Morgan Housel: The Cost of Ego - [Glue Guys, EP.13]
4 Nov 2025 · 69 min
Podcast conversation (Glue Guys hosts Ravi Gupta, Shane Battier, Alex Smith) with Morgan Housel about his unconventional path from competitive ski racing to finance writing and authorship. Morgan recounts an interrupted education, traumatic events that ended his ski career, early jobs (valet) that sparked an aspiration toward finance, and a slow apprenticeship as a writer (Motley Fool, blogging with harsh feedback). Central themes: the need to toggle between humility and confidence (ego management), money as a window into identity and psychology, pressures faced by professional athletes entering wealth (keeping up with peers, family obligations), the value of short feedback loops, and the importance of defining the "game" you are playing (peak-end rule and finishing on your own terms). Conversation mixes personal anecdotes (e.g., publishers initially rejected Psychology of Money), practical advice about financial behavior and life decisions, and reflections on social comparison amplified by social media.
Chapters
I've always had the split personality that's been helpful. Of, on one hand, I feel like I can toggle between personalities. Of, on one hand, high ego. And like, I'm, I'm. I'm the shit. I'm really good at what I do. And then the next minute be like, no, what am I talking about? I have no idea what I'm doing. And I think if you can balance those that, like Jekyll and Hyde personality, you have the humility of knowing that you're a nobody, which is very healthy, and knowing that you need to work your ass off because you are a nobody. But then you have the confidence to be like, actually, like, I'm going to take a risk and try to become somebody. I think if you're always one or the other, you don't go anywhere. If you always. If you have. If you have low confidence, you're never going to get out of bed. And if you have high confidence, you're going to run off a cliff and everybody hates you. And so I think you need to be able to toggle between those really cleanly.
Welcome to Glue Guys. We're your hosts, Shane Battier, Ravi Gupta, and Alex Smith.
And we're bringing you behind the scenes of the wa. CL rooms, the boardrooms, and the living rooms that taught us everything we know about what it takes to be great leaders and even better teammates and friends.
We hope the conversation helps you bring more ambition and more joy to your own work, life and relationships. It certainly has for us.
Today we have my friend, Morgan Housel. For those of you that don't know Morgan, he is a brilliant author and a great friend. He has written multiple books. He has an amazing blog that I can give him the high compliment of. I have never read something that Morgan has written that I haven't liked, which is a crazy thing to say, but every single thing you've written I really like. And it's like, required reading for me. And my favorite thing, if I had to choose one, was Psychology of Money. Shane, I can't remember. Did you give it to me or did I give it to you?
We might have given it to each other. That's what it was.
There are so many things in that that, like, again, and it actually reminded me of what you said, Ravi, when you were talking about, like, you try to be the mirror for people, right? And you talk about that a lot, and I actually think that's really great. But, like, the book actually was kind of a giant mirror for me. It, like, kept making me think about Myself. And so often we're the other way. We live life, looking around, right? The grass is always greener. And again, even on social media makes it more obviously such a larger universe. But, like, the book was just this kind of giant mirror on my psychology and my ego and the choices that I've made and how those things are intertwined.
I read the book and I went through it again, but just being reminded that, like, everybody's journey is their own, and especially when it comes to money, it's hard. You're like, hey, what are you doing? What are you invested in?
Right?
And, you know, obviously you have buddies that may have a. Have a huge, you know, private equity deal that hits, or a crypto coin that hits, or a stock that hits. And there is the FOMO is a real thing. Until you step back and you're like, no, you know what? I'm good for what I do. You have to remind yourself, hey, run your own race.
Morgan, welcome. Thanks for joining us.
Thanks, Ravi. Thanks, guys. Happy to be here.
But I wanted to start with something that really surprised me, which is when I met you, I kind of thought that you were a kid who always knew he was going to be a writer about finance and about humans and about the human condition. And it was like, preordained. And I was shocked to hear that that path was not really the way it went. Would you mind just sharing a bit about your background? And one of the things we kind of focus on is the roads aren't always as clear as one might think. Would you mind telling us a little bit about your road to getting here?
Yeah. It was not. It was not planned in the slightest. And it took me years and years of doing it before I decided that this is what I want to keep doing for the rest of my career. Part of my background, which was pretty unique, I grew up as a competitive ski racer in Lake Tahoe. And because of that, ski racing is one of the only sports that views education in high school as a nuisance that you should try to avoid. And then so I and all of my other ski racing peers, I did this with more or less bypassed high school. We did an independent study program that was a joke. We did nothing for it. We got a piece of paper when we were 16 that said diploma, but we did. We did nothing for it. And so I spent my entire teenage years skiing, 10 months a year all over the world. And then when I ended my ski racing career, I was 18, the time most people go to college. I effectively had an eighth grade education. @ that point, I basically missed everything. Educationally, I had amazing childhood with great parents and such a good experience skiing all over the world. But educationally, going off to college, forget about it. I was an idiot. And then so I had to start at the very, very bottom of the educational world, like the most remedial math and reading and work my way up and went to a couple of junior colleges and then finally worked my way up, ended up getting my degree at usc. But even when I graduated, I was older than most people. I think I was 25 when I graduated, maybe just excited. I had so much time to catch up and really didn't know what I needed to do. But my education was important because I always had a chip on my shoulder of maybe I made it to a good school, but I'm an idiot. Everyone else is so much smarter than me because they went to high school, something basic like that. So I always had, I think looking back, I had really low self confidence in this, in this area. And then I graduated college in 2008, which was a terrible time to be looking for a finance job because the world was on fire. Financial crisis, everything's melting down, every investment bank's going out of business. And so I wanted to be a hedge fund manager or an investment banker, but forget about it. In 2008, nobody's hiring. And then so out of desperation. That's the right word, I found a job as a writer writing about the stock market for the Motley Fool. And if I'm honest, I hated it. I think I was embarrassed about it. I was like, I want to be an investment banker. And now I'm a blogger. Like, how did this, how did this happen? It was humiliating, honestly. And, But I did that for a couple of years just out of desperation of like, I need a job, I need to pay my rent, and this is the only group willing to, to pay me right now. But as the years went on, I think I slowly started to enjoy it and like it and felt like I was actually pretty, pretty decent at it and. But it probably wasn't until I've been doing it for five years before I was like, oh, I actually think I'm pretty good at this. And I, and I really enjoy it. And so now I've been doing it for, I don't know, 17 years, I guess, and I feel like I enjoy it more every year, honestly, just because you figure out your own style, your own voice, you get a little bit better at digging into society's moods and emotions and trying to figure it Out. And I feel like money for everybody is a window into their identity and their soul and how they think about life, their self confidence. That I think is really fascinating. So some people view money and investing as like, oh, stock market charts, data, Excel spreadsheets. I've often just viewed it as like, no, it's a window into your psychology. It's a window into your identity, both you as an individual and society as a whole. And that's the part that I found so interesting over the years. And once I discovered that, it was like, oh, this is. I love doing this. I can't get enough of this. And this is what I want to keep doing.
Morgan, to go back to that, that five year period when you fell in love with writing. Like, can you, I mean, dive into that a little bit? Like, did. Was there a mentor? Like, how. How did you learn? I mean, was it just like a, you know, kind of baptism by fire? You just jumped in and went, and what about it, I guess, did you end up loving?
