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 dangles. I feel like I could rule the world and know I could be what I want to. I put my all in it like a day's all. Alright, 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 could 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 did you select that? Well, to get 7.5% with no effort and you're guaranteed, it's a no-brainer. It's absolutely no-brainer for me.
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. I have all the risk there. So let me ask you this, were you intending this to be someone who's 21 years old, straight out of 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, would you think that the survey was going to produce? Did you were you surprised by the ratio?
I'm surprised that the average show, I mean, in my followers are probably above the average show in terms of income. Maybe IQ, maybe not, I don't know, but they're typically a higher end. It looks, for sure, they're up there. They're very good. It's a very high, I would imagine it's a high educated, coastal crowd. And so anyway, 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 greater risk.
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 thought that that was shocking to me 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 risk.
So like they, they might go off if I just buy in video or Apple or whatever or Shopify, I mean, and the thing is in the short term, you almost certainly can. Over the next two or three years, you get lucky, pick one, pick a winner, but the rest of your life, that's the question. All right, everyone, a quick break. When you're starting a company, you basically duct tape together a ton of different pieces of software and different platforms.
And it's basically impossible to stay on top of everything and a ton of stuff breaks and it ruins things that you forgot that you even duct tape together. And that's why I use HubSpot for all of my projects because it does it all. So I don't actually have to use any duct tape, which means it doesn't break.
I can build my website on HubSpot. I can write my blog posts on HubSpot. I can collect leads on HubSpot. And then my salespeople can put those leads into the CRM and they can track those leads and build relationships with them. And it just makes life much easier. So if you're interested and want to say goodbye to the duct tape, trust me, you guys have to check it out HubSpot.com. It's free to get started. Now back to the pot.
So here's what I've done lately. I've been spending time in New York because I've got family here. And I call the email that did call outreach and I randomly met a bunch of people who work at hedge funds. And I'm like, hey, I'm not like a competitor. You don't ever have to worry about me. I'm just like a passionate, interesting, 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 wof a 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 four screens and they've got like incredibly complicated software.
And the average show 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 read a radio or 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 1500 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 your own 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 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 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 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.
And I think that is when you're new at something, you tend to hold things too tightly. Like I hold the drum stick too tightly. I hold the neck of the guitar too tightly. Anyone who's played any instrument will understand kind of where I'm getting what I'm coming from here. I supply drums. I know what you're talking about.
Okay, so you hold this stick really really. 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 you just, 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 in specially 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, 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. 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 are you trying to say?
Well, what I'm saying is you have a couple of decades of experience. 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 OK to loosen up. That's what they say a lot about men. They say, oh, well, she used to be intense. These 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. It's nice though in a different realm of something to find a metaphor. And in my head now, I am kind of thinking about this. Like loosen up your grip a little bit. What parts of life? Well, let's say business. I would say also like with my kids a little bit. I would say there's a way where I kind of wanted them to do certain things a certain way.
And it just creates this conflict like they're their own people on my own person. And you know, I want to encourage them to do certain things in a certain way. But I also got to 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 I just in general, I just feel better when I'm not gripping things so so tightly. And when I look out there, you know, on Twitter or anywhere linked in or whatever. And I'm looking at these like business stories. There's just 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.
Pay attention to a few things that matter and let it let things just be a little bit more. The best example that I've experienced 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 was the first thing that came out. I think my early words were I wanted to fight. And so if I met someone with a different political perspective, it was your wrong for these reasons that you're really stupid for that.
When I lived in San Francisco, I was I was significantly more combative than I am nowadays as I I I've been lucky that I was raised in Missouri and that I lived in San Francisco, lived in New York, lived in Texas. I think that 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 why do you feel that way.
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 one plus one equals five. I'll say well, I hope you have a really good day. And and that's a little bit about how 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 to how to infringe when 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 you know party typically walks away happy or satisfied. So loosening the grip for me is arguing less words. I'm not even going to judge you and I'm just going to I can recognize that you think this way and I think this way and it's cool.
