What Great Investors Do

27 Dec 2025 · 49 min · 21 chapters

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In short

Podcast Notes: Motley Fool Money - "What Great Investors Do"

Episode Overview Host: Robert Brokamp Guest: William Green, author of *Richer, Wiser, Happier: How the World's Greatest Investors Win in Markets and Life* Air Date: February 2023 Companies Mentioned: BRK.A, BRK.B, MKL

Episode Description In this episode, William Green shares insights from his book, focusing on:

  • The essence of successful investing
  • Key personality traits of top investors
  • Lessons from noted investors: Charlie Munger, Howard Marks, John Templeton, and Arnold Van Den Berg

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Key Themes & Discussions

The Nature of Successful Investing

  • Reality vs. Prediction: Green emphasizes that while predicting the future is impossible, one can adapt to current realities (inspired by Howard Marks).
  • Existential Questions: Green's motivation stems from a desire to understand how money contributes to a fulfilling life.

Personality Traits of Successful Investors

  • Maverick Spirit: Successful investors often blend learning from others (cloning) with unique, independent strategies.
  • Cloning vs. Originality: The contradiction between imitating successful investors (e.g., Monish Pabrai's cloning approach) and the independent thinking of investors like John Templeton.

Learning from Great Investors Charlie Munger

  • Munger’s emphasis on continuous learning and intellectual curiosity.
  • His philosophy of recognizing one’s own limitations and avoiding overconfidence.

Howard Marks

  • Marks advocates for understanding the impermanence of markets and adjusting one’s strategy accordingly.
  • The importance of surviving downturns and recognizing emotional biases in investing.

John Templeton

  • Templeton's counter-intuitive strategy of buying stocks during periods of maximum pessimism.
  • The lesson of humility in investing and avoiding emotional decisions.

Arnold Van Den Berg

  • A personal story of resilience, overcoming significant hardships to become a successful investor.
  • Emphasizes the importance of helping others and finding purpose beyond personal gains.

Investing Principles

Key Takeaways

  • Margin of Safety: Always invest with a safety buffer to mitigate risks.
  • Understanding Risk: Be aware of emotional fragility and the unpredictability of markets.
  • Continuous Learning: Great investors read extensively and foster a mindset of lifelong learning.
  • Probabilities and Odds: Successful investors utilize game theory and probability assessment in their decision-making processes.

Practical Applications for Investors

  • Simplicity in Strategy: Focus on simple, robust investing principles (e.g., stocks follow earnings).
  • Diversification: Don’t put all your eggs in one basket; maintain a well-rounded portfolio to withstand market fluctuations.
  • Self-Honesty: Recognize personal strengths and limitations in investing to make informed decisions.

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Conclusion William Green's discussions provide rich insights into the mindset and strategies of the world’s greatest investors. The episode highlights the importance of continuous learning, emotional resilience, and the ability to adapt to changing market conditions. By understanding these principles and applying them, individual investors can enhance their ability to navigate the complexities of the market.

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Disclaimer The content in this episode does not constitute financial advice. Listeners should conduct their own research and consult with financial advisors before making investment decisions.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Exploring Investor Mindsets

0:45 to 2:51

William Green discusses the characteristics of successful investors and their approaches to life and investing.

“So William, you've interviewed countless investors over your career through your writing, your own podcast, and you could have made this book just about cold, hard facts about investing, investing principles.”

Contradictions in Investing

2:51 to 5:36

Discussion on the balance between learning from others and forging one's own path in investing.

“And Bill, you know, had beaten the market famously for 15 years running.”

Pragmatism vs. Individuality

5:36 to 8:26

Insights into how great investors combine learning from others with their unique perspectives.

“And in a sense, the first chapter and the second chapter conflict with each other totally.”

The Nature of Great Investors

8:26 to 13:19

William elaborates on the obsessive nature of successful investors and their dedication to learning.

“And so when I'm studying Monish, I'm thinking, and Monish has become a good friend over the years.”

Lessons from History

13:19 to 14:03

Reflections on how historical lessons in investing can be applied to modern practices.

“And there's something sort of deeply subversive about me, I guess, that was drawn to these sort of slightly strange, subversive creatures who had sort of cracked the code of the markets.”

Growing Up and Rule-Breaking Insights

14:03 to 14:26

Learn about the speaker's background and their perspective on rule-breaking in investing.

“I went to which was, you know, this famous boarding school where we were literally locked up at 6.15 every evening.”

Historical Lessons from the Past

14:26 to 15:10

Understand the important lessons from Johann Rahl's story and its relevance to current decision-making.

“When Johann Rahl received the letter on Christmas Day, 1776, he put it away to read later.”

Investors on the Value and Growth Spectrum

15:10 to 15:24

Explore how different investors align themselves on the value and growth spectrum.

“Find us at constantpodcast.com or wherever you get your podcasts.”

Munger's Perspective on Value in Investing

15:24 to 16:40

Discover Charlie Munger's insights on successful investing and getting value for price.

“To the degree that investors can be classified along sort of the value and growth spectrum, I would say most of the investors that you profile lean toward value, not exclusively.”

Simplicity in Investing Strategies

16:40 to 18:55

Learn how simplicity can enhance investment decisions and reduce complexity.

“And Bill at one point a couple of years ago said to me that he was the single largest individual shareholder of Amazon, not named Bezos.”
Show all 21 chapters

Understanding Margin of Safety

18:55 to 21:57

Examine the concept of margin of safety in investing and its importance.

