The Tim Ferriss Show - #203: David Heinemeier Hansson on Digital Security, Company Culture, and the Value of Schooling

Episode Date: November 24, 2016

David "DHH" Heinemeier Hansson (@dhh) is 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." Listeners had a million questions we didn't get to last time, so he's back for round two because his episode is about to cross a million downloads -- and that's in barely two weeks! In this episode, DHH discusses: Digital security The value of schooling Three questions you should be able to answer Company culture How bladder relief happens in a 24-hour race And much, much more! Please enjoy my round 2 conversation with DHH! Show notes and links for this episode can be found at www.fourhourworkweek.com/podcast. This podcast is brought to you by 99Designs, the world's largest marketplace of graphic designers. I have used them for years to create some amazing designs. When your business needs a logo, website design, business card, or anything you can imagine, check out 99Designs. I used them to rapid prototype the cover for The 4-Hour Body, and I've also had them help with display advertising and illustrations. If you want a more personalized approach, I recommend their 1-on-1 service. You get original designs from designers around the world. The best part? You provide your feedback, and then you end up with a product that you're happy with or your money back. Click this link and get a free $99 upgrade. Give it a test run. This podcast is also brought to you by Wealthfront. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service led by technologists from places like Apple. It has exploded in popularity in the last two years and now has more than $2.5B under management. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it's all through smarter software instead of retail locations and bloated sales teams. Check out wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they'll show you for free the exact portfolio they'd put you in. If you want to just take their advice and do it yourself, you can. Well worth a few minutes to explore: wealthfront.com/tim. ***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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that you'd dig it a lot and you can, of course, easily subscribe any time. So easy peasy. Again, that's tim.blog forward slash Friday. And thanks for checking it out. If the spirit moves you. Hello, ladies and germs, boys and girls. This is Tim Ferriss, and welcome back in my creaky chair to another episode of The Tim Ferriss Show. As per usual, we'll be discussing the tactics, tools, habits of a brilliant individual, world-class performer, as I usually say, and this is no exception. You might remember our guest, David Hanemeyer Hansen,

often referred to as DHH from an earlier episode. He's back for round two because his episode is about to cross a million downloads and that's in barely two weeks. So had to bring him back. You had a million questions that we didn't get to last time. If you missed the first round, DHH, at DHH on Twitter, is the creator of Ruby on Rails. He's the co-founder and CTO at Basecamp, formerly known as 37signals, and is the best-selling co-author of Rework and Remote, subtitle Office Not Required. Because three hours wasn't enough the first time, it went really fast, DHH spent another hour answering your most popular questions, most upvoted questions. In this episode, he discusses digital security, the value of schooling, three questions you

should be able to answer, company culture, how the hell you piss if you are in a 24-hour car race, and much, much more. As always, please enjoy this episode with David Hannemeier Hansen. Shelton asks, what skills does he think are most important today? Is college or graduate degrees worth it? So I have a conflicted relationship with official schooling, whether that's even high school, but certainly also college. And I used to have perhaps a more unrefined opinion of it, which was, for example, as it pertains to business school, that it so totally was not worth it. I've come to appreciate some of the aspects

and some of the things that I was exposed to there more though over the years. But it's all in the context of how you acquire that knowledge. So for me in Denmark, college is not only free, it's you're getting paid to go. You get, let's see if I can do the math in my head you get like 400 bucks a minute actually more than that 600 bucks a month or something like that to um to to go to school maybe even a little more than that anyway enough that you can cover almost sort of your basic living expenses um most people supplement with some work on the side and i certainly did but it's not an overwhelming requirement and then there's also government assisted loans that have sort of a low cap that won't trap you into sort of debt trap so i'm evaluating my college experience against that

that i came out on the other side having being paid for the time i spent there and i did not end up with a mountain of debt. If you do the same thing in the US and you come out on the other side with $100,000 or $200,000 or any other amount in real student debt, these answers might not apply as directly, and self-study might be a better answer. But what I did like, to get back to the point about my college exposure, was all the things that I perhaps wouldn't just have gotten into on my own. I got a good basic understanding of organizational theory, organizational models, and Maslow's theory, and all these sort of the basic canon of business administration and the world that it is. And where we ended up with how to run Basecamp was in many ways the opposite, right? Like we didn't follow the prescriptions,

many of the prescriptions, but knowing about them was actually helpful in establishing where we would choose to be different and where we wouldn't, we wouldn't have to invent uh the deep dish again and we could just follow tradition and where we totally went well tradition is stupid um i gave a talk at stanford business school quite a few years ago now called unlearn your mba because what i got was sort of part of an mba uh lots of overlapping theory on both economics and organizational theory, and lots of the things that I learned. I'm glad that when I learned them, I wasn't an impressionable 18-year-old. I think that's one of the other differences about going to college in the US versus in Denmark. I didn't go to college right away. I stayed out of school for three or four years after high school

and worked in the internet industry, which was just enough time to get me totally jaded about organizational theory and innovation and disruption and all these other keywords and buzzwords that would then be thrown around in business school with a serious face. I was jaded enough to have a very critical mind. So I wasn't being programmed. I was trying to filter everything that I learned through the lens of real life and real experiences. And that made it much more effective, I think, in terms of figuring out what should stick and what shouldn't stick. And what should I not just have a skeptical opinion about, but be in direct opposition to. And I find that that's a great way to define who you are and what you believe is not just

