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 No. 409 "Brené Brown — Striving versus Self-Acceptance, Saving Marriages, and More" and episode No. 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:
[00:00] Start

[06:22] Notes about this supercombo format.

[07:25] Enter Brené Brown.

[07:46] Changing in a lasting, meaningful way.

[08:19] Is self-accepted complacency possible?

[11:09] My woo confession about a crux skill.

[13:22] Narcissism: the shame-based fear of being ordinary.

[14:22] Efficacy isn’t always efficient.

[16:04] Pathology as armor that can’t be discarded.

[16:44] What are you unwilling to feel?

[17:20] Discarding armor that no longer serves us.

[21:42] Curiosity as midlife’s superpower.

[23:09] There’s trauma for all of us.

[23:49] An 80/20 marriage hack.

[25:34] Decisions in a family-focused family.

[27:20] Parenting from compliance to commitment.

[29:47] Enter Edward O. Thorp.

[30:10] Edward’s background, and what drew him to apply mathematics to gambling.

[37:20] Edward’s first blackjack trip to Vegas, reference materials used, and his meeting with Claude Shannon at MIT.

[40:29] Edward and Claude devised a method to beat roulette using the first wearable computer, according to MIT.

[42:32] Despite being 89, Edward looks great for his age; he discusses his approach to staying in shape over the years.

[50:38] Edward explains how he got into finance and investing, and the people he met along the way.

[59:41] Edward shares what convinced him that Warren Buffett would one day be the richest man in the world after their first meeting.

[1:04:14] Edward discusses the frameworks he would teach in an investing seminar for modern students, including those without a strong math aptitude.

[1:09:08] Edward shares lessons learned from investing that are transferable to other areas of life.

[1:11:18] Edward, a long-term thinker at 89, offers advice for those who struggle to think beyond the short-term.

[1:15:56] Edward explains how he discovered something suspicious about the Madoff brothers’ business practices 17 years before others caught on.

[1:24:33] Exploring mental models of externalities, the tragedy of the commons, and fundamental attribution errors.

[1:33:48] Edward recommends reading and listening material for those who want to enact positive change in the world, politically or evolutionarily.

[1:39:07] Edward shares which investors, besides Warren Buffett, impress him and why.

[1:43:08] Edward discusses how he balanced growing a business with personal life and what led him to wind things down.

[1:48:12] Edward defines independence and shares how he spent his time after winding down the investment side of his life.

[1:49:46] Edward shares what he’s particularly curious about learning at the moment.

[1:51:56] Reflecting on a conversation between Joseph Heller and Kurt Vonnegut, and other parting thoughts.

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