“principles themselves are quite simple the application of the principle requires an amazing degree of intensity.”

Reducing Fragility in Investments

21:57 to 23:46

Explore methods to reduce fragility in investments and ensure financial stability.

“And so I think if you have all of your money in one asset class or all of your money in one bank account or one brokerage firm or one currency, you're playing with a loaded gun.”

Estimating Odds and Probabilities in Investing

23:46 to 24:45

Learn how successful investors estimate odds and probabilities, impacting their investment decisions.

“These are things where there's tremendous downside and limited upside.”

Applying Game Theory to Life and Investing

24:45 to 28:00

Understand how game theory concepts apply to both investing and life decisions.

“Another common theme with many of the folks you profiled was the ability to basically estimate odds and probabilities of something.”

Identifying Your Strengths in Investing

28:00 to 29:12

Learn the importance of aligning your investments with your personal strengths and interests.

“professional basketball player competing against people who are eight foot tall, you know, find something where you have a natural talent, where you have natural advantages and that you're obsessed with.”

Ed Thorpe's Roulette Strategy

29:12 to 30:56

Explore how Ed Thorpe turned chance into skill in investing and the implications for personal finance.

“I have to point out, and you explain this in your book how Ed Thorpe managed to play Roulette's.”

Lessons from John Templeton

30:56 to 37:06

Understand the unique investing principles of John Templeton and how they can guide your own strategy.

“Let's dig a little deeper into a few of the characters that you discuss in the book.”

Howard Marks and Embracing Change

37:06 to 41:20

Discover Howard Marks' philosophy on unpredictability and how to navigate market changes.

“That's so funny, especially for someone who, by the way, was also very religious.”

Arnold Vandenberg: A Unique Perspective

41:20 to 42:00

Meet Arnold Vandenberg and learn about his extraordinary journey and insights on success in investing.

“overestimate their knowledge by something like 30%.”

The Inspiring Journey of Arnold Vandenberg

42:00 to 45:35

Learn about Arnold Vandenberg's incredible life story and resilience.

“And this is one of those things where you just want to remind yourself, if you're a man, that we should be particularly aware of our capacity for overestimating what we know.”

Lessons from Arnold: Giving Beyond Self

45:35 to 47:51

Discover how Arnold's mission to help others leads to true happiness.

“And he's continued to be a great role model to me.”
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Transcript

Automatic transcript. May contain errors.

0:00The lesson in some ways that I drew from Howard that's been life changing for me is you can't predict the future but what you can do is accommodate yourself to accommodate yourself to reality. as it is.

0:16I'm Robert Prokamp, and that was William Green, the author of Richer, Wiser, Happier, How the World's Greatest Investors Win in Markets and Life. Really one of the best books about investing and investors that I've read over the past few years. In this replay of an interview from February of this year, I caught up with William to discuss what successful investing comes down to, personality traits of market beaters, and the investing lessons from Charlie Munger, Howard Marks, John Templeton, and Arnold Vandenberg, an investor you may not know about, but you should.

0:54So William, you've interviewed countless investors over your career through your writing, your own podcast, and you could have made this book just about cold, hard facts about investing, investing principles. But it's not just that, right? You do many sort of mini biographies of famous investors and not quite such famous investors. You explore their life stories, their work habits, psychology, in some cases, spirituality. What led you to choose that path for this book? I think part of it is just that I'm so full of existential angst that I'm always trying to figure out how we're supposed to live.

1:32And so part of that, obviously, is figuring out what role money plays in our life. You know, how can I create a life where I'm free to do what I love to do? How can I have financial independence and financial security? But I think all of us sense that that's not enough. And so I'm always looking at these questions and thinking, yeah, but so then what actually will constitute a rich life? What will constitute an abundant life? Is it possible to live in a way that's truly aligned with who you are and yet also be part of the group? Is it possible to live with integrity and honor and truthfulness?

2:11Or is that kind of naive in a brutally Darwinian, capitalistic, dog-eat-dog environment? Or how do you deal with the fact that the future is unknowable and yet we have to make decisions about the future? So for me, a lot of what's happening is that I'm actually wrestling with these questions myself. And I just happen to be in this very unusual position that I've had extraordinary access over really the last 30 years to these incredible investors who are so thoughtful. So when I was full of existential doubt and I was wrestling with one of these questions, I would get to talk to them about it. So I would get to talk to someone like Bill Miller, for example, who I've probably interviewed for the best part of 100 hours over the last 25 years or so.

3:00And Bill, you know, had beaten the market famously for 15 years running. And so I interviewed him at the height of his fame when everything was going beautifully. But then I also interviewed him when it all fell apart during the financial crisis. And then I also interviewed him when he rebounded massively. So I would go see Bill after the financial crisis, for example, when I was going through pain myself because I had edited the international editions of Time magazine and then got laid off in the middle of the financial crisis. And I would say to Bill, so how do you deal with pain and suffering and failure and public humiliation?

3:43You know, how do you wrestle with it? And here I would have one of the smartest, most thoughtful people who'd gone from managing$77 billion at his pinnacle to something like$800 million. And he would say to me, well, look, you know, I studied the Stoic philosophers for many years. And he was actually he was in a Ph.D. philosophy program many years ago. and he said to me, I know from the Stoics that I can't control my reputation or what people say about me, but I can control my own actions, my own behavior, my willingness to deal with my mistakes and be honest about them and learn from them. And so really for me, I just had this crazy access to people like that.