It was definitely baptism by fire because it's, it's pretty rare today. But back then, every blog had a comment section and, and you guys will be familiar with this. If you, if I wrote a bad blog post, people let me know in no uncertain terms how, how awful it was. And that could be jarring. If you, if you have thin skin, that can really hurt. But for me, since I had to do it, this was not blogging for fun. It was like, this is so I can pay my rent. I can't quit. I have to keep doing this. That feedback, that brutally honest feedback from readers, if you pay enough attention to it, you just start getting better over time. And it was like, okay, I wrote this piece and it got filleted. People hated it. So what can I learn from that? What did I do that was so bad that I can try not to do again? And I think just that very slow adaptation over time, you figured it out. But I think what I loved about it, as time went on, which is what I hated about it early on, which was I was embarrassed that I was not a hedge fund manager. I was not an investment banker. I was not a big, powerful Wall street guy like I wanted to be. I was a blogger. And over time, I actually liked that, that I was not in the trenches, so to speak. I was an outside observer. Because I think people in it that are in the trenches are persuaded by a lot of biases, their professional biases. Like, if you're a hedge fund manager, you have to say that your strategy Works, even if you know in your heart that it doesn't just because your career incentives force you to say certain things. And so I love the idea that as an observer, up, up in the bleachers, I could say whatever I wanted. I could just sit there and watch with my binoculars what the economy was doing and try to figure out what was going on. And I was not persuaded one way or another to have an opinion. And that's, that's what I liked about it. Now, there's a lot of downsides to that. You know, there are people like Ravi who are in the trenches, who underthent, who understand things that I don't. But I actually liked being on the outside and just watching everybody interact and trying to figure out what people were thinking.
I find that super fascinating against the backdrop of your racing career.
Right?
So you came from. All you knew is competition. Do you make your time? Do you, first of all, do not crash? Do you not wind up in a hospital? Right? But, you know, you're, you're, you're playing a sport which is life threatening, all right? It's based on adrenaline, speed, and precision. And you go into this world of writing, of blogging, you know, and we talk about transition a lot on a lot of our, a lot of our guests. So talk about that. Talk about going from the need for speed and racing and competition to, you know, having some guy in his underwear. Talk bad about your columns. I mean, that's quite a contrast, is it not?
Yeah, I've written about this a little bit, but my, my ski racing career ended. I was, I guess I was 18 when two, two horrible things happened. My two best friends were killed in an avalanche while skiing. I was with them at the time. And then two months after that, I broke my back skiing didn't do any nerve damage, but really screwed me up. And both of those events were, you know, I was 17 or 18 years old. It had a huge impact on my entire life. And so, and that was the, at that age of ski racing, 18, there's kind of a, or get off the pot moment. You either made the US Ski team or you didn't. And for me, there's some people who go on and ski race for a college team, but it's actually more rare. It was definitely pretty common in my situation that it was like, hey, you didn't make it to the very top. It's time to move on. But since I didn't have an educational background, I was like, move on to what am I supposed to do with my life? Now and then I had this jarring experience of having my two best friends die skiing in an avalanche, and then I'm hobbling around with a broken back, and I was like, what am I doing with my life now? And I think that added to the chip on my shoulder of, like, everyone else who I knew went to high school, and now they're going off to college with a plan. And they even had a plan, like, after college, I'm going to go work for KPMG and I'm going to build, work my way up. And I was just floundering, like, what. What am I doing with my life? Looking back, I think that sense of fear was actually the best thing that ever happened to me. And I think a lot of those people, they're great people, but if you have a perfect high school experience, you. You go to a good college, you get hired by kpmg, I think that kind of just cushy. Even if they're working hard and doing it, never having to wake up in the middle of the morning and say, what the fuck am I doing with my life? What am I doing next? This is terrifying. I have no idea where I'm going. If you never experience that, I think you. You don't really fully understand how risk works and whatnot. So looking back, even if it was terrifying and I hated it, having that couple year period of my life where I really had no idea what I was doing, and I was terrified, and I knew the path of least resistance was me working for $8 an hour in a service job somewhere. That was. That was the road I was heading on for my career. Being that scared, I think did a lot for me. I think people deal with that fear in two different ways. They either become consumed by it and they can't make any decisions. They're like, I'm not going anywhere in life, and I'm too scared to try anything. I'm a loser. I'm not going anywhere. Or they are like, I'm going to run as fast as I can in the other direction. And I think actually most of the time I was in the former camp, I was like, I'm an idiot. I don't know anything. I have no skills. I'm gonna. I'm gonna be busting dishes. Dishes for my entire career. But I think there was a part of it where I got a little bit of escape velocity, and I was like, no, I'm gonna. I'm so scared of being there. I'm gonna run as fast as I can in the other direction.
I hear you on insecurity, and I feel like it. It does, like, strike, you know, certainly such a personal nerve for me. Cause, like, there's this idea, especially even back then, like, these resume kids. I've talked about it with, like, Ravi. Like, I was that kid. I was, like, senior class president and, like, had amazing grades and got into a bunch of great schools. And there's this idea that you look around and everybody has a plan, right? And they got it figured out. And I remember in my own head, it was like, I have no fucking idea what I want to do with my life. Right? Like. But you, like, try to display this, like, you got it together thing. Do you think, though, like, when you. Obviously, after you decided, you know, you're skiing, your competitive skiing career ends, and you've been going around the world, and you've kind of been independent, right, at this point? I mean, do you think that. That there's an element of confidence that I see in your story, where it's like, yeah, to go run the other direction and that you can go figure that out? Do you think that came from, though, this kind of. I know you didn't get a formal education skiing and chasing that to that kind of depth, but, like, certainly there was a life education, right? Traveling the world and even, you know, even. Even the learning experience, obviously, of your two close friends and then breaking your own back of, like, as scared, like, in that moment of fear. But also, like, I do have some control over this, and I'm gonna go. I'm gonna go. You know, the confidence to go chase it.
Well, here's what's. What's interesting, Alex. As I look back, there were about a dozen of us who were on the same ski team at the time. Same age, same educational background, everything. And. And. And I think all of us, except for the one or two who kind of made it out and became pro skiers, all of us, at age 18, had the same feeling of, what do I do now? I have no idea what I'm doing next. And if I'm honest, obviously won't name any names, but a lot of them did not make it out in good shape, and I think so. I think I've always had the split personality that's been helpful. Of, on one hand, I feel like I can toggle between personalities of, on one hand, high ego. And, like, I'm. I'm. I'm the shit. I'm really good at what I do. And then the next minute be like, no, what am I talking about? I have no idea. What I'm doing. And I think if you can balance those that, like Jekyll and Hyde personality, you have the humility of knowing that you're a nobody, which is very healthy, and knowing that you need to work your ass off because you are a nobody. But then you have the confidence to be like, actually, like, I'm gonna take a risk and try to become somebody. I think if you're always one or the other, you don't go anywhere. If you always, if you have, if you have low confidence, you're never going to get out of bed. And if you have high confidence, you're going to run off a cliff and everybody hates you. And so I think you need to be able to toggle between those really cleanly. A recent example, just a couple of years ago, when I had the idea to write the Psychology of Money, every publisher in the United States rejected it. Every single publisher who looked at it said, that's never going to work and we're not going to do it. So literally every American publisher turned it down and a small publisher in the uk, Herriman House, who ended up publishing it. But at that time, when publisher rejected it, I could very cleanly toggle between. One day, I would say those publishers have no idea what they're talking about. This is going to be a great book and I'm going to crush this thing. And then the next day I'd be like, of course they know what they're talking about. This is CEO of the largest publisher in America. Of course he knows what he's talking about. And this book sucks. But I think toggling between those two is actually a very healthy relationship to have. It's like the humility to know that you need to work hard and that you are a nobody and the confidence to know that if you put one foot in front of the other, you can actually improve your circumstances.
This is so helpful. And I think that like, I like the toggling point of it's not about being in the middle. It's not about like middle level confidence. Right. And happy medium. It's the toggling between the extremes. I think that's like a really helpful, you know, point just to keep in our minds. The other thing though that I was thinking about when you were talking about your story is I, I brought you up the other day to a friend of mine who's a father as well, right. And I, I think that a friend, you know, he's talking about how it's this idea of like, how do I make sure my Son is motivated enough to do what I know he can do. And I actually brought you up as an example, which is like, hey, listen, like, it's not always obvious when they're 14 years old or when they're 16 years old. Like, things can change later. And, like, you know, look at Morgan. Like, you know, my impression is that even at 18, it wasn't like you broke your back, snap your fingers. Okay, cool. I'm going to go work hard. Like, you were kind of bouncing around even before you graduated and did all that stuff. Like, what were the things that kind of brought you back to, like, going and working really hard, you know what I'm saying? Were there people that influenced you? And almost, if you think about it as like, what would you tell a parent who's kind of wondering what to do to help motivate their child, right? Who they're not sure if they're on the right track. How do they know if it's too far that they're demotivated? Do you see what I'm saying?
