Sam Parr sits down with Jason Fried, co-founder of 37signals/Basecamp, who has been building the same company for 25 years. They explore what founders learn over decades: how to loosen your grip on business and life, the unique role of the founder as risk-injector, what makes co-founder relationships last, how to talk about money with family, and why staying off the cutting edge of fast-moving trends is often smarter than pouncing early.
Speakers: Sam Parr (host, co-founder of The Hustle), Jason Fried (guest, co-founder of 37signals/Basecamp)
The 7.5% Guaranteed Return Poll [00:00:00]
Sam: All right, today’s episode we’re going to talk about things that interest us. One thing that I tweeted out the other day — I wasn’t surprised by the result, but it still made me sad. I tweeted: if you could guarantee a 7.5% real return for the rest of your life, every year, guaranteed, but you can’t invest in any individual stocks forever — however, you can start your own business, and you can only invest $10,000 into that business — or you can invest actively, and some years maybe you’ll get plus 50%, some years you’re going to get minus 50%. Which would you choose, option A or option B?
Sam: 40% of my 300,000 followers selected option B. And you replied and said option A, all day, easy. Why did you select that?
Jason: To get 7.5% with no effort and it’s guaranteed? It’s a no-brainer. It’s an absolute no-brainer for me. I mean, I’ve got a business, I have a lot of risk in my own business, so that might be part of it. I have all the risk there.
Sam: So let me ask you this — were you intending this to be like someone who’s 21 years old, straight out of school, never invested before, has nothing else going on? Or is it just at any point in your life?
Jason: I think at any point in your life, that’s still the right decision. I still turn that switch on in a second. That’s a ridiculous return — in a good way — and a consistent return. The way that would compound over time would be fantastic. There’s nothing boring about that. Well, it is boring actually, but also an incredible thing. So yeah.
Sam: Were you surprised by the ratio? Were you surprised by what the poll produced?
Jason: I’m surprised that the average Joe — and my followers are probably above average in terms of income, maybe IQ, maybe not, I don’t know. They’re typically a higher-educated crowd. I would have thought they would have seen the fallacy, that they probably can’t beat the market, particularly with all the others who have a much better advantage. The idea that everyone else fails at getting this return, but I, in my little office, part-time, just me, can somehow beat all the others — that’s what surprised me. That they thought they were exceptional at that.
Sam: Yeah, well that’s pretty common. I think everyone thinks they’re exceptional in some way. The thing people don’t take into consideration is risk. They might go, well, if I just buy Nvidia or Apple or Shopify — and in the short term you almost certainly can, over the next two or three years, get lucky and pick a winner. But the rest of your life? That’s the question.
Sam: Here’s what I’ve done lately. I’ve been spending time in New York because I’ve got family here, and I cold emailed and did cold outreach to people who work at hedge funds. I’m like, hey, I’m not a competitor, you don’t ever have to worry about me. I’m just a passionate, interested person. Can I just see your office? Can I sit at your computer and have you show me your software? I just want to see what you do all day.
Sam: You go to some of these offices, and I would have thought they’d be Wolf of Wall Street — buzzing, phones ringing. It’s really quiet. It’s usually just a bunch of nerds looking at a computer screen, but they’ve got four screens and incredibly complicated software. The average person there is getting paid hundreds of thousands, sometimes tens of millions of dollars to be good at this one thing. And then I think about how Bobby Lee in whatever Missouri, where I’m from, on his Robinhood app is possibly going to have an edge on all these resources.
Sam: And these people, with all these resources, they’re still not that good. I talked to a guy who worked at Bridgewater recently and I was like, Bridgewater — I’ve read Ray Dalio, aren’t you guys like the best? He’s like, sometimes we’re the best, but the last 15 years we’ve sucked, we’ve underperformed the market. And I’m like, that’s insane. 1,500 employees, hundreds of billions under management, the best there is — you still can’t beat it. That’s kind of where I’m coming from.
Jason: Yeah. It’s also like Vegas. You go to Vegas, you’re on a hot streak for 30 minutes, but the longer you play the less you’re going to win. The house is going to win over the long term. People have this idea of short-term performance in the market feeling like, I can do this forever. Just like in Vegas, you can’t. You will begin to lose. And the same thing is true in the market. So yeah, lock it in.
Loosening the Grip [00:08:00]
Sam: What’s this thing about loosening the grip on the stick?
Jason: Yeah, so I got a drum set recently. I used to kind of want to play drums, I did a little bit, stopped for many years, and recently just picked it up again. As I’ve been playing I learned this very quick lesson — and it’s also true when I tried to learn guitar — when you’re new at something, you tend to hold things too tightly. I hold the drumstick too tightly. I hold the neck of the guitar too tightly. Anyone who’s played any instrument will understand where I’m coming from.
