Modern Wisdom - #818 - Andrew Wilkinson - How To Stop Feeling Like Your Success Is Never Enough

Episode Date: July 29, 2024

Andrew Wilkinson is an entrepreneur, co-founder of Tiny Capital, and an investor. "I'll be happy when..." is the beginning of many people's mindsets about life and happiness. We assume that happiness sits on the other side of the next set of goals, even though right now we're on the other side of our last set of goals. So the question is, what if you're a billionaire? Does this pattern ever stop? Expect to learn whether successful people are just disordered, if SSRIs aren’t actually that bad, what Andrew learned from Warren Buffett, whether there's a number you reach in your bank account to feel like you ‘made it’, why wealthy people distort reality, where to find smart people to hire for your business, how to learn to trust your entrepreneurial gut and much more... Sponsors: See discounts for all the products I use and recommend: https://chriswillx.com/deals Get up to 20% discount on the best supplements from Momentous at https://livemomentous.com/modernwisdom (automatically applied at checkout) Get a 20% discount on Nomatic’s amazing luggage at https://nomatic.com/modernwisdom (use code MW20) Get a 20% discount on your first order from Maui Nui Venison by going to https://mauinuivenison.com/modernwisdom (use code MODERNWISDOM) Sign up for a one-dollar-per-month trial period from Shopify at https://shopify.com/modernwisdom (automatically applied at checkout) Extra Stuff: Get my free reading list of 100 books to read before you die: https://chriswillx.com/books Try my productivity energy drink Neutonic: https://neutonic.com/modernwisdom Episodes You Might Enjoy: #577 - David Goggins - This Is How To Master Your Life: https://tinyurl.com/43hv6y59 #712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: https://tinyurl.com/2rtz7avf #700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: https://tinyurl.com/3ccn5vkp - Get In Touch: Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx YouTube: https://www.youtube.com/modernwisdompodcast Email: https://chriswillx.com/contact - Learn more about your ad choices. Visit megaphone.fm/adchoices

Hello everybody, welcome back to the show. My guest today is Andrew Wilkinson. He's an entrepreneur, co-founder of Tiny Capital and an investor. I'll be happy when is the beginning of many people's mindsets about life and happiness. We assume that happiness sits on the other side of the next set of goals, even though right now we're on the other side of our last set of goals. So the question is, what if you're a billionaire? Does this pattern ever stop? Expect to learn whether successful people are just disordered, if SSRIs aren't actually

that bad, what Andrew learned from Warren Buffett, whether there's a number you reach in your bank account to finally feel like you've made it, why wealthy people distort reality around them, where to find smart people to hire for your business, how to learn to trust your entrepreneurial gut and much more. The conversation around rich people can be miserable too. Look at this guy that's worth a ton of money and he's still not happy. I understand that that's kind of old hat.

And that's why I quite like Andrew's approach. Well, he's done a ton of inner work. He's really sort of grappled with his pathologies, his problems, his psychological insufficiencies and the framing that he has around the world. And he just happens to be a billionaire on the other side of it. And I think it's just reassuring to hear someone talk

about lots of problems that you will probably face on a day to day basis. And it kind of just answers that not necessarily money won't make you happy, but money won't fix your problems. And it's reassuring and interesting. And I've found him very, very compelling. So I hope you take turns away from this one. But now ladies and gentlemen, please welcome Andrew Wilkinson. You've got a quote that says most successful people are just a walking anxiety disorder harnessed for productivity. Why do you say that? So all my life I've had this feeling that when I wake up, I need to do something. I'm just constantly whipping myself. I basically feel like if I don do something. I'm just constantly whipping myself.

I basically feel like if I don't achieve, I'm a piece of shit. I don't know where it comes from, but I am just obsessed with solving problems and I'm hyper aware of problems. Like at any given time, my brain is five steps ahead of all the things that could go wrong. And my game, if you will, is to try and prevent

all the terrible things from happening. And I think that makes me a good entrepreneur, but it makes me kind of a miserable person. How have you learned to balance those two, given that you want to maximize your effectiveness entrepreneurially, but presumably not do it at the price of your sanity? Well, I think, you know, understanding when you're in a sprint and when to use that, I think,

you know, an elite athlete would understand that if they run into full sprint constantly, they're going to get injured. And I think in my twenties, you know, when it really mattered, I embraced it. And in my thirties, I started realizing that I've achieved the goal I want. I've made enough money that I'm happy. And it's not that I want to coast, but I just want to turn the volume down on that stress a little bit because I've learned how to achieve leverage using delegation and other people and buying businesses and all those other things.

And so, um, I think one of the problems with the way people think is that they imagine that when X then I'll feel good. Right? So you often hear people say, you know, I just want to leave it all behind and move to Bali. Forget it all. The problem with moving to Bali is that your brain comes with you and your brain is anxious. If you're programmed in the way that I am, it doesn't matter where in the world I am. I'm just thinking about problems. And so for me, actually, it's been chemical. I started taking SSRI about three years ago. And I remember about a week after I started to take it, I would hear the anxious voice and all the concerns to it to creep in. And it was just a little bit quieter, a little bit more distant.

So for me, meditation, exercise, being in a healthy relationship, all those form the groundwork, but actually it was a chemical problem to some degree. What have been the positives and negatives of the SSRIs? You often hear many nightmare stories and also success stories. What's the real world review? So I was terrified. First of all, I never thought of myself as an anxious person. CB. Must be a difficult admission to make. AC. Yeah. I mean, to realize that you are acting irrational. You are obsessing over silly things. So in my business life, very functional. In my personal life, I would become obsessed over, okay, I'm taking this vitamin. Could this vitamin have a negative consequence? Oh my God, is my tap water filled with PFAS? Do I need a new type of filter?

Uh, am I in unintentionally exposing my kids to, you know, radon gas in the basement, whatever obsessive thoughts like that, like OCD kind of stuff. And, um, so I started realizing at a certain point that while I had everything, I was miserable inside. I was a dust bowl farmer inside of my head. And so I recognized that and I went to my doctor and I said, Hey, what can I do about this? And he prescribed me an SSRI.

And then I went on Reddit and on Reddit, you only get the extremes. You get the people who say this is amazing. And then you get even more people that say this ruined my life. Five star reviews and one star reviews only. Exactly. And so I was really scared to take it and it sat on my nightstand for a year. And finally I started digging into it more and I said, okay, how do I ensure that I don't have issues with this? And I realized that a lot of people who take SSRIs have a meta, they have a, they basically metabolize drugs differently. So if you look at your 23andme data,

you can actually see if you are a hyper metabolizer or not. And I realized I was a hyper metabolizer. And so if you think about it, it's kind of like, you know, you do a drug, let's say you do a massive amount of psychedelics or something like that. There's always that moment where it hits you and it's like, oh my God, this is, I need to go to the ER, this is crazy. And then it kind of mellows out. And I think that same thing happens to a lot of people with SSRIs.

And so I found that I had that genetic polymorphism and I actually found a drug that was a newer class, a different class that I could metabolize properly called vortioxetine, which not that many people know about. I mean, it's called Trintelex, Sprintelix and Vortioxetine depends on where you are in the world. And it's been incredible for me. The only downside that I've had is that my stomach sometimes gets a little nauseous when I took it. It helps, gets impacted a little bit.

A little bit, but honestly, I mean, it's, there's such a stigma around, I think, admitting you have anxiety less and less over time. Um, and then taking a drug, not that many people come out and say, Hey, I take a drug every day, I take a pill and that helps me function. And, uh, you know, what's funny is they'll also take an allergy pill and not think twice.

And that's changing systems in your body and reducing histamine and histamines in your brain. I mean, the Lord knows what it's doing, but for some reason, when it's serotonin and dopamine, people panic. I think there is a, and rightly so, a concern about over prescription around a Gen Z relying on these drugs to buttress their mental health. When they're not eating well, they're not getting eight hours of sleep at night. They don't have a good social circle. They're not exercising.

They're not all of those things. Um, is very interesting to consider. Okay, I've gone through these steps and this is something which genuinely had a net positive impact. I was aware of what the potential externalities were and I just decided to go through it. I done it all. So I built a rigorous exercise regimen. I had a 45 minute meditation every day. I had, you know, I was eating a very strict diet and it was one of those things where if I did everything perfectly, I'd feel fine. But as soon as one thing broke down, I would, I would break down myself. And so I realized, you know, that's not functional.

It's not. How much of that do you think was the impact of the things that you were doing? And how much of that do you think was the story that you told yourself about being the sort of person that did all of those things? A lot of it was the story. You know, I think if somebody tells you, you know, if, if, if somebody told you, look, every time you fly in a plane, you increase your risk of getting brain cancer by X amount. You're going to obsess over it and think about it.

At least certain people that are tuned in anxious way will. And what's fascinating is now I will listen to the same podcast I was listening to before. I'll listen to Rhonda Patrick or Peter Atiyah and they'll talk about some problem or medical issue or whatever. And now my brain goes, oh, that's interesting. Okay. Maybe I'll- As opposed to, I might have that brain goes, Oh, that's interesting. Okay. Maybe

I'll- I might have that. I've probably got that. Exactly. Wow. So going back to the successful people are walking anxiety disorders, harness for productivity. You have been around an awful lot of hyper successful people. Is this part of the course in your experience, the upper echelons of the richest, most successful people on the planet, are they also on average driven by that same sort of compulsion? Well, I think this is a really annoying word right now, but trauma, right? A parent who mistreated you, a teacher who told you couldn't do it, everybody has a chip on their shoulder.

And the investor, Josh Wolf has a great thing. He says, chips on shoulders, put chips in pockets. Right. So often people who have a chip on their shoulder go to achieve great things because they're trying to prove something to the world. And I think that some people have upper case T trauma and some people have lower case T trauma. For me, I have lower case T trauma. My dad didn't make

enough money growing up. My parents fought about money. My solution to that was make money and everything will be good. Well, it didn't work out that way. But I think that you have someone like Elon Musk who he is on the spectrum and his dad was physically and emotionally abusive to him. He's just way more successful than I am. And so I think what I've found is that most people are a result of something complex inside of them and, uh, you know, who, who else, but a complex person spends their entire life trying to launch rockets into space or, you know, Bezos trying to deliver a package slightly faster than everybody else. What did you expect?

Yeah. What did I expect? Like what would you expect of this? Would you expect them to just be a simple, happy-go-lucky human? They don't ever notice any concerns. How many people have you found that have managed to achieve some degree of worldly success in the well-balanced,

I'm driven by a desire to do well, but not a sense of insufficiency. There's no hypervigilance. There's no underlying anxiety disorder. How rare has it been to find people like that? I think they exist, but I think if you asked their kids, they would tell you that they're crazy in some way. I think a lot of people are very good at appearing that way.