the positive things. I am for this, but also I'm against this. I want to do the opposite of that. I think I actually learned more from business school by saying, oh yeah, all these things, I'm not going to do that. We're not going to work like that. I think that's stupid or mean or bad in any form and we're going to do something else. So I think that really was worth it. And so was the exposure to philosophy and um i'd say where i got the least out of it actually was on um on the computer science part um as i said it was joint degree in computer science and business administration and the computer science part just was i found more value in self-study i think the opportunities that we had even at that time early 2000s of open source software and tinkering on your own and building your own systems was a

much better way for me to learn in large part because I learned my technical things or skills through using them in anger. It wasn't like I sat down for a lecture and then like, oh, yeah, okay, I wonder how I can use this one day. No, no, it was trying to build this specific thing. What do I need to learn to do that? So that worked really well for the specific technical attributes of it. But that doesn't work that well for philosophy, right? Like it's harder to figure out what you don't know about what you don't know, right?

And getting exposed to the disciplines of liberal arts and life in that sense was really helpful. goes for economics and organizational theory, that there are some practical theories and models and ways of thinking that you may not want to use them, but your mind is better by knowing them. I guess, I mean, I shouldn't slander programming and computer science totally in that boat. There's also plenty of value in computer science about knowing different models and paradigms of thought. If you know functional programming versus procedural programming and object-oriented programming, understanding sort of the broad tectonic plates in your domain is definitely very helpful.

So I've warmed up to schooling over time. And perhaps part of that is because I realized more of it stuck than i thought that i would sit through some lecture and i think during the lecture jesus this is stupid i'm never going to use this and years later it would come up that oh that's actually similar to that one thing and i would at least have knowledge of which thread to pull on further like i wouldn't necessarily remember the whole lecture, but I'd know where to go to learn more and inform myself more about these things. So I think the main value there

is just opening your mind to a broader window on the world and a broader window on life, to be honest, especially as it comes to these softer skills um it's stem is a big uh rah-rah moment for a lot of people in um technology and lots of people make fun of history or philosophy or languages and so on and i go like you're wrong um my number one takeaway from going to college and spending time there and so on was to come out on the other side not as a more efficient worker but as a better human as a more well-rounded human being for a long life. And that notion of the long life is quite accurate.

There were several times during the three-year degree where I went like, oh, shit, I'm wasting my time. But you know what? Really, over three years compared to what, the next 80, there's probably limits to just how much I'm wasting my time. And when there weren't limits, when I really thought something was a complete and other waste of time, I just wouldn't pay attention. I'd just accept my bad grades and I'd spend that time on something else.

And that was wonderful, too. But yeah, there we go. Rodolfo Giant asks, does DHH believe that self-writing code will be a reality soon? AI writing its own code like Skynet? If so, when would that be? That's a really interesting question that traces back a long time. When I was going through business school, I have a joint degree in computer science and business school, one of the things we looked at at the time was something called case tools, where you would basically outline your requirements for a piece of software, and then the software would try to figure out how to write that piece of code

for you. And that has a long tradition going back 90s and the 80s, where people thought, we're just on the cusp of figuring out when humans don't need to note code anymore. And we will then arrive at a place where they can just describe their requirements and voila, the software will be produced for them. And I can totally see the appeal of that, obviously, right? And we have moved there to some extent. Computer programming started as an assembler and punch cards and a very low level way of describing your program until we build abstraction upon abstraction upon abstraction on top of it. And now today we're sitting with software and environments like Ruby, where you are describing what you want to happen at a very high level, right?

But obviously, that's still a fair jump to sort of just a natural English description of a software so that's where it really breaks down for me or that's why I don't see computer-ridden software as something that's just around the corner because writing software is really about making decisions and you can really only have something auto-generated for you if you're willing to seed a certain set of decisions. And we've already gotten pretty good, I'd say, at building those abstraction levels up to a point

where the decisions we're left to deal with, and certainly this is my aspiration with Ruby on Rails, are the decisions we care about. If you find a set of decisions that you just don't care about, you just don't care about how that level of the code is implemented, well, then you can abstract and build on top of it. But you can't just say to a computer, hey, can you make me a Basecamp? It needs to have messages and some chat and blah, blah, blah, blah, blah, right? Because you're not going to get the base camp that we have. The base camp that we have is the product of tens of thousands of little decisions

that all, at least in our eyes, matter. Because if they didn't matter, then someone else would have had to figure that out, which I guess is a little bit like if you're not writing your own software, if you're asking someone else to write your software for you, you kind of try to do this, right? You pretend that you can tell another group of people through a set of requirements, can you build me this thing? And then they'll build you something that's close enough to what you want. Ask most programmers or designers how well that typically goes. It's a very painful process for a lot of consultants

and people who live off trying to implement other people's requirements because it's a really fuzzy process. It's really fuzzy to narrow down what it is that you really want. And it turns out, certainly for us when we're software builders, the thing that we really want is those 10,000 decisions all made right. It's not just one or two or three things. So even if we could get to the point where AI could write software on its own, how would we specify the requirements? That's where it really stops for me. Again, that doesn't mean this won't happen and maybe AI will become so smart

