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:

[00:00] Start

[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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