The Glory & Perils Of Becoming A Billionaire - Andrew Wilkinson

1. 0:00 – 7:27

   Andrew’s Experience With Anxiety

   1. CWChris Williamson0:00

      I'm indoors and some people may be noticing that I'm wearing sunglasses. Look at this. Uh, this is not a ad for Ray-Ban's Meta glasses, but my friend bought me these the other day and I can record you front on. So no one will ever usually get to see what this looks like from the other side. But this is my view. This is what it's like to-

   2. AWAndrew Wilkinson0:20

      Bizarre.

   3. CWChris Williamson0:20

      This is what it's like to be me. Anyway, you've got a quote that says, "Most successful people are just a walking anxiety disorder harnessed for productivity." Why do you say that?

   4. AWAndrew Wilkinson0:31

      So, um, all my life I've had this feeling that when I wake up, I need to do something. Um, 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, um, 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, 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.

   5. CWChris Williamson1:10

      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?

   6. AWAndrew Wilkinson1:21

      Well, I think, um, 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 at a full sprint constantly, they're gonna get injured. And I think in my 20s, you know, when it really mattered, I embraced it. And in my 30s, 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 wanna coast, but I just wanna 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 wanna 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 a 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 concern start to creep in. And it was just a little bit quieter, a little bit more distant. So for me, the, you know, meditation, exercise, being in a healthy relationship, all those, those, you know, form the groundwork, but actually it was a chemical problem to some degree.

   7. CWChris Williamson2:44

      What have been the positives and negatives of the SSRIs? You often hear many nightmare stories and also success stories. What's the, the real world review?

   8. AWAndrew Wilkinson2:53

      So I was terrified. Um, first of all, I never thought of myself as an anxious person. Um...

   9. CWChris Williamson3:00

      Must be a difficult admission to make.

   10. AWAndrew Wilkinson3:01

       Yeah. I mean, to realize that you are acting irrational, you know, you are obsessing over silly things. So in my business life, very functional. In my personal life, um, I would become obsessed over, okay, I'm taking this vitamin. What... Could this vitamin, uh, have a negative consequence? Oh my God, is my tap water filled with PFAS? Do I need a new type of filter? Uh, are, 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.

   11. CWChris Williamson3:46

       Yep.

   12. AWAndrew Wilkinson3:46

       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."

   13. CWChris Williamson4:02

       Five star reviews and one star reviews only.

   14. AWAndrew Wilkinson4:04

       Exactly. And so I was really scared to take it. And it sat on my, um, sat on my, you know, 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, uh, 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, um, 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-

   15. CWChris Williamson5:00

       Mm-hmm.

   16. AWAndrew Wilkinson5:00

       ... called Vortioxetine, which not that many people know about. I mean, it's called Trintellix, Brintelix, and Vortioxetine, depends on where you are in the world. Um, 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 take it.

   17. CWChris Williamson5:16

       Gut health gets impacted a little bit.

   18. AWAndrew Wilkinson5:17

       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-"

   19. CWChris Williamson5:30

       Yeah.

   20. AWAndrew Wilkinson5:30

       "... and it 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, Lord knows what it's doing, but, uh, for some reason when it's serotonin and dopamine, people panic.

   21. CWChris Williamson5:46

       I think there is a, and rightly so, a concern about overprescription around 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 a night, they don't have a good social circle, they're not exercising, they're not all of those things. Um-But that, that 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.

   22. AWAndrew Wilkinson6:16

       I, um, I'd done it all, so I'd built a rigorous exercise regimen, I had a 45-minute meditation every day, I had, mm, you know, I was eating a very strict diet, and it was one of those things where if I did everything perfectly-

   23. CWChris Williamson6:31

       Mm-hmm.

   24. AWAndrew Wilkinson6:31

       ... 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. That's not...

   25. CWChris Williamson6:40

       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?

   26. AWAndrew Wilkinson6:49

       A lot of it was the story. You know, I think if somebody tells you, um, you know, if, if s- 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 gonna obsess over it and think about it. At least certain people that are tuned in an anxious way will. And what's fascinating is now I will listen to the same podcast I was listening before. I'll listen to Rhonda Patrick or Peter Attia and they'll talk about some problem or, you know, medical issue or whatever, and now my brain goes, "Oh, that's interesting. Okay." Maybe I'll-

   27. CWChris Williamson7:22

       As opposed to-

   28. AWAndrew Wilkinson7:23

       I'll-

   29. CWChris Williamson7:23

       ... "I might have that. I've probably got that."

   30. AWAndrew Wilkinson7:24

       Exactly.
2. 7:27 – 13:21

   Are Most Successful People Driven By Anxiety?