4:24And so anytime I was going through anything, I would want to ask them about it. And then I wanted to share what I learned with the readers. So in some way, I sort of almost think of it as a stealth spiritual book or almost like a self-help book for investors, where you're wrestling with these profound questions about how to live, how to think, whether you can construct a really happy and abundant life, what habits are required to get you there, how you should behave and how you should think more wisely. Yeah, I think there's no doubt that anyone who reads the book will certainly come away with some investing lessons, but with definitely some life lessons as well.

5:05When I look through the people that you profiled and the things that they believe, it struck me that there were two things that came out in almost all of their lives, and they're somewhat contradictory. One is they spend a lot of time learning about other investors from other investors, maybe even cloning what they have done. But then number two, the best investors are also mavericks. They're really blazing their own path. So let's start with that and talk a little bit about the cloning aspect. Yeah, it's a very perceptive comment. And in a sense, the first chapter and the second chapter conflict with each other totally.

5:44because the first chapter is about Monish Pabrai and the idea that really, instead of trying to reinvent the wheel, what you should do is study people who are wiser and smarter and more experienced than you, reverse engineer what they did and figure out how to clone it. And the second chapter is about Sir John Templeton, who's a total emblem of being non-tribal, free thinking. When I asked him if anyone had influenced him, he said, no, nobody at all. And I said, not even his parents. Yeah. He's like, yeah, not even my parents. And, and so in a way, those two chapters are contradictory, but I think there's, there's something, and look, this goes back to that beautiful line from F.

6:28Scott Fitzgerald, where he talked about the ability to hold two contradictory ideas in mind without going crazy, that that's sort of a mark of intelligence. And I think that's true, that usually the great truths are contradictory. So I think with the great investors, one of the things that struck me about them that makes them such a good filter to study the world is that they're great pragmatists. And so they'll just do whatever works. So for a lot of them, even if they're very independent spirited and non-tribal, they're just pragmatic enough that they're going to say, well, what's everyone figured out already?

7:06And so Monish, in a way, is a perfect example of this because he's someone who grew up very poor in the outskirts of Mumbai and discovered early on that he had an extraordinarily high IQ and then stumbles on a book by Peter Lynch in Heathrow airport that mentions Buffett and realizes that Buffett is the master of compounding and says, well, let me just reverse engineer this game and figure out how he compounded at such a rate. And so Monish kind of discovers that basically the principles of investing are almost as timeless as the principles of physics. And he says it really comes down to what Ben Graham taught Buffett, more or less, which is basically that, you know, the market is irrational, that it's bipolar and that you want to take advantage of that bipolar nature and buy stuff when it's very much out of favor and at a deep discount.

8:03And so then he looks around and he sees that almost nobody else is doing this, that the world is sort of made up of all of these people who are failing to understand the fundamental laws of investing. And he says, well, look, if nobody else is going to do it, the Indian will do it. And so he starts describing himself as a shameless cloner. So for me, this is one of those principles that goes very deeply through investing and life. And so when I'm studying Monish, I'm thinking, and Monish has become a good friend over the years. So I'm studying and I'm thinking, okay, so what can I learn about the way Monish not only invests, but the way he constructs his life?

8:42And one of the things that's so striking about Monish is that almost to an antisocial, you could say almost sociopathic level, Or he just says, I'm not going to do anything that I don't want to do. You know, he's like, I'm not interested in all of the mumbo jumbo related to marketing my funds. So I just don't have any meetings with prospective investors. And he'll have lunch with someone and he'll just say, well, did I enjoy that lunch or not? And he's like, if not, I'll never see that person again. And so he's basically cloned this from Buffett, who he realized just lives in a way that's deeply aligned with who he is.

9:20So I think you can take these principles and then say, well, yeah, so, okay, I want to learn how to clone as an investor, but I also want to learn how to clone in other areas of my life. And that kind of fascinated me that these master principles do run through every area of your life. I think not just investing, they turn out to be very helpful in other areas of life too. Yeah, one line you had when we talked a little bit about the Maverick side, you said, to beat the market, you must be brave enough, independent enough, and strange enough to stray from the crowd. Because after all, if you're going to beat the market, you have to be doing something different than the market.

9:56Yeah, and they are odd, these people. I mean, they really are. I think I've become more and more struck by this over the years, that they're so fanatical and so intense and so extreme in much of what they do. And I remember, you know, Monish went to Charlie Munger's house after the book came out. And he sent me a video where he said, Charlie, you know, what do you think of William's book? And Charlie said, I love the book. It's a great book. And Monish said, what did you find interesting? Were there any insights you found particularly interesting? And he said, yeah, how many of us got divorced or separated?

10:36And he said, it's totally understandable because the game was so absorbing that all of our spouses felt neglected. And I think that's true, that to be really extraordinary at something, you on the whole are going to be pretty extreme, pretty obsessive. there are a few of these people who are reasonably well adjusted and have great families and and a lovely people you'd like to sit next to at dinner but they and and i do like basically everyone i wrote about because i tended to focus on people i liked and admired as humans i wasn't just focusing on you know rapacious billionaires who you know the only talent they had was for making money i wanted to learn from people i thought were admirable as well that there was something special about the way they lived.