It's a great example actually. I hadn't thought about that, but that's another great example of just like holding on. It's not even holding on to tightly to a perspective because 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 or you're not even able to listen. Now I think the point about like being too grippy is is your your it's like you're spring under tension and if someone says something to you that you disagree with like you're going to
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 within 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 with cars and like we are.
Yeah, and we see like this this abyss and then we're just a silly blue thing in the middle of it and and it's like a lot of astronauts say it changes their perspective and it melons 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 stuff that I thought mattered doesn't matter.
For example, I remember with COVID happened and I was like we're never going to a concert ever again. And then three years later I'm like fuck that I forgot all about that. Do you know what I mean? Totally. Have you have you to that point about astronauts? Have you read that great passage from Carl's saying in 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's short. It's a paragraph. It is one of the most beautiful passages I've ever read but 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, I think he calls it like a moat 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 right. It's exactly what you're talking about in the most beautiful poetic way, which is all the stuff that we're worried about. All these things, very few of those things matter. Although, of course, they matter in your day to day life. They're real for you but they really don't matter that much. It's just a good reminder that all the things were just so fired up about.
Well, it's a paradox of like caring by not caring. Why do you not like comparing this stuff to business? Afterwards, I'll tell you my reason why I think it's good. Yes. This is an undeveloped thought of mine that's been on my mind. I don't know if it's a good idea or not. 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 then consult for companies about how to run teams or some great coach.
Coach is a great team and then they come and they bring to the business world. It's always like bringing it to the business world. And I'm like, what is the business world deserve the best lessons from things that are completely unrelated in the 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 sort of insecure in a way.
And it's like it's wants to listen to the Navy SEALs wants to listen to the great double or and see double a coach wants to listen because it's insecure in its own way. And also there's this there's a sense of like these other places and people they know better than us. So I were going to we're going to 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.
Does that make any sense? Yeah, is it just a weird idea? No, it makes sense, but my argument would be instead of the image that you've had it said you just painted is you've painted a 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 majority of the world will change, but I 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 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 a business as a very pat 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 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 with their filtering to. And maybe I'm wrong about this, but why aren't the Navy seals asking CEOs for advice.
Why sometimes they are if you look at like I don't maybe they are like Jack Welsh'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 you know, worst teams are.
But there's something it's like you would imagine this this entity this business thing that is absorbed everything would then be the definitive source of this wisdom. But I wonder is it one way street or is it a two way street and 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 I just wanted to give one example, but I was yeah, frankly, that's a nitpick example.
Totally. I don't 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. A quick break to tell you about another podcast that you have to check out. It's called create like the greats. And if you like learning about history, which by the way I do.
And you like learning about the creative process, then you're going to love this podcast. Each episode is a deep dive into the creative process that went into building some of the greatest companies and brands of all time. It's for anyone who wants to learn how to systemize their creativity like the best creators out there. So check it out create like the greats wherever you get your podcast. What was more fun early days or late days of the company? Oh, man. That's a really good question.
They're very fun in very different ways. So I mean, it's a bit of a cop out, but it's it's true. 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 going to starting from zero and you're building something and you don't know where it's going to be 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 what's hard actually is the middle. We've gotten to a place now being 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 that 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 like you're kind of in this sort of maintenance thing. Were you big enough at at 15 years where you're like like payroll is 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 have complaining, but this feels weird.
Yeah, and I'm not really complaining about it. Yeah, yeah, it's more like you know, Scott Scott, Scott Belski wrote a book called the messy middle. 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 like 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 like you're just going you're just moving.
Then you just play it place where you're like 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 like we've been doing this so long now that like if we took some crazy bets, and it just totally all fell apart like I don't want that to happen, but I'd be okay with that too like we're the 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 like I'd be okay with that too. So I feel like I'm at that place now what I wouldn't have been at 15 years. That makes any sense. So what your sense? I mean you started a bunch of stuff.
My sense is that so none of my things have had been as big as yours, but they've been big enough where we've had dozens or you know 50, 60 employees and we got outside of the like existential crisis moment where it's like things are working.
And everyone talks about focus. Focus is a very common thing and it's something I firmly believe in, but someone who likes to make things for my skill set, a company outside like maybe let's say three million in revenue or maybe maybe five million in revenue.