   1. CWChris Williamson7:27

      So going back to the, uh, Successful People Are Walking Anxiety Disorders Harnessed for Productivity, you have been around an awful lot of hyper-successful people. Is this par for the course in your experience? The upper echelons of the m- richest, most successful people on the planet, are they also, on average, driven by that same sort of compulsion?

   2. AWAndrew Wilkinson7:49

      Well, I think, um, this is a really annoying word right now, but trauma, right? You know, a parent who, um, mistreated you, a teacher who told you you couldn't do it, everybody has a chip on their shoulder. And the investor Josh Wolf has a great saying. 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 uppercase T Trauma and some people have lowercase t trauma. For me, I have lowercase t trauma. You know, 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, i- it didn't work out that way.

   3. CWChris Williamson8:31

      Yeah.

   4. AWAndrew Wilkinson8:31

      But, um, I think that, you know, you have someone like Elon Musk who he is on the spectrum and his dad, you know, was physically and emotionally abusive to him. He's just way more successful than I am.

   5. CWChris Williamson8:42

      (laughs)

   6. AWAndrew Wilkinson8:42

      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?

   7. CWChris Williamson9:01

      What did you expect?

   8. AWAndrew Wilkinson9:02

      Yeah. Oh, what did I-

   9. CWChris Williamson9:04

      H-

   10. AWAndrew Wilkinson9:04

       ... what did I expect?

   11. CWChris Williamson9:05

       N- like, what, what would you expect of would you expect them to just be a simple, happy-go-lucky human, they don't ever notice any concerns? W- 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?

   12. AWAndrew Wilkinson9:32

       I think they exist, but I think if you ask 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, the, the s-, you know, 10 houses, uh, go to the Oscar parties, whatever, and then you see people who wear the Casio watch and they're humble and they, you know, live in the house in Omaha or whatever it is, and I think there are two different forms of, uh, you know... They go e- one way or the other, right? And I think even the people who go, um, you know, grandiose humility-

   13. CWChris Williamson10:10

       Mm-hmm.

   14. AWAndrew Wilkinson10:10

       ... they still make a point of everybody seeing, "Look, I'm wearing the Casio watch. Aren't I so humble," right?

   15. CWChris Williamson10:15

       Mm-hmm.

   16. AWAndrew Wilkinson10:15

       Not to criticize. I think it's... You really only have two options. You can either be extreme or you can be...

   17. CWChris Williamson10:20

       Signal or counter-signal.

   18. AWAndrew Wilkinson10:21

       Exactly.

   19. CWChris Williamson10:21

       Choose your direction, Western man.

   20. AWAndrew Wilkinson10:23

       Yeah.

   21. CWChris Williamson10:24

       What did you learn? You've spent some time with Charlie Munger, Warren Buffett. Uh, what have you learned from being around guys that are so, uh, Lindy in the way that they've existed?

   22. AWAndrew Wilkinson10:37

       Well, I think that they have a singular obsession. You know, Warren Buffett, um, his wife ta- you know, talks about how he really had no- 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, um, and I think that's great for him, you know? But I think that when I read about Warren Buffett, I decided that I wanted to be like him. Um, 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 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.

   23. CWChris Williamson11:49

       Mm-hmm. And what about Charlie?

   24. AWAndrew Wilkinson11:52

       Charlie, um, 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. Um, you know, in LA, you know, I've gone, I've gone to lots of people's fancy houses in LA and usually somebody with his net worth, I think it was like six 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. You know, 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, uh, 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-

   25. CWChris Williamson12:51

       Mm.

   26. AWAndrew Wilkinson12:51

       ... 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.

   27. CWChris Williamson13:01

       You must have 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.

   28. AWAndrew Wilkinson13:13

       That was sad. I think it's, uh, I think it's really hard. They had such a great rapport, those two.

   29. CWChris Williamson13:20

       You tweeted something

3. 13:21 – 17:54

   The Downside of Taking Advice

   1. CWChris Williamson13:21

      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?

   2. AWAndrew Wilkinson13:32

      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 a- have actually been a result of taking advice from other people because defination- 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 gonna 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 overindex 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 gonna work, right? And so I think that people, um, 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 gonna work out for them, right? People don't change. They need to hit rock bottom first, and only once they hit rock bottom do they change. Um, one example, you know, I was an incredibly trusting person to the point where I would watch... I thought, I thought everyone was good, so I remember watching, um, you know, like Harry Potter movies and you see like Voldemort, or Die Hard and there's the bad guy. I would just think, "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-

   3. CWChris Williamson15:14

      Mm.

   4. AWAndrew Wilkinson15:15

      ... 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, m- my sons are running and fighting on the dock, and I know one of them's gonna get a splinter, and I know one of them's gonna fall in the water and cry, and I've gotta let them have that little flesh wound-

   5. CWChris Williamson15:42

      Mm.

