, this is, doesn't have to be monetary, but what is the best or most worthwhile investment that you've ever made? Or one that comes to mind. I'll give you an example. I mean, it could be money, time, energy, any other resource. For instance, I had this woman on my podcast, Amelia Boone, who's the world's most successful obstacle course racer. And she's also a full-time attorney, but she ponied up for her first toughest mudder competition. It was like 450 bucks. And that was a big deal at the time. I mean, that was quite an outflux of cash, but that created an entirely new career for

Starting point is 02:51:08 herself. So it could be just about any investment of any type of resource. Does anything come to mind or really? Yeah, yeah. About, so I've been into photography for, I don't know, 10 plus years. But I had an affliction point about three and a half years ago where I bought a Leica digital camera, which is, like, I was into photography, but I wasn't like, oh, yeah, let me spend $7,000 on a camera and another $3,000 on a lens. Like, $10,000 for a camera and another three thousand dollars on a lens you're like ten thousand dollars for a camera is fucking ridiculous right and after i bought that camera i have captured more memories in the last three years a better quality

Starting point is 02:51:59 of just feeling like i absolutely aced the shot than anything like I look back if I took one thing away from from the last three years that I would feel in 20 years it would be the Leica if I hadn't had that and if I hadn't dove into that world which then in turn led me to just care more about photography more about capturing precious moments especially with kids um i'd be really sad in 20 years and i'm like i'm just it's one of those things where a ton of money for uh for a camera especially since you can get good cameras even on your your phone today but the the difference it's meant to me to capture all those priceless moments on a just not just a good camera but a freaking amazing camera has been priceless well the price was $20,000 but like the value has been right

Starting point is 02:52:53 what did what is the model what were the uh yeah m240 m240 that's the camera and what is what is your preferred lens yeah it's it's a 50 millimeter summa lux 1.4 the good thing about uh like a is like i bought those things new and you don't have to do that uh obviously you can buy them used and save a good chunk and then they kind of retain their value that unlike a disposable canon something that's worth zero dollars in three years i can't or like a lenses actually retain their values pretty well. Part of it, like it's just the lens has been the same for,

Starting point is 02:53:30 I don't know, like it's been around for a hundred years or something. Well, actually literally a hundred years. I think they just celebrated their hundred year birthday and the lenses for a very long time have been around and can be used on all cameras. So it's a very sort of, I feel like investment kind of thing. And i've just been incredibly pleased with it so for anyone who kind

Starting point is 02:53:50 of i thought it was just totally weird like the weird thing about the like is it doesn't auto focus you have to focus the lens yourself and it does it through this weird system called the range finder where you look through the viewfinder and you see two images on top of each other they They're ghosted. It sounds absolutely bizarre when you try to explain it and it's hard to explain. And then you have to line these two ghost images up on top of each other. That's when you know the picture's in focus. And I had such a disbelief in that. I started reading this guy, Steve Huff. I think it's stevehuffphoto.com, who's a big Leica guy and got me hooked on this stuff. I started reading about it and I still couldn't wrap my head about it I but I saw his pictures and I saw the package like it's like a camera one of the advantages is that it's tiny like I had a big

Starting point is 02:54:35 honking camera or canon camera for a while and I ended up never using it because it just I don't want to carry around a kilo on my back um versus the the leica is a lot smaller and i just i couldn't get my head around it so i went to lensrentals.com and i rented the camera i think you can do that for like 150 bucks or something and i spent a weekend with it and it was i won't say it's the same as the ruby experience because it isn't but it smells a little like it it was one of those things where it just like oh this is totally awesome and just that weekend from that lens rental rental i have some of my favorite pictures of gold right away right and you just go like yeah this is totally worth it are there any resources that have helped you to improve your photography or habits or

Starting point is 02:55:27 exercises anything yeah i think um there's a couple of good books um i think it's called understanding exposure yeah that's what it's called that was probably one of the first primers i read on just like oh what are these these three angles of ISO and shutter speed and aperture, getting a basic understanding of that. But then part of it really, again, came with the tool, which, I mean, I've been interested in photography before at the Leica, and I thought I took pretty good pictures, but I just became much more interested in finding out how to do great photos with the Leicaica because I got a couple of hits where I went like oh shit this looks as great as any photographer I could have hired