And I think that one of the fascinating things about rich people is you see grandiosity and then you see grandiose humility. So what I mean by that is people who are grandiose, they have the $500 million yacht, 10 houses, go to the Oscar parties, whatever. And then you see people who wear the Castillo watch and they're humble and they live in the house in Omaha or whatever it is. And I think there are two different forms of, uh, you know, they go one way or the other. Right. And I think even the people who go, um, you know, grandiose humility, they still make a point of everybody seeing, look,

I'm wearing the Casio watch. Aren't I so humble? Right. Not to criticize. I think it's, you really only have two options. You can either be extreme or you can be- Signal or counter signal. Exactly. Choose your direction, Western man. Yeah. What did you learn? You've spent some time with Charlie Munger, Warren Buffett. What have you learned from being around guys that are so lindy in the way that they've existed?

Well, I think that they have a singular obsession. they've existed. Well, I think that they have a singular obsession. Warren Buffett, his wife, talks about how he really had nothing in his life outside of reading annual reports and running his business. He's so incredibly obsessed with being the world's best businessman and investor. I think that's great for him, but I think that when I read about Warren Buffett, I decided that I wanted to be like him. I, I was running all these companies and I was super stressed out and miserable and dealing with people problems constantly. And when I read about Buffett, I was like, Oh my God, this guy, he's abstracted business away.

All he does is read all day and relax. And then he buys a couple of companies every year. And I tried to do the same thing. I got an office and I was away from everybody and I had CEOs running all my companies. Well, I couldn't read an annual report for more than 30 minutes without losing my mind and wanting to go send a bunch of emails

and talk to people and do stuff. So I think that you wanna make sure you're playing a game where you would naturally play it either way. And in that instance, you know, that wasn't for me. I have a different version of investing that I enjoy and it's much more people centric. And what about Charlie? Charlie, he is truly somebody who did whatever he said, whatever he wanted. He did whatever he wanted. And he also just lived incredibly humbly. Like I remember going to his house, you know, in LA, you know, I've gotten, I've gotten lots of people's fancy houses in LA and usually somebody with his net worth,

I think it was like 6 billion or something at the time. They've got like helicopter pads and creepy statues and $20 million pieces of art everywhere or whatever. Munger lived like a wealthy dentist. He lived in a normal neighborhood in a house that he designed in the 1950s and really I think what he loved was building machines that worked and figuring out what didn't work and avoiding it. And he's just a learning machine. I mean, back to the point of building a life that you want, all he did was read.

That's all he did. Every time I'd go to his house, he's just sitting there with a stack of books. Uh, and he's just devouring, you know, four or five hours a day of reading. And not that many people can do that. There's a reason why they're so wise and so successful. You must've seen that clip that got circulated about a month ago where Warren was doing part of the report and then turns to his left and says, Charlie, you see this so sad, man.

That was sad. I think it's a, I think it's really hard. They had such a great rapport. Those two. You tweeted something out that I think is actually analogous to what we're talking about here. Uh, quote, here's the number I used to win the lottery sent by entrepreneurs giving advice. What's that mean? So I think that, um, you can't use somebody else's knowledge to achieve

your own goals. And I've, I've, I'd say that most of the bad choices I've made in life has actually been a result of taking advice from other people because definition, definitionally, let's say you talk to, let's say you talk to a podcaster who started in the era of this American life, they're going to say, Oh, you need to be on PRI and you need to do this and that and the other, you're in a different world, different competitive landscape. And so I think that people will over index on what other people did and say, if I just copy their cheat codes, it'll work. But as we all know, if you were to play the

lottery with the same numbers someone else used, it's not going to work. And so I think that people need to ultimately make their own decisions. They need to make their own mistakes and their life should be focused on making as many small errors as possible and then learning over time. I have never been able to tell somebody that something isn't going to work out for them. People don't change. They need to hit rock bottom first and only once they hit rock bottom do they change. One example, I was an incredibly trusting person to the point where I thought everyone was good. I remember watching Harry Potter movies and you see Voldemort or Die Hard and there's the bad guy. I would just think there's no such thing as bad people. There's misunderstood people, there's complicated people, but there's no such thing as bad people, right? There's misunderstood people, there's complicated people, but there's no such thing as like true bad guys. And then I had a few business experiences where I got defrauded or worked with

someone who had lied to me and was truly a bad actor. And from that point on, I was forever changed. From that point on, it was trust, but verify. I had been told over and over and over again, you can't do a good deal with a bad person or don't work with someone with the following qualities, but I really had to experience it in my body. And I think it's a little bit like with kids, you know, when you have kids, they're running around and they're, you know, my sons are running and fighting on the dock and I know

one of them is going to get a splinter and I know one of them is going to fall in the water and cry and I've got to let them have that little flesh wound so they don't have a mortal wound in the future. How much truth do you think there is in that equivalent? Uh, don't try to use the strategy somebody else did because it's very particular to their time, to their industry, et cetera, et cetera. Uh, when it comes to lifestyle design. So what you were talking about there, um, Charlie Munger, Warren Buffett, all

that they want to do is be the best business person in the world, or just spend five or six hours a day reading. Not everybody can do that. Therefore, not only is that not necessarily a successful strategy that's going to lead to them profiting over time, but it's also not even necessarily going to be a happy life. Like it's a life that is designed for those guys with their particular idiosyncrasies for what fulfills them and makes them feel like they're flourishing.

I think a lot of the time, both in personal and professional life, people are trying to, okay, give me the blueprint of what I need to do in order to be able to be wealthy and be happy. And both of those things are by design custom fit. Totally. I mean, look at lawyers, right? healthy and be happy. And both of those things are by design custom fit. Totally. I mean, look at lawyers, right? How many people do you know from school who said, I want to be a lawyer because my parents taught me that it's a good job and I can make a lot of money and I watched law and order and I thought it was cool.

Well, if you actually sat, you know, think about what most lawyers do. They're reviewing documents and it's documents for like a real estate transaction or like someone buying a company. They're looking through little clauses and then going to a legal reference. That is not necessarily the job that most of these people set out to do. And I think that ultimately people go for jobs that have external validation and they like the idea of, but they don't actually like the reality of it. I think that people, when they're choosing jobs or directions for themselves, instead of trying to imagine what's going to make them

happy, should instead have anti-goals. They should be thinking about, what do I hate? When am I maximum miserable? I'm maximum miserable when I'm having to read all the time, or I don't like doing paperwork, or I really don't like having a lot of meetings. I like a lot of time where I'm just quietly thinking and instead use those criteria to choose the life they want. Cause I don't think humans are very good at predicting what makes them happy, but they definitely know what makes them sad. So you're saying that it is more important to stop doing what you hate

than to focus on doing what you love. 100%. Dig into that for me. Tell me a little bit more. important to stop doing what you hate than to focus on doing what you love? A hundred percent. Dig into that for me. Tell me a little bit more. So, um, there was a time maybe five or six years ago where me and my business partner, Chris, were really unhappy at work. Uh, we found that we were traveling constantly. We were away from our kids.

Our calendars looked like a game of Tetris. Um, we were just not, we, we kind of had this moment of like, do we really want to keep doing this? We're just miserable. And Charlie Munger talks a lot about the idea of inversion. He says, invert, always invert, always try and twist something around. Instead of saying, how could I help the homeless much or how could I help the homeless the most? You say, what harms the homeless the most? You say what harms the homeless the most and then you design something accordingly. And so we started writing out this list

of all the things that make us miserable. Okay, so we don't like being scheduled. Well, we started saying, you know, we're not allowed to be booked on Tuesdays and Thursdays. And on those days we have lunch. We always want to sleep well. Okay, well, we're never agreeing to a morning meeting. We don't like owing people things. Okay, well, when we raise money for these companies, we're going to

do it in a very specific way so that we don't have to answer to people. And we really just started designing our lives around that. And we found pretty quickly, we were much happier just focusing on those things. Whereas what we've been doing before was going, well, when we're rich, then we'll be happy, right? When we have all these successful businesses or when we're more like Warren Buffett, that'll be when we arrive. And that has never, frankly, never delivered happiness for us.

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they will give you your money back. Right now you can get a 20% discount by going to the link in the show notes below or heading to livemomentous.com slash modern wisdom using the code modern wisdom at checkout. That's L I V E M O M E N T O U S dot com slash modern wisdom and modern wisdom at checkout. I think it's true to say that when you ask someone what makes a person happy, they will have maybe a vague idea about what's going on. But if you were to say, how would you

make a happy person miserable? That's pretty reliable. That's very, very easy. One of my favorite questions that I ask on the show is what do most people get wrong about X? What do most people get wrong about entrepreneurship? What do most people get wrong when starting a company? What do most people get wrong about entrepreneurship? What do most people get wrong when starting a company? What do most people get wrong when designing a hypertrophy

routine for the gym? Because that question is I think much higher ROI. Look, here are all of the places that you can fall into a huge hole. Don't do those and you will expedite success way more quickly than actually trying to expedite success. The same thing goes for happiness. The same thing goes for business. Totally.

expedite success. The same thing goes for happiness, the same thing goes for business. Totally. I wonder about the, I wonder about how to make avoiding doing things that you hate more sexy. You know, because there's this degree of pure written work ethic.

I know that I certainly have it. A lot of the people that listen to the show have it as well. You know, like a classic sort of working class mentality. I can grip my teeth and get through. I've heard that hard work and discipline and resilience are traits that I should try and push for. I value them in myself.

I think that if I work hard, maybe I can cultivate them. So I'll do that. But it, it's kind of like anti-leverage in a way it blinds you to how could I make this more fun? How can I make this more effective? How could I magnify the outcomes that I'm getting make this more fun? How can I make this more effective? How can I magnify the outcomes that I'm getting from this particular thing? I came up with this idea that I wrote about this week

called the productivity rain dance. So at the start of this year, I asked myself a question, what do I do that I think is productive but isn't? And what are the things that I do that I don't think are productive but are? And what I realized was I'd basically made this weird sort of sacred ritual where I'd kind of like wave the sage around and do, but it was sitting at my

desk when I'm not working, keeping Slack notifications down to zero, trying to sit on email, clearing off stuff that really doesn't matter, being on calls where there's no actual objective on the other side of it, they all felt like work, but the actual outcome that you got on the other side was nothing. The reverse, what are some things that are productive, but I don't realize are, was always saying yes to a coffee if somebody's coming through town for a brief period of time, organizing dinners with multiple friends from different friend groups, reading, going for a walk without anything in my ears and long drives. Those things were super productive when I actually looked at how it made me feel.

And even if you forget about productive, like what makes you feel good and what makes you feel terrible. And those were two buckets of things that managed to do both, both be productive and make me happier or be unproductive and make me feel miserable. And yeah, it was so very enlightening to see that.

And it's taken me six months to basically realize that I'd created this odd detachment from inputs and outcomes. And I'd focus so much on inputs, just I'm doing the thing. I'm doing the meditation. I'm doing the breath work. I'm doing the whatever. So yeah, but what's the, what are you trying to achieve here? And is it actually achieving anything at all?

Or are you just going through this sort of odd dance in the hopes that on the other side, at some point in future, good things will come? What's that Buddhist thing of like all suffering comes from attachment. And if you attach yourself to the idea that you have to have slack at zero, you've definitely definitely ruined your life because it'll constantly fill.