as to be basically that black box and perhaps we won't get exactly the software that we want, but it'll be close enough and it'll be so much more efficient. I don't see that as around the corner. And by around the corner, I mean 10, 20 years. Funnily enough, of course, that has been the horizon for ai in general it seems for about the existence of computer science and perhaps even before that that we thought oh yeah we're just like 10 or 20 years away from having

this ai and if you look at what ai is today I think that's a very flattering term for a lot of systems that really aren't that smart. Try to talk to your Amazon Echo or Google Home and pretty quickly the Turing test breaks down or rather just fails it. So who knows what's going to happen in 30 years i don't think anyone can predict that um but i don't see it on the close horizon i don't see wanting it as long as i care about all the thousands of little decisions that go into it um because i think we've arrived at a point where there are plenty of decisions i don't care about i don't care about decisions about memory management, largely speaking, until it's a major issue,

and it very rarely isn't the kind of work that I do. So I can abstract myself from, say, releasing memory by hand, as you used to do in some program languages that are closer to the metal, so to speak. Martin Shorter asks, what are his thoughts on building a company culture? Culture is one of those words that got almost too tainted to be useful

because culture is now sort of a slogan for all sorts of bullshit. And culture is a ping pong table culture is a mission statement culture is all these external artifacts which maybe those are results of culture i don't think they're culture itself i think a far more interesting definition of culture is the things that we do over and over again and it's hard to just write that up before and say these are the things we're going to be because what happens off is of course you don't live up to that stuff i find the definition of culture far more interesting as a historical expedition almost like these are the things that we do so you start doing a bunch of things as a historical expedition almost like these are the things that we do

so you start doing a bunch of things as a company and your definition of culture should be a retrospective of what are those things what are we doing as a company and as uh as the culture that we have and do we like that so culture becomes an iterative process where you keep looking back at what you did and then you make changes when you see things you don't like. And we certainly had a lot of that at Basecamp over the years where we would look back at certain policies or certain ways we were doing things and say, like, yeah, that's currently part of our culture, but they're not flattering parts of the culture. So let's change them. And then we would have other parts of the culture and go like, hey, that's really working. Like we should do more of that. And not only should we do more of that, we should spread that as a gospel to other companies

such that they too can benefit from this aspect of our culture. And that's what the books that we wrote, Remote and Rework, are about. They're taking the aspects of culture that Basecamp had and have and say, we can share those with other people in sort of snippets. And we can say, OK, we're going to have a culture of no overwork. We're not going to have a culture of workaholics. In fact, in Rework, we say, fire the workaholics. In fact, in rework, we say fire the workaholics. So we want to have a place of work where 40 hours less is what's expected of people. So that becomes part of our culture or is part of our culture. And then we sort of observe that and then extract it. I think there

are times where we say, okay, we have some aspirations, but they're based off, again, history of us looking at things we're doing and saying, that's not working. We want to do something else. But it doesn't really become part of the culture before we actually do that. I think a lot of people think

that you can just describe this utopia that you want. Oh, that's your culture. We ascribe to be the best in quality. Like we're all about quality. Well, that's a meaningless statement. It's worse than a meaningless statement if it's not true. There is nothing worse for the integrity of a culture than a description of culture that does not match.

It is incredibly corrosive to have company leaders or company descriptions that do not mirror reality. We just stumbled into this again at Basecamp when we hit 50 people and we realized that in addition to all the books we've written and so on, there are still all matters of culture and practical perceptions of things at Basecamp that are hard for a new person who comes in a new hire to learn in a quick order. We have a very much an oral culture at Basecamp and a historical culture where we did things at certain points and like that formed part of our ethos. But that takes a long time to adopt as someone new so we thought to make things a little more explicit and we wrote up an employee handbook and that employee handbook included all sorts of

different aspects of prescriptive culture but the most most important, I think, was a warning saying, if you're finding things in your actual work that does not match this description of things, you have to stand up and say so, that we will not become a company. And again, that's perhaps more prescription again than descriptor. Although, I don't know, I'm flattering myself. And that's always easy to do. But I'd like to think that we do sort of try to live that, that even when we have aspirations, and we don't live up to those aspirations, we're honest about it. And we can talk about how we failed such that we can get closer and try again. And we already got feedback on that. We wrote things up in that employee handbook where someone new joined the company and said like, you know what? That's not my experience. That's not what I saw. And I find

that that's just one of those unique, beautiful gifts that new employees and new eyes can give you. That they see things much closer to how they really are than the people who've been steeped in the culture for a long time and have sort of just accepted all the illusions and delusions that build up over time. When you get someone with fresh eyes in, they can just go like, hello, guys, this isn't right. This isn't working.

Or this isn't clear. Or on the flip side, this is really working. Like, wow, you guys are really different when it comes to this one aspect. I hadn't lived through that before. I think we have a fair amount of that at Basecamp too, where we need essentially cultural reprogramming, especially for people who've worked in more corporate environments, that Basecamp is quite different from those environments. And it can be hard when you transplant from one culture to another.

A lot of it is not just about learning the new culture. It's about unlearning the old culture. And you have to respect that. And you have to give that some time. And you have to be explicit about how those transitions happen and to say that they matter. And I think that that's sometimes the dichotomy that companies and people find themselves stuck between is that either they're paying lip service to culture and culture is a ping

pong table and culture is a mission statement or slogan, or they go over in the other ditch and say like, culture doesn't matter at all like it's just about the work which is funny enough one of the aspects of our culture and sort of a different area of the company um but culture is real and it matters and you can't just program it up front. It has to be run. It has to be actually lived to be real. Nate Berkopic asks, what things does he do to ensure his digital security, password managers, et cetera?

