There's a saying I heard one time that you only live once — YOLO — is just as good a reason to not do something, right, as it is to do something. That's a very... usually when people say that, like YOLO, they're like, 'Oh, just go do it.' Like, no, YOLO, don't do it, right? [laughter] Right. And so I think about that a lot. And no, I do take risks. Most of my money is invested. There's things that I do. But I always think about, like, not what is the average risk, but what is the worst-case scenario that I could avoid here. And sometimes in life, by definition, you can't avoid the biggest risk that you don't see coming. Making peace in your head with what the worst-case scenario could be, if you know you can't avoid it — just making peace with whatever it could be. I think for a lot of people it pushes them towards focusing on what really matters in life. They're so focused on the next promotion, their net worth, what it might be. Like, look, you got your family, you got your health — like, none of that's going to matter after that.
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I have really been looking forward to this episode of Icons and Ideas because I'm here with Morgan Housel. You're the only person that I have given a book to my clients and my kids and my parents and known all of them are going to absolutely love it, and they all did. And you've just written several books that have really resonated with people. As someone who's read hundreds and hundreds of financial books, you could tell when you read your books that there's something magical about them. But I have my ideas. Why do you think you resonate so much, and not just in the US, but all over the world? I mean, before we started shooting, you were talking about you're in Korea and you're in Brazil and you're going overseas all the time, and people want to hear what you have to say. What do you think?
Well, first, thanks for having me here. It's an honor to be here and meet you, and thanks for having me. I think I've tried to do two things somewhat different as an author. The first is I only write for myself. I want to be, in general in life, a selfless person, but when I sit down to write, I want to be the most selfish person in the world. In the sense of, I know there's an audience, I know people are going to read this book hopefully, but they're not the most important part. I want to write for problems that I have in my own life, and with stories that I find interesting. And the only person reading it, the only review that matters, is mine. The line between knowing your audience and pandering to your audience is very thin. And a lot of people, when they're writing — not just a book, but an email to someone — will always have in their mind, 'Who's reading this and what do they want to hear? What will they understand?' And I've tried to completely throw that out as a writer and just say, 'I like this chapter. I like this book. I'm proud of it.' And so I think most people are very good writers if they take that view. Most people, if they're writing a diary and they know they're the only one who's going to read this — there's no other audience — they'd be a very good writer. You'd be a very clear writer, a clear communicator. It's only when you get nervous about the audience that people start kind of going in different directions and using sentence structure that they wouldn't in any other format.
The other thing that I've tried to do is, most finance books are an analytical lecture. They're analytical because they're data and charts and formulas, and it's a very math-based topic. And they're lectures in the sense that they tell you explicitly or not — they say you're doing it wrong. If you're doing it wrong, you're an idiot, and here's the right way to do it. And most people don't want to read that. They don't want to be told that the way that they've been doing it their entire life is wrong, and you may have screwed up your entire retirement, and you should have been doing it differently, and you should change everything that you're comfortable with and do something else. They don't want to hear that. It's not fun to read. And so rather than giving a lecture on what you should do — I never give financial advice to anybody in a book or anyone. I'm not in the advice business. You are. But what I've tried to do is say, here's a couple stories about how people think about money, right? And you can read those stories and contextualize that within your own life, because I don't know you. I don't know your own risks and goals and whatnot. So here's how people think. You figure it out for yourself. And so I think that if it's a story and it's not analytical, it's a very different form of content.
Now I'll say it's a different form of content because when we set out to publish these books, you know, every single publisher rejected Psychology of Money. Every American publisher turned it down because of what I just told you. It was an analytical lecture. There was no direct advice. And it's such a profound idea in the financial media space that a lot of editors, publishers want every article, blog, podcast, book to end with 'and therefore you should go take this action.' They wanted to be very prescriptive, and I thought that was bogus. I wanted to do something totally different. I wanted to write a book that did not give anybody any advice whatsoever.
And it's smaller than the typical book. Is it shorter than the typical finance book? Is that another part — were you having a hard time selling it because of that as well?
