#1: The Greatest Speculator Of All Time: Jesse Livermore cover art

#1: The Greatest Speculator Of All Time: Jesse Livermore

#1: The Greatest Speculator Of All Time: Jesse Livermore

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This episode is about Jesse Livermore. The most legendary trader who ever lived, and the man behind Reminiscences of a Stock Operator.

He made $100 million shorting the 1929 crash (about $1.9 billion today), yet died broke just a decade later.
Livermore’s life reads like a novel: ambition, obsession, and lessons written in blood.

What to expect in this episode:

  • How Livermore discovered technical analysis before it even had a name
  • The boy who ran away at 14 to chase numbers on a ticker tape
  • Why he said: “The market does not beat them. They beat themselves.”
  • How he made his first fortune shorting the 1907 Panic — and his biggest one in 1929
  • The deadly enemies of every trader: ignorance, greed, fear, and hope
  • His rule for sitting tight — and why it’s harder than being right
  • How obsession turned from his greatest strength into his undoing
  • Why the game teaches you the game… and then breaks you

“It never was my thinking that made the big money for me. It always was my sitting.” — Jesse Livermore

Books Mentioned:

  • Reminiscences of a Stock Operator by Edwin Lefèvre
  • How to Trade in Stocks by Jesse Livermore

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→ Website: moneymenshow.com

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