Starting point is 02:56:11 took this photo let me really understand that um it's funny one of the great resources lately has been Instagram Instagram has really transitioned for me from when I first started using it and then stopped using it where it was just everyone posted pictures of like their shitty iPhone pictures of whatever that looked like in 2009 or whenever it premiered. I never thought that was that interesting. And now it's transitioned to it's more of a distribution channel that fantastic photographers using high end gear use Instagram to distribute the photos, which means it just makes it so easy to follow really good photographers and get super inspired by how they do composition or color or or anything else and that has led me to just be more interested in developing that eye um and developing the sensibilities for what is a good picture how does composition work what is balance, like all these things I sort of kind of knew, but didn't really practice. And then post like, I kind of went like, all right,

Starting point is 02:57:10 I'm not just going to know what these things are. I'm going to internalize what these things are. And I'm going to figure it out. And I'm going to take great photos. The I want to second the recommendation for understanding exposure. That's Brian Peterson with the BRY. That's a great book. And it's short. It's 176, beautifully illustrated, lots of great pictures. And it gives you the toolkit of basic vocabulary and concepts so that you can then be a self-sufficient learner. Yes. So on the subject of beauty, we could talk about photography, but I want to actually throw out a question from our mutual friend, Toby, the CEO of Shopify. He said, DHH is a software crafts person. And the question he wanted me to ask is, what is beautiful code to you and what makes it so? Great question, because it is one of those things where you can just keep on pulling on the thread, right?

Starting point is 02:58:07 I think there's a bunch of technical things in the same way that you can look at a good picture or a great lap on a racetrack where you can just go like, oh, there's the rule of thirds here. And like that places the subject just in this part of the photo. And like the white balance is set just so

Starting point is 02:58:25 and so on and so forth. With programming, we have these things called pattern languages where you can use to describe sort of aspects of the code and can talk about the different techniques that you use. For me, if I had to name just one, I'd say composed method, which is this notion of breaking down a piece of software such that everything within an individual unit, as we call them methods in object-oriented program, is on the same level of abstraction.

Starting point is 02:59:00 And that it keeps decomposing at the same level of abstraction. So when you're making a whole system, you start at a very high level telling the machine to do something, right? And then to actually have that done, you have to break that down and break that down and break that down and break that down. And I find that the most effective technique that I have for doing that is really composing the method system. We stay at the same level of abstraction. We stay in the same sort of visual style of what the code is. Some code is very mechanical of like, oh, we're adding one to an array or whatever. Something very machine-like and something is very high level as in describing the outcome we're searching for, like withdraw from account

Starting point is 02:59:38 or something like that, right? Like to withdraw a certain amount from an account, you need to do some mechanical steps. You need to deduct from this one, add to another one, maybe add to an event log, blah, blah, blah, blah, all these steps. But if you can describe the system in such a way that when you dive in, it's easy to understand, right? You don't have to understand everything down to the nut and bolt to understand the system at a high level. That's a very direct signal of quality to me that I open up any piece of code in Basecamp and it kind of reads like a great table of contents that you dive through. Okay, this is the argument they're trying to make. This is how it breaks down into individual steps. I can dive into any of the particular essays if I want, but I also don't have to, right?

Starting point is 03:00:31 Like I can still understand what's happening and what the program was trying to do from that concept. So that's one aspect that we've done sort of at conceptual level. And there's a bunch of these wonderful patterns that help describe how to conceptually make good code. There's a bunch of principles about low coupling and high cohesion. This is some of the sort of the classics. And then there's just sort of sometimes also the visual style, which to me matters greatly as well, which Ruby just does a really good job at in the sense that it removes a lot of what we like to call line noise. Like characters you have to add because that's easier for the system to interpret so for example when i started with php i don't know if this is true anymore every line had to end with a semicolon that's how the interpreter knew that like okay there's a new instruction

Starting point is 03:01:18 coming right there's no semicolons at the end of the line in Ruby. And just that simple change cleans things up a bunch. So what I like to do in Ruby code is to reduce every method or class to the least amount of mechanical noise. That what's left is a pure description of the conceptual work that needs to happen. Maybe that sounds a little floaty, but it's just that there aren't, like the bolts aren't exposed, right? Like it's like you're sort of like, we don't use 10 screws and we don't make them show if five screws can do and we can hide them under sort of