Sam: I used to play drums, I know what you’re talking about.
Jason: Okay. So you hold the stick really, really hard, and then you fatigue faster, you don’t have as much articulation on the stick, you can’t get certain ghost notes and tones out of things because you’re always hitting too hard and too firmly. There’s no finesse. And it kind of dawned on me recently that this is very, very true for most things in life — especially business. I realized that by simply loosening my grip a bit, by lightening up, you end up having better control, you end up playing better, you end up working better, you can do it longer, and you allow other things to happen that weren’t possible when you’re gripping so tightly.
Jason: I think this is true for business. When you’re starting a business you typically have a really tight grip on things, and it’s best at some point to loosen up a little bit and let the rest of the organization expand into itself versus you trying to control every last thing. I run into a lot of entrepreneurs who I think have not learned how to let go of the stick.
Sam: I think that’s also a young man’s thing, right? You learn this with age. What are you saying, what are you trying to say?
Jason: What I’m saying is, you have a couple decades of experience, and so do I, and as I’m getting older — which I’m not old, but neither are you — I’m learning it is okay to loosen up. That’s what they say about a lot of men: he used to be intense, but he’s mellowed out. And that’s usually what they’re referring to.
Sam: That’s a good point. The mellowing out is nice.
Jason: In a different realm — in music, finding a metaphor — I’m thinking about loosening up your grip a little bit. And what parts of life? Business, I would say. Also with my kids. I kind of wanted them to do certain things a certain way, and it just creates conflict. They’re their own people, I’m my own person. I want to encourage them to do certain things, but I also have to loosen up around that and let them find their own way. I kind of learned that pretty early in parenting.
Jason: In general I just feel better when I’m not gripping things so tightly. And when I look out there on Twitter or LinkedIn and I’m reading these business stories, there’s just a lot of grip, a lot of tension. People are trying to overoptimize and paying attention to every last little thing in a way where I feel like — just loosen up a little bit. Pay attention to a few things that matter and let things just be.
Sam: The best example I’ve experienced this in my real life is arguing with people. Before, it was like every word — fighting was the first thing that came out. Early words, I wanted to fight. If I met someone with a different political perspective it was, you’re wrong for these reasons, you’re really stupid for that. When I lived in San Francisco I was significantly more combative than I am nowadays. I’ve been lucky that I was raised in Missouri and that I lived in San Francisco, lived in New York, lived in Texas, and that has shaped me a bit politically — but it also bleeds to other points of life, which is instead of fighting when someone says something I disagree with, it’s now: well, why do you feel that way? That’s a really interesting perspective, tell me more.
Sam: I don’t know if this is just a clickbait thing, but Keanu Reeves had this quote where he was like, I used to argue with people, now I never argue. You could say one plus one equals five and I’ll say, well, I hope you have a really good day. And that’s a little bit about how it’s been. I’ll still catch myself arguing, but Dale Carnegie in his book How to Win Friends and Influence People has this famous teaching: basically just don’t argue with people, because no party typically walks away happy or satisfied. So loosening the grip for me is arguing less.
Jason: That’s a great example. Holding on too tightly to a perspective — because you can have a perspective you really believe in — but it’s like, don’t clench to where you’re not even able to listen. The point about being too grippy is that you’re like a spring under tension. If someone says something you disagree with, you’re going to boom, expand and explode. That’s kind of what an argument can be. Versus just already taking some of the tension out of that spring, and just bouncing with it, listening versus exploding.
Sam: Have you ever — there’s this term, I’ll have to figure out what it is, but there’s this phenomenon where astronauts go to space and see the Earth from far away, and many of them have reported a life-changing perspective. They think to themselves: the fact that we’re fighting over religion is ridiculous, the fact that we’re fighting over borders is ridiculous. Zoom down to the smaller things — the fact that we’re fighting over someone saying something rude to us is absolutely crazy, because we’re all just a bunch of monkeys on this floating thing. Monkeys with cars.
Jason: We are. And we see this abyss and then we’re just this silly blue thing in the middle of it.
Sam: A lot of astronauts say it changes their perspective and mellows them out. And I think when I read about that years ago it helped me calm down a little more. The stuff I thought mattered doesn’t matter. For example, I remember when COVID happened and I was like, we’re never going to a concert ever again. And then three years later I’m like, I forgot all about that.
Jason: Have you read that great passage from Carl Sagan, the Pale Blue Dot?
Sam: What does he say?