This is one of the things I've gotten a lot more interested in over the years. When I started with computers, I was completely ignorant of security and sort of thought that it was overstated and who would want to know my secrets, who would want to read my email. And I think even though before just starting to hear about other people getting hacked or getting this sense that this is real. And then I think, of course, Snowden and his revelations about how governments around the world, or in particular in the US, are invading everyone's security and privacy

really brought things to the forefront. And I think we've gotten, and I've gotten, a lot more serious about ensuring things don't go over email or other insecure ways. So for the specifics, i use one password i use one password both personally and with my wife and at the company and that's not a perfect story i think password managers especially the ones that share things through syncing still have ways to go but it's way better than trying to either, A, remember a thousand different passwords, which no one does anyway, or just use a small handful of passwords that you keep reusing

over and over again. So that was a pretty, not that reason, but a few years ago that switching to a password manager, I had some passwords for an embarrassingly long amount of time and just seeing site after site getting hacked really brought that to the forefront on top of that of course um encrypt everything uh this notion that when you turn off your computer or even it goes to sleep and the same with phone, that it could be lost is such a revelation. I remember when in college someone would lose their laptop and they'd go like, oh shit, I lost all my stuff, that person is going to have access to all my stuff. That was just such a terrible, terrible thing.

I think we've really moved forward as a society by now you can lose your computer or your phone and it doesn't mean losing all your data to some criminal and not worrying about who's going through your photos or who's going through your emails or whatever else so encryption on all the things um i find it really disappointing to be honest that uh when you buy a new Mac, full disk encryption is still not turned on. It's something that everyone should turn on immediately if they haven't. And that doesn't just go for laptops, but it also goes for your desktop computers. People have their houses broken into all the time. So go to system preferences, security and privacy, and then file vault and look to see whether that's turned on

and if it's not turned on turn it on immediately two-factor authentication is another huge one especially on your email account if you have an email account right now that's only secured by a password especially if that's not a strong password it's just the one you remember you remember. You're just waiting to get screwed. Because if someone gets into your email account, then they have access to everything, generally speaking. They can reset your password on any other site, and they can get into everything, and you will be owned. And it will be very, very painful. So I use Gmail and use their two-factor authentication, which basically just means when I'm trying to log into Gmail on a new computer or occasionally, I need a second device.

I need my phone to get a code, and then I can log in from there. So that's been a huge step up. I've turned that on. Everywhere you can turn it on, certainly turn it on for things like your bank and your email. And I have it on for Twitter, and you turn it on for your Apple ID, and you turn it off basically anywhere you can. And now it's at the point where if a site doesn't have 2FA,

I'm like, shit, I hope I don't have to put anything important in here. I'm really glad that we got 2FA into Basecamp quite a few years ago because I wouldn't feel good about using a service where I had to store important information without 2FA into Basecamp quite a few years ago because I wouldn't feel good about using a service where I had to store important information without 2FA there. And it's still shocking to me that to this day and age, I'll still sign up for a new service and maybe they won't even have 2FA, but they'll also put retarded restrictions on your password. Like, oh, it has to be only 12 characters. I'm like, like what i'm using one password i'm using a password manager let me have my 25 character mixed password and and put that in there

um so yeah uh encryption and two of a and a password manager i think that's sort of the basic trifecta that if you don't have those things in place right now, get them. Not just for the sake of if you should get hacked, but also just for the sake of ensuring that governments around the world have access to less of your stuff. Same goes, obviously, for instant messaging. Use iMessage, use WhatsApp, or even better, use Signal. Don't use things that send things as clear text or only encrypted in transit. Like Google's offerings, they have to have a special setting turned on for you to have

things encrypted I think that's terrible don't use that if you can avoid it and yeah I'd say those are those are the top things. Levi Belknap asks how did he and Jason Fried make the tough decisions to sell off the portfolio of products 37sals created, High Rise, Know Your Company, Backpack, Campfire, and so on, when rebranded as Basecamp and double down on that product. I'm especially interested in the process they used to think about the decision and the forces at play that they were facing. Yes, this was an interesting time for Basecamp. I think we were around just under 30 people and we were starting to feel stretched, thin. We had four plus products,

four major products and a lot of other psychoshefs going at the time. And we had fallen into this habit of basically just thinking, we're okay with high-rise right now, for example. Let's just put that on the shelf for six months or perhaps even longer, and then we'll just focus on backpack. We'll focus on base camp. And this rotation just meant that our products would kind of just languish for some time. And you don't feel it right away. Customers, generally speaking, wouldn't really complain like, oh, there hasn't been any new features for six months.

But it would still seep in. And worst of all, we felt bad about it. We didn't feel we were doing our products justice. That there was more that we could do and feel better about if our first instinct, we were more people so that led to the discussion of hey we're 30 or 40 people right now we have to be a lot more like if we have four major products and we all want to do them justice and we want to make native apps for all of them we want to do really good design that we think through. We want to do everything to the

peak of our abilities, the best products that we can make, write the best software that we know how. That's not possible with the company we have today. So we face the natural, I don't even call it dilemma, because for most people, it's not a dilemma. For most companies, it's not a dilemma. What you see is, hey, you have profitable products. They need more people. Just hire more people. That's the natural conclusion, right? Well, not for us.