Definitely shorter chapters. Yes. You know, before I published my first book, Psychology of Money, I had been a full-time professional blogger. And so I got good over the years at writing an 800-word blog post. You know, fairly short. And when I set out to write the book, I was like, 'Oh, well, now I'm writing a book.' Most chapters in non-fiction books are about 5,000 words, but I was used to writing 800 words at a time. And I really struggled with it. It was not a length that I was any good at. And so finally, near the end of my deadline of having to turn this thing in, I just said, 'You know what, I'm good at 800 to a thousand words. That's what I can do. That's as long as my chapters are going to be.' So the chapters are two or three pages long. It's: here's a little story, here's the idea from that story, here's how you can contextualize that into making better financial decisions. Boom. Move on to the next chapter.
Of all the stories, what story do people come back to you the most with? All the dozens and maybe hundreds now of stories you've written — when people want to have you tell one of them again, or teach an audience about it, which ones do you find coming to the surface the most?
I think there's two that stick out. One is kind of the opening story from The Psychology of Money, which is profiling two people. One was a janitor, just a very humble, no-education guy named Ronald Reed, who had the most humble life you can imagine and earned minimum wage almost his entire career. And when he died, it turned out that he had millions of dollars that he left to charity. And when they dug through what happened, it was like nothing happened here. He just saved like 20 bucks a month and invested in stocks and left it alone for eight decades, and that was his whole story. And then you contrast that with people who have the best educations from Harvard and University of Chicago and worked for the biggest investment banks and became vice chairman of Merrill Lynch — was the guy who I profiled — and went bankrupt at the same time. And the point I made is, like, there's no other industry where something like that happens, where the person who has no education and no background does better than the person with the best education. It doesn't happen in medicine or engineering or anything else. It's a very unique thing about finance where what really matters is not how smart you are or what you know. All that matters is how you behave. And so if you understand the behaviors, like, boom, that's all you need to know.
Yeah. So much of what you write about is behavior. I mean, and so when you're writing, you don't really think about it like, 'Hey, I'm going to take something complex and make it simple so somebody gets a lesson that hopefully they read on their own, they conclude they should change their behavior.' You don't think about it that way. You're writing for yourself.
I'm writing for myself. I don't have the intelligence to make it more complicated than the simple story that I tell. It really is. I just try to have a problem in my own life that I'm trying to solve. What am I trying to figure out about money and long-term investing and retirement that, like, 'Oh, I'm trying to figure out how I should do this personally, and what's a good story that resonates with me?' Boom. That's start to finish. That's what it is. I think it's actually not a rare form of doing art, which is what writing is. I think a lot of comedians are like that as well. They're not sitting down and saying, 'What does the audience find funny?' They sit by themselves or maybe with some of their other comedy friends and be like, 'Hey, that's pretty funny. Let's try that out tomorrow night.' It's just, if it makes sense to you, it probably makes sense to somebody else.
With The Psychology of Money, at what point — so you release it. At what point do you realize, 'Oh my god, this is taking on a life of its own'?
Oh, it was before it even came out. Really. The first print run was 5,000 copies, which, if you know something about the book industry, like, to get 5,000 people to pull out their credit card and pay for your work when there's free podcasts galore — it's actually, if you can sell 5,000 books, that's really good. And I think before the book even came out, it did like 25,000 pre-orders. So we were like, this is crazy. So now we need to print 25,000 copies. And that was — you print 25,000 copies, they're gone in 48 hours. Now we need to print 50 and then 100. It took probably two years before we caught up. We just kept expecting the demand to just stop. We just kept going and going and going, you know.
Did you feel pressure after that? Like, how did your life change?
If I broke my life up into like 10 different parts, I would say like seven of those parts didn't change at all. You know, like my kids don't love me more. My wife doesn't...
Your wife's not overly impressed. [laughter]
No, not at all. The big things don't change at all. A couple things got better and a couple things got worse.
Yeah. And I'm sure this is probably true for the success that you've had in your career as well. And it's impossible to contextualize what's going to get worse before it happens. And for me, I'm curious if this is true for you too. The biggest thing that changed were other people's expectations. And so when you're first starting and you haven't done anything yet, everyone else's expectation of you and your own expectation be very low. And exceeding that can be pretty easy. Once you've had some level of success, people are like, 'Oh, you used to be here. Now you're here. You better be here next time.' Right? And if you're not, we're gonna be disappointed in you. That's a tough thing to do.
