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David "DHH" Heinemeier Hansson — The Power of Being Outspoken | The Tim Ferriss Show

David “DHH” Heinemeier Hansson the creator of Ruby on Rails, founder and CTO at Basecamp (formerly 37signals), and the best-selling co-author of Rework and Remote: Office Not Required. Oh, and he went from not having a driver’s license at 25 to winning, at 34, the 24 Hours of Le Mans race, one of the most prestigious automobile races in the world. It is often called the “Grand Prix of endurance and efficiency.” David is one of the most outspoken technologists out there. He is not one to hide his opinions or mince words. Enjoy! Resources from this episode: https://tim.blog/2016/10/27/david-heinemeier-hansson/ Intro [00:00] How David and I first met. [07:29] From no driver’s license to racing cars [09:17] How David hacked learning to drive [15:35] Everything’s interesting if you dig deep enough. [17:09] Flow state while racing vs. flow state while programming [21:28] David’s big aha moment that led to Ruby on Rails [37:13] Is learning programming language like learning human language? [46:59] Why experienced programmers love Ruby on Rails [49:09] Jack of all trades or master of one? [53:28] Business ventures with Jason Fried +first principles [1:03:28] On keeping his business small and streamlined without being negligent [1:09:24] Does David consider himself a happy person? [1:18:34] “Expectations—not outcomes—govern the happiness of your perceived reality.” [1:27:00] From eschewing venture capital to accepting money from Jeff Bezos [1:31:49] The things that are more gratifying than retiring [1:36:06] How is money like alcohol? [1:38:33] Seneca on negative visualization [1:39:22] What has Jeff Bezos gained by investing in Basecamp? [1:40:42] On cultivating sustainable work/life balance habits [1:43:50] Bad luck vs. bad planning [1:54:21] An “almost pathological” distaste for repeating work makes a good programmer [2:01:03] Books David has been enjoying [2:05:56] How does David know when he’s being a good parent—and what common mistakes does he see other parents making? [2:10:55] Developing empathy as a parent [2:24:10] Who comes to mind when David thinks of the word “successful"? [2:28:21] Business idols [2:31:15] On meeting your heroes [2:33:55] Favorite documentaries and movies [2:38:25] Most gifted and recommended books [2:42:17] Favorite podcasts [2:44:25] A purchase of $100 or less that has had the most positive impact on his life [2:46:29] Most worthwhile investment [2:52:08] Photography resources [2:56:52] What is beautiful code? [2:59:18] What advice would David give his younger self? [3:14:15] A favorite failure [3:17:05] Connect with David Heinemeier Hansson: Like David Heinemeier Hansson on Facebook: https://www.facebook.com/David-Heinemeier-Hansson-202635783131044 Follow David Heinemeier Hansson on Twitter: https://twitter.com/dhh Follow David Heinemeier Hansson on Instagram: https://www.instagram.com/dhh79 David “DHH” Heinemeier Hansson: The Power of Being Outspoken Show Notes: http://fourhourworkweek.com/2016/10/27/david-heinemeier-hansson/ SUBSCRIBE: http://bit.ly/1dSzTkW About Tim Ferriss: Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 200 million downloads and been selected for “Best of iTunes” three years running. Connect with Tim Ferriss: Visit the Tim Ferriss PODCAST: https://bit.ly/2rYjUBr Visit the Tim Ferriss BLOG: http://bit.ly/17jDHw3 Like Tim Ferriss on FACEBOOK: http://on.fb.me/1avYUxq Follow Tim Ferriss on TWITTER: http://bit.ly/17d94TE Follow Tim Ferriss on INSTAGRAM: http://bit.ly/2IfH37J Follow Tim Ferriss on INSTAGRAM: http://bit.ly/2IfH37J

Tim FerrisshostDavid Heinemeier Hanssonguest
Nov 16, 20163h 34mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 4:18

    Cold open banter before the show

    1. TF

      Optimal minimal At this altitude, I can run flat-out for a half-mile before my hands start shaking.

    2. DH

      Can I ask you a personal question?

    3. TF

      Now would seem an appropriate time. What if I did the opposite?

    4. DH

      I'm a cybernetic organism, living tissue over metal endoskeleton.

    5. TF

      The Tim Ferriss Show. 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, which blew my mind in the best way [laughs] possible. It is mushroom coffee. What on earth is this? Well, it includes chaga mushroom, very powerful antioxidant, considered a superfood. I was introduced to chaga by Laird Hamilton, the king of big wave surfing of all things. And it includes another mushroom that is considered a nootropic, a smart drug, and this is lion's mane. In the entire packet, you just add it to hot water, it tastes like coffee. There is only 40 milligrams of caffeine, so less than half what you would find in a cup of coffee. So you, I do not get any jitters. I do not get any acid reflux or any type of stomach burn, and it put me on fire for an entire day, and I only had half of the packet. So [laughs] this stuff is really amazing. People are always asking me what I use for cognitive enhancement. Right now, this is the answer. So it is legal. It will not give you visuals [laughs] . That's something else. And you can try it right now by going to foursigmatic.com/tim. That is Four Sigmatic, S-I-G-M-A-T-I-C, foursigmatic.com/tim, and use the code Tim to get 20% off your first order. If you are in the experimental mindset, I do not think you'll be disappointed, foursigmatic.com/tim. 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 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/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 wanna 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, and little things that you may or may not be familiar with, like automatic tax loss harvesting, rebalancing your portfolio across more than 10 asset classes, and dividend reinvestment add up to very large amounts of money over longer periods of time. Wealthfront, as I mentioned, since it's using software instead of retail locations, et cetera, can offer all of this at low costs that were previously completely impossible. Right off the bat, you never pay commissions or account fees. For everything they charge, .25% per year on assets above the first 15,000, which is managed for free if you use my link, wealthfront.com/tim. That is less than $5 a month to invest a $30,000 account, for instance. Now, normally, when I have a sponsor on this show, it's because I 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, uh, 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

  2. 4:18 – 8:57

    Tim introduces DHH’s background and the episode’s scope (racing, business, code, philosophy)

    1. TF

      listener, you'll get $15,000 managed for free if you decide to open an account. But just start with seeing the portfolio that they would suggest for you. Take two minutes. Fill out their questionnaire at wealthfront.com/tim. It's fast. It's free. There's no downside that I can think of. Hello, boys and girls. Meow. This is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show, where it is my job to attempt to deconstruct world-class performers from all walks of life, whether that be sports, military, entertainment, business, finance, or otherwise. And this episode, we have the fearsome Dane himself, known as DHH, David Heinemeier Hansson, 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 37signals. He is also a best-selling 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 until he was 24 or 25. You can find him a number of places, on Twitter @dhh, Medium, where he writes longer form content @dhh as well, and on Instagram, uh, he does spend a lot of his Time taking photographs @dhh79. 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 relevant to what comes later because we're looking for, again, parallels across disciplines and first principles. So I'm not gonna dig into a bunch of stuff that you've heard 100 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.

    2. DH

      Thanks, man.

    3. TF

      Uh, it has been a long time since we've chatted, and, uh, we were, 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?

    4. DH

      Yeah, I think, uh, 2010 was when we started shopping our manuscript around, or maybe that was even when we published the book. It, it's so weird. It feels like it was just yesterday, and then six years later, here we are.

    5. TF

      [laughs]

    6. DH

      Um, but, I mean, it started in part i- in, in the same way that I start on learning a lot of things. I try to identify whoever in that domain I want to learn from and then figure out a way if I can either wor- learn from them directly or indirectly. And of course, if you can have a direct, uh, link, that's the best. And I had read 4-Hour Workweek, um, sometime in advance of that, and so had Jason, my business partner and co-author of, of Rework, and we were both just impressed with that and were like, "Hey, this is, this is kind of the path we wanna take. Let's see if there's a way we can learn from what you've done," and, "Oh, here's a connection. Oh, Jason knew Seth, and Seth knows..." And there we go.

  3. 8:57 – 13:00

    From no driver’s license to Le Mans podium: how the racing obsession started

    1. TF

      So w- we're gonna get into certainly programming and everything else, but since you talked about seeking out experts, I don't actually know the an- I don't know the answer to pretty much any question I'm gonna ask because then it'd be boring for me, but you ... I'm just looking at some cliff notes that I have here to go off of, but you d- I didn't know this part. So you did not have a driver's license at 25. Is that right? Around that-

    2. DH

      That's right

    3. TF

      ... negative?

