On today’s episode, Clay reviews Nassim Taleb’s book – Fooled by Randomness.

Nassim Taleb is a Lebanon-born American mathematician and statistician whose work concerns problems of randomness, probability, and uncertainty. He’s very well known for his popular books, including The Black Swan, Antifragile, Skin in the Game, and Fooled by Randomness.

IN THIS EPISODE YOU’LL LEARN:

00:00 - Intro.

01:37 - The role of luck in investing.

04:51 - Biases that get investors into trouble, such as the survivorship bias and the endowment effect.

10:09 - Why we should develop a sense of skepticism and humility.

15:52 - Why it’s so important to understand alternative histories.

30:47 - Why humans are more prone to make investment decisions based on emotions rather than facts and probabilities.

37:31 - What the firehouse effect is.

39:33 - The story of a trader who got married to his positions which ended up being a value trap.

48:08 - What chaos theory is.

58:54 - How Taleb’s investment strategy capitalizes on asymmetric opportunities.

62:06 - Distinguishing a good process from a good outcome.

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members.
Nassim Taleb’s books: Fooled by Randomness, Antifragile, The Black Swan, & Skin in the Game.
Episode Mentioned: TIP558: How Ackman & Taleb Profited Billions During Market Crashes w/ Scott Patterson | YouTube Video.
Episode Mentioned: TIP597: Darwin's Investing Lessons w/ Kyle Grieve | YouTube Video.
Episode Mentioned: TIP579: Big Mistakes by Michael Batnick | YouTube Video.
Follow Clay on Twitter.
Learn more about the Berkshire Summit by clicking here or emailing Clay at clay@theinvestorspodcast.com.
Check out all the books mentioned and discussed in our podcast episodes here.

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10.22.2025

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