Starting point is 03:02:06 a cover right and then not only that it's not just about making the veneer look good it's kind of like that quality of the unseen as you keep unwrapping and unpacking the code and diving deeper into it scratching the surface ever deeper it's just turtles all the way down it keeps sort of doing that all the way through to the final instruction at least the final instruction that the programmer can see um once the ruby interpreted takes over and produces something that becomes machine code perhaps that's completely impenetrable but at least the code that the programmer has to understand, like it just like a wonderful rabbit hole that you don't mind falling down through. And does, does, uh, do elegant, is there any correlation between elegant code and clean pros?

Starting point is 03:02:59 If you take someone who's a really, not just a functional coder, like you said, who can get the job done by using gum and band-aids, not that, but someone who's an elegant coder in your view, when they then write prose, let's just for the time being assume they're in English, is it also clean? Is it logical and flow well? That's what I find. I find that there's a high correlation between people who are able, at least in high level programming languages like Ruby, to produce elegant, beautiful code and people who are clear thinkers. And if you're a clear thinker at this level of abstraction, you tend also to be a clear writer. It's not always true and it's not true for all domains. There are certain, I think, areas of programming that are less about sort of juggling conceptual terms and finding just the right word for a class or method that are more mechanical in nature.

Starting point is 03:03:54 And that doesn't take anything away from the skill that it takes to do that. That's not the kind of programming that I'm interested in. That was the kind of programming that I thought I would never be interested in. That was the kind of programming that I thought I would never be interested in. The kind of programming that I fell in love with was this high conceptual level, where it really is a lot more like writing prose and phrasing and presenting your argument in a logical, methodical manner that's easy and clear to digest for a reader. Because I think at this level of abstraction, and probably at all levels of abstraction, but here more than other places, we're not writing for the machine. We're writing for your fellow programmer or for yourself in X amount of time from now, right? Again, that's true for all kinds of programming, but it's even more true the larger the system becomes and the more complex it is.

Starting point is 03:04:38 And modern information systems today are quite large and quite complex on all sorts of levels, right? And we are in a fight to push back against that complexity the natural state of complexity from a programmer taking a problem that they're trying to solve and then the first draft is very high the first draft of anything is shit that goes for pros it goes for i'm sure well for, I'm sure, well, I don't know. I'm assuming music. It goes for all sorts of creative endeavors. It's that the first draft, not often that good, right?

Starting point is 03:05:11 Like just like the first try of the joke. You have to refine it. And that's what I really love. I really love actually just getting something working. Like that's not the interesting part of me. Being the editor, refining it and improving it until it's as good as it can be, that mode of iteration is just awesome.

Starting point is 03:05:38 And that's where I extract all my flow on that. I think it's in that mode that I produce all the code that I'm proud of. It never happens that I write a piece of code and then I'm instantly proud of that. That's just not how it works. You have to go through the drafts and you have to go through the revisions to get to a place that truly shines. Now, I don't code, but I wonder if it works in the reverse as well. Meaning people who have really, everybody thinks, I shouldn't say everybody, a lot of people think they're good at writing. Very few people are really, really elegant and able to remove the extraneous thoughts and the equivalence of ums and ahs.

Starting point is 03:06:23 Yes. his thoughts and the equivalence of ums and ahs yes the if you had to pick or let me rephrase the question if you had to pull people from who were good at other disciplines to train them to code because you wanted them to learn really quickly or to be able to learn really quickly who would you pull from right so for instance, if I wanted to make good, I'm just making this up, but like good MMA fighters, but I couldn't pull from wrestling or anything else, who would I choose? I'd probably grab some gymnasts, right? Right. Because they have these attributes that I know will translate quite well.