Jason: I’m not going to say it because I want you to read it. I want you to have the experience. It’s short, it’s a paragraph. It is one of the most beautiful passages I’ve ever read. But it’s exactly what you were talking about with the astronauts — looking back at the Earth. It’s all about all the things that have ever happened — every leader, every religion, every point of view, every argument, every whatever — all beautifully written in beautiful prose, happened on this speck of dust. I think he calls it a mote of dust. It’s such a beautiful passage and it brings tears to my eyes. I try to read it a few times a year because it’s so right. It’s so spot-on. All the stuff we’re so fired up about — who cares. They’re real for you in your day-to-day life, but they really don’t matter that much. It’s just a good reminder.
Business as the Drain for All Wisdom [00:18:00]
Sam: Well, it’s a paradox of caring by not caring. Why do you not like comparing this to business? And I’ll tell you my reason why I think it’s good.
Jason: This is an undeveloped thought that’s been sort of on my mind. I don’t know if it’s a good idea, so just run with me here. It seems like every great lesson is then applied to business by someone. A Navy SEAL learns all this stuff in the military and comes to consult for companies about how to run teams. A great coach coaches a great team, and then comes to bring it to the business world. It’s always bringing it to the business world. And I’m like — what does the business world deserve the best lessons from things that are completely unrelated in many ways to business?
Jason: The main reason, in my opinion, is because the business world pays for that advice. It’s not that it deserves the advice, it’s not even that the advice is applicable, but that it pays for it. And the way I’ve been thinking about it is not as this shining beacon on a hill that business deserves all the greatest things, but actually as the drain that all these ideas drain down through. Because business is just willing to pay for it, and it’s sort of insecure in a way. It wants to listen to the Navy SEALs, it wants to listen to the great NCAA coach. It’s insecure in its own right. And there’s also this sense of like, these other places and people — they know better than us, so we’re going to bow down and take their advice.
Jason: I don’t know, again this is a little unformed. Does that make any sense or is this a weird idea?
Sam: It makes sense, but my argument would be: instead of the image you’ve painted — an upside-down triangle with all this beautiful stuff draining down into this bad thing — I’d turn that upside down and say it all flows up to this amazing thing. Here’s why.
Sam: Whether you like capitalism or don’t like capitalism, you cannot deny that it’s here to stay. At worst, it’s here to stay in the lifetime of everyone who’s alive. Therefore, I think that capitalism, and thus business building, is the most practical way to manifest a dream or a reality. Often times you can say, what about art? And I would agree, but at the end of the day you’re still making stuff that people want, you’re still selling tickets, you’re still trying to make some type of money off your art so you can continue doing it — or you’re going to have a rich person fund you so you’re able to do it. My opinion is business is the most practical way to actually put a dent in the world or to manifest a vision. I think of business as a bit of a spiritual journey of turning dreams into reality.
Jason: That’s an optimistic point of view, which I do understand. Here’s my question: if this entity called business is absorbing all of these lessons from all of these other realms — and they’re filtering in, maybe I’m wrong about this — why aren’t the Navy SEALs asking CEOs for advice?
Sam: Sometimes they are. If you look at Jack Welch’s book, Six Sigma — a lot of different types of organizations outside of business view that as the rules of the game.
Jason: Yeah. I might be uninformed about what the military is listening to, what sports teams are listening to. But there’s something about this — you would imagine this entity that has absorbed everything would then be the definitive source of this wisdom. But I wonder: is it a one-way street or a two-way street?
Sam: I think you’re more right than you are wrong. It’s definitely more one-way.
Jason: Yeah. I just wanted to give you the idea. It’s been floating in my head for a bit. It’s fun to air these things out.
Early Days vs. Late Days of the Company [00:24:00]
Sam: What was more fun — early days or late days of the company?
Jason: Oh man, that’s a really good question. They’re very fun in very different ways, so it’s a bit of a cop-out, but it’s true. What’s exciting about the early days is there’s a certain energy you can never capture again. You’re starting from zero, building something, you don’t know where it’s going to go, what’s possible, what isn’t, how long it’s going to last. There’s this hope, this possibility, this birth. You get a lot of new attention, you burst on the scene, and that’s exciting. Really exciting.
Jason: What’s hard, actually, is the middle. We’ve gotten to a place now, having done this for 25 years, where it’s become really fun again in a different way. But I would say 15 years in is a different story. Because at that point it’s like, we’ve been doing this for a while, I don’t know how much longer it’s going to last. You’re kind of in a maintenance mode.
Sam: Were you big enough at 15 years where payroll wasn’t an issue? Was there any outside pressure, or was it like, things are fine — I feel weird that I’m complaining?
