25 Years Of Founder WISDOM In 55 Minutes (ft. Jason Fried)

My job as a founder, it's to inject risk into the business. You can get away with certain things that other people simply can't because you own the damn place.

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 this result, but it still made me sad. I tweeted out, I said, 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 I think I even said you can, but you can only invest $10,000 into that business. Or you can invest actively. You can't really buy the index, but you can invest actively and do whatever you want. Some days maybe, or some years maybe you'll get plus 50%. Some years you're going to get minus 50%. Which would you choose? Option A or B? 40% of my 300,000 followers selected option B, and you replied and you said option A all day, easy. What, why did you select that?

Well, to get 7.5%, like with no effort and you're guaranteed, it's a no-brainer. It's an absolute no-brainer for me. I mean, now I've got a business, I have a lot of risk in my own business, so that might be part of it as well. Like I don't, I have all the risk there. So let me ask you this. Were you intending this to be like someone who's 21 years old, straight outta school, never invested before, has nothing else going on? Or is it just like at any point in your life?

I think at any point in your life, that's still the right decision.

I still turn that switch on in a second. Yeah. That's a ridiculous return in a good way and a consistent return. I mean, the way that would compound over time would be fantastic. And there's nothing boring about that. That's an incredible— I mean, it's boring actually, but also an incredible thing. So yeah. What would you think the survey was going to produce? Were you surprised by the ratio or?

I'm surprised that the average Joe, I mean, and my followers are probably above the average Joe in terms of income, maybe IQ, maybe not. I don't know, but for their, they're typically a higher looks for sure. They're, they're up there. They're very good looking. It's a very high, like I would imagine it's a high educated coastal crowd. And, and so anyway, I, I would have thought that they would have seen the fallacy that they probably can't beat all the others. Particularly the other people who have a much better advantage. And so the idea that although everyone else fails at getting this return, I, in my little office, in part-time with just me, can somehow beat all the others. And I, and I thought that that was shocking to me, that, that they thought that they were exceptional at that. That's what I was surprised at.

Yeah, well, that's pretty common. I think everyone thinks they're exceptional in some way. I mean, the thing people don't take into consideration is, is is, uh, is risk. So like, they, they might go, well, if I just buy Nvidia or Apple or whatever, or Shopify— I mean, and the thing is, in the short term, you almost certainly can. Over the next 2 or 3 years, you get lucky, pick one, pick a winner. But the rest of your life, that's the question.

So 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, and I randomly met a bunch of people who work at hedge funds. And I'm like, hey, like, I'm not like a competitor. You don't ever have to worry about me. I'm just like a passionate, interesting, uh, interested person. Can I just like see your office and just like, can I just sit at your computer and you just show me your software? And like, I just want to see like what you do all day. And you go to some of these offices and, you know, I would have thought like they were like Wolf of Wall Street where it's like buzzing and like the phones are ringing. It's really just a bunch. It's pretty quiet. And it's usually just like a bunch of nerds, like looking at a computer screen, but they got like 4 screens and they've got like incredibly complicated software and the average Joe is getting paid hundreds of thousands, sometimes tens of millions of dollars to be good at this one thing. And then I think about like, how is like Bobby Lee in whatever, Missouri, where I'm from on his Robinhood app possibly going to have like an edge on all these resources and these people with all these resources, they're still not that good. You know, I talked to a guy who worked at Bridgewater recently and I was like, Bridgewater, I've read up 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 that 1,500 employees, tens of billions or hundreds of billions under assets, you're all paid like the best there is. You still can't beat it. And so that kind of like, that's kind of where I'm coming from.

Yeah. It's also like Vegas. You go to Vegas and you know, you've got, you're on a hot streak. For 30 minutes. And you know, the longer you play, the less you're going to win. You're going to lose. Like you're going to lose. The house is going to win over the long term. So people, I think, have this idea of short-term performance in the market, feeling like I can do this forever. Just like in Vegas, you can't do that forever and you will begin to lose. And the same thing is true in the market. So yeah, lock it in.

What's this thing about loosening the grip on the stick?

Oh yeah. So I got a drum set recently. I used to kind of want to play drums. I kind of did for a little bit. I stopped for many years and I kind of just picked it up recently. My office is a bit of a mess, so I got to find a better place for it. But right now it's in the corner. And as I've been playing, I learned this very quick lesson. And actually it's true when I try to learn how to play guitar. I say try again because I'm not very good at these things, but I enjoy them. Is 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 kind of where I'm coming from here.

I used to play drums. I know what you're talking about.

Okay. So you hold the stick 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 and there's no finesse. And it kind of dawned on me recently that this is very, very true for most things in life, I think, especially business. I kind of, some ways I feel silly always bringing this back to business. Anyway, I realized that like by simply loosening my grip a bit, by lightening up, um, you end up having better control, you end up playing better, you end up working better, you can do it longer, um, and you allow other things to happen that weren't possible when you're gripping so tightly. I think this is true for business. I think when you're starting a business, you have a really tight grip on things typically, 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. And I run into a lot of entrepreneurs who I think have not learned how to let go of the stick.

I think that that's also a young man's thing to do, right? Like, you learn this with age.

What are you saying? What do you— what are you trying to say?

Well, what I'm saying is you, you, you have a couple decades of, uh, of experience and, and like, and so do I. And I think that as I'm getting older, which I'm not old, but neither are you, I'm learning it is okay to loosen up. And that's what they say a lot about, uh, men. They say, oh well, he used to be intense, but he's mellowed out, he's mellowed out. And that's usually what they're referring to.

