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:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

3:00 – Meeting Sir John Templeton in the Bahamas

5:12 – Templeton’s WWII stock strategy during market crash

14:00 – Wisdom vs survivorship bias in investing stories

17:38 – Why great investors recommend index funds

28:42 – Prioritizing freedom over wealth maximization

38:31 – Bogle’s client-first philosophy

51:32 – Living below means for market volatility

53:37 – HALT PS conditions leading to poor choices

1:01:07 – Using data for better decision making

1:07:01 – Bogle’s emphasis on simple investing

1:10:36 – Danoff’s “stocks follow earnings” strategy

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#576: The World’s Richest People Are Weird by Design, with William Green

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