Jason: Yeah, it’s more like — Scott Berkun wrote a book called The Messy Middle. I haven’t read the book actually, but I understand the idea of it. The middle of it is like, what do we want to be now? Where do we want to go now? Are we going to be a big company? Are we going to stay a small company? There are all these opportunities swirling around us versus when you’re starting, you’re just going, you’re just moving.
Jason: Then we get to this place now where we’re mellowed in a sense — to your point — although we’re actually getting very ambitious again, because we’ve been doing this so long that if we took some crazy bets and it all fell apart, I’d be okay with that too. We’re at the place now where it’s like, we’ve done plenty and we’ve had an incredible run. If it all ended with a bang because we tried some crazy stuff that didn’t work, I’d be okay with that. I feel like I’m at that place now where I wouldn’t have been at 15 years.
Sam: What’s your sense — I mean, you started a bunch of stuff. My sense is that none of my things have been as big as yours, but they’ve been big enough where we’ve had 50, 60 employees. We got outside of the existential crisis moment. Everyone talks about focus, and it’s something I firmly believe in. But as someone who likes to make things, for my skill set — a company outside of maybe $3 million or $5 million in revenue, like 15 employees or something — I’ve noticed consistently that I’m like, I don’t know what to do with my hands. I feel useless. I feel like a general behind the scenes just pointing.
Sam: And I’ve noticed something that I really dislike but think is normal: a company ebbs and flows, and I’ve noticed that this ebb and flow carries over to the rest of my life. I just had a child and I’m in this quiet time where I have to be present. There’s other times where you’re in war mode — action constantly, I’m on top of my game, we’re launching this new thing, we’re out fighting with the troops, in the trenches. And then there’s other times — sometimes this can last for years — where it’s just like, we’re doing the same thing over and over again. And that period can be a little depressing, even though everything is going well. It’s what they say about great investors: if you can watch paint dry, you’re going to be a good investor. The problem for a lot of entrepreneurs is that’s a really sad place to be in, even though everything is going well.
Sam: Have you had a lot of periods where you’re like, man, I’ve got to just do nothing for maybe years?
Jason: Yeah, I can totally identify with that. What you’re getting at is: in the early days you are very important as founder. Then there’s a point where you build an organization, and the organization is able — in a good way — to run without you to some degree. At that point you feel a little bit less valuable to your own thing that you made.
Jason: It’s a good thing, because it means there’s some stability and you’re not the bottleneck anymore. But for you personally, it feels like you’ve become detached from this thing you made. You’re now further from the creation phase and more in the maintenance phase. You’re dealing with internal politics, personalities, hiring, great people who just left and you’ve got to find new people, the culture is changing. That’s a pretty tumultuous time for a founder. I’ve gone through that many times. It comes and it goes.
The Founder’s Job Is to Inject Risk [00:32:00]
Jason: What I kind of discovered recently is that my job as the founder — I’m still a founder, I still started this company, I’m still in it after 25 years — my job is to inject risk into the business.
Jason: Most people, essentially everyone at your company, their job is to manage risk to some degree. To keep their job, to not push too hard or too far. You, ultimately, can get away with certain things that other people simply can’t, because you own the damn place. You are the original person.
Jason: So I found a lot more joy and excitement in revisiting this idea of injecting risk. And by the way, I don’t think you can change that about employees. For a long time I was like, why aren’t these people taking risks? I’ve got to force them. But it’s impossible to change. Even if you hire a great CEO to replace you — they might be an incredible CEO, great executive, trains are on time — but there’s that thing present in a founder simply because they were there from the beginning. They have an extra ounce of latitude that allows them to take risks nobody’s going to say no to.
Jason: So the way I found to return to flow versus the ebb is to inject more risk. For us, that means we’re going to build a lot more products this year. We’re going to do four products. We’re about to start working on two products simultaneously, which we’ve never done before. There’s a lot going on — different models, once-a-week subscriptions, SaaS — we’re going to do multiple versions of multiple things with different business models. We’re really off balance in a really healthy way at the moment, because we’re doing a bunch of new stuff. That gets me excited.
Jason: Now it makes some people internally nervous, understandably. But that’s how I have to run the business. Otherwise I will become bored. And at that point it won’t serve me or the business well if I’m in charge and I’m bored.
Sam: That’s like the main 9-to-5 thing. For Hampton I have a CEO, so I try to respect that relationship. On my nights and weekends, I created a new website for fun. It’s called Sam’s List, at samslist.co. The reason I did it: I tweeted out, “who’s got an accountant that they love?” because I just needed an accountant for something. I got like 300 replies. A lot of people bookmarked it, someone was like, I’m saving this for later to find an accountant. So I was like, this is interesting.
