This episode is a two-for-one, and that’s because the podcast recently hit its 10-year anniversary and passed one billion downloads. To celebrate, I’ve curated some of the best of the best—some of my favorites—from more than 700 episodes over the last decade. I could not be more excited. The episode features segments from episode #409 "Brené Brown — Striving versus Self-Acceptance, Saving Marriages, and More" and episode #596 "Edward O. Thorp, A Man for All Markets — Beating Blackjack and Roulette, Beating the Stock Market, Spotting Bernie Madoff Early, and Knowing When Enough Is Enough."

Please enjoy!

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Timestamps:

[06:06] Notes about this supercombo format.

[07:09] Enter Brené Brown.

[07:30] Changing in a lasting, meaningful way.

[08:03] Is self-accepted complacency possible?

[10:53] My woo confession about a crux skill.

[13:06] Narcissism: the shame-based fear of being ordinary.

[14:06] Efficacy isn’t always efficient.

[15:48] Pathology as armor that can’t be discarded.

[16:28] What are you unwilling to feel?

[17:04] Discarding armor that no longer serves us.

[21:26] Curiosity as midlife’s superpower.

[22:53] There’s trauma for all of us.

[23:33] An 80/20 marriage hack.

[25:18] Decisions in a family-focused family.

[27:04] Parenting from compliance to commitment.

[29:31] Enter Edward O. Thorp.

[29:54] Edward’s background, and what drew him to apply mathematics to gambling.

[37:04] Edward’s first blackjack trip to Vegas, reference materials used, and his meeting with Claude Shannon at MIT.

[40:13] Edward and Claude devised a method to beat roulette using the first wearable computer, according to MIT.

[42:16] Despite being 89, Edward looks great for his age; he discusses his approach to staying in shape over the years.

[50:22] Edward explains how he got into finance and investing, and the people he met along the way.

[59:25] Edward shares what convinced him that Warren Buffett would one day be the richest man in the world after their first meeting.

[1:03:58] Edward discusses the frameworks he would teach in an investing seminar for modern students, including those without a strong math aptitude.

[1:08:52] Edward shares lessons learned from investing that are transferable to other areas of life.

[1:11:02] Edward, a long-term thinker at 89, offers advice for those who struggle to think beyond the short-term.

[1:15:40] Edward explains how he discovered something suspicious about the Madoff brothers’ business practices 17 years before others caught on.

[1:24:17] Exploring mental models of externalities, the tragedy of the commons, and fundamental attribution errors.

[1:33:32] Edward recommends reading and listening material for those who want to enact positive change in the world, politically or evolutionarily.

[1:38:51] Edward shares which investors, besides Warren Buffett, impress him and why.

[1:42:52] Edward discusses how he balanced growing a business with personal life and what led him to wind things down.

[1:47:56] Edward defines independence and shares how he spent his time after winding down the investment side of his life.

[1:49:30] Edward shares what he’s particularly curious about learning at the moment.

[1:51:40] Reflecting on a conversation between Joseph Heller and Kurt Vonnegut, and other parting thoughts.

*

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Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more.

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