Yeah. No, I totally get it. Here's interesting about, about sports. The two ski racers from my generation who became international superstars are Lindsey Vaughn, who was back then named Lindsay Kildao, and Ted Liggety. Both of them won Olympic gold medals, became literally the best skiers of, of, of all time. What's so interesting about it is when Lindsay Kildow, or Lindsey Von, I should say, was five years old, she was in a different universe. You could, you could do. When she was five years old, she was in a different stratosphere than every other ski racer. It was so obvious where she was going. Ted Liggety, even when he was 16 years old, was good, not great. He was like a pretty good regional skier and then won the Olympic gold medal when he was like 21. And that's incredibly rare. I think Lindsay's situation for most athletes is more common. If you become a superstar, it was obvious from an early age that you were going to get there.
It's crazy. We have both those represented here of Shane was Lindsay, right? Fourth rated seventh grader in the country, and Alex was Ted.
Is that right? I love it.
Late bloomer.
I love it. And I have equal respect for, for Lindsay and Ted. But Ted, I think, is such a remarkable story of when he was 16. I think his coaches and his parents are like, oh, he's pretty good. Might have a, a career as a decent college athlete and became literally the greatest male giant slum skier in the history of ski racing. I think you have to have a certain mentality to do that with Ted being 16 years old, being like, I'm okay, but I'm going to wake up every morning and give this 10,000% to become the best skier in the world that I have a ton of respect for. For me, you asked like, what was my turning point. And I think it was very specific. After my ski racing career, I got a job as a valet at a high end hotel in Lake Tahoe. And that was my first experience with wealthy people. I had never experienced wealthy. I grew up in a middle class, maybe upper middle class family, but I never experienced a truly wealthy person or seen that. And so all of a sudden people are driving in, in Ferraris and Lamborghinis and I had never, I didn't know that those people existed in the world. World. And at the time I was like 18 or 19. So particularly through those eyes, I was like, whatever that guy's doing, I want that. Like whatever you're doing, that, that guy driving the yellow Ferrari, that's who I want to be. And as I looked into it, like virtually all of them worked in finance. They were hedge fund managers and investment bankers and honest, it sounds so trivial. But that was when I was like, great. I was like, I was like, that's. That's what I want to do. Great. Perfect. And that was my early now, I think as I dug into it more, I was like, oh, this actually does really fascinate me and interest me. But that was my shifting point of saying, I have no idea what I want to do to watching those people. And I was like, great. I still don't know what I want to do, but I want to be rich. Now. I think a lot of young men in particular have that. But it was not because I was interested in finance. It was more of like a lifestyle aspiration.
But the second half of that story is the most important part of that story, Morgan.
Right.
And the realization on that job as a valet. I love how you told the story and in Psychology of Money is that you realize that no one is looking at the dude in the car. They're just looking at the car. You know, that that guy could be, you know, that guy or that girl, they could be anybody. And like, I never thought about, like that. That was so well put to understand that, yeah, we're all chasing this, this, this crazy narrative of this life, but no one ever actually envies the person. They just envy the environment.
Everybody's thinking about themselves. Nobody's thinking about you because they're busy thinking about themselves. And even when they admire your car, what they're doing is imagining themselves with your car. They're not, they don't, they don't care about you. They could not care. I'm curious, Alex and Shane, if you have both seen that in sports where somebody's like, like overriding. No, but like specifically like their overriding drive was to become rich and, and they became good athletes, but what they really wanted was to become rich.
On that note, like, you know, obviously doing a little prep to get ready for this. Like, I think Psychology of Money should be required reading for, for everybody. But in particular, like every pro athlete, I think if you make a roster, should get handed a copy of the book and forced to read it because it is a fascinating environment. Just even observe like, listen, you are handing a boatload of money to young 20 year olds in an environment, right? Like, and then we've talked about this at length. The average career span is like under three years. In the NFL, basketball is short. Like even when you have a long career, you're, you retire when you're in your 30s, you got the rest of your life to like try to preserve this wealth. And, and you go into obviously at length in the book, the difference between making money and keeping money. Those are very different things. And this whole keeping up with the Joneses idea, and I totally identified with your valet story like you were talking about Shane. Like it was fascinating for you to put it like that because that's all it is it. You got all these rookies in there, they see all the vets pull up in their fancy cars and envision themselves in it and they go out and get it. They see the jewelry, they see like the, you know, going out and spending on dinners in the private plane and it's like, and they think they're living like this and it's, that's why the stats are unbelievable, right? Like, you know, it's something like over 80% of professional athletes go broke, right? Within like five years of their career ending, they get same thing. That's the same number for divorce, by the way. And it's all from a lifestyle standpoint. It's all this obviously the psychology that they carry with them when they come into money. So I think it's fascinating. I, I, I'm not sure if you, have you ever like dove into that as far as a, you know, a, a blog or a, you know, a piece to write about?
Yeah, there's two things I think about money with pro athletes. One is that everyone is impacted by keeping up with the Joneses. But for most Americans, the Joneses are literally their neighbors or their co workers. For pro athletes, the Joneses are lebron and Patrick at home. It's like a completely different universe.
They should change it.
Keeping up with the Jameses.
Right, Exactly. So even if. So if you are a rookie athlete making a million bucks a year. Incredible. A million dollars to play ball, like, amazing. But if there's people on your team who are making 35 million, then even if you're making a million, I guarantee you, you don't feel like you're doing that well. The other experience I had a couple years ago that was, had a huge impact on me was I did like a consulting session, I guess you'd call it, with a group of NBA rookies. And we were talking about the purpose was try to get these kids to not go bankrupt. And it was so fascinating because one of the players brought up this idea where he was like, look, everyone knows the stats about the percentage of athletes that go bankrupt. Well, people miss is that usually what causes an athlete to go bankrupt is not because they bought themselves a mansion and a flashy car. It's because they bought their fifth cousin a house, and they bought their, their grandmother a house and whatnot. And he was like, look, when you grow up in poverty and then all of a sudden you're making 5 million bucks, that's not your money. That's grandma's money. That's mom's money, that's dad's money, cousin's money, brother's money. You can't just tell the rest of your family and your crew to like, hey, I got mine. Good luck to you all back in the inner city. It doesn't work that way. So there's so much pressure when the extremes are so big. When you go from a lot of these guys growing up in poverty or middle class and all of a sudden they're making millions, that the pressure to hold on to that and, like, save it for a time is so, so incredibly hard. I think most of society doesn't have a lot of sympathy for that just because it's in the situation that they're in. But I, I, I empathize with the pressure that they have, Particularly at the age that they're in and the extreme numbers that they're dealing with. It's incredibly hard to manage. Right.
And Morgan, it's not even like, like the, the houses that you buy for your family members or your friends. It's like the small, like, like little costs that add up, you know, like, I don't know about you, Alex, but whenever you went to a. An opposing city, all right, you got hit up by everybody that knew you in that city. And they think that this giant, like, know a candy bowl of tickets in.
The middle, Tickets are free. You know, they just.
Candy bowl of tickets in the middle of the locker room. You know, what, Bring cousin Larry, you know, bring cousin George, you know, you know, like, like, we gotta pay for those tickets, right? And so you do that and you're spending out, you know, spending 2,000 bucks, 3,000 bucks again and again, city by city. Like, like those are things that add up when you go out to dinner, all right, every city, all right, Chuck comes around, everyone's looking at, looking at you, like, all right, like, and so, like these, like, no one's crying for, for us, and we did well. And, you know, I think both Alex and I, you know, live, live by the principles in your books and your blogs. But there is an immense pressure to say no. And that, that is, that is the message to any young athlete that, that first enters the league that I give them and say, you will be wealthy when you learn to say no. When, when no becomes the default. You will hold on to your money until that. Good luck, God bless.
