#313: Wall Street's Craziest Stories

#313: Wall Street's Craziest Stories

From Stock Club by MyWallSt

May 28, 2026 · 45 min · Episode 310

About this episode

Mike and Emmet share some of the craziest stories in stock market history.

This week, Mike and Emmet share some of the craziest stories in stock market history. Starting with a chimpanzee named Raven, who became a star during the dot-com bubble. After throwing darts at a board of internet stocks, her assembled portfolio returned 213% in 1999, making her the 22nd most successful money manager in the United States that year. Then there’s the story of Jonathan Lebed — essentially a 14-year-old version of Jordan Belfort. During the early internet era, Lebed made nearly $1 million running pump-and-dump schemes from his bedroom, buying penny stocks before hyping them up in online chat rooms using fake accounts. The strategy was wildly illegal… but also wildly effective. We also revisit one of the strangest moments of the post-COVID market frenzy: Hertz (HTZ). After filing for bankruptcy, the stock somehow surged nearly 9x as retail investors piled in. Even more bizarre? The company nearly raised fresh capital by selling shares in the bankrupt business — and investors who bought during the chaos actually ended up making money. From there, we move to one of the most famous short squeezes ever: Volkswagen (VOW3). What began as Porsche quietly building a stake in…

People in this episode

Hosts: Mike, Emmet

Topics covered

  • stock market history
  • crazy stock stories
  • pump-and-dump schemes
  • post-COVID market
  • short squeezes
  • investing strategies

Keywords

  • stock market
  • crazy stories
  • Hertz
  • Volkswagen
  • pump-and-dump
  • investing
  • dot-com bubble
  • Jonathan Lebed

Mentioned in this episode

Organizations: Hertz, Volkswagen, Porsche

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