Sam: I spent a few months calling every accountant on the list — finding out how much they charge, what services they provide, what services they don’t, who the ideal client is, who isn’t. Then I created a website called Sam’s List where I put all the information from my research on all these accountants. I think I got 8,000 people in the first week. This month, the first month it’s been live — I think it’s done $20,000. And the $20,000 I’ve made from that is more dopamine than let’s say a million or two million dollars a month from other things. It’s a total rush.
Jason: Why do you think that is?
Sam: It’s so fun when things start as silly jokes — the logo is a calculator that looks like Clippy from Microsoft, waving at you, it looks like Mickey Mouse. I used ChatGPT and said make a logo that looks like Clippy but it’s a calculator. It’s so fun to take silly, jokey stuff and turn it into real things that actually solve problems. It’s part trolling, part scheming. Like, isn’t it hilarious if we made this a thing? And then actually seeing it become a thing — I find that to be so exciting.
Sam: Also, when you have an idea — even a serious idea — and you start seeing customers truly like it, that’s a very invigorating feeling.
Jason: It’s the best. We have this internal saying — we don’t say it that much, but I’ve said it before — which is cool wears off, but useful never does. And what you’ve made is something that’s useful. That is one of the most beautiful things you can do for humanity: make something useful. And to have fun with it, to screw around and not take it so seriously. This goes back to your grip being loose on this. You’re having fun with it, you asked ChatGPT to make a logo and you’re goofing around, the name is just your name. Have some fun.
Jason: It’s a reminder that that’s what this should always feel like, as much as possible. It is totally valuable to do hard things, absolutely. But not everything should be hard. There should be plenty of easy things in your life too — things that flow, things you have fun doing, things that don’t feel hard. You don’t need to pile up and collect only hard things.
Jason: While some of your business ideas might be harder for other reasons, this one is so lighthearted and easy. It’s healthy, it’s good for you, and you rediscover why you do this stuff. There’s something, I’m guessing, in this where you’re like, I did this by myself.
Sam: Yeah, that feeling of accomplishment — I can still do something by myself, really by myself, and it’s useful. That’s very rewarding and hard to come by sometimes when we all think we need partners and co-founders and teams to pull things off.
Co-Founder Compatibility and Business Partnerships [00:42:00]
Jason: Do you and your partner get along beautifully?
Sam: We get along really well. We’re friends but we don’t see each other very often — we live in the same town and I see them maybe once every couple of months. We’re very good partners and friendly, but we just don’t hang out. Our families don’t hang out, not that we wouldn’t enjoy it.
Jason: There was a study where they looked at the most common reasons why couples get divorced. The most common reason was contempt. The most common reason for staying together was admiring the other person.
Sam: I hadn’t heard that, but it resonates. Resentment is just bad. And I think a lot of business partners resent each other actually.
Jason: Have you been in business with others?
Sam: I’ve got — the most I’ve had, I’ve had bad relationships. I’m currently in a very harmonious relationship with my co-founder Joe that I could see lasting a lifetime.
Jason: What feels different about it?
Sam: When we first started together we invested in startups together and had a great time. He previously helped me with my old company, The Hustle. I cold emailed him, he was like, if you’re in New York tomorrow just stop by the office and we could talk. I flew out there and hung out with him, and that’s how we became friends. Then we invested in startups together.
Sam: Then I had a really formal conversation with him — like I did with my wife early in our relationship, when we were thinking about whether this was something we wanted to make real. I sat down with my wife and we just walked through our life values and what type of life we wanted to have and whether they aligned. So I sat down with Joe and said: what sacrifices are you willing to make? What sacrifices are you not willing to make? What does a perfect day look like for you? What are you driven by?
Sam: For me, I was like, I’m driven by ego — it bothers me that people think I’m not good enough, so I always want to prove that I’m as good as I think I am. I’m driven by money. I work only 40 hours a week, I don’t want to work more than that. I’m not willing to sacrifice traveling. He named all of his things. We looked at everything and said: how much money do you want to have? How much money do I want to have? For everything agreed upon — awesome. For everything not agreed upon — is that a deal breaker? And they weren’t. We did a really good job of being very honest upfront about our wishes.
Sam: Now it’s much easier to address any issues because it’s like, he’ll be like, we got to get this done, and I was like, yeah, but — he’ll be like, you told me you don’t want to grind on a Saturday, so I’m not even going to ask you. It’s all good. We agreed to this. We respect one another and we had those conversations early on.
Jason: Do you feel like the conversations you had about that turn out to be true? Are those really the things you share?
Sam: For example, with money — we actually shared each other’s personal finances with each other.
Jason: Interesting.
