Renowned financial journalist and author Andrew Ross Sorkin joins Wilf on this week's episode of The Master Investor Podcast to dissect the mechanics, characters, and lessons of history’s most infamous market crash - 1929. Sorkin, the acclaimed CNBC anchor, creator of DealBook, and author of Too Big to Fail, reveals the eight-year odyssey behind his latest book, 1929: Inside the Greatest Crash in History and How It Shattered a Nation.

Sorkin reveals his meticulous process of piecing together lost diaries, newly uncovered archives, and never-before-released Federal Reserve minutes to bring to life the drama, innovation, and excess of the Roaring Twenties. The conversation explores the evolution of Wall Street, the advent of leverage for everyday Americans, and the dizzying rise of stock speculation that led to disaster. Sorkin and Frost draw striking parallels between the optimism and innovations of the 1920s and today’s markets, asking: could it happen again? Sorkin reveals that his big fear today is not knowing how much leverage is in the system - due to the explosion of private credit - because ultimately "the match that lights the fire of every crisis is the leverage".

You’ll hear stories of larger-than-life figures such as Charles Mitchell, John Raskob, John Pierpont Morgan and Winston Churchill, explore why things spiralled out of control, and discover why the aftermath of 1929 still reverberates through financial markets and economic policy now. Sorkin also shares candid insights on his writing journey, career lessons, and the enduring value of patience.

Whether you’re a seasoned investor, student of history, or just fascinated by great storytelling, this episode offers timely lessons and edge-of-your-seat reflections on risk, resilience, and the markets that shape our world.

Photo © Mike Cohen

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