11:23But they're deeply eccentric, very extreme. One thing that I took away from the book is that just about every one of them reads and reads and reads and reads, often to the exclusion of doing anything else, whether it's meeting other people or attending to their personal lives. Yeah, I think that's true. I mean, Munger would always talk about Buffett's strength being that he was a continuous learning machine. And I remember Monish describing to me how Munger would just sit there in this big lazy boy chair with these bright lights behind him with two stacks of books and journals and the like on either side.

12:05And he said it was just like this conveyor belt, just motoring through stuff, some of which he skimmed, some of which he read fully. but Monish claims that Munger would read about 500 books a year and and then if you if you add the fact that he had incredible recall there's I mean the way Monish put it was it was like he'd been alive for 300 years you know so so there's a huge advantage to this idea of of applying compounding not only to money but to things like the compounding of knowledge the compounding of wisdom. So in some way, it's like they're intellectual athletes rather than physical athletes.

12:47I think on the whole, I mean, I was joking about Tom Gaynor at some point, the CEO of Markel, about the fact that he would never be in an Olympic beach volleyball team. He was basically perfectly built for this game of kind of sitting and reading and thinking. And maybe because I'm pretty idle and indolent myself, this is one reason why I was so drawn to these people. I think I'm very drawn to the idea that you can sit around and think and read and learn, and that somehow gives you an advantage in life. And there's something sort of deeply subversive about me, I guess, that was drawn to these sort of slightly strange, subversive creatures who had sort of cracked the code of the markets.

13:34And they were, they're all sort of anti-authority in a way. They're all sort of thinking for themselves, questioning conventional wisdom and outwitting the market and outwitting their peers. And so I think for a journalist in a way like me, there's something very appealing about that because, you know, I mean, I'm calling you from a room in London where I'm staying for a few days. And I grew up in England. I went to which was, you know, this famous boarding school where we were literally locked up at 6.15 every evening. And so I just, I think I sort of bridle against rules. And there's something about these rule-breaking mavericks breaking the code that's deeply seductive to me.

14:26When Johann Rahl received the letter on Christmas Day, 1776, he put it away to read later. Maybe he thought it was a season's greeting and wanted to save it for the fireside. But what it actually was, was a warning, delivered to the Hessian colonel, letting him know that General George Washington was crossing the Delaware and would soon attack his forces. The next day, when Raw lost the Battle of Trenton and died from two Colonial Boxing Day musket balls, the letter was found, unopened in his vest pocket. As someone with 15 ,000 unread emails in his inbox, I feel like there's a lesson there. Oh well, this is the constant, a history of getting things wrong.

15:05I'm Mark Chrysler. Every episode, we look at the bad ideas, mistakes, and accidents that misshaped our world. Find us at constantpodcast.com or wherever you get your podcasts.

15:24To the degree that investors can be classified along sort of the value and growth spectrum, I would say most of the investors that you profile lean toward value, not exclusively. You do talk to Will Denhoff, the Fidelity Contra Fund, very successful fund. Bill Miller, I think, could be classified one way or the other. I mean, most of his net worth, I think, is an Amazon or something like that. Yeah. He's along the ways, you know, a little of both sides there. But so, first of all, to the degree that you, do you think that's a fair characterization? And if so, you know, value investing has been a tougher sell over the last five, 10 years.

15:59So are there principles these investors still offer us, even if their style of investing is out of favor? Yeah, these distinctions, as you know, between value and growth and the like are pretty nebulous. And the thing that Munger once said to me, I had this extraordinary two-hour Zoom call with people like Munger and Lou Simpson, a bunch of great investors like that, after the book came out. And one of the things that Munger said to me, and these are his exact words, I tried to sort of tattoo them on my forehead. He said, all investing that's successful comes from getting more value than you pay for.

16:35But then what he said is, look, there are a lot of different ways you can do that. So he said, you can do that like Bill Miller, where Bill went and figured out back in, you know, 1999, 2000, that Amazon, which most of his peers thought was going to go bankrupt, was actually incredibly valuable and would be worth an enormous amount. And Bill at one point a couple of years ago said to me that he was the single largest individual shareholder of Amazon, not named Bezos. So, I mean, you know, he's built an enormous fortune there, but he's also in recent years built an enormous fortune in Bitcoin. And so there's a kind of, there's a free thinking willingness among a lot of the great investors just to look for things that they think will be more valuable.

17:24And there's so many paths up the mountain. But I think, I mean, in terms of a takeaway for the rest of us, one thing that very much struck me, I wrote a chapter about simplicity. And I think it's very helpful to reduce the complexity of investing to a few simple rules that you basically are pretty sure are approximately true on average over time. And so for Danoff, when I went to visit him in Cambridge, Massachusetts, and I thought, oh, there's some great secret source to this guy managing over$200 billion with this amazing record over the last 30 years, he said, yeah, it all comes down to three words.

18:05He said, stocks follow earnings. And so he didn't really care about the valuation that much unless it really got absurd. He was just trying to buy companies that he felt that they're best in class companies. And over time, they're going to do great. And all things being equal, if their earnings double, their stock price will probably double. And so that led him to buy things like Microsoft and Tesla and Berkshire Hathaway, very high quality stuff. but he made it sound sort of simple and Bill Miller who's a good friend of Will Danoff said to me you know Will Danoff claims that he's not that smart and so he keeps it really simple and he's like that's nonsense he's like he's really smart and he's really driven and I think that's another thing that these guys there is this intensity and this ferocity so even if the principles themselves are quite simple the application of the principle requires an amazing degree of intensity.