Sam: Yeah, we were super transparent. Here’s all our finances. I’d like to go here one day — where would you like to go? To get there, we’re going to need — let’s say my goal is less than your goal — let’s hit your goal then. Here’s maybe what the numbers would need to look like. Is that something we both agree on? We were very transparent with each other.
Jason: That’s wild. I know you and I were talking on Twitter about how I’m super uncomfortable talking about money, and you’re sharing your personal finances with your co-founder. You don’t do that with your partner?
Sam: Well, our finances are tied together. Essentially the vast majority of our net worth is in our business, so we know what our distributions are. But yeah, we don’t talk about it beyond that.
Jason: I feel like as a Midwesterner — I’m a Midwesterner — my thing is don’t talk about it. I don’t know why, it’s ingrained in me. Were you like that at one point, and did you change?
Sam: I was always open about it, because I saw my family not be open and I was like, that’s so unhelpful. You’re not giving me a road map. I don’t have anything to strive for because I don’t even know what’s possible. My father owned a produce brokerage company — they sell, like over the course of his 20 or 30 year career, maybe $150 million worth of onions. But I’m like, how much is a lot? Is that $50 grand a year or $300,000 a year? I have no clue. And I always regretted that they weren’t open with me. So I was like, I’m just going to be open about it.
Jason: It’s so interesting. My folks never talked about money. I still to this day don’t know if they’re middle class, wealthy — I don’t really know.
Sam: You’re kidding me. You really have no idea?
Jason: Do you support them?
Sam: I have supported them. I gave them a big chunk of money at one point. They regretfully took it — they didn’t really want it. I don’t think they need it and I think I’m going to get it back when they pass, they’re not going to use it. They’ve always been very frugal.
Jason: My dad was an entrepreneur, worked for himself, a small business owner. He was a trader — he traded stocks on his own. I think he started out as a broker for a little bit, then was an individual investor. I think he did well for a while, I think he didn’t do well for a while. There wasn’t anything we couldn’t have, but we also didn’t strive for anything we couldn’t afford. I don’t really know. My parents have always been careful with this, so I absorbed that — just don’t really talk about it.
Sam: What are you going to do with your kids?
Jason: I struggle with this. My parents never really talked about it. We certainly act differently than my parents did growing up — we own a few homes, we’ve got some nice things — so it’s kind of obvious that we can afford things. But we just haven’t talked about it. That is an incredibly Midwestern and more traditional older set of values. My family had very Midwestern values. A lot of those values are great — hard work, don’t complain. I remember going to a restaurant and we ordered a pizza and they brought us a chicken salad, and I’m like, yeah, we’re not going to inconvenience you, whatever.
Sam: I’ve never sent a dish back in my life. Not a million years.
Jason: Exactly. Some of those values are great. But I think there’s many other values that are — and I don’t like using this word because it’s too loaded — but bad. For example, the stoicism that Midwesterners tend to have. I think it’s gotten you to where you want to go in a traditional success perspective, but not being transparent with certain people — I just don’t want my family to be left wanting more when I’m gone in the sense of, I wish they were more open with me.
Jason: I haven’t seen photos of my family when they were younger. I don’t know their grandparents’ names. I had to do 23andMe because when I asked my parents about my heritage they would just say, we’re white. And I’m like, yeah, but what flavor? I had to do Ancestry.com to understand who my grandparents were. What are you guys hiding? And it turns out I found out that an uncle is actually — my grandmother was married previously — and I’m like, why didn’t you guys tell me this? They’re like, oh, we didn’t want to bring it up. Little things like that. Just discuss it.
Sam: I admire that actually. And this is something I also admire about David — I’m sure you wouldn’t mind me telling you. When we had an office in Chicago, David used to drive to work in incredibly fancy cars. My Midwestern sensibility was like, dude, don’t do that. He’s like, why not? My sense was it sends a weird message. He’s like, what’s the message? Everyone here who works knows we’re doing well. Why would I hide that?
Jason: I agree with you on that one, by the way.
Sam: And he’s right. I mean — have you seen The Big Lebowski? He goes, “You’re not wrong, dude, you’re just an asshole.” So in my mind I’m like, but I still struggle with it because of how I was raised. The imagined messages — I’m imagining everyone’s looking at that car and going, what an asshole. But most people probably don’t care. They know the score. And if they’re not fine with it, that’s their problem. David’s point is: if they have a problem with me driving a nice car, that’s their problem, not mine. I’ve earned this, I enjoy this car, I buy it because I like it. I’m not going to hide the car.
Jason: And he’s right. But I just have a hard time with it still.