Starting point is 03:06:59 What is that for coding? Like if you could pull from any other discipline or for, say, learning Ruby or Ruby on Rails quickly, and you wanted to put together your team who had the highest likelihood of success in a short timeframe, who would they be? that's a subclass of good writers which are focused on sort of uncovering the mystery and the story and explaining it in the simplest terms possible is uh something that just at least intellectually appeals to me i haven't actually seen that um transposed that often i don't remember actually talking to that many uh journalists who turned programmers. There's been some, but not that many. But that's sort of like the idealized form, I think, where someone has the clear thinking to really investigate a problem deeply, and then also have the writing chops to present that to an audience. What I've seen more have been people coming from other sciences we've talked about the scientific method i think that's absolutely a huge leg up when people who have internalized the scientific method aren't as

Starting point is 03:08:14 likely to be the people who are just like well there's a bug like that's just a computer that's just how it works i don't know what's going on there's always an explanation nothing is magic nothing is voodoo it's just because you don't have the pieces yet. So if you have the discipline of following the scientific method, then you have a leg up in that department, that's for sure. And then at least some share of people who work in those domains are also really good and clear writers. So I think perhaps that's an even better combination of someone who has internalized the scientific method to a T and also happened to write things that are digestible for normal humans. Sometimes that's a little hard for people who work in academics, which is what I like about the Journalist Act angle is that usually that's more practical, more pragmatic in the sense you're not trying to impress some professor. You're trying to keep the attention of a reader who presumably should get something out of the story that they're left with.

Starting point is 03:09:15 So that's just off the cuff. I've met programmers, though, from all domains that have turned out to be excellent and programmers from all sorts of backgrounds that have turned out to not be so excellent. So I don't know if there's a direct correlation here other to say that perhaps programming of. Of all the sort of I don't know if you can characterize as scientific fields, but programming is very open to people from different walks of life. I've met people. It's such a wide span of backgrounds that end up doing well in programming that I really like that idea of like, this is what programmers look like. And then you see like all sorts of different people, shapes, sizes, colors, backgrounds, genders, whatever. And the machine doesn't care. Right.

Starting point is 03:10:08 Right? The machine doesn't care how tall you are or whatever. There's no discrimination in that sense. I mean, algorithms and so on encapsulate sometimes human biases and so forth. But at least in the purest sense of the programmer and the programming language, I think there's just such a discrimination-free zone between that direct interface. Then move outside of that, try to go to Hacker News

Starting point is 03:10:33 or sometimes GitHub pull requests, and you'll see the all-too-human side of people interacting, which is full of all the biases and bile and whatever else you'd expect out of humans. And programmers are no better, perhaps even worse in some regards in that aspect. So just a few more questions. I know we could keep going, but I want to let you get back to your family. So just two or three more. If you could have one gigantic billboard anywhere with anything on it,

Starting point is 03:11:07 what would you put on it? That is non-commercial. Yep, yep. So impart one message to a lot of people. I'm trying to see if... See, that's kind of like the on the spot kind of be brilliant like i wish i could just come up with uh like just do it and i was original in uh in saying that um we can unfortunately i i don't think i am well we can take a different uh direction uh to get to a

Starting point is 03:11:40 similar destination and that is you mentioned the coco Chanel quote earlier. Yep. Are there any other quotes or maxims that you think of often or refer to often in your life? Yeah. Let's try to see if we can find one that's positive. Because it's funny, you just mentioned it. The thing that pops into my mind is that Sinclair quote of, a man can't understand what his salary depends on him not understanding, but that's not exactly a motivational poster for the office.

Starting point is 03:12:14 That go for all right. I think I need more time, man. I need to do a full creative on that because you're like, yeah, get this one shot at a poster. Damn well, better be good, right? I don't want to just put up a poop emoji or something like that and have a laugh for a second. You're going to treat this with some sanctity. Yeah, this is a lifelong project. No rush for right now.

Starting point is 03:12:43 What advice would you give your say 20, 25 year old self, if anything, and if, if, if you do have an answer, what place where you are and what you're doing? Yeah, I think, uh, the answer I usually have to that is, is kind of like a meta answer or a cop out, but the trending on which angle you see it from and i'd say the answer is that there is no answer um that i find that this seal and and perhaps i've had that in the past as well is that you look for this trick you look for this like if i just knew this one thing everything would be great if i just somehow had this one event happen or whatever that people a lot of people embody too much into this just this one thing right when the answer is it's all of the things right and they're interdependent yeah yeah exactly not only the interdependent but

Starting point is 03:13:41 there's no one thing that's just really going to turn everything around. Like it just doesn't, life isn't that simple, unfortunately or fortunately. Because it also just makes it that much more interesting, right? Like the thread is really deep and you have to keep pulling. Maybe that's the quote we'll use. Got to keep pulling. Keep pulling the thread. What, not to interrupt, but maybe a better question is, what habit or habits do you wish you'd developed earlier in your life?