I'm not consistently a five 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 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 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 I just had a child and I'm like I'm in this 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 in more 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 at top my game.
And then there's other times sometimes I think can last for years maybe where it's just like it's 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. It's basically like what they say with a lot of great investors I think a manish said this on our papaya 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 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 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 I think what you're getting at is 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 but for you personally it feels a little bit like you've become detached from this thing that you made and you you're now further away typically from like the the creation phase.
And now you're more the maintenance phase of something and and you're dealing with internal politics and personalities and hiring and you've got some great people who just left and I get to find new people in the cultures changing and like that's a pretty tumultuous turbulent time for a founder. And I've gone through that many times and it comes comes in a goes what I've found is that what I kind of discovered actually recently is that my job as the founder I'm still 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 job is to manage risk to some degree to keep their job to not push too hard or too far ultimately.
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 found a lot more joy and and and excitement in is is revisiting this idea of injecting risk and for us that 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 a force and I'm like there you it's impossible that's impossible to change.
Even if you hire great great CEO to replace you with CEO like there they just don't have that there they might be incredible CEO great executive executing things trains run time incredible but there's that thing that's present in a founder simply because they were there from the beginning that they 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 is going to take risks.
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 my sense is the way I found to return to this sort of flow versus the the app 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 for products we're going to begin we're about to start working in two products simultaneously which we've never done before.
We've never built two 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 sass we got all these things we're going to do multiple versions of multiple things and different different business models and we're going to 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 a little bit trying new things but that's how I have to run the business otherwise I will become board and at that point it won't serve me or the business well if I'm in charge and board that's that's not a good thing for my professional life or for my main company that's like the main nine to five thing.
For Hampton I've not I do injectorist but I have a CEO and so I try to I have to like respect I got to respect that relationship and so yes on my nights and weekends I created a new website for fun I created this website called samslist 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 account for something.
It 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 someone was like I'm saving this for later to find in the county. 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 samslist where I reviewed or I like put all the information from all of my research for all these accountants created this website I think I got 8000 people to come in the first week and then I started figuring out how to monetize it and so this month the first month that's been live it's made 20 second when we're filming this I think it's done 20000 this month and the 20000 dollars that I've made from that is more dopamine.
More dopamine than let's say a million dollars a month or two million dollars 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 like just stupid like the calculator like the logo that we have is a calculator that has three numbers and a queue and it looks like clippy it looks like clippy from Microsoft like waving at you it looks like Mickey Mouse.
I just use chat to be a said make a logo that looks like clippy but it's a calculator and it's so fun to take silly joky 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 screaming like I love that like isn't it would 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 we have this. Internal say we don't say that much we've we I've said it before we kind of try to feel it which is that cool wears off but useful never does. And what you 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.
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 grip is loose on this you know you're having fun with it yes tragedy to make a logo and you're goofing around the name is just your name it's like. It's just have some fun 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 to 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.
Something probably in this that like you're like I did this by myself yeah that's like the feeling of accomplishment and 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 work or 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 them 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 there was a study where they looked at the most common reasons why couples get divorced. The most common reason was content and the most common the most common reason for divorce was content 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 I think you've been in business with others I'm assuming yeah I've got the most I've had bad relationships I'm currently in a very harmonious relationship with my co finder Joe that I could see lasting a lifetime.
What feels different about it so when we first started together we would we invested in startups together and we had a great time and he previously helped me with my old company the hustle I call email them 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 them 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 is 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 at me.
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 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 I'm not going to like get on 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 I know I'm not going to be happy.
Like I was like all of his things and we looked at the all the things they were 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 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're like cool we like did a really good job of being very honest upfront about our wishes and now it's a much easier to address like any issues we have because it's like hey you he'll be like hey we got to get this done and I was like yeah but I but I hope you like it.
And I was like, yeah, but I, but he'll be like, uh, but you told me that you don't want to like grind on a Saturday. So I'm not even going to ask you. It's all good. We agreed to this. Uh, things like that. And that makes the relationship really nice. Um, is that we, uh, respect one another and we had those conversations super early on. Do you feel like, uh, um, the list or the conversations you had about that, um, turn out to be true?