Sam: Not anymore with him — this was way back in the early years. But it still is something that’s in there. There’s a residual struggle with that degree of honesty around money. Similar to how people don’t talk about who they voted for. I think Chris Rock has a great bit on that. When I see someone with a political bumper sticker on their car, I’m like, you’re insane. And they’re probably like, why? I like this person, what — why do I have to hide my point of view? And they’re right too.
Jason: Deep down, their point of view is healthier. I still have a hard time with it. Maybe that’s my problem, maybe it’s not. I don’t really know.
Luck, Money, and What to Tell Your Kids [00:52:00]
Sam: Do you want to change, or do you not care?
Jason: I think my son, who’s older — my daughter’s five, she doesn’t recognize any of the stuff yet — but my son does, and he seems to be into expensive things. He’s not an idiot. Do I want to sit him down and say, hey son, we’ve got this and we’ve got that? That isn’t how I’d handle it. It’d be more like: I’ve worked hard, here’s what we have, we have some things, we’re going to enjoy these things, we share these things with friends. This is not just our stuff.
Jason: That’s kind of how I treat the house thing. When I renovate a nice old house and make it better — it’s our house, but it’s also all our friends’ house. People are free to stay there as much as they want. I have this property in Wisconsin, an old farmhouse, 160 acres — it’s a beautiful piece of land I’ve been working on for years. My friends use it more than I use it. I’m not even around there much anymore. My friends can just go up there whenever they want. It’s about: we’re clearly fortunate, and a big part of this is you want to share these things. You’re not fortunate if you hoard — there’s something kind of wrong about that. Share as much as you can. Share these experiences with other people.
Sam: The thing that I tell my friends and family — and this is something I couldn’t grasp earlier in my career, I refused to admit it — is that luck is real. It has played such an important part of any type of financial success. Just meeting the woman you spend your life with — just the fact that you’re in the same place at the same time. Luck is such a bigger component than I ever would have been willing to admit years ago.
Sam: What I’ll explain to my children is: look, I worked hard, but I frankly didn’t work harder than many other people. I’m smart, but I’m not that much smarter than the average person, if at all. The truth is I worked hard, I had a skill, but luck was like 50% of that, maybe even more. I hope I can help my family realize that. It just happened to work out because some timing thing worked out. Let’s say you started a business and you surged during COVID — I didn’t know that was going to happen. That was total luck. Things like that — it’s absolutely real.
Jason: 100% with you, and I think it’s way more than 50%. All the way back to: you didn’t choose your parents, you didn’t choose anything. You didn’t choose your mind. How’d you become the kind of person you are? A billion inputs you don’t know about.
Jason: One of the things I regret most in my career — regret is too strong a word, but one of the things I regret most — is getting on stage at Startup School. This is Y Combinator’s Startup School, years ago. I was only invited once because I was pretty anti-raising money.
Sam: I would have thought you’d be the opposite of their ethos.
Jason: I was. But Paul was kind enough to ask me to come up on stage and give a talk. And you and Paul seem quite similar, to be honest.
Sam: I appreciate that. I have a lot of admiration for his ability to put things together and think things through, and what he’s built.
Jason: He invited me on stage and there was a question from the audience about luck. Someone’s like, do you believe in luck? And I said, hell no, I don’t believe in luck. And I was such a prick.
Sam: How old were you?
Jason: Mid-20s. I was just such a prick. A young punk prick. And it’s so embarrassing. But you know, it’s like poetry you wrote in college — oh my God, I wrote that. Whatever it is. You just realize that’s part of growing up — totally misunderstanding the world and your position in it. And then hopefully you develop a bit more, you have some self-reflection, and you can call yourself out on the stuff that you thought. But that was also who you were at the time.
Staying Off the Cutting Edge — The “Must Know Now” Trap [01:00:00]
Jason: Last thing I wanted to ask you about was this: staying off versus staying up. You said, imagine all the things you felt you were falling behind on — if you didn’t learn about them last year, would it really have mattered if you started today instead? Watch out for the trap of “must know now.” What does that mean?
Sam: Right now, in the AI world we’re in — every once in a while in my feed on Twitter it’s like, “10 things you’ve got to know or you’re falling behind.” And this thing is brand new and moving faster than any human can pay attention to. I just keep seeing these stories about if you don’t know this, and if you’re not on top of this — no, it probably doesn’t matter that much. All the things that, if you would have read that feed a year ago you were supposed to know, it wouldn’t have mattered that much if you started now instead, or waited a year in some cases.