But to that point, that's such a good point. Thank you. I'm curious to, for both of you, if you are particularly a rookie and you have a big contract, but you're financially savvy, so you're like, I'm going to save this. Like, I'm not going to blow this check. And you show up to practice in a Honda Civic. Does that, does that work with your team? Like, are you accepted by your other teammates if that's the life you're living?
My rookie year, I drove for a year and a half. I drove a Jeep Cherokee, not a Grand Cherokee. All right? I got a Jeep Cherokee.
What was your contract, Shane?
I was the sixth pick in the 2001 draft. And so essentially my contract was five years, 15 million.
Okay?
So 3 million bucks a year for five years, and you're driving Cherokee 25 years.
So I show up to practice in this Jeep Cherokee, not a Grand Cherokee. All right? Jeep Cherokee, you know, barely manual shift. And I mean, my teammates clowned me, man. Like, what are you doing? Like, you're in the league, like, live a little. I mean, I had guys who had five, six cars, and I'm driving my little, you know, you know, wearing my baggy jeans back in 2001. And I was, you know, look, I was so terrified of being broke, all right? I came from nothing, all right? I always had education and love in my house. I didn't have much more than that. And so I was always like petrified, petrified that I was going to be one of those guys. So I was like super frugal and I was clipping coupons as a rookie. So I'm like, I'm not going back. You know, I made it and I want to, I want to live a nice life for the rest of my life, not just the next couple years. And so I look back at those days and I, I laugh now, but like, I didn't care. Like, I was never the cool kid. Never, ever, ever. Even though I was a great basketball player, people always clowned me. You know, people made fun of my wrinkle head. I went to Duke, they thought I was some stuck up kid from, you know, from, from the suburbs. And so like, I realized at an early age I had the advantage that I was never going to be cool, all right? And my narrative was lame and boring and, and stuck up. And so I didn't like, you know, I, I didn't care. I, I, I really didn't care. I cared about, I had, I had a great life and I could do the things I wanted to do and still take care of my family and my people, which I did. So I had the advantage that I didn't give a shit. But most guys can't say no to that pressure.
Morgan, I have to interject for a second because I'm about to give you a gift. Shane, when you said that your narrative is that you were lame, can you please tell us the J. Cole story now about what he said about you and then how he stepped in. I feel like you gotta, this is the moment. This is the moment.
So most kids, my son's age, he's 16, Zeke's 16. They know me from NBA 2K, okay? They don't know like I played for Duke. They don't know I played for the Miami Heat and won two championships and did all this stuff. And so they know me from the video game. Well, they also know me from, you know, the great rapper J. Cole, all right, Huge North Carolina Tar Heel fan who called me lame. He said, you know, stay in your lane, you're shambadier, you're lame, whatever the line is. I'm not a rap guy, all right? So like, you know, I, I caught a stray, I never met the guy. You know, I figured he's a Carolina fan. We used to beat Carolina on the reg. So I'm like, he was probably just mad, but you know what? I probably am lame. So like, I owned it. Like, I didn't care. But like, so like, if you, if you go on Twitter or Instagram, like, kids just, you know, recite lyrics and no baddie. Yeah, you're lame. So like, I became known as the lame guy. Well, I was having dinner in Miami this past summer, and the mayor D. Came up to me and said, hey, like, there's this gentleman who wants to come speak to you and apologize to you. And I'm like, okay. Like, how was I wrong? He's like, I think his name is like, J. Cole. And I'm like, okay, who's, who's bullshitting me here? Like, by the way, there's someone said.
That I didn't do this. Yes.
There's someone yanking my chain. Like, okay, haha, very fun, guys.
I get it.
I'm lame. I'm lame. I get it. And she's sure enough, I go over around the corners. J. Cole was way bigger than I thought. Real life basketball, he's like 6 5. He's a big dude. And he, he's like, hey, man, like, I was praying for this moment that we would have this moment to where I could say, you know what, man, My bad. I was young. I'm sorry for, you know, you know, for you catching a stray at that moment. Like, man, don't worry about it, man.
I get it.
You know, the rap game, tough game. But I appreciated the, you know, the humility of, of a guy who put me on blast. And I wasn't angry. I. I thought it was. Was funny, but it was, it was, it was a really good moment. I appreciate you, J. Cole, you know, and, you know, I told my, my son, we took a picture, sent it to my son, and he was like, oh man, you know, there's hope for the world. There's hope for the world. And that is so. Yes, I probably am lame. But again, I'm, I'm past that.
That's, that's, that's a great story. I. I think I respect people more who screw up and then own up to it and apologize. Morgan.
I was just going to say back then, the rookie, the rookie wage scales, like, were different in football. I mean, I was one of the highest paid players in the league and hadn't done anything. And my nickname given to me immediately was Dollar Bill. Like, in the locker room, I walked around, they'd be like, what's up, Dollar Bill? Like, that's you know, and, you know, and you were expect, like, no, and I was deliberately. I. I bought every meal with the guys, like, and that. And I'll never forget the first one. We didn't even go to like a fancy. I mean, it was like an okay restaurant. And it was like all the O line, the receivers, running backs, and I actually think they weren't, they weren't like crazy. Like some of these tabs you hear about, they're like 40 grand. Like, I think I. It was like $4,000, right? Like in. In retrospect, like, not that bad. I was shaking, like, signing that. Like, shaking. Like, you got to realize like a couple months before I was living off top Ramen.
Right, right.
Like, you know, like Little Caesars pizzas in college. Like, you're just like, I, like, was. And I was so scared to death. And the shaking comes from this giant fear. Like, Shane talked about that you heard the stories. Like you, you get told. There is an education process by all these leagues, and it's just this fear. Everybody fucking goes broke, everybody goes bankrupt, everybody's getting divorced. And you're just like, oh my God, I can't be the one. Like, I can't. And so you're scared to death you're gonna lose all your money. And in that, like that moment, like you're buying these meals and like, I. That I'm like, oh my God, it's me. Like, you know, and there's this huge pressure from a lifestyle standpoint. Yeah. You go, there's this player lot, right? So like everything you do, I don't know if it's like this in basketball, Shane, but in football, like, you park in the player lot, right? Like, and players have a designated parking area everywhere they go at the facility, on game day, at stadiums. And you pull in and it's, man, it is time to peacock, right? Like you. You bring out the biggest, baddest you wear, right? Like, you can see it on Instagram today. It's. It's all part of the deal. And so you pull into this lot. Like, there was immense pressure. Like, you're the frickin number one pick. You the starting quarterback for this team, for this billion dollar franchise. Like, you better, you know, like, you can't just be driving nothing. And so lots, lots of lifestyle pressure for sure. And I think the thing that I really liked, again, to go back to your book, that there were lots of people that were old adults. I felt like, right. Like we're like talking down to us, you know, about all the all the stats, right. About the things that can go wrong. And nobody connected and nobody actually made this whole, like, psychology of it. Like, what's motivating you to do this? Right. Like, and I really think that's what's fascinating about your book, is that that connection, that it was actually inside me that I needed to look inside about this entire process and not all these other people and what they're doing.
And Morgan, I will say, though, like, the climate in the locker room is way different than when Alex and I played. Okay. You know, with. There's some awesome examples now of business athletes, you know, Serena and LeBron and Steph and Carmelo and Kate, you know, all these people who are owners. Right. And. And there's talk of ownership. I wanna, I want, I don't want to be.
Just be a partner.