Yes, that's a good point. Yeah, the mellowing out. Um, it's nice though, in, in a different realm of something, to, to find a metaphor. And in my head now, I am kind of thinking about this, like, loosen, like, loosen up your grip a little bit.

In what parts of life?

Well, I'd say business. I would say also, like, with my kids a little bit. I, I would say there's a way where I kind of wanted, wanted them to do certain things a certain way, and I— and it's just, it creates this conflict. Like, they're their own people, I'm my own person, um, and, you know, I want to encourage them to do certain things in a certain way, but I also gotta loosen up a little bit around that and let them find their own way. And that's something I kind of learned pretty early in parenting. So there's a lot of things, but in general, I just feel better when I'm not gripping things so tightly. And when I look out there on Twitter or anywhere, LinkedIn or whatever, and I'm looking at these business stories, I'm reading a lot of grip. I'm reading a lot of tension. That, that, you know, people are trying to over-optimize and paying attention to every last little thing in a way where I feel like just loosen up a little bit, like pay attention to a few things that matter and let, let it, let things just be a little bit more.

All right. Look, the question that Sean and I get asked constantly is what skill set did we develop early on in our careers that kind of changed our business career? And that's an easy answer. It's copywriting. We've talked about copywriting and how it's changed our lives constantly on this podcast. And we give a ton of tips, a ton of techniques, a ton of frameworks throughout all the podcasts. Well, we decided to aggregate all of that into one simple document so you can read all of it. You can see how we've learned copywriting, but you can see the resources that we turn to on a daily basis. You can see the frameworks, the techniques we use. It's in a simple document. You can check it out in the link below. All right, now back to the show. The best example that I've experienced this in my real life is arguing with people. And so before it was like every word that I— like when I learned to talk, it was like, it was fight was the first word. Was the first thing that came out. You know, like my early words were I wanted to fight. And so if I met someone with a different political perspective, it was, you're wrong for these reasons, that you're really stupid for that. When I lived in San Francisco, I was significantly more combative than I am nowadays. As 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 also that it bleeds to other points of life, which is like, instead of someone saying something, when someone says something that I disagree with, it's more so instead of fighting, it's, uh, well, why do you feel that way? Uh, that, that's, that's a really interesting perspective. Tell me more about why you feel that way. And I think, 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 1 1 5 and I'll say, Well, I hope you have a really good day. And that's a little bit about how it's been where I just want to argue a bit less and I'll still catch myself arguing. But Dale Carnegie in this book, How to Win Influence— How to Win Friends and Influence People. He's got many famous lines, but one of the famous teachings is basically just don't argue with people because no party typically walks away happy or satisfied. And so loosening the grip for me is arguing less, where it's, I'm not even gonna judge you, and I'm just gonna— I can recognize that you think this way and I think this way, and it's cool.

It's a great example, actually. Uh, I hadn't thought about that, but that, that's another great example of just like holding on. It's not even holding on too tightly to a perspective, because you, you can have a perspective that you really believe in, but it's, it's, it's, you know, it's like, don't clench where you're not even able to listen. You know, I think that the point about like being too, uh, grippy is, is you're, you're, you're— it's like you're a spring under tension, and if someone says something to you that you disagree with, like, you're gonna boom, expand and like explode, right? Which is kind of what an argument can be, versus just already taking some of the tension out of that spring and just like bouncing with it and listening versus exploding out of it. I think that's a big difference.

Have you ever read— there's, there's this term, I'll have to figure out what the term is, but there's this term where astronauts go to space and they see the Earth from far away. And many of them have reported to have a life-changing perspective where they think to themselves, the fact that we're fighting over religion is ridiculous. The fact that we're fighting over borders is ridiculous. Now let's 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 like floating thing.

And it's like, monkeys with cars.

And like, yeah. And we see like this, this abyss. and then we're just this silly blue thing in the middle of it. And, and, and it's like a lot of astronauts say it changes their perspective and it mellows them out. And I think that when I read about that years ago, it kind of helped me calm down a little bit more to where you think not the, the stuff that I thought mattered doesn't matter. For example, I remember when COVID happened and I was like, we're never going to concerts ever again. And then 3 years later I'm like, fuck that. I forgot all about that. Do you know what I mean?

Totally. Have you, have you, uh, to that point about astronauts, have you, um, read that great passage from Carl Sagan, The Pale Blue Dot?

What's he say? No.

I mean, it's one of the most beautiful— I'm not going to say it because I want you to read it. I want you to have the experience of reading it. It's short. It's a paragraph. It is one of the most beautiful passages I've ever read, but it's, it's exactly kind of what you were talking about with the astronauts, like looking back at the Earth. It's all about all the things that have ever happened. I'm going to really generalize here because I want you to read the words, but all the things that have ever happened, every leader, every religion, every point of view, every argument, every whatever, right? Beautifully, in beautiful prose, happened on this speck of dust, basically. Or I think he calls it like a mote of dust. It's such a beautiful passage and it brings tears to my eyes. And I try to read it a few times a year because it's so right. It's so spot on, right? And it's exactly what you were talking about in the most beautiful poetic way, which is all the stuff that we're worried about, all these things, like very few of those things matter. Although of course they matter in your day-to-day life. So like they're real for you, but they really don't matter that much. And it's just a good reminder that, you know, all the things we're just so fired up about, who cares?

Well, it's a paradox of like caring by not caring. Why do you not like comparing this stuff to business? And afterwards, I'll tell you my reason why I think it's good. Yes.