We've always wanted to stay a small company. And for me in particular, I didn't want to run a big company. I didn't want to run a company of hundreds of people. And I saw just the jump that if we went from, let's say, 30 or 40 people to 80 or 100 people, we'd already be down that path of no return, that we could not then prevent the whole thing from ballooning ever further from there. And then we'd be 100 people, then we'd be 200 people. And I would wake up in the morning thinking, why am I doing this? Do I really want to keep doing this? And I'm quite sure my answer would have been no. So that led me to the obvious conclusion that the natural path of expansion, the natural path of just hiring more people to deal with more work

would lead to a place where I wouldn't want to be interested in this work anymore. I would want to get out. As so many people who work with startups and new companies do, they realize that they enjoy working with companies of a certain size, let's say 50 people or less or 30 people or less. And then they just go with the flow and then they end up with a large company and they think, oh, OK, it's time to start over. Well, I didn't want that. So we had some pretty heated discussions for a while. pretty discussions where jason in particular accurately said like hey we have these principles

of wanting to make the best products and work of our life and we cannot do that if we're stretched so thin so we need more people otherwise we can't do it and me going like yeah but no uh i don't want to run a big company push push push push, push, push, push, push. Well, Jason then called a small group of us together in Chicago to think about a big alternative. And that big alternative, of course, was becoming Basecamp. That we would take all these additional products that we have, all these extracurricular activities that were spreading us so thin, and we would simply get rid of them. Not get rid of them as just flush them down the toilet, but get rid of them as in spinning them off, as we did with Know Your Company and High Rise to great effect, or roll it

into the main product, as we did with Campfire, or even just shut it down in the sense of not accepting new customers, as we did with Campfire or even just shut it down in the sense of not accepting new customers as we did with Backpack. And we just sat at that meeting and thought, like, yes, this is the right thing to do. It's not the economically right thing to do. We could certainly have been better off and had a bigger business if we would just have said, you know what? We're just going to hire a bunch more people and we're going to direct those people to keep improving all products at the same time with no stalls and stops. But why? We're already a big enough company. We're already making enough money. Jason and I are interested in Basecamp because we want to be here for the rest of our working life.

Like that's been the goal from the get-go, that we wanted to design a company that we would be comfortable working at, not just comfortable, but happy working at for the rest of our lives. So that's how you get to these weird conclusions where you go like, hey, we have this awesome profitable business. Let's take HiRise, for example. HiRise was almost at the level where HiRise alone, we could have run the whole company off that. And we went like, well, we're going to spin it off. We're not going to work on it anymore. Backpack, which had made millions of dollars. We basically said, you know

what? That was a great run. It's now behind the times. We're going to park it. We're going to make it part of our legacy. And as part of that legacy, we came up with this saying that we're going to keep things around until the end of the internet. That someone, for example, who used a backpack was not going to wake up one morning to a sunset. They're not going to wake up to a fake sunset as it always is, of course, right? Like some sort of like, oh, it's been an incredible journey. Now pack your shit and get out of here because backpack is shutting down. I had seen all sorts of companies from Google, Google Reader, and many others, countless others, almost all others working in our industry.

When they decided they didn't want to work on something anymore, they just pulled the plug. And users be damned and workflows be damned. And that just was nuts. We still to this day have people using Backpack. We still to this day have people using TedDollList, which was a simple to-do list manager we launched in 2005 and shut down, I don't know, a couple of years later, and we still have people using it. And I'm really proud of that. I'm proud of the fact that we, years and years and years and years later, can maintain our legacy while still having one major focus, Basecamp, that one product. So those are some of the dynamics that are going on at the

time. And I think looking back at it now, I just go like, of course, of course, we should have done that. Of course, this was the right answer. Of course, we actually went too long. But that's how things change in business where we started out with the idea. We didn't know that Basecamp was just going to take off like this. We didn't know that Basecamp was just going to keep on growing, growing, growing, growing as it has. So when we started out, we were hedging our bets. We launched other products in part thinking, well, Basecamp might just be a fluke. It might just go out of business, and we better have some other ideas.

And that's a good strategy, I think, in the beginning as we were hedging our bets but then one of the bets just turned out to pay off so spectacularly that it was almost negligent to keep that strategy keep that original hedging bet strategy we needed to double down on the thing that was clearly working so much better than everything else um lest we let that slip through our fingers. So there it was. Levi Belknap also asks, he and Jason are both very opinionated. How have they managed their relationship as co-founders, especially being remote?

Can you share a story about the biggest fights they've had as co-founders and how they've resulted? General rules and processes to use when managing disagreement and conflict in their relationship. Sometimes things get heated. I think things get heated usually, actually, when we talk about specific product things, specific ways of attacking features or how to prioritize things.