I still try to stay in my own head. Like the own internal benchmark of, like, other people's view of me — I'd be lying if I said I don't care about it, but I'm mostly concerned with, like, 'I like that book.' I've published three books. The last two did not sell as well as the first one, but I really like the last two, especially my second book, Same as Ever. I loved it. I was so proud of it. And again, I think that's the benchmark that matters to me the most.
So in terms of most of the important things stayed the same — you know, family, wife, kids, friends, all that — but you're saying that the expectations got worse. Anything else, or is everything else better?
No, I think what maybe has gotten better is, you know, I think I had a tremendous amount of career anxiety before I started publishing books. I always felt like things are going okay now, but I am one email away from things being really not okay. And especially after I had kids, then it was like it's not just my own ego anymore. I got a family to take care of now. And that, I think for a lot of people, but maybe more for me than average, I had a lot of anxiety about, am I going to make this work? What's great about writing is that, I mean, it's a very unique career. How many of my friends from college went on to become bloggers and authors? Like zero. None of them. And so since there's not an obvious career path — if you want to go be an accountant or an investment banker, there's a clear career path. You do this for two years, you get promoted to this level, it's a very clear path. You may not make it, but it's clear what the path is. For an author, it's like, you just go figure it out for yourself. There's no path whatsoever. And because of that, I think I always had a lot of anxiety of like, I don't know if I'm going to be able to pull this off because I don't even know what this is. There's no path. I don't even know what I'm doing. Especially before I wrote books and people would ask me what I do and I'd say I'm a blogger, you know, for a lot of people, particularly older people, that I didn't know that was a profession. I didn't — like, people pay you for that? That's... And so that gave me a lot of anxiety, and erasing that... It's not that I'm happier. There's a difference between being happier and removing anxiety in life. So it's not happiness, but it's a higher quality of life when you take it away.
So, you're writing for yourself, but I'm just going to say I think a couple of your gifts — you have many — are: you make things simple and understandable. And I think most people, they think that they come across as smart if they use big words and make things very complex. And I find it to be quite the opposite. So I find everything you write to be refreshing because of that. And then second, because the message is really about the person, not the investments. To me, when I read them, it's — I'm telling you a story, but you can be a better person if you take a lesson from the story. So you might not be trying to make those things happen, but I think it's a big, big key to your success. I know that's why I give it to my kids and my clients and my parents. I want them to go, 'Hey, there's going to be lessons in here. They might not be the same ones I took away, but you can't read a collection of your works — which is what basically I see all your three books as, basically that — like, you can't read them and not walk away with a couple lessons that don't change the way you think about the world and yourself, or your attitude about the way that you approach things.'
Do you really — when you look at the investment world, and you don't give advice, but maybe you can give me some color. How do you see the investing world? All this stuff out there — private investments, public investments, active, not active, tax-managed, whatever. Do you have a personal just worldview on all of this, or is this just not something that you like?
No, I think in general we're very fortunate to live in a world where, in my view, we've solved investing. Now, that was not true 50 or 100 years ago. If you were a dentist 100 years ago and you wanted to invest, your options were pretty limited, and you would go to some stockbroker who was going to charge you who knows how much fee, and the stockbroker would put you in whatever choice stocks that they wanted to put you in or that they were getting kickbacks for. It was a very imperfect way to do it, and a lot of people didn't have very much success with it. And you fast forward to today, where you can literally open an account with $100 and buy a low-cost diversified index fund. We've solved investing. We've figured it out. We understand what works, what doesn't, and the products are there for everybody. Every single person on the street down there can invest in a low-cost diversified way. Amazing. But we've solved investing, we have not solved the investor, right? And like, the behavior is not only not better than it was — in many aspects it's worse, particularly for young people, where a lot of the investing platforms that are out there are explicitly geared around gambling and not long-term investing. It's like, how much can you trade and just flip it over as fast as you can, and products designed for that cohort. And so even if investing is solved, the investor is not. And maybe it's similar to something like nutrition. Like, we understand a lot about nutrition, but people still make choices about what they're going to eat — that part still hasn't been solved yet. I think it's a similar thing.