So this is an undeveloped thought of mine that's been sort of on my mind, and I don't know if it's a good idea or not. So just run with me here. I'm going to kind of— this is undeveloped. It seems like every great lesson is then applied to business by someone. So for example, a Navy SEAL learns all the stuff in the military and they come and they like then consult for companies about how to like run teams or some great coach coaches a great team and then they come and they bring it to the business world. It's always like bringing it to the business world. And I'm like, why does the business world deserve the best lessons from things that are completely unrelated in many ways to business? But why does it always come to the business world? And the main reason is why, 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 it's advice that's applicable, but that it pays for the advice. 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 business because business sort of just is willing to pay for it and listen to it and sort of have this this, this, um, it's sort of insecure in a way. So like, it's, it wants to listen to the Navy SEALs, it wants to listen to the great double or NCAA coach, it wants to listen because it, it's insecure in its own way. Um, and also there's this, there's a sense of like, um, these other places and people, they know better than us, so we're gonna, we're gonna just, you know, bow down for their advice. And I don't— again, this is a little bit unformed, but it's something that just bugs me a little bit. I don't know, does that make any sense, or is it just a weird idea?

No, it makes sense. But my argument would be, instead of the image that you've had— you just painted is you've painted an upside-down triangle with all of this beautiful stuff draining down into this bad thing.

Thank you.

I would turn that, turn that upside down and say it all is going up to this amazing thing, and here's why. Because I think that 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. Maybe America will change. Maybe, maybe the rest of the world, the majority of the world will change. But I, I wouldn't bet on that happening anytime soon. Therefore, I think that capitalism and thus business building is the most practical way to manifest a dream or a reality. And oftentimes you could say, well, what about art? And I would agree with that. But at the end of the day, you're still making stuff that people want and you're still selling tickets. You're still trying to make some type of money off of your art so you can continue doing it. Or you're just going to have a rich person who funds you. So you are, are able to do it. And so my opinion, business is the most practical way to actually kick a dent in the world or to manifest a vision. And so I think of business as a very pa— like I'm very passionate about it being a little bit of a spiritual journey of like turning dreams into reality.

That's an optimistic point of view, which I do understand. Here's my question. If this thing called business is absorbing all of these lessons from all of these other realms, right? And they're all like either filtering down or filtering up, but they're filtering to And maybe I'm wrong about this, but why aren't the Navy SEALs asking CEOs for advice?

Well, sometimes they are. If you look at like, I don't know, maybe they are like, uh, Jack Welch's book Six Sigma. Like a lot of different types of organizations outside of business, like view that book. I don't really like that book, but they view it as like the rules of the game. Yeah.

Okay.

Yeah.

I might be uninformed in a sense of like what, who the military is listening to and who sports teams are. But there's something, it's like you would imagine this entity, this business thing that has absorbed everything would then be the definitive source of this wisdom. But I wonder, is it a one-way street or is it a two-way street?

And it seems very one-way to me. I think you're more right than you are wrong. That's for sure. It's definitely more one-way. Yeah. No, I just wanted to give one example, but I was, yeah, frankly, that's a nitpick example.

Totally. I don't know. Again, I don't know if this is a good idea or not. It's just, it's been sort of floating in my head for a bit. So it's fun to air these things out.

What was more fun, early days or late days of the company?

Oh man, that's a really good question. Um, they're very fun in very different ways. So I'm going to, it's a bit of a cop-out, but it's, it's true. Um, but they're fun in different ways. What's exciting about the early days is there's a certain energy that you can never capture again. Which is the, the, there's so much more unknown. Like you're, you're, you're starting from zero and you're building something and you don't know where it's going to be and where it's going to go and what's possible and what isn't and how long it's going to last and all those things. Now you don't know how long it's ever going to last in a sense, but there's this, there's this hope, there's this possibility, there's this birth and, you know, it's like, boom, we're out in the world and here we are. And this is an incredible thing. And that's super fun. And then you get a lot of new attention and you're kind of burst on the scene and that's exciting, really exciting. I think what's hard actually is the middle. We've gotten to a place now, having done this for 25 years, it's become really fun again in a different way. But I would say like 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 this sort of maintenance thing.

Were you big enough at 15 years where you're like, payroll's not an issue? Like, were you out of like any type of outside pressure where it was like, things are fine? So it's like, I feel weird that I'm complaining, but this feels weird. Yeah.

And I'm not really complaining about it, but yeah, yeah. It's more like, you know, Scott Belsky wrote a book called The Messy Middle.

Yeah, it's great.

I have not read the book actually, but I understand the idea of it and it's kind of what I'm trying to get at, which is the middle of it is, it's like, what do we want to be now and where do we want to go now? And are we going to be a big company? Are we going to stay a small company? There's all these opportunities that are surrounding us now and swirling around us versus when you're starting, you're just going, you're just moving. Then you get to this place where you're kind of evaluating. And now we're in this place where we're just sort of mellowed in a sense, to your point, although we're actually getting very ambitious again because we have this sense of we've been doing this so long now that if we took some crazy bets or made, placed some crazy bets and it just totally all fell apart, I don't want that to happen, but I'd be okay with that too. We're at a place where it's like we've done plenty and we've had an incredible run. And if it all ended with a bang because we tried some crazy stuff that didn't work, I'd be okay with that too. So I feel like I'm at that place now where I wouldn't have been at 15 years, if that makes any sense.

What's your sense?

I mean, you've started a bunch of stuff.