Starting point is 03:14:16 Yeah, I hate to be a cop-out on that too. One of the things I look back on as I look back on time is, I'm trying to um what was it jason bispart had a good uh saying about this about i think it was native americans who i'm butchering this um but when they were preparing i think it was like a carpet or something right like an intricate carpet that was sewn like they left the errors in because sort of as a reflection of that, that time has passed and the errors of those ways or how we got to where we are. So I don't think I would have gotten to where I am. Well, this is kind of a truism in itself too. I wouldn't

Starting point is 03:14:59 have gotten to where I am if I had taken different paths. And I don't know if I want to be somewhere else. Well, actually I do know I if i want to be somewhere else well actually i do know i don't want to be somewhere else i want to be where i am right so if i want to be where i am i had to take the path i took to get there um i mean that's kind of like a yoda quote complete bullshit but i i think that's actually true that's why I try not to look back on anything with regret. My regret minimization framework is basically to not treat anything as regrets, including regrets. So on that then, do you have a favorite failure of yours? In other words, is there a failure or an apparent failure that set you up for later success?

Starting point is 03:15:43 Oh yeah, that's good. Let's see. Well, I tried to, when I was just starting with the university again, I tried to get a job at a number of software organizations in Denmark as a student helper, right? And I was so fucking blatantly overambitious that I blew every interview because I was like, oh, yeah. So we're talking about this entry-level programming position. What possibilities are there for me to basically inflict the overall strategy of the organization?

Starting point is 03:16:23 And people would go like, what? What the fuck are you talking about? What are you talking about, kid? You just what? What the fuck are you talking about? What are you talking about, kid? You just, you know, what are you talking about? You're just here to, like, program this web part or something, right? Like, you're not setting any direction for any IT or whatever, right? And of course, I mean, it was a very reasonable reply.

Starting point is 03:16:39 And I was being completely unreasonable in my request. But I'm glad that happened. I'm glad I didn't end up sort of just taking a job somewhere that I was unemployable for a while, at least until I met up with Jason. And I tell, we started working together as more like peers than sort of me being an employee i i don't think i would make that actually i don't think i know i wouldn't make that well good of an employee i i worked

Starting point is 03:17:12 at a fair number of places before i ended up working with base with jason at base camp and like i i don't know if i was always seen upon that positively because i kind of would stir shit way too often and and be perhaps way too critical about things that I didn't have any power or authority to change anyway. We just ended up just in a situation that perhaps didn't make things better. So I'm kind of glad that like it didn't work out right. Like I it's funny I remember just yesterday I saw this Jack Ma quote. I think he's CEO of Alibaba in China.

Starting point is 03:17:48 And he said when KFC first came to China, they needed to hire 35 people or something. And 36 people applied. I was number 36. He didn't get the job at KFC. He ended up instead running the biggest internet company in China, right? So sometimes the failures we have, I'm a big believer of this, many of the failures we have are flip side of the strengths we have. And the other side, way around too. Some of our best strengths are also some of our greatest failures. And it's all about the context that you happen to

Starting point is 03:18:24 put those in. Sometimes you put in a context where all your strengths turn up as just failures and weaknesses. And sometimes you're put in a context where the opposite is true and you really thrive. Right. So that's what I, a number of times when we've had to say goodbye to someone at base camp, I'm always like, this isn't because like you can't find somewhere else to be fantastic.

Starting point is 03:18:50 This is because right now in this role at this time, at this company, like the strengths that you have, they're not showing up as strengths. And I mean, I truly believe that I don't, that's not just like, Oh,

Starting point is 03:19:02 let's say something nice to the person who's going out the door. It's because I've seen it time and again, I've seen it in myself. I've seen myself fail in all sorts of situations for the same reasons that I would later succeed under whatever definition of success you want to use, at least my own personal definition of success, right? When it came to that. And I checked that all the way back.