   6. AWAndrew Wilkinson15:42

      ... so they don't have a mortal wound in the future.

   7. CWChris Williamson15:44

      Mm. 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. Uh, I think a lot of the time, both in personal and professional life, people are trying to, "Okay, what, w- 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.

   8. AWAndrew Wilkinson16:41

      Totally. I mean, look at lawyers, right? How many people do you know from school who said, "I wanna be a lawyer because my parents taught me that it's a good job and I can make a lot of money, and I watch Law & Order and I thought it was cool"? Well, if you actually sat, you know, think about what do 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 gonna make them happy, should instead have anti-goals. They should be thinking about, "What do I hate? When am I maximum miserable?" Right? So, "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.

   9. CWChris Williamson17:53

      Mm.

4. 17:54 – 27:24

   Stop Doing What You Hate

   1. CWChris Williamson17:54

      So you're saying that it is more important to stop doing what you hate than to focus on doing what you love?

   2. AWAndrew Wilkinson18:01

      100%.

   3. CWChris Williamson18:02

      Dig into that for me. Tell me a little bit more.

   4. AWAndrew Wilkinson18:04

      So, there was a time, maybe five or six years ago, where me and my business partner, Chris, were really unhappy at work. We found that we were traveling constantly. We were away from our kids. Our calendars looked like a game of Tetris. 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?" 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 s- 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.

   5. CWChris Williamson19:31

      We'll get back to talking to Andrew in one minute. But first, I need to tell you about Momentous. You might have heard me say that I took my testosterone from 495 to 1006 last year, and one of the supplements that I used throughout that was Tongkat Ali. I first heard Doctor Andrew Huberman talk about the really impressive effects, which sound great until you realize that most Tongkat Ali supplements don't actually contain what they're advertising. Momentous make the only NSF-certified Tongkat Ali on the planet. That means that it's tested so rigorously that even Olympic athletes can use it. And that is why I partnered with them, because they make the most carefully tested and highest-quality supplements on Earth. So if you're not performing in the gym or the bedroom the way that you would like, or if you're just looking to improve your testosterone levels naturally, Tongkat Ali is a great research-backed place to start. Best of all, there is a 30-day money-back guarantee, so you can buy it completely risk-free, use it, and if you do not like it for any reason, 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/modernwisdom using the code MODERNWISDOM at checkout. That's L-I-V-E-M-O-M-E-N-T-O-U-S.com/modernwisdom, and MODERNWISDOM 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 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.

   6. AWAndrew Wilkinson21:20

      Totally.

   7. CWChris Williamson21:22

      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 Puritan 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 grit 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 from this particular thing?" I came up with this idea that I wrote about this week called the Productivity Raindance. 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... Sitting 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 groups of 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 this, 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?

   8. AWAndrew Wilkinson23:47

      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 definitionally ruined your life because it'll constantly fill.

   9. CWChris Williamson24:00

      (laughs)

   10. AWAndrew Wilkinson24:00

       One thing I think people miss about entrepreneurship, in my opinion, entrepreneurship is about laziness. The initial laziness is about fixing a problem. 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?

   11. CWChris Williamson24:24

       Mm-hmm.

   12. AWAndrew Wilkinson24:24

       Out of laziness, out of seeing this problem, we've created-

   13. CWChris Williamson24:27

       Where is someone's pain?

   14. AWAndrew Wilkinson24:28

       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 wanna get to a point where you don't do anything. Your job is to fire yourself as an entrepreneur, right?

   15. CWChris Williamson24:55

       Hmm.

   16. AWAndrew Wilkinson24:55

       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-

   17. CWChris Williamson25:11

       Hmm.

   18. AWAndrew Wilkinson25:11

       ... 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 communiqué 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 wanna be a great entrepreneur, you wanna be Teflon for tasks. You wanna let everything that you don't enjoy go away.

   19. CWChris Williamson25:55

       Hmm.

   20. AWAndrew Wilkinson25:55

       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 wanna do is build a machine and then pour your bi- whatever your contribution is, you wanna pour it into the machine and then have money come out the other side. And then hopefully, you wanna take that money and you wanna 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, 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, ch- 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, uh, of Warren Buffett as an investor, and it's like, no, no, no, he's an entrepreneur. He's just delegated absolutely everything to the point where he has 500,000 employees in hundreds of companies.

   21. CWChris Williamson27:22

       Mm.

5. 27:24 – 34:04

   Moving From Operator to Executive

   1. CWChris Williamson27:24

      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, I- I, you may even be able to say, "Oh, it's when you get around about eight people in the team," or whatever it might be. Um, but, you know, I- I ran businesses for my entire life. At 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 n- not without money, uh, or in an environment that praises hard work and 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- 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 kinda hilarious, was if it was the middle of November in the northeast of the UK, freezing cold, you know, it's, uh, wet, it's- it's awful, uh, but the venue manager of the nightclub that you were running your event at, they'd expect you to be stood there in the front door with them because they are. They're freezing their tits off, uh, on a quiet Wednesday in November in Newcastle upon Tyne. "Stand next to me. Prove that you're invested in this thing." Uh, and that, um, 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 bi-, uh, 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, uh, 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?