19:02And I remember Bill Miller telling me once that when he first met Will Danoff, something like 30 years ago, I think they went to some meeting in Phoenix where they were introduced. And they're both really likable guys, right? And someone says to Bill, oh, meet Will. And Bill holds out his hand and says, hi, Will, nice to meet you. And Will Danoff doesn't extend his hand and says, I'm going to beat you, man. I'm going to beat you. And I think that gets at the intensity of it. That gives you a sense that I think at one point in the book, I write something like that sometimes the real secret of success is nothing more mysterious than the fervency of a person's desire.

19:45And so I don't think it's that the principles are that hard. I think the application can be very, very difficult. But again and again, you come back to the idea with people like Howard Marks or Joel Greenblatt or Charlie Munger, that it's really about buying things at a discount to what they're worth. And so that fundamental principle of the margin of safety, I think, is probably about as resilient and timeless and robust a principle as there is in investing. Now, let's talk a little bit more about that margin of safety, because many of the investors you profile did talk about why it's important to understand the risks you're taking, not to take too much risk, and to always be in a situation where you are going to be okay no matter what happens.

20:33The term, unfragile, was used. Talk a little bit about how they think about which investments to buy, the right sizing, and maybe how much to have in cash, so that no matter what happens, they're still going to be okay. I think the most fundamental rule, in a sense, is that you've got to stay in the game. And so you have to set yourself up to survive, despite the fact that the future is unknowable and that anything can happen. And so one of the things that Howard Marks talked to me about is just the importance of not overreaching. He would say, look, given the fact that you don't know what the future holds, you have to ask yourself, will I be able to survive an uncertain future?

21:18So that requires you to set aside enough cash, not to have leverage, not to have too much debt, not to be living beyond your capability. But also he pointed out, it's very important not to underestimate how emotionally and psychologically fragile you might be. And his view, of course, is that people say that they'll be fine if the market goes down 20, 30, 50%. But then when it actually happens, they tend not to be. So this question of, I think, figuring out how you'll cope in drawdowns is hugely important, and just not deluding yourself. So I think one thing that I started to ask myself is, where am I fragile, both in my portfolio and my life?

22:05And how can I reduce that fragility? And so I think if you have all of your money in one asset class or all of your money in one bank account or one brokerage firm or one currency, you're playing with a loaded gun. And so you just want to assume that terrible stuff can happen. And I remember Charlie Munger at one point, I went to a Daily Journal meeting, the company he was chairman of back in 2017. And I remember him saying that that he had had four drawdowns of 50 % over the course of his lifetime. And he said, and Berkshire itself had gone down 50 % three times. And so he said, you have to set yourself up so that you can survive those drawdowns with grace and aplomb.

22:56And he said, if you don't have a drawdown like that, the chances are that you're not taking enough risk, you're not being aggressive enough. So I think this idea of just setting yourself up to survive both emotionally and financially is really key. And I think of this a lot in terms of my own life. I'll often think, this is very much a clone from Charlie Munger. I think about trying to avoid situations with asymmetric risk on the downside that can be catastrophic. So think of things like driving while drunk or texting while you're driving or cheating on your taxes or cheating on your spouse if you happen to love your spouse and don't want to wreck your marriage, you know, things like that.

23:46These are things where there's tremendous downside and limited upside. And so I think just this idea that you want to remove fragility is very important. And there's a beautiful line from Nassim Taleb. You know, I stole the phrase anti-fragile from Nassim Taleb. There's a beautiful bit in one of his books where he says, the fragile breaks with time. And so I think one of the things we learned from Howard Marks is we don't know when something will break and we don't know if it will break. But the longer you go on doing stuff that makes you fragile, the more you're playing with fire. So if you cheat on your expenses once, you'll probably get away with it.

24:30Cheat on your expenses or on your spouse, whatever, 50 times. Sooner or later, you're likely to get into trouble. And so I think, again, these principles that are very powerful in investing turn out to be incredibly helpful in life. Another common theme with many of the folks you profiled was the ability to basically estimate odds and probabilities of something. And that's partially what investing is. right? I'm going to put my money here because I think it's going to be worth more in the future, but I have to assign some sort of probability to that. And for many of them, they basically learned this from playing games, whether it was playing poker.

25:07A lot of them love bridge. Yeah. In some ways, the greatest emblem and icon of this is Ed Thorpe, who I write about in the introduction to the book. And Ed, I often think of as the greatest gambler in history, the greatest game player in the history of investing. I mean, this is the guy who not only figured out how to beat the casino at blackjack, but then figured out how to beat the casino at roulette, and then figured out how to set up this hedge fund that basically didn't have a losing quarter in 20 years. So when I talked to Ed, one of the things that I was trying to figure out is not only how you succeed in investing, but how you apply that kind of game player's approach to life.

