Navigating Risk: Insights from Trading to Theory

In this chapter, two distinguished guests discuss the nuances of risk and uncertainty in financial markets, transitioning from hands-on trading to scholarly exploration. They delve into personal experiences with market crises, the significance of tail risk management, and the evolution of their professional identities amidst changing landscapes. The conversation emphasizes the need for refined thinking in finance, illustrating how insights gained from trading can inform broader decision-making processes.

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Nassim Nicholas Taleb (@nntaleb) spent 21 years as a risk-taker (quantitative trader) before becoming a researcher in philosophical, mathematical, and (mostly) practical problems with probability.

Taleb is the author of a multivolume essay, the Incerto (The Black Swan, Fooled by Randomness, Antifragile, The Bed of Procrustes, and Skin in the Game), covering broad facets of uncertainty. His work has been published into 49 languages.

In addition to his trader life, Taleb has also written, as a backup of the Incerto, more than 70 technical and scholarly papers in mathematical statistics, genetics, quantitative finance, statistical physics, medicine, philosophy, ethics, economics, and international affairs around the notion of risk and probability (grouped in the Technical Incerto).

Taleb is currently Distinguished Professor of Risk Engineering at NYU's Tandon School of Engineering (retired). His current focus is on the properties of systems that can handle disorder ("antifragile").

Scott Patterson (@pattersonscott) is an investigative reporter for The Wall Street Journal, currently based in Washington DC, working on climate and energy policy. His new book is Chaos Kings: How Wall Street Traders Make Billions in the New Age of Crisis, a profile of the rise of “black-swan traders,” such as Nassim Taleb and Mark Spitznagel, as well as a survey of the many perils the world faces today—and how we might fix them.

Scott has covered everything from Berkshire Hathaway to stock exchanges to high-speed traders to the financial regulators. His first book, The Quants, describes the rise of mathematical finance and delves into its role in the 2008 financial blowup. Dark Pools, his second book, tells how computer traders took control of the U.S. stock market, starting from the birth of computer trading in the 1980s to the explosion of high-frequency trading in the late 2000s.

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[09:44] How Scott and Nassim first connected.

[12:02] Why Nassim would rather be remembered as a scholar than a trader.

[14:01] You can’t forge a new friendship without breaking a few eggs.

[16:22] Silent risk, tail events, and one-trick ponies.

[25:56] What prompted Scott to write Chaos Kings?

[33:41] Pseudo-efficiency, pseudo-optimization, and pseudo-sorries.

[36:49] The joy of writing a preemptive resignation letter.

[37:39] Developing resilience against criticism.

[40:33] Recurring patterns in successful investors.

[44:15] Nassim: contrarian, or simply independent?

[46:44] Jiving with skeptical turkeys.

[51:53] Living in the polycrisis.