#313: Wall Street's Craziest Stories

#313: Wall Street's Craziest Stories

Author: MyWallSt May 28, 2026 Duration: 45:23

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 the automaker spiraled into absolute panic on Wall Street, as hedge funds crowded into what they believed was a “risk-free” arbitrage trade. Instead, Volkswagen briefly became the most valuable company in the world as the stock exploded over three days.

And finally, we tell the story of the “ramen-eating hermit” who made $20 million in 10 minutes.After a catastrophic trading error at Mizuho Securities triggered chaos on the Tokyo Stock Exchange, one obscure retail trader spotted the mistake faster than institutional investors, bought aggressively, and walked away with a fortune. Meanwhile, the brokerage firm behind the error lost an estimated $347 million.

Stay until the end to hear which story the lads love most.

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00:00 Intro

02:22 Chimp Beats Wall Street

08:19 Teen Jordan Belfort

14:25 Hertz Bankrupt Stock Surge

21:58 Investicon announcement

25:08 Volkswagan Short Squeeze

37:23 Ramen Trader Windfall

43:38 Favorite Story and Wrap



Each week on Stock Club, the team from MyWallSt gathers to break down the movements and ideas shaping the market. This isn't about hype or frantic trading tips; it's a grounded conversation focused on understanding how investing actually works. You'll hear them analyze specific stock news and discuss the strategies behind building lasting wealth, all with the aim of making you a more thoughtful and confident investor. The discussion in this podcast naturally evolves from the week's most significant events, offering clarity on complex financial stories without relying on jargon. Tuning in feels like being part of a straightforward, informed discussion where the priority is long-term perspective over short-term noise. For anyone looking to deepen their grasp of the business and investing landscape, Stock Club provides a consistent, reliable space to learn. It’s the regular check-in that helps demystify the market's shifts, emphasizing education and insight as the true foundations for success. You can find Stock Club wherever you listen to podcasts.
Author: Language: English Episodes: 100

Stock Club
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