25:48Like if If you were approaching life, how would you stack the odds in your favor so that it was likely to work out? And he used the example of health. And he said, look, there are certain illnesses or predispositions you might have, and those are like the cards you're dealt. But then it's your choice whether you get vaccines, whether you get a checkup every year, whether you eat well, whether you exercise and the like. And so it's really all about how you play the hand you're dealt. and that's been really helpful to me because again it goes back to what bill miller was talking about with the stoic philosophers you have to distinguish between what you can and can't control and so i think what they're doing a lot of the great investors is just that they're focusing on what they can control and so for for you know when ed thorpe when i when i was fact checking the book i was asking him how he dealt with um with the covid crisis and and he was like oh thank you for asking.

26:43And it turned out to be unbelievable the way he dealt with it. Like really early on, before there was a single reported death in the US, he'd analyzed the data from Wuhan in China and figured out, you know, what this meant, but also by drawing on deductions from what had happened during the Spanish flu in 1918, which had killed his grandfather. And so he figures out before anyone had been reported dead in the US, that something like 200 to 500 ,000 people were likely to die over the next year. And so he puts himself in isolation with his new wife before, you know, anything happened, basically, and buys masks and buys, you know, detergent and the like.

27:27And so, again, it's like this insistence on analyzing the data for yourself, thinking for yourself independently, looking and giving total primacy to staying in the game and what could be more fundamental than staying in the game by actually literally surviving. And so I just thought that was a beautiful emblem of how to think about life. And similarly, Munger would often talk about only playing games that you're equipped to win. You know, Munger, when he was asked for career advice, said at one point, look, if you're five foot three, don't become a professional basketball player competing against people who are eight foot tall, you know, find something where you have a natural talent, where you have natural advantages and that you're obsessed with.

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28:13And so that again, super practical advice, just in both in investing in life to stick with games that you're equipped to win. So for someone like me, who's not really interested in sitting around reading annual reports all day long, and it's not very numbers oriented, I'm much more of a of a word person. It just doesn't make sense to me to be, you know, buying individual tech stocks and the like. So I have to be very realistic in looking at my own strengths and weaknesses and then stick to games that I can play.

29:13Fucking free or available numbers. I have to point out, and you explain this in your book how Ed Thorpe managed to play Roulette's. And he basically had a computer he made of his own and was of help with somebody else and was activated by his toe, which gave him basically an estimate of the velocity of the ball, which increased his odds of picking the right place where the ball would land. It's such a beautiful example because really what he did is he turned a game of total chance into a game of skill by giving himself a little bit of extra information. And so then you think about how to apply that to investing and you say, well, So is there any reason to think that I have an advantage over someone like Will Danoff or Bill Miller in picking individual stocks?

30:02And if I don't, if there's no reason, I mean, I asked Ed Thorpe this. I said, you know, how do I know if I have an edge? And he's like, well, basically, look, if you have to ask that question, the odds are that you don't have an edge. And so this is not really an admission of failure. It's really liberating. Once you look at yourself with self-honesty, you can say, well, okay, so there's a great default position here. I can just invest in an index fund. And that's absolutely fine. I don't need to be the best in order to succeed. What I need to do is keep my expenses down, stay in the market for the long term, keep adding to the pot, not erode my gains by doing stupid stuff like trying to time the market.

30:47And so in some strange way, it's hugely empowering to recognize your own limitations. Let's dig a little deeper into a few of the characters that you discuss in the book. And maybe you could talk a little bit about their lives and then what you think are the most important lessons investors should take for them. And let's start with someone you've already mentioned, John Templeton. Yeah, Templeton was a deeply eccentric figure. And I got a glimpse of this when I was, he lived in the Bahamas in this beautiful gated community called Lyford Key, where people like Princess Grace of Monaco and Sean Connery, aka James Bond, lived.

31:31And I remember walking on the beach once and I went there a couple of times and I remember sort of hiding behind a palm tree and sort of watching this strange looking figure, this old man, then about 85, with a hat with a visor and ear flaps and his face just slathered with white sun cream. And he's pumping his arms and legs up and down in the ocean to exercise. And he apparently would do this about 45 minutes a day. and i remember thinking god this is so strange here i am i've come to see this great sage you know this guy who i think he'd average something like 14 and a half percent a year for 38 years i mean this incredible return which i think means you turn like a hundred thousand into 17 million or something i mean a really truly great investor and i'm thinking oh it's going to be like you know going to meet this profit and here he is this really odd duck you know um pumping his arms in the water wearing a ridiculous visor.

32:28And then when I get back to New York, I interviewed someone who said, you know, the thing that people like Templeton and Buffett and Soros have in common is this willingness to be lonely, this willingness to do things that make them not look that smart. And that for me was incredibly helpful, you know, to realize that someone like Templeton just had no problem at all diverging from the crowd. And he had done this extraordinary bet back in World War II, after Nazi Germany had invaded France, and the world really seemed like it was coming to an end. I mean, I think the Dow got down to something like 381 at some point, if I remember rightly, around 1942.

33:09He buys 104 companies that are all, 104 stocks that are all trading under a dollar. And this broker says to him, well, obviously, we didn't buy the 37 for you that were in bankruptcy. And he's like, no, no, I want those too. And so just the courage of this guy to buy what he regarded as the point of maximum pessimism. It's an extraordinary thing. And then, you know, to hold them through the chaos of World War II until basically he got to a point where he'd made five times his money off these things. And so I think in a way, it gives you a sense that to outperform, you've got to have this ability to think for yourself, to keep your emotions in check when other people are either, you know, madly exuberant or panicking and desperate and selling.