Like are those really the things that, that you guys share together? Was that sort of what you imagined you would share? Yeah. For example, 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 matter? 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's, 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 interesting. It's interesting. Well, you don't do that with your partner. You don't do that with your partner. Like, well, you guys, your guys as finances are probably so tied together, but you know, they are tied together.
I mean, yeah, basically all of our, you know, essentially the vast majority of our net worth is tied in our business. So we know what our distributions are and all that stuff. But yeah, we don't, I mean, we don't talk about that ever. But it's interesting. Like I also like your Midwestern or I'm a Midwestern or like I feel like my thing is like, don't talk about it. I don't know why like 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. And 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, 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, I have no clue about this. And so I, and 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 switching 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, 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, they, they like regretfully took it. They didn't really want it. Then I don't think they needed it. And I think I'm going to get it back when they pass.
I don't think like I, they're not going to use it, you know? 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 broke. 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. 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. I guess I've always been careful with it. So I kind of absorb that, like, just don't really talk about it. And it didn't limit me though. It's not like, I just felt like we were, everything was sort of fine as how it felt to me. What are you going to do?
What are you going to do at 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 are growing up. You know, we own a few homes. You know, we've a couple nice things. So it's like, it's, it's, it's kind of obvious that like we can afford things and do things. But we just don't, we haven't talked about it.
I think that's, that's an incredibly Midwestern and a, 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. Make people work for like a, 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 coming. Just deal. We're not going to inconvenience you. Whatever. Just giving it like, I'll eat that.
Yeah. Yeah. And that's like the attitude. I've never sent a dish back in my life. Not in a million years. Never ever. Never steal. 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. 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 in a traditional success 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. Like I don't have any. Your parents?
Yeah, my parents. My parents were young. I'm like, I don't even know their grandparents' name. I don't know. I had to do 23 of me because I'm like, I want to ask them what my heritage was. They would go, we're white. I'm like, yes. Yeah. Okay, but what flavor? Like, go ahead. I need some more. And so, 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 find out that an uncle is actually a, my grandmother was married previously. And I'm like, why don't you guys tell me to this? And they're like, oh, we didn't want to bring it up. You know, like little things like that. And I'm like, that's weird. Just like, just discuss it. Just tell me. Yeah, that's weird. 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. 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 like incredibly fancy cars. Yeah. And my midwestern sensibilities like, dude, don't do that. He's like, why not?
I'm like, my sense was like, it just, it sends a weird message. He's like, what's the message? I mean, everyone knows like, everyone here who works, like they know we're doing well, like why would I hide that from you? I agree with you in 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 it was brought up. And the amount of 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. Like, 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. Like, 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 like way back in the early, early years. But it still is something that's in there. There's a residual struggle with that degree of honesty around money in a similar way that people like, you know, in a very like, who'd you vote for? Like, I don't talk about who I vote about.
Same. Chris Rock has a great bit on that. It's so funny. Like, when I see someone with a political bumper sticker on their car, I'm like, you're insane. You're a crazy person. Yeah. And they're probably like, why? I like this guy or like that guy or like her. I was like, what, why am I have to have to hide my point of view? And they're right too. You know, so deep down, your point of view is healthier.
I still have a hard time with it, not, 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 at least my son who's older. My daughter's five. She doesn't recognize any of the stuff yet. But my son does and my son's really into like, it seems to be into expensive things. He like has this craving for expensive things.
So I mean, he's got to know what's going on to some degrees, not an idiot. Do I want to sit him down and go, hey son, we've got this and we've got that. And like 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. They free people are free to stay there as much as they want, visit as much as they want. I have this property in Wisconsin. It's old farm house, 160 acres. It's 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 about like, we're fortunate, clearly fortunate and lucky.
And a big part of this is you want to share these things. You're not fortunate if you hoard the things. Then there's something I think kind of wrong about it, in my point of view. So share as much as you can. Share these experience with other people. And we're fortunate. That's kind of how I sort of left it at this point. I don't know. We'll see. The thing that I tell my friends and family is I try to let them know, 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, like just meeting the woman who you spend your life with. Like this is the fact that we are 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. 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.