I think the tragedy for the younger investor is they're just bombarded with the wrong information. I think that, like, not just are there more things out there that are gambling-oriented — not just pure gambling, but even some of the investments, many of cryptocurrencies, if not all, but at least many of them, they're just gambling. And then you have the people that are getting the most attention and the most influence online are people that are promoting things that are just absolutely ridiculous. And it's so frustrating to watch, you know, a billionaire promote a cryptocurrency that everyone knows isn't going to work out. I'm not talking about Bitcoin. I'm talking about like stuff that everyone knows is — and just to get some clicks. And then some kid — you know, I'll be talking to a university and all the time someone will raise their hand and go, 'But so-and-so online says...' And it just — you know, that if you're getting a lot of your information that way, and there's nothing wrong with getting information online, it's just the people giving it to you, their incentives aren't aligned with you. And I just — it's a treacherous world, I think, if you don't have somebody that you can really learn from helping you navigate all of it.
Yeah, I mean, if your take on the market is buy a low-cost diversified portfolio and leave it alone to the point of neglect for 30 years — watch how many times you get asked to go on TV. Watch how many newsletters you sell. It's not going to sell whatsoever. It's the person who pounds the table with a sense of not only confidence, but 'this is going to happen, this stock is going to double' — that's who gets it all the time. There's a lot of problem with pundits is like, people think they want good advice, but what they really want is advice that sounds good. That's a Jason Zweig quote. I love that idea. And the advice that sounds the best is never going to be the advice that you actually need over time, right?
And particularly for a 19-year-old who doesn't have the experience of understanding how this works, their brain isn't even fully developed at that point. And there's two theories for why Gen Z is so gambling-oriented right now. One is that there's a well-known thing in psychology where if you think all of your options are bad, you become very risk-seeking. And so through the mind of a 22-year-old, let's say, if they think that they can go get a job and work hard and get promoted and buy a house when they're 28, they will do that. If they think that option is not available to them, they'll throw it all on black. Why not? And so that's one theory of it. The other theory...
Hopelessness. You think the generation — a significant part of the generation has hopelessness.
I think it's true. I think a lot of that is documented in the surveys of how they feel about it relative to other generations. Now, I also think if you went back to the 1970s, the baby boomers were very pessimistic on the state of the world when there was Vietnam, inflation, whatnot. My generation, kind of post-9/11, financial crisis — that was not a fun time to be looking at just the state of the world. Is it any different now? Like, most people, when they graduate college and they realize how real the stakes are in front of them and how uncertain and fragile the world is, and their childhood is over — that can be a difficult time for every generation. I don't think Gen Z is any different. And maybe to that point, I think if my generation, the parents' generation, if they had access to Robinhood, Kalshi, Polymarket, they would have done the same thing. So it's nothing unique to Gen Z today. It's just they have the opportunity to gamble in ways that previous generations did not.
So, we were talking about stories earlier and you mentioned a couple of them. One story that I think — I don't know if it was a breakthrough story for you, but it definitely — you blogged about it at first and it seemed to me to get a huge amount of attention. And you put it in your book, the avalanche story. And I know it's a tragic story. You probably don't love telling it, but I think you've referenced it as shaping your thinking quite a bit, right? Do you mind sharing that?
So, I grew up as a ski racer in Lake Tahoe, California. That was my whole childhood, teenage years. And it was an awesome, awesome childhood. We really — myself and my friends who did it — more or less bypassed high school so we could ski six days a week. We did like an independent study program that pretended was high school, but we skied six days a week, 10 months out of the year. Went to New Zealand and South America during our summer, their winter. It was an awesome, awesome upbringing. And you know, we were very good skiers and we were teenage boys at the time. So you put those two things together, we took enormous risks that we didn't really think that much about because we were 17. And so a lot of what we did was skiing out of bounds, where you duck under the ropes that say 'do not cross,' and that's where the good skiing is. It's like untracked. You get the place to yourself. And when you get to the bottom of an out-of-bounds area, there's no chairlift. So we would do this all the time. And you get to the bottom, we'd hitchhike back. And so we'd ski out of bounds, hitchhike home. It was like so cool. We had this feeling of being a rebel. And it was the good skiing. It was really cool. So we did this quite a bit.
And this was February 2001. There was a huge storm that came through Lake Tahoe, and the layering of the storm was really important. The base, the bottom layer of snow was very light and fluffy, and then it was a wet storm that came on top of that. A heavy, heavy storm of snow on top of the light snow. That makes the mountain very fragile. It makes the snow very avalanche-prone. So my two best friends and I were skiing out of bounds. And as we're skiing out of bounds, we triggered a small avalanche — like, came up to our knees — and we were like, 'All right, this is awesome.' Just like it was like a roller coaster going down. And it's a crazy feeling. You have no control over your skis at that point. The snow is pushing you...
