The trader who made $100mn from the 1929 crash — only to lose it all

The Story of Money

Manuela Saragosa

Finance, Business, Banking, News, History, Markets, Investing, Crypto

4.4 • 409 Ratings

🗓️ 22 July 2026

⏱️ 55 minutes

🔗️ Recording | Apple Podcasts | RSS

🧾️ Download transcript

Summary

Jesse Livermore was a legendary trader who made and lost several fortunes in the early 20th century, most famously by shorting the Wall Street crash of 1929. His early life was immortalised in the roman à clef Reminiscences of a Stock Operator by Edwin Lefèvre, and his trading insights and stunning successes continue to inspire professional traders and would-be traders to this day. But his life also contains cautionary tales about the ease with which success can morph into failure, and what happens when the buzz of the markets is no longer enough. Host Robin Wigglesworth and the FT's US financial commentator Robert Armstrong explore the extraordinary life of the greatest day trader in history.

Content note: This episode includes discussion of suicide and mental health.

Transcript

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0:00.0	He would walk into stockbroker's offices and they'd think he was a naive kid when, in fact,
0:05.4	he was an absolute shark and would clean the place out.
0:09.4	I mean, I found this great quote that apparently he gave to his kids, the only way to get
0:13.5	a real education in life is to examine each and every one of your mistakes.
0:18.3	Yeah. And isn't that the truth on Wall Street in life? I know. I know.
0:23.0	I know. I think what's so compelling about Jesse Livermore is that he does learn from his mistakes,
0:28.1	most of the time at least. Bad investors, what they do and what I've done when I've made mistakes
0:34.7	is you think you lost because it was a coincidence.
0:38.8	Livermore never does that.
0:40.4	Yeah.
0:40.8	The only thing that is winning is making money.
0:43.7	And if you lose and lose money, it's because you were wrong.
0:47.0	Not because you were unlucky.
0:59.9	Today. Today on The Story of Money.
1:08.6	How do you make a hundred million bucks when Marx are crashing and everyone else is losing their shirt and then somehow blow it all?
1:15.2	Well, today we're going to be talking about one of history's most legendary traders, Jesse Livermore.
1:19.8	He made a cool $100 million in the great crash of 1929.
1:24.1	And that's actually $1.5 billion in today's money.
1:28.4	Or if you want to scale it relative to the size of the U economy back then and now, around $30 billion, one of the biggest trading halls in history. He was a larger
1:36.3	than life character who went from Massachusetts farm boy to champagne-soaked parties in New York.
1:43.4	He even helped inspire F. Scott Fitzgerald's Jay Gatsby.
1:47.5	He's basically the patron saint of day traders everywhere.
	...

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