1929 vs 2025: Andrew Ross Sorkin on Crashes, Bubbles & Lessons Learned artwork

1929 vs 2025: Andrew Ross Sorkin on Crashes, Bubbles & Lessons Learned

All-In with Chamath, Jason, Sacks & Friedberg

October 16, 2025

(0:00) Chamath and Friedberg welcome Andrew Ross Sorkin to discuss his new book, "1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation" (0:38) Why he chose this time period (3:22) The setup: what led to the 1929 crash (19:24) The characters: major players in the...
Speakers: Chamath Palihapitiya, Andrew Ross Sorkin, Jason Calacanis
**Chamath Palihapitiya** (0:00)
Hey, Sorkin, I just went through the comments. The one question keeps coming up over again. Why the f*** are you writing this book? Jesus Christ, what a party pooper.

**Andrew Ross Sorkin** (0:09)
What a party pooper? I don't know, man. I think the book is supposed to be like a beach read.

**Chamath Palihapitiya** (0:15)
A beach read? Yes.

**Jason Calacanis** (0:16)
Chamath, did you read it?

**Chamath Palihapitiya** (0:17)
My God, no. I saw the title. I was like, skip.

**Jason Calacanis** (0:34)
What did you guys think? That was fun.

**Andrew Ross Sorkin** (0:38)
Chamath, you're going to love these characters. I kid you not. I kid you not. The people who are involved in this at that time, like the main character.

**Chamath Palihapitiya** (0:48)
I totally agree with you. I am a huge, to be honest, I've studied this period for a while. Actually, I think it's great that you wrote this book. I think it's incredibly fascinating.

**Jason Calacanis** (0:56)
We're here with Andrew Ross Sorkin, Chamath and I, with another All-In interview riveting. Today, we're going to talk about Andrew's new book, 1929, and specifically cover why Andrew got into it, what the history teaches us, and are we looking at another 1929 or something different this day and age? As a lot of people may speculate, but Andrew, thanks for joining Chamath and I to talk about this.

**Andrew Ross Sorkin** (1:21)
Thank you for having me, and I love your background there.

**Jason Calacanis** (1:26)
Thank you.

**Andrew Ross Sorkin** (1:27)
A true image of what was actually happening in October of 1929, crazily enough.

**Jason Calacanis** (1:33)
That's right, and it was colorized by some AI or something, I think. But yeah, great. How and why did you get into this era of 1929, the great stock market crash of 1929? You're a busy guy, you're on TV every day, we see you all over, you're at conferences. I saw you at a conference in Southern California this week, then you're at another conference and you're back in New York. You're very busy. At what point did you say, hey, I want to sit down and write a book about this era?

**Andrew Ross Sorkin** (1:59)
Okay, so here's what happened to me. So I've written that book, Too Big to Fail, about the 2008 financial crisis.

**Jason Calacanis** (2:05)
Right.

**Andrew Ross Sorkin** (2:05)
And people used to always say to me after that, they'd get into these very in-depth conversations about 1929, or they'd want to know more about 1929 And most people know that something terrible happened in 1929, they know there was a crash in 1929, they oftentimes think it like is the Great Depression or leads to the Great Depression. But if you were to ever ask most people, now Chamath and you are maybe in a different category and say, well, who were the people who actually were engaged in this? What were they saying to each other? Who was sleeping with who? Who was trying to f**k over who? What was actually happening here? And what were the incentives and what were the motivations that led to what clearly were some poor decisions?
I couldn't find that. So I went on a vacation like 10 years ago with my wife, very nerdy, and I downloaded all these books to my Kindle. And there's some great books, by the way, about this period. Don't get me wrong. But they didn't have the sort of character-driven story. Like I loved Den of Thieves. I loved Barbarians at the Gate. I loved stories about people.

**Chamath Palihapitiya** (3:07)
Fabulous books. Fabulous books.

**Jason Calacanis** (3:08)
What did your wife think when you ignored her the entire vacation, you guys were just reading books on your Kindle?

**Andrew Ross Sorkin** (3:14)
I mean, I think she thought it was out of my mind. But no, so I read these books and I was like, okay, where's the story? Where's the where the people?

**Chamath Palihapitiya** (3:22)
Before you get to the people, can you can you give people a concise tick? Like I was going to ask you for a tick tock of the overarching economic issues before we get to the sort of the characters? Because I think, yeah, because I think what to your point, which is an important one, people think it was like, okay, stocks went down.
But the other things like the overproduction of the economy, tightening interest rates, the war debt, like all of this stuff was just co-mingled and nobody fully understands that. Can you maybe give folks a precise representation of the setup?

**Andrew Ross Sorkin** (4:00)
Okay, so let's just go back, even let's go back to 1919, because actually I think that's a critical year. So prior to 1919 in America, people did not really borrow money. It was like a moral sin to get credit. People didn't do it. In 1919, General Motors says, you know what, we're going to start lending people money so that you can buy a car. And that was actually like a major inflection point in America, because then Sears Roebuck clocks what's going on and says, okay, we're going to do this too for appliances. And then a guy named Charlie Mitchell, who ran a bank called National City, which becomes Citigroup, says, you know what, we can do this for stocks.

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