    4. DH

      Yep.

    5. TF

      Okay. [laughs] And then, uh, uh, let's flash forward. What happened at 34?

    6. DH

      Um, I got to stand on the podium after 24 hours of racing in a town in France called Le Mans, uh, in the greatest endurance motor race in the world-

    7. TF

      [laughs]

    8. DH

      ... fulfilling my, um, dream of not only just completing that race but, but winning our class there.

    9. TF

      [laughs]

    10. DH

      And all that in, in nine years, from not having a driver's license to getting a driver's license, learning how to drive a normal car, um, and then getting into racing and climbing the ladders of racing until you're at the top.

    11. TF

      So [laughs] if, if we were to try to find the parallel example to you reaching out to me, and I'm sure other people, about publishing, two questions. One is how did you decide? Like, was there a moment or a dinner or a conversation where you said, "Yes, this is what I want to do"? And then second, how did you start trying to figure out how to go about it?

    12. DH

      Sure. So one thing I'd ... Since the mid-'90s, I had, on Danish television, just tuned into this race, the 24 Hours of Le Mans, caught it, uh, a number of years, and always 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 just found it that absolutely fascinating. And then in the late '90s and early 2000s, a fellow Dane, um, we're talking about Denmark here. This is a population of six million people, six million Danes total, so when another Dane does something remarkable on the world stage, um, 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 gonna have someone who reaches the peak, and we had. Tom Kristensen, uh, who now goes by the name Mr. Le Mans because he's won the race nine times, uh, 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. Um, then a Dane started winning it all the time. This is still before I even have a, a driver's license. But this just plants the seed, right?

    13. TF

      Mm-hmm.

    14. DH

      I'd already been playing lots of racing games. I loved, uh, racing games all the way from the Commodore 64 to, uh, Sega and Nintendos 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'm, I wanna 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 wanna arrive there and you wanna rent a car. The funny thing is, like, I wouldn't even think about 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.

    15. TF

      [laughs]

    16. DH

      Um, and that seemed to be well sufficient. Copenhagen is not that big of a town. It's very well-equipped for people who wanna bike or rollerblade or whatever. Um, so it wasn't even to use it in my own country. It was like, "I wanna go on vacation, and I want to be able to rent a car." So I learned how to, uh, drive a car in Copenhagen, um, which was in itself a, a funny process because most people, even in Copenhagen, I, 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, like, kind of, like, new and exciting

  4. 13:00 – 21:35

    Learning style: the “running narrator,” slow starts, and obsession with precision

    1. DH

      or what have you. And here I am, 25, I'm trying to learn how to drive a car, and I... At that point, I already knew programming. I had, um, already worked on a, 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, um, was remarking on the fact I was self-commentating. I didn't even realize that at the time.

    2. TF

      [laughs] Wait, wait, so-

    3. DH

      Like, the, the guy who's grading me whether I pass or I, I don't pass sitting right next to me in the car, right? I'm driving around, and I'm like, "Oh, I should've turned in a little sooner there. Oh, I should've turned on the blinkers there." And it was funny. He told me after-

    4. TF

      [laughs]

    5. DH

      ... "Oh, you pass, of course, but what was really remarkable was that you were narrating the whole process."

    6. TF

      [laughs]

    7. DH

      And I was like, "Oh, yeah. Actually, I don't know, maybe that wasn't so smart." I guess it worked out in that case.

    8. TF

      [laughs]

    9. DH

      But I was basically pointing out all my own flaws because that's how I learn. So that's how I learned how to drive a car. Then, um, skip forward just a little bit. I'm, I moved to the-

    10. TF

      Well, actually, you know what, David? I'm sorry, I'm gonna interrupt just for a second.

    11. DH

      Sure.

    12. TF

      So two things. The first is, do you do that self-commentary for a lot of things?

    13. DH

      Yes.

    14. TF

      You do?

    15. DH

      There's, like, a running narrator just running in my head when I'm trying to learn something, constantly pointing out, "Oh, you could've done that a little better," or, "Let's try this next thing on the, 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. And you-

    16. TF

      Right, you have a take two.

    17. DH

      Yeah, exactly. You have a take two and a take three and a take four. And by having that running commentary, I'm kinda taking notes on this is what I have to tweak next time around. Uh, and I, 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."

    18. TF

      Mm-hmm.

    19. DH

      "Okay, take three. Let's make this beautiful. Okay, take three... or take four. Let's simplify this. Okay, take five." Like, just having that commentary all the time about where can I improve, where can I get better?

    20. TF

      Mm-hmm.

    21. DH

      That's... I, I don't know where it comes from, but that's just how I've always gone about learning things.

    22. TF

      Did either of your parents do that or i- any... I don't know if you have siblings, but-

    23. DH

      A lot of these things on, on learning techniques, I've talked with other people around them. Like, these things have been codified, and I'm gonna 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, I think I just stumbled over the fact that, oh, if I do this, I learn faster.

    24. TF

      Mm-hmm.

    25. DH

      Oh, let me just do more of that.

    26. TF

      Right. Of course. No, that makes, that makes perfect sense. So I, I interrupted you, though. Oh, the, 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 anything that you, that you recall doing differently or focusing on in particular?

    27. DH

      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 understanding it and then do it well. And I remember in Copenhagen, all the cars we were, um, being taught to drive in 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 fussy process. Like, he couldn't tell me how much do I have to lift my leg-

    28. TF

      [laughs]

    29. DH

      ... to get the right clutch engagement. He's just like, "Oh, just go on the feel of it." And I'm like, "No, no. I wanna know, like, is it 30 degrees? Is it 70 degrees? Like, how far does the clutch have to come up the floor?"

    30. TF

      [laughs]

  5. 21:35 – 24:29

    First taste of the track: immediate feedback loops and “bottled flow”

    1. DH

      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 US was because I met a guy online, um, Jason Fried, uh, through a blog, um, and an email, and we got working together, and, and a couple years later I moved to the US to work with him full time. And here's another guy I met online on a forum, a discussion board for cars, um, who said, "Hey, I, um, I know of this racetrack that's just 45 minutes out of Chicago. Do you wanna come?" And I was like, "Cool. That 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'd ... I don't even remember. Maybe I'd driven once with, like a, 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 kinda look like miniature Formula 1 cars. Um, 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 track, you drive around for 30 minutes. Or maybe it was even just 20 minutes. And it felt like it took 30 seconds.

    2. TF

      [laughs]

    3. DH

      Because I would just see the flag right away and it'd be like, "Wait, what? I have to come in? I just started." Um-

    4. TF

      [laughs]

    5. DH

      So time was already being distorted, which is when you know you have a good time, is when you can't-

    6. TF

      Definitely

    7. DH

      ... keep track of time, right? And not only that, I was just absolutely fascinated 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, one more time, and it's one minute 30.8, and you go like, "Man, I just shaved off 6/10. This is the most exciting thing in the world."

    8. TF

      [laughs]

    9. DH

      And I mean, that's even taking it beside the fact that it's, it's exciting. It's a loud car, and it'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. I mean, it was, it's, it was kinda like, um, 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 I, 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.

  6. 24:29 – 30:51

    Why flow arrived later in programming: mastery, stakes, and details

    1. TF

      Why do you think it was more, 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?

    2. DH

      I think part of it with racing was just the intensity level was at 100% right away You had, as soon as you stepped into the car, you had maximum danger. Actually, you had more danger in the beginning than you will have later on because it's much more dangerous to drive a car on a 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. 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 an- can the PHP page render? Oh no, I get an error. Let me try something else." That was fun. Um, there was glimpses of flow, but the real moments of flow, uh, I wouldn't get until I was much better. Where with, 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 it a little bit on a, on a pin, but it was life and death, right?

    3. TF

      Mm-hmm.

    4. DH

      Like, you, you're going 160 mile an hour. If you don't get this next turn right, at the very least it's gonna be expensive, uh, and then it only gets worse from there, right? Either it's gonna hurt or it's gonna be [laughs] really, really bad or there's gonna be an ambulance involved or something else like that. And I think there's just a survival instinct that sharpens the mind in that sense, um, that, I mean, when I'm trying to get, make a PHP p- page work, i- 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.