My sense is that, um, so none of my things have, uh, have been as big as yours, but they've been big enough where we've had dozens or, you know, 50, 60 employees and it, it, we got outside of the like existential crisis moment where it's like things are working. My, uh, and everyone talks about focus. Focus is a very common thing and it's something I firmly believe in. But as someone who likes to make things for my skillset, a company outside, like maybe let's say $3 million in revenue or maybe, maybe $5 million in revenue. I've noticed consistently at $5 million in revenue and like 15 employees, something like that. I'm like, I don't know what to do with my hands. Like I'm just sitting here. Like what, how do, what do I do? I feel useless and I feel like sometimes a general behind the scenes just pointing. And I've noticed something that I, I, I really dislike, but I think it's normal, is a company ebbs and flows. And I've noticed that this ebb and flow carries over to the rest of my life where, uh, I just had a child and I'm like, I'm in this, uh, quiet time for a moment where I have to be present. Whereas there's other times where you're dating or something like that and you're like, I'm in, I'm, I'm in war mode a little bit where it's like there's, it's action constantly. Or like I'm on top of my game and I gotta be on top of my game. Same with business where it's like we're launching this new thing, we're, we're out fighting, uh, with the troops, we're in the trenches. And then there's other times, sometimes this I think can last for years maybe, where it's just like we're just doing the same thing over and over and over again. And that period can be a little depressing even though everything is going well. It's a very saddening period because you lack action. Uh, it's basically like what they say with a lot of great investors. Uh, I think, uh, uh, Mohnish said this on our, uh, Pabrai on our last podcast, he was like, if you can watch paint dry, you're going to be a good investor. The problem with that for a lot of entrepreneurs or a lot of like go-getters is that's a really sad place to be in. Even though everything is going well, it's really uncomfortable to be in that feeling. And so have you guys had a lot of, have you had a lot where you're like, man, I just got to kind of unfortunately have to do nothing for maybe years?

Yeah, I can totally identify with that. And I think what you're getting at with entrepreneurs is that what you're describing is in the early days, you are very important as a founder.

Yeah.

Then there's a point where you build an organization and then the organization is able to, in some ways, in a good way, run without you to some degree. And at that point you kind of feel a little bit less valuable.

Yeah.

To your own thing that you made. It's a good thing, but for you, it's a good thing because it means there's some stability and you're not the bottleneck and you're not the only person that matters here anymore, obviously. But for you personally, it feels a little bit like you've become detached from this thing that you made and you're now further away typically from the creation phase and now you're more in the maintenance phase of something and you're dealing with internal politics and personalities and hiring and you've got some great people who just left and now you got to find new people and the culture's changing and That's a pretty tumultuous, turbulent time for a founder. And I've gone through that many times and it comes and it goes. What I've found is that, what I've kind of discovered actually recently is that my job as the founder, I'm still a founder. I still started this company. I'm still in it 25 years. My job as a founder, what I've realized is it's to inject risk into the business. Most people, everyone pretty much at your company's job is to manage risk to some degree, to keep their job, to not push too hard or too far. Ultimately, um, you can get away with certain things that other people simply can't because you own the damn place. You are the original person. So what I've found a lot more joy and, and, um, and excitement in is, is revisiting this idea of injecting risk. And for us, that means—

and by the way, I don't think you could change that. I think like for a long time I was like, why aren't these people taking risks? I got to force them. And I'm like, there you go. It's impossible. That's impossible to change.

Even if you hire a great, great CEO to replace you as CEO, like they're— they just don't have that. They might be an incredible CEO, great executive executing things, trains run on time. Incredible. But there's that thing that's present in a founder simply because they were there from the beginning. That they have an extra ounce of— it's not even that they're, they're not better than they just have an extra ounce of latitude that allows them to take risks that nobody's going to say no to. Maybe if you have a board, maybe someone's going to say no, but they'll still give you more latitude than a hired hand, basically, in a sense. So my sense is the way I found to return to this sort of flow versus the ebb is like, is to inject more risk, which for us means we're going to build a lot more products. Like this year we're going to do 4 products. We're going to begin, we're about to start working on 2 products simultaneously, which we've never done before. We've never built 2 things at the same time. And like this, there's a lot of stuff going on. We got different models. We got once, we got SaaS, we got all these things. We're going to do multiple versions of multiple things and different business models. And we're really off balance in a really healthy way at the moment. Because like we're doing a bunch of new stuff and that gets me excited. Now it makes some people internally nervous, understandably so. It's like, well, this is different now. We're kind of off balance a little bit and we're trying new things, 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 bored. That's not a good—

that's not a good thing for my professional life or for my main company. That's like the main 9-to-5 thing for Hampton. I've not, I do inject risk, but I have a CEO. And so, uh, I try to, I have to like respect, uh, I gotta respect that relationship. And so, yes, on my nights and weekends, I, um, I created a new website for fun. I created this website called Sam's List. It's samslist.co.

Nice.

And the reason I did it was I tweeted out like, who's got an accountant that they love? Because I just needed an accountant for something. Yeah, I got like 300 replies and I was like, wait, something's interesting here because this tweet got so many bookmarks. Like a lot of people bookmark it and someone was like, oh, I'm saving this for later to find an accountant. So I was like, this is interesting. So I spent a few months calling every accountant on the list, finding out how much they charged, what services they provide, what services they don't provide, who the ideal client is, who isn't the ideal client, whatever. And then I created a website called Sam's List where I reviewed, or I, uh, like put all the information from all of my research for all these accountants, created this website. I think I got 8,000 people to come in the first week. And then I, uh, started figuring out how to monetize it. And so this month, the first month it's been live, it's May 22nd when we're filming this, I think it's done $20,000 this month. And the $20,000 that I've made from that is more dopamine than, let's say, $1 million a month or $2 million a month that I've gotten from other things. It's a total rush and I love it.

Why is it— why do you think that— why do you think that's so exciting for you?