Sam: One of the things I was doing for a while — I’m not doing anymore but I should go back to it, and it was easier during the pandemic — was to go back and listen to podcasts that are a year old. So today is May 22nd, 2024 — I go back and listen to May 22nd, 2023 podcasts. During the pandemic it was great because you hear all these experts talking about this and that, everyone so certain of everything, and you go back and you’re like, man, we are so wrong about so many things. So many of the things we were worried about never happened anyway. If this political issue and that political issue — if this guy gets in office this is going to happen — turns out very, very few things actually happen.
Sam: It’s a nice exercise to go back and listen to old podcasts and old interviews of substance and realize that the sense of urgency in these podcasts is so misplaced. Most things don’t need to happen right now. You don’t need to be up on this right now, and you shouldn’t feel bad about not being on the cutting edge of X, Y, or Z — especially an edge that is resharpening itself every few months. I try to stay a bit out of things. I’d like to let things settle in a little bit more before I really start to dig in.
Jason: Do you read any biographies?
Sam: A few. I really love the idea of biographies. I have a hard time reading long books — I’ve got a limit at around 500 pages or less, though I’ll do a long one every once in a while. But I read a fair bit, not because I’m in a competition — it’s just an hour a night, which is typically a book a week. I read a lot of biographies. I like business biographies, I love history, so a lot of World War II leaders, a lot of American Titans of Industry.
Sam: I have this process. I’ve got a spreadsheet — I only read on Kindle, and any time I see something interesting I highlight it. At the end of the book I create a timeline: here’s where they were born, here’s where they died, and then anything I highlighted that happened in a given year. Then I go to this website called Newspapers.com. Newspapers.com has archived pretty much every newspaper ever, back to like the 1600s.
Sam: What I like to do is — let’s say I read a biography about Ted Turner. Ted Turner is the guy who started CNN. He’s the biggest land owner in the United States. I go back to my Kindle and my spreadsheet and I see: in this year he decided he wanted to buy land. I go read a newspaper article that wrote about him during that period. And I want to see what he said about his interests, why he’s doing it. Did he say, for example, one day I hope to own 5,000 acres? Turns out he owns millions of acres. So I like to read what the predictions were, as well as what people were saying about the person at the time, so you don’t get revisionist history.
Sam: What you notice when you do this is that you’ll read a biography and think, this was obvious — who wouldn’t have predicted this was going to happen? World War II — Churchill was like, the world’s going to end, we are going to die. We felt that way during COVID. But if you read a lot of history, there have been many times where we’ve felt this exact same feeling. I remember recently reading JFK’s account of the Missile Crisis — it was like the world’s over. And I go to Newspapers.com and read the predictions. And what you notice is that people are wrong more than they’re right.
Sam: To reiterate your point — you don’t actually have to be that fast to pounce on certain things. The Model T came out, I think, around 1912 or 1916. The internet is something like 35 years old commercially — basically like a car company in 1940. So it’s really fascinating to read all these biographies and use Newspapers.com to see: what were the predictions, and how have they come true? I already know the answer, but I want to know what they were saying at the time. That’s my version of what you do with 2023 podcasts.
Jason: I love that. I didn’t know that site existed.
Sam: There’s also an X account I follow called Pessimists Archive. It’s a great one to follow. And the thing that’s a little bit interesting about right now, the time we’re in, is that there are so many people saying so many things — all wearing the expert uniform. Some people are experts, like there are experts in this world. But many people act and play as one based on their ability to communicate on platforms. And there’s just so much certainty layered into their suggestions and demands. It’s very healthy to go: every time you see “you must” — I always back up and go, probably not. The more forward they are about being certain and right about something, sort of the less interested I am in the short term. I’d rather stand back and see how it plays out.
Sam: At the end of the day, there’s plenty of opportunity in a lot of different areas. You don’t need to pounce on everything as it’s happening. In many cases it’s best to wait a little bit and see how things settle out. Think about all the companies that began to implement AI stuff early on, and then OpenAI just wiped them out in a lot of ways. When you build on other people’s platforms, you’re very much at risk of things changing — tectonic plates shifting very quickly. You might have been better off waiting and seeing how things shake out.
Closing [01:10:00]
Sam: Anyway, I wanted you to come on here and just talk, because I’ve read your work for years, I’ve been a fan of yours for years. Someone told me you should just ask people what’s interesting to them. That’s what I wanted to do with you, because you’re an interesting person and I respect your opinion on so many things. I appreciate you just coming on and riffing with me and telling me what’s intriguing to you. It’s been very valuable for me just to see how you think and what grabs your attention.
Jason: Thanks for the invitation. It was really fun. As I mentioned earlier, I just want to make useful things. And hopefully this is a useful conversation for us and for anyone listening. So thanks for inviting me, it was a real pleasure.
Sam: All right, that’s the pod.