And we see things differently. But that heat dissipates incredibly quickly between Jason and I, I'd say, because we always come back to the fundamentals, the fundamentally shared principles we have for the kind of company we want to build and for the kind of product that we want to build. So when you sort of strip things back to first principles and see like wait a minute um how deep does this disagreement go we find that most of our disagreements actually lay at the surface and if you just keep digging and you keep scratching as we talked about on the podcast then you find the common ground it might just be buried a little further down but it's there because if it's not

there then you have deeper problems anyway right like then things wouldn't last for this long. But on top of that, we've used all sorts of specific tactics to resolve these surface tensions. And one of the tactics that I particularly like and we've used for a long time is who cares most. So when we go into a disagreement, sometimes the heat can get pretty hot, but usually there's one person

who cares more than the other person. And we've just set up a give and take system where whoever cares most, if the discussion goes long, wins. That means that sometimes I can care a fair amount about something and then just still say, all right, I'm going to let it go. Jason, you do it. And then he does it. And then the next time, perhaps I'm the one who cares the most. And then we go with my side of things. And the majority of the time, we then argue, argue, argue, get heated, heated, heated. Then everything calms down. We perhaps take a day away from it, come back to it, and then we're all on the same page. So even those areas or times where we have to basically just concede a point, they're pretty rare. And when they happen, it's fine. It'll play fine. Over 12 years, you'll have some, I'll have some, everything will be just fine.

Another tactic to use when you have disagreement is who's going to do the work. If I have strong opinions about how a piece of design is supposed to be implemented, well, if it's Jason who actually has to do the work and corral the troops of designers that he's working with, well, he just has a natural advantage here. He has naturally higher ground. Doesn't mean he's always right. Doesn't mean we'll always go that way. But I'll concede the point more often than not when it falls into his specific wheelhouse, which is design. Same thing goes with programming. We talked about lots of features in Basecamp where it's mostly a technical challenge. And as the technical person or the programmer of the two of us, I get to have the higher ground when it comes to technical matters. So I think we have a great respect, mutual respect for that expertise that each of us hold.

Well, then, of course, we also have the overlap areas where it's about generally running the company or marketing or anything else like that. We can't really use higher ground in those scenarios because it's more even ground we're being met on. But that also means that either we use that other principle of who cares more about it, or as it happens in most cases, neither of us end up being that passionate that if you talk about it for just a little while longer, then it resolves itself. And finally, I'd say we employ the same tactic that we encourage everyone at the company to employ, which is to stop talking and start making. When we have disagreements about which way to go, just trying it usually resolves things very quickly. So if it's about a feature in Basecamp, then you have to implement it and see how it feels and see how it works.

If it's about a marketing strategy, just find the smallest way you can get a disprovable test going and then try it. Again, if I think something is not going to work and we try it and it doesn't work, okay, so what? What, we wasted a little bit of time?

We wasted a little bit of money? No big deal. If we try something I don't think is going to work and it works, again, I win. So if you look at it from that perspective, you can quote unquote win. You can get to the great outcome in all cases. Whether you're right or whether you're wrong you still win if you're right then we don't carry on with that idea if you're wrong then hey that great idea made it through even with your position levi belknap asks uh david is proud father i would love to hear about his

most important lessons learned the things he does as a father that work well for him and his children. How does he know that he's being a good father? How does he measure himself? Well, we talked about this at some length on the podcast, but I look at this on the broad scale at the top level in much the same way I look at everything else, which I'm sure is a limitation. And I have one pair of glasses to see most of the world, which is how would I feel if I was in cold shoes? I, for whatever reason, have a pretty good memory of what it was like being a four year old and the things that I found unreasonable.

So to me, it's not that much of a stretch to put myself in Colt's shoes and to see where things go from there. So I try to think about things from that angle. Is this reasonable or is this not reasonable? And even when it's not reasonable, which is a lot of times when you're dealing with three and four year olds or smaller kids, can we just let it play out anyway? Like, what's the worst that can happen here? If the worst that can happen is Colt is going to get materially hurt, as in broken bones and blood spouting all over the place or death, okay, you don't get to make that call, right?

If you can just get a little bit hurt, like you can bang your head or you can scratch your knee or whatever, fine. Experience that on your own self. See how it goes. If you want to stay up past, quote unquote, your bedtime, which is this thing that adults impose on kids to tell them when it's convenient for the adults to go to sleep, fine. You can do that that you can choose on your own and sometimes i'll say like if you want to just keep being on your ipad you can do that you just you get to sit in the living room by yourself i'm going to bed because i cherish and

value my sleep immensely so if it's uh if it's time to me to go to bed anyway well i'm just going to do that and you can figure out what you want to do. And what usually happens is he'll continue playing for another 10, 15 minutes and then he will want to go to sleep too. So I think there's a lot of wins to be had when you don't have to win everything and you don't have to win right now. And you accept that kids are not only people, but that they have to form their own first-hand experiences. You can't tell a kid in most cases that, oh, well, if you eat another gummy bear, you're going to have a tummy ache. Much better for him to just gouge himself on those gummy bears and get that tummy ache and learn from himself that eating a whole bag isn't that great. Same thing with the sleep

thing if he wakes up and he's tired in the morning well there's some feedback getting those first-hand feedback loops playing is a far better strategy in my mind than trying to teach them teaching those things don't really work that well I find what you can do is offer commentary, suggestions, and so forth, such that not that they'll work in the moment, but that when the natural feedback loop plays out, perhaps it'll ring a bell. Like, oh, actually, he said something about me being tired if I stay up all night, or I'll have a tummy ache if I eat this, or some ways for Colt to put things into perspective once he gets those consequences and smack in the face of himself.