Um, one thing I think people miss about entrepreneurship, in my opinion, entrepreneurship is about laziness. The initial laziness is about fixing a problem. Um, I was just talking to somebody who's a mom and we were brainstorming a business idea and she was saying, you know, I hate packing my kids lunches in the morning, it's so stressful.

And we were like, Oh, it'd be cool if there was a service that did that. Laziness, right? Out of laziness, out of seeing this problem. Where is someone's pain? There's a business, right? So it's embracing laziness there and saying, let's make this thing easier. Everything that a great entrepreneur does from that point on is about building a machine.

It's not about whipping themselves and pushing a boulder up a hill. It's actually about getting the right people on the bus and building a machine that involves people and systems and process. And you actually want to get to a point where you don't do anything. Your job is to fire yourself as an entrepreneur, right? Steve Ells from Chipotle is not on the line making burritos, right? He built a machine and then he scaled the machine. Um, and I think that, uh, embracing that laziness is something that a lot of people really struggle with. A lot of people think that they need to whip themselves and work harder. And I know that was certainly true of me in the early days.

I used to think I'm not a good manager of people. You know, I always found that once I was managing about 15 people I hated it I hated giving speeches and writing big communique emails and building systems and doing HR I just never liked that stuff and I would just book I would read book after book after book trying to become a great manager of people and Eventually, I just realized oh my god, there's people who love managing people. I'll hire an HR person. Eventually I'll hire a CEO. And I think that you ultimately, if you want to be a great entrepreneur, you want to be Teflon for tasks. You want to let everything that you

don't enjoy go away. And when you do enjoy something and you're doing it, you have to say, am I the best person to do this? And ultimately, what you want to do is build a machine and then pour your buy whatever your contribution is, you want to pour it into the machine and then have money come out the other side. And then hopefully, you want to take that money and you want to put it into another machine and so on and so forth. That to me is what entrepreneurship is. And if you think about what Warren Buffett does, think about what Warren Buffett does, let's say that, um, let's say you wanted to sail from Seattle to Hawaii. Most people go down to the beach with their buddies.

They find a bunch of logs, they tie them all together. They build a little sail and they basically have a little raft and they hope that they drift to Hawaii. Well, that doesn't work, right? Starting a company usually fails. It's really hard. You don't know what you're doing in the beginning. Warren Buffett gets on a cruise ship. He finds a great cruise ship with a great captain. He buys a ticket, a stock certificate. He boards and he just lies in the sun reading the entire time. And when I saw that, I was like, oh my God, this is the laziest, most successful person in the world who has abstracted business away to the most incredible degree. And that to me is the ultimate entrepreneurship, right?

I think people think of Warren Buffett as an investor and it's like, no, no, no, he's not an entrepreneur. He's just delegated absolutely everything to the point where he has 500,000 employees and hundreds of companies. We were talking before we got started about something I think a lot of people feel the pain of, which is this transition from operator to executive. And you know, you may even be able to say, when you get around about eight people in the team or whatever it might be. But, you know, I ran businesses for my entire life.

18 years old, I sat next to my then would be business partner for the next decade and a half in my first ever seminar at university. And if you have grown up, maybe not without money or in an environment that praises hard work and a sort of Puritan work ethic, or if there's an expectation that you kind of need to signal being busy, which is also kind of like a sort of puritan work ethic. Uh, or if there's an expectation that you kind of need to signal being

busy, which is also, um, kind of like a proof of work that you put in front of both the subordinates to say, I'm here with you. I remember I ran nightclubs and, um, one of the things that we used to have to do, which was kind of hilarious was if it was the middle of November in the Northeast of the UK, freezing cold, you know, it's wet, it's awful. But the venue manager of the nightclub that you were running your event at, they'd expect you to be stood there on the front door with them because they are. They're freezing their tits off on a quiet Wednesday in November in Newcastle upon Tyne, stand next to me, prove that you're invested

in this thing. And that mentality, that my suffering is somehow in accordance with how hard I've worked, which is, and how hard I work is going to bear fruits. Eventually you can quite quickly actually bypass the how hard I work thing and just do straight suffering equals outcome on the other side. So what is there to say for someone who feels like, okay, the thing that I am doing

or even the situation I'm hoping to get myself into at some point in the not too distant future, I can start to see the murmurings of feeling overworked, feeling a little bit burned out, calendar being too busy. I feel like I'm doing tasks that I shouldn't be doing. I need to maybe upgrade from operator ground floor to executive. How do people psychologically, structurally, professionally, how do they go through that?

So, um, I started a web design agency about 20 years ago and originally it was me in my underwear in my apartment. And then I had a client ask me for, um, a co to do some coding that I didn't know how to do. And so I went, oh my God, I panicked and ran around like a chicken with my head cut off and tried to learn it and it was too confusing. And I finally realized that my girlfriend's, uh, best friend's boyfriend knew how to code. And so I went to him and I said, Hey, how much would you charge to do this?

And he said 500 bucks. And so I went to the client and I said a thousand bucks cause I wasn't sure if I was gonna get negotiated down and they just said yes. And in that magic moment, I was like, oh my God I've just made money and I didn't do the work myself. Right, so that's the most basic form of delegation. And then you get into the next phase

which I call hire one to hire 10. So you could go and say, I want to build a marketing department. I'm going to go hire an affiliate marketer, a PPC marketer, an email marketer, blah, blah, blah, blah. Or you can hire one person, a VP of marketing. That VP's job is to go and build the org and hire them and manage them. That's the next level of delegation where you now have this leverage where you hired this one person and they own an entire part of your business. And then the final phase is really firing yourself fully to say, to dare to say, I think someone else can do my job better as CEO.

And that for me was one of the hardest things to let go because my ego was tied up in it. My identity was that I was an entrepreneur and like you, I had this work ethic of I'm being lazy and I shouldn't do this, but it was one of the best things I've ever done because it allowed me to achieve crazy amounts of leverage by 40 different companies and do all the stuff that I've done since then. But it's a really hard, sad thing. And I don't know that it's necessarily something I recommend for everybody. I think that some people should be in their underwear in their apartment freelancing. I think that's great. I think if you can make good money and you're happy and you like being an individual contributor,

that's awesome. Other people want a company with three people. Other people have grand ambitions and they want a single track and just dominate and do an amazing job in one industry and one company. And then there's other people like me who are an inch deep in a mile wide, and they want to be all over the map. And I think like, if you look at your personal life, if you're somebody who buys way too many books, you know, more books than you can ever read in a lifetime,

you have a overwhelmed Netflix queue, your letterbox is crazy. You probably want to consider having a life where you have a lot of variety and you're doing a lot of different things and you have to embrace that and say, you know what, I'm doing a focused job being a CEO of one company and yet I'm a distractible person who likes a lot of variety in their life. And so I think embracing that one logical and other people, not I always talk about, do you know the movie Jiro Dreams of Sushi? So there's this guy who's a master sushi chef. Oh my God, that's so hard to say. Master sushi chef. He has a tiny little restaurant in the bottom of a subway, uh, station in Japan, very unassuming. And he's considered, um, the best in the world.

He's got, I think three Michelin stars. People wait sometimes up to a year to go there. And in this documentary, there's a movie called Jiro dreams of sushi. That's amazing. In the documentary you see he's so obsessed with making sushi that he doesn't allow anyone to cook the rice, but him. And people are not even allowed to touch the eggs until they've worked there for like 10 years. He's very, very rigorous and strict. And I think he is a craftsman. Now on the flip side, going back to, I mentioned

Steve Ells from Chipotle. Well, he came up with an idea. He built a machine. He scaled it to thousands of locations. You don't need to wait 10 years before you touch the eggs. Exactly. But his life is probably Excel spreadsheets. It's management, it's board meetings. Jiro, he's a craftsman.

He spends all his time making sushi. That's what he loves. He spends all his time making sushi. That's what he loves. He's the best in the world. And I think this is the challenge of entrepreneurship is often you start in a place where you love it. You know, you're doing a thing you love. And when you start delegating, you stop doing the thing you love. And sometimes you can end up somewhere that you didn't

necessarily expect to end up. Um, it's, it's a, it's a really, you know, it's like one of those be careful what you wish for things. I know you mentioned that most lessons, most important lessons in business and life kind of can't be learned through somebody else. They have to be learned through your own pain. Have there been any books or which are the books

when you look back, you go, okay, that really did sort of expedite my insight or at least it gave me a different sort of view. Michael Gerber's, the E-Myth Revisited, for instance, makes me think when you're talking about that. Is there anything else that comes to mind? The E-Myth was huge for me. I would say most of my most valuable reading hasn't been business. It's actually been psychology. I read a book called Influence by Robert Cialdini, which kind of, it's kind of a broad overview of all of the most common causes of human misjudgment. And it talks a lot about how human psychology is wielded against us in sales and marketing. And so that was an incredibly valuable book in terms

of just understanding like, how do people work and why, you know, why do I keep seeing these odd behaviors from the people I work with, that kind of stuff. One of the most impactful books that I recommend to every entrepreneur is a book called How to Get Rich. It is by a guy named Felix Dennis, who is a magazine publishing mogul, a British guy, and the cover and the title are extremely douchey. So, uh, it's called how to get rich and it's him looking like wearing some very posh clothing and he's in this big throne, uh, and he's laughing

maniacally. And so you look at this book and you go, fuck this guy, I don't want to read this. Yep. Um, but it's fascinating because he is a guy who really came from nothing and started selling Bruce Lee posters at the time. Bruce Lee was really popular, I think in the sixties or seventies and somehow stumbled his incompetent way into owning this massive publishing empire and making

hundreds of millions of dollars. And he starts the book by saying, look, I'm going to teach you how to get rich. I'm going to tell you what I did and tell you my cheat codes, but you actually don't want to get rich. I'm actually miserable. I'm old and miserable. And I wish that I'd become a poet when I was 35 because I had enough money to do so. So I find that is one of the most fascinating books because it really drives home the fact that you don't

necessarily want the thing you crave. Most people think they want to get rich when really they just want to make 500 grand a year or a million dollars a year. They don't need to go be a billionaire to achieve that. And in fact, being a billionaire has tons of weird downsides that nobody thinks about. And so his book was really helpful at inverting for me. And I didn't listen to any of the advice because he, I went, what do you, what do you know old man? Yeah. Payback for you.

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you have enough money? I started asking people this maybe 10 years ago, do you have enough money? And I found that people with $500,000 always said, well, I'd like a million. And then you'd see people with 10 million. They'd say, I want 20, you see a hundred and they want 250 and so on and so forth. And as I continued to meet more and more successful people until I got into this really upper echelon of business people where I'm meeting people that are worth, you know, two, five, $20 billion, I noticed that they were still striving. And I remember I was having this conversation with a billionaire and they said, um, Oh man, uh, Jeff Bezos, he's so rich.

And I said, well, what can Jeff Bezos do that you can't, you know, this person was worth 2 billion or something. And Bezos at the time was maybe worth 40. And he just goes, he can buy a super yacht. And I was just like, what a bizarre world, right? That you're still striving. You can buy a crazy yacht and you just can't buy like an extra big yacht with like four helipads and a tennis court and you're feeling hard done by. And I realized that the reason that he felt hard done by is because human nature is comparison and he was existing in this weird world where he's the poorest guy in the room sometimes, right?