It's a total rush because what started— it's so fun. It's so fun for things that start as silly jokes, like, uh, like just stupid. Like the calcul— like the, the logo that we have is a calculator that has 3 numbers and a Q, and it looks like Clippy. It looks like Clippy from Microsoft, like waving at you. It looks like Mickey Mouse. And I just used ChatGPT. I said, make a logo that looks like Clippy, but it's a calculator. And it's so fun to take silly, jokey stuff and turn it into real things that actually solve problems. And I find that to be almost like part trolling, part like shit-eating grin, like scheming. Like, I love that. Like, isn't it? Would it be hilarious if we made this a thing? And then actually seeing it become a thing, I find to be so exciting. I also think that when you're, when you have a silly idea, even if it's like a serious idea and you start seeing customers truly like it, that's a very invigorating feeling.

It's the best. And we have this internal saying, we don't say it that much. We've, I've said it before and we kind of try to feel it, which is that cool wears off, but useful never does. And what you've made is something that's useful. And that is one of the most beautiful things I think you can do for humanity is to make something useful. Um, and, and to have fun with it and to screw around and not like take it so seriously. This is going back to the thing, your, your grip is loose on this. You know, you're having fun with it. You asked ChatGPT to make a logo and you're goofing around and the name is just your name. It's like, it's just have some fun. And, and 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 that you have fun doing, things that don't feel hard. You don't need to pile up and collect only hard things. And so while some of your business ideas might be harder to pull off for other reasons, this one is so lighthearted and easy. It's healthy. It's good for you. And you rediscover like why you do this sort of stuff. And it's also fun. I think there's something probably, I'm guessing, there's something probably in this that like, you're like, I did this by myself.

Yeah.

That's like the feeling of accomplishment and go, I, you know, I can still, I can still do something by myself, like really by myself. And that's useful is, is, is very rewarding and hard to come by sometimes when we all think we need to have partners and co-founders and teams and stuff to pull things off.

Do you and your partner get along like beautifully?

We get along really well. We're not like, we're friends, but we don't see each other very often. We live in the same town and we don't see each other. I see him once every, I don't know, couple months. We're very good partners and we're friendly, but we just don't, we don't hang out. Like our families don't hang out. It's not that we wouldn't enjoy it.

We just like, we just don't. There was a study where they looked at the most common reasons why couples get divorced. The most common reason was contempt and the most common, the most common reason for divorce was contempt. The most common reason for staying together was you admired the other person.

Oh, I hadn't heard that, but it resonates. Like resentment is just bad. And I think a lot of business partners resent each other actually. Have you, you've been in business with others, I'm assuming?

Yeah, I've got, uh, the most, 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.

What feels different about it?

So when we first started together, we invested in startups together and we had a great time. And he previously helped me with my old company, The Hustle. I cold emailed him and he was like, hey, if you're in New York tomorrow, just stop by the office and we could talk. And I was like, yeah, I'll be there. And I like flew out there and like hung out with him. And that's how we became friends. And then we invested in startups together. And then I was like, I took like a really formal conversation with him. I was like, Joe, I love working with you. Something I did with my wife early in our relationship when we were like thinking like, hey, is this something that we want to like make real and like get married and have a family? And I sat down with my wife and I was like, let's just like walk through our life values and like what type of life do we want to have? And let's see if like they kind of align and that's okay if things change eventually, but let's just say, let's just see if the direction is similar. And so I sat down with Joe and we said, hey, let's just outline like what sacrifices are you willing to make? What sacrifices are you not willing to make? What's a perfect day look like for you? What are you driven by? And like, for example, for me, I was like, you know, I'm driven by ego. Like, I, it bothers me that people think I'm not good enough. So like, I always want to prove that I'm as good as I think I am, or I'm driven by money. I was like, I work only 40 hours a week. I don't really want to work more than that. I'm not willing to sacrifice traveling. I'm not going to like get outta my house often if I have a family. And he like named all of his things and we looked at the, all the things and we're like, how much money do you want to have? How much money do I want to have? We looked at all of the things and we're like, uh, for everything that is agreed upon, awesome. For everything that's not agreed upon, do we think that that's like a deal breaker? And we, they weren't. And we were like, cool. We like did a really good job of being very honest upfront about our wishes. And now it's much easier to address like any issues we have because it's like, hey, you, he'll be like, hey, we gotta get this done. And I was like, yeah, but I, but he'll be like, but you told me that you don't wanna like grind on a Saturday, so I'm not even gonna ask you. It's all good. We agreed to this, things like that. And that makes the relationship really nice is that we respect one another and we had those conversations super early on.

Do you feel like the list or the conversations you had about that turn out to be true? Like, are those really the things that, that you guys share together, or is that sort of what you imagined you would share?

Yeah, for example, for, for the money, let's just do the money one. That's a really easy one. We actually shared each other's personal finances with each other.

And interesting.

Yeah, we were like super transparent. We're like, here's all of our finances, uh, what matters. Like, I would like to go here one day, where would you like to go? It's like, all right, well, to go there We're going to be like, let's say that my goal is less than your goal. Let's hit your goal then. And if we need to hit your goal, here's maybe what the numbers would need to look like and here's what we'd have to make. So like that, you know, is that like something we both agree upon? Do you know what I mean? Like we were very transparent with each other.

That's wild. I mean, this is, I know you and I were talking on Twitter a little bit about like how I'm super uncomfortable talking about money and you're like sharing your personal finances with your founder and kind of, it's, it's interesting.