Right. So how does that really play into measuring yourself as a good father? Is there a scoreboard you can keep? Probably not. You probably won't know to a large extent. you'll know the first-hand responses right like you'll know whether um you're having a good time and a good relationship in the moment do you know how that's going to play out over the next 20 years no you don't um so you have to sort of just go with with your best judgment on that and my best judgment is how would i feel in his shoes and is this reasonable can we just let it play out can we just let it slide um which i'm sure for many parents not only am i sure i've witnessed and heard it from many other parents sound like overly permissive

and lax and all sorts of other things you know what i'm okay with that um if for no other reason that one of the guiding principles i have would call it is um how to raise a rebel i do not want a compliant kid a lot of parenting is about having compliant kids who will do what they are told and sit still when you ask them to and be proper and blah, blah, blah. You know what? That's not that high on my list of priorities. This came to the forefront in part when we tried a Montessori school, of all things, in Spain.

And we thought at first, well, Jamie had read up a bunch on Montessori and she'd given me a good recount. This sounds great. Like this sounds much better than traditional schooling and playtime and so on. So we take three-year-old Colt there and he absolutely just hates it, right? He absolutely hates it. Cries and kicks and screams like don't want to go, don't want to go. And it's not the first day, not just the second day for like a week and a half.

And after a week and a half, we're like, this is not getting better. What is going on here? And then we had some conversations with the specific school. And they're like, oh, no, it's going to be okay. But like, let me tell you a little bit about our school. Our number one word here is respect. And I just went like, oh, shit. Of course, that's not going to work.

Really, your number one word for three-year-olds is respect as in that they should respect their teachers and they should respect the rules and like yes this is not going to work we are otherwise following a path here on how to raise a rebel and um that's just not a good fit for for our kid so we learn from that that uh even if you, oh, they have all the right wooden toys with no bad paint and they can play out in the yard and so on. There's some structural frameworks about how teachers and adults think about the relationship to kids that are very much at odds with different ways of thinking. So this is one of those cases where we went, this is not the right thing for our family. And then we put Colt in a basically a play school where there was no structured learning, where all he did all day was run around on

these little motorcycles and play with kids in the yard and sort of painting and other things that were not structured in the same sense and he loved it and had a great time and i thought like hey we did a good job as parents here like we did not subject our kid to just like you have to continue doing this even if you hate it for weeks on end just because we think this is the right thing for you trillies and madison has self-opinion as a kid Smart than the rest? Different? Not really? Hmm

When I think back I definitely had lots of domains Where I certainly did not feel smart And ironically enough The one I ended up doing Professionally, programming Was one of those Because most of the time growing up I had older friends and they were into computers

and quite a few of them were programmers and they were really good. So what I saw was this huge jump in skill that just seemed insurmountable for me. That this was not me. I couldn't do those things. In part because I tried somewhat a little bit and hadn't succeeded on the first go as though anyone ever does. But then I saw the comparison to these friends I had who were just really good at what they were doing. And I thought, geez, this is too hard. Like, I got to do something else.

So I never had this. I'm smarter than everyone else. What I did have, though, was an innate sense that if a large enough group of people can figure this out, so can I. Like, I'm not dumber than everyone else. That's for sure. I don't sort of ascribe to like, oh, yeah, I'm just a dummy. I can't figure this out. No, no.

I can figure this out if I apply myself well enough to it. I'm not gifted with something special here i don't have like some innate talent to do this that gives me a leg up um and some domains i thought like yeah maybe i could become a program but i'm just not going to put in the time that looks really really hard and i can spend my time on other things that perhaps look easier to me and i'll try my hand of those first so it was kind of a dichotomy between thinking like i'm not actually that good at a bunch of things but at the same time i can also become good enough if i just apply myself and when it came to programming then it was an interesting switch when i then learned how to program and again i didn't think of myself as a programmer when i first learned to program then i started working in

open source and then after a couple of years i got exposed enough to see that the code that i was putting out and the way i was running projects was working and that was really a comparison that wasn't available in the same way before the internet and before open source and before getting involved with all those things i didn't have a good way of measuring my progress i would just measure my progress against books or my own sense of self-worth and that wasn't always in in tune. So for a long time, I absolutely did not have any delusions that I was doing anything that noteworthy. It wasn't until I got a chance to compare myself openly against a lot of other people and a lot of other projects

and a lot of other code that I thought like, oh, wait a minute, perhaps this isn't so shabby after all the same went with things like driving a race car like when i first started to drive i thought like oh geez i'm actually not that good at this i'm finishing quite far down the totem pole but a lot of that was pitting myself early against people who were just really good i think it's um otherwise easy to fall into the trap where you're just comparing yourself to some little local circle and thinking like oh i'm the best of my local gang at either programming or playing magic to gathering or mortal combat or the racetrack and then resting assured and happy and satisfied with that um as we've talked about earlier

that was never that never had an appeal to me um so i'd rather just think like hey i'm no different than anyone else but if i apply myself hard enough uh not so much just through like oh you just gotta put in hard work but i don't even it's it's hard to find the right words for this because then I want to say like, oh, be smart enough about it. But that's a misnomer too, because as I just said, I didn't think about myself as particularly smart. But I did think that there are ways of learning that are smart. It's not so much that I'm smart, but that there are some smart techniques and I can just pull those techniques off the shelf and I can apply them. And I can end up in a different place through that. Ian McRae asks, how does he prep for Le Mans? How does he stay alert behind the