    5. TF

      [laughs]

    6. DH

      Um, 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, and webpages. But as, 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 and 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," to ... Which to me then became uninteresting, right? Like, any programmer worth their salt, generally speaking, can get something to work, right? Like, can get the program to roughly perform the task it's supposed to do. Um, at least in information systems where the domain itself isn't, like, that novel perhaps, uh, 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, uh, simple, all these other pleasures you derive from code as pros, code as writing, not code as putting mechanical things together.

    7. TF

      Mm-hmm.

    8. DH

      Um, and with, with racing, um, you, you had the sort of interest right from the get-go because you had this criticality, really high criticality. Um, 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 ride height, and you start appreciating the differences between two millimeters up front and two millimeters on the rear or tire pressures, it, it becomes really interesting in a, 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, 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, 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, um, just is, is, is the path to flow, is the path to flow. Details. Uh, developing an eye, that's for me the most reliable way I've found to cultivate flow.

    9. TF

      And, and like you said, if you, if you haven't found something that grabs your interest about a given topic, just keep scratching, right? You haven't, you haven't dug deep enough. For instance, I wanted to do ... get involved with archery for a very long time in a, in a serious capacity, and I only started doing it about a month ... Uh, let's see. Three months ago. And part of what triggered it was an Olympic, uh, archery coach who suggested I get, I get a book called Shooting with Back Tension. [laughs] I, I think I'm getting the title right. It's an entire book about how to use mid-back tension [laughs] to fire more accurately and make the process more replicable. And for whatever reason, I just found this so fascinating [laughs] that that is what enabled me to finally take it seriously because that was the hook. That was the lure that I needed to bite. Uh, 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, uh, to put some of this in context. The story of not wanting to be inconvenienced in, say, Brazil or US with- by not being able to drive, that was, sounds like at least one of the primary catalysts for getting a driver's license, that, uh, sort of potential frustration. Uh, correct me if I'm wrong here, but it, y- the programming came out of, uh, starting a gaming news website. You mentioned the, the racing games earlier. Is that ... How, how did that come to be? How did you start coding?

  7. 30:51 – 37:51

    Programming origin story: self-sufficiency, gaming sites, and avoiding helplessness

    1. DH

      It was actually exactly the same thing. As I said, like, I learned how to drive a car because I didn't wanna be in Brazil or in the US stranded or reliant on buses or whatever that would make it hard for me to sort of 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, uh, with a lot of programmers as friends. Um, and I was involved with computers, not as a programmer, but around the edges of it. I ran a, um, what was called a ware site, a, um, BBS, a bulletin board system before the internet-

    2. TF

      Mm-hmm

    3. DH

      ... where we'd trade pirated software and so on. I was, 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 kinda looks like math, and math is interesting, but it's not really what I wanna spend my time on. Programming's 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 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. Um, and they would help me, and I would kinda 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 way as that I wouldn't want to arrive in the US or in Brazil or whatever I had imagined of these destinations were, 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 in why I choose to do certain things. I have a, definitely a streak for wanting to be self-sufficient.

    4. TF

      Mm-hmm.

    5. DH

      And that self-sufficiency then led me to think like, "Ugh, okay, fine. I'll learn ASP," or whatever the Microsoft thing was that we were using at the time. And then after that, "Okay, fine. I'll learn this PHP thing just such that I can make the other thing that I really want happen." I wanted to make this game, right?

    6. TF

      So it wasn't a decision to become a programmer. It was like, "All right. You know what?"

    7. DH

      Absolutely not.

    8. TF

      "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."

    9. DH

      Exactly. That was it. It was, it was a tool thing. It wasn't like, "Oh, this is my new pursuit. I'm gonna be a programmer." Absolutely not. It was I wanted some programs. I wanted some websites actually, and I found out, oh, you kinda need to do some programs to do that. I had taught myself HTML and CSS and JavaScript to, 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 con- 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 things that actually, it's programming, but it's a very different domain than working on information systems. So I picked up this tool trade in much the same way as someone goes like, "Oh, I have to put this piece of furniture together. Uh, which screwdriver do I have to use? Oh, 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?

    10. TF

      [laughs] Right.

    11. DH

      Just trying to-

    12. TF

      Right

    13. DH

      ... "Hey, I just want this, uh, 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 with race car driving, for example, like, there was a 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, um, I'm done with this gaming website I had been building for a Danish incubator. There was a lot of, uh, [laughs] Danish-

    14. TF

      [laughs]

    15. DH

      ... um, uh, 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 kinda saw the writing on the wall, um, painted pretty clearly when dot-com bubble bursted in the US, and I thought, "Eh, let 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 100% sure what else I'm gonna do. I'm not gonna 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, that it was, it was kinda 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. And, um, I hid away in, in university for three years getting this degree, and, and at the same time, I, I... Then I really got into it, right? Not so much because of the schooling, because schooling was all about some nonsense Java stuff, um, where I guess it was good to get exposed to that. That, that did provide influences for later work. But it wasn't the schoolwork that was interesting. It wasn't because we were getting exci- assignments that I thought were so, so fascinating. 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 tails 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 k-" Kind of interesting to like, oh, it, this is actually pretty interesting, to all the way until 2003 when I finally finds, find the love of my programming, uh, language life in Ruby and go, "Oh, actually, this is what I wanna do with my life."

    16. TF

      How did you, uh, experience those jumps? In other words, what made it interesting? Right? Because there are certain moments in time where I can pinpoint for different skills or topics, like it went from not interesting to interesting, right? It's kinda like it not boiling, boiling. There was a really clear-

    17. DH

      Yep

    18. TF

      ... shift. For you, what was that for programming? And then, and then why... I mean, I'm, I'm sure you're might be sick of explaining this [laughs] but the s- so the first is why programming generally. Like, when was it like, "Oh, shit, this is really interesting"? And the second is why Ruby?

  8. 37:51 – 47:45

    Falling in love with Ruby: rapid onboarding, depth, and building Rails while making Basecamp

    1. DH

      Sure. So the first thing certainly came first, which was why is this interesting, and the first big aha moment I had was when I reached self-sufficiency, when I got to a level 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 w- served its purpose. I could put things on it. It wouldn't fall down, and I'd go like, "Huh, that's actually pretty cool." Like, you can take something, you can take an idea, and you can start writing things in a text editor, and all of a sudden 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 the 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, a- another jump when I started working with other people. Um, I started working with Jason. Uh, Jason Fried, um, as I said, was, uh, not only a business partner at Basecamp, but he was also the first guy who paid me to program. All these other endeavors I had to program were more like side chefs. They were not the main thing I was supposed to do. I was doing this programming 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, had gotten self-sufficient enough that I kinda knew my way around PHP at the time. And then Jason, um, I, I ended up connecting with him and he ended up hiring me, paying me the grand sum of $15 an hour-

    2. TF

      [laughs]

    3. DH

      ... which, um, I was gonna say back when the dollar was worth something. Um, now the dollar's actually worth, uh, a lot more again. Um, but, uh, 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 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 by the way, funny anecdote on that, it wasn't even 15 bucks an hour because I... Back then you couldn't really easily send money. Um-

    4. TF

      [laughs] So you got like a-

    5. DH

      So-

    6. TF

      ... 20% [laughs] transactional cost or whatever.

    7. DH

      He w- exactly. He would send goods. He would send Apple goods.

    8. TF

      [laughs]

    9. DH

      So he would send, like, the very first iPod was part of my payment. I got an iBook, uh, a bunch of kind of stuff like that. Anyway, just fun to think back about.