   2. AWAndrew Wilkinson29:26

      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- d- 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 f- 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, "1,000 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 ten. So you could go and say, "I wanna build a marketing department. I'm gonna 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. And that VP's job is to go and build the org and hire them and manage them, and 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, um, and then, you know, the final phase is really firing yourself fully to say, to dare to say, um, "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, you know, my ego was tied up in it. And I'd always... You know, my identity was that I was an entrepreneur and, like you, I had this kind of 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, buy 40 different companies and, you know, do all this stuff that I've done since then. Um, 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.

   3. CWChris Williamson31:32

      Mm-hmm.

   4. AWAndrew Wilkinson31:32

      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 and a mile wide, and they want to be all over the map. And I, 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 could ever read in a lifetime, you have a overwhelmed Netflix queue, your Letterboxd is, you know, crazy, um, you probably wanna 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, uh, variety in their life." And so I think embracing that when logical, and other people not. I, I always talk about, um... Do you know the movie Jiro Dreams of Sushi?

   5. CWChris Williamson32:31

      No.

   6. AWAndrew Wilkinson32:31

      So there's this guy who's a, he's a master sushi sh- sushi chef. Oh my God, that's so hard to say.

   7. CWChris Williamson32:36

      Mm-hmm.

   8. AWAndrew Wilkinson32:37

      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.

   9. CWChris Williamson33:14

      Mm-hmm.

   10. AWAndrew Wilkinson33:14

       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, he-

   11. CWChris Williamson33:27

       You don't need to wait 10 years before you touch-

   12. AWAndrew Wilkinson33:28

       Don't need to wait.

   13. CWChris Williamson33:29

       ... the eggs.

   14. AWAndrew Wilkinson33:30

       Exactly. But his life is probably Excel spreadsheets. You know, it's, 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'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.

   15. CWChris Williamson33:58

       Mm-hmm.

   16. AWAndrew Wilkinson33:59

       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.

6. 34:04 – 37:56

   Books That Helped Andrew

   1. AWAndrew Wilkinson34:04

   2. CWChris Williamson34:04

      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 m- a, a different sort of view. Uh, Michael Gerber's The E-Myth Revisited, for instance, makes me think when you're talking about-

   3. AWAndrew Wilkinson34:28

      Totally.

   4. CWChris Williamson34:29

      ... about that. Is there anything else that comes to mind?

   5. AWAndrew Wilkinson34:31

      The E-Myth was huge for me. Um, 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, um, 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 value book, valuable book in terms of just understanding, like, how do people work and why. You know, why do I keep seeing these, uh, 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 was 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.

   6. CWChris Williamson35:32

      Mm-hmm.

   7. AWAndrew Wilkinson35:33

      And so you look at this book and you go, "Fuck this guy. Don't wanna read this."

   8. CWChris Williamson35:36

      Yep. Yep.

   9. AWAndrew Wilkinson35:36

      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 '60s or '70s, 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 gonna teach you how to get rich. I'm gonna tell you what I did and tell you my cheat codes, but you actually don't wanna get rich. I'm actually miserable. I'm old and miserable and I wished that I'd become a poet when I was 35 'cause 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. You know, most people think they wanna get rich when really they just wanna make 500 grand a year, or a million dollars a year. Uh, 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, yeah, really helpful at inverting for me, and I didn't listen to any of the advice 'cause he-

   10. CWChris Williamson36:45

       (laughs)

   11. AWAndrew Wilkinson36:46

       ... I went, "What do you, what do you know, old man?"

   12. CWChris Williamson36:50

       Yeah, payback for you. In other news, this episode is brought to you by Nomatic. I just got back from Nashville this morning, and this was the bag that came with me, the Nomatic travel pack. It is an absolute game changer. Their 14 liter for daily use or their 20 liter if you are traveling. I can't describe the difference in the quality of your life when you start to use a proper, well-designed backpack. If you have a well-designed bag that's got tons of pockets, it's not over-engineered, it's got a lifetime guarantee. So, it is literally the final backpack you will ever need to buy, because for the rest of time, they will replace or fix it if anything breaks. There's a 30-day money back guarantee. I keep harping on about them, and I partnered with them because I love the things that they make. They are the best quality backpacks and luggage on the planet, and you should go and buy it. Right now, you can get a 20% discount by going to the link in the show notes below or heading to nomadic.com/modernwisdom and using the code MW20 at checkout. That's nomadic.com/modernwisdom and MW20 at checkout. What does

7. 37:56 – 48:23

   What Does ‘Never Enough’ Mean?