If you live in the Hamptons, being a billionaire is kind of run of the mill. You really wanna be more like Bezos. And I just found that profoundly depressing as I observed it. And I observed found that profoundly depressing as I observed it. And I observed it in myself. I could see in these people and I could judge them. But then when I actually looked inside,

I was the exact same way. And so the book is really me trying to grapple with that and ask the question of like, okay, well, when is it enough? And then not only that, but what do you do with it? You know, you build all these money machines and you have this byproduct of money. Well, what are you supposed to do? What's the ethical thing to do with the money? Is it, is it okay to buy a super yacht or is it better to give it to children in

Africa? Can you buy a super yacht and give it to children in Africa? Like what do you, what do you do here? Uh, and so it's, yeah, it's my journey going through that crazy experience. What does it feel like to become a billionaire? Um, well, I remember the moment that I did the mental math. I was sitting reading captain underpants with my kids and my phone dinged. And I saw, you know, as my business partner telling me that we had received an unsolicited offer on one of our businesses and it was a pretty big number.

And I did the math in my head because at the time we're private, there's no stock price. And I went, oh my God, that means I'm a billionaire. And then I felt exactly the same and I went on reading the book with my kids. And I had the same weird moment where, weird moment where I took my company public about a year ago and I was standing in line in a coffee shop and I saw the ticker pop up and saw this huge number in my trading account. And I realized to my point earlier about Bali, brain chemistry is the same, still going through the day. I'll never forget I had an Irish client, this guy, Jerry Kennelly, lovely Irish guy. Awesome.

Great Irish name. Strong Irish name. Awesome. And he is from the south of Ireland in County Kerry, and he invited me there for a meeting. And so I went down to this tiny little Irish town and everybody knows each other and he's like the capitalist mayor, right? He's pointing out, he's like, I own that building and that building and that building. And everybody I could just see accords him so much respect. Everyone's saying hi to him and stuff. And at this point in my career, this is probably 15 years ago, I wanted to be him.

I was just like, oh my God, this guy has it made. And I asked him, we sat down in a pub, we ordered some beer and, uh, I said, what does it feel like? What does it feel like to have all that money and all that success? And he just goes, well, I'm drinking the same pint you are. And I was like, Oh my God, like this is, you know, he, I didn't want to hear it. It's like the sad truth of like people who have a lot of money still fight with their spouse. They still make awkward small talk with the barista. They're still anxious. They're still dealing with, you

know, issues at home and their kids. And at the end of the day, like the money doesn't actually do anything. In fact, it magnifies the misery in many ways. CB Why? AC Well, I think that when you have a large amount of money, it becomes a burden. I'll never forget my agency, MediLab, had a client who was a very, very wealthy person and they were doing a lot of philanthropy. And I had breakfast with this person. And on the day that I had breakfast with them, there'd been a school shooting. And I'd read the news about the school shooting and I thought it was really, really sad and terrible, but I was able to move on with my day

because it was a far away problem. And they were profoundly affected by this problem. They were really, really shook up and I started asking like, oh, you know, this is really upsetting like what's going on for you. And they said, I've been working on gun rights for the last five years. I was trying to pass a bill to ban the weapon that was used in that shooting. And I think that is the part of the burden. I think if you're a good person and you have a

lot of money, you see problems in the world and you sometimes foolishly, sometimes realistically believe that you could have actually solved that or made that go away. I think that someone like Bill Gates hears about climate change and goes, oh my god, like, I got to figure this out. Whereas you and I, we hear about that and we go, eh, you know, and I have nothing I can do about it, right? So I think that's one piece. And then the other piece is

the management of it. You know, it's this big thing that you have to have people to manage and, and people are constantly trying to get it from you and manipulate you in various ways to get access to it. And then it also perverts relationships. In the book I talk about how when I first made money, I was always kind of a mooch in high school. I'd be the kid who's like, hey, can I borrow two bucks? I need to go buy a Pepsi or something like that.

And so when I started making money, I really wanted to pay it forward and be generous. And I found that if I went out for dinner with a friend and his girlfriend, for example, and I didn't pay for the bill, I was being a dick because I'm rich. I should pay the bill. But if I did pay the bill, I was showing off and I was trying to put them down. And so I find that there's many of these catch 22s around wealth where if you do philanthropy and you talk about it, you're a douche because

you should just be humble and not talk about it. And if you don't talk about it, you're criticized for not doing philanthropy. There's just so many of these weird issues like that around money. And it really is a perverting force in your day-to-day life. And then even as you have kids and family, I think it can really cause strife within the family. I mean, we've all seen succession. That's an extreme case, but I think that a lot of wealthy families are

torn apart by money. CB Why? What's happening there? AC I think that the kids can't individuate. They are living based on who is in the good graces of the parents and who's going to inherit the money. And I think that there's a lot of, it becomes like a court. It's like a royal family or something like that. Who's going to be the king and who's going to take over the business and who's going to inherit what? And even something as simple, I was talking to a wealthy friend and I have this beautiful lake house that is like my special place where I escaped to with the family. And I said, I'm so excited that when my kids are older, they're going to have this for their kids.

And he said, well, are you sure you want to give it to your kids? Because typically what happens with these vacation houses is you give it to your kids, but then they have the grandkids and then the grandkids can't agree on what to do and who gets the house. And then they all start fighting. And he had told me a story of another family that actually had this huge feud over their vacation property. So I just think that there's a lot of these odd second order consequences that people don't think about.

You're sowing the seeds of future strife by doing something that in the moment feels good. Yeah. I mean, it's so fascinating to me to hear these stories and the internet really has a problem with it, which kind of makes me a bit, um, makes me feel annoyed. It frustrates me that, me that hearing stories about people who seemingly have it altogether financially and say, and I'm still miserable and my son killed

himself and I am on a ton of drugs or I'm dependent in this way on my relationships are breaking down or whatever. The response to another human saying, I am suffering is not, I'm really sorry that that's happened to you. It's look at all of the things that you've got. This isn't true. How, you know, how, what chattering class luxury belief bullshit is this that, you know, do they not know there's people that are starving and so on and so forth?

Uh, I have come to believe that this is a lesson. The money and success won't make you fulfilled, the external validation won't fix the internal void, that that is a lesson which is in the category that we talked about earlier on, which is one that cannot be learned without experiencing it. Well, I would assume it's a lot like fame, right?

You know, you probably have people that are stalkers or you've had, you know, I'm sure lots of weird experiences and then you get recognized all over the place. And I bet sometimes you're sitting in a cafe and you just want to have a quiet moment to yourself, but three or four people walk up and say, Hey, I like your podcast. And in a way that's a privilege and it's wonderful, but it also is a double edged sword. It comes with a lot of-

How ungrateful to say that this is something that I don't want you, you fucking did this. I wrote this a little while ago and it's a strange inflection point. And it has been the last probably 18 months for me personally, that that has been the period that I've gone from like absolute sort of nobody nobody to now degenerate niche, micro niche influence of fame or whatever it is.

And if I'm out and about walking, maybe every 15 minutes or so, someone will say something nice, dude, like an Amazon driver or lean out of the window, Chris, love the podcast. It's really lovely. It's really cool. But it is getting just the last week was the first time it ever felt like it was a tiny bit much.

Like it was just almost everybody. And you know, again, this is what a luxury problem to have all the rest of it, but almost everybody on the planet has less money and less fame than they would like. They want to be richer and better known. And therefore all of the sympathy flows down to the people that have less. The total addressable market for sympathy is basically zero. Also the total addressable market for advice is basically zero. There's an unlimited amount of content on the internet about how to become rich and basically none about how to be rich. Unlimited amount of content about how to become famous and none

about how to be famous. And quite rightly, the people who don't have the thing, don't have the thing. Are they not worthy of more sympathy? It's like, well, yeah, but there's still suffering that happens up there. So in your, again, you'll have managed to, I guess, straddle groups of people who are rich, people who are famous, and people who are rich and famous. What's the reality distortion of money compared with fame status? And what about when you throw those two together? How do you think about that? Well, Morgan Housel has this great, it's like, I think it was just a podcast that he did where he talks about what you really want is to be rich and anonymous. There's a great Bill Murray quote

where he says something like, if you think you want to be famous, try being rich first and see if that covers it. And I think there's a lot of truth to that. And I'm experiencing that in a much smaller way than you are. I have, you know, 250,000 Twitter followers now, and I get recognized from podcasts here and there. And at first, it was this really lovely thing where I made new friends. You know, I'd be sitting in a cafe and someone would turn over and say, Hey, I'm an entrepreneur. I heard you on the podcast and it was very positive. And then, you know, I just, you naturally just

meet interesting people. Now about a year and a half ago, two years ago, I walked out onto my back patio and my house and I live in a very secluded part of the city. I live on the waterfront. It's very hard to access. And there's a man in my backyard and he's staring at me and he tells me

that he really needs to tell me about his business idea and I am fucking terrified. I, you know, give him my email really quickly and say, Hey, I'd really prefer if you email me. And I go back inside my house and about an hour later, I get an email from him and it's not completely deranged. And I'm like, okay, few, this is just an

entrepreneur who's taken hustle a little bit too far. So the next day, I drive out my gate and my gate opens. And at the end of the driveway, same guy, fist spared, furious that I didn't respond to his email yet. And I just sped away and called the police. Like I was totally freaked out. And that's me barely being famous, right? I can't even imagine what legitimately famous people are dealing with.

You mentioned that thing of like, you need to always be in those moments too. You always need to be grateful and recognize that to this person, this is an exciting thing or whatever. Jennifer, what's her name from Hunger Games? Jennifer Lawrence told a story where she goes, I can be a princess to 99 people, but I'm a bitch once because I'm in the middle of a fight with my boyfriend and I'm a bitch forever. And everyone's talking about it on Reddit. I do not envy people who are famous. And ultimately I think being famous in a niche, like I think being famous, but anonymous, like imagine the Cohen brothers, you know the name, you know, like Joel Cohen, if you met him, you'd be like, Oh my God, he's so incredible. And if he

goes to a film conference, he's amazing. But if you walk by him on the street, you wouldn't recognize him. To me, I think that's actually the optimal amount of fame. In other news, this episode is brought to you by Maui Nui Venison. Maui Nui Venison brings the healthiest red meat on the planet directly to your door. These venison sticks make it so much easier to hit your protein goals. No one stumbles into hitting their protein goals. And this has made it so much more simple every single day. If you're on the road, if you don't have time to get a protein shake-in, this is perfect.

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delivered directly to your door and get a 20% discount on your first order by going to the link in the show notes below or heading to Maui Nui Venison.com slash modern wisdom. Using the code modern wisdom at checkout that's M A U I N U I venison.com slash modern wisdom and modern wisdom. A checkout. My housemate is a big musician and he said, LCD sound system, uh, as a good example, I think they headlined some huge festivals, Coachella or something like that, you know, they played to some obscene, a country's worth of people.