Starting point is 03:19:23 I remember when I was in high school, I would take great pride in the f's i got i got an f in a number of subjects including math in like senior year and i would say like yeah i deserve an f i put in no effort here i intend to put in no effort i have yes um and same time, I would say, well, that A plus or whatever I just got in this topic. Yeah, I'm really proud of that because I put in the effort and I wanted to do it and I was good at it. And sometimes I'd go like, C, awesome. I put in 2% of the effort and I got C. That's more than fair. You're being generous, sir. So I think that you really have to look at that. And I look at that in public personas too, right? You have a lot of people who end up changing either a community or an industry or a country or the world. And a lot of people will go like, well,

Starting point is 03:20:19 that person is crazy or they're really a bad person in these all these sorts of ways right and you go like yeah like most sane people well-adjusted wouldn't put themselves in this situation most sane well-adjusted people don't get up on the stage in the way that people who end up changing things do right because they're sane and well-adjusted and like their swings aren't as big both their positives and the negatives right it's kind's kind of like if you look at the curve, like if you want to stay around the medium, like you just, you don't swing that much. But if you want to reach the peak, you also got to take the bottom. Yeah, you got to take the valley. Yes.

Starting point is 03:20:56 And then it's all about choosing to be response able. And that's where, I mean, there are so many tools that at least I've found, and it sounds like you've found helpful, like stoicism and trying to put those into practice so that you can try to get the benefits of that pendulum without suffering through necessarily. Which I think at least just being aware, right? At least being aware. Exactly. I know that like, okay, I have strength in certain areas that they're kind of like genes. They can express themselves in terrible negatives, right?

Starting point is 03:21:30 Like sometimes I truly do wish I could just keep my damn mouth shut, right? Like life would be a lot easier for me and a whole lot of other people if I could just shut the fuck up. But also, I mean, at least the positive contributions I've made sometimes have come because i can't shut the fuck up right so i just you gotta accept it in full honesty that like okay the good things come with the bad things yeah like if you want that then and that's not justification it's not that you shouldn't try to work on it like i i try to work on it and and then still sometimes you regress to to your habits and and your sort of uh proclivities but yeah it's the self-awareness and uh and being able to like you said develop that self-awareness at the very least put yourself

Starting point is 03:22:20 in situations where you express the better side of it more often right like i don't for example like oh i have self-awareness that i'm a jerk all the time justifies you being a jerk all the time right right hey if you know that there are certain situations that sort of express that part of you try to not put yourself in those situations as much as possible yeah i mean it's uh i was i was being interviewed recently and uh this part didn't make it to print, but I was asked a bunch of short questions. And one was, you know, if you had to attribute your success to an attribute, what would it be? And I said, impatience. And then they, like three, four questions later, they said, what do you think you most need to work on?

Starting point is 03:23:01 And I said, impatience. And what I've realized about myself is that I'm better at designing systems than I am at hands-on managing people. I just don't have a soft touch. I'm too indelicate. And that means I just need to have good systems and then say, hire one person who doesn't require the kid gloves and have them manage people. Fantastic. Then it works out. But if I put myself in circumstances that require a lot of tact and diplomacy, well, it's going to be a shit show. Exactly. Oh, man. Well, this has been really fun to catch up. Where can people learn more about you, learn more about Basecamp?

Starting point is 03:23:48 Are there any things or places that you'd like them to check out? Sure. So as we just talked about, I have that pillow I scream in with some regularity on Twitter. It's at DHH. I'm also at DHH on Medium.com, where I kind of scream for longer periods of time into the pillow. Long form screaming. Yeah. Long form screaming. I'm an Instagram at DHH 79. That's a little more uplifting. I have posted some of my photography and a bunch of other people's photography, a lot about cars and racing and other things i find beautiful and pretty um and then of course uh my life's work base camp it's basecamp.com um anyone who's trying

Starting point is 03:24:33 to sort of get their company organized and put things on the right track and are tired of being stuck in email and unread counters and chat room treadmills. You should really give that a try. Ruby on Rails, if you're into programming or want to learn how to be a programmer, now has never been a better time. It's never been easier to get started. Just as hard as ever to become an expert, but it's never been easier to get started.