   1. CWChris Williamson37:56

      never enough mean to you?

   2. AWAndrew Wilkinson37:59

      Well, it's a phenomenon that I see in everything. Um, you know, if you think about, um, when you talk to people and you say, "Do 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 100 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 two 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 heli pads and a tennis court and you're feeling hard done by? And I realized that the reason that he felt hard done by because, 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. Um, and I just found that profoundly depressing as I observed it, and I observed it in myself. I could see it in these people and I could judge them, but then when I actually looked inside, I was the exact same way. Um, 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-

   3. CWChris Williamson40:02

      Mm-hmm.

   4. AWAndrew Wilkinson40:02

      ... 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, you know, give it to children in Africa?

   5. CWChris Williamson40:13

      Mm-hmm.

   6. AWAndrew Wilkinson40:13

      Can you buy a super yacht and give it to children in Africa? Like, wha- what do you, what do you do here? Uh, and so it's, yeah, it's my journey going through that crazy experience.

   7. CWChris Williamson40:23

      What does it feel like to become a billionaire?

   8. AWAndrew Wilkinson40:26

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

   9. CWChris Williamson41:28

      Great Irish name.

   10. AWAndrew Wilkinson41:29

       Awesome.

   11. CWChris Williamson41:29

       Strong Irish name.

   12. AWAndrew Wilkinson41:31

       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, 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, um, accords him so much respect-

   13. CWChris Williamson41:53

       Hm.

   14. AWAndrew Wilkinson41:54

       Uh, everyone's saying hi to him and stuff. And at this point in my career, this is probably 15 years ago, um, 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?"

   15. CWChris Williamson42:13

       Own the town.

   16. AWAndrew Wilkinson42:14

       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.

   17. CWChris Williamson42:40

       Why?

   18. AWAndrew Wilkinson42:41

       Well, I think that when you have a large amount of money, it becomes a burden, right? I think that, um... I'll never forget there was a client, uh, when my, my agency, Metalab, 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, uh, 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, you know, it, it was a far away problem. And they were profoundly affected by this problem. They were, um, really, really shook up and I started asking like, "Oh, you know, wh- this is really upsetting. Like, what, what's going on for you?" And they said, "I've been working on gun rights for the last five years. Um, 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-

   19. CWChris Williamson43:55

       Mm.

   20. AWAndrew Wilkinson43:56

       ... made that go away. I think that someone like Bill Gates hears about climate change and goes, "Oh my God." Like, "I gotta figure this out." Whereas you and I, we hear about that and we go, "Ah," you know, and "I've nothing I can do about it," right? So, I think that's one piece. And then the other piece is, um, 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. Um, and then it also perverts relationships. Uh, in the book, I talk about how, you know, when I first made money, I w- I was always, um, I was always kind of a mooch in high school. Um, you know, 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-

   21. CWChris Williamson44:57

       (laughs)

   22. AWAndrew Wilkinson44:57

       ... 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-

   23. CWChris Williamson45:15

       Mm.

   24. AWAndrew Wilkinson45:15

       ... many of these weird issues like that around money, and it really is a perverting force, uh, 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. Uh, that's an extreme case, but I think that a lot of wealthy families are torn apart by money.

   25. CWChris Williamson45:37

       Why? What's happening there?

   26. AWAndrew Wilkinson45:38

       I think that, um, the kids can't individuate. They are living based on who, who is in the good graces of the parents and who's gonna inherit the money. And I think that there's a lot of... It becomes like a court, you know? It's like a royal family or something like that. Who's gonna, who's gonna be the king and who's gonna take over the business and who's gonna inherit what? And even something as simple, um... I was talking to a wealthy friend and I have this beautiful lake house that is like my special place where I escape to with the family, and I said, "I'm so excited that when my kids are older, they're gonna have this for their kids." And he said, "Well, are you sure you wanna 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.

   27. CWChris Williamson46:43

       Mm. You're sowing the seeds of future strife by doing something that in the moment feels good.

   28. AWAndrew Wilkinson46:48

       Totally.

   29. CWChris Williamson46:48

       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... It makes me feel, uh, annoyed. It, it, it frustrates me that, uh, hearing stories about people who seemingly have it all together financially and say, "And I'm still miserable and my son killed himself and I, and I'm on a ton of drugs or I'm dependent in this way or 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 happening to you." It's, "Look at all of the things that you've got. This isn't true." How, you know, how, uh, 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, that external validation won't fix the internal void, uh, 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.