I want to be an owner. Right. And so the education level has been elevated, the conversation has been elevated. Even though the mechanics are still maybe a little bit nebulous, there's a hunger and a desire to learn. Hey, what's franchising about? What's this private equity game? You know, I want to raise a fund. What's that look like? And that's maybe the most encouraging thing. So, yes, there are still people making poor choices in every industry, but at least I think there's. Now there's some. A little more hunger to be more sophisticated. And it's fun to see and I'm proud of these young guys for, for seeking that out.
There's a story from, from, From Kobe. What he talked about, he was like, once he saw that players became independently wealthy, they got lazy. And Kobe was like, I'm going to, I'm going to stomp all over these guys. They're fat and lazy now. It's going to be the easiest thing in the world. And if you, if you take someone like Kobe who just wanted. Wanted to be the best basketball player, like, and the money just comes naturally from that, then of course he was going to stomp all over him. I think you see that in every career too. You see with a lot of entrepreneurs, I'm sure you're right. Seen it all the time. You have your first startup, you're. You're. You're starving, you're hungry, you're going to work as hard as you can, and then you sell your business, you make a boatload of money, and you try to do another one and you can't. You don't have that motivation once you become independently wealthy. I think it happens to a lot of People happens to a lot of businesses. And that's why Boeing, General Electric, IBM, these, these companies that used to be the absolute dominators of their industry are not anymore. When you become that wealthy and you have wealth, no constraints on what you can do, you're just. You have money just, just dumped in your pocket. It. It helps to wake up every morning being a little bit scared. And once you take that away from a lot of these people, like, they lose what made them great to begin with.
And this is why there are, like, there are good analogies in business and sports of like, like Zuck is like, whether it's Kobe or MJ or somebody like that who just is relentless. Like, this guy is worth infinite, infinite money, right? And he is grinding, you know, because he just can't stop. And it doesn't matter that he made all the money. Doesn't matter. He has all the stuff. He just is going to go and he's going. And he happens to play in a game where he can play forever, right? He can just go. And it's so unique. But then to your point on the businesses thing, it's the same as ever point. Like, the reason they keep turning over, right, the top companies, is because they end up getting beat by somebody who's desperate and actually goes and builds something better. And I actually think that the relationship here is that the feedback loop gets.
To be too long.
Tying it back to your blogging point. You wrote something when you wrote for Motley Fool. People can comment, you know, immediately if it sucks, right? Immediately. When you run a big business and you're super profitable because of work that people did 10 years ago, when you don't get the feedback quickly enough that you stink, right? And as a result, it's just, you can be bad for too long and therefore, like you, you never kind of like, hit the field. You know what I'm saying? And so what you need is a quick feedback loop that tells you when you're no good. And what these businesses have and what, honestly, what people get sometimes when they're rich is like, the feedback loop extends too long or doesn't exist. And then therefore, they don't have any accountability. And as a result, like, they, you know, become shadows of themselves. And I think that, like, this is why you have to seek out real feedback and short feedback loop.
And then you go from thinking you're. You're a superstar to waking up one morning and realizing you're done, you're out. It just happened. It seemed like. It seemed like it happened overnight. But it was just a slow progression to that. I had a guy tell me once, he was like, every business should have a little bit of debt. Like, no business should be debt free because debt keeps you focused, it keeps you on. You're like, I have, I have debt to repay next year. We have to make this, we have to make these numbers work. Not too much debt, but it keeps you focused a little bit. And I'm curious, with these three guys, I would be lying if I said that didn't happen a little bit in my own career. That once I had a little bit of that, like once, once I had a little bit of financial success in my own life.
Love the honesty.
Yeah. Do I work as hard as I did 10 years ago? I think the answer is probably not now. I could also say that the reason I don't is because I only want to do my best work now. I don't need to grind for the paycheck that's going to pay for my groceries anymore. So I only want to work on the big projects. But I think there's probably, at least, there are days, maybe weeks, maybe months where I'm like, I'm not, I'm not doing that much anymore because I don't need to like I used to do. And I don't think that's good. I'm not proud of that, but I think it's realistic.
Do you think, though, on that note, because football, sports are different, right? Like football, we toe the line every week. The feedback loop is, is short and for Shane it's even shorter. It's every, you know, when you play basketball, it's every two days, like, and you're really only as good as your last game. And that's kind of probably what's fascinating about that, right? You be fricking Tom Brady. You go suck it up for a couple weeks, like you're going to hear about it, right? You know, look, look what Aaron Rodgers is going through. I mean, he is a first ballot hall of Famer, one of the greatest quarterback talents of all time. And it's just right, you just, you toe the line, you go stink out there, man. It's like they don't give a crap. But to go back to your point, don't, don't you feel like the goal is different for you though, Morgan? Now, like, given everything that you've accomplished, the bar is higher, right? And so to your point, like, you, you can't turn out something every week with that, that high of a goal, right? Like the, the product you turn out you have such high standards for yourself that, that it is going to be fewer and far between. But the demand then that when I do put something out, man, it's right like what I expect out of myself is probably very different than what you expected out of yourself 17 years ago.
Yeah, I think I experienced this with my second book, same as ever. Which, it's, it's, it's all subjective, but in my mind it was a better book than Psychology of Money. But the reviews do not say that in the slightest because I think what probably happened, at least for a lot of people, is the expectations were set for Psychology of Money and they're like, oh, his second book's going to be even better. And I'm like, ah, it's really hard to recreate that, you guys. I can't just keep doing that over and over again. But once you set, once you set those expectations and I imagine of course that's true for athletes as well. Of like someone who used to be 10 out of 10 and now they're 9 out of 10, they're still incredible. But the expectation was set up here and that's what people are always going to anchor to. And so that's a blessing and a curse. Nobody has, you know, feels bad for those people. But it's true that people are always going to measure you against the best version of your former self.
I was going to tell you, I think that it's interesting if I go to the startup world on the money side, it to me there's this very delicate balance. Okay. So there are some people who are just, they find motivations other than money and great like cool, like they, they, they that's, that's unique. And I think that most of the best founders ultimately because of the duration and longevity required, they have to have some other motivation other than money. Right. But I think what's interesting on what you said is it's almost like a little bit of secondary often is good for a founder, right. Because actually allows them to not be just overwhelmed by the fear of like, oh, foundation. It's zero. If this doesn't work, it gives them a little bit where they're kind of like, okay, like it's going to be okay. Now I can really be risk seeking, you know what I'm saying? But I think to answer your question for you know, me personally or whatever, you know, my, my version of this was when I worked at kkr. I was there when KKR went public and I mean I had nothing to do with like anything that good that happened there, but I was there, right? And so I got to, you know, be given some shares. And I think that for me, getting that first bit of, like, being there when KK went public, it actually allowed me to go to Instacart. It was a little bit like that secondary thing I'm talking about, where the fact that it was gonna be okay by whatever definition we decided of okay, that's what allowed me to take the pay cut, be more risk seeking, and go out and get it. And so I think that, I guess Morgan, in my experience, that was a little bit, it was more of an unlock having a little bit more financial flexibility. Because the specific question Avni asked me when I was like, you know, thinking about going to Instacart was like, do we have to sell our house? And I was like, no, we don't. And then she was like, can we still send our kids to private school? And I was like, well, I don't know if we can keep the house and send them to private school. You know, if I go to this thing. And then she was kind of like, okay, fine, like you, you can still go. But I think that, you know, it, it unlocked a little bit more risk seeking for me. I guess when I think about that.
There'S this really great quote from Warren Buffett who was once asked, give money to your kids without spoiling them and ruining them. And he said, leave your kids enough money so they can do anything, but not so much money that they can do nothing. And I think that's true for all of us in our careers. Once you gain enough money so that you can do nothing and, and, and keep everything up, including like your, your, your sense of self worth up, then that's. That, that, that, that's when it really starts to decline. Now, obviously, there are plenty of athletes and entrepreneurs who have enough money to do nothing and, and keep working as hard as they ever can. But I think it's rare. I do think it's the path of least resistance for most people that once they gain enough money to slow down, they're naturally going to slow down. And, and that's why I admire the people who don't even more.