    10. TF

      [laughs]

    11. DH

      And then I s- I worked with Jason for a couple years on a variety of, uh, client projects. Um, 37signals, which was the name of the company before we changed it to Basecamp, was doing client work, uh, 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, um, I think maybe in 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. Um, we had worked on some other stuff earlier, uh, a site to keep track of your, was it, yeah, your books, uh, called Single File that I had made in PHP and, and that was good fun. It was a good learning experience. 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, um, 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. It's, 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?" Like, "I can't find it. Oh, did you tell Peter about this?" "Oh, no, I thought you..." And, like, "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-

    12. TF

      Yeah

    13. DH

      ... 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. So as I s- we started on a 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 t- technology we have to use about this." And I had read about Ruby from some other programmers that I respected, uh, Dave Thomas and 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, I can use a brand-new programming language. Let's just give it a try." And I set myself this challenge, basically. If in, 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 gonna 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 and-

    14. TF

      [laughs]

    15. DH

      I, I have this, uh, this, uh, uh, GIF of the guy that just goes like where his mind is blown and he sees the galaxy and, and so forth. That was a little, without over-dramatizing it even more than that-

    16. TF

      [laughs]

    17. DH

      ... that, uh, what I felt like, right?

    18. TF

      Yeah.

    19. DH

      That this is what I've been working for.

    20. TF

      Yeah.

    21. DH

      This was the, the glove, and it just fit my brain so perfectly.

    22. TF

      Huh.

    23. DH

      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.

    24. TF

      Right.

    25. DH

      I just kept going and going and going. I read more and more of the standard library for Ruby. 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, 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 sort of like this is a beautiful tree, like, uh, this is the sort I wanna use for it, 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 Ruby on Rails. Um, and that was, that was basically my first project in Ruby, and I'd been a professional, quote unquote, programmer, as 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." And it di- really, seriously, it didn't take that long, maybe a couple 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, it was just... I, I really felt like I'd found something like you're not supposed to.

    26. TF

      [laughs]

    27. DH

      It has been 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'd, I'd never felt like that.

    28. TF

      Now, you, you mentioned... There, there are a bunch of things I wanna dig into 'cause I love this story. So the first is, and, and for anyone who's wondering does Tim program, I, I'm not a programmer. But I did have, uh, as an aside, a very fun experience with Chad Fowler. He's not related to the Martin that you mentioned, is he?

    29. DH

      Nope.

    30. TF

      Okay.

  9. 47:45 – 56:05

    Why Ruby felt familiar: language “families,” remixing ideas, and the flexibility theme

    1. DH

      I, I don't think I'm that much of an anomaly because like natural languages, there are kind of families of languages.

    2. TF

      Mm-hmm.

    3. DH

      And, uh, so Latin languages or whatever, you can jump from one to another-

    4. TF

      Right

    5. DH

      ... with, with much greater ease than if you jump to a completely different family of languages like Japanese, for example, right? 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 kinda have a good baseline, right? And, and perhaps that is kind of like learning Latin and then trying to learn other languages from there.

    6. TF

      Mm-hmm.

    7. DH

      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, uh, as far as I really know. What it did was it was like the, the master mixtape. It was the greatest hits-

    8. TF

      [laughs]

    9. DH

      ... of all the programming languages that went before it, mixed together by the most amazing DJ you've ever heard. 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 just, it's a new experience." So I kept recognizing all these angles of it, "Oh, this is kinda similar to that, but whoa, what a way they've chosen to express it." Um, so the onboarding was quite easy, and I think that that's one of the areas of s- real success that Ruby has had is that for a lot of programmers who've had some experience with programming, it instantly feels familiar.

    10. TF

      Right. The switching cost is really low.

    11. DH

      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, 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.

    12. TF

      Mm-hmm.

    13. DH

      Like, you're like, "Oh, in two minutes I really wanna see the rest of this movie." Like, it's still gonna 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, um, what was going on. And I think in terms of learning that new language, um, when you f- you see something that's, uh, both it, it has some recognition and it also challenges you in some ways. I didn't certainly know all the concepts that, uh, 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 Smalltalk and the way those languages work, they were far more radical, right? Which it, 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 of just all the greatest hits. Ruby didn't come up with very much, uh, original content in that sense. Um, 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-

    14. TF

      Mm-hmm

    15. DH

      ... 'cause it doesn't, it doesn't bend, it 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, and you go like, "Okay, for that one problem, this probably is the best language in the world." It's just problem is a little, little narrow. And then if you try to apply that same 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. Um, where with Ruby, it was just really, really good. Never perhaps the best in the world on any individual task, but so flexible, so, uh, well remixed that it was just exceptionally good at a lot of different things. And I find that trait to be something that runs as a, a line through a lot of the things I get interested in. Um, with Basecamp, for example, the product that I built with, uh, with Ruby, we were never the best at any individual thing. Basecamp is, is a DJ remix of the best tools. Like, oh, we got chat, we got message boards, we got all these different things, then that fit together, and then it offers a solution, right? Not just like I'm just gonna be the best in the world at this 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 gonna fit well, and it's, it's gonna work out great. And to tie it to the racing we've been talking about, uh, I am ... 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, uh, 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 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. I've gotten into photography. I-- There's a lot of things you can do. Well, not a lot of things. There's a sum of things you can do, and then you can do those things really well. I think, uh, the 80/20 thing where I'd much rather have ... You can get 100% for 100% of the effort, right? Okay, fine. If you wanna be the very, very, very best in the world, you have to spend 100% of you to get there. I just find that int- uninteresting. I'd rather have five things where I'm, like, in the top 80th percentile.

    16. TF

      Well, s- I want to underscore that 'cause I think it's a really important point, and it's something that, uh, a number of folks, um, ha- have spoken about with me, and it's, it's a pattern, I think, worth highlighting for, for those people listening. And that is, if you want to, and S- Scott Adams, who, the creator of Dilbert, wrote about this, uh, on his blog as, I think it's just career advice. He said it, your options for achieving greatness, so to speak, are sort of, uh, 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, Ruby. Um, and Marc Andreessen has also talked about this, uh, who's, who's, um- Of course, created a, more than a handful of, of impressive things, and has reinvented himself as an investor. But the, uh, 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 for 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. Uh, quick thing, and, and there's, uh, what you said about Ruby made me think of gaming actually, and I'm gonna bastardize this, I'm sure. But the easy to learn, hard to master, and, uh, I believe that's also Bushnell's law, um, from Atari, which was a good game, is easy to learn, hard to master. And, um, Ruby itself, I had a question on, what is...

  10. 56:05 – 1:03:06

    Naming Ruby on Rails: homages, constraints, and domain availability

    1. TF

      And I, I could look this up on Wikipedia, but since I have you [laughs] here, w- what or who is Ruby, and then why did you use the, the words on Rails?

    2. DH

      Yeah. So first I'd say that absolutely agree with that. Like, that is the ideal, both for, for Basecamp and for Ruby and for Rails, all the things I'm working on. This notion that things should be welcoming. Like, 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-

    3. TF

      Right

    4. DH

      ... in non-human language form, right? Like, it really has to be decoded by people to extract that wisdom. I find that to be just unnecessary. Like, the best things, the things that I get really interested in, like, they're approachable. You can get in, into, say, programming Ruby, or even driving a race car, or any of these other things that I've gotten into, photography. Um, they're, they're quite approachable, and, and they've never been more approachable, but they're still really hard to, 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. And I'd say that some of those domains that I, I left behind that for me didn't do it for me, didn't pull all the tricks were like, uh, I 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 wanna 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 the firestorm that's gonna start otherwise, a reflection of how things are. Let's just say that that's caveted to how things used to be. The thread 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. [laughs]

    5. TF

      [laughs] Well, that's because my question was like a 17-parter. I asked you the, uh, the, at the very tail end, I asked about the origins of Ruby, like who-

    6. DH

      Oh, yep

    7. TF

      ... or what was it named after? And then how you used on Rails, why you used on Rails.

    8. DH

      Sure, sure. Yeah, so it's funny because it really ties... There, there's so many of these trends that are overlapping and interlinked even when they're applied at different scales and at 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, Matz, the Japanese creator of, um, Ruby, was inspired by Perl. Um-

    9. TF

      Hmm

    10. DH

      ... the language that went before it, uh, served as an inspiration, but even the name itself served as an inspiration.

    11. TF

      Yeah. P- P-E-R-L, right?

    12. DH

      Yeah, exactly.

    13. TF

      Yeah.

    14. DH

      Um, and he went like, "Oh, it's a short name. That's cool. It's kind of a precious," um, I guess you'd say stone, even though I guess a, a pearl is not a stone.

    15. TF

      Right.