33:59And what was amazing is when he started in his career, there was only really one book that he had read on investing. I mean, nothing was available. And so he figured this stuff out for himself. And so I think part of what he had done is he'd lived through the Great Depression when people like his father lost almost everything. I mean, his father said to him at one point when he was at Yale, his father said, I can't even contribute$1 to your education. And so I think Templeton had seen all of these people in rural Tennessee, where he was from, who had lost everything. And he realized the best time to buy an asset is when other people are desperately selling.

34:37And so one of the things that I got from Templeton was just this idea that you want to stay away from your own emotion, beware of your own emotion, Beware of your own ignorance. Beware of your overconfidence. You know, I remember him once saying, he said to me, in quite a, I would say kind of a slightly mean way, I felt a little bit like he was slapping me around the head. He said something like, you know, why would you think that you could choose the best asset manager, the best fund, the best asset class? You know, just have a little humility. And so he said to me, basically, what you want to do for the regular investor, you want to own about five or six funds that give you exposure to different asset class, different parts of the market, rather than assuming that you can choose the one thing.

35:29And that's been hugely helpful to me in practical terms. I've often, whenever I get carried away, I sort of remind myself of that simple idea of, let me have about five or six assets that are not totally correlated. And I'm more likely to survive than if I roll the dice and put everything on red. Yeah, I would say he's probably the person most associated with the idea of being optimistic when everyone else is pessimistic. And then the other way around, as you write in the book, he did that during the dot-com craze when everyone was overly optimistic. And he shorts a bunch of IPOs. And then, of course, he turns out right and makes millions of dollars.

36:15Yeah, I think he made something like$90 million, if I remember rightly. And I'm friends with his great niece, Lauren Teppleton, who is a hedge fund manager as well. And I do one thing that's interesting that Lauren told me a year or so ago when we were in Switzerland together at a ValueX event there. I asked her something about Buffett. And she said that whenever Buffett's name came up, his face would drop. And she said he really admired Buffett tremendously, but he was so competitive that it sort of pained him to hear Buffett's name. So I think that's really revealing. Like even someone who is brilliantly clever like Templeton and unbelievably successful, you know, turns himself into a multibillionaire.

37:04He was still so competitive that the mention of Buffett's name was a source of pain. That's so funny, especially for someone who, by the way, was also very religious. Yeah. Let's move on to Howard Marks, co-founder of Oaktree, who you call the philosopher king of finance. Yeah, Howard has this extraordinary background where he went to Wharton and was very artistic. and he wanted to study art and he got thrown out of the art class immediately because they basically were oversubscribed and they said um you know where do you study what's your name and he said you know howard marx warden school of finance and they said right you're the first out and so he had to figure out what to do and and he flukes his way into a japanese studies class where he discovers this concept of mujo, which is basically about impermanence.

38:02It's the idea that everything changes. Nothing stays the same. And this turned out to be an incredible stroke of fortune because it becomes a kind of guiding principle in his investing career. And he would attribute it in large part as a great source of his success. So the lesson in some ways that I drew from Howard that's been life-changing for me is you can't predict the future, but what you can do is accommodate yourself to reality as it is. So you look at reality and you say, okay, everything is changing. Everything is in flux. Nothing stays the same. You know, companies that were once powerful will die.

38:43Industries that were out of favor will rise again. Countries that were in power will fall apart. And so you just recognize this fundamental buddhist truth right this zen buddhist or tibetan buddhist truth that everything is in the state of flux and then you say okay so if that's the case let me accommodate myself to reality as it is so when the conditions are too ebullient for example and everyone is just throwing caution to the wind you want to accommodate yourself to that reality by saying well let me drive a little more carefully you know it's as if you're driving on thin ice and you just want to make sure that you drive 30 miles an hour, not 70 miles an hour.

39:24And likewise, when there's too much pessimism priced into the market, then paradoxically, the market is possibly less risky and you want to gun the engine. And so he did this during the financial crisis and made something like$9 billion, if I remember rightly, by betting on toxic things that nobody else would touch. And so I think this, again, it's a very powerful principle, not only for investing, but for life. You know, you're looking at the reality as it is. You know, a friend of mine got, you know, a really bad health scare recently. And I'm trying to convince him, you know, these are the cards you've been dealt.

40:06Now you have to adjust to it. You can't, you know, one of the things that Howard often quotes is from Peter Bernstein, who's an amazing author who wrote this book Against the Gods about the history of risk. And Peter said something like, the market is not a very accommodating machine. It won't provide you with great returns just because you need them. And so I think just in investing and life, just to look at reality as it is in this unvarnished way and adjust your behavior accordingly is very realistic. And then the other thing about Howard that I really admire is that he's very wary of what I would call master of the universe syndrome, where you start to actually think because you've become hugely successful, but you know, and this is one of the great risks in investing, you know, is overconfidence.

40:58And, and so just to keep reminding yourself of your own good fortune and your own capacity for overconfidence and hubris is very, very powerful. So I think for the rest of us, particularly for men, it's worth remembering that men have a particular capacity for overconfidence. There's actually a study that I think they did at Columbia University where they found that men systematically overestimate their knowledge by something like 30%. And I remember talking about this to Samantha Macklemore, who's Bill Miller's successor, the terrific fund manager and very wise and thoughtful person. And we were laughing about a great story related to this that Michael Lewis had discussed on his podcast.