The weird thing is, like, it was actually the goal, right? Like when you're playing, you're like, oh, if I can make enough money to do nothing, right? That was the goal.
Not above me, Morgan. It was not above me to say, yeah, I want, I want to make a lot of money, all right? I, I've been the other side. I want to Say, see how the other side lives. So 100%, that was a motivation for me. But it's funny though because like when I sign my big extension, you know, when I got to the NBA, I signed my, my five year deal, my rookie deal, you know, 15 million bucks, which is life changing obviously, but you know, as soon as you sign it, you're always, you're always okay, when's the next deal? Just get me to my next deal. Just get me to my next deal. Then every then everything is going to be good, right? And I'm sure it was like this for you, Alex. And so when I finally signed my contract, funny actually, funny story about that. The late Jerry west was my general manager and you know, obviously hall of Famer executive. And I was, you know, so nervous about signing my extension. He's, please get me to my extension. Please, please, please. And so my agent called Jerry and Jerry was very volatile and you never knew what Jerry was going to say. And so my, my agent, Lon baby calls him when I was up for an extension after my, my, my fourth year and he says, you know, hey Jerry, Shane loves it in Memphis. You know, his first year was, was with the Memphis Grizzlies and the franchise and he had grown up together, wants to spend, you know, many more years there. We think he's worth the mid level, the full mid level exception, which at the time was about 6 million bucks a year. And that, that the mid level exception is the average MBA salary. Okay, Take all the NBA salaries, you average them and like, that's like, so I was like the epitome of like an average player in my agent's eyes. And Jerry west may rest in peace, said I would never pay that, that he can't dribble, he's slow, he can't create his own shot. Like, you got to be smoking something, Lon, to think I'm gonna give bad a. The mid level exception. So my agent Lon calls me after that and I'm like, I'm out of there. Like, trade me. He doesn't appreciate me. Like, I've, I've let this team the playoffs. I bet for this team. Like, get me out of there. I'm, I'm out. I want trade. And Lon's like, we all know Jerry is kind of like, you know, a little volatile sometimes. Let's give him a, let's give him a break here. So my agent calls Jerry back a week later, a week later, one week later, and says, you know, hey Jerry, you know, we talked last week you know, about Shane, we still think he's worth the full mid level exception for six years. And Jerry was like, I couldn't agree more.
Let's do it.
So, so my agent hangs up, calls me back and tells me what Jerry said. I'm like, sign it.
Let's go.
Let's go right now. Let's sign it. So, you know, I was like, I don't care. Like, no more negotiation. I'm happy with that. Let's go. So the day I was supposed to sign the deal, like July 1, whatever, 2005, whatever, there was like a blackout, a citywide blackout in the city of Memphis. And I'm like, oh, hell no. Hell no. I'm, I'm walking over there, you know, someone, you know, fire up the candlelight. We are signing this contract today. And so when I finally signed the contract today, I was the last, the last class to be able to get a six year deal. You're like, I, I'd made it, I'd made it. I mean, 36 million bucks for next six years. And like all my dreams came true. And it's funny when that happens. I was one of those guys, Alex, who just loved hooping, you know, whether the NBA was there or not, I was gonna hoop. And, and so what that did. And I think you say it so eloquently, Morgan, in your books, you know, it. That allowed me to have the feeling to do what I want with who I want, for how long I want it.
Yeah, that's so well put. And I think being able to quit on your own terms is a huge part of whatever you do. Like, all of our careers are not gonna last forever. And being able to leave when you want to rather than getting a phone call that you don't want to have is so enormous. I respect the hell out of Jerry Seinfeld for this. Of On Top of the World, the biggest show ever. And NBC was going to pay him personally $100 million for one more season. And he said, no, we're done, show's over. And I have, I have more respect than that and anything else of that I've seen in that field to just be like, no, like, I did what I wanted to do. I completed everything. And he was asked later why he quit when the show was on top. And he said, the only way, you know, where the top is is to experience the downfall, experience the decline. And I have no interest in that. So he was like, look there, there might be more upside, but I'm, I'm cool right here. This is, this is all I need. This is enough. I have so much respect for that. I saw this happen to my dad too, who he retired on his own terms and some of his colleagues did not. Some of his colleagues were forced out and told, you're too old to keep working. You can't do this. The psychological impact on that could not be more stark of my dad feeling like he left on top, so proud of his career and his colleagues being like, I'm, I'm, I'm a failure. I got forced out.
We literally, like, you know, just a couple of weeks ago, we did. We were talking about transitions and we all brought up this idea of whether it's in sports or whether it's in business, whatever it is. All of us had this big important thing if we want to end on our own terms, whatever it was. And I actually will say, and like, it's obvious we all agree with this. I do think there is something to like, dig into there of, like, why do we care so much about that? Because if you really walk it through, like those other people who got cut, they, they chose to stay, right. They still had all those highs and then they just kept going and they kind of like wrung out every ounce of the towel, you know what I'm saying? And it's just all, all of this lives in our own heads of like, if you didn't walk away on your own terms, it's. I do think that there's, I suspect that says something about us still caring about what other people think or something of like, you know what I'm saying? Even though we say it's on our own terms, it's really so that like, we can tell other people, you know, I never got kicked out. And that's just kind of something that I absolutely. I do wonder about if it's still kind of like. Well, it's not really your own terms. Right?
Yeah.
So you can like seem cool to other people.
I totally know what you're saying. I think that's right, but I think it's just self preservation of your identity that like. Yes.
Yeah.
I want to be able to tell other people the. Jerry Seinfeld is an interesting example too, because since he left on top of. He was known when he left as the greatest comedian of all time and that allowed him to pursue a career afterwards in which he's probably literally made a billion dollars post show because he was known as the greatest. And there's a thing in psychology called the peak end rule, which broadly says your memory of an event is heavily influenced by how you felt at the very end of that event. So how you. So how you're going to remember a vacation is how you felt on the last day of that vacation. And you can imagine in sports, if your last game you get a standing O and people are like, greatest of all time, great career versus if you get cut in the off season and that's the end of it. Of course that's how you're going to remember, like, even if you had an amazing career, but you go out in poor terms, that's how you're going to remember everything, and that's how everyone's going to remember you as well.
One of the things I really like about what you just said, though, is like, I actually think a lot of what I've gotten out of your writing or your blogs or books is like, you don't have to, like, conquer your psychology as much as you have to be aware of it, right? Like, it is okay if you're like, look, man, like, part of the reason I want to do this is because of the peak end. Like, I'm going to remember it differently based on how it ends. I'm like, whatever that is, fine. I don't need to, like, conquer that. I just got to behave accordingly. And that's why so much of the value I get from this is like, helping me name it and be like, okay, do I want to try and change that or am I going to, like, live with that? You know, like, that's okay. And so I think about it. So much of the way I get to, like, hard decisions is like, what would I tell my kids to do? Right? And the real answer of, like, what would I tell them to do on, like, ending something? I'd be like, what is going to make you feel good about ending it? Right? Like, and do it that way. You don't need to do it for someone else's purposes. If going out on your own terms is going to make you happy, great, do it that way. But I think it's like a recognition of the psychology and it's like overcoming some of them. But, like, you putting words to it is something. I think that's a real gift.
Well, thank you. And I think so much of this that you. That you hinted at there is realizing how flawed all of us are. You, me, everybody. And don't pretend like you're going to find like, oh, this is the right way to do it. I think it's fine if you do things that look irrational because you should look in the Mirror and say, yes, I'm an irrational person. I'm not a spreadsheet. I'm not a calculator. I'm a hormonal, emotional, insecure person. And that's fine to manage reality around those constraints. I think once you accept that and you just embrace it, you're like, yeah, I'm not perfectly rational. I do have. I am a little insecure. I do have a little bit of an ego. We all do. Then you can manage those decisions around that reality rather than. Than pretending they don't exist.