And that dude could have easily got off stage and walked through and no one would have known who the fuck he was. No, normal looking dude. Um, do you think about that with yourself? Cause your face is everywhere on YouTube and with YouTube, especially you can go down rabbit holes, right? So, you know, if you talk about one top, let's say you mentioned the deep state randomly, it's like, you could go down the algorithm and

suddenly you have deep state people, you know, it's like you just have you experienced that? Yeah, it's a, it's, it's an interesting challenge. Like this transition has been interesting. And I think I have quite a naturally anxious disposition as well, very hyper-vigilant around sorts of things. So great at problem solving, great at coming up with designs for products and making sure that all of the grammar and stuff is perfect.

Not so good for relinquishing this ambient sense of surveillance that you kind of just feel is following you around. And, uh, you know, I've really tried to be as open as possible with the audience without triggering the must be nice sort of response, but I feel like if that's the first thing that you come to when people a few steps down the path that you're trying to get along, tell you about thorns that they've encountered. If your primary responses must be nice, as opposed to must be interesting. I think that I just don't think that you belong here.

Like this isn't the show for you. This isn't the audience for you. This isn't the podcast for you, but it has been very interesting, um, to make that change and to sort of reflect on what do I actually want, what makes me happy, um, because I think we look at, you know, Jordan Peterson is a good example, right, of somebody that was kind of plucked from obscurity, this sort of dusty academic working in Canada. And then, you know, from 2015, 16,

through to 2019, just has this obscene amount of growth, probably quicker than anybody else of that ilk and people are very passionate. It's not just like, I dunno, being a pop star or something, which has it's the kind of obsession about it, but not maybe the emotional connection. They don't feel philosophically connected to, you know, some DJs music or something like Tiesto walks through a club, would it be cool to get a photo with Tiesto? Yeah.

But like, do I actually have an opinion on Tiësto as a person? Probably not. And, um, I, I really do think, and I assumed this as well, that at some point on the journey toward becoming either as rich or as famous or as powerful or whatever, as you want that someone stepped in and gave you some sort of training course. That there was like a guy that came to your door and knocked and said, hello, sir. I'm here to explain to you how to deal with all of those things. You go, you're just the same person that you've always been. You've got all of the same concerns and idiosyncrasies and fears and the

other side is you see yourself the same. You see yourself like the same person, but the world sees you as something different. The documentary that was done, I really, really enjoyed sort of famous, famous Scottish singer in this documentary was done on Netflix and, you know, he's trying to write the second album and he's really, really struggling and, uh, you know, Universal Studios are stepping on his shoulders and saying, you really need to get this sorted. We need, we need this to be good. And, uh, he develops a nervous tick and he's got this, it's Lewis Capaldi

and he's got this huge, huge increase in fame. And, uh, he turns to the camera halfway through and he says, fame doesn't change you. It just changes everybody around you. And in my experience, based on what I've seen, it's probably not strictly true because I've, I know some people who've become famous and become more sort of asshole-ish than they were previously. But for the most part, it's this huge sort of discordance between who am I?

How do I see me? The exact same. Who am I to the world? How does that see me? Totally different. It's one of the scariest things I think about wealth or fame is that people will behave differently than they would otherwise. I always think back to, um, when I was in high school,

I had a really rich friend and I noticed he was a nerd. Him and I, the reason we got along is cause we were both into computers and I found that the way that he was treated by the cool kids versus the way I was treated was very different. And I always found that weird. And then I realized it, I was like, Oh my God, it's cause he's rich and like they want to go to

his house and he's got an Nintendo and a pool and all this great stuff. And, um, I think my fear inside is that I'm going to be treated differently. Like I noticed that people who were kind of dicks in high school now will suck up to me or try to sell me real estate or a car or something like that.

And so that is the weirdest part, I think, is, and there's, what's the Drake song or whatever it is, No New Friends, right? I think there's a lot of truth in that. That's the sad part about it. It is. And I asked someone, I've asked a lot of people this question, because again, the total addressable market for advice on how to deal with

things like this is basically zero. And the total number of people that you can learn from is also basically zero. But I asked a couple of people about, okay, what's the solution, given the fact that you have this reality distortion field that follows you around, what do you do? Well, then you end up hanging out with only other hyper successful, wealthy people or famous people because they understand your problems. And the fear there is you end up in a bubble and you have no sense of what reality is. So it's like this sad reality that as people become more successful or wealthier, they just only hang out with people in that world, compare themselves to those people,

feel sorry for themselves. And then one of the treadmill, which keeps it going, keeps it going, keeps it going. Yeah. I mean, am I right in saying, therefore in your experience that the hedonic treadmill just runs all the way up, even the naught point naught naught naught 1% of people still don't feel like they've got enough. Still going. Yeah.

And even, even though I wrote the book, I know it all, I've been through it. I know what I should do, but I still have the dust bowl farmer in my head saying, what's next? How are you gonna achieve today? How could you lose it all? What could go wrong?

And I've noticed that, you know, if you have anxiety, it's like a, a homing beacon looking for problems. And if the financial side is solved, let's say that you've gotten super rich. Well, then you go to health, right? I mentioned before, I started obsessing over health. Um, sometimes you become a prepper or sometimes you'd get obsessed with politics or whatever toxic garbage you like to consume. And so, yeah, that energy is going to go somewhere. What else have you found as a prophylactic against the hedonic treadmill beyond SSRIs, make sure that you train, make sure that you eat well and get eight hours sleep a night? The biggest thing is awareness. I've noticed that people are stressed out only by problems they're aware of. So if you think about the human brain,

500 years ago, if you were in a tribe or not a tribe, 500 years ago, if you're living in a village, you'd be aware of your neighbors problems and you'd be aware of the problems that affect your village. And at any given time, there'd be a couple problems. And I think the problem with the internet is that our brains are not designed to be aware of all problems globally at all times, because I think it can create a narrative that things are terrible when in reality, it's not that things are terrible. It's that things are always terrible somewhere at some point in time.

And so the way that I cope is actually by not looking at news, not allowing myself very much social media, and being very, very cautious about how I work and when I work. So I actually treat myself like a drug addict. I say, you know, if you were trying to get off alcohol, you wouldn't keep a bunch of alcohol in your house. So for example, I have my phone locked down and limited and my girlfriend has the password to screen time. Uh, I can't do email on my phone. I can't look at news.

The screen just goes blank. When I do. What app are you using to control that? Screen time and Opal. So for example, like Twitter has been a wonderful thing for my life and I really benefit a lot from it, but it left my own devices. I'll go on it and this endlessly. And so I allow myself five sessions a day and then it's over.

And after a certain time of day, I'm just not allowed to use it. And so by drawing those boundary boxes around myself, I find that my mental health is better and that I'm less stressed. And I think that ultimately one of the most challenging things about being public, so for example, having a public company is that your stock goes up and down, like yesterday, I lost $50 million on paper and it's like, you know, I didn't, to reassure you, I didn't feel anything, right?

It's just a number. It's a number. And I was talking to a friend about this the other day, and you know, if you own a house, your house is probably your biggest investment for most people. Your house goes up and down in value every day. You just don't see it.

You're not aware of it. You're not getting it revalued every day. There's no stock ticker. And so I think ultimately my goal is to have as few tickers in my life as possible. And what I mean by that is like news, social media, anything that can go red or green, things are good or things are bad. I just don't want that. I want to be as present as possible and only think about what I want to think about in the moment, not allow those things to hijack my brain. It's interesting sort of thinking about

the brain of a hyper-vigilant person, that you can worry about things that you don't yet know about. You're able to invent worries quite well, but if you artificially inject a bunch by exposing yourself to news or by having a lot of different things that you're tracking in one form or another, that is, it's like,

oh, this fire's burning, might as well throw some kerosene on it as well. It's very interesting to sort of purposefully restrict what you're exposed to, especially if you're a curious person as well. If you want to learn things, you go, okay, well, how can I sift through the bullshit that makes me feel bad?

But look at all of the, like these little slivers of gold that I keep on getting. Or, you know, it's good for connecting with people. I wouldn't mind being able to grow my business. And maybe I'll get to speak to somebody that I really respect and that'll be fun. Uh, but yeah, finding that balance I think is, is very, very important. There's a great book called dopamine nation by Dr. Anna Lamke. She's amazing.

She's awesome. And I love this idea that the way the dopamine system works is that you can get addicted to anything, whether it's chocolate cake or heroin, or the example she gives in the book is vampire novels. And I think if you're a anxious person, it's very easy to go down the rabbit hole and get hooked

into anything. And for me, it's like health podcasts. If I don't restrict my access to health podcasts, I will start beating myself up every single day that I'm not doing my VO2 max training and I'm not taking sulfur. I did my Norwegian four by four this morning. Exactly. Right.

There's always something. And, uh, and yeah, I think that you really have to be very careful about what goes in. Think of Andrew Huberman's RPM. Like you are negatively impacting how much money he makes from his AdSense account. So maybe you do need to start watching again. You just leave it on in the background

and make sure that you keep on paying him that sweet cash. But yeah, man, I really do think this sort of insight that we are hopelessly outgunned by the amount of information that we're getting in. We are hopelessly mismatched mentally, psychologically, our predisposition, our source code as humans is not built to observe the entire world's news and catastrophes 24 hours a day fed directly into our brains. And then for us to actually be able to respond.

And that's when you see people that blow up because you just have this frictionless brain to fingertip to world filter where people toilet tweet things that is observed by the rest of the planet as some indication of exactly who they are. Oh, you know, this is a synthesis. It's like, dude, he, he slept four hours last night and was, you know, taking a dump in between two flights in, in Barbara Jordan Airport terminal or whatever. Like it's not that at all, but just leverage works in both ways.

