Business History How to Make Billions When the Bubble Bursts: Lessons from 1929
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Dec 10, 2025 Explore the high-stakes world of Jesse Livermore, who mastered the art of trading and betting against the market. Hear about his uncanny knack for numbers and his rise to fame before the devastating 1929 crash. Discover how he thrived on volatility and manipulated stocks, and learn about his covert short positions leading up to the bubble burst. The episode delves into Livermore's massive $100 million trade, his subsequent isolation, and the tragic decline of his life, along with the lasting impacts on market regulations that followed.
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From Chalkboards To Wall Street
- Jesse Livermore started as a chalkboard boy and learned patterns by writing quotes all day.
- He parlayed that skill into bucket-shop wins, then moved to Wall Street to trade with real stakes.
Banned From The Bucket Shops
- Livermore traded in bucket shops where bets mimicked stock moves without actual ownership.
- He was so good he got banned and then used disguises to keep playing until he joined Wall Street firms.
Speed As A Trading Edge
- Faster access to information created durable trading advantages in Livermore's era.
- Private tickers and wired communication let him beat the public ticker and capture early moves.