Starting point is 03:25:00 And finally, we have a great podcast at Basecamp called The Distance, thedistance.com. You can find it on iTunes as well, where we profile companies who've been around, stuck around for 30 years or more, as we like to, Jason calls them stay-ups. The easiest thing in business is to start. The hardest thing is to stay. So that's what we aspire to ourselves. Basecamp, through the lineage of 37 Seals has been around for 17 years now. As we've talked about, I've worked on Basecamp itself for like

Starting point is 03:25:33 13 years now and same with Ruby on Rails. I really believe in staying the distance and going the distance. Perhaps that's also why I love endurance racing so much. But, um, yeah, I think that's a good summary of, uh, of the places to find me and, uh, my screams in the pillow. Well, David, thank you so much for the, uh, the time. There's so many more things I'd love to ask, but, uh, this has been a great catch up and hopefully, I mean, you've done so much racing and I know we were exchanging, uh, some messages probably, I guess it catch up. And hopefully, I mean, you've done so much racing and I know we were exchanging some messages. Probably, I guess it was yesterday. And you mentioned that you haven't done yet any rally racing.

Starting point is 03:26:13 I think you would love it. So we should definitely make some time for maybe doing a Team O'Neill in New England or something like that at some point in the future. I think you'd immediately kick my ass, which I'm totally okay with, but it's so much fun. I think you'd just have a blast because of, for all the reasons you already enjoy the racing, I think you would love it. But I want to let you get back to your evening and thanks for being so generous with your time. Thanks for having me, man. This was a blast. And for everybody listening, the show notes, as usual, will include links to everything that David mentioned at the end.

Starting point is 03:26:53 And certainly the books and so on, resources that he mentioned throughout, we'll dig up as much as possible. So you can find that at 4hourworkweek.com, all spelled out, forward slash podcast. And until next time, and as always, thank you for listening. Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email from me every Friday that provides a little morsel of fun before the weekend.

Starting point is 03:27:26 And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to 4hourworkweek.com. That's 4hourworkweek.com all spelled out and just drop in your email and

Starting point is 03:28:06 you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by Wealthfront. And this is a very unique sponsor. Wealthfront is a massively disruptive, in a good way, set it and forget it investing service led by technologists from places like Apple and world famous investors. It has exploded in popularity in the last two years, and they now have more than $2.5 billion under management. In fact, some of my very good friends, investors in Silicon Valley, have millions of their own money in Wealthfront. So the question is why? Why is it so popular? Why is it unique? Because you can get services previously reserved for the ultra-wealthy but only pay pennies on the dollar

Starting point is 03:28:44 for them. And this is because they use smarter software instead of retail locations, bloated sales teams, et cetera. And I'll come back to that in a second. I suggest you check out wealthfront.com forward slash Tim, take the risk assessment quiz, which only takes two to five minutes, and they'll show you for free exactly the portfolio they'd put you in. And if you just want to take their advice, run with it, do it yourself, you can do that. Or as I would, you can set it and forget it. And here's why. The value of Wealthfront is in the automation of habits and strategies that investors should be using on a regular basis, but normally aren't. Great investing is a marathon, not a sprint,

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Starting point is 03:30:01 use them and recommend them. In this case, it's a little different. I don't use Wealthfront yet because I'm not allowed to. Here's the deal. They wanted to sponsor this podcast, but because of SEC regulations, companies that invest your money are not allowed to use client testimonials. So I couldn't be a user and have them on the podcast. But I've been so impressed by Wealthfront that I've invested a significant amount of my own money, at least for me, in the team and the company itself. So I am an investor and hope to soon use it as a client. Now back to the recommendation. As a Tim Ferriss Show listener, you'll get $15,000 managed for free if you decide to open an account.

Starting point is 03:30:38 But just start with seeing the portfolio that they would suggest for you. Take two minutes, fill out their questionnaire at wealthfront.com forward slash Tim. It's fast, it's free. There's no downside that I can think of. This episode is brought to you by Four Sigmatic. I reached out to these Finnish entrepreneurs after a very talented acrobat introduced me to one of their products,

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The Tim Ferriss Show - #195: David Heinemeier Hansson: The Power of Being Outspoken

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Pet Camera - EBO Air 2

The Tim Ferriss Show - #195: David Heinemeier Hansson: The Power of Being Outspoken

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.