And I think that you need to be very cautious about what you're sort of leveraging into yourself as well as how you're spending your efforts. I wonder when it comes to, we talked before about kind of how programming changes the way that you look at the world, puritan work ethic coming from particular backgrounds. What's your insight on how childhood experiences impact your view of money, of wealth information, of the way that you relate to wealth and making money and stuff like that? Well, I can only speak to my own experience, but what I've seen is that whatever is put on a pedestal or whatever is a problem when you're a kid, I think it's hard-coded into you. And money was a four letter word in my house. I mean, my dad was, um,

uh, entrepreneur and struggling and he was optimistic and chaotic. And, you know, he's the kind of guy who would say, you know what, like let's just buy a family computer for $2,000 and we'll put it on credit. And my mom is like a total hardcore budget or spend thrift. We're looking at our finances and saying, we can't do that. And so those two things, they created this like, you know, vinegar and baking soda explosion. And all I knew that would make my parents happy and make them stop fighting and to be clear, they weren't, you know, they're not screaming at each other. They're just fighting. There's friction in the household. Um, I felt that, okay, I'll just pour money on

this and that'll resolve it. Um, and so that was, I don't know that's somewhere deep inside me, this idea that money is the solution to problems. And obviously I have a very different perspective, but even as we speak today, when I think about protecting myself or when I think about problems, I always am thinking about how can I use money to

stack, you know, to stack up a wall of money around myself so nobody can make me do things I don't want to do or how can I ensure that I have money tucked away if I ever need it for this emergency or that emergency or whatever it is. So, yeah, I do and I, and I, and I am, I'm very grateful that, you know, it wasn't that my parents were alcoholics or hitting each other or whatever it is, because something different would be hard coded for me then, and, you know, maybe I'd be more like Elon or, or maybe I'd be dysfunctional and doing

drugs. I don't know. Yeah. Um, that's, that's what I find so fascinating about, you think about capitalism and we talked about machines earlier. Capitalism is a machine that takes crazy people and greed and builds benefit for all of us. I find it so funny. The same people that hate Jeff Bezos, to be clear, Jeff Bezos, I believe he was an orphan or he was, uh, I believe

his, uh, his dad walked out on him when he was very young. Like so many of these complex billionaire types have very difficult stories, very traumatic childhoods. And they'll criticize someone like Bezos or Elon. And then at the same time, they're still using, they're driving a Tesla and they're love Amazon prime and they don't seem to make that disconnect of like, okay, that crazy person that went and blew their brains out that we all hate on created all these wonderful innovations that we all appreciate today. And I think that's kind of

what's wonderful about capitalism and that people miss. It's this engine for human greed and suffering that does great things. We'll get back to talking to Andrew in one minute, but first I need to tell you about Shopify. Shopify powers 10% of all e-commerce in the United States. They are the global force behind Gymshark, Allbirds and Nutanix. Shopify is the e-commerce platform that helps you sell at every stage of your business. If any of your friends have tried to start a business online, they will know the nightmare that is building a website and learning to code and where does my hosting go

and how do I do inventory management. Shopify gets all of that out of the way so that you can focus on the thing that matters most, which is designing and advertising an awesome product. Just bring your best ideas and Shopify will help you open up shop. Plus, Shopify has got award-winning help there to support your success every single step of the way.

They are your no excuses business partner and it just makes selling things on the internet way easier. Best of all, right now you can sign up for a $1 per month trial period at shopify.com slash modern wisdom or lowercase that shopify.com slash modern wisdom now to grow your business, no matter what stage you're in. Yeah, that is very interesting. It's like alchemy in a way.

You know, you take this thing that left to its own devices without capitalism would disrupt the local tribe or would cause some sort of catastrophe or would just be misery for that one person. But now that person's misery can be mutated into benefit for many other people downstream. We even like think about them, narcissists and psychopaths, right? Cause I've had a few run-ins with various challenging personalities, dark triad types,

and they're really scary, but they may have a, there may be a reason they're here, right? You know, it might be beneficial to have somebody do a crazy thing like that because who else is going to do it, but for a psychopath or a narcissist. And I do think some of these people who are hyper successful do follow that pattern as well. I don't, I don't want to say everyone's anxious. What I've seen is people are either anxious and anxious planners, they're narcissistic or they're

psychopathic. Those are kind of the, the arc, the three most kind of common traits of successful people, the hyper, hyper successful people. To be clear, I've met a lot of very successful, wealthy people in my experience. Most of them have been lovely. You know, I write about in the book, this

experience of going on a trip down the West Coast and meeting progressively wealthier and wealthier people. They were all really nice in different ways and they all have great businesses. But in the book, I talk about how they're all still just miserable and frustrated and adding zeros. Who's got it right? The most right of the people that you've met to say, this is someone that I think has achieved a degree of success, but also they've just, you know, that their,

their mind rests where their feet are. They've found presence. To me, well, so I was in New Zealand and- Prepping? No, kind of, kind of actually. I knew it. It's the only reason billionaires go to New Zealand. Yeah, I actually was in New Zealand for a, it was a conference relating to getting citizenship. So yes, guilty as charged. And prepping. I do love New Zealand though. Um, but anyway, I was, I was thinking about who do I know in Wellington where I was staying.

And I remember this guy that I'd met named Derek Sivers. Are you familiar with Derek? He's been on the show. Yeah. He's amazing. And I had met him and he had been so kind to me when I was a brand new, I was a young pop. I had just started my company and I met him at a conference and he was just so kind and engaged with me and hadn't seen him in almost 20 years. So I looked him up and we went out for coffee and I didn't actually know that much about him. I knew that he had sold his company, but I didn't really know how he'd structured his life and stuff. And he basically, I was opining about everything I was dealing with and all my stress and running the businesses and all the complexities of money. And he said, well,

when I sold my company, CD Baby, for $20 million, I put it in a trust and the trust pays me 5% a year, but I can't access it. So I don't have the burden of the money. I just get the 5% a year from index funds and municipal bonds or whatever it is, but it's not his money and he can never get it back. And he said, I didn't want to play the same game again. I had gone and I had done entrepreneurship.

I'd started a company. I had won gold and my brain was telling me you got to win gold again, you know? And it's like one of these things where it's like, if you win gold, you win gold, like you made it, you don't need to prove to everyone you can win it again. But I think a lot of us go, they, they want to keep playing the same game and winning over and over again. That wasn't a fluke. No, exactly. And so Derek said, you know what? I'm just going to write. I really love writing and I'm going to tinker and start new businesses, but none of it's going to be about money.

I'm post economic. And he, the way he put it to me was I burned the boats. You know, I really drew a demarcation in the sand where I said, I'm done with money. It's tucked away. It's not my money anymore. And I just get enough. I got, I think it's a million dollars a year or something, which is a hell of a lot of money. It's awesome.

Um, so I admire, I admire Derek a lot because he spends his time thinking and reading and meeting interesting people and writing about his thoughts and he still tinkers, but he's taken away money from the picture, which I really admire. And I can think of a few people like that. And I think that the people I admire the most are actually people who prioritize relationships that are friend billionaires, not billionaires. They have a huge broad collection of interesting people that love them and that they love.

And they have great families. Those are the people ultimately, which is such a cheesy answer, but those are the people ultimately that I admire, I think. So interesting, man. I really wonder whether or not it's ever going to be possible to preclude or warn everybody, myself included, and you about chasing down something which is like running toward the horizon, that each step that you get toward it

is it gets one step further away. Morgan Housel says that the only way to win the game is to stop moving the goalposts. It's like, okay, the first thing that you need to do is, okay, where am I going to get to? And at that point stop. But how many people get there and go, well, you know, if I've managed to make whatever

this number is, or I've got my first house, or I've got the dream house that I want to get, it's like, yeah, but it could be a little bit bigger. Yeah, there could be a second car in the driveway. What about a holiday home? I wonder, and I've been thinking about this a bit recently as well to do with capitalism. It's such a fucking good game, man.

Oh my God, is it a good game? So many people have been turned from it. The ancient Greek word for work was translated as not at leisure. So the ancient Greeks saw work as an aberration and leisure as the set point. And now in the modern world, we've sort of done the opposite. We have, uh, this productivity purgatory where even the walk that you do on a morning isn't to enjoy being in nature. It's because Andrew Cuban told you that you're 10% more productive if you get

sunlight in your eyes for the first 15 minutes of the day or whatever. And, uh, yeah, I just wonder, I wonder about all of the different ways that we can shortcut that realization to get to, maybe you should stop working so hard. There is absolutely a group of people out there who are type B personalities that don't have a leverage problem. They have a work ethic problem and they need to just step their foot on the gas. But there's an awful lot of people, most of whom will be listening to this podcast who are type A people who don't have a work ethic problem.

They have a leverage problem or they just have a chill the fuck out problem. And trying to get them to some sort of a stage. I don't know what it is, if we could inject something into the water. I wonder whether this sort of new generation of GLP-1 agonists downstream will maybe have an impact on this. They definitely seem to be able to change a lot of obsessive behaviors, social media addiction, gambling addiction, marijuana addiction, and a couple of friends, mutual friends of ours are using sort of second generation and third generation versions of these.

And a couple of them have said to me that stuff that they didn't think at all would be associated with this, the amount of time that they spend scrolling Twitter has gone down. Uh, one of them said, it turns out that willpower is a drug and the dosage is around about 25 micrograms per day or something like that. Uh, so maybe that'll step in, you know, maybe we're going to be pharmacologically sort of neutered away from this, but I don't know. I really do hope that there is a way.

Selfishly for myself to be able to see, okay, where's enough? And where does that end? Because it is a bottomless game. Yeah, I think with money, not enough people think about what the number they want in terms of income should be every year. And I think if you, Derek was like, look, okay, I make a million dollars a year and that's more than I ever could spend. And that's a great amount of money. But if people worked backwards from there instead, I think they could aim a lot lower and probably have much happier lives and say, I don't need to go and start the next great billion dollar business.

I'm not damaged enough for that. I don't have enough trauma. And instead I'm going to go out and start a pipe fitting business or I'm going to own a bunch of chain restaurants or something like that. I don't believe that people have any awareness of what's going to make them happy in the end. And with money, I think that they really are just moving the goalposts that they, they don't think about what is actually going to derive real lasting benefit. They think about adding the cars and the boats and all that stuff. And, you know,

I've explored all that stuff. I've bought silly cars and I've chartered yachts and all that. And, you know, really it's all empty because you adapt to it just like anything else. I love the idea of the GLP-1 inhibitor to my point of, you know, if you, if you are unhappy sitting alone in a room, you know, why would that be different if you're in another part of the world or whatever?

And, you know, for me taking the SSRI has been helpful on the anxiety point, but I do wonder about taking a GLP-1 inhibitor now. You got me thinking, maybe I will. Yeah, I think it's... When we look at people that are diabetics, we don't say, why can't you just work harder to process insulin? But because everything else has some degree of willpower,

depending on how determined and impilled you are, some degree of willpower and agency that we have over that. So we just assume that anything that's a shortcut is bad. And I'm big into agency. I'm big into people doing things for themselves and not relying on external buttresses and stuff like that. But the way that everybody should look at the richest people in the world

or the most successful people in the world is this bizarre manifestation of a pathology. It's like, wow, I wonder what's broken inside of them that caused them to do that thing. You can't, you can't hope for extraordinary outcomes without having extraordinary inputs. But this is, this is not only true in, in wealth and business, but think about artists, think about, you know, Amy Winehouse was bipolar.

Kanye West is bipolar. Salvatore Dali. Salvatore Dali, all these amazing artists and really, really fucked up people create amazing things. It's just that Thomas Edison didn't have Twitter, right? He wasn't posting from the toilet at three in the morning. He was probably just as insane as Elon Musk and you just didn't have access to him. He was a black and white photo in the newspaper.

And for all we know, people did think he was crazy back then. Who knows. And for all we know, he may have been miserable. Totally. He went to bed on a nighttime. Totally. Yeah. It's a, you said before about people don't change.