    16. DH

      But it's a precious stone of some sort. Um, is there another word like that that's also short, that's kind of in the same family? It was kind of paying homage and, uh, respect to the things that went before Ruby and where Ruby drew its inspiration. So Ruby was born, I think, in '95. Maybe, uh, I seem to remember maybe he even started working on it already in '93, but the first release at least I believe was, uh, was '95. So it's been around for 21 years, and Matz is still working on the language, which is just something else I truly admire, respect, and aspire to, which is going the distance. Not just kicking off a ball and then running out of the room, but sticking with it over the long, long haul, right? Like, I've been working with, uh, Basecamp now for 12 years, with Ruby for 14. I mean, you're looking at endeavors that, like, most of my adult experience have been with these, uh, tools. I've been even, even race car driving now. It's like on the one hand, yeah, I got started quickly and got going, but I've been going at it now for 10 years. It's still a, 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, um, with Rails. So, uh, obviously we had Ruby, right? And I went like, "Okay, let's, let's play off that. Let's pay some homage to that with an R." Like, I, I wanna 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. [laughs] I really want to do basically the opposite of what this is doing in a whole different lots of areas. But I find that's often just as valuable inspiration as the things you wanna clone.

    17. TF

      Definitely.

    18. DH

      It is just as valuable to look at something and say, "Oh, that's what I don't wanna do. That's what I don't wanna be." I've learned Perhaps more about running a, 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 had kind of this construction feel to it, right? And I went like, "Oh, that's kinda cool." And then I went R, like, oh, Rails, like that's kind of similar. Like, it has some fun plays on like, oh, you, you kinda put your development on rails, that it kinda just goes, it's fast, and so forth. And then I went to whatever site I was using to reserve domain names back then. I went rails.com. Taken. Oh, damn, I can't get rails.com. Rails.org? Nope, taken. Rails.net? Nope, taken.

    19. TF

      [laughs]

    20. DH

      Rails. all sorts of other things, taken, taken, taken, taken, taken, taken, taken, right? Like, all those singular words were already taken long since. And then I went like, "Oh, okay. Well, I guess I need a domain name." Ruby on Rails then. Oh, free. Rubyonrails.com.

    21. TF

      And that's... [laughs] And there you go.

    22. DH

      So that's how it ended up with the name, not out of any other... I mean, I ended up actually liking it even better, um, 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. So that was, 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 loved that I could fit that as part of the name, and that kinda became a, became a thing.

  11. 1:03:06 – 1:19:19

    Building Basecamp differently: first principles, small teams, and avoiding venture time bombs

    1. TF

      You mentioned learning from bad examples. Um, 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. Um, let's look at business. So you, you come to the US, you're working with Jason, and at the time, 37signals, now Basecamp. What do you guys do differently?

    2. DH

      That's a broad question that, uh-

    3. TF

      [laughs]

    4. DH

      ... I'll try to answer in a meta way-

    5. TF

      It is, yeah

    6. DH

      ... 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 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, that's just the way things are. That's just how we're doing things. Like, that's how other companies do things. Like, 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 s- 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 gonna run our own company, we're gonna 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 gonna work 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, 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 don't, they aren't clear about what they want those principles to be, be, except if they're these overly broad, "Oh, we want to do good work for the wor- or 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 points of-

    7. TF

      Where reasonable people can disagree. Could you elaborate on that?

    8. DH

      Yeah, I think where, where there's, um... 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 gonna disagree with that? Like, it... basically anything that's on a corporate Fortune 500 motivational-

    9. TF

      Poster [laughs]

    10. DH

      ... poster, like you'd go, like, no one would say the opposite, right?

    11. TF

      Right.

    12. DH

      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? To be-

    13. TF

      Well, not, not... Yeah. I was just gonna 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 insomuch as, like, if, if it's not a falsifiable hypothesis, [laughs] it's like, it's just like, what are you doing? You're just, uh, kind of-

    14. DH

      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, uh, it's 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, um, or what we believe has a falsifiable version of it, where it's a, like, oh, well, what you believe actually didn't work, right? Like, if we can't arrive at that conclusion, it's not an interesting thing to believe, um, because then either anyone would believe it or it's not actually driving your actions. Because if, if this principle can lead you to both sides of, 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, um- 'Cause that's where we make progress. Uh, 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, for Jason and I owning the company, for all the employees that we have, and for all the customers that we have. And it's, it's again, it's, it's this systems thinking that we're trying to improve the system and, and, and, um, 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. Um, that's not so interesting to me. I, I mean, sure, we've had our fair share of luck. Of course we have. 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 the 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. Um, 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 have 50 people running Basecamp? Like, that's a laughably small company." And to me it's like this huge organization, 'cause my origins was, uh, and perhaps to some extent my preferences are a, a smaller thing put together really well.

    15. TF

      And do you, uh, I... So I'm definitely gonna, gonna come back to the beauty and elegance, or just beauty and elegance as concepts. But I wanna ask you first, since you brought it up, uh, 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, Basecamp not to exceed X number of people. Or is there any thinking along those lines? And if so-

    16. DH

      I, I think it's more a principle of c- let's try to stay as small as we possibly can while still not feeling negligent about the things that we cannot do. Like, it's all good and well to say, "Oh, you're 50 people now." Like, what if we were 30 people and we just, like, didn't answer customers' emails? You can be a smaller company if you just don't wanna respond to, to feedback, and you might still sell your product and so forth, but that seems negligent. So I wanna be as small as is not negligent to be. And of course, like that, I mean, to some extent perhaps that's a, not a scientific statement, because how is that falsifiable? But there's just a sense that, um, 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. Um, I see lots of companies, uh, many times our size where I go, "Where is that effort going?" Like, I'm not seeing it. It's not visible. Maybe it's behind the scenes, and it's always easy to compare yourself in flattering ways to stories where you don't know the full st- backstory. But I think there's still something to be said from the idea of just trying to, to optimize your company to be your best product.

    17. TF

      Mm-hmm.

    18. DH

      And if you do that, then, uh, rejigging it... And, like, I look at, for example, when I, I write, um, 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 there's, let's just take policies, for example. Um, lots of companies have all sorts of elaborate co- policies on, on spending, on how you can justify, um, uh, expense reports and so on and so forth, where, which is like, is there a way we can get away without that? Um, 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 spend it wisely. The end, right?

    19. TF

      [laughs] Right.

    20. DH

      Um, and then, okay, forward your, uh, receipts, uh, if they're on email to this email address that we have that no one looks at, but just in case we get audited or something. And then that's not a perfect solution. It 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%, and you deal with it then.

    21. TF

      Mm-hmm.

    22. DH

      Compared to what you sort of just save in 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?

    23. TF

      Mm-hmm.

    24. DH

      Because if you look at companies and you look at company growth, if you're, uh, four people and you hire, uh, four more people, um, 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, 5%, 7%? Like, the complexity curve is not linear. When you, uh, 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. Um, so that's one of the things that I've just on a personal level have been interested in. Like, how can we maintain- maximum efficiency. And to some extent, and s- 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 when we had zero money at all, and, uh, we had to be just four people and so forth, we had to be maximum efficient because didn't have anyone else's money to spend. 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'm, I appreciate that idea. A- 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, um, something you always have at the back of your mind and something you try to derive decisions from still leaves you to a very different place than where we would have been if we had gone the standard route of, oh, here's a new software company. We have a product that's taking off. Let's get a lot of venture capital money invested. Let's hire a bunch of people. Let's 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. 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 wanna work at in 20 years. Like, I actually, uh, 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 you 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. And if I want to do that, if, then I can't install all sorts of time bombs in my business. I can't install, like, okay, if I take X amount of money from these people, then they want it back in seven years, and they want a 10X, so we have to swing for the fences to get that. Otherwise, we're gonna 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, and so forth. Then secondly, um, I wanna do this because I want some modicum of success. Like, I don't need to be a billionaire. I don't need to be even a hundreds millionaire. I just need to be, uh, comfortable in knowing that, like, okay, we, we got to some baseline, right? Like, I like to compare the fact that the difference between having $0 and $1 million is extremely large in terms of sort of basic comforts of, of living. The difference between having $1 million and $2 million, 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 inspirations. Yes, if your biggest dream in the world is to own the New York Jets as, uh, Gary Vee wants to do [laughs] or you want to send people to Mars like, uh, Elon Musk or any of those kind of wild dreams, okay, fine, you need billions of dollars. And, and you should pursue strategies that are compatible with that. I perhaps have more, it sounds funny, but modest. It's only in comparison [laughs] to those outliers. Modest ideas of it. So I wanna optimize my chances for that. So part of that was, like, I wanna 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, you look at the world s- stage, like incredibly rare thing, right? And an 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 that's been driving a lot of how I approach where do I wanna be. Like, if you take where do you wanna be in programming, where do you wanna do, be in racing, where do you wanna do in business? I'm like, I f- it's such an oxymoron, but I feel like I modestly just wanna be in the top 5%, right? Like, I don't need to be, again, as we talked about, I don't n- need to put in 100% to, to be Michael Jordan. I don't need-- Because it's even worse than that, right? Again, that's the reason I don't wanna do it. I don't wanna put in 100% to have a really, really poor chance of becoming Michael Jordan. So many Michael Jordan. Lots and lots and lots of other people who, if you just take the baseball or basketball metaphor, that are good base, basketball players, right? And can make a good living and get to play in the NBA, and, like, that's pretty amazing, right? I just wanna make it to the NBA. I don't have to be Michael Jordan.

