What’s Too Big to Fail Now? with Andrew Ross Sorkin

October 20, 2026

AI Summary

5 min read

What’s Too Big to Fail Now? Andrew Ross Sorkin on 1929, AI Bubbles, and the Wild Card Nobody’s Talking About

Andrew Ross Sorkin, the New York Times DealBook columnist and CNBC Squawk Box co-anchor, spent eight years writing 1929, a book about the crash that launched the Great Depression. But he’s not trying to say we’re about to repeat it. “I don’t think we’re in 1929,” he says. “I probably think we’re more like the 1990s—maybe 1996 or ’97.” The question, he adds, is whether whatever comes next has to be cataclysmic like 2008. He’s hoping it won’t be. But he has one wild card that could make it worse than all of them.

The 1920s Were Not a Simple Cautionary Tale

The popular image of 1929—a single terrible day in October, then the Great Depression—is wrong. The stock market that year ended down only 17 percent. The real damage came from leverage. People had bought stocks on margin, taking out massive loans. When prices fell, banks didn’t let them wait for a rebound. They demanded repayment. Homes were sold. Savings vanished. That was the first domino.

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What you'll learn

1 (01:00) **Episode Introduction & Guest Welcome** - Naima introduces the episode and her guest, Andrew Ross Sorkin, discussing his book "1929" and his work at DealBook and CNBC.
2 (03:36) **The 1920s Context & The Crash** - Sorkin explains the backdrop of the Roaring 20s, the democratization of the stock market, and the initial crash of October 1929.
3 (06:35) **Are We in 1929 Now?** - Sorkin directly addresses whether the current economy mirrors the pre-crash 1920s, offering a nuanced comparison.
4 (11:27) **The Shift in American Values** - Naima presents a chart showing a decline in patriotism and religion and a rise in the importance of money from 1998 to 2023.
5 (16:01) **Elon Musk's AI Utopia & The Reality of Capitalism** - The conversation analyzes Elon Musk's prediction that AI and robotics will eliminate poverty and make work optional.
6 (19:16) **The 1920s Corollary: John Raskob** - Sorkin profiles John Raskob, the General Motors executive who invented consumer credit and the five-day work week.
7 (21:37) **The Rise of the Financier as Celebrity** - The discussion shifts to how financiers became celebrities for the first time in the 1920s.

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Guests on this episode

Andrew Ross Sorkin

Show Notes

We’re playing you one of our favourite episodes: a conversation with Andrew Ross Sorkin from January 2026. Nayeema asks: When did money become God? Are we due another market crash? What did we learn (or fail to learn) from the 1929, 2008 and other economic crises? And would they bail out OpenAI and Anthropic now — is AI the new “too big to fail?”

Make sure to get Andrew’s book (which Nayeema thinks is “actually great.”

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