Yeah, I mean, like, I'm like a investor professionally, who does not care that much about investing his personal account. Like, it's just a. Okay, fine, I don't care. I'm not gonna. Do you see what I'm saying? Like, fine, like that. That is something that. Just, like, I find it less interesting than I do. Like, but I really find investing, like, professionally interesting. Well, like, I don't know. That's irrational. I worked at a private equity firm. We, like, did. We took on a lot of debt. I, like, am really nervous about taking on anything personally, even though, like, I understand mathematically why it has so much potential and so much goodness. I'm like, I don't know. I don't want any of that. And so that's okay. I don't care. It's fine that it's irrational. It works for me.
And I think you become happier once you embrace your faults rather than pretend they don't exist.
Morgan, what have. What have you changed in your mind or thought about differently since you started writing anything either in finance or psychology that, you know, that you may read that you wrote at some point, and then you cringe like. Like we all did with our first podcast. You know, what do you think differently about today than you did, you know, early in your journey?
I think I'm much more open to the idea that there is not one way to invest or save or spend money, that everyone is different and we are investing in saving based off of. It's a reflection of our identities and who we are, which are based off of our experiences in life. So if I grew up an impoverished inner city child, would I spend money the same way that I do today? Of course not. Even if I had the same subsequent experiences and had the same knowledge and whatnot, I'd be a completely different person. If you grew up in China or Africa or Australia, would. Would you think about money the same way you do? No, of course you wouldn't. We're all just mirrors of what we've experienced in life. And since what you've experienced is different from what I've experienced, we are never going to spend or invest money the same way. And that's okay. It's not because I'm doing it right and you're doing it wrong or vice versa. It's just everyone's a little bit different. So I don't judge as much as I used to. I still judge a little bit, of course. But if you find a way to spend money and invest money that works for you and you understand the risks you're taking and you're getting some pleasure out of it, then great, even if it's very different from what I do. But I think that's a hard concept for a lot of people to understand. So it's very common to look at somebody doing things different than you. They spend more money, they invest differently and say, I'm doing it right and you're doing it wrong. I, I, I clearly know something you don't, or the opposite. You look at them and you're like, maybe they know something I don't and I should be spending more money. And I think usually that's, that's the wrong way to frame it.
So how, how do you look at the industry of advising? You know, and if you're giving advice to someone and say, well, if no one knows really, my, my spending habits and my saving habits, or my, my ethos on work, life, balance, yada, yada, yada, yada, how in the hell am I supposed to find anybody who gets me and can tailor something to suit my philosophy and my mindset?
I think money is such a personal thing that you can't expect anybody, particularly a stranger, to give you advice early on that's going to be suitable for you. And if you were looking for a spouse and you met a stranger and they said, well, this is what you should look for, this is who you should find. You'd be like, you don't, you don't know, you don't know me. You don't know what I'm looking for. And that would make sense. But a lot of people will meet a financial advisor and 10 minutes later they say, this is exactly what you should do with your money. And they think because there should be one right answer for what you should do with your money. So they think, oh, this advisor has that one answer and I should go follow it. But the truth is, like, for a financial advisor to really give you good advice, they need to know you for a long time. And maybe this is a dangerous thing I'm about to say, but I think it's probably true.
We love the angel.
A non financial professional who knows you might give you better money advice than a financial professional who doesn't know you. And I think, I think that's, I think there's probably a lot of truth with that, that your, your mom, your dad who knows you, even if they're not financial professionals will be like, no, like I, I know your personality and this is what's going to make you happy versus a financial advisor who just says this is what the textbooks say, this is what the spreadsheet says you can do. That's, that's not where you're going to find good advice. There's this great saying in social work. My brother's a social worker, he works, or my brother in law, I should say works with very disadvantaged kids who are in broken homes and abused at home. And a lot of those kids, not surprisingly, do not do well at school. They're always getting into trouble. They don't do their homework, they don't show up for school. And he said it's very easy for the teachers to look at those kids and say, what are you thinking? Why are you behaving like this? I don't understand what's going through your head. And then in social work they say all behavior makes sense with enough information that if you understood what that kid was dealing with at home, you would understand why they're picking fights on the playground. All behavior makes sense with enough information. And I think that line you can apply to almost anything in life, including like money and finance. And so when you see someone in a midlife crisis driving a yellow Lambo, you can be like, something happened. There's a story.
Alex, the day after he turned 40, he picked one up and he's been cruising around Woodside.
Banana yellow. I hear banana yellow.
I hear yellow cybertruc rolling around Woodside.
You know it is, it's true that people who have a strong desire to peacock, there's a story behind that. And I don't judge that story because I might do the same if I had their experience in life. And people who are extreme savers and always think that their career is going to, there's a story behind that. And everyone is like how they spend their money. It's just a reflection of what they've dealt with. And all behavior makes sense with enough information.
I like that. The thing that I was thinking about when you guys were talking a few different things, it like oscillates Between. When you think about, like, what do they know that I don't, right? When somebody that. When. When something gets hot that you don't understand, you know, you kind of oscillate depending on your confidence level of like, no, like, all these people are idiots or, oh, my God, I'm an idiot. Just this exact same thing of this dichotomy of, like, what. What do they know that I don't? And one of our partners talks about it. It moves between, you know, fomo, fear of missing out to fols, fear of looking stupid, and it just sort of like goes back and forth between those. But they're all. They're both based on fear, right? There's still some element of, like, you know, what are you thinking there? I think, you know, I was thinking about you, Morgan, on this. I have a lot of family that's in medicine, right? And one time, you know, when I was working at kkr, I was working in, like, the energy sector, and one of my cousins, who's a doctor, was asking me about, like, some oil and gas investment that, you know, had been presented to him. And I was like, look, man, here, I don't know anything about this investment, but here's. I'll tell you, in the oil and gas industry, they literally talk about, like, doctor and dentist money. And, like, you're a doctor, and they don't say it kindly, like, when they're going to go get the doctor and dentist money, right? So, like, I don't know anything about this deal. I'm just telling you, like, they don't. They don't say it nicely, you know, so, like, they generally don't think it's smart money. And you know what was interesting? It was just like a pretty clear recognition of. It's like, it wasn't about the risk return. It was sort of like being in the game, you know, it was an amount of money that he could lose, and he just kind of wanted. He didn't want to be on the sidelines. He kind of wanted to play, you know, and I think that, like, we talk about this all the time, and you talk about it in the book of, like, why do people try to beat the market? The market actually can provide. Exactly how much money do you want to have? Like, you actually, if you just put it in there and you went to sleep, you actually might have that amount of money. But the real thing I think that happens is people sometimes are not super clear on what game they're playing, and they just want to, like, win it, and they haven't spent enough time, I think, thinking about, like, what are you trying to accomplish? And then sometimes they have, and sometimes they're just like, it's, I'm not trying to maximize my dollars. I'm trying to play in a fucking game because I don't want to be bored. And I think that one thing I do poorly is like, asking people what game they're playing. You know, before I give the advice, I just like, assume I know what game they're playing and I give my advice and that doesn't work.
But who knows what game they're playing? I mean, if you ask that question of the founders that, that you're, you're working, you're working with or your fellow board members, like, how many people really know the game that they're playing versus playing a game that might seem like the thing to do, Right. Who has that talk about that self awareness? How many, how many people really know the game they're. That they're playing or want to play.
At least, by the way, real quick, I think that's what like also is kind of the core of your book, Morgan.
Like, figure out the game like I did. But here's what I don't think I mentioned this in the book, but I've learned over the years, is that the game shifts in your own life. The game that I was playing completely changed when I got married. It changed again when I became a father. It changed again when I bought a house. Like, it's always shifting. So even if you can, even if you're smart enough to define the game you're playing, you have to understand that it's always a moving target. And of course, I'm at age 40, I know things about life that I didn't know at age 20. And at age 60, I hope I'm going to know more than I do today and become wiser and smarter and look back at myself today and say, look at that foolishness. I hope that's the case. So it's always a shifting target. But I think people become so attached to, like, no, I figured life out and this is how they do it, that they become anchored on one game and they have no ability to grow and adapt and figure out the different game that they're playing.
