Intro

This chapter examines the distinctive traits of the world's greatest investors through anecdotes from years of interviews. It highlights how their unconventional mindsets and diverging strategies, particularly in times of crisis, have led to significant financial successes.

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#576: The world's greatest investors have a secret: they're weird.

When one young fund manager met Bill Miller for the first time, he refused to shake hands. Instead, he locked eyes and declared: "I'm going to beat you, man."

William Green joins us to share what he's learned from decades of conversations with investing legends — from the hyper-competitive to the deeply philosophical.

These conversations reveal that success isn't just about strategy; it's about understanding yourself and playing to your strengths.

The best investors are mavericks who think differently. They're willing to look strange, be lonely, and diverge from the crowd.

Templeton demonstrated this during WWII. When Germany invaded France and markets crashed, he bought 104 stocks trading under $1 — including 37 bankrupt companies. His contrarian bet paid off 5x when markets recovered.

But Green emphasizes this isn't just about getting rich.

His decades of interviews reveal deeper wisdom about building a good life:

Great investors focus on what they can control. They can't predict markets, but they can manage their behavior and emotions.
They embrace simplicity. Jack Bogle advocated owning low-cost index funds rather than chasing complex strategies.
They understand odds and risk. Howard Marks asks "What's the consequence if I'm wrong?" before making decisions.
They play to their strengths. Charlie Munger says if you're 5'3", don't try to be a pro basketball player.
They live below their means. As investor Tom Gaynor notes, "If you're living within your means, you're already rich."

Green shares a practical framework called HALT PS — don't make important decisions when Hungry, Angry, Lonely, Tired, in Pain, or Stressed. This applies beyond investing to daily life.

The conversation explores how to build resilience before market crashes through healthy habits, self-awareness, and preparation. Green notes that many successful investors practice meditation and read widely across disciplines.

Even legends make mistakes. Bill Miller saw his assets drop from $77 billion to $800 million during the 2008 crisis. But he rebounded by staying true to his principles and learning from failure.

Green's key message? Focus less on getting rich and more on building an "anti-fragile" life aligned with your values and strengths.

The best investors aren't just good at making money — they're skilled at creating lives of meaning and purpose.

Find more from William Green at williamgreenwrites.com or on his podcast Richer, Wiser, Happier, featured on the We Study Billionaires feed.

Timestamps:

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(01:00) Meeting Sir John Templeton in the Bahamas

(04:02) Templeton's WWII stock strategy during market crash

(12:00) Wisdom vs survivorship bias in investing stories

(14:55) Why great investors recommend index funds

(23:34) Prioritizing freedom over wealth maximization

(39:27) Bogle's client-first philosophy

(51:32) Living below means for market volatility

(01:01:37) HALT PS conditions leading to poor choices

(01:06:45) Using data for better decision making

(01:11:13) Bogle's emphasis on simple investing

(01:14:30) Danoff's "stocks follow earnings" strategy

For more information, visit the show notes at https://affordanything.com/episode576