Um, dig into that a little bit for me. Sort of what have you learned about that, given that you are trying to change yourself, you want to become better yourself, but what have you learned about the human capacity to make changes? So this has mostly been in a business context, but I've found that the path to misery

is trying to change those around you. And I've found, I've hired a lot of people and I've realized that ultimately when you work with somebody, you are ultimately the rider on an elephant. The elephant is really big and it's going to go wherever the hell it wants. And you can maybe put some peanuts down and hope that they go in the direction that you want, but no amount of, you know, hitting it or doing whatever is going to affect that. The elephant is going to go where the elephant is going to go. And so I have just accepted that, um, you know, generally when you, like, like, let me, let me tell a story. So, um,

we had a CEO and they said, uh, you like, like, let me tell a story. So, um, we had a CEO and they said, uh, you know, I want to go and I want to pursue this strategy to grow the business. And I said, well, we've tried this before we've, you know, we've already done X, Y, Z. Here's all my logic for why it wouldn't work. Now, psychologically, when you challenge someone directly, they double down. So often, if you, let's say you said you're a Trump supporter and I said, well, Trump's stupid and he's a criminal and all this stuff, you actually are going to double down on your belief and hammer it in.

And so, you know, what I used to do is I would go back and argue with this person and try and change them. They would say, no, they doubled down. And then I would wait a year and they would try the strategy and it would fail. And then I would try not to say, I told you so. And I would accept that the person had to learn the lesson on my watch, on my clock. And it was going to cost me a bit of money,

but ultimately they had to hit rock bottom. They had to get to that point where they realized that it didn't work. And then if I intervened, they would just be like, Oh my God, Andrew swooped in and he took away my agency and it would have worked and I hate him. So I've seen that in business and then I've also seen it in my personal life. I've found that very rarely can you go to somebody and say, here's a big list of all the ways you need to change and have them go and do it. I think ultimately you need to watch them fail. Like the kid falling off the dock, they have to go and hit a breaking point or

get called out by a friend or have something bad happen. And then maybe if you're really lucky and they're self reflective, they'll change a bit. I was going to say even after failure, how much change have you found? Well, even then I think, um, it's rare that people will blame themselves. I do this myself, right? I will always have a narrative as to why something I did didn't work and how it's other people's fault. And I always need to check that in myself. I think that generally, you always have a charitable picture of yourself. You know what your intentions were and you went in and you were trying to help

this person and then there's a misunderstanding and a bad thing happened or whatever it is. And we all build charitable narratives because that's how we function. People can't function going through life thinking that they've upset everybody or been a bad person. It's not fun to have your nose rubbed in your shit. and so I think that challenging that protection, um, that kind of innate desire to protect yourself is a hard thing and a lot of people struggle with that, it's a lot easier to say, well, the world was unfair to me and therefore I don't need to change. Can you tell me that story about when you lost $10 million?

Yeah. Um, so I was running my digital agency and digital agencies are wonderful businesses sometimes and really, really hard at others. So you're always in this position where you have too much demand. You've got tons of clients wanting you, but you don't have enough staffing and capacity or you staff up and then the demand goes down. So you're riding this roller coaster constantly. And I heard about all these people starting SaaS software companies. And when you own a SaaS software company,

you have thousands of people paying you every single month and it's very, very steady eddy and just kind of goes up into the right over time. And I went, okay, that's the business that I wanna own. And so I started a project management software company called Flow and we started basically what was, so basically we started Asana before Asana came out and it was very well designed and very cool.

And I funded it all myself. I put, you know, by this point, I put $2 million into it and it was quite successful in the beginning, you know, within six months, I think we're making $2 million a year or something. And then the founder of Facebook left Facebook and started a company called Asana. And I looked at their product and I said, we're, we're better than them. You know, we're designers. Uh, we have more soul. We're going to out-compete these guys will be the scrappy upstart. And, um,

very quickly he raised a hundred million dollars and he built an incredible team of marketers and salespeople and product people. And they outgunned us very quickly within two years. They had more features than us, a better product overall. And, and we were like a fart in the wind. You know, nobody knew about us. Everyone knew about Asana because they were buying ads. And I was really pigheaded and I kept saying,

no, we're gonna win. We're gonna bootstrap our way to this. And in retrospect, I was like Fiji trying to invade the United States. There was never a chance. But because I didn't know what I was doing, I had all this conviction around it. And I ended up losing $10 million of my own money, which, you know, if I had just invested it, this was probably 10 years ago. If I just invested it,

I'd have $30 million more or something like that. Instead, I have zero. CB What was the lessons that you took away from that? Um, well, I think in business you want to Charlie Munger and Warren Buffett talk about jumping over one foot hurdles or Munger has this great line where he says, my idea of shooting fish in a barrel is draining the barrel first. Right. So finding businesses that are high certainty where you have a very good chance of success. And then Munger has another quote, which is fish where the fish are. And the idea there is he talks about there's all these big fishing ponds with tons of incredible fish in

them, but those fishing ponds attract thousands of other fishermen and they all have amazing lures and you're all elbowing each other. He recommends wandering into the forest and finding a tiny little pond with great fish, but only a few other fishermen because you have much higher chances of success. And I think what I was doing there was fishing, uh, fishing in the overfished pond. I had too much competition. It was like, I owned a pizzeria and, uh, venture capital decided to open 10 pizzerias all around me and sell pizza for free. How do you compete with that?

So you mentioned before about the difficulty in getting people to change. Presumably that means that hiring well is the most important thing in the business. Okay. well is the most important thing in business? Okay. Talk me through the process that you use. How do you think about hires? How do you assess candidates?

How do you ensure that the people that you hire do the thing that you want them to under a good fit? So generally the only hires I make these days are CEOs. The way that I do it is I try and find somebody who's run a same or similar business and they've done it at two times the scale. So I'm not looking for somebody who, let's say that I've got a, let's say I have a pizzeria and I want to franchise it. I don't go and hire the guy from Pizza Hut who runs Pizza Hut today.

That's too big. I go and I find the guy who's got, he's currently working at another pizzeria franchise that's five locations or something. And then I talk to them and if I'm nodding along with what they say they would do with the business with no suggestion from me, that is a very good sign because going back to the idea of an elephant, the elephant is going to go where they go to a man with a hammer. Everything looks like a nail. And so if they come in and they say, I'm going to grow this business by franchising it,

and I'm going to go to five locations and here's where I'm thinking. And I'm nodding along and thinking, this is what I would do. That's awesome. And I will rowing in the same direction. Totally. So the number one thing is are they rowing in the same direction? And I've learned this lesson over and over and over. If someone comes in and they say, actually, I don't think franchising is the way to do it. I think you should own all the locations.

And I don't agree with that. Even if I hire them and I try and convince them, that's not the case. They will sabotage. They won't do that. Presumably even if that person's very well credentialed and super competent and all the rest of it. Doesn't matter. They always do what they, whatever their program to do, whatever their thing is. And this is true. I think, you know, everyone has their hammer. Um, and from that point on, I will make an offer. Uh, I try and incentivize them

so that they have skin in the game. They have downside. And ultimately if I win, they win, and if I lose, they lose alongside me. And I think a lot of people miss that. They'll often pay someone a flat salary or something like that, where they wonder why this person doesn't care as much as them. And often it's about alignment. That's something that I didn't understand in the early days. I used to pay somebody, I'll never forget, I had a designer who worked for me and I told him, great news, we just closed a $20,000 contract and we've got all this great design work. And he was kind of nonplussed and I was like, why isn't he excited? And then I realized he doesn't make any more money, whether or not we achieve this, it's just more work for him. And so from that point on, I started trying to align people with

whatever the output was. What's a typical way that you structure the remuneration package? Well, it's usually, it depends on the person. Some people are simple and they just want cash. And so you say something like, if we make $2 million a profit, you get a $250,000 bonus, or you get 5% of profit, whatever that profit number is. Other people say, I need ownership. I'm long-term. And those people, I will often say, okay, do you have cash? You can buy into the business and I'll buy you out if you ever leave. Or sometimes I'll say, I'll loan you the money and then you can invest. But I like people to have this sense that they have actually sacrificed something. I find people don't value things unless they have to dig into their own

pocket. And then the final stage, you know, going back to having bad experiences with people, now I do a really, really deep background check. And we have a group of guys who's actually former CIA that you get deep. They go really well, it's not really PIs, but what they do is they go really far back in people's history. You know, did they graduate from the school? They said, did they work at all the places they said they call the references that aren't given the, you know, Oh, it, you know, it looks like Chris was at a ACME corp, but he didn't include that in his resume.

Let's make sure we call those people. Um, and you know, most of the time people check out, but occasionally you find out that someone's sketchy and you avoid them. Go back for me, where are you finding smart people? What are your favorite pathways to find them? And then what does the assessment period look like? So when I was starting out, I was doing it

and I would just go on LinkedIn and I would say, what are five companies that I admire that are similar to this business? And then I would look at LinkedIn and say, who's the CEO, president, COO. And I would just cold outreach to those people. Um, over time I've actually started using recruiters and I hated recruiters. I hated the idea of paying a whole bunch of money for someone else to go on LinkedIn. But now I look at it as a leverage point because the recruiter will go and interview people and I get them to record the Zoom call. And then I

watched the Zoom recording and I think we both know like, you know, within a minute, and then you're thinking, oh my God, I'm wasting 30 minutes with this dingus if you don't like the person. So it's a great hack to kind of accelerate that process. And what about the, uh, you bring them in and getting them to work alongside somebody. Is there any sort of, no, there's no. In the pool, sink or swim. And I don't mean that in some sort of like harsh way. It's literally just, I want to hire people who are fully formed.

Don't get me wrong. I take chances on people all the time. And when I start small businesses, I will take chances on some random kid and you know, I'll, again, I'll throw them in or I might mentor them a little bit, but when it comes to CEOs, it really is just here's, you know, here, let's get us aligned. Um, that's like a magnet and you know, let's, uh, let's make sure that you are a,

you know, doing hiring a new CEO is like a brain transplant for a company. You want to make sure that the brain will not be rejected. Naturally the brain is rejected. And so you really have to select carefully to ensure you're a DNA match. Um, but you know, those things being right. And then, you know, here's what we care about. Let's go. We just throw them in and don't talk to them.

Ben Francis, the founder of Gymshark now currently CEO of Gymshark again, after he left and then came back, we were walking through Manchester a few years ago. And I was asking him about his approach, especially for sort of C-suite type things, and I think his, his idea was, uh, high well incentivize appropriately and then crush them with, with workload. And he has, it's almost like a wartime general approach to a lot of what he does. That people are close to the best paid that you would be for this level in your industry at this time, et cetera. Uh, but then the amount of work that is thrown on you and it's, it's, as you said,

sink or swim, it's, uh, there's a dude called Bournemouth Barbell in the UK. He's a powerlifting coach. He only works with people for free. Works with people for completely free, but he has created some of the strongest people in the United Kingdom for a very long time and he's in his 70s and he does it because he loves it and presumably he's got enough money to sort of keep things taking over, but he works with people for free. And one of my friends started working with him and I said, dude, that's really

impressive, you know, you've been selected kind of thing to invite only sort of underground hero type guy. Uh, and then I realized over time why this particular guy had such great outcomes. And it's that he basically doubled the training volume of every athlete that worked with him. So in the space of a year, you'd made two years worth of progress. Now, what you didn't get to see through survivorship bias

was the attrition rate. You didn't get to see all of the people who were burned out or injured or gave up on the sport because this crazy guy from the South Coast of the UK was fucking crushing them with double workouts. But what you did see was who were the victories that came out on the other side. Now, in a world where the externality of bringing someone in and crushing them with a high amount of workload isn't injury or, you know, like the end of their career.