Yeah. I think, Shane, to answer your question, in my experience, I think I kind of have in honor of Morgan here, kind of a dichotomous answer. I think the reason I like how will you measure your life so much that Clay Christensen book is because I do think it sort of Asks the ultimate question of what game are you playing? And I think that there, I do think that that can be consistent over some period of time of like, the love of the people who love you, like the Bob Myers quote, the people that know you the best should love you the most. I think that would be like an amazing way to measure your life. And I, I do think you could sort of like have that be consistent. So I love that book because I think it asked that question. And I think to answer your question, I don't think that many people could answer it that well. Right. I think that the way that I approach though, like founders, board members, anyone who I get to work with, I try now a lot more to like hold up the mirror to them so that they can figure out what game they're playing rather than trying to assert it and try to help them figure it out and then try to help them see are you behaving in a way that's consistent with that? And I would tell you, like, I think one of the things I do well of something I'm proud of is I think I can help people figure out what game they're playing as a friend or as a board member or as a partner. And I think that that helps them figure out what they want to go do rather than be like, just go do this. And so, no, I don't think that people always know, but I think if you ask three or four good questions, you actually can help them figure it out. And that's something I really enjoy doing of just like, hopefully helping them figure out what game they're playing.
One thing I think is true to that point too is a lot of people, if they don't know what game they're playing or they're unhappy with life, a very easy knee jerk answer is, I want more money. That's the easiest answer. It's very tangible. You can put a figure on it. I want, I want to make a million more dollars. Very tangible. And it's, it's such an easy answer because if I said I want to make a million dollars, that's easy to wrap my head around. If I said I want to become happier, well, what the hell does that mean? How, how do I do that? So they end up chasing more money because it's, it's the easiest thing to chase. It's the most obvious thing to chase. And for some people, that really is the hole they're trying to fill. But I think a lot of people, once they get that money, they realize the hole's still there because what they, they were unhappy with life, not because they didn't have enough money. It was because they didn't have any purpose. Nobody loved them. They weren't exercising their brain, whatever it might be. And so I think a lot of people that can be like, no one feels bad for rich people, of course, but there, I think there are a lot of rich people who make a ton of money and they're more depressed when they get there because they realize it did not fill the hole their entire life. They're like, as soon as my net worth is X dollars, I'm not gonna have any more problems. And then they get there and they're like, I have more problems than ever. And then they've lost hope. They had hope for years that money would solve their problems, and now it's gone. And so that's, I think that happens to a lot of people. It's easy to chase money when you're just putting a band aid over the bigger problems.
Well, I think Patrick Collison from Stripe has this thing, and I will kind of butcher the quote, but it's basically like, just because it's easy to measure doesn't mean it's the right thing to measure.
One way to frame this is which. Which of these people would you rather be? Would you rather make a hundred thousand dollars a year and have a great marriage? Your kids love you, your community loves you, everyone, you have tons of great friends, you're in good health, or would you rather make a million dollars a year, be divorced? Your kids don't love you, your community despises you, you're in poor health. It's so obvious what should be the right answer. So once you add more variables to the equation of like, which life would you rather live, rich and miserable or poorer, or like doing okay enough, but everybody loves you and you're sleeping well and you're. And you're health happy and healthy. It's so obvious which one I would, which one of those lives I would rather have. But it's always the case that because it's easy to measure, you're just going to say, no, I want more money. I think just in terms of evolution too, we're wired to. It's a competition for resources. And the truth is when you're competing for resources, it doesn't matter how much money that I have. What matters is, is that I have more money than you. That's how the competition works. It's just relative to other people. And one of the challenges of being in such a Wealthy society is no matter how much you're making, there's probably someone who's making more money to you. And then no matter, no matter where you are, your gaze is always just at the next person and you're just on this perpetual hamster wheel.
Where does the role of social media play in that? I mean, obviously it throws a lot of gasoline on that, on that, on that fire. How has that changed the discussion? How does that change the narrative around money? Even from the pre social media days of, of our childhood?
I think it's, I think there's two ways that make it infinitely harder. One is that the Joneses, as we talked about, used to be your neighbors and your coworkers, and now the Joneses is, are a curated highlight reel of the entire planet. And the people who are going to show up in your feed on Instagram and TikTok are the people whose posts have statistically generated the most fomo, among others. That's who then now all of a sudden, that's your benchmark. And, and the other thing is like, it used to be that when you are looking at your neighbors, you probably got a pretty decent, accurate snapshot of their life. You actually saw the car that they're driving. You saw them when they were angry, you saw them when they were sad. You saw them yelling at their spouse, heard them yelling at their spouse versus on Instagram. It's, it's all fake. It's all faux happiness, faux beauty, faux success. And so not only is it like, way you've expanded the people that you compare yourselves to, but you're comparing yourselves to a fake version of their life always. And I think everybody does this. I post, I post cute pictures of my kids on Instagram. I don't post pictures of them screaming. So everybody does this.
Totally.
Totally. And I think everybody knows too, the couple that in real, on Instagram, they post pictures and they're like, I love my sweetie, so happy to have you in my life. And you're like, and if you know them, you're like, what, you guys are on the verge of divorce? What are you guys talking about here? Everybody knows that when you, when you actually know somebody, you see the gap between reality and social media and they.
You only see the result. Again to like Morgan's point, like, all anybody sees is like this, you know, world famous author, right? And it like, it just was, this must have been destined to be. And, and everybody you talk to and you like, we don't get to see the struggle or the real fight or the real Story or the things they went through that shaped them. Jim Harbaugh would put up, and he still does this at the Chargers. I know this because I just went down there like every front of, on top of everybody's locker. He would put their senior class picture and they would, he would put your rankings, your recruiting rankings. So he would put like, wow, your, your rankings in your state and nationally at your position and overall. So you had like, you had like five or six scores up there. Right? And it was fascinating to walk around your point, Morgan. Like, it was pretty evenly split. 50, 50. You could walk around and see like highly, highly recruited high school seniors had, had fulfilled their destiny and become a professional. And there were just as many, if not more that were like zeros. Zeros, you know, recruit, you know, ranking, you know, two star, this, the thousandth ranked, whatever in their state or nationally. Like there were just as many. And I wonder, and I, and I bet that applies to every industry. I bet that applies to writers. I bet it applies to, you know, entrepreneurs and investors. And again, I think sometimes it gets lost in that all our paths are obviously so difficult.
Like, but the point is that doesn't matter.
Like, yeah, I was the fourth rated seventh grader in the country, but it didn't matter. I didn't like when I was out there. No one cared that I, what my radio was. Exactly. So I was fighting like, you know, just as hard as anybody just to like stay in the game and, and thinking, oh my gosh, I'm not good enough.
Right.
And so I, I don't like that, that feeling of like, okay, the haves and the have nots.
Right?
It doesn't matter how you get in.
The dance Morgan taught us is like, yeah, each group is envious of the other ones route because that's the human condition, which is to like, look at someone else and think that, you know, they must have had it easier or better or we have nostalgia or whatever. And I think the thing to recognize is like, no, like, you know, the only race that matters is the one you're running. Right. And to know yourself well enough. And I think, Morgan, what I'll tell you is you have helped me know myself better. You, I really believe this. You've helped me be a better friend. You've helped me be a better parent, better husband. Because I feel like I, I see myself in the writing that you do. And so many of the people that I love and respect do that too. And so I am genuinely grateful for our friendship. I'm grateful you responded to my cold email. You know, when we first got to be friends. And we are very grateful that you spent time with us on our podcast.
Right back at you guys has been so much fun to all three of you. Thank you. This has been a blast.
Thanks for tuning in to Glue Guys. We're on social media at Glue Guys Underscore Podcast, and we'll be back next week.
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