   30. AWAndrew Wilkinson47:54

       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 wanna 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-
8. 48:23 – 59:28

   The Perils of Being Rich & Famous

   1. CWChris Williamson48:23

      I, 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 influencer fame or whatever it is. Uh, and if I'm out and about walking, maybe every 15 minutes or so someone will say something nice. "Dude, love the..." Like an Amazon driver'll lean out of the window, "Chris, love the podcast." It's really lovely, it's really cool. But it is getting just... The, the last week was the first time it ever felt like it was a tiny bit much. Like it was just, e- almost everybody... And, uh, 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 i- in your... A- 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. Uh, how does... Wha- 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?

   2. AWAndrew Wilkinson49:59

      Well, um, Morgan Housel has this great, um, it's like a, 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 wanna be famous, try being rich first and see if that covers it." Um, 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 in my house, and I live in a very secluded part of, um, 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, phew, this is just an entrepreneur who's taken hustle a little bit too far."

   3. CWChris Williamson51:23

      Mm. Mm.

   4. AWAndrew Wilkinson51:23

      Um, so the next day, uh, I drive out my gate and my gate opens, and at the end of the driveway, same guy. Fists bared, 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-

   5. CWChris Williamson51:45

      Mm.

   6. AWAndrew Wilkinson51:46

      ... what legitimately famous people are dealing with.

   7. CWChris Williamson51:48

      Hmm.

   8. AWAndrew Wilkinson51:49

      Um, you know, you mentioned that thing of like you need to always be in those moments too, you always need to be grateful and recognize that, you know, to this person this is an exciting thing or whatever. Jennifer, um, what's her name from Hunger Games? Jennifer...

   9. CWChris Williamson52:05

      Lawrence.

   10. AWAndrew Wilkinson52:05

       Jennifer Lawrence told a story where she goes, "I can be a princess to 99 people, but I'm a bitch once 'cause I'm in the middle of a fight with my boyfriend."

   11. CWChris Williamson52:13

       Mm-hmm.

   12. AWAndrew Wilkinson52:14

       "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, um, being famous but anonymous, like imagine the Coen brothers. You know the name. You know, like Joel Coen, 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 walked by him on the street you wouldn't recognize him.

   13. CWChris Williamson52:38

       Mm-hmm.

   14. AWAndrew Wilkinson52:38

       To me I think that's actually the optimal amount of fame.

   15. CWChris Williamson52:41

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   16. AWAndrew Wilkinson53:55

       Totally.

   17. CWChris Williamson53:56

       Normal, normal-looking dude. Um-

   18. AWAndrew Wilkinson53:58

       Do you think about that with yourself? 'Cause your face is everywhere on YouTube. And with YouTube especially you can go down rabbit holes.

   19. CWChris Williamson54:05

       Mm-hmm.

   20. AWAndrew Wilkinson54:06

       Right? So, you know, if you talk about one top... Let's say you mention the deep state randomly-

   21. CWChris Williamson54:11

       Mm-hmm. Mm-hmm.

   22. AWAndrew Wilkinson54:11

       ... it's like you could go down the algorithm and suddenly you have deep state people, you know?

   23. CWChris Williamson54:15

       Mm-hmm.

   24. AWAndrew Wilkinson54:15

       It's like you just, have you experienced that?

   25. CWChris Williamson54:18

       Yeah, it's, uh...It's- it's an interesting challenge. Like, this transition has been interesting and I think I have quite a- a naturally anxious disposition as well. Um, very hypervigilant around sorts of things. So great at problem-solving, uh, great at coming up with designs for products and making sure that all of the grammar and stuff is- is perfect. Uh, not so good for relinquishing this ambient sense of surveillance that you kind of just feel is following you around. And, uh, you know, th- I've really tried to be as open as possible with the audience without triggering the must-be-nice sort of response. But I- 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 response is must be nice as opposed to must be interesting, I think that... I- 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 podcaster 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's 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 o- o- of that ilk. And people are very passionate. It's not just like, I don't know, being a- a pop star or something, which has its... The kind of obsession about it, but not maybe the emotional connection. They don't feel philosophically connected to, you know, some DJ's 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 Tiesto 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 in... 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. I, the, uh, documentary that was done that 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 tic 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, uh, in my experience, based on what I've seen, that it... 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.

   26. AWAndrew Wilkinson57:40

       It's one of the scariest things I think about, um, 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're 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 wanna go to his house and he's got Nintendo and a pool and all this great stuff. And, um, I think my fear inside is that I'm gonna be treated differently. Like, I notice that people who were kind of dicks in high school now will suck up to me or try to sell me real estate or, you know, a car or something like that. And so that is the weirdest part, I think-

   27. CWChris Williamson58:31

       Mm-hmm.

   28. AWAndrew Wilkinson58:32

       ... is... And there's, you know, what's that? 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.

