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Overleveraged, Overconfident
Hosted by a former Fed insider who helped close 200+ failed banks during the financial crisis, Overleveraged, Overconfident dives deep into the biggest ego-fueled flameouts in finance. From hedge fund collapses to crypto pipe dreams, each episode unpacks the toxic mix of ambition, arrogance, and denial that drives smart people to make spectacularly dumb decisions.
Follow the Journey from Hubris to Bankruptcy
Overleveraged, Overconfident
Cafeteria Fight Club: When Billionaires Act Like 7th Graders
What do you get when two Wall Street titans turn a financial feud into a public spectacle? An activist-investing meltdown that plays out like middle school drama—with $1 billion on the line. In this episode, we dive into the infamous slugfest between Carl Icahn and Bill Ackman over Herbalife, the company Ackman called a pyramid scheme—and Icahn called a golden opportunity to make him squirm.
Expect:
- CNBC’s live on-air slap fight that left moderators speechless
- A 330-slide presentation that feels more like a cry for help
- Carl’s refusal to be bullied—and his parting shots, delivered with the enthusiasm of a 12-year-old.
- And the moment this grudge stopped being about Herbalife and started being about ego
This is not just finance—it’s personal. And petty. And perfect.
This episode was researched and written by Cherise Lloyd. Some music was created by using UDO. You can find show notes, transcripts, and sources at www.overleveragedoverconfident.com. Follow us on Instagram at Overleveraged Overconfident. Support the show on Patreon and help us keep deep-diving into those spectacular financial fails.. Overleveraged Overconfident is part of Seven Seven Spider, which specializes in deep dive research and financial storytelling. All research uses publicly available sources, so no confidential or regulatory information, just my keen sense of spotting nonsense.