41:42And basically, there was some woman who was saying that she was descended from Marie Curie, who had won, I think, a Nobel Prize for economics and a Nobel Prize for physics. And some idiot man helpfully pipes up and says to her, it's actually pronounced Mariah Carey. And this is one of those things where you just want to remind yourself, if you're a man, that we should be particularly aware of our capacity for overestimating what we know. Let's move on to a third person. Probably most people aren't familiar with him, but you had mentioned that he may be the person you admire most, and I have to agree with you.

42:22So introduce the world to Arnold Vandenberg. Yeah, Arnold is such a wonderful human being. And the way I think of Arnold is that he's not the most successful investor I've ever met, but he's the most successful human being I've met in the investment business. And part of it is that he was dealt such an awful hand. So he started off, he was sort of least likely to succeed, right? Most of these people were sort of born three feet from the finish line. You know, they were, they went to Wharton or Harvard or, you know, were incredibly clever already. And they were born in the U.S. where they had great advantages riding the fantastic economy for decades.

43:06Arnold had exactly the opposite. Arnold was born on the same street as Anne Frank in Amsterdam. It was a Jewish kid in 1939. And so he was in hiding for the first couple of years of his life behind a fake wall in the closet of a Christian family who hid his family. And then he was sent to an orphanage. And amazingly, a 17-year-old girl who didn't know his family risked her life to take him into the countryside to hide him in a Christian orphanage. And he more or less starved to death there. I mean, he was, by the time, by the time he got out of the orphanage at the age of six, he told me that basically he couldn't walk.

43:50He was just sort of shuffling along on his knees because he was so malnourished. And then he comes out and his, his parents had actually been sent to Auschwitz during the Holocaust, but unbelievably, both of them survived and they come and pick him up and they, they, they take him home. And he said, I couldn't even recognize them at that point. And he said, I just didn't even care. He's like, you know, I would have gone with anyone to get out of that place. And so they moved to East Los Angeles to a very rough neighborhood where on his first day at school, his mother sends him to this really rough school dressed in lederhosen.

44:23So he gets beaten up at school constantly. And he's this thin, emaciated, malnourished kid. And he barely makes it through high school. I mean, someone, he overhears his mother talking to a psychologist who basically says, look, he's probably got brain damage from having been so malnourished. And so he grows up thinking that he's stupid, knowing that 39 members of his family have been killed by the Nazis. So he's full of rage. Then he gets married to his high school sweetheart who runs off with another man. So he's full of rage and disappointment. And he turns around his life in the most extraordinary way that is such a triumph of the human spirit and becomes a very successful investor over decades.

45:12And you look at this and you just think, well, wait a second, with my minor problems in comparison, what can't I do to gain control of my life, to turn things around? And so part of why I end the book with Arnold is because I think he's such a beautiful role model for actually how to live and how to play your cards in the best possible way. And he's continued to be a great role model to me. He called me, he keeps calling me to give me advice so he knows how idle I am. And so he would do things like sending me a trampoline because he wanted me to exercise more on the trampoline. Or he would, a couple of weeks ago, he called me and he said, I'm working on a program for you William I'm putting together various books about nutrition and health and he's so excited about you know here's a guy in his mid-80s very successful guy and he just wants to help and there's something so beautiful about that and I I don't know I I think this is one of really the secrets of life is when when you look at who among the great investors is happiest, consistently I see that it's people who have some mission beyond their own ego, beyond themselves, right?

46:31They're trying to lift up other people. And Arnold is such a beautiful example of that. He just gets such joy out of helping people. And actually, he said to me again and again, I mean, so many times, he says, because of your book, I've been able to help so many people because people reach out to me and I've been able to help them. And so last time he said this, he said, so thank you, thank you, thank you for helping to fulfill my dream of helping other people. So you listen to that, and you're like, well, what a spectacular human being. The dream was not to make billions of dollars and lord it over other people by being in his fabulous mansion and driving around in his Lamborghini.

47:11It's like, no, he has a house in Texas that cost him like 300 and something thousand dollars decades ago and he he drove like the world's cheapest car for many years but then his his wife who he adores bought him a lexus and he said i i was too embarrassed to want to drive it at first but i saw how much pleasure it gave her and after a while i got used to it and so i look at that and i just think this is this is a guy i actually want to be more like i you know if If I could be less selfish, kinder, use whatever gifts I have to lift up other people, I'm likely to be happier. Well, William, this has been a fascinating discussion.

47:55Thank you so much for joining us. It's been such a delight. Thanks for the opportunity to chat with you.

48:03As always, people on the program may have interest in the stocks they talk about. The Motley Fool may have formal recommendations for or against. So don't buy or sell stocks based solely on what you hear. All personal finance content follows Motley Fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosure, please check out our show notes. I'm Robert Brokamp. Fool on, everybody.

From the publisher

William Green is the author of “Richer, Wiser, Happier: How the World's Greatest Investors Win in Markets and Life.” Green also hosts a podcast with the same title. In this replay of an interview from February of this year, Robert Brokamp caught up with William for a conversation about:

- What successful investing comes down to.- The personality traits of market beaters.- Investing lessons from Charlie Munger, Howard Marks, John Templeton, and Arnold Van Den Berg (an investor you may not know about, but should)

Companies mentioned: BRK.A, BRK.B, MKL

Host: Robert BrokampGuest: William GreenEngineer: Bart Shannon

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