The Financial Mistake We Keep Making and How to Stop

August 25, 2026

AI Summary

5 min read

In 1929, the stock market didn't just collapse. Awareness collapsed first—a loss of collective memory about how easily booms turn to busts. That is the through line Andrew Ross Sorkin, financial columnist and CNBC co-anchor, brings to his eight-year project on the Great Crash. On The Oprah Podcast, he explains why the 1929 story is not about rates or regulation but about human nature: the same impulses that drove the Roaring Twenties—fear of missing out, easy credit, and the dressing up of hope as certainty—are alive today.

The Crash as a Mirror, Not a History Lesson

Sorkin wrote 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation as a novelistic drama, not a textbook. He wanted readers to feel the personalities: the hubris, the egos, the bankers who had no regulators looking over their shoulders. Insider trading was legal. The SEC did not exist. People did not know where the line was, which gave Sorkin, oddly, some empathy for them. The parallels to the present are uncanny. The meme stock frenzy around GameStop in 2021? That was 1929 with a smartphone. The excitement about AI and Nvidia? That is the radio stock RCA—the meme stock of its era. Tariffs in 2025? That echoes 1930. Sorkin did not set out to write a warning, but as he worked on news stories while writing the book, he kept thinking, "Oh my goodness, this is exactly like 1929.

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What you'll learn

1 (00:00) **Why the 1929 Crash Still Matters Today** - Andrew Ross Sorkin explains that the story of 1929 is not just about market collapse, but the collapse of collective awareness and why it feels like looking in a mirror for our current moment.
2 (03:45) **The Roaring '20s Were Driven by FOMO** - The cultural phenomenon of "fear of missing out" was the primary driver of the 1929 bubble, even though the term didn't exist yet.
3 (06:22) **Modern Parallels: Meme Stocks, Tariffs, and AI Hype** - Sorkin describes realizing while writing the book that current events were eerily echoing 1929, from the GameStop frenzy to the excitement around AI.
4 (07:52) **The Biggest Lesson: Humility and the Danger of Debt** - The core lesson from 1929 is the need for humility, as overconfidence and the willingness to take on excessive debt led to the crash.
5 (08:47) **The Cassandra Problem: Why Warnings Go Unheeded** - There are always voices of caution, but they are dismissed because being right too early looks like being wrong in the moment.
6 (11:44) **Current Warning Signs That Give Sorkin Pause** - Sorkin lists specific cultural and financial patterns he sees today that mirror pre-crash 1929, including excessive optimism and a betting culture.
7 (13:09) **Is AI a New Story or a Sophisticated Version of the Same Old One?** - Sorkin argues that the AI boom requires a "dream" to make the math work, which makes him cautious despite the genuine potential.

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Guests on this episode

Andrew Ross Sorkin

Show Notes

BUY THE BOOK!

'1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation' by Andrew Ross Sorkin

Are we headed for a financial crash like the one in 1929? Oprah sits down with Andrew Ross Sorkin, financial columnist for The New York Times, co-anchor of CNBC's Squawk Box and bestselling author of 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation, for a thought-provoking conversation about money, human nature and the warning signs we may be missing right now. From the irrational exuberance of the Roaring Twenties to meme stocks, A.I. and today’s “YOLO” culture Andrew explores the surprising parallels between then and now and why every generation eventually faces a financial reckoning. Andrew answers audience questions about whether we could be headed for another major downturn and what that could mean for everyday Americans. Plus, he shares some of his most important money lessons: from why women may be better investors and the six-month savings rule to teaching kids the value of a dollar and preparing for an uncertain financial future.

00:00:00 - Welcome Andrew Ross Sorkin, author of “1929”

00:04:50 - Credit didn’t exist

00:07:00 - How 1929 parallels today

00:08:33 - Biggest lessons from 1929

00:12:09 - The patterns that give Andrew pause

00:14:20 - Andrew was daunted by writing this book

00:17:50 - The financial crash is coming

00:20:12 - America would have been better off with women in charge

00:22:00 - Retirement is a woman’s issue

00:23:15 - Advice for recession

00:25:20 - Most Americans are not ready

00:27:25 - Will AI delay life milestones?