And you have no fear at this point.
At that point, yeah. No, we had — it was the first time I had experienced an avalanche. But again, it came up to our knees. We're like, 'Ah, it's not, you know, it's fun.' We get down to the bottom, we hitchhike back. My two friends, Brendan and Brian, said, 'That was awesome. Let's go do it again.' And I said — I don't know why I said this. It was probably that the hitchhiking always freaked me out. The avalanche didn't freak me out. The hitchhiking did. And so I said, 'Hey, I don't want to do it again. Brendan, Brian, why don't you go do it again? And instead of hitchhiking back, I'll drive around the mountain and pick you up.' So we went our separate ways. 20 minutes later, I go to pick them up and they weren't there. And I didn't think anything of it. This was before cell phones. If you didn't know where your buddy was, you didn't think twice about it. Before cell phones, it was like nobody knew where anybody was, right? And so I figured they hitchhiked back. I was a little bit late picking them up. They already left. Didn't think anything of it.
Later in the day, no one had seen them. No one had seen them. Several hours later, Brian, one of the guys, his mom called me at home and she said, 'Hey, Brian didn't show up for work today.' And Brendan, my other friend, didn't show up for a dentist appointment. Do you know where they are? And I said, you know, we skied on the out-of-bounds backside of Squaw, and I was going to pick them up, but they never showed up, and I haven't seen them yet. And Brian's mom, who's an expert skier, she instantly pieced together what almost certainly happened here. And so it was a couple hours later, I remember we called — someone called the police, and the police came and they're like, 'Look, 99% of the time this happens, the guy ran off with a girl for a night or they're drunk at a party or something.' And then I remember we were sitting in the ski team locker room and I said, 'That's — I can guarantee you that's not what happened because their sneakers are right there.' And at this point it was like 10 o'clock at night. And I was like, 'Their sneakers are right there. That means their ski boots are on their feet and it's 10:00 at night, pitch dark outside. Piece everything together.' They got search and rescue involved, went out on mountain at like midnight. They had these giant floodlights to go look for them. And as soon as search and rescue got up to the out-of-bounds area where they skied, they flipped on the floodlights and it was like half the mountain had been torn away. Like the fresh scars from what had clearly just been a massive avalanche that had just occurred. And it only took them a couple hours. They brought the search dogs out, and the search dogs kind of homed in on an area, and the rescuers had these probe poles. They just probed down and they found them the next morning, dead. They were under six feet of snow. And so we were 17 at the time.
And I think I always have to tell the story that, like, whenever I tell this story, like, you and everyone listening has lost somebody. Like, I'm not unique in that sense. Maybe the circumstances were interesting, but everyone's lost somebody in a tragic accident, you know. But one of the things that I did think about — and I didn't want to be too cheesy to, like, tie this to an investing lesson — like, but we knew when we were 17 that what we were doing was dangerous, but we thought the cost of the risks that we were taking, the downside was that we'd get caught. That was the downside that we were trying to protect against — was like, someone might catch us skiing out of bounds and arrest us. Never did we think the consequences of the risks that we would take were that we'd die. Like, never, ever, ever did that ever cross our minds. And so it's this idea that, like, the average risk in your life that you're thinking about probably doesn't matter. It's the out-of-the-blue one-in-a-million risk that you need to focus on avoiding. And that could be true for a lot of things in life. For investing, like, the average loss doesn't matter. Getting wiped out because you invested on margin — that will change your life. That's what you need to avoid. Like, the big tail events are the only thing that matter in life and investing. And sometimes you'll learn that the hard way.
So you touched on investing. Tell me, in life, what other tail risks do you think about now differently, having been shaped that way at such a young age?