It's just that this isn't the right fit for you. You actually can continue to cycle through until you go, okay, I found an athlete or a CEO whose work capacity is so great that they are going to be able to make us move at twice the speed or three times the speed as we would have done previously. It kind of made me think about that. Well, I think, yes, but only through leverage of other people. Like I do want to hire to the point before about putting yourself out of a job. The thing I hate to see actually is when the CEO works really hard. I want a CEO who's lazy and has built the company into a machine and don't get me wrong.

I want the CEO to be a, you know, wartime CEO and run into battle if they need to, if things are looking bad. But at the end of the day, I actually really love seeing a CEO taking vacations, working normal hours, because to me, that tells me that their company is actually humming and they're running it well. It's the ones that are driving maniacally where I go, hmm.

They're not using leverage approach. They're not using leverage. Exactly. By definition. What about, um, what are your thoughts on using your entrepreneurial gut? This is something that people talk about an awful lot. I think that your gut is only as good as your experiences. I think my entrepreneurial gut would tell me to start every business under the sun. Going back to, I was talking to my friend about the lunch business, right?

Oh, why don't I make kids, why don't, you know, start a company doing kids lunches? Well, 20 years ago I would have started that business and been excited about it. Now I know how complex it would be, how low margin it would be. Because I've been in food service businesses and I've seen similar companies, I can go into my mental models in my head and just go immediate no. Right. And I think that, uh, ultimately your gut is built only from experience.

And, you know, even like reading, like I, I'm a big reader. I think reading is probably the number one recommendation I give to entrepreneurs. If you just read all the time, you'll be fine. Um, but even when you read about stuff, it's not the same as experiencing it. There's been numerous things where I've read

about entrepreneurs who have done stuff that they've made mistakes that I, I, you know, would go on to make. And I still had to learn from that, from actually having the pain. Right. Is that a, uh, is that a sad realization? You know, so much of what we've spoken about today is just this kind of endless inability for humans to learn from the mistakes of others, no matter how cool that quote is. Well, I think, um, without the pain, you don't have the motivation. So, um, you know, when I read the E-myth, I was in pain.

I was in acute pain. I remember specifically reading a passage and it said, uh, it was giving an example of somebody who ran a bakery and they were staying up all night baking and then they're running covered in flour and trying to peck into the cash register, you know, try and serve customers. And it was just such a perfect picture of where I was at in that moment that I was just trying to do everything. I was trying to hold up the world. Um, and so pain plus reading equals success, right?

You need the pain. And you know, my son, I play guitar very badly and I really love the idea of playing guitar with my son. And so I got him guitar lessons and he just was checked out. He didn't really care. He said, daddy, this is boring. And I was a little bit disappointed.

So he stopped doing the guitar lessons. And then the other night we watched School of Rock. And in School of Rock, you see these kids and they're Mohawks and they're playing Led Zeppelin and suddenly my son is super excited to learn guitar. And I think like you have to find that moment where you have this passion and excitement or a problem and motivation to learn. And often the most successful is the pain part, right? Because it's impossible to hide away from. There's a lot of things that seduce you all the time. That thing could be cool. That thing could be interesting. But there's far fewer things that are actually very painful that occur in your life. I mean, imagine it's like the way we teach math today. I find it insane. You teach kids math

and you don't explain why they would ever use it. Right? It's like, why would I, I'm in finance now and I got 48% in math 11. I passed because I begged my teacher to give me 2% and I ended up passing. Uh, and therefore I can graduate high school. And today I know all the math that I was learning in math 11 and I'm really good at it, but I didn't know it at the time because I was going, why would I learn this? It's like teaching somebody to go back to guitar. It's teaching someone guitar when they've never heard Led Zeppelin. You gotta know that you can have a mohawk. You gotta hear Led Zeppelin or you gotta be rejected by the girl who likes guys

who play guitar. That's the best motivation. So moving forward for you, you know, having spent an awful lot of time thinking You gotta hear Led Zeppelin or you gotta be rejected by the girl who likes guys who play guitar. That's the best motivation. So moving forward for you, having spent an awful lot of time thinking about the hedonic treadmill tuned all the way up to multiple billions of dollars, what do you sort of hope for yourself over the next few years?

What are you working on to sort of, presumably you've kind of set yourself a bar that you need to be reminded of. Like you've written the book, like you can't, there's an obligation, right? That you have to yourself now, having spent so much time thinking about what do I actually want? What makes people happy? How much can I keep on trying to use the same solution to fix a problem that doesn't seem to go away? What are you hoping to do over the next few years? Well, we talked about learning about psychology and one of the most powerful psychological effects is consistency and commitment bias. So that would be, I tell you, I'm really into rock climbing or

I'm going to get fit this year. I'm far more likely to achieve it if I go and I tell all my friends. And so I think writing the book was a way for me to muddle through my own feelings, synthesize it into a book, which there's a nice benefit. Other people can read the book and hopefully benefit a little bit from it, or they'll be in acute pain and maybe learn from it. But then there's also a level of consistency and commitment. In the book, I talk about burning the boats, giving it all away, signing the giving pledge, and I've made that intention really clear that I'm gonna give away all my money

and my kids are not gonna inherit large amounts of money, and I've really made a commitment publicly. So I think part of it is that, and then also working through what to do with the byproduct, right? Going back to that thing of you is that, and then also, um, working through what to do with the by-product, right? Going back to that thing of you have this, it's like having a farm and the farm creates vegetables and then they're all just sitting in a warehouse or something. No, don't get me wrong.

They compound and you know, there's all the, um, Warren Buffett stuff, but really trying to think about what's the maximum good you can do with this byproduct of money. What about from a personal standpoint, a value is a drive. What are you looking to achieve there? I would love to get to a point where I do not ask myself what's next. And I don't know if that's possible. Maybe if I inject enough GLP-1, maybe I can get there. But I would love to deprogram myself. I think that I have this very,

very loud voice that screams at me every day. What are you doing? How are you being productive? What's coming next? And it really does not enable me to appreciate what I have in the moment. I don't know if that's achievable. To be honest, I'm quite happy with where I've landed now and I feel like I'm in a good place, but I don't know if I will ever have enough mentally, you know? I mean, in the end of the book, I kind of say like, I'm still going, like I'm still building my business and doing all these things, but hopefully because I've created more meaning out of it in that I'm not doing it for myself anymore because I have enough

myself. And now the, you know, if I was to write a second book, it would be, well, what do you do with it? How do you give it away effectively? Right. And that's what I'm investigating right now. That's what I'm fascinated by is how do you do effective philanthropy? What is the most Sam Mancman Fried? He was the guy.

He was your savior. And, you know, wrongly, as I think, incarcerated, get him out, free Sam, and then he can look after your money. He'd do great. Interestingly, I, uh, I read the Michael Lewis book and I went, here's a guy who is just really odd and who you know, it's so interesting. Like it's so easy to twist Sam Bankman Fried and say, you know, he's this horrible guy and all this stuff.

But like so much of what he was doing was like giving huge amounts of money away to charity. Like who does that if they're like a true psychopath that wants to do bad things and defraud people? Again, I mean, he broke the law. He, maybe he should be in jail. I don't know. I, you know, I don't necessarily, I don't know him and I don't have any major opinions there, but it is an odd thing like to hear somebody was committing fraud to give money to charity. That's kind of a bizarre, you know, that's like the, I can't criticize that, you know, as much as I can, someone who's running a Ponzi scheme to go buy a hundred Ferraris.

Yeah. William McCaskill, the guy that came up with effective altruism, uh, you know, it was only maybe six months after that, I saw him and I thought, you know, this is a philosophy that you championed that even if you weren't the original originator of you kind of would at least the face from a philosophy perspective. I think William was the youngest ever philosophy, tenured philosophy professor in history, uh, this kid, tenured philosophy professor in history. Uh, this kid, Scottish guy, really lovely guy. And, uh, you have this guy that comes in and effective altruism, good branding,

good name sort of does what it says on the tin. And I wonder how long it's going to, I wonder if that, if EA will ever get back to where it was or whether the sort of FTX, Sam Bankman freed to buckle has been so cancerous from a brand perspective that EA now needs to be, it needs to be something new. It needs to be effective philanthropy. It needs to be EP or something like that. What a weird world though, where one bad egg ruins something that's so simple and pure,

which is simply the idea of maximizing every dollar to do as much good as you possibly can. I mean, I don't know specifically what Sam Bankman Fried was funding, but most effective altruists are paying for malarial bed netting and vaccines or things like that that benefit people so massively. I think it's kind of crazy to criticize something like that. I think the problem, or at least one of the reasons that it was fertile ground for criticism is that a lot of people in EA, it's sort of, from the outside, it seemed almost purposefully obfuscative.

It was kind of a holier than thou, speaking down from on high, there was sort of in lingo. It was, you know, it was a high IQ fucking movement. Well, any movement that says, how dare you buy those shoes? You know, let's say you have a thousand dollar shoes. How dare you buy those shoes? You don't have any malaria nets you could have got for that. You could have saved a life, right?

It's gonna be judgy. I think it's gonna be judgy. Yeah. Yeah. Interesting, man. I, you know, it will be a shame if there is no, uh, better version of, of charity that is done, uh, you know, Warren Buffett, Charlie Munger yourself, eventually these big chunks of cash are going to get passed down to somewhere. Uh, and if we don't have a better vehicle to pass them down to it's, I mean,

you know, this is the big, this was the big criticism that EA came out of, which is look at where your dollars go when they go to normal charities. I think the last time that I checked, maybe effective altruism had eight or 10 charitable organizations that met its criteria of does what it says on the tin. Actually does the thing, the money is used in an appropriate and responsible way. And there's not an exec island where all of the guys are just business expensing their way around the world

and being sort of super frivolous with things. And you go, oh, that's kind of sad. In the United States, you might have experienced this contrast between England and the United States, but might have experienced this contrast between England and the United States, but my friends in England say when you tell someone about an idea in England, they say, why would you do that? Why would you take that risk? And in the US, they say, that's incredible. There's a culture of excitement and failure is okay. And I find it so interesting that in entrepreneurship, failure is okay, but in philanthropy, no amount of failure is okay. And I find it so interesting that in entrepreneurship, failure is okay.

But in philanthropy, no amount of failure is okay. They point to that one example where there was a fraud and people donated money or they overspent on marketing or whatever the gotcha moment is. And then they cast that net across everything. And that same thing is true with EA with Bankman Freed where it's like, look, I know people who are big in EA and they're lovely people doing incredible work and saving a lot of lives. And I can't criticize them. And just

because somebody who is a bad egg potentially, you know, gave money there, it doesn't, doesn't ruin the whole bunch. It's ridiculous. Very interesting. Andrew Wilkinson, ladies and gentlemen, why should people go? They want to keep up to date with the things that you're doing. Well, they can follow me on X or Twitter. I don't know what we're calling it these days. A Wilkinson, or they can go check out my book. It's never enough.com.

And yeah, I would love to hear what people think. Hell yeah, appreciate you man. Thank you. Thanks dude.