Wait, you don't do that with your partner? You don't do that with your partner? Well, your guys' finances are probably so tied together, but you don't—

Oh, they are tied together. I mean, yeah, basically all of our, essentially the vast majority of our net worth is tied into our business. So we know what our distributions are and all that stuff. But yeah, we don't talk about that ever. But it's interesting, also, you're Midwesterner, I'm a Midwesterner. I feel like my thing is don't talk about it. I don't know why it's ingrained in me. Were you, were you like that at one point? Or did you change?

Or I was always open about it because I saw my family like that. And I was like, that's so unhelpful for me because you're not telling me, you're not giving me a roadmap. You're not, I don't have anything to strive for because I don't even know what's possible. My father owned a produce brokerage company, which like, uh, it's like a small business, but they sell like, let's just say over the course of his 30 or 20 year career, he sold like $150 million worth of onions. But like, I'm like, how much is a lot of money? Is a lot of money like $50 grand a year or like $300,000 a year? Like, I have no clue about this. And so I always regretted that, that they weren't open with me. And so I was like, I'm just going to be open about it.

It's so interesting. My folks never talked about money. I don't, still to this day, don't know if they're middle class, wealthy. I don't really know. You're kidding me.

Do you really? You have no idea. That's weird. Do you support them?

I have supported them. I gave them a big chunk of money at one point, but They regretfully took it. They didn't really want it. Then I don't think they need it. And I think I'm going to get it back when they pass kind of thing. They're not going to use it. They've always been very frugal. We don't talk about it. My dad was an entrepreneur, worked for himself.

Like a small business owner?

He was a trader. So he traded stocks on his own. He wasn't a broker. I think he started out as a broker for a little bit, but then he was on his own, individual investor basically. I think he did well for a while. I think he didn't do well for a while. I think, you know, that's, that's a tough road in a lot of ways. Um, he wasn't a day trader, but there wasn't anything we couldn't have, but we also didn't strive for anything that we couldn't afford. It just, I don't really know. My parents have always been careful with this. So I, I kind of absorbed that, like, just don't really talk about it. And, um, it didn't limit me though. It's not like I, I just felt like we, we were, everything was sort of fine is how it felt to me.

What are you going to do with your, what are you going to do with your kids?

I struggle with this. Like, my parents never really talked about it. We don't talk about it, but we certainly act differently than my parents did growing up. We own a few homes, we have a couple nice things. So it's kind of obvious that we can afford things and do things, but we just don't, we haven't talked about it.

I think that's an incredibly Midwestern and an incredibly more traditional, older set of values. My family had very Midwestern values, and I think a lot of those values are great. Hard work, don't complain, don't make people work for you. Like I remember going to like a restaurant and like we ordered a pizza and they brought us like a chicken salad and I'm like, we're not going to inconvenience you, whatever, just give me it. Uh, like, I'll eat that. Yeah, exactly. Yeah, that's like the attitude.

I've never sent a dish back in my life.

Not in a million years.

Not ever.

Not in a million years.

Whatever.

Yeah. And so like, I actually think some of those values are great. I think there's many other values that are like— I don't like using this word because it's too loaded, but toxic, bad. Uh, there are a lot of values that are bad. For example, I think the stoicism that Midwesterners tend to have, that you definitely have, I think that it's gotten you to where you wanted to go, uh, in a traditional success, uh, perspective, but also like not being transparent with certain people. I think I just don't want my family to be left wanting more when I'm gone in the sense of like, I wish that they were more open with me. For example, I've not seen photos of my family really when they were younger, or like, I don't have any—

your parents, you mean?

Yeah, my parents. When my parents were younger, I'm like, and I don't even know their grandparents' name. I don't know. I had to do 23andMe because I'm like, when I asked them what my heritage was, they would just go, we're white. I'm like, yes. Yeah. Okay. But what flavor? Like, come on. I need some more. And so, or, or I had to do ancestry.com in order to understand like who my grandparents were. Like, what are you guys hiding? And I, turns out I found out that an uncle is actually, uh, my grandmother was married previously. And I'm like, why didn't you guys tell me this? And they're like, oh, we didn't want to bring it up. You know, like little things, like little things like that. And I'm like, that's weird. Just like, just discuss it.

Just tell me.

Yeah. Right. That's weird. Uh, so anyway, I think that is actually bad though. And I pray that I don't fall into that, into that trap. And so that's why with my family, I've been overly transparent with a lot of things. Uh, and I just think that that like lightens, lightens things up a little bit.

I admire that actually. And this is something I actually also admire about David. I'm sure you wouldn't mind me telling you this. David used to, when we were in Chicago, when we had an office, he used to drive to work in incredibly fancy cars. And my Midwestern sensibility is like, "Dude, don't do that." He's like, "Why not?" I'm like, my sense was like, "It sends a weird message." And he's like, "What's the message? I mean, everyone knows, everyone here who works, they they know we're doing well. Like, why would I hide that from you?

I agree with you on that one, by the way.

And it's so funny because he's right, I think.

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 just because of how I was raised and how I was brought up and the imagined messages. Like, the whole point is like, I'm imagining that everyone's looking at that and going, 'What an asshole.' It's like, most people probably don't care. They don't care. They know the score. They're fine with it. And if they're not, that's their problem. David's point is like, if they have a problem with me driving a nice car, that's their problem. It's not my problem. I've earned this. I enjoy this car. I buy this car because I like the car. I'm not going to hide the car. And he's right. But I just have a hard time with it still. Not anymore with him. This is way back in the early years. But it still is something that's in there. There's a residual like struggle with that degree of honesty around money in a similar way that people are like, you know, in America, like, who'd you vote for? Like, I don't talk about who I voted for.