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 in 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. Oh, 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 did 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? What is it? I don't regret 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 why combinators start up school years ago. I forget when I was invited to speak. I was only invited once because I was pretty anti raising money.
Yeah, so to say, I thought you're like the opposite of their ethos. I was, but Paul was kind enough to ask me to come up on stage and give a talk. But you and Paul seem quite similar to be honest. Well, I appreciate that. I mean, I have a lot of admiration for his ability to put ideas together and think things through what he's built. But he invited me to stage and there was a question from the audience about luck. Someone's 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 was it? Early, I'm mid-20s. Mid-20s, I think it was. What? And I was just such a prick, but a young punk prick, you know, kind of like, and it's so embarrassing. But you know, like a lot of things are, you look back on like poetry, you wrote in college, like, oh my god, I wrote that or whatever.
Like what ever it is, you know, and you know, it's like you just realized 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 of the bullshit that you thought. But also like, that's who you were at the time and that's that. New York, Austin, Chicago, and San Francisco.
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It's awesome. So again, joinhampton.com. Now, back to the pot. 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. Everyone's throwing like in my four-you feed and Twitter.
It's like ten things you got to know or you're falling behind. It's like, there's just like this, everyone's falling behind. I mean, while this thing is brand new and moving fast with 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.
And all the things that if you would have read that feed a year ago that you were supposed to know, it wouldn't have mattered that much if you didn't. Most things, some things would be handy to know, but like, 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 was actually easier to do during the pandemic.
Was to go back and so today is May 22nd, 2024. Just to go back and all the podcasts I listened to and listen to May 22nd, 2023. So listen to podcasts that are 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 to, man, we are 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 an office, this is going to happen. If they get an office, this is going to happen. It ends up 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 re-sharpening 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 what 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 of the time, the geographies tend to be very long. I've got a limit where it's like 500 pages or less. Yes. But I'll do a long one every once in a while. And I read a fair bit, not because I'm in a competition. It's just an hour and a night is typically a book a week.
Great. And I read a lot of biographies. I like business biographies. I love history. So a lot of the World War II leaders, a lot of the American 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're 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 like the 1600s. And what I like to do is let's say I read this biography about Ted Turner. Ted Turner is the guy who started CNN. He was a fascinating guy to me. Let's actually explain it in the United States. Biggest thing.
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, 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 often times that you'll read a biography and you'll think this was obvious that this person was going to do this or they're who wouldn't have predicted that this was going to happen. And or here's another example.
World War II, Churchill was like basically he was like the world's going to end. Like we are going to die. The world's over. 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 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 read Henry Ford's biography about cars or Henry Ford's 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 at your point, you don't actually have to be that fast to pounce on certain things.
It's really quite fascinating. And to put it in some perspective, the Ford came out with the Model T. I think in 1912 or 1916. So the internet right now is something like 30 years old. So that is basically like how old would you say the internet is? Or like the modern it day internet? The commercial internet. Yeah. Like 95, 96 is one like really, Mizzila or Netscape kind of came out and really kind of made it happen. It's basically basically older than that because it's a research thing. Right.
Commercial, yeah. 35 years. It's basically like a car company in 1940. Do you know what I mean? 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. Just to see what are interesting 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 side existed too. That's fastening. It there's an ex account I follow for like pessimists archive. Love it. I love that one. It's a great one to follow and just like and the thing is this thing that's a little bit interesting about right now. The time we're in is that there's so many people saying so many things all wearing the expert uniform. Some people are experts like lit there are experts in this world.
But many people act and play as one based on just their ability to communicate on platforms. And there's just so much certainty layered into their suggestions and requirements and requests and demands. But it's just it's very healthy to go every time you see that. Every time there's like a you must I always buy haven't go probably not like the more forward they are about being certain and right about something. Sort of the less interested I am in this 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 balance on everything as it's happening. And in many cases, it's 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 open AI is just like wipe 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 and 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 this guy named Dylan just said, you should just ask people what's interesting to them. And that's what I wanted to do 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 to you.
And it's 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 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. I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off.
I thought I'd roll, let's travel, never looking back.