EPISODE · May 28, 2026 · 45 MIN
#313: Wall Street's Craziest Stories
from Stock Club · host MyWallSt
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.Psssst…. We don’t think you’ll want to miss this year’s Investicon. Grab your early bird tickets now: https://www.investicon.ie/Prophet, MyWallSt's latest investing service, is focused on delivering market-beating in less than 5 minutes a month.Click here to join now or email [email protected] for a deal.Become a successful investor by checking out all the content MyWallSt has to offer:📩 Email us: [email protected]📚 Learn the fundamentals of investing by downloading our free Learn app: https://bit.ly/3DXPOz7💻 Keep updated on stock market news by visiting our blog: https://mywallst.com/blog/🎧 Tune in to our podcast Stock Club to stay updated on weekly news: https://mywallst.com/stock-investment-podcast/🎉 Follow MyWallSt on social:❌ X: @MyWallStHQ💃 TikTok: @MyWallSt📸 Instagram: @MyWallSt🖥️ Facebook: @MyWallSt👔 LinkedIn: MyWallSt00:00 Intro02:22 Chimp Beats Wall Street08:19 Teen Jordan Belfort14:25 Hertz Bankrupt Stock Surge21:58 Investicon announcement25:08 Volkswagan Short Squeeze37:23 Ramen Trader Windfall43:38 Favorite Story and Wrap
What this episode covers
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.Psssst…. We don’t think you’ll want to miss this year’s Investicon. Grab your early bird tickets now: https://www.investicon.ie/Prophet, MyWallSt's latest investing service, is focused on delivering market-beating in less than 5 minutes a month.Click here to join now or email [email protected] for a deal.Become a successful investor by checking out all the content MyWallSt has to offer:📩 Email us: [email protected]📚 Learn the fundamentals of investing by downloading our free Learn app: https://bit.ly/3DXPOz7💻 Keep updated on stock market news by visiting our blog: https://mywallst.com/blog/🎧 Tune in to our podcast Stock Club to stay updated on weekly news: https://mywallst.com/stock-investment-podcast/🎉 Follow MyWallSt on social:❌ X: @MyWallStHQ💃 TikTok: @MyWallSt📸 Instagram: @MyWallSt🖥️ Facebook: @MyWallSt👔 LinkedIn: MyWallSt00:00 Intro02:22 Chimp Beats Wall Street08:19 Teen Jordan Belfort14:25 Hertz Bankrupt Stock Surge21:58 Investicon announcement25:08 Volkswagan Short Squeeze37:23 Ramen Trader Windfall43:38 Favorite Story and Wrap
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#313: Wall Street's Craziest Stories
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