   29. CWChris Williamson58:39

       It is. And I, you know, 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. Uh, and the total number of people that you can learn from is also basically zero. Um, 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? Uh-

   30. AWAndrew Wilkinson59:00

       Well, then you end up hanging out with only other hyper-successful wealthy people or famous people because they understand your problems.
9. 59:28 – 1:06:17

   People At the Top Still Don’t Feel Enough

   1. CWChris Williamson59:28

      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-

   2. AWAndrew Wilkinson59:35

      Still going.

   3. CWChris Williamson59:35

      ... still don't feel like they've got enough?

   4. AWAndrew Wilkinson59:37

      Still going. Yeah. And even, even though I wrote the book, you know, 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-

   5. CWChris Williamson59:52

      Mm-hmm.

   6. AWAndrew Wilkinson59:52

      ... saying, "What's next? How are you gonna achieve today? Um, 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, uh, homing beacon looking for problems.

   7. CWChris Williamson1:00:07

      Mm-hmm. Mm-hmm.

   8. AWAndrew Wilkinson1:00:07

      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- I started obsessing over health. Um, sometimes you become a prepper or sometimes you get obsessed with politics or-

   9. CWChris Williamson1:00:20

      Mm-hmm.

   10. AWAndrew Wilkinson1:00:20

       ... whatever toxic garbage you like to consume. And so, um, yeah, that energy is gonna go somewhere.

   11. CWChris Williamson1:00:25

       What else have you found...... as a prophylactic against the hedonic treadmill, beyond SSRIs, make sure that you train, make sure that you, uh, eat well and get eight hours of sleep a night?

   12. AWAndrew Wilkinson1:00:38

       The biggest thing is awareness. I've noticed that, um, 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, but 500 years ago, if you were living in a village, um, you'd be a- aware of your neighbors' problems and you'd be aware of the problems that affect your village. And at any- 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 the- it's not that things are terrible, it's that things are always terrible somewhere, some- at some point in the- uh, in time. And so the way that I cope is actually by not looking at news, not allowing myself very much social media, um, and being very, very cautious about how I work and when I work. So I actually treat myself like a drug addict. I say, um, 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.

   13. CWChris Williamson1:01:52

       (laughs)

   14. AWAndrew Wilkinson1:01:52

       Uh, I can't do email on my phone. I can't look at news. The screen just goes blank when I do.

   15. CWChris Williamson1:01:58

       What app are you using to control that?

   16. AWAndrew Wilkinson1:02:00

       Screen Time and Opal. So-

   17. CWChris Williamson1:02:02

       Yeah, Opal's great.

   18. AWAndrew Wilkinson1:02:02

       ... for- for example, like, you know-

   19. CWChris Williamson1:02:03

       Been a big fan of Opal.

   20. AWAndrew Wilkinson1:02:04

       ... Twitter has been a wonderful thing for my life, and I really benefit a lot from it, but left to my own devices, I'll go on it endis- 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.

   21. CWChris Williamson1:02:17

       Hmm.

   22. AWAndrew Wilkinson1:02:18

       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.

   23. CWChris Williamson1:02:38

       No. (laughs)

   24. AWAndrew Wilkinson1:02:38

       Right? And it's like, you know, I didn't... T- to- to reassure you, I didn't feel anything, right? It's just a number.

   25. CWChris Williamson1:02:44

       Okay, well, that's good.

   26. AWAndrew Wilkinson1:02:44

       It's a number.

   27. CWChris Williamson1:02:44

       Yeah.

   28. AWAndrew Wilkinson1:02:45

       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.

   29. CWChris Williamson1:02:53

       Hmm.

   30. AWAndrew Wilkinson1:02:54

       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-
10. 1:06:17 – 1:12:19

    How Childhood Impacts Views on Wealth

    1. CWChris Williamson1:06:17

       when it comes to... We- we talked before about kind of how programming changes the way that you look at the world, uh, Puritan work ethic, coming from particular backgrounds, what's your...Insight on how childhood experiences impact your view of money, of, uh, wealth information, of the way that you relate to, to wealth and making money and stuff like that?

    2. AWAndrew Wilkinson1:06:43

       Well, I can only speak to my own experience, but what I've seen is that whatever, whatever is put on a pedestal or whatever is a problem when you're a kid, I think it's hardcoded into you, and money was a four-letter word in my house. I mean, my dad was, um, a entrepreneur and struggling, and he was optimistic and chaotic and, you know, he's the kinda 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 budgeter spendthrift, 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 it, 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.

    3. CWChris Williamson1:07:53

       Mm.

    4. AWAndrew Wilkinson1:07:53

       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 wanna 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, um, yeah, I d- 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 hardcoded for me then. And, you know, maybe I'd be more like Elon or-

    5. CWChris Williamson1:08:32

       Mm-hmm. Mm-hmm.