Same.

I think Chris Rock has a great bit on that. It's, it's so funny.

Um, like when I see someone with a, with a political bumper sticker on their car, I'm like, you're insane. You're, you're a crazy person. Yeah.

And they're probably like, why? I like this guy or I like that guy or I like her. It's like, what, why am I have to, why do I have to hide my point of view? And they're right too. So deep down, your point of view is healthier. I still have a hard time with it, and that's probably my problem, or maybe it's not. I don't really know. I don't really know. It's very interesting.

Do you want to change or do you not care?

Well, I think the truth is my kids have a, or at least my son who's older, my daughter's 5, she doesn't recognize any of this stuff yet, but my son does. And my son's really into, it seems to be into expensive things. He has this craving for expensive things. So, I mean, he's got to know what's going on to some degree. He's not an idiot. Do I want to sit him down and go, "Hey son, we've got this and we've got that." And that isn't how I would 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." And that's kind of how I treat, for example, the house thing. When I renovate a nice old house and I make it better, like, it's our house, but it's also all of our friends' house. The free people are free to stay there as much as they want, visit as much as they want. I have this property in Wisconsin, this old farmhouse, 160 acres. It's a beautiful piece of land. I've been working on it for years. My friends use it more than I use it. I don't use it anymore. I'm not even around there. My friends can just go up there whenever they want and use it. So it's, it's about like we're fortunate, clearly fortunate and lucky. And a big part of this is you want to share these things. There's, there's, you're not fortunate if you hoard the things, then there's something I think kind of wrong about it from my point of view. So share as much as you can, share these experiences with other people. And, uh, and, and we're fortunate, you know, that's kind of how I sort of left it at this point.

I don't know.

We'll see.

Um, the, the thing that I tell my, uh, friends and family, um, is I try to let them know, I don't, I, and this is something that I couldn't grasp earlier on in my career. I refused to admit this one thing, which was luck is real. And it has played such an important part of any type of financial, uh, uh, like just meeting the woman who you spend your life with. Like just the fact that we are in the same place at the same time. Luck is such a bigger component than I ever would've been willing to admit years ago. And I think that what I'll explain to my children is like, look, I worked hard, but I frankly didn't work harder than many other people.

That's right.

I'm smart, but I'm not that much smarter, if at all, than the average person. The truth is, is that I worked hard, I had a skill, but I got like 50% of luck was like part of that, or maybe even more than 50%. Luck is such a huge, huge component. And I hope that I can put that on my family to realize that luck was real. It just happened to work out because some timing thing worked out. Like, let's say you started a business and you surged during COVID You're like, dude, I just kicked ass because something I had nothing, which I did. Our business killed it during COVID I'm like, I didn't know that was going to happen. That was just total luck. Or, you know what I mean? Like things like that. It's absolutely real. And I need, and I hope my family will understand that.

100% with you, and I think it's way more than 50%. I mean, all the way back to you didn't choose your parents, you didn't choose anything, right? You didn't choose your mind. How'd you become the kind of person who is the way you are? There's a million inputs, a billion inputs that you don't know about, all the things. One of the— I don't— regret's too strong a word, but one of the things I regret most in my career is Getting on stage at Startup School. So this is like, um, Y Combinator Startup School years ago. I forget when I was invited to speak. I was only invited once because I was pretty anti-raising money.

Yeah, I was going to say, I thought, I thought you're like the opposite of their ethos.

I, I was, but, uh, Paul was kind enough to ask me to come up on stage and, and give a talk.

But you and Paul seem quite similar, to be honest.

Well, I appreciate that. I mean, I, I have a lot of admiration for his ability to, to put ideas together and think things through and what he's built. But he invited me on stage and there was a question from the audience about luck. Someone was like, "Do you believe in luck?" I'm like, "Hell no. I don't believe in luck." Wow. And I was such a prick.

How old were you?

Early, mid-20s. Mid-20s, I think it was, whenever it was. And I was just such a prick, but a young punk prick, kind of like— And it's so embarrassing, but a lot of things are. You look back on poetry you wrote in college, you're like, oh my God, I wrote that or whatever, like whatever it is. And it's like you just realize that's part of growing up is totally misunderstanding the world and your position in it. And then hopefully, hopefully you get to the place in your world where you develop a bit more and you have some self-reflection and you can call yourself out on the bullshit that you thought. But also that's who you were at the time. And that's, That's that.

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's that mean?

Right now, this is like in the AI world we're in right now. Every once in a while, like in my For You feed in Twitter, it's like, 10 things you got to know or you're falling behind. It's like, it's just like this, everyone's falling behind. Meanwhile, this thing is brand new and moving faster than any human can pay attention. Like, I just keep seeing these stories about like, if you don't know this and they're doing that, and if you're not on top of this, it's like, no, probably doesn't matter that much. Um, and all the things that if you would have read that feed a year ago that you were supposed to know, uh, it wouldn't have mattered that much if you didn't. Most things. Some things would be handy to know, but it probably wouldn't have mattered that much if you started now instead or waited a year in some cases. One of the things I was doing for a while, I'm not doing anymore, but I should go back to doing it again. This is actually easier to do during the pandemic, was to go back. And so today is May 22nd, 2024, is to go back and all the podcasts I listen to and listen to May 22nd, 2023. So listen to podcasts that are a year old. And during the pandemic, it was great because you hear all these experts talking about this and talking about that, and everyone's so certain of everything. And you go back and listen, you're like, man, we were so wrong about so many things. And so many of the things we were worried about never happened anyway. And this political issue and that political issue. And if this guy gets in office, this is going to happen. If they get in office, this is going to happen. Turns out very, very few things actually happened. And it's really a nice exercise to go back and listen to old podcasts and old interviews of substance and realize that like there's some stuff that was right, some stuff that was wrong, but man, the sense of urgency in these podcasts is so misplaced because 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 recutting itself and resharpening itself every few months. So that's what I'm saying. I try to stay a bit out of things. I don't want to be on the edge of things. I like to let things settle in a little bit more before I really start to dig in.