    25. TF

      [laughs] No, definitely. And I want to just emphasize something that, um, I think, 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, the belly of the beast. And, uh, you run into folks who maybe they have hundreds of millions of dollars, and they are 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, 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 [laughs] if they're incompatible, you're basically just sowing the seeds of your own destruction. And so I wanted to

  12. 1:19:19 – 1:45:48

    Happiness, tranquility, and expectations: stoicism, negative visualization, and the Bezos deal

    1. TF

      ask you, do you consider yourself a happy person?

    2. DH

      Yes.

    3. TF

      You do?

    4. DH

      Absolutely. And part of it is because I work at that. Like, that is, is, is one of the explicit goals of hire, tribe, retire decisions. Is this gonna make me a happier person? Um, I- Jeff Bezos has sort of the reverse of it, which is his regret minimization framework [laughs] which sounds like just something Jeff Bezos would come up with, where he's like-

    5. TF

      [laughs]

    6. DH

      ... "I'm just gonna t- 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 ha- happiness is also sort of a fuzzy term, right? Like, one of the things I know that you've been interested in too and, and has really spoken to me is, um, stoicism and this notion of tranquility. To be in this state of contentment and tranquility. It's ... Happiness has some sort of, like, connotations as though I'm running around all the time laughing my ass off. Like, [laughs] "Oh, isn't this a wonderful life? [laughs] " Right?

    7. TF

      [laughs]

    8. DH

      Like, that's not ... I don't aspire to that. That's not how most days are. But I do have a sense of-

    9. TF

      [laughs]

    10. DH

      ... deep tranquility and contentment with the situation that, uh, I'm in. And part of that is actually going all the way back to the beginning. My key takeaway from The 4-Hour Workweek was the concept of lifestyle design.

    11. TF

      Mm-hmm.

    12. DH

      That there's so many people who just follow ... We're on rails in the negative sense of the word of, like, how things are supposed to go. Okay, first I get my, this education. I perhaps don't even really care that much for the subject, but it'll lead to a good job. Then I'll get the good job, then I'll get married, then I'll, like, da, da, da, da, da. And then at 65 I'll retire, and then I can really live life. What? Are you crazy?

    13. TF

      Mm.

    14. DH

      Um, first of all, good chance you won't make it to 65 and then everything was wasted between, uh, getting born and not getting there. Um, second of all, why would you waste or wait until the worst decades of your life in terms of physical mobility and, and capabilities otherwise to start enjoying life? And that's the problem I really have with a lot of the startup ethos and work spirit in general in the US and in Silicon Valley in particular, this notion, like, let's compress working life. If you could just, like, work like a madman or madwoman for 120 hours a week for, like, seven years straight, then nirvana will be waiting on the other side-

    15. TF

      [laughs]

    16. DH

      ... 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 ... Do you know what? I know people who've gone exactly through that, and after two weeks on the beach they went like, "Wait, what? Wasn't this supposed to be winning? This is miserable."

    17. TF

      [laughs]

    18. DH

      "I hate it. I don't wanna be here." Like, "That was not actually my destination. The thing I gave up all sorts of valuable things to arrive at is a miserable place to be."

    19. TF

      Mm.

    20. DH

      "And I don't wanna..." It's easy to trivialize these things, and especially easy when you actually already are a millionaire, to trivialize, um, sort of the struggles and, and the aspirations of, of someone where money can make a big difference. But when you're talking about people who already made it and wanna make it more, right? It's incredible how often the people end up sucked into this notion that like, "Oh, if I just make it to the next step, then I'm gonna be happy. Then happiness awaits me." When just a false treadmill. It's ... Not only is it a hedonic treadmill in 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, 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 w- when someone asks me, "Are you happy?" I think back of when I sat in Copenhagen in 2001 in my, what, 350 square me- or, uh, square feet apartment. Tiny, tiny little apartment in Copenhagen. I was going to school at the time, I was learning, uh, PHP. I had all sorts of things I was worried about, like rent and so on. Not on an existential level, but still in, in a normal sense of it, right? Also t- sorts of thing. I'm still happy.

    21. TF

      Mm-hmm.

    22. DH

      I was within margins of where things are today.

    23. TF

      Mm-hmm.

    24. DH

      And if you look at those two situations otherwise from a level of possessions or quote-unquote success, like, they're pretty different [laughs] places to be.

    25. TF

      Mm.

    26. DH

      And yet they don't feel that different. And part of that is to have that focus on the inner journey, on the inner strive of this ... Uh, another quote I, I love just pulling out whenever context fits or not is, uh, Coco Chanel, "The best things in life are free, and the next best things are very expensive."

    27. TF

      [laughs]

    28. DH

      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, uh, once you adopt the philosophy of life that allows you to view it from that angle, it really puts things into perspective. It gets it so much easier to get to tranquility.

    29. TF

      And I, I think that, uh, tranquility is in a lot of respects a better goal than happiness, which has been ... The, the word is so overused to have become almost meaningless. I wanted to use it just 'cause it's a, it's a more straightforward term and more familiar term. But it's, it seems to me also that if we're talking about, say, flow states, if we're talking about tranquility, uh, it relates to developing an internal locus of control or an internal, metric is probably too quantitative a term, uh, 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 a, another Jones [laughs] who's willing to sacrifice more than you are if, um, th- If you're kind of chasing, as you said, this pot of gold at the end of the rainbow. The, the, uh, all of which relates to stoicism, but I wanted to, uh, also reiterate one thing that you mentioned, which is this 7 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, uh, you know, the, uh, praise, uh, praise God, here's nirvana. The, the disconnect, I think, for a lot of folks, or the question that they'd be well-served to ask is, am I develop- am I developing attributes now that I can use in multiple states, in multiple endeavors, right? Because what people fail to realize is that if you are going to stand a snowball's chance in hell of actually creating the next unicorn or whatever it might be and cashing out in 7 to 10 years [sniffs] , the work habits and so on that you're going to have to develop are completely incompatible with sitting on that beach-

    30. DH

      Yes

  13. 1:45:48 – 1:54:58

    Deep work and anti-interruption design: resisting the “ASAP culture” and building Work Can Wait

    1. DH

      I think if you look at the French, which also it's a reason to laugh at the French, but this is not one of them in my opinion. There was a proposal in their parliament, uh, last year I believe it was, where they said, like, employees should have the right to disconnect, that they ha- should have the right not to receive emails that their boss expects them to answer on Saturdays.

    2. TF

      Mm-hmm.

    3. DH

      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 it's kind of implied that you have to deal with even though it's not that important. There's just such an ASAP culture, um, all over the world, but in the US in particular, where everyone thinks that it's their right to have access to everyone 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. Um, there's a lot of new pressures, uh, 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.

    4. TF

      No.