    6. AWAndrew Wilkinson1:08:33

       ... or maybe I'd be dysfunctional and doing drugs, I don't know.

    7. CWChris Williamson1:08:35

       Yeah.

    8. AWAndrew Wilkinson1:08:36

       Um, that's, that's what I find so fascinating about, you think about capitalism and we talked about machines earlier, right? Well, capitalism is a machine that takes crazy people and greed and builds benefit for all of us, right? I find it so funny, like, 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 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-

    9. CWChris Williamson1:09:27

       Mm-hmm. Mm-hmm.

    10. AWAndrew Wilkinson1:09:27

        ... 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 and for human greed and suffering that, you know, does great things.

    11. CWChris Williamson1:09:41

        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 Nutonic. 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/modernwisdom, all lowercase. That's shopify.com/modernwisdom 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, for that one person, but now that person's misery can be, uh, mutated into benefit for many (laughs) -

    12. AWAndrew Wilkinson1:11:03

        Totally.

    13. CWChris Williamson1:11:03

        ... for many other people downstream. Yeah.

    14. AWAndrew Wilkinson1:11:05

        Well, even like, think about, um, narcissists and psychopaths, right? 'Cause I, I've had a few run-ins with various challenging personalities, dark triad types.

    15. CWChris Williamson1:11:13

        Mm.

    16. AWAndrew Wilkinson1:11:14

        And, um, you know, they're really scary, but they may have a f- 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 gonna 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 wanna say everyone's anxious.

    17. CWChris Williamson1:11:38

        Hm.

    18. AWAndrew Wilkinson1:11:38

        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-

    19. CWChris Williamson1:11:47

        Oh.

    20. AWAndrew Wilkinson1:11:47

        ... the three most kind of common traits of successful people, the hyper, hyper successful people.

    21. CWChris Williamson1:11:52

        Yeah.

    22. AWAndrew Wilkinson1:11:52

        To be clear, I've met a lot of very successful wealthy people. In my experience, most of 'em have been lovely.

    23. CWChris Williamson1:11:59

        Hm.

    24. AWAndrew Wilkinson1:11:59

        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.

    25. CWChris Williamson1:12:05

        (laughs)

    26. AWAndrew Wilkinson1:12:05

        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.

    27. CWChris Williamson1:12:17

        Who's got it right,

11. 1:12:19 – 1:21:37

    The People Andrew Admires

    1. CWChris Williamson1:12:19

       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, their, their, their mind rests where their feet are, they've found presence?

    2. AWAndrew Wilkinson1:12:32

       To me, um...Well, so I was in New Zealand and-

    3. CWChris Williamson1:12:37

       Prepping?

    4. AWAndrew Wilkinson1:12:38

       No. Kind of.

    5. CWChris Williamson1:12:39

       (laughs)

    6. AWAndrew Wilkinson1:12:39

       Kind of actually. Kind of. I- I- I-

    7. CWChris Williamson1:12:41

       I knew it. It's the only reason billionaires go to New Zealand.

    8. AWAndrew Wilkinson1:12:42

       Yeah. I actually was in New Zealand for a ... It was a conference relating to getting citizenship, so yes, guilty as charged.

    9. CWChris Williamson1:12:48

       Been prepping.

    10. AWAndrew Wilkinson1:12:49

        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 remembered this guy that I'd met named Derek Sivers. Are you familiar with Derek?

    11. CWChris Williamson1:13:01

        He's been on the show, yeah.

    12. AWAndrew Wilkinson1:13:02

        He's amazing. And, uh, I had met him and he had been so kind to me when I was a ... I was a brand new ... I was a young pup. I had just started my company and I met him at a conference, and he was just so kind and engaged with me and, uh, I 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. Um, 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- 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."

    13. CWChris Williamson1:13:55

        Mm-hmm, mm-hmm.

    14. AWAndrew Wilkinson1:13:55

        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'd done entrepreneurship, I'd started a company, I had won gold and my brain was telling me, "You gotta win gold again."

    15. CWChris Williamson1:14:11

        Mm-hmm, mm-hmm.

    16. AWAndrew Wilkinson1:14:12

        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.

    17. CWChris Williamson1:14:22

        It wasn't a fluke.

    18. AWAndrew Wilkinson1:14:23

        No, exactly. And so Derek said, "You know what? I'm just gonna write. I really love writing and I'm gonna tinker and start new businesses, but none of it's gonna 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 get, I think, it's a million dollars a year or something, which is a hell of a lot of money. It's awesome.

    19. CWChris Williamson1:14:51

        Mm-hmm.

    20. AWAndrew Wilkinson1:14:51

        Um, so I admired m- I- I admired 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, um, 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. You know, those are the people ultimately, which is such a cheesy answer, but those are the people ultimately that I admire, I think.

Episode duration: 1:50:48