Do you read any biographies?

A few. I've read a few. I really love the idea of biographies. I have a hard time reading long books. Yeah. And most biographies tend to be very long.

I've got like a limit where it's like 500 pages or less. Yes. But I'll do long, I'll do a long one every once in a while. But I, and I read a fair bit, not because I'm in a competition, it's just an hour a night is typically a book a week. And I read a lot of biographies. I like business biographies. I love history. So like a lot of the World War II leaders, a lot of the American like titans of industry, a lot of just random people. I love biographies. And I have this process of what I do. I've got this spreadsheet where if I only read on Kindle and anytime I see something interesting, I highlight it. And at the end of the book, I'll like insert, I'll create a timeline. Here's where they were born, here's where they died. And then anything that I highlighted that happened in this year, that happened in this year. And then what I do is I go to this website called newspapers.com. Newspapers.com has archived pretty much every newspaper ever back until, back until like the 1600s. And what I like to do is let's say, um, I read this biography about, uh, Ted Turner. Ted Turner is the guy who started CNN. He was a fascinating guy to me, or let's actually use landowner in the United States. Biggest landowner. Yeah. And he's done a lot of fascinating things. And the reason why I use newspapers.com is I like to go back to my Kindle and my spreadsheet and I see, all right, in this year he decided that he wanted to buy land. You know, I'm going to 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. And like, did he say it? Like, for example, uh, maybe he'll say like, one day I hope to own like 5,000 acres. Turns out he owns millions and millions and millions of acres. And so I like to read what the predictions were as well as what the people were saying about the person at the time. So you don't get revisionist history. And what you notice when you do this is there's oftentimes that you'll read a biography and you'll think this was obvious that this person was going to do this, or they're ob— who wouldn't have predicted that this was going to happen? And, or here's another example. Uh, World War II, Churchill was like, basically he was like, the, the world's going to end. Like we are going to die. The world's over. Uh, we felt that way during COVID but if you read a lot of history, there's been many times where we have felt this exact same feeling and we had this exact same prediction. You know, I remember I, I recently read JFK's book and like with the Cuban Missile Crisis, it was like the world's over. And I go to newspaper.com and I'll go and read what the predictions are. And what you notice is that people are wrong more than they're right. And so what you're saying about things moving too fast, I, I, I, I read, uh, Henry Ford's biography about cars. Or a Henry Ford biography. And I, so I got interested in cars and I went and read like what people were saying in 1912 when the Model T was coming out. And like the predictions are just ridiculous. And it's so funny that you don't, to reiterate on your point, you don't actually have to be that fast to pounce on certain things. It's really quite fascinating. And to put this in perspective, the Ford came out with the Model T, I think in 1912 or 1916. 2015. So the internet right now is something like 30 years old. Uh, so that is basically like, how old would you say the internet is? Or like the modern day internet?

The commercial internet. Yeah. Like '95, '96 is when like, you know, really Mozilla or Netscape kind of came out and really kind of made it happen.

It's basically, basically, it's older than that because it's a research thing.

But yeah, commercially. Yeah. 35 years.

It's basically like a car company in 1940. Uh, do you know what I mean? Yeah, yeah, yeah. And so what's really fascinating is to like read all these biographies and use newspaper.com. It's one of my favorite things to use and to see what are interesting, uh, predictions and how have they come true. Because I already know the answer, but I want to know what were they saying at the time. And so that's my version of what you do with 2023's podcast.

I love that. That's— I didn't know that site existed too. That, that's fascinating. It— there's, um uh, uh, an X account I follow called like Pessimists Archive or something like that.

I love that one.

It's a great, it's a great one to follow. And just, you know, like, and the thing is, is the thing that's a little bit interesting about right now, the time we're in is that, um, there's 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 just their ability to communicate on platforms. And, uh, there's just so much, um, certainty, uh, layered into their suggestions and requirements and requests and demands that it's just, it's very healthy to go, every time you see that, every time there's like a, you must, I, I always back off and go, probably not. Like the more forward they are about being certain and right about something, sort of the less interested I am in the short term. And I'd rather just sort of stand back and see how it all plays out. And At the end of the day, you know, there's plenty of opportunity in a lot of different areas. You don't need to just pounce on everything as it's happening. And in many cases, it's best to wait a little bit and see how things settle out. I mean, I just think about like with AI, like all the companies that began to implement AI stuff early on and then OpenAI has just like wiped them out in a lot of ways for a lot of different reasons. And when you build on other people's platforms, you're very, 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. So anyway, who knows.

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. I've seen you do a bunch of interviews, and I just wanted— someone told me, uh, this guy named Dylan just said you should just ask people what's interesting to them. And that's what I wanted to do, uh, with you because you're an interesting person and I respect your opinion on so many things. And so I appreciate you just coming on and just riffing with me and just telling me what's intriguing been a lot of— it's been very valuable for me just to see how you think and what grabs your attention.

Well, thanks for the invitation. It was really fun. And as I mentioned earlier, I just, I want to make useful things and hopefully this is a useful conversation for us and for anyone listening. So thanks for inviting me and it was a real pleasure.

All right. That's the pod.