    5. DH

      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. I, 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 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 then respond to every meme within two minutes is 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, I'm reading right now, uh, Michael Foley, The Age of Absurdity, that draws on a lot of these-

    6. TF

      [laughs]

    7. DH

      ... uh, things we've talked about, stoicism included, and on this current, uh, and accelerating culture of just constant interruption and, quote-unquote, "multitasking," which it really isn't. It's task-switching. Um, I think it's just terrible, and we gotta do something to push back.

    8. TF

      No, I agree. Uh, and I think it has to start, uh, 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?

    9. DH

      I try to have it every day. I, I get that question from people all the time where they 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."

    10. TF

      [laughs]

    11. DH

      I just happen to configure my life and my business in such a way that, uh, most of the time I have long, uninterrupted stretches of time.

    12. TF

      Mm-hmm.

    13. DH

      And when you every day can get, like, a three-hour block or whatever, um, you just get a lot of stuff done.

    14. TF

      Yeah.

    15. DH

      And it doesn't feel like it. What feels, uh-

    16. TF

      Well, it doesn't feel rushed, right?

    17. DH

      It, 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 else and like, "How did they get all that done? How did they create and maintain Ruby on Rails? How did they keep Basecamp running with the, uh, 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, uh, "I don't know what we're looking at. 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 workweek. Uh, 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. Um, and most people just produce really crappy quality, really shitty hours. 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 hours.

    18. TF

      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 [laughs] 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 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, 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, and I was thinking about this yesterday in fact, because 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, I... The good news is if I have those blocks of time, and, uh, this may sound odd, but it's like if 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 gonna make everything else easier or irrelevant. I only really need two days a week where I get-

    19. DH

      Yes

    20. TF

      ... my shit done properly. And-

    21. DH

      Yes

    22. TF

      ... it creates the illusion of having done a ton of other things because I'm hitting the right dominoes in the right orders.

    23. DH

      I, I have that feeling all the time. 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." [laughs]

    24. TF

      [laughs]

    25. DH

      I look on a timeline of, for example, what we got done at the company in a year. Like we just, we released, uh, Basecamp 3, an 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?

    26. TF

      Mm-hmm.

    27. DH

      Um, but it's just the compound nature of good habits, compound nature of tranquility, compound nature of sustained 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. [laughs] Linear growth is still pretty damn good if you can just keep drawing long enough. It moves-

    28. TF

      Well, it comes down to your expectations line, right?

    29. DH

      Yes.

    30. TF

      I mean, it's, and because you say expectations, not outcomes, govern the happiness. Uh, but it also governs, uh, a lot more than that. I mean, if, if you, the timeline with, uh, 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, I'm, I'm a player and I have been historically a player in that game, so I'm not gonna totally slam every aspect of it, but w- there are quite a few-

  14. 1:54:58 – 2:10:56

    Accountability as systems thinking: ‘It’s Always Your Fault’ and learning from mistakes

    1. DH

      Yeah, it's a, it's a good question. I think one of the, uh, things I've always tried to do, 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. All, well, it's kind of like a truism, right? Like, 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. Um, it's one of the things I keep trying to hammer into race teams as well. Uh, race teams, a lot of times they, they love these things of like, "Oh yeah, just happened." I mean, you, 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-

    2. TF

      Bad planning [laughs]

    3. DH

      ... system, bad, bad planning, bad design, bad all sorts of things. 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 gonna make anything better? How are you gonna prevent the, quote-unquote, bad luck from happening next time? That is just one of the things I cannot take, I cannot stand for. 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, uh, I go through. And that has happened, uh, enough in both, uh, company and, 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, let's say something breaks on the car because someone didn't set up in, in the right way. That's not m-... I mean, I didn't do it, right? Like, I didn't swing that wrench, but it's my fault for, let's say, uh, 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 the team or of the people who are on the team, uh, not doing enough work on debriefs and s- postmortems 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. 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, uh, version control, before Git and CVS and Subversions and so on, I would sometimes overwrite my files, right?

    4. TF

      Yes.

    5. DH

      I would have spent four hours on a piece of code, and then I would make a mistake, and I would delete the file. Like, 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 ver- working feature, and I somehow killed it, and I just never made it again.

    6. TF

      [laughs]

    7. DH

      I simply could not stand to redo the work again. So that has carried over, and it's just even amplified with mistakes because mistakes are just extra painful, right? Like, and these mistakes, especially as, as a, a company, uh, size of Basecamp, like I'm not just responsible for my own mistake, I'm responsible for everyone else's mistake, 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.

    8. TF

      Yeah.

    9. DH

      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 in, uh, at, at Basecamp, and, and I think perhaps in part just because every single time someone have brought that up, I've of weakness kind of perhaps lost my cool a little bit on that-

    10. TF

      [laughs]

    11. DH

      ... which in itself is a failure that you should learn from and correct from and, and so forth. Uh, it's certainly not bad luck. But yeah, I just, I, I can't take it, and we gotta accept that responsibility, and we gotta do it all. Uh, the closer you are to the system... For example, um, like I tweet a fair amount about politics, and I tweet mostly about US politics. Why do I tweet about US politics and not about the politics of, I don't know, Iran or, uh, Georgia or Russia or something else? Well, partly because I've paid millions in taxes, so I kinda 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 w- right to, uh, to vote, uh, I still feel like-

    12. TF

      [laughs]

    13. DH

      ... a, this is the closest area where I have complicity.

    14. TF

      Mm-hmm.

    15. DH

      I have complicity in these actions, and I have, uh, some chance of kind of affecting that.

    16. TF

      Yeah.

    17. DH

      It's so much easier to just call shit out when there, when there's no personal complicity, right? Like, it's-

    18. TF

      For sure

    19. DH

      ... the, the speck in your neighbor's eye and, and all that stuff. So yeah.

    20. TF

      Do you think your impatience, uh, well, I shouldn't say impatience, your, um, distaste [laughs] for repeating work is part of what made you a good programmer?

    21. DH

      Absolutely. I think it, it's almost pathological actually, um, that I have such an aversion to doing 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 in 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. Uh, I might fear that I'll see it again, but until I actually see it again, let's, let's not, uh, overreact here-

    22. TF

      [laughs]

    23. DH

      ... and build some huge honking framework to, 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, but there's a pattern. There's an outline that's similar, and when I spot those similar outlines, uh, and I come up with an extraction that kind of m- 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 because I've solved all these problems. I've put all these tools into the toolkit of, of Basecamp." And I... This is one of the things with negative visualization where I have this, I don't know, nightmare or fantasy, however you wanna 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, right? Like, I imagine this whole thing, and I pack this backpack. I gave a, a talk at the RailsConf I think last year about the survival kit that Rails is for me. I, 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? And that's my mission for Rails, and it's always been. Like, 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 a, just such an important driver to the pathological level. And I mean-

    24. TF

      [laughs]

    25. DH

      ... good things have come out of it, and, and sometimes not so good things come out of it, too. I think it's, it's... There are good things to think about, like how can you rely on and depend on other people? But hey, uh, I carry that cross and, and deal with that and, and just try to maximize the benefits and minimize the, 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 want to enable other people who wanna do it like we did it, tiny team, no external money, to have a chance to compete.

    26. TF

      Yeah.

    27. DH

      Because it u- 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 an 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, I just love that. And, I mean-

    28. TF

      Yeah

    29. DH

      ... it's funny. We're lowering the barriers of entry, which in some sense makes it perhaps harder because there's more people competing, 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 gonna be okay."

    30. TF

      Mm-hmm. No, it... I mean, I've used Basecamp for the last three book launches, and am going to be doing so again shortly, in about, uh, a month and a half. And, uh, I'm asked all the time, "How many people do you have on your team?" And I'm like, "Uh, one, maybe two really full-time employees, and then the rest are all contracted and everyone's distributed." Uh, so it's, it has n- I think it's never been easier from the standpoint of having a low barrier to 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, uh, 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, uh, you know, 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 to entry was mediated primarily by finances, like, if you don't have the money, you're fucked, you know? [laughs] Like, if you don't have 500 grand to start, you know, to, to, 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 other abilities. Um, but I could go, go on and on. I, I wanted to, uh... You mentioned the age of absurdity. Do you have any other favorite philosophers or writers?

  15. 2:10:56 – 2:28:11

    Parenting principles: empathy, independence, and skepticism about screen-time panic

    1. TF

      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? Uh, and/or are there mistakes you think that are very common among parents, aside from the over-rewarding? Maybe they go together.