There's a saying I heard one time that you only live once — YOLO — is just as good a reason to not do something, right, as it is to do something. That's a very — people say that, like YOLO, they're like, 'Oh, just go do it.' Like, no, YOLO, don't do it, right? [laughter] And so I have perspective about that a lot. And no, I do take risks. Most of my money is invested. There's things that I do. But I always think about, like, not what is the average risk, but what is the worst-case scenario that I could avoid here. And sometimes in life, by definition, you can't avoid the biggest risk that you don't see coming. Making peace in your head with what the worst-case scenario could be. If you know you can't avoid it, just making peace with whatever it could be. I think for a lot of people it pushes them towards focusing on what really matters in life. They're so focused on the next promotion, their net worth, what it might be. And like, look, you got your family, you got your health — like, none of that's going to matter after that.
You've got a very stoic view of the world. Is that a fair...
You try. Stoic is much easier said than done.
You know, the actual Stoics used to, like, daily envision what it would be like if their children died, right?
That's for them, not me. They would do it on the idea that, like, prepare for every opportunity that could happen, and then when it does happen, you're okay with it. So they got really extreme with this stuff. So I think I like stoic light.
Yeah. That almost feels like inviting unnecessary suffering. I'll pass on that.
I think they intentionally suffered so that when a real risk happened, they didn't even know it.
Interesting. So you talk about risks and tail risks, and you were talking earlier about, hey, we solved the investing problem, but not the investor problem. What is it you think about wealthy people that blow up? We hear story after story about the wealthy person that lost everything. What do you think it is that drives that?
I think for a lot of people, it's not necessarily being rich that they like. It's the process of becoming rich that feels really good. And because of that, what they like is the upward slope. Right. And so if there is no finish line at which you're like, 'Oh, now I've got enough. Now this is enough,' they're always going to keep going and keep going and keep going. And for a lot of those people, keep going will mean they take too much risk that blows up in their face. They had too much ambition and then their personal life falls apart. It'll be something where they misunderstood the cost of the ambition that they had. Will Smith, the actor, had this really good framing where he said, 'Becoming famous is the most amazing feeling in the world. Being famous is merely okay, and losing fame is one of the most miserable experiences [laughter] that you can have.' But I think wealth is like a very similar thing. You only enjoy the upswing, or you enjoy it more than you do having the actual...
wealth. And so if there is no satiation, there's no sense of enough, you just keep going. But you think there should be, and you constantly tell yourself, you know, when you're young, you're like, if I had a million dollars, all my problems would go away. And then you get there, and like 10 million, okay, 100 million. You just keep going because you're always telling yourself that at the next marker, then you're going to be good, then everything's going to be great.
A lot of it is, I think, money is such a tangible way to measure how you're doing in life that we use it as the ultimate metric even if you know it's not. And so if I said I want to become a 10% better dad, it's a very good goal. I'd love to be a 10% better dad. But what does that even mean? How do you track that? How do you compare my dad score to yours? Like, there's no way to do that. But if I said I want to increase my net worth by 10%, I can track it down to the penny and compare mine to yours. Like, it's so tangible that it becomes the ultimate yardstick of how you're doing in life, even when you know it should not be.
And so for a lot of wealthy people, I think it can drive them crazy if they're like, look, by this metric I'm off the charts, but by health, family, purpose, whatever it might be, I'm merely okay, if not struggling. And that can drive them crazy if by the ultimate metric they're doing great.
I learned this from my clients, is that when they've got a successful business or they're making partner in their firm, and all of that stuff is so fun, exciting and exhilarating, and then they get there and then people are coming after them, and so a little bit of the glow is off, or now everyone's got an opinion, you know, so there's praise, but now there's criticism that comes with it. When you're not so successful, there's not that criticism, and then you're worried about losing that position. And so you see these people, I'm sure that's what Will Smith is talking about. So whether you're looking at fame or politics or business or sports, I mean, the path to the top, it's got to be so much fun. But for a lot of people, and I've just seen this with my clients, when you're there, you look around and go, the friendships haven't changed, my family hasn't changed, but this maybe isn't everything I thought it was cracked up to be. And maybe if you're too ambitious, as you said, you paid the price with the family and the friendship.
Yeah. For the vast majority of very wealthy people, the reason they got very wealthy is because they made enormous sacrifices in other aspects of their life. Not everybody, but the majority, that's the case. You know the podcast Founders by David Senra? Phenomenal podcast. He's interviewed, or he's profiled, I should say, 400 of the greatest entrepreneurs of all time. And of those 400, David will tell you there was only one guy named Ed Thorp that he genuinely said, 'I wish I had his life.'