wheel for such long periods of time? So Le Mans is a 24-hour race in France that happens once a year. It's a whole week of fun and game and exhausting times um they start by doing the scrutineering as it's called the check of the cars the technical check that they live up to all your regulations in the town center on like the sunday and then the race is that saturday so it's a really long week and it's a really exhausting time and you do have to prepare for that um and it's it's a interesting sort of way that you do prepare one of the greatest way i think to prepare for le mans is to just do a bunch of racing before it there really is no other exercise like actually being on a racetrack that will stand in for that that doesn't mean that that's the only thing you do um usually in ahead of every season

i have a fairly rigorous training program maybe three times a week i certainly did this year where i work with a personal trainer for one hour three times a week and we do strength training and we do endurance training and so forth just to have a general good fitness level that's certainly important it's certainly important to just be in a in a in a good shape i don't take it that extreme i mean there are definitely professional drivers certainly the ones that race in the top prototype class lmp1 that has the toughest physical requirements that do just intensive non-stop training on their bike and do all these other things. Well, I'm not a full-time athlete. That's, to be honest, I don't enjoy it that much.

I exercise because I know it's good for me. I know afterwards that it feels better. I know that I'm going to be sort of in better overall shape, not just physically, but mentally as a human being. And because I want things, I want to be competitive at Le Mans. So these are the things I have to do. And I've just found that those things just don't happen automatically for me. I'm not the person who just like says, oh, there's an hour, let me just go work out. So that's where having a trainer and working on appointment with something,

with someone has been really helpful to me. So I do that. And then it's the funny thing with Le Mans is that a lot of it is still mental too. It's not just about the physical preparation for it. I've seen plenty of drivers who were in great physical condition, still absolutely bomb at Le Mans because they just can't keep the mental game together. And part of the mental game is, if you're leading, if you're close to leading, is the pressure of not making a mistake for that many hours, just going around, around, around, going to get to you. Are you trying to reach

too high and for too much such that you get yourself into one of those mistakes? There's a lot of patience to be played. And it's easy to have that patience, perhaps, in the first stint or the second stint, but perhaps a little harder to have that later in the game. And that's when a lot of people make mistakes um you also of course have the fact that it is 24 hours and when you say 24 hours it's not really 24 hours it's more like 36 hours or 40 hours because you get up pretty early that morning the race doesn't start until three o'clock so you've already been up for a long time by the time the race starts um so there's just a lot of sleep deprivation that actually goes into that specific day.

On top of the fact that you've already been at Le Mans for a whole week and that's tough and that's physical and that's challenging. So you just have to bring that in because the actual time when you sit in the car and you're going at it, adrenaline just kicks in. It doesn't really matter how tired you are. Like it's not like you'll have trouble keeping your eyes awake going 300 kilometers an hour i've had that driving a normal street car where you just go i am too tired to actually do that no matter how much will i apply to this problem it's really hard for me to stay awake you don't really have that same problem in a race car thankfully you could say i've never heard of someone falling asleep at the wheel when you're actually going at it things just happen too quickly but that can

sometimes give you a false sense of security that just because you can keep your eyes open that your mind is open too and that you're making all the adjustments to your routine as circumstances demand them because driving around a racetrack for 24 hours it means that the track changes you have all sorts of things people go off track people who are not you they pull on gravel onto the track you have to make constant alterations so you have to not just be awake but be have an open mind to changing things and changing things up and i think that is probably one of the hardest things for a lot of drivers, that just keeping in that open mode, not just putting it on autopilot,

because on autopilot, that's when you make a mistake. And the next time you come around for some corner, there's a car that's dragged something onto the track, or the track itself just changes. Over the 24 hours, it changes immensely. More rubber goes down, or if you have weather, or any of these other things. So that's some of the considerations I put into it.

That is why I think Le Mans is just the greatest race in the world because it brings these challenges you don't usually feel when you do a six-hour race or 45-minute race for that matter. It's a unique challenge to make no mistakes and stay on your game for 24 hours. Stuart Hart Smith asks, where do you take a piss when racing a 24-hour Le Mans race? Well, in the seat. That is the honest truth. I have never in my six years of racing had to pee that bad that I went in my seat. But I guarantee you that lots and lots of drivers have. I was just actually in a 10-hour race in the US a couple months ago, and my co-driver goddamn peed in the seat. And he was in the start of his stint. He's been out for an hour. And I think the

realization that he had to be in the car for another two and a half hours, he just went, fuck it, I'm peeing in my seat and of course the team is laughing and laughing laughing and why are they laughing well they don't have to go into the seat after him i had to go into the seat after him and the guy um one of the mechanics were like oh you're gonna have such a monkey butt when you get out because apparently when you sit in other people's pee for a couple of hours like that's not that great for your skin it soaks in through your suit and well generally it's just disgusting i think that that is one of the drawbacks of team racing when you have multiple drivers in the lineup who have to share a car together

well it's more on the other guys if you pee in your seat at least if you pee it's your own pee so people simply just go um doesn't happen all the time uh doesn't happen frequently but it does happen often enough that absolutely the consequences is something that most race teams have been in business for a while they know all about hey guys this is tim again Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week.

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