    2. DH

      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. Oh, you just have this kid commanding their parents around. But I think that's a stereotype, a cutout board that people use to excuse just forcing their will on little people who can't really do anything about it.

    3. TF

      Mm-hmm.

    4. DH

      And that's one of the main things that I've, uh, sort of tried to just constantly put me, myself in the s- 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, uh, transplantation, but I found that a lot of people, I don't know, they, they have a lot of lo-... 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, it's overprotecting and things that are convenient for the parent that, oh, uh, it'd actually be great for me right now if you did these things, and then I'll couch it in-

    5. TF

      Right

    6. DH

      ... language and justification as, oh, I'm doing what's best for you.

    7. TF

      Right. I'll rationalize the conven-

    8. DH

      Exactly.

    9. TF

      The convenience for myself.

    10. DH

      Yes. And like, oh, it's best for me right now if you do what I say. [laughs] Yeah, of course, that's best for you. Um, that doesn't mean that's best for the kid. The other thing, uh, uh, trend that I've been sort of just alarmed about is this notion of basically criminalizing independence, and especially in the US, um, this war on kids basically being by themselves or doing anything that even looks remotely dangerous, 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, of parenting and, 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, and 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 t- parent that tells your kids what's right for them. So just take one simple example. Sometimes, like, your kid doesn't wanna eat the things that they're supposed to eat, right? Like, they just wanna eat candy all day. Well, you can tell them, "If you eat all that candy, you're gonna get a stomach ache," 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 fucking let your kid eat the bag of candy and get a tummy ache 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 after that too. You know what? After the third time, I found, uh, well, sample size two-

    11. TF

      [laughs]

    12. DH

      ... in direct exposure and sample size somewhat larger in indirect exposure. 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 gonna happen if you do that," and then prevent them from doing that. Like, that's not a very persuasive technique. Um, so I've tried perhaps to sometimes an extreme degree to say like, "Hey, by the way, this is my [laughs] assessment of the situation. I think this is what's gonna happen." Like, one thing that a lot of people have been freaking out about is screen time, right? You can't have your kid get an iPad and just sit on it for as long as they want because, like, then they're just gonna be addicted to that and they're gonna sit on that eight hours a day. Mm, I don't... First of all, I found that to be categorically untrue with my sample size. Um, but I've also find it to be an unpersuasive argument in the grand scheme of things. I, 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?

    13. TF

      Mm-hmm.

    14. DH

      And sort of the rat would just go over and eat cocaine until the rat die. 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 on the wheel. They could drink water. They could do all sorts of other things, right? Guess what? That mouse didn't just eat cocaine until it died, right? Like, oftentimes, uh, 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.

    15. TF

      [laughs] You're not providing-

    16. DH

      Perhaps-

    17. TF

      ... ample, uh, rich environment

    18. DH

      ... poor parents who just wanna engage. Perhaps you don't wanna read to your kids. Perhaps you don't wanna take them anywhere. Perhaps you then just wanna enforce this idyllic version of what you think, oh, they should just play with wooden blocks all day, and like, that's really good for them. You know what? Fuck you.

    19. TF

      [laughs]

    20. DH

      I, I mean, it's just, it- I find it so lacking in basic understanding and compassion of like, what would you wanna do in that situation? And what then perhaps more interesting is that I've tried to then say like there's n- 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. 'Cause you know what? Kids are pretty good at self-regulating. Again, sample size two. Um, in my experience that if you have other interesting things and choices and opportunities that they can choose to partake in, they will.

    21. TF

      Mm-hmm.

    22. DH

      And this mania of like, oh, iPads are the new devil, it's just... I just find it hilarious. There's a good, um, Twitter account. I forget what it's called. Something about like, uh, terrors from the past or something where we go like... 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 mind." And then it was like-

    23. TF

      [laughs]

    24. DH

      ... comic books are terrible, or Dungeons & Dragons is terrible. And, eh, okay. Like, at least there's a pattern of history here where people decrying new technologies or new forms of entertainments that 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-

    25. TF

      [laughs]

    26. DH

      ... thought that was a good time? So.

    27. TF

      [laughs] Yeah, there's, uh, hysteria never goes out of style. Uh, the, um, question of habits. So you, you mentioned a few things, uh, empathy being one of them. Uh, I'll give you yet another two-part question 'cause I seem to be, uh, for whatever reason, too much, too much caffeine maybe on the, on the two-part thread today. But, uh, first is, uh, uh, 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?

    28. DH

      Um-

    29. TF

      With your children specifically maybe.

    30. DH

      Yep. I think angry is, um, is a funny word to me because, like, even when I'm going off, like I generally don't feel angry in the... Sometimes I do. I, I... 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? Like, I'm just, just processing these things, for example, uh, 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 can get 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. Um, so I think it, it's one of those things where I forget what the novel was, but there's this ... concept of s- what you see in a person on the outside is, is often not the reflection of what's going on in their inner life.

  16. 2:28:11 – 2:36:15

    Rapid-fire favorites: books, podcasts, purchases, photography investment, and ‘beautiful code’

    1. TF

      When, uh, I'm gonna z- I'm gonna jump into, if you have the time, I'd love to go through some, some rapid fire questions.

    2. DH

      Sure. Yeah.

    3. TF

      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?

    4. DH

      Um, there's a bunch of que- or names that come to mind. One that's kinda trite is my, is my mom. Um, and the reason I say that is she has such an upbeat, happy outlook on... Like, she is the perfect unknowing stoic. She's ac- actually a Catholic, but I think she's exceptionally good at many stoic principles of, uh, tranquility and so on, and, 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.

    5. TF

      Mm-hmm.

    6. DH

      And that's definitely an inspiration. But I've, I've 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, "Whoa, I'm jealous." Like, I feel like I'm doing pretty good on that scale and, and I've certainly met people, uh, friends where I'd still go like, "You're really rocking it, aren't you?" Um-

    7. TF

      When you mean, when you say internal life-

    8. DH

      And the more I-

    9. TF

      ... what do you mean by that?

    10. DH

      Like, I've never seen-

    11. TF

      Is it-

    12. DH

      I, I mean that they, they, they have that sense of tranquility, right?

    13. TF

      I see.

    14. DH

      Like 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, in some cases, like you face some real adversities, right? And it's just impressive to me. And w- I mean, that doesn't, it's not to say that that doesn't happen on the other end too, that someone who does have outward success, um, can also have that. I've just found that there's v- there's al- basically no correlation that I've found.

    15. TF

      Yeah. No, I agree.

    16. DH

      Like people have the-

    17. TF

      Yeah

    18. DH

      ... best, most tranquil inner lives and content-ness. Like, there's no correlation to where they are in that outward 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, I'm still sort of searching for what that is. But at least for me, uh, getting conscious about that fact and, uh, being diligent about having a phil- a philosophy of life, having a framework and working on these things, I mean, that has made a difference to me. Um, so maybe that's also, a- I mean, I should probably inquiry more about this because I find it endlessly fascinating, especially since you can't find that statistically correlation like, oh, it's this one thing that they do.

    19. TF

      Mm-hmm.

    20. DH

      Um, no, it's all inside the head.

    21. TF

      Is there, um, 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 wanna spend more time or learn from that person."

    22. DH

      Good question. Um, one of the early business idols that I have that I'd still love to meet, I heard that he just mentioned Basecamp in something unrelated, um, which made me all sort of fanboy flutter, was, um, Ricardo Semler.

    23. TF

      Oh, yeah, from Semco in Bra- Brazil.

    24. DH

      Yep. 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 just giving us-

    25. TF

      To me, to me as well. [laughs]

    26. DH

      Giving the confidence of like, Jesus, if this guy with 8,000 employees running a industrial company producing pumps for oil tanks can be this radical and this, uh, incisive about how to design a company, like surely we as a software company with no fixed assets in the 21st century can be just a little more radical than what we think is possible, right?

    27. TF

      [laughs]

    28. DH

      So I think that that, uh Yeah, Ricardo Semler 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." Okay. Yeah.

    29. TF

      Well, you started with Ri- Ricardo Semler.

    30. DH

      Yeah.

Episode duration: 3:34:12

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